2391 lines
261 KiB
XML
2391 lines
261 KiB
XML
<document id="1FF290FFC82CDE48D13D0B812E284389" ID-DOI="10.1016/j.phytochem.2019.112181" ID-ISSN="1873-3700" ID-Zenodo-Dep="8160259" IM.illustrations_approvedBy="juliana" IM.tables_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1689690816695" checkinUser="felipe" docAuthor="Pham, Ha Thanh Tung, Ryu, Byeol, Cho, Hyo Moon, Lee, Ba-Wool, Yang, Woo Young, Park, Eun Jin, Tran, Van On & Oh, Won Keun" docDate="2020" docId="03C48791EF54FFAEFFEEFE45FD6BFB15" docLanguage="en" docName="Phytochemistry.170.112181.pdf" docOrigin="Phytochemistry (112181) 170" docSource="http://dx.doi.org/10.1016/j.phytochem.2019.112181" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.3:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="3" docTitle="Gymnema latifolium subsp. wall Wight" docType="treatment" docVersion="2" lastPageNumber="7" masterDocId="FFFDFFE9EF55FFA9FF8AFF96FFD6FF8B" masterDocTitle="Oleanane hemiacetal glycosides from Gymnema latifolium and their inhibitory effects on protein tyrosine phosphatase 1 B" masterLastPageNumber="112181" masterPageNumber="112181" pageNumber="2" updateTime="1689769133516" updateUser="ExternalLinkService">
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<mods:title id="F40CECEC4AD573AE2ECBF1783C19C5A7">Oleanane hemiacetal glycosides from Gymnema latifolium and their inhibitory effects on protein tyrosine phosphatase 1 B</mods:title>
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<mods:namePart id="82460D635D1391D51604BF5E0DBEC4BA">Pham, Ha Thanh Tung</mods:namePart>
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<mods:affiliation id="18D73EBE7E1BA293CF95993B8AFD1EB4">, Byeol Ryu &, Hyo Moon Cho &, Ba-Wool Lee &, Woo Young Yang &, &, Van On Tran & ∗ & Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 08826, Republic of Korea</mods:affiliation>
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<mods:namePart id="B051A2AD877E3672CEB292907AA0C832">Ryu, Byeol</mods:namePart>
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<mods:namePart id="0C9E721AF4B8438D5EA6FC7FF6CED618">Cho, Hyo Moon</mods:namePart>
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<mods:namePart id="3B96B06F43E4128E17AF0921E15119E5">Tran, Van On</mods:namePart>
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<mods:namePart id="CB73DCD20AC09AF98E9F8034330AF01C">Oh, Won Keun</mods:namePart>
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<mods:date id="D44F668515C50026A784D78283A4B94C">2020</mods:date>
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<mods:number id="1B7E6FD803FD4235D2778314788746AF">2020-02-29</mods:number>
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<mods:number id="2FB5FFC6987FAD3BD7B37090385447BA">170</mods:number>
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<mods:url id="07DBDDB8AAD98D2D4B55907232E24212">http://dx.doi.org/10.1016/j.phytochem.2019.112181</mods:url>
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<mods:classification id="5A933728FA94304947AD708635E44FBC">journal article</mods:classification>
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<mods:identifier id="AABB118D72C9B2134A9FDA1AABA3D10B" type="DOI">10.1016/j.phytochem.2019.112181</mods:identifier>
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<treatment id="03C48791EF54FFAEFFEEFE45FD6BFB15" ID-DOI="http://doi.org/10.5281/zenodo.8163777" ID-Zenodo-Dep="8163777" LSID="urn:lsid:plazi:treatment:03C48791EF54FFAEFFEEFE45FD6BFB15" httpUri="http://treatment.plazi.org/id/03C48791EF54FFAEFFEEFE45FD6BFB15" lastPageId="7" lastPageNumber="7" pageId="1" pageNumber="2">
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<subSubSection id="C377650CEF54FFA8FFEEFE45FDA5FE6D" box="[100,627,467,486]" pageId="1" pageNumber="2" type="nomenclature">
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<paragraph id="8BD23687EF54FFA8FFEEFE45FDA5FE6D" blockId="1.[100,627,467,486]" box="[100,627,467,486]" pageId="1" pageNumber="2">
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<heading id="D09A81EBEF54FFA8FFEEFE45FDA5FE6D" bold="true" box="[100,627,467,486]" fontSize="36" level="1" pageId="1" pageNumber="2" reason="1">
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<emphasis id="B919EA95EF54FFA8FFEEFE45FDA5FE6D" bold="true" box="[100,627,467,486]" italics="true" pageId="1" pageNumber="2">
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2.1. Authentication of
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<taxonomicName id="4C6D4D04EF54FFA8FEBEFE45FDA5FE6D" authority="Wall. ex Wight" authorityName="Wight" box="[308,627,467,486]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="subSpecies" species="latifolium" subSpecies="wall">Gymnema latifolium wall ex. Wight</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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<subSubSection id="C377650CEF54FFAEFF0FFD9DFD6BFB15" lastPageId="7" lastPageNumber="8" pageId="1" pageNumber="2" type="description">
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<paragraph id="8BD23687EF54FFA8FF0FFD9DFECAFA58" blockId="1.[100,771,523,1491]" pageId="1" pageNumber="2">
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The whole plant contains bright yellow latex and the lianas are up to
|
||
<quantity id="4C959B62EF54FFA8FFEEFDB1FF50FDB1" box="[100,134,551,570]" metricMagnitude="0" metricUnit="m" metricValue="6.0" pageId="1" pageNumber="2" unit="m" value="6.0">6 m</quantity>
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high. The stem was corky lenticellate, and old stem was changed basally wing-like corky. The young branchlets are yellowish green and densely pubescent, and stalks have densely hairy. Leaves opposite with broadly ovate is
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||
<quantity id="4C959B62EF54FFA8FE8DFDECFE80FD05" box="[263,342,634,654]" metricMagnitude="-1" metricUnit="m" metricValue="1.05" metricValueMax="1.3" metricValueMin="0.8" pageId="1" pageNumber="2" unit="cm" value="10.5" valueMax="13.0" valueMin="8.0">8–13 cm</quantity>
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×
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<quantity id="4C959B62EF54FFA8FEF9FDECFE6FFD05" box="[371,441,634,654]" metricMagnitude="-2" metricUnit="m" metricValue="6.5" metricValueMax="8.0" metricValueMin="5.0" pageId="1" pageNumber="2" unit="cm" value="6.5" valueMax="8.0" valueMin="5.0">5–8 cm</quantity>
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. Apex and base truncate have the rounded, and margin entire is orange-yellow pubescent abaxially with 5–7 lateral veins per side. Petiole with
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<quantity id="4C959B62EF54FFA8FD8CFD24FD8DFD4D" box="[518,603,690,710]" metricMagnitude="-2" metricUnit="m" metricValue="2.75" metricValueMax="4.0" metricValueMin="1.5" pageId="1" pageNumber="2" unit="cm" value="2.75" valueMax="4.0" valueMin="1.5">1.5–4 cm</quantity>
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long is densely pubescent. Inflorescences are paired at node, multi-flowered, umbrellashape cymes and pubescent. Flowers are yellow with
|
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<quantity id="4C959B62EF54FFA8FDDEFD7CFD5EFD76" box="[596,648,746,765]" metricMagnitude="-3" metricUnit="m" metricValue="3.0" pageId="1" pageNumber="2" unit="mm" value="3.0">3 mm</quantity>
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×
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<quantity id="4C959B62EF54FFA8FD2CFD7CFD0CFD76" box="[678,730,746,765]" metricMagnitude="-3" metricUnit="m" metricValue="3.0" pageId="1" pageNumber="2" unit="mm" value="3.0">3 mm</quantity>
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and corolla is a yellowish campanulate with a dense pubescent inside without glabrous. Gynostegium is concealed in corolla, slightly swollen base in cylindrical form, and has ten oval nectary patches. Pollinia is a oblong, erect and top enlargement, and ovary has dense pubescent. Stigma conical divided into two. Follicles are in pair or solitary, lanceolate cylindrical, beaked,
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<quantity id="4C959B62EF54FFA8FEE0FC07FE6FFC2E" box="[362,441,913,933]" metricMagnitude="-2" metricUnit="m" metricValue="8.5" metricValueMax="10.0" metricValueMin="7.0" pageId="1" pageNumber="2" unit="cm" value="8.5" valueMax="10.0" valueMin="7.0">7–10 cm</quantity>
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long,
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<quantity id="4C959B62EF54FFA8FE79FC07FD8FFC2E" box="[499,601,913,933]" metricMagnitude="-3" metricUnit="m" metricValue="4.5" metricValueMax="6.0" metricValueMin="3.0" pageId="1" pageNumber="2" unit="cm" value="0.44999999999999996" valueMax="0.6" valueMin="0.3">0.3–0.6 cm</quantity>
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in diameter, apex acuminate, base dilated and dense pubescent. There are many seeds, oblong-lanceolate and winged with a thin edge (
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<figureCitation id="13562A02EF54FFA8FDC8FC5FFDACFC57" box="[578,634,969,988]" captionStart="Fig" captionStartId="2.[100,130,1651,1668]" captionTargetBox="[229,1357,156,1625]" captionTargetId="figure-190@2.[225,1362,152,1628]" captionTargetPageId="2" captionText="Fig. 1. Morphological characteristics of Gymnema latifolium Wall ex. Wight. (a) Old stem showing wing-like cork (b) Living form; (c) Young branch with pairs of inflorescensces; (d) Adaxial leaf; (e) Abaxial leaf; (f) Inflorescence; (g) Dense bronze hairs on the young leaf; (h) A flower; (i) Calyx; (j) Corolla; (k) Gynostegium cylindric; (l) Pollinarium; (m) Stigma head; (n) Follicles." figureDoi="http://doi.org/10.5281/zenodo.8160261" httpUri="https://zenodo.org/record/8160261/files/figure.png" pageId="1" pageNumber="2">Fig. 1</figureCitation>
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). All of these external morphology are closely matched the description of
|
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<taxonomicName id="4C6D4D04EF54FFA8FD22FC73FF6FFB9F" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="latifolium">
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<emphasis id="B919EA95EF54FFA8FD22FC73FF6FFB9F" bold="true" italics="true" pageId="1" pageNumber="2">Gymnema latifolium</emphasis>
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</taxonomicName>
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by Flora of
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<collectingCountry id="F37A7617EF54FFA8FEBDFB97FEB8FB9F" box="[311,366,1025,1044]" name="China" pageId="1" pageNumber="2">China</collectingCountry>
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(
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<bibRefCitation id="EFFC4B76EF54FFA8FEF5FB97FD9BFB9F" author="Wu, Z. Y. & Raven, P. H." box="[383,589,1025,1044]" pageId="1" pageNumber="2" refId="ref12278" refString="Wu, Z. Y., Raven, P. H., 1995. Flora of China, vol. 16 (Gentianaceae through Boraginaceae). Science Press, Beijing, and Missouri Botanical Garden Press, St. Louis." type="book" year="1995">Wu and Raven, 1995</bibRefCitation>
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) with a slight difference on the fruit shape (
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<quantity id="4C959B62EF54FFA8FE0EFB8BFE02FBBB" box="[388,468,1053,1072]" metricMagnitude="-2" metricUnit="m" metricValue="8.5" metricValueMax="10.0" metricValueMin="7.0" pageId="1" pageNumber="2" unit="cm" value="8.5" valueMax="10.0" valueMin="7.0">7–10 cm</quantity>
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×
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<quantity id="4C959B62EF54FFA8FE78FB8BFD8DFBBB" box="[498,603,1053,1072]" metricMagnitude="-3" metricUnit="m" metricValue="4.5" metricValueMax="6.0" metricValueMin="3.0" pageId="1" pageNumber="2" unit="cm" value="0.44999999999999996" valueMax="0.6" valueMin="0.3">0.3–0.6 cm</quantity>
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) compared with 4.5–5.5 ×
|
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<quantity id="4C959B62EF54FFA8FF42FBAFFEF6FBC7" box="[200,288,1081,1100]" metricMagnitude="-2" metricUnit="m" metricValue="1.75" metricValueMax="2.0" metricValueMin="1.5" pageId="1" pageNumber="2" unit="cm" value="1.75" valueMax="2.0" valueMin="1.5">1.5–2 cm</quantity>
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. The morphological characteristic of wing-like cork was not mentioned in Flora of
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<collectingCountry id="F37A7617EF54FFA8FE03FBC3FE14FBE3" box="[393,450,1109,1128]" name="China" pageId="1" pageNumber="2">China</collectingCountry>
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, but the descriptions of
|
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<taxonomicName id="4C6D4D04EF54FFA8FD22FBC2FE12FB0F" authority="(Deokule et al., 2013)" baseAuthorityName="Deokule" baseAuthorityYear="2013" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="khadalense">
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<emphasis id="B919EA95EF54FFA8FD22FBC2FF10FB08" bold="true" italics="true" pageId="1" pageNumber="2">Gymnema khadalense</emphasis>
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(
|
||
<bibRefCitation id="EFFC4B76EF54FFA8FF55FBE7FE6AFB0F" author="Deokule, S. S. & Kavade, S. P. & Lakshminarasimhan, P. & Berde, V. B." box="[223,444,1137,1156]" pageId="1" pageNumber="2" pagination="4598 - 4600" refId="ref10995" refString="Deokule, S. S., Kavade, S. P., Lakshminarasimhan, P., Berde, V. B., 2013. An endemic and critically endangered species, Gymnema khandalense Santapau (Apocynaceae: Asclepiadoideae) - a new record to Goa State, India. J. Threat 5, 4598 - 4600. https: // doi. org / 10.11609 / JoTT. o 3438.4598 - 600." type="journal article" year="2013">Deokule et al., 2013</bibRefCitation>
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||
)
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||
</taxonomicName>
|
||
and
|
||
<taxonomicName id="4C6D4D04EF54FFA8FD82FBE6FE31FB14" authority="(Ramachandran and Viswanathan, 2009)" baseAuthorityName="Ramachandran and Viswanathan" baseAuthorityYear="2009" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="kollimalayanum">
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||
<emphasis id="B919EA95EF54FFA8FD82FBE6FCD7FB08" bold="true" box="[520,769,1136,1155]" italics="true" pageId="1" pageNumber="2">Gymnema kollimalayanum</emphasis>
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||
(
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||
<bibRefCitation id="EFFC4B76EF54FFA8FFE6FB1AFE09FB14" author="Ramachandran, A. & Viswanathan, M. B. G." box="[108,479,1164,1183]" pageId="1" pageNumber="2" pagination="407 - 411" refId="ref11854" refString="Ramachandran, A., Viswanathan, M. B. G., 2009. A new species of Gymnema (asclepiadaceae) from the Kollihills in Peninsular India. Adansonia 31, 407 - 411. https: // doi. org / 10.5252 / a 2009 n 2 a 10." type="journal article" year="2009">Ramachandran and Viswanathan, 2009</bibRefCitation>
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||
)
|
||
</taxonomicName>
|
||
are found. These two species,
|
||
<taxonomicName id="4C6D4D04EF54FFA8FFEEFB3EFEEFFB30" box="[100,313,1192,1211]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="khandalense">
|
||
<emphasis id="B919EA95EF54FFA8FFEEFB3EFEEFFB30" bold="true" box="[100,313,1192,1211]" italics="true" pageId="1" pageNumber="2">Gymnema khandalense</emphasis>
|
||
</taxonomicName>
|
||
and
|
||
<emphasis id="B919EA95EF54FFA8FEFEFB3EFDB9FB30" bold="true" box="[372,623,1192,1211]" italics="true" pageId="1" pageNumber="2">
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||
<taxonomicName id="4C6D4D04EF54FFA8FEFEFB3EFDBDFB30" baseAuthorityName="Ramachandran and Viswanathan" baseAuthorityYear="2009" box="[372,619,1192,1211]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="kollimalayanum">Gymnema kollimalayanum</taxonomicName>
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||
,
|
||
</emphasis>
|
||
were also reported as synonyms of
|
||
<taxonomicName id="4C6D4D04EF54FFA8FEB0FB52FD2AFB5C" authority="(Meve and Alejandro, 2011)" baseAuthorityName="Meve and Alejandro" baseAuthorityYear="2011" box="[314,764,1220,1240]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="latifolium">
|
||
<emphasis id="B919EA95EF54FFA8FEB0FB52FE39FB5C" bold="true" box="[314,495,1220,1239]" italics="true" pageId="1" pageNumber="2">Gymnema latifolium</emphasis>
|
||
(
|
||
<bibRefCitation id="EFFC4B76EF54FFA8FE76FB53FD22FB5C" author="Meve, U. & Alejandro, G. J." box="[508,756,1220,1240]" pageId="1" pageNumber="2" pagination="81 - 86" refId="ref11502" refString="Meve, U., Alejandro, G. J., 2011. Taxonomy of the asian Gymnema latifolium (Apocynaceae, Asclepiadoideae, Marsdenieae), including lectotypification of the synonymous. G. khandalense. Will. 43, 81 - 86. https: // doi. org / 10.3372 / wi. 43.43108." type="journal article" year="2011">Meve and Alejandro, 2011</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
. Thus, by comparing the descriptive morphological characteristics with the specimens of
|
||
<typeStatus id="54D68825EF54FFA8FE8FFB6AFE98FA84" box="[261,334,1276,1295]" pageId="1" pageNumber="2">syntype</typeStatus>
|
||
K000872841 (
|
||
<figureCitation id="13562A02EF54FFA8FE53FB6AFDCFFA84" box="[473,537,1276,1295]" captionStart="Fig" captionStartId="2.[100,130,1651,1668]" captionTargetBox="[229,1357,156,1625]" captionTargetId="figure-190@2.[225,1362,152,1628]" captionTargetPageId="2" captionText="Fig. 1. Morphological characteristics of Gymnema latifolium Wall ex. Wight. (a) Old stem showing wing-like cork (b) Living form; (c) Young branch with pairs of inflorescensces; (d) Adaxial leaf; (e) Abaxial leaf; (f) Inflorescence; (g) Dense bronze hairs on the young leaf; (h) A flower; (i) Calyx; (j) Corolla; (k) Gynostegium cylindric; (l) Pollinarium; (m) Stigma head; (n) Follicles." figureDoi="http://doi.org/10.5281/zenodo.8160261" httpUri="https://zenodo.org/record/8160261/files/figure.png" pageId="1" pageNumber="2">Fig. S1</figureCitation>
|
||
) and
|
||
<typeStatus id="54D68825EF54FFA8FDC5FB6AFD73FA84" box="[591,677,1276,1295]" pageId="1" pageNumber="2">lectotype</typeStatus>
|
||
specimen K000872839 (
|
||
<figureCitation id="13562A02EF54FFA8FF61FA8EFEFDFAA0" box="[235,299,1304,1323]" captionStart="Fig" captionStartId="3.[416,446,1259,1276]" captionTargetBox="[264,1323,152,1236]" captionTargetPageId="3" captionText="Fig. 2. Chemical structure of isolated compounds 1–9 isolated from Gymnema latifolium." figureDoi="http://doi.org/10.5281/zenodo.8160263" httpUri="https://zenodo.org/record/8160263/files/figure.png" pageId="1" pageNumber="2">Fig. S2</figureCitation>
|
||
) of
|
||
<taxonomicName id="4C6D4D04EF54FFA8FEDBFA8EFDD0FAA0" baseAuthorityName="Meve and Alejandro" baseAuthorityYear="2011" box="[337,518,1304,1323]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="latifolium">
|
||
<emphasis id="B919EA95EF54FFA8FEDBFA8EFDD0FAA0" bold="true" box="[337,518,1304,1323]" italics="true" pageId="1" pageNumber="2">Gymnema latifolium</emphasis>
|
||
</taxonomicName>
|
||
stored in the herbarium at the Royal Botanic Gardens Kew and the description by
|
||
<bibRefCitation id="EFFC4B76EF54FFA8FD2AFAA2FEDBFAE8" author="Meve, U. & Alejandro, G. J." pageId="1" pageNumber="2" pagination="81 - 86" refId="ref11502" refString="Meve, U., Alejandro, G. J., 2011. Taxonomy of the asian Gymnema latifolium (Apocynaceae, Asclepiadoideae, Marsdenieae), including lectotypification of the synonymous. G. khandalense. Will. 43, 81 - 86. https: // doi. org / 10.3372 / wi. 43.43108." type="journal article" year="2011">Meve and Alejandro (2011)</bibRefCitation>
|
||
, the studied sample was finally authenticated as
|
||
<taxonomicName id="4C6D4D04EF54FFA8FFEEFAFDFE1DFAF4" authority="Wall. ex Wight. In" authorityName="Wight. In" box="[100,459,1387,1407]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="latifolium">
|
||
<emphasis id="B919EA95EF54FFA8FFEEFAFDFECFFAF5" bold="true" box="[100,281,1387,1406]" italics="true" pageId="1" pageNumber="2">Gymnema latifolium</emphasis>
|
||
Wall. ex Wight. In
|
||
</taxonomicName>
|
||
addition, a DNA sequence of the ITS1-5.8S-ITS2 internal transcribed spacer of the sample was also deposited at Genbank (National Institutes of Health) with the accession number KP163979.
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF54FFA8FFEEFA6EFD21F980" blockId="1.[100,759,1528,1547]" box="[100,759,1528,1547]" pageId="1" pageNumber="2">
|
||
<emphasis id="B919EA95EF54FFA8FFEEFA6EFD21F980" bold="true" box="[100,759,1528,1547]" italics="true" pageId="1" pageNumber="2">
|
||
2.2. Isolation and structural elucidation of compounds from
|
||
<taxonomicName id="4C6D4D04EF54FFA8FD0DFA6EFD21F980" ID-CoL="3HPQM" ID-ENA="485208" box="[647,759,1528,1547]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="latifolium">G. latifolium</taxonomicName>
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF54FFA8FF0FF9A6FF79F8B5" blockId="1.[100,771,1584,1993]" pageId="1" pageNumber="2">
|
||
A 70% EtOH extract of
|
||
<taxonomicName id="4C6D4D04EF54FFA8FEE2F9A6FE0FF9C8" box="[360,473,1584,1603]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="latifolium">
|
||
<emphasis id="B919EA95EF54FFA8FEE2F9A6FE0FF9C8" bold="true" box="[360,473,1584,1603]" italics="true" pageId="1" pageNumber="2">G. latifolium</emphasis>
|
||
</taxonomicName>
|
||
was subjected to various chromatographic columns and then to purification by preparative highperformance liquid chromatography (HPLC) to afford seven previously undescribed oleanane triterpenoid glycosides, gymlatinosides GL1-GL7 (
|
||
<emphasis id="B919EA95EF54FFA8FFE6F909FF59F938" bold="true" box="[108,143,1695,1715]" pageId="1" pageNumber="2">1–7</emphasis>
|
||
) and two known compounds, gymnemic acid IX (
|
||
<emphasis id="B919EA95EF54FFA8FDFFF909FD57F939" bold="true" box="[629,641,1695,1714]" pageId="1" pageNumber="2">8</emphasis>
|
||
) and gymnemagenin (
|
||
<emphasis id="B919EA95EF54FFA8FF4EF92DFF06F945" bold="true" box="[196,208,1723,1742]" pageId="1" pageNumber="2">9</emphasis>
|
||
) (
|
||
<bibRefCitation id="EFFC4B76EF54FFA8FF6DF92DFEA0F945" author="Liu, H. - M. & Kiuchi, F. & Tsuda, Y." box="[231,374,1723,1743]" pageId="1" pageNumber="2" pagination="1366 - 1375" refId="ref11443" refString="Liu, H. - M., Kiuchi, F., Tsuda, Y., 1992. Isolation and structure elucidation of gymnemic acids, antisweet principles of Gymnema sylvestre. Chem. Pharm. Bull. 40, 1366 - 1375. https: // doi. org / 10.1248 / cpb. 40.1366." type="journal article" year="1992">Liu et al., 1992</bibRefCitation>
|
||
) (
|
||
<figureCitation id="13562A02EF54FFA8FE06F92DFE14F945" box="[396,450,1723,1742]" captionStart="Fig" captionStartId="3.[416,446,1259,1276]" captionTargetBox="[264,1323,152,1236]" captionTargetPageId="3" captionText="Fig. 2. Chemical structure of isolated compounds 1–9 isolated from Gymnema latifolium." figureDoi="http://doi.org/10.5281/zenodo.8160263" httpUri="https://zenodo.org/record/8160263/files/figure.png" pageId="1" pageNumber="2">Fig. 2</figureCitation>
|
||
). The structures of the previously undescribed compounds were elucidated by 2D-NMR, while known compounds were determined using
|
||
<superScript id="7C189BCFEF54FFA8FE46F979FE03F970" attach="right" box="[460,469,1775,1787]" fontSize="5" pageId="1" pageNumber="2">1</superScript>
|
||
H and
|
||
<superScript id="7C189BCFEF54FFA8FDAAF979FDE4F970" attach="right" box="[544,562,1775,1787]" fontSize="5" pageId="1" pageNumber="2">13</superScript>
|
||
C NMR analysis and comparing the physical and spectroscopic data with those in the literature.
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF54FFABFF0FF8D1FB97F808" blockId="1.[100,771,1584,1993]" lastBlockId="2.[818,1488,1761,1978]" lastPageId="2" lastPageNumber="3" pageId="1" pageNumber="2">
|
||
Gymlatinoside GL1 (
|
||
<emphasis id="B919EA95EF54FFA8FEDAF8D1FE8AF8D1" bold="true" box="[336,348,1863,1882]" pageId="1" pageNumber="2">1</emphasis>
|
||
), obtained as a white amorphous powder, with []
|
||
<subScript id="17E934C2EF54FFA8FF38F8FFFF6BF8FC" attach="left" box="[178,189,1897,1911]" fontSize="6" pageId="1" pageNumber="2">D</subScript>
|
||
<superScript id="7C189BCFEF54FFA8FF38F8CAFF17F8E1" attach="left" box="[178,193,1884,1898]" fontSize="6" pageId="1" pageNumber="2">25</superScript>
|
||
+15.2 (
|
||
<emphasis id="B919EA95EF54FFA8FE97F8F7FEF0F8FF" bold="true" box="[285,294,1889,1908]" italics="true" pageId="1" pageNumber="2">c</emphasis>
|
||
0.2, MeOH), was found to possess a molecular formula of C
|
||
<subScript id="17E934C2EF54FFA8FF53F810FF3DF819" attach="both" box="[217,235,1926,1938]" fontSize="5" pageId="1" pageNumber="2">49</subScript>
|
||
H
|
||
<subScript id="17E934C2EF54FFA8FF71F813FEDBF81A" attach="both" box="[251,269,1925,1937]" fontSize="5" pageId="1" pageNumber="2">76</subScript>
|
||
O
|
||
<subScript id="17E934C2EF54FFA8FE97F810FEF9F819" attach="left" box="[285,303,1926,1938]" fontSize="5" pageId="1" pageNumber="2">19</subScript>
|
||
and twelve indices of hydrogen deficiency (IHDs) based on the high-resolution electrospray ionization mass spectrometry (HRESIMS) ion peak at
|
||
<emphasis id="B919EA95EF54FFA8FECEF823FE82F843" bold="true" box="[324,340,1973,1992]" italics="true" pageId="1" pageNumber="2">m</emphasis>
|
||
/
|
||
<emphasis id="B919EA95EF54FFA8FED5F823FEBEF843" bold="true" box="[351,360,1973,1992]" italics="true" pageId="1" pageNumber="2">z</emphasis>
|
||
967.4896 [M − H]
|
||
<superScript id="7C189BCFEF54FFA8FDAEF827FDE2F836" attach="left" box="[548,564,1969,1981]" fontSize="5" pageId="1" pageNumber="2">−</superScript>
|
||
(calcd for C
|
||
<subScript id="17E934C2EF54FFA8FD22F82BFD6CF842" attach="both" box="[680,698,1981,1993]" fontSize="5" pageId="1" pageNumber="2">49</subScript>
|
||
H
|
||
<subScript id="17E934C2EF54FFA8FD40F82BFD0AF842" attach="both" box="[714,732,1981,1993]" fontSize="5" pageId="1" pageNumber="2">75</subScript>
|
||
O
|
||
<subScript id="17E934C2EF54FFA8FD61F82BFCD5F842" attach="left" box="[747,771,1981,1993]" fontSize="5" pageId="1" pageNumber="2">19,</subScript>
|
||
967.4903). The broad IR absorption at
|
||
<quantity id="4C959B62EF54FFA8FB38FF09FAD4FF38" box="[1202,1282,159,179]" metricMagnitude="1" metricUnit="m" metricValue="3.389" pageId="1" pageNumber="2" unit="cm" value="3389.0">3389 cm</quantity>
|
||
<superScript id="7C189BCFEF54FFA8FA88FF0DFACDFF2C" attach="left" box="[1282,1307,155,167]" fontSize="5" pageId="1" pageNumber="2">−1</superScript>
|
||
indicated the presence of hydroxy groups, and the absorption at
|
||
<quantity id="4C959B62EF54FFA8FB67FF2DFAEBFF45" box="[1261,1341,187,206]" metricMagnitude="1" metricUnit="m" metricValue="1.641" pageId="1" pageNumber="2" unit="cm" value="1641.0">1641 cm</quantity>
|
||
<superScript id="7C189BCFEF54FFA8FAB7FF21FA80FF48" attach="left" box="[1341,1366,183,195]" fontSize="5" pageId="1" pageNumber="2">−1</superScript>
|
||
revealed the existence of carboxylic moieties. The
|
||
<superScript id="7C189BCFEF54FFA8FB05FF45FB4EFF54" attach="right" box="[1167,1176,211,223]" fontSize="5" pageId="1" pageNumber="2">1</superScript>
|
||
H NMR spectrum exhibited seven methyl singlets at
|
||
<emphasis id="B919EA95EF54FFA8FC6BFF65FC3AFE8D" bold="true" box="[993,1004,243,262]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC61FF6AFC21FE83" attach="left" box="[1003,1015,252,264]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.94, 1.27, 1.20, 1.05, 1.04, 0.92 and 0.90 (each 3H). The most downfield resonance (
|
||
<emphasis id="B919EA95EF54FFA8FB25FE99FB6CFEA9" bold="true" box="[1199,1210,271,290]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB33FE8EFB13FEAF" attach="left" box="[1209,1221,280,292]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.94) is the signal of an acetoxy, and the others suggested an oleanane backbone. Two other methyls can be observed at
|
||
<emphasis id="B919EA95EF54FFA8FBB8FED0FBEBFED2" bold="true" box="[1074,1085,326,345]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FBB7FEC6FB9FFED7" attach="left" box="[1085,1097,336,348]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.23 (3H, d,
|
||
<emphasis id="B919EA95EF54FFA8FB49FED1FB1BFED1" bold="true" box="[1219,1229,327,346]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 7.0 Hz) and
|
||
<emphasis id="B919EA95EF54FFA8FAD1FED0FAB0FED2" bold="true" box="[1371,1382,326,345]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FAECFEC6FAA4FED7" attach="left" box="[1382,1394,336,348]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
0.97 (3H, t,
|
||
<emphasis id="B919EA95EF54FFA8FCCCFEF5FC86FEFD" bold="true" box="[838,848,355,374]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 7.0 Hz) (
|
||
<tableCitation id="C6EF033CEF54FFA8FC4AFEF4FBD1FEFE" box="[960,1031,354,373]" captionStart="Table 1" captionStartId="4.[100,150,161,177]" captionTargetPageId="4" captionText="Table 1 1H NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" httpUri="http://table.plazi.org/id/DF12660FEF51FFADFFEEFF37FE05FF46" pageId="1" pageNumber="2" tableUuid="DF12660FEF51FFADFFEEFF37FE05FF46">Table 1</tableCitation>
|
||
). The
|
||
<superScript id="7C189BCFEF54FFA8FBCCFEC9FB8EFEE0" attach="right" box="[1094,1112,351,363]" fontSize="5" pageId="1" pageNumber="2">13</superScript>
|
||
C NMR spectrum showed signals for 49 carbons, including three carboxylic groups at
|
||
<emphasis id="B919EA95EF54FFA8FA89FEE8FAD8FE1A" bold="true" box="[1283,1294,382,401]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FA87FE11FAC1FE18" attach="left" box="[1293,1303,391,403]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
176.8, 171.6 and 171.1; two olefinic carbon signals at
|
||
<emphasis id="B919EA95EF54FFA8FB07FE0CFB4EFE26" bold="true" box="[1165,1176,410,429]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB12FE35FB74FE24" attach="left" box="[1176,1186,419,431]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
141.5 and 124.9; two anomeric carbons at
|
||
<emphasis id="B919EA95EF54FFA8FC11FE20FC70FE42" bold="true" box="[923,934,438,457]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC2CFE29FC66FE40" attach="left" box="[934,944,447,459]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
106.8 and 97.4; fifteen oxygenated carbons in the range from
|
||
<emphasis id="B919EA95EF54FFA8FCEDFE44FCA4FE6E" bold="true" box="[871,882,466,485]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FCF8FE4DFCAAFE6C" attach="left" box="[882,892,475,487]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
62.6 to 94.1, and others are methine, methylene and methyl signals (
|
||
<tableCitation id="C6EF033CEF54FFA8FC0EFE78FC19FD8A" box="[900,975,494,513]" captionStart="Table 2" captionStartId="5.[100,150,161,177]" captionTargetPageId="5" captionText="Table 2 13C NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" pageId="1" pageNumber="2">Table 2</tableCitation>
|
||
). The COSY, HSQC and HMBC spectra indicated a planar structure of oleanane-type triterpene possessing six hydroxy groups substituted at C-3, 16, 21, 22, 23 and 28 for the main aglycone of
|
||
<emphasis id="B919EA95EF54FFA8FCC1FDD7FC81FDDF" bold="true" box="[843,855,577,596]" pageId="1" pageNumber="2">1</emphasis>
|
||
(
|
||
<figureCitation id="13562A02EF54FFA8FCEDFDD7FC4BFDDE" box="[871,925,577,597]" captionStart="Fig" captionStartId="6.[491,521,1297,1314]" captionTargetBox="[151,1436,152,1275]" captionTargetId="graphics-624@6.[151,1436,152,1274]" captionTargetPageId="6" captionText="Fig. 3. Key COSY and HMBC correlations of compounds 1, 5, 6 and 7." figureDoi="http://doi.org/10.5281/zenodo.8160265" httpUri="https://zenodo.org/record/8160265/files/figure.png" pageId="1" pageNumber="2">Fig. 3</figureCitation>
|
||
). Comparing chemical shifts of
|
||
<emphasis id="B919EA95EF54FFA8FB45FDD7FB0DFDDF" bold="true" box="[1231,1243,577,596]" pageId="1" pageNumber="2">1</emphasis>
|
||
with gymnemic acid VIII and gymnemic acid X suggested gymnemagenin to be the main aglycone (
|
||
<bibRefCitation id="EFFC4B76EF54FFA8FCE1FDEFFC2CFD07" author="Liu, H. - M. & Kiuchi, F. & Tsuda, Y." box="[875,1018,633,653]" pageId="1" pageNumber="2" pagination="1366 - 1375" refId="ref11443" refString="Liu, H. - M., Kiuchi, F., Tsuda, Y., 1992. Isolation and structure elucidation of gymnemic acids, antisweet principles of Gymnema sylvestre. Chem. Pharm. Bull. 40, 1366 - 1375. https: // doi. org / 10.1248 / cpb. 40.1366." type="journal article" year="1992">Liu et al., 1992</bibRefCitation>
|
||
). A series of NOESY correlations between H-3 (
|
||
<emphasis id="B919EA95EF54FFA8FA32FDEFFA15FD07" bold="true" box="[1464,1475,633,652]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FA49FD15FA19FD04" attach="left" box="[1475,1487,643,655]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.26 dd,
|
||
<emphasis id="B919EA95EF54FFA8FC00FD03FC42FD23" bold="true" box="[906,916,661,680]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 12.3, 4.5 Hz), H-23 [(
|
||
<emphasis id="B919EA95EF54FFA8FB09FD03FB58FD23" bold="true" box="[1155,1166,661,680]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB04FD08FB4CFD21" attach="left" box="[1166,1178,670,682]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
3.70 d,
|
||
<emphasis id="B919EA95EF54FFA8FB61FD03FB23FD23" bold="true" box="[1259,1269,661,680]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 10.5 Hz);
|
||
<emphasis id="B919EA95EF54FFA8FAFAFD03FAADFD23" bold="true" box="[1392,1403,661,680]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FAF1FD08FA51FD21" attach="left" box="[1403,1415,670,682]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.32 d,
|
||
<emphasis id="B919EA95EF54FFA8FCB8FD27FCEAFD4F" bold="true" box="[818,828,689,708]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 10.5 Hz)], H-5 (
|
||
<emphasis id="B919EA95EF54FFA8FC65FD27FC2CFD4F" bold="true" box="[1007,1018,689,708]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC70FD2CFBD0FD4D" attach="left" box="[1018,1030,698,710]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.64, overlap), H-9 (
|
||
<emphasis id="B919EA95EF54FFA8FB44FD27FB0FFD4F" bold="true" box="[1230,1241,689,708]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB53FD2CFB33FD4D" attach="left" box="[1241,1253,698,710]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.64, overlap), H-27 (
|
||
<emphasis id="B919EA95EF54FFA8FA32FD27FA15FD4F" bold="true" box="[1464,1475,689,708]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FA49FD2CFA19FD4D" attach="left" box="[1475,1487,698,710]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.27, s), H-16 (
|
||
<emphasis id="B919EA95EF54FFA8FC5FFD5BFC36FD6B" bold="true" box="[981,992,717,736]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC55FD40FC3DFD69" attach="left" box="[991,1003,726,738]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
5.09, dd,
|
||
<emphasis id="B919EA95EF54FFA8FBD5FD5BFBBFFD6B" bold="true" box="[1119,1129,717,736]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 11.0, 5.2 Hz), H-21 (
|
||
<emphasis id="B919EA95EF54FFA8FAD7FD5BFABEFD6B" bold="true" box="[1373,1384,717,736]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FAE2FD40FAA2FD69" attach="left" box="[1384,1396,726,738]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
5.67, d,
|
||
<emphasis id="B919EA95EF54FFA8FCB8FD7FFCEAFD77" bold="true" box="[818,828,745,764]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 10.5 Hz) and H-29 (
|
||
<emphasis id="B919EA95EF54FFA8FB91FD7FFBF0FD77" bold="true" box="[1051,1062,745,764]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FBACFD64FBE4FD75" attach="left" box="[1062,1074,754,766]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.04, s) confirmed the
|
||
<emphasis id="B919EA95EF54FFA8FA93FD7FFAF3FD77" bold="true" box="[1305,1317,745,764]" italics="true" pageId="1" pageNumber="2">α</emphasis>
|
||
configuration for these protons. Meanwhile, the series of NOESY cross peaks between H-24 (
|
||
<emphasis id="B919EA95EF54FFA8FCD0FCB6FCB3FCB8" bold="true" box="[858,869,800,819]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FCEFFCBCFCA7FCBD" attach="left" box="[869,881,810,822]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
0.92, s), H-25 (
|
||
<emphasis id="B919EA95EF54FFA8FB9BFCB6FBCAFCB8" bold="true" box="[1041,1052,800,819]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB96FCBCFBFEFCBD" attach="left" box="[1052,1064,810,822]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
0.92, s), H-26 (
|
||
<emphasis id="B919EA95EF54FFA8FB43FCB6FB02FCB8" bold="true" box="[1225,1236,800,819]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB59FCBCFB09FCBD" attach="left" box="[1235,1247,810,822]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.05, s), H-28 (
|
||
<emphasis id="B919EA95EF54FFA8FA0AFCB6FA5DFCB8" bold="true" box="[1408,1419,800,819]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FA01FCBCFA41FCBD" attach="left" box="[1419,1431,810,822]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.57, overlap;
|
||
<emphasis id="B919EA95EF54FFA8FC0FFCAAFC46FCC4" bold="true" box="[901,912,828,847]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC1AFCD0FC4AFCD9" attach="left" box="[912,924,838,850]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.99 d,
|
||
<emphasis id="B919EA95EF54FFA8FC60FCABFC22FCDB" bold="true" box="[1002,1012,829,848]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 10.5 Hz), H-18 (
|
||
<emphasis id="B919EA95EF54FFA8FB27FCAAFB6EFCC4" bold="true" box="[1197,1208,828,847]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB3DFCD0FB15FCD9" attach="left" box="[1207,1219,838,850]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
2.84, dd,
|
||
<emphasis id="B919EA95EF54FFA8FAADFCABFAE7FCDB" bold="true" box="[1319,1329,829,848]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 13.7, 3.9 Hz), H-22 (
|
||
<emphasis id="B919EA95EF54FFA8FCF8FCCEFCABFCE0" bold="true" box="[882,893,856,875]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FCF7FCF4FC5FFCE5" attach="left" box="[893,905,866,878]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.50, overlap) and H-30 (
|
||
<emphasis id="B919EA95EF54FFA8FB1AFCCEFB4DFCE0" bold="true" box="[1168,1179,856,875]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB11FCF4FB71FCE5" attach="left" box="[1179,1191,866,878]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.20, s) demonstrated their
|
||
<emphasis id="B919EA95EF54FFA8FA4EFCCEFA19FCE0" bold="true" box="[1476,1487,856,875]" italics="true" pageId="1" pageNumber="2">β</emphasis>
|
||
configurations (
|
||
<figureCitation id="13562A02EF54FFA8FC42FCE2FC28FC03" box="[968,1022,884,904]" captionStart="Fig" captionStartId="7.[100,130,966,983]" captionTargetBox="[151,1436,152,942]" captionTargetPageId="7" captionText="Fig. 4. Key NOESY correlations of compounds 1 (a: the aglycone, b: sugar moiety), 5 and 6. Fig. 4 c showed the chemical shifts and coupling constants of the protons on the glycosides. HMBC correlations bridging two sugar moieties were measured. All the discussions about COSY, NOESY and the coupling constant rules to identify the relative configuration of the sugar moiety were suggested at Results and discussion of compound 1." figureDoi="http://doi.org/10.5281/zenodo.8160267" httpUri="https://zenodo.org/record/8160267/files/figure.png" pageId="1" pageNumber="2">Fig. 4</figureCitation>
|
||
). Furthermore, the acid hydrolysis of
|
||
<emphasis id="B919EA95EF54FFA8FAE6FCE2FAAEFC0C" bold="true" box="[1388,1400,884,903]" pageId="1" pageNumber="2">1</emphasis>
|
||
afforded an aglycone which exhibited the same retention time and mass fragmentation with the standard gymnemagenin on LC-MS analysis. Two carboxylic groups were identified to be a 2-methylbutyryl (
|
||
<emphasis id="B919EA95EF54FFA8FAFEFC5EFAA9FC50" bold="true" box="[1396,1407,968,987]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FAF5FC47FA5FFC56" attach="left" box="[1407,1417,977,989]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
176.8) and an acetyl (
|
||
<emphasis id="B919EA95EF54FFA8FC30FC72FC13FC7C" bold="true" box="[954,965,996,1015]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC4FFC7BFC19FC72" attach="left" box="[965,975,1005,1017]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
171.1) substitutions by comparing with those reported in literature (
|
||
<bibRefCitation id="EFFC4B76EF54FFA8FC38FB96FB5DFB98" author="Yoshikawa, K. & Nakagama, M. & Yamamoto, R. & Arihara, S. & Matsuura, K." box="[946,1163,1024,1043]" pageId="1" pageNumber="2" pagination="1779 - 1782" refId="ref12450" refString="Yoshikawa, K., Nakagama, M., Yamamoto, R., Arihara, S., Matsuura, K., 1992. Antisweet natural products. V. Structures of gymnemic acids VIII-XII from Gymnema sylvestre R. Br. Chem. Pharm. Bull. 40, 1779 - 1782. https: // doi. org / 10.1248 / cpb. 40.1779." type="journal article" year="1992">Yoshikawa et al., 1992</bibRefCitation>
|
||
). Compared with gymnemagenin, the acylation shifts can be observed at C-28 (
|
||
<emphasis id="B919EA95EF54FFA8FB5EFB8AFB09FBA4" bold="true" box="[1236,1247,1052,1071]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB54FBB3FB3EFBBA" attach="left" box="[1246,1256,1061,1073]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
62.6, +4.1 ppm) and C-21 (
|
||
<emphasis id="B919EA95EF54FFA8FCDDFBAEFCB4FBC0" bold="true" box="[855,866,1080,1099]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FCE8FBD7FCBAFBC6" attach="left" box="[866,876,1089,1101]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
78.6, +1.4 ppm) (
|
||
<bibRefCitation id="EFFC4B76EF54FFA8FB94FBAEFB7CFBC0" author="Liu, H. - M. & Kiuchi, F. & Tsuda, Y." box="[1054,1194,1080,1099]" pageId="1" pageNumber="2" pagination="1366 - 1375" refId="ref11443" refString="Liu, H. - M., Kiuchi, F., Tsuda, Y., 1992. Isolation and structure elucidation of gymnemic acids, antisweet principles of Gymnema sylvestre. Chem. Pharm. Bull. 40, 1366 - 1375. https: // doi. org / 10.1248 / cpb. 40.1366." type="journal article" year="1992">Liu et al., 1992</bibRefCitation>
|
||
). The protons at C-21 and C-28 also showed significant downfield shifts from those of gymnemagenin [(H-21:
|
||
<emphasis id="B919EA95EF54FFA8FCF6FBF9FC51FB09" bold="true" box="[892,903,1135,1154]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC0DFBEFFC45FB0E" attach="left" box="[903,915,1145,1157]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.04 →
|
||
<emphasis id="B919EA95EF54FFA8FC6BFBF9FC3AFB09" bold="true" box="[993,1004,1135,1154]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC66FBEFFC2EFB0E" attach="left" box="[1004,1016,1145,1157]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
5.67) and (H-28:
|
||
<emphasis id="B919EA95EF54FFA8FB17FBF9FB7EFB09" bold="true" box="[1181,1192,1135,1154]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB22FBEFFB62FB0E" attach="left" box="[1192,1204,1145,1157]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.07 →
|
||
<emphasis id="B919EA95EF54FFA8FA89FBF9FAD8FB09" bold="true" box="[1283,1294,1135,1154]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FA84FBEFFACCFB0E" attach="left" box="[1294,1306,1145,1157]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.57;
|
||
<emphasis id="B919EA95EF54FFA8FAD9FBF9FA88FB09" bold="true" box="[1363,1374,1135,1154]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FAD4FBEFFABCFB0E" attach="left" box="[1374,1386,1145,1157]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.71 →
|
||
<emphasis id="B919EA95EF54FFA8FA32FBF9FA15FB09" bold="true" box="[1464,1475,1135,1154]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FA49FBEFFA19FB0E" attach="left" box="[1475,1487,1145,1157]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.99)]. The HMBC correlations from H-21 (
|
||
<emphasis id="B919EA95EF54FFA8FB5AFB1DFB0DFB15" bold="true" box="[1232,1243,1163,1182]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB51FB02FB31FB2B" attach="left" box="[1243,1255,1172,1184]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
5.67, d,
|
||
<emphasis id="B919EA95EF54FFA8FAB4FB1AFA9EFB14" bold="true" box="[1342,1352,1164,1183]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 10.5 Hz) to C-1
|
||
<superScript id="7C189BCFEF54FFA8FCD8FB35FC57FB24" attach="left" box="[850,897,1187,1199]" fontSize="5" pageId="1" pageNumber="2">M−21</superScript>
|
||
(
|
||
<emphasis id="B919EA95EF54FFA8FC1EFB31FC49FB31" bold="true" box="[916,927,1191,1210]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC15FB26FC7FFB37" attach="left" box="[927,937,1200,1212]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
176.8), and H-28 [(
|
||
<emphasis id="B919EA95EF54FFA8FBF2FB31FB55FB31" bold="true" box="[1144,1155,1191,1210]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB09FB26FB59FB37" attach="left" box="[1155,1167,1200,1212]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.99, d,
|
||
<emphasis id="B919EA95EF54FFA8FB65FB3EFB2FFB30" bold="true" box="[1263,1273,1192,1211]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 10.5 Hz); (
|
||
<emphasis id="B919EA95EF54FFA8FAF4FB31FA5FFB31" bold="true" box="[1406,1417,1191,1210]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FA03FB26FA43FB37" attach="left" box="[1417,1429,1200,1212]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.57, overlap)] to C-1
|
||
<superScript id="7C189BCFEF54FFA8FC44FB29FC2DFB40" attach="left" box="[974,1019,1215,1227]" fontSize="5" pageId="1" pageNumber="2">A−28</superScript>
|
||
(
|
||
<emphasis id="B919EA95EF54FFA8FB86FB55FBC1FB5D" bold="true" box="[1036,1047,1219,1238]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB9DFB5AFBF7FB53" attach="left" box="[1047,1057,1228,1240]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
171.1) confirmed the linkages of the 2-methylbutyryl to C-21 and the acetyl to C-28. NMR chemical shifts of the 2-methylbutyryl portion in compound
|
||
<emphasis id="B919EA95EF54FFA8FB20FB6DFB60FA85" bold="true" box="[1194,1206,1275,1294]" pageId="1" pageNumber="2">1</emphasis>
|
||
were similar to the data reported by Yoshikawa, where the absolute configuration of 2-methylbutyryl in gymnemic acid II isolated from
|
||
<taxonomicName id="4C6D4D04EF54FFA8FB32FAA5FACBFACE" box="[1208,1309,1330,1350]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="sylvestre">
|
||
<emphasis id="B919EA95EF54FFA8FB32FAA5FACBFACE" bold="true" box="[1208,1309,1330,1350]" italics="true" pageId="1" pageNumber="2">G. sylvestre</emphasis>
|
||
</taxonomicName>
|
||
is 2(
|
||
<emphasis id="B919EA95EF54FFA8FAC3FAA5FA82FACD" bold="true" box="[1353,1364,1331,1350]" italics="true" pageId="1" pageNumber="2">S</emphasis>
|
||
) (
|
||
<bibRefCitation id="EFFC4B76EF54FFA8FAE0FAA5FC77FAE9" author="Yoshikawa, K. & Amimoto, K. & Arihara, S. & Matsuura, K." pageId="1" pageNumber="2" pagination="1103 - 1106" refId="ref12389" refString="Yoshikawa, K., Amimoto, K., Arihara, S., Matsuura, K., 1989. Structure studies of new antisweet constituents from Gymnema sylvestre. Tetrahedron Lett. 30, 1103 - 1106. https: // doi. org / 10.1016 / S 0040 - 4039 (01) 80371 - 3." type="journal article" year="1989">Yoshikawa et al., 1989</bibRefCitation>
|
||
). Since the plants
|
||
<taxonomicName id="4C6D4D04EF54FFA8FBD2FAD9FB1CFAEA" box="[1112,1226,1358,1378]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="latifolium">
|
||
<emphasis id="B919EA95EF54FFA8FBD2FAD9FB1CFAEA" bold="true" box="[1112,1226,1358,1378]" italics="true" pageId="1" pageNumber="2">G. latifolium</emphasis>
|
||
</taxonomicName>
|
||
and
|
||
<taxonomicName id="4C6D4D04EF54FFA8FB74FAD9FAB0FAEA" box="[1278,1382,1358,1378]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="sylvestre">
|
||
<emphasis id="B919EA95EF54FFA8FB74FAD9FAB0FAEA" bold="true" box="[1278,1382,1358,1378]" italics="true" pageId="1" pageNumber="2">G. sylvestre</emphasis>
|
||
</taxonomicName>
|
||
have been classified in the same genus, it is suggested that they possess similar biosynthesis pathway for 2(
|
||
<emphasis id="B919EA95EF54FFA8FBB5FA10FB9CFA12" bold="true" box="[1087,1098,1414,1433]" italics="true" pageId="1" pageNumber="2">S</emphasis>
|
||
)-methylbutyryl. In addition, the configuration of the 2(
|
||
<emphasis id="B919EA95EF54FFA8FC5EFA34FC09FA3E" bold="true" box="[980,991,1442,1461]" italics="true" pageId="1" pageNumber="2">S</emphasis>
|
||
)-methylbutyryl moiety in compound
|
||
<emphasis id="B919EA95EF54FFA8FAC6FA34FA8EFA3E" bold="true" box="[1356,1368,1442,1461]" pageId="1" pageNumber="2">1</emphasis>
|
||
was further confirmed by the clear NOESY correlation between H-21 (
|
||
<emphasis id="B919EA95EF54FFA8FAECFA28FAA7FA5A" bold="true" box="[1382,1393,1470,1489]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FAFBFA51FAABFA58" attach="left" box="[1393,1405,1479,1491]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
5.67, d,
|
||
<emphasis id="B919EA95EF54FFA8FCB8FA4CFCEAFA66" bold="true" box="[818,828,1498,1517]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 10.5 Hz) to H-2
|
||
<superScript id="7C189BCFEF54FFA8FC66FA40FBCAFA69" attach="left" box="[1004,1052,1494,1506]" fontSize="5" pageId="1" pageNumber="2">M−21</superScript>
|
||
(
|
||
<emphasis id="B919EA95EF54FFA8FBA1FA4CFBE0FA66" bold="true" box="[1067,1078,1498,1517]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FBBCFA75FB94FA64" attach="left" box="[1078,1090,1507,1519]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
2.56, sextet,
|
||
<emphasis id="B919EA95EF54FFA8FB4EFA4CFB18FA66" bold="true" box="[1220,1230,1498,1517]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 6.0 Hz) and the absence of NOESY correlation between H-21 and H-5
|
||
<superScript id="7C189BCFEF54FFA8FA9AFA64FAE9FA75" attach="left" box="[1296,1343,1522,1534]" fontSize="5" pageId="1" pageNumber="2">M−21</superScript>
|
||
(
|
||
<emphasis id="B919EA95EF54FFA8FADDFA60FAB4F982" bold="true" box="[1367,1378,1526,1545]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FAE8FA69FAB8F980" attach="left" box="[1378,1390,1535,1547]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
1.23, d,
|
||
<emphasis id="B919EA95EF54FFA8FCB8F987FCEAF9AF" bold="true" box="[818,828,1553,1572]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 7.0 Hz). The distance 2.016 Å between H-21 and H-2
|
||
<superScript id="7C189BCFEF54FFA8FACFF99BFAA3F992" attach="left" box="[1349,1397,1549,1561]" fontSize="5" pageId="1" pageNumber="2">M−21</superScript>
|
||
observed in a 3D geometry model optimized using MM2 minimized energy force field also supported this configuration (Fig. S10B). The COSY and dimensional (2D)
|
||
<emphasis id="B919EA95EF54FFA8FC47F9F2FC01F9FC" bold="true" box="[973,983,1636,1655]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
-resolved NMR spectra allowed the detection of two sugar chains, and the precise assignment of the coupling constants of their sugar protons (
|
||
<tableCitation id="C6EF033CEF54FFA8FC65F90AFBE2F924" box="[1007,1076,1692,1711]" captionStart="Table 1" captionStartId="4.[100,150,161,177]" captionTargetPageId="4" captionText="Table 1 1H NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" httpUri="http://table.plazi.org/id/DF12660FEF51FFADFFEEFF37FE05FF46" pageId="1" pageNumber="2" tableUuid="DF12660FEF51FFADFFEEFF37FE05FF46">Table 1</tableCitation>
|
||
). A doublet signal at
|
||
<emphasis id="B919EA95EF54FFA8FB70F90AFAD3F924" bold="true" box="[1274,1285,1692,1711]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FA8FF933FAC7F93A" attach="left" box="[1285,1297,1701,1713]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
5.17 (d,
|
||
<emphasis id="B919EA95EF54FFA8FAEEF90AFAB8F924" bold="true" box="[1380,1390,1692,1711]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 7.5 Hz) can be assigned to a
|
||
<emphasis id="B919EA95EF54FFA8FC76F92EFBD1F940" bold="true" box="[1020,1031,1720,1739]" italics="true" pageId="1" pageNumber="2">β</emphasis>
|
||
-isomer anomeric proton H-1′, corresponding to the anomeric carbon signal at C-1′ (
|
||
<emphasis id="B919EA95EF54FFA8FBF7F942FB5EF96C" bold="true" box="[1149,1160,1748,1767]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB02F94BFB44F962" attach="left" box="[1160,1170,1757,1769]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
106.8). The appearance of proton H-5′ (
|
||
<emphasis id="B919EA95EF54FFA8FCEDF966FCA4F888" bold="true" box="[871,882,1776,1795]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FCF8F96FFCA8F88E" attach="left" box="[882,894,1785,1797]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
4.51) as a doublet (
|
||
<emphasis id="B919EA95EF54FFA8FBB0F966FB92F888" bold="true" box="[1082,1092,1776,1795]" italics="true" pageId="1" pageNumber="2">J</emphasis>
|
||
= 10.5 Hz) and its HMBC cross peak with C-6′ (
|
||
<emphasis id="B919EA95EF54FFA8FCE2F89DFCA5F895" bold="true" box="[872,883,1803,1822]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FCF9F883FCABF8AA" attach="left" box="[883,893,1813,1825]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
171.6) suggested that the first sugar moiety is a glucuronic acid. The second anomeric proton H-1′′ (
|
||
<emphasis id="B919EA95EF54FFA8FB24F8B1FB6FF8B1" bold="true" box="[1198,1209,1831,1850]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FB33F8A7FB13F8B6" attach="left" box="[1209,1221,1841,1853]" fontSize="5" pageId="1" pageNumber="2">H</subScript>
|
||
5.32) which correlated with C-1′′ (
|
||
<emphasis id="B919EA95EF54FFA8FCE4F8D5FCAFF8DD" bold="true" box="[878,889,1859,1878]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FCF3F8DBFC55F8D2" attach="left" box="[889,899,1869,1881]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
97.4) on HSQC spectrum and the signal of the quaternary carbon C-2′′ (
|
||
<emphasis id="B919EA95EF54FFA8FC3BF8C9FC6AF8F9" bold="true" box="[945,956,1887,1906]" italics="true" pageId="1" pageNumber="2">δ</emphasis>
|
||
<subScript id="17E934C2EF54FFA8FC31F8FEFC13F8FF" attach="left" box="[955,965,1896,1908]" fontSize="5" pageId="1" pageNumber="2">C</subScript>
|
||
94.1) are the characteristics of a 2-oxo-hexose which is forming an intramolecular hemiacetal with another hydroxy group (
|
||
<bibRefCitation id="EFFC4B76EF54FFA8FA3BF8EDFC77F821" author="Liu, H. - M. & Kiuchi, F. & Tsuda, Y." pageId="1" pageNumber="2" pagination="1366 - 1375" refId="ref11443" refString="Liu, H. - M., Kiuchi, F., Tsuda, Y., 1992. Isolation and structure elucidation of gymnemic acids, antisweet principles of Gymnema sylvestre. Chem. Pharm. Bull. 40, 1366 - 1375. https: // doi. org / 10.1248 / cpb. 40.1366." type="journal article" year="1992">Liu et al., 1992</bibRefCitation>
|
||
). The existence of this 2-oxo-glucose portion was also recognizable by a fragment loss of 160 amu in the positive mass fragmentation. Furthermore, the
|
||
<superScript id="7C189BCFEF57FFABFE2FF977FE61F966" attach="right" box="[421,439,1761,1773]" fontSize="5" pageId="2" pageNumber="3">13</superScript>
|
||
C-NMR data of the sugar portions were almost identical to those of gymnemic acid VIII (
|
||
<bibRefCitation id="EFFC4B76EF57FFABFDEFF896FD22F89F" author="Liu, H. - M. & Kiuchi, F. & Tsuda, Y." box="[613,756,1792,1812]" pageId="2" pageNumber="3" pagination="1366 - 1375" refId="ref11443" refString="Liu, H. - M., Kiuchi, F., Tsuda, Y., 1992. Isolation and structure elucidation of gymnemic acids, antisweet principles of Gymnema sylvestre. Chem. Pharm. Bull. 40, 1366 - 1375. https: // doi. org / 10.1248 / cpb. 40.1366." type="journal article" year="1992">Liu et al., 1992</bibRefCitation>
|
||
). The HMBC correlation from H-4′ (
|
||
<emphasis id="B919EA95EF57FFABFE34F88AFE1FF8A4" bold="true" box="[446,457,1820,1839]" italics="true" pageId="2" pageNumber="3">δ</emphasis>
|
||
<subScript id="17E934C2EF57FFABFE43F8B0FE03F8B9" attach="left" box="[457,469,1830,1842]" fontSize="5" pageId="2" pageNumber="3">H</subScript>
|
||
5.21, t,
|
||
<emphasis id="B919EA95EF57FFABFDB9F88AFDEBF8A4" bold="true" box="[563,573,1820,1839]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 10.5 Hz) to C-2″, which was not detected by Liu, but finally could be observed in a high resolution HMBC NMR experiment. This HMBC correlation further confirmed the existence dioxane ring between two sugar moieties (
|
||
<figureCitation id="13562A02EF57FFABFFE6F81AFF72F814" box="[108,164,1932,1951]" captionStart="Fig" captionStartId="6.[491,521,1297,1314]" captionTargetBox="[151,1436,152,1275]" captionTargetId="graphics-624@6.[151,1436,152,1274]" captionTargetPageId="6" captionText="Fig. 3. Key COSY and HMBC correlations of compounds 1, 5, 6 and 7." figureDoi="http://doi.org/10.5281/zenodo.8160265" httpUri="https://zenodo.org/record/8160265/files/figure.png" pageId="2" pageNumber="3">Fig. 3</figureCitation>
|
||
). Coupling constants and NOESY correlations confirmed the
|
||
<emphasis id="B919EA95EF57FFABFD7DF81DFCD4F815" bold="true" box="[759,770,1931,1950]" italics="true" pageId="2" pageNumber="3">β</emphasis>
|
||
configurations for H-2′ and 4′, and
|
||
<emphasis id="B919EA95EF57FFABFE3BF83EFE6BF830" bold="true" box="[433,445,1960,1979]" italics="true" pageId="2" pageNumber="3">α</emphasis>
|
||
orientations for H-1′, 3′, 5′, 1″, 3″ and 5′′. The
|
||
<superScript id="7C189BCFEF57FFABFC39F977FC6AF966" attach="right" box="[947,956,1761,1773]" fontSize="5" pageId="2" pageNumber="3">3</superScript>
|
||
<emphasis id="B919EA95EF57FFABFC36F973FC10F973" bold="true" box="[956,966,1765,1784]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
coupling constant (
|
||
<emphasis id="B919EA95EF57FFABFB07F973FB41F973" bold="true" box="[1165,1175,1765,1784]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
= 10.0 Hz) observed by dimensional (2D)
|
||
<emphasis id="B919EA95EF57FFABFC28F897FC7AF89F" bold="true" box="[930,940,1793,1812]" italics="true" pageId="2" pageNumber="3">J</emphasis>
|
||
-resolved NMR indicated the antiperiplanar conformation between H-3″ and H-4″ and thus verified the axial orientation of H-4′′. Taken together, compound
|
||
<emphasis id="B919EA95EF57FFABFBBFF8AEFB97F8C0" bold="true" box="[1077,1089,1848,1867]" pageId="2" pageNumber="3">1</emphasis>
|
||
was deduced as 21-
|
||
<emphasis id="B919EA95EF57FFABFB75F8AEFAD8F8C0" bold="true" box="[1279,1294,1848,1867]" italics="true" pageId="2" pageNumber="3">O</emphasis>
|
||
-2(
|
||
<emphasis id="B919EA95EF57FFABFAA3F8AEFAE2F8C0" bold="true" box="[1321,1332,1848,1867]" italics="true" pageId="2" pageNumber="3">S</emphasis>
|
||
)-methylbutyryl-28-
|
||
<emphasis id="B919EA95EF57FFABFCDAF8C2FC89F8EC" bold="true" box="[848,863,1876,1895]" italics="true" pageId="2" pageNumber="3">O</emphasis>
|
||
-acetyl-gymnemagenin 3-
|
||
<emphasis id="B919EA95EF57FFABFBD7F8C2FBA8F8EC" bold="true" box="[1117,1150,1876,1895]" italics="true" pageId="2" pageNumber="3">O -β</emphasis>
|
||
-D-arabino-2-hexulopyranosyl-(1 → 3)-
|
||
<emphasis id="B919EA95EF57FFABFCC6F8E6FC81F808" bold="true" box="[844,855,1904,1923]" italics="true" pageId="2" pageNumber="3">β</emphasis>
|
||
-D-glucuronopyranoside.
|
||
</paragraph>
|
||
<caption id="DF12660FEF57FFABFFEEF9E5FD9CF93C" ID-DOI="http://doi.org/10.5281/zenodo.8160261" ID-Zenodo-Dep="8160261" httpUri="https://zenodo.org/record/8160261/files/figure.png" pageId="2" pageNumber="3" startId="2.[100,130,1651,1668]" targetBox="[229,1357,156,1625]" targetPageId="2" targetType="figure">
|
||
<paragraph id="8BD23687EF57FFABFFEEF9E5FD9CF93C" blockId="2.[100,1487,1650,1719]" pageId="2" pageNumber="3">
|
||
<emphasis id="B919EA95EF57FFABFFEEF9E5FF48F90F" bold="true" box="[100,158,1651,1668]" pageId="2" pageNumber="3">Fig. 1.</emphasis>
|
||
Morphological characteristics of
|
||
<taxonomicName id="4C6D4D04EF57FFABFE34F9E5FD46F90F" authority="Wall" authorityName="Wall" box="[446,656,1651,1668]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="latifolium">
|
||
<emphasis id="B919EA95EF57FFABFE34F9E5FDB4F90F" bold="true" box="[446,610,1651,1668]" italics="true" pageId="2" pageNumber="3">Gymnema latifolium</emphasis>
|
||
Wall
|
||
</taxonomicName>
|
||
ex. Wight. (a) Old stem showing wing-like cork (b) Living form; (c) Young branch with pairs of inflorescensces; (d) Adaxial leaf; (e) Abaxial leaf; (f) Inflorescence; (g) Dense bronze hairs on the young leaf; (h) A flower; (i) Calyx; (j) Corolla; (k) Gynostegium cylindric; (l) Pollinarium; (m) Stigma head; (n) Follicles.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8BD23687EF57FFAAFCD9F81AFEA2F9E4" blockId="2.[818,1488,1761,1978]" lastBlockId="3.[100,770,1318,1980]" lastPageId="3" lastPageNumber="4" pageId="2" pageNumber="3">
|
||
Gymlatinoside GL2 (
|
||
<emphasis id="B919EA95EF57FFABFB9EF81AFBF6F814" bold="true" box="[1044,1056,1932,1951]" pageId="2" pageNumber="3">2</emphasis>
|
||
) was obtained as a white amorphous powder, with []
|
||
<subScript id="17E934C2EF57FFABFC0EF83AFC59F831" attach="left" box="[900,911,1964,1978]" fontSize="6" pageId="2" pageNumber="3">D</subScript>
|
||
<superScript id="7C189BCFEF57FFABFC0EF809FC45F826" attach="left" box="[900,915,1951,1965]" fontSize="6" pageId="2" pageNumber="3">25</superScript>
|
||
+9.6 (
|
||
<emphasis id="B919EA95EF57FFABFC66F832FC23F83C" bold="true" box="[1004,1013,1956,1975]" italics="true" pageId="2" pageNumber="3">c</emphasis>
|
||
0.2, MeOH). Its HRESIMS showed a pseudo molecular ion peak at
|
||
<emphasis id="B919EA95EF56FFAAFEB6FABCFE9AFAB6" bold="true" box="[316,332,1322,1341]" italics="true" pageId="3" pageNumber="4">m</emphasis>
|
||
/
|
||
<emphasis id="B919EA95EF56FFAAFEDCFABCFE89FAB6" bold="true" box="[342,351,1322,1341]" italics="true" pageId="3" pageNumber="4">z</emphasis>
|
||
965.4752 [M − H]
|
||
<superScript id="7C189BCFEF56FFAAFDAAFAB0FDE6FAB9" attach="left" box="[544,560,1318,1330]" fontSize="5" pageId="3" pageNumber="4">−</superScript>
|
||
(calcd for C
|
||
<subScript id="17E934C2EF56FFAAFD2DFAA4FD6FFAB5" attach="right" box="[679,697,1330,1342]" fontSize="5" pageId="3" pageNumber="4">49</subScript>
|
||
H
|
||
<subScript id="17E934C2EF56FFAAFD42FAA4FD0CFAB5" attach="both" box="[712,730,1330,1342]" fontSize="5" pageId="3" pageNumber="4">73</subScript>
|
||
O
|
||
<subScript id="17E934C2EF56FFAAFD60FAA4FD2AFAB5" attach="left" box="[746,764,1330,1342]" fontSize="5" pageId="3" pageNumber="4">19</subScript>
|
||
, 965.4746), indicating a molecular formula of C
|
||
<subScript id="17E934C2EF56FFAAFDB2FAD8FD9CFAD1" attach="both" box="[568,586,1358,1370]" fontSize="5" pageId="3" pageNumber="4">49</subScript>
|
||
H
|
||
<subScript id="17E934C2EF56FFAAFDD0FAD8FDBAFAD1" attach="both" box="[602,620,1358,1370]" fontSize="5" pageId="3" pageNumber="4">74</subScript>
|
||
O
|
||
<subScript id="17E934C2EF56FFAAFDF1FAD8FD5BFAD1" attach="left" box="[635,653,1358,1370]" fontSize="5" pageId="3" pageNumber="4">19</subScript>
|
||
and twelve IHDs. The
|
||
<superScript id="7C189BCFEF56FFAAFF47FACBFF00FAE2" attach="right" box="[205,214,1373,1385]" fontSize="5" pageId="3" pageNumber="4">1</superScript>
|
||
H and
|
||
<superScript id="7C189BCFEF56FFAAFE93FACBFEFDFAE2" attach="right" box="[281,299,1373,1385]" fontSize="5" pageId="3" pageNumber="4">13</superScript>
|
||
C NMR spectroscopic data of
|
||
<emphasis id="B919EA95EF56FFAAFDC6FAF7FD8EFAFF" bold="true" box="[588,600,1377,1396]" pageId="3" pageNumber="4">2</emphasis>
|
||
(
|
||
<tableCitation id="C6EF033CEF56FFAAFDE3FAF7FD6CFAFF" box="[617,698,1377,1396]" captionStart="Table 1" captionStartId="4.[100,150,161,177]" captionTargetPageId="4" captionText="Table 1 1H NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" httpUri="http://table.plazi.org/id/DF12660FEF51FFADFFEEFF37FE05FF46" pageId="3" pageNumber="4" tableUuid="DF12660FEF51FFADFFEEFF37FE05FF46">Tables 1</tableCitation>
|
||
and
|
||
<tableCitation id="C6EF033CEF56FFAAFD64FAF7FD2CFAFF" box="[750,762,1377,1396]" captionStart="Table 2" captionStartId="5.[100,150,161,177]" captionTargetPageId="5" captionText="Table 2 13C NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" pageId="3" pageNumber="4">2</tableCitation>
|
||
) showed similar resonances to those of
|
||
<emphasis id="B919EA95EF56FFAAFE5DFAEBFE35FA1B" bold="true" box="[471,483,1405,1424]" pageId="3" pageNumber="4">1</emphasis>
|
||
, apart from the signals of the 2(
|
||
<emphasis id="B919EA95EF56FFAAFFF2FA0FFF55FA27" bold="true" box="[120,131,1433,1452]" italics="true" pageId="3" pageNumber="4">S</emphasis>
|
||
)-methylbutyryl moiety which were replaced by the chemical shifts of a tigloyl moiety (
|
||
<bibRefCitation id="EFFC4B76EF56FFAAFEABFA23FE1EFA43" author="Pham, H. T. T. & Hoang, M. C. & Ha, T. K. Q. & Dang, L. H. & Tran, V. O. & Nguyen, T. B. T. & Lee, C. H. & Oh, W. K." box="[289,456,1461,1480]" pageId="3" pageNumber="4" pagination="12 - 22" refId="ref11747" refString="Pham, H. T. T., Hoang, M. C., Ha, T. K. Q., Dang, L. H., Tran, V. O., Nguyen, T. B. T., Lee, C. H., Oh, W. K., 2018. Discrimination of different geographic varieties of Gymnema sylvestre, an anti-sweet plant used for the treatment of type 2 diabetes. Phytochemistry 150, 12 - 22. https: // doi. org / 10.1016 / j. phytochem. 2018.02.013." type="journal article" year="2018">Pham et al., 2018</bibRefCitation>
|
||
). A neutral fragmentation loss of 82 amu observed in positive mode of mass spectrum also established the occurrence of the tigloyl, and its linkage to C-21 was demonstrated by the HMBC correlation from H-21 [
|
||
<emphasis id="B919EA95EF56FFAAFE51F99EFE30F990" bold="true" box="[475,486,1544,1563]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFE6CF984FE24F995" attach="left" box="[486,498,1554,1566]" fontSize="5" pageId="3" pageNumber="4">H</subScript>
|
||
5.76, d,
|
||
<emphasis id="B919EA95EF56FFAAFDDAF99FFD8CF997" bold="true" box="[592,602,1545,1564]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
= 10.5 Hz) to C-1
|
||
<superScript id="7C189BCFEF56FFAAFFFAF9B6FF4AF9A7" attach="left" box="[112,156,1568,1580]" fontSize="5" pageId="3" pageNumber="4">T−21</superScript>
|
||
(
|
||
<emphasis id="B919EA95EF56FFAAFF21F9B2FF60F9BC" bold="true" box="[171,182,1572,1591]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFF3CF9BBFF16F9B2" attach="left" box="[182,192,1581,1593]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
168.4). Therefore, compound
|
||
<emphasis id="B919EA95EF56FFAAFE6EF9B2FE26F9BC" bold="true" box="[484,496,1572,1591]" pageId="3" pageNumber="4">2</emphasis>
|
||
was defined as 21-
|
||
<emphasis id="B919EA95EF56FFAAFD23F9B2FD6EF9BC" bold="true" box="[681,696,1572,1591]" italics="true" pageId="3" pageNumber="4">O</emphasis>
|
||
-tigloyl-28-
|
||
<emphasis id="B919EA95EF56FFAAFF09F9D6FF44F9D8" bold="true" box="[131,146,1600,1619]" italics="true" pageId="3" pageNumber="4">O</emphasis>
|
||
-acetyl-gymnemagenin 3-
|
||
<emphasis id="B919EA95EF56FFAAFE05F9D6FE66F9D8" bold="true" box="[399,432,1600,1620]" italics="true" pageId="3" pageNumber="4">O -β</emphasis>
|
||
-D-arabino-2-hexulopyranosyl-(1 → 3)-
|
||
<emphasis id="B919EA95EF56FFAAFFF5F9CAFF5CF9E4" bold="true" box="[127,138,1628,1647]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
-D-glucuronopyranoside.
|
||
</paragraph>
|
||
<caption id="DF12660FEF56FFAAFE2AFB7DFB43FB70" ID-DOI="http://doi.org/10.5281/zenodo.8160263" ID-Zenodo-Dep="8160263" box="[416,1173,1258,1276]" httpUri="https://zenodo.org/record/8160263/files/figure.png" pageId="3" pageNumber="4" startId="3.[416,446,1259,1276]" targetBox="[264,1323,152,1236]" targetPageId="3" targetType="figure">
|
||
<paragraph id="8BD23687EF56FFAAFE2AFB7DFB43FB70" blockId="3.[416,1173,1258,1276]" box="[416,1173,1258,1276]" pageId="3" pageNumber="4">
|
||
<emphasis id="B919EA95EF56FFAAFE2AFB7DFE0FFB77" bold="true" box="[416,473,1259,1276]" pageId="3" pageNumber="4">Fig. 2.</emphasis>
|
||
Chemical structure of isolated compounds
|
||
<emphasis id="B919EA95EF56FFAAFCC7FB7DFCBBFB77" bold="true" box="[845,877,1259,1276]" pageId="3" pageNumber="4">1–9</emphasis>
|
||
isolated from
|
||
<taxonomicName id="4C6D4D04EF56FFAAFC60FB7DFB47FB70" box="[1002,1169,1258,1276]" class="Magnoliopsida" family="Apocynaceae" genus="Gymnema" kingdom="Plantae" order="Gentianales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="latifolium">Gymnema latifolium</taxonomicName>
|
||
.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8BD23687EF56FFAAFF0FF9EEFA8EFAD3" blockId="3.[100,770,1318,1980]" lastBlockId="3.[816,1488,1321,1980]" pageId="3" pageNumber="4">
|
||
Gymlatinoside GL3 (
|
||
<emphasis id="B919EA95EF56FFAAFECDF9EEFE85F900" bold="true" box="[327,339,1656,1675]" pageId="3" pageNumber="4">3</emphasis>
|
||
) was obtained as a white amorphous powder, with []
|
||
<subScript id="17E934C2EF56FFAAFF25F90CFF6CF923" attach="left" box="[175,186,1690,1704]" fontSize="6" pageId="3" pageNumber="4">D</subScript>
|
||
<superScript id="7C189BCFEF56FFAAFF25F91BFF68F910" attach="left" box="[175,190,1677,1691]" fontSize="6" pageId="3" pageNumber="4">25</superScript>
|
||
+10.1 (
|
||
<emphasis id="B919EA95EF56FFAAFE9EF904FECBF92E" bold="true" box="[276,285,1682,1701]" italics="true" pageId="3" pageNumber="4">c</emphasis>
|
||
0.2, MeOH). Its HRESIMS showed a pseudo molecular ion peak at
|
||
<emphasis id="B919EA95EF56FFAAFE94F938FEF8F94A" bold="true" box="[286,302,1710,1729]" italics="true" pageId="3" pageNumber="4">m</emphasis>
|
||
/
|
||
<emphasis id="B919EA95EF56FFAAFEB3F938FE94F94A" bold="true" box="[313,322,1710,1729]" italics="true" pageId="3" pageNumber="4">z</emphasis>
|
||
987.4581 [M − H]
|
||
<superScript id="7C189BCFEF56FFAAFD99F93CFDF5F93D" attach="left" box="[531,547,1706,1718]" fontSize="5" pageId="3" pageNumber="4">−</superScript>
|
||
(calcd for C
|
||
<subScript id="17E934C2EF56FFAAFD2DF921FD6FF948" attach="right" box="[679,697,1719,1731]" fontSize="5" pageId="3" pageNumber="4">51</subScript>
|
||
H
|
||
<subScript id="17E934C2EF56FFAAFD42F921FD0CF948" attach="both" box="[712,730,1719,1731]" fontSize="5" pageId="3" pageNumber="4">71</subScript>
|
||
O
|
||
<subScript id="17E934C2EF56FFAAFD60F921FD2AF948" attach="left" box="[746,764,1719,1731]" fontSize="5" pageId="3" pageNumber="4">19</subScript>
|
||
, 987.4590), indicating a molecular formula of C
|
||
<subScript id="17E934C2EF56FFAAFDBFF945FD91F954" attach="both" box="[565,583,1747,1759]" fontSize="5" pageId="3" pageNumber="4">51</subScript>
|
||
H
|
||
<subScript id="17E934C2EF56FFAAFDDDF945FDBFF954" attach="both" box="[599,617,1747,1759]" fontSize="5" pageId="3" pageNumber="4">71</subScript>
|
||
O
|
||
<subScript id="17E934C2EF56FFAAFDF2F945FD5CF954" attach="left" box="[632,650,1747,1759]" fontSize="5" pageId="3" pageNumber="4">19</subScript>
|
||
and sixteen IHDs. The
|
||
<superScript id="7C189BCFEF56FFAAFF47F974FF00F965" attach="right" box="[205,214,1762,1774]" fontSize="5" pageId="3" pageNumber="4">1</superScript>
|
||
H and
|
||
<superScript id="7C189BCFEF56FFAAFE93F974FEFDF965" attach="right" box="[281,299,1762,1774]" fontSize="5" pageId="3" pageNumber="4">13</superScript>
|
||
C NMR spectroscopic data of
|
||
<emphasis id="B919EA95EF56FFAAFDC6F973FD8EF973" bold="true" box="[588,600,1765,1784]" pageId="3" pageNumber="4">3</emphasis>
|
||
(
|
||
<tableCitation id="C6EF033CEF56FFAAFDE3F973FD6CF972" box="[617,698,1765,1785]" captionStart="Table 1" captionStartId="4.[100,150,161,177]" captionTargetPageId="4" captionText="Table 1 1H NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" httpUri="http://table.plazi.org/id/DF12660FEF51FFADFFEEFF37FE05FF46" pageId="3" pageNumber="4" tableUuid="DF12660FEF51FFADFFEEFF37FE05FF46">Tables 1</tableCitation>
|
||
and
|
||
<tableCitation id="C6EF033CEF56FFAAFD64F970FD2CF972" box="[750,762,1766,1785]" captionStart="Table 2" captionStartId="5.[100,150,161,177]" captionTargetPageId="5" captionText="Table 2 13C NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" pageId="3" pageNumber="4">2</tableCitation>
|
||
) exhibited generally similar resonances to those of
|
||
<emphasis id="B919EA95EF56FFAAFDCEF897FD86F89F" bold="true" box="[580,592,1793,1812]" pageId="3" pageNumber="4">1</emphasis>
|
||
, except for the replacement of signals of the 2(
|
||
<emphasis id="B919EA95EF56FFAAFE01F88BFE40F8BB" bold="true" box="[395,406,1821,1840]" italics="true" pageId="3" pageNumber="4">S</emphasis>
|
||
)-methylbutyryl moiety with the chemical shifts of a benzoyl moiety (
|
||
<bibRefCitation id="EFFC4B76EF56FFAAFE15F8AFFD90F8C7" author="Pham, H. T. T. & Hoang, M. C. & Ha, T. K. Q. & Dang, L. H. & Tran, V. O. & Nguyen, T. B. T. & Lee, C. H. & Oh, W. K." box="[415,582,1849,1869]" pageId="3" pageNumber="4" pagination="12 - 22" refId="ref11747" refString="Pham, H. T. T., Hoang, M. C., Ha, T. K. Q., Dang, L. H., Tran, V. O., Nguyen, T. B. T., Lee, C. H., Oh, W. K., 2018. Discrimination of different geographic varieties of Gymnema sylvestre, an anti-sweet plant used for the treatment of type 2 diabetes. Phytochemistry 150, 12 - 22. https: // doi. org / 10.1016 / j. phytochem. 2018.02.013." type="journal article" year="2018">Pham et al., 2018</bibRefCitation>
|
||
). The positive mass fragment loss Δ
|
||
<emphasis id="B919EA95EF56FFAAFF7FF8C8FEC6F8E1" bold="true" box="[245,272,1886,1898]" italics="true" pageId="3" pageNumber="4">
|
||
<subScript id="17E934C2EF56FFAAFF7FF8C8FEC6F8E1" attach="left" box="[245,272,1886,1898]" fontSize="5" pageId="3" pageNumber="4">m/z</subScript>
|
||
</emphasis>
|
||
= 104 amu observed in
|
||
<emphasis id="B919EA95EF56FFAAFE72F8C3FDD2F8E3" bold="true" box="[504,516,1877,1896]" pageId="3" pageNumber="4">3</emphasis>
|
||
confirmed the existence of benzoyl. The downfield shift of C-21 (
|
||
<emphasis id="B919EA95EF56FFAAFE4EF8E7FE19F80F" bold="true" box="[452,463,1905,1924]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFE45F8ECFE0FF80D" attach="left" box="[463,473,1914,1926]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
80.3) and the HMBC cross peak from H-21 (
|
||
<emphasis id="B919EA95EF56FFAAFF5FF81BFF36F82B" bold="true" box="[213,224,1933,1952]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFF6AF800FF3AF829" attach="left" box="[224,236,1942,1954]" fontSize="5" pageId="3" pageNumber="4">H</subScript>
|
||
5.77, d,
|
||
<emphasis id="B919EA95EF56FFAAFEC9F81BFE9BF82B" bold="true" box="[323,333,1933,1952]" italics="true" pageId="3" pageNumber="4">J</emphasis>
|
||
= 10.5 Hz) to C–1
|
||
<superScript id="7C189BCFEF56FFAAFE74F81FFDFCF81E" attach="left" box="[510,554,1929,1941]" fontSize="5" pageId="3" pageNumber="4">B−21</superScript>
|
||
(
|
||
<emphasis id="B919EA95EF56FFAAFDB3F81BFD92F82B" bold="true" box="[569,580,1933,1952]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFDCEF800FD98F829" attach="left" box="[580,590,1942,1954]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
167.2) established the connection of the benzoyl to C-21. Therefore, compound
|
||
<emphasis id="B919EA95EF56FFAAFD4DF83FFD05F837" bold="true" box="[711,723,1961,1980]" pageId="3" pageNumber="4">3</emphasis>
|
||
was elucidated as 21-
|
||
<emphasis id="B919EA95EF56FFAAFC69FABFFC24FAB7" bold="true" box="[995,1010,1321,1340]" italics="true" pageId="3" pageNumber="4">O</emphasis>
|
||
-benzoyl-28-
|
||
<emphasis id="B919EA95EF56FFAAFBEDFABFFBA0FAB7" bold="true" box="[1127,1142,1321,1340]" italics="true" pageId="3" pageNumber="4">O</emphasis>
|
||
-acetyl-gymnemagenin 3-
|
||
<emphasis id="B919EA95EF56FFAAFAE7FABFFA58FAB7" bold="true" box="[1389,1422,1321,1341]" italics="true" pageId="3" pageNumber="4">O -β</emphasis>
|
||
-D-arabino-2-hexulopyranosyl-(1 → 3)-
|
||
<emphasis id="B919EA95EF56FFAAFBEEFAD3FBB9FAD3" bold="true" box="[1124,1135,1349,1368]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
-D-glucuronopyranoside.
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF56FFAAFCD9FAF7FA48F956" blockId="3.[816,1488,1321,1980]" pageId="3" pageNumber="4">
|
||
Gymlatinoside GL4 (
|
||
<emphasis id="B919EA95EF56FFAAFB9EFAF7FBF6FAFF" bold="true" box="[1044,1056,1377,1396]" pageId="3" pageNumber="4">4</emphasis>
|
||
) was obtained as a white amorphous powder, with []
|
||
<subScript id="17E934C2EF56FFAAFCF4FA15FC5FFA1A" attach="left" box="[894,905,1411,1425]" fontSize="6" pageId="3" pageNumber="4">D</subScript>
|
||
<superScript id="7C189BCFEF56FFAAFCF4FAE0FC5BFA0F" attach="left" box="[894,909,1398,1412]" fontSize="6" pageId="3" pageNumber="4">25</superScript>
|
||
+ 22.1 (
|
||
<emphasis id="B919EA95EF56FFAAFC78FAEDFC2DFA05" bold="true" box="[1010,1019,1403,1422]" italics="true" pageId="3" pageNumber="4">c</emphasis>
|
||
0.2, MeOH), was found to possess a molecular formula of C
|
||
<subScript id="17E934C2EF56FFAAFC24FA36FC16FA27" attach="both" box="[942,960,1440,1452]" fontSize="5" pageId="3" pageNumber="4">51</subScript>
|
||
H
|
||
<subScript id="17E934C2EF56FFAAFC5AFA36FC34FA27" attach="both" box="[976,994,1440,1452]" fontSize="5" pageId="3" pageNumber="4">76</subScript>
|
||
O
|
||
<subScript id="17E934C2EF56FFAAFC7BFA36FBD5FA27" attach="left" box="[1009,1027,1440,1452]" fontSize="5" pageId="3" pageNumber="4">20</subScript>
|
||
and fourteen IHDs based on the HRESIMS ion peak at
|
||
<emphasis id="B919EA95EF56FFAAFCF5FA25FC59FA4D" bold="true" box="[895,911,1459,1478]" italics="true" pageId="3" pageNumber="4">m</emphasis>
|
||
/
|
||
<emphasis id="B919EA95EF56FFAAFC10FA25FC75FA4D" bold="true" box="[922,931,1459,1478]" italics="true" pageId="3" pageNumber="4">z</emphasis>
|
||
1007.4826 [M − H]
|
||
<superScript id="7C189BCFEF56FFAAFBFBFA39FB57FA30" attach="left" box="[1137,1153,1455,1467]" fontSize="5" pageId="3" pageNumber="4">−</superScript>
|
||
(calcd for C
|
||
<subScript id="17E934C2EF56FFAAFB73FA2AFADDFA43" attach="right" box="[1273,1291,1468,1480]" fontSize="5" pageId="3" pageNumber="4">51</subScript>
|
||
H
|
||
<subScript id="17E934C2EF56FFAAFA91FA2AFAFBFA43" attach="both" box="[1307,1325,1468,1480]" fontSize="5" pageId="3" pageNumber="4">75</subScript>
|
||
O
|
||
<subScript id="17E934C2EF56FFAAFAB6FA2AFA98FA43" attach="left" box="[1340,1358,1468,1480]" fontSize="5" pageId="3" pageNumber="4">20</subScript>
|
||
, 1007.4852). Mass fragmentation in the positive mode showed the neutral losses of two acetyls (2 × 42 amu) and one tigloyl (82 amu). The
|
||
<superScript id="7C189BCFEF56FFAAFAE9FA71FABAFA78" attach="right" box="[1379,1388,1511,1523]" fontSize="5" pageId="3" pageNumber="4">1</superScript>
|
||
H and
|
||
<superScript id="7C189BCFEF56FFAAFA3AFA71FA14FA78" attach="right" box="[1456,1474,1511,1523]" fontSize="5" pageId="3" pageNumber="4">13</superScript>
|
||
C NMR spectroscopic data of
|
||
<emphasis id="B919EA95EF56FFAAFBC3F990FB83F992" bold="true" box="[1097,1109,1542,1561]" pageId="3" pageNumber="4">4</emphasis>
|
||
(
|
||
<tableCitation id="C6EF033CEF56FFAAFBE3F990FB6BF992" box="[1129,1213,1542,1561]" captionStart="Table 1" captionStartId="4.[100,150,161,177]" captionTargetPageId="4" captionText="Table 1 1H NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" httpUri="http://table.plazi.org/id/DF12660FEF51FFADFFEEFF37FE05FF46" pageId="3" pageNumber="4" tableUuid="DF12660FEF51FFADFFEEFF37FE05FF46">Tables 1</tableCitation>
|
||
and
|
||
<tableCitation id="C6EF033CEF56FFAAFB7DF990FAD5F992" box="[1271,1283,1542,1561]" captionStart="Table 2" captionStartId="5.[100,150,161,177]" captionTargetPageId="5" captionText="Table 2 13C NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" pageId="3" pageNumber="4">2</tableCitation>
|
||
) showed similar resonances to those of
|
||
<quantity id="4C959B62EF56FFAAFC7FF9B4FBCCF9BE" box="[1013,1050,1570,1589]" metricMagnitude="-2" metricUnit="m" metricValue="5.08" pageId="3" pageNumber="4" unit="in" value="2.0">
|
||
<emphasis id="B919EA95EF56FFAAFC7FF9B4FBD7F9BE" bold="true" box="[1013,1025,1570,1589]" pageId="3" pageNumber="4">2</emphasis>
|
||
in
|
||
</quantity>
|
||
the aglycone and glycosyl moieties with some differences occurred in the positions of acyl substitutions. Further investigation of the acylation shifts and HMBC spectra revealed that the tigloyl was attached to C-21 (
|
||
<emphasis id="B919EA95EF56FFAAFBC2F9E0FB85F902" bold="true" box="[1096,1107,1654,1673]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFBD9F9E9FB8BF900" attach="left" box="[1107,1117,1663,1675]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
76.7) and two acetyls were substituted to C-16 (
|
||
<emphasis id="B919EA95EF56FFAAFC08F904FC5BF92E" bold="true" box="[898,909,1682,1701]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFC07F90DFC41F92C" attach="left" box="[909,919,1691,1703]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
68.7) and C-22 (
|
||
<emphasis id="B919EA95EF56FFAAFBBEF904FBE9F92E" bold="true" box="[1076,1087,1682,1701]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFBB5F90DFB9FF92C" attach="left" box="[1087,1097,1691,1703]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
72.0), respectively. Therefore, compound
|
||
<emphasis id="B919EA95EF56FFAAFCB8F938FCE8F94A" bold="true" box="[818,830,1710,1729]" pageId="3" pageNumber="4">4</emphasis>
|
||
was determined as 21-
|
||
<emphasis id="B919EA95EF56FFAAFB9CF938FBF3F94A" bold="true" box="[1046,1061,1710,1729]" italics="true" pageId="3" pageNumber="4">O</emphasis>
|
||
-tigloyl-16,22-
|
||
<emphasis id="B919EA95EF56FFAAFB21F938FB6CF94A" bold="true" box="[1195,1210,1710,1729]" italics="true" pageId="3" pageNumber="4">O</emphasis>
|
||
-diacetyl gymnemagenin 3-
|
||
<emphasis id="B919EA95EF56FFAAFA33F938FCEBF957" bold="true" italics="true" pageId="3" pageNumber="4">O - β</emphasis>
|
||
-D-arabino-2-hexulopyranosyl-(1 → 3)-
|
||
<emphasis id="B919EA95EF56FFAAFB23F95FFB62F957" bold="true" box="[1193,1204,1737,1756]" italics="true" pageId="3" pageNumber="4">β</emphasis>
|
||
-D-glucuronopyranoside.
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF56FFAFFCD9F973FF47F981" blockId="3.[816,1488,1321,1980]" lastBlockId="6.[100,770,1360,1991]" lastPageId="6" lastPageNumber="7" pageId="3" pageNumber="4">
|
||
<materialsCitation id="3B053CDAEF56FFAFFCD9F973FF5AF981" collectionCode="M, H, C, HSQC, NMR, J, HMBC, O" lastPageId="6" lastPageNumber="7" pageId="3" pageNumber="4" specimenCode="GL5, C42, H70, O13, H69, 781.4738, C 16.1, C 33.3, C 24.4, C 17.4, H 1.03, H 1.32, C 28.6, H 1.35, C 27.5, C12-13, C 107.3, C 89.2, C 78.7" specimenCount="1">
|
||
Gymlatinoside
|
||
<specimenCode id="DBCB9EFCEF56FFAAFC6BF973FBD1F973" box="[993,1031,1765,1784]" collectionCode="GL" country="United Kingdom" lsid="urn:lsid:biocol.org:col:14516" name="University of Glasgow" pageId="3" pageNumber="4" type="Herbarium">GL5</specimenCode>
|
||
(
|
||
<emphasis id="B919EA95EF56FFAAFB9FF970FBF7F972" bold="true" box="[1045,1057,1766,1785]" pageId="3" pageNumber="4">5</emphasis>
|
||
) was obtained as an amorphous powder with []
|
||
<subScript id="17E934C2EF56FFAAFCC0F89EFC83F89D" attach="left" box="[842,853,1800,1814]" fontSize="6" pageId="3" pageNumber="4">D</subScript>
|
||
<superScript id="7C189BCFEF56FFAAFCC0F96CFC8FF883" attach="left" box="[842,857,1786,1800]" fontSize="6" pageId="3" pageNumber="4">25</superScript>
|
||
+13.4 (
|
||
<emphasis id="B919EA95EF56FFAAFC25F896FC6EF898" bold="true" box="[943,952,1792,1811]" italics="true" pageId="3" pageNumber="4">c</emphasis>
|
||
0.2, MeOH). The molecular formula
|
||
<specimenCode id="DBCB9EFCEF56FFAAFA97F969FAEAF89F" box="[1309,1340,1791,1812]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
C
|
||
<subScript id="17E934C2EF56FFAAFAA0F89EFAEAF89F" attach="both" box="[1322,1340,1800,1812]" fontSize="5" pageId="3" pageNumber="4">42</subScript>
|
||
</specimenCode>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFAB6F896FA88F89F" box="[1340,1374,1792,1812]" collectionCode="H" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">
|
||
H
|
||
<subScript id="17E934C2EF56FFAAFAC6F89EFA88F89F" attach="both" box="[1356,1374,1800,1812]" fontSize="5" pageId="3" pageNumber="4">70</subScript>
|
||
</specimenCode>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFAD4F969FA56F89F" box="[1374,1408,1791,1812]" collectionCode="O" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="3" pageNumber="4" type="Herbarium">
|
||
O
|
||
<subScript id="17E934C2EF56FFAAFAE4F89EFA56F89F" attach="left" box="[1390,1408,1800,1812]" fontSize="5" pageId="3" pageNumber="4">13</subScript>
|
||
</specimenCode>
|
||
was determined by a quasimolecular ion peak at
|
||
<emphasis id="B919EA95EF56FFAAFB32F88DFB0BF8A5" bold="true" box="[1208,1245,1819,1838]" italics="true" pageId="3" pageNumber="4">m/z</emphasis>
|
||
781.4746 [
|
||
<collectionCode id="ED7CAE42EF56FFAAFACFF88AFA8DF8A4" box="[1349,1371,1820,1839]" country="Germany" lsid="urn:lsid:biocol.org:col:15637" name="Botanische Staatssammlung München" pageId="3" pageNumber="4" type="Herbarium">M</collectionCode>
|
||
–
|
||
<collectionCode id="ED7CAE42EF56FFAAFAFAF88AFA55F8A4" box="[1392,1411,1820,1839]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
|
||
]
|
||
<superScript id="7C189BCFEF56FFAAFA03F881FA47F8A8" attach="left" box="[1417,1425,1815,1827]" fontSize="5" pageId="3" pageNumber="4">–</superScript>
|
||
(calcd for
|
||
<specimenCode id="DBCB9EFCEF56FFAAFCDEF8A1FCA2F8C7" box="[852,884,1847,1868]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
C
|
||
<subScript id="17E934C2EF56FFAAFCE8F8D6FCA2F8C7" attach="right" box="[866,884,1856,1868]" fontSize="5" pageId="3" pageNumber="4">42</subScript>
|
||
</specimenCode>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFCFEF8AEFC43F8C7" box="[884,917,1848,1868]" collectionCode="H" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">
|
||
H
|
||
<subScript id="17E934C2EF56FFAAFC09F8D6FC43F8C7" attach="both" box="[899,917,1856,1868]" fontSize="5" pageId="3" pageNumber="4">69</subScript>
|
||
</specimenCode>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFC1FF8A1FC61F8C7" box="[917,951,1847,1868]" collectionCode="O" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="3" pageNumber="4" type="Herbarium">
|
||
O
|
||
<subScript id="17E934C2EF56FFAAFC2FF8D6FC61F8C7" attach="left" box="[933,951,1856,1868]" fontSize="5" pageId="3" pageNumber="4">13</subScript>
|
||
</specimenCode>
|
||
,
|
||
<specimenCode id="DBCB9EFCEF56FFAAFC4FF8A1FBF6F8C1" box="[965,1056,1847,1866]" collectionCode="O" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="3" pageNumber="4" type="Herbarium">781.4738</specimenCode>
|
||
) in HRESIMS.
|
||
<superScript id="7C189BCFEF56FFAAFB3AF8A5FB6FF8B4" attach="right" box="[1200,1209,1843,1855]" fontSize="5" pageId="3" pageNumber="4">1</superScript>
|
||
<collectionCode id="ED7CAE42EF56FFAAFB33F8AEFB1DF8C0" box="[1209,1227,1848,1867]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
|
||
,
|
||
<superScript id="7C189BCFEF56FFAAFB5CF8A5FB3EF8B4" attach="right" box="[1238,1256,1843,1855]" fontSize="5" pageId="3" pageNumber="4">13</superScript>
|
||
<collectionCode id="ED7CAE42EF56FFAAFB62F8A1FB23F8C1" box="[1256,1269,1847,1866]" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">C</collectionCode>
|
||
and
|
||
<collectionCode id="ED7CAE42EF56FFAAFAA2F8A1FAB6F8C1" box="[1320,1376,1847,1866]" pageId="3" pageNumber="4">HSQC</collectionCode>
|
||
<collectionCode id="ED7CAE42EF56FFAAFAE2F8AEFA4EF8C0" box="[1384,1432,1848,1867]" country="Netherlands" httpUri="http://grbio.org/cool/jyde-k516" name="Natuurhistorisch Museum" pageId="3" pageNumber="4">NMR</collectionCode>
|
||
spectroscopic data of the aglycone (
|
||
<tableCitation id="C6EF033CEF56FFAAFBE2F8C5FB6CF8ED" box="[1128,1210,1875,1894]" captionStart="Table 1" captionStartId="4.[100,150,161,177]" captionTargetPageId="4" captionText="Table 1 1H NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" httpUri="http://table.plazi.org/id/DF12660FEF51FFADFFEEFF37FE05FF46" pageId="3" pageNumber="4" tableUuid="DF12660FEF51FFADFFEEFF37FE05FF46">Tables 1</tableCitation>
|
||
and
|
||
<tableCitation id="C6EF033CEF56FFAAFB64F8C5FB2CF8ED" box="[1262,1274,1875,1894]" captionStart="Table 2" captionStartId="5.[100,150,161,177]" captionTargetPageId="5" captionText="Table 2 13C NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" pageId="3" pageNumber="4">2</tableCitation>
|
||
) exhibited signals for seven methyl groups: (
|
||
<emphasis id="B919EA95EF56FFAAFB8CF8F9FBC7F809" bold="true" box="[1030,1041,1903,1922]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFB9BF8EEFBCBF80F" attach="left" box="[1041,1053,1912,1924]" fontSize="5" pageId="3" pageNumber="4">
|
||
<collectionCode id="ED7CAE42EF56FFAAFB9BF8EEFBCBF80F" box="[1041,1053,1912,1924]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
|
||
</subScript>
|
||
0.87,
|
||
<emphasis id="B919EA95EF56FFAAFBDDF8F9FBB4F809" bold="true" box="[1111,1122,1903,1922]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFBE8F8EEFB48F809" box="[1122,1182,1903,1924]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFBE8F8EEFBBAF80F" attach="left" box="[1122,1132,1912,1924]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
16.1
|
||
</specimenCode>
|
||
), (
|
||
<emphasis id="B919EA95EF56FFAAFB3DF8F9FB14F809" bold="true" box="[1207,1218,1903,1922]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFB48F8EEFB18F80F" attach="left" box="[1218,1230,1912,1924]" fontSize="5" pageId="3" pageNumber="4">
|
||
<collectionCode id="ED7CAE42EF56FFAAFB48F8EEFB18F80F" box="[1218,1230,1912,1924]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
|
||
</subScript>
|
||
0.93,
|
||
<emphasis id="B919EA95EF56FFAAFA83F8F9FAC2F809" bold="true" box="[1289,1300,1903,1922]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFA9EF8EEFA86F809" box="[1300,1360,1903,1924]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFA9EF8EEFAC8F80F" attach="left" box="[1300,1310,1912,1924]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
33.3
|
||
</specimenCode>
|
||
), (
|
||
<emphasis id="B919EA95EF56FFAAFAE3F8F9FAA2F809" bold="true" box="[1385,1396,1903,1922]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFAF9F8EEFAA9F80F" attach="left" box="[1395,1407,1912,1924]" fontSize="5" pageId="3" pageNumber="4">
|
||
<collectionCode id="ED7CAE42EF56FFAAFAF9F8EEFAA9F80F" box="[1395,1407,1912,1924]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
|
||
</subScript>
|
||
0.95,
|
||
<emphasis id="B919EA95EF56FFAAFA30F8F9FA13F809" bold="true" box="[1466,1477,1903,1922]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFA4FF8EEFC89F815" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFA4FF8EEFA19F80F" attach="left" box="[1477,1487,1912,1924]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
24.4
|
||
</specimenCode>
|
||
), (
|
||
<emphasis id="B919EA95EF56FFAAFCFDF81DFC54F815" bold="true" box="[887,898,1931,1950]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<subScript id="17E934C2EF56FFAAFC08F802FC58F82B" attach="left" box="[898,910,1940,1952]" fontSize="5" pageId="3" pageNumber="4">
|
||
<collectionCode id="ED7CAE42EF56FFAAFC08F802FC58F82B" box="[898,910,1940,1952]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
|
||
</subScript>
|
||
0.98,
|
||
<emphasis id="B919EA95EF56FFAAFC40F81DFC03F815" bold="true" box="[970,981,1931,1950]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFC5EF802FBC7F815" box="[980,1041,1931,1952]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFC5EF802FC08F82B" attach="left" box="[980,990,1940,1952]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
17.4
|
||
</specimenCode>
|
||
), (
|
||
<emphasis id="B919EA95EF56FFAAFBA0F81DFBE3F815" bold="true" box="[1066,1077,1931,1950]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFBBFF802FBA5F815" box="[1077,1139,1931,1952]" collectionCode="H" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFBBFF802FB97F82B" attach="left" box="[1077,1089,1940,1952]" fontSize="5" pageId="3" pageNumber="4">H</subScript>
|
||
1.03
|
||
</specimenCode>
|
||
,
|
||
<emphasis id="B919EA95EF56FFAAFBF6F81DFB51F815" bold="true" box="[1148,1159,1931,1950]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFB0DF802FB12F815" box="[1159,1220,1931,1952]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFB0DF802FB47F82B" attach="left" box="[1159,1169,1940,1952]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
17.4
|
||
</specimenCode>
|
||
), (
|
||
<emphasis id="B919EA95EF56FFAAFB57F81DFB3EF815" bold="true" box="[1245,1256,1931,1950]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFB62F802FAF3F815" box="[1256,1317,1931,1952]" collectionCode="H" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFB62F802FB22F82B" attach="left" box="[1256,1268,1940,1952]" fontSize="5" pageId="3" pageNumber="4">H</subScript>
|
||
1.32
|
||
</specimenCode>
|
||
,
|
||
<emphasis id="B919EA95EF56FFAAFAA5F81DFAECF815" bold="true" box="[1327,1338,1931,1950]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFAB0F802FAA1F815" box="[1338,1399,1931,1952]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFAB0F802FA92F82B" attach="left" box="[1338,1348,1940,1952]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
28.6
|
||
</specimenCode>
|
||
), and (
|
||
<emphasis id="B919EA95EF56FFAAFA32F81DFA15F815" bold="true" box="[1464,1475,1931,1950]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFA49F802FC88F831" collectionCode="H" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFA49F802FA19F82B" attach="left" box="[1475,1487,1940,1952]" fontSize="5" pageId="3" pageNumber="4">H</subScript>
|
||
1.35
|
||
</specimenCode>
|
||
,
|
||
<emphasis id="B919EA95EF56FFAAFCE1F831FCA0F831" bold="true" box="[875,886,1959,1978]" italics="true" pageId="3" pageNumber="4">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF56FFAAFCFCF826FC6EF831" box="[886,952,1959,1980]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
<subScript id="17E934C2EF56FFAAFCFCF826FC56F837" attach="left" box="[886,896,1968,1980]" fontSize="5" pageId="3" pageNumber="4">C</subScript>
|
||
27.5
|
||
</specimenCode>
|
||
). The double bond at
|
||
<specimenCode id="DBCB9EFCEF56FFAAFB12F831FB18F837" box="[1176,1230,1959,1980]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="3" pageNumber="4" type="Herbarium">
|
||
C
|
||
<subScript id="17E934C2EF56FFAAFB2FF826FB18F837" attach="left" box="[1189,1230,1968,1980]" fontSize="5" pageId="3" pageNumber="4">12-13</subScript>
|
||
</specimenCode>
|
||
was demonstrated by the signals of olefinic group [
|
||
<emphasis id="B919EA95EF50FFACFEDEF8F8FE89F80A" bold="true" box="[340,351,1902,1921]" italics="true" pageId="5" pageNumber="6">δ</emphasis>
|
||
<subScript id="17E934C2EF50FFACFED5F8E1FE57F808" attach="left" box="[351,385,1911,1923]" fontSize="5" pageId="5" pageNumber="6">H-12</subScript>
|
||
5.24 (br s),
|
||
<emphasis id="B919EA95EF50FFACFE7FF8F8FDD6F80A" bold="true" box="[501,512,1902,1921]" italics="true" pageId="5" pageNumber="6">δ</emphasis>
|
||
<subScript id="17E934C2EF50FFACFD8AF8E1FDF7F808" attach="left" box="[512,545,1911,1923]" fontSize="5" pageId="5" pageNumber="6">C-12</subScript>
|
||
123.3] and
|
||
<subScript id="17E934C2EF50FFACFD1EF8F8FD17F808" attach="left" box="[660,705,1902,1923]" fontSize="5" pageId="5" pageNumber="6">δC-13</subScript>
|
||
143.8. Signals of fifteen oxygenated carbons can be observed including two anomeric carbons at
|
||
<emphasis id="B919EA95EF50FFACFEADF833FEE4F833" bold="true" box="[295,306,1957,1976]" italics="true" pageId="5" pageNumber="6">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF50FFACFEB8F839FEA1F832" box="[306,375,1958,1979]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="5" pageNumber="6" type="Herbarium">
|
||
<subScript id="17E934C2EF50FFACFEB8F839FEEAF830" attach="left" box="[306,316,1967,1979]" fontSize="5" pageId="5" pageNumber="6">C</subScript>
|
||
107.3
|
||
</specimenCode>
|
||
and 106.2, ten other glycosyl carbons and three others of the main skeleton. These
|
||
<collectionCode id="ED7CAE42EF50FFACFB53F8F8FADFF80A" box="[1241,1289,1902,1921]" country="Netherlands" httpUri="http://grbio.org/cool/jyde-k516" name="Natuurhistorisch Museum" pageId="5" pageNumber="6">NMR</collectionCode>
|
||
data suggested the structure of a longispinogenin moiety with two attached sugars (
|
||
<bibRefCitation id="EFFC4B76EF50FFACFA10F81CFC4BF832" author="Pham, H. T. T. & Hoang, M. C. & Ha, T. K. Q. & Dang, L. H. & Tran, V. O. & Nguyen, T. B. T. & Lee, C. H. & Oh, W. K." pageId="5" pageNumber="6" pagination="12 - 22" refId="ref11747" refString="Pham, H. T. T., Hoang, M. C., Ha, T. K. Q., Dang, L. H., Tran, V. O., Nguyen, T. B. T., Lee, C. H., Oh, W. K., 2018. Discrimination of different geographic varieties of Gymnema sylvestre, an anti-sweet plant used for the treatment of type 2 diabetes. Phytochemistry 150, 12 - 22. https: // doi. org / 10.1016 / j. phytochem. 2018.02.013." type="journal article" year="2018">Pham et al., 2018</bibRefCitation>
|
||
). Sugar analysis and
|
||
<collectionCode id="ED7CAE42EF50FFACFBE2F830FB4EF832" box="[1128,1176,1958,1977]" country="Netherlands" httpUri="http://grbio.org/cool/jyde-k516" name="Natuurhistorisch Museum" pageId="5" pageNumber="6">NMR</collectionCode>
|
||
data suggested the sugar
|
||
<typeStatus id="54D68825EF50FFACFA07F830FA60F832" box="[1421,1462,1958,1977]" pageId="5" pageNumber="6">type</typeStatus>
|
||
of this structure is glucose which is identified to be in
|
||
<emphasis id="B919EA95EF53FFAFFDD9FAC6FD88FAE8" bold="true" box="[595,606,1360,1379]" italics="true" pageId="6" pageNumber="7">β</emphasis>
|
||
-configuration by the coupling constant
|
||
<emphasis id="B919EA95EF53FFAFFEB1FAFAFE93FAF4" bold="true" box="[315,325,1388,1407]" italics="true" pageId="6" pageNumber="7">
|
||
<collectionCode id="ED7CAE42EF53FFAFFEB1FAFAFE93FAF4" box="[315,325,1388,1407]" country="South Africa" lsid="urn:lsid:biocol.org:col:14647" name="University of the Witwatersrand" pageId="6" pageNumber="7" type="Herbarium">J</collectionCode>
|
||
</emphasis>
|
||
= 7.5 Hz of their anomeric protons. Their positions at C-3 and C-28 were evident by the
|
||
<collectionCode id="ED7CAE42EF53FFAFFD8AFA1EFDEBFA10" box="[512,573,1416,1435]" pageId="6" pageNumber="7">HMBC</collectionCode>
|
||
correlations from H-1′ (4.97, d,
|
||
<emphasis id="B919EA95EF53FFAFFF59FA32FF0BFA3C" bold="true" box="[211,221,1444,1463]" italics="true" pageId="6" pageNumber="7">
|
||
<collectionCode id="ED7CAE42EF53FFAFFF59FA32FF0BFA3C" box="[211,221,1444,1463]" country="South Africa" lsid="urn:lsid:biocol.org:col:14647" name="University of the Witwatersrand" pageId="6" pageNumber="7" type="Herbarium">J</collectionCode>
|
||
</emphasis>
|
||
= 7.5 Hz) to C-3 (
|
||
<emphasis id="B919EA95EF53FFAFFE04FA35FE4FFA3D" bold="true" box="[398,409,1443,1462]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF53FFAFFE13FA3BFE02FA3C" box="[409,468,1444,1465]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="7" type="Herbarium">
|
||
<subScript id="17E934C2EF53FFAFFE13FA3BFE75FA32" attach="left" box="[409,419,1453,1465]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
89.2
|
||
</specimenCode>
|
||
) and H-1′′ (4.94, d,
|
||
<emphasis id="B919EA95EF53FFAFFD1CFA32FD76FA3C" bold="true" box="[662,672,1444,1463]" italics="true" pageId="6" pageNumber="7">
|
||
<collectionCode id="ED7CAE42EF53FFAFFD1CFA32FD76FA3C" box="[662,672,1444,1463]" country="South Africa" lsid="urn:lsid:biocol.org:col:14647" name="University of the Witwatersrand" pageId="6" pageNumber="7" type="Herbarium">J</collectionCode>
|
||
</emphasis>
|
||
= 7.5 Hz) to C-28 (
|
||
<emphasis id="B919EA95EF53FFAFFF3CFA29FF17FA59" bold="true" box="[182,193,1471,1490]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<specimenCode id="DBCB9EFCEF53FFAFFF4BFA5EFF2AFA58" box="[193,252,1472,1492]" collectionCode="C" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="7" type="Herbarium">
|
||
<subScript id="17E934C2EF53FFAFFF4BFA5EFF1DFA5F" attach="left" box="[193,203,1480,1492]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
78.7
|
||
</specimenCode>
|
||
) (
|
||
<figureCitation id="13562A02EF53FFAFFE9AFA29FE93FA58" box="[272,325,1471,1491]" captionStart="Fig" captionStartId="6.[491,521,1297,1314]" captionTargetBox="[151,1436,152,1275]" captionTargetId="graphics-624@6.[151,1436,152,1274]" captionTargetPageId="6" captionText="Fig. 3. Key COSY and HMBC correlations of compounds 1, 5, 6 and 7." figureDoi="http://doi.org/10.5281/zenodo.8160265" httpUri="https://zenodo.org/record/8160265/files/figure.png" pageId="6" pageNumber="7">Fig. 3</figureCitation>
|
||
). Consequently, compound
|
||
<emphasis id="B919EA95EF53FFAFFDC6FA56FD8EFA58" bold="true" box="[588,600,1472,1491]" pageId="6" pageNumber="7">5</emphasis>
|
||
was elucidated as 3-
|
||
<emphasis id="B919EA95EF53FFAFFFFDFA4DFF4EFA65" bold="true" box="[119,152,1499,1519]" italics="true" pageId="6" pageNumber="7">
|
||
<collectionCode id="ED7CAE42EF53FFAFFFFDFA4DFF50FA65" box="[119,134,1499,1518]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="6" pageNumber="7" type="Herbarium">O</collectionCode>
|
||
-β
|
||
</emphasis>
|
||
-D-glucopyranosyl longispinogenin 28-
|
||
<emphasis id="B919EA95EF53FFAFFD97FA4DFDE8FA65" bold="true" box="[541,574,1499,1519]" italics="true" pageId="6" pageNumber="7">
|
||
<collectionCode id="ED7CAE42EF53FFAFFD97FA4DFDFAFA65" box="[541,556,1499,1518]" country="Norway" lsid="urn:lsid:biocol.org:col:13093" name="Botanical Museum - University of Oslo" pageId="6" pageNumber="7" type="Herbarium">O</collectionCode>
|
||
-β
|
||
</emphasis>
|
||
-D-glucuronopyranoside
|
||
</materialsCitation>
|
||
.
|
||
</paragraph>
|
||
<caption id="DF12660FEF51FFADFFEEFF37FE05FF46" ID-Table-UUID="DF12660FEF51FFADFFEEFF37FE05FF46" httpUri="http://table.plazi.org/id/DF12660FEF51FFADFFEEFF37FE05FF46" pageId="4" pageNumber="5" startId="4.[100,150,161,177]" targetBox="[116,1456,222,1905]" targetIsTable="true" targetPageId="4" targetType="table">
|
||
<paragraph id="8BD23687EF51FFADFFEEFF37FF7EFF39" blockId="4.[100,640,161,205]" box="[100,168,161,178]" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFFEEFF37FF7EFF39" bold="true" box="[100,168,161,178]" pageId="4" pageNumber="5">Table 1</emphasis>
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF51FFADFFEEFF20FD56FF40" blockId="4.[100,640,161,205]" box="[100,640,182,203]" pageId="4" pageNumber="5">
|
||
<superScript id="7C189BCFEF51FFADFFEEFF20FFBAFF49" attach="right" box="[100,108,182,194]" fontSize="5" pageId="4" pageNumber="5">1</superScript>
|
||
H NMR spectroscopic data (in Pyridine-
|
||
<emphasis id="B919EA95EF51FFADFE4BFF2CFE1DFF40" bold="true" box="[449,459,186,203]" italics="true" pageId="4" pageNumber="5">d</emphasis>
|
||
) of compounds 1-7.
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF51FFADFE41FF57FE05FF46" blockId="4.[100,640,161,205]" box="[459,467,193,205]" pageId="4" pageNumber="5">
|
||
<subScript id="17E934C2EF51FFADFE41FF57FE05FF46" attach="left" box="[459,467,193,205]" fontSize="5" pageId="4" pageNumber="5">5</subScript>
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8BD23687EF51FFADFFFEFF75FD89F8FA" pageId="4" pageNumber="5">
|
||
<table id="F96DC427EF510056FFFEFF48FA66F8FA" box="[116,1456,222,1905]" colsContinueIn="5.[116,1455,222,1793]" gridcols="8" gridrows="65" pageId="4" pageNumber="5">
|
||
<tr id="355D34C5EF510056FFFEFF48FA66FF7A" box="[116,1456,222,241]" gridrow="0" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFF48FF46FF7A" box="[116,144,222,241]" gridcol="0" gridrow="0" pageId="4" pageNumber="5">No.</th>
|
||
<th id="768C5DB9EF510056FF3FFF48FE9CFF7A" box="[181,330,222,241]" gridcol="1" gridrow="0" pageId="4" pageNumber="5">1a</th>
|
||
<th id="768C5DB9EF510056FEFAFF48FDD3FF7A" box="[368,517,222,241]" gridcol="2" gridrow="0" pageId="4" pageNumber="5">2a</th>
|
||
<th id="768C5DB9EF510056FDA6FF48FD17FF7A" box="[556,705,222,241]" gridcol="3" gridrow="0" pageId="4" pageNumber="5">3a</th>
|
||
<th id="768C5DB9EF510056FD6DFF48FCAAFF7A" box="[743,892,222,241]" gridcol="4" gridrow="0" pageId="4" pageNumber="5">4b</th>
|
||
<th id="768C5DB9EF510056FC29FF48FBEEFF7A" box="[931,1080,222,241]" gridcol="5" gridrow="0" pageId="4" pageNumber="5">5a</th>
|
||
<th id="768C5DB9EF510056FBD4FF48FB25FF7A" box="[1118,1267,222,241]" gridcol="6" gridrow="0" pageId="4" pageNumber="5">6a</th>
|
||
<th id="768C5DB9EF510056FA90FF48FA66FF7A" box="[1306,1456,222,241]" gridcol="7" gridrow="0" pageId="4" pageNumber="5">7 b</th>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFE98FA66FE97" box="[116,1456,270,284]" gridrow="1" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFE98FF46FE97" box="[116,144,270,284]" gridcol="0" gridrow="1" pageId="4" pageNumber="5">1</th>
|
||
<td id="768C5DB9EF510056FF3FFE98FE9CFE97" box="[181,330,270,284]" gridcol="1" gridrow="1" pageId="4" pageNumber="5">0.88, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFE98FDD3FE97" box="[368,517,270,284]" gridcol="2" gridrow="1" pageId="4" pageNumber="5">0.90, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FE98FD17FE97" box="[556,705,270,284]" gridcol="3" gridrow="1" pageId="4" pageNumber="5">0.98, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFE98FCAAFE97" box="[743,892,270,284]" gridcol="4" gridrow="1" pageId="4" pageNumber="5">0.89, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FE98FBEEFE97" box="[931,1080,270,284]" gridcol="5" gridrow="1" pageId="4" pageNumber="5">0.90, ovelap</td>
|
||
<td id="768C5DB9EF510056FBD4FE98FB25FE97" box="[1118,1267,270,284]" gridcol="6" gridrow="1" pageId="4" pageNumber="5">0.88, ovelap</td>
|
||
<td id="768C5DB9EF510056FA90FE98FA66FE97" box="[1306,1456,270,284]" gridcol="7" gridrow="1" pageId="4" pageNumber="5">0.88, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFEB3FA66FEB8" box="[116,1456,293,307]" gridrow="2" pageId="4" pageNumber="5" rowspan-0="1">
|
||
<td id="768C5DB9EF510056FF3FFEB3FE9CFEB8" box="[181,330,293,307]" gridcol="1" gridrow="2" pageId="4" pageNumber="5">1.38, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFEB3FDD3FEB8" box="[368,517,293,307]" gridcol="2" gridrow="2" pageId="4" pageNumber="5">1.42, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FEB3FD17FEB8" box="[556,705,293,307]" gridcol="3" gridrow="2" pageId="4" pageNumber="5">1.41, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFEB3FCAAFEB8" box="[743,892,293,307]" gridcol="4" gridrow="2" pageId="4" pageNumber="5">1.41, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FEB3FBEEFEB8" box="[931,1080,293,307]" gridcol="5" gridrow="2" pageId="4" pageNumber="5">1.43, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FEB3FB25FEB8" box="[1118,1267,293,307]" gridcol="6" gridrow="2" pageId="4" pageNumber="5">1.41, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FEB3FA66FEB8" box="[1306,1456,293,307]" gridcol="7" gridrow="2" pageId="4" pageNumber="5">1.38, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFEAAFA66FEC1" box="[116,1456,316,330]" gridrow="3" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFEAAFF46FEC1" box="[116,144,316,330]" gridcol="0" gridrow="3" pageId="4" pageNumber="5">2</th>
|
||
<td id="768C5DB9EF510056FF3FFEAAFE9CFEC1" box="[181,330,316,330]" gridcol="1" gridrow="3" pageId="4" pageNumber="5">1.95, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFEAAFDD3FEC1" box="[368,517,316,330]" gridcol="2" gridrow="3" pageId="4" pageNumber="5">1.96, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FEAAFD17FEC1" box="[556,705,316,330]" gridcol="3" gridrow="3" pageId="4" pageNumber="5">1.95, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFEAAFCAAFEC1" box="[743,892,316,330]" gridcol="4" gridrow="3" pageId="4" pageNumber="5">1.95, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FEAAFBEEFEC1" box="[931,1080,316,330]" gridcol="5" gridrow="3" pageId="4" pageNumber="5">2.24, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FEAAFB25FEC1" box="[1118,1267,316,330]" gridcol="6" gridrow="3" pageId="4" pageNumber="5">2.29, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FEAAFA66FEC1" box="[1306,1456,316,330]" gridcol="7" gridrow="3" pageId="4" pageNumber="5">1.95, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFEC5FA66FEEA" box="[116,1456,339,353]" gridrow="4" pageId="4" pageNumber="5" rowspan-0="1">
|
||
<td id="768C5DB9EF510056FF3FFEC5FE9CFEEA" box="[181,330,339,353]" gridcol="1" gridrow="4" pageId="4" pageNumber="5">2.19, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFEC5FDD3FEEA" box="[368,517,339,353]" gridcol="2" gridrow="4" pageId="4" pageNumber="5">2.21, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FEC5FD17FEEA" box="[556,705,339,353]" gridcol="3" gridrow="4" pageId="4" pageNumber="5">2.21, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFEC5FCAAFEEA" box="[743,892,339,353]" gridcol="4" gridrow="4" pageId="4" pageNumber="5">2.23, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FEC5FBEEFEEA" box="[931,1080,339,353]" gridcol="5" gridrow="4" pageId="4" pageNumber="5">1.84, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FEC5FB25FEEA" box="[1118,1267,339,353]" gridcol="6" gridrow="4" pageId="4" pageNumber="5">1.86, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FEC5FA66FEEA" box="[1306,1456,339,353]" gridcol="7" gridrow="4" pageId="4" pageNumber="5">2.19, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFEFCFA66FEF3" box="[116,1456,362,376]" gridrow="5" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFEFCFF46FEF3" box="[116,144,362,376]" gridcol="0" gridrow="5" pageId="4" pageNumber="5">3</th>
|
||
<td id="768C5DB9EF510056FF3FFEFCFE9CFEF3" box="[181,330,362,376]" gridcol="1" gridrow="5" pageId="4" pageNumber="5">4.26, dd (12.3, 4.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFEFCFDD3FEF3" box="[368,517,362,376]" gridcol="2" gridrow="5" pageId="4" pageNumber="5">4.28, dd (12.3, 4.5)</td>
|
||
<td id="768C5DB9EF510056FDA6FEFCFD17FEF3" box="[556,705,362,376]" gridcol="3" gridrow="5" pageId="4" pageNumber="5">4.26, dd (12.3, 4.5)</td>
|
||
<td id="768C5DB9EF510056FD6DFEFCFCAAFEF3" box="[743,892,362,376]" gridcol="4" gridrow="5" pageId="4" pageNumber="5">4.28, dd (12.3, 4.5)</td>
|
||
<td id="768C5DB9EF510056FC29FEFCFBEEFEF3" box="[931,1080,362,376]" gridcol="5" gridrow="5" pageId="4" pageNumber="5">3.40, dd (11.5, 4.5)</td>
|
||
<td id="768C5DB9EF510056FBD4FEFCFB25FEF3" box="[1118,1267,362,376]" gridcol="6" gridrow="5" pageId="4" pageNumber="5">3.41, dd (11.5, 4.5)</td>
|
||
<td id="768C5DB9EF510056FA90FEFCFA66FEF3" box="[1306,1456,362,376]" gridcol="7" gridrow="5" pageId="4" pageNumber="5">4.26, dd (12.3, 4.5)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFE16FA66FE04" box="[116,1456,384,399]" gridrow="6" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFE16FF46FE04" box="[116,144,384,399]" gridcol="0" gridrow="6" pageId="4" pageNumber="5">5</th>
|
||
<td id="768C5DB9EF510056FF3FFE16FE9CFE04" box="[181,330,384,399]" gridcol="1" gridrow="6" pageId="4" pageNumber="5">1.64, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFE16FDD3FE04" box="[368,517,384,399]" gridcol="2" gridrow="6" pageId="4" pageNumber="5">1.64, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FE16FD17FE04" box="[556,705,384,399]" gridcol="3" gridrow="6" pageId="4" pageNumber="5">1.65, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFE16FCAAFE04" box="[743,892,384,399]" gridcol="4" gridrow="6" pageId="4" pageNumber="5">1.64, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FE16FBEEFE04" box="[931,1080,384,399]" gridcol="5" gridrow="6" pageId="4" pageNumber="5">0.78, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FE16FB25FE04" box="[1118,1267,384,399]" gridcol="6" gridrow="6" pageId="4" pageNumber="5">0.75, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FE16FA66FE04" box="[1306,1456,384,399]" gridcol="7" gridrow="6" pageId="4" pageNumber="5">1.64, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFE01FA66FE2E" box="[116,1456,407,421]" gridrow="7" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFE01FF46FE2E" box="[116,144,407,421]" gridcol="0" gridrow="7" pageId="4" pageNumber="5">6</th>
|
||
<td id="768C5DB9EF510056FF3FFE01FE9CFE2E" box="[181,330,407,421]" gridcol="1" gridrow="7" pageId="4" pageNumber="5">1.31, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFE01FDD3FE2E" box="[368,517,407,421]" gridcol="2" gridrow="7" pageId="4" pageNumber="5">1.33, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FE01FD17FE2E" box="[556,705,407,421]" gridcol="3" gridrow="7" pageId="4" pageNumber="5">1.32, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFE01FCAAFE2E" box="[743,892,407,421]" gridcol="4" gridrow="7" pageId="4" pageNumber="5">1.31, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FE01FBEEFE2E" box="[931,1080,407,421]" gridcol="5" gridrow="7" pageId="4" pageNumber="5">1.50, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FE01FB25FE2E" box="[1118,1267,407,421]" gridcol="6" gridrow="7" pageId="4" pageNumber="5">1.51, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FE01FA66FE2E" box="[1306,1456,407,421]" gridcol="7" gridrow="7" pageId="4" pageNumber="5">1.31, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFE38FA66FE37" box="[116,1456,430,444]" gridrow="8" pageId="4" pageNumber="5" rowspan-0="1">
|
||
<td id="768C5DB9EF510056FF3FFE38FE9CFE37" box="[181,330,430,444]" gridcol="1" gridrow="8" pageId="4" pageNumber="5">1.65, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFE38FDD3FE37" box="[368,517,430,444]" gridcol="2" gridrow="8" pageId="4" pageNumber="5">1.67, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FE38FD17FE37" box="[556,705,430,444]" gridcol="3" gridrow="8" pageId="4" pageNumber="5">1.67, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFE38FCAAFE37" box="[743,892,430,444]" gridcol="4" gridrow="8" pageId="4" pageNumber="5">1.73, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FE38FBEEFE37" box="[931,1080,430,444]" gridcol="5" gridrow="8" pageId="4" pageNumber="5">1.30, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FE38FB25FE37" box="[1118,1267,430,444]" gridcol="6" gridrow="8" pageId="4" pageNumber="5">1.29, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FE38FA66FE37" box="[1306,1456,430,444]" gridcol="7" gridrow="8" pageId="4" pageNumber="5">1.65, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFE53FA66FE58" box="[116,1456,453,467]" gridrow="9" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFE53FF46FE58" box="[116,144,453,467]" gridcol="0" gridrow="9" pageId="4" pageNumber="5">7</th>
|
||
<td id="768C5DB9EF510056FF3FFE53FE9CFE58" box="[181,330,453,467]" gridcol="1" gridrow="9" pageId="4" pageNumber="5">1.24, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFE53FDD3FE58" box="[368,517,453,467]" gridcol="2" gridrow="9" pageId="4" pageNumber="5">1.24, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FE53FD17FE58" box="[556,705,453,467]" gridcol="3" gridrow="9" pageId="4" pageNumber="5">1.22, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFE53FCAAFE58" box="[743,892,453,467]" gridcol="4" gridrow="9" pageId="4" pageNumber="5">1.16, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FE53FBEEFE58" box="[931,1080,453,467]" gridcol="5" gridrow="9" pageId="4" pageNumber="5">1.50, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FE53FB25FE58" box="[1118,1267,453,467]" gridcol="6" gridrow="9" pageId="4" pageNumber="5">1.50, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FE53FA66FE58" box="[1306,1456,453,467]" gridcol="7" gridrow="9" pageId="4" pageNumber="5">1.24, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFE4AFA66FE61" box="[116,1456,476,490]" gridrow="10" pageId="4" pageNumber="5" rowspan-0="1">
|
||
<td id="768C5DB9EF510056FF3FFE4AFE9CFE61" box="[181,330,476,490]" gridcol="1" gridrow="10" pageId="4" pageNumber="5">1.63, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFE4AFDD3FE61" box="[368,517,476,490]" gridcol="2" gridrow="10" pageId="4" pageNumber="5">1.65, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FE4AFD17FE61" box="[556,705,476,490]" gridcol="3" gridrow="10" pageId="4" pageNumber="5">1.65, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFE4AFCAAFE61" box="[743,892,476,490]" gridcol="4" gridrow="10" pageId="4" pageNumber="5">1.56, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FE4AFBEEFE61" box="[931,1080,476,490]" gridcol="5" gridrow="10" pageId="4" pageNumber="5">1.26, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FE4AFB25FE61" box="[1118,1267,476,490]" gridcol="6" gridrow="10" pageId="4" pageNumber="5">1.26, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FE4AFA66FE61" box="[1306,1456,476,490]" gridcol="7" gridrow="10" pageId="4" pageNumber="5">1.63, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFE65FA66FD8A" box="[116,1456,499,513]" gridrow="11" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFE65FF46FD8A" box="[116,144,499,513]" gridcol="0" gridrow="11" pageId="4" pageNumber="5">9</th>
|
||
<td id="768C5DB9EF510056FF3FFE65FE9CFD8A" box="[181,330,499,513]" gridcol="1" gridrow="11" pageId="4" pageNumber="5">1.63, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFE65FDD3FD8A" box="[368,517,499,513]" gridcol="2" gridrow="11" pageId="4" pageNumber="5">1.63 overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FE65FD17FD8A" box="[556,705,499,513]" gridcol="3" gridrow="11" pageId="4" pageNumber="5">1.63, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFE65FCAAFD8A" box="[743,892,499,513]" gridcol="4" gridrow="11" pageId="4" pageNumber="5">1.63, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FE65FBEEFD8A" box="[931,1080,499,513]" gridcol="5" gridrow="11" pageId="4" pageNumber="5">1.56, t (9.0)</td>
|
||
<td id="768C5DB9EF510056FBD4FE65FB25FD8A" box="[1118,1267,499,513]" gridcol="6" gridrow="11" pageId="4" pageNumber="5">1.52, t (9.0)</td>
|
||
<td id="768C5DB9EF510056FA90FE65FA66FD8A" box="[1306,1456,499,513]" gridcol="7" gridrow="11" pageId="4" pageNumber="5">1.63, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFD9FFA66FD93" box="[116,1456,521,536]" gridrow="12" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFD9FFF46FD93" box="[116,144,521,536]" gridcol="0" gridrow="12" pageId="4" pageNumber="5">11</th>
|
||
<td id="768C5DB9EF510056FF3FFD9FFE9CFD93" box="[181,330,521,536]" gridcol="1" gridrow="12" pageId="4" pageNumber="5">1.66, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFD9FFDD3FD93" box="[368,517,521,536]" gridcol="2" gridrow="12" pageId="4" pageNumber="5">1.66, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FD9FFD17FD93" box="[556,705,521,536]" gridcol="3" gridrow="12" pageId="4" pageNumber="5">1.66, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFD9FFCAAFD93" box="[743,892,521,536]" gridcol="4" gridrow="12" pageId="4" pageNumber="5">1.34, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FD9FFBEEFD93" box="[931,1080,521,536]" gridcol="5" gridrow="12" pageId="4" pageNumber="5">1.84, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FD9FFB25FD93" box="[1118,1267,521,536]" gridcol="6" gridrow="12" pageId="4" pageNumber="5">1.82, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FD9FFA66FD93" box="[1306,1456,521,536]" gridcol="7" gridrow="12" pageId="4" pageNumber="5">1.66, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFDB6FA66FDA5" box="[116,1456,544,558]" gridrow="13" pageId="4" pageNumber="5" rowspan-0="1">
|
||
<td id="768C5DB9EF510056FF3FFDB6FE9CFDA5" box="[181,330,544,558]" gridcol="1" gridrow="13" pageId="4" pageNumber="5">1.80, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFDB6FDD3FDA5" box="[368,517,544,558]" gridcol="2" gridrow="13" pageId="4" pageNumber="5">1.84, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FDB6FD17FDA5" box="[556,705,544,558]" gridcol="3" gridrow="13" pageId="4" pageNumber="5">1.84, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFDB6FCAAFDA5" box="[743,892,544,558]" gridcol="4" gridrow="13" pageId="4" pageNumber="5">1.73, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FDB6FBEEFDA5" box="[931,1080,544,558]" gridcol="5" gridrow="13" pageId="4" pageNumber="5">1.56, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FDB6FB25FDA5" box="[1118,1267,544,558]" gridcol="6" gridrow="13" pageId="4" pageNumber="5">1.56, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FDB6FA66FDA5" box="[1306,1456,544,558]" gridcol="7" gridrow="13" pageId="4" pageNumber="5">1.80, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFDA1FA66FDCD" box="[116,1456,567,582]" gridrow="14" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFDA1FF46FDCD" box="[116,144,567,582]" gridcol="0" gridrow="14" pageId="4" pageNumber="5">12</th>
|
||
<td id="768C5DB9EF510056FF3FFDA1FE9CFDCD" box="[181,330,567,582]" gridcol="1" gridrow="14" pageId="4" pageNumber="5">5.36, t (3.3)</td>
|
||
<td id="768C5DB9EF510056FEFAFDA1FDD3FDCD" box="[368,517,567,582]" gridcol="2" gridrow="14" pageId="4" pageNumber="5">5.38, t (3.3)</td>
|
||
<td id="768C5DB9EF510056FDA6FDA1FD17FDCD" box="[556,705,567,582]" gridcol="3" gridrow="14" pageId="4" pageNumber="5">5.37, t (3.3)</td>
|
||
<td id="768C5DB9EF510056FD6DFDA1FCAAFDCD" box="[743,892,567,582]" gridcol="4" gridrow="14" pageId="4" pageNumber="5">5.37, t (3.3)</td>
|
||
<td id="768C5DB9EF510056FC29FDA1FBEEFDCD" box="[931,1080,567,582]" gridcol="5" gridrow="14" pageId="4" pageNumber="5">5.24, t (3.0)</td>
|
||
<td id="768C5DB9EF510056FBD4FDA1FB25FDCD" box="[1118,1267,567,582]" gridcol="6" gridrow="14" pageId="4" pageNumber="5">5.39, t (3.0)</td>
|
||
<td id="768C5DB9EF510056FA90FDA1FA66FDCD" box="[1306,1456,567,582]" gridcol="7" gridrow="14" pageId="4" pageNumber="5">5.38, t (3.0)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFDD8FA66FDD7" box="[116,1456,590,604]" gridrow="15" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFDD8FF46FDD7" box="[116,144,590,604]" gridcol="0" gridrow="15" pageId="4" pageNumber="5">15</th>
|
||
<td id="768C5DB9EF510056FF3FFDD8FE9CFDD7" box="[181,330,590,604]" gridcol="1" gridrow="15" pageId="4" pageNumber="5">1.50, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFDD8FDD3FDD7" box="[368,517,590,604]" gridcol="2" gridrow="15" pageId="4" pageNumber="5">1.54, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FDD8FD17FDD7" box="[556,705,590,604]" gridcol="3" gridrow="15" pageId="4" pageNumber="5">1.54, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFDD8FCAAFDD7" box="[743,892,590,604]" gridcol="4" gridrow="15" pageId="4" pageNumber="5">1.41, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FDD8FBEEFDD7" box="[931,1080,590,604]" gridcol="5" gridrow="15" pageId="4" pageNumber="5">2.20, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FDD8FB25FDD7" box="[1118,1267,590,604]" gridcol="6" gridrow="15" pageId="4" pageNumber="5">1.89, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FDD8FA66FDD7" box="[1306,1456,590,604]" gridcol="7" gridrow="15" pageId="4" pageNumber="5">1.88, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFDF3FA66FDF8" box="[116,1456,613,627]" gridrow="16" pageId="4" pageNumber="5" rowspan-0="1">
|
||
<td id="768C5DB9EF510056FF3FFDF3FE9CFDF8" box="[181,330,613,627]" gridcol="1" gridrow="16" pageId="4" pageNumber="5">2.00, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFDF3FDD3FDF8" box="[368,517,613,627]" gridcol="2" gridrow="16" pageId="4" pageNumber="5">2.02, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FDF3FD17FDF8" box="[556,705,613,627]" gridcol="3" gridrow="16" pageId="4" pageNumber="5">2.02, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFDF3FCAAFDF8" box="[743,892,613,627]" gridcol="4" gridrow="16" pageId="4" pageNumber="5">1.88, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FDF3FBEEFDF8" box="[931,1080,613,627]" gridcol="5" gridrow="16" pageId="4" pageNumber="5">1.74, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FDF3FB25FDF8" box="[1118,1267,613,627]" gridcol="6" gridrow="16" pageId="4" pageNumber="5">1.45, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FDF3FA66FDF8" box="[1306,1456,613,627]" gridcol="7" gridrow="16" pageId="4" pageNumber="5">1.42, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFDEAFA66FD01" box="[116,1456,636,650]" gridrow="17" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFDEAFF46FD01" box="[116,144,636,650]" gridcol="0" gridrow="17" pageId="4" pageNumber="5">16</th>
|
||
<td id="768C5DB9EF510056FF3FFDEAFE9CFD01" box="[181,330,636,650]" gridcol="1" gridrow="17" pageId="4" pageNumber="5">5.09, dd (11.0, 5.2)</td>
|
||
<td id="768C5DB9EF510056FEFAFDEAFDD3FD01" box="[368,517,636,650]" gridcol="2" gridrow="17" pageId="4" pageNumber="5">5.12, dd (11.0,5.2)</td>
|
||
<td id="768C5DB9EF510056FDA6FDEAFD17FD01" box="[556,705,636,650]" gridcol="3" gridrow="17" pageId="4" pageNumber="5">5.12, dd (11.0,5.2)</td>
|
||
<td id="768C5DB9EF510056FD6DFDEAFCAAFD01" box="[743,892,636,650]" gridcol="4" gridrow="17" pageId="4" pageNumber="5">6.31, dd (11.5,5.5)</td>
|
||
<td id="768C5DB9EF510056FC29FDEAFBEEFD01" box="[931,1080,636,650]" gridcol="5" gridrow="17" pageId="4" pageNumber="5">4.57, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FDEAFB25FD01" box="[1118,1267,636,650]" gridcol="6" gridrow="17" pageId="4" pageNumber="5">6.31, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FDEAFA66FD01" box="[1306,1456,636,650]" gridcol="7" gridrow="17" pageId="4" pageNumber="5">6.30, dd (11.0, 5.5)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFD05FA66FD2A" box="[116,1456,659,673]" gridrow="18" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFD05FF46FD2A" box="[116,144,659,673]" gridcol="0" gridrow="18" pageId="4" pageNumber="5">18</th>
|
||
<td id="768C5DB9EF510056FF3FFD05FE9CFD2A" box="[181,330,659,673]" gridcol="1" gridrow="18" pageId="4" pageNumber="5">2.84, dd (13.7, 3.9)</td>
|
||
<td id="768C5DB9EF510056FEFAFD05FDD3FD2A" box="[368,517,659,673]" gridcol="2" gridrow="18" pageId="4" pageNumber="5">2.87, dd (13.7, 3.9)</td>
|
||
<td id="768C5DB9EF510056FDA6FD05FD17FD2A" box="[556,705,659,673]" gridcol="3" gridrow="18" pageId="4" pageNumber="5">2.89, dd (13.7, 3.9)</td>
|
||
<td id="768C5DB9EF510056FD6DFD05FCAAFD2A" box="[743,892,659,673]" gridcol="4" gridrow="18" pageId="4" pageNumber="5">3.28, dd (14.0, 4.0)</td>
|
||
<td id="768C5DB9EF510056FC29FD05FBEEFD2A" box="[931,1080,659,673]" gridcol="5" gridrow="18" pageId="4" pageNumber="5">2.30, dd (13.8, 4.0)</td>
|
||
<td id="768C5DB9EF510056FBD4FD05FB25FD2A" box="[1118,1267,659,673]" gridcol="6" gridrow="18" pageId="4" pageNumber="5">3.27, dd (14.0, 4.0)</td>
|
||
<td id="768C5DB9EF510056FA90FD05FA66FD2A" box="[1306,1456,659,673]" gridcol="7" gridrow="18" pageId="4" pageNumber="5">3.30, dd (14.4, 4.0)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFD3FFA66FD33" box="[116,1456,681,696]" gridrow="19" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFD3FFF46FD33" box="[116,144,681,696]" gridcol="0" gridrow="19" pageId="4" pageNumber="5">19</th>
|
||
<td id="768C5DB9EF510056FF3FFD3FFE9CFD33" box="[181,330,681,696]" gridcol="1" gridrow="19" pageId="4" pageNumber="5">1.30, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFD3FFDD3FD33" box="[368,517,681,696]" gridcol="2" gridrow="19" pageId="4" pageNumber="5">1.32, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FD3FFD17FD33" box="[556,705,681,696]" gridcol="3" gridrow="19" pageId="4" pageNumber="5">1.32, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFD3FFCAAFD33" box="[743,892,681,696]" gridcol="4" gridrow="19" pageId="4" pageNumber="5">1.31, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FD3FFBEEFD33" box="[931,1080,681,696]" gridcol="5" gridrow="19" pageId="4" pageNumber="5">1.88, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FD3FFB25FD33" box="[1118,1267,681,696]" gridcol="6" gridrow="19" pageId="4" pageNumber="5">2.27, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FD3FFA66FD33" box="[1306,1456,681,696]" gridcol="7" gridrow="19" pageId="4" pageNumber="5">2.26, t (14.0)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFD56FA66FD45" box="[116,1456,704,718]" gridrow="20" pageId="4" pageNumber="5" rowspan-0="1">
|
||
<td id="768C5DB9EF510056FF3FFD56FE9CFD45" box="[181,330,704,718]" gridcol="1" gridrow="20" pageId="4" pageNumber="5">2.17, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAFD56FDD3FD45" box="[368,517,704,718]" gridcol="2" gridrow="20" pageId="4" pageNumber="5">2.21, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FD56FD17FD45" box="[556,705,704,718]" gridcol="3" gridrow="20" pageId="4" pageNumber="5">2.21, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFD56FCAAFD45" box="[743,892,704,718]" gridcol="4" gridrow="20" pageId="4" pageNumber="5">2.28, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FD56FBEEFD45" box="[931,1080,704,718]" gridcol="5" gridrow="20" pageId="4" pageNumber="5">1.16, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FD56FB25FD45" box="[1118,1267,704,718]" gridcol="6" gridrow="20" pageId="4" pageNumber="5">1.34, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FD56FA66FD45" box="[1306,1456,704,718]" gridcol="7" gridrow="20" pageId="4" pageNumber="5">1.34, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFD78FA66FD77" box="[116,1456,750,764]" gridrow="21" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFD78FF46FD77" box="[116,144,750,764]" gridcol="0" gridrow="21" pageId="4" pageNumber="5">21</th>
|
||
<td id="768C5DB9EF510056FF3FFD78FE9CFD77" box="[181,330,750,764]" gridcol="1" gridrow="21" pageId="4" pageNumber="5">5.67, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFD78FDD3FD77" box="[368,517,750,764]" gridcol="2" gridrow="21" pageId="4" pageNumber="5">5.76, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FDA6FD78FD17FD77" box="[556,705,750,764]" gridcol="3" gridrow="21" pageId="4" pageNumber="5">5.77, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FD6DFD78FCAAFD77" box="[743,892,750,764]" gridcol="4" gridrow="21" pageId="4" pageNumber="5">5.70, d (11.0)</td>
|
||
<td id="768C5DB9EF510056FC29FD78FBEEFD77" box="[931,1080,750,764]" gridcol="5" gridrow="21" pageId="4" pageNumber="5">1.23, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FD78FB25FD77" box="[1118,1267,750,764]" gridcol="6" gridrow="21" pageId="4" pageNumber="5">5.61, d (11.0)</td>
|
||
<td id="768C5DB9EF510056FA90FD78FA66FD77" box="[1306,1456,750,764]" gridcol="7" gridrow="21" pageId="4" pageNumber="5">5.69, d (11.0)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFC93FA66FC98" box="[116,1456,773,787]" gridrow="22" pageId="4" pageNumber="5" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1" rowspan-7="1">
|
||
<td id="768C5DB9EF510056FC29FC93FBEEFC98" box="[931,1080,773,787]" gridcol="5" gridrow="22" pageId="4" pageNumber="5">1.63, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFCA5FA66FCCA" box="[116,1456,819,833]" gridrow="23" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFCA5FF46FCCA" box="[116,144,819,833]" gridcol="0" gridrow="23" pageId="4" pageNumber="5">22</th>
|
||
<td id="768C5DB9EF510056FF3FFCA5FE9CFCCA" box="[181,330,819,833]" gridcol="1" gridrow="23" pageId="4" pageNumber="5">4.50, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFCA5FDD3FCCA" box="[368,517,819,833]" gridcol="2" gridrow="23" pageId="4" pageNumber="5">4.62, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FCA5FD17FCCA" box="[556,705,819,833]" gridcol="3" gridrow="23" pageId="4" pageNumber="5">4.6, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFCA5FCAAFCCA" box="[743,892,819,833]" gridcol="4" gridrow="23" pageId="4" pageNumber="5">6.22, d (11.0)</td>
|
||
<td id="768C5DB9EF510056FC29FCA5FBEEFCCA" box="[931,1080,819,833]" gridcol="5" gridrow="23" pageId="4" pageNumber="5">1.83, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FCA5FB25FCCA" box="[1118,1267,819,833]" gridcol="6" gridrow="23" pageId="4" pageNumber="5">5.16, d (11.0)</td>
|
||
<td id="768C5DB9EF510056FA90FCA5FA66FCCA" box="[1306,1456,819,833]" gridcol="7" gridrow="23" pageId="4" pageNumber="5">6.23, d (11.0)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFCDFFA66FCDC" box="[116,1456,841,855]" gridrow="24" pageId="4" pageNumber="5" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1" rowspan-7="1">
|
||
<td id="768C5DB9EF510056FC29FCDFFBEEFCDC" box="[931,1080,841,855]" gridcol="5" gridrow="24" pageId="4" pageNumber="5">1.35, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFCE1FA66FC0E" box="[116,1456,887,901]" gridrow="25" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFCE1FF46FC0E" box="[116,144,887,901]" gridcol="0" gridrow="25" pageId="4" pageNumber="5">23</th>
|
||
<td id="768C5DB9EF510056FF3FFCE1FE9CFC0E" box="[181,330,887,901]" gridcol="1" gridrow="25" pageId="4" pageNumber="5">3.70, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFCE1FDD3FC0E" box="[368,517,887,901]" gridcol="2" gridrow="25" pageId="4" pageNumber="5">3.72, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FDA6FCE1FD17FC0E" box="[556,705,887,901]" gridcol="3" gridrow="25" pageId="4" pageNumber="5">3.70 d (10.5)</td>
|
||
<td id="768C5DB9EF510056FD6DFCE1FCAAFC0E" box="[743,892,887,901]" gridcol="4" gridrow="25" pageId="4" pageNumber="5">3.74, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FC29FCE1FBEEFC0E" box="[931,1080,887,901]" gridcol="5" gridrow="25" pageId="4" pageNumber="5">1.32, s</td>
|
||
<td id="768C5DB9EF510056FBD4FCE1FB25FC0E" box="[1118,1267,887,901]" gridcol="6" gridrow="25" pageId="4" pageNumber="5">1.32, s</td>
|
||
<td id="768C5DB9EF510056FA90FCE1FA66FC0E" box="[1306,1456,887,901]" gridcol="7" gridrow="25" pageId="4" pageNumber="5">4.36, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFC18FA66FC17" box="[116,1456,910,924]" gridrow="26" pageId="4" pageNumber="5" rowspan-0="1" rowspan-5="1" rowspan-6="1">
|
||
<td id="768C5DB9EF510056FF3FFC18FE9CFC17" box="[181,330,910,924]" gridcol="1" gridrow="26" pageId="4" pageNumber="5">4.32, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFC18FDD3FC17" box="[368,517,910,924]" gridcol="2" gridrow="26" pageId="4" pageNumber="5">4.36, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FC18FD17FC17" box="[556,705,910,924]" gridcol="3" gridrow="26" pageId="4" pageNumber="5">4.18, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFC18FCAAFC17" box="[743,892,910,924]" gridcol="4" gridrow="26" pageId="4" pageNumber="5">4.36, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FC18FA66FC17" box="[1306,1456,910,924]" gridcol="7" gridrow="26" pageId="4" pageNumber="5">3.73, d (10.4)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFC33FA66FC38" box="[116,1456,933,947]" gridrow="27" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFC33FF46FC38" box="[116,144,933,947]" gridcol="0" gridrow="27" pageId="4" pageNumber="5">24</th>
|
||
<td id="768C5DB9EF510056FF3FFC33FE9CFC38" box="[181,330,933,947]" gridcol="1" gridrow="27" pageId="4" pageNumber="5">0.92, s</td>
|
||
<td id="768C5DB9EF510056FEFAFC33FDD3FC38" box="[368,517,933,947]" gridcol="2" gridrow="27" pageId="4" pageNumber="5">0.93, s</td>
|
||
<td id="768C5DB9EF510056FDA6FC33FD17FC38" box="[556,705,933,947]" gridcol="3" gridrow="27" pageId="4" pageNumber="5">0.91, s</td>
|
||
<td id="768C5DB9EF510056FD6DFC33FCAAFC38" box="[743,892,933,947]" gridcol="4" gridrow="27" pageId="4" pageNumber="5">0.95, s</td>
|
||
<td id="768C5DB9EF510056FC29FC33FBEEFC38" box="[931,1080,933,947]" gridcol="5" gridrow="27" pageId="4" pageNumber="5">1.03, s</td>
|
||
<td id="768C5DB9EF510056FBD4FC33FB25FC38" box="[1118,1267,933,947]" gridcol="6" gridrow="27" pageId="4" pageNumber="5">0.99, s</td>
|
||
<td id="768C5DB9EF510056FA90FC33FA66FC38" box="[1306,1456,933,947]" gridcol="7" gridrow="27" pageId="4" pageNumber="5">0.96, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFC2DFA66FC41" box="[116,1456,955,970]" gridrow="28" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFC2DFF46FC41" box="[116,144,955,970]" gridcol="0" gridrow="28" pageId="4" pageNumber="5">25</th>
|
||
<td id="768C5DB9EF510056FF3FFC2DFE9CFC41" box="[181,330,955,970]" gridcol="1" gridrow="28" pageId="4" pageNumber="5">0.90, s</td>
|
||
<td id="768C5DB9EF510056FEFAFC2DFDD3FC41" box="[368,517,955,970]" gridcol="2" gridrow="28" pageId="4" pageNumber="5">0.89, s</td>
|
||
<td id="768C5DB9EF510056FDA6FC2DFD17FC41" box="[556,705,955,970]" gridcol="3" gridrow="28" pageId="4" pageNumber="5">0.87, s</td>
|
||
<td id="768C5DB9EF510056FD6DFC2DFCAAFC41" box="[743,892,955,970]" gridcol="4" gridrow="28" pageId="4" pageNumber="5">0.88, s</td>
|
||
<td id="768C5DB9EF510056FC29FC2DFBEEFC41" box="[931,1080,955,970]" gridcol="5" gridrow="28" pageId="4" pageNumber="5">0.87, s</td>
|
||
<td id="768C5DB9EF510056FBD4FC2DFB25FC41" box="[1118,1267,955,970]" gridcol="6" gridrow="28" pageId="4" pageNumber="5">0.78, s</td>
|
||
<td id="768C5DB9EF510056FA90FC2DFA66FC41" box="[1306,1456,955,970]" gridcol="7" gridrow="28" pageId="4" pageNumber="5">0.89,s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFC44FA66FC6A" box="[116,1456,978,993]" gridrow="29" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFC44FF46FC6A" box="[116,144,978,993]" gridcol="0" gridrow="29" pageId="4" pageNumber="5">26</th>
|
||
<td id="768C5DB9EF510056FF3FFC44FE9CFC6A" box="[181,330,978,993]" gridcol="1" gridrow="29" pageId="4" pageNumber="5">1.05, s</td>
|
||
<td id="768C5DB9EF510056FEFAFC44FDD3FC6A" box="[368,517,978,993]" gridcol="2" gridrow="29" pageId="4" pageNumber="5">1.06, s</td>
|
||
<td id="768C5DB9EF510056FDA6FC44FD17FC6A" box="[556,705,978,993]" gridcol="3" gridrow="29" pageId="4" pageNumber="5">1.05, s</td>
|
||
<td id="768C5DB9EF510056FD6DFC44FCAAFC6A" box="[743,892,978,993]" gridcol="4" gridrow="29" pageId="4" pageNumber="5">0.90, s</td>
|
||
<td id="768C5DB9EF510056FC29FC44FBEEFC6A" box="[931,1080,978,993]" gridcol="5" gridrow="29" pageId="4" pageNumber="5">0.98, s</td>
|
||
<td id="768C5DB9EF510056FBD4FC44FB25FC6A" box="[1118,1267,978,993]" gridcol="6" gridrow="29" pageId="4" pageNumber="5">0.86, s</td>
|
||
<td id="768C5DB9EF510056FA90FC44FA66FC6A" box="[1306,1456,978,993]" gridcol="7" gridrow="29" pageId="4" pageNumber="5">0.90, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFC7FFA66FC73" box="[116,1456,1001,1016]" gridrow="30" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFC7FFF46FC73" box="[116,144,1001,1016]" gridcol="0" gridrow="30" pageId="4" pageNumber="5">27</th>
|
||
<td id="768C5DB9EF510056FF3FFC7FFE9CFC73" box="[181,330,1001,1016]" gridcol="1" gridrow="30" pageId="4" pageNumber="5">1.27, s</td>
|
||
<td id="768C5DB9EF510056FEFAFC7FFDD3FC73" box="[368,517,1001,1016]" gridcol="2" gridrow="30" pageId="4" pageNumber="5">1.28, s</td>
|
||
<td id="768C5DB9EF510056FDA6FC7FFD17FC73" box="[556,705,1001,1016]" gridcol="3" gridrow="30" pageId="4" pageNumber="5">1.28, s</td>
|
||
<td id="768C5DB9EF510056FD6DFC7FFCAAFC73" box="[743,892,1001,1016]" gridcol="4" gridrow="30" pageId="4" pageNumber="5">1.35, s</td>
|
||
<td id="768C5DB9EF510056FC29FC7FFBEEFC73" box="[931,1080,1001,1016]" gridcol="5" gridrow="30" pageId="4" pageNumber="5">1.35, s</td>
|
||
<td id="768C5DB9EF510056FBD4FC7FFB25FC73" box="[1118,1267,1001,1016]" gridcol="6" gridrow="30" pageId="4" pageNumber="5">1.41, s</td>
|
||
<td id="768C5DB9EF510056FA90FC7FFA66FC73" box="[1306,1456,1001,1016]" gridcol="7" gridrow="30" pageId="4" pageNumber="5">1.37, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFB96FA66FB84" box="[116,1456,1024,1039]" gridrow="31" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFB96FF46FB84" box="[116,144,1024,1039]" gridcol="0" gridrow="31" pageId="4" pageNumber="5">28</th>
|
||
<td id="768C5DB9EF510056FF3FFB96FE9CFB84" box="[181,330,1024,1039]" gridcol="1" gridrow="31" pageId="4" pageNumber="5">4.57, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFB96FDD3FB84" box="[368,517,1024,1039]" gridcol="2" gridrow="31" pageId="4" pageNumber="5">4.64, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FB96FD17FB84" box="[556,705,1024,1039]" gridcol="3" gridrow="31" pageId="4" pageNumber="5">4.62, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFB96FCAAFB84" box="[743,892,1024,1039]" gridcol="4" gridrow="31" pageId="4" pageNumber="5">4.00, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FB96FBEEFB84" box="[931,1080,1024,1039]" gridcol="5" gridrow="31" pageId="4" pageNumber="5">4.03, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FB96FB25FB84" box="[1118,1267,1024,1039]" gridcol="6" gridrow="31" pageId="4" pageNumber="5">3.99, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FB96FA66FB84" box="[1306,1456,1024,1039]" gridcol="7" gridrow="31" pageId="4" pageNumber="5">4.01, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFB81FA66FBAE" box="[116,1456,1047,1061]" gridrow="32" pageId="4" pageNumber="5" rowspan-0="1">
|
||
<td id="768C5DB9EF510056FF3FFB81FE9CFBAE" box="[181,330,1047,1061]" gridcol="1" gridrow="32" pageId="4" pageNumber="5">4.99, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFB81FDD3FBAE" box="[368,517,1047,1061]" gridcol="2" gridrow="32" pageId="4" pageNumber="5">5.07, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FDA6FB81FD17FBAE" box="[556,705,1047,1061]" gridcol="3" gridrow="32" pageId="4" pageNumber="5">5.07, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FD6DFB81FCAAFBAE" box="[743,892,1047,1061]" gridcol="4" gridrow="32" pageId="4" pageNumber="5">4.02, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FB81FBEEFBAE" box="[931,1080,1047,1061]" gridcol="5" gridrow="32" pageId="4" pageNumber="5">4.25, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FB81FB25FBAE" box="[1118,1267,1047,1061]" gridcol="6" gridrow="32" pageId="4" pageNumber="5">4.00, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FB81FA66FBAE" box="[1306,1456,1047,1061]" gridcol="7" gridrow="32" pageId="4" pageNumber="5">4.25, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFBB8FA66FBB7" box="[116,1456,1070,1084]" gridrow="33" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFBB8FF46FBB7" box="[116,144,1070,1084]" gridcol="0" gridrow="33" pageId="4" pageNumber="5">29</th>
|
||
<td id="768C5DB9EF510056FF3FFBB8FE9CFBB7" box="[181,330,1070,1084]" gridcol="1" gridrow="33" pageId="4" pageNumber="5">1.04, s</td>
|
||
<td id="768C5DB9EF510056FEFAFBB8FDD3FBB7" box="[368,517,1070,1084]" gridcol="2" gridrow="33" pageId="4" pageNumber="5">1.04, s</td>
|
||
<td id="768C5DB9EF510056FDA6FBB8FD17FBB7" box="[556,705,1070,1084]" gridcol="3" gridrow="33" pageId="4" pageNumber="5">1.04, s</td>
|
||
<td id="768C5DB9EF510056FD6DFBB8FCAAFBB7" box="[743,892,1070,1084]" gridcol="4" gridrow="33" pageId="4" pageNumber="5">0.95, s</td>
|
||
<td id="768C5DB9EF510056FC29FBB8FBEEFBB7" box="[931,1080,1070,1084]" gridcol="5" gridrow="33" pageId="4" pageNumber="5">0.93, s</td>
|
||
<td id="768C5DB9EF510056FBD4FBB8FB25FBB7" box="[1118,1267,1070,1084]" gridcol="6" gridrow="33" pageId="4" pageNumber="5">0.96, s</td>
|
||
<td id="768C5DB9EF510056FA90FBB8FA66FBB7" box="[1306,1456,1070,1084]" gridcol="7" gridrow="33" pageId="4" pageNumber="5">0.98, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFBD3FA66FBD8" box="[116,1456,1093,1107]" gridrow="34" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFBD3FF46FBD8" box="[116,144,1093,1107]" gridcol="0" gridrow="34" pageId="4" pageNumber="5">30</th>
|
||
<td id="768C5DB9EF510056FF3FFBD3FE9CFBD8" box="[181,330,1093,1107]" gridcol="1" gridrow="34" pageId="4" pageNumber="5">1.20, s</td>
|
||
<td id="768C5DB9EF510056FEFAFBD3FDD3FBD8" box="[368,517,1093,1107]" gridcol="2" gridrow="34" pageId="4" pageNumber="5">1.23, s</td>
|
||
<td id="768C5DB9EF510056FDA6FBD3FD17FBD8" box="[556,705,1093,1107]" gridcol="3" gridrow="34" pageId="4" pageNumber="5">1.23, s</td>
|
||
<td id="768C5DB9EF510056FD6DFBD3FCAAFBD8" box="[743,892,1093,1107]" gridcol="4" gridrow="34" pageId="4" pageNumber="5">1.23, s</td>
|
||
<td id="768C5DB9EF510056FC29FBD3FBEEFBD8" box="[931,1080,1093,1107]" gridcol="5" gridrow="34" pageId="4" pageNumber="5">0.95, s</td>
|
||
<td id="768C5DB9EF510056FBD4FBD3FB25FBD8" box="[1118,1267,1093,1107]" gridcol="6" gridrow="34" pageId="4" pageNumber="5">1.20, s</td>
|
||
<td id="768C5DB9EF510056FA90FBD3FA66FBD8" box="[1306,1456,1093,1107]" gridcol="7" gridrow="34" pageId="4" pageNumber="5">1.24, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFBCDFA66FBE2" box="[116,1456,1115,1129]" gridrow="35" pageId="4" pageNumber="5" rowspan-0="1">
|
||
<td id="768C5DB9EF510056FF3FFBCDFE9CFBE2" box="[181,330,1115,1129]" gridcol="1" gridrow="35" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFF3FFBCDFF2EFBE2" bold="true" box="[181,248,1115,1129]" italics="true" pageId="4" pageNumber="5">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FEFAFBCDFDD3FBE2" box="[368,517,1115,1129]" gridcol="2" gridrow="35" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFEFAFBCDFE65FBE2" bold="true" box="[368,435,1115,1129]" italics="true" pageId="4" pageNumber="5">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FDA6FBCDFD17FBE2" box="[556,705,1115,1129]" gridcol="3" gridrow="35" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFDA6FBCDFDB9FBE2" bold="true" box="[556,623,1115,1129]" italics="true" pageId="4" pageNumber="5">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FD6DFBCDFCAAFBE2" box="[743,892,1115,1129]" gridcol="4" gridrow="35" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFD6DFBCDFCFCFBE2" bold="true" box="[743,810,1115,1129]" italics="true" pageId="4" pageNumber="5">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FC29FBCDFBEEFBE2" box="[931,1080,1115,1129]" gridcol="5" gridrow="35" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFC29FBCDFC0DFBE2" bold="true" box="[931,987,1115,1129]" italics="true" pageId="4" pageNumber="5">3-O-Glc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FBD4FBCDFB25FBE2" box="[1118,1267,1115,1129]" gridcol="6" gridrow="35" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFBD4FBCDFB77FBE2" bold="true" box="[1118,1185,1115,1129]" italics="true" pageId="4" pageNumber="5">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FA90FBCDFA66FBE2" box="[1306,1456,1115,1129]" gridcol="7" gridrow="35" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFA90FBCDFA8BFBE2" bold="true" box="[1306,1373,1115,1129]" italics="true" pageId="4" pageNumber="5">3-O-GlcA</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFB1EFA66FB1C" box="[116,1456,1160,1175]" gridrow="36" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFB1EFF46FB1C" box="[116,144,1160,1175]" gridcol="0" gridrow="36" pageId="4" pageNumber="5">1ʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFB1EFE9CFB1C" box="[181,330,1160,1175]" gridcol="1" gridrow="36" pageId="4" pageNumber="5">5.17, d (7.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFB1EFDD3FB1C" box="[368,517,1160,1175]" gridcol="2" gridrow="36" pageId="4" pageNumber="5">5.20, d (7.5)</td>
|
||
<td id="768C5DB9EF510056FDA6FB1EFD17FB1C" box="[556,705,1160,1175]" gridcol="3" gridrow="36" pageId="4" pageNumber="5">5.15, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFB1EFCAAFB1C" box="[743,892,1160,1175]" gridcol="4" gridrow="36" pageId="4" pageNumber="5">5.19, d (7.5)</td>
|
||
<td id="768C5DB9EF510056FC29FB1EFBEEFB1C" box="[931,1080,1160,1175]" gridcol="5" gridrow="36" pageId="4" pageNumber="5">4.97, d (7.5)</td>
|
||
<td id="768C5DB9EF510056FBD4FB1EFB25FB1C" box="[1118,1267,1160,1175]" gridcol="6" gridrow="36" pageId="4" pageNumber="5">5.19, d (7.5)</td>
|
||
<td id="768C5DB9EF510056FA90FB1EFA66FB1C" box="[1306,1456,1160,1175]" gridcol="7" gridrow="36" pageId="4" pageNumber="5">5.27, d (7.5)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFB09FA66FB25" box="[116,1456,1183,1198]" gridrow="37" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFB09FF46FB25" box="[116,144,1183,1198]" gridcol="0" gridrow="37" pageId="4" pageNumber="5">2ʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFB09FE9CFB25" box="[181,330,1183,1198]" gridcol="1" gridrow="37" pageId="4" pageNumber="5">4.20, dd (10.0, 7.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFB09FDD3FB25" box="[368,517,1183,1198]" gridcol="2" gridrow="37" pageId="4" pageNumber="5">4.20, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FB09FD17FB25" box="[556,705,1183,1198]" gridcol="3" gridrow="37" pageId="4" pageNumber="5">4.21, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFB09FCAAFB25" box="[743,892,1183,1198]" gridcol="4" gridrow="37" pageId="4" pageNumber="5">4.21, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FB09FBEEFB25" box="[931,1080,1183,1198]" gridcol="5" gridrow="37" pageId="4" pageNumber="5">4.01, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FB09FB25FB25" box="[1118,1267,1183,1198]" gridcol="6" gridrow="37" pageId="4" pageNumber="5">4.21, overlap</td>
|
||
<td id="768C5DB9EF510056FA90FB09FA66FB25" box="[1306,1456,1183,1198]" gridcol="7" gridrow="37" pageId="4" pageNumber="5">4.18, t (6.8)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFB20FA66FB4E" box="[116,1456,1206,1221]" gridrow="38" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFB20FF46FB4E" box="[116,144,1206,1221]" gridcol="0" gridrow="38" pageId="4" pageNumber="5">3ʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFB20FE9CFB4E" box="[181,330,1206,1221]" gridcol="1" gridrow="38" pageId="4" pageNumber="5">4.89, t (10.0)</td>
|
||
<td id="768C5DB9EF510056FEFAFB20FDD3FB4E" box="[368,517,1206,1221]" gridcol="2" gridrow="38" pageId="4" pageNumber="5">4.91, t (9.5)</td>
|
||
<td id="768C5DB9EF510056FDA6FB20FD17FB4E" box="[556,705,1206,1221]" gridcol="3" gridrow="38" pageId="4" pageNumber="5">4.89, t (9.5)</td>
|
||
<td id="768C5DB9EF510056FD6DFB20FCAAFB4E" box="[743,892,1206,1221]" gridcol="4" gridrow="38" pageId="4" pageNumber="5">4.91, t (9.5)</td>
|
||
<td id="768C5DB9EF510056FC29FB20FBEEFB4E" box="[931,1080,1206,1221]" gridcol="5" gridrow="38" pageId="4" pageNumber="5">4.26, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FB20FB25FB4E" box="[1118,1267,1206,1221]" gridcol="6" gridrow="38" pageId="4" pageNumber="5">4.91, t (9.5)</td>
|
||
<td id="768C5DB9EF510056FA90FB20FA66FB4E" box="[1306,1456,1206,1221]" gridcol="7" gridrow="38" pageId="4" pageNumber="5">4.26, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFB5BFA66FB57" box="[116,1456,1229,1244]" gridrow="39" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFB5BFF46FB57" box="[116,144,1229,1244]" gridcol="0" gridrow="39" pageId="4" pageNumber="5">4ʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFB5BFE9CFB57" box="[181,330,1229,1244]" gridcol="1" gridrow="39" pageId="4" pageNumber="5">5.21, t (10.0)</td>
|
||
<td id="768C5DB9EF510056FEFAFB5BFDD3FB57" box="[368,517,1229,1244]" gridcol="2" gridrow="39" pageId="4" pageNumber="5">5.24, t (9.5)</td>
|
||
<td id="768C5DB9EF510056FDA6FB5BFD17FB57" box="[556,705,1229,1244]" gridcol="3" gridrow="39" pageId="4" pageNumber="5">4.36, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFB5BFCAAFB57" box="[743,892,1229,1244]" gridcol="4" gridrow="39" pageId="4" pageNumber="5">5.21, t (9.5)</td>
|
||
<td id="768C5DB9EF510056FC29FB5BFBEEFB57" box="[931,1080,1229,1244]" gridcol="5" gridrow="39" pageId="4" pageNumber="5">4.22, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FB5BFB25FB57" box="[1118,1267,1229,1244]" gridcol="6" gridrow="39" pageId="4" pageNumber="5">5.21, t (9.5)</td>
|
||
<td id="768C5DB9EF510056FA90FB5BFA66FB57" box="[1306,1456,1229,1244]" gridcol="7" gridrow="39" pageId="4" pageNumber="5">4.59, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFB72FA66FB78" box="[116,1456,1252,1267]" gridrow="40" pageId="4" pageNumber="5">
|
||
<th id="768C5DB9EF510056FFFEFB72FF46FB78" box="[116,144,1252,1267]" gridcol="0" gridrow="40" pageId="4" pageNumber="5">5ʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFB72FE9CFB78" box="[181,330,1252,1267]" gridcol="1" gridrow="40" pageId="4" pageNumber="5">4.53, d (10.0)</td>
|
||
<td id="768C5DB9EF510056FEFAFB72FDD3FB78" box="[368,517,1252,1267]" gridcol="2" gridrow="40" pageId="4" pageNumber="5">4.54, d (9.5)</td>
|
||
<td id="768C5DB9EF510056FDA6FB72FD17FB78" box="[556,705,1252,1267]" gridcol="3" gridrow="40" pageId="4" pageNumber="5">4.54, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFB72FCAAFB78" box="[743,892,1252,1267]" gridcol="4" gridrow="40" pageId="4" pageNumber="5">4.55, d (9.5)</td>
|
||
<td id="768C5DB9EF510056FC29FB72FBEEFB78" box="[931,1080,1252,1267]" gridcol="5" gridrow="40" pageId="4" pageNumber="5">4.02, overlap</td>
|
||
<td id="768C5DB9EF510056FBD4FB72FB25FB78" box="[1118,1267,1252,1267]" gridcol="6" gridrow="40" pageId="4" pageNumber="5">4.55, d (9.5)</td>
|
||
<td id="768C5DB9EF510056FA90FB72FA66FB78" box="[1306,1456,1252,1267]" gridcol="7" gridrow="40" pageId="4" pageNumber="5">4.59, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFB6CFA66FA82" box="[116,1456,1274,1289]" gridrow="41" pageId="4" pageNumber="5" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEFB6CFF46FA82" box="[116,144,1274,1289]" gridcol="0" gridrow="41" pageId="4" pageNumber="5">6ʹ</th>
|
||
<td id="768C5DB9EF510056FC29FB6CFBEEFA82" box="[931,1080,1274,1289]" gridcol="5" gridrow="41" pageId="4" pageNumber="5">4.40, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFA84FA66FAAB" box="[116,1456,1298,1312]" gridrow="42" pageId="4" pageNumber="5" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1" rowspan-7="1">
|
||
<td id="768C5DB9EF510056FC29FA84FBEEFAAB" box="[931,1080,1298,1312]" gridcol="5" gridrow="42" pageId="4" pageNumber="5">4.59, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFABFFA66FABC" box="[116,1456,1321,1335]" gridrow="43" pageId="4" pageNumber="5" rowspan-0="1" rowspan-6="1" rowspan-7="1">
|
||
<td id="768C5DB9EF510056FF3FFABFFE9CFABC" box="[181,330,1321,1335]" gridcol="1" gridrow="43" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFF3FFABFFEC1FABC" bold="true" box="[181,279,1321,1335]" italics="true" pageId="4" pageNumber="5">3ʹ-O-2-oxoglc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FEFAFABFFDD3FABC" box="[368,517,1321,1335]" gridcol="2" gridrow="43" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFEFAFABFFE04FABC" bold="true" box="[368,466,1321,1335]" italics="true" pageId="4" pageNumber="5">3ʹ-O-2-oxoglc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FDA6FABFFD17FABC" box="[556,705,1321,1335]" gridcol="3" gridrow="43" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFDA6FABFFD58FABC" bold="true" box="[556,654,1321,1335]" italics="true" pageId="4" pageNumber="5">3ʹ-O-2-oxoglc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FD6DFABFFCAAFABC" box="[743,892,1321,1335]" gridcol="4" gridrow="43" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFD6DFABFFC9FFABC" bold="true" box="[743,841,1321,1335]" italics="true" pageId="4" pageNumber="5">3ʹ-O-2-oxoglc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FC29FABFFBEEFABC" box="[931,1080,1321,1335]" gridcol="5" gridrow="43" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFC29FABFFC32FABC" bold="true" box="[931,996,1321,1335]" italics="true" pageId="4" pageNumber="5">28-O-Glc</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFAC3FA66FAEE" box="[116,1456,1365,1381]" gridrow="44" pageId="4" pageNumber="5" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEFAC3FF46FAEE" box="[116,144,1365,1381]" gridcol="0" gridrow="44" pageId="4" pageNumber="5">1ʹʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFAC3FE9CFAEE" box="[181,330,1365,1381]" gridcol="1" gridrow="44" pageId="4" pageNumber="5">5.32, s</td>
|
||
<td id="768C5DB9EF510056FEFAFAC3FDD3FAEE" box="[368,517,1365,1381]" gridcol="2" gridrow="44" pageId="4" pageNumber="5">5.34, s</td>
|
||
<td id="768C5DB9EF510056FDA6FAC3FD17FAEE" box="[556,705,1365,1381]" gridcol="3" gridrow="44" pageId="4" pageNumber="5">5.31, s</td>
|
||
<td id="768C5DB9EF510056FD6DFAC3FCAAFAEE" box="[743,892,1365,1381]" gridcol="4" gridrow="44" pageId="4" pageNumber="5">5.34, s</td>
|
||
<td id="768C5DB9EF510056FC29FAC3FBEEFAEE" box="[931,1080,1365,1381]" gridcol="5" gridrow="44" pageId="4" pageNumber="5">4.94, d (7.5)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFAFAFA66FAF0" box="[116,1456,1388,1403]" gridrow="45" pageId="4" pageNumber="5" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEFAFAFF46FAF0" box="[116,144,1388,1403]" gridcol="0" gridrow="45" pageId="4" pageNumber="5">2ʹʹ</th>
|
||
<td id="768C5DB9EF510056FC29FAFAFBEEFAF0" box="[931,1080,1388,1403]" gridcol="5" gridrow="45" pageId="4" pageNumber="5">4.01, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFA15FA66FA19" box="[116,1456,1411,1426]" gridrow="46" pageId="4" pageNumber="5" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEFA15FF46FA19" box="[116,144,1411,1426]" gridcol="0" gridrow="46" pageId="4" pageNumber="5">3ʹʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFA15FE9CFA19" box="[181,330,1411,1426]" gridcol="1" gridrow="46" pageId="4" pageNumber="5">4.21, d (10.0)</td>
|
||
<td id="768C5DB9EF510056FEFAFA15FDD3FA19" box="[368,517,1411,1426]" gridcol="2" gridrow="46" pageId="4" pageNumber="5">4.24, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FA15FD17FA19" box="[556,705,1411,1426]" gridcol="3" gridrow="46" pageId="4" pageNumber="5">4.22, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFA15FCAAFA19" box="[743,892,1411,1426]" gridcol="4" gridrow="46" pageId="4" pageNumber="5">4.23, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FA15FBEEFA19" box="[931,1080,1411,1426]" gridcol="5" gridrow="46" pageId="4" pageNumber="5">4.26, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFA0CFA66FA22" box="[116,1456,1434,1449]" gridrow="47" pageId="4" pageNumber="5" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEFA0CFF46FA22" box="[116,144,1434,1449]" gridcol="0" gridrow="47" pageId="4" pageNumber="5">4ʹʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFA0CFE9CFA22" box="[181,330,1434,1449]" gridcol="1" gridrow="47" pageId="4" pageNumber="5">4.35, dd (10.0, 7.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFA0CFDD3FA22" box="[368,517,1434,1449]" gridcol="2" gridrow="47" pageId="4" pageNumber="5">4.38, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FA0CFD17FA22" box="[556,705,1434,1449]" gridcol="3" gridrow="47" pageId="4" pageNumber="5">5.21, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFA0CFCAAFA22" box="[743,892,1434,1449]" gridcol="4" gridrow="47" pageId="4" pageNumber="5">4.36, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FA0CFBEEFA22" box="[931,1080,1434,1449]" gridcol="5" gridrow="47" pageId="4" pageNumber="5">4.22, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFA27FA66FA4B" box="[116,1456,1457,1472]" gridrow="48" pageId="4" pageNumber="5" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEFA27FF46FA4B" box="[116,144,1457,1472]" gridcol="0" gridrow="48" pageId="4" pageNumber="5">5ʹʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFA27FE9CFA4B" box="[181,330,1457,1472]" gridcol="1" gridrow="48" pageId="4" pageNumber="5">4.01 d (10.0, 7.0)</td>
|
||
<td id="768C5DB9EF510056FEFAFA27FDD3FA4B" box="[368,517,1457,1472]" gridcol="2" gridrow="48" pageId="4" pageNumber="5">4.04, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FA27FD17FA4B" box="[556,705,1457,1472]" gridcol="3" gridrow="48" pageId="4" pageNumber="5">4.03, t (7.5)</td>
|
||
<td id="768C5DB9EF510056FD6DFA27FCAAFA4B" box="[743,892,1457,1472]" gridcol="4" gridrow="48" pageId="4" pageNumber="5">4.02, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FA27FBEEFA4B" box="[931,1080,1457,1472]" gridcol="5" gridrow="48" pageId="4" pageNumber="5">4.02, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFA5EFA66FA5C" box="[116,1456,1480,1495]" gridrow="49" pageId="4" pageNumber="5" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEFA5EFF46FA5C" box="[116,144,1480,1495]" gridcol="0" gridrow="49" pageId="4" pageNumber="5">6ʹʹ</th>
|
||
<td id="768C5DB9EF510056FF3FFA5EFE9CFA5C" box="[181,330,1480,1495]" gridcol="1" gridrow="49" pageId="4" pageNumber="5">4.33, d (10.5, 7.0)</td>
|
||
<td id="768C5DB9EF510056FEFAFA5EFDD3FA5C" box="[368,517,1480,1495]" gridcol="2" gridrow="49" pageId="4" pageNumber="5">4.36, overlap</td>
|
||
<td id="768C5DB9EF510056FDA6FA5EFD17FA5C" box="[556,705,1480,1495]" gridcol="3" gridrow="49" pageId="4" pageNumber="5">4.61, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFA5EFCAAFA5C" box="[743,892,1480,1495]" gridcol="4" gridrow="49" pageId="4" pageNumber="5">4.34, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FA5EFBEEFA5C" box="[931,1080,1480,1495]" gridcol="5" gridrow="49" pageId="4" pageNumber="5">4.40, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFA49FA66FA66" box="[116,1456,1503,1517]" gridrow="50" pageId="4" pageNumber="5" rowspan-0="1" rowspan-3="1" rowspan-6="1" rowspan-7="1">
|
||
<td id="768C5DB9EF510056FF3FFA49FE9CFA66" box="[181,330,1503,1517]" gridcol="1" gridrow="50" pageId="4" pageNumber="5">4.61, d (10.5)</td>
|
||
<td id="768C5DB9EF510056FEFAFA49FDD3FA66" box="[368,517,1503,1517]" gridcol="2" gridrow="50" pageId="4" pageNumber="5">4.60, overlap</td>
|
||
<td id="768C5DB9EF510056FD6DFA49FCAAFA66" box="[743,892,1503,1517]" gridcol="4" gridrow="50" pageId="4" pageNumber="5">4.62, overlap</td>
|
||
<td id="768C5DB9EF510056FC29FA49FBEEFA66" box="[931,1080,1503,1517]" gridcol="5" gridrow="50" pageId="4" pageNumber="5">4.59, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEFA60FA66F98F" box="[116,1456,1526,1540]" gridrow="51" pageId="4" pageNumber="5" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<td id="768C5DB9EF510056FD6DFA60FCAAF98F" box="[743,892,1526,1540]" gridcol="4" gridrow="51" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFD6DFA60FCF2F98F" bold="true" box="[743,804,1526,1540]" italics="true" pageId="4" pageNumber="5">16-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FBD4FA60FB25F98F" box="[1118,1267,1526,1540]" gridcol="6" gridrow="51" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFBD4FA60FB4DF98F" bold="true" box="[1118,1179,1526,1540]" italics="true" pageId="4" pageNumber="5">16-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FA90FA60FA66F98F" box="[1306,1456,1526,1540]" gridcol="7" gridrow="51" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFA90FA60FA81F98F" bold="true" box="[1306,1367,1526,1540]" italics="true" pageId="4" pageNumber="5">16-O-Ac</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF99BFA66F990" box="[116,1456,1549,1563]" gridrow="52" pageId="4" pageNumber="5" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<th id="768C5DB9EF510056FFFEF99BFF46F990" box="[116,144,1549,1563]" gridcol="0" gridrow="52" pageId="4" pageNumber="5">2</th>
|
||
<td id="768C5DB9EF510056FD6DF99BFCAAF990" box="[743,892,1549,1563]" gridcol="4" gridrow="52" pageId="4" pageNumber="5">2.02, s</td>
|
||
<td id="768C5DB9EF510056FBD4F99BFB25F990" box="[1118,1267,1549,1563]" gridcol="6" gridrow="52" pageId="4" pageNumber="5">2.11, s</td>
|
||
<td id="768C5DB9EF510056FA90F99BFA66F990" box="[1306,1456,1549,1563]" gridcol="7" gridrow="52" pageId="4" pageNumber="5">2.03, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF9B2FA66F9B9" box="[116,1456,1572,1586]" gridrow="53" pageId="4" pageNumber="5" rowspan-0="1" rowspan-5="1">
|
||
<td id="768C5DB9EF510056FF3FF9B2FE9CF9B9" box="[181,330,1572,1586]" gridcol="1" gridrow="53" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFF3FF9B2FF23F9B9" bold="true" box="[181,245,1572,1586]" italics="true" pageId="4" pageNumber="5">21-O-Mb</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FEFAF9B2FDD3F9B9" box="[368,517,1572,1586]" gridcol="2" gridrow="53" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFEFAF9B2FE66F9B9" bold="true" box="[368,432,1572,1586]" italics="true" pageId="4" pageNumber="5">21-O-Tig</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FDA6F9B2FD17F9B9" box="[556,705,1572,1586]" gridcol="3" gridrow="53" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFDA6F9B2FDBEF9B9" bold="true" box="[556,616,1572,1586]" italics="true" pageId="4" pageNumber="5">21-O-Bz</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FD6DF9B2FCAAF9B9" box="[743,892,1572,1586]" gridcol="4" gridrow="53" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFD6DF9B2FCFEF9B9" bold="true" box="[743,808,1572,1586]" italics="true" pageId="4" pageNumber="5">21-O-Tig</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FBD4F9B2FB25F9B9" box="[1118,1267,1572,1586]" gridcol="6" gridrow="53" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFBD4F9B2FB4DF9B9" bold="true" box="[1118,1179,1572,1586]" italics="true" pageId="4" pageNumber="5">21-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FA90F9B2FA66F9B9" box="[1306,1456,1572,1586]" gridcol="7" gridrow="53" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFA90F9B2FA8CF9B9" bold="true" box="[1306,1370,1572,1586]" italics="true" pageId="4" pageNumber="5">21-O-Tig</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF9C7FA66F9EB" box="[116,1456,1617,1632]" gridrow="54" pageId="4" pageNumber="5" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEF9C7FF46F9EB" box="[116,144,1617,1632]" gridcol="0" gridrow="54" pageId="4" pageNumber="5">2</th>
|
||
<td id="768C5DB9EF510056FF3FF9C7FE9CF9EB" box="[181,330,1617,1632]" gridcol="1" gridrow="54" pageId="4" pageNumber="5">2.56, sextet (6.0)</td>
|
||
<td id="768C5DB9EF510056FBD4F9C7FB25F9EB" box="[1118,1267,1617,1632]" gridcol="6" gridrow="54" pageId="4" pageNumber="5">2.17, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF9FEFA66F9FC" box="[116,1456,1640,1655]" gridrow="55" pageId="4" pageNumber="5" rowspan-5="1" rowspan-6="1">
|
||
<th id="768C5DB9EF510056FFFEF9FEFF46F9FC" box="[116,144,1640,1655]" gridcol="0" gridrow="55" pageId="4" pageNumber="5">3</th>
|
||
<td id="768C5DB9EF510056FF3FF9FEFE9CF9FC" box="[181,330,1640,1655]" gridcol="1" gridrow="55" pageId="4" pageNumber="5">1.53, overlap</td>
|
||
<td id="768C5DB9EF510056FEFAF9FEFDD3F9FC" box="[368,517,1640,1655]" gridcol="2" gridrow="55" pageId="4" pageNumber="5">7.03, q (7.0)</td>
|
||
<td id="768C5DB9EF510056FDA6F9FEFD17F9FC" box="[556,705,1640,1655]" gridcol="3" gridrow="55" pageId="4" pageNumber="5">8.27, d (7.5)</td>
|
||
<td id="768C5DB9EF510056FD6DF9FEFCAAF9FC" box="[743,892,1640,1655]" gridcol="4" gridrow="55" pageId="4" pageNumber="5">7.04, q (7.0)</td>
|
||
<td id="768C5DB9EF510056FA90F9FEFA66F9FC" box="[1306,1456,1640,1655]" gridcol="7" gridrow="55" pageId="4" pageNumber="5">7.04, q (6.8)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF9E9FA66F906" box="[116,1456,1663,1677]" gridrow="56" pageId="4" pageNumber="5" rowspan-0="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<td id="768C5DB9EF510056FF3FF9E9FE9CF906" box="[181,330,1663,1677]" gridcol="1" gridrow="56" pageId="4" pageNumber="5">1.86, overlap</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF900FA66F92F" box="[116,1456,1686,1700]" gridrow="57" pageId="4" pageNumber="5" rowspan-5="1" rowspan-6="1">
|
||
<th id="768C5DB9EF510056FFFEF900FF46F92F" box="[116,144,1686,1700]" gridcol="0" gridrow="57" pageId="4" pageNumber="5">4</th>
|
||
<td id="768C5DB9EF510056FF3FF900FE9CF92F" box="[181,330,1686,1700]" gridcol="1" gridrow="57" pageId="4" pageNumber="5">0.97, t (7.0)</td>
|
||
<td id="768C5DB9EF510056FEFAF900FDD3F92F" box="[368,517,1686,1700]" gridcol="2" gridrow="57" pageId="4" pageNumber="5">1.88, s</td>
|
||
<td id="768C5DB9EF510056FDA6F900FD17F92F" box="[556,705,1686,1700]" gridcol="3" gridrow="57" pageId="4" pageNumber="5">7.43, t (7.5)</td>
|
||
<td id="768C5DB9EF510056FD6DF900FCAAF92F" box="[743,892,1686,1700]" gridcol="4" gridrow="57" pageId="4" pageNumber="5">1.90, s</td>
|
||
<td id="768C5DB9EF510056FA90F900FA66F92F" box="[1306,1456,1686,1700]" gridcol="7" gridrow="57" pageId="4" pageNumber="5">1.90, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF93BFA66F930" box="[116,1456,1709,1723]" gridrow="58" pageId="4" pageNumber="5" rowspan-5="1" rowspan-6="1">
|
||
<th id="768C5DB9EF510056FFFEF93BFF46F930" box="[116,144,1709,1723]" gridcol="0" gridrow="58" pageId="4" pageNumber="5">5</th>
|
||
<td id="768C5DB9EF510056FF3FF93BFE9CF930" box="[181,330,1709,1723]" gridcol="1" gridrow="58" pageId="4" pageNumber="5">1.23, d (7.0)</td>
|
||
<td id="768C5DB9EF510056FEFAF93BFDD3F930" box="[368,517,1709,1723]" gridcol="2" gridrow="58" pageId="4" pageNumber="5">1.61, d (7.0)</td>
|
||
<td id="768C5DB9EF510056FDA6F93BFD17F930" box="[556,705,1709,1723]" gridcol="3" gridrow="58" pageId="4" pageNumber="5">7.51, t (7.5)</td>
|
||
<td id="768C5DB9EF510056FD6DF93BFCAAF930" box="[743,892,1709,1723]" gridcol="4" gridrow="58" pageId="4" pageNumber="5">1.63, d (7.0)</td>
|
||
<td id="768C5DB9EF510056FA90F93BFA66F930" box="[1306,1456,1709,1723]" gridcol="7" gridrow="58" pageId="4" pageNumber="5">1.63, d (7.2)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF952FA66F959" box="[116,1456,1732,1746]" gridrow="59" pageId="4" pageNumber="5" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEF952FF46F959" box="[116,144,1732,1746]" gridcol="0" gridrow="59" pageId="4" pageNumber="5">6</th>
|
||
<td id="768C5DB9EF510056FDA6F952FD17F959" box="[556,705,1732,1746]" gridcol="3" gridrow="59" pageId="4" pageNumber="5">7.43, t (7.5)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF94CFA66F962" box="[116,1456,1754,1769]" gridrow="60" pageId="4" pageNumber="5" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEF94CFF46F962" box="[116,144,1754,1769]" gridcol="0" gridrow="60" pageId="4" pageNumber="5">7</th>
|
||
<td id="768C5DB9EF510056FDA6F94CFD17F962" box="[556,705,1754,1769]" gridcol="3" gridrow="60" pageId="4" pageNumber="5">8.27, d (7.5)</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF967FA66F974" box="[116,1456,1777,1791]" gridrow="61" pageId="4" pageNumber="5" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<td id="768C5DB9EF510056FD6DF967FCAAF974" box="[743,892,1777,1791]" gridcol="4" gridrow="61" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFD6DF967FCF2F974" bold="true" box="[743,804,1777,1791]" italics="true" pageId="4" pageNumber="5">22-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FBD4F967FB25F974" box="[1118,1267,1777,1791]" gridcol="6" gridrow="61" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFBD4F967FB4DF974" bold="true" box="[1118,1179,1777,1791]" italics="true" pageId="4" pageNumber="5">22-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FA90F967FA66F974" box="[1306,1456,1777,1791]" gridcol="7" gridrow="61" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFA90F967FA81F974" bold="true" box="[1306,1367,1777,1791]" italics="true" pageId="4" pageNumber="5">22-O-Ac</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF889FA66F8A6" box="[116,1456,1823,1837]" gridrow="62" pageId="4" pageNumber="5" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<th id="768C5DB9EF510056FFFEF889FF46F8A6" box="[116,144,1823,1837]" gridcol="0" gridrow="62" pageId="4" pageNumber="5">2</th>
|
||
<td id="768C5DB9EF510056FD6DF889FCAAF8A6" box="[743,892,1823,1837]" gridcol="4" gridrow="62" pageId="4" pageNumber="5">2.12, s</td>
|
||
<td id="768C5DB9EF510056FBD4F889FB25F8A6" box="[1118,1267,1823,1837]" gridcol="6" gridrow="62" pageId="4" pageNumber="5">2.08, s</td>
|
||
<td id="768C5DB9EF510056FA90F889FA66F8A6" box="[1306,1456,1823,1837]" gridcol="7" gridrow="62" pageId="4" pageNumber="5">2.13, s</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF8A0FA66F8CF" box="[116,1456,1846,1860]" gridrow="63" pageId="4" pageNumber="5" rowspan-0="1" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<td id="768C5DB9EF510056FF3FF8A0FE9CF8CF" box="[181,330,1846,1860]" gridcol="1" gridrow="63" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFF3FF8A0FF27F8CF" bold="true" box="[181,241,1846,1860]" italics="true" pageId="4" pageNumber="5">28-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FEFAF8A0FDD3F8CF" box="[368,517,1846,1860]" gridcol="2" gridrow="63" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFEFAF8A0FE7BF8CF" bold="true" box="[368,429,1846,1860]" italics="true" pageId="4" pageNumber="5">28-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF510056FDA6F8A0FD17F8CF" box="[556,705,1846,1860]" gridcol="3" gridrow="63" pageId="4" pageNumber="5">
|
||
<emphasis id="B919EA95EF51FFADFDA6F8A0FDBEF8CF" bold="true" box="[556,616,1846,1860]" italics="true" pageId="4" pageNumber="5">28-O-Ac</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF510056FFFEF8F5FA66F8FA" box="[116,1456,1891,1905]" gridrow="64" pageId="4" pageNumber="5" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF510056FFFEF8F5FF46F8FA" box="[116,144,1891,1905]" gridcol="0" gridrow="64" pageId="4" pageNumber="5">2</th>
|
||
<td id="768C5DB9EF510056FF3FF8F5FE9CF8FA" box="[181,330,1891,1905]" gridcol="1" gridrow="64" pageId="4" pageNumber="5">1.94, s</td>
|
||
<td id="768C5DB9EF510056FEFAF8F5FDD3F8FA" box="[368,517,1891,1905]" gridcol="2" gridrow="64" pageId="4" pageNumber="5">2.02, s</td>
|
||
<td id="768C5DB9EF510056FDA6F8F5FD17F8FA" box="[556,705,1891,1905]" gridcol="3" gridrow="64" pageId="4" pageNumber="5">1.96, s</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF51FFADFFFDF81AFF47F813" blockId="4.[119,313,1932,1979]" box="[119,145,1932,1944]" pageId="4" pageNumber="5">
|
||
<superScript id="7C189BCFEF51FFADFFFDF81AFF47F813" attach="right" box="[119,145,1932,1944]" fontSize="5" pageId="4" pageNumber="5">a 1</superScript>
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF51FFADFF1BF807FEEEF829" blockId="4.[119,313,1932,1979]" box="[145,312,1936,1954]" pageId="4" pageNumber="5">H NMR (500 MHz).</paragraph>
|
||
<paragraph id="8BD23687EF51FFADFFFDF833FEEFF830" blockId="4.[119,313,1932,1979]" box="[119,313,1957,1979]" pageId="4" pageNumber="5">
|
||
<superScript id="7C189BCFEF51FFADFFFDF833FF47F839" attach="right" box="[119,145,1957,1970]" fontSize="5" pageId="4" pageNumber="5">b 1</superScript>
|
||
H NMR (600 MHz).
|
||
</paragraph>
|
||
<caption id="DF12660FEF50FFACFFEEFF37FE0FFF46" pageId="5" pageNumber="6" startId="5.[100,150,161,177]" targetBox="[116,1455,222,1793]" targetIsTable="true" targetPageId="5" targetType="table">
|
||
<paragraph id="8BD23687EF50FFACFFEEFF37FF7EFF39" blockId="5.[100,646,161,205]" box="[100,168,161,178]" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFFEEFF37FF7EFF39" bold="true" box="[100,168,161,178]" pageId="5" pageNumber="6">Table 2</emphasis>
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF50FFACFFEEFF20FD50FF40" blockId="5.[100,646,161,205]" box="[100,646,182,203]" pageId="5" pageNumber="6">
|
||
<superScript id="7C189BCFEF50FFACFFEEFF20FFA2FF49" attach="right" box="[100,116,182,194]" fontSize="5" pageId="5" pageNumber="6">13</superScript>
|
||
C NMR spectroscopic data (in Pyridine-
|
||
<emphasis id="B919EA95EF50FFACFE4DFF2CFE07FF40" bold="true" box="[455,465,186,203]" italics="true" pageId="5" pageNumber="6">d</emphasis>
|
||
) of compounds 1-7.
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF50FFACFE5BFF57FE0FFF46" blockId="5.[100,646,161,205]" box="[465,473,193,205]" pageId="5" pageNumber="6">
|
||
<subScript id="17E934C2EF50FFACFE5BFF57FE0FFF46" attach="left" box="[465,473,193,205]" fontSize="5" pageId="5" pageNumber="6">5</subScript>
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8BD23687EF50FFACFFFEFF75FD78F88A" pageId="5" pageNumber="6">
|
||
<table id="F96DC427EF500056FFFEFF48FA79F88A" box="[116,1455,222,1793]" colsContinueFrom="4.[116,1456,222,1905]" gridcols="8" gridrows="62" pageId="5" pageNumber="6">
|
||
<tr id="355D34C5EF500056FFFEFF48FA79FF7A" box="[116,1455,222,241]" gridrow="0" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFF48FF46FF7A" box="[116,144,222,241]" gridcol="0" gridrow="0" pageId="5" pageNumber="6">No.</th>
|
||
<th id="768C5DB9EF500056FF63FF48FE9AFF7A" box="[233,332,222,241]" gridcol="1" gridrow="0" pageId="5" pageNumber="6">1a</th>
|
||
<th id="768C5DB9EF500056FE2DFF48FDDFFF7A" box="[423,521,222,241]" gridcol="2" gridrow="0" pageId="5" pageNumber="6">2a</th>
|
||
<th id="768C5DB9EF500056FDEEFF48FD1FFF7A" box="[612,713,222,241]" gridcol="3" gridrow="0" pageId="5" pageNumber="6">3a</th>
|
||
<th id="768C5DB9EF500056FCAEFF48FC50FF7A" box="[804,902,222,241]" gridcol="4" gridrow="0" pageId="5" pageNumber="6">4b</th>
|
||
<th id="768C5DB9EF500056FC6BFF48FBF8FF7A" box="[993,1070,222,241]" gridcol="5" gridrow="0" pageId="5" pageNumber="6">5a</th>
|
||
<th id="768C5DB9EF500056FB03FF48FB38FF7A" box="[1161,1262,222,241]" gridcol="6" gridrow="0" pageId="5" pageNumber="6">6a</th>
|
||
<th id="768C5DB9EF500056FAC0FF48FA79FF7A" box="[1354,1455,222,241]" gridcol="7" gridrow="0" pageId="5" pageNumber="6">7 b</th>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFE98FA79FE94" box="[116,1455,270,287]" gridrow="1" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFE98FF46FE94" box="[116,144,270,287]" gridcol="0" gridrow="1" pageId="5" pageNumber="6">1</th>
|
||
<td id="768C5DB9EF500056FF63FE98FE9AFE94" box="[233,332,270,287]" gridcol="1" gridrow="1" pageId="5" pageNumber="6">39.0, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFE98FDDFFE94" box="[423,521,270,287]" gridcol="2" gridrow="1" pageId="5" pageNumber="6">39.0, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFE98FD1FFE94" box="[612,713,270,287]" gridcol="3" gridrow="1" pageId="5" pageNumber="6">39.1, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFE98FC50FE94" box="[804,902,270,287]" gridcol="4" gridrow="1" pageId="5" pageNumber="6">39.0, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFE98FBF8FE94" box="[993,1070,270,287]" gridcol="5" gridrow="1" pageId="5" pageNumber="6">39.2, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FE98FB38FE94" box="[1161,1262,270,287]" gridcol="6" gridrow="1" pageId="5" pageNumber="6">39.0, CH2</td>
|
||
<td id="768C5DB9EF500056FAC0FE98FA79FE94" box="[1354,1455,270,287]" gridcol="7" gridrow="1" pageId="5" pageNumber="6">39.1, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFEB3FA79FEBD" box="[116,1455,293,310]" gridrow="2" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFEB3FF46FEBD" box="[116,144,293,310]" gridcol="0" gridrow="2" pageId="5" pageNumber="6">2</th>
|
||
<td id="768C5DB9EF500056FF63FEB3FE9AFEBD" box="[233,332,293,310]" gridcol="1" gridrow="2" pageId="5" pageNumber="6">26.4, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFEB3FDDFFEBD" box="[423,521,293,310]" gridcol="2" gridrow="2" pageId="5" pageNumber="6">26.4, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFEB3FD1FFEBD" box="[612,713,293,310]" gridcol="3" gridrow="2" pageId="5" pageNumber="6">26.4, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFEB3FC50FEBD" box="[804,902,293,310]" gridcol="4" gridrow="2" pageId="5" pageNumber="6">26.4, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFEB3FBF8FEBD" box="[993,1070,293,310]" gridcol="5" gridrow="2" pageId="5" pageNumber="6">27.0, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FEB3FB38FEBD" box="[1161,1262,293,310]" gridcol="6" gridrow="2" pageId="5" pageNumber="6">26.9, CH2</td>
|
||
<td id="768C5DB9EF500056FAC0FEB3FA79FEBD" box="[1354,1455,293,310]" gridcol="7" gridrow="2" pageId="5" pageNumber="6">26.4, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFEAAFA79FEC1" box="[116,1455,316,330]" gridrow="3" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFEAAFF46FEC1" box="[116,144,316,330]" gridcol="0" gridrow="3" pageId="5" pageNumber="6">3</th>
|
||
<td id="768C5DB9EF500056FF63FEAAFE9AFEC1" box="[233,332,316,330]" gridcol="1" gridrow="3" pageId="5" pageNumber="6">82.1, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFEAAFDDFFEC1" box="[423,521,316,330]" gridcol="2" gridrow="3" pageId="5" pageNumber="6">82.2, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFEAAFD1FFEC1" box="[612,713,316,330]" gridcol="3" gridrow="3" pageId="5" pageNumber="6">82.2, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFEAAFC50FEC1" box="[804,902,316,330]" gridcol="4" gridrow="3" pageId="5" pageNumber="6">82.2, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFEAAFBF8FEC1" box="[993,1070,316,330]" gridcol="5" gridrow="3" pageId="5" pageNumber="6">89.2, CH</td>
|
||
<td id="768C5DB9EF500056FB03FEAAFB38FEC1" box="[1161,1262,316,330]" gridcol="6" gridrow="3" pageId="5" pageNumber="6">89.1, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FEAAFA79FEC1" box="[1354,1455,316,330]" gridcol="7" gridrow="3" pageId="5" pageNumber="6">82.2, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFEC5FA79FEEA" box="[116,1455,339,353]" gridrow="4" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFEC5FF46FEEA" box="[116,144,339,353]" gridcol="0" gridrow="4" pageId="5" pageNumber="6">4</th>
|
||
<td id="768C5DB9EF500056FF63FEC5FE9AFEEA" box="[233,332,339,353]" gridcol="1" gridrow="4" pageId="5" pageNumber="6">43.8, C</td>
|
||
<td id="768C5DB9EF500056FE2DFEC5FDDFFEEA" box="[423,521,339,353]" gridcol="2" gridrow="4" pageId="5" pageNumber="6">43.9, C</td>
|
||
<td id="768C5DB9EF500056FDEEFEC5FD1FFEEA" box="[612,713,339,353]" gridcol="3" gridrow="4" pageId="5" pageNumber="6">43.9, C</td>
|
||
<td id="768C5DB9EF500056FCAEFEC5FC50FEEA" box="[804,902,339,353]" gridcol="4" gridrow="4" pageId="5" pageNumber="6">43.9, C</td>
|
||
<td id="768C5DB9EF500056FC6BFEC5FBF8FEEA" box="[993,1070,339,353]" gridcol="5" gridrow="4" pageId="5" pageNumber="6">39.9, C</td>
|
||
<td id="768C5DB9EF500056FB03FEC5FB38FEEA" box="[1161,1262,339,353]" gridcol="6" gridrow="4" pageId="5" pageNumber="6">39.8, C</td>
|
||
<td id="768C5DB9EF500056FAC0FEC5FA79FEEA" box="[1354,1455,339,353]" gridcol="7" gridrow="4" pageId="5" pageNumber="6">43.9, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFEFCFA79FEF3" box="[116,1455,362,376]" gridrow="5" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFEFCFF46FEF3" box="[116,144,362,376]" gridcol="0" gridrow="5" pageId="5" pageNumber="6">5</th>
|
||
<td id="768C5DB9EF500056FF63FEFCFE9AFEF3" box="[233,332,362,376]" gridcol="1" gridrow="5" pageId="5" pageNumber="6">47.2, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFEFCFDDFFEF3" box="[423,521,362,376]" gridcol="2" gridrow="5" pageId="5" pageNumber="6">47.3, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFEFCFD1FFEF3" box="[612,713,362,376]" gridcol="3" gridrow="5" pageId="5" pageNumber="6">47.5, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFEFCFC50FEF3" box="[804,902,362,376]" gridcol="4" gridrow="5" pageId="5" pageNumber="6">47.3, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFEFCFBF8FEF3" box="[993,1070,362,376]" gridcol="5" gridrow="5" pageId="5" pageNumber="6">56.1, CH</td>
|
||
<td id="768C5DB9EF500056FB03FEFCFB38FEF3" box="[1161,1262,362,376]" gridcol="6" gridrow="5" pageId="5" pageNumber="6">55.8, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FEFCFA79FEF3" box="[1354,1455,362,376]" gridcol="7" gridrow="5" pageId="5" pageNumber="6">47.7, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFE16FA79FE1A" box="[116,1455,384,401]" gridrow="6" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFE16FF46FE1A" box="[116,144,384,401]" gridcol="0" gridrow="6" pageId="5" pageNumber="6">6</th>
|
||
<td id="768C5DB9EF500056FF63FE16FE9AFE1A" box="[233,332,384,401]" gridcol="1" gridrow="6" pageId="5" pageNumber="6">18.3, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFE16FDDFFE1A" box="[423,521,384,401]" gridcol="2" gridrow="6" pageId="5" pageNumber="6">18.4, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFE16FD1FFE1A" box="[612,713,384,401]" gridcol="3" gridrow="6" pageId="5" pageNumber="6">18.4, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFE16FC50FE1A" box="[804,902,384,401]" gridcol="4" gridrow="6" pageId="5" pageNumber="6">18.3, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFE16FBF8FE1A" box="[993,1070,384,401]" gridcol="5" gridrow="6" pageId="5" pageNumber="6">18.8, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FE16FB38FE1A" box="[1161,1262,384,401]" gridcol="6" gridrow="6" pageId="5" pageNumber="6">18.6, CH2</td>
|
||
<td id="768C5DB9EF500056FAC0FE16FA79FE1A" box="[1354,1455,384,401]" gridcol="7" gridrow="6" pageId="5" pageNumber="6">18.3, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFE01FA79FE23" box="[116,1455,407,424]" gridrow="7" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFE01FF46FE23" box="[116,144,407,424]" gridcol="0" gridrow="7" pageId="5" pageNumber="6">7</th>
|
||
<td id="768C5DB9EF500056FF63FE01FE9AFE23" box="[233,332,407,424]" gridcol="1" gridrow="7" pageId="5" pageNumber="6">32.8, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFE01FDDFFE23" box="[423,521,407,424]" gridcol="2" gridrow="7" pageId="5" pageNumber="6">32.8, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFE01FD1FFE23" box="[612,713,407,424]" gridcol="3" gridrow="7" pageId="5" pageNumber="6">32.9, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFE01FC50FE23" box="[804,902,407,424]" gridcol="4" gridrow="7" pageId="5" pageNumber="6">32.8, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFE01FBF8FE23" box="[993,1070,407,424]" gridcol="5" gridrow="7" pageId="5" pageNumber="6">33.1, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FE01FB38FE23" box="[1161,1262,407,424]" gridcol="6" gridrow="7" pageId="5" pageNumber="6">33.0, CH2</td>
|
||
<td id="768C5DB9EF500056FAC0FE01FA79FE23" box="[1354,1455,407,424]" gridcol="7" gridrow="7" pageId="5" pageNumber="6">32.8, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFE38FA79FE37" box="[116,1455,430,444]" gridrow="8" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFE38FF46FE37" box="[116,144,430,444]" gridcol="0" gridrow="8" pageId="5" pageNumber="6">8</th>
|
||
<td id="768C5DB9EF500056FF63FE38FE9AFE37" box="[233,332,430,444]" gridcol="1" gridrow="8" pageId="5" pageNumber="6">40.5, C</td>
|
||
<td id="768C5DB9EF500056FE2DFE38FDDFFE37" box="[423,521,430,444]" gridcol="2" gridrow="8" pageId="5" pageNumber="6">40.6, C</td>
|
||
<td id="768C5DB9EF500056FDEEFE38FD1FFE37" box="[612,713,430,444]" gridcol="3" gridrow="8" pageId="5" pageNumber="6">40.6, C</td>
|
||
<td id="768C5DB9EF500056FCAEFE38FC50FE37" box="[804,902,430,444]" gridcol="4" gridrow="8" pageId="5" pageNumber="6">40.6, C</td>
|
||
<td id="768C5DB9EF500056FC6BFE38FBF8FE37" box="[993,1070,430,444]" gridcol="5" gridrow="8" pageId="5" pageNumber="6">40.5, C</td>
|
||
<td id="768C5DB9EF500056FB03FE38FB38FE37" box="[1161,1262,430,444]" gridcol="6" gridrow="8" pageId="5" pageNumber="6">40.5, C</td>
|
||
<td id="768C5DB9EF500056FAC0FE38FA79FE37" box="[1354,1455,430,444]" gridcol="7" gridrow="8" pageId="5" pageNumber="6">40.6, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFE53FA79FE58" box="[116,1455,453,467]" gridrow="9" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFE53FF46FE58" box="[116,144,453,467]" gridcol="0" gridrow="9" pageId="5" pageNumber="6">9</th>
|
||
<td id="768C5DB9EF500056FF63FE53FE9AFE58" box="[233,332,453,467]" gridcol="1" gridrow="9" pageId="5" pageNumber="6">47.6, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFE53FDDFFE58" box="[423,521,453,467]" gridcol="2" gridrow="9" pageId="5" pageNumber="6">47.6, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFE53FD1FFE58" box="[612,713,453,467]" gridcol="3" gridrow="9" pageId="5" pageNumber="6">47.7, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFE53FC50FE58" box="[804,902,453,467]" gridcol="4" gridrow="9" pageId="5" pageNumber="6">47.6, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFE53FBF8FE58" box="[993,1070,453,467]" gridcol="5" gridrow="9" pageId="5" pageNumber="6">47.3, CH</td>
|
||
<td id="768C5DB9EF500056FB03FE53FB38FE58" box="[1161,1262,453,467]" gridcol="6" gridrow="9" pageId="5" pageNumber="6">47.2, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FE53FA79FE58" box="[1354,1455,453,467]" gridcol="7" gridrow="9" pageId="5" pageNumber="6">47.9, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFE4AFA79FE61" box="[116,1455,476,490]" gridrow="10" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFE4AFF46FE61" box="[116,144,476,490]" gridcol="0" gridrow="10" pageId="5" pageNumber="6">10</th>
|
||
<td id="768C5DB9EF500056FF63FE4AFE9AFE61" box="[233,332,476,490]" gridcol="1" gridrow="10" pageId="5" pageNumber="6">36.7, C</td>
|
||
<td id="768C5DB9EF500056FE2DFE4AFDDFFE61" box="[423,521,476,490]" gridcol="2" gridrow="10" pageId="5" pageNumber="6">36.7, C</td>
|
||
<td id="768C5DB9EF500056FDEEFE4AFD1FFE61" box="[612,713,476,490]" gridcol="3" gridrow="10" pageId="5" pageNumber="6">36.7, C</td>
|
||
<td id="768C5DB9EF500056FCAEFE4AFC50FE61" box="[804,902,476,490]" gridcol="4" gridrow="10" pageId="5" pageNumber="6">37.1, C</td>
|
||
<td id="768C5DB9EF500056FC6BFE4AFBF8FE61" box="[993,1070,476,490]" gridcol="5" gridrow="10" pageId="5" pageNumber="6">37.3, C</td>
|
||
<td id="768C5DB9EF500056FB03FE4AFB38FE61" box="[1161,1262,476,490]" gridcol="6" gridrow="10" pageId="5" pageNumber="6">36.9, C</td>
|
||
<td id="768C5DB9EF500056FAC0FE4AFA79FE61" box="[1354,1455,476,490]" gridcol="7" gridrow="10" pageId="5" pageNumber="6">36.9, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFE65FA79FD88" box="[116,1455,499,515]" gridrow="11" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFE65FF46FD88" box="[116,144,499,515]" gridcol="0" gridrow="11" pageId="5" pageNumber="6">11</th>
|
||
<td id="768C5DB9EF500056FF63FE65FE9AFD88" box="[233,332,499,515]" gridcol="1" gridrow="11" pageId="5" pageNumber="6">24.2, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFE65FDDFFD88" box="[423,521,499,515]" gridcol="2" gridrow="11" pageId="5" pageNumber="6">24.3, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFE65FD1FFD88" box="[612,713,499,515]" gridcol="3" gridrow="11" pageId="5" pageNumber="6">24.3, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFE65FC50FD88" box="[804,902,499,515]" gridcol="4" gridrow="11" pageId="5" pageNumber="6">24.2, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFE65FBF8FD88" box="[993,1070,499,515]" gridcol="5" gridrow="11" pageId="5" pageNumber="6">24.2, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FE65FB38FD88" box="[1161,1262,499,515]" gridcol="6" gridrow="11" pageId="5" pageNumber="6">24.1, CH2</td>
|
||
<td id="768C5DB9EF500056FAC0FE65FA79FD88" box="[1354,1455,499,515]" gridcol="7" gridrow="11" pageId="5" pageNumber="6">24.2, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFD9FFA79FD93" box="[116,1455,521,536]" gridrow="12" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFD9FFF46FD93" box="[116,144,521,536]" gridcol="0" gridrow="12" pageId="5" pageNumber="6">12</th>
|
||
<td id="768C5DB9EF500056FF63FD9FFE9AFD93" box="[233,332,521,536]" gridcol="1" gridrow="12" pageId="5" pageNumber="6">124.9, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFD9FFDDFFD93" box="[423,521,521,536]" gridcol="2" gridrow="12" pageId="5" pageNumber="6">124.9, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFD9FFD1FFD93" box="[612,713,521,536]" gridcol="3" gridrow="12" pageId="5" pageNumber="6">125.0, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFD9FFC50FD93" box="[804,902,521,536]" gridcol="4" gridrow="12" pageId="5" pageNumber="6">125.0, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFD9FFBF8FD93" box="[993,1070,521,536]" gridcol="5" gridrow="12" pageId="5" pageNumber="6">123.3, CH</td>
|
||
<td id="768C5DB9EF500056FB03FD9FFB38FD93" box="[1161,1262,521,536]" gridcol="6" gridrow="12" pageId="5" pageNumber="6">125.0, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FD9FFA79FD93" box="[1354,1455,521,536]" gridcol="7" gridrow="12" pageId="5" pageNumber="6">125.0, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFDB6FA79FDA5" box="[116,1455,544,558]" gridrow="13" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFDB6FF46FDA5" box="[116,144,544,558]" gridcol="0" gridrow="13" pageId="5" pageNumber="6">13</th>
|
||
<td id="768C5DB9EF500056FF63FDB6FE9AFDA5" box="[233,332,544,558]" gridcol="1" gridrow="13" pageId="5" pageNumber="6">141.5, C</td>
|
||
<td id="768C5DB9EF500056FE2DFDB6FDDFFDA5" box="[423,521,544,558]" gridcol="2" gridrow="13" pageId="5" pageNumber="6">141.6, C</td>
|
||
<td id="768C5DB9EF500056FDEEFDB6FD1FFDA5" box="[612,713,544,558]" gridcol="3" gridrow="13" pageId="5" pageNumber="6">141.6, C</td>
|
||
<td id="768C5DB9EF500056FCAEFDB6FC50FDA5" box="[804,902,544,558]" gridcol="4" gridrow="13" pageId="5" pageNumber="6">140.9, C</td>
|
||
<td id="768C5DB9EF500056FC6BFDB6FBF8FDA5" box="[993,1070,544,558]" gridcol="5" gridrow="13" pageId="5" pageNumber="6">143.8, C</td>
|
||
<td id="768C5DB9EF500056FB03FDB6FB38FDA5" box="[1161,1262,544,558]" gridcol="6" gridrow="13" pageId="5" pageNumber="6">140.8, C</td>
|
||
<td id="768C5DB9EF500056FAC0FDB6FA79FDA5" box="[1354,1455,544,558]" gridcol="7" gridrow="13" pageId="5" pageNumber="6">140.9, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFDA1FA79FDCE" box="[116,1455,567,581]" gridrow="14" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFDA1FF46FDCE" box="[116,144,567,581]" gridcol="0" gridrow="14" pageId="5" pageNumber="6">14</th>
|
||
<td id="768C5DB9EF500056FF63FDA1FE9AFDCE" box="[233,332,567,581]" gridcol="1" gridrow="14" pageId="5" pageNumber="6">43.0, C</td>
|
||
<td id="768C5DB9EF500056FE2DFDA1FDDFFDCE" box="[423,521,567,581]" gridcol="2" gridrow="14" pageId="5" pageNumber="6">43.0, C</td>
|
||
<td id="768C5DB9EF500056FDEEFDA1FD1FFDCE" box="[612,713,567,581]" gridcol="3" gridrow="14" pageId="5" pageNumber="6">43.0, C</td>
|
||
<td id="768C5DB9EF500056FCAEFDA1FC50FDCE" box="[804,902,567,581]" gridcol="4" gridrow="14" pageId="5" pageNumber="6">43.2, C</td>
|
||
<td id="768C5DB9EF500056FC6BFDA1FBF8FDCE" box="[993,1070,567,581]" gridcol="5" gridrow="14" pageId="5" pageNumber="6">44.3, C</td>
|
||
<td id="768C5DB9EF500056FB03FDA1FB38FDCE" box="[1161,1262,567,581]" gridcol="6" gridrow="14" pageId="5" pageNumber="6">43.1, C</td>
|
||
<td id="768C5DB9EF500056FAC0FDA1FA79FDCE" box="[1354,1455,567,581]" gridcol="7" gridrow="14" pageId="5" pageNumber="6">43.2, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFDD8FA79FDD4" box="[116,1455,590,607]" gridrow="15" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFDD8FF46FDD4" box="[116,144,590,607]" gridcol="0" gridrow="15" pageId="5" pageNumber="6">15</th>
|
||
<td id="768C5DB9EF500056FF63FDD8FE9AFDD4" box="[233,332,590,607]" gridcol="1" gridrow="15" pageId="5" pageNumber="6">36.8, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFDD8FDDFFDD4" box="[423,521,590,607]" gridcol="2" gridrow="15" pageId="5" pageNumber="6">36.9, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFDD8FD1FFDD4" box="[612,713,590,607]" gridcol="3" gridrow="15" pageId="5" pageNumber="6">37.0, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFDD8FC50FDD4" box="[804,902,590,607]" gridcol="4" gridrow="15" pageId="5" pageNumber="6">33.9, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFDD8FBF8FDD4" box="[993,1070,590,607]" gridcol="5" gridrow="15" pageId="5" pageNumber="6">37.3, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FDD8FB38FDD4" box="[1161,1262,590,607]" gridcol="6" gridrow="15" pageId="5" pageNumber="6">33.8, CH2</td>
|
||
<td id="768C5DB9EF500056FAC0FDD8FA79FDD4" box="[1354,1455,590,607]" gridcol="7" gridrow="15" pageId="5" pageNumber="6">33.9, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFDF3FA79FDF8" box="[116,1455,613,627]" gridrow="16" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFDF3FF46FDF8" box="[116,144,613,627]" gridcol="0" gridrow="16" pageId="5" pageNumber="6">16</th>
|
||
<td id="768C5DB9EF500056FF63FDF3FE9AFDF8" box="[233,332,613,627]" gridcol="1" gridrow="16" pageId="5" pageNumber="6">67.8, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFDF3FDDFFDF8" box="[423,521,613,627]" gridcol="2" gridrow="16" pageId="5" pageNumber="6">67.8, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFDF3FD1FFDF8" box="[612,713,613,627]" gridcol="3" gridrow="16" pageId="5" pageNumber="6">67.9, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFDF3FC50FDF8" box="[804,902,613,627]" gridcol="4" gridrow="16" pageId="5" pageNumber="6">68.7, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFDF3FBF8FDF8" box="[993,1070,613,627]" gridcol="5" gridrow="16" pageId="5" pageNumber="6">66.5, CH</td>
|
||
<td id="768C5DB9EF500056FB03FDF3FB38FDF8" box="[1161,1262,613,627]" gridcol="6" gridrow="16" pageId="5" pageNumber="6">68.6, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FDF3FA79FDF8" box="[1354,1455,613,627]" gridcol="7" gridrow="16" pageId="5" pageNumber="6">68.7, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFDEAFA79FD01" box="[116,1455,636,650]" gridrow="17" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFDEAFF46FD01" box="[116,144,636,650]" gridcol="0" gridrow="17" pageId="5" pageNumber="6">17</th>
|
||
<td id="768C5DB9EF500056FF63FDEAFE9AFD01" box="[233,332,636,650]" gridcol="1" gridrow="17" pageId="5" pageNumber="6">46.0, C</td>
|
||
<td id="768C5DB9EF500056FE2DFDEAFDDFFD01" box="[423,521,636,650]" gridcol="2" gridrow="17" pageId="5" pageNumber="6">46.0, C</td>
|
||
<td id="768C5DB9EF500056FDEEFDEAFD1FFD01" box="[612,713,636,650]" gridcol="3" gridrow="17" pageId="5" pageNumber="6">46.0, C</td>
|
||
<td id="768C5DB9EF500056FCAEFDEAFC50FD01" box="[804,902,636,650]" gridcol="4" gridrow="17" pageId="5" pageNumber="6">47.9, C</td>
|
||
<td id="768C5DB9EF500056FC6BFDEAFBF8FD01" box="[993,1070,636,650]" gridcol="5" gridrow="17" pageId="5" pageNumber="6">41.7, C</td>
|
||
<td id="768C5DB9EF500056FB03FDEAFB38FD01" box="[1161,1262,636,650]" gridcol="6" gridrow="17" pageId="5" pageNumber="6">47.8, C</td>
|
||
<td id="768C5DB9EF500056FAC0FDEAFA79FD01" box="[1354,1455,636,650]" gridcol="7" gridrow="17" pageId="5" pageNumber="6">47.4, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFD05FA79FD2A" box="[116,1455,659,673]" gridrow="18" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFD05FF46FD2A" box="[116,144,659,673]" gridcol="0" gridrow="18" pageId="5" pageNumber="6">18</th>
|
||
<td id="768C5DB9EF500056FF63FD05FE9AFD2A" box="[233,332,659,673]" gridcol="1" gridrow="18" pageId="5" pageNumber="6">42.8, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFD05FDDFFD2A" box="[423,521,659,673]" gridcol="2" gridrow="18" pageId="5" pageNumber="6">42.8, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFD05FD1FFD2A" box="[612,713,659,673]" gridcol="3" gridrow="18" pageId="5" pageNumber="6">42.9, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFD05FC50FD2A" box="[804,902,659,673]" gridcol="4" gridrow="18" pageId="5" pageNumber="6">42.5, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFD05FBF8FD2A" box="[993,1070,659,673]" gridcol="5" gridrow="18" pageId="5" pageNumber="6">45.1, CH</td>
|
||
<td id="768C5DB9EF500056FB03FD05FB38FD2A" box="[1161,1262,659,673]" gridcol="6" gridrow="18" pageId="5" pageNumber="6">42.4, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FD05FA79FD2A" box="[1354,1455,659,673]" gridcol="7" gridrow="18" pageId="5" pageNumber="6">42.5, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFD3FFA79FD31" box="[116,1455,681,698]" gridrow="19" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFD3FFF46FD31" box="[116,144,681,698]" gridcol="0" gridrow="19" pageId="5" pageNumber="6">19</th>
|
||
<td id="768C5DB9EF500056FF63FD3FFE9AFD31" box="[233,332,681,698]" gridcol="1" gridrow="19" pageId="5" pageNumber="6">46.0, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFD3FFDDFFD31" box="[423,521,681,698]" gridcol="2" gridrow="19" pageId="5" pageNumber="6">46.1, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFD3FFD1FFD31" box="[612,713,681,698]" gridcol="3" gridrow="19" pageId="5" pageNumber="6">46.2, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFD3FFC50FD31" box="[804,902,681,698]" gridcol="4" gridrow="19" pageId="5" pageNumber="6">46.1, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFD3FFBF8FD31" box="[993,1070,681,698]" gridcol="5" gridrow="19" pageId="5" pageNumber="6">47.1, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FD3FFB38FD31" box="[1161,1262,681,698]" gridcol="6" gridrow="19" pageId="5" pageNumber="6">46.0, CH2</td>
|
||
<td id="768C5DB9EF500056FAC0FD3FFA79FD31" box="[1354,1455,681,698]" gridcol="7" gridrow="19" pageId="5" pageNumber="6">46.1, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFD56FA79FD45" box="[116,1455,704,718]" gridrow="20" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFD56FF46FD45" box="[116,144,704,718]" gridcol="0" gridrow="20" pageId="5" pageNumber="6">20</th>
|
||
<td id="768C5DB9EF500056FF63FD56FE9AFD45" box="[233,332,704,718]" gridcol="1" gridrow="20" pageId="5" pageNumber="6">36.9, C</td>
|
||
<td id="768C5DB9EF500056FE2DFD56FDDFFD45" box="[423,521,704,718]" gridcol="2" gridrow="20" pageId="5" pageNumber="6">37.0, C</td>
|
||
<td id="768C5DB9EF500056FDEEFD56FD1FFD45" box="[612,713,704,718]" gridcol="3" gridrow="20" pageId="5" pageNumber="6">37.0, C</td>
|
||
<td id="768C5DB9EF500056FCAEFD56FC50FD45" box="[804,902,704,718]" gridcol="4" gridrow="20" pageId="5" pageNumber="6">37.0, C</td>
|
||
<td id="768C5DB9EF500056FC6BFD56FBF8FD45" box="[993,1070,704,718]" gridcol="5" gridrow="20" pageId="5" pageNumber="6">37.0, C</td>
|
||
<td id="768C5DB9EF500056FB03FD56FB38FD45" box="[1161,1262,704,718]" gridcol="6" gridrow="20" pageId="5" pageNumber="6">36.8, C</td>
|
||
<td id="768C5DB9EF500056FAC0FD56FA79FD45" box="[1354,1455,704,718]" gridcol="7" gridrow="20" pageId="5" pageNumber="6">37.1, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFD41FA79FD63" box="[116,1455,727,744]" gridrow="21" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFD41FF46FD63" box="[116,144,727,744]" gridcol="0" gridrow="21" pageId="5" pageNumber="6">21</th>
|
||
<td id="768C5DB9EF500056FF63FD41FE9AFD63" box="[233,332,727,744]" gridcol="1" gridrow="21" pageId="5" pageNumber="6">78.6, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFD41FDDFFD63" box="[423,521,727,744]" gridcol="2" gridrow="21" pageId="5" pageNumber="6">79.2, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFD41FD1FFD63" box="[612,713,727,744]" gridcol="3" gridrow="21" pageId="5" pageNumber="6">80.3, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFD41FC50FD63" box="[804,902,727,744]" gridcol="4" gridrow="21" pageId="5" pageNumber="6">76.7, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFD41FBF8FD63" box="[993,1070,727,744]" gridcol="5" gridrow="21" pageId="5" pageNumber="6">34.5, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FD41FB38FD63" box="[1161,1262,727,744]" gridcol="6" gridrow="21" pageId="5" pageNumber="6">76.7, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FD41FA79FD63" box="[1354,1455,727,744]" gridcol="7" gridrow="21" pageId="5" pageNumber="6">76.7, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFD78FA79FD74" box="[116,1455,750,767]" gridrow="22" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFD78FF46FD74" box="[116,144,750,767]" gridcol="0" gridrow="22" pageId="5" pageNumber="6">22</th>
|
||
<td id="768C5DB9EF500056FF63FD78FE9AFD74" box="[233,332,750,767]" gridcol="1" gridrow="22" pageId="5" pageNumber="6">71.7, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFD78FDDFFD74" box="[423,521,750,767]" gridcol="2" gridrow="22" pageId="5" pageNumber="6">71.9, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFD78FD1FFD74" box="[612,713,750,767]" gridcol="3" gridrow="22" pageId="5" pageNumber="6">71.9, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFD78FC50FD74" box="[804,902,750,767]" gridcol="4" gridrow="22" pageId="5" pageNumber="6">72.0, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFD78FBF8FD74" box="[993,1070,750,767]" gridcol="5" gridrow="22" pageId="5" pageNumber="6">27.5, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FD78FB38FD74" box="[1161,1262,750,767]" gridcol="6" gridrow="22" pageId="5" pageNumber="6">71.9, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FD78FA79FD74" box="[1354,1455,750,767]" gridcol="7" gridrow="22" pageId="5" pageNumber="6">72.0, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFC93FA79FC9E" box="[116,1455,773,789]" gridrow="23" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFC93FF46FC9E" box="[116,144,773,789]" gridcol="0" gridrow="23" pageId="5" pageNumber="6">23</th>
|
||
<td id="768C5DB9EF500056FF63FC93FE9AFC9E" box="[233,332,773,789]" gridcol="1" gridrow="23" pageId="5" pageNumber="6">64.5, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFC93FDDFFC9E" box="[423,521,773,789]" gridcol="2" gridrow="23" pageId="5" pageNumber="6">64.5, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFC93FD1FFC9E" box="[612,713,773,789]" gridcol="3" gridrow="23" pageId="5" pageNumber="6">64.5, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFC93FC50FC9E" box="[804,902,773,789]" gridcol="4" gridrow="23" pageId="5" pageNumber="6">64.5, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFC93FBF8FC9E" box="[993,1070,773,789]" gridcol="5" gridrow="23" pageId="5" pageNumber="6">28.6, CH3</td>
|
||
<td id="768C5DB9EF500056FB03FC93FB38FC9E" box="[1161,1262,773,789]" gridcol="6" gridrow="23" pageId="5" pageNumber="6">28.4, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FC93FA79FC9E" box="[1354,1455,773,789]" gridcol="7" gridrow="23" pageId="5" pageNumber="6">64.7, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFC8AFA79FCA7" box="[116,1455,796,812]" gridrow="24" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFC8AFF46FCA7" box="[116,144,796,812]" gridcol="0" gridrow="24" pageId="5" pageNumber="6">24</th>
|
||
<td id="768C5DB9EF500056FF63FC8AFE9AFCA7" box="[233,332,796,812]" gridcol="1" gridrow="24" pageId="5" pageNumber="6">13.9, CH3</td>
|
||
<td id="768C5DB9EF500056FE2DFC8AFDDFFCA7" box="[423,521,796,812]" gridcol="2" gridrow="24" pageId="5" pageNumber="6">13.9, CH3</td>
|
||
<td id="768C5DB9EF500056FDEEFC8AFD1FFCA7" box="[612,713,796,812]" gridcol="3" gridrow="24" pageId="5" pageNumber="6">14.0, CH3</td>
|
||
<td id="768C5DB9EF500056FCAEFC8AFC50FCA7" box="[804,902,796,812]" gridcol="4" gridrow="24" pageId="5" pageNumber="6">14.0, CH3</td>
|
||
<td id="768C5DB9EF500056FC6BFC8AFBF8FCA7" box="[993,1070,796,812]" gridcol="5" gridrow="24" pageId="5" pageNumber="6">17.4, CH3</td>
|
||
<td id="768C5DB9EF500056FB03FC8AFB38FCA7" box="[1161,1262,796,812]" gridcol="6" gridrow="24" pageId="5" pageNumber="6">17.2, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FC8AFA79FCA7" box="[1354,1455,796,812]" gridcol="7" gridrow="24" pageId="5" pageNumber="6">14.0, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFCA5FA79FCC8" box="[116,1455,819,835]" gridrow="25" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFCA5FF46FCC8" box="[116,144,819,835]" gridcol="0" gridrow="25" pageId="5" pageNumber="6">25</th>
|
||
<td id="768C5DB9EF500056FF63FCA5FE9AFCC8" box="[233,332,819,835]" gridcol="1" gridrow="25" pageId="5" pageNumber="6">16.5, CH3</td>
|
||
<td id="768C5DB9EF500056FE2DFCA5FDDFFCC8" box="[423,521,819,835]" gridcol="2" gridrow="25" pageId="5" pageNumber="6">16.5, CH3</td>
|
||
<td id="768C5DB9EF500056FDEEFCA5FD1FFCC8" box="[612,713,819,835]" gridcol="3" gridrow="25" pageId="5" pageNumber="6">16.6, CH3</td>
|
||
<td id="768C5DB9EF500056FCAEFCA5FC50FCC8" box="[804,902,819,835]" gridcol="4" gridrow="25" pageId="5" pageNumber="6">16.5, CH3</td>
|
||
<td id="768C5DB9EF500056FC6BFCA5FBF8FCC8" box="[993,1070,819,835]" gridcol="5" gridrow="25" pageId="5" pageNumber="6">16.1, CH3</td>
|
||
<td id="768C5DB9EF500056FB03FCA5FB38FCC8" box="[1161,1262,819,835]" gridcol="6" gridrow="25" pageId="5" pageNumber="6">15.8, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FCA5FA79FCC8" box="[1354,1455,819,835]" gridcol="7" gridrow="25" pageId="5" pageNumber="6">16.5, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFCDFFA79FCD1" box="[116,1455,841,858]" gridrow="26" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFCDFFF46FCD1" box="[116,144,841,858]" gridcol="0" gridrow="26" pageId="5" pageNumber="6">26</th>
|
||
<td id="768C5DB9EF500056FF63FCDFFE9AFCD1" box="[233,332,841,858]" gridcol="1" gridrow="26" pageId="5" pageNumber="6">17.4, CH3</td>
|
||
<td id="768C5DB9EF500056FE2DFCDFFDDFFCD1" box="[423,521,841,858]" gridcol="2" gridrow="26" pageId="5" pageNumber="6">17.4, CH3</td>
|
||
<td id="768C5DB9EF500056FDEEFCDFFD1FFCD1" box="[612,713,841,858]" gridcol="3" gridrow="26" pageId="5" pageNumber="6">17.5, CH3</td>
|
||
<td id="768C5DB9EF500056FCAEFCDFFC50FCD1" box="[804,902,841,858]" gridcol="4" gridrow="26" pageId="5" pageNumber="6">17.3, CH3</td>
|
||
<td id="768C5DB9EF500056FC6BFCDFFBF8FCD1" box="[993,1070,841,858]" gridcol="5" gridrow="26" pageId="5" pageNumber="6">17.4, CH3</td>
|
||
<td id="768C5DB9EF500056FB03FCDFFB38FCD1" box="[1161,1262,841,858]" gridcol="6" gridrow="26" pageId="5" pageNumber="6">17.1, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FCDFFA79FCD1" box="[1354,1455,841,858]" gridcol="7" gridrow="26" pageId="5" pageNumber="6">17.3, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFCF6FA79FCFA" box="[116,1455,864,881]" gridrow="27" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFCF6FF46FCFA" box="[116,144,864,881]" gridcol="0" gridrow="27" pageId="5" pageNumber="6">27</th>
|
||
<td id="768C5DB9EF500056FF63FCF6FE9AFCFA" box="[233,332,864,881]" gridcol="1" gridrow="27" pageId="5" pageNumber="6">27.7, CH3</td>
|
||
<td id="768C5DB9EF500056FE2DFCF6FDDFFCFA" box="[423,521,864,881]" gridcol="2" gridrow="27" pageId="5" pageNumber="6">27.8, CH3</td>
|
||
<td id="768C5DB9EF500056FDEEFCF6FD1FFCFA" box="[612,713,864,881]" gridcol="3" gridrow="27" pageId="5" pageNumber="6">27.8, CH3</td>
|
||
<td id="768C5DB9EF500056FCAEFCF6FC50FCFA" box="[804,902,864,881]" gridcol="4" gridrow="27" pageId="5" pageNumber="6">27.7, CH3</td>
|
||
<td id="768C5DB9EF500056FC6BFCF6FBF8FCFA" box="[993,1070,864,881]" gridcol="5" gridrow="27" pageId="5" pageNumber="6">27.5, CH3</td>
|
||
<td id="768C5DB9EF500056FB03FCF6FB38FCFA" box="[1161,1262,864,881]" gridcol="6" gridrow="27" pageId="5" pageNumber="6">27.6, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FCF6FA79FCFA" box="[1354,1455,864,881]" gridcol="7" gridrow="27" pageId="5" pageNumber="6">27.7, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFCE1FA79FC03" box="[116,1455,887,904]" gridrow="28" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFCE1FF46FC03" box="[116,144,887,904]" gridcol="0" gridrow="28" pageId="5" pageNumber="6">28</th>
|
||
<td id="768C5DB9EF500056FF63FCE1FE9AFC03" box="[233,332,887,904]" gridcol="1" gridrow="28" pageId="5" pageNumber="6">62.6, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFCE1FDDFFC03" box="[423,521,887,904]" gridcol="2" gridrow="28" pageId="5" pageNumber="6">62.7, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFCE1FD1FFC03" box="[612,713,887,904]" gridcol="3" gridrow="28" pageId="5" pageNumber="6">62.7, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFCE1FC50FC03" box="[804,902,887,904]" gridcol="4" gridrow="28" pageId="5" pageNumber="6">58.2, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFCE1FBF8FC03" box="[993,1070,887,904]" gridcol="5" gridrow="28" pageId="5" pageNumber="6">78.7, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FCE1FB38FC03" box="[1161,1262,887,904]" gridcol="6" gridrow="28" pageId="5" pageNumber="6">58.2, CH2</td>
|
||
<td id="768C5DB9EF500056FAC0FCE1FA79FC03" box="[1354,1455,887,904]" gridcol="7" gridrow="28" pageId="5" pageNumber="6">58.2, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFC18FA79FC14" box="[116,1455,910,927]" gridrow="29" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFC18FF46FC14" box="[116,144,910,927]" gridcol="0" gridrow="29" pageId="5" pageNumber="6">29</th>
|
||
<td id="768C5DB9EF500056FF63FC18FE9AFC14" box="[233,332,910,927]" gridcol="1" gridrow="29" pageId="5" pageNumber="6">29.7, CH3</td>
|
||
<td id="768C5DB9EF500056FE2DFC18FDDFFC14" box="[423,521,910,927]" gridcol="2" gridrow="29" pageId="5" pageNumber="6">29.7, CH3</td>
|
||
<td id="768C5DB9EF500056FDEEFC18FD1FFC14" box="[612,713,910,927]" gridcol="3" gridrow="29" pageId="5" pageNumber="6">29.7, CH3</td>
|
||
<td id="768C5DB9EF500056FCAEFC18FC50FC14" box="[804,902,910,927]" gridcol="4" gridrow="29" pageId="5" pageNumber="6">29.5, CH3</td>
|
||
<td id="768C5DB9EF500056FC6BFC18FBF8FC14" box="[993,1070,910,927]" gridcol="5" gridrow="29" pageId="5" pageNumber="6">33.3, CH3</td>
|
||
<td id="768C5DB9EF500056FB03FC18FB38FC14" box="[1161,1262,910,927]" gridcol="6" gridrow="29" pageId="5" pageNumber="6">29.4, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FC18FA79FC14" box="[1354,1455,910,927]" gridcol="7" gridrow="29" pageId="5" pageNumber="6">29.5, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFC33FA79FC3E" box="[116,1455,933,949]" gridrow="30" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFC33FF46FC3E" box="[116,144,933,949]" gridcol="0" gridrow="30" pageId="5" pageNumber="6">30</th>
|
||
<td id="768C5DB9EF500056FF63FC33FE9AFC3E" box="[233,332,933,949]" gridcol="1" gridrow="30" pageId="5" pageNumber="6">20.9, CH3</td>
|
||
<td id="768C5DB9EF500056FE2DFC33FDDFFC3E" box="[423,521,933,949]" gridcol="2" gridrow="30" pageId="5" pageNumber="6">20.1, CH3</td>
|
||
<td id="768C5DB9EF500056FDEEFC33FD1FFC3E" box="[612,713,933,949]" gridcol="3" gridrow="30" pageId="5" pageNumber="6">20.2, CH3</td>
|
||
<td id="768C5DB9EF500056FCAEFC33FC50FC3E" box="[804,902,933,949]" gridcol="4" gridrow="30" pageId="5" pageNumber="6">20.1, CH3</td>
|
||
<td id="768C5DB9EF500056FC6BFC33FBF8FC3E" box="[993,1070,933,949]" gridcol="5" gridrow="30" pageId="5" pageNumber="6">24.4, CH3</td>
|
||
<td id="768C5DB9EF500056FB03FC33FB38FC3E" box="[1161,1262,933,949]" gridcol="6" gridrow="30" pageId="5" pageNumber="6">20.0, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FC33FA79FC3E" box="[1354,1455,933,949]" gridcol="7" gridrow="30" pageId="5" pageNumber="6">20.1, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFC2DFA79FC42" box="[116,1455,955,969]" gridrow="31" pageId="5" pageNumber="6" rowspan-0="1">
|
||
<td id="768C5DB9EF500056FF63FC2DFE9AFC42" box="[233,332,955,969]" gridcol="1" gridrow="31" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFF63FC2DFEFAFC42" bold="true" box="[233,300,955,969]" italics="true" pageId="5" pageNumber="6">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FE2DFC2DFDDFFC42" box="[423,521,955,969]" gridcol="2" gridrow="31" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFE2DFC2DFE3CFC42" bold="true" box="[423,490,955,969]" italics="true" pageId="5" pageNumber="6">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FDEEFC2DFD1FFC42" box="[612,713,955,969]" gridcol="3" gridrow="31" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFDEEFC2DFD71FC42" bold="true" box="[612,679,955,969]" italics="true" pageId="5" pageNumber="6">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FCAEFC2DFC50FC42" box="[804,902,955,969]" gridcol="4" gridrow="31" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFCAEFC2DFCB1FC42" bold="true" box="[804,871,955,969]" italics="true" pageId="5" pageNumber="6">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FC6BFC2DFBF8FC42" box="[993,1070,955,969]" gridcol="5" gridrow="31" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFC6BFC2DFBCFFC42" bold="true" box="[993,1049,955,969]" italics="true" pageId="5" pageNumber="6">3-O-Glc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FB03FC2DFB38FC42" box="[1161,1262,955,969]" gridcol="6" gridrow="31" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFB03FC2DFB1AFC42" bold="true" box="[1161,1228,955,969]" italics="true" pageId="5" pageNumber="6">3-O-GlcA</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FAC0FC2DFA79FC42" box="[1354,1455,955,969]" gridcol="7" gridrow="31" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFAC0FC2DFA5BFC42" bold="true" box="[1354,1421,955,969]" italics="true" pageId="5" pageNumber="6">3-O-GlcA</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFC7EFA79FC7C" box="[116,1455,1000,1015]" gridrow="32" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFC7EFF46FC7C" box="[116,144,1000,1015]" gridcol="0" gridrow="32" pageId="5" pageNumber="6">1ʹ</th>
|
||
<td id="768C5DB9EF500056FF63FC7EFE9AFC7C" box="[233,332,1000,1015]" gridcol="1" gridrow="32" pageId="5" pageNumber="6">106.8, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFC7EFDDFFC7C" box="[423,521,1000,1015]" gridcol="2" gridrow="32" pageId="5" pageNumber="6">106.8, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFC7EFD1FFC7C" box="[612,713,1000,1015]" gridcol="3" gridrow="32" pageId="5" pageNumber="6">106.9, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFC7EFC50FC7C" box="[804,902,1000,1015]" gridcol="4" gridrow="32" pageId="5" pageNumber="6">106.8, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFC7EFBF8FC7C" box="[993,1070,1000,1015]" gridcol="5" gridrow="32" pageId="5" pageNumber="6">107.3, CH</td>
|
||
<td id="768C5DB9EF500056FB03FC7EFB38FC7C" box="[1161,1262,1000,1015]" gridcol="6" gridrow="32" pageId="5" pageNumber="6">107.5, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FC7EFA79FC7C" box="[1354,1455,1000,1015]" gridcol="7" gridrow="32" pageId="5" pageNumber="6">106.6, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFC69FA79FB85" box="[116,1455,1023,1038]" gridrow="33" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFC69FF46FB85" box="[116,144,1023,1038]" gridcol="0" gridrow="33" pageId="5" pageNumber="6">2ʹ</th>
|
||
<td id="768C5DB9EF500056FF63FC69FE9AFB85" box="[233,332,1023,1038]" gridcol="1" gridrow="33" pageId="5" pageNumber="6">72.5, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFC69FDDFFB85" box="[423,521,1023,1038]" gridcol="2" gridrow="33" pageId="5" pageNumber="6">72.5, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFC69FD1FFB85" box="[612,713,1023,1038]" gridcol="3" gridrow="33" pageId="5" pageNumber="6">72.5, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFC69FC50FB85" box="[804,902,1023,1038]" gridcol="4" gridrow="33" pageId="5" pageNumber="6">72.5, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFC69FBF8FB85" box="[993,1070,1023,1038]" gridcol="5" gridrow="33" pageId="5" pageNumber="6">76.2, CH</td>
|
||
<td id="768C5DB9EF500056FB03FC69FB38FB85" box="[1161,1262,1023,1038]" gridcol="6" gridrow="33" pageId="5" pageNumber="6">75.8, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FC69FA79FB85" box="[1354,1455,1023,1038]" gridcol="7" gridrow="33" pageId="5" pageNumber="6">75.8, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFB80FA79FBAE" box="[116,1455,1046,1061]" gridrow="34" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFB80FF46FBAE" box="[116,144,1046,1061]" gridcol="0" gridrow="34" pageId="5" pageNumber="6">3ʹ</th>
|
||
<td id="768C5DB9EF500056FF63FB80FE9AFBAE" box="[233,332,1046,1061]" gridcol="1" gridrow="34" pageId="5" pageNumber="6">74.2, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFB80FDDFFBAE" box="[423,521,1046,1061]" gridcol="2" gridrow="34" pageId="5" pageNumber="6">74.2, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFB80FD1FFBAE" box="[612,713,1046,1061]" gridcol="3" gridrow="34" pageId="5" pageNumber="6">74.2, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFB80FC50FBAE" box="[804,902,1046,1061]" gridcol="4" gridrow="34" pageId="5" pageNumber="6">74.2, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFB80FBF8FBAE" box="[993,1070,1046,1061]" gridcol="5" gridrow="34" pageId="5" pageNumber="6">78.7, CH</td>
|
||
<td id="768C5DB9EF500056FB03FB80FB38FBAE" box="[1161,1262,1046,1061]" gridcol="6" gridrow="34" pageId="5" pageNumber="6">78.5, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FB80FA79FBAE" box="[1354,1455,1046,1061]" gridcol="7" gridrow="34" pageId="5" pageNumber="6">78.5, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFBBBFA79FBB7" box="[116,1455,1069,1084]" gridrow="35" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFBBBFF46FBB7" box="[116,144,1069,1084]" gridcol="0" gridrow="35" pageId="5" pageNumber="6">4ʹ</th>
|
||
<td id="768C5DB9EF500056FF63FBBBFE9AFBB7" box="[233,332,1069,1084]" gridcol="1" gridrow="35" pageId="5" pageNumber="6">69.9, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFBBBFDDFFBB7" box="[423,521,1069,1084]" gridcol="2" gridrow="35" pageId="5" pageNumber="6">69.9, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFBBBFD1FFBB7" box="[612,713,1069,1084]" gridcol="3" gridrow="35" pageId="5" pageNumber="6">69.9, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFBBBFC50FBB7" box="[804,902,1069,1084]" gridcol="4" gridrow="35" pageId="5" pageNumber="6">69.9, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFBBBFBF8FBB7" box="[993,1070,1069,1084]" gridcol="5" gridrow="35" pageId="5" pageNumber="6">72.2, CH</td>
|
||
<td id="768C5DB9EF500056FB03FBBBFB38FBB7" box="[1161,1262,1069,1084]" gridcol="6" gridrow="35" pageId="5" pageNumber="6">73.8, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FBBBFA79FBB7" box="[1354,1455,1069,1084]" gridcol="7" gridrow="35" pageId="5" pageNumber="6">73.8, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFBD2FA79FBD8" box="[116,1455,1092,1107]" gridrow="36" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFBD2FF46FBD8" box="[116,144,1092,1107]" gridcol="0" gridrow="36" pageId="5" pageNumber="6">5ʹ</th>
|
||
<td id="768C5DB9EF500056FF63FBD2FE9AFBD8" box="[233,332,1092,1107]" gridcol="1" gridrow="36" pageId="5" pageNumber="6">75.6, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFBD2FDDFFBD8" box="[423,521,1092,1107]" gridcol="2" gridrow="36" pageId="5" pageNumber="6">75.6, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFBD2FD1FFBD8" box="[612,713,1092,1107]" gridcol="3" gridrow="36" pageId="5" pageNumber="6">75.7, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFBD2FC50FBD8" box="[804,902,1092,1107]" gridcol="4" gridrow="36" pageId="5" pageNumber="6">75.6, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFBD2FBF8FBD8" box="[993,1070,1092,1107]" gridcol="5" gridrow="36" pageId="5" pageNumber="6">79.1, CH</td>
|
||
<td id="768C5DB9EF500056FB03FBD2FB38FBD8" box="[1161,1262,1092,1107]" gridcol="6" gridrow="36" pageId="5" pageNumber="6">77.9, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FBD2FA79FBD8" box="[1354,1455,1092,1107]" gridcol="7" gridrow="36" pageId="5" pageNumber="6">78.2, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFBCDFA79FBE7" box="[116,1455,1115,1132]" gridrow="37" pageId="5" pageNumber="6">
|
||
<th id="768C5DB9EF500056FFFEFBCDFF46FBE7" box="[116,144,1115,1132]" gridcol="0" gridrow="37" pageId="5" pageNumber="6">6ʹ</th>
|
||
<td id="768C5DB9EF500056FF63FBCDFE9AFBE7" box="[233,332,1115,1132]" gridcol="1" gridrow="37" pageId="5" pageNumber="6">171.6, C</td>
|
||
<td id="768C5DB9EF500056FE2DFBCDFDDFFBE7" box="[423,521,1115,1132]" gridcol="2" gridrow="37" pageId="5" pageNumber="6">171.6, C</td>
|
||
<td id="768C5DB9EF500056FDEEFBCDFD1FFBE7" box="[612,713,1115,1132]" gridcol="3" gridrow="37" pageId="5" pageNumber="6">171.6, COOH</td>
|
||
<td id="768C5DB9EF500056FCAEFBCDFC50FBE7" box="[804,902,1115,1132]" gridcol="4" gridrow="37" pageId="5" pageNumber="6">171.6, C</td>
|
||
<td id="768C5DB9EF500056FC6BFBCDFBF8FBE7" box="[993,1070,1115,1132]" gridcol="5" gridrow="37" pageId="5" pageNumber="6">63.4, CH2</td>
|
||
<td id="768C5DB9EF500056FB03FBCDFB38FBE7" box="[1161,1262,1115,1132]" gridcol="6" gridrow="37" pageId="5" pageNumber="6">173.3, COOH</td>
|
||
<td id="768C5DB9EF500056FAC0FBCDFA79FBE7" box="[1354,1455,1115,1132]" gridcol="7" gridrow="37" pageId="5" pageNumber="6">173.3, COOH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFBE4FA79FB0B" box="[116,1455,1138,1152]" gridrow="38" pageId="5" pageNumber="6" rowspan-0="1" rowspan-6="1" rowspan-7="1">
|
||
<td id="768C5DB9EF500056FF63FBE4FE9AFB0B" box="[233,332,1138,1152]" gridcol="1" gridrow="38" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFF63FBE4FE9AFB0B" bold="true" box="[233,332,1138,1152]" italics="true" pageId="5" pageNumber="6">3ʹ-O-2-oxoglc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FE2DFBE4FDDFFB0B" box="[423,521,1138,1152]" gridcol="2" gridrow="38" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFE2DFBE4FDDFFB0B" bold="true" box="[423,521,1138,1152]" italics="true" pageId="5" pageNumber="6">3ʹ-O-2-oxoglc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FDEEFBE4FD1FFB0B" box="[612,713,1138,1152]" gridcol="3" gridrow="38" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFDEEFBE4FD10FB0B" bold="true" box="[612,710,1138,1152]" italics="true" pageId="5" pageNumber="6">3ʹ-O-2-oxoglc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FCAEFBE4FC50FB0B" box="[804,902,1138,1152]" gridcol="4" gridrow="38" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFCAEFBE4FC50FB0B" bold="true" box="[804,902,1138,1152]" italics="true" pageId="5" pageNumber="6">3ʹ-O-2-oxoglc</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FC6BFBE4FBF8FB0B" box="[993,1070,1138,1152]" gridcol="5" gridrow="38" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFC6BFBE4FBF5FB0B" bold="true" box="[993,1059,1138,1152]" italics="true" pageId="5" pageNumber="6">28-O-Glc</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFB09FA79FB25" box="[116,1455,1183,1198]" gridrow="39" pageId="5" pageNumber="6" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEFB09FF46FB25" box="[116,144,1183,1198]" gridcol="0" gridrow="39" pageId="5" pageNumber="6">1ʹʹ</th>
|
||
<td id="768C5DB9EF500056FF63FB09FE9AFB25" box="[233,332,1183,1198]" gridcol="1" gridrow="39" pageId="5" pageNumber="6">97.4, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFB09FDDFFB25" box="[423,521,1183,1198]" gridcol="2" gridrow="39" pageId="5" pageNumber="6">97.5, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFB09FD1FFB25" box="[612,713,1183,1198]" gridcol="3" gridrow="39" pageId="5" pageNumber="6">97.5, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFB09FC50FB25" box="[804,902,1183,1198]" gridcol="4" gridrow="39" pageId="5" pageNumber="6">97.5, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFB09FBF8FB25" box="[993,1070,1183,1198]" gridcol="5" gridrow="39" pageId="5" pageNumber="6">106.2, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFB20FA79FB4E" box="[116,1455,1206,1221]" gridrow="40" pageId="5" pageNumber="6" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEFB20FF46FB4E" box="[116,144,1206,1221]" gridcol="0" gridrow="40" pageId="5" pageNumber="6">2ʹʹ</th>
|
||
<td id="768C5DB9EF500056FF63FB20FE9AFB4E" box="[233,332,1206,1221]" gridcol="1" gridrow="40" pageId="5" pageNumber="6">94.1, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFB20FDDFFB4E" box="[423,521,1206,1221]" gridcol="2" gridrow="40" pageId="5" pageNumber="6">94.2, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFB20FD1FFB4E" box="[612,713,1206,1221]" gridcol="3" gridrow="40" pageId="5" pageNumber="6">94.2, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFB20FC50FB4E" box="[804,902,1206,1221]" gridcol="4" gridrow="40" pageId="5" pageNumber="6">94.2, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFB20FBF8FB4E" box="[993,1070,1206,1221]" gridcol="5" gridrow="40" pageId="5" pageNumber="6">75.4, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFB5AFA79FB50" box="[116,1455,1228,1243]" gridrow="41" pageId="5" pageNumber="6" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEFB5AFF46FB50" box="[116,144,1228,1243]" gridcol="0" gridrow="41" pageId="5" pageNumber="6">3ʹʹ</th>
|
||
<td id="768C5DB9EF500056FF63FB5AFE9AFB50" box="[233,332,1228,1243]" gridcol="1" gridrow="41" pageId="5" pageNumber="6">80.2, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFB5AFDDFFB50" box="[423,521,1228,1243]" gridcol="2" gridrow="41" pageId="5" pageNumber="6">80.2, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFB5AFD1FFB50" box="[612,713,1228,1243]" gridcol="3" gridrow="41" pageId="5" pageNumber="6">80.2, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFB5AFC50FB50" box="[804,902,1228,1243]" gridcol="4" gridrow="41" pageId="5" pageNumber="6">80.2, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFB5AFBF8FB50" box="[993,1070,1228,1243]" gridcol="5" gridrow="41" pageId="5" pageNumber="6">78.4, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFB75FA79FB79" box="[116,1455,1251,1266]" gridrow="42" pageId="5" pageNumber="6" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEFB75FF46FB79" box="[116,144,1251,1266]" gridcol="0" gridrow="42" pageId="5" pageNumber="6">4ʹʹ</th>
|
||
<td id="768C5DB9EF500056FF63FB75FE9AFB79" box="[233,332,1251,1266]" gridcol="1" gridrow="42" pageId="5" pageNumber="6">70.1, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFB75FDDFFB79" box="[423,521,1251,1266]" gridcol="2" gridrow="42" pageId="5" pageNumber="6">70.1, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFB75FD1FFB79" box="[612,713,1251,1266]" gridcol="3" gridrow="42" pageId="5" pageNumber="6">70.2, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFB75FC50FB79" box="[804,902,1251,1266]" gridcol="4" gridrow="42" pageId="5" pageNumber="6">70.1, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFB75FBF8FB79" box="[993,1070,1251,1266]" gridcol="5" gridrow="42" pageId="5" pageNumber="6">72.0, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFB6CFA79FA82" box="[116,1455,1274,1289]" gridrow="43" pageId="5" pageNumber="6" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEFB6CFF46FA82" box="[116,144,1274,1289]" gridcol="0" gridrow="43" pageId="5" pageNumber="6">5ʹʹ</th>
|
||
<td id="768C5DB9EF500056FF63FB6CFE9AFA82" box="[233,332,1274,1289]" gridcol="1" gridrow="43" pageId="5" pageNumber="6">79.9, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFB6CFDDFFA82" box="[423,521,1274,1289]" gridcol="2" gridrow="43" pageId="5" pageNumber="6">80.0, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFB6CFD1FFA82" box="[612,713,1274,1289]" gridcol="3" gridrow="43" pageId="5" pageNumber="6">80.0, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFB6CFC50FA82" box="[804,902,1274,1289]" gridcol="4" gridrow="43" pageId="5" pageNumber="6">80.0, CH</td>
|
||
<td id="768C5DB9EF500056FC6BFB6CFBF8FA82" box="[993,1070,1274,1289]" gridcol="5" gridrow="43" pageId="5" pageNumber="6">79.1, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFA87FA79FAA9" box="[116,1455,1297,1314]" gridrow="44" pageId="5" pageNumber="6" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEFA87FF46FAA9" box="[116,144,1297,1314]" gridcol="0" gridrow="44" pageId="5" pageNumber="6">6ʹʹ</th>
|
||
<td id="768C5DB9EF500056FF63FA87FE9AFAA9" box="[233,332,1297,1314]" gridcol="1" gridrow="44" pageId="5" pageNumber="6">63.2, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFA87FDDFFAA9" box="[423,521,1297,1314]" gridcol="2" gridrow="44" pageId="5" pageNumber="6">63.2, CH2</td>
|
||
<td id="768C5DB9EF500056FDEEFA87FD1FFAA9" box="[612,713,1297,1314]" gridcol="3" gridrow="44" pageId="5" pageNumber="6">63.3, CH2</td>
|
||
<td id="768C5DB9EF500056FCAEFA87FC50FAA9" box="[804,902,1297,1314]" gridcol="4" gridrow="44" pageId="5" pageNumber="6">63.2, CH2</td>
|
||
<td id="768C5DB9EF500056FC6BFA87FBF8FAA9" box="[993,1070,1297,1314]" gridcol="5" gridrow="44" pageId="5" pageNumber="6">63.1, CH2</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFABFFA79FABC" box="[116,1455,1321,1335]" gridrow="45" pageId="5" pageNumber="6" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<td id="768C5DB9EF500056FCAEFABFFC50FABC" box="[804,902,1321,1335]" gridcol="4" gridrow="45" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFCAEFABFFCB7FABC" bold="true" box="[804,865,1321,1335]" italics="true" pageId="5" pageNumber="6">16-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FB03FABFFB38FABC" box="[1161,1262,1321,1335]" gridcol="6" gridrow="45" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFB03FABFFB10FABC" bold="true" box="[1161,1222,1321,1335]" italics="true" pageId="5" pageNumber="6">16-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FAC0FABFFA79FABC" box="[1354,1455,1321,1335]" gridcol="7" gridrow="45" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFAC0FABFFA51FABC" bold="true" box="[1354,1415,1321,1335]" italics="true" pageId="5" pageNumber="6">16-O-Ac</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFAC3FA79FAEF" box="[116,1455,1365,1380]" gridrow="46" pageId="5" pageNumber="6" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<th id="768C5DB9EF500056FFFEFAC3FF46FAEF" box="[116,144,1365,1380]" gridcol="0" gridrow="46" pageId="5" pageNumber="6">1ʹʹʹ</th>
|
||
<td id="768C5DB9EF500056FCAEFAC3FC50FAEF" box="[804,902,1365,1380]" gridcol="4" gridrow="46" pageId="5" pageNumber="6">170.2, C</td>
|
||
<td id="768C5DB9EF500056FB03FAC3FB38FAEF" box="[1161,1262,1365,1380]" gridcol="6" gridrow="46" pageId="5" pageNumber="6">170.5, C</td>
|
||
<td id="768C5DB9EF500056FAC0FAC3FA79FAEF" box="[1354,1455,1365,1380]" gridcol="7" gridrow="46" pageId="5" pageNumber="6">170.3, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFAFAFA79FAF6" box="[116,1455,1388,1405]" gridrow="47" pageId="5" pageNumber="6" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<th id="768C5DB9EF500056FFFEFAFAFF46FAF6" box="[116,144,1388,1405]" gridcol="0" gridrow="47" pageId="5" pageNumber="6">2ʹʹʹ</th>
|
||
<td id="768C5DB9EF500056FCAEFAFAFC50FAF6" box="[804,902,1388,1405]" gridcol="4" gridrow="47" pageId="5" pageNumber="6">21.4, CH3</td>
|
||
<td id="768C5DB9EF500056FB03FAFAFB38FAF6" box="[1161,1262,1388,1405]" gridcol="6" gridrow="47" pageId="5" pageNumber="6">21.3, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FAFAFA79FAF6" box="[1354,1455,1388,1405]" gridcol="7" gridrow="47" pageId="5" pageNumber="6">21.9, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFA12FA79FA19" box="[116,1455,1412,1426]" gridrow="48" pageId="5" pageNumber="6" rowspan-0="1" rowspan-5="1">
|
||
<td id="768C5DB9EF500056FF63FA12FE9AFA19" box="[233,332,1412,1426]" gridcol="1" gridrow="48" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFF63FA12FEFCFA19" bold="true" box="[233,298,1412,1426]" italics="true" pageId="5" pageNumber="6">21-O-Mb</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FE2DFA12FDDFFA19" box="[423,521,1412,1426]" gridcol="2" gridrow="48" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFE2DFA12FE31FA19" bold="true" box="[423,487,1412,1426]" italics="true" pageId="5" pageNumber="6">21-O-Tig</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FDEEFA12FD1FFA19" box="[612,713,1412,1426]" gridcol="3" gridrow="48" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFDEEFA12FD49FA19" bold="true" box="[612,671,1412,1426]" italics="true" pageId="5" pageNumber="6">21-O-Bz</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FCAEFA12FC50FA19" box="[804,902,1412,1426]" gridcol="4" gridrow="48" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFCAEFA12FCB2FA19" bold="true" box="[804,868,1412,1426]" italics="true" pageId="5" pageNumber="6">21-O-Tig</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FB03FA12FB38FA19" box="[1161,1262,1412,1426]" gridcol="6" gridrow="48" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFB03FA12FB10FA19" bold="true" box="[1161,1222,1412,1426]" italics="true" pageId="5" pageNumber="6">21-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FAC0FA12FA79FA19" box="[1354,1455,1412,1426]" gridcol="7" gridrow="48" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFAC0FA12FA5CFA19" bold="true" box="[1354,1418,1412,1426]" italics="true" pageId="5" pageNumber="6">21-O-Tig</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFA27FA79FA34" box="[116,1455,1457,1471]" gridrow="49" pageId="5" pageNumber="6" rowspan-5="1">
|
||
<th id="768C5DB9EF500056FFFEFA27FF46FA34" box="[116,144,1457,1471]" gridcol="0" gridrow="49" pageId="5" pageNumber="6">1</th>
|
||
<td id="768C5DB9EF500056FF63FA27FE9AFA34" box="[233,332,1457,1471]" gridcol="1" gridrow="49" pageId="5" pageNumber="6">176.8, C</td>
|
||
<td id="768C5DB9EF500056FE2DFA27FDDFFA34" box="[423,521,1457,1471]" gridcol="2" gridrow="49" pageId="5" pageNumber="6">168.4, C</td>
|
||
<td id="768C5DB9EF500056FDEEFA27FD1FFA34" box="[612,713,1457,1471]" gridcol="3" gridrow="49" pageId="5" pageNumber="6">167.2, C</td>
|
||
<td id="768C5DB9EF500056FCAEFA27FC50FA34" box="[804,902,1457,1471]" gridcol="4" gridrow="49" pageId="5" pageNumber="6">167.6, C</td>
|
||
<td id="768C5DB9EF500056FB03FA27FB38FA34" box="[1161,1262,1457,1471]" gridcol="6" gridrow="49" pageId="5" pageNumber="6">170.3, C</td>
|
||
<td id="768C5DB9EF500056FAC0FA27FA79FA34" box="[1354,1455,1457,1471]" gridcol="7" gridrow="49" pageId="5" pageNumber="6">167.6, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFA5EFA79FA52" box="[116,1455,1480,1497]" gridrow="50" pageId="5" pageNumber="6" rowspan-5="1">
|
||
<th id="768C5DB9EF500056FFFEFA5EFF46FA52" box="[116,144,1480,1497]" gridcol="0" gridrow="50" pageId="5" pageNumber="6">2</th>
|
||
<td id="768C5DB9EF500056FF63FA5EFE9AFA52" box="[233,332,1480,1497]" gridcol="1" gridrow="50" pageId="5" pageNumber="6">42.4, CH</td>
|
||
<td id="768C5DB9EF500056FE2DFA5EFDDFFA52" box="[423,521,1480,1497]" gridcol="2" gridrow="50" pageId="5" pageNumber="6">129.9, C</td>
|
||
<td id="768C5DB9EF500056FDEEFA5EFD1FFA52" box="[612,713,1480,1497]" gridcol="3" gridrow="50" pageId="5" pageNumber="6">131.9, C</td>
|
||
<td id="768C5DB9EF500056FCAEFA5EFC50FA52" box="[804,902,1480,1497]" gridcol="4" gridrow="50" pageId="5" pageNumber="6">129.3, C</td>
|
||
<td id="768C5DB9EF500056FB03FA5EFB38FA52" box="[1161,1262,1480,1497]" gridcol="6" gridrow="50" pageId="5" pageNumber="6">21.8, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FA5EFA79FA52" box="[1354,1455,1480,1497]" gridcol="7" gridrow="50" pageId="5" pageNumber="6">129.3, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFA49FA79FA64" box="[116,1455,1503,1519]" gridrow="51" pageId="5" pageNumber="6" rowspan-5="1" rowspan-6="1">
|
||
<th id="768C5DB9EF500056FFFEFA49FF46FA64" box="[116,144,1503,1519]" gridcol="0" gridrow="51" pageId="5" pageNumber="6">3</th>
|
||
<td id="768C5DB9EF500056FF63FA49FE9AFA64" box="[233,332,1503,1519]" gridcol="1" gridrow="51" pageId="5" pageNumber="6">27.6, CH2</td>
|
||
<td id="768C5DB9EF500056FE2DFA49FDDFFA64" box="[423,521,1503,1519]" gridcol="2" gridrow="51" pageId="5" pageNumber="6">137.2, CH</td>
|
||
<td id="768C5DB9EF500056FDEEFA49FD1FFA64" box="[612,713,1503,1519]" gridcol="3" gridrow="51" pageId="5" pageNumber="6">130.4, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFA49FC50FA64" box="[804,902,1503,1519]" gridcol="4" gridrow="51" pageId="5" pageNumber="6">137.9, CH</td>
|
||
<td id="768C5DB9EF500056FAC0FA49FA79FA64" box="[1354,1455,1503,1519]" gridcol="7" gridrow="51" pageId="5" pageNumber="6">137.9, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEFA60FA79F98D" box="[116,1455,1526,1542]" gridrow="52" pageId="5" pageNumber="6" rowspan-5="1" rowspan-6="1">
|
||
<th id="768C5DB9EF500056FFFEFA60FF46F98D" box="[116,144,1526,1542]" gridcol="0" gridrow="52" pageId="5" pageNumber="6">4</th>
|
||
<td id="768C5DB9EF500056FF63FA60FE9AF98D" box="[233,332,1526,1542]" gridcol="1" gridrow="52" pageId="5" pageNumber="6">12.3, CH3</td>
|
||
<td id="768C5DB9EF500056FE2DFA60FDDFF98D" box="[423,521,1526,1542]" gridcol="2" gridrow="52" pageId="5" pageNumber="6">12.8, CH3</td>
|
||
<td id="768C5DB9EF500056FDEEFA60FD1FF98D" box="[612,713,1526,1542]" gridcol="3" gridrow="52" pageId="5" pageNumber="6">129.2, CH</td>
|
||
<td id="768C5DB9EF500056FCAEFA60FC50F98D" box="[804,902,1526,1542]" gridcol="4" gridrow="52" pageId="5" pageNumber="6">12.6, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0FA60FA79F98D" box="[1354,1455,1526,1542]" gridcol="7" gridrow="52" pageId="5" pageNumber="6">12.6, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEF99BFA79F996" box="[116,1455,1549,1565]" gridrow="53" pageId="5" pageNumber="6" rowspan-5="1" rowspan-6="1">
|
||
<th id="768C5DB9EF500056FFFEF99BFF46F996" box="[116,144,1549,1565]" gridcol="0" gridrow="53" pageId="5" pageNumber="6">5</th>
|
||
<td id="768C5DB9EF500056FF63F99BFE9AF996" box="[233,332,1549,1565]" gridcol="1" gridrow="53" pageId="5" pageNumber="6">17.5, CH3</td>
|
||
<td id="768C5DB9EF500056FE2DF99BFDDFF996" box="[423,521,1549,1565]" gridcol="2" gridrow="53" pageId="5" pageNumber="6">14.5, CH3</td>
|
||
<td id="768C5DB9EF500056FDEEF99BFD1FF996" box="[612,713,1549,1565]" gridcol="3" gridrow="53" pageId="5" pageNumber="6">133.5, CH</td>
|
||
<td id="768C5DB9EF500056FCAEF99BFC50F996" box="[804,902,1549,1565]" gridcol="4" gridrow="53" pageId="5" pageNumber="6">14.6, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0F99BFA79F996" box="[1354,1455,1549,1565]" gridcol="7" gridrow="53" pageId="5" pageNumber="6">14.6, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEF9B5FA79F9B9" box="[116,1455,1571,1586]" gridrow="54" pageId="5" pageNumber="6" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEF9B5FF46F9B9" box="[116,144,1571,1586]" gridcol="0" gridrow="54" pageId="5" pageNumber="6">6</th>
|
||
<td id="768C5DB9EF500056FDEEF9B5FD1FF9B9" box="[612,713,1571,1586]" gridcol="3" gridrow="54" pageId="5" pageNumber="6">129.2, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEF9ACFA79F9C2" box="[116,1455,1594,1609]" gridrow="55" pageId="5" pageNumber="6" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEF9ACFF46F9C2" box="[116,144,1594,1609]" gridcol="0" gridrow="55" pageId="5" pageNumber="6">7</th>
|
||
<td id="768C5DB9EF500056FDEEF9ACFD1FF9C2" box="[612,713,1594,1609]" gridcol="3" gridrow="55" pageId="5" pageNumber="6">130.4, CH</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEF9C7FA79F9D4" box="[116,1455,1617,1631]" gridrow="56" pageId="5" pageNumber="6" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<td id="768C5DB9EF500056FCAEF9C7FC50F9D4" box="[804,902,1617,1631]" gridcol="4" gridrow="56" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFCAEF9C7FCB7F9D4" bold="true" box="[804,865,1617,1631]" italics="true" pageId="5" pageNumber="6">22-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FB03F9C7FB38F9D4" box="[1161,1262,1617,1631]" gridcol="6" gridrow="56" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFB03F9C7FB10F9D4" bold="true" box="[1161,1222,1617,1631]" italics="true" pageId="5" pageNumber="6">22-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FAC0F9C7FA79F9D4" box="[1354,1455,1617,1631]" gridcol="7" gridrow="56" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFAC0F9C7FA50F9D4" bold="true" box="[1354,1414,1617,1631]" italics="true" pageId="5" pageNumber="6">22-O-Ac</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEF9E8FA79F906" box="[116,1455,1662,1677]" gridrow="57" pageId="5" pageNumber="6" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<th id="768C5DB9EF500056FFFEF9E8FF46F906" box="[116,144,1662,1677]" gridcol="0" gridrow="57" pageId="5" pageNumber="6">1ʹʹʹ</th>
|
||
<td id="768C5DB9EF500056FCAEF9E8FC50F906" box="[804,902,1662,1677]" gridcol="4" gridrow="57" pageId="5" pageNumber="6">170.8, C</td>
|
||
<td id="768C5DB9EF500056FB03F9E8FB38F906" box="[1161,1262,1662,1677]" gridcol="6" gridrow="57" pageId="5" pageNumber="6">170.8, C</td>
|
||
<td id="768C5DB9EF500056FAC0F9E8FA79F906" box="[1354,1455,1662,1677]" gridcol="7" gridrow="57" pageId="5" pageNumber="6">170.8, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEF903FA79F92D" box="[116,1455,1685,1702]" gridrow="58" pageId="5" pageNumber="6" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
|
||
<th id="768C5DB9EF500056FFFEF903FF46F92D" box="[116,144,1685,1702]" gridcol="0" gridrow="58" pageId="5" pageNumber="6">2ʹʹʹ</th>
|
||
<td id="768C5DB9EF500056FCAEF903FC50F92D" box="[804,902,1685,1702]" gridcol="4" gridrow="58" pageId="5" pageNumber="6">21.9, CH3</td>
|
||
<td id="768C5DB9EF500056FB03F903FB38F92D" box="[1161,1262,1685,1702]" gridcol="6" gridrow="58" pageId="5" pageNumber="6">21.0, CH3</td>
|
||
<td id="768C5DB9EF500056FAC0F903FA79F92D" box="[1354,1455,1685,1702]" gridcol="7" gridrow="58" pageId="5" pageNumber="6">21.4, CH3</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEF93AFA79F931" box="[116,1455,1708,1722]" gridrow="59" pageId="5" pageNumber="6" rowspan-0="1" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<td id="768C5DB9EF500056FF63F93AFE9AF931" box="[233,332,1708,1722]" gridcol="1" gridrow="59" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFF63F93AFEF0F931" bold="true" box="[233,294,1708,1722]" italics="true" pageId="5" pageNumber="6">28-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FE2DF93AFDDFF931" box="[423,521,1708,1722]" gridcol="2" gridrow="59" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFE2DF93AFE35F931" bold="true" box="[423,483,1708,1722]" italics="true" pageId="5" pageNumber="6">28-O-Ac</emphasis>
|
||
</td>
|
||
<td id="768C5DB9EF500056FDEEF93AFD1FF931" box="[612,713,1708,1722]" gridcol="3" gridrow="59" pageId="5" pageNumber="6">
|
||
<emphasis id="B919EA95EF50FFACFDEEF93AFD76F931" bold="true" box="[612,672,1708,1722]" italics="true" pageId="5" pageNumber="6">28-O-Ac</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEF94FFA79F963" box="[116,1455,1753,1768]" gridrow="60" pageId="5" pageNumber="6" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEF94FFF46F963" box="[116,144,1753,1768]" gridcol="0" gridrow="60" pageId="5" pageNumber="6">1ʹʹʹ</th>
|
||
<td id="768C5DB9EF500056FF63F94FFE9AF963" box="[233,332,1753,1768]" gridcol="1" gridrow="60" pageId="5" pageNumber="6">171.1, C</td>
|
||
<td id="768C5DB9EF500056FE2DF94FFDDFF963" box="[423,521,1753,1768]" gridcol="2" gridrow="60" pageId="5" pageNumber="6">171.2, C</td>
|
||
<td id="768C5DB9EF500056FDEEF94FFD1FF963" box="[612,713,1753,1768]" gridcol="3" gridrow="60" pageId="5" pageNumber="6">170.8, C</td>
|
||
</tr>
|
||
<tr id="355D34C5EF500056FFFEF966FA79F88A" box="[116,1455,1776,1793]" gridrow="61" pageId="5" pageNumber="6" rowspan-4="1" rowspan-5="1" rowspan-6="1" rowspan-7="1">
|
||
<th id="768C5DB9EF500056FFFEF966FF46F88A" box="[116,144,1776,1793]" gridcol="0" gridrow="61" pageId="5" pageNumber="6">2ʹʹʹ</th>
|
||
<td id="768C5DB9EF500056FF63F966FE9AF88A" box="[233,332,1776,1793]" gridcol="1" gridrow="61" pageId="5" pageNumber="6">20.0, CH3</td>
|
||
<td id="768C5DB9EF500056FE2DF966FDDFF88A" box="[423,521,1776,1793]" gridcol="2" gridrow="61" pageId="5" pageNumber="6">21.1, CH3</td>
|
||
<td id="768C5DB9EF500056FDEEF966FD1FF88A" box="[612,713,1776,1793]" gridcol="3" gridrow="61" pageId="5" pageNumber="6">21.0, CH3</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF50FFACFFFDF88CFF4FF8AD" blockId="5.[119,318,1818,1865]" box="[119,153,1818,1830]" pageId="5" pageNumber="6">
|
||
<superScript id="7C189BCFEF50FFACFFFDF88CFF4FF8AD" attach="right" box="[119,153,1818,1830]" fontSize="5" pageId="5" pageNumber="6">a 13</superScript>
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF50FFACFF13F889FEE8F8A4" blockId="5.[119,318,1818,1865]" box="[153,318,1821,1840]" pageId="5" pageNumber="6">C NMR (125 MHz).</paragraph>
|
||
<paragraph id="8BD23687EF50FFACFFFDF8A5FEE8F8C2" blockId="5.[119,318,1818,1865]" box="[119,318,1843,1865]" pageId="5" pageNumber="6">
|
||
<superScript id="7C189BCFEF50FFACFFFDF8A5FF4FF8B4" attach="right" box="[119,153,1843,1855]" fontSize="5" pageId="5" pageNumber="6">b 13</superScript>
|
||
C NMR (150 MHz).
|
||
</paragraph>
|
||
<caption id="DF12660FEF53FFAFFE61FA87FB9EFAAA" ID-DOI="http://doi.org/10.5281/zenodo.8160265" ID-Zenodo-Dep="8160265" box="[491,1096,1297,1314]" httpUri="https://zenodo.org/record/8160265/files/figure.png" pageId="6" pageNumber="7" startId="6.[491,521,1297,1314]" targetBox="[151,1436,152,1275]" targetPageId="6" targetType="figure">
|
||
<paragraph id="8BD23687EF53FFAFFE61FA87FB9EFAAA" blockId="6.[491,1096,1297,1314]" box="[491,1096,1297,1314]" pageId="6" pageNumber="7">
|
||
<emphasis id="B919EA95EF53FFAFFE61FA87FDF3FAA9" bold="true" box="[491,549,1297,1314]" pageId="6" pageNumber="7">Fig. 3.</emphasis>
|
||
Key COSY and HMBC correlations of compounds
|
||
<emphasis id="B919EA95EF53FFAFFC59FA87FC08FAA9" bold="true" box="[979,990,1297,1314]" pageId="6" pageNumber="7">1</emphasis>
|
||
,
|
||
<emphasis id="B919EA95EF53FFAFFC60FA87FC23FAAA" bold="true" box="[1002,1013,1297,1313]" pageId="6" pageNumber="7">5</emphasis>
|
||
,
|
||
<emphasis id="B919EA95EF53FFAFFB8BFA87FBDAFAA9" bold="true" box="[1025,1036,1297,1314]" pageId="6" pageNumber="7">6</emphasis>
|
||
and
|
||
<emphasis id="B919EA95EF53FFAFFBB2FA87FB95FAAA" bold="true" box="[1080,1091,1297,1313]" pageId="6" pageNumber="7">7</emphasis>
|
||
.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8BD23687EF53FFAFFF0FF987FC15F9F1" blockId="6.[100,770,1360,1991]" lastBlockId="6.[818,1488,1360,1992]" pageId="6" pageNumber="7">
|
||
Gymlatinoside GL6 (
|
||
<emphasis id="B919EA95EF53FFAFFECFF987FE87F9AF" bold="true" box="[325,337,1553,1572]" pageId="6" pageNumber="7">6</emphasis>
|
||
), obtained as an amorphous powder with []
|
||
<subScript id="17E934C2EF53FFAFFD78F98CFD2BF9A3" attach="left" box="[754,765,1562,1576]" fontSize="6" pageId="6" pageNumber="7">D</subScript>
|
||
<superScript id="7C189BCFEF53FFAFFD78F99AFCD7F991" attach="none" box="[754,769,1548,1562]" fontSize="6" pageId="6" pageNumber="7">25</superScript>
|
||
+5.4 (
|
||
<emphasis id="B919EA95EF53FFAFFF2DF9BBFF66F9CB" bold="true" box="[167,176,1581,1600]" italics="true" pageId="6" pageNumber="7">c</emphasis>
|
||
0.2, MeOH). The HRESIMS of this compound revealed an ion peak at
|
||
<emphasis id="B919EA95EF53FFAFFF3CF9DFFF10F9D7" bold="true" box="[182,198,1609,1628]" italics="true" pageId="6" pageNumber="7">m</emphasis>
|
||
/
|
||
<emphasis id="B919EA95EF53FFAFFF5BF9DFFF0CF9D7" bold="true" box="[209,218,1609,1628]" italics="true" pageId="6" pageNumber="7">z</emphasis>
|
||
791.4225 [M – H]
|
||
<superScript id="7C189BCFEF53FFAFFE12F9D3FE76F9DA" attach="left" box="[408,416,1605,1617]" fontSize="5" pageId="6" pageNumber="7">–</superScript>
|
||
(calcd for C
|
||
<subScript id="17E934C2EF53FFAFFD94F9C4FDE6F9D5" attach="both" box="[542,560,1618,1630]" fontSize="5" pageId="6" pageNumber="7">42</subScript>
|
||
H
|
||
<subScript id="17E934C2EF53FFAFFDCAF9C4FD84F9D5" attach="both" box="[576,594,1618,1630]" fontSize="5" pageId="6" pageNumber="7">63</subScript>
|
||
O
|
||
<subScript id="17E934C2EF53FFAFFDEBF9C4FDA5F9D5" attach="left" box="[609,627,1618,1630]" fontSize="5" pageId="6" pageNumber="7">14</subScript>
|
||
, 791.4218). It suggested a molecular formula C
|
||
<subScript id="17E934C2EF53FFAFFE1FF9F8FE71F9F1" attach="both" box="[405,423,1646,1658]" fontSize="5" pageId="6" pageNumber="7">42</subScript>
|
||
H
|
||
<subScript id="17E934C2EF53FFAFFE3DF9F8FE1FF9F1" attach="both" box="[439,457,1646,1658]" fontSize="5" pageId="6" pageNumber="7">64</subScript>
|
||
O
|
||
<subScript id="17E934C2EF53FFAFFE52F9F8FE3CF9F1" attach="left" box="[472,490,1646,1658]" fontSize="5" pageId="6" pageNumber="7">14</subScript>
|
||
and indicated the presence of 11 IHDs. The
|
||
<superScript id="7C189BCFEF53FFAFFF63F9EBFF24F902" attach="right" box="[233,242,1661,1673]" fontSize="5" pageId="6" pageNumber="7">1</superScript>
|
||
H-NMR spectrum of
|
||
<emphasis id="B919EA95EF53FFAFFE3CF916FE14F918" bold="true" box="[438,450,1664,1683]" pageId="6" pageNumber="7">6</emphasis>
|
||
showed seven methyl groups (
|
||
<emphasis id="B919EA95EF53FFAFFD61F916FD20F918" bold="true" box="[747,758,1664,1683]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFD7CF91CFCD4F91D" attach="left" box="[758,770,1674,1686]" fontSize="5" pageId="6" pageNumber="7">H</subScript>
|
||
0.78, 0.86, 0.96, 0.99, 1.20, 1.32 and 1.41), and twelve oxymethine protons (
|
||
<tableCitation id="C6EF033CEF53FFAFFF31F92EFED4F940" box="[187,258,1720,1739]" captionStart="Table 1" captionStartId="4.[100,150,161,177]" captionTargetPageId="4" captionText="Table 1 1H NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" httpUri="http://table.plazi.org/id/DF12660FEF51FFADFFEEFF37FE05FF46" pageId="6" pageNumber="7" tableUuid="DF12660FEF51FFADFFEEFF37FE05FF46">Table 1</tableCitation>
|
||
). The signals in the
|
||
<superScript id="7C189BCFEF53FFAFFE4DF922FE0FF94B" attach="right" box="[455,473,1716,1728]" fontSize="5" pageId="6" pageNumber="7">13</superScript>
|
||
C NMR spectrum together with HSQC analysis could be assigned as eleven quaternary carbons (four carboxylic acids at
|
||
<emphasis id="B919EA95EF53FFAFFE90F966FEF3F888" bold="true" box="[282,293,1776,1795]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFEAFF96FFEF9F88E" attach="left" box="[293,303,1785,1797]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
173.3, 170.8, 170.5, 170.3 and one olefinic at
|
||
<emphasis id="B919EA95EF53FFAFFD67F966FD2EF888" bold="true" box="[749,760,1776,1795]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFD72F96FFCD4F88E" attach="left" box="[760,770,1785,1797]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
140.8), thirteen tertiary carbons (nine oxygenated methines, one olefinic carbon at
|
||
<emphasis id="B919EA95EF53FFAFFF75F8BEFEDCF8B0" bold="true" box="[255,266,1832,1851]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFE80F8A7FEC2F8B6" attach="left" box="[266,276,1841,1853]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
125.0), eight secondary carbons (one oxygenated methylene at
|
||
<emphasis id="B919EA95EF53FFAFFF6FF8D2FF26F8DC" bold="true" box="[229,240,1860,1879]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFF7AF8DBFF2CF8D2" attach="left" box="[240,250,1869,1881]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
68.6) and ten methyl carbons (
|
||
<tableCitation id="C6EF033CEF53FFAFFDAEF8D2FDBCF8DC" box="[548,618,1860,1879]" captionStart="Table 2" captionStartId="5.[100,150,161,177]" captionTargetPageId="5" captionText="Table 2 13C NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" pageId="6" pageNumber="7">Table 2</tableCitation>
|
||
). Comparing its resonances with literature, together with the NOESY experiment (
|
||
<figureCitation id="13562A02EF53FFAFFFE6F8EAFF77F804" box="[108,161,1916,1935]" captionStart="Fig" captionStartId="7.[100,130,966,983]" captionTargetBox="[151,1436,152,942]" captionTargetPageId="7" captionText="Fig. 4. Key NOESY correlations of compounds 1 (a: the aglycone, b: sugar moiety), 5 and 6. Fig. 4 c showed the chemical shifts and coupling constants of the protons on the glycosides. HMBC correlations bridging two sugar moieties were measured. All the discussions about COSY, NOESY and the coupling constant rules to identify the relative configuration of the sugar moiety were suggested at Results and discussion of compound 1." figureDoi="http://doi.org/10.5281/zenodo.8160267" httpUri="https://zenodo.org/record/8160267/files/figure.png" pageId="6" pageNumber="7">Fig. 4</figureCitation>
|
||
), suggested that
|
||
<emphasis id="B919EA95EF53FFAFFEB5F8EDFE9DF805" bold="true" box="[319,331,1915,1934]" pageId="6" pageNumber="7">6</emphasis>
|
||
has a marsglobiferin aglycone which possesses two
|
||
<emphasis id="B919EA95EF53FFAFFF1BF801FF4AF821" bold="true" box="[145,156,1943,1962]" italics="true" pageId="6" pageNumber="7">β</emphasis>
|
||
-oriented hydroxyl group substituted at C-16, C-21 and one
|
||
<emphasis id="B919EA95EF53FFAFFD65F80EFD2DF820" bold="true" box="[751,763,1944,1963]" italics="true" pageId="6" pageNumber="7">α</emphasis>
|
||
- oriented hydroxyl group at C-22 (
|
||
<bibRefCitation id="EFFC4B76EF53FFAFFE14F825FDA4F84D" author="Yoshikawa, K. & Taninaka, H. & Kan, Y. & Arihara, S." box="[414,626,1971,1991]" pageId="6" pageNumber="7" pagination="2023 - 2027" refId="ref12520" refString="Yoshikawa, K., Taninaka, H., Kan, Y., Arihara, S., 1994. Antisweet natural products. X. Structures of sitakisosides I-V from Stephanotis lutchuensis Koidz. var. japonica. Chem. Pharm. Bull. 42, 2023 - 2027." type="journal article" year="1994">Yoshikawa et al., 1994</bibRefCitation>
|
||
). Furthermore, positive fragment ions exhibited a glucuronic fragment loss (176 amu) and three acetyl substitutions (3 × 42 amu). The HMBC correlations from H-16 (
|
||
<emphasis id="B919EA95EF53FFAFFC29FA11FC78FA11" bold="true" box="[931,942,1415,1434]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFC24FA07FC6CFA16" attach="left" box="[942,954,1425,1437]" fontSize="5" pageId="6" pageNumber="7">H</subScript>
|
||
6.31, overlap) to C-1
|
||
<superScript id="7C189BCFEF53FFAFFB02FA12FB62FA1B" attach="left" box="[1160,1204,1412,1424]" fontSize="5" pageId="6" pageNumber="7">A−16</superScript>
|
||
(
|
||
<emphasis id="B919EA95EF53FFAFFB4EFA11FB19FA11" bold="true" box="[1220,1231,1415,1434]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFB45FA07FB0FFA16" attach="left" box="[1231,1241,1425,1437]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
179.5), H-21 (
|
||
<emphasis id="B919EA95EF53FFAFFAE2FA11FAA5FA11" bold="true" box="[1384,1395,1415,1434]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFAF9FA07FAA9FA16" attach="left" box="[1395,1407,1425,1437]" fontSize="5" pageId="6" pageNumber="7">H</subScript>
|
||
5.61, d,
|
||
<emphasis id="B919EA95EF53FFAFFCB8FA32FCEAFA3C" bold="true" box="[818,828,1444,1463]" italics="true" pageId="6" pageNumber="7">J</emphasis>
|
||
= 11.0 Hz) to C-1
|
||
<superScript id="7C189BCFEF53FFAFFC62FA36FBC2FA27" attach="left" box="[1000,1044,1440,1452]" fontSize="5" pageId="6" pageNumber="7">A−21</superScript>
|
||
(
|
||
<emphasis id="B919EA95EF53FFAFFBA8FA35FBFBFA3D" bold="true" box="[1058,1069,1443,1462]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFBA7FA3BFBE1FA32" attach="left" box="[1069,1079,1453,1465]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
170.3), and H-22 [
|
||
<emphasis id="B919EA95EF53FFAFFB67FA35FB2EFA3D" bold="true" box="[1261,1272,1443,1462]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFB72FA3BFAD2FA32" attach="left" box="[1272,1284,1453,1465]" fontSize="5" pageId="6" pageNumber="7">H</subScript>
|
||
5.16, d,
|
||
<emphasis id="B919EA95EF53FFAFFADDFA32FAB7FA3C" bold="true" box="[1367,1377,1444,1463]" italics="true" pageId="6" pageNumber="7">J</emphasis>
|
||
= 11.0 Hz] to C-1
|
||
<superScript id="7C189BCFEF53FFAFFCE0FA2DFC41FA4C" attach="left" box="[874,919,1467,1479]" fontSize="5" pageId="6" pageNumber="7">A−22</superScript>
|
||
(
|
||
<emphasis id="B919EA95EF53FFAFFC2FFA29FC66FA59" bold="true" box="[933,944,1471,1490]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFC3AFA5EFC6CFA5F" attach="left" box="[944,954,1480,1492]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
170.8) confirmed the acylated linkage positions at C-16, 21 and 22. The connection of the
|
||
<emphasis id="B919EA95EF53FFAFFB00FA4DFB43FA65" bold="true" box="[1162,1173,1499,1518]" italics="true" pageId="6" pageNumber="7">β</emphasis>
|
||
glucuronic acid to C-3 was determined by the coupling constant
|
||
<emphasis id="B919EA95EF53FFAFFB08FA61FB5AF981" bold="true" box="[1154,1164,1527,1546]" italics="true" pageId="6" pageNumber="7">J</emphasis>
|
||
= 7.5 Hz of the anomeric proton, the glycosylated chemical shift of C-3 (
|
||
<emphasis id="B919EA95EF53FFAFFB2EF985FB79F9AD" bold="true" box="[1188,1199,1555,1574]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFB25F98AFB6FF9A3" attach="left" box="[1199,1209,1564,1576]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
89.1, +11.1) and the HMBC correlation from H-1′ (
|
||
<emphasis id="B919EA95EF53FFAFFB83F9B9FBC2F9C9" bold="true" box="[1033,1044,1583,1602]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFB9EF9AEFBF6F9CF" attach="left" box="[1044,1056,1592,1604]" fontSize="5" pageId="6" pageNumber="7">H</subScript>
|
||
4.97) to C-3 (
|
||
<figureCitation id="13562A02EF53FFAFFB2DF9B9FB0BF9C9" box="[1191,1245,1583,1602]" captionStart="Fig" captionStartId="6.[491,521,1297,1314]" captionTargetBox="[151,1436,152,1275]" captionTargetId="graphics-624@6.[151,1436,152,1274]" captionTargetPageId="6" captionText="Fig. 3. Key COSY and HMBC correlations of compounds 1, 5, 6 and 7." figureDoi="http://doi.org/10.5281/zenodo.8160265" httpUri="https://zenodo.org/record/8160265/files/figure.png" pageId="6" pageNumber="7">Fig. 3</figureCitation>
|
||
). Therefore, compound
|
||
<emphasis id="B919EA95EF53FFAFFA49F9B9FA19F9C9" bold="true" box="[1475,1487,1583,1602]" pageId="6" pageNumber="7">6</emphasis>
|
||
was elucidated as 16,21,22-
|
||
<emphasis id="B919EA95EF53FFAFFBB4F9DDFB9BF9D5" bold="true" box="[1086,1101,1611,1630]" italics="true" pageId="6" pageNumber="7">O</emphasis>
|
||
-triacetyl marsglobiferin 3-
|
||
<emphasis id="B919EA95EF53FFAFFAC5F9DDFAA6F9D6" bold="true" box="[1359,1392,1610,1630]" italics="true" pageId="6" pageNumber="7">O -β</emphasis>
|
||
-D-glucuronopyranoside.
|
||
</paragraph>
|
||
<paragraph id="8BD23687EF53FFAEFCD9F916FD6BFB15" blockId="6.[818,1488,1360,1992]" lastBlockId="7.[100,770,1079,1183]" lastPageId="7" lastPageNumber="8" pageId="6" pageNumber="7">
|
||
Gymlatinoside GL7 (
|
||
<emphasis id="B919EA95EF53FFAFFB99F917FBC9F91F" bold="true" box="[1043,1055,1665,1684]" pageId="6" pageNumber="7">7</emphasis>
|
||
), obtained as an amorphous powder with []
|
||
<subScript id="17E934C2EF53FFAFFA4AF91FFA1DF91C" attach="left" box="[1472,1483,1673,1687]" fontSize="6" pageId="6" pageNumber="7">D</subScript>
|
||
<superScript id="7C189BCFEF53FFAFFA4AF9EAFA19F901" attach="none" box="[1472,1487,1660,1674]" fontSize="6" pageId="6" pageNumber="7">25</superScript>
|
||
+12.4 (
|
||
<emphasis id="B919EA95EF53FFAFFC09F90BFC5AF93B" bold="true" box="[899,908,1693,1712]" italics="true" pageId="6" pageNumber="7">c</emphasis>
|
||
0.2, MeOH), possessed a molecular formula of C
|
||
<subScript id="17E934C2EF53FFAFFAF0F933FA5AF93A" attach="both" box="[1402,1420,1701,1713]" fontSize="5" pageId="6" pageNumber="7">45</subScript>
|
||
H
|
||
<subScript id="17E934C2EF53FFAFFA16F933FA78F93A" attach="both" box="[1436,1454,1701,1713]" fontSize="5" pageId="6" pageNumber="7">68</subScript>
|
||
O
|
||
<subScript id="17E934C2EF53FFAFFA37F933FA19F93A" attach="left" box="[1469,1487,1701,1713]" fontSize="5" pageId="6" pageNumber="7">15</subScript>
|
||
based on HRESIMS ion peaks at
|
||
<emphasis id="B919EA95EF53FFAFFBF0F92EFB49F940" bold="true" box="[1146,1183,1720,1739]" italics="true" pageId="6" pageNumber="7">m/z</emphasis>
|
||
847.4508 [M – H]
|
||
<superScript id="7C189BCFEF53FFAFFAD5F923FAB1F94A" attach="left" box="[1375,1383,1717,1729]" fontSize="5" pageId="6" pageNumber="7">–</superScript>
|
||
(calcd for C
|
||
<subScript id="17E934C2EF53FFAFFCB5F94BFC87F962" attach="both" box="[831,849,1757,1769]" fontSize="5" pageId="6" pageNumber="7">45</subScript>
|
||
H
|
||
<subScript id="17E934C2EF53FFAFFCEBF94BFCA5F962" attach="both" box="[865,883,1757,1769]" fontSize="5" pageId="6" pageNumber="7">67</subScript>
|
||
O
|
||
<subScript id="17E934C2EF53FFAFFC08F94BFC42F962" attach="left" box="[898,916,1757,1769]" fontSize="5" pageId="6" pageNumber="7">15</subScript>
|
||
, 847.4480). The LC-MS experiment in positive mode showed key ions of gymnemagenin (489, 471, 453 and 435) and neutral losses of a glucuronic acid (176 amu), a tigloyl (82 amu) and two acetyls (2 × 42 amu). The
|
||
<superScript id="7C189BCFEF53FFAFFC79F8B2FC2AF8BB" attach="right" box="[1011,1020,1828,1840]" fontSize="5" pageId="6" pageNumber="7">1</superScript>
|
||
H,
|
||
<superScript id="7C189BCFEF53FFAFFB91F8B2FBFBF8BB" attach="right" box="[1051,1069,1828,1840]" fontSize="5" pageId="6" pageNumber="7">13</superScript>
|
||
C and HSQC NMR spectroscopic data confirmed the structure of aglycone gymnemagenin similar with compound
|
||
<emphasis id="B919EA95EF53FFAFFCB8F8C9FCE8F8F9" bold="true" box="[818,830,1887,1906]" pageId="6" pageNumber="7">1</emphasis>
|
||
(
|
||
<tableCitation id="C6EF033CEF53FFAFFCC4F8F6FC48F8F8" box="[846,926,1888,1907]" captionStart="Table 1" captionStartId="4.[100,150,161,177]" captionTargetPageId="4" captionText="Table 1 1H NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" httpUri="http://table.plazi.org/id/DF12660FEF51FFADFFEEFF37FE05FF46" pageId="6" pageNumber="7" tableUuid="DF12660FEF51FFADFFEEFF37FE05FF46">Tables 1</tableCitation>
|
||
and
|
||
<tableCitation id="C6EF033CEF53FFAFFC5AF8F6FC0AF8F8" box="[976,988,1888,1907]" captionStart="Table 2" captionStartId="5.[100,150,161,177]" captionTargetPageId="5" captionText="Table 2 13C NMR spectroscopic data (in Pyridine-d) of compounds 1-7. 5" pageId="6" pageNumber="7">2</tableCitation>
|
||
). Meanwhile, its
|
||
<superScript id="7C189BCFEF53FFAFFB0EF8CAFB40F8E3" attach="right" box="[1156,1174,1884,1896]" fontSize="5" pageId="6" pageNumber="7">13</superScript>
|
||
C-NMR showed similar acylation chemical shifts for C-16 (
|
||
<emphasis id="B919EA95EF53FFAFFBA2F8EDFBE5F805" bold="true" box="[1064,1075,1915,1934]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFBB8F813FBEAF81A" attach="left" box="[1074,1084,1925,1937]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
68.7), C-21 (
|
||
<emphasis id="B919EA95EF53FFAFFB4BF8EDFB1AF805" bold="true" box="[1217,1228,1915,1934]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFB46F813FB00F81A" attach="left" box="[1228,1238,1925,1937]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
76.7) and C-22 (
|
||
<emphasis id="B919EA95EF53FFAFFA0AF8EDFA5DF805" bold="true" box="[1408,1419,1915,1934]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFA01F813FA43F81A" attach="left" box="[1419,1429,1925,1937]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
72.0) compared with
|
||
<emphasis id="B919EA95EF53FFAFFC40F801FC00F821" bold="true" box="[970,982,1943,1962]" pageId="6" pageNumber="7">4</emphasis>
|
||
, and the sugar portion showed was superimposable with compound
|
||
<emphasis id="B919EA95EF53FFAFFC46F825FC0EF84D" bold="true" box="[972,984,1971,1990]" pageId="6" pageNumber="7">6</emphasis>
|
||
. The glycosylated chemical shift of C-3 (
|
||
<emphasis id="B919EA95EF53FFAFFAD3F825FAB2F84D" bold="true" box="[1369,1380,1971,1990]" italics="true" pageId="6" pageNumber="7">δ</emphasis>
|
||
<subScript id="17E934C2EF53FFAFFAEEF82AFAB8F843" attach="left" box="[1380,1390,1980,1992]" fontSize="5" pageId="6" pageNumber="7">C</subScript>
|
||
82.2) and HMBC cross peak from anomeric proton H-1′ (
|
||
<emphasis id="B919EA95EF52FFAEFDACFBAEFDE7FBC0" bold="true" box="[550,561,1080,1099]" italics="true" pageId="7" pageNumber="8">δ</emphasis>
|
||
<subScript id="17E934C2EF52FFAEFDBBFBD7FDEBFBC6" attach="left" box="[561,573,1089,1101]" fontSize="5" pageId="7" pageNumber="8">H</subScript>
|
||
5.27, d,
|
||
<emphasis id="B919EA95EF52FFAEFD1CFBAEFD76FBC0" bold="true" box="[662,672,1080,1099]" italics="true" pageId="7" pageNumber="8">J</emphasis>
|
||
= 7.5 Hz) indicated the presence of a
|
||
<emphasis id="B919EA95EF52FFAEFE0FFBC5FE46FBED" bold="true" box="[389,400,1107,1126]" italics="true" pageId="7" pageNumber="8">β</emphasis>
|
||
-D-glucuronic acid substituted at C-3 (
|
||
<figureCitation id="13562A02EF52FFAEFFE6FBE6FF70FB08" box="[108,166,1136,1155]" captionStart="Fig" captionStartId="6.[491,521,1297,1314]" captionTargetBox="[151,1436,152,1275]" captionTargetId="graphics-624@6.[151,1436,152,1274]" captionTargetPageId="6" captionText="Fig. 3. Key COSY and HMBC correlations of compounds 1, 5, 6 and 7." figureDoi="http://doi.org/10.5281/zenodo.8160265" httpUri="https://zenodo.org/record/8160265/files/figure.png" pageId="7" pageNumber="8">Fig. 3</figureCitation>
|
||
). Accordingly, compound
|
||
<emphasis id="B919EA95EF52FFAEFE25FBE6FE6DFB08" bold="true" box="[431,443,1136,1155]" pageId="7" pageNumber="8">7</emphasis>
|
||
was determined as 21-
|
||
<emphasis id="B919EA95EF52FFAEFD23FBE6FD6EFB08" bold="true" box="[681,696,1136,1155]" italics="true" pageId="7" pageNumber="8">O</emphasis>
|
||
-tigloyl-16,22-
|
||
<emphasis id="B919EA95EF52FFAEFF2BFB1DFF66FB15" bold="true" box="[161,176,1163,1182]" italics="true" pageId="7" pageNumber="8">O</emphasis>
|
||
-diacetyl gymnemagenin 3-
|
||
<emphasis id="B919EA95EF52FFAEFE38FB1DFE05FB15" bold="true" box="[434,467,1163,1183]" italics="true" pageId="7" pageNumber="8">O -β</emphasis>
|
||
-D-glucuronopyranoside.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |