2663 lines
264 KiB
XML
2663 lines
264 KiB
XML
<document id="78C9C95EE3B14F1AEB2D79184892F2E8" ID-DOI="10.1016/j.phytochem.2015.07.003" ID-ISSN="1873-3700" ID-Zenodo-Dep="10486278" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="jonas" IM.materialsCitations_approvedBy="jonas" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="jonas" IM.taxonomicNames_approvedBy="jonas" IM.treatments_approvedBy="jonas" checkinTime="1704948142945" checkinUser="felipe" docAuthor="Jin, Yu-Jing, Lin, Cha-Chi, Lu, Tzy-Ming, Li, Jih-Heng, Chen, Ih-Sheng, Kuo, Yueh-Hsiung & Ko, Horng-Huey" docDate="2015" docId="B67887E1FFD12862BA61056A58BC59F1" docLanguage="en" docName="Phytochemistry.117.424-435.pdf" docOrigin="Phytochemistry 117" docSource="http://dx.doi.org/10.1016/j.phytochem.2015.07.003" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Artocarpus xanthocarpus Merr." docType="treatment" docVersion="2" lastPageNumber="431" masterDocId="4A41FF99FFD02865BA13017C5B4C5914" masterDocTitle="Chemical constituents derived from Artocarpus xanthocarpus as inhibitors of melanin biosynthesis" masterLastPageNumber="435" masterPageNumber="424" pageNumber="425" updateTime="1705590817812" updateUser="ExternalLinkService">
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<mods:mods id="DD46FEE79F40EC075871E7E0D6CE7D66" xmlns:mods="http://www.loc.gov/mods/v3">
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<mods:titleInfo id="DC47674B150F20DF91C2EE950137E25A">
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<mods:title id="CEFCD1F3144E2F9C70925552E42EE98F">Chemical constituents derived from Artocarpus xanthocarpus as inhibitors of melanin biosynthesis</mods:title>
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<mods:name id="D274AED4C6083A15382D5667AF2D7774" type="personal">
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<mods:namePart id="97A1F03BB5BD51CBDC6E241A1EB765F3">Jin, Yu-Jing</mods:namePart>
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<mods:affiliation id="371ABD8F0C0E949C39EB95BFCE711CD5">Department of Fragrance and Cosmetic Science, Kaohsiung Medical University, Kaohsiung 807, Taiwan</mods:affiliation>
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<mods:name id="56B114319EAEDADDD4D0A022841C5BCD" type="personal">
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<mods:roleTerm id="BB86CB2D21E32E6F37C93C1792762010">Author</mods:roleTerm>
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<mods:namePart id="0ADBA8504062388ADD233B38193D5A8B">Lin, Cha-Chi</mods:namePart>
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<mods:namePart id="A589C4506FD9AB6FEA8B23EC73214D0A">Lu, Tzy-Ming</mods:namePart>
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<mods:roleTerm id="B262854B41ECB3107F8653B92FA103A5">Author</mods:roleTerm>
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<mods:namePart id="7B3D7B63815B95C3E68330C4E45D2691">Li, Jih-Heng</mods:namePart>
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</mods:name>
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<mods:namePart id="F5EA1B2626C45F26B1C79E4076E81508">Chen, Ih-Sheng</mods:namePart>
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<mods:namePart id="7FED8128E6CC6F966B250941BC701CD4">Kuo, Yueh-Hsiung</mods:namePart>
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<mods:namePart id="3F9D2414BFE295AA1228A0D47D5868B7">Ko, Horng-Huey</mods:namePart>
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<mods:typeOfResource id="9EE83BF609C799358A613B56189CD15D">text</mods:typeOfResource>
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<mods:title id="03E2F9DEE41211CE6ACF04FB10C08EA9">Phytochemistry</mods:title>
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<mods:part id="6C39C2E644FE56DF4C7417C1D52B6381">
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<mods:date id="32D1404D500547325DFAEB94FD7E705A">2015</mods:date>
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<mods:number id="E1C4BAE60DE6C679A23E5278DD8549AD">2015-09-30</mods:number>
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<mods:number id="A2D4087D0404BD5E09FE572DB4ABF79A">117</mods:number>
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<mods:url id="0C764C4C5C9327FC499E1B57472E211D">http://dx.doi.org/10.1016/j.phytochem.2015.07.003</mods:url>
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<mods:classification id="258FCA66336AB1E692EB0DF3324AB264">journal article</mods:classification>
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<mods:identifier id="6A788A410F5595B886C5AEFA4B1B2AED" type="DOI">10.1016/j.phytochem.2015.07.003</mods:identifier>
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<mods:identifier id="3164388796730981BA3E9917D9F499DD" type="ISSN">1873-3700</mods:identifier>
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<treatment id="B67887E1FFD12862BA61056A58BC59F1" LSID="urn:lsid:plazi:treatment:B67887E1FFD12862BA61056A58BC59F1" httpUri="http://treatment.plazi.org/id/B67887E1FFD12862BA61056A58BC59F1" lastPageId="7" lastPageNumber="431" pageId="1" pageNumber="425">
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<subSubSection id="76CB657CFFD12864BA61056A5A0D5D52" pageId="1" pageNumber="425" type="nomenclature">
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<emphasis id="0CA5EAE5FFD12864BA61056A5A0D5D52" italics="true" pageId="1" pageNumber="425">
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2.1. Chemical and structural characterization of compounds isolated
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<heading id="6526819BFFD12864BA62054E5A0D5D52" box="[113,321,1074,1094]" fontSize="8" level="3" pageId="1" pageNumber="425" reason="8">
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from
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<taxonomicName id="F9D14D74FFD12864BAB5054E5A0D5D52" ID-CoL="684FL" authority="Merr." authorityName="Merr." box="[166,321,1074,1094]" class="Magnoliopsida" family="Moraceae" genus="Artocarpus" kingdom="Plantae" order="Rosales" pageId="1" pageNumber="425" phylum="Tracheophyta" rank="species" species="xanthocarpus">A. xanthocarpus</taxonomicName>
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</heading>
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</emphasis>
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</paragraph>
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</subSubSection>
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<subSubSection id="76CB657CFFD12862BA82051758BC59F1" lastPageId="7" lastPageNumber="431" pageId="1" pageNumber="425" type="biology_ecology">
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<paragraph id="3E6E36F7FFD12864BA8205175AA95E23" blockId="1.[113,783,1127,2015]" pageId="1" pageNumber="425">
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Compound
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<emphasis id="0CA5EAE5FFD12864BB1705175A5D5D6A" bold="true" box="[260,273,1131,1150]" pageId="1" pageNumber="425">1</emphasis>
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was obtained as fine yellowish needles, [
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<emphasis id="0CA5EAE5FFD12864B8B8051559F45D6A" box="[683,696,1129,1150]" italics="true" pageId="1" pageNumber="425">OE</emphasis>
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]
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<emphasis id="0CA5EAE5FFD12864B8CB051759A55D69" box="[728,745,1131,1149]" italics="true" pageId="1" pageNumber="425">—</emphasis>
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206 (
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<emphasis id="0CA5EAE5FFD12864BA6905FA5BC85D8E" box="[122,132,1158,1178]" italics="true" pageId="1" pageNumber="425">c</emphasis>
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0.01, methanol). The molecular formula C
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H
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O
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<subScript id="A25534B2FFD12864B8A105EC59F75D88" attach="both" box="[690,699,1168,1180]" fontSize="5" pageId="1" pageNumber="425">7</subScript>
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Na was deduced from HRESIMS (
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<emphasis id="0CA5EAE5FFD12864BB6305DD5ACF5DA1" box="[368,387,1185,1205]" italics="true" pageId="1" pageNumber="425">m</emphasis>
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/
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<emphasis id="0CA5EAE5FFD12864BB9805DD5AD95DA1" box="[395,405,1185,1205]" italics="true" pageId="1" pageNumber="425">z</emphasis>
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461.1573 [M+Na]
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<superScript id="C9A49BBFFFD12864B85F05E359195DBF" attach="none" box="[588,597,1183,1195]" fontSize="5" pageId="1" pageNumber="425">+</superScript>
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). The IR spectrum exhibited absorption peaks attributable to a hydroxy group (
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<emphasis id="0CA5EAE5FFD12864BAC305AB5B905DF7" box="[208,220,1239,1251]" italics="true" pageId="1" pageNumber="425">—</emphasis>
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1
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</superScript>
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), a conjugated carbonyl group (
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<superScript id="C9A49BBFFFD12864B89F05AB59ED5DF6" attach="left" box="[652,673,1238,1251]" fontSize="5" pageId="1" pageNumber="425">
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<emphasis id="0CA5EAE5FFD12864B89F05AB59D45DF7" box="[652,664,1239,1251]" italics="true" pageId="1" pageNumber="425">—</emphasis>
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1
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), and aromatic rings (1613, 1562, and
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<quantity id="F9299B12FFD12864BBD5058A59515C1E" box="[454,541,1270,1290]" metricMagnitude="1" metricUnit="m" metricValue="1.464" pageId="1" pageNumber="425" unit="cm" value="1464.0">1464 cm</quantity>
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<superScript id="C9A49BBFFFD12864B80E058F597E5DEA" attach="left" box="[541,562,1266,1279]" fontSize="5" pageId="1" pageNumber="425">
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<emphasis id="0CA5EAE5FFD12864B80E058F59655DEB" box="[541,553,1267,1279]" italics="true" pageId="1" pageNumber="425">—</emphasis>
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1
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</superScript>
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). The UV spectrum showed absorbance maxima at 340 and
|
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<quantity id="F9299B12FFD12864B805046E59285C31" box="[534,612,1298,1317]" metricMagnitude="-7" metricUnit="m" metricValue="2.7" pageId="1" pageNumber="425" unit="nm" value="270.0">270 nm</quantity>
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, typical of a flavone skeleton (
|
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<bibRefCitation id="5A404B06FFD12864BB0204525ABE5C55" author="Musthapa, I. & Juliawaty, L. D. & Syah, Y. M. & Hakim, E. H. & Latip, J. & Ghisalberti, E. L." box="[273,498,1326,1345]" pageId="1" pageNumber="425" pagination="191 - 194" refId="ref14899" refString="Musthapa, I., Juliawaty, L. D., Syah, Y. M., Hakim, E. H., Latip, J., Ghisalberti, E. L., 2009. An oxepinoflavone from Artocarpus elasticus with cytotoxic activity against P- 388 cells. Arch. Pharm. Res. 32, 191 - 194." type="journal article" year="2009">Musthapa et al., 2009</bibRefCitation>
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). The
|
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|
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H NMR spectrum of
|
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<emphasis id="0CA5EAE5FFD12864BA6204365B325C49" bold="true" box="[113,126,1354,1373]" pageId="1" pageNumber="425">1</emphasis>
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(
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<tableCitation id="7353034CFFD12864BA9D04365B955C49" box="[142,217,1354,1373]" captionStart="Table 1" captionStartId="2.[87,131,183,197]" captionTargetPageId="2" captionText="Table 1 1H (400 MHz) and 13C NMR (100 MHz) spectroscopic data of compounds 1, 2, and 6." httpUri="http://table.plazi.org/id/6AAE667FFFD22867BA4401CB59BB59C8" pageId="1" pageNumber="425" tableUuid="6AAE667FFFD22867BA4401CB59BB59C8">Table 1</tableCitation>
|
||
) indicated the presence of a 3,3-dimethylallyl group at
|
||
<emphasis id="0CA5EAE5FFD12864BA62041A5B305C6D" box="[113,124,1382,1401]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
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1.65 (3H, s,
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-17), 1.78 (3H, s,
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<subScript id="A25534B2FFD12864BBE204135AB65C6F" attach="left" box="[497,506,1391,1403]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
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-18), 3.36 (2H, d,
|
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<emphasis id="0CA5EAE5FFD12864B8BE041959F85C6D" box="[685,692,1381,1401]" italics="true" pageId="1" pageNumber="425">J</emphasis>
|
||
= 7.2 Hz, H-14), and 5.28 (1H, br t,
|
||
<emphasis id="0CA5EAE5FFD12864BB9204FD5AC45C81" box="[385,392,1409,1429]" italics="true" pageId="1" pageNumber="425">J</emphasis>
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= 7.2 Hz, H-15). The UV spectrum did not show a bathochromic shift after addition of a AlCl
|
||
<subScript id="A25534B2FFD12864B8DF04DB59995CA7" attach="left" box="[716,725,1447,1459]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
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||
shift reagent, suggesting a C-6 substitution pattern on the prenyl group (
|
||
<bibRefCitation id="5A404B06FFD12864BA6904AA5A0D5CFC" author="Nomura, T. & Fukai, T. & Yamada, S. & Katayanagi, M." box="[122,321,1493,1513]" pageId="1" pageNumber="425" pagination="1394 - 1402" refId="ref14964" refString="Nomura, T., Fukai, T., Yamada, S., Katayanagi, M., 1978. Studies on the constituents of the cultivated mulberry tree. I. Three new prenylflavones from the root bark of Morus alba L. Chem. Pharm. Bull. 26, 1394 - 1402." type="journal article" year="1978">Nomura et al., 1978</bibRefCitation>
|
||
). An ABX coupling system with resonances at
|
||
<emphasis id="0CA5EAE5FFD12864BA62048E5B305F11" box="[113,124,1522,1541]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
6.67 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD12864BB14048C5A425F10" box="[263,270,1520,1540]" italics="true" pageId="1" pageNumber="425">J</emphasis>
|
||
= 2.4 Hz, H-3
|
||
<emphasis id="0CA5EAE5FFD12864BB8404935AD75CEF" box="[407,411,1519,1531]" italics="true" pageId="1" pageNumber="425">
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<superScript id="C9A49BBFFFD12864BB8404935AD75CEF" attach="none" box="[407,411,1519,1531]" fontSize="5" pageId="1" pageNumber="425">0</superScript>
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</emphasis>
|
||
), 6.72 (1H, dd,
|
||
<emphasis id="0CA5EAE5FFD12864B853048C590B5F10" box="[576,583,1520,1540]" italics="true" pageId="1" pageNumber="425">J</emphasis>
|
||
= 8.8, 2.4 Hz, H-5
|
||
<emphasis id="0CA5EAE5FFD12864B8EE0493584D5CEF" box="[765,769,1519,1531]" italics="true" pageId="1" pageNumber="425">
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</emphasis>
|
||
), and 7.92 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD12864BB3D07705A795F34" box="[302,309,1548,1568]" italics="true" pageId="1" pageNumber="425">J</emphasis>
|
||
= 8.8 Hz, H-6
|
||
<emphasis id="0CA5EAE5FFD12864BBD207775A895F03" box="[449,453,1547,1559]" italics="true" pageId="1" pageNumber="425">
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</emphasis>
|
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) was assigned as ring
|
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<collectionCode id="58C0AE32FFD12864B8D6077259985F35" box="[709,724,1550,1569]" country="Germany" lsid="urn:lsid:biocol.org:col:15534" name="Botanischer Garten und Botanisches Museum Berlin-Dahlem, Zentraleinrichtung der Freien Universitaet" pageId="1" pageNumber="425" type="Herbarium">B</collectionCode>
|
||
. Two methyl groups at
|
||
<emphasis id="0CA5EAE5FFD12864BB3907555A795F28" box="[298,309,1577,1596]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
1.34 (3H, s,
|
||
<collectingCountry id="46C67667FFD12864BBA907555A9B5F28" box="[442,471,1577,1596]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864BBCB074E5AAD5F2A" attach="right" box="[472,481,1586,1598]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-12) and 1.36 (3H, s,
|
||
<collectingCountry id="46C67667FFD12864B8AD075559975F28" box="[702,731,1577,1596]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864B8C8074E59A85F2A" attach="left" box="[731,740,1586,1598]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-13) and an AMX coupling system at
|
||
<emphasis id="0CA5EAE5FFD12864BBDE07395A945F4C" box="[461,472,1605,1624]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
2.59 (1H, dd,
|
||
<emphasis id="0CA5EAE5FFD12864B860073859365F4C" box="[627,634,1604,1624]" italics="true" pageId="1" pageNumber="425">J</emphasis>
|
||
= 16.4, 9.6 Hz, H-9a), 3.51 (1H, dd,
|
||
<emphasis id="0CA5EAE5FFD12864BB44071C5A125F60" box="[343,350,1632,1652]" italics="true" pageId="1" pageNumber="425">J</emphasis>
|
||
= 16.4, 2.0 Hz, H-9b), and 4.02 (1H, dd,
|
||
<emphasis id="0CA5EAE5FFD12864BA6207005B345F84" box="[113,120,1660,1680]" italics="true" pageId="1" pageNumber="425">J</emphasis>
|
||
= 9.6, 2.0 Hz, H-10) suggested the characteristics of an oxepin ring (
|
||
<bibRefCitation id="5A404B06FFD12864BA6907E55A785FB8" author="Hakim, E. H. & Fahriyati, A. & Kau, M. S. & Achmad, S. A. & Makmur, L. & Ghisalberti, E. L. & Nomura, T." box="[122,308,1689,1708]" pageId="1" pageNumber="425" pagination="613 - 615" refId="ref13557" refString="Hakim, E. H., Fahriyati, A., Kau, M. S., Achmad, S. A., Makmur, L., Ghisalberti, E. L., Nomura, T., 1999. Artoindonesianins A and B, two new prenylated flavones from the root of Artocarpus champeden. J. Nat. Prod. 62, 613 - 615." type="journal article" year="1999">Hakim et al., 1999</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="5A404B06FFD12864BB2D07E559595FB8" author="Musthapa, I. & Juliawaty, L. D. & Syah, Y. M. & Hakim, E. H. & Latip, J. & Ghisalberti, E. L." box="[318,533,1689,1708]" pageId="1" pageNumber="425" pagination="191 - 194" refId="ref14899" refString="Musthapa, I., Juliawaty, L. D., Syah, Y. M., Hakim, E. H., Latip, J., Ghisalberti, E. L., 2009. An oxepinoflavone from Artocarpus elasticus with cytotoxic activity against P- 388 cells. Arch. Pharm. Res. 32, 191 - 194." type="journal article" year="2009">Musthapa et al., 2009</bibRefCitation>
|
||
). The
|
||
<superScript id="C9A49BBFFFD12864B84007E9592A5FB5" attach="right" box="[595,614,1685,1697]" fontSize="5" pageId="1" pageNumber="425">13</superScript>
|
||
C NMR signals at
|
||
<emphasis id="0CA5EAE5FFD12864BA6207C95B305FDC" box="[113,124,1717,1736]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
25.7(C-9), 92.3(C-10), and 73.1 (C-11) were similar to those of artelastinin (
|
||
<bibRefCitation id="5A404B06FFD12864BAE507AC5AFC5FF0" author="Kijjoa, A. & Cidade, H. M. & Gonzalez, M. J. T. G. & Afonso, C. M. & Silva, A. M. S. & Herz, W." box="[246,432,1744,1764]" pageId="1" pageNumber="425" pagination="875 - 878" refId="ref14008" refString="Kijjoa, A., Cidade, H. M., Gonzalez, M. J. T. G., Afonso, C. M., Silva, A. M. S., Herz, W., 1998. Further prenylflavonoids from Artocarpus elasticus. Phytochemistry 47, 875 - 878." type="journal article" year="1998">Kijjoa et al., 1998</bibRefCitation>
|
||
), indicating that the prenyl side-chain at C-3 is cyclized with a hydroxy group at C-2
|
||
<emphasis id="0CA5EAE5FFD12864B88E079659ED5FE2" box="[669,673,1770,1782]" italics="true" pageId="1" pageNumber="425">
|
||
<superScript id="C9A49BBFFFD12864B88E079659ED5FE2" attach="none" box="[669,673,1770,1782]" fontSize="5" pageId="1" pageNumber="425">0</superScript>
|
||
</emphasis>
|
||
. Based on these observations, compound
|
||
<emphasis id="0CA5EAE5FFD12864BBBD06745AF75E0F" bold="true" box="[430,443,1800,1819]" pageId="1" pageNumber="425">1</emphasis>
|
||
could be assigned as shown, and is designated artoxanthocarpuone A.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD12864BA82063C5E915AAF" blockId="1.[113,783,1127,2015]" lastBlockId="1.[831,1501,182,2015]" pageId="1" pageNumber="425">
|
||
Compound
|
||
<emphasis id="0CA5EAE5FFD12864BB17063C5A5D5E47" bold="true" box="[260,273,1856,1875]" pageId="1" pageNumber="425">2</emphasis>
|
||
was obtained as a yellowish powder with a molecular formula of C
|
||
<subScript id="A25534B2FFD12864BB0A06195A605E65" attach="right" box="[281,300,1893,1905]" fontSize="5" pageId="1" pageNumber="425">31</subScript>
|
||
H
|
||
<subScript id="A25534B2FFD12864BB2F06195A025E65" attach="right" box="[316,334,1893,1905]" fontSize="5" pageId="1" pageNumber="425">30</subScript>
|
||
O
|
||
<subScript id="A25534B2FFD12864BB4D06195A2B5E65" attach="left" box="[350,359,1893,1905]" fontSize="5" pageId="1" pageNumber="425">8</subScript>
|
||
, as deduced from HRESIMS ([M+H]
|
||
<superScript id="C9A49BBFFFD12864B8D7062459815E70" attach="left" box="[708,717,1880,1892]" fontSize="5" pageId="1" pageNumber="425">+</superScript>
|
||
at
|
||
<emphasis id="0CA5EAE5FFD12864B8F8062759B25E7B" box="[747,766,1883,1903]" italics="true" pageId="1" pageNumber="425">m</emphasis>
|
||
/
|
||
<emphasis id="0CA5EAE5FFD12864B916062758435E7B" box="[773,783,1883,1903]" italics="true" pageId="1" pageNumber="425">z</emphasis>
|
||
531.2016). Its IR spectrum showed absorption bands attributable to a hydroxy (
|
||
<quantity id="F9299B12FFD12864BAE206E85A065EB3" box="[241,330,1940,1959]" metricMagnitude="1" metricUnit="m" metricValue="3.4489999999999994" pageId="1" pageNumber="425" unit="cm" value="3449.0">3449 cm</quantity>
|
||
<superScript id="C9A49BBFFFD12864BB5A06EC5A135E88" attach="left" box="[329,351,1936,1948]" fontSize="5" pageId="1" pageNumber="425">
|
||
<emphasis id="0CA5EAE5FFD12864BB5A06EC5A195E88" box="[329,341,1936,1948]" italics="true" pageId="1" pageNumber="425">—</emphasis>
|
||
1
|
||
</superScript>
|
||
), carbonyl in cyclopentanone and ester (
|
||
<quantity id="F9299B12FFD12864BA6A06CC5B9D5ED7" box="[121,209,1968,1987]" metricMagnitude="1" metricUnit="m" metricValue="1.734" pageId="1" pageNumber="425" unit="cm" value="1734.0">1734 cm</quantity>
|
||
<superScript id="C9A49BBFFFD12864BAC306D05BAA5EAC" attach="left" box="[208,230,1964,1976]" fontSize="5" pageId="1" pageNumber="425">
|
||
<emphasis id="0CA5EAE5FFD12864BAC306D05B905EAC" box="[208,220,1964,1976]" italics="true" pageId="1" pageNumber="425">—</emphasis>
|
||
1
|
||
</superScript>
|
||
), conjugated carbonyl (
|
||
<quantity id="F9299B12FFD12864BBE406D359035ED7" box="[503,591,1967,1987]" metricMagnitude="1" metricUnit="m" metricValue="1.652" pageId="1" pageNumber="425" unit="cm" value="1652.0">1652 cm</quantity>
|
||
<superScript id="C9A49BBFFFD12864B85C06D059285EAC" attach="left" box="[591,612,1964,1976]" fontSize="5" pageId="1" pageNumber="425">
|
||
<emphasis id="0CA5EAE5FFD12864B85C06D059175EAC" box="[591,603,1964,1976]" italics="true" pageId="1" pageNumber="425">—</emphasis>
|
||
1
|
||
</superScript>
|
||
), and benzene (1604 and
|
||
<quantity id="F9299B12FFD12864BAF606B05A705ECB" box="[229,316,1996,2015]" metricMagnitude="1" metricUnit="m" metricValue="1.47" pageId="1" pageNumber="425" unit="cm" value="1470.0">1470 cm</quantity>
|
||
<superScript id="C9A49BBFFFD12864BB2F06B45A1D5EC0" attach="left" box="[316,337,1992,2004]" fontSize="5" pageId="1" pageNumber="425">
|
||
<emphasis id="0CA5EAE5FFD12864BB2F06B45A045EC0" box="[316,328,1992,2004]" italics="true" pageId="1" pageNumber="425">—</emphasis>
|
||
1
|
||
</superScript>
|
||
) functional groups. The UV spectrum of
|
||
<emphasis id="0CA5EAE5FFD12864B91106B758435ECA" bold="true" box="[770,783,1995,2014]" pageId="1" pageNumber="425">2</emphasis>
|
||
was similar to that of artoindonesianin C (
|
||
<bibRefCitation id="5A404B06FFD12864BF1301CA5E9859DD" author="Makmur, L. & Syamsurizal, S. & Tukiran, T. & Achmad, S. A. & Aimi, N. & Hakim, E. H. & Kitajima, M. & Takayama, H." box="[1280,1492,182,202]" pageId="1" pageNumber="425" pagination="243 - 244" refId="ref14830" refString="Makmur, L., Syamsurizal, S., Tukiran, T., Achmad, S. A., Aimi, N., Hakim, E. H., Kitajima, M., Takayama, H., 2000. Artoindonesianin C, a new xanthone derivative from Artocarpus teysmanii. J. Nat. Prod. 63, 243 - 244." type="journal article" year="2000">Makmur et al., 2000</bibRefCitation>
|
||
) and was consistent with a xanthone skeleton (
|
||
<bibRefCitation id="5A404B06FFD12864BF3801AF5E8359F1" author="Zou, Y. S. & Hou, A. J. & Zhu, G. F." box="[1323,1487,210,230]" pageId="1" pageNumber="425" pagination="131 - 138" refId="ref15733" refString="Zou, Y. S., Hou, A. J., Zhu, G. F., 2005. Isoprenylated xanthones and flavonoids from Cudrania tricuspidata. Chem. Biodivers. 2, 131 - 138." type="journal article" year="2005">Zou et al., 2005</bibRefCitation>
|
||
). The
|
||
<superScript id="C9A49BBFFFD12864B9780196583859E2" attach="right" box="[875,884,234,246]" fontSize="5" pageId="1" pageNumber="425">1</superScript>
|
||
H and
|
||
<superScript id="C9A49BBFFFD12864B9A80196588259E2" attach="right" box="[955,974,234,246]" fontSize="5" pageId="1" pageNumber="425">13</superScript>
|
||
C NMR spectra of
|
||
<emphasis id="0CA5EAE5FFD12864BE9A01925FDA5815" bold="true" box="[1161,1174,238,257]" pageId="1" pageNumber="425">2</emphasis>
|
||
(
|
||
<tableCitation id="7353034CFFD12864BEB501925FBD5815" box="[1190,1265,238,257]" captionStart="Table 1" captionStartId="2.[87,131,183,197]" captionTargetPageId="2" captionText="Table 1 1H (400 MHz) and 13C NMR (100 MHz) spectroscopic data of compounds 1, 2, and 6." httpUri="http://table.plazi.org/id/6AAE667FFFD22867BA4401CB59BB59C8" pageId="1" pageNumber="425" tableUuid="6AAE667FFFD22867BA4401CB59BB59C8">Table 1</tableCitation>
|
||
) were similar to those of artoindonesianin C, (
|
||
<bibRefCitation id="5A404B06FFD12864BE3500765FA15809" author="Makmur, L. & Syamsurizal, S. & Tukiran, T. & Achmad, S. A. & Aimi, N. & Hakim, E. H. & Kitajima, M. & Takayama, H." box="[1062,1261,266,285]" pageId="1" pageNumber="425" pagination="243 - 244" refId="ref14830" refString="Makmur, L., Syamsurizal, S., Tukiran, T., Achmad, S. A., Aimi, N., Hakim, E. H., Kitajima, M., Takayama, H., 2000. Artoindonesianin C, a new xanthone derivative from Artocarpus teysmanii. J. Nat. Prod. 63, 243 - 244." type="journal article" year="2000">Makmur et al., 2000</bibRefCitation>
|
||
) including the presence of a 2,2-dimethylpyran ring, an isopropenyl group, two methylene protons, and one methoxy group. An aromatic proton at
|
||
<emphasis id="0CA5EAE5FFD12864BF8F003E5EEB5841" box="[1436,1447,322,341]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
8.22 (1H, s, H-8) displayed a carbonyl anisotropic effect, which is characteristic of a xanthone skeleton. In addition, the two hydroxy signals at
|
||
<emphasis id="0CA5EAE5FFD12864B94E00EA582458BD" box="[861,872,406,425]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
5.52 and 12.95 were exchangeable with D
|
||
<subScript id="A25534B2FFD12864BF2600E25E7258BE" attach="both" box="[1333,1342,414,426]" fontSize="5" pageId="1" pageNumber="425">2</subScript>
|
||
O, and the C-1 hydroxy group was shifted downfield at
|
||
<emphasis id="0CA5EAE5FFD12864BEF200CD5FA058D0" box="[1249,1260,433,452]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
12.95 (1H, br s, OH-1), due to a hydrogen bond interaction with the C-9 carbonyl group. By comparison with the spectrum of artoindonesianin C, compound
|
||
<emphasis id="0CA5EAE5FFD12864B92C037958005B0C" bold="true" box="[831,844,517,536]" pageId="1" pageNumber="425">2</emphasis>
|
||
includes a 3,3-dimethylallyl group as characterized by resonances at
|
||
<emphasis id="0CA5EAE5FFD12864B944035D582E5B20" box="[855,866,545,564]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
1.65 (3H, s,
|
||
<collectingCountry id="46C67667FFD12864B9C8035D58B45B20" box="[987,1016,545,564]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864B9EB03565F4D5B22" attach="left" box="[1016,1025,554,566]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-19), 1.87 (3H, s,
|
||
<collectingCountry id="46C67667FFD12864BEBA035D5F8A5B20" box="[1193,1222,545,564]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864BED403565F9C5B22" attach="right" box="[1223,1232,554,566]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-20), 3.61 (2H, d,
|
||
<emphasis id="0CA5EAE5FFD12864BF68035C5ECE5B20" box="[1403,1410,544,564]" italics="true" pageId="1" pageNumber="425">J</emphasis>
|
||
= 7.2 Hz, H-16), and 5.39 (1H, br t,
|
||
<emphasis id="0CA5EAE5FFD12864BE4003405F165B44" box="[1107,1114,572,592]" italics="true" pageId="1" pageNumber="425">J</emphasis>
|
||
= 7.2 Hz, H-17). The HMBC spectrum (
|
||
<figureCitation id="A6EA2A72FFD12864B954032558335B78" box="[839,895,601,620]" captionStart="Fig" captionStartId="3.[338,364,1722,1736]" captionTargetBox="[310,1306,183,1689]" captionTargetId="graphics-612@3.[675,888,748,963]" captionTargetPageId="3" captionText="Fig. 1. Structures of compounds 1–22. Key information obtained from HMQC and HMBC spectra of 2–6 are shown." figureDoi="http://doi.org/10.5281/zenodo.10528886" httpUri="https://zenodo.org/record/10528886/files/figure.png" pageId="1" pageNumber="425">Fig. 1</figureCitation>
|
||
) established the location of the 3,3-dimethylallyl group at C-4 based on connectivities from the resonance at
|
||
<emphasis id="0CA5EAE5FFD12864BF4103095E115B9C" box="[1362,1373,629,648]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
3.61 (H-16) to
|
||
<emphasis id="0CA5EAE5FFD12864B94A03ED58285BB0" box="[857,868,657,676]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
110.0 (C-4), 155.3 (C-4a), and 160.5 (C-3). The NOESY correlations between
|
||
<collectingCountry id="46C67667FFD12864B9C503D058BF5BAB" box="[982,1011,684,703]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864B9E003C958B05BD5" attach="left" box="[1011,1020,693,705]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-19/H-17 and
|
||
<collectingCountry id="46C67667FFD12864BE9E03D05FE75BAB" box="[1165,1195,684,703]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864BEB803C95FF85BD5" attach="left" box="[1195,1204,693,705]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-20/H-16 indicated that
|
||
<collectingCountry id="46C67667FFD12864BFBE03D05E865BAB" box="[1453,1482,684,703]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864BFD903C95E9F5BD5" attach="left" box="[1482,1491,693,705]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
- 19 is
|
||
<emphasis id="0CA5EAE5FFD12864B96F03BB58D95BCF" box="[892,917,711,731]" italics="true" pageId="1" pageNumber="425">cis</emphasis>
|
||
and
|
||
<collectingCountry id="46C67667FFD12864B9DD03B458A75BCF" box="[974,1003,712,731]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864B9F803AD58B85BC9" attach="left" box="[1003,1012,721,733]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-20 is
|
||
<emphasis id="0CA5EAE5FFD12864BE2903BB5F275BCF" box="[1082,1131,711,731]" italics="true" pageId="1" pageNumber="425">trans</emphasis>
|
||
to H-17. A 2,2-dimethylpyran ring was fused along C-2 and C-3, as indicated by HMBC correlations from
|
||
<emphasis id="0CA5EAE5FFD12864B964027C58CE5A07" box="[887,898,768,787]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
6.68 (H-11) to
|
||
<emphasis id="0CA5EAE5FFD12864BE36027C5F7C5A07" box="[1061,1072,768,787]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
80.1 (C-13), 106.4 (C-2), 157.2 (C-1), and 160.5 (C-3). The presence of an isopropenyl group located at C-7 was deduced from the presence of HMBC correlations between
|
||
<emphasis id="0CA5EAE5FFD12864BFC202445E905A5F" box="[1489,1500,824,843]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
2.18 (
|
||
<collectingCountry id="46C67667FFD12864B969022858D65A73" box="[890,922,852,871]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864B98A022158EE5A7D" attach="left" box="[921,930,861,873]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-25) and
|
||
<emphasis id="0CA5EAE5FFD12864BE1602285F5C5A73" box="[1029,1040,852,871]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
118.6 (C-26), 139.6 (C-24), and 143.4 (C-7) and the methylene protons (
|
||
<emphasis id="0CA5EAE5FFD12864BE7A020C5F385A97" box="[1129,1140,880,899]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
5.04 and 5.25, H
|
||
<subScript id="A25534B2FFD12864BF3A02055E7E5A91" attach="left" box="[1321,1330,889,901]" fontSize="5" pageId="1" pageNumber="425">2</subScript>
|
||
-26) with
|
||
<emphasis id="0CA5EAE5FFD12864BF8E020C5EE45A97" box="[1437,1448,880,899]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
25.9 (C-25), 139.6 (C-24), and 143.4 (C-7). Based on these observations,
|
||
<emphasis id="0CA5EAE5FFD12864B92C02DB58005AAE" bold="true" box="[831,844,935,954]" pageId="1" pageNumber="425">2</emphasis>
|
||
can be assigned as shown, and was named artoxanthocarpuone
|
||
<collectionCode id="58C0AE32FFD12864BFD902D45E955AAF" box="[1482,1497,936,955]" country="Germany" lsid="urn:lsid:biocol.org:col:15534" name="Botanischer Garten und Botanisches Museum Berlin-Dahlem, Zentraleinrichtung der Freien Universitaet" pageId="1" pageNumber="425" type="Herbarium">B</collectionCode>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD12864B94D02BF5FA95FB8" blockId="1.[831,1501,182,2015]" pageId="1" pageNumber="425">
|
||
Compound
|
||
<emphasis id="0CA5EAE5FFD12864B9C002BF58AC5AC2" bold="true" box="[979,992,963,982]" pageId="1" pageNumber="425">3</emphasis>
|
||
, a colorless crystal, was assigned a molecular formula of C
|
||
<subScript id="A25534B2FFD12864B9B1029458F85AE0" attach="both" box="[930,948,1000,1012]" fontSize="5" pageId="1" pageNumber="425">26</subScript>
|
||
H
|
||
<subScript id="A25534B2FFD12864B9D6029458945AE0" attach="both" box="[965,984,1000,1012]" fontSize="5" pageId="1" pageNumber="425">32</subScript>
|
||
O
|
||
<subScript id="A25534B2FFD12864B9F4029458BC5AE0" attach="both" box="[999,1008,1000,1012]" fontSize="5" pageId="1" pageNumber="425">5</subScript>
|
||
Na by HRESIMS ([M+Na]
|
||
<superScript id="C9A49BBFFFD12864BEFF02A75FB95AF3" attach="left" box="[1260,1269,987,999]" fontSize="5" pageId="1" pageNumber="425">+</superScript>
|
||
at
|
||
<emphasis id="0CA5EAE5FFD12864BF0B02A25E675AE6" box="[1304,1323,990,1010]" italics="true" pageId="1" pageNumber="425">m</emphasis>
|
||
/
|
||
<emphasis id="0CA5EAE5FFD12864BF2002A25E715AE6" box="[1331,1341,990,1010]" italics="true" pageId="1" pageNumber="425">z</emphasis>
|
||
447.2145). The UV spectrum of
|
||
<emphasis id="0CA5EAE5FFD12864B9F4028758B85D1A" bold="true" box="[999,1012,1019,1038]" pageId="1" pageNumber="425">3</emphasis>
|
||
resembled those of lakoochin A (
|
||
<emphasis id="0CA5EAE5FFD12864BF5E02875E165D1A" bold="true" box="[1357,1370,1019,1038]" pageId="1" pageNumber="425">8</emphasis>
|
||
) and 2-arylbenzofuran derivatives (
|
||
<bibRefCitation id="5A404B06FFD12864BE2E056B5E5A5D3E" author="Shen, H. & Hou, A. J." box="[1085,1302,1047,1066]" pageId="1" pageNumber="425" pagination="1451 - 1456" refId="ref15413" refString="Shen, H., Hou, A. J., 2008. Prenylated 2 - arylbenzofurans from Artocarpus petelotii. Nat. Prod. Res. 22, 1451 - 1456." type="journal article" year="2008">Shen and Hou, 2008</bibRefCitation>
|
||
). The IR spectrum showed absorption bands typical of a hydroxy group (
|
||
<quantity id="F9299B12FFD12864BF74054F5EF35D52" box="[1383,1471,1075,1094]" metricMagnitude="1" metricUnit="m" metricValue="3.3989999999999996" pageId="1" pageNumber="425" unit="cm" value="3399.0">3399 cm</quantity>
|
||
<superScript id="C9A49BBFFFD12864BFAC05535E985D2F" attach="left" box="[1471,1492,1071,1083]" fontSize="5" pageId="1" pageNumber="425">
|
||
<emphasis id="0CA5EAE5FFD12864BFAC05535E875D2F" box="[1471,1483,1071,1083]" italics="true" pageId="1" pageNumber="425">—</emphasis>
|
||
1
|
||
</superScript>
|
||
) and an aromatic ring (
|
||
<quantity id="F9299B12FFD12864BE3805335FCF5D76" box="[1067,1155,1103,1122]" metricMagnitude="1" metricUnit="m" metricValue="1.585" pageId="1" pageNumber="425" unit="cm" value="1585.0">1585 cm</quantity>
|
||
<superScript id="C9A49BBFFFD12864BE9005375FD45D43" attach="left" box="[1155,1176,1099,1111]" fontSize="5" pageId="1" pageNumber="425">
|
||
<emphasis id="0CA5EAE5FFD12864BE9005375FC35D43" box="[1155,1167,1099,1111]" italics="true" pageId="1" pageNumber="425">—</emphasis>
|
||
1
|
||
</superScript>
|
||
). The
|
||
<superScript id="C9A49BBFFFD12864BECE05375FAA5D43" attach="right" box="[1245,1254,1099,1111]" fontSize="5" pageId="1" pageNumber="425">1</superScript>
|
||
H and
|
||
<superScript id="C9A49BBFFFD12864BF3C05375E0E5D43" attach="right" box="[1327,1346,1099,1111]" fontSize="5" pageId="1" pageNumber="425">13</superScript>
|
||
C NMR spectra of
|
||
<emphasis id="0CA5EAE5FFD12864B94C051758205D6A" bold="true" box="[863,876,1131,1150]" pageId="1" pageNumber="425">3</emphasis>
|
||
(
|
||
<tableCitation id="7353034CFFD12864B9930517589C5D6A" box="[896,976,1131,1150]" captionStart="Table 2" captionStartId="4.[87,131,183,197]" captionTargetPageId="4" captionText="Table 2 1H (400 MHz) and 13C NMR (100 MHz) spectroscopic data of compounds 3–5." httpUri="http://table.plazi.org/id/6AAE667FFFD42861BA4401CB598D59C8" pageId="1" pageNumber="425" tableUuid="6AAE667FFFD42861BA4401CB598D59C8">Table 2</tableCitation>
|
||
) were similar to those of
|
||
<emphasis id="0CA5EAE5FFD12864BEEA05175E4A5D6A" bold="true" box="[1273,1286,1131,1150]" pageId="1" pageNumber="425">8</emphasis>
|
||
(
|
||
<bibRefCitation id="5A404B06FFD12864BF090517583D5D8E" author="Puntumchai, A. & Kittakoop, P. & Rajviroongit, S. & Vimuttipong, S. & Likhitwitayawuid, K. & Thebtaranonth, Y." pageId="1" pageNumber="425" pagination="485 - 486" refId="ref15253" refString="Puntumchai, A., Kittakoop, P., Rajviroongit, S., Vimuttipong, S., Likhitwitayawuid, K., Thebtaranonth, Y., 2004. Lakoochins A and B, new antimycobacterial stilbene derivatives from Artocarpus lakoocha. J. Nat. Prod. 67, 485 - 486." type="journal article" year="2004">Puntumchai et al., 2004</bibRefCitation>
|
||
), including two methoxy groups, two singlet aromatic protons, a set of ABX coupling systems, and a 3,3-dimethylallyl group. The identification of
|
||
<collectingCountry id="46C67667FFD12864BE3705C35F0D5DC6" box="[1060,1089,1215,1234]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864BE5205BB5F065DC7" attach="left" box="[1089,1098,1223,1235]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-11 and -12 on the 3,3-dimethylallyl group were deduced from the NOESY correlations of
|
||
<collectingCountry id="46C67667FFD12864BF7605A65ECF5DF9" box="[1381,1411,1242,1261]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864BF90059F5EC05DFB" attach="left" box="[1411,1420,1251,1263]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-11/H-8 and
|
||
<collectingCountry id="46C67667FFD12864B978058A58C45C1D" box="[875,904,1270,1289]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864B99A058358DE5C1F" attach="right" box="[905,914,1279,1291]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-12/H-9. In addition, the presence of resonances at
|
||
<emphasis id="0CA5EAE5FFD12864BF8C058A5EE65C1D" box="[1439,1450,1270,1289]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
0.98 (6H, s,
|
||
<collectingCountry id="46C67667FFD12864B99F046E58E55C31" box="[908,937,1298,1317]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864B9BA046758FE5C33" attach="left" box="[937,946,1307,1319]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-16 and 17), 1.59-1.63 (2H, m, H-14), and 2.42–2.47 (2H, m, H-13) and an oxygenated quaternary carbon resonance at
|
||
<emphasis id="0CA5EAE5FFD12864B92C043658065C49" box="[831,842,1354,1373]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
<quantity id="F9299B12FFD12864B941043658D65C49" box="[850,922,1354,1373]" metricMagnitude="0" metricUnit="m" metricValue="1.79832" pageId="1" pageNumber="425" unit="in" value="70.8">70.8 in</quantity>
|
||
the DEPT spectrum collectively suggest that
|
||
<emphasis id="0CA5EAE5FFD12864BF6104365E335C49" bold="true" box="[1394,1407,1354,1373]" pageId="1" pageNumber="425">3</emphasis>
|
||
contains a γ- hydroxyisoamyl chain. The other resonances at C-2 to C-12, C-1
|
||
<emphasis id="0CA5EAE5FFD12864B972040358295C9F" box="[865,869,1407,1419]" italics="true" pageId="1" pageNumber="425">
|
||
<superScript id="C9A49BBFFFD12864B972040358295C9F" attach="left" box="[865,869,1407,1419]" fontSize="5" pageId="1" pageNumber="425">0</superScript>
|
||
</emphasis>
|
||
to C-6
|
||
<emphasis id="0CA5EAE5FFD12864B9A2040358F95C9F" box="[945,949,1407,1419]" italics="true" pageId="1" pageNumber="425">
|
||
<superScript id="C9A49BBFFFD12864B9A2040358F95C9F" attach="none" box="[945,949,1407,1419]" fontSize="5" pageId="1" pageNumber="425">0</superScript>
|
||
</emphasis>
|
||
, and two methoxy groups at C-3
|
||
<emphasis id="0CA5EAE5FFD12864BF0704035E545C9F" box="[1300,1304,1407,1419]" italics="true" pageId="1" pageNumber="425">
|
||
<superScript id="C9A49BBFFFD12864BF0704035E545C9F" attach="left" box="[1300,1304,1407,1419]" fontSize="5" pageId="1" pageNumber="425">0</superScript>
|
||
</emphasis>
|
||
and -5
|
||
<emphasis id="0CA5EAE5FFD12864BF7404035E275C9F" box="[1383,1387,1407,1419]" italics="true" pageId="1" pageNumber="425">
|
||
<superScript id="C9A49BBFFFD12864BF7404035E275C9F" attach="left" box="[1383,1387,1407,1419]" fontSize="5" pageId="1" pageNumber="425">0</superScript>
|
||
</emphasis>
|
||
in the
|
||
<superScript id="C9A49BBFFFD12864BFAF04025E835C9E" attach="right" box="[1468,1487,1406,1418]" fontSize="5" pageId="1" pageNumber="425">13</superScript>
|
||
C NMR (
|
||
<tableCitation id="7353034CFFD12864B99C04E258A55CA5" box="[911,1001,1438,1457]" captionStart="Table 2" captionStartId="4.[87,131,183,197]" captionTargetPageId="4" captionText="Table 2 1H (400 MHz) and 13C NMR (100 MHz) spectroscopic data of compounds 3–5." httpUri="http://table.plazi.org/id/6AAE667FFFD42861BA4401CB598D59C8" pageId="1" pageNumber="425" tableUuid="6AAE667FFFD42861BA4401CB598D59C8">Table 2</tableCitation>
|
||
) spectrum closely resembled those of
|
||
<emphasis id="0CA5EAE5FFD12864BFDC04E15E905CA4" bold="true" box="[1487,1500,1437,1456]" pageId="1" pageNumber="425">8</emphasis>
|
||
(
|
||
<bibRefCitation id="5A404B06FFD12864B95404C55F765CD8" author="Puntumchai, A. & Kittakoop, P. & Rajviroongit, S. & Vimuttipong, S. & Likhitwitayawuid, K. & Thebtaranonth, Y." box="[839,1082,1465,1485]" pageId="1" pageNumber="425" pagination="485 - 486" refId="ref15253" refString="Puntumchai, A., Kittakoop, P., Rajviroongit, S., Vimuttipong, S., Likhitwitayawuid, K., Thebtaranonth, Y., 2004. Lakoochins A and B, new antimycobacterial stilbene derivatives from Artocarpus lakoocha. J. Nat. Prod. 67, 485 - 486." type="journal article" year="2004">Puntumchai et al., 2004</bibRefCitation>
|
||
). The hydroxy group was assigned to be at C-15 based on HMBC correlations from
|
||
<emphasis id="0CA5EAE5FFD12864BEE304AA5FB75CFD" box="[1264,1275,1494,1513]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
0.98 (
|
||
<collectingCountry id="46C67667FFD12864BF2804A95E175CFC" box="[1339,1371,1493,1512]" name="Switzerland" pageId="1" pageNumber="425">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD12864BF4804A25E285CFE" attach="left" box="[1371,1380,1502,1514]" fontSize="5" pageId="1" pageNumber="425">3</subScript>
|
||
-16 and 17) and 1.59–1.63 (H-14) to
|
||
<emphasis id="0CA5EAE5FFD12864BE56048E5F1C5F11" box="[1093,1104,1522,1541]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
70.8 (C-15). Furthermore, the attachment of the γ- hydroxyisoamyl chain to C-6
|
||
<emphasis id="0CA5EAE5FFD12864BF1B07775E405F03" box="[1288,1292,1547,1559]" italics="true" pageId="1" pageNumber="425">
|
||
<superScript id="C9A49BBFFFD12864BF1B07775E405F03" attach="left" box="[1288,1292,1547,1559]" fontSize="5" pageId="1" pageNumber="425">0</superScript>
|
||
</emphasis>
|
||
was established by comparison with the spectra for compound
|
||
<emphasis id="0CA5EAE5FFD12864BF1707555E5D5F28" bold="true" box="[1284,1297,1577,1596]" pageId="1" pageNumber="425">8</emphasis>
|
||
and was confirmed by the observation of HMBC correlations from
|
||
<emphasis id="0CA5EAE5FFD12864BF3007395E625F4C" box="[1315,1326,1605,1624]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
2.45 (H-13) to
|
||
<emphasis id="0CA5EAE5FFD12864BFC207395E905F4C" box="[1489,1500,1605,1624]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
46.1 (C-14), 70.8 (C-15), 125.6 (C-6
|
||
<emphasis id="0CA5EAE5FFD12864BEAA07235FF15F7F" box="[1209,1213,1631,1643]" italics="true" pageId="1" pageNumber="425">
|
||
<superScript id="C9A49BBFFFD12864BEAA07235FF15F7F" attach="none" box="[1209,1213,1631,1643]" fontSize="5" pageId="1" pageNumber="425">0</superScript>
|
||
</emphasis>
|
||
), and 133.5 (C-1
|
||
<emphasis id="0CA5EAE5FFD12864BF6707235E345F7F" box="[1396,1400,1631,1643]" italics="true" pageId="1" pageNumber="425">
|
||
<superScript id="C9A49BBFFFD12864BF6707235E345F7F" attach="none" box="[1396,1400,1631,1643]" fontSize="5" pageId="1" pageNumber="425">0</superScript>
|
||
</emphasis>
|
||
) (
|
||
<figureCitation id="A6EA2A72FFD12864BF86071D5E835F60" box="[1429,1487,1633,1652]" captionStart="Fig" captionStartId="3.[338,364,1722,1736]" captionTargetBox="[310,1306,183,1689]" captionTargetId="graphics-612@3.[675,888,748,963]" captionTargetPageId="3" captionText="Fig. 1. Structures of compounds 1–22. Key information obtained from HMQC and HMBC spectra of 2–6 are shown." figureDoi="http://doi.org/10.5281/zenodo.10528886" httpUri="https://zenodo.org/record/10528886/files/figure.png" pageId="1" pageNumber="425">Fig. 1</figureCitation>
|
||
). Since compound
|
||
<emphasis id="0CA5EAE5FFD12864B9E2070158B25F84" bold="true" box="[1009,1022,1661,1680]" pageId="1" pageNumber="425">3</emphasis>
|
||
is the C-15 hydration product of lakoochin A (
|
||
<emphasis id="0CA5EAE5FFD12864B95407E558185FB8" bold="true" box="[839,852,1689,1708]" pageId="1" pageNumber="425">8</emphasis>
|
||
), it was named as hydroxylakoochin A.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD12867B94D07C85B995E79" blockId="1.[831,1501,182,2015]" lastBlockId="2.[87,757,1603,2013]" lastPageId="2" lastPageNumber="426" pageId="1" pageNumber="425">
|
||
Compound
|
||
<emphasis id="0CA5EAE5FFD12864B9C607C858AE5FD3" bold="true" box="[981,994,1716,1735]" pageId="1" pageNumber="425">4</emphasis>
|
||
was isolated as an off-whitish powder and [
|
||
<emphasis id="0CA5EAE5FFD12864BFA607CF5E8E5FDC" box="[1461,1474,1715,1736]" italics="true" pageId="1" pageNumber="425">OE</emphasis>
|
||
]
|
||
<subScript id="A25534B2FFD12864BFD907C25E995FDE" attach="left" box="[1482,1493,1726,1738]" fontSize="5" pageId="1" pageNumber="425">D</subScript>
|
||
<superScript id="C9A49BBFFFD12864BFD907CC5E915FA8" attach="none" box="[1482,1501,1712,1724]" fontSize="5" pageId="1" pageNumber="425">25</superScript>
|
||
+3.7 (
|
||
<emphasis id="0CA5EAE5FFD12864B96E07B358CB5FF7" box="[893,903,1743,1763]" italics="true" pageId="1" pageNumber="425">c</emphasis>
|
||
0.09, methanol). Its molecular formula was assigned as C
|
||
<subScript id="A25534B2FFD12864B95F078958135E15" attach="both" box="[844,863,1781,1793]" fontSize="5" pageId="1" pageNumber="425">27</subScript>
|
||
H
|
||
<subScript id="A25534B2FFD12864B97C078958CD5E15" attach="right" box="[879,897,1781,1793]" fontSize="5" pageId="1" pageNumber="425">34</subScript>
|
||
O
|
||
<subScript id="A25534B2FFD12864B982078958D65E15" attach="both" box="[913,922,1781,1793]" fontSize="5" pageId="1" pageNumber="425">6</subScript>
|
||
Na based on HRESIMS ([M+Na]
|
||
<superScript id="C9A49BBFFFD12864BEF107955FA75FE1" attach="left" box="[1250,1259,1769,1781]" fontSize="5" pageId="1" pageNumber="425">+</superScript>
|
||
at
|
||
<emphasis id="0CA5EAE5FFD12864BF0007975E6A5FEB" box="[1299,1318,1771,1791]" italics="true" pageId="1" pageNumber="425">m</emphasis>
|
||
/
|
||
<emphasis id="0CA5EAE5FFD12864BF3D07975E745FEB" box="[1326,1336,1771,1791]" italics="true" pageId="1" pageNumber="425">z</emphasis>
|
||
477.2255). The UV spectrum was typical for a 2-arylbenzofuran derivative (
|
||
<bibRefCitation id="5A404B06FFD12864BFB8067458945E23" author="Shen, H. & Hou, A. J." pageId="1" pageNumber="425" pagination="1451 - 1456" refId="ref15413" refString="Shen, H., Hou, A. J., 2008. Prenylated 2 - arylbenzofurans from Artocarpus petelotii. Nat. Prod. Res. 22, 1451 - 1456." type="journal article" year="2008">Shen and Hou, 2008</bibRefCitation>
|
||
) and was similar to that of compound
|
||
<emphasis id="0CA5EAE5FFD12864BF6D06585EC75E23" bold="true" box="[1406,1419,1828,1847]" pageId="1" pageNumber="425">3</emphasis>
|
||
. The IR spectrum showed absorption values attributable to a hydroxy group (
|
||
<quantity id="F9299B12FFD12864B99D062058AA5E7B" box="[910,998,1884,1903]" metricMagnitude="1" metricUnit="m" metricValue="3.3689999999999998" pageId="1" pageNumber="425" unit="cm" value="3369.0">3369 cm</quantity>
|
||
<superScript id="C9A49BBFFFD12864B9F5062458B75E70" attach="left" box="[998,1019,1880,1892]" fontSize="5" pageId="1" pageNumber="425">
|
||
<emphasis id="0CA5EAE5FFD12864B9F5062458BE5E70" box="[998,1010,1880,1892]" italics="true" pageId="1" pageNumber="425">—</emphasis>
|
||
1
|
||
</superScript>
|
||
) and aromatic rings (1624 and
|
||
<quantity id="F9299B12FFD12864BF7006205EF65E7B" box="[1379,1466,1884,1903]" metricMagnitude="1" metricUnit="m" metricValue="1.5859999999999999" pageId="1" pageNumber="425" unit="cm" value="1586.0">1586 cm</quantity>
|
||
<superScript id="C9A49BBFFFD12864BFAA06245E835E70" attach="left" box="[1465,1487,1880,1892]" fontSize="5" pageId="1" pageNumber="425">
|
||
<emphasis id="0CA5EAE5FFD12864BFAA06245E895E70" box="[1465,1477,1880,1892]" italics="true" pageId="1" pageNumber="425">—</emphasis>
|
||
1
|
||
</superScript>
|
||
). The
|
||
<superScript id="C9A49BBFFFD12864B97E0608583A5E94" attach="right" box="[877,886,1908,1920]" fontSize="5" pageId="1" pageNumber="425">1</superScript>
|
||
H NMR spectrum of
|
||
<emphasis id="0CA5EAE5FFD12864BE4006045F2C5E9F" bold="true" box="[1107,1120,1912,1931]" pageId="1" pageNumber="425">4</emphasis>
|
||
was similar to that of compound
|
||
<emphasis id="0CA5EAE5FFD12864BFDC06045E905E9F" bold="true" box="[1487,1500,1912,1931]" pageId="1" pageNumber="425">3</emphasis>
|
||
except for an oxymethine proton (
|
||
<emphasis id="0CA5EAE5FFD12864BEAE06E85F845EB3" box="[1213,1224,1940,1959]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
3.59–3.63, 1H, m, H-14) instead of methylene protons (
|
||
<emphasis id="0CA5EAE5FFD12864BE6F06CC5FCB5ED7" box="[1148,1159,1968,1987]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
1.59–1.63, 2H, m, H-14) at C-14, and the presence of an additional methoxy group at
|
||
<emphasis id="0CA5EAE5FFD12864BF4B06B05E2F5ECB" box="[1368,1379,1996,2015]" italics="true" pageId="1" pageNumber="425">δ</emphasis>
|
||
2.99 (3H, s, OCH
|
||
<subScript id="A25534B2FFD22867BA9707305BC15F4C" attach="left" box="[132,141,1612,1624]" fontSize="5" pageId="2" pageNumber="426">3</subScript>
|
||
-14). The spectra suggested that the methoxy group was on the γ- hydroxyisoamyl chain, and this was confirmed by multiple HMBC correlations, including OCH
|
||
<subScript id="A25534B2FFD22867BBA407F85A8C5F84" attach="right" box="[439,448,1668,1680]" fontSize="5" pageId="2" pageNumber="426">3</subScript>
|
||
-14 (
|
||
<emphasis id="0CA5EAE5FFD22867BBE107075AB15F9A" box="[498,509,1659,1678]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
2.99)/C-14 (
|
||
<emphasis id="0CA5EAE5FFD22867B893070759C75F9A" box="[640,651,1659,1678]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
77.9),
|
||
<subScript id="A25534B2FFD22867B8C0070759B95F9A" attach="right" box="[723,757,1659,1680]" fontSize="5" pageId="2" pageNumber="426">Ha-</subScript>
|
||
13 (
|
||
<emphasis id="0CA5EAE5FFD22867BA9207EB5BC05FBE" box="[129,140,1687,1706]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
2.58) and
|
||
<subScript id="A25534B2FFD22867BAEF07EB5A525FBE" attach="left" box="[252,286,1687,1707]" fontSize="5" pageId="2" pageNumber="426">Hb-</subScript>
|
||
13 (
|
||
<emphasis id="0CA5EAE5FFD22867BB5B07EB5A1F5FBE" box="[328,339,1687,1706]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
2.74)/C-14 (
|
||
<emphasis id="0CA5EAE5FFD22867BBC607EB5AAC5FBE" box="[469,480,1687,1706]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
77.9), and
|
||
<collectingCountry id="46C67667FFD22867B84507EB59385FBE" box="[598,628,1687,1706]" name="Switzerland" pageId="2" pageNumber="426">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD22867B86007DC59305FB8" attach="left" box="[627,636,1696,1708]" fontSize="5" pageId="2" pageNumber="426">3</subScript>
|
||
-16 (
|
||
<emphasis id="0CA5EAE5FFD22867B8BC07EB59F65FBE" box="[687,698,1687,1706]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
0.93) and -17 (
|
||
<emphasis id="0CA5EAE5FFD22867BAAB07CF5B8F5FD2" box="[184,195,1715,1734]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
0.96)/C-15 (
|
||
<emphasis id="0CA5EAE5FFD22867BB5407CF5A1E5FD2" box="[327,338,1715,1734]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
78.3) (
|
||
<figureCitation id="A6EA2A72FFD22867BB8D07CE5A9A5FD1" box="[414,470,1714,1733]" captionStart="Fig" captionStartId="3.[338,364,1722,1736]" captionTargetBox="[310,1306,183,1689]" captionTargetId="graphics-612@3.[675,888,748,963]" captionTargetPageId="3" captionText="Fig. 1. Structures of compounds 1–22. Key information obtained from HMQC and HMBC spectra of 2–6 are shown." figureDoi="http://doi.org/10.5281/zenodo.10528886" httpUri="https://zenodo.org/record/10528886/files/figure.png" pageId="2" pageNumber="426">Fig. 1</figureCitation>
|
||
). The HMBC correlations of H-13 to C-6
|
||
<emphasis id="0CA5EAE5FFD22867BADD07B05B9E5FCC" box="[206,210,1740,1752]" italics="true" pageId="2" pageNumber="426">
|
||
<superScript id="C9A49BBFFFD22867BADD07B05B9E5FCC" attach="left" box="[206,210,1740,1752]" fontSize="5" pageId="2" pageNumber="426">0</superScript>
|
||
</emphasis>
|
||
(
|
||
<emphasis id="0CA5EAE5FFD22867BAF107B35BA15FF6" box="[226,237,1743,1762]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
122.7), C-1
|
||
<emphasis id="0CA5EAE5FFD22867BB7107B05A2A5FCC" box="[354,358,1740,1752]" italics="true" pageId="2" pageNumber="426">
|
||
<superScript id="C9A49BBFFFD22867BB7107B05A2A5FCC" attach="left" box="[354,358,1740,1752]" fontSize="5" pageId="2" pageNumber="426">0</superScript>
|
||
</emphasis>
|
||
(
|
||
<emphasis id="0CA5EAE5FFD22867BB6507B35ACD5FF6" box="[374,385,1743,1762]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
134.5), and C-5
|
||
<emphasis id="0CA5EAE5FFD22867B83107B0596A5FCC" box="[546,550,1740,1752]" italics="true" pageId="2" pageNumber="426">
|
||
<superScript id="C9A49BBFFFD22867B83107B0596A5FCC" attach="left" box="[546,550,1740,1752]" fontSize="5" pageId="2" pageNumber="426">0</superScript>
|
||
</emphasis>
|
||
(
|
||
<emphasis id="0CA5EAE5FFD22867B82507B3590D5FF6" box="[566,577,1743,1762]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
158.5) confirmed that the β- methoxy-γ- hydroxyisoamyl unit was attached to C-6
|
||
<emphasis id="0CA5EAE5FFD22867B8E3079459B85FE0" box="[752,756,1768,1780]" italics="true" pageId="2" pageNumber="426">
|
||
<superScript id="C9A49BBFFFD22867B8E3079459B85FE0" attach="none" box="[752,756,1768,1780]" fontSize="5" pageId="2" pageNumber="426">0</superScript>
|
||
</emphasis>
|
||
(
|
||
<figureCitation id="A6EA2A72FFD22867BA4C067A5BD65E0D" box="[95,154,1798,1817]" captionStart="Fig" captionStartId="3.[338,364,1722,1736]" captionTargetBox="[310,1306,183,1689]" captionTargetId="graphics-612@3.[675,888,748,963]" captionTargetPageId="3" captionText="Fig. 1. Structures of compounds 1–22. Key information obtained from HMQC and HMBC spectra of 2–6 are shown." figureDoi="http://doi.org/10.5281/zenodo.10528886" httpUri="https://zenodo.org/record/10528886/files/figure.png" pageId="2" pageNumber="426">Fig. 1</figureCitation>
|
||
). The
|
||
<superScript id="C9A49BBFFFD22867BAF1067E5BB95E1A" attach="right" box="[226,245,1794,1806]" fontSize="5" pageId="2" pageNumber="426">13</superScript>
|
||
C NMR spectroscopic data (
|
||
<tableCitation id="7353034CFFD22867B80F067A59265E0D" box="[540,618,1798,1817]" captionStart="Table 2" captionStartId="4.[87,131,183,197]" captionTargetPageId="4" captionText="Table 2 1H (400 MHz) and 13C NMR (100 MHz) spectroscopic data of compounds 3–5." httpUri="http://table.plazi.org/id/6AAE667FFFD42861BA4401CB598D59C8" pageId="2" pageNumber="426" tableUuid="6AAE667FFFD42861BA4401CB598D59C8">Table 2</tableCitation>
|
||
) and ESI-MS results also supported the structure shown for
|
||
<emphasis id="0CA5EAE5FFD22867B893065E59C15E21" bold="true" box="[640,653,1826,1845]" pageId="2" pageNumber="426">4</emphasis>
|
||
(
|
||
<figureCitation id="A6EA2A72FFD22867B8B5065E59A45E21" box="[678,744,1826,1845]" captionStart="Fig" captionStartId="3.[338,364,1722,1736]" captionTargetBox="[310,1306,183,1689]" captionTargetId="graphics-612@3.[675,888,748,963]" captionTargetPageId="3" captionText="Fig. 1. Structures of compounds 1–22. Key information obtained from HMQC and HMBC spectra of 2–6 are shown." figureDoi="http://doi.org/10.5281/zenodo.10528886" httpUri="https://zenodo.org/record/10528886/files/figure.png" pageId="2" pageNumber="426">Fig. 1</figureCitation>
|
||
). Collectively, these findings indicated that compound
|
||
<emphasis id="0CA5EAE5FFD22867B878064259345E45" bold="true" box="[619,632,1854,1873]" pageId="2" pageNumber="426">4</emphasis>
|
||
is methoxylakoochin A.
|
||
</paragraph>
|
||
<caption id="6AAE667FFFD22867BA4401CB59BB59C8" ID-Table-UUID="6AAE667FFFD22867BA4401CB59BB59C8" httpUri="http://table.plazi.org/id/6AAE667FFFD22867BA4401CB59BB59C8" pageId="2" pageNumber="426" startId="2.[87,131,183,197]" targetBox="[110,1452,243,1455]" targetIsTable="true" targetPageId="2" targetType="table">
|
||
<paragraph id="3E6E36F7FFD22867BA4401CB59BB59C8" blockId="2.[87,759,183,220]" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867BA4401CB5BDF59D1" bold="true" box="[87,147,183,197]" pageId="2" pageNumber="426">Table 1</emphasis>
|
||
<superScript id="C9A49BBFFFD22867BA4401B65B1259C0" attach="right" box="[87,94,202,212]" fontSize="4" pageId="2" pageNumber="426">1</superScript>
|
||
H (400 MHz) and
|
||
<superScript id="C9A49BBFFFD22867BAFE01B65BB059C0" attach="right" box="[237,252,202,212]" fontSize="4" pageId="2" pageNumber="426">13</superScript>
|
||
C NMR (100 MHz) spectroscopic data of compounds
|
||
<emphasis id="0CA5EAE5FFD22867B8B301B159E659CF" bold="true" box="[672,682,205,219]" pageId="2" pageNumber="426">1</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD22867B8A001B159F159CF" bold="true" box="[691,701,205,219]" pageId="2" pageNumber="426">2</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD22867B8FA01B159BF59CF" bold="true" box="[745,755,205,219]" pageId="2" pageNumber="426">6</emphasis>
|
||
.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="3E6E36F7FFD22867BA7D018858FB5CBB" pageId="2" pageNumber="426">
|
||
<table id="4CD1C457FFD2D79ABA7D018F5EE05CBB" box="[110,1452,243,1455]" gridcols="7" gridrows="50" pageId="2" pageNumber="426">
|
||
<tr id="80E134B5FFD2D79ABA7D018F5EE05810" box="[110,1452,243,260]" gridrow="0" pageId="2" pageNumber="426" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D018F5BFC5810" box="[110,176,243,260]" gridcol="0" gridrow="0" pageId="2" pageNumber="426">Position</th>
|
||
<th id="C3305DC9FFD2D79ABB1C018F5ACF5810" box="[271,387,243,260]" gridcol="1" gridrow="0" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867BB1C01885A555816" bold="true" box="[271,281,244,258]" pageId="2" pageNumber="426">1</emphasis>
|
||
(acetone-
|
||
<emphasis id="0CA5EAE5FFD22867BB78018F5A395816" box="[363,373,243,258]" italics="true" pageId="2" pageNumber="426">d</emphasis>
|
||
6)
|
||
</th>
|
||
<th id="C3305DC9FFD2D79AB8A5018F58655810" box="[694,809,243,260]" gridcol="3" gridrow="0" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867B8A50188598C5816" bold="true" box="[694,704,244,258]" pageId="2" pageNumber="426">2</emphasis>
|
||
(acetone-
|
||
<emphasis id="0CA5EAE5FFD22867B901018F58505816" box="[786,796,243,258]" italics="true" pageId="2" pageNumber="426">d</emphasis>
|
||
6)
|
||
</th>
|
||
<th id="C3305DC9FFD2D79ABE77018F5F945810" box="[1124,1240,243,260]" gridcol="5" gridrow="0" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867BE7701885F225816" bold="true" box="[1124,1134,244,258]" pageId="2" pageNumber="426">6</emphasis>
|
||
(acetone-
|
||
<emphasis id="0CA5EAE5FFD22867BED2018F5F875816" box="[1217,1227,243,258]" italics="true" pageId="2" pageNumber="426">d</emphasis>
|
||
6)
|
||
</th>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D00695EE05832" box="[110,1452,277,294]" gridrow="1" pageId="2" pageNumber="426" rowspan-0="1">
|
||
<td id="C3305DC9FFD2D79ABB1C00695ACF5832" box="[271,387,277,294]" gridcol="1" gridrow="1" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867BB1C00695A545830" box="[271,280,277,292]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
C, mult.
|
||
</td>
|
||
<td id="C3305DC9FFD2D79ABBAD0069591B5832" box="[446,599,277,294]" gridcol="2" gridrow="1" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867BBAD00695A8B5830" box="[446,455,277,292]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
H (
|
||
<emphasis id="0CA5EAE5FFD22867BBCF00695AAD5830" box="[476,481,277,292]" italics="true" pageId="2" pageNumber="426">J</emphasis>
|
||
in Hz)
|
||
</td>
|
||
<td id="C3305DC9FFD2D79AB8A5006958655832" box="[694,809,277,294]" gridcol="3" gridrow="1" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867B8A5006959F35830" box="[694,703,277,292]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
C, mult.
|
||
</td>
|
||
<td id="C3305DC9FFD2D79AB97F00695F495832" box="[876,1029,277,294]" gridcol="4" gridrow="1" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867B97F006958395830" box="[876,885,277,292]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
H (
|
||
<emphasis id="0CA5EAE5FFD22867B999006958C35830" box="[906,911,277,292]" italics="true" pageId="2" pageNumber="426">J</emphasis>
|
||
in Hz)
|
||
</td>
|
||
<td id="C3305DC9FFD2D79ABE7700695F945832" box="[1124,1240,277,294]" gridcol="5" gridrow="1" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867BE7700695F215830" box="[1124,1133,277,292]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
C, mult.
|
||
</td>
|
||
<td id="C3305DC9FFD2D79ABF0000695EE05832" box="[1299,1452,277,294]" gridcol="6" gridrow="1" pageId="2" pageNumber="426">
|
||
<emphasis id="0CA5EAE5FFD22867BF0000695E505830" box="[1299,1308,277,292]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
H (
|
||
<emphasis id="0CA5EAE5FFD22867BF2200695E7A5830" box="[1329,1334,277,292]" italics="true" pageId="2" pageNumber="426">J</emphasis>
|
||
in Hz)
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D004B5EE05851" box="[110,1452,311,325]" gridrow="2" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D004B5BFC5851" box="[110,176,311,325]" gridcol="0" gridrow="2" pageId="2" pageNumber="426">1</th>
|
||
<td id="C3305DC9FFD2D79AB8A5004B58655851" box="[694,809,311,325]" gridcol="3" gridrow="2" pageId="2" pageNumber="426">157.2, C</td>
|
||
<td id="C3305DC9FFD2D79ABE77004B5F945851" box="[1124,1240,311,325]" gridcol="5" gridrow="2" pageId="2" pageNumber="426">157.0, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D00325EE05848" box="[110,1452,334,348]" gridrow="3" pageId="2" pageNumber="426" rowspan-2="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D00325BFC5848" box="[110,176,334,348]" gridcol="0" gridrow="3" pageId="2" pageNumber="426">2</th>
|
||
<td id="C3305DC9FFD2D79ABB1C00325ACF5848" box="[271,387,334,348]" gridcol="1" gridrow="3" pageId="2" pageNumber="426">160.7, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A5003258655848" box="[694,809,334,348]" gridcol="3" gridrow="3" pageId="2" pageNumber="426">106.4, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7700325F945848" box="[1124,1240,334,348]" gridcol="5" gridrow="3" pageId="2" pageNumber="426">107.8, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0000325EE05848" box="[1299,1452,334,348]" gridcol="6" gridrow="3" pageId="2" pageNumber="426">6.18, d (2.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D00195EE05867" box="[110,1452,357,371]" gridrow="4" pageId="2" pageNumber="426" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D00195BFC5867" box="[110,176,357,371]" gridcol="0" gridrow="4" pageId="2" pageNumber="426">3</th>
|
||
<td id="C3305DC9FFD2D79ABB1C00195ACF5867" box="[271,387,357,371]" gridcol="1" gridrow="4" pageId="2" pageNumber="426">118.0, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A5001958655867" box="[694,809,357,371]" gridcol="3" gridrow="4" pageId="2" pageNumber="426">160.5, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7700195F945867" box="[1124,1240,357,371]" gridcol="5" gridrow="4" pageId="2" pageNumber="426">156.9, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D00005EE0589E" box="[110,1452,380,394]" gridrow="5" pageId="2" pageNumber="426" rowspan-2="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D00005BFC589E" box="[110,176,380,394]" gridcol="0" gridrow="5" pageId="2" pageNumber="426">4</th>
|
||
<td id="C3305DC9FFD2D79ABB1C00005ACF589E" box="[271,387,380,394]" gridcol="1" gridrow="5" pageId="2" pageNumber="426">182.4, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A500005865589E" box="[694,809,380,394]" gridcol="3" gridrow="5" pageId="2" pageNumber="426">110.0, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7700005F94589E" box="[1124,1240,380,394]" gridcol="5" gridrow="5" pageId="2" pageNumber="426">102.1, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0000005EE0589E" box="[1299,1452,380,394]" gridcol="6" gridrow="5" pageId="2" pageNumber="426">6.15, d (2.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D00EF5EE058B5" box="[110,1452,403,417]" gridrow="6" pageId="2" pageNumber="426" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D00EF5BFC58B5" box="[110,176,403,417]" gridcol="0" gridrow="6" pageId="2" pageNumber="426">4a</th>
|
||
<td id="C3305DC9FFD2D79ABB1C00EF5ACF58B5" box="[271,387,403,417]" gridcol="1" gridrow="6" pageId="2" pageNumber="426">104.7, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A500EF586558B5" box="[694,809,403,417]" gridcol="3" gridrow="6" pageId="2" pageNumber="426">155.3, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7700EF5F9458B5" box="[1124,1240,403,417]" gridcol="5" gridrow="6" pageId="2" pageNumber="426">147.0, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D00DA5EE058AC" box="[110,1452,422,440]" gridrow="7" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D00DA5BFC58AC" box="[110,176,422,440]" gridcol="0" gridrow="7" pageId="2" pageNumber="426">4b</th>
|
||
<td id="C3305DC9FFD2D79ABE7700DA5F9458AC" box="[1124,1240,422,440]" gridcol="5" gridrow="7" pageId="2" pageNumber="426">35.1, CH a</td>
|
||
<td id="C3305DC9FFD2D79ABF0000DA5EE058AC" box="[1299,1452,422,440]" gridcol="6" gridrow="7" pageId="2" pageNumber="426">3.45, br s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D00C05EE058DB" box="[110,1452,444,463]" gridrow="8" pageId="2" pageNumber="426" rowspan-2="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D00C05BFC58DB" box="[110,176,444,463]" gridcol="0" gridrow="8" pageId="2" pageNumber="426">5</th>
|
||
<td id="C3305DC9FFD2D79ABB1C00C05ACF58DB" box="[271,387,444,463]" gridcol="1" gridrow="8" pageId="2" pageNumber="426">157.1, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A500C0586558DB" box="[694,809,444,463]" gridcol="3" gridrow="8" pageId="2" pageNumber="426">126.7, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7700C05F9458DB" box="[1124,1240,444,463]" gridcol="5" gridrow="8" pageId="2" pageNumber="426">40.0, CH b</td>
|
||
<td id="C3305DC9FFD2D79ABF0000C05EE058DB" box="[1299,1452,444,463]" gridcol="6" gridrow="8" pageId="2" pageNumber="426">3.57, br s b</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D00AB5EE058E8" box="[110,1452,471,508]" gridrow="9" pageId="2" pageNumber="426" rowspan-2="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D00AB5BFC58E8" box="[110,176,471,508]" gridcol="0" gridrow="9" pageId="2" pageNumber="426">6</th>
|
||
<td id="C3305DC9FFD2D79ABB1C00AB5ACF58E8" box="[271,387,471,508]" gridcol="1" gridrow="9" pageId="2" pageNumber="426">104.7, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A500AB586558E8" box="[694,809,471,508]" gridcol="3" gridrow="9" pageId="2" pageNumber="426">159.5, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7700AB5F9458E8" box="[1124,1240,471,508]" gridcol="5" gridrow="9" pageId="2" pageNumber="426">43.8, CH2</td>
|
||
<td id="C3305DC9FFD2D79ABF0000AB5EE058E8" box="[1299,1452,471,508]" gridcol="6" gridrow="9" pageId="2" pageNumber="426">2.21, br s 2.42, dd (15.6, 3.2)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D03795EE05B07" box="[110,1452,517,531]" gridrow="10" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D03795BFC5B07" box="[110,176,517,531]" gridcol="0" gridrow="10" pageId="2" pageNumber="426">6a</th>
|
||
<td id="C3305DC9FFD2D79ABE7703795F945B07" box="[1124,1240,517,531]" gridcol="5" gridrow="10" pageId="2" pageNumber="426">142.2, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D03605EE05B3E" box="[110,1452,540,554]" gridrow="11" pageId="2" pageNumber="426" rowspan-2="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D03605BFC5B3E" box="[110,176,540,554]" gridcol="0" gridrow="11" pageId="2" pageNumber="426">7</th>
|
||
<td id="C3305DC9FFD2D79ABB1C03605ACF5B3E" box="[271,387,540,554]" gridcol="1" gridrow="11" pageId="2" pageNumber="426">162.9, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A5036058655B3E" box="[694,809,540,554]" gridcol="3" gridrow="11" pageId="2" pageNumber="426">143.4, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7703605F945B3E" box="[1124,1240,540,554]" gridcol="5" gridrow="11" pageId="2" pageNumber="426">107.2, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0003605EE05B3E" box="[1299,1452,540,554]" gridcol="6" gridrow="11" pageId="2" pageNumber="426">5.92, d (2.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D034F5EE05B55" box="[110,1452,563,577]" gridrow="12" pageId="2" pageNumber="426" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D034F5BFC5B55" box="[110,176,563,577]" gridcol="0" gridrow="12" pageId="2" pageNumber="426">8</th>
|
||
<td id="C3305DC9FFD2D79ABB1C034F5ACF5B55" box="[271,387,563,577]" gridcol="1" gridrow="12" pageId="2" pageNumber="426">94.2, CH</td>
|
||
<td id="C3305DC9FFD2D79ABBAD034F591B5B55" box="[446,599,563,577]" gridcol="2" gridrow="12" pageId="2" pageNumber="426">6.57, s</td>
|
||
<td id="C3305DC9FFD2D79AB8A5034F58655B55" box="[694,809,563,577]" gridcol="3" gridrow="12" pageId="2" pageNumber="426">133.2, CH</td>
|
||
<td id="C3305DC9FFD2D79AB97F034F5F495B55" box="[876,1029,563,577]" gridcol="4" gridrow="12" pageId="2" pageNumber="426">8.22, s</td>
|
||
<td id="C3305DC9FFD2D79ABE77034F5F945B55" box="[1124,1240,563,577]" gridcol="5" gridrow="12" pageId="2" pageNumber="426">156.8, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D03355EE05B4C" box="[110,1452,585,600]" gridrow="13" pageId="2" pageNumber="426" rowspan-2="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D03355BFC5B4C" box="[110,176,585,600]" gridcol="0" gridrow="13" pageId="2" pageNumber="426">8a</th>
|
||
<td id="C3305DC9FFD2D79ABB1C03355ACF5B4C" box="[271,387,585,600]" gridcol="1" gridrow="13" pageId="2" pageNumber="426">159.2, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A5033558655B4C" box="[694,809,585,600]" gridcol="3" gridrow="13" pageId="2" pageNumber="426">122.6, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D031C5EE05B91" box="[110,1452,608,645]" gridrow="14" pageId="2" pageNumber="426" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D031C5BFC5B91" box="[110,176,608,645]" gridcol="0" gridrow="14" pageId="2" pageNumber="426">9</th>
|
||
<td id="C3305DC9FFD2D79ABB1C031C5ACF5B91" box="[271,387,608,645]" gridcol="1" gridrow="14" pageId="2" pageNumber="426">25.7, CH2</td>
|
||
<td id="C3305DC9FFD2D79ABBAD031C591B5B91" box="[446,599,608,645]" gridcol="2" gridrow="14" pageId="2" pageNumber="426">2.59, dd (16.4, 9.6) 3.51, dd (16.4, 2.0)</td>
|
||
<td id="C3305DC9FFD2D79AB8A5031C58655B91" box="[694,809,608,645]" gridcol="3" gridrow="14" pageId="2" pageNumber="426">181.2, C</td>
|
||
<td id="C3305DC9FFD2D79ABE77031C5F945B91" box="[1124,1240,608,645]" gridcol="5" gridrow="14" pageId="2" pageNumber="426">107.1, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF00031C5EE05B91" box="[1299,1452,608,645]" gridcol="6" gridrow="14" pageId="2" pageNumber="426">6.07, d (2.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D03F25EE05B88" box="[110,1452,654,668]" gridrow="15" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D03F25BFC5B88" box="[110,176,654,668]" gridcol="0" gridrow="15" pageId="2" pageNumber="426">9a</th>
|
||
<td id="C3305DC9FFD2D79AB8A503F258655B88" box="[694,809,654,668]" gridcol="3" gridrow="15" pageId="2" pageNumber="426">105.0, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D03D95EE05BA7" box="[110,1452,677,691]" gridrow="16" pageId="2" pageNumber="426" rowspan-3="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D03D95BFC5BA7" box="[110,176,677,691]" gridcol="0" gridrow="16" pageId="2" pageNumber="426">10</th>
|
||
<td id="C3305DC9FFD2D79ABB1C03D95ACF5BA7" box="[271,387,677,691]" gridcol="1" gridrow="16" pageId="2" pageNumber="426">92.3, CH</td>
|
||
<td id="C3305DC9FFD2D79ABBAD03D9591B5BA7" box="[446,599,677,691]" gridcol="2" gridrow="16" pageId="2" pageNumber="426">4.02, dd (9.6, 2.0)</td>
|
||
<td id="C3305DC9FFD2D79ABE7703D95F945BA7" box="[1124,1240,677,691]" gridcol="5" gridrow="16" pageId="2" pageNumber="426">157.0, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D03C05EE05BDE" box="[110,1452,700,714]" gridrow="17" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D03C05BFC5BDE" box="[110,176,700,714]" gridcol="0" gridrow="17" pageId="2" pageNumber="426">10a</th>
|
||
<td id="C3305DC9FFD2D79AB8A503C058655BDE" box="[694,809,700,714]" gridcol="3" gridrow="17" pageId="2" pageNumber="426">152.2, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7703C05F945BDE" box="[1124,1240,700,714]" gridcol="5" gridrow="17" pageId="2" pageNumber="426">117.8, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D03B35EE05BF5" box="[110,1452,719,737]" gridrow="18" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D03B35BFC5BF5" box="[110,176,719,737]" gridcol="0" gridrow="18" pageId="2" pageNumber="426">10b</th>
|
||
<td id="C3305DC9FFD2D79ABE7703B35F945BF5" box="[1124,1240,719,737]" gridcol="5" gridrow="18" pageId="2" pageNumber="426">39.9, CH b</td>
|
||
<td id="C3305DC9FFD2D79ABF0003B35EE05BF5" box="[1299,1452,719,737]" gridcol="6" gridrow="18" pageId="2" pageNumber="426">3.57, br s b</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D03955EE05BEC" box="[110,1452,745,760]" gridrow="19" pageId="2" pageNumber="426" rowspan-2="1">
|
||
<th id="C3305DC9FFD2D79ABA7D03955BFC5BEC" box="[110,176,745,760]" gridcol="0" gridrow="19" pageId="2" pageNumber="426">11</th>
|
||
<td id="C3305DC9FFD2D79ABB1C03955ACF5BEC" box="[271,387,745,760]" gridcol="1" gridrow="19" pageId="2" pageNumber="426">73.1, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A5039558655BEC" box="[694,809,745,760]" gridcol="3" gridrow="19" pageId="2" pageNumber="426">116.4, CH</td>
|
||
<td id="C3305DC9FFD2D79AB97F03955F495BEC" box="[876,1029,745,760]" gridcol="4" gridrow="19" pageId="2" pageNumber="426">6.68, d (10.0)</td>
|
||
<td id="C3305DC9FFD2D79ABE7703955F945BEC" box="[1124,1240,745,760]" gridcol="5" gridrow="19" pageId="2" pageNumber="426">48.2, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0003955EE05BEC" box="[1299,1452,745,760]" gridcol="6" gridrow="19" pageId="2" pageNumber="426">4.40, br s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D027C5EE05A1B" box="[110,1452,768,783]" gridrow="20" pageId="2" pageNumber="426">
|
||
<th id="C3305DC9FFD2D79ABA7D027C5BFC5A1B" box="[110,176,768,783]" gridcol="0" gridrow="20" pageId="2" pageNumber="426">12</th>
|
||
<td id="C3305DC9FFD2D79ABB1C027C5ACF5A1B" box="[271,387,768,783]" gridcol="1" gridrow="20" pageId="2" pageNumber="426">25.8, Me</td>
|
||
<td id="C3305DC9FFD2D79ABBAD027C591B5A1B" box="[446,599,768,783]" gridcol="2" gridrow="20" pageId="2" pageNumber="426">1.34, s</td>
|
||
<td id="C3305DC9FFD2D79AB8A5027C58655A1B" box="[694,809,768,783]" gridcol="3" gridrow="20" pageId="2" pageNumber="426">129.7, CH</td>
|
||
<td id="C3305DC9FFD2D79AB97F027C5F495A1B" box="[876,1029,768,783]" gridcol="4" gridrow="20" pageId="2" pageNumber="426">5.79, d (10.0)</td>
|
||
<td id="C3305DC9FFD2D79ABE77027C5F945A1B" box="[1124,1240,768,783]" gridcol="5" gridrow="20" pageId="2" pageNumber="426">40.3, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF00027C5EE05A1B" box="[1299,1452,768,783]" gridcol="6" gridrow="20" pageId="2" pageNumber="426">4.93, br s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D026B5EE05A31" box="[110,1452,791,805]" gridrow="21" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D026B5BFC5A31" box="[110,176,791,805]" gridcol="0" gridrow="21" pageId="2" pageNumber="426">12a</th>
|
||
<td id="C3305DC9FFD2D79ABE77026B5F945A31" box="[1124,1240,791,805]" gridcol="5" gridrow="21" pageId="2" pageNumber="426">118.2, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D02525EE05A28" box="[110,1452,814,828]" gridrow="22" pageId="2" pageNumber="426" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D02525BFC5A28" box="[110,176,814,828]" gridcol="0" gridrow="22" pageId="2" pageNumber="426">13</th>
|
||
<td id="C3305DC9FFD2D79ABB1C02525ACF5A28" box="[271,387,814,828]" gridcol="1" gridrow="22" pageId="2" pageNumber="426">27.9, Me</td>
|
||
<td id="C3305DC9FFD2D79ABBAD0252591B5A28" box="[446,599,814,828]" gridcol="2" gridrow="22" pageId="2" pageNumber="426">1.36, s</td>
|
||
<td id="C3305DC9FFD2D79AB8A5025258655A28" box="[694,809,814,828]" gridcol="3" gridrow="22" pageId="2" pageNumber="426">80.1, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7702525F945A28" box="[1124,1240,814,828]" gridcol="5" gridrow="22" pageId="2" pageNumber="426">126.4, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D02395EE05A41" box="[110,1452,837,853]" gridrow="23" pageId="2" pageNumber="426" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D02395BFC5A41" box="[110,176,837,853]" gridcol="0" gridrow="23" pageId="2" pageNumber="426">14</th>
|
||
<td id="C3305DC9FFD2D79ABB1C02395ACF5A41" box="[271,387,837,853]" gridcol="1" gridrow="23" pageId="2" pageNumber="426">22.7, CH2</td>
|
||
<td id="C3305DC9FFD2D79ABBAD0239591B5A41" box="[446,599,837,853]" gridcol="2" gridrow="23" pageId="2" pageNumber="426">3.36, d (7.2)</td>
|
||
<td id="C3305DC9FFD2D79AB8A5023958655A41" box="[694,809,837,853]" gridcol="3" gridrow="23" pageId="2" pageNumber="426">29.3, Me</td>
|
||
<td id="C3305DC9FFD2D79AB97F02395F495A41" box="[876,1029,837,853]" gridcol="4" gridrow="23" pageId="2" pageNumber="426">1.52, s</td>
|
||
<td id="C3305DC9FFD2D79ABE7702395F945A41" box="[1124,1240,837,853]" gridcol="5" gridrow="23" pageId="2" pageNumber="426">156.0, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D02205EE05A7E" box="[110,1452,860,874]" gridrow="24" pageId="2" pageNumber="426">
|
||
<th id="C3305DC9FFD2D79ABA7D02205BFC5A7E" box="[110,176,860,874]" gridcol="0" gridrow="24" pageId="2" pageNumber="426">15</th>
|
||
<td id="C3305DC9FFD2D79ABB1C02205ACF5A7E" box="[271,387,860,874]" gridcol="1" gridrow="24" pageId="2" pageNumber="426">124.0, CH</td>
|
||
<td id="C3305DC9FFD2D79ABBAD0220591B5A7E" box="[446,599,860,874]" gridcol="2" gridrow="24" pageId="2" pageNumber="426">5.28, br t (7.2)</td>
|
||
<td id="C3305DC9FFD2D79AB8A5022058655A7E" box="[694,809,860,874]" gridcol="3" gridrow="24" pageId="2" pageNumber="426">29.2, Me</td>
|
||
<td id="C3305DC9FFD2D79AB97F02205F495A7E" box="[876,1029,860,874]" gridcol="4" gridrow="24" pageId="2" pageNumber="426">1.51, s</td>
|
||
<td id="C3305DC9FFD2D79ABE7702205F945A7E" box="[1124,1240,860,874]" gridcol="5" gridrow="24" pageId="2" pageNumber="426">104.4, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0002205EE05A7E" box="[1299,1452,860,874]" gridcol="6" gridrow="24" pageId="2" pageNumber="426">6.43, d (2.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D020E5EE05A97" box="[110,1452,882,899]" gridrow="25" pageId="2" pageNumber="426" rowspan-2="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D020E5BFC5A97" box="[110,176,882,899]" gridcol="0" gridrow="25" pageId="2" pageNumber="426">16</th>
|
||
<td id="C3305DC9FFD2D79ABB1C020E5ACF5A97" box="[271,387,882,899]" gridcol="1" gridrow="25" pageId="2" pageNumber="426">132.3, C</td>
|
||
<td id="C3305DC9FFD2D79AB8A5020E58655A97" box="[694,809,882,899]" gridcol="3" gridrow="25" pageId="2" pageNumber="426">22.6, CH2</td>
|
||
<td id="C3305DC9FFD2D79AB97F020E5F495A97" box="[876,1029,882,899]" gridcol="4" gridrow="25" pageId="2" pageNumber="426">3.61, d (7.2)</td>
|
||
<td id="C3305DC9FFD2D79ABE77020E5F945A97" box="[1124,1240,882,899]" gridcol="5" gridrow="25" pageId="2" pageNumber="426">157.6, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D02F55EE05A8C" box="[110,1452,905,920]" gridrow="26" pageId="2" pageNumber="426">
|
||
<th id="C3305DC9FFD2D79ABA7D02F55BFC5A8C" box="[110,176,905,920]" gridcol="0" gridrow="26" pageId="2" pageNumber="426">17</th>
|
||
<td id="C3305DC9FFD2D79ABB1C02F55ACF5A8C" box="[271,387,905,920]" gridcol="1" gridrow="26" pageId="2" pageNumber="426">26.5, Me</td>
|
||
<td id="C3305DC9FFD2D79ABBAD02F5591B5A8C" box="[446,599,905,920]" gridcol="2" gridrow="26" pageId="2" pageNumber="426">1.65, s</td>
|
||
<td id="C3305DC9FFD2D79AB8A502F558655A8C" box="[694,809,905,920]" gridcol="3" gridrow="26" pageId="2" pageNumber="426">123.9, CH</td>
|
||
<td id="C3305DC9FFD2D79AB97F02F55F495A8C" box="[876,1029,905,920]" gridcol="4" gridrow="26" pageId="2" pageNumber="426">5.39, br t (7.2)</td>
|
||
<td id="C3305DC9FFD2D79ABE7702F55F945A8C" box="[1124,1240,905,920]" gridcol="5" gridrow="26" pageId="2" pageNumber="426">108.6, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0002F55EE05A8C" box="[1299,1452,905,920]" gridcol="6" gridrow="26" pageId="2" pageNumber="426">6.21, dd (8.4, 2.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D02DC5EE05ABB" box="[110,1452,928,943]" gridrow="27" pageId="2" pageNumber="426" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D02DC5BFC5ABB" box="[110,176,928,943]" gridcol="0" gridrow="27" pageId="2" pageNumber="426">18</th>
|
||
<td id="C3305DC9FFD2D79ABB1C02DC5ACF5ABB" box="[271,387,928,943]" gridcol="1" gridrow="27" pageId="2" pageNumber="426">18.6, Me</td>
|
||
<td id="C3305DC9FFD2D79ABBAD02DC591B5ABB" box="[446,599,928,943]" gridcol="2" gridrow="27" pageId="2" pageNumber="426">1.78, s</td>
|
||
<td id="C3305DC9FFD2D79AB8A502DC58655ABB" box="[694,809,928,943]" gridcol="3" gridrow="27" pageId="2" pageNumber="426">132.7, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7702DC5F945ABB" box="[1124,1240,928,943]" gridcol="5" gridrow="27" pageId="2" pageNumber="426">128.3, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0002DC5EE05ABB" box="[1299,1452,928,943]" gridcol="6" gridrow="27" pageId="2" pageNumber="426">6.64, d (8.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D02CB5EE05AD1" box="[110,1452,951,965]" gridrow="28" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D02CB5BFC5AD1" box="[110,176,951,965]" gridcol="0" gridrow="28" pageId="2" pageNumber="426">19</th>
|
||
<td id="C3305DC9FFD2D79AB8A502CB58655AD1" box="[694,809,951,965]" gridcol="3" gridrow="28" pageId="2" pageNumber="426">26.6, Me</td>
|
||
<td id="C3305DC9FFD2D79AB97F02CB5F495AD1" box="[876,1029,951,965]" gridcol="4" gridrow="28" pageId="2" pageNumber="426">1.65, s</td>
|
||
<td id="C3305DC9FFD2D79ABE7702CB5F945AD1" box="[1124,1240,951,965]" gridcol="5" gridrow="28" pageId="2" pageNumber="426">149.6, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D02B25EE05AC8" box="[110,1452,974,988]" gridrow="29" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1">
|
||
<th id="C3305DC9FFD2D79ABA7D02B25BFC5AC8" box="[110,176,974,988]" gridcol="0" gridrow="29" pageId="2" pageNumber="426">20</th>
|
||
<td id="C3305DC9FFD2D79AB8A502B258655AC8" box="[694,809,974,988]" gridcol="3" gridrow="29" pageId="2" pageNumber="426">18.9, Me</td>
|
||
<td id="C3305DC9FFD2D79AB97F02B25F495AC8" box="[876,1029,974,988]" gridcol="4" gridrow="29" pageId="2" pageNumber="426">1.87, s</td>
|
||
<td id="C3305DC9FFD2D79ABE7702B25F945AC8" box="[1124,1240,974,988]" gridcol="5" gridrow="29" pageId="2" pageNumber="426">108.9, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0002B25EE05AC8" box="[1299,1452,974,988]" gridcol="6" gridrow="29" pageId="2" pageNumber="426">6.09, d (2.0)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D02995EE05AE7" box="[110,1452,997,1011]" gridrow="30" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D02995BFC5AE7" box="[110,176,997,1011]" gridcol="0" gridrow="30" pageId="2" pageNumber="426">21</th>
|
||
<td id="C3305DC9FFD2D79AB8A5029958655AE7" box="[694,809,997,1011]" gridcol="3" gridrow="30" pageId="2" pageNumber="426">198.3, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7702995F945AE7" box="[1124,1240,997,1011]" gridcol="5" gridrow="30" pageId="2" pageNumber="426">159.1, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D02805EE05D18" box="[110,1452,1020,1036]" gridrow="31" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1">
|
||
<th id="C3305DC9FFD2D79ABA7D02805BFC5D18" box="[110,176,1020,1036]" gridcol="0" gridrow="31" pageId="2" pageNumber="426">22</th>
|
||
<td id="C3305DC9FFD2D79AB8A5028058655D18" box="[694,809,1020,1036]" gridcol="3" gridrow="31" pageId="2" pageNumber="426">54.0, CH2</td>
|
||
<td id="C3305DC9FFD2D79AB97F02805F495D18" box="[876,1029,1020,1036]" gridcol="4" gridrow="31" pageId="2" pageNumber="426">3.28, 2.83, d (18.4)</td>
|
||
<td id="C3305DC9FFD2D79ABE7702805F945D18" box="[1124,1240,1020,1036]" gridcol="5" gridrow="31" pageId="2" pageNumber="426">101.5, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0002805EE05D18" box="[1299,1452,1020,1036]" gridcol="6" gridrow="31" pageId="2" pageNumber="426">6.12, br t (2.0)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D056E5EE05D35" box="[110,1452,1042,1057]" gridrow="32" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D056E5BFC5D35" box="[110,176,1042,1057]" gridcol="0" gridrow="32" pageId="2" pageNumber="426">23</th>
|
||
<td id="C3305DC9FFD2D79AB8A5056E58655D35" box="[694,809,1042,1057]" gridcol="3" gridrow="32" pageId="2" pageNumber="426">78.3, C</td>
|
||
<td id="C3305DC9FFD2D79ABE77056E5F945D35" box="[1124,1240,1042,1057]" gridcol="5" gridrow="32" pageId="2" pageNumber="426">159.1, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D05555EE05D23" box="[110,1452,1065,1079]" gridrow="33" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D05555BFC5D23" box="[110,176,1065,1079]" gridcol="0" gridrow="33" pageId="2" pageNumber="426">24</th>
|
||
<td id="C3305DC9FFD2D79AB8A5055558655D23" box="[694,809,1065,1079]" gridcol="3" gridrow="33" pageId="2" pageNumber="426">139.6, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7705555F945D23" box="[1124,1240,1065,1079]" gridcol="5" gridrow="33" pageId="2" pageNumber="426">108.9, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0005555EE05D23" box="[1299,1452,1065,1079]" gridcol="6" gridrow="33" pageId="2" pageNumber="426">6.09, d (2.0)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D053C5EE05D5B" box="[110,1452,1088,1103]" gridrow="34" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D053C5BFC5D5B" box="[110,176,1088,1103]" gridcol="0" gridrow="34" pageId="2" pageNumber="426">25</th>
|
||
<td id="C3305DC9FFD2D79AB8A5053C58655D5B" box="[694,809,1088,1103]" gridcol="3" gridrow="34" pageId="2" pageNumber="426">25.9, Me</td>
|
||
<td id="C3305DC9FFD2D79AB97F053C5F495D5B" box="[876,1029,1088,1103]" gridcol="4" gridrow="34" pageId="2" pageNumber="426">2.18, s</td>
|
||
<td id="C3305DC9FFD2D79ABE77053C5F945D5B" box="[1124,1240,1088,1103]" gridcol="5" gridrow="34" pageId="2" pageNumber="426">127.4, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D052B5EE05D7C" box="[110,1452,1111,1128]" gridrow="35" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D052B5BFC5D7C" box="[110,176,1111,1128]" gridcol="0" gridrow="35" pageId="2" pageNumber="426">26</th>
|
||
<td id="C3305DC9FFD2D79AB8A5052B58655D7C" box="[694,809,1111,1128]" gridcol="3" gridrow="35" pageId="2" pageNumber="426">118.6, CH2</td>
|
||
<td id="C3305DC9FFD2D79AB97F052B5F495D7C" box="[876,1029,1111,1128]" gridcol="4" gridrow="35" pageId="2" pageNumber="426">5.04, 5.25, s</td>
|
||
<td id="C3305DC9FFD2D79ABE77052B5F945D7C" box="[1124,1240,1111,1128]" gridcol="5" gridrow="35" pageId="2" pageNumber="426">157.3, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D05125EE05D68" box="[110,1452,1134,1148]" gridrow="36" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D05125BFC5D68" box="[110,176,1134,1148]" gridcol="0" gridrow="36" pageId="2" pageNumber="426">27</th>
|
||
<td id="C3305DC9FFD2D79AB8A5051258655D68" box="[694,809,1134,1148]" gridcol="3" gridrow="36" pageId="2" pageNumber="426">174.8, C</td>
|
||
<td id="C3305DC9FFD2D79ABE7705125F945D68" box="[1124,1240,1134,1148]" gridcol="5" gridrow="36" pageId="2" pageNumber="426">103.7, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0005125EE05D68" box="[1299,1452,1134,1148]" gridcol="6" gridrow="36" pageId="2" pageNumber="426">6.35, d (2.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D05F95EE05D87" box="[110,1452,1157,1171]" gridrow="37" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D05F95BFC5D87" box="[110,176,1157,1171]" gridcol="0" gridrow="37" pageId="2" pageNumber="426">28</th>
|
||
<td id="C3305DC9FFD2D79ABE7705F95F945D87" box="[1124,1240,1157,1171]" gridcol="5" gridrow="37" pageId="2" pageNumber="426">157.5, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D05E75EE05DBE" box="[110,1452,1179,1194]" gridrow="38" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D05E75BFC5DBE" box="[110,176,1179,1194]" gridcol="0" gridrow="38" pageId="2" pageNumber="426">29</th>
|
||
<td id="C3305DC9FFD2D79ABE7705E75F945DBE" box="[1124,1240,1179,1194]" gridcol="5" gridrow="38" pageId="2" pageNumber="426">107.1, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0005E75EE05DBE" box="[1299,1452,1179,1194]" gridcol="6" gridrow="38" pageId="2" pageNumber="426">6.09, dd (2.4, 8.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D05CE5EE05DD5" box="[110,1452,1202,1217]" gridrow="39" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD2D79ABA7D05CE5BFC5DD5" box="[110,176,1202,1217]" gridcol="0" gridrow="39" pageId="2" pageNumber="426">30</th>
|
||
<td id="C3305DC9FFD2D79ABE7705CE5F945DD5" box="[1124,1240,1202,1217]" gridcol="5" gridrow="39" pageId="2" pageNumber="426">130.4, CH</td>
|
||
<td id="C3305DC9FFD2D79ABF0005CE5EE05DD5" box="[1299,1452,1202,1217]" gridcol="6" gridrow="39" pageId="2" pageNumber="426">6.33, d (8.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D05AD5EE05DF5" box="[110,1452,1233,1249]" gridrow="40" pageId="2" pageNumber="426" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D05AD5BFC5DF5" box="[110,176,1233,1249]" gridcol="0" gridrow="40" pageId="2" pageNumber="426">
|
||
1
|
||
<emphasis id="0CA5EAE5FFD22867BA6B05AD5B305DCE" box="[120,124,1233,1242]" italics="true" pageId="2" pageNumber="426">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD2D79ABB1C05AD5ACF5DF5" box="[271,387,1233,1249]" gridcol="1" gridrow="40" pageId="2" pageNumber="426">115.7, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D05945EE05DEC" box="[110,1452,1256,1272]" gridrow="41" pageId="2" pageNumber="426" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D05945BFC5DEC" box="[110,176,1256,1272]" gridcol="0" gridrow="41" pageId="2" pageNumber="426">
|
||
2
|
||
<emphasis id="0CA5EAE5FFD22867BA6B05945B305DE5" box="[120,124,1256,1265]" italics="true" pageId="2" pageNumber="426">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD2D79ABB1C05945ACF5DEC" box="[271,387,1256,1272]" gridcol="1" gridrow="41" pageId="2" pageNumber="426">161.6, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D05825EE05C1B" box="[110,1452,1278,1295]" gridrow="42" pageId="2" pageNumber="426" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D05825BFC5C1B" box="[110,176,1278,1295]" gridcol="0" gridrow="42" pageId="2" pageNumber="426">
|
||
3
|
||
<emphasis id="0CA5EAE5FFD22867BA6B05825B305C13" box="[120,124,1278,1287]" italics="true" pageId="2" pageNumber="426">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD2D79ABB1C05825ACF5C1B" box="[271,387,1278,1295]" gridcol="1" gridrow="42" pageId="2" pageNumber="426">109.3, CH</td>
|
||
<td id="C3305DC9FFD2D79ABBAD0582591B5C1B" box="[446,599,1278,1295]" gridcol="2" gridrow="42" pageId="2" pageNumber="426">6.67, d (2.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D04695EE05C32" box="[110,1452,1301,1318]" gridrow="43" pageId="2" pageNumber="426" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D04695BFC5C32" box="[110,176,1301,1318]" gridcol="0" gridrow="43" pageId="2" pageNumber="426">
|
||
4
|
||
<emphasis id="0CA5EAE5FFD22867BA6B04695B305C0A" box="[120,124,1301,1310]" italics="true" pageId="2" pageNumber="426">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD2D79ABB1C04695ACF5C32" box="[271,387,1301,1318]" gridcol="1" gridrow="43" pageId="2" pageNumber="426">163.1, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D04505EE05C29" box="[110,1452,1324,1341]" gridrow="44" pageId="2" pageNumber="426" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D04505BFC5C29" box="[110,176,1324,1341]" gridcol="0" gridrow="44" pageId="2" pageNumber="426">
|
||
5
|
||
<emphasis id="0CA5EAE5FFD22867BA6B04505B305C21" box="[120,124,1324,1333]" italics="true" pageId="2" pageNumber="426">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD2D79ABB1C04505ACF5C29" box="[271,387,1324,1341]" gridcol="1" gridrow="44" pageId="2" pageNumber="426">112.5, CH</td>
|
||
<td id="C3305DC9FFD2D79ABBAD0450591B5C29" box="[446,599,1324,1341]" gridcol="2" gridrow="44" pageId="2" pageNumber="426">6.72, dd (8.8, 2.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D043F5EE05C47" box="[110,1452,1347,1363]" gridrow="45" pageId="2" pageNumber="426" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D043F5BFC5C47" box="[110,176,1347,1363]" gridcol="0" gridrow="45" pageId="2" pageNumber="426">
|
||
6
|
||
<emphasis id="0CA5EAE5FFD22867BA6B043F5B305C58" box="[120,124,1347,1356]" italics="true" pageId="2" pageNumber="426">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD2D79ABB1C043F5ACF5C47" box="[271,387,1347,1363]" gridcol="1" gridrow="45" pageId="2" pageNumber="426">131.7, CH</td>
|
||
<td id="C3305DC9FFD2D79ABBAD043F591B5C47" box="[446,599,1347,1363]" gridcol="2" gridrow="45" pageId="2" pageNumber="426">7.92, d (8.8)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D04205EE05C7F" box="[110,1452,1372,1387]" gridrow="46" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D04205BFC5C7F" box="[110,176,1372,1387]" gridcol="0" gridrow="46" pageId="2" pageNumber="426">OMe-27</th>
|
||
<td id="C3305DC9FFD2D79AB8A5042058655C7F" box="[694,809,1372,1387]" gridcol="3" gridrow="46" pageId="2" pageNumber="426">54.0, Me</td>
|
||
<td id="C3305DC9FFD2D79AB97F04205F495C7F" box="[876,1029,1372,1387]" gridcol="4" gridrow="46" pageId="2" pageNumber="426">3.73, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D040F5EE05C96" box="[110,1452,1395,1410]" gridrow="47" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D040F5BFC5C96" box="[110,176,1395,1410]" gridcol="0" gridrow="47" pageId="2" pageNumber="426">OH-1</th>
|
||
<td id="C3305DC9FFD2D79AB97F040F5F495C96" box="[876,1029,1395,1410]" gridcol="4" gridrow="47" pageId="2" pageNumber="426">12.95, br s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D04F65EE05C8C" box="[110,1452,1418,1432]" gridrow="48" pageId="2" pageNumber="426" rowspan-1="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D04F65BFC5C8C" box="[110,176,1418,1432]" gridcol="0" gridrow="48" pageId="2" pageNumber="426">OH-5</th>
|
||
<td id="C3305DC9FFD2D79ABBAD04F6591B5C8C" box="[446,599,1418,1432]" gridcol="2" gridrow="48" pageId="2" pageNumber="426">13.35, br s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD2D79ABA7D04DD5EE05CBB" box="[110,1452,1441,1455]" gridrow="49" pageId="2" pageNumber="426" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD2D79ABA7D04DD5BFC5CBB" box="[110,176,1441,1455]" gridcol="0" gridrow="49" pageId="2" pageNumber="426">OH-23</th>
|
||
<td id="C3305DC9FFD2D79AB97F04DD5F495CBB" box="[876,1029,1441,1455]" gridcol="4" gridrow="49" pageId="2" pageNumber="426">5.52, br s</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD22867BA4404B45AB45F17" blockId="2.[87,1249,1480,1540]" pageId="2" pageNumber="426">
|
||
<tableNote id="C3373779FFD22867BA4404B45AB45F17" pageId="2" pageNumber="426" targetBox="[110,1452,243,1455]" targetPageId="2">
|
||
The attached proton number of each carbon signal was verified by DEPT pulse sequence and confirmed by HMQC and HMBC 2D NMR spectra.
|
||
<superScript id="C9A49BBFFFD22867BA7404A75B225CF0" attach="right" box="[103,110,1499,1508]" fontSize="4" pageId="2" pageNumber="426">a</superScript>
|
||
This signal was not identified in the HMQC spectrum;
|
||
<superScript id="C9A49BBFFFD22867BA75048D5B215CEF" attach="right" box="[102,109,1521,1531]" fontSize="4" pageId="2" pageNumber="426">b</superScript>
|
||
These signals were overlapped in each column.
|
||
</tableNote>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD22866BA65060A59185E6D" blockId="2.[87,757,1603,2013]" lastBlockId="3.[113,783,1808,1998]" lastPageId="3" lastPageNumber="427" pageId="2" pageNumber="426">
|
||
Compound
|
||
<emphasis id="0CA5EAE5FFD22867BAFD060A5BB75E9D" bold="true" box="[238,251,1910,1929]" pageId="2" pageNumber="426">5</emphasis>
|
||
was isolated as a yellowish amorphous powder and [
|
||
<emphasis id="0CA5EAE5FFD22867BA8106EC5BD35EB1" box="[146,159,1936,1957]" italics="true" pageId="2" pageNumber="426">OE</emphasis>
|
||
]
|
||
<subScript id="A25534B2FFD22867BAB406E75BFE5EB3" attach="left" box="[167,178,1947,1959]" fontSize="5" pageId="2" pageNumber="426">D</subScript>
|
||
<superScript id="C9A49BBFFFD22867BAB406F25BF65E8E" attach="left" box="[167,186,1934,1946]" fontSize="5" pageId="2" pageNumber="426">25</superScript>
|
||
+38.2 (
|
||
<emphasis id="0CA5EAE5FFD22867BB0006ED5A515EB1" box="[275,285,1937,1957]" italics="true" pageId="2" pageNumber="426">c</emphasis>
|
||
0.01, methanol). The molecular formula of C
|
||
<subScript id="A25534B2FFD22867BA7706CA5B3B5ED6" attach="both" box="[100,119,1974,1986]" fontSize="5" pageId="2" pageNumber="426">27</subScript>
|
||
H
|
||
<subScript id="A25534B2FFD22867BA9406CA5BD65ED6" attach="both" box="[135,154,1974,1986]" fontSize="5" pageId="2" pageNumber="426">32</subScript>
|
||
O
|
||
<subScript id="A25534B2FFD22867BABA06CA5BFE5ED6" attach="both" box="[169,178,1974,1986]" fontSize="5" pageId="2" pageNumber="426">6</subScript>
|
||
Na was determined by HRESIMS ([M+Na]
|
||
<superScript id="C9A49BBFFFD22867B89C06D659D45EA2" attach="left" box="[655,664,1962,1974]" fontSize="5" pageId="2" pageNumber="426">+</superScript>
|
||
at
|
||
<emphasis id="0CA5EAE5FFD22867B8C306D059AF5ED4" box="[720,739,1964,1984]" italics="true" pageId="2" pageNumber="426">m</emphasis>
|
||
/
|
||
<emphasis id="0CA5EAE5FFD22867B8F806D059B95ED4" box="[747,757,1964,1984]" italics="true" pageId="2" pageNumber="426">z</emphasis>
|
||
475.2093). The UV and IR spectra were typical for a 2-arylbenzofuran derivative (
|
||
<bibRefCitation id="5A404B06FFD22867BE55073F5E415F42" author="Shen, H. & Hou, A. J." box="[1094,1293,1603,1622]" pageId="2" pageNumber="426" pagination="1451 - 1456" refId="ref15413" refString="Shen, H., Hou, A. J., 2008. Prenylated 2 - arylbenzofurans from Artocarpus petelotii. Nat. Prod. Res. 22, 1451 - 1456." type="journal article" year="2008">Shen and Hou, 2008</bibRefCitation>
|
||
) and were similar to those of compounds
|
||
<emphasis id="0CA5EAE5FFD22867BE0507235F6F5F66" bold="true" box="[1046,1059,1631,1650]" pageId="2" pageNumber="426">3</emphasis>
|
||
and
|
||
<emphasis id="0CA5EAE5FFD22867BE4407235F285F66" bold="true" box="[1111,1124,1631,1650]" pageId="2" pageNumber="426">4</emphasis>
|
||
. The
|
||
<superScript id="C9A49BBFFFD22867BE8F07275FE95F73" attach="right" box="[1180,1189,1627,1639]" fontSize="5" pageId="2" pageNumber="426">1</superScript>
|
||
H and
|
||
<superScript id="C9A49BBFFFD22867BEF907275FB15F73" attach="right" box="[1258,1277,1627,1639]" fontSize="5" pageId="2" pageNumber="426">13</superScript>
|
||
C NMR spectra of
|
||
<emphasis id="0CA5EAE5FFD22867BFA607235E8E5F66" bold="true" box="[1461,1474,1631,1650]" pageId="2" pageNumber="426">5</emphasis>
|
||
(
|
||
<tableCitation id="7353034CFFD22867B93E070758365F9A" box="[813,890,1659,1678]" captionStart="Table 2" captionStartId="4.[87,131,183,197]" captionTargetPageId="4" captionText="Table 2 1H (400 MHz) and 13C NMR (100 MHz) spectroscopic data of compounds 3–5." httpUri="http://table.plazi.org/id/6AAE667FFFD42861BA4401CB598D59C8" pageId="2" pageNumber="426" tableUuid="6AAE667FFFD42861BA4401CB598D59C8">Table 2</tableCitation>
|
||
) were similar to those of compounds
|
||
<emphasis id="0CA5EAE5FFD22867BF0507065E6F5F99" bold="true" box="[1302,1315,1658,1677]" pageId="2" pageNumber="426">3</emphasis>
|
||
and
|
||
<emphasis id="0CA5EAE5FFD22867BF4E07065E265F99" bold="true" box="[1373,1386,1658,1677]" pageId="2" pageNumber="426">4</emphasis>
|
||
. The
|
||
<superScript id="C9A49BBFFFD22867BFBB070B5EFD5F97" attach="right" box="[1448,1457,1655,1667]" fontSize="5" pageId="2" pageNumber="426">1</superScript>
|
||
H NMR spectrum indicated the presence of two methyl groups (
|
||
<emphasis id="0CA5EAE5FFD22867BFA407EB5E8E5FBE" box="[1463,1474,1687,1706]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
0.94 and 1.18) and two oxymethine protons (
|
||
<emphasis id="0CA5EAE5FFD22867BEE307CF5FB75FD2" box="[1264,1275,1715,1734]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
3.36 and 4.04) that were not present in
|
||
<emphasis id="0CA5EAE5FFD22867B9FC07B258B05FF5" bold="true" box="[1007,1020,1742,1761]" pageId="2" pageNumber="426">3</emphasis>
|
||
or
|
||
<emphasis id="0CA5EAE5FFD22867BE0E07B25F665FF5" bold="true" box="[1053,1066,1742,1761]" pageId="2" pageNumber="426">4</emphasis>
|
||
, and the spectrum of
|
||
<emphasis id="0CA5EAE5FFD22867BF1607B25E5E5FF5" bold="true" box="[1285,1298,1742,1761]" pageId="2" pageNumber="426">5</emphasis>
|
||
did not have resonances corresponding to the 3,3-dimethylallyl side-chain in
|
||
<emphasis id="0CA5EAE5FFD22867BFA607965E8E5FE9" bold="true" box="[1461,1474,1770,1789]" pageId="2" pageNumber="426">8</emphasis>
|
||
(
|
||
<bibRefCitation id="5A404B06FFD22867B93E067A5F6E5E0D" author="Puntumchai, A. & Kittakoop, P. & Rajviroongit, S. & Vimuttipong, S. & Likhitwitayawuid, K. & Thebtaranonth, Y." box="[813,1058,1798,1818]" pageId="2" pageNumber="426" pagination="485 - 486" refId="ref15253" refString="Puntumchai, A., Kittakoop, P., Rajviroongit, S., Vimuttipong, S., Likhitwitayawuid, K., Thebtaranonth, Y., 2004. Lakoochins A and B, new antimycobacterial stilbene derivatives from Artocarpus lakoocha. J. Nat. Prod. 67, 485 - 486." type="journal article" year="2004">Puntumchai et al., 2004</bibRefCitation>
|
||
). The
|
||
<superScript id="C9A49BBFFFD22867BE75067E5F235E1A" attach="right" box="[1126,1135,1794,1806]" fontSize="5" pageId="2" pageNumber="426">1</superScript>
|
||
H–
|
||
<superScript id="C9A49BBFFFD22867BE9F067E5FD95E1A" attach="right" box="[1164,1173,1794,1806]" fontSize="5" pageId="2" pageNumber="426">1</superScript>
|
||
H COSY and HMQC data of
|
||
<emphasis id="0CA5EAE5FFD22867BFA6067A5E8E5E0D" bold="true" box="[1461,1474,1798,1817]" pageId="2" pageNumber="426">5</emphasis>
|
||
established the connectivities of H-13 (
|
||
<emphasis id="0CA5EAE5FFD22867BED3065E5F875E21" box="[1216,1227,1826,1845]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
4.04)/H-14 (
|
||
<emphasis id="0CA5EAE5FFD22867BF40065E5E125E21" box="[1363,1374,1826,1845]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
3.36), H-13 (
|
||
<emphasis id="0CA5EAE5FFD22867B942064258105E45" box="[849,860,1854,1873]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
4.04)/C-13 (
|
||
<emphasis id="0CA5EAE5FFD22867B9F0064258A25E45" box="[995,1006,1854,1873]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
79.4), and H-14 (
|
||
<emphasis id="0CA5EAE5FFD22867BEA106425FF15E45" box="[1202,1213,1854,1873]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
3.36)/C-14 (
|
||
<emphasis id="0CA5EAE5FFD22867BF5706425E035E45" box="[1348,1359,1854,1873]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
66.7). The HMBC correlations of
|
||
<collectingCountry id="46C67667FFD22867BE1F06265F655E79" box="[1036,1065,1882,1901]" name="Switzerland" pageId="2" pageNumber="426">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD22867BE3A061F5F7E5E7B" attach="left" box="[1065,1074,1891,1903]" fontSize="5" pageId="2" pageNumber="426">3</subScript>
|
||
-16 and -17 (
|
||
<emphasis id="0CA5EAE5FFD22867BED106265F815E79" box="[1218,1229,1882,1901]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
0.94 and 1.18)/C-15 (
|
||
<emphasis id="0CA5EAE5FFD22867BFA406265E8E5E79" box="[1463,1474,1882,1901]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
56.8),
|
||
<collectingCountry id="46C67667FFD22867B976060A58CE5E9D" box="[869,898,1910,1929]" name="Switzerland" pageId="2" pageNumber="426">CH</collectingCountry>
|
||
<subScript id="A25534B2FFD22867B990060358C05E9F" attach="right" box="[899,908,1919,1931]" fontSize="5" pageId="2" pageNumber="426">3</subScript>
|
||
-16 and -17/C-14 (
|
||
<emphasis id="0CA5EAE5FFD22867BE43060A5F175E9D" box="[1104,1115,1910,1929]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
66.7), H-13 (
|
||
<emphasis id="0CA5EAE5FFD22867BEFB060A5FBF5E9D" box="[1256,1267,1910,1929]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
4.04)/C-15 (
|
||
<emphasis id="0CA5EAE5FFD22867BF65060A5ECD5E9D" box="[1398,1409,1910,1929]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
56.8), C-14 (
|
||
<emphasis id="0CA5EAE5FFD22867B97606EE583C5EB1" box="[869,880,1938,1957]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
66.7), and OMe-13 (
|
||
<emphasis id="0CA5EAE5FFD22867BE5E06EE5F145EB1" box="[1101,1112,1938,1957]" italics="true" pageId="2" pageNumber="426">δ</emphasis>
|
||
57.0) confirmed the presence of a 2,3-epoxy-3,3-dimethyl-1-oxygenerated propane moiety (
|
||
<bibRefCitation id="5A404B06FFD22867BF9806D258D45EC9" author="Jeong, S. H. & Ryu, Y. B. & Curtis-Long, M. J. & Ryu, H. W. & Baek, Y. S. & Kang, J. E. & Lee, W. S. & Park, K. H." pageId="2" pageNumber="426" pagination="1195 - 1203" refId="ref13928" refString="Jeong, S. H., Ryu, Y. B., Curtis-Long, M. J., Ryu, H. W., Baek, Y. S., Kang, J. E., Lee, W. S., Park, K. H., 2009. Tyrosinase inhibitory polyphenols from roots of Morus lhou. J. Agric. Food Chem. 57, 1195 - 1203." type="journal article" year="2009">Jeong et al., 2009</bibRefCitation>
|
||
). Furthermore, the HMBC correlations between H-13 (
|
||
<emphasis id="0CA5EAE5FFD32866BA69066E5BC95E31" box="[122,133,1810,1829]" italics="true" pageId="3" pageNumber="427">δ</emphasis>
|
||
4.04)/C-6
|
||
<emphasis id="0CA5EAE5FFD32866BAFA066C5BA15E08" box="[233,237,1808,1820]" italics="true" pageId="3" pageNumber="427">
|
||
<superScript id="C9A49BBFFFD32866BAFA066C5BA15E08" attach="left" box="[233,237,1808,1820]" fontSize="5" pageId="3" pageNumber="427">0</superScript>
|
||
</emphasis>
|
||
(
|
||
<emphasis id="0CA5EAE5FFD32866BAED066E5A455E31" box="[254,265,1810,1829]" italics="true" pageId="3" pageNumber="427">δ</emphasis>
|
||
119.7), C-1
|
||
<emphasis id="0CA5EAE5FFD32866BB93066C5AC85E08" box="[384,388,1808,1820]" italics="true" pageId="3" pageNumber="427">
|
||
<superScript id="C9A49BBFFFD32866BB93066C5AC85E08" attach="left" box="[384,388,1808,1820]" fontSize="5" pageId="3" pageNumber="427">0</superScript>
|
||
</emphasis>
|
||
(
|
||
<emphasis id="0CA5EAE5FFD32866BB87066E5AD35E31" box="[404,415,1810,1829]" italics="true" pageId="3" pageNumber="427">δ</emphasis>
|
||
132.9), and C-5
|
||
<emphasis id="0CA5EAE5FFD32866B850066C590B5E08" box="[579,583,1808,1820]" italics="true" pageId="3" pageNumber="427">
|
||
<superScript id="C9A49BBFFFD32866B850066C590B5E08" attach="left" box="[579,583,1808,1820]" fontSize="5" pageId="3" pageNumber="427">0</superScript>
|
||
</emphasis>
|
||
(
|
||
<emphasis id="0CA5EAE5FFD32866B84B066E592F5E31" box="[600,611,1810,1829]" italics="true" pageId="3" pageNumber="427">δ</emphasis>
|
||
157.1) indicated that the 2,3-epoxy-3,3-dimethyl-1-methoxy propanyl moiety was attached to C-6
|
||
<emphasis id="0CA5EAE5FFD32866BB01063B5A5A5E47" box="[274,278,1863,1875]" italics="true" pageId="3" pageNumber="427">
|
||
<superScript id="C9A49BBFFFD32866BB01063B5A5A5E47" attach="none" box="[274,278,1863,1875]" fontSize="5" pageId="3" pageNumber="427">0</superScript>
|
||
</emphasis>
|
||
. Hence, it was concluded that compound
|
||
<emphasis id="0CA5EAE5FFD32866B8C2063659925E49" bold="true" box="[721,734,1866,1885]" pageId="3" pageNumber="427">5</emphasis>
|
||
was as shown, and it was named epoxylakoochin A.
|
||
</paragraph>
|
||
<caption id="6AAE667FFFD32866BB4107C65FB15FDC" ID-DOI="http://doi.org/10.5281/zenodo.10528886" ID-Zenodo-Dep="10528886" box="[338,1277,1722,1737]" httpUri="https://zenodo.org/record/10528886/files/figure.png" pageId="3" pageNumber="427" startId="3.[338,364,1722,1736]" targetBox="[310,1306,183,1689]" targetPageId="3" targetType="figure">
|
||
<paragraph id="3E6E36F7FFD32866BB4107C65FB15FDC" blockId="3.[338,1277,1722,1737]" box="[338,1277,1722,1737]" pageId="3" pageNumber="427">
|
||
<emphasis id="0CA5EAE5FFD32866BB4107C65AC95FDC" bold="true" box="[338,389,1722,1736]" pageId="3" pageNumber="427">Fig. 1.</emphasis>
|
||
Structures of compounds
|
||
<emphasis id="0CA5EAE5FFD32866B84D07C659CA5FDC" bold="true" box="[606,646,1722,1737]" pageId="3" pageNumber="427">1–22</emphasis>
|
||
. Key information obtained from HMQC and HMBC spectra of
|
||
<emphasis id="0CA5EAE5FFD32866BE6D07C65FD15FDC" bold="true" box="[1150,1181,1722,1737]" pageId="3" pageNumber="427">2–6</emphasis>
|
||
are shown.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="3E6E36F7FFD32861BA8206FD58105D87" blockId="3.[113,783,1808,1998]" lastBlockId="4.[805,1475,1124,2008]" lastPageId="4" lastPageNumber="428" pageId="3" pageNumber="427">
|
||
Compound
|
||
<emphasis id="0CA5EAE5FFD32866BB1406FD5A585E80" bold="true" box="[263,276,1921,1940]" pageId="3" pageNumber="427">6</emphasis>
|
||
was obtained as a brownish amorphous powder, [
|
||
<emphasis id="0CA5EAE5FFD32866BA6A06E05BCA5EA5" box="[121,134,1948,1969]" italics="true" pageId="3" pageNumber="427">OE</emphasis>
|
||
]
|
||
<subScript id="A25534B2FFD32866BA9D06DA5BD55EA6" attach="left" box="[142,153,1958,1970]" fontSize="5" pageId="3" pageNumber="427">D</subScript>
|
||
<superScript id="C9A49BBFFFD32866BA9D06E55BED5EB1" attach="left" box="[142,161,1945,1957]" fontSize="5" pageId="3" pageNumber="427">25</superScript>
|
||
<emphasis id="0CA5EAE5FFD32866BAA806E25B805EA4" box="[187,204,1950,1968]" italics="true" pageId="3" pageNumber="427">—</emphasis>
|
||
3.1 (
|
||
<emphasis id="0CA5EAE5FFD32866BB1F06E05A5A5EA4" box="[268,278,1948,1968]" italics="true" pageId="3" pageNumber="427">c</emphasis>
|
||
0.05, methanol). The molecular formula C
|
||
<subScript id="A25534B2FFD32866BA6C06BE5BDE5EDA" attach="right" box="[127,146,1986,1998]" fontSize="5" pageId="3" pageNumber="427">36</subScript>
|
||
H
|
||
<subScript id="A25534B2FFD32866BAB206BE5BFF5EDA" attach="both" box="[161,179,1986,1998]" fontSize="5" pageId="3" pageNumber="427">30</subScript>
|
||
O
|
||
<subScript id="A25534B2FFD32866BAD006BE5B995EDA" attach="both" box="[195,213,1986,1998]" fontSize="5" pageId="3" pageNumber="427">10</subScript>
|
||
Na was deduced from HRESIMS ([M+Na]
|
||
<superScript id="C9A49BBFFFD32866B8B906C959FF5ED5" attach="left" box="[682,691,1973,1985]" fontSize="5" pageId="3" pageNumber="427">+</superScript>
|
||
at
|
||
<emphasis id="0CA5EAE5FFD32866B8F806C459B25ED8" box="[747,766,1976,1996]" italics="true" pageId="3" pageNumber="427">m</emphasis>
|
||
/
|
||
<emphasis id="0CA5EAE5FFD32866B91606C458435ED8" box="[773,783,1976,1996]" italics="true" pageId="3" pageNumber="427">z</emphasis>
|
||
645.1734). The IR spectrum showed characteristic absorption bands of a hydroxy group (
|
||
<quantity id="F9299B12FFD32866BE4406525FE35E55" box="[1111,1199,1838,1857]" metricMagnitude="1" metricUnit="m" metricValue="3.342" pageId="3" pageNumber="427" unit="cm" value="3342.0">3342 cm</quantity>
|
||
<superScript id="C9A49BBFFFD32866BEBC06565F885E22" attach="left" box="[1199,1220,1834,1846]" fontSize="5" pageId="3" pageNumber="427">
|
||
<emphasis id="0CA5EAE5FFD32866BEBC06565FF75E22" box="[1199,1211,1834,1846]" italics="true" pageId="3" pageNumber="427">—</emphasis>
|
||
1
|
||
</superScript>
|
||
) and a benzene ring (1612 and
|
||
<quantity id="F9299B12FFD32866B9790635588D5E49" box="[874,961,1865,1885]" metricMagnitude="1" metricUnit="m" metricValue="1.516" pageId="3" pageNumber="427" unit="cm" value="1516.0">1516 cm</quantity>
|
||
<superScript id="C9A49BBFFFD32866B9D3063A589A5E46" attach="left" box="[960,982,1862,1874]" fontSize="5" pageId="3" pageNumber="427">
|
||
<emphasis id="0CA5EAE5FFD32866B9D3063A58805E46" box="[960,972,1862,1874]" italics="true" pageId="3" pageNumber="427">—</emphasis>
|
||
1
|
||
</superScript>
|
||
). The UV spectrum of
|
||
<emphasis id="0CA5EAE5FFD32866BEA006355F8C5E48" bold="true" box="[1203,1216,1865,1884]" pageId="3" pageNumber="427">6</emphasis>
|
||
was similar to that of alboctalol (
|
||
<emphasis id="0CA5EAE5FFD32866B96E061958C65E6C" bold="true" box="[893,906,1893,1912]" pageId="3" pageNumber="427">9</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD32866B9B1061A5F145E6D" author="Royer, M. & Herbette, G. & Eparvier, V. & Beauchene, J. & Thibaut, B. & Stien, D." box="[930,1112,1893,1913]" pageId="3" pageNumber="427" pagination="1708 - 1713" refId="ref15355" refString="Royer, M., Herbette, G., Eparvier, V., Beauchene, J., Thibaut, B., Stien, D., 2010. Secondary metabolites of Bagassa guianensis Aubl. wood: a study of the chemotaxonomy of the Moraceae family. Phytochemistry 71, 1708 - 1713." type="journal article" year="2010">Royer et al., 2010</bibRefCitation>
|
||
). The
|
||
<superScript id="C9A49BBFFFD32866BE8F061E5FE95E7A" attach="right" box="[1180,1189,1890,1902]" fontSize="5" pageId="3" pageNumber="427">1</superScript>
|
||
H NMR spectrum showed one pair of methylene protons at
|
||
<emphasis id="0CA5EAE5FFD32866BE6F06FE5FCB5E81" box="[1148,1159,1922,1941]" italics="true" pageId="3" pageNumber="427">δ</emphasis>
|
||
2.21 (1H, br s,
|
||
<subScript id="A25534B2FFD32866BF2406FE5E2C5E80" attach="left" box="[1335,1376,1921,1943]" fontSize="5" pageId="3" pageNumber="427">Hax-</subScript>
|
||
6) and 2.42 (1H, dd,
|
||
<emphasis id="0CA5EAE5FFD32866B98D06E058E95EA4" box="[926,933,1948,1968]" italics="true" pageId="3" pageNumber="427">J</emphasis>
|
||
= 15.6, 3.2 Hz,
|
||
<subScript id="A25534B2FFD32866BE5506E25F3C5EA4" attach="left" box="[1094,1136,1949,1970]" fontSize="5" pageId="3" pageNumber="427">Heq-</subScript>
|
||
6), five methine protons at
|
||
<emphasis id="0CA5EAE5FFD32866BF8806E25EEA5EA5" box="[1435,1446,1950,1969]" italics="true" pageId="3" pageNumber="427">δ</emphasis>
|
||
3.45 (1H, br s, H-4b), 3.57 (2H, br s, H-5 and H-10b), 4.40 (1H, br s, H-11), and 4.93 (1H, br s, H-12). The hydroxy signals at
|
||
<emphasis id="0CA5EAE5FFD42861B86C051959C65D6C" box="[639,650,1125,1144]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
6.92, 7.40, 7.71, 7.81, 7.97 and 8.14 were exchangeable by adding D
|
||
<subScript id="A25534B2FFD42861B8AB05F5598D5D81" attach="both" box="[696,705,1161,1173]" fontSize="5" pageId="4" pageNumber="428">2</subScript>
|
||
O. In addition, five aromatic systems including three dihydoxylated phenyls and two tetra-substituted benzenes were identified according to the resonances in the
|
||
<superScript id="C9A49BBFFFD42861BB5E05AC5A1A5DC8" attach="right" box="[333,342,1232,1244]" fontSize="5" pageId="4" pageNumber="428">1</superScript>
|
||
H NMR, as well as in the
|
||
<superScript id="C9A49BBFFFD42861B85C05AC592E5DC8" attach="right" box="[591,610,1232,1244]" fontSize="5" pageId="4" pageNumber="428">13</superScript>
|
||
C NMR spectra of
|
||
<emphasis id="0CA5EAE5FFD42861BA60058C5BCC5C17" bold="true" box="[115,128,1264,1283]" pageId="4" pageNumber="428">6</emphasis>
|
||
. From the
|
||
<superScript id="C9A49BBFFFD42861BAE205905BB65DEC" attach="right" box="[241,250,1260,1272]" fontSize="5" pageId="4" pageNumber="428">1</superScript>
|
||
H NMR spectrum of
|
||
<emphasis id="0CA5EAE5FFD42861BBDC058C5A905C17" bold="true" box="[463,476,1264,1283]" pageId="4" pageNumber="428">6</emphasis>
|
||
, three dihydroxylated phenyls were verified as one 3,5-dihydroxyphenyl [comprising resonances at
|
||
<emphasis id="0CA5EAE5FFD42861BAD204545B805C2F" box="[193,204,1320,1339]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
6.09 (2H, d,
|
||
<emphasis id="0CA5EAE5FFD42861BB47045B5A175C2F" box="[340,347,1319,1339]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 2.0 Hz, H-20 & H-24) and 6.12 (1H, t,
|
||
<emphasis id="0CA5EAE5FFD42861BA44043E5B125C42" box="[87,94,1346,1366]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 2.0 Hz, H-22)] and two 2,4-dihydroxyphenyls [resonances at
|
||
<emphasis id="0CA5EAE5FFD42861B8F9043859B95C43" box="[746,757,1348,1367]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
6.09 (1H, dd,
|
||
<emphasis id="0CA5EAE5FFD42861BAF404225BA25C66" box="[231,238,1374,1394]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 8.4, 2.4 Hz, H-29), 6.33 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD42861B8580422591E5C66" box="[587,594,1374,1394]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 8.4 Hz, H-30), and 6.35 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD42861BB1904065A5D5C9A" box="[266,273,1402,1422]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 2.4 Hz, H-27) as one system, as well as at
|
||
<emphasis id="0CA5EAE5FFD42861B8F9040759B95C9A" box="[746,757,1403,1422]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
6.21 (1H, dd,
|
||
<emphasis id="0CA5EAE5FFD42861BAF404EA5BA25CBE" box="[231,238,1430,1450]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 8.4, 2.4 Hz, H-17), 6.43 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD42861B85804EA591E5CBE" box="[587,594,1430,1450]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 2.4 Hz, H-15), and 6.64 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD42861BB0404CE5A525CD2" box="[279,286,1458,1478]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 8.4 Hz, H-18) as another system]. The
|
||
<superScript id="C9A49BBFFFD42861B8C804D359A85CAF" attach="right" box="[731,740,1455,1467]" fontSize="5" pageId="4" pageNumber="428">1</superScript>
|
||
H NMR resonances of the two 1,3,5,6-tetra-substituted benzenes were identified at
|
||
<emphasis id="0CA5EAE5FFD42861BB0B04975A6F5CEA" box="[280,291,1515,1534]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
5.92 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD42861BBBE04965AF85CEA" box="[429,436,1514,1534]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 2.4 Hz, H-7) and 6.07 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD42861BA44077A5B125F0E" box="[87,94,1542,1562]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 2.4 Hz, H-9), as well as at
|
||
<emphasis id="0CA5EAE5FFD42861BB82077B5AD05F0E" box="[401,412,1543,1562]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
6.15 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD42861B83F077A597F5F0E" box="[556,563,1542,1562]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 2.4 Hz, H-4) and 6.18 (1H, d,
|
||
<emphasis id="0CA5EAE5FFD42861BACE075E5BA85F22" box="[221,228,1570,1590]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
= 2.4 Hz, H-2). The above evidence suggested that compound
|
||
<emphasis id="0CA5EAE5FFD42861BADA07425B9A5F45" bold="true" box="[201,214,1598,1617]" pageId="4" pageNumber="428">6</emphasis>
|
||
had a polycyclic ring system substituted by four phenolic hydroxys and three dihydroxylated phenyls. The COSY spectrum of
|
||
<emphasis id="0CA5EAE5FFD42861BAB9070A5BFB5F9D" bold="true" box="[170,183,1654,1673]" pageId="4" pageNumber="428">6</emphasis>
|
||
showed cross-peaks of
|
||
<emphasis id="0CA5EAE5FFD42861BBBB070B5AFF5F9E" box="[424,435,1655,1674]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
3.45 (H-4b) with 3.57 (H-5 and H-10b),
|
||
<emphasis id="0CA5EAE5FFD42861BABF07EF5BFB5FB2" box="[172,183,1683,1702]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
3.57 (H-10b) with 4.40 (H-11), and
|
||
<emphasis id="0CA5EAE5FFD42861B82707EF59735FB2" box="[564,575,1683,1702]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
4.40 (H-11) with 4.93 (H-12) that correlated with these aliphatic signals, implying that compound
|
||
<emphasis id="0CA5EAE5FFD42861BAE507B65A4F5FC9" bold="true" box="[246,259,1738,1757]" pageId="4" pageNumber="428">6</emphasis>
|
||
contained a 4b,5,6,10b,11,12-hexahydrochrysene scaffold substituted by three dihydroxylated phenyls (
|
||
<bibRefCitation id="5A404B06FFD42861B865079A5BC65E01" author="Collins, D. J. & Cullen, J. D. & Stone, G. M." pageId="4" pageNumber="428" pagination="745 - 756" refId="ref13392" refString="Collins, D. J., Cullen, J. D., Stone, G. M., 1988. The structure and function of estrogens. 10. Synthesis of 5,5 - dimethyl-cis- 4 b, 5,6,10 b, 11,12 - hexahydrochrysene- 2,8 - diol - the estrogenic activity of this and of related c-methylated hydrochrysenediols. Aust. J. Chem. 41, 745 - 756." type="journal article" year="1988">Collins et al., 1988</bibRefCitation>
|
||
). After the validation of each proton–carbon attached signals in the HMQC spectrum, the structure of
|
||
<emphasis id="0CA5EAE5FFD42861B8170662595D5E25" bold="true" box="[516,529,1822,1841]" pageId="4" pageNumber="428">6</emphasis>
|
||
was then established as 1,3,8,10-tetrahydroxy-5,12-di-(2,4-dihydroxyphenyl)-11-(3,5- dihydroxyphenyl)-4b,5,6,10b,11,12-hexahydrochrysene, namely artoxanthol (
|
||
<emphasis id="0CA5EAE5FFD42861BAF7060D5BBD5E90" bold="true" box="[228,241,1905,1924]" pageId="4" pageNumber="428">6</emphasis>
|
||
), by advanced information obtained from the HMBC spectrum shown in
|
||
<figureCitation id="A6EA2A72FFD42861BB6206F15AE65EB4" box="[369,426,1933,1952]" captionStart="Fig" captionStartId="3.[338,364,1722,1736]" captionTargetBox="[310,1306,183,1689]" captionTargetId="graphics-612@3.[675,888,748,963]" captionTargetPageId="3" captionText="Fig. 1. Structures of compounds 1–22. Key information obtained from HMQC and HMBC spectra of 2–6 are shown." figureDoi="http://doi.org/10.5281/zenodo.10528886" httpUri="https://zenodo.org/record/10528886/files/figure.png" pageId="4" pageNumber="428">Fig. 1</figureCitation>
|
||
. The relative configuration of
|
||
<emphasis id="0CA5EAE5FFD42861B8FB06F159B95EB4" bold="true" box="[744,757,1933,1952]" pageId="4" pageNumber="428">6</emphasis>
|
||
at H-4b, H-5, H-10b, H-11, and H-12 were found to be all
|
||
<emphasis id="0CA5EAE5FFD42861B88B06D559E85EA8" box="[664,676,1961,1980]" italics="true" pageId="4" pageNumber="428">β</emphasis>
|
||
according to the NOESY experiments illustrated in
|
||
<figureCitation id="A6EA2A72FFD42861B83506B959125ECC" box="[550,606,1989,2008]" captionStart="Fig" captionStartId="5.[113,139,635,649]" captionTargetBox="[150,748,185,602]" captionTargetId="figure-453@5.[146,752,181,606]" captionTargetPageId="5" captionText="Fig. 2. Key information from NOESY experiments of artoxanthol (6). The molecular model was established by MMF94 minimization (ChemBio3D 11.0®)." figureDoi="http://doi.org/10.5281/zenodo.10486280" httpUri="https://zenodo.org/record/10486280/files/figure.png" pageId="4" pageNumber="428">Fig. 2</figureCitation>
|
||
. However, the absolute configuration of
|
||
<emphasis id="0CA5EAE5FFD42861BE3805185F745D63" bold="true" box="[1067,1080,1124,1143]" pageId="4" pageNumber="428">6</emphasis>
|
||
is still unidentified because of limited yield.
|
||
</paragraph>
|
||
<caption id="6AAE667FFFD42861BA4401CB598D59C8" ID-Table-UUID="6AAE667FFFD42861BA4401CB598D59C8" httpUri="http://table.plazi.org/id/6AAE667FFFD42861BA4401CB598D59C8" pageId="4" pageNumber="428" startId="4.[87,131,183,197]" targetBox="[110,1451,243,998]" targetIsTable="true" targetPageId="4" targetType="table">
|
||
<paragraph id="3E6E36F7FFD42861BA4401CB598D59C8" blockId="4.[87,705,183,220]" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861BA4401CB5BDF59D1" bold="true" box="[87,147,183,197]" pageId="4" pageNumber="428">Table 2</emphasis>
|
||
<superScript id="C9A49BBFFFD42861BA4401B65B1259C0" attach="right" box="[87,94,202,212]" fontSize="4" pageId="4" pageNumber="428">1</superScript>
|
||
H (400 MHz) and
|
||
<superScript id="C9A49BBFFFD42861BAFE01B65BB059C0" attach="right" box="[237,252,202,212]" fontSize="4" pageId="4" pageNumber="428">13</superScript>
|
||
C NMR (100 MHz) spectroscopic data of compounds
|
||
<emphasis id="0CA5EAE5FFD42861B8B301B159F259C8" bold="true" box="[672,702,205,220]" pageId="4" pageNumber="428">3–5</emphasis>
|
||
.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="3E6E36F7FFD42861BA7D018858EC5AF2" pageId="4" pageNumber="428">
|
||
<table id="4CD1C457FFD4D79ABA7D018F5EE75AF2" box="[110,1451,243,998]" gridcols="7" gridrows="31" pageId="4" pageNumber="428">
|
||
<tr id="80E134B5FFD4D79ABA7D018F5EE75810" box="[110,1451,243,260]" gridrow="0" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D018F5BFD5810" box="[110,177,243,260]" gridcol="0" gridrow="0" pageId="4" pageNumber="428">Position</th>
|
||
<th id="C3305DC9FFD4D79ABB03018F5ACF5810" box="[272,387,243,260]" gridcol="1" gridrow="0" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861BB0301885A565816" bold="true" box="[272,282,244,258]" pageId="4" pageNumber="428">3</emphasis>
|
||
(acetone-
|
||
<emphasis id="0CA5EAE5FFD42861BB78018F5A395816" box="[363,373,243,258]" italics="true" pageId="4" pageNumber="428">d</emphasis>
|
||
6)
|
||
</th>
|
||
<th id="C3305DC9FFD4D79AB8BB018F58575810" box="[680,795,243,260]" gridcol="3" gridrow="0" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861B8BB018859FE5816" bold="true" box="[680,690,244,258]" pageId="4" pageNumber="428">4</emphasis>
|
||
(acetone-
|
||
<emphasis id="0CA5EAE5FFD42861B917018F58425816" box="[772,782,243,258]" italics="true" pageId="4" pageNumber="428">d</emphasis>
|
||
6)
|
||
</th>
|
||
<th id="C3305DC9FFD4D79ABE62018F5FB35810" box="[1137,1279,243,260]" gridcol="5" gridrow="0" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861BE6201885F375816" bold="true" box="[1137,1147,244,258]" pageId="4" pageNumber="428">5</emphasis>
|
||
(chloroform-
|
||
<emphasis id="0CA5EAE5FFD42861BEFB018F5FBE5816" box="[1256,1266,243,258]" italics="true" pageId="4" pageNumber="428">d</emphasis>
|
||
1)
|
||
</th>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D00695EE75832" box="[110,1451,277,294]" gridrow="1" pageId="4" pageNumber="428" rowspan-0="1">
|
||
<td id="C3305DC9FFD4D79ABB0300695ACF5832" box="[272,387,277,294]" gridcol="1" gridrow="1" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861BB0300695A555830" box="[272,281,277,292]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
C, mult.
|
||
</td>
|
||
<td id="C3305DC9FFD4D79ABBAF006959065832" box="[444,586,277,294]" gridcol="2" gridrow="1" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861BBAF00695A895830" box="[444,453,277,292]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
H (
|
||
<emphasis id="0CA5EAE5FFD42861BBC900695A935830" box="[474,479,277,292]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
in Hz)
|
||
</td>
|
||
<td id="C3305DC9FFD4D79AB8BB006958575832" box="[680,795,277,294]" gridcol="3" gridrow="1" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861B8BB006959FD5830" box="[680,689,277,292]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
C, mult.
|
||
</td>
|
||
<td id="C3305DC9FFD4D79AB94600695F5F5832" box="[853,1043,277,294]" gridcol="4" gridrow="1" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861B946006958125830" box="[853,862,277,292]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
H (
|
||
<emphasis id="0CA5EAE5FFD42861B960006958345830" box="[883,888,277,292]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
in Hz)
|
||
</td>
|
||
<td id="C3305DC9FFD4D79ABE6200695FB35832" box="[1137,1279,277,294]" gridcol="5" gridrow="1" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861BE6200695F365830" box="[1137,1146,277,292]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
C, mult.
|
||
</td>
|
||
<td id="C3305DC9FFD4D79ABF0E00695EE75832" box="[1309,1451,277,294]" gridcol="6" gridrow="1" pageId="4" pageNumber="428">
|
||
<emphasis id="0CA5EAE5FFD42861BF0E00695E6A5830" box="[1309,1318,277,292]" italics="true" pageId="4" pageNumber="428">δ</emphasis>
|
||
H (
|
||
<emphasis id="0CA5EAE5FFD42861BF2F00695E0D5830" box="[1340,1345,277,292]" italics="true" pageId="4" pageNumber="428">J</emphasis>
|
||
in Hz)
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D004B5EE75851" box="[110,1451,311,325]" gridrow="2" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D004B5BFD5851" box="[110,177,311,325]" gridcol="0" gridrow="2" pageId="4" pageNumber="428">2</th>
|
||
<td id="C3305DC9FFD4D79ABB03004B5ACF5851" box="[272,387,311,325]" gridcol="1" gridrow="2" pageId="4" pageNumber="428">154.3, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB004B58575851" box="[680,795,311,325]" gridcol="3" gridrow="2" pageId="4" pageNumber="428">154.1, C</td>
|
||
<td id="C3305DC9FFD4D79ABE62004B5FB35851" box="[1137,1279,311,325]" gridcol="5" gridrow="2" pageId="4" pageNumber="428">152.1, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D00325EE75849" box="[110,1451,334,349]" gridrow="3" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D00325BFD5849" box="[110,177,334,349]" gridcol="0" gridrow="3" pageId="4" pageNumber="428">3</th>
|
||
<td id="C3305DC9FFD4D79ABB0300325ACF5849" box="[272,387,334,349]" gridcol="1" gridrow="3" pageId="4" pageNumber="428">107.6, CH</td>
|
||
<td id="C3305DC9FFD4D79ABBAF003259065849" box="[444,586,334,349]" gridcol="2" gridrow="3" pageId="4" pageNumber="428">6.62, s</td>
|
||
<td id="C3305DC9FFD4D79AB8BB003258575849" box="[680,795,334,349]" gridcol="3" gridrow="3" pageId="4" pageNumber="428">108.6, CH</td>
|
||
<td id="C3305DC9FFD4D79AB94600325F5F5849" box="[853,1043,334,349]" gridcol="4" gridrow="3" pageId="4" pageNumber="428">6.71, s</td>
|
||
<td id="C3305DC9FFD4D79ABE6200325FB35849" box="[1137,1279,334,349]" gridcol="5" gridrow="3" pageId="4" pageNumber="428">107.5, CH</td>
|
||
<td id="C3305DC9FFD4D79ABF0E00325EE75849" box="[1309,1451,334,349]" gridcol="6" gridrow="3" pageId="4" pageNumber="428">6.61, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D00195EE75867" box="[110,1451,357,371]" gridrow="4" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D00195BFD5867" box="[110,177,357,371]" gridcol="0" gridrow="4" pageId="4" pageNumber="428">3a</th>
|
||
<td id="C3305DC9FFD4D79ABB0300195ACF5867" box="[272,387,357,371]" gridcol="1" gridrow="4" pageId="4" pageNumber="428">122.8, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB001958575867" box="[680,795,357,371]" gridcol="3" gridrow="4" pageId="4" pageNumber="428">122.8, C</td>
|
||
<td id="C3305DC9FFD4D79ABE6200195FB35867" box="[1137,1279,357,371]" gridcol="5" gridrow="4" pageId="4" pageNumber="428">122.1, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D00005EE7589E" box="[110,1451,380,394]" gridrow="5" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D00005BFD589E" box="[110,177,380,394]" gridcol="0" gridrow="5" pageId="4" pageNumber="428">4</th>
|
||
<td id="C3305DC9FFD4D79ABB0300005ACF589E" box="[272,387,380,394]" gridcol="1" gridrow="5" pageId="4" pageNumber="428">122.3, CH</td>
|
||
<td id="C3305DC9FFD4D79ABBAF00005906589E" box="[444,586,380,394]" gridcol="2" gridrow="5" pageId="4" pageNumber="428">7.42, d (8.4)</td>
|
||
<td id="C3305DC9FFD4D79AB8BB00005857589E" box="[680,795,380,394]" gridcol="3" gridrow="5" pageId="4" pageNumber="428">122.3, CH</td>
|
||
<td id="C3305DC9FFD4D79AB94600005F5F589E" box="[853,1043,380,394]" gridcol="4" gridrow="5" pageId="4" pageNumber="428">7.42, d (8.4)</td>
|
||
<td id="C3305DC9FFD4D79ABE6200005FB3589E" box="[1137,1279,380,394]" gridcol="5" gridrow="5" pageId="4" pageNumber="428">121.1, CH</td>
|
||
<td id="C3305DC9FFD4D79ABF0E00005EE7589E" box="[1309,1451,380,394]" gridcol="6" gridrow="5" pageId="4" pageNumber="428">7.39, d (8.4)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D00EF5EE758B5" box="[110,1451,403,417]" gridrow="6" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D00EF5BFD58B5" box="[110,177,403,417]" gridcol="0" gridrow="6" pageId="4" pageNumber="428">5</th>
|
||
<td id="C3305DC9FFD4D79ABB0300EF5ACF58B5" box="[272,387,403,417]" gridcol="1" gridrow="6" pageId="4" pageNumber="428">113.4, CH</td>
|
||
<td id="C3305DC9FFD4D79ABBAF00EF590658B5" box="[444,586,403,417]" gridcol="2" gridrow="6" pageId="4" pageNumber="428">6.82, dd (8.4, 2.0)</td>
|
||
<td id="C3305DC9FFD4D79AB8BB00EF585758B5" box="[680,795,403,417]" gridcol="3" gridrow="6" pageId="4" pageNumber="428">113.5, CH</td>
|
||
<td id="C3305DC9FFD4D79AB94600EF5F5F58B5" box="[853,1043,403,417]" gridcol="4" gridrow="6" pageId="4" pageNumber="428">6.80, dd (8.4, 2.0)</td>
|
||
<td id="C3305DC9FFD4D79ABE6200EF5FB358B5" box="[1137,1279,403,417]" gridcol="5" gridrow="6" pageId="4" pageNumber="428">111.9, CH</td>
|
||
<td id="C3305DC9FFD4D79ABF0E00EF5EE758B5" box="[1309,1451,403,417]" gridcol="6" gridrow="6" pageId="4" pageNumber="428">6.77, dd (8.4, 2.0)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D00D55EE758AC" box="[110,1451,425,440]" gridrow="7" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D00D55BFD58AC" box="[110,177,425,440]" gridcol="0" gridrow="7" pageId="4" pageNumber="428">6</th>
|
||
<td id="C3305DC9FFD4D79ABB0300D55ACF58AC" box="[272,387,425,440]" gridcol="1" gridrow="7" pageId="4" pageNumber="428">156.8, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB00D5585758AC" box="[680,795,425,440]" gridcol="3" gridrow="7" pageId="4" pageNumber="428">156.8, C</td>
|
||
<td id="C3305DC9FFD4D79ABE6200D55FB358AC" box="[1137,1279,425,440]" gridcol="5" gridrow="7" pageId="4" pageNumber="428">153.4, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D00BC5EE758DB" box="[110,1451,448,463]" gridrow="8" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D00BC5BFD58DB" box="[110,177,448,463]" gridcol="0" gridrow="8" pageId="4" pageNumber="428">7</th>
|
||
<td id="C3305DC9FFD4D79ABB0300BC5ACF58DB" box="[272,387,448,463]" gridcol="1" gridrow="8" pageId="4" pageNumber="428">99.1, CH</td>
|
||
<td id="C3305DC9FFD4D79ABBAF00BC590658DB" box="[444,586,448,463]" gridcol="2" gridrow="8" pageId="4" pageNumber="428">6.96, d (2.0)</td>
|
||
<td id="C3305DC9FFD4D79AB8BB00BC585758DB" box="[680,795,448,463]" gridcol="3" gridrow="8" pageId="4" pageNumber="428">99.1, CH</td>
|
||
<td id="C3305DC9FFD4D79AB94600BC5F5F58DB" box="[853,1043,448,463]" gridcol="4" gridrow="8" pageId="4" pageNumber="428">6.95, d (2.0)</td>
|
||
<td id="C3305DC9FFD4D79ABE6200BC5FB358DB" box="[1137,1279,448,463]" gridcol="5" gridrow="8" pageId="4" pageNumber="428">98.2, CH</td>
|
||
<td id="C3305DC9FFD4D79ABF0E00BC5EE758DB" box="[1309,1451,448,463]" gridcol="6" gridrow="8" pageId="4" pageNumber="428">6.94, d (2.0)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D00AB5EE758F2" box="[110,1451,471,486]" gridrow="9" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D00AB5BFD58F2" box="[110,177,471,486]" gridcol="0" gridrow="9" pageId="4" pageNumber="428">7a</th>
|
||
<td id="C3305DC9FFD4D79ABB0300AB5ACF58F2" box="[272,387,471,486]" gridcol="1" gridrow="9" pageId="4" pageNumber="428">157.4, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB00AB585758F2" box="[680,795,471,486]" gridcol="3" gridrow="9" pageId="4" pageNumber="428">157.4, C</td>
|
||
<td id="C3305DC9FFD4D79ABE6200AB5FB358F2" box="[1137,1279,471,486]" gridcol="5" gridrow="9" pageId="4" pageNumber="428">155.4, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D00925EE758EB" box="[110,1451,494,511]" gridrow="10" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D00925BFD58EB" box="[110,177,494,511]" gridcol="0" gridrow="10" pageId="4" pageNumber="428">8</th>
|
||
<td id="C3305DC9FFD4D79ABB0300925ACF58EB" box="[272,387,494,511]" gridcol="1" gridrow="10" pageId="4" pageNumber="428">27.8, CH2</td>
|
||
<td id="C3305DC9FFD4D79ABBAF0092590658EB" box="[444,586,494,511]" gridcol="2" gridrow="10" pageId="4" pageNumber="428">3.14, d (7.2)</td>
|
||
<td id="C3305DC9FFD4D79AB8BB0092585758EB" box="[680,795,494,511]" gridcol="3" gridrow="10" pageId="4" pageNumber="428">27.9, CH2</td>
|
||
<td id="C3305DC9FFD4D79AB94600925F5F58EB" box="[853,1043,494,511]" gridcol="4" gridrow="10" pageId="4" pageNumber="428">3.15, m</td>
|
||
<td id="C3305DC9FFD4D79ABE6200925FB358EB" box="[1137,1279,494,511]" gridcol="5" gridrow="10" pageId="4" pageNumber="428">26.6, CH2</td>
|
||
<td id="C3305DC9FFD4D79ABF0E00925EE758EB" box="[1309,1451,494,511]" gridcol="6" gridrow="10" pageId="4" pageNumber="428">3.02-3.16, m</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D03795EE75B07" box="[110,1451,517,531]" gridrow="11" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D03795BFD5B07" box="[110,177,517,531]" gridcol="0" gridrow="11" pageId="4" pageNumber="428">9</th>
|
||
<td id="C3305DC9FFD4D79ABB0303795ACF5B07" box="[272,387,517,531]" gridcol="1" gridrow="11" pageId="4" pageNumber="428">125.4, CH</td>
|
||
<td id="C3305DC9FFD4D79ABBAF037959065B07" box="[444,586,517,531]" gridcol="2" gridrow="11" pageId="4" pageNumber="428">5.05, br t (7.2)</td>
|
||
<td id="C3305DC9FFD4D79AB8BB037958575B07" box="[680,795,517,531]" gridcol="3" gridrow="11" pageId="4" pageNumber="428">125.5, CH</td>
|
||
<td id="C3305DC9FFD4D79AB94603795F5F5B07" box="[853,1043,517,531]" gridcol="4" gridrow="11" pageId="4" pageNumber="428">5.06, br t (7.2)</td>
|
||
<td id="C3305DC9FFD4D79ABE6203795FB35B07" box="[1137,1279,517,531]" gridcol="5" gridrow="11" pageId="4" pageNumber="428">123.1, CH</td>
|
||
<td id="C3305DC9FFD4D79ABF0E03795EE75B07" box="[1309,1451,517,531]" gridcol="6" gridrow="11" pageId="4" pageNumber="428">5.01, br t (7.2)</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D03605EE75B3E" box="[110,1451,540,554]" gridrow="12" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D03605BFD5B3E" box="[110,177,540,554]" gridcol="0" gridrow="12" pageId="4" pageNumber="428">10</th>
|
||
<td id="C3305DC9FFD4D79ABB0303605ACF5B3E" box="[272,387,540,554]" gridcol="1" gridrow="12" pageId="4" pageNumber="428">130.9, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB036058575B3E" box="[680,795,540,554]" gridcol="3" gridrow="12" pageId="4" pageNumber="428">130.9, C</td>
|
||
<td id="C3305DC9FFD4D79ABE6203605FB35B3E" box="[1137,1279,540,554]" gridcol="5" gridrow="12" pageId="4" pageNumber="428">130.7, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D034F5EE75B55" box="[110,1451,563,577]" gridrow="13" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D034F5BFD5B55" box="[110,177,563,577]" gridcol="0" gridrow="13" pageId="4" pageNumber="428">11</th>
|
||
<td id="C3305DC9FFD4D79ABB03034F5ACF5B55" box="[272,387,563,577]" gridcol="1" gridrow="13" pageId="4" pageNumber="428">18.4, Me</td>
|
||
<td id="C3305DC9FFD4D79ABBAF034F59065B55" box="[444,586,563,577]" gridcol="2" gridrow="13" pageId="4" pageNumber="428">1.37, s</td>
|
||
<td id="C3305DC9FFD4D79AB8BB034F58575B55" box="[680,795,563,577]" gridcol="3" gridrow="13" pageId="4" pageNumber="428">18.4, Me</td>
|
||
<td id="C3305DC9FFD4D79AB946034F5F5F5B55" box="[853,1043,563,577]" gridcol="4" gridrow="13" pageId="4" pageNumber="428">1.38, s</td>
|
||
<td id="C3305DC9FFD4D79ABE62034F5FB35B55" box="[1137,1279,563,577]" gridcol="5" gridrow="13" pageId="4" pageNumber="428">17.6, Me</td>
|
||
<td id="C3305DC9FFD4D79ABF0E034F5EE75B55" box="[1309,1451,563,577]" gridcol="6" gridrow="13" pageId="4" pageNumber="428">1.38, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D03355EE75B4C" box="[110,1451,585,600]" gridrow="14" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D03355BFD5B4C" box="[110,177,585,600]" gridcol="0" gridrow="14" pageId="4" pageNumber="428">12</th>
|
||
<td id="C3305DC9FFD4D79ABB0303355ACF5B4C" box="[272,387,585,600]" gridcol="1" gridrow="14" pageId="4" pageNumber="428">26.5, Me</td>
|
||
<td id="C3305DC9FFD4D79ABBAF033559065B4C" box="[444,586,585,600]" gridcol="2" gridrow="14" pageId="4" pageNumber="428">1.54, s</td>
|
||
<td id="C3305DC9FFD4D79AB8BB033558575B4C" box="[680,795,585,600]" gridcol="3" gridrow="14" pageId="4" pageNumber="428">26.5, Me</td>
|
||
<td id="C3305DC9FFD4D79AB94603355F5F5B4C" box="[853,1043,585,600]" gridcol="4" gridrow="14" pageId="4" pageNumber="428">1.54, s</td>
|
||
<td id="C3305DC9FFD4D79ABE6203355FB35B4C" box="[1137,1279,585,600]" gridcol="5" gridrow="14" pageId="4" pageNumber="428">25.7, Me</td>
|
||
<td id="C3305DC9FFD4D79ABF0E03355EE75B4C" box="[1309,1451,585,600]" gridcol="6" gridrow="14" pageId="4" pageNumber="428">1.57, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D031C5EE75B91" box="[110,1451,608,645]" gridrow="15" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D031C5BFD5B91" box="[110,177,608,645]" gridcol="0" gridrow="15" pageId="4" pageNumber="428">13</th>
|
||
<td id="C3305DC9FFD4D79ABB03031C5ACF5B91" box="[272,387,608,645]" gridcol="1" gridrow="15" pageId="4" pageNumber="428">24.4, CH2</td>
|
||
<td id="C3305DC9FFD4D79ABBAF031C59065B91" box="[444,586,608,645]" gridcol="2" gridrow="15" pageId="4" pageNumber="428">2.42-2.47, m</td>
|
||
<td id="C3305DC9FFD4D79AB8BB031C58575B91" box="[680,795,608,645]" gridcol="3" gridrow="15" pageId="4" pageNumber="428">30.5, CH2</td>
|
||
<td id="C3305DC9FFD4D79AB946031C5F5F5B91" box="[853,1043,608,645]" gridcol="4" gridrow="15" pageId="4" pageNumber="428">2.58, dd (13.6, 10.4) 2.74, dd (13.6, 2.4)</td>
|
||
<td id="C3305DC9FFD4D79ABE62031C5FB35B91" box="[1137,1279,608,645]" gridcol="5" gridrow="15" pageId="4" pageNumber="428">79.4, CH</td>
|
||
<td id="C3305DC9FFD4D79ABF0E031C5EE75B91" box="[1309,1451,608,645]" gridcol="6" gridrow="15" pageId="4" pageNumber="428">4.04, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D03F25EE75B8B" box="[110,1451,654,671]" gridrow="16" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D03F25BFD5B8B" box="[110,177,654,671]" gridcol="0" gridrow="16" pageId="4" pageNumber="428">14</th>
|
||
<td id="C3305DC9FFD4D79ABB0303F25ACF5B8B" box="[272,387,654,671]" gridcol="1" gridrow="16" pageId="4" pageNumber="428">46.1, CH2</td>
|
||
<td id="C3305DC9FFD4D79ABBAF03F259065B8B" box="[444,586,654,671]" gridcol="2" gridrow="16" pageId="4" pageNumber="428">1.59-1.63, m</td>
|
||
<td id="C3305DC9FFD4D79AB8BB03F258575B8B" box="[680,795,654,671]" gridcol="3" gridrow="16" pageId="4" pageNumber="428">77.9, CH</td>
|
||
<td id="C3305DC9FFD4D79AB94603F25F5F5B8B" box="[853,1043,654,671]" gridcol="4" gridrow="16" pageId="4" pageNumber="428">3.59-3.63, m (10.4, 2.4)</td>
|
||
<td id="C3305DC9FFD4D79ABE6203F25FB35B8B" box="[1137,1279,654,671]" gridcol="5" gridrow="16" pageId="4" pageNumber="428">66.7, CH</td>
|
||
<td id="C3305DC9FFD4D79ABF0E03F25EE75B8B" box="[1309,1451,654,671]" gridcol="6" gridrow="16" pageId="4" pageNumber="428">3.36, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D03D95EE75BA7" box="[110,1451,677,691]" gridrow="17" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D03D95BFD5BA7" box="[110,177,677,691]" gridcol="0" gridrow="17" pageId="4" pageNumber="428">15</th>
|
||
<td id="C3305DC9FFD4D79ABB0303D95ACF5BA7" box="[272,387,677,691]" gridcol="1" gridrow="17" pageId="4" pageNumber="428">70.8, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB03D958575BA7" box="[680,795,677,691]" gridcol="3" gridrow="17" pageId="4" pageNumber="428">78.3, C</td>
|
||
<td id="C3305DC9FFD4D79ABE6203D95FB35BA7" box="[1137,1279,677,691]" gridcol="5" gridrow="17" pageId="4" pageNumber="428">56.8, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D03C05EE75BDE" box="[110,1451,700,714]" gridrow="18" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D03C05BFD5BDE" box="[110,177,700,714]" gridcol="0" gridrow="18" pageId="4" pageNumber="428">16</th>
|
||
<td id="C3305DC9FFD4D79ABB0303C05ACF5BDE" box="[272,387,700,714]" gridcol="1" gridrow="18" pageId="4" pageNumber="428">29.9, Me</td>
|
||
<td id="C3305DC9FFD4D79ABBAF03C059065BDE" box="[444,586,700,714]" gridcol="2" gridrow="18" pageId="4" pageNumber="428">0.98, s</td>
|
||
<td id="C3305DC9FFD4D79AB8BB03C058575BDE" box="[680,795,700,714]" gridcol="3" gridrow="18" pageId="4" pageNumber="428">21.3, Me</td>
|
||
<td id="C3305DC9FFD4D79AB94603C05F5F5BDE" box="[853,1043,700,714]" gridcol="4" gridrow="18" pageId="4" pageNumber="428">0.93, s</td>
|
||
<td id="C3305DC9FFD4D79ABE6203C05FB35BDE" box="[1137,1279,700,714]" gridcol="5" gridrow="18" pageId="4" pageNumber="428">19.6, Me</td>
|
||
<td id="C3305DC9FFD4D79ABF0E03C05EE75BDE" box="[1309,1451,700,714]" gridcol="6" gridrow="18" pageId="4" pageNumber="428">0.94, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D03AF5EE75BF5" box="[110,1451,723,737]" gridrow="19" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D03AF5BFD5BF5" box="[110,177,723,737]" gridcol="0" gridrow="19" pageId="4" pageNumber="428">17</th>
|
||
<td id="C3305DC9FFD4D79ABB0303AF5ACF5BF5" box="[272,387,723,737]" gridcol="1" gridrow="19" pageId="4" pageNumber="428">29.9, Me</td>
|
||
<td id="C3305DC9FFD4D79ABBAF03AF59065BF5" box="[444,586,723,737]" gridcol="2" gridrow="19" pageId="4" pageNumber="428">0.98, s</td>
|
||
<td id="C3305DC9FFD4D79AB8BB03AF58575BF5" box="[680,795,723,737]" gridcol="3" gridrow="19" pageId="4" pageNumber="428">22.1, Me</td>
|
||
<td id="C3305DC9FFD4D79AB94603AF5F5F5BF5" box="[853,1043,723,737]" gridcol="4" gridrow="19" pageId="4" pageNumber="428">0.96, s</td>
|
||
<td id="C3305DC9FFD4D79ABE6203AF5FB35BF5" box="[1137,1279,723,737]" gridcol="5" gridrow="19" pageId="4" pageNumber="428">24.8, Me</td>
|
||
<td id="C3305DC9FFD4D79ABF0E03AF5EE75BF5" box="[1309,1451,723,737]" gridcol="6" gridrow="19" pageId="4" pageNumber="428">1.18, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D038D5EE75A16" box="[110,1451,753,770]" gridrow="20" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D038D5BFD5A16" box="[110,177,753,770]" gridcol="0" gridrow="20" pageId="4" pageNumber="428">
|
||
1
|
||
<emphasis id="0CA5EAE5FFD42861BA6B038D5B305BEE" box="[120,124,753,762]" italics="true" pageId="4" pageNumber="428">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD4D79ABB03038D5ACF5A16" box="[272,387,753,770]" gridcol="1" gridrow="20" pageId="4" pageNumber="428">133.5, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB038D58575A16" box="[680,795,753,770]" gridcol="3" gridrow="20" pageId="4" pageNumber="428">134.5, C</td>
|
||
<td id="C3305DC9FFD4D79ABE62038D5FB35A16" box="[1137,1279,753,770]" gridcol="5" gridrow="20" pageId="4" pageNumber="428">132.9, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D02745EE75A0C" box="[110,1451,776,792]" gridrow="21" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D02745BFD5A0C" box="[110,177,776,792]" gridcol="0" gridrow="21" pageId="4" pageNumber="428">
|
||
2
|
||
<emphasis id="0CA5EAE5FFD42861BA6B02745B305A05" box="[120,124,776,785]" italics="true" pageId="4" pageNumber="428">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD4D79ABB0302745ACF5A0C" box="[272,387,776,792]" gridcol="1" gridrow="21" pageId="4" pageNumber="428">123.8, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB027458575A0C" box="[680,795,776,792]" gridcol="3" gridrow="21" pageId="4" pageNumber="428">124.2, C</td>
|
||
<td id="C3305DC9FFD4D79ABE6202745FB35A0C" box="[1137,1279,776,792]" gridcol="5" gridrow="21" pageId="4" pageNumber="428">124.0, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D02615EE75A3B" box="[110,1451,797,815]" gridrow="22" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D02615BFD5A3B" box="[110,177,797,815]" gridcol="0" gridrow="22" pageId="4" pageNumber="428">
|
||
3
|
||
<emphasis id="0CA5EAE5FFD42861BA6B02635B305A3C" box="[120,124,799,808]" italics="true" pageId="4" pageNumber="428">0</emphasis>
|
||
a
|
||
</th>
|
||
<td id="C3305DC9FFD4D79ABB0302615ACF5A3B" box="[272,387,797,815]" gridcol="1" gridrow="22" pageId="4" pageNumber="428">157.8, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB026158575A3B" box="[680,795,797,815]" gridcol="3" gridrow="22" pageId="4" pageNumber="428">158.2, C</td>
|
||
<td id="C3305DC9FFD4D79ABE6202615FB35A3B" box="[1137,1279,797,815]" gridcol="5" gridrow="22" pageId="4" pageNumber="428">158.2, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D024A5EE75A52" box="[110,1451,822,838]" gridrow="23" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D024A5BFD5A52" box="[110,177,822,838]" gridcol="0" gridrow="23" pageId="4" pageNumber="428">
|
||
4
|
||
<emphasis id="0CA5EAE5FFD42861BA6B024A5B305A2B" box="[120,124,822,831]" italics="true" pageId="4" pageNumber="428">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD4D79ABB03024A5ACF5A52" box="[272,387,822,838]" gridcol="1" gridrow="23" pageId="4" pageNumber="428">98.6, CH</td>
|
||
<td id="C3305DC9FFD4D79ABBAF024A59065A52" box="[444,586,822,838]" gridcol="2" gridrow="23" pageId="4" pageNumber="428">6.80, s</td>
|
||
<td id="C3305DC9FFD4D79AB8BB024A58575A52" box="[680,795,822,838]" gridcol="3" gridrow="23" pageId="4" pageNumber="428">98.7, CH</td>
|
||
<td id="C3305DC9FFD4D79AB946024A5F5F5A52" box="[853,1043,822,838]" gridcol="4" gridrow="23" pageId="4" pageNumber="428">6.82, s</td>
|
||
<td id="C3305DC9FFD4D79ABE62024A5FB35A52" box="[1137,1279,822,838]" gridcol="5" gridrow="23" pageId="4" pageNumber="428">97.2, CH</td>
|
||
<td id="C3305DC9FFD4D79ABF0E024A5EE75A52" box="[1309,1451,822,838]" gridcol="6" gridrow="23" pageId="4" pageNumber="428">6.60, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D02375EE75A49" box="[110,1451,843,861]" gridrow="24" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D02375BFD5A49" box="[110,177,843,861]" gridcol="0" gridrow="24" pageId="4" pageNumber="428">
|
||
5
|
||
<emphasis id="0CA5EAE5FFD42861BA6B02305B305A41" box="[120,124,844,853]" italics="true" pageId="4" pageNumber="428">0</emphasis>
|
||
a
|
||
</th>
|
||
<td id="C3305DC9FFD4D79ABB0302375ACF5A49" box="[272,387,843,861]" gridcol="1" gridrow="24" pageId="4" pageNumber="428">158.0, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB023758575A49" box="[680,795,843,861]" gridcol="3" gridrow="24" pageId="4" pageNumber="428">158.5, C</td>
|
||
<td id="C3305DC9FFD4D79ABE6202375FB35A49" box="[1137,1279,843,861]" gridcol="5" gridrow="24" pageId="4" pageNumber="428">157.1, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D021F5EE75A60" box="[110,1451,867,884]" gridrow="25" pageId="4" pageNumber="428" rowspan-2="1" rowspan-4="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D021F5BFD5A60" box="[110,177,867,884]" gridcol="0" gridrow="25" pageId="4" pageNumber="428">
|
||
6
|
||
<emphasis id="0CA5EAE5FFD42861BA6B021F5B305A78" box="[120,124,867,876]" italics="true" pageId="4" pageNumber="428">0</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD4D79ABB03021F5ACF5A60" box="[272,387,867,884]" gridcol="1" gridrow="25" pageId="4" pageNumber="428">125.6, C</td>
|
||
<td id="C3305DC9FFD4D79AB8BB021F58575A60" box="[680,795,867,884]" gridcol="3" gridrow="25" pageId="4" pageNumber="428">122.7, C</td>
|
||
<td id="C3305DC9FFD4D79ABE62021F5FB35A60" box="[1137,1279,867,884]" gridcol="5" gridrow="25" pageId="4" pageNumber="428">119.7, C</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D02005EE75A9F" box="[110,1451,892,907]" gridrow="26" pageId="4" pageNumber="428" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1">
|
||
<th id="C3305DC9FFD4D79ABA7D02005BFD5A9F" box="[110,177,892,907]" gridcol="0" gridrow="26" pageId="4" pageNumber="428">OMe-13</th>
|
||
<td id="C3305DC9FFD4D79ABE6202005FB35A9F" box="[1137,1279,892,907]" gridcol="5" gridrow="26" pageId="4" pageNumber="428">57.0, Me</td>
|
||
<td id="C3305DC9FFD4D79ABF0E02005EE75A9F" box="[1309,1451,892,907]" gridcol="6" gridrow="26" pageId="4" pageNumber="428">3.36, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D02EF5EE75AB6" box="[110,1451,915,930]" gridrow="27" pageId="4" pageNumber="428" rowspan-1="1" rowspan-2="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D02EF5BFD5AB6" box="[110,177,915,930]" gridcol="0" gridrow="27" pageId="4" pageNumber="428">OMe-14</th>
|
||
<td id="C3305DC9FFD4D79AB8BB02EF58575AB6" box="[680,795,915,930]" gridcol="3" gridrow="27" pageId="4" pageNumber="428">50.0, Me</td>
|
||
<td id="C3305DC9FFD4D79AB94602EF5F5F5AB6" box="[853,1043,915,930]" gridcol="4" gridrow="27" pageId="4" pageNumber="428">2.99, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D02DA5EE75AAD" box="[110,1451,934,953]" gridrow="28" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D02DA5BFD5AAD" box="[110,177,934,953]" gridcol="0" gridrow="28" pageId="4" pageNumber="428">
|
||
OMe-3
|
||
<emphasis id="0CA5EAE5FFD42861BAB602D45BE55AA5" box="[165,169,936,945]" italics="true" pageId="4" pageNumber="428">0</emphasis>
|
||
b
|
||
</th>
|
||
<td id="C3305DC9FFD4D79ABB0302DA5ACF5AAD" box="[272,387,934,953]" gridcol="1" gridrow="28" pageId="4" pageNumber="428">56.8, Me</td>
|
||
<td id="C3305DC9FFD4D79ABBAF02DA59065AAD" box="[444,586,934,953]" gridcol="2" gridrow="28" pageId="4" pageNumber="428">3.90, s</td>
|
||
<td id="C3305DC9FFD4D79AB8BB02DA58575AAD" box="[680,795,934,953]" gridcol="3" gridrow="28" pageId="4" pageNumber="428">56.9, Me</td>
|
||
<td id="C3305DC9FFD4D79AB94602DA5F5F5AAD" box="[853,1043,934,953]" gridcol="4" gridrow="28" pageId="4" pageNumber="428">3.90, s</td>
|
||
<td id="C3305DC9FFD4D79ABE6202DA5FB35AAD" box="[1137,1279,934,953]" gridcol="5" gridrow="28" pageId="4" pageNumber="428">56.1, Me</td>
|
||
<td id="C3305DC9FFD4D79ABF0E02DA5EE75AAD" box="[1309,1451,934,953]" gridcol="6" gridrow="28" pageId="4" pageNumber="428">3.88, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D02C15EE75ADB" box="[110,1451,957,975]" gridrow="29" pageId="4" pageNumber="428">
|
||
<th id="C3305DC9FFD4D79ABA7D02C15BFD5ADB" box="[110,177,957,975]" gridcol="0" gridrow="29" pageId="4" pageNumber="428">
|
||
OMe-5
|
||
<emphasis id="0CA5EAE5FFD42861BAB602C35BE55ADC" box="[165,169,959,968]" italics="true" pageId="4" pageNumber="428">0</emphasis>
|
||
b
|
||
</th>
|
||
<td id="C3305DC9FFD4D79ABB0302C15ACF5ADB" box="[272,387,957,975]" gridcol="1" gridrow="29" pageId="4" pageNumber="428">56.8, Me</td>
|
||
<td id="C3305DC9FFD4D79ABBAF02C159065ADB" box="[444,586,957,975]" gridcol="2" gridrow="29" pageId="4" pageNumber="428">3.91, s</td>
|
||
<td id="C3305DC9FFD4D79AB8BB02C158575ADB" box="[680,795,957,975]" gridcol="3" gridrow="29" pageId="4" pageNumber="428">57.0, Me</td>
|
||
<td id="C3305DC9FFD4D79AB94602C15F5F5ADB" box="[853,1043,957,975]" gridcol="4" gridrow="29" pageId="4" pageNumber="428">3.91, s</td>
|
||
<td id="C3305DC9FFD4D79ABE6202C15FB35ADB" box="[1137,1279,957,975]" gridcol="5" gridrow="29" pageId="4" pageNumber="428">55.7, Me</td>
|
||
<td id="C3305DC9FFD4D79ABF0E02C15EE75ADB" box="[1309,1451,957,975]" gridcol="6" gridrow="29" pageId="4" pageNumber="428">3.88, s</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD4D79ABA7D02A45EE75AF2" box="[110,1451,984,998]" gridrow="30" pageId="4" pageNumber="428" rowspan-1="1" rowspan-3="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="C3305DC9FFD4D79ABA7D02A45BFD5AF2" box="[110,177,984,998]" gridcol="0" gridrow="30" pageId="4" pageNumber="428">OH-6</th>
|
||
<td id="C3305DC9FFD4D79ABBAF02A459065AF2" box="[444,586,984,998]" gridcol="2" gridrow="30" pageId="4" pageNumber="428">8.50, br s</td>
|
||
<td id="C3305DC9FFD4D79AB94602A45F5F5AF2" box="[853,1043,984,998]" gridcol="4" gridrow="30" pageId="4" pageNumber="428">8.50, br s</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD42861BA44028359545D30" blockId="4.[87,1249,1023,1060]" pageId="4" pageNumber="428">
|
||
<tableNote id="C3373779FFD42861BA44028359545D30" pageId="4" pageNumber="428" targetBox="[110,1451,243,998]" targetPageId="4">
|
||
The attached proton number of each carbon signal was verified by DEPT pulse sequence and confirmed by HMQC and HMBC 2D NMR spectra.
|
||
<superScript id="C9A49BBFFFD42861BA4F056E5B225D08" attach="left" box="[92,110,1042,1052]" fontSize="4" pageId="4" pageNumber="428">a,b</superScript>
|
||
These values in each column may be interchanged.
|
||
</tableNote>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD42861B95705E058A75FD5" blockId="4.[805,1475,1124,2008]" pageId="4" pageNumber="428">
|
||
Although 4b,5,6,10b,11,12-hexahydrochrysene derivatives are known synthetic estrogens (
|
||
<bibRefCitation id="5A404B06FFD42861BE5F05C45E5C5DDF" author="Collins, D. J. & Cullen, J. D. & Stone, G. M." box="[1100,1296,1208,1227]" pageId="4" pageNumber="428" pagination="745 - 756" refId="ref13392" refString="Collins, D. J., Cullen, J. D., Stone, G. M., 1988. The structure and function of estrogens. 10. Synthesis of 5,5 - dimethyl-cis- 4 b, 5,6,10 b, 11,12 - hexahydrochrysene- 2,8 - diol - the estrogenic activity of this and of related c-methylated hydrochrysenediols. Aust. J. Chem. 41, 745 - 756." type="journal article" year="1988">Collins et al., 1988</bibRefCitation>
|
||
), compound
|
||
<emphasis id="0CA5EAE5FFD42861BF8805C45EE45DDF" bold="true" box="[1435,1448,1208,1227]" pageId="4" pageNumber="428">6</emphasis>
|
||
is the first identified triphenylated hexahydrochrysene at least from a natural source. Apparently, compound
|
||
<emphasis id="0CA5EAE5FFD42861BEDB058C5F995C17" bold="true" box="[1224,1237,1264,1283]" pageId="4" pageNumber="428">6</emphasis>
|
||
is stilbene oligomer of that may have been constructed through a Diels–Alder
|
||
<typeStatus id="E16A8855FFD42861BF4804705EC45C0B" box="[1371,1416,1292,1311]" pageId="4" pageNumber="428">type</typeStatus>
|
||
reaction, whereby enzymatic catalysis has recently been proved to be efficient (
|
||
<bibRefCitation id="5A404B06FFD42861B99B043F5F7D5C43" author="Kim, H. J. & Ruszczycky, M. W. & Choi, S. - H. & Liu, Y. - N. & Liu, H. - W." box="[904,1073,1347,1367]" pageId="4" pageNumber="428" pagination="109 - 112" refId="ref14189" refString="Kim, H. J., Ruszczycky, M. W., Choi, S. - H., Liu, Y. - N., Liu, H. - W., 2011. Enzymecatalysed [4 + 2] cycloaddition is a key step in the biosynthesis of spinosyn A. Nature 473, 109 - 112." type="journal article" year="2011">Kim et al., 2011</bibRefCitation>
|
||
). The enzyme, namely Diels–Alderase, is now a highlight in chemical biology (
|
||
<bibRefCitation id="5A404B06FFD42861BEA404235E115C67" author="Townsend, C. A." box="[1207,1373,1375,1395]" pageId="4" pageNumber="428" pagination="2267 - 2269" refId="ref15523" refString="Townsend, C. A., 2011. A '' Diels - Alderase' ' at last. Chem. Bio. Chem. 12, 2267 - 2269." type="journal article" year="2011">Townsend, 2011</bibRefCitation>
|
||
). A possible biosynthetic process to
|
||
<emphasis id="0CA5EAE5FFD42861BE2D04075F075C9A" bold="true" box="[1086,1099,1403,1422]" pageId="4" pageNumber="428">6</emphasis>
|
||
was proposed as shown in
|
||
<figureCitation id="A6EA2A72FFD42861BF7904075EED5C9A" box="[1386,1441,1403,1422]" captionStart="Fig" captionStartId="5.[569,595,1999,2013]" captionTargetBox="[255,1287,1091,1967]" captionTargetId="graphics-775@5.[586,916,1450,1604]" captionTargetPageId="5" captionText="Fig. 3. Suggested biosynthetic pathway to artoxanthol (6)." figureDoi="http://doi.org/10.5281/zenodo.10486282" httpUri="https://zenodo.org/record/10486282/files/figure.png" pageId="4" pageNumber="428">Fig. 3</figureCitation>
|
||
. In this proposal, two molecules of oxyresveratrol experienced a [4 + 2] Diels–Alder
|
||
<typeStatus id="E16A8855FFD42861B9FB04C85F595CD3" box="[1000,1045,1460,1479]" pageId="4" pageNumber="428">type</typeStatus>
|
||
reaction to give alboctalol (
|
||
<emphasis id="0CA5EAE5FFD42861BF2704CF5E0D5CD2" bold="true" box="[1332,1345,1459,1478]" pageId="4" pageNumber="428">9</emphasis>
|
||
) and/or epialboctalol (
|
||
<bibRefCitation id="5A404B06FFD42861B98704B35F0C5CF6" author="Royer, M. & Herbette, G. & Eparvier, V. & Beauchene, J. & Thibaut, B. & Stien, D." box="[916,1088,1487,1506]" pageId="4" pageNumber="428" pagination="1708 - 1713" refId="ref15355" refString="Royer, M., Herbette, G., Eparvier, V., Beauchene, J., Thibaut, B., Stien, D., 2010. Secondary metabolites of Bagassa guianensis Aubl. wood: a study of the chemotaxonomy of the Moraceae family. Phytochemistry 71, 1708 - 1713." type="journal article" year="2010">Royer et al., 2010</bibRefCitation>
|
||
), which is then followed by a phenolic oxidative de-resorcinol elimination process, forming another ligand (
|
||
<bibRefCitation id="5A404B06FFD42861B967077B5F485F0E" author="Li, X. M. & Huang, K. S. & Lin, M. & Zhou, L. X." box="[884,1028,1543,1562]" pageId="4" pageNumber="428" pagination="4405 - 4413" refId="ref14651" refString="Li, X. M., Huang, K. S., Lin, M., Zhou, L. X., 2003. Studies on formic acid-catalyzed dimerization of isorhapontigenin and of resveratrol to tetralins. Tetrahedron 59, 4405 - 4413." type="journal article" year="2003">Li et al., 2003</bibRefCitation>
|
||
) for an additional [4 + 2] reaction that led consequently to the formation of artoxanthol (
|
||
<emphasis id="0CA5EAE5FFD42861BF06075F5E6E5F22" bold="true" box="[1301,1314,1571,1590]" pageId="4" pageNumber="428">6</emphasis>
|
||
). Although the existence of a Diels–Alderase in
|
||
<taxonomicName id="F9D14D74FFD42861BE6007415E435F45" box="[1139,1295,1597,1618]" class="Magnoliopsida" family="Moraceae" genus="Artocarpus" kingdom="Plantae" order="Rosales" pageId="4" pageNumber="428" phylum="Tracheophyta" rank="species" species="xanthocarpus">
|
||
<emphasis id="0CA5EAE5FFD42861BE6007415FCC5F45" box="[1139,1152,1597,1617]" italics="true" pageId="4" pageNumber="428">A</emphasis>
|
||
.
|
||
<emphasis id="0CA5EAE5FFD42861BE9E07415E435F45" box="[1165,1295,1597,1617]" italics="true" pageId="4" pageNumber="428">xanthocarpus</emphasis>
|
||
</taxonomicName>
|
||
is still unknown, at least three Diels–Alder
|
||
<typeStatus id="E16A8855FFD42861BE2B07275F295F7A" box="[1080,1125,1627,1646]" pageId="4" pageNumber="428">type</typeStatus>
|
||
adducts, namely artoxanthol (
|
||
<emphasis id="0CA5EAE5FFD42861BFBB07265EF95F79" bold="true" box="[1448,1461,1626,1645]" pageId="4" pageNumber="428">6</emphasis>
|
||
), artoxanthochromane (
|
||
<emphasis id="0CA5EAE5FFD42861BE1B070A5F595F9D" bold="true" box="[1032,1045,1654,1673]" pageId="4" pageNumber="428">7</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD42861BE3F070B5FF35F9D" author="Ko, H. H. & Jin, Y. J. & Lu, T. M. & Chen, I. S." box="[1068,1215,1654,1674]" pageId="4" pageNumber="428" pagination="1269 - 1275" refId="ref14308" refString="Ko, H. H., Jin, Y. J., Lu, T. M., Chen, I. S., 2013. A novel monoterpene-stilbene adduct with a 4,4 - dimethyl- 2 - 3 - dipenylchromane skeleton from Artocarpus xanthocarpus. Chem. Biodivers. 10, 1269 - 1275." type="journal article" year="2013">Ko et al., 2013</bibRefCitation>
|
||
), and alboctalol (
|
||
<emphasis id="0CA5EAE5FFD42861BF62070A5E325F9D" bold="true" box="[1393,1406,1654,1673]" pageId="4" pageNumber="428">9</emphasis>
|
||
), have been identified from this plant and other Moraceous plants (
|
||
<bibRefCitation id="5A404B06FFD42861B93E07D358915FD5" author="Royer, M. & Herbette, G. & Eparvier, V. & Beauchene, J. & Thibaut, B. & Stien, D." box="[813,989,1710,1730]" pageId="4" pageNumber="428" pagination="1708 - 1713" refId="ref15355" refString="Royer, M., Herbette, G., Eparvier, V., Beauchene, J., Thibaut, B., Stien, D., 2010. Secondary metabolites of Bagassa guianensis Aubl. wood: a study of the chemotaxonomy of the Moraceae family. Phytochemistry 71, 1708 - 1713." type="journal article" year="2010">Royer et al., 2010</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD42860B95707B659815A87" blockId="4.[805,1475,1124,2008]" lastBlockId="5.[113,783,701,915]" lastPageId="5" lastPageNumber="429" pageId="4" pageNumber="428">
|
||
The structure of
|
||
<emphasis id="0CA5EAE5FFD42861B9E007B65F4C5FC9" bold="true" box="[1011,1024,1738,1757]" pageId="4" pageNumber="428">1</emphasis>
|
||
was determined by 1D NMR spectroscopy, whereas, compounds
|
||
<emphasis id="0CA5EAE5FFD42861BE14079A5F615FED" bold="true" box="[1031,1069,1766,1785]" pageId="4" pageNumber="428">2–6</emphasis>
|
||
were determined by 1D and 2D NMR spectra and by comparing with those of reported analogs. Although compounds
|
||
<emphasis id="0CA5EAE5FFD42861B9EC06625F695E25" bold="true" box="[1023,1061,1822,1841]" pageId="4" pageNumber="428">1–6</emphasis>
|
||
possess stereogenic centers, the available data did not allow the determination of the stereochemical configuration of these compounds. The other known compounds, including artoxanthochromane (
|
||
<emphasis id="0CA5EAE5FFD42861BE2B060E5F095E91" bold="true" box="[1080,1093,1906,1925]" pageId="4" pageNumber="428">7</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD42861BE72060E5E4F5E91" author="Ko, H. H. & Jin, Y. J. & Lu, T. M. & Chen, I. S." box="[1121,1283,1905,1925]" pageId="4" pageNumber="428" pagination="1269 - 1275" refId="ref14308" refString="Ko, H. H., Jin, Y. J., Lu, T. M., Chen, I. S., 2013. A novel monoterpene-stilbene adduct with a 4,4 - dimethyl- 2 - 3 - dipenylchromane skeleton from Artocarpus xanthocarpus. Chem. Biodivers. 10, 1269 - 1275." type="journal article" year="2013">Ko et al., 2013</bibRefCitation>
|
||
), lakoochin A (
|
||
<emphasis id="0CA5EAE5FFD42861BFBE060D5EF65E90" bold="true" box="[1453,1466,1905,1924]" pageId="4" pageNumber="428">8</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD42861B93E06F15F595EB4" author="Puntumchai, A. & Kittakoop, P. & Rajviroongit, S. & Vimuttipong, S. & Likhitwitayawuid, K. & Thebtaranonth, Y." box="[813,1045,1933,1953]" pageId="4" pageNumber="428" pagination="485 - 486" refId="ref15253" refString="Puntumchai, A., Kittakoop, P., Rajviroongit, S., Vimuttipong, S., Likhitwitayawuid, K., Thebtaranonth, Y., 2004. Lakoochins A and B, new antimycobacterial stilbene derivatives from Artocarpus lakoocha. J. Nat. Prod. 67, 485 - 486." type="journal article" year="2004">Puntumchai et al., 2004</bibRefCitation>
|
||
), alboctalol (
|
||
<emphasis id="0CA5EAE5FFD42861BE8506F15FEF5EB4" bold="true" box="[1174,1187,1933,1952]" pageId="4" pageNumber="428">9</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD42861BEA406F25E2C5EB4" author="Royer, M. & Herbette, G. & Eparvier, V. & Beauchene, J. & Thibaut, B. & Stien, D." box="[1207,1376,1933,1953]" pageId="4" pageNumber="428" pagination="1708 - 1713" refId="ref15355" refString="Royer, M., Herbette, G., Eparvier, V., Beauchene, J., Thibaut, B., Stien, D., 2010. Secondary metabolites of Bagassa guianensis Aubl. wood: a study of the chemotaxonomy of the Moraceae family. Phytochemistry 71, 1708 - 1713." type="journal article" year="2010">Royer et al., 2010</bibRefCitation>
|
||
), (
|
||
<emphasis id="0CA5EAE5FFD42861BF6906F25EC75EB4" box="[1402,1419,1934,1952]" italics="true" pageId="4" pageNumber="428">—</emphasis>
|
||
)-catechin (
|
||
<emphasis id="0CA5EAE5FFD42861B97906D558CF5EA8" bold="true" box="[874,899,1961,1980]" pageId="4" pageNumber="428">10</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD42861B98806D65F7F5EA8" author="Lee, M. W. & Morimoto, S. & Nonaka, G. I. & Nishioka, I." box="[923,1075,1961,1981]" pageId="4" pageNumber="428" pagination="2117 - 2121" refId="ref14426" refString="Lee, M. W., Morimoto, S., Nonaka, G. I., Nishioka, I., 1992. Flavan- 3 - ol gallates and proanthocyanidins from Pithecellobium lobatum. Phytochemistry 31, 2117 - 2121." type="journal article" year="1992">Lee et al., 1992</bibRefCitation>
|
||
), steppogenin (
|
||
<emphasis id="0CA5EAE5FFD42861BEC206D55FA65EA8" bold="true" box="[1233,1258,1961,1980]" pageId="4" pageNumber="428">11</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD42861BF1206D55EF95EA8" author="Arung, E. T. & Shimizu, K. & Kondo, R." box="[1281,1461,1961,1981]" pageId="4" pageNumber="428" pagination="2166 - 2171" refId="ref12902" refString="Arung, E. T., Shimizu, K., Kondo, R., 2007. Structure - activity relationship of prenylsubstituted polyphenols from Artocarpus heterophyllus as inhibitors of melanin biosynthesis in cultured melanoma cells. Chem. Biodivers. 4, 2166 - 2171." type="journal article" year="2007">Arung et al., 2007</bibRefCitation>
|
||
), norartocarpetin (
|
||
<emphasis id="0CA5EAE5FFD42861B9C706B958A15ECC" bold="true" box="[980,1005,1989,2008]" pageId="4" pageNumber="428">12</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD42861BE1406B95FF15ECC" author="Jeong, S. H. & Ryu, Y. B. & Curtis-Long, M. J. & Ryu, H. W. & Baek, Y. S. & Kang, J. E. & Lee, W. S. & Park, K. H." box="[1031,1213,1989,2008]" pageId="4" pageNumber="428" pagination="1195 - 1203" refId="ref13928" refString="Jeong, S. H., Ryu, Y. B., Curtis-Long, M. J., Ryu, H. W., Baek, Y. S., Kang, J. E., Lee, W. S., Park, K. H., 2009. Tyrosinase inhibitory polyphenols from roots of Morus lhou. J. Agric. Food Chem. 57, 1195 - 1203." type="journal article" year="2009">Jeong et al., 2009</bibRefCitation>
|
||
), isoetin 5
|
||
<emphasis id="0CA5EAE5FFD42861BF3D06BF5E7E5EDB" box="[1326,1330,1987,1999]" italics="true" pageId="4" pageNumber="428">
|
||
<superScript id="C9A49BBFFFD42861BF3D06BF5E7E5EDB" attach="none" box="[1326,1330,1987,1999]" fontSize="5" pageId="4" pageNumber="428">0</superScript>
|
||
</emphasis>
|
||
-methyl ether (
|
||
<emphasis id="0CA5EAE5FFD52860BA6903C15BDF5BC4" bold="true" box="[122,147,701,720]" pageId="5" pageNumber="429">13</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860BABB03C15AD35BC4" author="Rahman, M. A. A. & Moon, S. S." box="[168,415,701,720]" pageId="5" pageNumber="429" pagination="1261 - 1264" refId="ref15310" refString="Rahman, M. A. A., Moon, S. S., 2007. Isoetin 5 0 - methyl ether, a cytotoxic flavone from Trichosanthes kirilowii. Bull. Korean Chem. Soc. 28, 1261 - 1264." type="journal article" year="2007">Rahman and Moon, 2007</bibRefCitation>
|
||
), morusin (
|
||
<emphasis id="0CA5EAE5FFD52860B80203C159665BC4" bold="true" box="[529,554,701,720]" pageId="5" pageNumber="429">14</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860B85303C1584E5BC4" author="Nomura, T. & Fukai, T. & Yamada, S. & Katayanagi, M." box="[576,770,701,720]" pageId="5" pageNumber="429" pagination="1394 - 1402" refId="ref14964" refString="Nomura, T., Fukai, T., Yamada, S., Katayanagi, M., 1978. Studies on the constituents of the cultivated mulberry tree. I. Three new prenylflavones from the root bark of Morus alba L. Chem. Pharm. Bull. 26, 1394 - 1402." type="journal article" year="1978">Nomura et al., 1978</bibRefCitation>
|
||
), cyclocommunol (
|
||
<emphasis id="0CA5EAE5FFD52860BB3303A45A755BFF" bold="true" box="[288,313,728,747]" pageId="5" pageNumber="429">15</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860BB4203A459555BF8" author="Lin, C. N. & Shieh, W. L." box="[337,537,728,748]" pageId="5" pageNumber="429" pagination="2922 - 2924" refId="ref14741" refString="Lin, C. N., Shieh, W. L., 1992. Pyranoflavonoids from Artocarpus communis. Phytochemistry 31, 2922 - 2924." type="journal article" year="1992">Lin and Shieh, 1992</bibRefCitation>
|
||
), albanin A (
|
||
<emphasis id="0CA5EAE5FFD52860B88F03A459F95BFF" bold="true" box="[668,693,728,747]" pageId="5" pageNumber="429">16</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860B8DF03A45BA55A1C" author="Ferrari, F. & Messana, I." pageId="5" pageNumber="429" pagination="70 - 72" refId="ref13509" refString="Ferrari, F., Messana, I., de Araujo, Mdo. C., 1989. Structures of three new flavone derivatives, brosimones G, H, and I, from Brosimopsis oblongifolia. Planta Med. 55, 70 - 72." type="journal article" year="1989">Ferrari et al., 1989</bibRefCitation>
|
||
), cudraflavone C (
|
||
<emphasis id="0CA5EAE5FFD52860BBBF03885A895A13" bold="true" box="[428,453,756,775]" pageId="5" pageNumber="429">17</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860BBCC038959DA5A1C" author="Hano, Y. & Matsumoto, Y. & Shinohara, K. & Sun, J. Y. & Nomura, T." box="[479,662,756,776]" pageId="5" pageNumber="429" pagination="1339 - 1341" refId="ref13773" refString="Hano, Y., Matsumoto, Y., Shinohara, K., Sun, J. Y., Nomura, T., 1990. Cudraflavones C and D, two new prenylflavones from the root bark of Cudrania tricuspidata (Carr.) Bur. Heterocycles 31, 1339 - 1341." type="journal article" year="1990">Hano et al., 1990</bibRefCitation>
|
||
), artonin A (
|
||
<emphasis id="0CA5EAE5FFD52860BA69026C5BDF5A37" bold="true" box="[122,147,784,803]" pageId="5" pageNumber="429">18</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860BAA2026D5A3D5A37" author="Hano, Y. & Aida, M. & Shiina, M. & Nomura, T. & Kawai, T. & Ohe, H. & Kagei, K." box="[177,369,784,804]" pageId="5" pageNumber="429" pagination="1447 - 1453" refId="ref13712" refString="Hano, Y., Aida, M., Shiina, M., Nomura, T., Kawai, T., Ohe, H., Kagei, K., 1989. Artonins A and B, two new prenylflavones from the root bark of Artocarpus heterophyllus Lamk. Heterocycles 29, 1447 - 1453." type="journal article" year="1989">Hano et al., 1989</bibRefCitation>
|
||
), resveratrol (
|
||
<emphasis id="0CA5EAE5FFD52860B81D026C596B5A37" bold="true" box="[526,551,784,803]" pageId="5" pageNumber="429">19</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860B856026C584E5A37" author="Chen, R. S. & Wu, P. L. & Chiou, R. Y. Y." box="[581,770,784,804]" pageId="5" pageNumber="429" pagination="1665 - 1667" refId="ref13163" refString="Chen, R. S., Wu, P. L., Chiou, R. Y. Y., 2002. Peanut roots as a source of resveratrol. J. Agric. Food Chem. 50, 1665 - 1667." type="journal article" year="2002">Chen et al., 2002</bibRefCitation>
|
||
), oxyresveratrol (
|
||
<emphasis id="0CA5EAE5FFD52860BB0D02505A7B5A2B" bold="true" box="[286,311,812,831]" pageId="5" pageNumber="429">20</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860BB48025059635A2B" author="Zhaxi, M. & Chen, L. & Li, X. & Komatsu, K. & Yao, X. & Qiu, F." box="[347,559,812,832]" pageId="5" pageNumber="429" pagination="362 - 364" refId="ref15615" refString="Zhaxi, M., Chen, L., Li, X., Komatsu, K., Yao, X., Qiu, F., 2010. Three major metabolites of mulberroside A in rat intestinal contents and feces. Planta Med. 76, 362 - 364." type="journal article" year="2010">Zhaxi et al., 2010</bibRefCitation>
|
||
), chlorophorin (
|
||
<emphasis id="0CA5EAE5FFD52860B8FD0250584B5A2B" bold="true" box="[750,775,812,831]" pageId="5" pageNumber="429">21</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860BA6902345A285A4F" author="Christensen, L. P. & Lam, J. & Sigsgaard, T." box="[122,356,840,860]" pageId="5" pageNumber="429" pagination="3014 - 3016" refId="ref13356" refString="Christensen, L. P., Lam, J., Sigsgaard, T., 1988. A novel stilbene from the wood of Chlorophora excelsa. Phytochemistry 27, 3014 - 3016." type="journal article" year="1988">Christensen et al., 1988</bibRefCitation>
|
||
), scopoletin (
|
||
<emphasis id="0CA5EAE5FFD52860BBFF023459495A4F" bold="true" box="[492,517,840,859]" pageId="5" pageNumber="429">22</emphasis>
|
||
) (
|
||
<bibRefCitation id="5A404B06FFD52860B808023559F15A4F" author="Lee, J. & Kim, N. H. & Nam, J. W. & Lee, Y. M. & Jang, D. S. & Kim, Y. S. & Nam, S. H. & Seo, E. K. & Yang, M. S. & Kim, J. S." box="[539,701,840,860]" pageId="5" pageNumber="429" pagination="1317 - 1323" refId="ref14548" refString="Lee, J., Kim, N. H., Nam, J. W., Lee, Y. M., Jang, D. S., Kim, Y. S., Nam, S. H., Seo, E. K., Yang, M. S., Kim, J. S., 2010 b. Scopoletin from the flower buds of Magnolia fargesii inhibits protein glycation, aldose reductase, and cataractogenesis ex vivo. Arch. Pharm. Res. 33, 1317 - 1323." type="journal article" year="2010">Lee et al., 2010b</bibRefCitation>
|
||
), protocatechuic acid, and
|
||
<emphasis id="0CA5EAE5FFD52860BB2F02185A045A63" box="[316,328,868,887]" italics="true" pageId="5" pageNumber="429">β</emphasis>
|
||
-sitosterol, were identified by comparison of their physical and spectroscopic data with literature values.
|
||
</paragraph>
|
||
<caption id="6AAE667FFFD52860BA62030759D15BB4" ID-DOI="http://doi.org/10.5281/zenodo.10486280" ID-Zenodo-Dep="10486280" httpUri="https://zenodo.org/record/10486280/files/figure.png" pageId="5" pageNumber="429" startId="5.[113,139,635,649]" targetBox="[150,748,185,602]" targetPageId="5" targetType="figure">
|
||
<paragraph id="3E6E36F7FFD52860BA62030759D15BB4" blockId="5.[113,783,635,673]" pageId="5" pageNumber="429">
|
||
<emphasis id="0CA5EAE5FFD52860BA6203075BEF5B9D" bold="true" box="[113,163,635,649]" pageId="5" pageNumber="429">Fig. 2.</emphasis>
|
||
Key information from NOESY experiments of artoxanthol (
|
||
<emphasis id="0CA5EAE5FFD52860B891030759C05B9D" bold="true" box="[642,652,635,649]" pageId="5" pageNumber="429">6</emphasis>
|
||
). The molecular model was established by MMF94 minimization (
|
||
<emphasis id="0CA5EAE5FFD52860B81503ED592C5BB5" box="[518,608,657,673]" italics="true" pageId="5" pageNumber="429">ChemBio3D</emphasis>
|
||
11.0
|
||
<emphasis id="0CA5EAE5FFD52860B89B03F259DE5B8C" box="[648,658,654,664]" italics="true" pageId="5" pageNumber="429">
|
||
<superScript id="C9A49BBFFFD52860B89B03F259DE5B8C" attach="right" box="[648,658,654,664]" fontSize="4" pageId="5" pageNumber="429">®</superScript>
|
||
</emphasis>
|
||
).
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="3E6E36F7FFD52860BA6102BD58425AC1" blockId="5.[114,782,961,981]" box="[114,782,961,981]" pageId="5" pageNumber="429">
|
||
<heading id="6526819BFFD52860BA6102BD58425AC1" box="[114,782,961,981]" centered="true" fontSize="36" level="2" pageId="5" pageNumber="429" reason="3">
|
||
<emphasis id="0CA5EAE5FFD52860BA6102BD58425AC1" box="[114,782,961,981]" italics="true" pageId="5" pageNumber="429">
|
||
2.2. Antioxidant activity of compounds isolated from
|
||
<taxonomicName id="F9D14D74FFD52860B86702BD58425AC1" ID-CoL="684FL" box="[628,782,961,981]" class="Magnoliopsida" family="Moraceae" genus="Artocarpus" kingdom="Plantae" order="Rosales" pageId="5" pageNumber="429" phylum="Tracheophyta" rank="species" species="xanthocarpus">A. xanthocarpus</taxonomicName>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD52860BA820287589958E8" blockId="5.[113,783,1018,1066]" lastBlockId="5.[831,1501,182,509]" pageId="5" pageNumber="429">
|
||
DPPH, ABTS, and superoxide anion radical-scavenging assays were used to evaluate the antioxidant activities of each of the isolated compounds. Compound
|
||
<emphasis id="0CA5EAE5FFD52860BE8701CA5FE159DD" bold="true" box="[1172,1197,182,201]" pageId="5" pageNumber="429">18</emphasis>
|
||
exhibited strong DPPH radical-scavenging activity comparable to the ascorbic acid positive control (
|
||
<tableCitation id="7353034CFFD52860B986019258925815" box="[917,990,238,257]" captionStart="Table 3" captionStartId="6.[87,131,183,197]" captionTargetPageId="6" captionText="Table 3 Antioxidant activities and mushroom tyrosinase inhibitory effect of compounds from A. xanthocarpus. a" httpUri="http://table.plazi.org/id/6AAE667FFFD62863BA4401CB58CA59C7" pageId="5" pageNumber="429" tableUuid="6AAE667FFFD62863BA4401CB58CA59C7">Table 3</tableCitation>
|
||
). Compounds
|
||
<emphasis id="0CA5EAE5FFD52860BE7C01925F305815" bold="true" box="[1135,1148,238,257]" pageId="5" pageNumber="429">3</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BE9401925FD85815" bold="true" box="[1159,1172,238,257]" pageId="5" pageNumber="429">4</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BE8C01925FE05815" bold="true" box="[1183,1196,238,257]" pageId="5" pageNumber="429">6</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BEA401925FA55815" bold="true" box="[1207,1257,238,257]" pageId="5" pageNumber="429">8–10</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD52860BF3301925E135815" bold="true" box="[1312,1375,238,257]" pageId="5" pageNumber="429">19–21</emphasis>
|
||
had moderate or weak DPPH radical-scavenging activity. In the ABTS cation radical-scavenging assay, compounds
|
||
<emphasis id="0CA5EAE5FFD52860BED8005A5F94582D" bold="true" box="[1227,1240,294,313]" pageId="5" pageNumber="429">6</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BEF4005A5FB8582D" bold="true" box="[1255,1268,294,313]" pageId="5" pageNumber="429">9</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BF17005A5E51582D" bold="true" box="[1284,1309,294,313]" pageId="5" pageNumber="429">10</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BF3E005A5E0A582D" bold="true" box="[1325,1350,294,313]" pageId="5" pageNumber="429">14</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD52860BF95005A5ED3582D" bold="true" box="[1414,1439,294,313]" pageId="5" pageNumber="429">20</emphasis>
|
||
were quite potent, with SC
|
||
<subScript id="A25534B2FFD52860BE3700375F7A5843" attach="left" box="[1060,1078,331,343]" fontSize="5" pageId="5" pageNumber="429">50</subScript>
|
||
values of 7.6 ± 0.1, 6.5 ± 0.9, 22.7 ± 0.6, 28.0 ± 1.7, and 28.8 ± 0.6 µM, respectively, whereas compounds
|
||
<emphasis id="0CA5EAE5FFD52860BFD900225E9B5865" bold="true" box="[1482,1495,350,369]" pageId="5" pageNumber="429">4</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860B92C000658005899" bold="true" box="[831,844,378,397]" pageId="5" pageNumber="429">7</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860B945000558235898" bold="true" box="[854,879,377,396]" pageId="5" pageNumber="429">18</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860B969000558DF5898" bold="true" box="[890,915,377,396]" pageId="5" pageNumber="429">19</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD52860B9DB000558AD5898" bold="true" box="[968,993,377,396]" pageId="5" pageNumber="429">21</emphasis>
|
||
showed only moderate activity. The relative activities of these compounds to scavenge superoxide anions are also shown in
|
||
<tableCitation id="7353034CFFD52860B9B400CD58BF58D0" box="[935,1011,433,452]" captionStart="Table 3" captionStartId="6.[87,131,183,197]" captionTargetPageId="6" captionText="Table 3 Antioxidant activities and mushroom tyrosinase inhibitory effect of compounds from A. xanthocarpus. a" httpUri="http://table.plazi.org/id/6AAE667FFFD62863BA4401CB58CA59C7" pageId="5" pageNumber="429" tableUuid="6AAE667FFFD62863BA4401CB58CA59C7">Table 3</tableCitation>
|
||
. Notably, compound
|
||
<emphasis id="0CA5EAE5FFD52860BEC200CD5FA658D0" bold="true" box="[1233,1258,433,452]" pageId="5" pageNumber="429">10</emphasis>
|
||
(SC
|
||
<subScript id="A25534B2FFD52860BF0700C65E6A58D2" attach="left" box="[1300,1318,442,454]" fontSize="5" pageId="5" pageNumber="429">50</subScript>
|
||
of 11.1 ± 0.5 µM) was more potent than the ascorbic acid control (SC
|
||
<subScript id="A25534B2FFD52860BFB700AA5EFA58F6" attach="left" box="[1444,1462,470,482]" fontSize="5" pageId="5" pageNumber="429">50</subScript>
|
||
of 20.6 ± 1.6 µM).
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD52860B92C0351588C5B49" blockId="5.[831,1487,557,605]" pageId="5" pageNumber="429">
|
||
<emphasis id="0CA5EAE5FFD52860B92C03515E835B55" box="[831,1487,557,577]" italics="true" pageId="5" pageNumber="429">
|
||
2.3. Mushroom tyrosinase inhibition by compounds isolated from
|
||
<taxonomicName id="F9D14D74FFD52860BFAF0351588C5B49" class="Magnoliopsida" family="Moraceae" genus="Artocarpus" kingdom="Plantae" order="Rosales" pageId="5" pageNumber="429" phylum="Tracheophyta" rank="species" species="xanthocarpus">
|
||
A.
|
||
<heading id="6526819BFFD52860B92C0335588C5B49" box="[831,960,585,605]" fontSize="8" level="3" pageId="5" pageNumber="429" reason="8">
|
||
<emphasis id="0CA5EAE5FFD52860B92C0335588C5B49" box="[831,960,585,605]" italics="true" pageId="5" pageNumber="429">xanthocarpus</emphasis>
|
||
</heading>
|
||
</taxonomicName>
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD52860B94D03FE5FE35A60" blockId="5.[831,1501,642,885]" pageId="5" pageNumber="429">
|
||
The inhibitory activity of each compound against mushroom tyrosinase was also evaluated for each compound. Compounds
|
||
<emphasis id="0CA5EAE5FFD52860BFD903E25E9B5BA5" bold="true" box="[1482,1495,670,689]" pageId="5" pageNumber="429">6</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860B92C03C658005BD9" bold="true" box="[831,844,698,717]" pageId="5" pageNumber="429">9</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860B94A03C6583E5BD9" bold="true" box="[857,882,698,717]" pageId="5" pageNumber="429">11</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860B96C03C658D45BD9" bold="true" box="[895,920,698,717]" pageId="5" pageNumber="429">12</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD52860B9C703C65F5F5BD9" bold="true" box="[980,1043,698,717]" pageId="5" pageNumber="429">19–21</emphasis>
|
||
were potent tyrosinase inhibitors, with IC
|
||
<subScript id="A25534B2FFD52860BFD903BF5E905BDB" attach="left" box="[1482,1500,707,719]" fontSize="5" pageId="5" pageNumber="429">50</subScript>
|
||
values of 5.7 ± 0.3, 6.4 ± 0.3, 1.9 ± 0.1, 0.9 ± 0.1, 4.9 ± 0.3, 1.0 ± 0.5, and 2.5 ± 0.4 µM, respectively. Compounds
|
||
<emphasis id="0CA5EAE5FFD52860BEE8038D5E445A10" bold="true" box="[1275,1288,753,772]" pageId="5" pageNumber="429">1</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BF06038D5E6E5A10" bold="true" box="[1301,1314,753,772]" pageId="5" pageNumber="429">3</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BF3C038E5E705A11" bold="true" box="[1327,1340,754,773]" pageId="5" pageNumber="429">7</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BF5B038D5E2D5A10" bold="true" box="[1352,1377,753,772]" pageId="5" pageNumber="429">14</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD52860BF7C038D5EC45A10" bold="true" box="[1391,1416,753,772]" pageId="5" pageNumber="429">16</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD52860BFD0038D5E905A10" bold="true" box="[1475,1500,753,772]" pageId="5" pageNumber="429">17</emphasis>
|
||
also showed strong inhibitory effects against mushroom tyrosinase (
|
||
<tableCitation id="7353034CFFD52860B954025558DF5A29" box="[839,915,809,829]" captionStart="Table 3" captionStartId="6.[87,131,183,197]" captionTargetPageId="6" captionText="Table 3 Antioxidant activities and mushroom tyrosinase inhibitory effect of compounds from A. xanthocarpus. a" httpUri="http://table.plazi.org/id/6AAE667FFFD62863BA4401CB58CA59C7" pageId="5" pageNumber="429" tableUuid="6AAE667FFFD62863BA4401CB58CA59C7">Table 3</tableCitation>
|
||
). Indeed, these compounds were more potent inhibitors than ascorbic acid/arbutin/kojic acid, a well-known whitening agent used in cosmetic applications.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD52860B92C02D95F705AC1" blockId="5.[831,1500,933,981]" pageId="5" pageNumber="429">
|
||
<emphasis id="0CA5EAE5FFD52860B92C02D95F705AC1" italics="true" pageId="5" pageNumber="429">
|
||
2.4. Effect of compounds isolated from
|
||
<taxonomicName id="F9D14D74FFD52860BEBE02D95E0A5AAD" box="[1197,1350,933,953]" class="Magnoliopsida" family="Moraceae" genus="Artocarpus" kingdom="Plantae" order="Rosales" pageId="5" pageNumber="429" phylum="Tracheophyta" rank="species" species="xanthocarpus">A. xanthocarpus</taxonomicName>
|
||
on cell viability
|
||
<heading id="6526819BFFD52860B92C02BD5F705AC1" box="[831,1084,961,981]" fontSize="8" level="3" pageId="5" pageNumber="429" reason="8">of B16F10 melanoma cells</heading>
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD52860B94D02865E905D3E" blockId="5.[831,1500,1018,1066]" pageId="5" pageNumber="429">B16F10 melanoma cells were treated with various concentrations of each compound for 48 h, with an XTT assay used to</paragraph>
|
||
<caption id="6AAE667FFFD52860B82A06B35F595EC9" ID-DOI="http://doi.org/10.5281/zenodo.10486282" ID-Zenodo-Dep="10486282" box="[569,1045,1999,2013]" httpUri="https://zenodo.org/record/10486282/files/figure.png" pageId="5" pageNumber="429" startId="5.[569,595,1999,2013]" targetBox="[255,1287,1091,1967]" targetPageId="5" targetType="figure">
|
||
<paragraph id="3E6E36F7FFD52860B82A06B35F595EC9" blockId="5.[569,1045,1999,2013]" box="[569,1045,1999,2013]" pageId="5" pageNumber="429">
|
||
<emphasis id="0CA5EAE5FFD52860B82A06B359275EC9" bold="true" box="[569,619,1999,2013]" pageId="5" pageNumber="429">Fig. 3.</emphasis>
|
||
Suggested biosynthetic pathway to artoxanthol (
|
||
<emphasis id="0CA5EAE5FFD52860BE1306B35F465EC9" bold="true" box="[1024,1034,1999,2013]" pageId="5" pageNumber="429">6</emphasis>
|
||
).
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="6AAE667FFFD62863BA4401CB58CA59C7" ID-Table-UUID="6AAE667FFFD62863BA4401CB58CA59C7" httpUri="http://table.plazi.org/id/6AAE667FFFD62863BA4401CB58CA59C7" pageId="6" pageNumber="430" startId="6.[87,131,183,197]" targetBox="[110,1452,240,874]" targetIsTable="true" targetPageId="6" targetType="table">
|
||
<paragraph id="3E6E36F7FFD62863BA4401CB5BDF59D1" blockId="6.[87,902,183,220]" box="[87,147,183,197]" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA4401CB5BDF59D1" bold="true" box="[87,147,183,197]" pageId="6" pageNumber="430">Table 3</emphasis>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD62863BA4401B258CA59C7" blockId="6.[87,902,183,220]" box="[87,902,202,220]" pageId="6" pageNumber="430">
|
||
Antioxidant activities and mushroom tyrosinase inhibitory effect of compounds from
|
||
<taxonomicName id="F9D14D74FFD62863B91101B1583659C8" box="[770,890,205,220]" class="Magnoliopsida" family="Moraceae" genus="Artocarpus" kingdom="Plantae" order="Rosales" pageId="6" pageNumber="430" phylum="Tracheophyta" rank="species" species="xanthocarpus">
|
||
<emphasis id="0CA5EAE5FFD62863B91101B1583659C8" box="[770,890,205,220]" italics="true" pageId="6" pageNumber="430">A. xanthocarpus</emphasis>
|
||
</taxonomicName>
|
||
.
|
||
<superScript id="C9A49BBFFFD62863B96C01B658CA59C7" attach="right" box="[895,902,202,211]" fontSize="4" pageId="6" pageNumber="430">a</superScript>
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="3E6E36F7FFD62863BA7D01885EEE5A7E" pageId="6" pageNumber="430">
|
||
<table id="4CD1C457FFD6D79ABA7D018C5EE05A7E" box="[110,1452,240,874]" gridcols="5" gridrows="27" pageId="6" pageNumber="430">
|
||
<tr id="80E134B5FFD6D79ABA7D018C5EE05810" box="[110,1452,240,260]" gridrow="0" pageId="6" pageNumber="430" rowspan-2="1" rowspan-3="1">
|
||
<th id="C3305DC9FFD6D79ABA7D018C5B935810" box="[110,223,240,260]" gridcol="0" gridrow="0" pageId="6" pageNumber="430">Compounds</th>
|
||
<th id="C3305DC9FFD6D79ABBA5018C59425810" box="[438,526,240,260]" gridcol="1" gridrow="0" pageId="6" pageNumber="430">SC (µM)b 50</th>
|
||
<th id="C3305DC9FFD6D79ABF47018C5EE05810" box="[1364,1452,240,260]" gridcol="4" gridrow="0" pageId="6" pageNumber="430">IC (µM)b 50</th>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D006D5EE05832" box="[110,1452,273,294]" gridrow="1" pageId="6" pageNumber="430" rowspan-0="1">
|
||
<td id="C3305DC9FFD6D79ABBA5006D59425832" box="[438,526,273,294]" gridcol="1" gridrow="1" pageId="6" pageNumber="430">DPPH</td>
|
||
<td id="C3305DC9FFD6D79AB8F7006D580A5832" box="[740,838,273,294]" gridcol="2" gridrow="1" pageId="6" pageNumber="430">ABTS +.</td>
|
||
<td id="C3305DC9FFD6D79ABE0F006D5F325832" box="[1052,1150,273,294]" gridcol="3" gridrow="1" pageId="6" pageNumber="430">
|
||
O
|
||
<emphasis id="0CA5EAE5FFD62863BE3B006E5F7E580F" box="[1064,1074,274,283]" italics="true" pageId="6" pageNumber="430">—</emphasis>
|
||
. 2
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABF47006D5EE05832" box="[1364,1452,273,294]" gridcol="4" gridrow="1" pageId="6" pageNumber="430">Tyrosinase</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D004B5EE05852" box="[110,1452,311,326]" gridrow="2" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D004B5B935852" box="[110,223,311,326]" gridcol="0" gridrow="2" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D004B5B345851" bold="true" box="[110,120,311,325]" pageId="6" pageNumber="430">1</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5004B59425852" box="[438,526,311,326]" gridcol="1" gridrow="2" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F7004B580A5852" box="[740,838,311,326]" gridcol="2" gridrow="2" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABE0F004B5F325852" box="[1052,1150,311,326]" gridcol="3" gridrow="2" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABF47004B5EE05852" box="[1364,1452,311,326]" gridcol="4" gridrow="2" pageId="6" pageNumber="430">59.3 ± 3.7</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D00325EE05848" box="[110,1452,334,348]" gridrow="3" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D00325B935848" box="[110,223,334,348]" gridcol="0" gridrow="3" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D00325B345848" bold="true" box="[110,120,334,348]" pageId="6" pageNumber="430">2</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5003259425848" box="[438,526,334,348]" gridcol="1" gridrow="3" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F70032580A5848" box="[740,838,334,348]" gridcol="2" gridrow="3" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABE0F00325F325848" box="[1052,1150,334,348]" gridcol="3" gridrow="3" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF4700325EE05848" box="[1364,1452,334,348]" gridcol="4" gridrow="3" pageId="6" pageNumber="430">nd</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D00195EE05867" box="[110,1452,357,371]" gridrow="4" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D00195B935867" box="[110,223,357,371]" gridcol="0" gridrow="4" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D00195B345867" bold="true" box="[110,120,357,371]" pageId="6" pageNumber="430">3</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5001959425867" box="[438,526,357,371]" gridcol="1" gridrow="4" pageId="6" pageNumber="430">139.3 ± 6.2</td>
|
||
<td id="C3305DC9FFD6D79AB8F70019580A5867" box="[740,838,357,371]" gridcol="2" gridrow="4" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABE0F00195F325867" box="[1052,1150,357,371]" gridcol="3" gridrow="4" pageId="6" pageNumber="430">67.2 ± 8.2</td>
|
||
<td id="C3305DC9FFD6D79ABF4700195EE05867" box="[1364,1452,357,371]" gridcol="4" gridrow="4" pageId="6" pageNumber="430">97.5 ± 1.5</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D00005EE0589E" box="[110,1452,380,394]" gridrow="5" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D00005B93589E" box="[110,223,380,394]" gridcol="0" gridrow="5" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D00005B34589E" bold="true" box="[110,120,380,394]" pageId="6" pageNumber="430">4</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA500005942589E" box="[438,526,380,394]" gridcol="1" gridrow="5" pageId="6" pageNumber="430">140.4 ± 1.7</td>
|
||
<td id="C3305DC9FFD6D79AB8F70000580A589E" box="[740,838,380,394]" gridcol="2" gridrow="5" pageId="6" pageNumber="430">83.5 ± 5.8</td>
|
||
<td id="C3305DC9FFD6D79ABE0F00005F32589E" box="[1052,1150,380,394]" gridcol="3" gridrow="5" pageId="6" pageNumber="430">49.2 ± 3.3</td>
|
||
<td id="C3305DC9FFD6D79ABF4700005EE0589E" box="[1364,1452,380,394]" gridcol="4" gridrow="5" pageId="6" pageNumber="430">135.3 ± 6.4</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D00EF5EE058B5" box="[110,1452,403,417]" gridrow="6" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D00EF5B9358B5" box="[110,223,403,417]" gridcol="0" gridrow="6" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D00EF5B3458B5" bold="true" box="[110,120,403,417]" pageId="6" pageNumber="430">5</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA500EF594258B5" box="[438,526,403,417]" gridcol="1" gridrow="6" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79AB8F700EF580A58B5" box="[740,838,403,417]" gridcol="2" gridrow="6" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABE0F00EF5F3258B5" box="[1052,1150,403,417]" gridcol="3" gridrow="6" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF4700EF5EE058B5" box="[1364,1452,403,417]" gridcol="4" gridrow="6" pageId="6" pageNumber="430">nd</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D00D55EE058AC" box="[110,1452,425,440]" gridrow="7" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D00D55B9358AC" box="[110,223,425,440]" gridcol="0" gridrow="7" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D00D55B3458A3" bold="true" box="[110,120,425,439]" pageId="6" pageNumber="430">6</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA500D5594258AC" box="[438,526,425,440]" gridcol="1" gridrow="7" pageId="6" pageNumber="430">28.7 ± 1.2</td>
|
||
<td id="C3305DC9FFD6D79AB8F700D5580A58AC" box="[740,838,425,440]" gridcol="2" gridrow="7" pageId="6" pageNumber="430">7.6 ± 0.1</td>
|
||
<td id="C3305DC9FFD6D79ABE0F00D55F3258AC" box="[1052,1150,425,440]" gridcol="3" gridrow="7" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF4700D55EE058AC" box="[1364,1452,425,440]" gridcol="4" gridrow="7" pageId="6" pageNumber="430">5.7 ± 0.3</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D00BC5EE058DB" box="[110,1452,448,463]" gridrow="8" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D00BC5B9358DB" box="[110,223,448,463]" gridcol="0" gridrow="8" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D00BC5B3458DA" bold="true" box="[110,120,448,462]" pageId="6" pageNumber="430">7</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA500BC594258DB" box="[438,526,448,463]" gridcol="1" gridrow="8" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F700BC580A58DB" box="[740,838,448,463]" gridcol="2" gridrow="8" pageId="6" pageNumber="430">55.0 ± 8.2</td>
|
||
<td id="C3305DC9FFD6D79ABE0F00BC5F3258DB" box="[1052,1150,448,463]" gridcol="3" gridrow="8" pageId="6" pageNumber="430">71.0 ± 4.0</td>
|
||
<td id="C3305DC9FFD6D79ABF4700BC5EE058DB" box="[1364,1452,448,463]" gridcol="4" gridrow="8" pageId="6" pageNumber="430">85.8 ± 0.1</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D00AB5EE058F2" box="[110,1452,471,486]" gridrow="9" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D00AB5B9358F2" box="[110,223,471,486]" gridcol="0" gridrow="9" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D00AB5B3458F1" bold="true" box="[110,120,471,485]" pageId="6" pageNumber="430">8</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA500AB594258F2" box="[438,526,471,486]" gridcol="1" gridrow="9" pageId="6" pageNumber="430">47.6 ± 12.7</td>
|
||
<td id="C3305DC9FFD6D79AB8F700AB580A58F2" box="[740,838,471,486]" gridcol="2" gridrow="9" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABE0F00AB5F3258F2" box="[1052,1150,471,486]" gridcol="3" gridrow="9" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABF4700AB5EE058F2" box="[1364,1452,471,486]" gridcol="4" gridrow="9" pageId="6" pageNumber="430">nd</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D00925EE058E9" box="[110,1452,494,509]" gridrow="10" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D00925B9358E9" box="[110,223,494,509]" gridcol="0" gridrow="10" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D00925B3458E8" bold="true" box="[110,120,494,508]" pageId="6" pageNumber="430">9</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA50092594258E9" box="[438,526,494,509]" gridcol="1" gridrow="10" pageId="6" pageNumber="430">64.3 ± 8.0</td>
|
||
<td id="C3305DC9FFD6D79AB8F70092580A58E9" box="[740,838,494,509]" gridcol="2" gridrow="10" pageId="6" pageNumber="430">6.5 ± 0.9</td>
|
||
<td id="C3305DC9FFD6D79ABE0F00925F3258E9" box="[1052,1150,494,509]" gridcol="3" gridrow="10" pageId="6" pageNumber="430">63.3 ± 4.4</td>
|
||
<td id="C3305DC9FFD6D79ABF4700925EE058E9" box="[1364,1452,494,509]" gridcol="4" gridrow="10" pageId="6" pageNumber="430">6.4 ± 0.3</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D03795EE05B07" box="[110,1452,517,531]" gridrow="11" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D03795B935B07" box="[110,223,517,531]" gridcol="0" gridrow="11" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D03795BCE5B07" bold="true" box="[110,130,517,531]" pageId="6" pageNumber="430">10</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5037959425B07" box="[438,526,517,531]" gridcol="1" gridrow="11" pageId="6" pageNumber="430">99.7 ± 2.8</td>
|
||
<td id="C3305DC9FFD6D79AB8F70379580A5B07" box="[740,838,517,531]" gridcol="2" gridrow="11" pageId="6" pageNumber="430">22.7 ± 0.6</td>
|
||
<td id="C3305DC9FFD6D79ABE0F03795F325B07" box="[1052,1150,517,531]" gridcol="3" gridrow="11" pageId="6" pageNumber="430">11.1 ± 0.5</td>
|
||
<td id="C3305DC9FFD6D79ABF4703795EE05B07" box="[1364,1452,517,531]" gridcol="4" gridrow="11" pageId="6" pageNumber="430">247.3 ± 1.5</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D03605EE05B3E" box="[110,1452,540,554]" gridrow="12" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D03605B935B3E" box="[110,223,540,554]" gridcol="0" gridrow="12" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D03605BCE5B3E" bold="true" box="[110,130,540,554]" pageId="6" pageNumber="430">11</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5036059425B3E" box="[438,526,540,554]" gridcol="1" gridrow="12" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F70360580A5B3E" box="[740,838,540,554]" gridcol="2" gridrow="12" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABE0F03605F325B3E" box="[1052,1150,540,554]" gridcol="3" gridrow="12" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF4703605EE05B3E" box="[1364,1452,540,554]" gridcol="4" gridrow="12" pageId="6" pageNumber="430">1.9 ± 0.1</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D034F5EE05B55" box="[110,1452,563,577]" gridrow="13" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D034F5B935B55" box="[110,223,563,577]" gridcol="0" gridrow="13" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D034F5BCE5B55" bold="true" box="[110,130,563,577]" pageId="6" pageNumber="430">12</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5034F59425B55" box="[438,526,563,577]" gridcol="1" gridrow="13" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F7034F580A5B55" box="[740,838,563,577]" gridcol="2" gridrow="13" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABE0F034F5F325B55" box="[1052,1150,563,577]" gridcol="3" gridrow="13" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABF47034F5EE05B55" box="[1364,1452,563,577]" gridcol="4" gridrow="13" pageId="6" pageNumber="430">0.9 ± 0.1</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D03355EE05B4C" box="[110,1452,585,600]" gridrow="14" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D03355B935B4C" box="[110,223,585,600]" gridcol="0" gridrow="14" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D03355BCE5B43" bold="true" box="[110,130,585,599]" pageId="6" pageNumber="430">13</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5033559425B4C" box="[438,526,585,600]" gridcol="1" gridrow="14" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F70335580A5B4C" box="[740,838,585,600]" gridcol="2" gridrow="14" pageId="6" pageNumber="430">286.1 ± 15.2</td>
|
||
<td id="C3305DC9FFD6D79ABE0F03355F325B4C" box="[1052,1150,585,600]" gridcol="3" gridrow="14" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF4703355EE05B4C" box="[1364,1452,585,600]" gridcol="4" gridrow="14" pageId="6" pageNumber="430">nd</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D031C5EE05B7B" box="[110,1452,608,623]" gridrow="15" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D031C5B935B7B" box="[110,223,608,623]" gridcol="0" gridrow="15" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D031C5BCE5B7A" bold="true" box="[110,130,608,622]" pageId="6" pageNumber="430">14</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5031C59425B7B" box="[438,526,608,623]" gridcol="1" gridrow="15" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F7031C580A5B7B" box="[740,838,608,623]" gridcol="2" gridrow="15" pageId="6" pageNumber="430">28.0 ± 1.7</td>
|
||
<td id="C3305DC9FFD6D79ABE0F031C5F325B7B" box="[1052,1150,608,623]" gridcol="3" gridrow="15" pageId="6" pageNumber="430">93.6 ± 5.8</td>
|
||
<td id="C3305DC9FFD6D79ABF47031C5EE05B7B" box="[1364,1452,608,623]" gridcol="4" gridrow="15" pageId="6" pageNumber="430">75.0 ± 4.1</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D030B5EE05B91" box="[110,1452,631,645]" gridrow="16" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D030B5B935B91" box="[110,223,631,645]" gridcol="0" gridrow="16" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D030B5BCE5B91" bold="true" box="[110,130,631,645]" pageId="6" pageNumber="430">15</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5030B59425B91" box="[438,526,631,645]" gridcol="1" gridrow="16" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F7030B580A5B91" box="[740,838,631,645]" gridcol="2" gridrow="16" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABE0F030B5F325B91" box="[1052,1150,631,645]" gridcol="3" gridrow="16" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF47030B5EE05B91" box="[1364,1452,631,645]" gridcol="4" gridrow="16" pageId="6" pageNumber="430">167.6 ± 5.2</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D03F25EE05B88" box="[110,1452,654,668]" gridrow="17" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D03F25B935B88" box="[110,223,654,668]" gridcol="0" gridrow="17" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D03F25BCE5B88" bold="true" box="[110,130,654,668]" pageId="6" pageNumber="430">16</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA503F259425B88" box="[438,526,654,668]" gridcol="1" gridrow="17" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F703F2580A5B88" box="[740,838,654,668]" gridcol="2" gridrow="17" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABE0F03F25F325B88" box="[1052,1150,654,668]" gridcol="3" gridrow="17" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF4703F25EE05B88" box="[1364,1452,654,668]" gridcol="4" gridrow="17" pageId="6" pageNumber="430">58.2 ± 5.1</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D03D95EE05BA7" box="[110,1452,677,691]" gridrow="18" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D03D95B935BA7" box="[110,223,677,691]" gridcol="0" gridrow="18" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D03D95BCE5BA7" bold="true" box="[110,130,677,691]" pageId="6" pageNumber="430">17</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA503D959425BA7" box="[438,526,677,691]" gridcol="1" gridrow="18" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F703D9580A5BA7" box="[740,838,677,691]" gridcol="2" gridrow="18" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79ABE0F03D95F325BA7" box="[1052,1150,677,691]" gridcol="3" gridrow="18" pageId="6" pageNumber="430">63.9 ± 1.9</td>
|
||
<td id="C3305DC9FFD6D79ABF4703D95EE05BA7" box="[1364,1452,677,691]" gridcol="4" gridrow="18" pageId="6" pageNumber="430">40.8 ± 1.9</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D03C05EE05BDE" box="[110,1452,700,714]" gridrow="19" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D03C05B935BDE" box="[110,223,700,714]" gridcol="0" gridrow="19" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D03C05BCE5BDE" bold="true" box="[110,130,700,714]" pageId="6" pageNumber="430">18</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA503C059425BDE" box="[438,526,700,714]" gridcol="1" gridrow="19" pageId="6" pageNumber="430">18.7 ± 5.5</td>
|
||
<td id="C3305DC9FFD6D79AB8F703C0580A5BDE" box="[740,838,700,714]" gridcol="2" gridrow="19" pageId="6" pageNumber="430">60.5 ± 0.1</td>
|
||
<td id="C3305DC9FFD6D79ABE0F03C05F325BDE" box="[1052,1150,700,714]" gridcol="3" gridrow="19" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF4703C05EE05BDE" box="[1364,1452,700,714]" gridcol="4" gridrow="19" pageId="6" pageNumber="430">nd</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D03AF5EE05BF5" box="[110,1452,723,737]" gridrow="20" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D03AF5B935BF5" box="[110,223,723,737]" gridcol="0" gridrow="20" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D03AF5BCE5BF5" bold="true" box="[110,130,723,737]" pageId="6" pageNumber="430">19</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA503AF59425BF5" box="[438,526,723,737]" gridcol="1" gridrow="20" pageId="6" pageNumber="430">86.9 ± 3.3</td>
|
||
<td id="C3305DC9FFD6D79AB8F703AF580A5BF5" box="[740,838,723,737]" gridcol="2" gridrow="20" pageId="6" pageNumber="430">50.1 ± 2.2</td>
|
||
<td id="C3305DC9FFD6D79ABE0F03AF5F325BF5" box="[1052,1150,723,737]" gridcol="3" gridrow="20" pageId="6" pageNumber="430">102.1 ± 6.2</td>
|
||
<td id="C3305DC9FFD6D79ABF4703AF5EE05BF5" box="[1364,1452,723,737]" gridcol="4" gridrow="20" pageId="6" pageNumber="430">4.9 ± 0.3</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D03955EE05BEC" box="[110,1452,745,760]" gridrow="21" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D03955B935BEC" box="[110,223,745,760]" gridcol="0" gridrow="21" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D03955BCE5BE3" bold="true" box="[110,130,745,759]" pageId="6" pageNumber="430">20</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5039559425BEC" box="[438,526,745,760]" gridcol="1" gridrow="21" pageId="6" pageNumber="430">47.7 ± 3.9</td>
|
||
<td id="C3305DC9FFD6D79AB8F70395580A5BEC" box="[740,838,745,760]" gridcol="2" gridrow="21" pageId="6" pageNumber="430">28.8 ± 0.6</td>
|
||
<td id="C3305DC9FFD6D79ABE0F03955F325BEC" box="[1052,1150,745,760]" gridcol="3" gridrow="21" pageId="6" pageNumber="430">90.8 ± 0.4</td>
|
||
<td id="C3305DC9FFD6D79ABF4703955EE05BEC" box="[1364,1452,745,760]" gridcol="4" gridrow="21" pageId="6" pageNumber="430">1.0 ± 0.5</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D027C5EE05A1B" box="[110,1452,768,783]" gridrow="22" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D027C5B935A1B" box="[110,223,768,783]" gridcol="0" gridrow="22" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D027C5BCE5A1A" bold="true" box="[110,130,768,782]" pageId="6" pageNumber="430">21</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5027C59425A1B" box="[438,526,768,783]" gridcol="1" gridrow="22" pageId="6" pageNumber="430">38.7 ± 3.0</td>
|
||
<td id="C3305DC9FFD6D79AB8F7027C580A5A1B" box="[740,838,768,783]" gridcol="2" gridrow="22" pageId="6" pageNumber="430">34.0 ± 0.6</td>
|
||
<td id="C3305DC9FFD6D79ABE0F027C5F325A1B" box="[1052,1150,768,783]" gridcol="3" gridrow="22" pageId="6" pageNumber="430">220.2 ± 9.7</td>
|
||
<td id="C3305DC9FFD6D79ABF47027C5EE05A1B" box="[1364,1452,768,783]" gridcol="4" gridrow="22" pageId="6" pageNumber="430">2.5 ± 0.4</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D026B5EE05A31" box="[110,1452,791,805]" gridrow="23" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D026B5B935A31" box="[110,223,791,805]" gridcol="0" gridrow="23" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D026B5BCE5A31" bold="true" box="[110,130,791,805]" pageId="6" pageNumber="430">22</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABBA5026B59425A31" box="[438,526,791,805]" gridcol="1" gridrow="23" pageId="6" pageNumber="430">>300</td>
|
||
<td id="C3305DC9FFD6D79AB8F7026B580A5A31" box="[740,838,791,805]" gridcol="2" gridrow="23" pageId="6" pageNumber="430">101.9 ± 4.0</td>
|
||
<td id="C3305DC9FFD6D79ABE0F026B5F325A31" box="[1052,1150,791,805]" gridcol="3" gridrow="23" pageId="6" pageNumber="430">151.0 ± 10.4</td>
|
||
<td id="C3305DC9FFD6D79ABF47026B5EE05A31" box="[1364,1452,791,805]" gridcol="4" gridrow="23" pageId="6" pageNumber="430">239.4 ± 8.4</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D02565EE05A28" box="[110,1452,810,828]" gridrow="24" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D02565B935A28" box="[110,223,810,828]" gridcol="0" gridrow="24" pageId="6" pageNumber="430">Ascorbic acid c</th>
|
||
<td id="C3305DC9FFD6D79ABBA5025659425A28" box="[438,526,810,828]" gridcol="1" gridrow="24" pageId="6" pageNumber="430">19.9 ± 1.2</td>
|
||
<td id="C3305DC9FFD6D79AB8F70256580A5A28" box="[740,838,810,828]" gridcol="2" gridrow="24" pageId="6" pageNumber="430">28.2 ± 0.4</td>
|
||
<td id="C3305DC9FFD6D79ABE0F02565F325A28" box="[1052,1150,810,828]" gridcol="3" gridrow="24" pageId="6" pageNumber="430">20.6 ± 1.6</td>
|
||
<td id="C3305DC9FFD6D79ABF4702565EE05A28" box="[1364,1452,810,828]" gridcol="4" gridrow="24" pageId="6" pageNumber="430">105.0 ± 3.7</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D023D5EE05A47" box="[110,1452,833,851]" gridrow="25" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D023D5B935A47" box="[110,223,833,851]" gridcol="0" gridrow="25" pageId="6" pageNumber="430">Arbutin c</th>
|
||
<td id="C3305DC9FFD6D79ABBA5023D59425A47" box="[438,526,833,851]" gridcol="1" gridrow="25" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79AB8F7023D580A5A47" box="[740,838,833,851]" gridcol="2" gridrow="25" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABE0F023D5F325A47" box="[1052,1150,833,851]" gridcol="3" gridrow="25" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF47023D5EE05A47" box="[1364,1452,833,851]" gridcol="4" gridrow="25" pageId="6" pageNumber="430">81.8 ± 2.3</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D02245EE05A7E" box="[110,1452,856,874]" gridrow="26" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D02245B935A7E" box="[110,223,856,874]" gridcol="0" gridrow="26" pageId="6" pageNumber="430">Kojic acid c</th>
|
||
<td id="C3305DC9FFD6D79ABBA5022459425A7E" box="[438,526,856,874]" gridcol="1" gridrow="26" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79AB8F70224580A5A7E" box="[740,838,856,874]" gridcol="2" gridrow="26" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABE0F02245F325A7E" box="[1052,1150,856,874]" gridcol="3" gridrow="26" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABF4702245EE05A7E" box="[1364,1452,856,874]" gridcol="4" gridrow="26" pageId="6" pageNumber="430">63.7 ± 4.5</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<tableNote id="C3373779FFD62863BA4402FE5A145D17" pageId="6" pageNumber="430" targetBox="[110,1452,240,874]" targetPageId="6">
|
||
<paragraph id="3E6E36F7FFD62863BA4402FE5BB25A84" blockId="6.[87,1475,898,1027]" box="[87,254,898,913]" pageId="6" pageNumber="430">Nd: not determined.</paragraph>
|
||
<paragraph id="3E6E36F7FFD62863BA7402EA5E615AB3" blockId="6.[87,1475,898,1027]" box="[103,1325,918,936]" pageId="6" pageNumber="430">
|
||
<superScript id="C9A49BBFFFD62863BA7402EA5B225A8B" attach="left" box="[103,110,918,927]" fontSize="4" pageId="6" pageNumber="430">a</superScript>
|
||
The purity of each tested compounds was
|
||
<emphasis id="0CA5EAE5FFD62863BBC202E45AAE5ABC" bold="true" box="[465,482,920,936]" italics="true" pageId="6" pageNumber="430">À</emphasis>
|
||
98% according to LC-MS data. Each value represents the mean ± S.D. of three independent experiments.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD62863BA7502D059795AC1" blockId="6.[87,1475,898,1027]" pageId="6" pageNumber="430">
|
||
<superScript id="C9A49BBFFFD62863BA7502D05B215AA2" attach="right" box="[102,109,940,950]" fontSize="4" pageId="6" pageNumber="430">b</superScript>
|
||
SC is the concentration of the compounds required to scavenge 50% of the radicals; IC is the concentration of the compounds required to inhibit 50% of the enzyme;
|
||
<subScript id="A25534B2FFD62863BA9802CB58055AD5" attach="left" box="[139,841,951,961]" fontSize="4" pageId="6" pageNumber="430">50 50</subScript>
|
||
nd: not determined due to poor solubility or limited yield.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD62863BA7402A65A145D17" blockId="6.[87,1475,898,1027]" pageId="6" pageNumber="430">
|
||
<superScript id="C9A49BBFFFD62863BA7402A65B215AF7" attach="right" box="[103,109,986,995]" fontSize="4" pageId="6" pageNumber="430">c</superScript>
|
||
Ascorbic acid (vitamin C) is used as positive control of both free radical scavenger and tyrosinase inhibitor and, however, arbutin as well as kojic acid are used as positive controls of tyrosinase inhibitor.
|
||
</paragraph>
|
||
</tableNote>
|
||
<caption id="6AAE667FFFD62863BA4405D75FC15DC4" ID-Table-UUID="6AAE667FFFD62863BA4405D75FC15DC4" httpUri="http://table.plazi.org/id/6AAE667FFFD62863BA4405D75FC15DC4" pageId="6" pageNumber="430" startId="6.[87,131,1195,1209]" targetBox="[110,1451,1252,1875]" targetIsTable="true" targetPageId="6" targetType="table">
|
||
<paragraph id="3E6E36F7FFD62863BA4405D75FC15DC4" blockId="6.[87,1165,1195,1232]" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA4405D75BDF5DAD" bold="true" box="[87,147,1195,1209]" pageId="6" pageNumber="430">Table 4</emphasis>
|
||
Effect of compounds isolated from
|
||
<taxonomicName id="F9D14D74FFD62863BB7D05BD5AAB5DC4" box="[366,487,1217,1232]" class="Magnoliopsida" family="Moraceae" genus="Artocarpus" kingdom="Plantae" order="Rosales" pageId="6" pageNumber="430" phylum="Tracheophyta" rank="species" species="xanthocarpus">
|
||
<emphasis id="0CA5EAE5FFD62863BB7D05BD5AAB5DC4" box="[366,487,1217,1232]" italics="true" pageId="6" pageNumber="430">A. xanthocarpus</emphasis>
|
||
</taxonomicName>
|
||
on melanin content, tyrosinase activity, and cell viability of B16F10 melanoma cells.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="3E6E36F7FFD62863BA7D05945FB35E5E" pageId="6" pageNumber="430">
|
||
<table id="4CD1C457FFD6D79ABA7D05985EE75E47" box="[110,1451,1252,1875]" gridcols="5" gridrows="27" pageId="6" pageNumber="430">
|
||
<tr id="80E134B5FFD6D79ABA7D05985EE75DE3" box="[110,1451,1252,1271]" gridrow="0" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D05985B825DE3" box="[110,206,1252,1271]" gridcol="0" gridrow="0" pageId="6" pageNumber="430">Compounds</th>
|
||
<th id="C3305DC9FFD6D79ABB3005985AF25DE3" box="[291,446,1252,1271]" gridcol="1" gridrow="0" pageId="6" pageNumber="430">Concentration (µµ)</th>
|
||
<th id="C3305DC9FFD6D79AB800059859BE5DE3" box="[531,754,1252,1271]" gridcol="2" gridrow="0" pageId="6" pageNumber="430">Cell viability (% of control) a</th>
|
||
<th id="C3305DC9FFD6D79AB95405985F095DE3" box="[839,1093,1252,1271]" gridcol="3" gridrow="0" pageId="6" pageNumber="430">Melanin content (% of control)b</th>
|
||
<th id="C3305DC9FFD6D79ABE8905985EE75DE3" box="[1178,1451,1252,1271]" gridcol="4" gridrow="0" pageId="6" pageNumber="430">Tyrosinase activity (% of control)b</th>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04765EE75C0C" box="[110,1451,1290,1304]" gridrow="1" pageId="6" pageNumber="430" rowspan-1="1">
|
||
<th id="C3305DC9FFD6D79ABA7D04765B825C0C" box="[110,206,1290,1304]" gridcol="0" gridrow="1" pageId="6" pageNumber="430">Control</th>
|
||
<td id="C3305DC9FFD6D79AB800047659BE5C0C" box="[531,754,1290,1304]" gridcol="2" gridrow="1" pageId="6" pageNumber="430">100.0 ± 0.9</td>
|
||
<td id="C3305DC9FFD6D79AB95404765F095C0C" box="[839,1093,1290,1304]" gridcol="3" gridrow="1" pageId="6" pageNumber="430">100.0 ± 3.1</td>
|
||
<td id="C3305DC9FFD6D79ABE8904765EE75C0C" box="[1178,1451,1290,1304]" gridcol="4" gridrow="1" pageId="6" pageNumber="430">100.0 ± 3.0</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04615EE75C24" box="[110,1451,1309,1328]" gridrow="2" pageId="6" pageNumber="430" rowspan-1="1">
|
||
<th id="C3305DC9FFD6D79ABA7D04615B825C24" box="[110,206,1309,1328]" gridcol="0" gridrow="2" pageId="6" pageNumber="430">OE- MSH</th>
|
||
<td id="C3305DC9FFD6D79AB800046159BE5C24" box="[531,754,1309,1328]" gridcol="2" gridrow="2" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79AB95404615F095C24" box="[839,1093,1309,1328]" gridcol="3" gridrow="2" pageId="6" pageNumber="430">123.3 ± 10.5 #</td>
|
||
<td id="C3305DC9FFD6D79ABE8904615EE75C24" box="[1178,1451,1309,1328]" gridcol="4" gridrow="2" pageId="6" pageNumber="430">122.1 ± 12.3 #</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04495EE75C52" box="[110,1451,1333,1350]" gridrow="3" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D04495B825C52" box="[110,206,1333,1350]" gridcol="0" gridrow="3" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D04445B345C52" bold="true" box="[110,120,1336,1350]" pageId="6" pageNumber="430">1</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3004495AF25C52" box="[291,446,1333,1350]" gridcol="1" gridrow="3" pageId="6" pageNumber="430">40</td>
|
||
<td id="C3305DC9FFD6D79AB800044959BE5C52" box="[531,754,1333,1350]" gridcol="2" gridrow="3" pageId="6" pageNumber="430">110.1 ± 3.7</td>
|
||
<td id="C3305DC9FFD6D79AB95404495F095C52" box="[839,1093,1333,1350]" gridcol="3" gridrow="3" pageId="6" pageNumber="430">
|
||
63.2 ± 9.4
|
||
<emphasis id="0CA5EAE5FFD62863B987044958ED5C29" bold="true" box="[916,929,1333,1341]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8904495EE75C52" box="[1178,1451,1333,1350]" gridcol="4" gridrow="3" pageId="6" pageNumber="430">
|
||
78.7 ± 13.9
|
||
<emphasis id="0CA5EAE5FFD62863BEE104495FB35C29" bold="true" box="[1266,1279,1333,1341]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04305EE75C49" box="[110,1451,1356,1373]" gridrow="4" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D04305B825C49" box="[110,206,1356,1373]" gridcol="0" gridrow="4" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D04325B345C48" bold="true" box="[110,120,1358,1372]" pageId="6" pageNumber="430">2</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3004305AF25C49" box="[291,446,1356,1373]" gridcol="1" gridrow="4" pageId="6" pageNumber="430">40</td>
|
||
<td id="C3305DC9FFD6D79AB800043059BE5C49" box="[531,754,1356,1373]" gridcol="2" gridrow="4" pageId="6" pageNumber="430">95.5 ± 4.3</td>
|
||
<td id="C3305DC9FFD6D79AB95404305F095C49" box="[839,1093,1356,1373]" gridcol="3" gridrow="4" pageId="6" pageNumber="430">
|
||
50.8 ± 8.5
|
||
<emphasis id="0CA5EAE5FFD62863B987043058ED5C40" bold="true" box="[916,929,1356,1364]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8904305EE75C49" box="[1178,1451,1356,1373]" gridcol="4" gridrow="4" pageId="6" pageNumber="430">
|
||
105.8 ± 4.9
|
||
<emphasis id="0CA5EAE5FFD62863BEE104305FB35C40" bold="true" box="[1266,1279,1356,1364]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D041E5EE75C60" box="[110,1451,1378,1396]" gridrow="5" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D041E5B825C60" box="[110,206,1378,1396]" gridcol="0" gridrow="5" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D04195B345C67" bold="true" box="[110,120,1381,1395]" pageId="6" pageNumber="430">3</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB30041E5AF25C60" box="[291,446,1378,1396]" gridcol="1" gridrow="5" pageId="6" pageNumber="430">10</td>
|
||
<td id="C3305DC9FFD6D79AB800041E59BE5C60" box="[531,754,1378,1396]" gridcol="2" gridrow="5" pageId="6" pageNumber="430">105.1 ± 2.4</td>
|
||
<td id="C3305DC9FFD6D79AB954041E5F095C60" box="[839,1093,1378,1396]" gridcol="3" gridrow="5" pageId="6" pageNumber="430">
|
||
64.3 ± 9.4
|
||
<emphasis id="0CA5EAE5FFD62863B987041E58ED5C7E" bold="true" box="[916,929,1378,1386]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE89041E5EE75C60" box="[1178,1451,1378,1396]" gridcol="4" gridrow="5" pageId="6" pageNumber="430">111.7 ± 11.0</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04055EE75C9E" box="[110,1451,1401,1418]" gridrow="6" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D04055B825C9E" box="[110,206,1401,1418]" gridcol="0" gridrow="6" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D04005B345C9E" bold="true" box="[110,120,1404,1418]" pageId="6" pageNumber="430">4</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3004055AF25C9E" box="[291,446,1401,1418]" gridcol="1" gridrow="6" pageId="6" pageNumber="430">10</td>
|
||
<td id="C3305DC9FFD6D79AB800040559BE5C9E" box="[531,754,1401,1418]" gridcol="2" gridrow="6" pageId="6" pageNumber="430">97.3 ± 0.4</td>
|
||
<td id="C3305DC9FFD6D79AB95404055F095C9E" box="[839,1093,1401,1418]" gridcol="3" gridrow="6" pageId="6" pageNumber="430">
|
||
65.7 ± 4.7
|
||
<emphasis id="0CA5EAE5FFD62863B987040558ED5C95" bold="true" box="[916,929,1401,1409]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8904055EE75C9E" box="[1178,1451,1401,1418]" gridcol="4" gridrow="6" pageId="6" pageNumber="430">
|
||
100.8 ± 6.4
|
||
<emphasis id="0CA5EAE5FFD62863BEE204055FB45C95" bold="true" box="[1265,1272,1401,1409]" italics="true" pageId="6" pageNumber="430">⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04EF5EE75CB5" box="[110,1451,1427,1441]" gridrow="7" pageId="6" pageNumber="430" rowspan-1="1">
|
||
<th id="C3305DC9FFD6D79ABA7D04EF5B825CB5" box="[110,206,1427,1441]" gridcol="0" gridrow="7" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D04EF5B345CB5" bold="true" box="[110,120,1427,1441]" pageId="6" pageNumber="430">5</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79AB80004EF59BE5CB5" box="[531,754,1427,1441]" gridcol="2" gridrow="7" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79AB95404EF5F095CB5" box="[839,1093,1427,1441]" gridcol="3" gridrow="7" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABE8904EF5EE75CB5" box="[1178,1451,1427,1441]" gridcol="4" gridrow="7" pageId="6" pageNumber="430">nd</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04D65EE75CAC" box="[110,1451,1450,1464]" gridrow="8" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D04D65B825CAC" box="[110,206,1450,1464]" gridcol="0" gridrow="8" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D04D65B345CAC" bold="true" box="[110,120,1450,1464]" pageId="6" pageNumber="430">6</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3004D65AF25CAC" box="[291,446,1450,1464]" gridcol="1" gridrow="8" pageId="6" pageNumber="430">80</td>
|
||
<td id="C3305DC9FFD6D79AB80004D659BE5CAC" box="[531,754,1450,1464]" gridcol="2" gridrow="8" pageId="6" pageNumber="430">99.5 ± 7.8</td>
|
||
<td id="C3305DC9FFD6D79AB95404D65F095CAC" box="[839,1093,1450,1464]" gridcol="3" gridrow="8" pageId="6" pageNumber="430">113.9 ± 12.6</td>
|
||
<td id="C3305DC9FFD6D79ABE8904D65EE75CAC" box="[1178,1451,1450,1464]" gridcol="4" gridrow="8" pageId="6" pageNumber="430">135.5 ± 3.0</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04C25EE75CDB" box="[110,1451,1470,1487]" gridrow="9" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D04C25B825CDB" box="[110,206,1470,1487]" gridcol="0" gridrow="9" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D04BD5B345CDB" bold="true" box="[110,120,1473,1487]" pageId="6" pageNumber="430">7</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3004C25AF25CDB" box="[291,446,1470,1487]" gridcol="1" gridrow="9" pageId="6" pageNumber="430">80</td>
|
||
<td id="C3305DC9FFD6D79AB80004C259BE5CDB" box="[531,754,1470,1487]" gridcol="2" gridrow="9" pageId="6" pageNumber="430">97.9 ± 0.7</td>
|
||
<td id="C3305DC9FFD6D79AB95404C25F095CDB" box="[839,1093,1470,1487]" gridcol="3" gridrow="9" pageId="6" pageNumber="430">
|
||
96.0 ± 9.6
|
||
<emphasis id="0CA5EAE5FFD62863B98704C258D75CD2" bold="true" box="[916,923,1470,1478]" italics="true" pageId="6" pageNumber="430">⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8904C25EE75CDB" box="[1178,1451,1470,1487]" gridcol="4" gridrow="9" pageId="6" pageNumber="430">109.3 ± 18.4</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04A95EE75CF2" box="[110,1451,1493,1510]" gridrow="10" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D04A95B825CF2" box="[110,206,1493,1510]" gridcol="0" gridrow="10" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D04A45B345CF2" bold="true" box="[110,120,1496,1510]" pageId="6" pageNumber="430">8</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3004A95AF25CF2" box="[291,446,1493,1510]" gridcol="1" gridrow="10" pageId="6" pageNumber="430">20</td>
|
||
<td id="C3305DC9FFD6D79AB80004A959BE5CF2" box="[531,754,1493,1510]" gridcol="2" gridrow="10" pageId="6" pageNumber="430">102.0 ± 3.0</td>
|
||
<td id="C3305DC9FFD6D79AB95404A95F095CF2" box="[839,1093,1493,1510]" gridcol="3" gridrow="10" pageId="6" pageNumber="430">
|
||
67.8 ± 111.6
|
||
<emphasis id="0CA5EAE5FFD62863B9BB04A958F95CC9" bold="true" box="[936,949,1493,1501]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8904A95EE75CF2" box="[1178,1451,1493,1510]" gridcol="4" gridrow="10" pageId="6" pageNumber="430">
|
||
86.6 ± 3.1
|
||
<emphasis id="0CA5EAE5FFD62863BEFB04A95FA35CC9" bold="true" box="[1256,1263,1493,1501]" italics="true" pageId="6" pageNumber="430">⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D04925EE75CE9" box="[110,1451,1518,1533]" gridrow="11" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D04925B825CE9" box="[110,206,1518,1533]" gridcol="0" gridrow="11" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D04925B345CE8" bold="true" box="[110,120,1518,1532]" pageId="6" pageNumber="430">9</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3004925AF25CE9" box="[291,446,1518,1533]" gridcol="1" gridrow="11" pageId="6" pageNumber="430">80</td>
|
||
<td id="C3305DC9FFD6D79AB800049259BE5CE9" box="[531,754,1518,1533]" gridcol="2" gridrow="11" pageId="6" pageNumber="430">102.4 ± 8.4</td>
|
||
<td id="C3305DC9FFD6D79AB95404925F095CE9" box="[839,1093,1518,1533]" gridcol="3" gridrow="11" pageId="6" pageNumber="430">111.8 ± 10.9</td>
|
||
<td id="C3305DC9FFD6D79ABE8904925EE75CE9" box="[1178,1451,1518,1533]" gridcol="4" gridrow="11" pageId="6" pageNumber="430">134.3 ± 7.7</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D077E5EE75F00" box="[110,1451,1538,1556]" gridrow="12" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D077E5B825F00" box="[110,206,1538,1556]" gridcol="0" gridrow="12" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D07795BCE5F07" bold="true" box="[110,130,1541,1555]" pageId="6" pageNumber="430">10</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB30077E5AF25F00" box="[291,446,1538,1556]" gridcol="1" gridrow="12" pageId="6" pageNumber="430">80</td>
|
||
<td id="C3305DC9FFD6D79AB800077E59BE5F00" box="[531,754,1538,1556]" gridcol="2" gridrow="12" pageId="6" pageNumber="430">100.5 ± 0.4</td>
|
||
<td id="C3305DC9FFD6D79AB954077E5F095F00" box="[839,1093,1538,1556]" gridcol="3" gridrow="12" pageId="6" pageNumber="430">
|
||
100.0 ± 14.0
|
||
<emphasis id="0CA5EAE5FFD62863B9BB077E58E35F1E" bold="true" box="[936,943,1538,1546]" italics="true" pageId="6" pageNumber="430">⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE89077E5EE75F00" box="[1178,1451,1538,1556]" gridcol="4" gridrow="12" pageId="6" pageNumber="430">176.5 ± 4.9</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D07605EE75F3E" box="[110,1451,1564,1578]" gridrow="13" pageId="6" pageNumber="430" rowspan-1="1">
|
||
<th id="C3305DC9FFD6D79ABA7D07605B825F3E" box="[110,206,1564,1578]" gridcol="0" gridrow="13" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D07605BCE5F3E" bold="true" box="[110,130,1564,1578]" pageId="6" pageNumber="430">11</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79AB800076059BE5F3E" box="[531,754,1564,1578]" gridcol="2" gridrow="13" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79AB95407605F095F3E" box="[839,1093,1564,1578]" gridcol="3" gridrow="13" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABE8907605EE75F3E" box="[1178,1451,1564,1578]" gridcol="4" gridrow="13" pageId="6" pageNumber="430">nd</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D074C5EE75F55" box="[110,1451,1584,1601]" gridrow="14" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D074C5B825F55" box="[110,206,1584,1601]" gridcol="0" gridrow="14" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D074F5BCE5F55" bold="true" box="[110,130,1587,1601]" pageId="6" pageNumber="430">12</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB30074C5AF25F55" box="[291,446,1584,1601]" gridcol="1" gridrow="14" pageId="6" pageNumber="430">20</td>
|
||
<td id="C3305DC9FFD6D79AB800074C59BE5F55" box="[531,754,1584,1601]" gridcol="2" gridrow="14" pageId="6" pageNumber="430">94.0 ± 1.3</td>
|
||
<td id="C3305DC9FFD6D79AB954074C5F095F55" box="[839,1093,1584,1601]" gridcol="3" gridrow="14" pageId="6" pageNumber="430">112.6 ± 19.3</td>
|
||
<td id="C3305DC9FFD6D79ABE89074C5EE75F55" box="[1178,1451,1584,1601]" gridcol="4" gridrow="14" pageId="6" pageNumber="430">
|
||
141.4 ± 12.2
|
||
<emphasis id="0CA5EAE5FFD62863BEEF074C5E4F5F2C" bold="true" box="[1276,1283,1584,1592]" italics="true" pageId="6" pageNumber="430">⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D073B5EE75F4C" box="[110,1451,1607,1624]" gridrow="15" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D073B5B825F4C" box="[110,206,1607,1624]" gridcol="0" gridrow="15" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D07365BCE5F4C" bold="true" box="[110,130,1610,1624]" pageId="6" pageNumber="430">13</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB30073B5AF25F4C" box="[291,446,1607,1624]" gridcol="1" gridrow="15" pageId="6" pageNumber="430">80</td>
|
||
<td id="C3305DC9FFD6D79AB800073B59BE5F4C" box="[531,754,1607,1624]" gridcol="2" gridrow="15" pageId="6" pageNumber="430">100.9 ± 5.3</td>
|
||
<td id="C3305DC9FFD6D79AB954073B5F095F4C" box="[839,1093,1607,1624]" gridcol="3" gridrow="15" pageId="6" pageNumber="430">
|
||
134.9 ± 13.9
|
||
<emphasis id="0CA5EAE5FFD62863B9BB073B58F95F5B" bold="true" box="[936,949,1607,1615]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE89073B5EE75F4C" box="[1178,1451,1607,1624]" gridcol="4" gridrow="15" pageId="6" pageNumber="430">160.2 ± 38.5</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D07225EE75F7B" box="[110,1451,1630,1647]" gridrow="16" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D07225B825F7B" box="[110,206,1630,1647]" gridcol="0" gridrow="16" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D071C5BCE5F7A" bold="true" box="[110,130,1632,1646]" pageId="6" pageNumber="430">14</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3007225AF25F7B" box="[291,446,1630,1647]" gridcol="1" gridrow="16" pageId="6" pageNumber="430">20</td>
|
||
<td id="C3305DC9FFD6D79AB800072259BE5F7B" box="[531,754,1630,1647]" gridcol="2" gridrow="16" pageId="6" pageNumber="430">106.7 ± 0.5</td>
|
||
<td id="C3305DC9FFD6D79AB95407225F095F7B" box="[839,1093,1630,1647]" gridcol="3" gridrow="16" pageId="6" pageNumber="430">
|
||
79.1 ± 3.4
|
||
<emphasis id="0CA5EAE5FFD62863B987072258D75F72" bold="true" box="[916,923,1630,1638]" italics="true" pageId="6" pageNumber="430">⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8907225EE75F7B" box="[1178,1451,1630,1647]" gridcol="4" gridrow="16" pageId="6" pageNumber="430">122.9 ± 16.5</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D07085EE75F92" box="[110,1451,1652,1670]" gridrow="17" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D07085B825F92" box="[110,206,1652,1670]" gridcol="0" gridrow="17" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D070B5BCE5F91" bold="true" box="[110,130,1655,1669]" pageId="6" pageNumber="430">15</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3007085AF25F92" box="[291,446,1652,1670]" gridcol="1" gridrow="17" pageId="6" pageNumber="430">10</td>
|
||
<td id="C3305DC9FFD6D79AB800070859BE5F92" box="[531,754,1652,1670]" gridcol="2" gridrow="17" pageId="6" pageNumber="430">75.2 ± 9.5#</td>
|
||
<td id="C3305DC9FFD6D79AB95407085F095F92" box="[839,1093,1652,1670]" gridcol="3" gridrow="17" pageId="6" pageNumber="430">nd</td>
|
||
<td id="C3305DC9FFD6D79ABE8907085EE75F92" box="[1178,1451,1652,1670]" gridcol="4" gridrow="17" pageId="6" pageNumber="430">nd</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D07F05EE75F89" box="[110,1451,1676,1693]" gridrow="18" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D07F05B825F89" box="[110,206,1676,1693]" gridcol="0" gridrow="18" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D07F25BCE5F88" bold="true" box="[110,130,1678,1692]" pageId="6" pageNumber="430">16</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3007F05AF25F89" box="[291,446,1676,1693]" gridcol="1" gridrow="18" pageId="6" pageNumber="430">20</td>
|
||
<td id="C3305DC9FFD6D79AB80007F059BE5F89" box="[531,754,1676,1693]" gridcol="2" gridrow="18" pageId="6" pageNumber="430">104.4 ± 8.6</td>
|
||
<td id="C3305DC9FFD6D79AB95407F05F095F89" box="[839,1093,1676,1693]" gridcol="3" gridrow="18" pageId="6" pageNumber="430">
|
||
92.6 ± 8.2
|
||
<emphasis id="0CA5EAE5FFD62863B98707F058ED5F80" bold="true" box="[916,929,1676,1684]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8907F05EE75F89" box="[1178,1451,1676,1693]" gridcol="4" gridrow="18" pageId="6" pageNumber="430">120.2 ± 11.2</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D07DE5EE75FA0" box="[110,1451,1698,1716]" gridrow="19" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D07DE5B825FA0" box="[110,206,1698,1716]" gridcol="0" gridrow="19" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D07D95BCE5FA7" bold="true" box="[110,130,1701,1715]" pageId="6" pageNumber="430">17</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3007DE5AF25FA0" box="[291,446,1698,1716]" gridcol="1" gridrow="19" pageId="6" pageNumber="430">10</td>
|
||
<td id="C3305DC9FFD6D79AB80007DE59BE5FA0" box="[531,754,1698,1716]" gridcol="2" gridrow="19" pageId="6" pageNumber="430">107.0 ± 11.0</td>
|
||
<td id="C3305DC9FFD6D79AB95407DE5F095FA0" box="[839,1093,1698,1716]" gridcol="3" gridrow="19" pageId="6" pageNumber="430">
|
||
75.9 ± 3.5
|
||
<emphasis id="0CA5EAE5FFD62863B98707DE58ED5FBE" bold="true" box="[916,929,1698,1706]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8907DE5EE75FA0" box="[1178,1451,1698,1716]" gridcol="4" gridrow="19" pageId="6" pageNumber="430">
|
||
75.6 ± 7.2
|
||
<emphasis id="0CA5EAE5FFD62863BEFB07DE5FB95FBE" bold="true" box="[1256,1269,1698,1706]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D07C55EE75FDE" box="[110,1451,1721,1738]" gridrow="20" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D07C55B825FDE" box="[110,206,1721,1738]" gridcol="0" gridrow="20" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D07C05BCE5FDE" bold="true" box="[110,130,1724,1738]" pageId="6" pageNumber="430">18</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3007C55AF25FDE" box="[291,446,1721,1738]" gridcol="1" gridrow="20" pageId="6" pageNumber="430">10</td>
|
||
<td id="C3305DC9FFD6D79AB80007C559BE5FDE" box="[531,754,1721,1738]" gridcol="2" gridrow="20" pageId="6" pageNumber="430">99.7 ± 1.9</td>
|
||
<td id="C3305DC9FFD6D79AB95407C55F095FDE" box="[839,1093,1721,1738]" gridcol="3" gridrow="20" pageId="6" pageNumber="430">
|
||
72.0 ± 12.4
|
||
<emphasis id="0CA5EAE5FFD62863B98D07C558E75FD5" bold="true" box="[926,939,1721,1729]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8907C55EE75FDE" box="[1178,1451,1721,1738]" gridcol="4" gridrow="20" pageId="6" pageNumber="430">
|
||
81.9 ± 11.9
|
||
<emphasis id="0CA5EAE5FFD62863BEE107C55FB35FD5" bold="true" box="[1266,1279,1721,1729]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D07AC5EE75FF5" box="[110,1451,1744,1761]" gridrow="21" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D07AC5B825FF5" box="[110,206,1744,1761]" gridcol="0" gridrow="21" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D07AF5BCE5FF5" bold="true" box="[110,130,1747,1761]" pageId="6" pageNumber="430">19</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3007AC5AF25FF5" box="[291,446,1744,1761]" gridcol="1" gridrow="21" pageId="6" pageNumber="430">40</td>
|
||
<td id="C3305DC9FFD6D79AB80007AC59BE5FF5" box="[531,754,1744,1761]" gridcol="2" gridrow="21" pageId="6" pageNumber="430">99.7 ± 1.9</td>
|
||
<td id="C3305DC9FFD6D79AB95407AC5F095FF5" box="[839,1093,1744,1761]" gridcol="3" gridrow="21" pageId="6" pageNumber="430">
|
||
91.8 ± 7.8
|
||
<emphasis id="0CA5EAE5FFD62863B98707AC58ED5FCC" bold="true" box="[916,929,1744,1752]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8907AC5EE75FF5" box="[1178,1451,1744,1761]" gridcol="4" gridrow="21" pageId="6" pageNumber="430">
|
||
91.0 ± 10.8
|
||
<emphasis id="0CA5EAE5FFD62863BEE207AC5FB45FCC" bold="true" box="[1265,1272,1744,1752]" italics="true" pageId="6" pageNumber="430">⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D079B5EE75FEC" box="[110,1451,1767,1784]" gridrow="22" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D079B5B825FEC" box="[110,206,1767,1784]" gridcol="0" gridrow="22" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D07965BCE5FEC" bold="true" box="[110,130,1770,1784]" pageId="6" pageNumber="430">20</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB30079B5AF25FEC" box="[291,446,1767,1784]" gridcol="1" gridrow="22" pageId="6" pageNumber="430">80</td>
|
||
<td id="C3305DC9FFD6D79AB800079B59BE5FEC" box="[531,754,1767,1784]" gridcol="2" gridrow="22" pageId="6" pageNumber="430">103.4 ± 7.2</td>
|
||
<td id="C3305DC9FFD6D79AB954079B5F095FEC" box="[839,1093,1767,1784]" gridcol="3" gridrow="22" pageId="6" pageNumber="430">
|
||
90.6 ± 3.5
|
||
<emphasis id="0CA5EAE5FFD62863B987079B58ED5FFB" bold="true" box="[916,929,1767,1775]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE89079B5EE75FEC" box="[1178,1451,1767,1784]" gridcol="4" gridrow="22" pageId="6" pageNumber="430">
|
||
144.3 ± 4.8
|
||
<emphasis id="0CA5EAE5FFD62863BEE1079B5FB55FFB" bold="true" box="[1266,1273,1767,1775]" italics="true" pageId="6" pageNumber="430">⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D07825EE75E1B" box="[110,1451,1790,1807]" gridrow="23" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D07825B825E1B" box="[110,206,1790,1807]" gridcol="0" gridrow="23" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D067C5BCE5E1A" bold="true" box="[110,130,1792,1806]" pageId="6" pageNumber="430">21</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB3007825AF25E1B" box="[291,446,1790,1807]" gridcol="1" gridrow="23" pageId="6" pageNumber="430">40</td>
|
||
<td id="C3305DC9FFD6D79AB800078259BE5E1B" box="[531,754,1790,1807]" gridcol="2" gridrow="23" pageId="6" pageNumber="430">95.2 ± 3.4</td>
|
||
<td id="C3305DC9FFD6D79AB95407825F095E1B" box="[839,1093,1790,1807]" gridcol="3" gridrow="23" pageId="6" pageNumber="430">
|
||
64.6 ± 8.9
|
||
<emphasis id="0CA5EAE5FFD62863B987078258ED5E12" bold="true" box="[916,929,1790,1798]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8907825EE75E1B" box="[1178,1451,1790,1807]" gridcol="4" gridrow="23" pageId="6" pageNumber="430">
|
||
72.2 ± 7.5
|
||
<emphasis id="0CA5EAE5FFD62863BEFB07825FB95E12" bold="true" box="[1256,1269,1790,1798]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D066B5EE75E32" box="[110,1451,1815,1830]" gridrow="24" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D066B5B825E32" box="[110,206,1815,1830]" gridcol="0" gridrow="24" pageId="6" pageNumber="430">
|
||
<emphasis id="0CA5EAE5FFD62863BA7D066B5BCE5E31" bold="true" box="[110,130,1815,1829]" pageId="6" pageNumber="430">22</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD6D79ABB30066B5AF25E32" box="[291,446,1815,1830]" gridcol="1" gridrow="24" pageId="6" pageNumber="430">80</td>
|
||
<td id="C3305DC9FFD6D79AB800066B59BE5E32" box="[531,754,1815,1830]" gridcol="2" gridrow="24" pageId="6" pageNumber="430">98.5 ± 1.6</td>
|
||
<td id="C3305DC9FFD6D79AB954066B5F095E32" box="[839,1093,1815,1830]" gridcol="3" gridrow="24" pageId="6" pageNumber="430">108.5 ± 12.4</td>
|
||
<td id="C3305DC9FFD6D79ABE89066B5EE75E32" box="[1178,1451,1815,1830]" gridcol="4" gridrow="24" pageId="6" pageNumber="430">118.1 ± 11.3</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D06575EE75E29" box="[110,1451,1835,1853]" gridrow="25" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D06575B825E29" box="[110,206,1835,1853]" gridcol="0" gridrow="25" pageId="6" pageNumber="430">Arbutin c</th>
|
||
<td id="C3305DC9FFD6D79ABB3006575AF25E29" box="[291,446,1835,1853]" gridcol="1" gridrow="25" pageId="6" pageNumber="430">300</td>
|
||
<td id="C3305DC9FFD6D79AB800065759BE5E29" box="[531,754,1835,1853]" gridcol="2" gridrow="25" pageId="6" pageNumber="430">100.4 ± 0.7</td>
|
||
<td id="C3305DC9FFD6D79AB95406575F095E29" box="[839,1093,1835,1853]" gridcol="3" gridrow="25" pageId="6" pageNumber="430">
|
||
76.4 ± 6.3
|
||
<emphasis id="0CA5EAE5FFD62863B987065758ED5E27" bold="true" box="[916,929,1835,1843]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE8906575EE75E29" box="[1178,1451,1835,1853]" gridcol="4" gridrow="25" pageId="6" pageNumber="430">
|
||
73.8 ± 5.4
|
||
<emphasis id="0CA5EAE5FFD62863BEFB06575FB95E27" bold="true" box="[1256,1269,1835,1843]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD6D79ABA7D063D5EE75E47" box="[110,1451,1857,1875]" gridrow="26" pageId="6" pageNumber="430">
|
||
<th id="C3305DC9FFD6D79ABA7D063D5B825E47" box="[110,206,1857,1875]" gridcol="0" gridrow="26" pageId="6" pageNumber="430">Kojic acid c</th>
|
||
<td id="C3305DC9FFD6D79ABB30063D5AF25E47" box="[291,446,1857,1875]" gridcol="1" gridrow="26" pageId="6" pageNumber="430">300</td>
|
||
<td id="C3305DC9FFD6D79AB800063D59BE5E47" box="[531,754,1857,1875]" gridcol="2" gridrow="26" pageId="6" pageNumber="430">98.9 ± 1.1</td>
|
||
<td id="C3305DC9FFD6D79AB954063D5F095E47" box="[839,1093,1857,1875]" gridcol="3" gridrow="26" pageId="6" pageNumber="430">
|
||
85.8 ± 6.8
|
||
<emphasis id="0CA5EAE5FFD62863B987063E58ED5E5E" bold="true" box="[916,929,1858,1866]" italics="true" pageId="6" pageNumber="430">⁄⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD6D79ABE89063D5EE75E47" box="[1178,1451,1857,1875]" gridcol="4" gridrow="26" pageId="6" pageNumber="430">81.1 ± 13.7⁄⁄</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<tableNote id="C3373779FFD62863BA4406105BB75EC1" pageId="6" pageNumber="430" targetBox="[110,1451,1252,1875]" targetPageId="6">
|
||
<paragraph id="3E6E36F7FFD62863BA4406105F6E5E85" blockId="6.[87,1474,1896,2005]" pageId="6" pageNumber="430">
|
||
Nd: not determined due to being inactive in mushroom tyrosinase inhibition or limited yield. Data represents the mean ± S.D. (
|
||
<emphasis id="0CA5EAE5FFD62863BE9206175FC75E6E" box="[1153,1163,1899,1914]" italics="true" pageId="6" pageNumber="430">n</emphasis>
|
||
= 3–6). (
|
||
<superScript id="C9A49BBFFFD62863BEC706145F915E65" attach="none" box="[1236,1245,1896,1905]" fontSize="4" pageId="6" pageNumber="430">#</superScript>
|
||
) <0.05 indicates significant differences from the control group. (
|
||
<emphasis id="0CA5EAE5FFD62863BB9306FC5ACB5E9C" bold="true" box="[384,391,1920,1928]" italics="true" pageId="6" pageNumber="430">
|
||
<superScript id="C9A49BBFFFD62863BB9306FC5ACB5E9C" attach="none" box="[384,391,1920,1928]" fontSize="4" pageId="6" pageNumber="430">⁄</superScript>
|
||
</emphasis>
|
||
) <0.05,
|
||
<emphasis id="0CA5EAE5FFD62863BBDF06FC5A955E9C" bold="true" box="[460,473,1920,1928]" italics="true" pageId="6" pageNumber="430">
|
||
<superScript id="C9A49BBFFFD62863BBDF06FC5A955E9C" attach="right" box="[460,473,1920,1928]" fontSize="4" pageId="6" pageNumber="430">⁄⁄</superScript>
|
||
</emphasis>
|
||
<emphasis id="0CA5EAE5FFD62863BBCA06FE5AAF5E85" box="[473,483,1922,1937]" italics="true" pageId="6" pageNumber="430">p</emphasis>
|
||
<0.01 indicates significant differences from the OE- MSH treated group.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD62863BA7406EA59CE5EBC" blockId="6.[87,1474,1896,2005]" box="[103,642,1942,1960]" pageId="6" pageNumber="430">
|
||
<superScript id="C9A49BBFFFD62863BA7406EA5B225E8B" attach="left" box="[103,110,1942,1951]" fontSize="4" pageId="6" pageNumber="430">a</superScript>
|
||
Effect of compounds on cell viability of B16F10 melanoma cells.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD62863BA7506D15F265EAB" blockId="6.[87,1474,1896,2005]" box="[102,1130,1965,1984]" pageId="6" pageNumber="430">
|
||
<superScript id="C9A49BBFFFD62863BA7506D15B215EA3" attach="left" box="[102,109,1965,1975]" fontSize="4" pageId="6" pageNumber="430">b</superScript>
|
||
The inhibitory effect on melanin production and tyrosinase activity in B16F10 melanoma cells stimulated by 50 nM OE- MSH.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD62863BA7406B85BB75EC1" blockId="6.[87,1474,1896,2005]" box="[103,251,1988,2005]" pageId="6" pageNumber="430">
|
||
<superScript id="C9A49BBFFFD62863BA7406B85B215ED9" attach="left" box="[103,109,1988,1997]" fontSize="4" pageId="6" pageNumber="430">c</superScript>
|
||
Positive control.
|
||
</paragraph>
|
||
</tableNote>
|
||
<caption id="6AAE667FFFD72862BA6101CB5AC259E6" ID-Table-UUID="6AAE667FFFD72862BA6101CB5AC259E6" httpUri="http://table.plazi.org/id/6AAE667FFFD72862BA6101CB5AC259E6" pageId="7" pageNumber="431" startId="7.[114,158,183,197]" targetBox="[136,721,267,543]" targetIsTable="true" targetPageId="7" targetType="table">
|
||
<paragraph id="3E6E36F7FFD72862BA6101CB5BE259D1" blockId="7.[113,783,183,242]" box="[114,174,183,197]" pageId="7" pageNumber="431">
|
||
<emphasis id="0CA5EAE5FFD72862BA6101CB5BE259D1" bold="true" box="[114,174,183,197]" pageId="7" pageNumber="431">Table 5</emphasis>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD72862BA6201B25AC259E6" blockId="7.[113,783,183,242]" pageId="7" pageNumber="431">Effect of selected compounds on melanin content, tyrosinase activity, and cell viability in B16F10 melanoma cells.</paragraph>
|
||
</caption>
|
||
<paragraph id="3E6E36F7FFD72862BA9B007759F05B02" pageId="7" pageNumber="431">
|
||
<table id="4CD1C457FFD7D79ABA9B0077599D5B0B" box="[136,721,267,543]" gridcols="5" gridrows="10" pageId="7" pageNumber="431">
|
||
<tr id="80E134B5FFD7D79ABA9B0077599D5852" box="[136,721,267,326]" gridrow="0" pageId="7" pageNumber="431">
|
||
<th id="C3305DC9FFD7D79ABA9B00775BA45852" box="[136,232,267,326]" gridcol="0" gridrow="0" pageId="7" pageNumber="431">Compounds</th>
|
||
<th id="C3305DC9FFD7D79ABAEC00775A685852" box="[255,292,267,326]" gridcol="1" gridrow="0" pageId="7" pageNumber="431">Con. (µµ)</th>
|
||
<th id="C3305DC9FFD7D79ABB2D00775AFD5852" box="[318,433,267,326]" gridcol="2" gridrow="0" pageId="7" pageNumber="431">Cell viability (% of control)a</th>
|
||
<th id="C3305DC9FFD7D79ABBD9007759035852" box="[458,591,267,326]" gridcol="3" gridrow="0" pageId="7" pageNumber="431">Melanin content (% of control)b</th>
|
||
<th id="C3305DC9FFD7D79AB87B0077599D5852" box="[616,721,267,326]" gridcol="4" gridrow="0" pageId="7" pageNumber="431">Tyrosinase activity (% of control)b</th>
|
||
</tr>
|
||
<tr id="80E134B5FFD7D79ABA9B0026599D587C" box="[136,721,346,360]" gridrow="1" pageId="7" pageNumber="431" rowspan-1="1">
|
||
<th id="C3305DC9FFD7D79ABA9B00265BA4587C" box="[136,232,346,360]" gridcol="0" gridrow="1" pageId="7" pageNumber="431">Control</th>
|
||
<td id="C3305DC9FFD7D79ABB2D00265AFD587C" box="[318,433,346,360]" gridcol="2" gridrow="1" pageId="7" pageNumber="431">100.0 ± 1.7</td>
|
||
<td id="C3305DC9FFD7D79ABBD900265903587C" box="[458,591,346,360]" gridcol="3" gridrow="1" pageId="7" pageNumber="431">100.0 ± 2.5</td>
|
||
<td id="C3305DC9FFD7D79AB87B0026599D587C" box="[616,721,346,360]" gridcol="4" gridrow="1" pageId="7" pageNumber="431">100.0 ± 1.2</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD7D79ABA9B0011599D5894" box="[136,721,365,384]" gridrow="2" pageId="7" pageNumber="431" rowspan-1="1">
|
||
<th id="C3305DC9FFD7D79ABA9B00115BA45894" box="[136,232,365,384]" gridcol="0" gridrow="2" pageId="7" pageNumber="431">OE- MSH</th>
|
||
<td id="C3305DC9FFD7D79ABB2D00115AFD5894" box="[318,433,365,384]" gridcol="2" gridrow="2" pageId="7" pageNumber="431">nd</td>
|
||
<td id="C3305DC9FFD7D79ABBD9001159035894" box="[458,591,365,384]" gridcol="3" gridrow="2" pageId="7" pageNumber="431">121.1 ± 11.5 #</td>
|
||
<td id="C3305DC9FFD7D79AB87B0011599D5894" box="[616,721,365,384]" gridcol="4" gridrow="2" pageId="7" pageNumber="431">120.5 ± 4.3 #</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD7D79ABA9B00F9599D5882" box="[136,721,389,406]" gridrow="3" pageId="7" pageNumber="431">
|
||
<th id="C3305DC9FFD7D79ABA9B00F95BA45882" box="[136,232,389,406]" gridcol="0" gridrow="3" pageId="7" pageNumber="431">
|
||
<emphasis id="0CA5EAE5FFD72862BA9B00F45BD05882" bold="true" box="[136,156,392,406]" pageId="7" pageNumber="431">12</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD7D79ABAEC00F95A685882" box="[255,292,389,406]" gridcol="1" gridrow="3" pageId="7" pageNumber="431">10</td>
|
||
<td id="C3305DC9FFD7D79ABB2D00F95AFD5882" box="[318,433,389,406]" gridcol="2" gridrow="3" pageId="7" pageNumber="431">101.0 ± 1.7</td>
|
||
<td id="C3305DC9FFD7D79ABBD900F959035882" box="[458,591,389,406]" gridcol="3" gridrow="3" pageId="7" pageNumber="431">
|
||
105.7 ± 2.3
|
||
<emphasis id="0CA5EAE5FFD72862B83100F959655899" bold="true" box="[546,553,389,397]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD7D79AB87B00F9599D5882" box="[616,721,389,406]" gridcol="4" gridrow="3" pageId="7" pageNumber="431">
|
||
137.2 ± 6.1
|
||
<emphasis id="0CA5EAE5FFD72862B8AC00F9598A5899" bold="true" box="[703,710,389,397]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD7D79ABA9B00E0599D58B9" box="[136,721,412,429]" gridrow="4" pageId="7" pageNumber="431">
|
||
<th id="C3305DC9FFD7D79ABA9B00E05BA458B9" box="[136,232,412,429]" gridcol="0" gridrow="4" pageId="7" pageNumber="431">
|
||
<emphasis id="0CA5EAE5FFD72862BA9B00E25BD058B8" bold="true" box="[136,156,414,428]" pageId="7" pageNumber="431">16</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD7D79ABAEC00E05A6858B9" box="[255,292,412,429]" gridcol="1" gridrow="4" pageId="7" pageNumber="431">10</td>
|
||
<td id="C3305DC9FFD7D79ABB2D00E05AFD58B9" box="[318,433,412,429]" gridcol="2" gridrow="4" pageId="7" pageNumber="431">93.9 ± 9.5</td>
|
||
<td id="C3305DC9FFD7D79ABBD900E0590358B9" box="[458,591,412,429]" gridcol="3" gridrow="4" pageId="7" pageNumber="431">
|
||
101.0 ± 8.0
|
||
<emphasis id="0CA5EAE5FFD72862B83200E0596458B0" bold="true" box="[545,552,412,420]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD7D79AB87B00E0599D58B9" box="[616,721,412,429]" gridcol="4" gridrow="4" pageId="7" pageNumber="431">117.8 ± 8.5</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD7D79ABA9B00CF599D58D0" box="[136,721,435,452]" gridrow="5" pageId="7" pageNumber="431">
|
||
<th id="C3305DC9FFD7D79ABA9B00CF5BA458D0" box="[136,232,435,452]" gridcol="0" gridrow="5" pageId="7" pageNumber="431">
|
||
<emphasis id="0CA5EAE5FFD72862BA9B00C95BD058D7" bold="true" box="[136,156,437,451]" pageId="7" pageNumber="431">17</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD7D79ABAEC00CF5A6858D0" box="[255,292,435,452]" gridcol="1" gridrow="5" pageId="7" pageNumber="431">10</td>
|
||
<td id="C3305DC9FFD7D79ABB2D00CF5AFD58D0" box="[318,433,435,452]" gridcol="2" gridrow="5" pageId="7" pageNumber="431">107.0 ± 11.0</td>
|
||
<td id="C3305DC9FFD7D79ABBD900CF590358D0" box="[458,591,435,452]" gridcol="3" gridrow="5" pageId="7" pageNumber="431">
|
||
76.3 ± 2.9
|
||
<emphasis id="0CA5EAE5FFD72862B80B00CF595358AF" bold="true" box="[536,543,435,443]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD7D79AB87B00CF599D58D0" box="[616,721,435,452]" gridcol="4" gridrow="5" pageId="7" pageNumber="431">
|
||
75.2 ± 8.8
|
||
<emphasis id="0CA5EAE5FFD72862B8A600CF59F058AF" bold="true" box="[693,700,435,443]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD7D79ABA9B00B5599D58CF" box="[136,721,457,475]" gridrow="6" pageId="7" pageNumber="431">
|
||
<th id="C3305DC9FFD7D79ABA9B00B55BA458CF" box="[136,232,457,475]" gridcol="0" gridrow="6" pageId="7" pageNumber="431">
|
||
<emphasis id="0CA5EAE5FFD72862BA9B00B05BD058CE" bold="true" box="[136,156,460,474]" pageId="7" pageNumber="431">18</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD7D79ABAEC00B55A6858CF" box="[255,292,457,475]" gridcol="1" gridrow="6" pageId="7" pageNumber="431">10</td>
|
||
<td id="C3305DC9FFD7D79ABB2D00B55AFD58CF" box="[318,433,457,475]" gridcol="2" gridrow="6" pageId="7" pageNumber="431">99.7 ± 1.9</td>
|
||
<td id="C3305DC9FFD7D79ABBD900B5590358CF" box="[458,591,457,475]" gridcol="3" gridrow="6" pageId="7" pageNumber="431">
|
||
70.8 ± 1.5
|
||
<emphasis id="0CA5EAE5FFD72862B80B00B5595358C5" bold="true" box="[536,543,457,465]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD7D79AB87B00B5599D58CF" box="[616,721,457,475]" gridcol="4" gridrow="6" pageId="7" pageNumber="431">
|
||
88.7 ± 10.1
|
||
<emphasis id="0CA5EAE5FFD72862B8AC00B5598A58C5" bold="true" box="[703,710,457,465]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD7D79ABA9B009C599D58E5" box="[136,721,480,497]" gridrow="7" pageId="7" pageNumber="431">
|
||
<th id="C3305DC9FFD7D79ABA9B009C5BA458E5" box="[136,232,480,497]" gridcol="0" gridrow="7" pageId="7" pageNumber="431">
|
||
<emphasis id="0CA5EAE5FFD72862BA9B009F5BD058E5" bold="true" box="[136,156,483,497]" pageId="7" pageNumber="431">19</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD7D79ABAEC009C5A6858E5" box="[255,292,480,497]" gridcol="1" gridrow="7" pageId="7" pageNumber="431">40</td>
|
||
<td id="C3305DC9FFD7D79ABB2D009C5AFD58E5" box="[318,433,480,497]" gridcol="2" gridrow="7" pageId="7" pageNumber="431">99.7 ± 1.9</td>
|
||
<td id="C3305DC9FFD7D79ABBD9009C590358E5" box="[458,591,480,497]" gridcol="3" gridrow="7" pageId="7" pageNumber="431">
|
||
92.0 ± 15.2
|
||
<emphasis id="0CA5EAE5FFD72862B831009C596558FC" bold="true" box="[546,553,480,488]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD7D79AB87B009C599D58E5" box="[616,721,480,497]" gridcol="4" gridrow="7" pageId="7" pageNumber="431">
|
||
89.2 ± 6.8
|
||
<emphasis id="0CA5EAE5FFD72862B8A6009C59F058FC" bold="true" box="[693,700,480,488]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD7D79ABA9B0086599D5B1C" box="[136,721,506,520]" gridrow="8" pageId="7" pageNumber="431">
|
||
<th id="C3305DC9FFD7D79ABA9B00865BA45B1C" box="[136,232,506,520]" gridcol="0" gridrow="8" pageId="7" pageNumber="431">
|
||
<emphasis id="0CA5EAE5FFD72862BA9B00865BD05B1C" bold="true" box="[136,156,506,520]" pageId="7" pageNumber="431">20</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD7D79ABAEC00865A685B1C" box="[255,292,506,520]" gridcol="1" gridrow="8" pageId="7" pageNumber="431">40</td>
|
||
<td id="C3305DC9FFD7D79ABB2D00865AFD5B1C" box="[318,433,506,520]" gridcol="2" gridrow="8" pageId="7" pageNumber="431">99.7 ± 9.4</td>
|
||
<td id="C3305DC9FFD7D79ABBD9008659035B1C" box="[458,591,506,520]" gridcol="3" gridrow="8" pageId="7" pageNumber="431">107.4 ± 10.7</td>
|
||
<td id="C3305DC9FFD7D79AB87B0086599D5B1C" box="[616,721,506,520]" gridcol="4" gridrow="8" pageId="7" pageNumber="431">127.6 ± 3.6</td>
|
||
</tr>
|
||
<tr id="80E134B5FFD7D79ABA9B0372599D5B0B" box="[136,721,526,543]" gridrow="9" pageId="7" pageNumber="431">
|
||
<th id="C3305DC9FFD7D79ABA9B03725BA45B0B" box="[136,232,526,543]" gridcol="0" gridrow="9" pageId="7" pageNumber="431">
|
||
<emphasis id="0CA5EAE5FFD72862BA9B036D5BD05B0B" bold="true" box="[136,156,529,543]" pageId="7" pageNumber="431">21</emphasis>
|
||
</th>
|
||
<td id="C3305DC9FFD7D79ABAEC03725A685B0B" box="[255,292,526,543]" gridcol="1" gridrow="9" pageId="7" pageNumber="431">40</td>
|
||
<td id="C3305DC9FFD7D79ABB2D03725AFD5B0B" box="[318,433,526,543]" gridcol="2" gridrow="9" pageId="7" pageNumber="431">95.2 ± 3.4</td>
|
||
<td id="C3305DC9FFD7D79ABBD9037259035B0B" box="[458,591,526,543]" gridcol="3" gridrow="9" pageId="7" pageNumber="431">
|
||
58.0 ± 2.2
|
||
<emphasis id="0CA5EAE5FFD72862B80B037259535B02" bold="true" box="[536,543,526,534]" italics="true" pageId="7" pageNumber="431">⁄</emphasis>
|
||
</td>
|
||
<td id="C3305DC9FFD7D79AB87B0372599D5B0B" box="[616,721,526,543]" gridcol="4" gridrow="9" pageId="7" pageNumber="431">69.2 ± 4.0⁄</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<tableNote id="C3373779FFD72862BA6203445AA85BAC" pageId="7" pageNumber="431" targetBox="[136,721,267,543]" targetPageId="7">
|
||
<paragraph id="3E6E36F7FFD72862BA620344595E5B67" blockId="7.[113,783,564,697]" pageId="7" pageNumber="431">
|
||
Nd: not determined. Data represents the mean ± S.D. (
|
||
<emphasis id="0CA5EAE5FFD72862B83F034B597A5B52" box="[556,566,567,582]" italics="true" pageId="7" pageNumber="431">n</emphasis>
|
||
= 3–6). (
|
||
<superScript id="C9A49BBFFFD72862B86E034859CA5B29" attach="none" box="[637,646,564,573]" fontSize="4" pageId="7" pageNumber="431">#</superScript>
|
||
) <0.05 indicates significant differences from the control group. (
|
||
<emphasis id="0CA5EAE5FFD72862B811033759455B47" bold="true" box="[514,521,587,595]" italics="true" pageId="7" pageNumber="431">
|
||
<superScript id="C9A49BBFFFD72862B811033759455B47" attach="none" box="[514,521,587,595]" fontSize="4" pageId="7" pageNumber="431">⁄</superScript>
|
||
</emphasis>
|
||
) <0.05,
|
||
<superScript id="C9A49BBFFFD72862B843033659175B40" attach="right" box="[592,603,586,596]" fontSize="4" pageId="7" pageNumber="431">**</superScript>
|
||
<emphasis id="0CA5EAE5FFD72862B848033259295B49" box="[603,613,590,605]" italics="true" pageId="7" pageNumber="431">p</emphasis>
|
||
<0.01 indicates significant differences from the OE- MSH treated group.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD72862BA92030459D05B9E" blockId="7.[113,783,564,697]" box="[129,668,632,650]" pageId="7" pageNumber="431">
|
||
<superScript id="C9A49BBFFFD72862BA9203045BC45B95" attach="left" box="[129,136,632,641]" fontSize="4" pageId="7" pageNumber="431">a</superScript>
|
||
Effect of compounds on cell viability of B16F10 melanoma cells.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD72862BA9303F35AA85BAC" blockId="7.[113,783,564,697]" pageId="7" pageNumber="431">
|
||
<superScript id="C9A49BBFFFD72862BA9303F35BCB5B8D" attach="right" box="[128,135,655,665]" fontSize="4" pageId="7" pageNumber="431">b</superScript>
|
||
The inhibitory effect on melanin production and tyrosinase activity in B16F10 melanoma cells stimulated by 50 nM OE- MSH.
|
||
</paragraph>
|
||
</tableNote>
|
||
<paragraph id="3E6E36F7FFD72862BA6202595AFD5D26" blockId="7.[113,784,805,1074]" pageId="7" pageNumber="431">
|
||
quantify their effect on viability (cell viability details are shown in the Supporting Information). Compounds
|
||
<emphasis id="0CA5EAE5FFD72862B807023C59775A40" bold="true" box="[532,571,832,852]" pageId="7" pageNumber="431">6–7</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B856023C593B5A47" bold="true" box="[581,631,832,852]" pageId="7" pageNumber="431">9–10</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B891023C59D75A47" bold="true" box="[642,667,832,851]" pageId="7" pageNumber="431">13</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B8B5023C59895A47" bold="true" box="[678,709,832,851]" pageId="7" pageNumber="431">20,</emphasis>
|
||
and
|
||
<emphasis id="0CA5EAE5FFD72862B8E6023C58425A47" bold="true" box="[757,782,832,851]" pageId="7" pageNumber="431">22</emphasis>
|
||
had no significant effect on B16–F10 melanoma cell proliferation at concentrations up to 80 µM (
|
||
<tableCitation id="7353034CFFD72862BB8802045AA95A9F" box="[411,485,888,907]" captionStart="Table 4" captionStartId="6.[87,131,1195,1209]" captionTargetPageId="6" captionText="Table 4 Effect of compounds isolated from A. xanthocarpus on melanin content, tyrosinase activity, and cell viability of B16F10 melanoma cells." httpUri="http://table.plazi.org/id/6AAE667FFFD62863BA4405D75FC15DC4" pageId="7" pageNumber="431" tableUuid="6AAE667FFFD62863BA4405D75FC15DC4">Table 4</tableCitation>
|
||
). Compounds
|
||
<emphasis id="0CA5EAE5FFD72862B86B020459D35A9F" bold="true" box="[632,671,888,908]" pageId="7" pageNumber="431">3–4</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B8B9020459FB5A9F" bold="true" box="[682,695,888,907]" pageId="7" pageNumber="431">8</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B8D0020459905A9F" bold="true" box="[707,732,888,907]" pageId="7" pageNumber="431">12</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B8FA02045BDC5AB3" bold="true" pageId="7" pageNumber="431">16– 17,</emphasis>
|
||
and
|
||
<emphasis id="0CA5EAE5FFD72862BAD402E85BAC5AB3" bold="true" box="[199,224,916,935]" pageId="7" pageNumber="431">18</emphasis>
|
||
did not affect cell viability at low concentrations (10 or 20 µM). Compound
|
||
<emphasis id="0CA5EAE5FFD72862BB4E02CC5A3A5AD7" bold="true" box="[349,374,944,963]" pageId="7" pageNumber="431">15</emphasis>
|
||
reduced cell viability to 75% at 10 µM, and it was therefore deemed unsuitable for further evaluation. Based on these data, the effects of each compound on melanoma cells were evaluated at non-toxic concentrations in the subsequently described experiments.
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD72862BA6105FA59EC5DA1" blockId="7.[113,770,1158,1205]" pageId="7" pageNumber="431">
|
||
<emphasis id="0CA5EAE5FFD72862BA6105FA59EC5DA1" italics="true" pageId="7" pageNumber="431">
|
||
2.5. Effects of compounds isolated from
|
||
<taxonomicName id="F9D14D74FFD72862BBE005FA59C25D8E" box="[499,654,1158,1178]" class="Magnoliopsida" family="Moraceae" genus="Artocarpus" kingdom="Plantae" order="Rosales" pageId="7" pageNumber="431" phylum="Tracheophyta" rank="species" species="xanthocarpus">A. xanthocarpus</taxonomicName>
|
||
on melanin
|
||
<heading id="6526819BFFD72862BA6205DD59EC5DA1" box="[113,672,1185,1205]" fontSize="8" level="3" pageId="7" pageNumber="431" reason="8">content and tyrosinase activity in B16F10 melanoma cells</heading>
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="3E6E36F7FFD72862BA8205A758BC59F1" blockId="7.[113,784,1242,2015]" lastBlockId="7.[831,1500,182,229]" pageId="7" pageNumber="431">
|
||
To determine the inhibitory effect of compounds on melanin formation and tyrosinase activity, B16F10 melanoma cells were stimulated with 50 nM OE- melanocyte-stimulating hormone (OE- MSH) for 24 h and were then treated with either a vehicle or the compounds at concentrations known to be non-toxic. Importantly, compounds
|
||
<emphasis id="0CA5EAE5FFD72862BB61041A5AD45C6D" bold="true" box="[370,408,1382,1401]" pageId="7" pageNumber="431">1–4</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862BBB7041A5A865C6D" bold="true" box="[420,458,1382,1401]" pageId="7" pageNumber="431">7–8</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862BBC5041A5AA35C6D" bold="true" box="[470,495,1382,1401]" pageId="7" pageNumber="431">10</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862BBE8041A59585C6D" bold="true" box="[507,532,1382,1401]" pageId="7" pageNumber="431">14</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD72862B85E041A59C05C6D" bold="true" box="[589,652,1382,1401]" pageId="7" pageNumber="431">16–21</emphasis>
|
||
significantly decreased melanin production compared to cells treated with OE- MSH alone (
|
||
<tableCitation id="7353034CFFD72862BAFC04E25A755CA5" box="[239,313,1438,1457]" captionStart="Table 4" captionStartId="6.[87,131,1195,1209]" captionTargetPageId="6" captionText="Table 4 Effect of compounds isolated from A. xanthocarpus on melanin content, tyrosinase activity, and cell viability of B16F10 melanoma cells." httpUri="http://table.plazi.org/id/6AAE667FFFD62863BA4405D75FC15DC4" pageId="7" pageNumber="431" tableUuid="6AAE667FFFD62863BA4405D75FC15DC4">Table 4</tableCitation>
|
||
). Among these, compounds
|
||
<emphasis id="0CA5EAE5FFD72862B84904E159CD5CA4" bold="true" box="[602,641,1437,1457]" pageId="7" pageNumber="431">1–4</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B89F04E159D55CA4" bold="true" box="[652,665,1437,1456]" pageId="7" pageNumber="431">8</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B8B604E159F25CA4" bold="true" box="[677,702,1437,1456]" pageId="7" pageNumber="431">14</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B8D804E159A85CA4" bold="true" box="[715,740,1437,1456]" pageId="7" pageNumber="431">17</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B8E304E158455CA4" bold="true" box="[752,777,1437,1456]" pageId="7" pageNumber="431">18</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD72862BA8C04C55BF45CD8" bold="true" box="[159,184,1465,1484]" pageId="7" pageNumber="431">21</emphasis>
|
||
significantly reduced melanin content to a level less than that observed for control-, OE- MSH-, or positive control-treated cells. Since compound
|
||
<emphasis id="0CA5EAE5FFD72862BB49048D5A3F5F10" bold="true" box="[346,371,1521,1540]" pageId="7" pageNumber="431">13</emphasis>
|
||
significantly increased melanin production and tyrosinase activity in cellular assays, it can be concluded that it is not a suitable anti-melanogenesis component. Compounds
|
||
<emphasis id="0CA5EAE5FFD72862BAE107395A545F4C" bold="true" box="[242,280,1605,1624]" pageId="7" pageNumber="431">1–2</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862BB3607395A7E5F4C" bold="true" box="[293,306,1605,1624]" pageId="7" pageNumber="431">4</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862BB2C07395A005F4C" bold="true" box="[319,332,1605,1624]" pageId="7" pageNumber="431">8</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862BB4907395AD55F4C" bold="true" box="[346,409,1605,1624]" pageId="7" pageNumber="431">17–19</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD72862BBC607395AA25F4C" bold="true" box="[469,494,1605,1624]" pageId="7" pageNumber="431">21</emphasis>
|
||
also significantly decreased the OE- MSH-induced stimulation of melanin biosynthesis, possibly through a mechanism that involves inhibition of tyrosinase activity. Interestingly, some compounds reduced the melanin content but increased tyrosinase activity (e.g.,
|
||
<emphasis id="0CA5EAE5FFD72862BBEA07C8595E5FD3" bold="true" box="[505,530,1716,1735]" pageId="7" pageNumber="431">10</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B80D07C8597B5FD3" bold="true" box="[542,567,1716,1735]" pageId="7" pageNumber="431">12</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B85707C859115FD3" bold="true" box="[580,605,1716,1735]" pageId="7" pageNumber="431">14</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD72862B88507C859E35FD3" bold="true" box="[662,687,1716,1735]" pageId="7" pageNumber="431">20</emphasis>
|
||
). Further experiments will be needed to clarify the mechanism of this activity. To quantitatively assess the importance of the prenyl moiety in anti-melanogenesis activity, several compounds with similar skeletons were evaluated in B16F10 cells at the same concentration. Among the flavonoids, the effects of compounds
|
||
<emphasis id="0CA5EAE5FFD72862B88E063C59FA5E47" bold="true" box="[669,694,1856,1875]" pageId="7" pageNumber="431">12</emphasis>
|
||
,
|
||
<emphasis id="0CA5EAE5FFD72862B8D0063C59905E47" bold="true" box="[707,732,1856,1875]" pageId="7" pageNumber="431">16</emphasis>
|
||
, and
|
||
<emphasis id="0CA5EAE5FFD72862BA6206205BC65E7B" bold="true" box="[113,138,1884,1903]" pageId="7" pageNumber="431">17</emphasis>
|
||
, which contain a resorcinol group in the B ring and varying numbers of prenyl groups, were evaluated at 10 µM. Among the stilbenoids, compounds
|
||
<emphasis id="0CA5EAE5FFD72862BB7906E85AE55EB3" bold="true" box="[362,425,1940,1959]" pageId="7" pageNumber="431">19–21</emphasis>
|
||
, with different numbers of hydroxy/prenyl groups, were evaluated at 40 µM. At the concentrations tested, compounds
|
||
<emphasis id="0CA5EAE5FFD72862BB5706B75A115ECA" bold="true" box="[324,349,1995,2014]" pageId="7" pageNumber="431">17</emphasis>
|
||
and
|
||
<emphasis id="0CA5EAE5FFD72862BB8D06B75AFB5ECA" bold="true" box="[414,439,1995,2014]" pageId="7" pageNumber="431">21</emphasis>
|
||
with a lipophilic prenyl group exhibited potent inhibition of melanin production and tyrosinase activity (
|
||
<tableCitation id="7353034CFFD72862B98A01AE58AF59F1" box="[921,995,210,229]" captionStart="Table 5" captionStartId="7.[114,158,183,197]" captionTargetPageId="7" captionText="Table 5 Effect of selected compounds on melanin content, tyrosinase activity, and cell viability in B16F10 melanoma cells." httpUri="http://table.plazi.org/id/6AAE667FFFD72862BA6101CB5AC259E6" pageId="7" pageNumber="431" tableUuid="6AAE667FFFD72862BA6101CB5AC259E6">Table 5</tableCitation>
|
||
).
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |