2530 lines
289 KiB
XML
2530 lines
289 KiB
XML
<document id="AEAA87A9ACD0970EBE9F1E572CBB0141" ID-DOI="10.1016/j.phytochem.2021.112983" ID-ISSN="1873-3700" ID-Zenodo-Dep="8235151" IM.bibliography_approvedBy="carolina" IM.illustrations_approvedBy="carolina" IM.materialsCitations_approvedBy="carolina" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="carolina" IM.taxonomicNames_approvedBy="carolina" IM.treatments_approvedBy="carolina" checkinTime="1691689614589" checkinUser="felipe" docAuthor="Chakraborty, Kajal, Kizhakkekalam, Vinaya Kizhakkepatt & Joy, Minju" docDate="2022" docId="40239D056F769B45FCF71CAB8C43C83F" docLanguage="en" docName="Phytochemistry.193.112983.pdf" docOrigin="Phytochemistry (112983) 193" docSource="http://dx.doi.org/10.1016/j.phytochem.2021.112983" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Bacillus amyloliquefaciens L. M. Liao 1987" docType="treatment" docVersion="2" lastPageNumber="7" masterDocId="BC1AE57D6F779B42FFC5185A884ECE60" masterDocTitle="Polyketide-derived macrobrevins from marine macroalga-associated Bacillus amyloliquefaciens as promising antibacterial agents against pathogens causing nosocomial infections" masterLastPageNumber="13" masterPageNumber="1" pageNumber="2" updateTime="1691778999268" updateUser="ExternalLinkService">
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<mods:title id="2C623A2F75504109B246F439DFCB160B">Polyketide-derived macrobrevins from marine macroalga-associated Bacillus amyloliquefaciens as promising antibacterial agents against pathogens causing nosocomial infections</mods:title>
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<mods:name id="3DD480BB7BB72FAB1E94DBACFD4333F9" type="personal">
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<mods:namePart id="97DA20DFD110DE6C0A3C7C757E4EE546">Chakraborty, Kajal</mods:namePart>
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<mods:affiliation id="45A4186580A49A7D11A46193ED567DA7">* & Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P. B. No. 1603, Cochin, Kerala State, India</mods:affiliation>
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<mods:namePart id="AAFCEF4B6E4629189868EAA5A10AA2EF">Kizhakkekalam, Vinaya Kizhakkepatt</mods:namePart>
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<mods:namePart id="44464F02E5E75F7923C2F23834D0AE7E">Joy, Minju</mods:namePart>
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<mods:title id="1CB0E5C44E37E40991BAB92A76E59F31">Phytochemistry</mods:title>
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<mods:part id="37744A6B7AFC522CDDF42DE596B2F62E">
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<mods:date id="9911942AF5A4684CBAF96C76A4401227">2022</mods:date>
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<mods:title id="DC65431ED716989B9F549BB81DB7CF31">112983</mods:title>
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<mods:number id="3585B5873B1ACDEE75433CBC57EE65BF">2022-01-31</mods:number>
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<mods:number id="D5C795A42A5E5C714F70B84C7B529417">193</mods:number>
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<treatment id="40239D056F769B45FCF71CAB8C43C83F" ID-DOI="http://doi.org/10.5281/zenodo.8239908" ID-Zenodo-Dep="8239908" LSID="urn:lsid:plazi:treatment:40239D056F769B45FCF71CAB8C43C83F" httpUri="http://treatment.plazi.org/id/40239D056F769B45FCF71CAB8C43C83F" lastPageId="7" lastPageNumber="7" pageId="1" pageNumber="2">
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<subSubSection id="80907F986F769B43FCF71CAB8D0BCB64" box="[818,1349,1265,1284]" pageId="1" pageNumber="2" type="nomenclature">
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<paragraph id="C8352C136F769B43FCF71CAB8D0BCB64" blockId="1.[818,1349,1265,1284]" box="[818,1349,1265,1284]" pageId="1" pageNumber="2">
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<heading id="937D9B7F6F769B43FCF71CAB8D0BCB64" bold="true" box="[818,1349,1265,1284]" fontSize="36" level="1" pageId="1" pageNumber="2" reason="1">
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<emphasis id="FAFEF0016F769B43FCF71CAB8D0BCB64" bold="true" box="[818,1349,1265,1284]" italics="true" pageId="1" pageNumber="2">
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2.2. Characterization of the bioactive
|
||
<taxonomicName id="0F8A57906F769B43FB481CAB8D0BCB64" ID-CoL="K8MZ" ID-ENA="1390" authority="Priest et al., 1987" authorityName="L. M. Liao" authorityYear="1987" baseAuthorityName="ex. Fukumoto" baseAuthorityYear="1943" box="[1165,1349,1265,1284]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="1" pageNumber="2" phylum="Firmicutes" rank="species" species="amyloliquefaciens">B. amyloliquefaciens</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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</subSubSection>
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<subSubSection id="80907F986F769B46FC941D738DCDCAD6" lastPageId="4" lastPageNumber="5" pageId="1" pageNumber="2" type="description">
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<paragraph id="C8352C136F769B43FC941D738C4FC9DE" blockId="1.[818,1488,1321,1982]" pageId="1" pageNumber="2">
|
||
The bacterial strain isolated from the rhodophytan marine macroalgae
|
||
<taxonomicName id="0F8A57906F769B43FCAE1D1F8B9CCB38" box="[875,978,1349,1368]" class="Florideophyceae" family="Solieriaceae" genus="Kappaphycus" kingdom="Plantae" order="Gigartinales" pageId="1" pageNumber="2" phylum="Rhodophyta" rank="species" species="alvarezii">
|
||
<emphasis id="FAFEF0016F769B43FCAE1D1F8B9CCB38" bold="true" box="[875,978,1349,1368]" italics="true" pageId="1" pageNumber="2">K. alvarezii</emphasis>
|
||
</taxonomicName>
|
||
, with promising antibacterial activity, was identified by inclusive phenotypic and genotypic characterization (
|
||
<bibRefCitation id="AC1B51E26F769B43FA831D3B8B2CCBF0" author="Krieg, N. R. & Holt, J. G." pageId="1" pageNumber="2" pagination="161 - 172" refId="ref16384" refString="Krieg, N. R., Holt, J. G., 1984. Bergey' s Manual of Systematic Bacteriology, vol. 1. The Williams and Wilkins Co, Baltimore, pp. 161 - 172." type="book chapter" year="1984">Krieg and Holt 1984</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="AC1B51E26F769B43FCAB1D278C7DCBF0" author="Thilakan, B. & Chakraborty, K. & Chakraborty, R. D." box="[878,1075,1405,1424]" pageId="1" pageNumber="2" pagination="668 - 681" refId="ref17460" refString="Thilakan, B., Chakraborty, K., Chakraborty, R. D., 2016. Antimicrobial properties of cultivable bacteria associated with seaweeds in the Gulf of Mannar on the southeast coast of India. Can. J. Microbiol. 62 (8), 668 - 681. https: // doi. org / 10.1139 / cjm- 2015 - 0769." type="journal article" year="2016">Thilakan et al., 2016</bibRefCitation>
|
||
), as Gram-positive bacterium with amylase activity. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-
|
||
<emphasis id="FAFEF0016F769B43FBC11DEF8C68CBA8" bold="true" box="[1028,1062,1461,1480]" italics="true" pageId="1" pageNumber="2">ToF</emphasis>
|
||
MS) score of 1.92 and 99% similarity in 16S rRNA sequence (KX272633) coupled with membrane fatty acid composition characterized the bacterial strain as
|
||
<taxonomicName id="0F8A57906F769B43FACA1DB78D87CB9F" box="[1295,1481,1516,1536]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="1" pageNumber="2" phylum="Firmicutes" rank="species" species="amyloliquefaciens">
|
||
<emphasis id="FAFEF0016F769B43FACA1DB78D87CB9F" bold="true" box="[1295,1481,1516,1536]" italics="true" pageId="1" pageNumber="2">B. amyloliquefaciens</emphasis>
|
||
</taxonomicName>
|
||
, which was deposited as
|
||
<taxonomicName id="0F8A57906F769B43FBCB1E528D4DC87B" authority="MTCC" authorityName="MTCC" box="[1038,1283,1544,1563]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="1" pageNumber="2" phylum="Firmicutes" rank="species" species="amyloliquefaciens">
|
||
<emphasis id="FAFEF0016F769B43FBCB1E528C8AC87B" bold="true" box="[1038,1220,1544,1563]" italics="true" pageId="1" pageNumber="2">B. amyloliquefaciens</emphasis>
|
||
MTCC
|
||
</taxonomicName>
|
||
<quantity id="0F7281F66F769B43FAC21E528D14C87B" box="[1287,1370,1544,1563]" metricMagnitude="2" metricUnit="m" metricValue="3.2291019999999997" pageId="1" pageNumber="2" unit="in" value="12713.0">12713 in</quantity>
|
||
the Institute of Microbial Technology (a Budapest Treaty recognized microbial repository of
|
||
<collectingCountry id="B09D6C836F769B43FC641E1A8B98C833" box="[929,982,1600,1619]" name="India" pageId="1" pageNumber="2">India</collectingCountry>
|
||
). Consistent with the preceding reports amongst the order
|
||
<taxonomicName id="0F8A57906F769B43FCAF1E068B8BC80F" authorityName="Prevot" authorityYear="1953" box="[874,965,1628,1647]" class="Bacilli" kingdom="Bacteria" order="Bacillales" pageId="1" pageNumber="2" phylum="Firmicutes" rank="order">Bacillales</taxonomicName>
|
||
,
|
||
<taxonomicName id="0F8A57906F769B43FC0A1E068C7BC80F" box="[975,1077,1628,1647]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="1" pageNumber="2" phylum="Firmicutes" rank="species" species="undetermined">
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||
<emphasis id="FAFEF0016F769B43FC0A1E068C5AC80F" bold="true" box="[975,1044,1628,1647]" italics="true" pageId="1" pageNumber="2">Bacillus</emphasis>
|
||
sp.
|
||
</taxonomicName>
|
||
were predominantly extant as heterotrophs with a number of marine macroalgae (
|
||
<bibRefCitation id="AC1B51E26F769B43FB6F1E228DD8C8EB" author="Chakraborty, K. & Thilakan, B. & Raola, V. K." box="[1194,1430,1656,1675]" pageId="1" pageNumber="2" pagination="12194 - 12208" refId="ref15360" refString="Chakraborty, K., Thilakan, B., Raola, V. K., 2014. Polyketide family of novel antibacterial 7 - O-methyl- 5 ' - hydroxy- 3 ' - heptenoate-macrolactin from seaweed-associated Bacillus subtilis MTCC 10403. J. Agric. Food Chem. 62 (50), 12194 - 12208. https: // doi. org / 10.1021 / jf 504845 m." type="journal article" year="2014">Chakraborty et al., 2014</bibRefCitation>
|
||
), and were documented as promising antibacterial agents (
|
||
<bibRefCitation id="AC1B51E26F769B43FAF21ECE8B2CC8A3" author="Li, J. W. & Vederas, J. C." pageId="1" pageNumber="2" pagination="161 - 165" refId="ref16494" refString="Li, J. W., Vederas, J. C., 2009. Drug discovery and natural products: end of an era or an endless frontier? Science 325 (5937), 161 - 165. https: // doi. org / 10.1126 / science. 1168243." type="journal article" year="2009">Li and Vederas, 2009</bibRefCitation>
|
||
). The
|
||
<taxonomicName id="0F8A57906F769B43FC641EF58BA8C8A2" box="[929,998,1711,1730]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="1" pageNumber="2" phylum="Firmicutes" rank="genus">
|
||
<emphasis id="FAFEF0016F769B43FC641EF58BA8C8A2" bold="true" box="[929,998,1711,1730]" italics="true" pageId="1" pageNumber="2">Bacillus</emphasis>
|
||
</taxonomicName>
|
||
strains harboring in the distinctive niches of intertidal or deep-water environments, could yield beneficial bioactive metabolites on account of having the innate ability to acclimatize in the extreme surroundings (
|
||
<bibRefCitation id="AC1B51E26F769B43FBCA1F598C94C976" author="Li, J. W. & Vederas, J. C." box="[1039,1242,1795,1814]" pageId="1" pageNumber="2" pagination="161 - 165" refId="ref16494" refString="Li, J. W., Vederas, J. C., 2009. Drug discovery and natural products: end of an era or an endless frontier? Science 325 (5937), 161 - 165. https: // doi. org / 10.1126 / science. 1168243." type="journal article" year="2009">Li and Vederas, 2009</bibRefCitation>
|
||
). Several reports claimed the promising biological activities of polyketide composites produced by marine
|
||
<taxonomicName id="0F8A57906F769B43FCBD1F618B90C92E" box="[888,990,1851,1870]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="1" pageNumber="2" phylum="Firmicutes" rank="species" species="undetermined">
|
||
<emphasis id="FAFEF0016F769B43FCBD1F618BF3C92E" bold="true" box="[888,957,1851,1870]" italics="true" pageId="1" pageNumber="2">Bacillus</emphasis>
|
||
sp.
|
||
</taxonomicName>
|
||
with bioactive
|
||
<emphasis id="FAFEF0016F769B43FBAE1F618CC1C92E" bold="true" box="[1131,1167,1851,1870]" italics="true" pageId="1" pageNumber="2">pks-</emphasis>
|
||
gene clusters (
|
||
<bibRefCitation id="AC1B51E26F769B43FAD11F618D87C92E" author="Mondol, M. A. & Shahidullah Tareq, F. & Kim, J. H. & Lee, M. A. & Lee, H. S. & Lee, J. S. & Lee, Y. J. & Shin, H. J." box="[1300,1481,1851,1870]" pageId="1" pageNumber="2" pagination="89 - 95" refId="ref16671" refString="Mondol, M. A., Shahidullah Tareq, F., Kim, J. H., Lee, M. A., Lee, H. S., Lee, J. S., Lee, Y. J., Shin, H. J., 2013. New antimicrobial compounds from a marine-derived Bacillus sp. J. Antibiot. (Tokyo) 66 (2), 89 - 95. https: // doi. org / 10.1038 / ja. 2012.102." type="journal article" year="2013">Mondol et al., 2013</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="AC1B51E26F769B43FCF71F0D8BADC90A" author="Nagao, T. & Adachi, K. & Sakai, M. & Nishijima, M. & Sano, H." box="[818,995,1879,1898]" pageId="1" pageNumber="2" pagination="333 - 339" refId="ref16808" refString="Nagao, T., Adachi, K., Sakai, M., Nishijima, M., Sano, H., 2001. Novel macrolactins as antibiotic lactones from a marine bacterium. J. Antibiot. (Tokyo) 54 (4), 333 - 339. https: // doi. org / 10.7164 / antibiotics. 54.333." type="journal article" year="2001">Nagao et al., 2001</bibRefCitation>
|
||
). Therefore, marine heterotrophic
|
||
<taxonomicName id="0F8A57906F769B43FAF71F0C8DD4C90A" box="[1330,1434,1878,1898]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="1" pageNumber="2" phylum="Firmicutes" rank="species" species="undetermined">
|
||
<emphasis id="FAFEF0016F769B43FAF71F0C8D39C909" bold="true" box="[1330,1399,1878,1897]" italics="true" pageId="1" pageNumber="2">Bacillus</emphasis>
|
||
sp.
|
||
</taxonomicName>
|
||
were endowed with promising antibacterial properties to develop successful management approaches against pathogens of biomedical significance (
|
||
<bibRefCitation id="AC1B51E26F769B43FCFF1FF18BBDC9DE" author="Mondol, M. A. & Kim, J. H. & Lee, H. S. & Lee, Y. J. & Shin, H. J." box="[826,1011,1963,1982]" pageId="1" pageNumber="2" pagination="3832 - 3835" refId="ref16590" refString="Mondol, M. A., Kim, J. H., Lee, H. S., Lee, Y. J., Shin, H. J., 2011. Macrolactin W, a new antibacterial macrolide from a marine Bacillus sp. Bioorg. Med. Chem. Lett 21 (12), 3832 - 3835. https: // doi. org / 10.1016 / j. bmcl. 2010.12.050." type="journal article" year="2011">Mondol et al., 2011</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="C8352C136F759B40FFA118CE897ECEA2" blockId="2.[100,679,147,167]" lastBlockId="2.[100,304,175,194]" pageId="2" pageNumber="3">
|
||
<emphasis id="FAFEF0016F759B40FFA118CE897ECEA2" bold="true" italics="true" pageId="2" pageNumber="3">
|
||
<heading id="937D9B7F6F759B40FFA118CE8AE9CEC6" bold="true" box="[100,679,147,167]" fontSize="36" level="1" pageId="2" pageNumber="3" reason="1">2.3. Purification and structural characterization of antibacterial</heading>
|
||
<heading id="937D9B7F6F759B40FFA118F5897ECEA2" box="[100,304,175,194]" fontSize="8" level="3" pageId="2" pageNumber="3" reason="8">macrobrevin analogues</heading>
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F759B40FF4118BD88E1CF0A" blockId="2.[100,770,231,1341]" pageId="2" pageNumber="3">
|
||
Organic extract of
|
||
<taxonomicName id="0F8A57906F759B40FEFF18B28A78CE9B" authority="MTCC" authorityName="MTCC" box="[314,566,231,251]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="2" pageNumber="3" phylum="Firmicutes" rank="species" species="amyloliquefaciens">
|
||
<emphasis id="FAFEF0016F759B40FEFF18B289BACE9A" bold="true" box="[314,500,231,251]" italics="true" pageId="2" pageNumber="3">B. amyloliquefaciens</emphasis>
|
||
MTCC
|
||
</taxonomicName>
|
||
12713 (~
|
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<quantity id="0F7281F66F759B40FD5D18BD8A80CE9B" box="[664,718,231,251]" metricMagnitude="-3" metricUnit="kg" metricValue="5.1" pageId="2" pageNumber="3" unit="g" value="5.1">5.1 g</quantity>
|
||
) was fractionated through flash and sequential preparatory high-pressure liquid chromatographic (HPLC) separation techniques to isolate four homogenous macrobrevin classes of compounds (with ≥98% yield) (
|
||
<figureCitation id="50B130966F759B40FFA9190D88ECCF0A" box="[108,162,343,362]" captionStart="Fig" captionStartId="2.[100,130,1862,1879]" captionTargetBox="[189,1398,1409,1833]" captionTargetId="figure-1003@2.[188,1400,1406,1835]" captionTargetPageId="2" captionText="Fig. 1. Structural representation of (A) trihydroxy-decahydro-37-methyl-macrobrevin (compound 1), (B) hexahydro-macrobrevin (compound 2), (C) hexahydro-41- hydroxy-macrobrevin-31-acetate (compound 3), and (D) hexahydro-28-nor-methyl-5-methoxy-macrobrevin (compound 4) isolated from marine macroalgaassociated B. amyloliquefaciens MTCC 12713. (E) The zone of inhibition (34 mm) observed with hexahydro-41-hydroxy-macrobrevin-31-acetate (compound 3) against VREfs as visualized on Mueller Hinton agar plates by disc diffusion assay was illustrated. The amounts of compound 3 and chloramphenicol were 30 μg per disc. Chloramphenicol and ethyl acetate, which were used as the positive and negative control, were denoted with (+) and (), respectively." figureDoi="http://doi.org/10.5281/zenodo.8235153" httpUri="https://zenodo.org/record/8235153/files/figure.png" pageId="2" pageNumber="3">Fig. 1</figureCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="C8352C136F759B40FF4119298D45CDF8" blockId="2.[100,770,231,1341]" lastBlockId="2.[818,1488,148,1341]" pageId="2" pageNumber="3">
|
||
The first in the series of macrobrevin class of compounds was characterized as 4, 27, 39-trihydroxy-decahydro-37-methyl-macrobrevin (compound
|
||
<emphasis id="FAFEF0016F759B40FF1F19F088A8CFDD" bold="true" box="[218,230,426,445]" pageId="2" pageNumber="3">1</emphasis>
|
||
). Its molecular formula was obtained as C
|
||
<subScript id="540E2E566F759B40FD5119E88AE8CFA0" attach="both" box="[660,678,434,448]" fontSize="6" pageId="2" pageNumber="3">43</subScript>
|
||
H
|
||
<subScript id="540E2E566F759B40FD7319E88A86CFA0" attach="both" box="[694,712,434,448]" fontSize="6" pageId="2" pageNumber="3">78</subScript>
|
||
O
|
||
<subScript id="540E2E566F759B40FD1219E88AAECFA0" attach="left" box="[727,736,434,448]" fontSize="6" pageId="2" pageNumber="3">9</subScript>
|
||
by mass spectroscopic experiment (HRESIMS
|
||
<emphasis id="FAFEF0016F759B40FE37199C8A58CFB9" bold="true" box="[498,534,454,473]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
739.5728 [M+H]
|
||
<superScript id="3FFF815B6F759B40FD7A199B8A85CFAF" attach="none" box="[703,715,449,463]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
), and NMR/IR data (
|
||
<tableCitation id="850819A86F759B40FF3619B88905CF96" box="[243,331,482,502]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetPageId="3" captionText="Table 1A NMR spectroscopic data of macrobrevin analogues, 1–2." httpUri="http://table.plazi.org/id/9CF57C9B6F749B41FFA118CC8A0CCEA0" pageId="2" pageNumber="3" tableUuid="9CF57C9B6F749B41FFA118CC8A0CCEA0">Table 1A</tableCitation>
|
||
;
|
||
<figureCitation id="50B130966F759B40FE9019B889D3CF96" box="[341,413,482,502]" captionStart="Fig" captionStartId="4.[100,130,768,785]" captionTargetBox="[268,1323,152,739]" captionTargetId="figure-868@4.[263,1324,148,741]" captionTargetPageId="4" captionText="Fig. 2. 1H–1H COSY/HMBC (A-D) correlations of macrobrevin analogues (1–4). Key 1H–1H COSY correlations and HMBC pairings were characterized by bold-faced bonds and double-barbed arrows, respectively." figureDoi="http://doi.org/10.5281/zenodo.8235155" httpUri="https://zenodo.org/record/8235155/files/figure.png" pageId="2" pageNumber="3">Fig. 2A</figureCitation>
|
||
;
|
||
<figureCitation id="50B130966F759B40FE6219B889B4CF96" box="[423,506,482,502]" captionStart="Fig" captionStartId="2.[100,130,1862,1879]" captionTargetBox="[189,1398,1409,1833]" captionTargetId="figure-1003@2.[188,1400,1406,1835]" captionTargetPageId="2" captionText="Fig. 1. Structural representation of (A) trihydroxy-decahydro-37-methyl-macrobrevin (compound 1), (B) hexahydro-macrobrevin (compound 2), (C) hexahydro-41- hydroxy-macrobrevin-31-acetate (compound 3), and (D) hexahydro-28-nor-methyl-5-methoxy-macrobrevin (compound 4) isolated from marine macroalgaassociated B. amyloliquefaciens MTCC 12713. (E) The zone of inhibition (34 mm) observed with hexahydro-41-hydroxy-macrobrevin-31-acetate (compound 3) against VREfs as visualized on Mueller Hinton agar plates by disc diffusion assay was illustrated. The amounts of compound 3 and chloramphenicol were 30 μg per disc. Chloramphenicol and ethyl acetate, which were used as the positive and negative control, were denoted with (+) and (), respectively." figureDoi="http://doi.org/10.5281/zenodo.8235153" httpUri="https://zenodo.org/record/8235153/files/figure.png" pageId="2" pageNumber="3">Fig. S1-S</figureCitation>
|
||
12). The
|
||
<superScript id="3FFF815B6F759B40FD9719878A2ACF8B" attach="right" box="[594,612,477,491]" fontSize="6" pageId="2" pageNumber="3">13</superScript>
|
||
C/
|
||
<superScript id="3FFF815B6F759B40FDB919878AD9CF8B" attach="right" box="[636,663,477,491]" fontSize="6" pageId="2" pageNumber="3">135</superScript>
|
||
DEPT NMR represented 43 carbons that included two non-protonated carbons, eight methyls, fourteen methylenes and nineteen methines. Basic framework of macrobrevin skeleton was deduced from spin systems obtained through COSYs at H-2/H-3; H-5/H-14, H-15/H-29 and H-30/H-34, and was further confirmed through the HMBCs. The 21-membered macrocyclic lactone ring was formed between the oxygenated end of ester at C- 1 (
|
||
<emphasis id="FAFEF0016F759B40FF461AFC88C3CCD9" bold="true" box="[131,141,678,697]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FF481AF788D9CCDB" attach="left" box="[141,151,685,699]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
166.2) and methine at C-21 (
|
||
<emphasis id="FAFEF0016F759B40FE091AFC8998CCD9" bold="true" box="[460,470,678,697]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FE131AF789ACCCDB" attach="left" box="[470,482,685,699]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
3.92/
|
||
<emphasis id="FAFEF0016F759B40FDE41AFC8A65CCD9" bold="true" box="[545,555,678,697]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FDEE1AF78A7BCCDB" attach="left" box="[555,565,685,699]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
70.2), and this was ascribed through HMBCs from
|
||
<emphasis id="FAFEF0016F759B40FE401A9B89C1CCB4" bold="true" box="[389,399,705,724]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FE4A1A9389D5CCB7" attach="left" box="[399,411,713,727]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
6.05 (H-2), 7.09 (H-3), 3.92 (H-21) to
|
||
<emphasis id="FAFEF0016F759B40FFA11A878820CC90" bold="true" box="[100,110,733,752]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FFAB1ABF8836CC93" attach="left" box="[110,120,741,755]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
166.2 (C-1). Previously reported 24-membered macrocyclic lactones exhibited chemical shifts of
|
||
<emphasis id="FAFEF0016F759B40FEB41AA38935CD6C" bold="true" box="[369,379,761,780]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FEBE1B5B89CBCD6F" attach="left" box="[379,389,769,783]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
167 (C-1),
|
||
<emphasis id="FAFEF0016F759B40FE301AA389B1CD6C" bold="true" box="[501,511,761,780]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FE3A1B5B8A45CD6F" attach="left" box="[511,523,769,783]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
5.5/
|
||
<emphasis id="FAFEF0016F759B40FDFF1AA38A0ACD6C" bold="true" box="[570,580,761,780]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FD811B5B8A00CD6F" attach="left" box="[580,590,769,783]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
117–118 (C-2),
|
||
<emphasis id="FAFEF0016F759B40FD291AA38AB8CD6C" bold="true" box="[748,758,761,780]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FD331B5B8B4CCD6F" attach="left" box="[758,770,769,783]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
6.6/
|
||
<emphasis id="FAFEF0016F759B40FF481B4F88D9CD48" bold="true" box="[141,151,789,808]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FF531B4688EECD4A" attach="left" box="[150,160,796,810]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
145 (C-3),
|
||
<emphasis id="FAFEF0016F759B40FECC1B4F895DCD48" bold="true" box="[265,275,789,808]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FED61B478951CD4B" attach="left" box="[275,287,797,811]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
7.2/
|
||
<emphasis id="FAFEF0016F759B40FE891B4F8918CD48" bold="true" box="[332,342,789,808]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FE931B46892ECD4A" attach="left" box="[342,352,796,810]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
129–130 (C-4),
|
||
<emphasis id="FAFEF0016F759B40FE321B4F8A4FCD48" bold="true" box="[503,513,789,808]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FDC41B478A43CD4B" attach="left" box="[513,525,797,811]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
6.1/
|
||
<emphasis id="FAFEF0016F759B40FDFF1B4F8A0ACD48" bold="true" box="[570,580,789,808]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FD811B468A00CD4A" attach="left" box="[580,590,796,810]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
140–142 (C-5) and
|
||
<emphasis id="FAFEF0016F759B40FFA11B6B8820CD24" bold="true" box="[100,110,817,836]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FFAB1B638834CD27" attach="left" box="[110,122,825,839]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
5.08/
|
||
<emphasis id="FAFEF0016F759B40FF7C1B6B888DCD24" bold="true" box="[185,195,817,836]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FF071B638880CD27" attach="left" box="[194,206,825,839]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
71 (C-23) (
|
||
<bibRefCitation id="AC1B51E26F759B40FE8C1B6B89A2CD24" author="Gao, C. H. & Tian, X. P. & Qi, S. H. & Luo, X. M. & Wang, P. & Zhang, S." box="[329,492,817,837]" pageId="2" pageNumber="3" pagination="191 - 193" refId="ref15776" refString="Gao, C. H., Tian, X. P., Qi, S. H., Luo, X. M., Wang, P., Zhang, S., 2010. Antibacterial and antilarval compounds from marine gorgonian-associated bacterium Bacillus amyloliquefaciens SCSIO 00856. J. Antibiot. (Tokyo) 63 (4), 191 - 193. https: // doi. org / 10.1038 / ja. 2010.7." type="journal article" year="2010">Gao et al., 2010</bibRefCitation>
|
||
), which resembled to those recorded in the studied compound
|
||
<emphasis id="FAFEF0016F759B40FE701B17898FCD00" bold="true" box="[437,449,845,864]" pageId="2" pageNumber="3">1</emphasis>
|
||
, as also with another compound, named as bacvalactones showing chemical shifts of
|
||
<emphasis id="FAFEF0016F759B40FDA71B338A22CD1C" bold="true" box="[610,620,873,892]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FDA91B2A8A38CD1E" attach="left" box="[620,630,880,894]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
166 (C-1),
|
||
<emphasis id="FAFEF0016F759B40FD291B338AB8CD1C" bold="true" box="[748,758,873,892]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FD331B2A8B4CCD1E" attach="left" box="[758,770,880,894]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
5.7/
|
||
<emphasis id="FAFEF0016F759B40FF481BDF88D9CDF8" bold="true" box="[141,151,901,920]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FF531BD688EECDFA" attach="left" box="[150,160,908,922]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
121–125 (C-2),
|
||
<emphasis id="FAFEF0016F759B40FEF31BDF890ECDF8" bold="true" box="[310,320,901,920]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FE851BD68902CDFA" attach="left" box="[320,332,908,922]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
6.1/
|
||
<emphasis id="FAFEF0016F759B40FEBD1BDF89CCCDF8" bold="true" box="[376,386,901,920]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FE471BD689C2CDFA" attach="left" box="[386,396,908,922]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
141–143 (C-3) and
|
||
<emphasis id="FAFEF0016F759B40FD861BDF8A03CDF8" bold="true" box="[579,589,901,920]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FD881BD68A17CDFA" attach="left" box="[589,601,908,922]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
4.13/
|
||
<emphasis id="FAFEF0016F759B40FD541BDF8AD5CDF8" bold="true" box="[657,667,901,920]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FD5E1BD68AEBCDFA" attach="left" box="[667,677,908,922]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
72 (C-23) (
|
||
<bibRefCitation id="AC1B51E26F759B40FFA91BFB8901CDD4" author="Chakraborty, K. & Kizhakkekalam, V. K. & Joy, M. & Chakraborty, R. D." box="[108,335,929,948]" pageId="2" pageNumber="3" pagination="7117 - 7130" refId="ref15224" refString="Chakraborty, K., Kizhakkekalam, V. K., Joy, M., Chakraborty, R. D., 2020. Moving away from traditional antibiotic treatment: can macrocyclic lactones from marine macroalga-associated heterotroph be the alternatives? Appl. Microbiol. Biotechnol. 104 (16), 7117 - 7130. https: // doi. org / 10.1007 / s 00253 - 020 - 10658 - 0." type="journal article" year="2020">Chakraborty et al., 2020</bibRefCitation>
|
||
). In particular, the proton chemical shift value of
|
||
<emphasis id="FAFEF0016F759B40FF451BE688C4CDAF" bold="true" box="[128,138,956,975]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FF4F1B9E88D8CDB2" attach="left" box="[138,150,964,978]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
3.92 at H-
|
||
<quantity id="0F7281F66F759B40FEC21BE78976CDB0" box="[263,312,957,976]" metricMagnitude="-1" metricUnit="m" metricValue="5.334" pageId="2" pageNumber="3" unit="in" value="21.0">21 in</quantity>
|
||
the present 21-membered macrocyclic lactone showed change in
|
||
<emphasis id="FAFEF0016F759B40FED11B828950CD8B" bold="true" box="[276,286,984,1003]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
of about ~1–2 ppm as compared to the previously reported 24-membered macrocyclic lactones (
|
||
<bibRefCitation id="AC1B51E26F759B40FDD01BAE8AB2CA68" author="Chakraborty, K. & Kizhakkekalam, V. K. & Joy, M. & Chakraborty, R. D." box="[533,764,1012,1032]" pageId="2" pageNumber="3" pagination="7117 - 7130" refId="ref15224" refString="Chakraborty, K., Kizhakkekalam, V. K., Joy, M., Chakraborty, R. D., 2020. Moving away from traditional antibiotic treatment: can macrocyclic lactones from marine macroalga-associated heterotroph be the alternatives? Appl. Microbiol. Biotechnol. 104 (16), 7117 - 7130. https: // doi. org / 10.1007 / s 00253 - 020 - 10658 - 0." type="journal article" year="2020">Chakraborty et al., 2020</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="AC1B51E26F759B40FFA11C4B88B6CA44" author="Gao, C. H. & Tian, X. P. & Qi, S. H. & Luo, X. M. & Wang, P. & Zhang, S." box="[100,248,1040,1060]" pageId="2" pageNumber="3" pagination="191 - 193" refId="ref15776" refString="Gao, C. H., Tian, X. P., Qi, S. H., Luo, X. M., Wang, P., Zhang, S., 2010. Antibacterial and antilarval compounds from marine gorgonian-associated bacterium Bacillus amyloliquefaciens SCSIO 00856. J. Antibiot. (Tokyo) 63 (4), 191 - 193. https: // doi. org / 10.1038 / ja. 2010.7." type="journal article" year="2010">Gao et al., 2010</bibRefCitation>
|
||
). This might be due to the absence of conjugated dienes at C-4/C-5 and lesser number of carbon atoms involved in the cyclization of the oxygenated end of ester at C-1 and carboxylated end of methine at C-21. The titled compound was comparable to the previously reported macrobrevin compounds enclosing the alkenes at C-2 = C-3, C-7 = C-8, and C-10 = C-11, C-14 = C-15, C-16 = C-17, C-25 = C-26, C-27 = C-28 and C-29 = C-30 positions (
|
||
<bibRefCitation id="AC1B51E26F759B40FE231CE28AEDCAAB" author="Helfrich, E. J. N. & Vogel, C. M. & Ueoka, R. & Ryffel, F. & Muller, D. B. & Probst, S. & Kreuzer, M. & Piel, J. & Vorholt, J. A." box="[486,675,1208,1227]" pageId="2" pageNumber="3" pagination="909 - 919" refId="ref16029" refString="Helfrich, E. J. N., Vogel, C. M., Ueoka, R., Sch ¨ afer, M., Ryffel, F., Muller, D. B., Probst, S., Kreuzer, M., Piel, J., Vorholt, J. A., 2018. Bipartite interactions, antibiotic production and biosynthetic potential of the Arabidopsis leaf microbiome. Nat. Microbiol. 3 (8), 909 - 919. https: // doi. org / 10.1038 / s 41564 - 018 - 0200 - 0." type="journal article" year="2018">Helfrich et al., 2018</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="AC1B51E26F759B40FD6A1CE28881CA87" author="Soldatou, S. & Eldjarn, G. H. & Huerta-Uribe, A. & Rogers, S. & Duncan, K. R." pageId="2" pageNumber="3" pagination="142" refId="ref17331" refString="Soldatou, S., Eldjarn, G. H., Huerta-Uribe, A., Rogers, S., Duncan, K. R., 2019. Linking biosynthetic and chemical space to accelerate microbial secondary metabolite discovery. FEMS Microbiol. Lett. 366 (13), fnz 142. https: // doi. org / 10.1093 / femsle / fnz 142." type="journal article" year="2019">Soldatou et al., 2019</bibRefCitation>
|
||
). The alkenic protons with greater coupling constants (
|
||
<emphasis id="FAFEF0016F759B40FD1D1C8E8AACCA87" bold="true" box="[728,738,1236,1255]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
) at
|
||
<emphasis id="FAFEF0016F759B40FFA11CB58820CB62" bold="true" box="[100,110,1263,1282]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FFAB1CAD8834CB65" attach="left" box="[110,122,1271,1285]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
6.05 (
|
||
<emphasis id="FAFEF0016F759B40FF701CAA88F1CB63" bold="true" box="[181,191,1264,1283]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 13.8 Hz, H-2),
|
||
<emphasis id="FAFEF0016F759B40FEA41CB58925CB62" bold="true" box="[353,363,1263,1282]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FEAE1CAD8939CB65" attach="left" box="[363,375,1271,1285]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
7.09 (
|
||
<emphasis id="FAFEF0016F759B40FE771CAA89F2CB63" bold="true" box="[434,444,1264,1283]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 12.1 Hz, H-3),
|
||
<emphasis id="FAFEF0016F759B40FD981CB58A29CB62" bold="true" box="[605,615,1263,1282]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FDA21CAD8A3DCB65" attach="left" box="[615,627,1271,1285]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
5.48 (
|
||
<emphasis id="FAFEF0016F759B40FD6B1CAA8AF6CB63" bold="true" box="[686,696,1264,1283]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 13.1, 2.4 Hz, H-14),
|
||
<emphasis id="FAFEF0016F759B40FF2E1D5188BBCB7E" bold="true" box="[235,245,1291,1310]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FF301D49894FCB41" attach="left" box="[245,257,1299,1313]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
5.52 (
|
||
<emphasis id="FAFEF0016F759B40FEFE1D56890BCB7F" bold="true" box="[315,325,1292,1311]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 12.5, 2.1 Hz, H-15), and
|
||
<emphasis id="FAFEF0016F759B40FD841D518A05CB7E" bold="true" box="[577,587,1291,1310]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FD8E1D498A19CB41" attach="left" box="[587,599,1299,1313]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
5.32 (
|
||
<emphasis id="FAFEF0016F759B40FD541D568AD5CB7F" bold="true" box="[657,667,1292,1311]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 13.0 Hz, H-29),
|
||
<emphasis id="FAFEF0016F759B40FF751D7D88F4CB5A" bold="true" box="[176,186,1319,1338]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FF7F1D758888CB5D" attach="left" box="[186,198,1327,1341]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
5.41 (
|
||
<emphasis id="FAFEF0016F759B40FED31D72896ECB5B" bold="true" box="[278,288,1320,1339]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 10.2 Hz, H-30) positions designated their
|
||
<emphasis id="FAFEF0016F759B40FCF718CE8B2BCEC7" bold="true" box="[818,869,148,167]" italics="true" pageId="2" pageNumber="3">trans-</emphasis>
|
||
orientation (
|
||
<emphasis id="FAFEF0016F759B40FC1918CE8BA6CEC7" bold="true" box="[988,1000,148,167]" italics="true" pageId="2" pageNumber="3">E</emphasis>
|
||
). Compound
|
||
<emphasis id="FAFEF0016F759B40FBAC18CE8C3BCEC7" bold="true" box="[1129,1141,148,167]" pageId="2" pageNumber="3">1</emphasis>
|
||
enclosed a hydroxylated quaternary carbon at C-4 (
|
||
<emphasis id="FAFEF0016F759B40FC0518F58B84CEA2" bold="true" box="[960,970,175,194]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FC0C18ED8B9DCEA5" attach="left" box="[969,979,183,197]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
81.2), which was substantiated through HMBCs from
|
||
<emphasis id="FAFEF0016F759B40FCF718918B72CEBE" bold="true" box="[818,828,203,222]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FCFE18898B09CE81" attach="left" box="[827,839,211,225]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
6.05 (H-2), 3.35 (H-5) to
|
||
<emphasis id="FAFEF0016F759B40FBF818918C09CEBE" bold="true" box="[1085,1095,203,222]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FB8218898C1FCE81" attach="left" box="[1095,1105,211,225]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
81.2 (C-4). The dispositions at C-13 and C-22 enclosed ethyl and hydroxymethylene linkages, respectively through HMBCs from
|
||
<emphasis id="FAFEF0016F759B40FC3A19598C47CF76" bold="true" box="[1023,1033,259,278]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FBCC19518C5BCF79" attach="left" box="[1033,1045,267,281]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
0.93 (H-37a) to
|
||
<emphasis id="FAFEF0016F759B40FB7719598CF2CF76" bold="true" box="[1202,1212,259,278]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FB7E19518C8BCF79" attach="left" box="[1211,1221,267,281]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
28.1 (C-37) {COSYs
|
||
<emphasis id="FAFEF0016F759B40FA4F19598DDACF76" bold="true" box="[1418,1428,259,278]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FA5119518DEECF79" attach="left" box="[1428,1440,267,281]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
1.41 (H-37)/0.93 (H-37a)} and
|
||
<emphasis id="FAFEF0016F759B40FBEF19458C7ACF52" bold="true" box="[1066,1076,287,306]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FBF1197D8C0ECF55" attach="left" box="[1076,1088,295,309]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
3.63 (H-39) to
|
||
<emphasis id="FAFEF0016F759B40FB0A19458C97CF52" bold="true" box="[1231,1241,287,306]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FB1C197C8CADCF54" attach="left" box="[1241,1251,294,308]" fontSize="6" pageId="2" pageNumber="3">C</subScript>
|
||
34.9 (C-22), 38.6 (C-23), respectively. Based upon comprehensive spectral analyses and comparing the similarities and variations with basic core of previously reported macrobrevin analogues (
|
||
<bibRefCitation id="AC1B51E26F759B40FBB619298D7DCFE6" author="Helfrich, E. J. N. & Vogel, C. M. & Ueoka, R. & Ryffel, F. & Muller, D. B. & Probst, S. & Kreuzer, M. & Piel, J. & Vorholt, J. A." box="[1139,1331,371,390]" pageId="2" pageNumber="3" pagination="909 - 919" refId="ref16029" refString="Helfrich, E. J. N., Vogel, C. M., Ueoka, R., Sch ¨ afer, M., Ryffel, F., Muller, D. B., Probst, S., Kreuzer, M., Piel, J., Vorholt, J. A., 2018. Bipartite interactions, antibiotic production and biosynthetic potential of the Arabidopsis leaf microbiome. Nat. Microbiol. 3 (8), 909 - 919. https: // doi. org / 10.1038 / s 41564 - 018 - 0200 - 0." type="journal article" year="2018">Helfrich et al., 2018</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="AC1B51E26F759B40FA8519298B2CCFC2" author="Soldatou, S. & Eldjarn, G. H. & Huerta-Uribe, A. & Rogers, S. & Duncan, K. R." pageId="2" pageNumber="3" pagination="142" refId="ref17331" refString="Soldatou, S., Eldjarn, G. H., Huerta-Uribe, A., Rogers, S., Duncan, K. R., 2019. Linking biosynthetic and chemical space to accelerate microbial secondary metabolite discovery. FEMS Microbiol. Lett. 366 (13), fnz 142. https: // doi. org / 10.1093 / femsle / fnz 142." type="journal article" year="2019">Soldatou et al., 2019</bibRefCitation>
|
||
), the compound
|
||
<emphasis id="FAFEF0016F759B40FBC419D58C43CFC2" bold="true" box="[1025,1037,399,418]" pageId="2" pageNumber="3">1</emphasis>
|
||
was characterized as 4, 27, 39-trihydroxy-decahydro-37-methyl-macrobrevin. The compound
|
||
<emphasis id="FAFEF0016F759B40FB3919F08D46CFDD" bold="true" box="[1276,1288,426,445]" pageId="2" pageNumber="3">1</emphasis>
|
||
was not previously known, and found to be the derivative of basic skeleton of already known macrobrevins with functional group variations in their structure, and therefore, it could be considered as previously undisclosed macrobrevin analogue. Relative stereochemical assignments of the protons were assigned by NOESYs and earlier reports (
|
||
<bibRefCitation id="AC1B51E26F759B40FB3E1A6C8D8FCC29" author="Helfrich, E. J. N. & Vogel, C. M. & Ueoka, R. & Ryffel, F. & Muller, D. B. & Probst, S. & Kreuzer, M. & Piel, J. & Vorholt, J. A." box="[1275,1473,566,586]" pageId="2" pageNumber="3" pagination="909 - 919" refId="ref16029" refString="Helfrich, E. J. N., Vogel, C. M., Ueoka, R., Sch ¨ afer, M., Ryffel, F., Muller, D. B., Probst, S., Kreuzer, M., Piel, J., Vorholt, J. A., 2018. Bipartite interactions, antibiotic production and biosynthetic potential of the Arabidopsis leaf microbiome. Nat. Microbiol. 3 (8), 909 - 919. https: // doi. org / 10.1038 / s 41564 - 018 - 0200 - 0." type="journal article" year="2018">Helfrich et al., 2018</bibRefCitation>
|
||
). NOEs from
|
||
<emphasis id="FAFEF0016F759B40FC641A088BE5CC05" bold="true" box="[929,939,594,613]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FC6F1A008BF8CC08" attach="left" box="[938,950,602,616]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
1.83 (H-32)/2.42 (H-28)/1.69 (H-24)/3.92 (H-21)/1.33 (H-35)/3.35 (H-5)/1.78 (H-10)/0.99 (H-38) were attributed for adjacent spatial apportionments that supported their equivalent plane of alignments, and consequently, assigned as
|
||
<emphasis id="FAFEF0016F759B40FB0E1AFC8C98CCD9" bold="true" box="[1227,1238,678,697]" italics="true" pageId="2" pageNumber="3">β</emphasis>
|
||
-oriented. Similarly, NOEs between
|
||
<emphasis id="FAFEF0016F759B40FC491A9B8BD8CCB4" bold="true" box="[908,918,705,724]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FC531A938BECCCB7" attach="left" box="[918,930,713,727]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
3.97 (H-31)/0.88 (H-42)/1.03 (H-41)/0.95 (H-40)/2.21 (H-22)/3.44 (H-19)/1.72 (H-18)/2.15 (H-13)/1.02 (H-36)/3.15 (H-9) were recognized for their adjacent spatial distributions that reinforced their comparable plane of alignments, and accordingly, designated as
|
||
<emphasis id="FAFEF0016F759B40FCF71B6B8B70CD26" bold="true" box="[818,830,817,838]" italics="true" pageId="2" pageNumber="3">α</emphasis>
|
||
-oriented. The mass spectrum exhibited a molecular ion peak at
|
||
<emphasis id="FAFEF0016F759B40FA6E1B6B8D81CD24" bold="true" box="[1451,1487,817,836]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
738, and the base peak was deduced as 2,2-dihydroxyethen-1-ylium cation at
|
||
<emphasis id="FAFEF0016F759B40FC4B1B338BFDCD1C" bold="true" box="[910,947,873,892]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
59 (
|
||
<emphasis id="FAFEF0016F759B40FC261B338BBFCD1C" bold="true" box="[995,1009,873,892]" pageId="2" pageNumber="3">K</emphasis>
|
||
), which could form by successive fragmentations including McLafferty rearrangements (Fig.
|
||
<collectionCode id="AE9BB4D66F759B40FB021BDF8C9DCDF8" box="[1223,1235,901,920]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="2" pageNumber="3" type="Herbarium">S</collectionCode>
|
||
9-10).
|
||
</paragraph>
|
||
<paragraph id="C8352C136F759B41FC941BFB8BF0C903" blockId="2.[818,1488,148,1341]" lastBlockId="3.[818,1487,1648,1977]" lastPageId="3" lastPageNumber="4" pageId="2" pageNumber="3">
|
||
Another previously undisclosed macrobrevin analogue polyketidespanned macrolactone (macrobrevin
|
||
<emphasis id="FAFEF0016F759B40FB041BE78C83CDB0" bold="true" box="[1217,1229,957,976]" pageId="2" pageNumber="3">2</emphasis>
|
||
) was characterized as 7,8,16,17,25,26-hexahydro-macrobrevin. Its molecular formula was deduced as C
|
||
<subScript id="540E2E566F759B40FC681BA68BF1CA6A" attach="right" box="[941,959,1020,1034]" fontSize="6" pageId="2" pageNumber="3">42</subScript>
|
||
H
|
||
<subScript id="540E2E566F759B40FC0A1BA68BAFCA6A" attach="both" box="[975,993,1020,1034]" fontSize="6" pageId="2" pageNumber="3">72</subScript>
|
||
O
|
||
<subScript id="540E2E566F759B40FC351BA18BB7CA69" attach="left" box="[1008,1017,1019,1033]" fontSize="6" pageId="2" pageNumber="3">6</subScript>
|
||
by mass spectroscopic experiment (HRESIMS
|
||
<emphasis id="FAFEF0016F759B40FA6E1BAE8D81CA67" bold="true" box="[1451,1487,1012,1031]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
found 673.5410 [M+H]
|
||
<superScript id="3FFF815B6F759B40FBD41C518C53CA79" attach="none" box="[1041,1053,1035,1049]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
), and combination of NMR/IR data (
|
||
<tableCitation id="850819A86F759B40FAB31C4A8D82CA44" box="[1398,1484,1040,1060]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetPageId="3" captionText="Table 1A NMR spectroscopic data of macrobrevin analogues, 1–2." httpUri="http://table.plazi.org/id/9CF57C9B6F749B41FFA118CC8A0CCEA0" pageId="2" pageNumber="3" tableUuid="9CF57C9B6F749B41FFA118CC8A0CCEA0">Table 1A</tableCitation>
|
||
;
|
||
<figureCitation id="50B130966F759B40FCF71C768B3ACA20" box="[818,884,1068,1088]" captionStart="Fig" captionStartId="4.[100,130,768,785]" captionTargetBox="[268,1323,152,739]" captionTargetId="figure-868@4.[263,1324,148,741]" captionTargetPageId="4" captionText="Fig. 2. 1H–1H COSY/HMBC (A-D) correlations of macrobrevin analogues (1–4). Key 1H–1H COSY correlations and HMBC pairings were characterized by bold-faced bonds and double-barbed arrows, respectively." figureDoi="http://doi.org/10.5281/zenodo.8235155" httpUri="https://zenodo.org/record/8235155/files/figure.png" pageId="2" pageNumber="3">Fig. 2B</figureCitation>
|
||
; Fig.
|
||
<collectionCode id="AE9BB4D66F759B40FC611C768BFECA5F" box="[932,944,1068,1087]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="2" pageNumber="3" type="Herbarium">S</collectionCode>
|
||
13-
|
||
<collectionCode id="AE9BB4D66F759B40FC091C768B96CA5F" box="[972,984,1068,1087]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="2" pageNumber="3" type="Herbarium">S</collectionCode>
|
||
24).
|
||
<superScript id="3FFF815B6F759B40FBC61C7D8C5BCA55" attach="right" box="[1027,1045,1063,1077]" fontSize="6" pageId="2" pageNumber="3">13</superScript>
|
||
C/
|
||
<superScript id="3FFF815B6F759B40FBE91C7C8C09CA54" attach="right" box="[1068,1095,1062,1076]" fontSize="6" pageId="2" pageNumber="3">135</superScript>
|
||
DEPT NMR represented 42 carbons, which included three non-protonated carbons, nine methyls, ten methylenes and twenty methines. Similar to the previous compound
|
||
<emphasis id="FAFEF0016F759B40FAAE1C3E8D39CA17" bold="true" box="[1387,1399,1124,1143]" pageId="2" pageNumber="3">1</emphasis>
|
||
, the 21- membered macrobrevin was deduced by COSYs through H-2/H-9; H-11/H-14, H-15/H-27 and H-29/H-34, and side chain attachment at C-21 was confirmed through HMBC. The titled compound enclosed the alkenic groups only at C-2 = C-3, C-10 = C-11, C-14 = C-15, C-27 = C-28 and C-29 = C-30 positions, when compared to the previously reported macrobrevins (
|
||
<bibRefCitation id="AC1B51E26F759B40FC7A1D518C32CB7E" author="Helfrich, E. J. N. & Vogel, C. M. & Ueoka, R. & Ryffel, F. & Muller, D. B. & Probst, S. & Kreuzer, M. & Piel, J. & Vorholt, J. A." box="[959,1148,1291,1311]" pageId="2" pageNumber="3" pagination="909 - 919" refId="ref16029" refString="Helfrich, E. J. N., Vogel, C. M., Ueoka, R., Sch ¨ afer, M., Ryffel, F., Muller, D. B., Probst, S., Kreuzer, M., Piel, J., Vorholt, J. A., 2018. Bipartite interactions, antibiotic production and biosynthetic potential of the Arabidopsis leaf microbiome. Nat. Microbiol. 3 (8), 909 - 919. https: // doi. org / 10.1038 / s 41564 - 018 - 0200 - 0." type="journal article" year="2018">Helfrich et al., 2018</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="AC1B51E26F759B40FB4D1D518D02CB7E" author="Soldatou, S. & Eldjarn, G. H. & Huerta-Uribe, A. & Rogers, S. & Duncan, K. R." box="[1160,1356,1291,1311]" pageId="2" pageNumber="3" pagination="142" refId="ref17331" refString="Soldatou, S., Eldjarn, G. H., Huerta-Uribe, A., Rogers, S., Duncan, K. R., 2019. Linking biosynthetic and chemical space to accelerate microbial secondary metabolite discovery. FEMS Microbiol. Lett. 366 (13), fnz 142. https: // doi. org / 10.1093 / femsle / fnz 142." type="journal article" year="2019">Soldatou et al., 2019</bibRefCitation>
|
||
). The alkenes with greater coupling constants at
|
||
<emphasis id="FAFEF0016F759B40FBB11D7D8C30CB5A" bold="true" box="[1140,1150,1319,1338]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FBB81D758CC7CB5D" attach="left" box="[1149,1161,1327,1341]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
5.82 (
|
||
<emphasis id="FAFEF0016F759B40FB031D728C9ECB5B" bold="true" box="[1222,1232,1320,1339]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 13.1 Hz, H-2),
|
||
<emphasis id="FAFEF0016F759B40FAB61D7D8D33CB5A" bold="true" box="[1395,1405,1319,1338]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="540E2E566F759B40FAB81D758DC7CB5D" attach="left" box="[1405,1417,1327,1341]" fontSize="6" pageId="2" pageNumber="3">H</subScript>
|
||
6.89 (
|
||
<emphasis id="FAFEF0016F759B40FA001D728D81CB5B" bold="true" box="[1477,1487,1320,1339]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 12.1, 4.1 Hz, H-3),
|
||
<emphasis id="FAFEF0016F749B41FEE91E2A8978C8E3" bold="true" box="[300,310,1648,1667]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FEF31E22890CC8E6" attach="left" box="[310,322,1656,1670]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
5.19 (
|
||
<emphasis id="FAFEF0016F749B41FEBB1E2B89C6C8E4" bold="true" box="[382,392,1649,1668]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
= 10.5 Hz, H-11),
|
||
<emphasis id="FAFEF0016F749B41FDFD1E2A8A0CC8E3" bold="true" box="[568,578,1648,1667]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FD871E228A00C8E6" attach="left" box="[578,590,1656,1670]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
5.46 (
|
||
<emphasis id="FAFEF0016F749B41FD4F1E2B8ADAC8E4" bold="true" box="[650,660,1649,1668]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
= 13.0, 2.1 Hz, H-14),
|
||
<emphasis id="FAFEF0016F749B41FF0F1ED6889AC8FF" bold="true" box="[202,212,1676,1695]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FF111ECE88AEC8C2" attach="left" box="[212,224,1684,1698]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
5.68 (
|
||
<emphasis id="FAFEF0016F749B41FEDE1ED7896BC8C0" bold="true" box="[283,293,1677,1696]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
= 12.1, 2.5 Hz, H-15),
|
||
<emphasis id="FAFEF0016F749B41FE381ED68A49C8FF" bold="true" box="[509,519,1676,1695]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FDC21ECE8A5DC8C2" attach="left" box="[519,531,1684,1698]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
6.00 (
|
||
<emphasis id="FAFEF0016F749B41FD8B1ED78A16C8C0" bold="true" box="[590,600,1677,1696]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
= 13.9 Hz, H-27), and
|
||
<emphasis id="FAFEF0016F749B41FF481EF288D9C8DB" bold="true" box="[141,151,1704,1723]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FF521EEA88EDC8DE" attach="left" box="[151,163,1712,1726]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
6.47 (
|
||
<emphasis id="FAFEF0016F749B41FF241EF288A5C8DB" bold="true" box="[225,235,1704,1723]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
= 13.1 Hz, H-29),
|
||
<emphasis id="FAFEF0016F749B41FE651EF289E4C8DB" bold="true" box="[416,426,1704,1723]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FE6F1EEA89F8C8DE" attach="left" box="[426,438,1712,1726]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
5.39 (
|
||
<emphasis id="FAFEF0016F749B41FE311EF289B0C8DB" bold="true" box="[500,510,1704,1723]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
= 10.2 Hz, H-30) positions attributed their
|
||
<emphasis id="FAFEF0016F749B41FF3A1E9E8962C8B7" bold="true" box="[255,300,1732,1751]" italics="true" pageId="3" pageNumber="4">trans</emphasis>
|
||
-orientation (
|
||
<emphasis id="FAFEF0016F749B41FE691E9E89F6C8B7" bold="true" box="[428,440,1732,1751]" italics="true" pageId="3" pageNumber="4">E</emphasis>
|
||
). A deshielded quaternary carbon was present in the previous compound
|
||
<emphasis id="FAFEF0016F749B41FE2A1EBA89B5C893" bold="true" box="[495,507,1760,1779]" pageId="3" pageNumber="4">1</emphasis>
|
||
at
|
||
<emphasis id="FAFEF0016F749B41FDE71EBA8A62C893" bold="true" box="[546,556,1760,1779]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FDE91EBD8A78C895" attach="left" box="[556,566,1767,1781]" fontSize="6" pageId="3" pageNumber="4">C</subScript>
|
||
81.2 (C-4), whereas compound
|
||
<emphasis id="FAFEF0016F749B41FF171EA68890C96F" bold="true" box="[210,222,1788,1807]" pageId="3" pageNumber="4">2</emphasis>
|
||
enclosed a shielded methine carbon at
|
||
<emphasis id="FAFEF0016F749B41FDAA1EA68A37C96F" bold="true" box="[623,633,1788,1807]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FDBD1F598ACAC971" attach="left" box="[632,644,1795,1809]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
37.5, which recognized the absence of hydroxyl at this position. Also, a higher chemical shift value of about ~3 ppm at H-27 (
|
||
<emphasis id="FAFEF0016F749B41FDD01F698A51C926" bold="true" box="[533,543,1843,1862]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FDDA1F618A65C929" attach="left" box="[543,555,1851,1865]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
6.00) in the compound
|
||
<emphasis id="FAFEF0016F749B41FFA11F15883EC902" bold="true" box="[100,112,1871,1890]" pageId="3" pageNumber="4">2</emphasis>
|
||
, when compared to that in
|
||
<emphasis id="FAFEF0016F749B41FE481F1589D7C902" bold="true" box="[397,409,1871,1890]" pageId="3" pageNumber="4">1</emphasis>
|
||
(
|
||
<emphasis id="FAFEF0016F749B41FE6E1F1589FBC902" bold="true" box="[427,437,1871,1890]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FE701F0D898FC905" attach="left" box="[437,449,1879,1893]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
3.57) suggested the presence of alkenic group in
|
||
<emphasis id="FAFEF0016F749B41FECD1F31895AC91E" bold="true" box="[264,276,1899,1918]" pageId="3" pageNumber="4">2</emphasis>
|
||
, in preference to the hydroxyl in
|
||
<emphasis id="FAFEF0016F749B41FD9B1F318A24C91E" bold="true" box="[606,618,1899,1918]" pageId="3" pageNumber="4">1</emphasis>
|
||
at this location (C-27). Lower chemical shift value of about ~3 ppm at H-39 (
|
||
<emphasis id="FAFEF0016F749B41FD761FDD8AF3C9FA" bold="true" box="[691,701,1927,1946]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FD781FD58A87C9FD" attach="left" box="[701,713,1935,1949]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
0.94) was observed in
|
||
<emphasis id="FAFEF0016F749B41FEC71FF98940C9D6" bold="true" box="[258,270,1955,1974]" pageId="3" pageNumber="4">2</emphasis>
|
||
when compared to that recorded in
|
||
<emphasis id="FAFEF0016F749B41FDAF1FF98A38C9D6" bold="true" box="[618,630,1955,1974]" pageId="3" pageNumber="4">1</emphasis>
|
||
(
|
||
<emphasis id="FAFEF0016F749B41FD401FF98AC1C9D6" bold="true" box="[645,655,1955,1974]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="540E2E566F749B41FD4B1FF18AD4C9D9" attach="left" box="[654,666,1963,1977]" fontSize="6" pageId="3" pageNumber="4">H</subScript>
|
||
3.63), and were attributed to the occurrences of hydroxyl in
|
||
<emphasis id="FAFEF0016F749B41FB3A1E2A8D45C8E3" bold="true" box="[1279,1291,1648,1667]" pageId="3" pageNumber="4">1</emphasis>
|
||
and terminal methyl in
|
||
<emphasis id="FAFEF0016F749B41FC951ED68B12C8FF" bold="true" box="[848,860,1676,1695]" pageId="3" pageNumber="4">2</emphasis>
|
||
. NOEs from H-32/H-24/H-21/H-39/H-38/H-37/H-5/H-35 were acknowledged for their
|
||
<emphasis id="FAFEF0016F749B41FBD01EF38C6EC8DC" bold="true" box="[1045,1056,1705,1724]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
-orientation (
|
||
<bibRefCitation id="AC1B51E26F749B41FB5B1EF28D10C8DB" author="Helfrich, E. J. N. & Vogel, C. M. & Ueoka, R. & Ryffel, F. & Muller, D. B. & Probst, S. & Kreuzer, M. & Piel, J. & Vorholt, J. A." box="[1182,1374,1704,1724]" pageId="3" pageNumber="4" pagination="909 - 919" refId="ref16029" refString="Helfrich, E. J. N., Vogel, C. M., Ueoka, R., Sch ¨ afer, M., Ryffel, F., Muller, D. B., Probst, S., Kreuzer, M., Piel, J., Vorholt, J. A., 2018. Bipartite interactions, antibiotic production and biosynthetic potential of the Arabidopsis leaf microbiome. Nat. Microbiol. 3 (8), 909 - 919. https: // doi. org / 10.1038 / s 41564 - 018 - 0200 - 0." type="journal article" year="2018">Helfrich et al., 2018</bibRefCitation>
|
||
), and those between H-9/H-36/H-13/H-18/H-19/H-22/H-40/H-41/H-42/H-31 could recognize their
|
||
<emphasis id="FAFEF0016F749B41FBC81EBA8C57C895" bold="true" box="[1037,1049,1760,1781]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
-positioning. The mass spectrum exhibited a molecular ion peak at
|
||
<emphasis id="FAFEF0016F749B41FBC81EA68C7CC96F" bold="true" box="[1037,1074,1788,1807]" italics="true" pageId="3" pageNumber="4">m/z</emphasis>
|
||
672, and the base peak was realized as 2, 2-dihydroxyethen-1-ylium cation at
|
||
<emphasis id="FAFEF0016F749B41FB491F428CFEC94B" bold="true" box="[1164,1200,1816,1835]" italics="true" pageId="3" pageNumber="4">m/z</emphasis>
|
||
59 (
|
||
<emphasis id="FAFEF0016F749B41FB251F428CA5C94B" bold="true" box="[1248,1259,1816,1835]" pageId="3" pageNumber="4">J</emphasis>
|
||
), which was formed by repeated fragmentations including McLafferty rearrangements (Fig.
|
||
<collectionCode id="AE9BB4D66F749B41FCA61F0A8B21C903" box="[867,879,1872,1891]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="3" pageNumber="4" type="Herbarium">S</collectionCode>
|
||
20-
|
||
<collectionCode id="AE9BB4D66F749B41FC4B1F0A8BD4C903" box="[910,922,1872,1891]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="3" pageNumber="4" type="Herbarium">S</collectionCode>
|
||
21).
|
||
</paragraph>
|
||
<caption id="9CF57C9B6F759B40FFA11F1C8D6EC9DD" ID-DOI="http://doi.org/10.5281/zenodo.8235153" ID-Zenodo-Dep="8235153" httpUri="https://zenodo.org/record/8235153/files/figure.png" pageId="2" pageNumber="3" startId="2.[100,130,1862,1879]" targetBox="[189,1398,1409,1833]" targetPageId="2" targetType="figure">
|
||
<paragraph id="C8352C136F759B40FFA11F1C8D6EC9DD" blockId="2.[100,1488,1862,1981]" pageId="2" pageNumber="3">
|
||
<emphasis id="FAFEF0016F759B40FFA11F1C88D2C937" bold="true" box="[100,156,1862,1879]" pageId="2" pageNumber="3">Fig. 1.</emphasis>
|
||
Structural representation of (
|
||
<emphasis id="FAFEF0016F759B40FE5E1F1C89E6C937" bold="true" box="[411,424,1862,1879]" pageId="2" pageNumber="3">A</emphasis>
|
||
) trihydroxy-decahydro-37-methyl-macrobrevin (compound
|
||
<emphasis id="FAFEF0016F759B40FC601F1C8BFEC937" bold="true" box="[933,944,1862,1879]" pageId="2" pageNumber="3">1</emphasis>
|
||
), (
|
||
<emphasis id="FAFEF0016F759B40FC0C1F1C8B9BC936" bold="true" box="[969,981,1862,1878]" pageId="2" pageNumber="3">B</emphasis>
|
||
) hexahydro-macrobrevin (compound
|
||
<emphasis id="FAFEF0016F759B40FAD21F1C8D6CC937" bold="true" box="[1303,1314,1862,1879]" pageId="2" pageNumber="3">2</emphasis>
|
||
), (
|
||
<emphasis id="FAFEF0016F759B40FAFE1F1C8D09C937" bold="true" box="[1339,1351,1862,1879]" pageId="2" pageNumber="3">C</emphasis>
|
||
) hexahydro-41- hydroxy-macrobrevin-31-acetate (compound
|
||
<emphasis id="FAFEF0016F759B40FE341F3A89B2C911" bold="true" box="[497,508,1888,1905]" pageId="2" pageNumber="3">3</emphasis>
|
||
), and (
|
||
<emphasis id="FAFEF0016F759B40FD821F3A8A1BC910" bold="true" box="[583,597,1888,1904]" pageId="2" pageNumber="3">D</emphasis>
|
||
) hexahydro-28-nor-methyl-5-methoxy-macrobrevin (compound
|
||
<emphasis id="FAFEF0016F759B40FB4F1F3A8CDBC911" bold="true" box="[1162,1173,1888,1905]" pageId="2" pageNumber="3">4</emphasis>
|
||
) isolated from marine macroalgaassociated
|
||
<taxonomicName id="0F8A57906F759B40FF061F2089E6C9EA" authority="MTCC" authorityName="MTCC" box="[195,424,1913,1930]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="2" pageNumber="3" phylum="Firmicutes" rank="species" species="amyloliquefaciens">
|
||
<emphasis id="FAFEF0016F759B40FF061F208922C9EA" bold="true" box="[195,364,1913,1930]" italics="true" pageId="2" pageNumber="3">B. amyloliquefaciens</emphasis>
|
||
MTCC
|
||
</taxonomicName>
|
||
12713. (
|
||
<emphasis id="FAFEF0016F759B40FE3E1F238A48C9E9" bold="true" box="[507,518,1913,1929]" pageId="2" pageNumber="3">E</emphasis>
|
||
) The zone of inhibition (34 mm) observed with hexahydro-41-hydroxy-macrobrevin-31-acetate (compound
|
||
<emphasis id="FAFEF0016F759B40FA781F238D86C9EA" bold="true" box="[1469,1480,1913,1930]" pageId="2" pageNumber="3">3</emphasis>
|
||
) against VRE
|
||
<emphasis id="FAFEF0016F759B40FF0F1FC98899C9C4" bold="true" box="[202,215,1939,1956]" italics="true" pageId="2" pageNumber="3">fs</emphasis>
|
||
as visualized on Mueller Hinton agar plates by disc diffusion assay was illustrated. The amounts of compound
|
||
<emphasis id="FAFEF0016F759B40FB431FC98CDFC9C4" bold="true" box="[1158,1169,1939,1956]" pageId="2" pageNumber="3">3</emphasis>
|
||
and chloramphenicol were 30 μg per disc. Chloramphenicol and ethyl acetate, which were used as the positive and negative control, were denoted with (+) and (), respectively.
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="9CF57C9B6F749B41FFA118CC8A0CCEA0" ID-Table-UUID="9CF57C9B6F749B41FFA118CC8A0CCEA0" httpUri="http://table.plazi.org/id/9CF57C9B6F749B41FFA118CC8A0CCEA0" pageId="3" pageNumber="4" startId="3.[100,150,150,166]" targetBox="[116,1471,454,1467]" targetIsTable="true" targetPageId="3" targetType="table">
|
||
<paragraph id="C8352C136F749B41FFA118CC88FBCEC7" blockId="3.[100,578,150,193]" box="[100,181,150,167]" pageId="3" pageNumber="4">
|
||
<emphasis id="FAFEF0016F749B41FFA118CC88FBCEC7" bold="true" box="[100,181,150,167]" pageId="3" pageNumber="4">Table 1A</emphasis>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F749B41FFA118EA8A0CCEA0" blockId="3.[100,578,150,193]" box="[100,578,176,193]" pageId="3" pageNumber="4">
|
||
NMR spectroscopic data of macrobrevin analogues,
|
||
<emphasis id="FAFEF0016F749B41FDD818EA8A73CEA1" bold="true" box="[541,573,176,193]" pageId="3" pageNumber="4">1–2</emphasis>
|
||
.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="C8352C136F749B41FFB119908DC6CBDB" pageId="3" pageNumber="4">
|
||
<table id="BA8ADEB36F7464BDFFB1199C8DF1CBDB" box="[116,1471,454,1467]" colsContinueIn="5.[116,1471,470,1506]" gridcols="10" gridrows="44" pageId="3" pageNumber="4">
|
||
<tr id="76BA2E516F7464BDFFB1199C8DF1CFB8" box="[116,1471,454,472]" gridrow="0" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB1199C88DECFB8" box="[116,144,454,472]" gridcol="0" gridrow="0" pageId="3" pageNumber="4">No.</th>
|
||
<th id="356B472D6F7464BDFF08199C88B6CFB8" box="[205,248,454,472]" gridcol="1" gridrow="0" pageId="3" pageNumber="4">13C</th>
|
||
<th id="356B472D6F7464BDFEF1199C89A4CFB8" box="[308,490,454,472]" gridcol="2" gridrow="0" pageId="3" pageNumber="4">
|
||
1H (mult., int.,
|
||
<emphasis id="FAFEF0016F749B41FE6D199089FECFB8" bold="true" box="[424,432,458,472]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
in Hz) a
|
||
</th>
|
||
<th id="356B472D6F7464BDFDE2199C8A32CFB8" box="[551,636,454,472]" gridcol="3" gridrow="0" pageId="3" pageNumber="4">COSY</th>
|
||
<th id="356B472D6F7464BDFD7D199C8B4FCFB8" box="[696,769,454,472]" gridcol="4" gridrow="0" pageId="3" pageNumber="4">HMBC</th>
|
||
<th id="356B472D6F7464BDFCF8199C8B17CFB8" box="[829,857,454,472]" gridcol="5" gridrow="0" pageId="3" pageNumber="4">No.</th>
|
||
<th id="356B472D6F7464BDFC51199C8BF1CFB8" box="[916,959,454,472]" gridcol="6" gridrow="0" pageId="3" pageNumber="4">13C</th>
|
||
<th id="356B472D6F7464BDFC3E199C8CFFCFB8" box="[1019,1201,454,472]" gridcol="7" gridrow="0" pageId="3" pageNumber="4">
|
||
1H (mult., int.,
|
||
<emphasis id="FAFEF0016F749B41FBAA19908C39CFB8" bold="true" box="[1135,1143,458,472]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
in Hz) a
|
||
</th>
|
||
<th id="356B472D6F7464BDFB2B199C8D0DCFB8" box="[1262,1347,454,472]" gridcol="8" gridrow="0" pageId="3" pageNumber="4">COSY</th>
|
||
<th id="356B472D6F7464BDFABA199C8DF1CFB8" box="[1407,1471,454,472]" gridcol="9" gridrow="0" pageId="3" pageNumber="4">HMBC</th>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB119B78DF1CF9B" box="[116,1471,493,507]" gridrow="1" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB119B788DECF9B" box="[116,144,493,507]" gridcol="0" gridrow="1" pageId="3" pageNumber="4">1</th>
|
||
<td id="356B472D6F7464BDFF0819B788B6CF9B" box="[205,248,493,507]" gridcol="1" gridrow="1" pageId="3" pageNumber="4">166.2</td>
|
||
<td id="356B472D6F7464BDFEF119B789A4CF9B" box="[308,490,493,507]" gridcol="2" gridrow="1" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFDE219B78A32CF9B" box="[551,636,493,507]" gridcol="3" gridrow="1" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D19B78B4FCF9B" box="[696,769,493,507]" gridcol="4" gridrow="1" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF819B78B17CF9B" box="[829,857,493,507]" gridcol="5" gridrow="1" pageId="3" pageNumber="4">1</td>
|
||
<td id="356B472D6F7464BDFC5119B78BF1CF9B" box="[916,959,493,507]" gridcol="6" gridrow="1" pageId="3" pageNumber="4">166.2</td>
|
||
<td id="356B472D6F7464BDFC3E19B78CFFCF9B" box="[1019,1201,493,507]" gridcol="7" gridrow="1" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFB2B19B78D0DCF9B" box="[1262,1347,493,507]" gridcol="8" gridrow="1" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA19B78DF1CF9B" box="[1407,1471,493,507]" gridcol="9" gridrow="1" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11A5E8DF1CC72" box="[116,1471,516,530]" gridrow="2" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11A5E88DECC72" box="[116,144,516,530]" gridcol="0" gridrow="2" pageId="3" pageNumber="4">2</th>
|
||
<td id="356B472D6F7464BDFF081A5E88B6CC72" box="[205,248,516,530]" gridcol="1" gridrow="2" pageId="3" pageNumber="4">122.9</td>
|
||
<td id="356B472D6F7464BDFEF11A5E89A4CC72" box="[308,490,516,530]" gridcol="2" gridrow="2" pageId="3" pageNumber="4">6.05 (d, 1H, 13.8)</td>
|
||
<td id="356B472D6F7464BDFDE21A5E8A32CC72" box="[551,636,516,530]" gridcol="3" gridrow="2" pageId="3" pageNumber="4">H-3</td>
|
||
<td id="356B472D6F7464BDFD7D1A5E8B4FCC72" box="[696,769,516,530]" gridcol="4" gridrow="2" pageId="3" pageNumber="4">C-1, 4</td>
|
||
<td id="356B472D6F7464BDFCF81A5E8B17CC72" box="[829,857,516,530]" gridcol="5" gridrow="2" pageId="3" pageNumber="4">2</td>
|
||
<td id="356B472D6F7464BDFC511A5E8BF1CC72" box="[916,959,516,530]" gridcol="6" gridrow="2" pageId="3" pageNumber="4">122.4</td>
|
||
<td id="356B472D6F7464BDFC3E1A5E8CFFCC72" box="[1019,1201,516,530]" gridcol="7" gridrow="2" pageId="3" pageNumber="4">5.82 (d, 1H, 13.1)</td>
|
||
<td id="356B472D6F7464BDFB2B1A5E8D0DCC72" box="[1262,1347,516,530]" gridcol="8" gridrow="2" pageId="3" pageNumber="4">H-3</td>
|
||
<td id="356B472D6F7464BDFABA1A5E8DF1CC72" box="[1407,1471,516,530]" gridcol="9" gridrow="2" pageId="3" pageNumber="4">C-1, 4</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11A408DF1CC49" box="[116,1471,538,553]" gridrow="3" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11A4088DECC49" box="[116,144,538,553]" gridcol="0" gridrow="3" pageId="3" pageNumber="4">3</th>
|
||
<td id="356B472D6F7464BDFF081A4088B6CC49" box="[205,248,538,553]" gridcol="1" gridrow="3" pageId="3" pageNumber="4">148.4</td>
|
||
<td id="356B472D6F7464BDFEF11A4089A4CC49" box="[308,490,538,553]" gridcol="2" gridrow="3" pageId="3" pageNumber="4">7.09 (d, 1H, 12.1)</td>
|
||
<td id="356B472D6F7464BDFDE21A408A32CC49" box="[551,636,538,553]" gridcol="3" gridrow="3" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1A408B4FCC49" box="[696,769,538,553]" gridcol="4" gridrow="3" pageId="3" pageNumber="4">C-1</td>
|
||
<td id="356B472D6F7464BDFCF81A408B17CC49" box="[829,857,538,553]" gridcol="5" gridrow="3" pageId="3" pageNumber="4">3</td>
|
||
<td id="356B472D6F7464BDFC511A408BF1CC49" box="[916,959,538,553]" gridcol="6" gridrow="3" pageId="3" pageNumber="4">155.2</td>
|
||
<td id="356B472D6F7464BDFC3E1A408CFFCC49" box="[1019,1201,538,553]" gridcol="7" gridrow="3" pageId="3" pageNumber="4">6.89 (dd, 1H, 12.1, 4.1)</td>
|
||
<td id="356B472D6F7464BDFB2B1A408D0DCC49" box="[1262,1347,538,553]" gridcol="8" gridrow="3" pageId="3" pageNumber="4">H-4</td>
|
||
<td id="356B472D6F7464BDFABA1A408DF1CC49" box="[1407,1471,538,553]" gridcol="9" gridrow="3" pageId="3" pageNumber="4">C-1</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11A6B8DF1CC20" box="[116,1471,561,576]" gridrow="4" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11A6B88DECC20" box="[116,144,561,576]" gridcol="0" gridrow="4" pageId="3" pageNumber="4">4</th>
|
||
<td id="356B472D6F7464BDFF081A6B88B6CC20" box="[205,248,561,576]" gridcol="1" gridrow="4" pageId="3" pageNumber="4">81.2</td>
|
||
<td id="356B472D6F7464BDFEF11A6B89A4CC20" box="[308,490,561,576]" gridcol="2" gridrow="4" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFDE21A6B8A32CC20" box="[551,636,561,576]" gridcol="3" gridrow="4" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1A6B8B4FCC20" box="[696,769,561,576]" gridcol="4" gridrow="4" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81A6B8B17CC20" box="[829,857,561,576]" gridcol="5" gridrow="4" pageId="3" pageNumber="4">4</td>
|
||
<td id="356B472D6F7464BDFC511A6B8BF1CC20" box="[916,959,561,576]" gridcol="6" gridrow="4" pageId="3" pageNumber="4">37.5</td>
|
||
<td id="356B472D6F7464BDFC3E1A6B8CFFCC20" box="[1019,1201,561,576]" gridcol="7" gridrow="4" pageId="3" pageNumber="4">2.65 (m, 1H, 2.1)</td>
|
||
<td id="356B472D6F7464BDFB2B1A6B8D0DCC20" box="[1262,1347,561,576]" gridcol="8" gridrow="4" pageId="3" pageNumber="4">H-5, H-35</td>
|
||
<td id="356B472D6F7464BDFABA1A6B8DF1CC20" box="[1407,1471,561,576]" gridcol="9" gridrow="4" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11A128DF1CC37" box="[116,1471,584,599]" gridrow="5" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11A1288DECC37" box="[116,144,584,599]" gridcol="0" gridrow="5" pageId="3" pageNumber="4">5</th>
|
||
<td id="356B472D6F7464BDFF081A1288B6CC37" box="[205,248,584,599]" gridcol="1" gridrow="5" pageId="3" pageNumber="4">79.8</td>
|
||
<td id="356B472D6F7464BDFEF11A1289A4CC37" box="[308,490,584,599]" gridcol="2" gridrow="5" pageId="3" pageNumber="4">
|
||
3.35 (t, 1H
|
||
<emphasis id="FAFEF0016F749B41FE421A1289DECC37" bold="true" box="[391,400,584,599]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
, 3.8)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21A128A32CC37" box="[551,636,584,599]" gridcol="3" gridrow="5" pageId="3" pageNumber="4">H-6</td>
|
||
<td id="356B472D6F7464BDFD7D1A128B4FCC37" box="[696,769,584,599]" gridcol="4" gridrow="5" pageId="3" pageNumber="4">C-3, 4, 7</td>
|
||
<td id="356B472D6F7464BDFCF81A128B17CC37" box="[829,857,584,599]" gridcol="5" gridrow="5" pageId="3" pageNumber="4">5</td>
|
||
<td id="356B472D6F7464BDFC511A128BF1CC37" box="[916,959,584,599]" gridcol="6" gridrow="5" pageId="3" pageNumber="4">79.6</td>
|
||
<td id="356B472D6F7464BDFC3E1A128CFFCC37" box="[1019,1201,584,599]" gridcol="7" gridrow="5" pageId="3" pageNumber="4">
|
||
3.40 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FB921A128C2ECC37" bold="true" box="[1111,1120,584,599]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1A128D0DCC37" box="[1262,1347,584,599]" gridcol="8" gridrow="5" pageId="3" pageNumber="4">H-6</td>
|
||
<td id="356B472D6F7464BDFABA1A128DF1CC37" box="[1407,1471,584,599]" gridcol="9" gridrow="5" pageId="3" pageNumber="4">C-3, 7</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11A058DF1CC0D" box="[116,1471,607,621]" gridrow="6" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11A0588DECC0D" box="[116,144,607,621]" gridcol="0" gridrow="6" pageId="3" pageNumber="4">6</th>
|
||
<td id="356B472D6F7464BDFF081A0588B6CC0D" box="[205,248,607,621]" gridcol="1" gridrow="6" pageId="3" pageNumber="4">31.0</td>
|
||
<td id="356B472D6F7464BDFEF11A0589A4CC0D" box="[308,490,607,621]" gridcol="2" gridrow="6" pageId="3" pageNumber="4">1.65 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21A058A32CC0D" box="[551,636,607,621]" gridcol="3" gridrow="6" pageId="3" pageNumber="4">H-7</td>
|
||
<td id="356B472D6F7464BDFD7D1A058B4FCC0D" box="[696,769,607,621]" gridcol="4" gridrow="6" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81A058B17CC0D" box="[829,857,607,621]" gridcol="5" gridrow="6" pageId="3" pageNumber="4">6</td>
|
||
<td id="356B472D6F7464BDFC511A058BF1CC0D" box="[916,959,607,621]" gridcol="6" gridrow="6" pageId="3" pageNumber="4">29.0</td>
|
||
<td id="356B472D6F7464BDFC3E1A058CFFCC0D" box="[1019,1201,607,621]" gridcol="7" gridrow="6" pageId="3" pageNumber="4">1.64 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFB2B1A058D0DCC0D" box="[1262,1347,607,621]" gridcol="8" gridrow="6" pageId="3" pageNumber="4">H-7</td>
|
||
<td id="356B472D6F7464BDFABA1A058DF1CC0D" box="[1407,1471,607,621]" gridcol="9" gridrow="6" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11A2C8DF1CCE4" box="[116,1471,630,644]" gridrow="7" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11A2C88DECCE4" box="[116,144,630,644]" gridcol="0" gridrow="7" pageId="3" pageNumber="4">7</th>
|
||
<td id="356B472D6F7464BDFF081A2C88B6CCE4" box="[205,248,630,644]" gridcol="1" gridrow="7" pageId="3" pageNumber="4">28.4</td>
|
||
<td id="356B472D6F7464BDFEF11A2C89A4CCE4" box="[308,490,630,644]" gridcol="2" gridrow="7" pageId="3" pageNumber="4">1.49 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21A2C8A32CCE4" box="[551,636,630,644]" gridcol="3" gridrow="7" pageId="3" pageNumber="4">H-8</td>
|
||
<td id="356B472D6F7464BDFD7D1A2C8B4FCCE4" box="[696,769,630,644]" gridcol="4" gridrow="7" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81A2C8B17CCE4" box="[829,857,630,644]" gridcol="5" gridrow="7" pageId="3" pageNumber="4">7</td>
|
||
<td id="356B472D6F7464BDFC511A2C8BF1CCE4" box="[916,959,630,644]" gridcol="6" gridrow="7" pageId="3" pageNumber="4">17.5</td>
|
||
<td id="356B472D6F7464BDFC3E1A2C8CFFCCE4" box="[1019,1201,630,644]" gridcol="7" gridrow="7" pageId="3" pageNumber="4">1.48 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFB2B1A2C8D0DCCE4" box="[1262,1347,630,644]" gridcol="8" gridrow="7" pageId="3" pageNumber="4">H-8</td>
|
||
<td id="356B472D6F7464BDFABA1A2C8DF1CCE4" box="[1407,1471,630,644]" gridcol="9" gridrow="7" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11AD78DF1CCFB" box="[116,1471,653,667]" gridrow="8" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11AD788DECCFB" box="[116,144,653,667]" gridcol="0" gridrow="8" pageId="3" pageNumber="4">8</th>
|
||
<td id="356B472D6F7464BDFF081AD788B6CCFB" box="[205,248,653,667]" gridcol="1" gridrow="8" pageId="3" pageNumber="4">37.5</td>
|
||
<td id="356B472D6F7464BDFEF11AD789A4CCFB" box="[308,490,653,667]" gridcol="2" gridrow="8" pageId="3" pageNumber="4">1.67 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21AD78A32CCFB" box="[551,636,653,667]" gridcol="3" gridrow="8" pageId="3" pageNumber="4">H-9</td>
|
||
<td id="356B472D6F7464BDFD7D1AD78B4FCCFB" box="[696,769,653,667]" gridcol="4" gridrow="8" pageId="3" pageNumber="4">C-6</td>
|
||
<td id="356B472D6F7464BDFCF81AD78B17CCFB" box="[829,857,653,667]" gridcol="5" gridrow="8" pageId="3" pageNumber="4">8</td>
|
||
<td id="356B472D6F7464BDFC511AD78BF1CCFB" box="[916,959,653,667]" gridcol="6" gridrow="8" pageId="3" pageNumber="4">36.8</td>
|
||
<td id="356B472D6F7464BDFC3E1AD78CFFCCFB" box="[1019,1201,653,667]" gridcol="7" gridrow="8" pageId="3" pageNumber="4">1.65 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFB2B1AD78D0DCCFB" box="[1262,1347,653,667]" gridcol="8" gridrow="8" pageId="3" pageNumber="4">H-9</td>
|
||
<td id="356B472D6F7464BDFABA1AD78DF1CCFB" box="[1407,1471,653,667]" gridcol="9" gridrow="8" pageId="3" pageNumber="4">C-6</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11AF88DF1CCD2" box="[116,1471,674,690]" gridrow="9" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11AF888DECCD2" box="[116,144,674,690]" gridcol="0" gridrow="9" pageId="3" pageNumber="4">9</th>
|
||
<td id="356B472D6F7464BDFF081AF888B6CCD2" box="[205,248,674,690]" gridcol="1" gridrow="9" pageId="3" pageNumber="4">73.1</td>
|
||
<td id="356B472D6F7464BDFEF11AF889A4CCD2" box="[308,490,674,690]" gridcol="2" gridrow="9" pageId="3" pageNumber="4">
|
||
3.15 (q, 1H
|
||
<emphasis id="FAFEF0016F749B41FE4F1AF889DDCCD2" bold="true" box="[394,403,674,690]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 2.7)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21AF88A32CCD2" box="[551,636,674,690]" gridcol="3" gridrow="9" pageId="3" pageNumber="4">H-10</td>
|
||
<td id="356B472D6F7464BDFD7D1AF88B4FCCD2" box="[696,769,674,690]" gridcol="4" gridrow="9" pageId="3" pageNumber="4">C-7, 10</td>
|
||
<td id="356B472D6F7464BDFCF81AF88B17CCD2" box="[829,857,674,690]" gridcol="5" gridrow="9" pageId="3" pageNumber="4">9</td>
|
||
<td id="356B472D6F7464BDFC511AF88BF1CCD2" box="[916,959,674,690]" gridcol="6" gridrow="9" pageId="3" pageNumber="4">75.4</td>
|
||
<td id="356B472D6F7464BDFC3E1AF88CFFCCD2" box="[1019,1201,674,690]" gridcol="7" gridrow="9" pageId="3" pageNumber="4">
|
||
4.32 (t, 1H
|
||
<emphasis id="FAFEF0016F749B41FB8B1AF88C19CCD2" bold="true" box="[1102,1111,674,690]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 2.7)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1AF88D0DCCD2" box="[1262,1347,674,690]" gridcol="8" gridrow="9" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1AF88DF1CCD2" box="[1407,1471,674,690]" gridcol="9" gridrow="9" pageId="3" pageNumber="4">C-7, 10</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11AE08DF1CCA9" box="[116,1471,698,713]" gridrow="10" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11AE088DECCA9" box="[116,144,698,713]" gridcol="0" gridrow="10" pageId="3" pageNumber="4">10</th>
|
||
<td id="356B472D6F7464BDFF081AE088B6CCA9" box="[205,248,698,713]" gridcol="1" gridrow="10" pageId="3" pageNumber="4">19.0</td>
|
||
<td id="356B472D6F7464BDFEF11AE089A4CCA9" box="[308,490,698,713]" gridcol="2" gridrow="10" pageId="3" pageNumber="4">
|
||
1.78 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FE551AE089D7CCA9" bold="true" box="[400,409,698,713]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21AE08A32CCA9" box="[551,636,698,713]" gridcol="3" gridrow="10" pageId="3" pageNumber="4">H-11, H-36</td>
|
||
<td id="356B472D6F7464BDFD7D1AE08B4FCCA9" box="[696,769,698,713]" gridcol="4" gridrow="10" pageId="3" pageNumber="4">C-8</td>
|
||
<td id="356B472D6F7464BDFCF81AE08B17CCA9" box="[829,857,698,713]" gridcol="5" gridrow="10" pageId="3" pageNumber="4">10</td>
|
||
<td id="356B472D6F7464BDFC511AE08BF1CCA9" box="[916,959,698,713]" gridcol="6" gridrow="10" pageId="3" pageNumber="4">138.6</td>
|
||
<td id="356B472D6F7464BDFC3E1AE08CFFCCA9" box="[1019,1201,698,713]" gridcol="7" gridrow="10" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFB2B1AE08D0DCCA9" box="[1262,1347,698,713]" gridcol="8" gridrow="10" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1AE08DF1CCA9" box="[1407,1471,698,713]" gridcol="9" gridrow="10" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11A8B8DF1CC80" box="[116,1471,721,736]" gridrow="11" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11A8B88DECC80" box="[116,144,721,736]" gridcol="0" gridrow="11" pageId="3" pageNumber="4">11</th>
|
||
<td id="356B472D6F7464BDFF081A8B88B6CC80" box="[205,248,721,736]" gridcol="1" gridrow="11" pageId="3" pageNumber="4">28.5</td>
|
||
<td id="356B472D6F7464BDFEF11A8B89A4CC80" box="[308,490,721,736]" gridcol="2" gridrow="11" pageId="3" pageNumber="4">1.38 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21A8B8A32CC80" box="[551,636,721,736]" gridcol="3" gridrow="11" pageId="3" pageNumber="4">H-12</td>
|
||
<td id="356B472D6F7464BDFD7D1A8B8B4FCC80" box="[696,769,721,736]" gridcol="4" gridrow="11" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81A8B8B17CC80" box="[829,857,721,736]" gridcol="5" gridrow="11" pageId="3" pageNumber="4">11</td>
|
||
<td id="356B472D6F7464BDFC511A8B8BF1CC80" box="[916,959,721,736]" gridcol="6" gridrow="11" pageId="3" pageNumber="4">127.6</td>
|
||
<td id="356B472D6F7464BDFC3E1A8B8CFFCC80" box="[1019,1201,721,736]" gridcol="7" gridrow="11" pageId="3" pageNumber="4">5.19 (t, 1H, 10.5)</td>
|
||
<td id="356B472D6F7464BDFB2B1A8B8D0DCC80" box="[1262,1347,721,736]" gridcol="8" gridrow="11" pageId="3" pageNumber="4">H-12</td>
|
||
<td id="356B472D6F7464BDFABA1A8B8DF1CC80" box="[1407,1471,721,736]" gridcol="9" gridrow="11" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11AB28DF1CC97" box="[116,1471,744,759]" gridrow="12" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11AB288DECC97" box="[116,144,744,759]" gridcol="0" gridrow="12" pageId="3" pageNumber="4">12</th>
|
||
<td id="356B472D6F7464BDFF081AB288B6CC97" box="[205,248,744,759]" gridcol="1" gridrow="12" pageId="3" pageNumber="4">32.4</td>
|
||
<td id="356B472D6F7464BDFEF11AB289A4CC97" box="[308,490,744,759]" gridcol="2" gridrow="12" pageId="3" pageNumber="4">1.44 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21AB28A32CC97" box="[551,636,744,759]" gridcol="3" gridrow="12" pageId="3" pageNumber="4">H-13</td>
|
||
<td id="356B472D6F7464BDFD7D1AB28B4FCC97" box="[696,769,744,759]" gridcol="4" gridrow="12" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81AB28B17CC97" box="[829,857,744,759]" gridcol="5" gridrow="12" pageId="3" pageNumber="4">12</td>
|
||
<td id="356B472D6F7464BDFC511AB28BF1CC97" box="[916,959,744,759]" gridcol="6" gridrow="12" pageId="3" pageNumber="4">40.5</td>
|
||
<td id="356B472D6F7464BDFC3E1AB28CFFCC97" box="[1019,1201,744,759]" gridcol="7" gridrow="12" pageId="3" pageNumber="4">2.07 (t, 2H, 1.2)</td>
|
||
<td id="356B472D6F7464BDFB2B1AB28D0DCC97" box="[1262,1347,744,759]" gridcol="8" gridrow="12" pageId="3" pageNumber="4">H-13</td>
|
||
<td id="356B472D6F7464BDFABA1AB28DF1CC97" box="[1407,1471,744,759]" gridcol="9" gridrow="12" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11AA78DF1CD6D" box="[116,1471,765,781]" gridrow="13" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11AA788DECD6D" box="[116,144,765,781]" gridcol="0" gridrow="13" pageId="3" pageNumber="4">13</th>
|
||
<td id="356B472D6F7464BDFF081AA788B6CD6D" box="[205,248,765,781]" gridcol="1" gridrow="13" pageId="3" pageNumber="4">45.2</td>
|
||
<td id="356B472D6F7464BDFEF11AA789A4CD6D" box="[308,490,765,781]" gridcol="2" gridrow="13" pageId="3" pageNumber="4">
|
||
2.15 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FE551AA789D7CD6D" bold="true" box="[400,409,765,781]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21AA78A32CD6D" box="[551,636,765,781]" gridcol="3" gridrow="13" pageId="3" pageNumber="4">H-14, H-37</td>
|
||
<td id="356B472D6F7464BDFD7D1AA78B4FCD6D" box="[696,769,765,781]" gridcol="4" gridrow="13" pageId="3" pageNumber="4">C-11, 37a</td>
|
||
<td id="356B472D6F7464BDFCF81AA78B17CD6D" box="[829,857,765,781]" gridcol="5" gridrow="13" pageId="3" pageNumber="4">13</td>
|
||
<td id="356B472D6F7464BDFC511AA78BF1CD6D" box="[916,959,765,781]" gridcol="6" gridrow="13" pageId="3" pageNumber="4">42.6</td>
|
||
<td id="356B472D6F7464BDFC3E1AA78CFFCD6D" box="[1019,1201,765,781]" gridcol="7" gridrow="13" pageId="3" pageNumber="4">
|
||
2.15 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FB921AA78C2ECD6D" bold="true" box="[1111,1120,765,781]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1AA78D0DCD6D" box="[1262,1347,765,781]" gridcol="8" gridrow="13" pageId="3" pageNumber="4">H-14, H-37</td>
|
||
<td id="356B472D6F7464BDFABA1AA78DF1CD6D" box="[1407,1471,765,781]" gridcol="9" gridrow="13" pageId="3" pageNumber="4">C-11, 37</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11B4C8DF1CD44" box="[116,1471,790,804]" gridrow="14" pageId="3" pageNumber="4" rowspan-8="1">
|
||
<th id="356B472D6F7464BDFFB11B4C88DECD44" box="[116,144,790,804]" gridcol="0" gridrow="14" pageId="3" pageNumber="4">14</th>
|
||
<td id="356B472D6F7464BDFF081B4C88B6CD44" box="[205,248,790,804]" gridcol="1" gridrow="14" pageId="3" pageNumber="4">130.3</td>
|
||
<td id="356B472D6F7464BDFEF11B4C89A4CD44" box="[308,490,790,804]" gridcol="2" gridrow="14" pageId="3" pageNumber="4">5.48 (dd, 1H, 13.1, 2.4)</td>
|
||
<td id="356B472D6F7464BDFDE21B4C8A32CD44" box="[551,636,790,804]" gridcol="3" gridrow="14" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1B4C8B4FCD44" box="[696,769,790,804]" gridcol="4" gridrow="14" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81B4C8B17CD44" box="[829,857,790,804]" gridcol="5" gridrow="14" pageId="3" pageNumber="4">14</td>
|
||
<td id="356B472D6F7464BDFC511B4C8BF1CD44" box="[916,959,790,804]" gridcol="6" gridrow="14" pageId="3" pageNumber="4">129.2</td>
|
||
<td id="356B472D6F7464BDFC3E1B4C8CFFCD44" box="[1019,1201,790,804]" gridcol="7" gridrow="14" pageId="3" pageNumber="4">5.46 (dd, 1H, 13.0, 2.1)</td>
|
||
<td id="356B472D6F7464BDFABA1B4C8DF1CD44" box="[1407,1471,790,804]" gridcol="9" gridrow="14" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11B778DF1CD5B" box="[116,1471,813,827]" gridrow="15" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11B7788DECD5B" box="[116,144,813,827]" gridcol="0" gridrow="15" pageId="3" pageNumber="4">15</th>
|
||
<td id="356B472D6F7464BDFF081B7788B6CD5B" box="[205,248,813,827]" gridcol="1" gridrow="15" pageId="3" pageNumber="4">131.6</td>
|
||
<td id="356B472D6F7464BDFEF11B7789A4CD5B" box="[308,490,813,827]" gridcol="2" gridrow="15" pageId="3" pageNumber="4">5.52 (dt, 1H, 12.5, 2.1)</td>
|
||
<td id="356B472D6F7464BDFDE21B778A32CD5B" box="[551,636,813,827]" gridcol="3" gridrow="15" pageId="3" pageNumber="4">H-16</td>
|
||
<td id="356B472D6F7464BDFD7D1B778B4FCD5B" box="[696,769,813,827]" gridcol="4" gridrow="15" pageId="3" pageNumber="4">C-17</td>
|
||
<td id="356B472D6F7464BDFCF81B778B17CD5B" box="[829,857,813,827]" gridcol="5" gridrow="15" pageId="3" pageNumber="4">15</td>
|
||
<td id="356B472D6F7464BDFC511B778BF1CD5B" box="[916,959,813,827]" gridcol="6" gridrow="15" pageId="3" pageNumber="4">130.4</td>
|
||
<td id="356B472D6F7464BDFC3E1B778CFFCD5B" box="[1019,1201,813,827]" gridcol="7" gridrow="15" pageId="3" pageNumber="4">5.68 (dt, 1H, 12.1, 2.5)</td>
|
||
<td id="356B472D6F7464BDFB2B1B778D0DCD5B" box="[1262,1347,813,827]" gridcol="8" gridrow="15" pageId="3" pageNumber="4">H-16</td>
|
||
<td id="356B472D6F7464BDFABA1B778DF1CD5B" box="[1407,1471,813,827]" gridcol="9" gridrow="15" pageId="3" pageNumber="4">C-17</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11B1E8DF1CD32" box="[116,1471,836,850]" gridrow="16" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11B1E88DECD32" box="[116,144,836,850]" gridcol="0" gridrow="16" pageId="3" pageNumber="4">16</th>
|
||
<td id="356B472D6F7464BDFF081B1E88B6CD32" box="[205,248,836,850]" gridcol="1" gridrow="16" pageId="3" pageNumber="4">30.4</td>
|
||
<td id="356B472D6F7464BDFEF11B1E89A4CD32" box="[308,490,836,850]" gridcol="2" gridrow="16" pageId="3" pageNumber="4">2.07 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21B1E8A32CD32" box="[551,636,836,850]" gridcol="3" gridrow="16" pageId="3" pageNumber="4">H-17</td>
|
||
<td id="356B472D6F7464BDFD7D1B1E8B4FCD32" box="[696,769,836,850]" gridcol="4" gridrow="16" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81B1E8B17CD32" box="[829,857,836,850]" gridcol="5" gridrow="16" pageId="3" pageNumber="4">16</td>
|
||
<td id="356B472D6F7464BDFC511B1E8BF1CD32" box="[916,959,836,850]" gridcol="6" gridrow="16" pageId="3" pageNumber="4">28.1</td>
|
||
<td id="356B472D6F7464BDFC3E1B1E8CFFCD32" box="[1019,1201,836,850]" gridcol="7" gridrow="16" pageId="3" pageNumber="4">2.04 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFB2B1B1E8D0DCD32" box="[1262,1347,836,850]" gridcol="8" gridrow="16" pageId="3" pageNumber="4">H-17</td>
|
||
<td id="356B472D6F7464BDFABA1B1E8DF1CD32" box="[1407,1471,836,850]" gridcol="9" gridrow="16" pageId="3" pageNumber="4">C-14</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11B008DF1CD09" box="[116,1471,858,873]" gridrow="17" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11B0088DECD09" box="[116,144,858,873]" gridcol="0" gridrow="17" pageId="3" pageNumber="4">17</th>
|
||
<td id="356B472D6F7464BDFF081B0088B6CD09" box="[205,248,858,873]" gridcol="1" gridrow="17" pageId="3" pageNumber="4">31.8</td>
|
||
<td id="356B472D6F7464BDFEF11B0089A4CD09" box="[308,490,858,873]" gridcol="2" gridrow="17" pageId="3" pageNumber="4">1.50 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21B008A32CD09" box="[551,636,858,873]" gridcol="3" gridrow="17" pageId="3" pageNumber="4">H-18</td>
|
||
<td id="356B472D6F7464BDFD7D1B008B4FCD09" box="[696,769,858,873]" gridcol="4" gridrow="17" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81B008B17CD09" box="[829,857,858,873]" gridcol="5" gridrow="17" pageId="3" pageNumber="4">17</td>
|
||
<td id="356B472D6F7464BDFC511B008BF1CD09" box="[916,959,858,873]" gridcol="6" gridrow="17" pageId="3" pageNumber="4">31.5</td>
|
||
<td id="356B472D6F7464BDFC3E1B008CFFCD09" box="[1019,1201,858,873]" gridcol="7" gridrow="17" pageId="3" pageNumber="4">1.50 (m, 1H)</td>
|
||
<td id="356B472D6F7464BDFB2B1B008D0DCD09" box="[1262,1347,858,873]" gridcol="8" gridrow="17" pageId="3" pageNumber="4">H-18</td>
|
||
<td id="356B472D6F7464BDFABA1B008DF1CD09" box="[1407,1471,858,873]" gridcol="9" gridrow="17" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11B2A8DF1CDE0" box="[116,1471,880,896]" gridrow="18" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11B2A88DECDE0" box="[116,144,880,896]" gridcol="0" gridrow="18" pageId="3" pageNumber="4">18</th>
|
||
<td id="356B472D6F7464BDFF081B2A88B6CDE0" box="[205,248,880,896]" gridcol="1" gridrow="18" pageId="3" pageNumber="4">36.8</td>
|
||
<td id="356B472D6F7464BDFEF11B2A89A4CDE0" box="[308,490,880,896]" gridcol="2" gridrow="18" pageId="3" pageNumber="4">
|
||
1.72 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FE551B2A89D7CDE0" bold="true" box="[400,409,880,896]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21B2A8A32CDE0" box="[551,636,880,896]" gridcol="3" gridrow="18" pageId="3" pageNumber="4">H-19, H-38</td>
|
||
<td id="356B472D6F7464BDFD7D1B2A8B4FCDE0" box="[696,769,880,896]" gridcol="4" gridrow="18" pageId="3" pageNumber="4">C-20</td>
|
||
<td id="356B472D6F7464BDFCF81B2A8B17CDE0" box="[829,857,880,896]" gridcol="5" gridrow="18" pageId="3" pageNumber="4">18</td>
|
||
<td id="356B472D6F7464BDFC511B2A8BF1CDE0" box="[916,959,880,896]" gridcol="6" gridrow="18" pageId="3" pageNumber="4">38.5</td>
|
||
<td id="356B472D6F7464BDFC3E1B2A8CFFCDE0" box="[1019,1201,880,896]" gridcol="7" gridrow="18" pageId="3" pageNumber="4">
|
||
1.78 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FB921B2A8C2ECDE0" bold="true" box="[1111,1120,880,896]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1B2A8D0DCDE0" box="[1262,1347,880,896]" gridcol="8" gridrow="18" pageId="3" pageNumber="4">H-19, H-38</td>
|
||
<td id="356B472D6F7464BDFABA1B2A8DF1CDE0" box="[1407,1471,880,896]" gridcol="9" gridrow="18" pageId="3" pageNumber="4">C-20</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11BDC8DF1CDF6" box="[116,1471,902,918]" gridrow="19" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11BDC88DECDF6" box="[116,144,902,918]" gridcol="0" gridrow="19" pageId="3" pageNumber="4">19</th>
|
||
<td id="356B472D6F7464BDFF081BDC88B6CDF6" box="[205,248,902,918]" gridcol="1" gridrow="19" pageId="3" pageNumber="4">70.9</td>
|
||
<td id="356B472D6F7464BDFEF11BDC89A4CDF6" box="[308,490,902,918]" gridcol="2" gridrow="19" pageId="3" pageNumber="4">
|
||
3.44 (q, 1H
|
||
<emphasis id="FAFEF0016F749B41FE4F1BDC89DDCDF6" bold="true" box="[394,403,902,918]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 3.1)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21BDC8A32CDF6" box="[551,636,902,918]" gridcol="3" gridrow="19" pageId="3" pageNumber="4">H-20</td>
|
||
<td id="356B472D6F7464BDFD7D1BDC8B4FCDF6" box="[696,769,902,918]" gridcol="4" gridrow="19" pageId="3" pageNumber="4">C-17, 21</td>
|
||
<td id="356B472D6F7464BDFCF81BDC8B17CDF6" box="[829,857,902,918]" gridcol="5" gridrow="19" pageId="3" pageNumber="4">19</td>
|
||
<td id="356B472D6F7464BDFC511BDC8BF1CDF6" box="[916,959,902,918]" gridcol="6" gridrow="19" pageId="3" pageNumber="4">71.3</td>
|
||
<td id="356B472D6F7464BDFC3E1BDC8CFFCDF6" box="[1019,1201,902,918]" gridcol="7" gridrow="19" pageId="3" pageNumber="4">
|
||
3.60 (q, 1H
|
||
<emphasis id="FAFEF0016F749B41FB971BDC8C15CDF6" bold="true" box="[1106,1115,902,918]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 2.2)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1BDC8D0DCDF6" box="[1262,1347,902,918]" gridcol="8" gridrow="19" pageId="3" pageNumber="4">H-20</td>
|
||
<td id="356B472D6F7464BDFABA1BDC8DF1CDF6" box="[1407,1471,902,918]" gridcol="9" gridrow="19" pageId="3" pageNumber="4">C-17, 21</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11BC58DF1CDCD" box="[116,1471,927,941]" gridrow="20" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11BC588DECDCD" box="[116,144,927,941]" gridcol="0" gridrow="20" pageId="3" pageNumber="4">20</th>
|
||
<td id="356B472D6F7464BDFF081BC588B6CDCD" box="[205,248,927,941]" gridcol="1" gridrow="20" pageId="3" pageNumber="4">37.9</td>
|
||
<td id="356B472D6F7464BDFEF11BC589A4CDCD" box="[308,490,927,941]" gridcol="2" gridrow="20" pageId="3" pageNumber="4">1.53 (t, 2H, 3.5)</td>
|
||
<td id="356B472D6F7464BDFDE21BC58A32CDCD" box="[551,636,927,941]" gridcol="3" gridrow="20" pageId="3" pageNumber="4">H-21</td>
|
||
<td id="356B472D6F7464BDFD7D1BC58B4FCDCD" box="[696,769,927,941]" gridcol="4" gridrow="20" pageId="3" pageNumber="4">C-21</td>
|
||
<td id="356B472D6F7464BDFCF81BC58B17CDCD" box="[829,857,927,941]" gridcol="5" gridrow="20" pageId="3" pageNumber="4">20</td>
|
||
<td id="356B472D6F7464BDFC511BC58BF1CDCD" box="[916,959,927,941]" gridcol="6" gridrow="20" pageId="3" pageNumber="4">37.8</td>
|
||
<td id="356B472D6F7464BDFC3E1BC58CFFCDCD" box="[1019,1201,927,941]" gridcol="7" gridrow="20" pageId="3" pageNumber="4">1.52 (t, 2H, 3.5)</td>
|
||
<td id="356B472D6F7464BDFB2B1BC58D0DCDCD" box="[1262,1347,927,941]" gridcol="8" gridrow="20" pageId="3" pageNumber="4">H-21</td>
|
||
<td id="356B472D6F7464BDFABA1BC58DF1CDCD" box="[1407,1471,927,941]" gridcol="9" gridrow="20" pageId="3" pageNumber="4">C-21</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11BEC8DF1CDA5" box="[116,1471,950,965]" gridrow="21" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11BEC88DECDA5" box="[116,144,950,965]" gridcol="0" gridrow="21" pageId="3" pageNumber="4">21</th>
|
||
<td id="356B472D6F7464BDFF081BEC88B6CDA5" box="[205,248,950,965]" gridcol="1" gridrow="21" pageId="3" pageNumber="4">70.2</td>
|
||
<td id="356B472D6F7464BDFEF11BEC89A4CDA5" box="[308,490,950,965]" gridcol="2" gridrow="21" pageId="3" pageNumber="4">
|
||
3.92 (q, 1H
|
||
<emphasis id="FAFEF0016F749B41FE4F1BEC89DDCDA5" bold="true" box="[394,403,950,965]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
, 4.8)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21BEC8A32CDA5" box="[551,636,950,965]" gridcol="3" gridrow="21" pageId="3" pageNumber="4">H-22</td>
|
||
<td id="356B472D6F7464BDFD7D1BEC8B4FCDA5" box="[696,769,950,965]" gridcol="4" gridrow="21" pageId="3" pageNumber="4">C-1</td>
|
||
<td id="356B472D6F7464BDFCF81BEC8B17CDA5" box="[829,857,950,965]" gridcol="5" gridrow="21" pageId="3" pageNumber="4">21</td>
|
||
<td id="356B472D6F7464BDFC511BEC8BF1CDA5" box="[916,959,950,965]" gridcol="6" gridrow="21" pageId="3" pageNumber="4">70.9</td>
|
||
<td id="356B472D6F7464BDFC3E1BEC8CFFCDA5" box="[1019,1201,950,965]" gridcol="7" gridrow="21" pageId="3" pageNumber="4">
|
||
3.91 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FB921BEC8C2ECDA5" bold="true" box="[1111,1120,950,965]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1BEC8D0DCDA5" box="[1262,1347,950,965]" gridcol="8" gridrow="21" pageId="3" pageNumber="4">H-22</td>
|
||
<td id="356B472D6F7464BDFABA1BEC8DF1CDA5" box="[1407,1471,950,965]" gridcol="9" gridrow="21" pageId="3" pageNumber="4">C-1</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11B918DF1CDBB" box="[116,1471,971,987]" gridrow="22" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11B9188DECDBB" box="[116,144,971,987]" gridcol="0" gridrow="22" pageId="3" pageNumber="4">22</th>
|
||
<td id="356B472D6F7464BDFF081B9188B6CDBB" box="[205,248,971,987]" gridcol="1" gridrow="22" pageId="3" pageNumber="4">34.9</td>
|
||
<td id="356B472D6F7464BDFEF11B9189A4CDBB" box="[308,490,971,987]" gridcol="2" gridrow="22" pageId="3" pageNumber="4">
|
||
2.21 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FE551B9189D7CDBB" bold="true" box="[400,409,971,987]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21B918A32CDBB" box="[551,636,971,987]" gridcol="3" gridrow="22" pageId="3" pageNumber="4">H-23, H-39</td>
|
||
<td id="356B472D6F7464BDFD7D1B918B4FCDBB" box="[696,769,971,987]" gridcol="4" gridrow="22" pageId="3" pageNumber="4">C-21, 24</td>
|
||
<td id="356B472D6F7464BDFCF81B918B17CDBB" box="[829,857,971,987]" gridcol="5" gridrow="22" pageId="3" pageNumber="4">22</td>
|
||
<td id="356B472D6F7464BDFC511B918BF1CDBB" box="[916,959,971,987]" gridcol="6" gridrow="22" pageId="3" pageNumber="4">33.1</td>
|
||
<td id="356B472D6F7464BDFC3E1B918CFFCDBB" box="[1019,1201,971,987]" gridcol="7" gridrow="22" pageId="3" pageNumber="4">
|
||
2.40 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FB921B918C2ECDBB" bold="true" box="[1111,1120,971,987]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1B918D0DCDBB" box="[1262,1347,971,987]" gridcol="8" gridrow="22" pageId="3" pageNumber="4">H-23, H-39</td>
|
||
<td id="356B472D6F7464BDFABA1B918DF1CDBB" box="[1407,1471,971,987]" gridcol="9" gridrow="22" pageId="3" pageNumber="4">C-21, 24</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11BB98DF1CD92" box="[116,1471,995,1010]" gridrow="23" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11BB988DECD92" box="[116,144,995,1010]" gridcol="0" gridrow="23" pageId="3" pageNumber="4">23</th>
|
||
<td id="356B472D6F7464BDFF081BB988B6CD92" box="[205,248,995,1010]" gridcol="1" gridrow="23" pageId="3" pageNumber="4">38.6</td>
|
||
<td id="356B472D6F7464BDFEF11BB989A4CD92" box="[308,490,995,1010]" gridcol="2" gridrow="23" pageId="3" pageNumber="4">1.27 (t, 2H, 3.0)</td>
|
||
<td id="356B472D6F7464BDFDE21BB98A32CD92" box="[551,636,995,1010]" gridcol="3" gridrow="23" pageId="3" pageNumber="4">H-24</td>
|
||
<td id="356B472D6F7464BDFD7D1BB98B4FCD92" box="[696,769,995,1010]" gridcol="4" gridrow="23" pageId="3" pageNumber="4">C-21</td>
|
||
<td id="356B472D6F7464BDFCF81BB98B17CD92" box="[829,857,995,1010]" gridcol="5" gridrow="23" pageId="3" pageNumber="4">23</td>
|
||
<td id="356B472D6F7464BDFC511BB98BF1CD92" box="[916,959,995,1010]" gridcol="6" gridrow="23" pageId="3" pageNumber="4">38.6</td>
|
||
<td id="356B472D6F7464BDFC3E1BB98CFFCD92" box="[1019,1201,995,1010]" gridcol="7" gridrow="23" pageId="3" pageNumber="4">1.27 (t, 2H, 2.5)</td>
|
||
<td id="356B472D6F7464BDFB2B1BB98D0DCD92" box="[1262,1347,995,1010]" gridcol="8" gridrow="23" pageId="3" pageNumber="4">H-24</td>
|
||
<td id="356B472D6F7464BDFABA1BB98DF1CD92" box="[1407,1471,995,1010]" gridcol="9" gridrow="23" pageId="3" pageNumber="4">C-21</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11BA08DF1CA69" box="[116,1471,1018,1033]" gridrow="24" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11BA088DECA69" box="[116,144,1018,1033]" gridcol="0" gridrow="24" pageId="3" pageNumber="4">24</th>
|
||
<td id="356B472D6F7464BDFF081BA088B6CA69" box="[205,248,1018,1033]" gridcol="1" gridrow="24" pageId="3" pageNumber="4">35.6</td>
|
||
<td id="356B472D6F7464BDFEF11BA089A4CA69" box="[308,490,1018,1033]" gridcol="2" gridrow="24" pageId="3" pageNumber="4">
|
||
1.69 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FE551BA089D7CA69" bold="true" box="[400,409,1018,1033]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21BA08A32CA69" box="[551,636,1018,1033]" gridcol="3" gridrow="24" pageId="3" pageNumber="4">H-25, H-40</td>
|
||
<td id="356B472D6F7464BDFD7D1BA08B4FCA69" box="[696,769,1018,1033]" gridcol="4" gridrow="24" pageId="3" pageNumber="4">C-26</td>
|
||
<td id="356B472D6F7464BDFCF81BA08B17CA69" box="[829,857,1018,1033]" gridcol="5" gridrow="24" pageId="3" pageNumber="4">24</td>
|
||
<td id="356B472D6F7464BDFC511BA08BF1CA69" box="[916,959,1018,1033]" gridcol="6" gridrow="24" pageId="3" pageNumber="4">35.3</td>
|
||
<td id="356B472D6F7464BDFC3E1BA08CFFCA69" box="[1019,1201,1018,1033]" gridcol="7" gridrow="24" pageId="3" pageNumber="4">
|
||
1.68 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FB921BA08C2ECA69" bold="true" box="[1111,1120,1018,1033]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1BA08D0DCA69" box="[1262,1347,1018,1033]" gridcol="8" gridrow="24" pageId="3" pageNumber="4">H-25, H-40</td>
|
||
<td id="356B472D6F7464BDFABA1BA08DF1CA69" box="[1407,1471,1018,1033]" gridcol="9" gridrow="24" pageId="3" pageNumber="4">C-26</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11C4B8DF1CA7F" box="[116,1471,1041,1055]" gridrow="25" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11C4B88DECA7F" box="[116,144,1041,1055]" gridcol="0" gridrow="25" pageId="3" pageNumber="4">25</th>
|
||
<td id="356B472D6F7464BDFF081C4B88B6CA7F" box="[205,248,1041,1055]" gridcol="1" gridrow="25" pageId="3" pageNumber="4">31.7</td>
|
||
<td id="356B472D6F7464BDFEF11C4B89A4CA7F" box="[308,490,1041,1055]" gridcol="2" gridrow="25" pageId="3" pageNumber="4">1.23 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21C4B8A32CA7F" box="[551,636,1041,1055]" gridcol="3" gridrow="25" pageId="3" pageNumber="4">H-26</td>
|
||
<td id="356B472D6F7464BDFD7D1C4B8B4FCA7F" box="[696,769,1041,1055]" gridcol="4" gridrow="25" pageId="3" pageNumber="4">C-23</td>
|
||
<td id="356B472D6F7464BDFCF81C4B8B17CA7F" box="[829,857,1041,1055]" gridcol="5" gridrow="25" pageId="3" pageNumber="4">25</td>
|
||
<td id="356B472D6F7464BDFC511C4B8BF1CA7F" box="[916,959,1041,1055]" gridcol="6" gridrow="25" pageId="3" pageNumber="4">30.2</td>
|
||
<td id="356B472D6F7464BDFC3E1C4B8CFFCA7F" box="[1019,1201,1041,1055]" gridcol="7" gridrow="25" pageId="3" pageNumber="4">1.25 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFB2B1C4B8D0DCA7F" box="[1262,1347,1041,1055]" gridcol="8" gridrow="25" pageId="3" pageNumber="4">H-26</td>
|
||
<td id="356B472D6F7464BDFABA1C4B8DF1CA7F" box="[1407,1471,1041,1055]" gridcol="9" gridrow="25" pageId="3" pageNumber="4">C-23</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11C728DF1CA56" box="[116,1471,1064,1078]" gridrow="26" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11C7288DECA56" box="[116,144,1064,1078]" gridcol="0" gridrow="26" pageId="3" pageNumber="4">26</th>
|
||
<td id="356B472D6F7464BDFF081C7288B6CA56" box="[205,248,1064,1078]" gridcol="1" gridrow="26" pageId="3" pageNumber="4">34.5</td>
|
||
<td id="356B472D6F7464BDFEF11C7289A4CA56" box="[308,490,1064,1078]" gridcol="2" gridrow="26" pageId="3" pageNumber="4">1.46 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21C728A32CA56" box="[551,636,1064,1078]" gridcol="3" gridrow="26" pageId="3" pageNumber="4">H-27</td>
|
||
<td id="356B472D6F7464BDFD7D1C728B4FCA56" box="[696,769,1064,1078]" gridcol="4" gridrow="26" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81C728B17CA56" box="[829,857,1064,1078]" gridcol="5" gridrow="26" pageId="3" pageNumber="4">26</td>
|
||
<td id="356B472D6F7464BDFC511C728BF1CA56" box="[916,959,1064,1078]" gridcol="6" gridrow="26" pageId="3" pageNumber="4">34.1</td>
|
||
<td id="356B472D6F7464BDFC3E1C728CFFCA56" box="[1019,1201,1064,1078]" gridcol="7" gridrow="26" pageId="3" pageNumber="4">1.46 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFB2B1C728D0DCA56" box="[1262,1347,1064,1078]" gridcol="8" gridrow="26" pageId="3" pageNumber="4">H-27</td>
|
||
<td id="356B472D6F7464BDFABA1C728DF1CA56" box="[1407,1471,1064,1078]" gridcol="9" gridrow="26" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11C658DF1CA2D" box="[116,1471,1087,1101]" gridrow="27" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11C6588DECA2D" box="[116,144,1087,1101]" gridcol="0" gridrow="27" pageId="3" pageNumber="4">27</th>
|
||
<td id="356B472D6F7464BDFF081C6588B6CA2D" box="[205,248,1087,1101]" gridcol="1" gridrow="27" pageId="3" pageNumber="4">71.7</td>
|
||
<td id="356B472D6F7464BDFEF11C6589A4CA2D" box="[308,490,1087,1101]" gridcol="2" gridrow="27" pageId="3" pageNumber="4">3.57 (q, 1H, 3.9)</td>
|
||
<td id="356B472D6F7464BDFDE21C658A32CA2D" box="[551,636,1087,1101]" gridcol="3" gridrow="27" pageId="3" pageNumber="4">H-28</td>
|
||
<td id="356B472D6F7464BDFD7D1C658B4FCA2D" box="[696,769,1087,1101]" gridcol="4" gridrow="27" pageId="3" pageNumber="4">C-28, 41</td>
|
||
<td id="356B472D6F7464BDFCF81C658B17CA2D" box="[829,857,1087,1101]" gridcol="5" gridrow="27" pageId="3" pageNumber="4">27</td>
|
||
<td id="356B472D6F7464BDFC511C658BF1CA2D" box="[916,959,1087,1101]" gridcol="6" gridrow="27" pageId="3" pageNumber="4">129.9</td>
|
||
<td id="356B472D6F7464BDFC3E1C658CFFCA2D" box="[1019,1201,1087,1101]" gridcol="7" gridrow="27" pageId="3" pageNumber="4">6.00 (t, 1H, 13.9)</td>
|
||
<td id="356B472D6F7464BDFB2B1C658D0DCA2D" box="[1262,1347,1087,1101]" gridcol="8" gridrow="27" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1C658DF1CA2D" box="[1407,1471,1087,1101]" gridcol="9" gridrow="27" pageId="3" pageNumber="4">C-28, 41</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11C0C8DF1CA05" box="[116,1471,1110,1125]" gridrow="28" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11C0C88DECA05" box="[116,144,1110,1125]" gridcol="0" gridrow="28" pageId="3" pageNumber="4">28</th>
|
||
<td id="356B472D6F7464BDFF081C0C88B6CA05" box="[205,248,1110,1125]" gridcol="1" gridrow="28" pageId="3" pageNumber="4">47.8</td>
|
||
<td id="356B472D6F7464BDFEF11C0C89A4CA05" box="[308,490,1110,1125]" gridcol="2" gridrow="28" pageId="3" pageNumber="4">
|
||
2.42 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FE551C0C89D7CA05" bold="true" box="[400,409,1110,1125]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21C0C8A32CA05" box="[551,636,1110,1125]" gridcol="3" gridrow="28" pageId="3" pageNumber="4">H-29, H-41</td>
|
||
<td id="356B472D6F7464BDFD7D1C0C8B4FCA05" box="[696,769,1110,1125]" gridcol="4" gridrow="28" pageId="3" pageNumber="4">C-30</td>
|
||
<td id="356B472D6F7464BDFCF81C0C8B17CA05" box="[829,857,1110,1125]" gridcol="5" gridrow="28" pageId="3" pageNumber="4">28</td>
|
||
<td id="356B472D6F7464BDFC511C0C8BF1CA05" box="[916,959,1110,1125]" gridcol="6" gridrow="28" pageId="3" pageNumber="4">133.7</td>
|
||
<td id="356B472D6F7464BDFC3E1C0C8CFFCA05" box="[1019,1201,1110,1125]" gridcol="7" gridrow="28" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFB2B1C0C8D0DCA05" box="[1262,1347,1110,1125]" gridcol="8" gridrow="28" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1C0C8DF1CA05" box="[1407,1471,1110,1125]" gridcol="9" gridrow="28" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11C378DF1CA1B" box="[116,1471,1133,1147]" gridrow="29" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11C3788DECA1B" box="[116,144,1133,1147]" gridcol="0" gridrow="29" pageId="3" pageNumber="4">29</th>
|
||
<td id="356B472D6F7464BDFF081C3788B6CA1B" box="[205,248,1133,1147]" gridcol="1" gridrow="29" pageId="3" pageNumber="4">133.3</td>
|
||
<td id="356B472D6F7464BDFEF11C3789A4CA1B" box="[308,490,1133,1147]" gridcol="2" gridrow="29" pageId="3" pageNumber="4">5.32 (t, 1H, 13.0)</td>
|
||
<td id="356B472D6F7464BDFDE21C378A32CA1B" box="[551,636,1133,1147]" gridcol="3" gridrow="29" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1C378B4FCA1B" box="[696,769,1133,1147]" gridcol="4" gridrow="29" pageId="3" pageNumber="4">C-27</td>
|
||
<td id="356B472D6F7464BDFCF81C378B17CA1B" box="[829,857,1133,1147]" gridcol="5" gridrow="29" pageId="3" pageNumber="4">29</td>
|
||
<td id="356B472D6F7464BDFC511C378BF1CA1B" box="[916,959,1133,1147]" gridcol="6" gridrow="29" pageId="3" pageNumber="4">135.8</td>
|
||
<td id="356B472D6F7464BDFC3E1C378CFFCA1B" box="[1019,1201,1133,1147]" gridcol="7" gridrow="29" pageId="3" pageNumber="4">6.47 (d, 1H, 13.1)</td>
|
||
<td id="356B472D6F7464BDFB2B1C378D0DCA1B" box="[1262,1347,1133,1147]" gridcol="8" gridrow="29" pageId="3" pageNumber="4">H-30</td>
|
||
<td id="356B472D6F7464BDFABA1C378DF1CA1B" box="[1407,1471,1133,1147]" gridcol="9" gridrow="29" pageId="3" pageNumber="4">C-27</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11CD98DF1CAF2" box="[116,1471,1155,1170]" gridrow="30" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11CD988DECAF2" box="[116,144,1155,1170]" gridcol="0" gridrow="30" pageId="3" pageNumber="4">30</th>
|
||
<td id="356B472D6F7464BDFF081CD988B6CAF2" box="[205,248,1155,1170]" gridcol="1" gridrow="30" pageId="3" pageNumber="4">135.4</td>
|
||
<td id="356B472D6F7464BDFEF11CD989A4CAF2" box="[308,490,1155,1170]" gridcol="2" gridrow="30" pageId="3" pageNumber="4">5.41 (t, 1H, 10.2)</td>
|
||
<td id="356B472D6F7464BDFDE21CD98A32CAF2" box="[551,636,1155,1170]" gridcol="3" gridrow="30" pageId="3" pageNumber="4">H-31</td>
|
||
<td id="356B472D6F7464BDFD7D1CD98B4FCAF2" box="[696,769,1155,1170]" gridcol="4" gridrow="30" pageId="3" pageNumber="4">C-31, 32</td>
|
||
<td id="356B472D6F7464BDFCF81CD98B17CAF2" box="[829,857,1155,1170]" gridcol="5" gridrow="30" pageId="3" pageNumber="4">30</td>
|
||
<td id="356B472D6F7464BDFC511CD98BF1CAF2" box="[916,959,1155,1170]" gridcol="6" gridrow="30" pageId="3" pageNumber="4">129.3</td>
|
||
<td id="356B472D6F7464BDFC3E1CD98CFFCAF2" box="[1019,1201,1155,1170]" gridcol="7" gridrow="30" pageId="3" pageNumber="4">5.39 (t, 1H, 10.2)</td>
|
||
<td id="356B472D6F7464BDFB2B1CD98D0DCAF2" box="[1262,1347,1155,1170]" gridcol="8" gridrow="30" pageId="3" pageNumber="4">H-31</td>
|
||
<td id="356B472D6F7464BDFABA1CD98DF1CAF2" box="[1407,1471,1155,1170]" gridcol="9" gridrow="30" pageId="3" pageNumber="4">C-31, 32</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11CC08DF1CAC9" box="[116,1471,1178,1193]" gridrow="31" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11CC088DECAC9" box="[116,144,1178,1193]" gridcol="0" gridrow="31" pageId="3" pageNumber="4">31</th>
|
||
<td id="356B472D6F7464BDFF081CC088B6CAC9" box="[205,248,1178,1193]" gridcol="1" gridrow="31" pageId="3" pageNumber="4">74.2</td>
|
||
<td id="356B472D6F7464BDFEF11CC089A4CAC9" box="[308,490,1178,1193]" gridcol="2" gridrow="31" pageId="3" pageNumber="4">
|
||
3.97 (t, 1H
|
||
<emphasis id="FAFEF0016F749B41FE421CC089DECAC9" bold="true" box="[391,400,1178,1193]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
, 4.1)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21CC08A32CAC9" box="[551,636,1178,1193]" gridcol="3" gridrow="31" pageId="3" pageNumber="4">H-32</td>
|
||
<td id="356B472D6F7464BDFD7D1CC08B4FCAC9" box="[696,769,1178,1193]" gridcol="4" gridrow="31" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81CC08B17CAC9" box="[829,857,1178,1193]" gridcol="5" gridrow="31" pageId="3" pageNumber="4">31</td>
|
||
<td id="356B472D6F7464BDFC511CC08BF1CAC9" box="[916,959,1178,1193]" gridcol="6" gridrow="31" pageId="3" pageNumber="4">76.2</td>
|
||
<td id="356B472D6F7464BDFC3E1CC08CFFCAC9" box="[1019,1201,1178,1193]" gridcol="7" gridrow="31" pageId="3" pageNumber="4">
|
||
3.96 (t, 1H
|
||
<emphasis id="FAFEF0016F749B41FB8B1CC08C19CAC9" bold="true" box="[1102,1111,1178,1193]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
, 3.2)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1CC08D0DCAC9" box="[1262,1347,1178,1193]" gridcol="8" gridrow="31" pageId="3" pageNumber="4">H-32</td>
|
||
<td id="356B472D6F7464BDFABA1CC08DF1CAC9" box="[1407,1471,1178,1193]" gridcol="9" gridrow="31" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11CEB8DF1CAA0" box="[116,1471,1201,1216]" gridrow="32" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11CEB88DECAA0" box="[116,144,1201,1216]" gridcol="0" gridrow="32" pageId="3" pageNumber="4">32</th>
|
||
<td id="356B472D6F7464BDFF081CEB88B6CAA0" box="[205,248,1201,1216]" gridcol="1" gridrow="32" pageId="3" pageNumber="4">45.5</td>
|
||
<td id="356B472D6F7464BDFEF11CEB89A4CAA0" box="[308,490,1201,1216]" gridcol="2" gridrow="32" pageId="3" pageNumber="4">
|
||
1.83 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FE551CEB89D7CAA0" bold="true" box="[400,409,1201,1216]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21CEB8A32CAA0" box="[551,636,1201,1216]" gridcol="3" gridrow="32" pageId="3" pageNumber="4">H-33, H-42</td>
|
||
<td id="356B472D6F7464BDFD7D1CEB8B4FCAA0" box="[696,769,1201,1216]" gridcol="4" gridrow="32" pageId="3" pageNumber="4">C-34</td>
|
||
<td id="356B472D6F7464BDFCF81CEB8B17CAA0" box="[829,857,1201,1216]" gridcol="5" gridrow="32" pageId="3" pageNumber="4">32</td>
|
||
<td id="356B472D6F7464BDFC511CEB8BF1CAA0" box="[916,959,1201,1216]" gridcol="6" gridrow="32" pageId="3" pageNumber="4">42.1</td>
|
||
<td id="356B472D6F7464BDFC3E1CEB8CFFCAA0" box="[1019,1201,1201,1216]" gridcol="7" gridrow="32" pageId="3" pageNumber="4">
|
||
1.81 (m, 1H
|
||
<emphasis id="FAFEF0016F749B41FB921CEB8C2ECAA0" bold="true" box="[1111,1120,1201,1216]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1CEB8D0DCAA0" box="[1262,1347,1201,1216]" gridcol="8" gridrow="32" pageId="3" pageNumber="4">H-33, H-42</td>
|
||
<td id="356B472D6F7464BDFABA1CEB8DF1CAA0" box="[1407,1471,1201,1216]" gridcol="9" gridrow="32" pageId="3" pageNumber="4">C-34</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11C928DF1CAB6" box="[116,1471,1224,1238]" gridrow="33" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11C9288DECAB6" box="[116,144,1224,1238]" gridcol="0" gridrow="33" pageId="3" pageNumber="4">33</th>
|
||
<td id="356B472D6F7464BDFF081C9288B6CAB6" box="[205,248,1224,1238]" gridcol="1" gridrow="33" pageId="3" pageNumber="4">23.3</td>
|
||
<td id="356B472D6F7464BDFEF11C9289A4CAB6" box="[308,490,1224,1238]" gridcol="2" gridrow="33" pageId="3" pageNumber="4">1.55 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21C928A32CAB6" box="[551,636,1224,1238]" gridcol="3" gridrow="33" pageId="3" pageNumber="4">H-34</td>
|
||
<td id="356B472D6F7464BDFD7D1C928B4FCAB6" box="[696,769,1224,1238]" gridcol="4" gridrow="33" pageId="3" pageNumber="4">C-31</td>
|
||
<td id="356B472D6F7464BDFCF81C928B17CAB6" box="[829,857,1224,1238]" gridcol="5" gridrow="33" pageId="3" pageNumber="4">33</td>
|
||
<td id="356B472D6F7464BDFC511C928BF1CAB6" box="[916,959,1224,1238]" gridcol="6" gridrow="33" pageId="3" pageNumber="4">24.7</td>
|
||
<td id="356B472D6F7464BDFC3E1C928CFFCAB6" box="[1019,1201,1224,1238]" gridcol="7" gridrow="33" pageId="3" pageNumber="4">1.54 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFB2B1C928D0DCAB6" box="[1262,1347,1224,1238]" gridcol="8" gridrow="33" pageId="3" pageNumber="4">H-34</td>
|
||
<td id="356B472D6F7464BDFABA1C928DF1CAB6" box="[1407,1471,1224,1238]" gridcol="9" gridrow="33" pageId="3" pageNumber="4">C-31</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11C858DF1CA8D" box="[116,1471,1247,1261]" gridrow="34" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11C8588DECA8D" box="[116,144,1247,1261]" gridcol="0" gridrow="34" pageId="3" pageNumber="4">34</th>
|
||
<td id="356B472D6F7464BDFF081C8588B6CA8D" box="[205,248,1247,1261]" gridcol="1" gridrow="34" pageId="3" pageNumber="4">11.5</td>
|
||
<td id="356B472D6F7464BDFEF11C8589A4CA8D" box="[308,490,1247,1261]" gridcol="2" gridrow="34" pageId="3" pageNumber="4">0.97 (t, 3H, 1.8)</td>
|
||
<td id="356B472D6F7464BDFDE21C858A32CA8D" box="[551,636,1247,1261]" gridcol="3" gridrow="34" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1C858B4FCA8D" box="[696,769,1247,1261]" gridcol="4" gridrow="34" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFCF81C858B17CA8D" box="[829,857,1247,1261]" gridcol="5" gridrow="34" pageId="3" pageNumber="4">34</td>
|
||
<td id="356B472D6F7464BDFC511C858BF1CA8D" box="[916,959,1247,1261]" gridcol="6" gridrow="34" pageId="3" pageNumber="4">11.3</td>
|
||
<td id="356B472D6F7464BDFC3E1C858CFFCA8D" box="[1019,1201,1247,1261]" gridcol="7" gridrow="34" pageId="3" pageNumber="4">0.96 (t, 3H, 1.7)</td>
|
||
<td id="356B472D6F7464BDFB2B1C858D0DCA8D" box="[1262,1347,1247,1261]" gridcol="8" gridrow="34" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1C858DF1CA8D" box="[1407,1471,1247,1261]" gridcol="9" gridrow="34" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11CAF8DF1CB64" box="[116,1471,1269,1284]" gridrow="35" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11CAF88DECB64" box="[116,144,1269,1284]" gridcol="0" gridrow="35" pageId="3" pageNumber="4">35</th>
|
||
<td id="356B472D6F7464BDFF081CAF88B6CB64" box="[205,248,1269,1284]" gridcol="1" gridrow="35" pageId="3" pageNumber="4">24.7</td>
|
||
<td id="356B472D6F7464BDFEF11CAF89A4CB64" box="[308,490,1269,1284]" gridcol="2" gridrow="35" pageId="3" pageNumber="4">
|
||
1.33 (s, 3H
|
||
<emphasis id="FAFEF0016F749B41FE4D1CAF89DFCB64" bold="true" box="[392,401,1269,1284]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21CAF8A32CB64" box="[551,636,1269,1284]" gridcol="3" gridrow="35" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1CAF8B4FCB64" box="[696,769,1269,1284]" gridcol="4" gridrow="35" pageId="3" pageNumber="4">C-4</td>
|
||
<td id="356B472D6F7464BDFCF81CAF8B17CB64" box="[829,857,1269,1284]" gridcol="5" gridrow="35" pageId="3" pageNumber="4">35</td>
|
||
<td id="356B472D6F7464BDFC511CAF8BF1CB64" box="[916,959,1269,1284]" gridcol="6" gridrow="35" pageId="3" pageNumber="4">24.5</td>
|
||
<td id="356B472D6F7464BDFC3E1CAF8CFFCB64" box="[1019,1201,1269,1284]" gridcol="7" gridrow="35" pageId="3" pageNumber="4">
|
||
1.33 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FB971CAF8C15CB64" bold="true" box="[1106,1115,1269,1284]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
, 2.4)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1CAF8D0DCB64" box="[1262,1347,1269,1284]" gridcol="8" gridrow="35" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1CAF8DF1CB64" box="[1407,1471,1269,1284]" gridcol="9" gridrow="35" pageId="3" pageNumber="4">C-4</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11D518DF1CB7B" box="[116,1471,1291,1307]" gridrow="36" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11D5188DECB7B" box="[116,144,1291,1307]" gridcol="0" gridrow="36" pageId="3" pageNumber="4">36</th>
|
||
<td id="356B472D6F7464BDFF081D5188B6CB7B" box="[205,248,1291,1307]" gridcol="1" gridrow="36" pageId="3" pageNumber="4">15.9</td>
|
||
<td id="356B472D6F7464BDFEF11D5189A4CB7B" box="[308,490,1291,1307]" gridcol="2" gridrow="36" pageId="3" pageNumber="4">
|
||
1.02 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FE4E1D5189DACB7B" bold="true" box="[395,404,1291,1307]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 2.8)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21D518A32CB7B" box="[551,636,1291,1307]" gridcol="3" gridrow="36" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1D518B4FCB7B" box="[696,769,1291,1307]" gridcol="4" gridrow="36" pageId="3" pageNumber="4">C-10</td>
|
||
<td id="356B472D6F7464BDFCF81D518B17CB7B" box="[829,857,1291,1307]" gridcol="5" gridrow="36" pageId="3" pageNumber="4">36</td>
|
||
<td id="356B472D6F7464BDFC511D518BF1CB7B" box="[916,959,1291,1307]" gridcol="6" gridrow="36" pageId="3" pageNumber="4">13.3</td>
|
||
<td id="356B472D6F7464BDFC3E1D518CFFCB7B" box="[1019,1201,1291,1307]" gridcol="7" gridrow="36" pageId="3" pageNumber="4">
|
||
0.98 (s, 3H
|
||
<emphasis id="FAFEF0016F749B41FB8A1D518C16CB7B" bold="true" box="[1103,1112,1291,1307]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1D518D0DCB7B" box="[1262,1347,1291,1307]" gridcol="8" gridrow="36" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1D518DF1CB7B" box="[1407,1471,1291,1307]" gridcol="9" gridrow="36" pageId="3" pageNumber="4">C-10</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11D798DF1CB52" box="[116,1471,1315,1330]" gridrow="37" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11D7988DECB52" box="[116,144,1315,1330]" gridcol="0" gridrow="37" pageId="3" pageNumber="4">37</th>
|
||
<td id="356B472D6F7464BDFF081D7988B6CB52" box="[205,248,1315,1330]" gridcol="1" gridrow="37" pageId="3" pageNumber="4">28.1</td>
|
||
<td id="356B472D6F7464BDFEF11D7989A4CB52" box="[308,490,1315,1330]" gridcol="2" gridrow="37" pageId="3" pageNumber="4">1.41 (m, 2H)</td>
|
||
<td id="356B472D6F7464BDFDE21D798A32CB52" box="[551,636,1315,1330]" gridcol="3" gridrow="37" pageId="3" pageNumber="4">H-37a</td>
|
||
<td id="356B472D6F7464BDFD7D1D798B4FCB52" box="[696,769,1315,1330]" gridcol="4" gridrow="37" pageId="3" pageNumber="4">C-14</td>
|
||
<td id="356B472D6F7464BDFCF81D798B17CB52" box="[829,857,1315,1330]" gridcol="5" gridrow="37" pageId="3" pageNumber="4">37</td>
|
||
<td id="356B472D6F7464BDFC511D798BF1CB52" box="[916,959,1315,1330]" gridcol="6" gridrow="37" pageId="3" pageNumber="4">23.3</td>
|
||
<td id="356B472D6F7464BDFC3E1D798CFFCB52" box="[1019,1201,1315,1330]" gridcol="7" gridrow="37" pageId="3" pageNumber="4">
|
||
1.02 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FB971D798C15CB52" bold="true" box="[1106,1115,1315,1330]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
, 2.1)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1D798D0DCB52" box="[1262,1347,1315,1330]" gridcol="8" gridrow="37" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1D798DF1CB52" box="[1407,1471,1315,1330]" gridcol="9" gridrow="37" pageId="3" pageNumber="4">C-14</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11D608DF1CB29" box="[116,1471,1338,1353]" gridrow="38" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11D6088DECB29" box="[116,144,1338,1353]" gridcol="0" gridrow="38" pageId="3" pageNumber="4">37a</th>
|
||
<td id="356B472D6F7464BDFF081D6088B6CB29" box="[205,248,1338,1353]" gridcol="1" gridrow="38" pageId="3" pageNumber="4">12.1</td>
|
||
<td id="356B472D6F7464BDFEF11D6089A4CB29" box="[308,490,1338,1353]" gridcol="2" gridrow="38" pageId="3" pageNumber="4">0.93 (t, 3H, 2.1)</td>
|
||
<td id="356B472D6F7464BDFDE21D608A32CB29" box="[551,636,1338,1353]" gridcol="3" gridrow="38" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1D608B4FCB29" box="[696,769,1338,1353]" gridcol="4" gridrow="38" pageId="3" pageNumber="4">C-37</td>
|
||
<td id="356B472D6F7464BDFCF81D608B17CB29" box="[829,857,1338,1353]" gridcol="5" gridrow="38" pageId="3" pageNumber="4">38</td>
|
||
<td id="356B472D6F7464BDFC511D608BF1CB29" box="[916,959,1338,1353]" gridcol="6" gridrow="38" pageId="3" pageNumber="4">16.0</td>
|
||
<td id="356B472D6F7464BDFC3E1D608CFFCB29" box="[1019,1201,1338,1353]" gridcol="7" gridrow="38" pageId="3" pageNumber="4">
|
||
0.97 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FB971D608C15CB29" bold="true" box="[1106,1115,1338,1353]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
, 2.2)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1D608D0DCB29" box="[1262,1347,1338,1353]" gridcol="8" gridrow="38" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1D608DF1CB29" box="[1407,1471,1338,1353]" gridcol="9" gridrow="38" pageId="3" pageNumber="4">C-18</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11D0B8DF1CB00" box="[116,1471,1361,1376]" gridrow="39" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11D0B88DECB00" box="[116,144,1361,1376]" gridcol="0" gridrow="39" pageId="3" pageNumber="4">38</th>
|
||
<td id="356B472D6F7464BDFF081D0B88B6CB00" box="[205,248,1361,1376]" gridcol="1" gridrow="39" pageId="3" pageNumber="4">16.1</td>
|
||
<td id="356B472D6F7464BDFEF11D0B89A4CB00" box="[308,490,1361,1376]" gridcol="2" gridrow="39" pageId="3" pageNumber="4">
|
||
0.99 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FE4E1D0B89DACB00" bold="true" box="[395,404,1361,1376]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
, 3.0)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21D0B8A32CB00" box="[551,636,1361,1376]" gridcol="3" gridrow="39" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1D0B8B4FCB00" box="[696,769,1361,1376]" gridcol="4" gridrow="39" pageId="3" pageNumber="4">C-18</td>
|
||
<td id="356B472D6F7464BDFCF81D0B8B17CB00" box="[829,857,1361,1376]" gridcol="5" gridrow="39" pageId="3" pageNumber="4">39</td>
|
||
<td id="356B472D6F7464BDFC511D0B8BF1CB00" box="[916,959,1361,1376]" gridcol="6" gridrow="39" pageId="3" pageNumber="4">13.8</td>
|
||
<td id="356B472D6F7464BDFC3E1D0B8CFFCB00" box="[1019,1201,1361,1376]" gridcol="7" gridrow="39" pageId="3" pageNumber="4">
|
||
0.94 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FB971D0B8C15CB00" bold="true" box="[1106,1115,1361,1376]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
, 1.6)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1D0B8D0DCB00" box="[1262,1347,1361,1376]" gridcol="8" gridrow="39" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1D0B8DF1CB00" box="[1407,1471,1361,1376]" gridcol="9" gridrow="39" pageId="3" pageNumber="4">C-22, 23</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11D3C8DF1CB16" box="[116,1471,1382,1398]" gridrow="40" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11D3C88DECB16" box="[116,144,1382,1398]" gridcol="0" gridrow="40" pageId="3" pageNumber="4">39</th>
|
||
<td id="356B472D6F7464BDFF081D3C88B6CB16" box="[205,248,1382,1398]" gridcol="1" gridrow="40" pageId="3" pageNumber="4">53.4</td>
|
||
<td id="356B472D6F7464BDFEF11D3C89A4CB16" box="[308,490,1382,1398]" gridcol="2" gridrow="40" pageId="3" pageNumber="4">3.63 (d, 2H, 1.6)</td>
|
||
<td id="356B472D6F7464BDFDE21D3C8A32CB16" box="[551,636,1382,1398]" gridcol="3" gridrow="40" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1D3C8B4FCB16" box="[696,769,1382,1398]" gridcol="4" gridrow="40" pageId="3" pageNumber="4">C-22, 23</td>
|
||
<td id="356B472D6F7464BDFCF81D3C8B17CB16" box="[829,857,1382,1398]" gridcol="5" gridrow="40" pageId="3" pageNumber="4">40</td>
|
||
<td id="356B472D6F7464BDFC511D3C8BF1CB16" box="[916,959,1382,1398]" gridcol="6" gridrow="40" pageId="3" pageNumber="4">22.7</td>
|
||
<td id="356B472D6F7464BDFC3E1D3C8CFFCB16" box="[1019,1201,1382,1398]" gridcol="7" gridrow="40" pageId="3" pageNumber="4">
|
||
0.92 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FB971D3C8C15CB16" bold="true" box="[1106,1115,1382,1398]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 2.1)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1D3C8D0DCB16" box="[1262,1347,1382,1398]" gridcol="8" gridrow="40" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1D3C8DF1CB16" box="[1407,1471,1382,1398]" gridcol="9" gridrow="40" pageId="3" pageNumber="4">C-24</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11D278DF1CBED" box="[116,1471,1405,1421]" gridrow="41" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11D2788DECBED" box="[116,144,1405,1421]" gridcol="0" gridrow="41" pageId="3" pageNumber="4">40</th>
|
||
<td id="356B472D6F7464BDFF081D2788B6CBED" box="[205,248,1405,1421]" gridcol="1" gridrow="41" pageId="3" pageNumber="4">21.2</td>
|
||
<td id="356B472D6F7464BDFEF11D2789A4CBED" box="[308,490,1405,1421]" gridcol="2" gridrow="41" pageId="3" pageNumber="4">
|
||
0.95 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FE4E1D2789DACBED" bold="true" box="[395,404,1405,1421]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 2.5)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21D278A32CBED" box="[551,636,1405,1421]" gridcol="3" gridrow="41" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1D278B4FCBED" box="[696,769,1405,1421]" gridcol="4" gridrow="41" pageId="3" pageNumber="4">C-24</td>
|
||
<td id="356B472D6F7464BDFCF81D278B17CBED" box="[829,857,1405,1421]" gridcol="5" gridrow="41" pageId="3" pageNumber="4">41</td>
|
||
<td id="356B472D6F7464BDFC511D278BF1CBED" box="[916,959,1405,1421]" gridcol="6" gridrow="41" pageId="3" pageNumber="4">12.1</td>
|
||
<td id="356B472D6F7464BDFC3E1D278CFFCBED" box="[1019,1201,1405,1421]" gridcol="7" gridrow="41" pageId="3" pageNumber="4">
|
||
1.01 (s, 3H
|
||
<emphasis id="FAFEF0016F749B41FB8A1D278C16CBED" bold="true" box="[1103,1112,1405,1421]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1D278D0DCBED" box="[1262,1347,1405,1421]" gridcol="8" gridrow="41" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1D278DF1CBED" box="[1407,1471,1405,1421]" gridcol="9" gridrow="41" pageId="3" pageNumber="4">C-28</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11DCE8DF1CBC4" box="[116,1471,1428,1444]" gridrow="42" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11DCE88DECBC4" box="[116,144,1428,1444]" gridcol="0" gridrow="42" pageId="3" pageNumber="4">41</th>
|
||
<td id="356B472D6F7464BDFF081DCE88B6CBC4" box="[205,248,1428,1444]" gridcol="1" gridrow="42" pageId="3" pageNumber="4">13.0</td>
|
||
<td id="356B472D6F7464BDFEF11DCE89A4CBC4" box="[308,490,1428,1444]" gridcol="2" gridrow="42" pageId="3" pageNumber="4">
|
||
1.03 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FE4E1DCE89DACBC4" bold="true" box="[395,404,1428,1444]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 2.8)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21DCE8A32CBC4" box="[551,636,1428,1444]" gridcol="3" gridrow="42" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1DCE8B4FCBC4" box="[696,769,1428,1444]" gridcol="4" gridrow="42" pageId="3" pageNumber="4">C-28</td>
|
||
<td id="356B472D6F7464BDFCF81DCE8B17CBC4" box="[829,857,1428,1444]" gridcol="5" gridrow="42" pageId="3" pageNumber="4">42</td>
|
||
<td id="356B472D6F7464BDFC511DCE8BF1CBC4" box="[916,959,1428,1444]" gridcol="6" gridrow="42" pageId="3" pageNumber="4">15.2</td>
|
||
<td id="356B472D6F7464BDFC3E1DCE8CFFCBC4" box="[1019,1201,1428,1444]" gridcol="7" gridrow="42" pageId="3" pageNumber="4">
|
||
0.83 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FB971DCE8C15CBC4" bold="true" box="[1106,1115,1428,1444]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 3.4)
|
||
</td>
|
||
<td id="356B472D6F7464BDFB2B1DCE8D0DCBC4" box="[1262,1347,1428,1444]" gridcol="8" gridrow="42" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1DCE8DF1CBC4" box="[1407,1471,1428,1444]" gridcol="9" gridrow="42" pageId="3" pageNumber="4">C-32</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7464BDFFB11DF18DF1CBDB" box="[116,1471,1451,1467]" gridrow="43" pageId="3" pageNumber="4">
|
||
<th id="356B472D6F7464BDFFB11DF188DECBDB" box="[116,144,1451,1467]" gridcol="0" gridrow="43" pageId="3" pageNumber="4">42</th>
|
||
<td id="356B472D6F7464BDFF081DF188B6CBDB" box="[205,248,1451,1467]" gridcol="1" gridrow="43" pageId="3" pageNumber="4">14.1</td>
|
||
<td id="356B472D6F7464BDFEF11DF189A4CBDB" box="[308,490,1451,1467]" gridcol="2" gridrow="43" pageId="3" pageNumber="4">
|
||
0.88 (d, 3H
|
||
<emphasis id="FAFEF0016F749B41FE4E1DF189DACBDB" bold="true" box="[395,404,1451,1467]" italics="true" pageId="3" pageNumber="4">α</emphasis>
|
||
, 3.4)
|
||
</td>
|
||
<td id="356B472D6F7464BDFDE21DF18A32CBDB" box="[551,636,1451,1467]" gridcol="3" gridrow="43" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFD7D1DF18B4FCBDB" box="[696,769,1451,1467]" gridcol="4" gridrow="43" pageId="3" pageNumber="4">C-32</td>
|
||
<td id="356B472D6F7464BDFCF81DF18B17CBDB" box="[829,857,1451,1467]" gridcol="5" gridrow="43" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFC511DF18BF1CBDB" box="[916,959,1451,1467]" gridcol="6" gridrow="43" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFC3E1DF18CFFCBDB" box="[1019,1201,1451,1467]" gridcol="7" gridrow="43" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFB2B1DF18D0DCBDB" box="[1262,1347,1451,1467]" gridcol="8" gridrow="43" pageId="3" pageNumber="4">–</td>
|
||
<td id="356B472D6F7464BDFABA1DF18DF1CBDB" box="[1407,1471,1451,1467]" gridcol="9" gridrow="43" pageId="3" pageNumber="4">–</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<tableNote id="356C2D9D6F749B41FFA11D8A8CE3C827" pageId="3" pageNumber="4" targetBox="[116,1471,454,1467]" targetPageId="3">
|
||
<paragraph id="C8352C136F749B41FFA11D8A8D7DCB9B" blockId="3.[100,1488,1484,1608]" pageId="3" pageNumber="4">
|
||
Nuclear magnetic resonance (NMR) assignments were made by means of correlation spectroscopy (
|
||
<superScript id="3FFF815B6F749B41FC6A1D968BF9CBB8" attach="right" box="[943,951,1484,1496]" fontSize="5" pageId="3" pageNumber="4">1</superScript>
|
||
H–
|
||
<superScript id="3FFF815B6F749B41FC0A1D968B99CBB8" attach="right" box="[975,983,1484,1496]" fontSize="5" pageId="3" pageNumber="4">1</superScript>
|
||
H COSY), nuclear Overhauser effect spectroscopy (NOESY), heteronuclear multiple-bond correlation spectroscopy (HMBC), and heteronuclear single-quantum correlation spectroscopy (HSQC) experiments.
|
||
</paragraph>
|
||
<paragraph id="C8352C136F749B41FFA11E598D35C874" blockId="3.[100,1488,1484,1608]" box="[100,1403,1539,1556]" pageId="3" pageNumber="4">NOESY relations have been represented by double-sided arrows, wherein the red and blue colored arrows indicated alpha and beta protons, respectively.</paragraph>
|
||
<paragraph id="C8352C136F749B41FFB61E428CE3C827" blockId="3.[100,1488,1484,1608]" pageId="3" pageNumber="4">
|
||
<superScript id="3FFF815B6F749B41FFB61E428834C844" attach="right" box="[115,122,1560,1572]" fontSize="5" pageId="3" pageNumber="4">a</superScript>
|
||
NMR spectra were recorded using Bruker AVANCE III 500 MHz (AV 500) spectrometer in CDCl as aprotic solvent at ambient temperature with TMS as the internal
|
||
<subScript id="540E2E566F749B41FC5D1E7E8BEEC850" attach="left" box="[920,928,1572,1584]" fontSize="5" pageId="3" pageNumber="4">3</subScript>
|
||
standard (
|
||
<emphasis id="FAFEF0016F749B41FF7E1E6C888AC827" bold="true" box="[187,196,1590,1607]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
0 ppm). Values in parts per million (ppm), multiplicity and coupling constants (
|
||
<emphasis id="FAFEF0016F749B41FCB41E6D8B34C827" bold="true" box="[881,890,1591,1607]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
= Hz) are indicated in parentheses.
|
||
</paragraph>
|
||
</tableNote>
|
||
<paragraph id="C8352C136F749B46FC941F318960C865" blockId="3.[818,1487,1648,1977]" lastBlockId="4.[100,770,846,1959]" lastPageId="4" lastPageNumber="5" pageId="3" pageNumber="4">
|
||
The molecular formula of previously undisclosed hexahydro 41-hydroxy-macrobrevin-31-acetate (compound
|
||
<emphasis id="FAFEF0016F749B41FB2F1FDD8CB8C9FA" bold="true" box="[1258,1270,1927,1946]" pageId="3" pageNumber="4">3</emphasis>
|
||
) was deduced as C
|
||
<subScript id="540E2E566F749B41FCFA1FF18B1FC9D9" attach="both" box="[831,849,1963,1977]" fontSize="6" pageId="3" pageNumber="4">44</subScript>
|
||
H
|
||
<subScript id="540E2E566F749B41FCA41FF18B3DC9D9" attach="both" box="[865,883,1963,1977]" fontSize="6" pageId="3" pageNumber="4">74</subScript>
|
||
O
|
||
<subScript id="540E2E566F749B41FC471FF18BC5C9D9" attach="left" box="[898,907,1963,1977]" fontSize="6" pageId="3" pageNumber="4">8</subScript>
|
||
by mass spectroscopic experiment {HRESIMS
|
||
<emphasis id="FAFEF0016F749B41FAAD1FF98DC2C9D6" bold="true" box="[1384,1420,1955,1974]" italics="true" pageId="3" pageNumber="4">m/z</emphasis>
|
||
found 731.5464 [M+H]
|
||
<superScript id="3FFF815B6F739B46FED51B148952CD3C" attach="none" box="[272,284,846,860]" fontSize="6" pageId="4" pageNumber="5">+</superScript>
|
||
}, and its structure was elucidated by IR/NMR (
|
||
<tableCitation id="850819A86F739B46FFA91B2A888BCDE3" box="[108,197,880,899]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetPageId="3" captionText="Table 1A NMR spectroscopic data of macrobrevin analogues, 1–2." httpUri="http://table.plazi.org/id/9CF57C9B6F749B41FFA118CC8A0CCEA0" pageId="4" pageNumber="5" tableUuid="9CF57C9B6F749B41FFA118CC8A0CCEA0">Table 1B</tableCitation>
|
||
;
|
||
<figureCitation id="50B130966F739B46FF171B2A8954CDE3" box="[210,282,880,899]" captionStart="Fig" captionStartId="4.[100,130,768,785]" captionTargetBox="[268,1323,152,739]" captionTargetId="figure-868@4.[263,1324,148,741]" captionTargetPageId="4" captionText="Fig. 2. 1H–1H COSY/HMBC (A-D) correlations of macrobrevin analogues (1–4). Key 1H–1H COSY correlations and HMBC pairings were characterized by bold-faced bonds and double-barbed arrows, respectively." figureDoi="http://doi.org/10.5281/zenodo.8235155" httpUri="https://zenodo.org/record/8235155/files/figure.png" pageId="4" pageNumber="5">Fig. 2C</figureCitation>
|
||
; Fig.
|
||
<collectionCode id="AE9BB4D66F739B46FE961B2A8911CDE3" box="[339,351,880,899]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="4" pageNumber="5" type="Herbarium">S</collectionCode>
|
||
25-
|
||
<collectionCode id="AE9BB4D66F739B46FEB81B2A89C7CDE3" box="[381,393,880,899]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="4" pageNumber="5" type="Herbarium">S</collectionCode>
|
||
36).
|
||
<superScript id="3FFF815B6F739B46FE721B308987CD18" attach="right" box="[439,457,874,888]" fontSize="6" pageId="4" pageNumber="5">13</superScript>
|
||
C/
|
||
<superScript id="3FFF815B6F739B46FE241B3089B2CD18" attach="right" box="[481,508,874,888]" fontSize="6" pageId="4" pageNumber="5">135</superScript>
|
||
DEPT NMR represented 44 carbons, which included four non-protonated carbons, nine methyls, eleven methylenes and twenty methines. The hydroxymethylene at C-28 was substantiated through HMBCs from H-41 to C-28, whereas an acetate linkage at C-31 was set forth through HMBCs from H-31 to C-31a; H-31b to C-31, C-31a. The higher chemical shift value of about ~1 ppm at H-31 (
|
||
<emphasis id="FAFEF0016F739B46FF5A1C4D88E7CA4A" bold="true" box="[159,169,1047,1066]" italics="true" pageId="4" pageNumber="5">δ</emphasis>
|
||
<subScript id="540E2E566F739B46FF6C1C4588FBCA4D" attach="left" box="[169,181,1055,1069]" fontSize="6" pageId="4" pageNumber="5">H</subScript>
|
||
4.65) in the compound
|
||
<emphasis id="FAFEF0016F739B46FE551C4D89D2CA4A" bold="true" box="[400,412,1047,1066]" pageId="4" pageNumber="5">3</emphasis>
|
||
, when compared to that in
|
||
<emphasis id="FAFEF0016F739B46FD521C4D8AEDCA4A" bold="true" box="[663,675,1047,1066]" pageId="4" pageNumber="5">1</emphasis>
|
||
(
|
||
<emphasis id="FAFEF0016F739B46FD751C4D8AF4CA4A" bold="true" box="[688,698,1047,1066]" italics="true" pageId="4" pageNumber="5">δ</emphasis>
|
||
<subScript id="540E2E566F739B46FD7F1C458A88CA4D" attach="left" box="[698,710,1055,1069]" fontSize="6" pageId="4" pageNumber="5">H</subScript>
|
||
3.97), ascribed the presence of highly electronegative oxygenated end of ester (acetate) in
|
||
<emphasis id="FAFEF0016F739B46FF131C1588ACCA02" bold="true" box="[214,226,1103,1122]" pageId="4" pageNumber="5">3</emphasis>
|
||
, whereas
|
||
<emphasis id="FAFEF0016F739B46FE861C158901CA02" bold="true" box="[323,335,1103,1122]" pageId="4" pageNumber="5">1</emphasis>
|
||
enclosed a hydroxyl at this position (C-27). A deshielded non-protonated carbon was present in
|
||
<emphasis id="FAFEF0016F739B46FDF81C318A07CA1E" bold="true" box="[573,585,1131,1150]" pageId="4" pageNumber="5">3</emphasis>
|
||
at
|
||
<emphasis id="FAFEF0016F739B46FDAC1C318A3DCA1E" bold="true" box="[617,627,1131,1150]" italics="true" pageId="4" pageNumber="5">δ</emphasis>
|
||
<subScript id="540E2E566F739B46FDB61C288A33CAE0" attach="left" box="[627,637,1138,1152]" fontSize="6" pageId="4" pageNumber="5">C</subScript>
|
||
143.8 (C-28), which was bonded to the hydroxymethyl, whereas the compound
|
||
<emphasis id="FAFEF0016F739B46FD301CDD8B4FCAFA" bold="true" box="[757,769,1159,1178]" pageId="4" pageNumber="5">1</emphasis>
|
||
enclosed a shielded methine at
|
||
<emphasis id="FAFEF0016F739B46FE521CF889EFCAD5" bold="true" box="[407,417,1186,1205]" italics="true" pageId="4" pageNumber="5">δ</emphasis>
|
||
<subScript id="540E2E566F739B46FE641CF089E3CAD8" attach="left" box="[417,429,1194,1208]" fontSize="6" pageId="4" pageNumber="5">H</subScript>
|
||
2.42 (C-28) attached to a terminal methyl group. Thus, the presence of an acetate linkage at C-31 and hydroxymethyl at C-
|
||
<quantity id="0F7281F66F739B46FEF41C81892ACA8D" box="[305,356,1242,1262]" metricMagnitude="-1" metricUnit="m" metricValue="7.112" pageId="4" pageNumber="5" unit="in" value="28.0">28 in</quantity>
|
||
<emphasis id="FAFEF0016F739B46FEAA1C808935CA8D" bold="true" box="[367,379,1242,1261]" pageId="4" pageNumber="5">3</emphasis>
|
||
were assigned, when compared to the presence of hydroxyl at C-31 and methyl at C-
|
||
<quantity id="0F7281F66F739B46FDFE1CAC8A20CB69" box="[571,622,1270,1289]" metricMagnitude="-1" metricUnit="m" metricValue="7.112" pageId="4" pageNumber="5" unit="in" value="28.0">28 in</quantity>
|
||
trihydroxy-37- methyl-macrobrevin (
|
||
<emphasis id="FAFEF0016F739B46FEFC1D48890BCB45" bold="true" box="[313,325,1298,1317]" pageId="4" pageNumber="5">1</emphasis>
|
||
). Similar to the previously discussed compounds
|
||
<emphasis id="FAFEF0016F739B46FF6B1D74889FCB21" bold="true" box="[174,209,1326,1346]" pageId="4" pageNumber="5">1–2</emphasis>
|
||
, the titled compound exhibited
|
||
<emphasis id="FAFEF0016F739B46FE391D748A67CB21" bold="true" box="[508,553,1326,1345]" italics="true" pageId="4" pageNumber="5">trans</emphasis>
|
||
-orientation (
|
||
<emphasis id="FAFEF0016F739B46FD601D748AFFCB21" bold="true" box="[677,689,1326,1345]" italics="true" pageId="4" pageNumber="5">E</emphasis>
|
||
) at their alkenic positions by reason of greater coupling constants. NOE couplings from H-35/H-5/H-37/H-38/H-21/H-24/H-32 and H-21/H-39 were acknowledged for their
|
||
<emphasis id="FAFEF0016F739B46FE831DD8891FCBF5" bold="true" box="[326,337,1410,1429]" italics="true" pageId="4" pageNumber="5">β</emphasis>
|
||
-alignment, and those between H-31/H-42/H-22/H-19/H-18/H-13/H-36/H-9 and H-22/H-40 deduced the
|
||
<emphasis id="FAFEF0016F739B46FD631DC78AFCCBD2" bold="true" box="[678,690,1437,1458]" italics="true" pageId="4" pageNumber="5">α</emphasis>
|
||
-orientation. The mass spectrum exhibited a molecular ion peak at
|
||
<emphasis id="FAFEF0016F739B46FD421DE08AE5CBAD" bold="true" box="[647,683,1466,1485]" italics="true" pageId="4" pageNumber="5">m/z</emphasis>
|
||
730, and the base peak was observed at
|
||
<emphasis id="FAFEF0016F739B46FE421D8F89E2CB88" bold="true" box="[391,428,1493,1512]" italics="true" pageId="4" pageNumber="5">m/z</emphasis>
|
||
59 (
|
||
<emphasis id="FAFEF0016F739B46FE121D8C89ADCB89" bold="true" box="[471,483,1494,1513]" pageId="4" pageNumber="5">L</emphasis>
|
||
) (2,2-dihydroxyethen-1-ylium cation) (Fig.
|
||
<collectionCode id="AE9BB4D66F739B46FF1B1DA888A4C865" box="[222,234,1522,1541]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="4" pageNumber="5" type="Herbarium">S</collectionCode>
|
||
33-34).
|
||
</paragraph>
|
||
<caption id="9CF57C9B6F739B46FFA11B5A89BBCD4B" ID-DOI="http://doi.org/10.5281/zenodo.8235155" ID-Zenodo-Dep="8235155" httpUri="https://zenodo.org/record/8235155/files/figure.png" pageId="4" pageNumber="5" startId="4.[100,130,768,785]" targetBox="[268,1323,152,739]" targetPageId="4" targetType="figure">
|
||
<paragraph id="C8352C136F739B46FFA11B5A89BBCD4B" blockId="4.[100,1487,764,811]" pageId="4" pageNumber="5">
|
||
<emphasis id="FAFEF0016F739B46FFA11B5A88D3CD71" bold="true" box="[100,157,768,785]" pageId="4" pageNumber="5">Fig. 2.</emphasis>
|
||
<superScript id="3FFF815B6F739B46FF631AA688E0CD68" attach="right" box="[166,174,764,776]" fontSize="5" pageId="4" pageNumber="5">1</superScript>
|
||
H–
|
||
<superScript id="3FFF815B6F739B46FF031AA68880CD68" attach="right" box="[198,206,764,776]" fontSize="5" pageId="4" pageNumber="5">1</superScript>
|
||
H COSY/HMBC (
|
||
<emphasis id="FAFEF0016F739B46FE9B1B5A8931CD71" bold="true" box="[350,383,768,785]" pageId="4" pageNumber="5">A-D</emphasis>
|
||
) correlations of macrobrevin analogues (
|
||
<emphasis id="FAFEF0016F739B46FD191B5A8AB2CD71" bold="true" box="[732,764,768,785]" pageId="4" pageNumber="5">1–4</emphasis>
|
||
). Key
|
||
<superScript id="3FFF815B6F739B46FCF61AA68B75CD68" attach="right" box="[819,827,764,776]" fontSize="5" pageId="4" pageNumber="5">1</superScript>
|
||
H–
|
||
<superScript id="3FFF815B6F739B46FC961AA68B15CD68" attach="right" box="[851,859,764,776]" fontSize="5" pageId="4" pageNumber="5">1</superScript>
|
||
H COSY correlations and HMBC pairings were characterized by bold-faced bonds and double-barbed arrows, respectively.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="C8352C136F739B46FF411E578DCDCAD6" blockId="4.[100,770,846,1959]" lastBlockId="4.[818,1487,852,1206]" pageId="4" pageNumber="5">
|
||
The molecular formula of the previously undisclosed hexahydro-28- nor-methyl-5-methoxy-macrobrevin (macrobrevin
|
||
<emphasis id="FAFEF0016F739B46FD8C1E738A1BC85C" bold="true" box="[585,597,1577,1596]" pageId="4" pageNumber="5">4</emphasis>
|
||
) was deduced as C
|
||
<subScript id="540E2E566F739B46FFB71E1688CAC83A" attach="right" box="[114,132,1612,1626]" fontSize="6" pageId="4" pageNumber="5">42</subScript>
|
||
H
|
||
<subScript id="540E2E566F739B46FF561E1688EBC83A" attach="both" box="[147,165,1612,1626]" fontSize="6" pageId="4" pageNumber="5">72</subScript>
|
||
O
|
||
<subScript id="540E2E566F739B46FF701E1688F0C83A" attach="left" box="[181,190,1612,1626]" fontSize="6" pageId="4" pageNumber="5">6</subScript>
|
||
by mass spectroscopic experiment (HRESIMS:
|
||
<emphasis id="FAFEF0016F739B46FD5E1E1F8AF1C838" bold="true" box="[667,703,1605,1624]" italics="true" pageId="4" pageNumber="5">m/z</emphasis>
|
||
found 673.5410 [M+H]
|
||
<superScript id="3FFF815B6F739B46FED51E018952C809" attach="none" box="[272,284,1627,1641]" fontSize="6" pageId="4" pageNumber="5">+</superScript>
|
||
), and combination of NMR/IR data (
|
||
<tableCitation id="850819A86F739B46FD671E3B8AB0C814" box="[674,766,1633,1652]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetPageId="3" captionText="Table 1A NMR spectroscopic data of macrobrevin analogues, 1–2." httpUri="http://table.plazi.org/id/9CF57C9B6F749B41FFA118CC8A0CCEA0" pageId="4" pageNumber="5" tableUuid="9CF57C9B6F749B41FFA118CC8A0CCEA0">Table 1B</tableCitation>
|
||
;
|
||
<figureCitation id="50B130966F739B46FFA11E2788E5C8F0" box="[100,171,1661,1680]" captionStart="Fig" captionStartId="4.[100,130,768,785]" captionTargetBox="[268,1323,152,739]" captionTargetId="figure-868@4.[263,1324,148,741]" captionTargetPageId="4" captionText="Fig. 2. 1H–1H COSY/HMBC (A-D) correlations of macrobrevin analogues (1–4). Key 1H–1H COSY correlations and HMBC pairings were characterized by bold-faced bonds and double-barbed arrows, respectively." figureDoi="http://doi.org/10.5281/zenodo.8235155" httpUri="https://zenodo.org/record/8235155/files/figure.png" pageId="4" pageNumber="5">Fig. 2D</figureCitation>
|
||
; Fig.
|
||
<collectionCode id="AE9BB4D66F739B46FF251E2788A2C8F0" box="[224,236,1661,1680]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="4" pageNumber="5" type="Herbarium">S</collectionCode>
|
||
37-
|
||
<collectionCode id="AE9BB4D66F739B46FECC1E27895BC8F0" box="[265,277,1661,1680]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="4" pageNumber="5" type="Herbarium">S</collectionCode>
|
||
47).
|
||
<superScript id="3FFF815B6F739B46FE871E2D891AC8E5" attach="right" box="[322,340,1655,1669]" fontSize="6" pageId="4" pageNumber="5">13</superScript>
|
||
C/
|
||
<superScript id="3FFF815B6F739B46FEA91E2D89C9C8E5" attach="right" box="[364,391,1655,1669]" fontSize="6" pageId="4" pageNumber="5">135</superScript>
|
||
DEPT NMR represented 42 carbons that included two non-protonated carbons, nine methyls, ten methylenes and twenty one methines. The titled compound enclosed methoxy linkage at C-5, whereas its homologue trihydroxy-37-methyl-macrobrevin (compound
|
||
<emphasis id="FAFEF0016F739B46FF621EB688FDC89F" bold="true" box="[167,179,1772,1791]" pageId="4" pageNumber="5">1</emphasis>
|
||
) enclosed a hydroxyl at C-5. A higher chemical shift value of about ~1 ppm at H-5 (
|
||
<emphasis id="FAFEF0016F739B46FEFE1F52890BC97B" bold="true" box="[315,325,1800,1819]" italics="true" pageId="4" pageNumber="5">δ</emphasis>
|
||
<subScript id="540E2E566F739B46FE801F4A891FC97E" attach="left" box="[325,337,1808,1822]" fontSize="6" pageId="4" pageNumber="5">H</subScript>
|
||
3.35) in compound
|
||
<emphasis id="FAFEF0016F739B46FDCA1F528A55C97B" bold="true" box="[527,539,1800,1819]" pageId="4" pageNumber="5">1</emphasis>
|
||
, when compared to that in
|
||
<emphasis id="FAFEF0016F739B46FF471F7E88C0C957" bold="true" box="[130,142,1828,1847]" pageId="4" pageNumber="5">4</emphasis>
|
||
(δ 2.84) attributed the presence of hydroxyl in
|
||
<emphasis id="FAFEF0016F739B46FDBA1F7E8AC5C957" bold="true" box="[639,651,1828,1847]" pageId="4" pageNumber="5">1</emphasis>
|
||
, whereas
|
||
<emphasis id="FAFEF0016F739B46FD301F7E8B4FC957" bold="true" box="[757,769,1828,1847]" pageId="4" pageNumber="5">4</emphasis>
|
||
enclosed
|
||
<emphasis id="FAFEF0016F739B46FF041F1A889EC933" bold="true" box="[193,208,1856,1875]" italics="true" pageId="4" pageNumber="5">O</emphasis>
|
||
-methyl end at this place (C-5). Occurrence of methoxy linkage at C-5 was deduced through HMBCs from H-5 to C-5a and H-5a to C-35. The greater chemical shift at H-28 (
|
||
<emphasis id="FAFEF0016F739B46FDC81F228A59C9EB" bold="true" box="[525,535,1912,1931]" italics="true" pageId="4" pageNumber="5">δ</emphasis>
|
||
<subScript id="540E2E566F739B46FDD31F258A6CC9ED" attach="left" box="[534,546,1919,1933]" fontSize="6" pageId="4" pageNumber="5">H</subScript>
|
||
6.05) in
|
||
<emphasis id="FAFEF0016F739B46FDBE1F228AC9C9EB" bold="true" box="[635,647,1912,1931]" pageId="4" pageNumber="5">4</emphasis>
|
||
ascribed the presence of alkene, whereas the previous compound
|
||
<emphasis id="FAFEF0016F739B46FD441FCE8AC3C9C7" bold="true" box="[641,653,1940,1959]" pageId="4" pageNumber="5">1</emphasis>
|
||
enclosed a methine functionality with shielded proton shift of about
|
||
<emphasis id="FAFEF0016F739B46FA871B0E8D02CD07" bold="true" box="[1346,1356,852,871]" italics="true" pageId="4" pageNumber="5">δ</emphasis>
|
||
<subScript id="540E2E566F739B46FA891B018D16CD09" attach="left" box="[1356,1368,859,873]" fontSize="6" pageId="4" pageNumber="5">H</subScript>
|
||
2.42 (H-28), which was attached to a terminal methyl group. The typical macrobrevin enclosed a methyl at C-28 position, whereas the titled compound was devoid of any methyl group at C-28, and therefore, named as normethyl macrobrevin analogue. Alkenic groups in the titled compound were found to be
|
||
<emphasis id="FAFEF0016F739B46FC341BBA8C50CD93" bold="true" box="[1009,1054,992,1011]" italics="true" pageId="4" pageNumber="5">trans</emphasis>
|
||
-orientated (
|
||
<emphasis id="FAFEF0016F739B46FB5C1BBA8CEBCD93" bold="true" box="[1177,1189,992,1011]" italics="true" pageId="4" pageNumber="5">E</emphasis>
|
||
) attributable to their greater coupling constants. NOE couplings from H-32/H-24/H-21/H-37/H-5/ H-35 and H-21/H-38 were acknowledged for their
|
||
<emphasis id="FAFEF0016F739B46FAE11C428D61CA4B" bold="true" box="[1316,1327,1048,1067]" italics="true" pageId="4" pageNumber="5">β</emphasis>
|
||
-orientation, and those between H-41/H-31/H-40/H-22/H-19/H-18/H-13/H-36/H-9 could attribute their
|
||
<emphasis id="FAFEF0016F739B46FC3D1C158C4ACA04" bold="true" box="[1016,1028,1103,1124]" italics="true" pageId="4" pageNumber="5">α</emphasis>
|
||
-orientation. The mass spectrum exhibited a molecular ion peak at
|
||
<emphasis id="FAFEF0016F739B46FC221C318C45CA1E" bold="true" box="[999,1035,1131,1150]" italics="true" pageId="4" pageNumber="5">m/z</emphasis>
|
||
730, and the base peak was observed at
|
||
<emphasis id="FAFEF0016F739B46FA481C318DFFCA1E" bold="true" box="[1421,1457,1131,1150]" italics="true" pageId="4" pageNumber="5">m/z</emphasis>
|
||
59 (
|
||
<emphasis id="FAFEF0016F739B46FCFF1CDD8B06CAFA" bold="true" box="[826,840,1159,1178]" pageId="4" pageNumber="5">K</emphasis>
|
||
, ethene-1, 1-diol cation), which could
|
||
<taxonomicName id="0F8A57906F739B46FB071CDD8D0CCAFA" box="[1218,1346,1159,1178]" form="through" pageId="4" pageNumber="5" rank="form">form through</taxonomicName>
|
||
repeated fragmentations through McLafferty rearrangements (Fig.
|
||
<collectionCode id="AE9BB4D66F739B46FAED1CF88D7DCAD5" box="[1320,1331,1186,1205]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="4" pageNumber="5" type="Herbarium">S</collectionCode>
|
||
44-
|
||
<collectionCode id="AE9BB4D66F739B46FA971CF88D13CAD5" box="[1362,1373,1186,1205]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="4" pageNumber="5" type="Herbarium">S</collectionCode>
|
||
45).
|
||
</paragraph>
|
||
</subSubSection>
|
||
<subSubSection id="80907F986F739B45FCF71CAB8C43C83F" lastPageId="7" lastPageNumber="8" pageId="4" pageNumber="5" type="discussion">
|
||
<paragraph id="C8352C136F739B46FCF71CAB8DFACB64" blockId="4.[818,1460,1264,1285]" box="[818,1460,1264,1285]" pageId="4" pageNumber="5">
|
||
<heading id="937D9B7F6F739B46FCF71CAB8DFACB64" bold="true" box="[818,1460,1264,1285]" fontSize="36" level="1" pageId="4" pageNumber="5" reason="1">
|
||
<emphasis id="FAFEF0016F739B46FCF71CAB8DFACB64" bold="true" box="[818,1460,1264,1285]" italics="true" pageId="4" pageNumber="5">2.4. Bioactivities of macrobrevin analogues 1–4 purified by bioactivity-</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F739B46FCF71D578DCFCB40" blockId="4.[818,1409,1293,1312]" box="[818,1409,1293,1312]" pageId="4" pageNumber="5">
|
||
<heading id="937D9B7F6F739B46FCF71D578DCFCB40" box="[818,1409,1293,1312]" fontSize="8" level="3" pageId="4" pageNumber="5" reason="8">
|
||
<emphasis id="FAFEF0016F739B46FCF71D578DCFCB40" bold="true" box="[818,1409,1293,1312]" italics="true" pageId="4" pageNumber="5">supported fractionation and structure-activity relationship analysis</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F739B46FC941D1F8BEACB9F" blockId="4.[818,1488,1349,1983]" pageId="4" pageNumber="5">
|
||
The column fractions derived by repeated chromatographic separation were evaluated for antibacterial properties against broad spectra of pathogens, and those with higher yield and activities were additionally purified to obtain the pure compounds (
|
||
<tableCitation id="850819A86F739B46FB611DC38CBACBCC" box="[1188,1268,1433,1452]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetPageId="3" captionText="Table 1A NMR spectroscopic data of macrobrevin analogues, 1–2." httpUri="http://table.plazi.org/id/9CF57C9B6F749B41FFA118CC8A0CCEA0" pageId="4" pageNumber="5" tableUuid="9CF57C9B6F749B41FFA118CC8A0CCEA0">Table S1</tableCitation>
|
||
). The fraction (BAM
|
||
<subScript id="540E2E566F739B46FA761DFA8D81CBCE" attach="left" box="[1459,1487,1440,1454]" fontSize="6" pageId="4" pageNumber="5">1-3-</subScript>
|
||
<subScript id="540E2E566F739B46FCF71DE68B75CBAA" attach="none" box="[818,827,1468,1482]" fontSize="6" pageId="4" pageNumber="5">1</subScript>
|
||
) with maximum antibacterial activity (~
|
||
<quantity id="0F7281F66F739B46FB0F1DEE8D78CBA8" box="[1226,1334,1460,1480]" metricMagnitude="-2" metricUnit="m" metricValue="2.7" metricValueMax="2.8" metricValueMin="2.6" pageId="4" pageNumber="5" unit="mm" value="27.0" valueMax="28.0" valueMin="26.0">26–28 mm</quantity>
|
||
zone diameter) was purified to isolate four homogenous macrobrevin classes of compounds.
|
||
</paragraph>
|
||
<paragraph id="C8352C136F739B47FC941E5289ADC868" blockId="4.[818,1488,1349,1983]" lastBlockId="5.[100,483,1527,1544]" lastPageId="5" lastPageNumber="6" pageId="4" pageNumber="5">
|
||
<taxonomicName id="0F8A57906F739B46FC941E528C04C87B" authority="MTCC" authorityName="MTCC" box="[849,1098,1544,1563]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="4" pageNumber="5" phylum="Firmicutes" rank="species" species="amyloliquefaciens">
|
||
<emphasis id="FAFEF0016F739B46FC941E528C47C87B" bold="true" box="[849,1033,1544,1563]" italics="true" pageId="4" pageNumber="5">B. amyloliquefaciens</emphasis>
|
||
MTCC
|
||
</taxonomicName>
|
||
12713 demonstrated a wide spectrum of antibacterial activities on spot-over-lawn assay against clinically relevant pathogens (
|
||
<emphasis id="FAFEF0016F739B46FC1F1E1A8BA4C833" box="[986,1002,1600,1619]" italics="true" pageId="4" pageNumber="5">></emphasis>
|
||
<quantity id="0F7281F66F739B46FC2E1E1A8C79C833" box="[1003,1079,1600,1619]" metricMagnitude="-2" metricUnit="m" metricValue="2.0" pageId="4" pageNumber="5" unit="mm" value="20.0">20 mm</quantity>
|
||
), on preliminary screening. The purified macrobrevins (
|
||
<emphasis id="FAFEF0016F739B46FC7B1E068BAFC80F" bold="true" box="[958,993,1628,1648]" pageId="4" pageNumber="5">
|
||
1
|
||
<emphasis id="FAFEF0016F739B46FC0E1E068B98C810" bold="true" box="[971,982,1628,1648]" italics="true" pageId="4" pageNumber="5">–</emphasis>
|
||
4
|
||
</emphasis>
|
||
) showed considerable antibacterial activities against the drug-resistant pathogenic strains tested, amongst which compound
|
||
<emphasis id="FAFEF0016F739B46FA061E228D81C8EB" bold="true" box="[1475,1487,1656,1675]" pageId="4" pageNumber="5">3</emphasis>
|
||
demonstrated promising inhibitory potential against MRSA (
|
||
<quantity id="0F7281F66F739B46FABE1ECE8D8DC8C7" box="[1403,1475,1684,1703]" metricMagnitude="-2" metricUnit="m" metricValue="2.4" pageId="4" pageNumber="5" unit="mm" value="24.0">24 mm</quantity>
|
||
), VRE
|
||
<emphasis id="FAFEF0016F739B46FC9F1EF58B27C8A2" bold="true" box="[858,873,1711,1730]" italics="true" pageId="4" pageNumber="5">fs</emphasis>
|
||
(
|
||
<quantity id="0F7281F66F739B46FCB31EEA8BF3C8A3" box="[886,957,1712,1731]" metricMagnitude="-2" metricUnit="m" metricValue="3.4" pageId="4" pageNumber="5" unit="mm" value="34.0">34 mm</quantity>
|
||
),
|
||
<taxonomicName id="0F8A57906F739B46FC081EEA8C0AC8A2" authorityName="Migula" authorityYear="1900" baseAuthorityName="Schroeter" baseAuthorityYear="1872" box="[973,1092,1711,1731]" class="Betaproteobacteria" family="Burkholderiaceae" genus="Pseudomonas" kingdom="Bacteria" order="Burkholderiales" pageId="4" pageNumber="5" phylum="Proteobacteria" rank="species" species="aeruginosa">
|
||
<emphasis id="FAFEF0016F739B46FC081EEA8C0AC8A2" bold="true" box="[973,1092,1711,1731]" italics="true" pageId="4" pageNumber="5">P. aeruginosa</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<quantity id="0F7281F66F739B46FB971EEA8CD9C8A3" box="[1106,1175,1712,1731]" metricMagnitude="-2" metricUnit="m" metricValue="2.3" pageId="4" pageNumber="5" unit="mm" value="23.0">23 mm</quantity>
|
||
) and
|
||
<taxonomicName id="0F8A57906F739B46FB091EEA8D1FC8A2" authorityName="Trevisan" authorityYear="1887" baseAuthorityName="Schroeter" baseAuthorityYear="1886" box="[1228,1361,1711,1731]" class="Gammaproteobacteria" family="Enterobacteriaceae" genus="Klebsiella" kingdom="Bacteria" order="Enterobacteriales" pageId="4" pageNumber="5" phylum="Proteobacteria" rank="species" species="pneumoniae">
|
||
<emphasis id="FAFEF0016F739B46FB091EEA8D1FC8A2" bold="true" box="[1228,1361,1711,1731]" italics="true" pageId="4" pageNumber="5">K. pneumoniae</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<quantity id="0F7281F66F739B46FA9B1EF58DEDC8A3" box="[1374,1443,1711,1731]" metricMagnitude="-2" metricUnit="m" metricValue="2.5" pageId="4" pageNumber="5" unit="mm" value="25.0">25 mm</quantity>
|
||
) (30 μg on disc) (
|
||
<figureCitation id="50B130966F739B46FC6C1E918B91C8BF" box="[937,991,1739,1759]" captionStart="Fig" captionStartId="2.[100,130,1862,1879]" captionTargetBox="[189,1398,1409,1833]" captionTargetId="figure-1003@2.[188,1400,1406,1835]" captionTargetPageId="2" captionText="Fig. 1. Structural representation of (A) trihydroxy-decahydro-37-methyl-macrobrevin (compound 1), (B) hexahydro-macrobrevin (compound 2), (C) hexahydro-41- hydroxy-macrobrevin-31-acetate (compound 3), and (D) hexahydro-28-nor-methyl-5-methoxy-macrobrevin (compound 4) isolated from marine macroalgaassociated B. amyloliquefaciens MTCC 12713. (E) The zone of inhibition (34 mm) observed with hexahydro-41-hydroxy-macrobrevin-31-acetate (compound 3) against VREfs as visualized on Mueller Hinton agar plates by disc diffusion assay was illustrated. The amounts of compound 3 and chloramphenicol were 30 μg per disc. Chloramphenicol and ethyl acetate, which were used as the positive and negative control, were denoted with (+) and (), respectively." figureDoi="http://doi.org/10.5281/zenodo.8235153" httpUri="https://zenodo.org/record/8235153/files/figure.png" pageId="4" pageNumber="5">Fig. 1</figureCitation>
|
||
;
|
||
<tableCitation id="850819A86F739B46FC291E918C7DC8BF" box="[1004,1075,1739,1759]" captionStart="Table 2" captionStartId="6.[100,150,150,166]" captionTargetPageId="6" captionText="Table 2 Antibacterial activities of macrobrevin analogues 1–4 and commercial standards against clinical pathogens." httpUri="http://table.plazi.org/id/9CF57C9B6F719B44FFA118CC8BB9CEA1" pageId="4" pageNumber="5" tableUuid="9CF57C9B6F719B44FFA118CC8BB9CEA1">Table 2</tableCitation>
|
||
). Notably, small halos do not always mean that MICs are high. Small halos along with low MICs could also occur due to differentiated diffusion of each antimicrobial compound. Vancomycin or teicoplanin are examples of this behavior. In addition, chloramphenicol (30 μg per disc) gave a negligible inhibition zone only against
|
||
<taxonomicName id="0F8A57906F739B46FC401F0D8C5AC90A" authorityName="Trevisan" authorityYear="1887" baseAuthorityName="Schroeter" baseAuthorityYear="1886" box="[901,1044,1879,1898]" class="Gammaproteobacteria" family="Enterobacteriaceae" genus="Klebsiella" kingdom="Bacteria" order="Enterobacteriales" pageId="4" pageNumber="5" phylum="Proteobacteria" rank="species" species="pneumoniae">
|
||
<emphasis id="FAFEF0016F739B46FC401F0D8C5AC90A" bold="true" box="[901,1044,1879,1898]" italics="true" pageId="4" pageNumber="5">K. pneumoniae</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<tableCitation id="850819A86F739B46FBE81F0D8C33C90A" box="[1069,1149,1879,1898]" captionStart="Table 2" captionStartId="6.[100,150,150,166]" captionTargetPageId="6" captionText="Table 2 Antibacterial activities of macrobrevin analogues 1–4 and commercial standards against clinical pathogens." httpUri="http://table.plazi.org/id/9CF57C9B6F719B44FFA118CC8BB9CEA1" pageId="4" pageNumber="5" tableUuid="9CF57C9B6F719B44FFA118CC8BB9CEA1">Table 2</tableCitation>
|
||
). Microdilution analysis showed considerable MICs with hexahydro-41-hydroxy-macrobrevin-31-acetate (compound
|
||
<emphasis id="FAFEF0016F739B46FC661FD58BE1C9C2" bold="true" box="[931,943,1935,1954]" pageId="4" pageNumber="5">3</emphasis>
|
||
) for MRSA, VRE
|
||
<emphasis id="FAFEF0016F739B46FB8B1FD48C13C9C1" bold="true" box="[1102,1117,1934,1953]" italics="true" pageId="4" pageNumber="5">fs</emphasis>
|
||
,
|
||
<taxonomicName id="0F8A57906F739B46FBAF1FD58CA1C9C2" authorityName="Trevisan" authorityYear="1887" baseAuthorityName="Schroeter" baseAuthorityYear="1886" box="[1130,1263,1935,1954]" class="Gammaproteobacteria" family="Enterobacteriaceae" genus="Klebsiella" kingdom="Bacteria" order="Enterobacteriales" pageId="4" pageNumber="5" phylum="Proteobacteria" rank="species" species="pneumoniae">
|
||
<emphasis id="FAFEF0016F739B46FBAF1FD58CA1C9C2" bold="true" box="[1130,1263,1935,1954]" italics="true" pageId="4" pageNumber="5">K. pneumoniae</emphasis>
|
||
</taxonomicName>
|
||
and
|
||
<taxonomicName id="0F8A57906F739B46FADA1FD58DD8C9C2" authorityName="Migula" authorityYear="1900" baseAuthorityName="Schroeter" baseAuthorityYear="1872" box="[1311,1430,1935,1954]" class="Betaproteobacteria" family="Burkholderiaceae" genus="Pseudomonas" kingdom="Bacteria" order="Burkholderiales" pageId="4" pageNumber="5" phylum="Proteobacteria" rank="species" species="aeruginosa">
|
||
<emphasis id="FAFEF0016F739B46FADA1FD58DD8C9C2" bold="true" box="[1311,1430,1935,1954]" italics="true" pageId="4" pageNumber="5">P. aeruginosa</emphasis>
|
||
</taxonomicName>
|
||
(1.56 μg/mL) compared to those displayed by positive controls Footnotes are same as given under
|
||
<tableCitation id="850819A86F729B47FE551DAD8991C868" box="[400,479,1527,1544]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetPageId="3" captionText="Table 1A NMR spectroscopic data of macrobrevin analogues, 1–2." httpUri="http://table.plazi.org/id/9CF57C9B6F749B41FFA118CC8A0CCEA0" pageId="5" pageNumber="6" tableUuid="9CF57C9B6F749B41FFA118CC8A0CCEA0">Table 1A</tableCitation>
|
||
.
|
||
</paragraph>
|
||
<caption id="9CF57C9B6F729B47FFA118CC8A0CCEA0" pageId="5" pageNumber="6" startId="5.[100,150,150,166]" targetBox="[116,1471,470,1506]" targetIsTable="true" targetPageId="5" targetType="table">
|
||
<paragraph id="C8352C136F729B47FFA118CC88FDCEC7" blockId="5.[100,578,150,193]" box="[100,179,150,167]" pageId="5" pageNumber="6">
|
||
<emphasis id="FAFEF0016F729B47FFA118CC88FDCEC7" bold="true" box="[100,179,150,167]" pageId="5" pageNumber="6">Table 1B</emphasis>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F729B47FFA118EA8A0CCEA0" blockId="5.[100,578,150,193]" box="[100,578,176,193]" pageId="5" pageNumber="6">
|
||
NMR spectroscopic data of macrobrevin analogues,
|
||
<emphasis id="FAFEF0016F729B47FDD818EA8A73CEA1" bold="true" box="[541,573,176,193]" pageId="5" pageNumber="6">3–4</emphasis>
|
||
.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="C8352C136F729B47FFB119808D31CB82" pageId="5" pageNumber="6">
|
||
<table id="BA8ADEB36F7264BDFFB1198C8DF1CB82" box="[116,1471,470,1506]" colsContinueFrom="3.[116,1471,454,1467]" gridcols="10" gridrows="45" pageId="5" pageNumber="6">
|
||
<tr id="76BA2E516F7264BDFFB1198C8DF1CF88" box="[116,1471,470,488]" gridrow="0" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB1198C88DFCF88" box="[116,145,470,488]" gridcol="0" gridrow="0" pageId="5" pageNumber="6">No.</th>
|
||
<th id="356B472D6F7264BDFF0E198C88B8CF88" box="[203,246,470,488]" gridcol="1" gridrow="0" pageId="5" pageNumber="6">13C</th>
|
||
<th id="356B472D6F7264BDFEF5198C89A8CF88" box="[304,486,470,488]" gridcol="2" gridrow="0" pageId="5" pageNumber="6">
|
||
1H (mult., int.,
|
||
<emphasis id="FAFEF0016F729B47FE61198089E2CF88" bold="true" box="[420,428,474,488]" italics="true" pageId="5" pageNumber="6">J</emphasis>
|
||
in Hz) a
|
||
</th>
|
||
<th id="356B472D6F7264BDFDE4198C8A3BCF88" box="[545,629,470,488]" gridcol="3" gridrow="0" pageId="5" pageNumber="6">COSY</th>
|
||
<th id="356B472D6F7264BDFD6A198C8B4DCF88" box="[687,771,470,488]" gridcol="4" gridrow="0" pageId="5" pageNumber="6">HMBC</th>
|
||
<th id="356B472D6F7264BDFCF8198C8B17CF88" box="[829,857,470,488]" gridcol="5" gridrow="0" pageId="5" pageNumber="6">No.</th>
|
||
<th id="356B472D6F7264BDFC57198C8BF3CF88" box="[914,957,470,488]" gridcol="6" gridrow="0" pageId="5" pageNumber="6">13C</th>
|
||
<th id="356B472D6F7264BDFC32198C8CE3CF88" box="[1015,1197,470,488]" gridcol="7" gridrow="0" pageId="5" pageNumber="6">
|
||
1H (mult., int.,
|
||
<emphasis id="FAFEF0016F729B47FBAE19808C3DCF88" bold="true" box="[1131,1139,474,488]" italics="true" pageId="5" pageNumber="6">J</emphasis>
|
||
in Hz) a
|
||
</th>
|
||
<th id="356B472D6F7264BDFB2D198C8D72CF88" box="[1256,1340,470,488]" gridcol="8" gridrow="0" pageId="5" pageNumber="6">COSY</th>
|
||
<th id="356B472D6F7264BDFAB3198C8DF1CF88" box="[1398,1471,470,488]" gridcol="9" gridrow="0" pageId="5" pageNumber="6">HMBC</th>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB119A78DF1CC6B" box="[116,1471,509,523]" gridrow="1" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB119A788DFCC6B" box="[116,145,509,523]" gridcol="0" gridrow="1" pageId="5" pageNumber="6">1</th>
|
||
<td id="356B472D6F7264BDFF0E19A788B8CC6B" box="[203,246,509,523]" gridcol="1" gridrow="1" pageId="5" pageNumber="6">166.3</td>
|
||
<td id="356B472D6F7264BDFEF519A789A8CC6B" box="[304,486,509,523]" gridcol="2" gridrow="1" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFDE419A78A3BCC6B" box="[545,629,509,523]" gridcol="3" gridrow="1" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A19A78B4DCC6B" box="[687,771,509,523]" gridcol="4" gridrow="1" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF819A78B17CC6B" box="[829,857,509,523]" gridcol="5" gridrow="1" pageId="5" pageNumber="6">1</td>
|
||
<td id="356B472D6F7264BDFC5719A78BF3CC6B" box="[914,957,509,523]" gridcol="6" gridrow="1" pageId="5" pageNumber="6">166.3</td>
|
||
<td id="356B472D6F7264BDFC3219A78CE3CC6B" box="[1015,1197,509,523]" gridcol="7" gridrow="1" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFB2D19A78D72CC6B" box="[1256,1340,509,523]" gridcol="8" gridrow="1" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB319A78DF1CC6B" box="[1398,1471,509,523]" gridcol="9" gridrow="1" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11A4E8DF1CC42" box="[116,1471,532,546]" gridrow="2" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11A4E88DFCC42" box="[116,145,532,546]" gridcol="0" gridrow="2" pageId="5" pageNumber="6">2</th>
|
||
<td id="356B472D6F7264BDFF0E1A4E88B8CC42" box="[203,246,532,546]" gridcol="1" gridrow="2" pageId="5" pageNumber="6">122.5</td>
|
||
<td id="356B472D6F7264BDFEF51A4E89A8CC42" box="[304,486,532,546]" gridcol="2" gridrow="2" pageId="5" pageNumber="6">5.87 (d, 1H, 12.8)</td>
|
||
<td id="356B472D6F7264BDFDE41A4E8A3BCC42" box="[545,629,532,546]" gridcol="3" gridrow="2" pageId="5" pageNumber="6">H-3</td>
|
||
<td id="356B472D6F7264BDFD6A1A4E8B4DCC42" box="[687,771,532,546]" gridcol="4" gridrow="2" pageId="5" pageNumber="6">C-1, 4</td>
|
||
<td id="356B472D6F7264BDFCF81A4E8B17CC42" box="[829,857,532,546]" gridcol="5" gridrow="2" pageId="5" pageNumber="6">2</td>
|
||
<td id="356B472D6F7264BDFC571A4E8BF3CC42" box="[914,957,532,546]" gridcol="6" gridrow="2" pageId="5" pageNumber="6">122.4</td>
|
||
<td id="356B472D6F7264BDFC321A4E8CE3CC42" box="[1015,1197,532,546]" gridcol="7" gridrow="2" pageId="5" pageNumber="6">5.85 (d, 1H, 12.9)</td>
|
||
<td id="356B472D6F7264BDFB2D1A4E8D72CC42" box="[1256,1340,532,546]" gridcol="8" gridrow="2" pageId="5" pageNumber="6">H-3</td>
|
||
<td id="356B472D6F7264BDFAB31A4E8DF1CC42" box="[1398,1471,532,546]" gridcol="9" gridrow="2" pageId="5" pageNumber="6">C-1, 4</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11A718DF1CC59" box="[116,1471,555,569]" gridrow="3" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11A7188DFCC59" box="[116,145,555,569]" gridcol="0" gridrow="3" pageId="5" pageNumber="6">3</th>
|
||
<td id="356B472D6F7264BDFF0E1A7188B8CC59" box="[203,246,555,569]" gridcol="1" gridrow="3" pageId="5" pageNumber="6">155.7</td>
|
||
<td id="356B472D6F7264BDFEF51A7189A8CC59" box="[304,486,555,569]" gridcol="2" gridrow="3" pageId="5" pageNumber="6">6.84 (dd, 1H, 12.6, 4.5)</td>
|
||
<td id="356B472D6F7264BDFDE41A718A3BCC59" box="[545,629,555,569]" gridcol="3" gridrow="3" pageId="5" pageNumber="6">H-4</td>
|
||
<td id="356B472D6F7264BDFD6A1A718B4DCC59" box="[687,771,555,569]" gridcol="4" gridrow="3" pageId="5" pageNumber="6">C-1, 5</td>
|
||
<td id="356B472D6F7264BDFCF81A718B17CC59" box="[829,857,555,569]" gridcol="5" gridrow="3" pageId="5" pageNumber="6">3</td>
|
||
<td id="356B472D6F7264BDFC571A718BF3CC59" box="[914,957,555,569]" gridcol="6" gridrow="3" pageId="5" pageNumber="6">155.9</td>
|
||
<td id="356B472D6F7264BDFC321A718CE3CC59" box="[1015,1197,555,569]" gridcol="7" gridrow="3" pageId="5" pageNumber="6">6.84 (dd, 1H, 12.1, 4.3)</td>
|
||
<td id="356B472D6F7264BDFB2D1A718D72CC59" box="[1256,1340,555,569]" gridcol="8" gridrow="3" pageId="5" pageNumber="6">H-4</td>
|
||
<td id="356B472D6F7264BDFAB31A718DF1CC59" box="[1398,1471,555,569]" gridcol="9" gridrow="3" pageId="5" pageNumber="6">C-1</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11A188DF1CC30" box="[116,1471,578,592]" gridrow="4" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11A1888DFCC30" box="[116,145,578,592]" gridcol="0" gridrow="4" pageId="5" pageNumber="6">4</th>
|
||
<td id="356B472D6F7264BDFF0E1A1888B8CC30" box="[203,246,578,592]" gridcol="1" gridrow="4" pageId="5" pageNumber="6">36.7</td>
|
||
<td id="356B472D6F7264BDFEF51A1889A8CC30" box="[304,486,578,592]" gridcol="2" gridrow="4" pageId="5" pageNumber="6">2.36 (m, 1H, 2.1)</td>
|
||
<td id="356B472D6F7264BDFDE41A188A3BCC30" box="[545,629,578,592]" gridcol="3" gridrow="4" pageId="5" pageNumber="6">H-5, H-35</td>
|
||
<td id="356B472D6F7264BDFD6A1A188B4DCC30" box="[687,771,578,592]" gridcol="4" gridrow="4" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81A188B17CC30" box="[829,857,578,592]" gridcol="5" gridrow="4" pageId="5" pageNumber="6">4</td>
|
||
<td id="356B472D6F7264BDFC571A188BF3CC30" box="[914,957,578,592]" gridcol="6" gridrow="4" pageId="5" pageNumber="6">36.8</td>
|
||
<td id="356B472D6F7264BDFC321A188CE3CC30" box="[1015,1197,578,592]" gridcol="7" gridrow="4" pageId="5" pageNumber="6">2.64 (m, 1H, 2.3)</td>
|
||
<td id="356B472D6F7264BDFB2D1A188D72CC30" box="[1256,1340,578,592]" gridcol="8" gridrow="4" pageId="5" pageNumber="6">H-5, H-35</td>
|
||
<td id="356B472D6F7264BDFAB31A188DF1CC30" box="[1398,1471,578,592]" gridcol="9" gridrow="4" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11A028DF1CC07" box="[116,1471,600,615]" gridrow="5" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11A0288DFCC07" box="[116,145,600,615]" gridcol="0" gridrow="5" pageId="5" pageNumber="6">5</th>
|
||
<td id="356B472D6F7264BDFF0E1A0288B8CC07" box="[203,246,600,615]" gridcol="1" gridrow="5" pageId="5" pageNumber="6">79.0</td>
|
||
<td id="356B472D6F7264BDFEF51A0289A8CC07" box="[304,486,600,615]" gridcol="2" gridrow="5" pageId="5" pageNumber="6">
|
||
3.34 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FE491A0289DBCC07" bold="true" box="[396,405,600,615]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41A028A3BCC07" box="[545,629,600,615]" gridcol="3" gridrow="5" pageId="5" pageNumber="6">H-6</td>
|
||
<td id="356B472D6F7264BDFD6A1A028B4DCC07" box="[687,771,600,615]" gridcol="4" gridrow="5" pageId="5" pageNumber="6">C-7</td>
|
||
<td id="356B472D6F7264BDFCF81A028B17CC07" box="[829,857,600,615]" gridcol="5" gridrow="5" pageId="5" pageNumber="6">5</td>
|
||
<td id="356B472D6F7264BDFC571A028BF3CC07" box="[914,957,600,615]" gridcol="6" gridrow="5" pageId="5" pageNumber="6">81.8</td>
|
||
<td id="356B472D6F7264BDFC321A028CE3CC07" box="[1015,1197,600,615]" gridcol="7" gridrow="5" pageId="5" pageNumber="6">
|
||
2.84 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FB971A028C15CC07" bold="true" box="[1106,1115,600,615]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1A028D72CC07" box="[1256,1340,600,615]" gridcol="8" gridrow="5" pageId="5" pageNumber="6">H-6</td>
|
||
<td id="356B472D6F7264BDFAB31A028DF1CC07" box="[1398,1471,600,615]" gridcol="9" gridrow="5" pageId="5" pageNumber="6">C-3, 7, 5a</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11A358DF1CC1E" box="[116,1471,623,638]" gridrow="6" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11A3588DFCC1E" box="[116,145,623,638]" gridcol="0" gridrow="6" pageId="5" pageNumber="6">6</th>
|
||
<td id="356B472D6F7264BDFF0E1A3588B8CC1E" box="[203,246,623,638]" gridcol="1" gridrow="6" pageId="5" pageNumber="6">31.3</td>
|
||
<td id="356B472D6F7264BDFEF51A3589A8CC1E" box="[304,486,623,638]" gridcol="2" gridrow="6" pageId="5" pageNumber="6">1.62 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFDE41A358A3BCC1E" box="[545,629,623,638]" gridcol="3" gridrow="6" pageId="5" pageNumber="6">H-7</td>
|
||
<td id="356B472D6F7264BDFD6A1A358B4DCC1E" box="[687,771,623,638]" gridcol="4" gridrow="6" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81A358B17CC1E" box="[829,857,623,638]" gridcol="5" gridrow="6" pageId="5" pageNumber="6">5a</td>
|
||
<td id="356B472D6F7264BDFC571A358BF3CC1E" box="[914,957,623,638]" gridcol="6" gridrow="6" pageId="5" pageNumber="6">57.4</td>
|
||
<td id="356B472D6F7264BDFC321A358CE3CC1E" box="[1015,1197,623,638]" gridcol="7" gridrow="6" pageId="5" pageNumber="6">3.48 (s, 3H)</td>
|
||
<td id="356B472D6F7264BDFB2D1A358D72CC1E" box="[1256,1340,623,638]" gridcol="8" gridrow="6" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31A358DF1CC1E" box="[1398,1471,623,638]" gridcol="9" gridrow="6" pageId="5" pageNumber="6">C-5</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11ADC8DF1CCF4" box="[116,1471,646,660]" gridrow="7" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11ADC88DFCCF4" box="[116,145,646,660]" gridcol="0" gridrow="7" pageId="5" pageNumber="6">7</th>
|
||
<td id="356B472D6F7264BDFF0E1ADC88B8CCF4" box="[203,246,646,660]" gridcol="1" gridrow="7" pageId="5" pageNumber="6">19.2</td>
|
||
<td id="356B472D6F7264BDFEF51ADC89A8CCF4" box="[304,486,646,660]" gridcol="2" gridrow="7" pageId="5" pageNumber="6">1.49 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFDE41ADC8A3BCCF4" box="[545,629,646,660]" gridcol="3" gridrow="7" pageId="5" pageNumber="6">H-8</td>
|
||
<td id="356B472D6F7264BDFD6A1ADC8B4DCCF4" box="[687,771,646,660]" gridcol="4" gridrow="7" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81ADC8B17CCF4" box="[829,857,646,660]" gridcol="5" gridrow="7" pageId="5" pageNumber="6">6</td>
|
||
<td id="356B472D6F7264BDFC571ADC8BF3CCF4" box="[914,957,646,660]" gridcol="6" gridrow="7" pageId="5" pageNumber="6">28.3</td>
|
||
<td id="356B472D6F7264BDFC321ADC8CE3CCF4" box="[1015,1197,646,660]" gridcol="7" gridrow="7" pageId="5" pageNumber="6">1.65 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFB2D1ADC8D72CCF4" box="[1256,1340,646,660]" gridcol="8" gridrow="7" pageId="5" pageNumber="6">H-7</td>
|
||
<td id="356B472D6F7264BDFAB31ADC8DF1CCF4" box="[1398,1471,646,660]" gridcol="9" gridrow="7" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11AC78DF1CCCB" box="[116,1471,669,683]" gridrow="8" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11AC788DFCCCB" box="[116,145,669,683]" gridcol="0" gridrow="8" pageId="5" pageNumber="6">8</th>
|
||
<td id="356B472D6F7264BDFF0E1AC788B8CCCB" box="[203,246,669,683]" gridcol="1" gridrow="8" pageId="5" pageNumber="6">36.8</td>
|
||
<td id="356B472D6F7264BDFEF51AC789A8CCCB" box="[304,486,669,683]" gridcol="2" gridrow="8" pageId="5" pageNumber="6">1.65 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFDE41AC78A3BCCCB" box="[545,629,669,683]" gridcol="3" gridrow="8" pageId="5" pageNumber="6">H-9</td>
|
||
<td id="356B472D6F7264BDFD6A1AC78B4DCCCB" box="[687,771,669,683]" gridcol="4" gridrow="8" pageId="5" pageNumber="6">C-10</td>
|
||
<td id="356B472D6F7264BDFCF81AC78B17CCCB" box="[829,857,669,683]" gridcol="5" gridrow="8" pageId="5" pageNumber="6">7</td>
|
||
<td id="356B472D6F7264BDFC571AC78BF3CCCB" box="[914,957,669,683]" gridcol="6" gridrow="8" pageId="5" pageNumber="6">19.1</td>
|
||
<td id="356B472D6F7264BDFC321AC78CE3CCCB" box="[1015,1197,669,683]" gridcol="7" gridrow="8" pageId="5" pageNumber="6">1.47 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFB2D1AC78D72CCCB" box="[1256,1340,669,683]" gridcol="8" gridrow="8" pageId="5" pageNumber="6">H-8</td>
|
||
<td id="356B472D6F7264BDFAB31AC78DF1CCCB" box="[1398,1471,669,683]" gridcol="9" gridrow="8" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11AE88DF1CCA2" box="[116,1471,690,706]" gridrow="9" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11AE888DFCCA2" box="[116,145,690,706]" gridcol="0" gridrow="9" pageId="5" pageNumber="6">9</th>
|
||
<td id="356B472D6F7264BDFF0E1AE888B8CCA2" box="[203,246,690,706]" gridcol="1" gridrow="9" pageId="5" pageNumber="6">75.3</td>
|
||
<td id="356B472D6F7264BDFEF51AE889A8CCA2" box="[304,486,690,706]" gridcol="2" gridrow="9" pageId="5" pageNumber="6">
|
||
4.37 (t, 1H
|
||
<emphasis id="FAFEF0016F729B47FE461AE889C2CCA2" bold="true" box="[387,396,690,706]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
, 2.1)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41AE88A3BCCA2" box="[545,629,690,706]" gridcol="3" gridrow="9" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1AE88B4DCCA2" box="[687,771,690,706]" gridcol="4" gridrow="9" pageId="5" pageNumber="6">C-7, 10, 36</td>
|
||
<td id="356B472D6F7264BDFCF81AE88B17CCA2" box="[829,857,690,706]" gridcol="5" gridrow="9" pageId="5" pageNumber="6">8</td>
|
||
<td id="356B472D6F7264BDFC571AE88BF3CCA2" box="[914,957,690,706]" gridcol="6" gridrow="9" pageId="5" pageNumber="6">37.3</td>
|
||
<td id="356B472D6F7264BDFC321AE88CE3CCA2" box="[1015,1197,690,706]" gridcol="7" gridrow="9" pageId="5" pageNumber="6">1.77 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFB2D1AE88D72CCA2" box="[1256,1340,690,706]" gridcol="8" gridrow="9" pageId="5" pageNumber="6">H-9</td>
|
||
<td id="356B472D6F7264BDFAB31AE88DF1CCA2" box="[1398,1471,690,706]" gridcol="9" gridrow="9" pageId="5" pageNumber="6">C-6</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11A938DF1CCB9" box="[116,1471,713,729]" gridrow="10" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11A9388DFCCB9" box="[116,145,713,729]" gridcol="0" gridrow="10" pageId="5" pageNumber="6">10</th>
|
||
<td id="356B472D6F7264BDFF0E1A9388B8CCB9" box="[203,246,713,729]" gridcol="1" gridrow="10" pageId="5" pageNumber="6">138.4</td>
|
||
<td id="356B472D6F7264BDFEF51A9389A8CCB9" box="[304,486,713,729]" gridcol="2" gridrow="10" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFDE41A938A3BCCB9" box="[545,629,713,729]" gridcol="3" gridrow="10" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1A938B4DCCB9" box="[687,771,713,729]" gridcol="4" gridrow="10" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81A938B17CCB9" box="[829,857,713,729]" gridcol="5" gridrow="10" pageId="5" pageNumber="6">9</td>
|
||
<td id="356B472D6F7264BDFC571A938BF3CCB9" box="[914,957,713,729]" gridcol="6" gridrow="10" pageId="5" pageNumber="6">75.1</td>
|
||
<td id="356B472D6F7264BDFC321A938CE3CCB9" box="[1015,1197,713,729]" gridcol="7" gridrow="10" pageId="5" pageNumber="6">
|
||
4.31 (t, 1H
|
||
<emphasis id="FAFEF0016F729B47FB8F1A938C1DCCB9" bold="true" box="[1098,1107,713,729]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
, 2.1)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1A938D72CCB9" box="[1256,1340,713,729]" gridcol="8" gridrow="10" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31A938DF1CCB9" box="[1398,1471,713,729]" gridcol="9" gridrow="10" pageId="5" pageNumber="6">C-10</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11ABB8DF1CC90" box="[116,1471,737,752]" gridrow="11" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11ABB88DFCC90" box="[116,145,737,752]" gridcol="0" gridrow="11" pageId="5" pageNumber="6">11</th>
|
||
<td id="356B472D6F7264BDFF0E1ABB88B8CC90" box="[203,246,737,752]" gridcol="1" gridrow="11" pageId="5" pageNumber="6">127.5</td>
|
||
<td id="356B472D6F7264BDFEF51ABB89A8CC90" box="[304,486,737,752]" gridcol="2" gridrow="11" pageId="5" pageNumber="6">5.27 (t, 1H, 10.4)</td>
|
||
<td id="356B472D6F7264BDFDE41ABB8A3BCC90" box="[545,629,737,752]" gridcol="3" gridrow="11" pageId="5" pageNumber="6">H-12</td>
|
||
<td id="356B472D6F7264BDFD6A1ABB8B4DCC90" box="[687,771,737,752]" gridcol="4" gridrow="11" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81ABB8B17CC90" box="[829,857,737,752]" gridcol="5" gridrow="11" pageId="5" pageNumber="6">10</td>
|
||
<td id="356B472D6F7264BDFC571ABB8BF3CC90" box="[914,957,737,752]" gridcol="6" gridrow="11" pageId="5" pageNumber="6">138.4</td>
|
||
<td id="356B472D6F7264BDFC321ABB8CE3CC90" box="[1015,1197,737,752]" gridcol="7" gridrow="11" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFB2D1ABB8D72CC90" box="[1256,1340,737,752]" gridcol="8" gridrow="11" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31ABB8DF1CC90" box="[1398,1471,737,752]" gridcol="9" gridrow="11" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11AA28DF1CD67" box="[116,1471,760,775]" gridrow="12" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11AA288DFCD67" box="[116,145,760,775]" gridcol="0" gridrow="12" pageId="5" pageNumber="6">12</th>
|
||
<td id="356B472D6F7264BDFF0E1AA288B8CD67" box="[203,246,760,775]" gridcol="1" gridrow="12" pageId="5" pageNumber="6">40.2</td>
|
||
<td id="356B472D6F7264BDFEF51AA289A8CD67" box="[304,486,760,775]" gridcol="2" gridrow="12" pageId="5" pageNumber="6">2.04 (t, 2H, 1.2)</td>
|
||
<td id="356B472D6F7264BDFDE41AA28A3BCD67" box="[545,629,760,775]" gridcol="3" gridrow="12" pageId="5" pageNumber="6">H-13</td>
|
||
<td id="356B472D6F7264BDFD6A1AA28B4DCD67" box="[687,771,760,775]" gridcol="4" gridrow="12" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81AA28B17CD67" box="[829,857,760,775]" gridcol="5" gridrow="12" pageId="5" pageNumber="6">11</td>
|
||
<td id="356B472D6F7264BDFC571AA28BF3CD67" box="[914,957,760,775]" gridcol="6" gridrow="12" pageId="5" pageNumber="6">127.5</td>
|
||
<td id="356B472D6F7264BDFC321AA28CE3CD67" box="[1015,1197,760,775]" gridcol="7" gridrow="12" pageId="5" pageNumber="6">5.18 (t, 1H, 10.4)</td>
|
||
<td id="356B472D6F7264BDFB2D1AA28D72CD67" box="[1256,1340,760,775]" gridcol="8" gridrow="12" pageId="5" pageNumber="6">H-12</td>
|
||
<td id="356B472D6F7264BDFAB31AA28DF1CD67" box="[1398,1471,760,775]" gridcol="9" gridrow="12" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11B548DF1CD7E" box="[116,1471,782,798]" gridrow="13" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11B5488DFCD7E" box="[116,145,782,798]" gridcol="0" gridrow="13" pageId="5" pageNumber="6">13</th>
|
||
<td id="356B472D6F7264BDFF0E1B5488B8CD7E" box="[203,246,782,798]" gridcol="1" gridrow="13" pageId="5" pageNumber="6">45.5</td>
|
||
<td id="356B472D6F7264BDFEF51B5489A8CD7E" box="[304,486,782,798]" gridcol="2" gridrow="13" pageId="5" pageNumber="6">
|
||
2.13 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FE491B5489DBCD7E" bold="true" box="[396,405,782,798]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41B548A3BCD7E" box="[545,629,782,798]" gridcol="3" gridrow="13" pageId="5" pageNumber="6">H-14, H-37</td>
|
||
<td id="356B472D6F7264BDFD6A1B548B4DCD7E" box="[687,771,782,798]" gridcol="4" gridrow="13" pageId="5" pageNumber="6">C-11, 37</td>
|
||
<td id="356B472D6F7264BDFCF81B548B17CD7E" box="[829,857,782,798]" gridcol="5" gridrow="13" pageId="5" pageNumber="6">12</td>
|
||
<td id="356B472D6F7264BDFC571B548BF3CD7E" box="[914,957,782,798]" gridcol="6" gridrow="13" pageId="5" pageNumber="6">40.4</td>
|
||
<td id="356B472D6F7264BDFC321B548CE3CD7E" box="[1015,1197,782,798]" gridcol="7" gridrow="13" pageId="5" pageNumber="6">2.07 (t, 2H, 1.1)</td>
|
||
<td id="356B472D6F7264BDFB2D1B548D72CD7E" box="[1256,1340,782,798]" gridcol="8" gridrow="13" pageId="5" pageNumber="6">H-13</td>
|
||
<td id="356B472D6F7264BDFAB31B548DF1CD7E" box="[1398,1471,782,798]" gridcol="9" gridrow="13" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11B7E8DF1CD54" box="[116,1471,804,820]" gridrow="14" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11B7E88DFCD54" box="[116,145,804,820]" gridcol="0" gridrow="14" pageId="5" pageNumber="6">14</th>
|
||
<td id="356B472D6F7264BDFF0E1B7E88B8CD54" box="[203,246,804,820]" gridcol="1" gridrow="14" pageId="5" pageNumber="6">129.2</td>
|
||
<td id="356B472D6F7264BDFEF51B7E89A8CD54" box="[304,486,804,820]" gridcol="2" gridrow="14" pageId="5" pageNumber="6">5.44 (dd, 1H, 13.4, 2.7)</td>
|
||
<td id="356B472D6F7264BDFDE41B7E8A3BCD54" box="[545,629,804,820]" gridcol="3" gridrow="14" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1B7E8B4DCD54" box="[687,771,804,820]" gridcol="4" gridrow="14" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81B7E8B17CD54" box="[829,857,804,820]" gridcol="5" gridrow="14" pageId="5" pageNumber="6">13</td>
|
||
<td id="356B472D6F7264BDFC571B7E8BF3CD54" box="[914,957,804,820]" gridcol="6" gridrow="14" pageId="5" pageNumber="6">42.6</td>
|
||
<td id="356B472D6F7264BDFC321B7E8CE3CD54" box="[1015,1197,804,820]" gridcol="7" gridrow="14" pageId="5" pageNumber="6">
|
||
2.14 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FB971B7E8C15CD54" bold="true" box="[1106,1115,804,820]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1B7E8D72CD54" box="[1256,1340,804,820]" gridcol="8" gridrow="14" pageId="5" pageNumber="6">H-14, H-37</td>
|
||
<td id="356B472D6F7264BDFAB31B7E8DF1CD54" box="[1398,1471,804,820]" gridcol="9" gridrow="14" pageId="5" pageNumber="6">C-11, 37</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11B678DF1CD2B" box="[116,1471,829,843]" gridrow="15" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11B6788DFCD2B" box="[116,145,829,843]" gridcol="0" gridrow="15" pageId="5" pageNumber="6">15</th>
|
||
<td id="356B472D6F7264BDFF0E1B6788B8CD2B" box="[203,246,829,843]" gridcol="1" gridrow="15" pageId="5" pageNumber="6">129.9</td>
|
||
<td id="356B472D6F7264BDFEF51B6789A8CD2B" box="[304,486,829,843]" gridcol="2" gridrow="15" pageId="5" pageNumber="6">5.55 (dt, 1H, 12.7, 2.5)</td>
|
||
<td id="356B472D6F7264BDFDE41B678A3BCD2B" box="[545,629,829,843]" gridcol="3" gridrow="15" pageId="5" pageNumber="6">H-16</td>
|
||
<td id="356B472D6F7264BDFD6A1B678B4DCD2B" box="[687,771,829,843]" gridcol="4" gridrow="15" pageId="5" pageNumber="6">C-17</td>
|
||
<td id="356B472D6F7264BDFCF81B678B17CD2B" box="[829,857,829,843]" gridcol="5" gridrow="15" pageId="5" pageNumber="6">14</td>
|
||
<td id="356B472D6F7264BDFC571B678BF3CD2B" box="[914,957,829,843]" gridcol="6" gridrow="15" pageId="5" pageNumber="6">130.3</td>
|
||
<td id="356B472D6F7264BDFC321B678CE3CD2B" box="[1015,1197,829,843]" gridcol="7" gridrow="15" pageId="5" pageNumber="6">5.45 (dd, 1H, 12.4, 2.3)</td>
|
||
<td id="356B472D6F7264BDFB2D1B678D72CD2B" box="[1256,1340,829,843]" gridcol="8" gridrow="15" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31B678DF1CD2B" box="[1398,1471,829,843]" gridcol="9" gridrow="15" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11B0E8DF1CD02" box="[116,1471,852,866]" gridrow="16" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11B0E88DFCD02" box="[116,145,852,866]" gridcol="0" gridrow="16" pageId="5" pageNumber="6">16</th>
|
||
<td id="356B472D6F7264BDFF0E1B0E88B8CD02" box="[203,246,852,866]" gridcol="1" gridrow="16" pageId="5" pageNumber="6">29.7</td>
|
||
<td id="356B472D6F7264BDFEF51B0E89A8CD02" box="[304,486,852,866]" gridcol="2" gridrow="16" pageId="5" pageNumber="6">2.01 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFDE41B0E8A3BCD02" box="[545,629,852,866]" gridcol="3" gridrow="16" pageId="5" pageNumber="6">H-17</td>
|
||
<td id="356B472D6F7264BDFD6A1B0E8B4DCD02" box="[687,771,852,866]" gridcol="4" gridrow="16" pageId="5" pageNumber="6">C-14</td>
|
||
<td id="356B472D6F7264BDFCF81B0E8B17CD02" box="[829,857,852,866]" gridcol="5" gridrow="16" pageId="5" pageNumber="6">15</td>
|
||
<td id="356B472D6F7264BDFC571B0E8BF3CD02" box="[914,957,852,866]" gridcol="6" gridrow="16" pageId="5" pageNumber="6">130.0</td>
|
||
<td id="356B472D6F7264BDFC321B0E8CE3CD02" box="[1015,1197,852,866]" gridcol="7" gridrow="16" pageId="5" pageNumber="6">5.52 (dt, 1H, 12.3, 2.5)</td>
|
||
<td id="356B472D6F7264BDFB2D1B0E8D72CD02" box="[1256,1340,852,866]" gridcol="8" gridrow="16" pageId="5" pageNumber="6">H-16</td>
|
||
<td id="356B472D6F7264BDFAB31B0E8DF1CD02" box="[1398,1471,852,866]" gridcol="9" gridrow="16" pageId="5" pageNumber="6">C-17</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11B308DF1CD19" box="[116,1471,874,889]" gridrow="17" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11B3088DFCD19" box="[116,145,874,889]" gridcol="0" gridrow="17" pageId="5" pageNumber="6">17</th>
|
||
<td id="356B472D6F7264BDFF0E1B3088B8CD19" box="[203,246,874,889]" gridcol="1" gridrow="17" pageId="5" pageNumber="6">31.5</td>
|
||
<td id="356B472D6F7264BDFEF51B3089A8CD19" box="[304,486,874,889]" gridcol="2" gridrow="17" pageId="5" pageNumber="6">1.53 (m, 1H)</td>
|
||
<td id="356B472D6F7264BDFDE41B308A3BCD19" box="[545,629,874,889]" gridcol="3" gridrow="17" pageId="5" pageNumber="6">H-18</td>
|
||
<td id="356B472D6F7264BDFD6A1B308B4DCD19" box="[687,771,874,889]" gridcol="4" gridrow="17" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81B308B17CD19" box="[829,857,874,889]" gridcol="5" gridrow="17" pageId="5" pageNumber="6">16</td>
|
||
<td id="356B472D6F7264BDFC571B308BF3CD19" box="[914,957,874,889]" gridcol="6" gridrow="17" pageId="5" pageNumber="6">28.1</td>
|
||
<td id="356B472D6F7264BDFC321B308CE3CD19" box="[1015,1197,874,889]" gridcol="7" gridrow="17" pageId="5" pageNumber="6">2.03 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFB2D1B308D72CD19" box="[1256,1340,874,889]" gridcol="8" gridrow="17" pageId="5" pageNumber="6">H-17</td>
|
||
<td id="356B472D6F7264BDFAB31B308DF1CD19" box="[1398,1471,874,889]" gridcol="9" gridrow="17" pageId="5" pageNumber="6">C-14</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11BDA8DF1CDF0" box="[116,1471,896,912]" gridrow="18" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11BDA88DFCDF0" box="[116,145,896,912]" gridcol="0" gridrow="18" pageId="5" pageNumber="6">18</th>
|
||
<td id="356B472D6F7264BDFF0E1BDA88B8CDF0" box="[203,246,896,912]" gridcol="1" gridrow="18" pageId="5" pageNumber="6">37.4</td>
|
||
<td id="356B472D6F7264BDFEF51BDA89A8CDF0" box="[304,486,896,912]" gridcol="2" gridrow="18" pageId="5" pageNumber="6">
|
||
1.71 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FE491BDA89DBCDF0" bold="true" box="[396,405,896,912]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41BDA8A3BCDF0" box="[545,629,896,912]" gridcol="3" gridrow="18" pageId="5" pageNumber="6">H-19, H-38</td>
|
||
<td id="356B472D6F7264BDFD6A1BDA8B4DCDF0" box="[687,771,896,912]" gridcol="4" gridrow="18" pageId="5" pageNumber="6">C-20</td>
|
||
<td id="356B472D6F7264BDFCF81BDA8B17CDF0" box="[829,857,896,912]" gridcol="5" gridrow="18" pageId="5" pageNumber="6">17</td>
|
||
<td id="356B472D6F7264BDFC571BDA8BF3CDF0" box="[914,957,896,912]" gridcol="6" gridrow="18" pageId="5" pageNumber="6">28.5</td>
|
||
<td id="356B472D6F7264BDFC321BDA8CE3CDF0" box="[1015,1197,896,912]" gridcol="7" gridrow="18" pageId="5" pageNumber="6">1.51 (m, 1H)</td>
|
||
<td id="356B472D6F7264BDFB2D1BDA8D72CDF0" box="[1256,1340,896,912]" gridcol="8" gridrow="18" pageId="5" pageNumber="6">H-18</td>
|
||
<td id="356B472D6F7264BDFAB31BDA8DF1CDF0" box="[1398,1471,896,912]" gridcol="9" gridrow="18" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11BCD8DF1CDC7" box="[116,1471,919,935]" gridrow="19" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11BCD88DFCDC7" box="[116,145,919,935]" gridcol="0" gridrow="19" pageId="5" pageNumber="6">19</th>
|
||
<td id="356B472D6F7264BDFF0E1BCD88B8CDC7" box="[203,246,919,935]" gridcol="1" gridrow="19" pageId="5" pageNumber="6">71.6</td>
|
||
<td id="356B472D6F7264BDFEF51BCD89A8CDC7" box="[304,486,919,935]" gridcol="2" gridrow="19" pageId="5" pageNumber="6">
|
||
3.39 (q, 1H
|
||
<emphasis id="FAFEF0016F729B47FE421BCD89DECDC7" bold="true" box="[391,400,919,935]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
, 2.6)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41BCD8A3BCDC7" box="[545,629,919,935]" gridcol="3" gridrow="19" pageId="5" pageNumber="6">H-20</td>
|
||
<td id="356B472D6F7264BDFD6A1BCD8B4DCDC7" box="[687,771,919,935]" gridcol="4" gridrow="19" pageId="5" pageNumber="6">C-17</td>
|
||
<td id="356B472D6F7264BDFCF81BCD8B17CDC7" box="[829,857,919,935]" gridcol="5" gridrow="19" pageId="5" pageNumber="6">18</td>
|
||
<td id="356B472D6F7264BDFC571BCD8BF3CDC7" box="[914,957,919,935]" gridcol="6" gridrow="19" pageId="5" pageNumber="6">37.7</td>
|
||
<td id="356B472D6F7264BDFC321BCD8CE3CDC7" box="[1015,1197,919,935]" gridcol="7" gridrow="19" pageId="5" pageNumber="6">
|
||
1.90 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FB971BCD8C15CDC7" bold="true" box="[1106,1115,919,935]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1BCD8D72CDC7" box="[1256,1340,919,935]" gridcol="8" gridrow="19" pageId="5" pageNumber="6">H-19, H-38</td>
|
||
<td id="356B472D6F7264BDFAB31BCD8DF1CDC7" box="[1398,1471,919,935]" gridcol="9" gridrow="19" pageId="5" pageNumber="6">C-20</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11BF48DF1CDDE" box="[116,1471,942,958]" gridrow="20" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11BF488DFCDDE" box="[116,145,942,958]" gridcol="0" gridrow="20" pageId="5" pageNumber="6">20</th>
|
||
<td id="356B472D6F7264BDFF0E1BF488B8CDDE" box="[203,246,942,958]" gridcol="1" gridrow="20" pageId="5" pageNumber="6">38.6</td>
|
||
<td id="356B472D6F7264BDFEF51BF489A8CDDE" box="[304,486,942,958]" gridcol="2" gridrow="20" pageId="5" pageNumber="6">1.56 (t, 2H, 3.5)</td>
|
||
<td id="356B472D6F7264BDFDE41BF48A3BCDDE" box="[545,629,942,958]" gridcol="3" gridrow="20" pageId="5" pageNumber="6">H-21</td>
|
||
<td id="356B472D6F7264BDFD6A1BF48B4DCDDE" box="[687,771,942,958]" gridcol="4" gridrow="20" pageId="5" pageNumber="6">C-21</td>
|
||
<td id="356B472D6F7264BDFCF81BF48B17CDDE" box="[829,857,942,958]" gridcol="5" gridrow="20" pageId="5" pageNumber="6">19</td>
|
||
<td id="356B472D6F7264BDFC571BF48BF3CDDE" box="[914,957,942,958]" gridcol="6" gridrow="20" pageId="5" pageNumber="6">71.0</td>
|
||
<td id="356B472D6F7264BDFC321BF48CE3CDDE" box="[1015,1197,942,958]" gridcol="7" gridrow="20" pageId="5" pageNumber="6">
|
||
3.39 (q, 1H
|
||
<emphasis id="FAFEF0016F729B47FB881BF48C18CDDE" bold="true" box="[1101,1110,942,958]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
, 2.4)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1BF48D72CDDE" box="[1256,1340,942,958]" gridcol="8" gridrow="20" pageId="5" pageNumber="6">H-20</td>
|
||
<td id="356B472D6F7264BDFAB31BF48DF1CDDE" box="[1398,1471,942,958]" gridcol="9" gridrow="20" pageId="5" pageNumber="6">C-17</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11B9C8DF1CDB5" box="[116,1471,966,981]" gridrow="21" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11B9C88DFCDB5" box="[116,145,966,981]" gridcol="0" gridrow="21" pageId="5" pageNumber="6">21</th>
|
||
<td id="356B472D6F7264BDFF0E1B9C88B8CDB5" box="[203,246,966,981]" gridcol="1" gridrow="21" pageId="5" pageNumber="6">70.5</td>
|
||
<td id="356B472D6F7264BDFEF51B9C89A8CDB5" box="[304,486,966,981]" gridcol="2" gridrow="21" pageId="5" pageNumber="6">
|
||
3.92 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FE491B9C89DBCDB5" bold="true" box="[396,405,966,981]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41B9C8A3BCDB5" box="[545,629,966,981]" gridcol="3" gridrow="21" pageId="5" pageNumber="6">H-22</td>
|
||
<td id="356B472D6F7264BDFD6A1B9C8B4DCDB5" box="[687,771,966,981]" gridcol="4" gridrow="21" pageId="5" pageNumber="6">C-1</td>
|
||
<td id="356B472D6F7264BDFCF81B9C8B17CDB5" box="[829,857,966,981]" gridcol="5" gridrow="21" pageId="5" pageNumber="6">20</td>
|
||
<td id="356B472D6F7264BDFC571B9C8BF3CDB5" box="[914,957,966,981]" gridcol="6" gridrow="21" pageId="5" pageNumber="6">38.6</td>
|
||
<td id="356B472D6F7264BDFC321B9C8CE3CDB5" box="[1015,1197,966,981]" gridcol="7" gridrow="21" pageId="5" pageNumber="6">1.53 (t, 2H, 3.3)</td>
|
||
<td id="356B472D6F7264BDFB2D1B9C8D72CDB5" box="[1256,1340,966,981]" gridcol="8" gridrow="21" pageId="5" pageNumber="6">H-21</td>
|
||
<td id="356B472D6F7264BDFAB31B9C8DF1CDB5" box="[1398,1471,966,981]" gridcol="9" gridrow="21" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11B818DF1CD8C" box="[116,1471,987,1004]" gridrow="22" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11B8188DFCD8C" box="[116,145,987,1004]" gridcol="0" gridrow="22" pageId="5" pageNumber="6">22</th>
|
||
<td id="356B472D6F7264BDFF0E1B8188B8CD8C" box="[203,246,987,1004]" gridcol="1" gridrow="22" pageId="5" pageNumber="6">34.1</td>
|
||
<td id="356B472D6F7264BDFEF51B8189A8CD8C" box="[304,486,987,1004]" gridcol="2" gridrow="22" pageId="5" pageNumber="6">
|
||
2.22 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FE491B8189DBCD8B" bold="true" box="[396,405,987,1003]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41B818A3BCD8C" box="[545,629,987,1004]" gridcol="3" gridrow="22" pageId="5" pageNumber="6">H-23, H-39</td>
|
||
<td id="356B472D6F7264BDFD6A1B818B4DCD8C" box="[687,771,987,1004]" gridcol="4" gridrow="22" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81B818B17CD8C" box="[829,857,987,1004]" gridcol="5" gridrow="22" pageId="5" pageNumber="6">21</td>
|
||
<td id="356B472D6F7264BDFC571B818BF3CD8C" box="[914,957,987,1004]" gridcol="6" gridrow="22" pageId="5" pageNumber="6">68.3</td>
|
||
<td id="356B472D6F7264BDFC321B818CE3CD8C" box="[1015,1197,987,1004]" gridcol="7" gridrow="22" pageId="5" pageNumber="6">
|
||
3.90 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FB971B878C15CD8C" bold="true" box="[1106,1115,989,1004]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1B818D72CD8C" box="[1256,1340,987,1004]" gridcol="8" gridrow="22" pageId="5" pageNumber="6">H-22</td>
|
||
<td id="356B472D6F7264BDFAB31B818DF1CD8C" box="[1398,1471,987,1004]" gridcol="9" gridrow="22" pageId="5" pageNumber="6">C-1</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11BA88DF1CA62" box="[116,1471,1010,1026]" gridrow="23" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11BA888DFCA62" box="[116,145,1010,1026]" gridcol="0" gridrow="23" pageId="5" pageNumber="6">23</th>
|
||
<td id="356B472D6F7264BDFF0E1BA888B8CA62" box="[203,246,1010,1026]" gridcol="1" gridrow="23" pageId="5" pageNumber="6">37.8</td>
|
||
<td id="356B472D6F7264BDFEF51BA889A8CA62" box="[304,486,1010,1026]" gridcol="2" gridrow="23" pageId="5" pageNumber="6">1.29 (t, 2H, 2.4)</td>
|
||
<td id="356B472D6F7264BDFDE41BA88A3BCA62" box="[545,629,1010,1026]" gridcol="3" gridrow="23" pageId="5" pageNumber="6">H-24</td>
|
||
<td id="356B472D6F7264BDFD6A1BA88B4DCA62" box="[687,771,1010,1026]" gridcol="4" gridrow="23" pageId="5" pageNumber="6">C-21</td>
|
||
<td id="356B472D6F7264BDFCF81BA88B17CA62" box="[829,857,1010,1026]" gridcol="5" gridrow="23" pageId="5" pageNumber="6">22</td>
|
||
<td id="356B472D6F7264BDFC571BA88BF3CA62" box="[914,957,1010,1026]" gridcol="6" gridrow="23" pageId="5" pageNumber="6">33.1</td>
|
||
<td id="356B472D6F7264BDFC321BA88CE3CA62" box="[1015,1197,1010,1026]" gridcol="7" gridrow="23" pageId="5" pageNumber="6">
|
||
2.37 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FB971BA88C15CA62" bold="true" box="[1106,1115,1010,1026]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1BA88D72CA62" box="[1256,1340,1010,1026]" gridcol="8" gridrow="23" pageId="5" pageNumber="6">H-23, H-39</td>
|
||
<td id="356B472D6F7264BDFAB31BA88DF1CA62" box="[1398,1471,1010,1026]" gridcol="9" gridrow="23" pageId="5" pageNumber="6">C-21, 24</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11C508DF1CA79" box="[116,1471,1034,1049]" gridrow="24" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11C5088DFCA79" box="[116,145,1034,1049]" gridcol="0" gridrow="24" pageId="5" pageNumber="6">24</th>
|
||
<td id="356B472D6F7264BDFF0E1C5088B8CA79" box="[203,246,1034,1049]" gridcol="1" gridrow="24" pageId="5" pageNumber="6">35.3</td>
|
||
<td id="356B472D6F7264BDFEF51C5089A8CA79" box="[304,486,1034,1049]" gridcol="2" gridrow="24" pageId="5" pageNumber="6">
|
||
1.69 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FE491C5089DBCA79" bold="true" box="[396,405,1034,1049]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41C508A3BCA79" box="[545,629,1034,1049]" gridcol="3" gridrow="24" pageId="5" pageNumber="6">H-25, H-40</td>
|
||
<td id="356B472D6F7264BDFD6A1C508B4DCA79" box="[687,771,1034,1049]" gridcol="4" gridrow="24" pageId="5" pageNumber="6">C-26</td>
|
||
<td id="356B472D6F7264BDFCF81C508B17CA79" box="[829,857,1034,1049]" gridcol="5" gridrow="24" pageId="5" pageNumber="6">23</td>
|
||
<td id="356B472D6F7264BDFC571C508BF3CA79" box="[914,957,1034,1049]" gridcol="6" gridrow="24" pageId="5" pageNumber="6">38.5</td>
|
||
<td id="356B472D6F7264BDFC321C508CE3CA79" box="[1015,1197,1034,1049]" gridcol="7" gridrow="24" pageId="5" pageNumber="6">1.26 (t, 2H, 2.2)</td>
|
||
<td id="356B472D6F7264BDFB2D1C508D72CA79" box="[1256,1340,1034,1049]" gridcol="8" gridrow="24" pageId="5" pageNumber="6">H-24</td>
|
||
<td id="356B472D6F7264BDFAB31C508DF1CA79" box="[1398,1471,1034,1049]" gridcol="9" gridrow="24" pageId="5" pageNumber="6">C-21</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11C7B8DF1CA50" box="[116,1471,1057,1072]" gridrow="25" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11C7B88DFCA50" box="[116,145,1057,1072]" gridcol="0" gridrow="25" pageId="5" pageNumber="6">25</th>
|
||
<td id="356B472D6F7264BDFF0E1C7B88B8CA50" box="[203,246,1057,1072]" gridcol="1" gridrow="25" pageId="5" pageNumber="6">31.9</td>
|
||
<td id="356B472D6F7264BDFEF51C7B89A8CA50" box="[304,486,1057,1072]" gridcol="2" gridrow="25" pageId="5" pageNumber="6">1.21 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFDE41C7B8A3BCA50" box="[545,629,1057,1072]" gridcol="3" gridrow="25" pageId="5" pageNumber="6">H-26</td>
|
||
<td id="356B472D6F7264BDFD6A1C7B8B4DCA50" box="[687,771,1057,1072]" gridcol="4" gridrow="25" pageId="5" pageNumber="6">C-23</td>
|
||
<td id="356B472D6F7264BDFCF81C7B8B17CA50" box="[829,857,1057,1072]" gridcol="5" gridrow="25" pageId="5" pageNumber="6">24</td>
|
||
<td id="356B472D6F7264BDFC571C7B8BF3CA50" box="[914,957,1057,1072]" gridcol="6" gridrow="25" pageId="5" pageNumber="6">36.0</td>
|
||
<td id="356B472D6F7264BDFC321C7B8CE3CA50" box="[1015,1197,1057,1072]" gridcol="7" gridrow="25" pageId="5" pageNumber="6">
|
||
1.81 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FB971C7B8C15CA50" bold="true" box="[1106,1115,1057,1072]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1C7B8D72CA50" box="[1256,1340,1057,1072]" gridcol="8" gridrow="25" pageId="5" pageNumber="6">H-25, H-40</td>
|
||
<td id="356B472D6F7264BDFAB31C7B8DF1CA50" box="[1398,1471,1057,1072]" gridcol="9" gridrow="25" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11C628DF1CA26" box="[116,1471,1080,1094]" gridrow="26" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11C6288DFCA26" box="[116,145,1080,1094]" gridcol="0" gridrow="26" pageId="5" pageNumber="6">26</th>
|
||
<td id="356B472D6F7264BDFF0E1C6288B8CA26" box="[203,246,1080,1094]" gridcol="1" gridrow="26" pageId="5" pageNumber="6">33.1</td>
|
||
<td id="356B472D6F7264BDFEF51C6289A8CA26" box="[304,486,1080,1094]" gridcol="2" gridrow="26" pageId="5" pageNumber="6">1.43 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFDE41C628A3BCA26" box="[545,629,1080,1094]" gridcol="3" gridrow="26" pageId="5" pageNumber="6">H-27</td>
|
||
<td id="356B472D6F7264BDFD6A1C628B4DCA26" box="[687,771,1080,1094]" gridcol="4" gridrow="26" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81C628B17CA26" box="[829,857,1080,1094]" gridcol="5" gridrow="26" pageId="5" pageNumber="6">25</td>
|
||
<td id="356B472D6F7264BDFC571C628BF3CA26" box="[914,957,1080,1094]" gridcol="6" gridrow="26" pageId="5" pageNumber="6">29.7</td>
|
||
<td id="356B472D6F7264BDFC321C628CE3CA26" box="[1015,1197,1080,1094]" gridcol="7" gridrow="26" pageId="5" pageNumber="6">1.24 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFB2D1C628D72CA26" box="[1256,1340,1080,1094]" gridcol="8" gridrow="26" pageId="5" pageNumber="6">H-26</td>
|
||
<td id="356B472D6F7264BDFAB31C628DF1CA26" box="[1398,1471,1080,1094]" gridcol="9" gridrow="26" pageId="5" pageNumber="6">C-23</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11C158DF1CA3D" box="[116,1471,1103,1117]" gridrow="27" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11C1588DFCA3D" box="[116,145,1103,1117]" gridcol="0" gridrow="27" pageId="5" pageNumber="6">27</th>
|
||
<td id="356B472D6F7264BDFF0E1C1588B8CA3D" box="[203,246,1103,1117]" gridcol="1" gridrow="27" pageId="5" pageNumber="6">131.8</td>
|
||
<td id="356B472D6F7264BDFEF51C1589A8CA3D" box="[304,486,1103,1117]" gridcol="2" gridrow="27" pageId="5" pageNumber="6">5.58 (t, 1H, 13.9)</td>
|
||
<td id="356B472D6F7264BDFDE41C158A3BCA3D" box="[545,629,1103,1117]" gridcol="3" gridrow="27" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1C158B4DCA3D" box="[687,771,1103,1117]" gridcol="4" gridrow="27" pageId="5" pageNumber="6">C-28, 41</td>
|
||
<td id="356B472D6F7264BDFCF81C158B17CA3D" box="[829,857,1103,1117]" gridcol="5" gridrow="27" pageId="5" pageNumber="6">26</td>
|
||
<td id="356B472D6F7264BDFC571C158BF3CA3D" box="[914,957,1103,1117]" gridcol="6" gridrow="27" pageId="5" pageNumber="6">35.3</td>
|
||
<td id="356B472D6F7264BDFC321C158CE3CA3D" box="[1015,1197,1103,1117]" gridcol="7" gridrow="27" pageId="5" pageNumber="6">1.42 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFB2D1C158D72CA3D" box="[1256,1340,1103,1117]" gridcol="8" gridrow="27" pageId="5" pageNumber="6">H-27</td>
|
||
<td id="356B472D6F7264BDFAB31C158DF1CA3D" box="[1398,1471,1103,1117]" gridcol="9" gridrow="27" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11C3C8DF1CA14" box="[116,1471,1126,1140]" gridrow="28" pageId="5" pageNumber="6" rowspan-4="1">
|
||
<th id="356B472D6F7264BDFFB11C3C88DFCA14" box="[116,145,1126,1140]" gridcol="0" gridrow="28" pageId="5" pageNumber="6">28</th>
|
||
<td id="356B472D6F7264BDFF0E1C3C88B8CA14" box="[203,246,1126,1140]" gridcol="1" gridrow="28" pageId="5" pageNumber="6">143.8</td>
|
||
<td id="356B472D6F7264BDFEF51C3C89A8CA14" box="[304,486,1126,1140]" gridcol="2" gridrow="28" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFDE41C3C8A3BCA14" box="[545,629,1126,1140]" gridcol="3" gridrow="28" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81C3C8B17CA14" box="[829,857,1126,1140]" gridcol="5" gridrow="28" pageId="5" pageNumber="6">27</td>
|
||
<td id="356B472D6F7264BDFC571C3C8BF3CA14" box="[914,957,1126,1140]" gridcol="6" gridrow="28" pageId="5" pageNumber="6">135.9</td>
|
||
<td id="356B472D6F7264BDFC321C3C8CE3CA14" box="[1015,1197,1126,1140]" gridcol="7" gridrow="28" pageId="5" pageNumber="6">5.61 (dt, 1H, 13.1, 4.1)</td>
|
||
<td id="356B472D6F7264BDFB2D1C3C8D72CA14" box="[1256,1340,1126,1140]" gridcol="8" gridrow="28" pageId="5" pageNumber="6">H-28</td>
|
||
<td id="356B472D6F7264BDFAB31C3C8DF1CA14" box="[1398,1471,1126,1140]" gridcol="9" gridrow="28" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11C278DF1CAEB" box="[116,1471,1149,1163]" gridrow="29" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11C2788DFCAEB" box="[116,145,1149,1163]" gridcol="0" gridrow="29" pageId="5" pageNumber="6">29</th>
|
||
<td id="356B472D6F7264BDFF0E1C2788B8CAEB" box="[203,246,1149,1163]" gridcol="1" gridrow="29" pageId="5" pageNumber="6">130.3</td>
|
||
<td id="356B472D6F7264BDFEF51C2789A8CAEB" box="[304,486,1149,1163]" gridcol="2" gridrow="29" pageId="5" pageNumber="6">6.26 (d, 1H, 13.1)</td>
|
||
<td id="356B472D6F7264BDFDE41C278A3BCAEB" box="[545,629,1149,1163]" gridcol="3" gridrow="29" pageId="5" pageNumber="6">H-30</td>
|
||
<td id="356B472D6F7264BDFD6A1C278B4DCAEB" box="[687,771,1149,1163]" gridcol="4" gridrow="29" pageId="5" pageNumber="6">C-27</td>
|
||
<td id="356B472D6F7264BDFCF81C278B17CAEB" box="[829,857,1149,1163]" gridcol="5" gridrow="29" pageId="5" pageNumber="6">28</td>
|
||
<td id="356B472D6F7264BDFC571C278BF3CAEB" box="[914,957,1149,1163]" gridcol="6" gridrow="29" pageId="5" pageNumber="6">129.2</td>
|
||
<td id="356B472D6F7264BDFC321C278CE3CAEB" box="[1015,1197,1149,1163]" gridcol="7" gridrow="29" pageId="5" pageNumber="6">6.05 (dd, 1H, 13.4, 3.5)</td>
|
||
<td id="356B472D6F7264BDFB2D1C278D72CAEB" box="[1256,1340,1149,1163]" gridcol="8" gridrow="29" pageId="5" pageNumber="6">H-29</td>
|
||
<td id="356B472D6F7264BDFAB31C278DF1CAEB" box="[1398,1471,1149,1163]" gridcol="9" gridrow="29" pageId="5" pageNumber="6">C-30</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11CCE8DF1CAC2" box="[116,1471,1172,1186]" gridrow="30" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11CCE88DFCAC2" box="[116,145,1172,1186]" gridcol="0" gridrow="30" pageId="5" pageNumber="6">30</th>
|
||
<td id="356B472D6F7264BDFF0E1CCE88B8CAC2" box="[203,246,1172,1186]" gridcol="1" gridrow="30" pageId="5" pageNumber="6">135.8</td>
|
||
<td id="356B472D6F7264BDFEF51CCE89A8CAC2" box="[304,486,1172,1186]" gridcol="2" gridrow="30" pageId="5" pageNumber="6">5.61 (t, 1H, 10.2)</td>
|
||
<td id="356B472D6F7264BDFDE41CCE8A3BCAC2" box="[545,629,1172,1186]" gridcol="3" gridrow="30" pageId="5" pageNumber="6">H-31</td>
|
||
<td id="356B472D6F7264BDFD6A1CCE8B4DCAC2" box="[687,771,1172,1186]" gridcol="4" gridrow="30" pageId="5" pageNumber="6">C-31, 32</td>
|
||
<td id="356B472D6F7264BDFCF81CCE8B17CAC2" box="[829,857,1172,1186]" gridcol="5" gridrow="30" pageId="5" pageNumber="6">29</td>
|
||
<td id="356B472D6F7264BDFC571CCE8BF3CAC2" box="[914,957,1172,1186]" gridcol="6" gridrow="30" pageId="5" pageNumber="6">128.7</td>
|
||
<td id="356B472D6F7264BDFC321CCE8CE3CAC2" box="[1015,1197,1172,1186]" gridcol="7" gridrow="30" pageId="5" pageNumber="6">6.46 (dd, 1H, 13.0, 3.2)</td>
|
||
<td id="356B472D6F7264BDFB2D1CCE8D72CAC2" box="[1256,1340,1172,1186]" gridcol="8" gridrow="30" pageId="5" pageNumber="6">H-30</td>
|
||
<td id="356B472D6F7264BDFAB31CCE8DF1CAC2" box="[1398,1471,1172,1186]" gridcol="9" gridrow="30" pageId="5" pageNumber="6">C-27</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11CF08DF1CAD9" box="[116,1471,1194,1209]" gridrow="31" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11CF088DFCAD9" box="[116,145,1194,1209]" gridcol="0" gridrow="31" pageId="5" pageNumber="6">31</th>
|
||
<td id="356B472D6F7264BDFF0E1CF088B8CAD9" box="[203,246,1194,1209]" gridcol="1" gridrow="31" pageId="5" pageNumber="6">75.5</td>
|
||
<td id="356B472D6F7264BDFEF51CF089A8CAD9" box="[304,486,1194,1209]" gridcol="2" gridrow="31" pageId="5" pageNumber="6">
|
||
4.65 (t, 1H
|
||
<emphasis id="FAFEF0016F729B47FE461CF089C2CAD9" bold="true" box="[387,396,1194,1209]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
, 3.2)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41CF08A3BCAD9" box="[545,629,1194,1209]" gridcol="3" gridrow="31" pageId="5" pageNumber="6">H-32</td>
|
||
<td id="356B472D6F7264BDFD6A1CF08B4DCAD9" box="[687,771,1194,1209]" gridcol="4" gridrow="31" pageId="5" pageNumber="6">C-31a</td>
|
||
<td id="356B472D6F7264BDFCF81CF08B17CAD9" box="[829,857,1194,1209]" gridcol="5" gridrow="31" pageId="5" pageNumber="6">30</td>
|
||
<td id="356B472D6F7264BDFC571CF08BF3CAD9" box="[914,957,1194,1209]" gridcol="6" gridrow="31" pageId="5" pageNumber="6">135.8</td>
|
||
<td id="356B472D6F7264BDFC321CF08CE3CAD9" box="[1015,1197,1194,1209]" gridcol="7" gridrow="31" pageId="5" pageNumber="6">5.70 (dd, 1H, 11.2, 3.6)</td>
|
||
<td id="356B472D6F7264BDFB2D1CF08D72CAD9" box="[1256,1340,1194,1209]" gridcol="8" gridrow="31" pageId="5" pageNumber="6">H-31</td>
|
||
<td id="356B472D6F7264BDFAB31CF08DF1CAD9" box="[1398,1471,1194,1209]" gridcol="9" gridrow="31" pageId="5" pageNumber="6">C-32</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11C9B8DF1CAB0" box="[116,1471,1217,1232]" gridrow="32" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11C9B88DFCAB0" box="[116,145,1217,1232]" gridcol="0" gridrow="32" pageId="5" pageNumber="6">31a</th>
|
||
<td id="356B472D6F7264BDFF0E1C9B88B8CAB0" box="[203,246,1217,1232]" gridcol="1" gridrow="32" pageId="5" pageNumber="6">170.3</td>
|
||
<td id="356B472D6F7264BDFEF51C9B89A8CAB0" box="[304,486,1217,1232]" gridcol="2" gridrow="32" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFDE41C9B8A3BCAB0" box="[545,629,1217,1232]" gridcol="3" gridrow="32" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1C9B8B4DCAB0" box="[687,771,1217,1232]" gridcol="4" gridrow="32" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81C9B8B17CAB0" box="[829,857,1217,1232]" gridcol="5" gridrow="32" pageId="5" pageNumber="6">31</td>
|
||
<td id="356B472D6F7264BDFC571C9B8BF3CAB0" box="[914,957,1217,1232]" gridcol="6" gridrow="32" pageId="5" pageNumber="6">75.7</td>
|
||
<td id="356B472D6F7264BDFC321C9B8CE3CAB0" box="[1015,1197,1217,1232]" gridcol="7" gridrow="32" pageId="5" pageNumber="6">3.57 (t, 1H, 3.3)</td>
|
||
<td id="356B472D6F7264BDFB2D1C9B8D72CAB0" box="[1256,1340,1217,1232]" gridcol="8" gridrow="32" pageId="5" pageNumber="6">H-32</td>
|
||
<td id="356B472D6F7264BDFAB31C9B8DF1CAB0" box="[1398,1471,1217,1232]" gridcol="9" gridrow="32" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11C828DF1CA87" box="[116,1471,1240,1255]" gridrow="33" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11C8288DFCA87" box="[116,145,1240,1255]" gridcol="0" gridrow="33" pageId="5" pageNumber="6">31b</th>
|
||
<td id="356B472D6F7264BDFF0E1C8288B8CA87" box="[203,246,1240,1255]" gridcol="1" gridrow="33" pageId="5" pageNumber="6">22.7</td>
|
||
<td id="356B472D6F7264BDFEF51C8289A8CA87" box="[304,486,1240,1255]" gridcol="2" gridrow="33" pageId="5" pageNumber="6">2.06 (s, 3H)</td>
|
||
<td id="356B472D6F7264BDFDE41C828A3BCA87" box="[545,629,1240,1255]" gridcol="3" gridrow="33" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1C828B4DCA87" box="[687,771,1240,1255]" gridcol="4" gridrow="33" pageId="5" pageNumber="6">C-31, 31a</td>
|
||
<td id="356B472D6F7264BDFCF81C828B17CA87" box="[829,857,1240,1255]" gridcol="5" gridrow="33" pageId="5" pageNumber="6">32</td>
|
||
<td id="356B472D6F7264BDFC571C828BF3CA87" box="[914,957,1240,1255]" gridcol="6" gridrow="33" pageId="5" pageNumber="6">45.5</td>
|
||
<td id="356B472D6F7264BDFC321C828CE3CA87" box="[1015,1197,1240,1255]" gridcol="7" gridrow="33" pageId="5" pageNumber="6">
|
||
1.93 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FB971C828C15CA87" bold="true" box="[1106,1115,1240,1255]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1C828D72CA87" box="[1256,1340,1240,1255]" gridcol="8" gridrow="33" pageId="5" pageNumber="6">H-33, H-41</td>
|
||
<td id="356B472D6F7264BDFAB31C828DF1CA87" box="[1398,1471,1240,1255]" gridcol="9" gridrow="33" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11CB58DF1CA9E" box="[116,1471,1263,1278]" gridrow="34" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11CB588DFCA9E" box="[116,145,1263,1278]" gridcol="0" gridrow="34" pageId="5" pageNumber="6">32</th>
|
||
<td id="356B472D6F7264BDFF0E1CB588B8CA9E" box="[203,246,1263,1278]" gridcol="1" gridrow="34" pageId="5" pageNumber="6">45.2</td>
|
||
<td id="356B472D6F7264BDFEF51CB589A8CA9E" box="[304,486,1263,1278]" gridcol="2" gridrow="34" pageId="5" pageNumber="6">
|
||
2.26 (m, 1H
|
||
<emphasis id="FAFEF0016F729B47FE491CB589DBCA9E" bold="true" box="[396,405,1263,1278]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41CB58A3BCA9E" box="[545,629,1263,1278]" gridcol="3" gridrow="34" pageId="5" pageNumber="6">H-33, H-42</td>
|
||
<td id="356B472D6F7264BDFD6A1CB58B4DCA9E" box="[687,771,1263,1278]" gridcol="4" gridrow="34" pageId="5" pageNumber="6">C-34</td>
|
||
<td id="356B472D6F7264BDFCF81CB58B17CA9E" box="[829,857,1263,1278]" gridcol="5" gridrow="34" pageId="5" pageNumber="6">33</td>
|
||
<td id="356B472D6F7264BDFC571CB58BF3CA9E" box="[914,957,1263,1278]" gridcol="6" gridrow="34" pageId="5" pageNumber="6">24.6</td>
|
||
<td id="356B472D6F7264BDFC321CB58CE3CA9E" box="[1015,1197,1263,1278]" gridcol="7" gridrow="34" pageId="5" pageNumber="6">1.37 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFB2D1CB58D72CA9E" box="[1256,1340,1263,1278]" gridcol="8" gridrow="34" pageId="5" pageNumber="6">H-34</td>
|
||
<td id="356B472D6F7264BDFAB31CB58DF1CA9E" box="[1398,1471,1263,1278]" gridcol="9" gridrow="34" pageId="5" pageNumber="6">C-31</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11D5C8DF1CB74" box="[116,1471,1286,1300]" gridrow="35" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11D5C88DFCB74" box="[116,145,1286,1300]" gridcol="0" gridrow="35" pageId="5" pageNumber="6">33</th>
|
||
<td id="356B472D6F7264BDFF0E1D5C88B8CB74" box="[203,246,1286,1300]" gridcol="1" gridrow="35" pageId="5" pageNumber="6">24.7</td>
|
||
<td id="356B472D6F7264BDFEF51D5C89A8CB74" box="[304,486,1286,1300]" gridcol="2" gridrow="35" pageId="5" pageNumber="6">1.59 (m, 2H)</td>
|
||
<td id="356B472D6F7264BDFDE41D5C8A3BCB74" box="[545,629,1286,1300]" gridcol="3" gridrow="35" pageId="5" pageNumber="6">H-34</td>
|
||
<td id="356B472D6F7264BDFD6A1D5C8B4DCB74" box="[687,771,1286,1300]" gridcol="4" gridrow="35" pageId="5" pageNumber="6">C-31</td>
|
||
<td id="356B472D6F7264BDFCF81D5C8B17CB74" box="[829,857,1286,1300]" gridcol="5" gridrow="35" pageId="5" pageNumber="6">34</td>
|
||
<td id="356B472D6F7264BDFC571D5C8BF3CB74" box="[914,957,1286,1300]" gridcol="6" gridrow="35" pageId="5" pageNumber="6">12.1</td>
|
||
<td id="356B472D6F7264BDFC321D5C8CE3CB74" box="[1015,1197,1286,1300]" gridcol="7" gridrow="35" pageId="5" pageNumber="6">0.96 (t, 3H, 2.5)</td>
|
||
<td id="356B472D6F7264BDFB2D1D5C8D72CB74" box="[1256,1340,1286,1300]" gridcol="8" gridrow="35" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31D5C8DF1CB74" box="[1398,1471,1286,1300]" gridcol="9" gridrow="35" pageId="5" pageNumber="6">C-32</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11D468DF1CB4B" box="[116,1471,1308,1323]" gridrow="36" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11D4688DFCB4B" box="[116,145,1308,1323]" gridcol="0" gridrow="36" pageId="5" pageNumber="6">34</th>
|
||
<td id="356B472D6F7264BDFF0E1D4688B8CB4B" box="[203,246,1308,1323]" gridcol="1" gridrow="36" pageId="5" pageNumber="6">11.3</td>
|
||
<td id="356B472D6F7264BDFEF51D4689A8CB4B" box="[304,486,1308,1323]" gridcol="2" gridrow="36" pageId="5" pageNumber="6">0.94 (t, 3H, 1.5)</td>
|
||
<td id="356B472D6F7264BDFDE41D468A3BCB4B" box="[545,629,1308,1323]" gridcol="3" gridrow="36" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1D468B4DCB4B" box="[687,771,1308,1323]" gridcol="4" gridrow="36" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFCF81D468B17CB4B" box="[829,857,1308,1323]" gridcol="5" gridrow="36" pageId="5" pageNumber="6">35</td>
|
||
<td id="356B472D6F7264BDFC571D468BF3CB4B" box="[914,957,1308,1323]" gridcol="6" gridrow="36" pageId="5" pageNumber="6">23.2</td>
|
||
<td id="356B472D6F7264BDFC321D468CE3CB4B" box="[1015,1197,1308,1323]" gridcol="7" gridrow="36" pageId="5" pageNumber="6">
|
||
1.34 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FB881D468C18CB4B" bold="true" box="[1101,1110,1308,1323]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1D468D72CB4B" box="[1256,1340,1308,1323]" gridcol="8" gridrow="36" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31D468DF1CB4B" box="[1398,1471,1308,1323]" gridcol="9" gridrow="36" pageId="5" pageNumber="6">C-4</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11D688DF1CB22" box="[116,1471,1330,1346]" gridrow="37" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11D6888DFCB22" box="[116,145,1330,1346]" gridcol="0" gridrow="37" pageId="5" pageNumber="6">35</th>
|
||
<td id="356B472D6F7264BDFF0E1D6888B8CB22" box="[203,246,1330,1346]" gridcol="1" gridrow="37" pageId="5" pageNumber="6">23.2</td>
|
||
<td id="356B472D6F7264BDFEF51D6889A8CB22" box="[304,486,1330,1346]" gridcol="2" gridrow="37" pageId="5" pageNumber="6">
|
||
1.35 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FE421D6989DECB22" bold="true" box="[391,400,1331,1346]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41D688A3BCB22" box="[545,629,1330,1346]" gridcol="3" gridrow="37" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1D688B4DCB22" box="[687,771,1330,1346]" gridcol="4" gridrow="37" pageId="5" pageNumber="6">C-4</td>
|
||
<td id="356B472D6F7264BDFCF81D688B17CB22" box="[829,857,1330,1346]" gridcol="5" gridrow="37" pageId="5" pageNumber="6">36</td>
|
||
<td id="356B472D6F7264BDFC571D688BF3CB22" box="[914,957,1330,1346]" gridcol="6" gridrow="37" pageId="5" pageNumber="6">15.8</td>
|
||
<td id="356B472D6F7264BDFC321D688CE3CB22" box="[1015,1197,1330,1346]" gridcol="7" gridrow="37" pageId="5" pageNumber="6">
|
||
0.97 (s, 3H
|
||
<emphasis id="FAFEF0016F729B47FB8E1D688C1ACB22" bold="true" box="[1099,1108,1330,1346]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1D688D72CB22" box="[1256,1340,1330,1346]" gridcol="8" gridrow="37" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31D688DF1CB22" box="[1398,1471,1330,1346]" gridcol="9" gridrow="37" pageId="5" pageNumber="6">C-10</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11D138DF1CB39" box="[116,1471,1353,1369]" gridrow="38" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11D1388DFCB39" box="[116,145,1353,1369]" gridcol="0" gridrow="38" pageId="5" pageNumber="6">36</th>
|
||
<td id="356B472D6F7264BDFF0E1D1388B8CB39" box="[203,246,1353,1369]" gridcol="1" gridrow="38" pageId="5" pageNumber="6">15.9</td>
|
||
<td id="356B472D6F7264BDFEF51D1389A8CB39" box="[304,486,1353,1369]" gridcol="2" gridrow="38" pageId="5" pageNumber="6">
|
||
0.97 (s, 3H
|
||
<emphasis id="FAFEF0016F729B47FE411D1389C3CB39" bold="true" box="[388,397,1353,1369]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41D138A3BCB39" box="[545,629,1353,1369]" gridcol="3" gridrow="38" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1D138B4DCB39" box="[687,771,1353,1369]" gridcol="4" gridrow="38" pageId="5" pageNumber="6">C-10</td>
|
||
<td id="356B472D6F7264BDFCF81D138B17CB39" box="[829,857,1353,1369]" gridcol="5" gridrow="38" pageId="5" pageNumber="6">37</td>
|
||
<td id="356B472D6F7264BDFC571D138BF3CB39" box="[914,957,1353,1369]" gridcol="6" gridrow="38" pageId="5" pageNumber="6">22.7</td>
|
||
<td id="356B472D6F7264BDFC321D138CE3CB39" box="[1015,1197,1353,1369]" gridcol="7" gridrow="38" pageId="5" pageNumber="6">
|
||
1.01 (s, 3H
|
||
<emphasis id="FAFEF0016F729B47FB8E1D108C1ACB39" bold="true" box="[1099,1108,1354,1369]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
, 2.3)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1D138D72CB39" box="[1256,1340,1353,1369]" gridcol="8" gridrow="38" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31D138DF1CB39" box="[1398,1471,1353,1369]" gridcol="9" gridrow="38" pageId="5" pageNumber="6">C-14</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11D3B8DF1CB10" box="[116,1471,1377,1392]" gridrow="39" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11D3B88DFCB10" box="[116,145,1377,1392]" gridcol="0" gridrow="39" pageId="5" pageNumber="6">37</th>
|
||
<td id="356B472D6F7264BDFF0E1D3B88B8CB10" box="[203,246,1377,1392]" gridcol="1" gridrow="39" pageId="5" pageNumber="6">22.5</td>
|
||
<td id="356B472D6F7264BDFEF51D3B89A8CB10" box="[304,486,1377,1392]" gridcol="2" gridrow="39" pageId="5" pageNumber="6">
|
||
1.02 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FE421D3B89DECB10" bold="true" box="[391,400,1377,1392]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
, 2.2)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41D3B8A3BCB10" box="[545,629,1377,1392]" gridcol="3" gridrow="39" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1D3B8B4DCB10" box="[687,771,1377,1392]" gridcol="4" gridrow="39" pageId="5" pageNumber="6">C-14</td>
|
||
<td id="356B472D6F7264BDFCF81D3B8B17CB10" box="[829,857,1377,1392]" gridcol="5" gridrow="39" pageId="5" pageNumber="6">38</td>
|
||
<td id="356B472D6F7264BDFC571D3B8BF3CB10" box="[914,957,1377,1392]" gridcol="6" gridrow="39" pageId="5" pageNumber="6">16.6</td>
|
||
<td id="356B472D6F7264BDFC321D3B8CE3CB10" box="[1015,1197,1377,1392]" gridcol="7" gridrow="39" pageId="5" pageNumber="6">
|
||
1.00 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FB881D3B8C18CB10" bold="true" box="[1101,1110,1377,1392]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
, 2.3)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1D3B8D72CB10" box="[1256,1340,1377,1392]" gridcol="8" gridrow="39" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31D3B8DF1CB10" box="[1398,1471,1377,1392]" gridcol="9" gridrow="39" pageId="5" pageNumber="6">C-18</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11D228DF1CBE7" box="[116,1471,1400,1415]" gridrow="40" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11D2288DFCBE7" box="[116,145,1400,1415]" gridcol="0" gridrow="40" pageId="5" pageNumber="6">38</th>
|
||
<td id="356B472D6F7264BDFF0E1D2288B8CBE7" box="[203,246,1400,1415]" gridcol="1" gridrow="40" pageId="5" pageNumber="6">17.5</td>
|
||
<td id="356B472D6F7264BDFEF51D2289A8CBE7" box="[304,486,1400,1415]" gridcol="2" gridrow="40" pageId="5" pageNumber="6">
|
||
0.99 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FE421D2289DECBE7" bold="true" box="[391,400,1400,1415]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
, 2.6)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41D228A3BCBE7" box="[545,629,1400,1415]" gridcol="3" gridrow="40" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1D228B4DCBE7" box="[687,771,1400,1415]" gridcol="4" gridrow="40" pageId="5" pageNumber="6">C-18</td>
|
||
<td id="356B472D6F7264BDFCF81D228B17CBE7" box="[829,857,1400,1415]" gridcol="5" gridrow="40" pageId="5" pageNumber="6">39</td>
|
||
<td id="356B472D6F7264BDFC571D228BF3CBE7" box="[914,957,1400,1415]" gridcol="6" gridrow="40" pageId="5" pageNumber="6">15.3</td>
|
||
<td id="356B472D6F7264BDFC321D228CE3CBE7" box="[1015,1197,1400,1415]" gridcol="7" gridrow="40" pageId="5" pageNumber="6">
|
||
0.93 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FB881D228C18CBE7" bold="true" box="[1101,1110,1400,1415]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
, 1.4)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1D228D72CBE7" box="[1256,1340,1400,1415]" gridcol="8" gridrow="40" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31D228DF1CBE7" box="[1398,1471,1400,1415]" gridcol="9" gridrow="40" pageId="5" pageNumber="6">C-22, 23</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11DD78DF1CBFE" box="[116,1471,1421,1438]" gridrow="41" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11DD788DFCBFE" box="[116,145,1421,1438]" gridcol="0" gridrow="41" pageId="5" pageNumber="6">39</th>
|
||
<td id="356B472D6F7264BDFF0E1DD788B8CBFE" box="[203,246,1421,1438]" gridcol="1" gridrow="41" pageId="5" pageNumber="6">12.0</td>
|
||
<td id="356B472D6F7264BDFEF51DD789A8CBFE" box="[304,486,1421,1438]" gridcol="2" gridrow="41" pageId="5" pageNumber="6">
|
||
0.91 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FE421DD589DECBFE" bold="true" box="[391,400,1423,1438]" italics="true" pageId="5" pageNumber="6">β</emphasis>
|
||
, 1.4)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41DD78A3BCBFE" box="[545,629,1421,1438]" gridcol="3" gridrow="41" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1DD78B4DCBFE" box="[687,771,1421,1438]" gridcol="4" gridrow="41" pageId="5" pageNumber="6">C-22, 23</td>
|
||
<td id="356B472D6F7264BDFCF81DD78B17CBFE" box="[829,857,1421,1438]" gridcol="5" gridrow="41" pageId="5" pageNumber="6">40</td>
|
||
<td id="356B472D6F7264BDFC571DD78BF3CBFE" box="[914,957,1421,1438]" gridcol="6" gridrow="41" pageId="5" pageNumber="6">21.3</td>
|
||
<td id="356B472D6F7264BDFC321DD78CE3CBFE" box="[1015,1197,1421,1438]" gridcol="7" gridrow="41" pageId="5" pageNumber="6">
|
||
0.92 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FB8B1DD78C19CBFD" bold="true" box="[1102,1111,1421,1437]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
, 1.4)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1DD78D72CBFE" box="[1256,1340,1421,1438]" gridcol="8" gridrow="41" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31DD78DF1CBFE" box="[1398,1471,1421,1438]" gridcol="9" gridrow="41" pageId="5" pageNumber="6">C-24</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11DFE8DF1CBD4" box="[116,1471,1444,1460]" gridrow="42" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11DFE88DFCBD4" box="[116,145,1444,1460]" gridcol="0" gridrow="42" pageId="5" pageNumber="6">40</th>
|
||
<td id="356B472D6F7264BDFF0E1DFE88B8CBD4" box="[203,246,1444,1460]" gridcol="1" gridrow="42" pageId="5" pageNumber="6">21.2</td>
|
||
<td id="356B472D6F7264BDFEF51DFE89A8CBD4" box="[304,486,1444,1460]" gridcol="2" gridrow="42" pageId="5" pageNumber="6">
|
||
0.89 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FE421DFE89DECBD4" bold="true" box="[391,400,1444,1460]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
, 1.6)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41DFE8A3BCBD4" box="[545,629,1444,1460]" gridcol="3" gridrow="42" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1DFE8B4DCBD4" box="[687,771,1444,1460]" gridcol="4" gridrow="42" pageId="5" pageNumber="6">C-24</td>
|
||
<td id="356B472D6F7264BDFCF81DFE8B17CBD4" box="[829,857,1444,1460]" gridcol="5" gridrow="42" pageId="5" pageNumber="6">41</td>
|
||
<td id="356B472D6F7264BDFC571DFE8BF3CBD4" box="[914,957,1444,1460]" gridcol="6" gridrow="42" pageId="5" pageNumber="6">16.1</td>
|
||
<td id="356B472D6F7264BDFC321DFE8CE3CBD4" box="[1015,1197,1444,1460]" gridcol="7" gridrow="42" pageId="5" pageNumber="6">
|
||
0.91 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FB8B1DFE8C19CBD4" bold="true" box="[1102,1111,1444,1460]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
, 2.1)
|
||
</td>
|
||
<td id="356B472D6F7264BDFB2D1DFE8D72CBD4" box="[1256,1340,1444,1460]" gridcol="8" gridrow="42" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31DFE8DF1CBD4" box="[1398,1471,1444,1460]" gridcol="9" gridrow="42" pageId="5" pageNumber="6">C-32</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11DE78DF1CBAB" box="[116,1471,1469,1483]" gridrow="43" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11DE788DFCBAB" box="[116,145,1469,1483]" gridcol="0" gridrow="43" pageId="5" pageNumber="6">41</th>
|
||
<td id="356B472D6F7264BDFF0E1DE788B8CBAB" box="[203,246,1469,1483]" gridcol="1" gridrow="43" pageId="5" pageNumber="6">68.5</td>
|
||
<td id="356B472D6F7264BDFEF51DE789A8CBAB" box="[304,486,1469,1483]" gridcol="2" gridrow="43" pageId="5" pageNumber="6">4.21 (s, 2H)</td>
|
||
<td id="356B472D6F7264BDFDE41DE78A3BCBAB" box="[545,629,1469,1483]" gridcol="3" gridrow="43" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1DE78B4DCBAB" box="[687,771,1469,1483]" gridcol="4" gridrow="43" pageId="5" pageNumber="6">C-28</td>
|
||
<td id="356B472D6F7264BDFCF81DE78B17CBAB" box="[829,857,1469,1483]" gridcol="5" gridrow="43" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFC571DE78BF3CBAB" box="[914,957,1469,1483]" gridcol="6" gridrow="43" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFC321DE78CE3CBAB" box="[1015,1197,1469,1483]" gridcol="7" gridrow="43" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFB2D1DE78D72CBAB" box="[1256,1340,1469,1483]" gridcol="8" gridrow="43" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31DE78DF1CBAB" box="[1398,1471,1469,1483]" gridcol="9" gridrow="43" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7264BDFFB11D888DF1CB82" box="[116,1471,1490,1506]" gridrow="44" pageId="5" pageNumber="6">
|
||
<th id="356B472D6F7264BDFFB11D8888DFCB82" box="[116,145,1490,1506]" gridcol="0" gridrow="44" pageId="5" pageNumber="6">42</th>
|
||
<td id="356B472D6F7264BDFF0E1D8888B8CB82" box="[203,246,1490,1506]" gridcol="1" gridrow="44" pageId="5" pageNumber="6">16.1</td>
|
||
<td id="356B472D6F7264BDFEF51D8889A8CB82" box="[304,486,1490,1506]" gridcol="2" gridrow="44" pageId="5" pageNumber="6">
|
||
0.83 (d, 3H
|
||
<emphasis id="FAFEF0016F729B47FE421D8889DECB82" bold="true" box="[391,400,1490,1506]" italics="true" pageId="5" pageNumber="6">α</emphasis>
|
||
, 2.2)
|
||
</td>
|
||
<td id="356B472D6F7264BDFDE41D888A3BCB82" box="[545,629,1490,1506]" gridcol="3" gridrow="44" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFD6A1D888B4DCB82" box="[687,771,1490,1506]" gridcol="4" gridrow="44" pageId="5" pageNumber="6">C-32</td>
|
||
<td id="356B472D6F7264BDFCF81D888B17CB82" box="[829,857,1490,1506]" gridcol="5" gridrow="44" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFC571D888BF3CB82" box="[914,957,1490,1506]" gridcol="6" gridrow="44" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFC321D888CE3CB82" box="[1015,1197,1490,1506]" gridcol="7" gridrow="44" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFB2D1D888D72CB82" box="[1256,1340,1490,1506]" gridcol="8" gridrow="44" pageId="5" pageNumber="6">–</td>
|
||
<td id="356B472D6F7264BDFAB31D888DF1CB82" box="[1398,1471,1490,1506]" gridcol="9" gridrow="44" pageId="5" pageNumber="6">–</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F729B47FFA11E6B8C6BC8D4" blockId="5.[100,770,1585,1968]" lastBlockId="5.[818,1487,1585,1716]" pageId="5" pageNumber="6">
|
||
(chloramphenicol and ampicillin with a range of MIC values from 6.25 to 12.5 μg/mL) and
|
||
<emphasis id="FAFEF0016F729B47FEF71E178970C800" bold="true" box="[306,318,1613,1632]" pageId="5" pageNumber="6">1</emphasis>
|
||
,
|
||
<emphasis id="FAFEF0016F729B47FE8B1E178914C800" bold="true" box="[334,346,1613,1632]" pageId="5" pageNumber="6">2</emphasis>
|
||
and
|
||
<emphasis id="FAFEF0016F729B47FE541E1789D3C800" bold="true" box="[401,413,1613,1632]" pageId="5" pageNumber="6">4</emphasis>
|
||
(MRSA/
|
||
<emphasis id="FAFEF0016F729B47FE311E178B4FC800" bold="true" box="[500,769,1613,1632]" italics="true" pageId="5" pageNumber="6">
|
||
<taxonomicName id="0F8A57906F729B47FE311E178A30C800" authorityName="Trevisan" authorityYear="1887" baseAuthorityName="Schroeter" baseAuthorityYear="1886" box="[500,638,1613,1632]" class="Gammaproteobacteria" family="Enterobacteriaceae" genus="Klebsiella" kingdom="Bacteria" order="Enterobacteriales" pageId="5" pageNumber="6" phylum="Proteobacteria" rank="species" species="pneumoniae">K. pneumoniae</taxonomicName>
|
||
/
|
||
<taxonomicName id="0F8A57906F729B47FD421E178B4FC800" authorityName="Migula" authorityYear="1900" baseAuthorityName="Schroeter" baseAuthorityYear="1872" box="[647,769,1613,1632]" class="Betaproteobacteria" family="Burkholderiaceae" genus="Pseudomonas" kingdom="Bacteria" order="Burkholderiales" pageId="5" pageNumber="6" phylum="Proteobacteria" rank="species" species="aeruginosa">P. aeruginosa</taxonomicName>
|
||
</emphasis>
|
||
3.12–6.25 μg/mL, VRE
|
||
<emphasis id="FAFEF0016F729B47FEFE1E338904C81C" bold="true" box="[315,330,1641,1660]" italics="true" pageId="5" pageNumber="6">fs</emphasis>
|
||
6.25 μg/mL). These results could infer greater antibacterial property of
|
||
<emphasis id="FAFEF0016F729B47FE8B1EDF8914C8F8" bold="true" box="[334,346,1669,1688]" pageId="5" pageNumber="6">3</emphasis>
|
||
when compared to the commercial standards and other studied compounds. Electronic parameters of titled macrobrevin analogues were found to play a significant role to effect greater bioactive potential. Herein, the electronic parameter, such as polarizability (Pl) of macrobrevin analogues
|
||
<emphasis id="FAFEF0016F729B47FE0E1EAF89A0C968" bold="true" box="[459,494,1781,1800]" pageId="5" pageNumber="6">1–4</emphasis>
|
||
were higher (76–84 × 10
|
||
<quantity id="0F7281F66F729B47FD351EB588CEC944" metricMagnitude="-1" metricUnit="m" metricValue="2.4" pageId="5" pageNumber="6" unit="cm" value="24.0">
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<superScript id="3FFF815B6F729B47FD351EB58B4CC89D" attach="right" box="[752,770,1775,1789]" fontSize="6" pageId="5" pageNumber="6">24</superScript>
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cm
|
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</quantity>
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<superScript id="3FFF815B6F729B47FF451F5188C7C979" attach="left" box="[128,137,1803,1817]" fontSize="6" pageId="5" pageNumber="6">3</superScript>
|
||
) than that of standard antibiotic, chloramphenicol (28.76 × 10
|
||
<quantity id="0F7281F66F729B47FD351F5188CEC920" metricMagnitude="-1" metricUnit="m" metricValue="2.4" pageId="5" pageNumber="6" unit="cm" value="24.0">
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<superScript id="3FFF815B6F729B47FD351F518B4CC979" attach="right" box="[752,770,1803,1817]" fontSize="6" pageId="5" pageNumber="6">24</superScript>
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cm
|
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</quantity>
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<superScript id="3FFF815B6F729B47FF451F7D88C7C955" attach="left" box="[128,137,1831,1845]" fontSize="6" pageId="5" pageNumber="6">3</superScript>
|
||
). Also, the electronic parameter as determined by total polar surface area (tPSA) of macrobrevin analogues
|
||
<emphasis id="FAFEF0016F729B47FE031F12899CC93B" bold="true" box="[454,466,1864,1883]" pageId="5" pageNumber="6">1</emphasis>
|
||
and
|
||
<emphasis id="FAFEF0016F729B47FE3B1F128A44C93B" bold="true" box="[510,522,1864,1883]" pageId="5" pageNumber="6">3</emphasis>
|
||
were greater (107–167) as compared to those of chloramphenicol (115.38) and other compounds in the series. In particular, higher electronic values of macrobrevin analogue
|
||
<emphasis id="FAFEF0016F729B47FF051FC68882C9CF" bold="true" box="[192,204,1948,1967]" pageId="5" pageNumber="6">3</emphasis>
|
||
were caused by the presence of greater number of electron-rich centres, including hydroxyls (four in numbers), two ester functionalities and non-conjugated/conjugated dienes. These results demonstrated the correlation among electronegative groups and higher
|
||
<emphasis id="FAFEF0016F729B47FCF71EDF8B3DC8F8" bold="true" box="[818,883,1669,1688]" italics="true" pageId="5" pageNumber="6">in vitro</emphasis>
|
||
antibacterial property of
|
||
<emphasis id="FAFEF0016F729B47FBAC1EDF8C3BC8F8" bold="true" box="[1129,1141,1669,1688]" pageId="5" pageNumber="6">3</emphasis>
|
||
compared to other macrobrevin analogues and the standard.
|
||
</paragraph>
|
||
<paragraph id="C8352C136F729B47FCF71EBD8C2DC976" blockId="5.[818,1471,1767,1787]" lastBlockId="5.[818,1123,1795,1814]" pageId="5" pageNumber="6">
|
||
<emphasis id="FAFEF0016F729B47FCF71EBD8C2DC976" bold="true" italics="true" pageId="5" pageNumber="6">
|
||
<heading id="937D9B7F6F729B47FCF71EBD8DF1C89A" bold="true" box="[818,1471,1767,1787]" centered="true" fontSize="36" level="1" pageId="5" pageNumber="6" reason="1">2.5. Core biosynthetic gene cluster associated with macrobrevin analogues</heading>
|
||
<heading id="937D9B7F6F729B47FCF71F598C2DC976" box="[818,1123,1795,1814]" fontSize="8" level="3" pageId="5" pageNumber="6" reason="8">and putative biosynthetic pathway</heading>
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F729B44FC941F61898DCB17" blockId="5.[818,1488,1851,1982]" lastBlockId="6.[100,771,655,1957]" lastPageId="6" lastPageNumber="7" pageId="5" pageNumber="6">
|
||
Of late, improvements to characterize the bacterial BGCs have revolutionized the dimensions to comprehend their capacities to produce antibacterial specialized metabolites. Recently, substantial efforts have been directed to relate the genomic information of bacteria to those of the specialized metabolites produced by those (
|
||
<bibRefCitation id="AC1B51E26F729B47FAC41FF18D8FC9DE" author="Soldatou, S. & Eldjarn, G. H. & Huerta-Uribe, A. & Rogers, S. & Duncan, K. R." box="[1281,1473,1963,1982]" pageId="5" pageNumber="6" pagination="142" refId="ref17331" refString="Soldatou, S., Eldjarn, G. H., Huerta-Uribe, A., Rogers, S., Duncan, K. R., 2019. Linking biosynthetic and chemical space to accelerate microbial secondary metabolite discovery. FEMS Microbiol. Lett. 366 (13), fnz 142. https: // doi. org / 10.1093 / femsle / fnz 142." type="journal article" year="2019">Soldatou et al., 2019</bibRefCitation>
|
||
). In the genome mining study, among the 34 biosynthetic gene clusters, a hybrid
|
||
<emphasis id="FAFEF0016F719B44FF6C1AF18898CCDE" bold="true" box="[169,214,683,702]" italics="true" pageId="6" pageNumber="7">trans</emphasis>
|
||
-acyltransferase (
|
||
<emphasis id="FAFEF0016F719B44FEB21AF189EACCDE" bold="true" box="[375,420,683,702]" italics="true" pageId="6" pageNumber="7">trans</emphasis>
|
||
-AT)
|
||
<emphasis id="FAFEF0016F719B44FE111AF08A6CCCDD" bold="true" box="[468,546,682,701]" italics="true" pageId="6" pageNumber="7">pks/nrps</emphasis>
|
||
gene cluster, which extends up to ~81 Kb, was recognized in the genome of
|
||
<taxonomicName id="0F8A57906F719B44FFA11AB9892DCC95" authority="MTCC" authorityName="MTCC" box="[100,355,738,758]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="amyloliquefaciens">
|
||
<emphasis id="FAFEF0016F719B44FFA11AB98951CC95" bold="true" box="[100,287,738,758]" italics="true" pageId="6" pageNumber="7">B. amyloliquefaciens</emphasis>
|
||
MTCC
|
||
</taxonomicName>
|
||
12713 (
|
||
<figureCitation id="50B130966F719B44FE7F1AB889BCCC95" box="[442,498,738,757]" captionStart="Fig" captionStartId="7.[100,130,937,954]" captionTargetBox="[228,1345,149,907]" captionTargetId="figure-266@7.[225,1362,148,909]" captionTargetPageId="7" captionText="Fig. 3. (A) Biosynthetic gene cluster coding for biosynthesis of macrobrevin analogues in B. amyloliquefaciens showing 46% similarity with macrobrevin biosynthetic gene cluster BGC0001470 (as elucidated by Known-Cluster-Blast prediction, the gene cluster also had 32% similarity with aurantinine and bacillaene with 100% similarity), (B) organization of genes in macrobrevin biosynthetic gene cluster of Brevibacillus sp. (C) Domain organization of the modules of trans-AT PKS gene cluster coding for bacillaene, which is 46% similar to macrobrevin biosynthetic gene cluster is shown. (D) The proposed functions of genes (1–16) contained in the biosynthetic gene cluster has been listed out, and are described as: (1) Biosynthetic additional (smcogs) SMCOG1170: metallo-β-lactamase family protein (score: 203; E-value: 5.4e-62); (2) biosynthetic trans-AT-PKS:PKS_AT biosynthetic additional SMCOG1021: malonyl CoA-acyl carrier protein transacylase (score: 400.8; E-value: 1.8e-121); (3) biosynthetic trans AT-PKS:PKS_AT biosynthetic additional SMCOG1021: malonyl CoA-acyl carrier protein transacylase (score: 232.8; E-value: 1.5e-70); (4) biosynthetic trans-AT-PKS:PKS_AT biosynthetic additional SMCOG1021:malonyl CoA-acyl carrier protein transacylase (score: 481.1; E-value: 9e-146); (5) biosynthetic additional PP-binding; (6) biosynthetic T3PKS:Chal_sti_synt_N biosynthetic additional SMCOG1043:hydroxymethylglutaryl-CoA synthase (score: 496.9; E-value: 6.5e-151); (7) biosynthetic additional SMCOG1023: enoyl-CoA hydratase (score: 228.4; E-value: 1.3e-69); (8) biosynthetic trans-AT-PKS:PP-binding biosynthetic trans-AT-PKS:tra_KS-biosynthetic trans AT-PKS:ATd-biosynthetic NRPS:AMP-binding biosynthetic-NRPS: condensation biosynthetic additional adh_short biosynthetic additional SMCOG1127: condensation domain-containing protein (score: 295.3; E-value: 1.6e-89); (9) biosynthetic additional-tra_KS biosyntheticadditional SMCOG1022: β-ketoacyl synthase (score: 160.9; E-value: 8.3e-49); (10) biosynthetic-trans-AT-PKS:PP-binding-biosynthetic-trans-AT-PKS:tra_KS-biosynthetic-trans-AT-KS:ATd-biosynthetic-additional-adh_short-biosynthetic-additional-SMCOG1001:short-chain-dehydrogenase/reductase SDR (score: 48.7; E-value: 1.2e-14); (11) biosynthetic-trans-AT-PKS:PP-binding-biosynthetic-trans-AT-PKS:tra_KS-biosynthetic-trans-AT-PKS:ATd-biosynthetic-additional-adh_short-biosynthetic-additional SMCOG1093: β-ketoacyl synthase (score: 73.2; E-value: 2.8e-22); (12) biosynthetic trans AT-PKS: PP-binding-biosynthetic-trans-AT-PKS:tra_KSbiosynthetic-trans-AT-PKS:ATd-biosynthetic-additional-adh biosynthetic-additional SMCOG1022: β-ketoacyl synthase (score: 222.6; E-value: 1.5e-67); (13) biosynthetic-additional-condensation biosynthetic-additional SMCOG1127:condensation domain-containing protein (score: 196.8; E-value: 1.3e-59); (14) biosynthetic-trans-AT-PKS:PP-binding-biosynthetic-trans-AT-PKS:tra_KS-biosynthetic-trans-AT-PKS:ATd-biosynthetic-NRPS-like:AMP-binding-biosynthetic-NRPS-like:PPbinding-biosynthetic-additional adh_short-biosynthetic-additional SMCOG1002: AMP-dependent synthetase and ligase (score: 373.7; E-value: 1.9e-113); (15) biosynthetic-additional-PP-binding-biosynthetic-additional-tra_KS-biosynthetic-additional MCOG1022: β-ketoacyl (score: 73.2; E-value: 2.8e-22); (16) biosynthetictrans-AT-PKS-like:tra_KS-biosynthetic-trans-AT-PKS-like:ATd-biosynthetic-additional-PP-binding-biosynthetic-additional SMCOG1022: β-ketoacyl synthase (score: 207.7; E-value: 5.1e-63)." figureDoi="http://doi.org/10.5281/zenodo.8235157" httpUri="https://zenodo.org/record/8235157/files/figure.png" pageId="6" pageNumber="7">Fig. 3</figureCitation>
|
||
). The
|
||
<emphasis id="FAFEF0016F719B44FDF21AB88ACACC95" bold="true" box="[567,644,738,757]" italics="true" pageId="6" pageNumber="7">pks/nrps</emphasis>
|
||
gene cluster disclosed 46% similarity to
|
||
<emphasis id="FAFEF0016F719B44FEA91AA489D7CD71" bold="true" box="[364,409,766,785]" italics="true" pageId="6" pageNumber="7">trans</emphasis>
|
||
-AT PKS-derived macrobrevin isolated from a mesophilic bacterium
|
||
<taxonomicName id="0F8A57906F719B44FE441B408A5ACD4E" box="[385,532,794,814]" class="Bacilli" family="Paenibacillaceae" genus="Brevibacillus" kingdom="Bacteria" order="Bacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="undetermined">
|
||
<emphasis id="FAFEF0016F719B44FE441B4089BFCD4D" bold="true" box="[385,497,794,813]" italics="true" pageId="6" pageNumber="7">Brevibacillus</emphasis>
|
||
sp.
|
||
</taxonomicName>
|
||
Leaf182 associated with the phyllosphere of the wild-type genotype of
|
||
<taxonomicName id="0F8A57906F719B44FD801B6C8B4FCD29" box="[581,769,822,841]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="6" pageNumber="7" phylum="Tracheophyta" rank="species" species="thaliana">
|
||
<emphasis id="FAFEF0016F719B44FD801B6C8B4FCD29" bold="true" box="[581,769,822,841]" italics="true" pageId="6" pageNumber="7">Arabidopsis thaliana</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<bibRefCitation id="AC1B51E26F719B44FFA91B088908CD05" author="Helfrich, E. J. N. & Vogel, C. M. & Ueoka, R. & Ryffel, F. & Muller, D. B. & Probst, S. & Kreuzer, M. & Piel, J. & Vorholt, J. A." box="[108,326,850,869]" pageId="6" pageNumber="7" pagination="909 - 919" refId="ref16029" refString="Helfrich, E. J. N., Vogel, C. M., Ueoka, R., Sch ¨ afer, M., Ryffel, F., Muller, D. B., Probst, S., Kreuzer, M., Piel, J., Vorholt, J. A., 2018. Bipartite interactions, antibiotic production and biosynthetic potential of the Arabidopsis leaf microbiome. Nat. Microbiol. 3 (8), 909 - 919. https: // doi. org / 10.1038 / s 41564 - 018 - 0200 - 0." type="journal article" year="2018">Helfrich et al., 2018</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="AC1B51E26F719B44FE9E1B088A75CD05" author="Soldatou, S. & Eldjarn, G. H. & Huerta-Uribe, A. & Rogers, S. & Duncan, K. R." box="[347,571,850,869]" pageId="6" pageNumber="7" pagination="142" refId="ref17331" refString="Soldatou, S., Eldjarn, G. H., Huerta-Uribe, A., Rogers, S., Duncan, K. R., 2019. Linking biosynthetic and chemical space to accelerate microbial secondary metabolite discovery. FEMS Microbiol. Lett. 366 (13), fnz 142. https: // doi. org / 10.1093 / femsle / fnz 142." type="journal article" year="2019">Soldatou et al., 2019</bibRefCitation>
|
||
). Furthermore, the “known-cluster-blast” was utilized to classify prospective products for the genetic clusters from MI-BiG database. Whole genome sequence of the candidate bacterium was submitted in the GenBank with an accession number of QKQQ00000000 (Supplementary material
|
||
<collectionCode id="AE9BB4D66F719B44FD4B1B988AD5CDB5" box="[654,667,962,981]" country="Sweden" lsid="urn:lsid:biocol.org:col:15668" name="Department of Botany, Swedish Museum of Natural History" pageId="6" pageNumber="7" type="Herbarium">S</collectionCode>
|
||
4). Though the BGC in the genome showed 100% similarity to the bacillaene gene cluster, the metabolic products were turned out to be the derivatives of macrobrevin. Most convincing answer for this switching over of metabolite production is that many specialized metabolite BGCs or individual genes in BGCs are expressed poorly, or not at all, under the laboratory growth conditions owing to their tight control (at the levels of transcription and/or translation) in response to either direct or indirect environmental signals (
|
||
<bibRefCitation id="AC1B51E26F719B44FE851CFB899DCAD4" author="Brakhage, A. A." box="[320,467,1185,1204]" pageId="6" pageNumber="7" pagination="21 - 32" refId="ref15182" refString="Brakhage, A. A., 2013. Regulation of fungal secondary metabolism. Nat. Rev. Microbiol. 11 (1), 21 - 32. https: // doi. org / 10.1038 / nrmicro 2916." type="journal article" year="2013">Brakhage, 2013</bibRefCitation>
|
||
). It was also reported that when microorganisms were grown in pure culture
|
||
<emphasis id="FAFEF0016F719B44FDCA1CE68A1FCAAF" bold="true" box="[527,593,1212,1231]" italics="true" pageId="6" pageNumber="7">in vitro</emphasis>
|
||
, many of the activating signals were presumably absent, and the expression of specialized metabolite BGCs or any regulatory gene was thus down regulated (
|
||
<bibRefCitation id="AC1B51E26F719B44FD0C1CAE897DCB43" author="van Wezel, G. P. & McDowall, K. J." pageId="6" pageNumber="7" pagination="1311 - 1333" refId="ref17595" refString="van Wezel, G. P., McDowall, K. J., 2011. The regulation of the secondary metabolism of Streptomyces: new links and experimental advances. Nat. Prod. Rep. 28 (7), 1311 - 1333. https: // doi. org / 10.1039 / c 1 np 00003 a." type="journal article" year="2011">Wezel and McDowall, 2011</bibRefCitation>
|
||
). It was reported that the elansolids are biosynthesized by
|
||
<emphasis id="FAFEF0016F719B44FF331D76896DCB5F" bold="true" box="[246,291,1324,1343]" italics="true" pageId="6" pageNumber="7">trans</emphasis>
|
||
-AT polyketide synthase of type-1
|
||
<emphasis id="FAFEF0016F719B44FDAD1D768ACBCB5F" bold="true" box="[616,645,1324,1343]" italics="true" pageId="6" pageNumber="7">pks</emphasis>
|
||
(
|
||
<bibRefCitation id="AC1B51E26F719B44FD511D768ABACB5F" author="Piel, J." box="[660,756,1324,1343]" pageId="6" pageNumber="7" pagination="996 - 1047" refId="ref17094" refString="Piel, J., 2010. Biosynthesis of polyketides by trans-AT polyketide synthases. Nat. Prod. Rep. 27 (7), 996 - 1047. https: // doi. org / 10.1039 / b 816430 b." type="journal article" year="2010">Piel, 2010</bibRefCitation>
|
||
). The proposed functions of genes (1–16) contained in the biosynthetic gene cluster were listed out in
|
||
<figureCitation id="50B130966F719B44FE421D3E89F3CB17" box="[391,445,1380,1399]" captionStart="Fig" captionStartId="7.[100,130,937,954]" captionTargetBox="[228,1345,149,907]" captionTargetId="figure-266@7.[225,1362,148,909]" captionTargetPageId="7" captionText="Fig. 3. (A) Biosynthetic gene cluster coding for biosynthesis of macrobrevin analogues in B. amyloliquefaciens showing 46% similarity with macrobrevin biosynthetic gene cluster BGC0001470 (as elucidated by Known-Cluster-Blast prediction, the gene cluster also had 32% similarity with aurantinine and bacillaene with 100% similarity), (B) organization of genes in macrobrevin biosynthetic gene cluster of Brevibacillus sp. (C) Domain organization of the modules of trans-AT PKS gene cluster coding for bacillaene, which is 46% similar to macrobrevin biosynthetic gene cluster is shown. (D) The proposed functions of genes (1–16) contained in the biosynthetic gene cluster has been listed out, and are described as: (1) Biosynthetic additional (smcogs) SMCOG1170: metallo-β-lactamase family protein (score: 203; E-value: 5.4e-62); (2) biosynthetic trans-AT-PKS:PKS_AT biosynthetic additional SMCOG1021: malonyl CoA-acyl carrier protein transacylase (score: 400.8; E-value: 1.8e-121); (3) biosynthetic trans AT-PKS:PKS_AT biosynthetic additional SMCOG1021: malonyl CoA-acyl carrier protein transacylase (score: 232.8; E-value: 1.5e-70); (4) biosynthetic trans-AT-PKS:PKS_AT biosynthetic additional SMCOG1021:malonyl CoA-acyl carrier protein transacylase (score: 481.1; E-value: 9e-146); (5) biosynthetic additional PP-binding; (6) biosynthetic T3PKS:Chal_sti_synt_N biosynthetic additional SMCOG1043:hydroxymethylglutaryl-CoA synthase (score: 496.9; E-value: 6.5e-151); (7) biosynthetic additional SMCOG1023: enoyl-CoA hydratase (score: 228.4; E-value: 1.3e-69); (8) biosynthetic trans-AT-PKS:PP-binding biosynthetic trans-AT-PKS:tra_KS-biosynthetic trans AT-PKS:ATd-biosynthetic NRPS:AMP-binding biosynthetic-NRPS: condensation biosynthetic additional adh_short biosynthetic additional SMCOG1127: condensation domain-containing protein (score: 295.3; E-value: 1.6e-89); (9) biosynthetic additional-tra_KS biosyntheticadditional SMCOG1022: β-ketoacyl synthase (score: 160.9; E-value: 8.3e-49); (10) biosynthetic-trans-AT-PKS:PP-binding-biosynthetic-trans-AT-PKS:tra_KS-biosynthetic-trans-AT-KS:ATd-biosynthetic-additional-adh_short-biosynthetic-additional-SMCOG1001:short-chain-dehydrogenase/reductase SDR (score: 48.7; E-value: 1.2e-14); (11) biosynthetic-trans-AT-PKS:PP-binding-biosynthetic-trans-AT-PKS:tra_KS-biosynthetic-trans-AT-PKS:ATd-biosynthetic-additional-adh_short-biosynthetic-additional SMCOG1093: β-ketoacyl synthase (score: 73.2; E-value: 2.8e-22); (12) biosynthetic trans AT-PKS: PP-binding-biosynthetic-trans-AT-PKS:tra_KSbiosynthetic-trans-AT-PKS:ATd-biosynthetic-additional-adh biosynthetic-additional SMCOG1022: β-ketoacyl synthase (score: 222.6; E-value: 1.5e-67); (13) biosynthetic-additional-condensation biosynthetic-additional SMCOG1127:condensation domain-containing protein (score: 196.8; E-value: 1.3e-59); (14) biosynthetic-trans-AT-PKS:PP-binding-biosynthetic-trans-AT-PKS:tra_KS-biosynthetic-trans-AT-PKS:ATd-biosynthetic-NRPS-like:AMP-binding-biosynthetic-NRPS-like:PPbinding-biosynthetic-additional adh_short-biosynthetic-additional SMCOG1002: AMP-dependent synthetase and ligase (score: 373.7; E-value: 1.9e-113); (15) biosynthetic-additional-PP-binding-biosynthetic-additional-tra_KS-biosynthetic-additional MCOG1022: β-ketoacyl (score: 73.2; E-value: 2.8e-22); (16) biosynthetictrans-AT-PKS-like:tra_KS-biosynthetic-trans-AT-PKS-like:ATd-biosynthetic-additional-PP-binding-biosynthetic-additional SMCOG1022: β-ketoacyl synthase (score: 207.7; E-value: 5.1e-63)." figureDoi="http://doi.org/10.5281/zenodo.8235157" httpUri="https://zenodo.org/record/8235157/files/figure.png" pageId="6" pageNumber="7">Fig. 3</figureCitation>
|
||
.
|
||
</paragraph>
|
||
<caption id="9CF57C9B6F719B44FFA118CC8BB9CEA1" ID-Table-UUID="9CF57C9B6F719B44FFA118CC8BB9CEA1" httpUri="http://table.plazi.org/id/9CF57C9B6F719B44FFA118CC8BB9CEA1" pageId="6" pageNumber="7" startId="6.[100,150,150,166]" targetBox="[116,1471,213,422]" targetIsTable="true" targetPageId="6" targetType="table">
|
||
<paragraph id="C8352C136F719B44FFA118CC88E9CEC7" blockId="6.[100,1015,150,193]" box="[100,167,150,167]" pageId="6" pageNumber="7">
|
||
<emphasis id="FAFEF0016F719B44FFA118CC88E9CEC7" bold="true" box="[100,167,150,167]" pageId="6" pageNumber="7">Table 2</emphasis>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F719B44FFA118EA8BB9CEA1" blockId="6.[100,1015,150,193]" box="[100,1015,176,193]" pageId="6" pageNumber="7">
|
||
Antibacterial activities of macrobrevin analogues
|
||
<emphasis id="FAFEF0016F719B44FDCE18EA8A65CEA1" bold="true" box="[523,555,176,193]" pageId="6" pageNumber="7">1–4</emphasis>
|
||
and commercial standards against clinical pathogens.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="C8352C136F719B44FFB1188F8DFBCFC6" pageId="6" pageNumber="7">
|
||
<table id="BA8ADEB36F7164BDFFB1188F8DF1CFC6" box="[116,1471,213,422]" gridcols="7" gridrows="9" pageId="6" pageNumber="7">
|
||
<tr id="76BA2E516F7164BDFFB1188F8DF1CE83" box="[116,1471,213,227]" gridrow="0" pageId="6" pageNumber="7">
|
||
<th id="356B472D6F7164BDFFB1188F8926CE83" box="[116,360,213,227]" gridcol="0" gridrow="0" pageId="6" pageNumber="7">Pathogens</th>
|
||
<th id="356B472D6F7164BDFE5D188F8A50CE83" box="[408,542,213,227]" gridcol="1" gridrow="0" pageId="6" pageNumber="7">1</th>
|
||
<th id="356B472D6F7164BDFD8A188F8A9BCE83" box="[591,725,213,227]" gridcol="2" gridrow="0" pageId="6" pageNumber="7">2</th>
|
||
<th id="356B472D6F7164BDFCC0188F8BC5CE83" box="[773,907,213,227]" gridcol="3" gridrow="0" pageId="6" pageNumber="7">3</th>
|
||
<th id="356B472D6F7164BDFC7E188F8C0FCE83" box="[955,1089,213,227]" gridcol="4" gridrow="0" pageId="6" pageNumber="7">4</th>
|
||
<th id="356B472D6F7164BDFBB4188F8D4ECE83" box="[1137,1280,213,227]" gridcol="5" gridrow="0" pageId="6" pageNumber="7">Chloramphenicol</th>
|
||
<th id="356B472D6F7164BDFAF5188F8DF1CE83" box="[1328,1471,213,227]" gridcol="6" gridrow="0" pageId="6" pageNumber="7">Ampicillin</th>
|
||
</tr>
|
||
<tr id="76BA2E516F7164BDFFB118AE8DF1CF66" box="[116,1471,244,262]" gridrow="1" pageId="6" pageNumber="7">
|
||
<th id="356B472D6F7164BDFFB118AE8926CF66" box="[116,360,244,262]" gridcol="0" gridrow="1" pageId="6" pageNumber="7">
|
||
<taxonomicName id="0F8A57906F719B44FFB118A288EFCF66" box="[116,161,248,262]" class="Bacilli" family="Enterococcaceae" genus="Enterococcus" kingdom="Bacteria" order="Lactobacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="coli">
|
||
<emphasis id="FAFEF0016F719B44FFB118A288EFCF66" bold="true" box="[116,161,248,262]" italics="true" pageId="6" pageNumber="7">E. coli</emphasis>
|
||
</taxonomicName>
|
||
(MTCC 443)
|
||
</th>
|
||
<td id="356B472D6F7164BDFE5D18AE8A50CF66" box="[408,542,244,262]" gridcol="1" gridrow="1" pageId="6" pageNumber="7">17b ± 0.05 (6.25)</td>
|
||
<td id="356B472D6F7164BDFD8A18AE8A9BCF66" box="[591,725,244,262]" gridcol="2" gridrow="1" pageId="6" pageNumber="7">23 a ± 0.01 (3.12)</td>
|
||
<td id="356B472D6F7164BDFCC018AE8BC5CF66" box="[773,907,244,262]" gridcol="3" gridrow="1" pageId="6" pageNumber="7">29 a ± 0.05 (3.12)</td>
|
||
<td id="356B472D6F7164BDFC7E18AE8C0FCF66" box="[955,1089,244,262]" gridcol="4" gridrow="1" pageId="6" pageNumber="7">24 a ± 0.10 (6.25)</td>
|
||
<td id="356B472D6F7164BDFBB418AE8D4ECF66" box="[1137,1280,244,262]" gridcol="5" gridrow="1" pageId="6" pageNumber="7">16b ± 0.02 (6.25)</td>
|
||
<td id="356B472D6F7164BDFAF518AE8DF1CF66" box="[1328,1471,244,262]" gridcol="6" gridrow="1" pageId="6" pageNumber="7">10 c ± 0.02 (6.25)</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7164BDFFB119518DF1CF7D" box="[116,1471,267,285]" gridrow="2" pageId="6" pageNumber="7">
|
||
<th id="356B472D6F7164BDFFB119518926CF7D" box="[116,360,267,285]" gridcol="0" gridrow="2" pageId="6" pageNumber="7">
|
||
<taxonomicName id="0F8A57906F719B44FFB119558948CF7C" box="[116,262,270,285]" class="Gammaproteobacteria" family="Vibrionaceae" genus="Vibrio" kingdom="Bacteria" order="Vibrionales" pageId="6" pageNumber="7" phylum="Proteobacteria" rank="species" species="parahaemolyticus">
|
||
<emphasis id="FAFEF0016F719B44FFB119558948CF7C" bold="true" box="[116,262,270,285]" italics="true" pageId="6" pageNumber="7">V. parahaemolyticus</emphasis>
|
||
</taxonomicName>
|
||
(MTCC 451)
|
||
</th>
|
||
<td id="356B472D6F7164BDFE5D19518A50CF7D" box="[408,542,267,285]" gridcol="1" gridrow="2" pageId="6" pageNumber="7">21b ± 0.34 (3.12)</td>
|
||
<td id="356B472D6F7164BDFD8A19518A9BCF7D" box="[591,725,267,285]" gridcol="2" gridrow="2" pageId="6" pageNumber="7">26 a ± 0.05 (1.56)</td>
|
||
<td id="356B472D6F7164BDFCC019518BC5CF7D" box="[773,907,267,285]" gridcol="3" gridrow="2" pageId="6" pageNumber="7">33 a ± 0.15 (1.56)</td>
|
||
<td id="356B472D6F7164BDFC7E19518C0FCF7D" box="[955,1089,267,285]" gridcol="4" gridrow="2" pageId="6" pageNumber="7">26 a ± 0.05 (3.12)</td>
|
||
<td id="356B472D6F7164BDFBB419518D4ECF7D" box="[1137,1280,267,285]" gridcol="5" gridrow="2" pageId="6" pageNumber="7">11 c ± 0.06 (6.25)</td>
|
||
<td id="356B472D6F7164BDFAF519518DF1CF7D" box="[1328,1471,267,285]" gridcol="6" gridrow="2" pageId="6" pageNumber="7">12 c ± 0.01 (6.25)</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7164BDFFB1197B8DF1CF54" box="[116,1471,289,308]" gridrow="3" pageId="6" pageNumber="7">
|
||
<th id="356B472D6F7164BDFFB1197B8926CF54" box="[116,360,289,308]" gridcol="0" gridrow="3" pageId="6" pageNumber="7">
|
||
<taxonomicName id="0F8A57906F719B44FFB1197C889ACF53" authorityName="Migula" authorityYear="1900" baseAuthorityName="Schroeter" baseAuthorityYear="1872" box="[116,212,293,308]" class="Betaproteobacteria" family="Burkholderiaceae" genus="Pseudomonas" kingdom="Bacteria" order="Burkholderiales" pageId="6" pageNumber="7" phylum="Proteobacteria" rank="species" species="aeruginosa">
|
||
<emphasis id="FAFEF0016F719B44FFB1197C889ACF53" bold="true" box="[116,212,293,308]" italics="true" pageId="6" pageNumber="7">P. aeruginosa</emphasis>
|
||
</taxonomicName>
|
||
(ATCC 27853)
|
||
</th>
|
||
<td id="356B472D6F7164BDFE5D197B8A50CF54" box="[408,542,289,308]" gridcol="1" gridrow="3" pageId="6" pageNumber="7">19b ± 0.03 (3.12)</td>
|
||
<td id="356B472D6F7164BDFD8A197B8A9BCF54" box="[591,725,289,308]" gridcol="2" gridrow="3" pageId="6" pageNumber="7">13c ± 0.20 (6.25)</td>
|
||
<td id="356B472D6F7164BDFCC0197B8BC5CF54" box="[773,907,289,308]" gridcol="3" gridrow="3" pageId="6" pageNumber="7">23a ± 0.25 (1.56)</td>
|
||
<td id="356B472D6F7164BDFC7E197B8C0FCF54" box="[955,1089,289,308]" gridcol="4" gridrow="3" pageId="6" pageNumber="7">22b ± 0.02 (3.12)</td>
|
||
<td id="356B472D6F7164BDFBB4197B8D4ECF54" box="[1137,1280,289,308]" gridcol="5" gridrow="3" pageId="6" pageNumber="7">11c ± 0.02 (12.50)</td>
|
||
<td id="356B472D6F7164BDFAF5197B8DF1CF54" box="[1328,1471,289,308]" gridcol="6" gridrow="3" pageId="6" pageNumber="7">11c ± 0.04 (12.50)</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7164BDFFB119628DF1CF2B" box="[116,1471,312,331]" gridrow="4" pageId="6" pageNumber="7">
|
||
<th id="356B472D6F7164BDFFB119628926CF2B" box="[116,360,312,331]" gridcol="0" gridrow="4" pageId="6" pageNumber="7">
|
||
<taxonomicName id="0F8A57906F719B44FFB119668890CF2A" authorityName="Trevisan" authorityYear="1887" baseAuthorityName="Schroeter" baseAuthorityYear="1886" box="[116,222,316,330]" class="Gammaproteobacteria" family="Enterobacteriaceae" genus="Klebsiella" kingdom="Bacteria" order="Enterobacteriales" pageId="6" pageNumber="7" phylum="Proteobacteria" rank="species" species="pneumoniae">
|
||
<emphasis id="FAFEF0016F719B44FFB119668890CF2A" bold="true" box="[116,222,316,330]" italics="true" pageId="6" pageNumber="7">K. pneumoniae</emphasis>
|
||
</taxonomicName>
|
||
(ATCC 13883)
|
||
</th>
|
||
<td id="356B472D6F7164BDFE5D19628A50CF2B" box="[408,542,312,331]" gridcol="1" gridrow="4" pageId="6" pageNumber="7">11c ± 0.04 (6.25)</td>
|
||
<td id="356B472D6F7164BDFD8A19628A9BCF2B" box="[591,725,312,331]" gridcol="2" gridrow="4" pageId="6" pageNumber="7">16b ± 0.05 (6.25)</td>
|
||
<td id="356B472D6F7164BDFCC019628BC5CF2B" box="[773,907,312,331]" gridcol="3" gridrow="4" pageId="6" pageNumber="7">25a ± 0.02 (1.56)</td>
|
||
<td id="356B472D6F7164BDFC7E19628C0FCF2B" box="[955,1089,312,331]" gridcol="4" gridrow="4" pageId="6" pageNumber="7">24a ± 0.06 (3.12)</td>
|
||
<td id="356B472D6F7164BDFBB419628D4ECF2B" box="[1137,1280,312,331]" gridcol="5" gridrow="4" pageId="6" pageNumber="7">7 d ± 0.04 (12.50)</td>
|
||
<td id="356B472D6F7164BDFAF519628DF1CF2B" box="[1328,1471,312,331]" gridcol="6" gridrow="4" pageId="6" pageNumber="7">9d ± 0.04 (12.50)</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7164BDFFB119158DF1CF02" box="[116,1471,335,354]" gridrow="5" pageId="6" pageNumber="7">
|
||
<th id="356B472D6F7164BDFFB119158926CF02" box="[116,360,335,354]" gridcol="0" gridrow="5" pageId="6" pageNumber="7">
|
||
<taxonomicName id="0F8A57906F719B44FFB119098957CF01" authority="(MTCC 2400)" baseAuthorityName="MTCC" baseAuthorityYear="2400" box="[116,281,339,353]" class="Bacilli" family="Enterococcaceae" genus="Enterococcus" kingdom="Bacteria" order="Lactobacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="tarda">
|
||
<emphasis id="FAFEF0016F719B44FFB1190988E0CF01" bold="true" box="[116,174,339,353]" italics="true" pageId="6" pageNumber="7">E. tarda</emphasis>
|
||
(MTCC 2400)
|
||
</taxonomicName>
|
||
</th>
|
||
<td id="356B472D6F7164BDFE5D19158A50CF02" box="[408,542,335,354]" gridcol="1" gridrow="5" pageId="6" pageNumber="7">20b ± 0.02 (6.25)</td>
|
||
<td id="356B472D6F7164BDFD8A19158A9BCF02" box="[591,725,335,354]" gridcol="2" gridrow="5" pageId="6" pageNumber="7">25 a ± 0.05 (3.12)</td>
|
||
<td id="356B472D6F7164BDFCC019158BC5CF02" box="[773,907,335,354]" gridcol="3" gridrow="5" pageId="6" pageNumber="7">27 a ± 0.03 (3.12)</td>
|
||
<td id="356B472D6F7164BDFC7E19158C0FCF02" box="[955,1089,335,354]" gridcol="4" gridrow="5" pageId="6" pageNumber="7">27 a ± 0.05 (3.12)</td>
|
||
<td id="356B472D6F7164BDFBB419158D4ECF02" box="[1137,1280,335,354]" gridcol="5" gridrow="5" pageId="6" pageNumber="7">14 c ± 0.01 (6.25)</td>
|
||
<td id="356B472D6F7164BDFAF519158DF1CF02" box="[1328,1471,335,354]" gridcol="6" gridrow="5" pageId="6" pageNumber="7">13 c ± 0.01 (6.25)</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7164BDFFB1193C8DF1CF18" box="[116,1471,358,376]" gridrow="6" pageId="6" pageNumber="7">
|
||
<th id="356B472D6F7164BDFFB1193C8926CF18" box="[116,360,358,376]" gridcol="0" gridrow="6" pageId="6" pageNumber="7">
|
||
<taxonomicName id="0F8A57906F719B44FFB119308978CF18" authority="(MTCC, 1924)" baseAuthorityName="MTCC" baseAuthorityYear="1924" box="[116,310,362,376]" class="Bacilli" family="Streptococcaceae" genus="Streptococcus" kingdom="Bacteria" order="Lactobacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="pyogenes">
|
||
<emphasis id="FAFEF0016F719B44FFB119308888CF18" bold="true" box="[116,198,362,376]" italics="true" pageId="6" pageNumber="7">S. pyogenes</emphasis>
|
||
(MTCC, 1924)
|
||
</taxonomicName>
|
||
</th>
|
||
<td id="356B472D6F7164BDFE5D193C8A50CF18" box="[408,542,358,376]" gridcol="1" gridrow="6" pageId="6" pageNumber="7">22b ± 0.01 (3.12)</td>
|
||
<td id="356B472D6F7164BDFD8A193C8A9BCF18" box="[591,725,358,376]" gridcol="2" gridrow="6" pageId="6" pageNumber="7">21b ± 0.02 (3.12)</td>
|
||
<td id="356B472D6F7164BDFCC0193C8BC5CF18" box="[773,907,358,376]" gridcol="3" gridrow="6" pageId="6" pageNumber="7">30 a ± 0.01 (1.56)</td>
|
||
<td id="356B472D6F7164BDFC7E193C8C0FCF18" box="[955,1089,358,376]" gridcol="4" gridrow="6" pageId="6" pageNumber="7">23 a ± 0.02 (6.25)</td>
|
||
<td id="356B472D6F7164BDFBB4193C8D4ECF18" box="[1137,1280,358,376]" gridcol="5" gridrow="6" pageId="6" pageNumber="7">15 c ± 0.03 (6.25)</td>
|
||
<td id="356B472D6F7164BDFAF5193C8DF1CF18" box="[1328,1471,358,376]" gridcol="6" gridrow="6" pageId="6" pageNumber="7">15 c ± 0.05 (6.25)</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7164BDFFB119278DF1CFEF" box="[116,1471,381,399]" gridrow="7" pageId="6" pageNumber="7">
|
||
<th id="356B472D6F7164BDFFB119278926CFEF" box="[116,360,381,399]" gridcol="0" gridrow="7" pageId="6" pageNumber="7">MRSA (ATCC 33592)</th>
|
||
<td id="356B472D6F7164BDFE5D19278A50CFEF" box="[408,542,381,399]" gridcol="1" gridrow="7" pageId="6" pageNumber="7">20b ± 0.15 (6.25)</td>
|
||
<td id="356B472D6F7164BDFD8A19278A9BCFEF" box="[591,725,381,399]" gridcol="2" gridrow="7" pageId="6" pageNumber="7">22b ± 0.01 (3.12)</td>
|
||
<td id="356B472D6F7164BDFCC019278BC5CFEF" box="[773,907,381,399]" gridcol="3" gridrow="7" pageId="6" pageNumber="7">24 a ± 0.10 (1.56)</td>
|
||
<td id="356B472D6F7164BDFC7E19278C0FCFEF" box="[955,1089,381,399]" gridcol="4" gridrow="7" pageId="6" pageNumber="7">21b ± 0.01 (3.12)</td>
|
||
<td id="356B472D6F7164BDFBB419278D4ECFEF" box="[1137,1280,381,399]" gridcol="5" gridrow="7" pageId="6" pageNumber="7">14 c ± 0.02 (6.25)</td>
|
||
<td id="356B472D6F7164BDFAF519278DF1CFEF" box="[1328,1471,381,399]" gridcol="6" gridrow="7" pageId="6" pageNumber="7">14 c ± 0.02 (12.50)</td>
|
||
</tr>
|
||
<tr id="76BA2E516F7164BDFFB119CE8DF1CFC6" box="[116,1471,404,422]" gridrow="8" pageId="6" pageNumber="7">
|
||
<th id="356B472D6F7164BDFFB119CE8926CFC6" box="[116,360,404,422]" gridcol="0" gridrow="8" pageId="6" pageNumber="7">
|
||
VRE
|
||
<emphasis id="FAFEF0016F719B44FF5019CD88EFCFC5" bold="true" box="[149,161,407,421]" italics="true" pageId="6" pageNumber="7">fs</emphasis>
|
||
(ATCC 51299)
|
||
</th>
|
||
<td id="356B472D6F7164BDFE5D19CE8A50CFC6" box="[408,542,404,422]" gridcol="1" gridrow="8" pageId="6" pageNumber="7">22b ± 0.20 (6.25)</td>
|
||
<td id="356B472D6F7164BDFD8A19CE8A9BCFC6" box="[591,725,404,422]" gridcol="2" gridrow="8" pageId="6" pageNumber="7">24 a ± 0.04 (6.25)</td>
|
||
<td id="356B472D6F7164BDFCC019CE8BC5CFC6" box="[773,907,404,422]" gridcol="3" gridrow="8" pageId="6" pageNumber="7">34 a ± 0.05 (1.56)</td>
|
||
<td id="356B472D6F7164BDFC7E19CE8C0FCFC6" box="[955,1089,404,422]" gridcol="4" gridrow="8" pageId="6" pageNumber="7">25 a ± 0.05 (6.25)</td>
|
||
<td id="356B472D6F7164BDFBB419CE8D4ECFC6" box="[1137,1280,404,422]" gridcol="5" gridrow="8" pageId="6" pageNumber="7">8d ± 0.01 (6.25)</td>
|
||
<td id="356B472D6F7164BDFAF519CE8DF1CFC6" box="[1328,1471,404,422]" gridcol="6" gridrow="8" pageId="6" pageNumber="7">11 c ± 0.05 (6.25)</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F719B44FFA119E68A85CF86" blockId="6.[100,1487,443,614]" pageId="6" pageNumber="7">Antibacterial activities were expressed in terms of minimum inhibitory concentration (MIC values were described in parentheses and expressed as μg/mL) and inhibitory zone (expressed in mm) against clinically relevant pathogens.</paragraph>
|
||
<paragraph id="C8352C136F719B44FFA119B089E2CC53" blockId="6.[100,1487,443,614]" pageId="6" pageNumber="7">
|
||
<superScript id="3FFF815B6F719B44FFA119B08836CF96" attach="left" box="[100,120,490,502]" fontSize="5" pageId="6" pageNumber="7">a-d</superScript>
|
||
Row-wise values with different superscripts of this
|
||
<typeStatus id="173192B16F719B44FDE619B58A06CF9F" box="[547,584,495,511]" pageId="6" pageNumber="7">type</typeStatus>
|
||
indicate statistically significant difference (
|
||
<emphasis id="FAFEF0016F719B44FC7119B58B9FCC60" box="[948,977,495,512]" italics="true" pageId="6" pageNumber="7">
|
||
<emphasis id="FAFEF0016F719B44FC7119B58BF3CF9F" bold="true" box="[948,957,495,511]" italics="true" pageId="6" pageNumber="7">p</emphasis>
|
||
<
|
||
</emphasis>
|
||
0.05). Triplicate values were taken and the variance analyses (ANOVA) were carried out (using Statistical Program for Social Sciences, ver. 13.0) for means of all parameters to examine the significance level (
|
||
<emphasis id="FAFEF0016F719B44FAFD1A528D18CC79" box="[1336,1366,520,537]" italics="true" pageId="6" pageNumber="7">
|
||
<emphasis id="FAFEF0016F719B44FAFD1A528D0FCC78" bold="true" box="[1336,1345,520,536]" italics="true" pageId="6" pageNumber="7">p</emphasis>
|
||
<
|
||
</emphasis>
|
||
0.05). Results were expressed as mean ± SD (n = 3).
|
||
</paragraph>
|
||
<paragraph id="C8352C136F719B44FFA11A618B0ECC2C" blockId="6.[100,1487,443,614]" box="[100,832,570,589]" pageId="6" pageNumber="7">
|
||
The macrobrevin analogues
|
||
<emphasis id="FAFEF0016F719B44FE901A61893ACC2C" bold="true" box="[341,372,571,588]" pageId="6" pageNumber="7">1–4</emphasis>
|
||
and commercial standards were taken 30 μg per disc.
|
||
</paragraph>
|
||
<paragraph id="C8352C136F719B44FFA11A0F8BD9CC05" blockId="6.[100,1487,443,614]" box="[100,919,596,614]" pageId="6" pageNumber="7">
|
||
Abbreviations: MRSA = Methicillin resistant
|
||
<taxonomicName id="0F8A57906F719B44FE261A0E8A15CC05" authority=", VRE" authorityName="VRE" box="[483,603,596,613]" class="Bacilli" family="Staphylococcaceae" genus="Staphylococcus" kingdom="Bacteria" order="Bacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="aureus">
|
||
<emphasis id="FAFEF0016F719B44FE261A0E8A63CC05" bold="true" box="[483,557,596,613]" italics="true" pageId="6" pageNumber="7">S. aureus</emphasis>
|
||
, VRE
|
||
</taxonomicName>
|
||
<emphasis id="FAFEF0016F719B44FD991A0E8A27CC05" bold="true" box="[604,617,596,613]" italics="true" pageId="6" pageNumber="7">fs</emphasis>
|
||
= Vancomycin resistant
|
||
<emphasis id="FAFEF0016F719B44FCFA1A0F8BD9CC05" bold="true" box="[831,919,596,613]" italics="true" pageId="6" pageNumber="7">
|
||
<taxonomicName id="0F8A57906F719B44FCFA1A0F8BDDCC05" authorityName="Schleifer & Kilpper-Bälz" authorityYear="1984" baseAuthorityName="Andrewes & Horder" baseAuthorityYear="1906" box="[831,915,596,613]" class="Bacilli" family="Enterococcaceae" genus="Enterococcus" kingdom="Bacteria" order="Lactobacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="feacalis">E. feacalis</taxonomicName>
|
||
.
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F719B44FF411DDA8B9FCDD8" blockId="6.[100,771,655,1957]" lastBlockId="6.[818,1488,655,1427]" pageId="6" pageNumber="7">
|
||
The putative biosynthetic pathway is a proposition based on comparisons with other organisms (
|
||
<bibRefCitation id="AC1B51E26F719B44FE5F1DC68A2ECBCF" author="Helfrich, E. J. N. & Vogel, C. M. & Ueoka, R. & Ryffel, F. & Muller, D. B. & Probst, S. & Kreuzer, M. & Piel, J. & Vorholt, J. A." box="[410,608,1436,1455]" pageId="6" pageNumber="7" pagination="909 - 919" refId="ref16029" refString="Helfrich, E. J. N., Vogel, C. M., Ueoka, R., Sch ¨ afer, M., Ryffel, F., Muller, D. B., Probst, S., Kreuzer, M., Piel, J., Vorholt, J. A., 2018. Bipartite interactions, antibiotic production and biosynthetic potential of the Arabidopsis leaf microbiome. Nat. Microbiol. 3 (8), 909 - 919. https: // doi. org / 10.1038 / s 41564 - 018 - 0200 - 0." type="journal article" year="2018">Helfrich et al., 2018</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="AC1B51E26F719B44FDAA1DC688DACBAB" author="Soldatou, S. & Eldjarn, G. H. & Huerta-Uribe, A. & Rogers, S. & Duncan, K. R." pageId="6" pageNumber="7" pagination="142" refId="ref17331" refString="Soldatou, S., Eldjarn, G. H., Huerta-Uribe, A., Rogers, S., Duncan, K. R., 2019. Linking biosynthetic and chemical space to accelerate microbial secondary metabolite discovery. FEMS Microbiol. Lett. 366 (13), fnz 142. https: // doi. org / 10.1093 / femsle / fnz 142." type="journal article" year="2019">Soldatou et al., 2019</bibRefCitation>
|
||
). Some of the genes (such as
|
||
<emphasis id="FAFEF0016F719B44FE721DE28993CBAB" bold="true" box="[439,477,1464,1483]" italics="true" pageId="6" pageNumber="7">nrps</emphasis>
|
||
) in the presented biosynthetic gene cluster might not function in macrobrevin biosynthesis as judged from the lack of amino acid moiety in the isolated macrobrevin compounds. At this instant, we have proposed a possible biosynthetic pathway through which the titled compounds
|
||
<emphasis id="FAFEF0016F719B44FDE91E7D8A01C85A" bold="true" box="[556,591,1575,1595]" pageId="6" pageNumber="7">1–4</emphasis>
|
||
might be formed. Putative biosynthetic origin of the titled macrobrevin analogues
|
||
<emphasis id="FAFEF0016F719B44FD731E198A97C836" bold="true" box="[694,729,1603,1623]" pageId="6" pageNumber="7">1–4</emphasis>
|
||
was found to be analogous to the biosynthesis of previously described macrobrevins from
|
||
<taxonomicName id="0F8A57906F719B44FF3E1E2089C0C8EE" box="[251,398,1658,1678]" class="Bacilli" family="Paenibacillaceae" genus="Brevibacillus" kingdom="Bacteria" order="Bacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="undetermined">
|
||
<emphasis id="FAFEF0016F719B44FF3E1E208925C8ED" bold="true" box="[251,363,1658,1677]" italics="true" pageId="6" pageNumber="7">Brevibacillus</emphasis>
|
||
sp.
|
||
</taxonomicName>
|
||
(
|
||
<bibRefCitation id="AC1B51E26F719B44FE5B1E218A2CC8EE" author="Helfrich, E. J. N. & Vogel, C. M. & Ueoka, R. & Ryffel, F. & Muller, D. B. & Probst, S. & Kreuzer, M. & Piel, J. & Vorholt, J. A." box="[414,610,1659,1678]" pageId="6" pageNumber="7" pagination="909 - 919" refId="ref16029" refString="Helfrich, E. J. N., Vogel, C. M., Ueoka, R., Sch ¨ afer, M., Ryffel, F., Muller, D. B., Probst, S., Kreuzer, M., Piel, J., Vorholt, J. A., 2018. Bipartite interactions, antibiotic production and biosynthetic potential of the Arabidopsis leaf microbiome. Nat. Microbiol. 3 (8), 909 - 919. https: // doi. org / 10.1038 / s 41564 - 018 - 0200 - 0." type="journal article" year="2018">Helfrich et al., 2018</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="AC1B51E26F719B44FDB51E2188DAC8CA" author="Soldatou, S. & Eldjarn, G. H. & Huerta-Uribe, A. & Rogers, S. & Duncan, K. R." pageId="6" pageNumber="7" pagination="142" refId="ref17331" refString="Soldatou, S., Eldjarn, G. H., Huerta-Uribe, A., Rogers, S., Duncan, K. R., 2019. Linking biosynthetic and chemical space to accelerate microbial secondary metabolite discovery. FEMS Microbiol. Lett. 366 (13), fnz 142. https: // doi. org / 10.1093 / femsle / fnz 142." type="journal article" year="2019">Soldatou et al., 2019</bibRefCitation>
|
||
). Herein, the 21-membered macrocyclic lactone part and its extender linear chain at C-21 were found to biosynthesize by the decarboxylative Claisen condensations (
|
||
<figureCitation id="50B130966F719B44FE251E948A58C882" box="[480,534,1742,1762]" captionStart="Fig" captionStartId="8.[1110,1140,149,166]" captionTargetBox="[102,1083,149,1887]" captionTargetId="figure-7@8.[100,1085,148,1888]" captionTargetPageId="8" captionText="Fig. 4. Proposed biosynthesis of 21- membered macrocyclic lactones classified as macrobrevin analogues (1–4) in B. amyloliquefaciens through successive decarboxylative Claisen condensation between acetyl-S-KS domain and malonate-S- ACP units. Claisen condensation was activated by acyl carrier protein (ACP), ketoreductase (KR), ketosynthase (KS), thioesterase (TE), dehydratase (DH), methyl transferase (MT), acyl transferase (AT), enoyl reductase (ER) and S-adenosyl-methionine (SAM). The elongation process comprised of 16 modules with KS, KR and ACP domains. The initial step includes the decarboxylative Claisen condensation between 2-methylbutanethioic-S-KS and malonate-S-ACP. The final step of macrobrevin formation could occur through the cyclization of linear chain of 21-membered carbon framework by TE. Consequently, alterations of 21-membered carbon framework classified as macrobrevin scaffold could result in the formation of macrobrevin analogues 1–4." figureDoi="http://doi.org/10.5281/zenodo.8235159" httpUri="https://zenodo.org/record/8235159/files/figure.png" pageId="6" pageNumber="7">Fig. 4</figureCitation>
|
||
). The biosynthetic route could be originated by condensation of malonate-S-ACP residue with 2-methylbutanethioic-S-KS catalyzed by ketosynthase-mediated decarboxylative Claisen condensation. In the formation of 2-methylbutanoyl-KS initiator group, the KS-assisted decarboxylative condensation was found to be the initial step, followed by methylation at C-2 by methyltransferase/S-adenosyl-methionine and KR-assisted reduction through the conversion of NADPH
|
||
<superScript id="3FFF815B6F719B44FE0B1FD68995C9FA" attach="left" box="[462,475,1932,1946]" fontSize="6" pageId="6" pageNumber="7">+</superScript>
|
||
to NADP
|
||
<superScript id="3FFF815B6F719B44FD801FD68A1CC9FA" attach="left" box="[581,594,1932,1946]" fontSize="6" pageId="6" pageNumber="7">+</superScript>
|
||
and DH-assisted dehydration. The elongation steps comprised of 16 modules with ketosynthase, ketoreductase, methyl transferase, dehydratase, enoyl reductase, thioesterase, and acyl carrier protein domains. Repeated additions of malonate groups through Claisen condensations including reduction and methylation could result in the formation of linear chain of 34-membered carbon framework with hydroxyls and methyls in association with C-1 carbonyl carbon. The C-1 carbonyl of the linear chain of 34-membered carbon framework could be cyclized to the nucleophilic hydroxyl at C-21 position through thioesterase-catalyzed biosynthesis leading to the formation of 21-membered macrocyclic lactone (macrobrevin) skeleton.
|
||
</paragraph>
|
||
<paragraph id="C8352C136F719B44FC941B9B8CE6CBF3" blockId="6.[818,1488,655,1427]" pageId="6" pageNumber="7">
|
||
The double bonds at C-7, C-10, C-16, C-25, and C-27 positions might be saturated through several enzyme-associated biosynthesis. Thereafter, the nucleophilic hydroxyl could be added to the electrophilic position C-27 through enzyme-assisted hydroxylation. The chain elongation at C-13 through various enzyme-assisted mechanism yielded the compound
|
||
<emphasis id="FAFEF0016F719B44FC591C178BE6CA00" bold="true" box="[924,936,1101,1120]" pageId="6" pageNumber="7">1</emphasis>
|
||
. Similarly, the double bonds at C-8, C-16, and C-25 positions could be saturated through the enzyme-assisted biosynthesis to afford compound
|
||
<emphasis id="FAFEF0016F719B44FC1D1CDF8BAACAF8" bold="true" box="[984,996,1157,1176]" pageId="6" pageNumber="7">2</emphasis>
|
||
. The latter upon hydroxylation at C-41 and addition of electrophilic acetyl group at the nucleophilic end of hydroxyl at C-31 through several pathways might result in the formation of compound
|
||
<emphasis id="FAFEF0016F719B44FA781CE68D87CAAF" bold="true" box="[1469,1481,1212,1231]" pageId="6" pageNumber="7">3</emphasis>
|
||
. The double bonds at C-8, C-16, and C-25 positions might be saturated and methyl group was eliminated from C-28 position through various enzymatic reactions. Enzyme-assisted methylation at the nucleophilic end of hydroxyl at C-5 might
|
||
<taxonomicName id="0F8A57906F719B44FB901D768CE6CB5F" box="[1109,1192,1324,1343]" form="the" pageId="6" pageNumber="7" rank="form">form the</taxonomicName>
|
||
compound
|
||
<emphasis id="FAFEF0016F719B44FADE1D768D69CB5F" bold="true" box="[1307,1319,1324,1343]" pageId="6" pageNumber="7">4</emphasis>
|
||
. Although it was predicted that the presented gene cluster could be involved in macrobrevin biosynthesis, more detailed analysis should be necessary for the elucidation of its biosynthetic pathway.
|
||
</paragraph>
|
||
<paragraph id="C8352C136F719B44FCF71D8A8D40CB83" blockId="6.[818,1294,1488,1507]" box="[818,1294,1488,1507]" pageId="6" pageNumber="7">
|
||
<heading id="937D9B7F6F719B44FCF71D8A8D40CB83" bold="true" box="[818,1294,1488,1507]" fontSize="36" level="1" pageId="6" pageNumber="7" reason="1">
|
||
<emphasis id="FAFEF0016F719B44FCF71D8A8D40CB83" bold="true" box="[818,1294,1488,1507]" italics="true" pageId="6" pageNumber="7">2.6. Molecular docking interaction and drug-likeness</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="C8352C136F719B45FC941E528C43C83F" blockId="6.[818,1488,1544,1982]" lastBlockId="7.[818,1487,1556,1631]" lastPageId="7" lastPageNumber="8" pageId="6" pageNumber="7">
|
||
As a means to assign the antibacterial properties of the studied polyketide-bridged macrobrevins (compounds
|
||
<emphasis id="FAFEF0016F719B44FB251E7E8CB1C857" bold="true" box="[1248,1279,1572,1592]" pageId="6" pageNumber="7">1-4</emphasis>
|
||
) from the marine algaassociated
|
||
<taxonomicName id="0F8A57906F719B44FC5C1E1A8C1CC833" box="[921,1106,1600,1619]" class="Bacilli" family="Bacillaceae" genus="Bacillus" kingdom="Bacteria" order="Bacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="amyloliquefaciens">
|
||
<emphasis id="FAFEF0016F719B44FC5C1E1A8C1CC833" bold="true" box="[921,1106,1600,1619]" italics="true" pageId="6" pageNumber="7">B. amyloliquefaciens</emphasis>
|
||
</taxonomicName>
|
||
against peptide deformylase (PDF), the enzyme PDF of
|
||
<taxonomicName id="0F8A57906F719B44FC021E068C54C80F" box="[967,1050,1628,1647]" class="Bacilli" family="Staphylococcaceae" genus="Staphylococcus" kingdom="Bacteria" order="Bacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="aureus">
|
||
<emphasis id="FAFEF0016F719B44FC021E068C54C80F" bold="true" box="[967,1050,1628,1647]" italics="true" pageId="6" pageNumber="7">S. aureus</emphasis>
|
||
</taxonomicName>
|
||
(1LQW) was docked with the ligands (macrobrevin derivatives). PDF has been labeled as a representative drug target based on the selectivity principles to demonstrate the antibacterial potential against drug-resistant
|
||
<taxonomicName id="0F8A57906F719B44FB891EF58CEEC8A3" box="[1100,1184,1711,1731]" class="Bacilli" family="Staphylococcaceae" genus="Staphylococcus" kingdom="Bacteria" order="Bacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="aureus">
|
||
<emphasis id="FAFEF0016F719B44FB891EF58CEEC8A3" bold="true" box="[1100,1184,1711,1731]" italics="true" pageId="6" pageNumber="7">S. aureus</emphasis>
|
||
</taxonomicName>
|
||
, as PDF is critical for bacterial survival. Interestingly, no corresponding functional protein is present in human beings (
|
||
<bibRefCitation id="AC1B51E26F719B44FC071EBD8C60C89A" author="Guay, D. R." box="[962,1070,1767,1786]" pageId="6" pageNumber="7" pagination="513 - 525" refId="ref15919" refString="Guay, D. R., 2007. Drug forecast - the peptide deformylase inhibitors as antibacterial agents. Therapeut. Clin. Risk Manag. 3 (4), 513 - 525. PMID: 18472972." type="journal article" year="2007">Guay, 2007</bibRefCitation>
|
||
). Additionally, deformylation is a conserved attribute around the eubacteria, and this would permit to characterize wide-ranging antibiotic compounds (
|
||
<bibRefCitation id="AC1B51E26F719B44FB501F458D12C952" author="Giglione, C. & Pierre, M. & Meinnel, T." box="[1173,1372,1823,1842]" pageId="6" pageNumber="7" pagination="1197 - 1205" refId="ref15858" refString="Giglione, C., Pierre, M., Meinnel, T., 2000. Peptide deformylase as a target for new generation, broad spectrum antimicrobial agents. Mol. Microbiol. 36 (6), 1197 - 1205. https: // doi. org / 10.1046 / j. 1365 - 2958.2000.01908. x." type="journal article" year="2000">Giglione et al., 2000</bibRefCitation>
|
||
). It was reported that macrolactin N could inhibit
|
||
<taxonomicName id="0F8A57906F719B44FB751F618D4DC92E" box="[1200,1283,1851,1870]" class="Bacilli" family="Staphylococcaceae" genus="Staphylococcus" kingdom="Bacteria" order="Bacillales" pageId="6" pageNumber="7" phylum="Firmicutes" rank="species" species="aureus">
|
||
<emphasis id="FAFEF0016F719B44FB751F618D4DC92E" bold="true" box="[1200,1283,1851,1870]" italics="true" pageId="6" pageNumber="7">S. aureus</emphasis>
|
||
</taxonomicName>
|
||
peptide deformylase. Considering that the chemical structure of macrobrevin-type compounds is similar to that of macrolactin N, macrobrevin-type compound might also inhibit peptide deformylase. The natural PDIs (peptide deformylase inhibitor), macrolactin N and actinonin were chosen as reference molecules with binding energies of 9.4 kcal/mol and 6.9 kcal/mol, respectively (
|
||
<bibRefCitation id="AC1B51E26F709B45FF271E6A89E4C823" author="Chen, D. & Yuan, Z." box="[226,426,1584,1603]" pageId="7" pageNumber="8" pagination="1107 - 1116" refId="ref15431" refString="Chen, D., Yuan, Z., 2005. Therapeutic potential of peptide deformylase inhibitors. Expet Opin. Invest. Drugs 14 (9), 1107 - 1116. https: // doi. org / 10.1517 / 13543784.14. 9.1107." type="journal article" year="2005">Chen and Yuan, 2005</bibRefCitation>
|
||
). Docking analysis demonstrated the binding energy for compound (
|
||
<emphasis id="FAFEF0016F709B45FE431E1689DCC83F" bold="true" box="[390,402,1612,1631]" pageId="7" pageNumber="8">3</emphasis>
|
||
) with PDF of 12.61 kcal/mol coupled with an inhibition constant (K
|
||
<emphasis id="FAFEF0016F709B45FE4B1E3589DCC81D" bold="true" box="[398,402,1647,1661]" italics="true" pageId="7" pageNumber="8">
|
||
<subScript id="540E2E566F709B45FE4B1E3589DCC81D" attach="left" box="[398,402,1647,1661]" fontSize="6" pageId="7" pageNumber="8">i</subScript>
|
||
</emphasis>
|
||
) of 573.34 pM (
|
||
<tableCitation id="850819A86F709B45FDFE1E328ACBC81B" box="[571,645,1640,1659]" captionStart="Table 3" captionStartId="9.[100,150,150,166]" captionTargetPageId="9" captionText="Table 3 In silico molecular docking parameters between titled macrobrevin analogues 1–4 with the active sites of peptide deformylase of S. aureus (SaPDF)." httpUri="http://table.plazi.org/id/9CF57C9B6F7E9B4BFFA118CC8D06CEA1" pageId="7" pageNumber="8" tableUuid="9CF57C9B6F7E9B4BFFA118CC8D06CEA1">Table 3</tableCitation>
|
||
), other than exhibiting maximum number of hydrogen bond interactions among the titled compounds (
|
||
<figureCitation id="50B130966F709B45FEFD1EFA8930C8D2" box="[312,382,1695,1715]" captionStart="Fig" captionStartId="9.[1035,1065,476,493]" captionTargetBox="[102,1008,481,1431]" captionTargetId="figure-392@9.[100,1010,475,1433]" captionTargetPageId="9" captionText="Fig. 5. (A) Molecular docking interfaces of 41-hydroxy-macrobrevin-31-acetate (compound 3) with S. aureus peptide deformylase (SaPDF). 3D docking analysis of the titled macrobrevin analogue (ligand) and S. aureus PDF crystal structure (PDB ID: 1LQW) were conformationally structured (Swiss-Pdb Viewer, SPDBV, version 4.1.0). The primary algorithm used by AutoDock for conformational searching was the Lamarckian Genetic Algorithm (LGA) showing four hydrogen bonds each (displayed as red and bluecoloured lines) in the binding site, whereas USCF Chimera (University of California, San Francisco, ver. 1.11.2) software reinforced the visualizations of the best molecular docking positions of the compound and target protein. The contact residues were shown and labeled by type and number in the background. Compound 3 exhibited least binding energy among the titled compounds. (B) Illustrative representation of 41-hydroxy-macrobrevin-31-acetate (compound 3) forming hydrogen bond interactions with the amino acyl residues in the active site of SaPDF. Compound (3) displayed maximum number of hydrogen bond interactions (GLN141 at 3.118 Å, LYS84 at 3.789 Å and 3.388 Å, and ARG143 at 3.483 Å). (C) Drug-likeness score obtained for the compound (3) with molsoft software. (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.8235161" httpUri="https://zenodo.org/record/8235161/files/figure.png" pageId="7" pageNumber="8">Fig. 5</figureCitation>
|
||
). These results demonstrated that hexahydro-41-hydroxy-macrobrevin-31-acetate (compound
|
||
<emphasis id="FAFEF0016F709B45FD701EE18A8FC8AE" bold="true" box="[693,705,1723,1742]" pageId="7" pageNumber="8">3</emphasis>
|
||
) had greater inhibition potential for PDF (
|
||
<taxonomicName id="0F8A57906F709B45FE0D1E8D8A52C88B" box="[456,540,1751,1771]" class="Bacilli" family="Staphylococcaceae" genus="Staphylococcus" kingdom="Bacteria" order="Bacillales" pageId="7" pageNumber="8" phylum="Firmicutes" rank="species" species="aureus">
|
||
<emphasis id="FAFEF0016F709B45FE0D1E8D8A52C88B" bold="true" box="[456,540,1751,1771]" italics="true" pageId="7" pageNumber="8">S. aureus</emphasis>
|
||
</taxonomicName>
|
||
) than that exhibited by natural PDIs. Further, drug-likeness score showed that the compound
|
||
<emphasis id="FAFEF0016F709B45FD301EA98B4FC966" bold="true" box="[757,769,1779,1798]" pageId="7" pageNumber="8">3</emphasis>
|
||
disclosed a drug-like quality (drug-likeness score, 0.11). The occurrence of greater number of electron-rich cores, including hydroxyls (four), two ester functionalities, and greater number of non-conjugated/conjugated dienes in macrobrevin analogue
|
||
<emphasis id="FAFEF0016F709B45FE671F3989E0C916" bold="true" box="[418,430,1891,1910]" pageId="7" pageNumber="8">3</emphasis>
|
||
, when compared to those of other macrobrevin analogues, might contribute to the greater antibacterial properties of the former. The results obtained from the molecular docking/drug-likeness studies affirmed the antibacterial potential of the titled macrobrevin derivatives, more precisely compound
|
||
<emphasis id="FAFEF0016F709B45FA961E6A8D11C823" bold="true" box="[1363,1375,1584,1603]" pageId="7" pageNumber="8">3</emphasis>
|
||
, as a promising antibacterial lead.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |