214 lines
21 KiB
XML
214 lines
21 KiB
XML
<document id="D9D1B461E07564E9EFC76BD9C647F05A" ID-DOI="10.1016/j.phytochem.2021.112909" ID-ISSN="1873-3700" ID-Zenodo-Dep="8258118" IM.bibliography_approvedBy="juliana" IM.illustrations_approvedBy="juliana" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1692305013203" checkinUser="felipe" docAuthor="Chakraborty, Kajal & Dhara, Shubhajit" docDate="2021" docId="03FB8795FF8EBD475D06BE59E37419F2" docLanguage="en" docName="Phytochemistry.191.112909.pdf" docOrigin="Phytochemistry (112909) 191" docSource="http://dx.doi.org/10.1016/j.phytochem.2021.112909" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Turbinaria conoides Kutzing" docType="treatment" docVersion="3" lastPageNumber="10" masterDocId="FFC2FFEDFF87BD4E5D62BD00E6061D71" masterDocTitle="Conoidecyclics A-C from marine macroalga Turbinaria conoides: Newly described natural macrolides with prospective bioactive properties" masterLastPageNumber="14" masterPageNumber="1" pageNumber="10" updateTime="1692621155424" updateUser="juliana">
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<mods:titleInfo id="89A571C86315BCBFA0C18EFB6093342A">
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<mods:title id="EA0B843B46A1E1243C339808EBFA5F3E">Conoidecyclics A-C from marine macroalga Turbinaria conoides: Newly described natural macrolides with prospective bioactive properties</mods:title>
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</mods:titleInfo>
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<mods:name id="6D6F1149FAB2A1DFB6CFA8E3742BDDEB" type="personal">
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<mods:namePart id="FF767249C6169E0B2C7994E132E1B558">Chakraborty, Kajal</mods:namePart>
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<mods:affiliation id="EFD4675914764C8DF486AE6D44530622">* & Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P. B. No. 1603, Cochin, Kerala State, & *</mods:affiliation>
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<mods:name id="933EA66EE69A17CF41BF1F49975D3711" type="personal">
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</mods:role>
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<mods:namePart id="ED5E7A66A1F4390480A0CDFAA2481588">Dhara, Shubhajit</mods:namePart>
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<mods:title id="4D857B330B6A90053D6585AD9871AE5C">Phytochemistry</mods:title>
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<mods:part id="18463A38C36B9BD8AA6171F228BE1B57">
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<mods:date id="CEDE21A18F9CB6325080E019F933729F">2021</mods:date>
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<mods:title id="801131B42AA20B5CA604C53163B4D08D">112909</mods:title>
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<mods:number id="DF9A87FD7BE76121DAFE2B1A9F26E6CA">2021-11-30</mods:number>
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<mods:number id="2B49145EB17A673EEDE2EFA18018C6B7">191</mods:number>
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<mods:url id="EC6D4DA4E89AD3EE7167585D3303ECF9">http://dx.doi.org/10.1016/j.phytochem.2021.112909</mods:url>
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<mods:classification id="5D432535F9C5951FB982120CBB363992">journal article</mods:classification>
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<mods:identifier id="1AC3386AAF8C0BF2D8E9B6FE42E6D5B0" type="DOI">10.1016/j.phytochem.2021.112909</mods:identifier>
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<mods:identifier id="3181A730BBC8D88234F7096872D8FF8D" type="ISSN">1873-3700</mods:identifier>
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<treatment id="03FB8795FF8EBD475D06BE59E37419F2" LSID="urn:lsid:plazi:treatment:03FB8795FF8EBD475D06BE59E37419F2" httpUri="http://treatment.plazi.org/id/03FB8795FF8EBD475D06BE59E37419F2" lastPageNumber="10" pageId="9" pageNumber="10">
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<subSubSection id="C3486508FF8EBD475D06BE59E4C01E1D" box="[100,710,857,876]" pageId="9" pageNumber="10" type="nomenclature">
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<paragraph id="8BED3683FF8EBD475D06BE59E4C01E1D" blockId="9.[100,710,857,876]" box="[100,710,857,876]" pageId="9" pageNumber="10">
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<heading id="D0A581EFFF8EBD475D06BE59E4C01E1D" bold="true" box="[100,710,857,876]" fontSize="36" level="1" pageId="9" pageNumber="10" reason="1">
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<emphasis id="B926EA91FF8EBD475D06BE59E4C01E1D" bold="true" box="[100,710,857,876]" italics="true" pageId="9" pageNumber="10">
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4.3. Chromatographic purification of organic extract of
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<taxonomicName id="4C524D00FF8EBD475F02BE59E4C01E1D" authority="(J. Agardh) Kutzing" authorityName="Kutzing" baseAuthorityName="J. Agardh" box="[608,710,857,876]" class="Anthozoa" family="Dendrophylliidae" genus="Turbinaria" kingdom="Animalia" order="Scleractinia" pageId="9" pageNumber="10" phylum="Cnidaria" rank="species" species="conoides">T. conoides</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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</subSubSection>
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<subSubSection id="C3486508FF8EBD475DE6BE91E37419F2" pageId="9" pageNumber="10" type="description">
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<paragraph id="8BED3683FF8EBD475DE6BE91E37419F2" blockId="9.[100,770,913,1964]" lastBlockId="9.[818,1488,857,1156]" pageId="9" pageNumber="10">
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The solvent extract of
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<taxonomicName id="4C524D00FF8EBD475C11BE91E7D91ED5" box="[371,479,913,932]" class="Anthozoa" family="Dendrophylliidae" genus="Turbinaria" kingdom="Animalia" order="Scleractinia" pageId="9" pageNumber="10" phylum="Cnidaria" rank="species" species="conoides">
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<emphasis id="B926EA91FF8EBD475C11BE91E7D91ED5" bold="true" box="[371,479,913,932]" italics="true" pageId="9" pageNumber="10">T. conoides</emphasis>
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</taxonomicName>
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(
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<quantity id="4CAA9B66FF8EBD475C91BE91E4201ED5" box="[499,550,913,932]" metricMagnitude="-2" metricUnit="kg" metricValue="3.0" pageId="9" pageNumber="10" unit="g" value="30.0">30 g</quantity>
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) was fractionated by sequential chromatographic procedures. The crude was mixed with the silica gel (60–120 mesh, 3.0 g) and loaded into a column of glass (
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<quantity id="4CAA9B66FF8EBD475FA9BEC9E5041EAD" box="[715,770,969,988]" metricMagnitude="-1" metricUnit="m" metricValue="1.0" pageId="9" pageNumber="10" unit="m" value="0.1">0.1 m</quantity>
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×
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<quantity id="4CAA9B66FF8EBD475D18BEE5E6BB1E89" box="[122,189,997,1016]" metricMagnitude="-2" metricUnit="m" metricValue="4.0" pageId="9" pageNumber="10" unit="mm" value="40.0">40 mm</quantity>
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) with silica gel (60–120 mesh,
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<quantity id="4CAA9B66FF8EBD475CBCBEE5E40C1E89" box="[478,522,997,1016]" metricMagnitude="-2" metricUnit="kg" metricValue="5.0" pageId="9" pageNumber="10" unit="g" value="50.0">50 g</quantity>
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). The elution was initiated with less polar solvent (
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<emphasis id="B926EA91FF8EBD475C28B901E7531965" bold="true" box="[330,341,1025,1044]" italics="true" pageId="9" pageNumber="10">n</emphasis>
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-hexane), followed by an increase of polarity (EtOAc to MeOH) to collect twenty-five fractions (10 mL/fraction), which were combined to five (TC
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<subScript id="17D634C6FF8EBD475CFCB940E7A1193F" attach="left" box="[414,423,1088,1102]" fontSize="6" pageId="9" pageNumber="10">1</subScript>
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through TC
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<subScript id="17D634C6FF8EBD475F7AB93FE427193C" attach="left" box="[536,545,1087,1101]" fontSize="6" pageId="9" pageNumber="10">5</subScript>
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) (
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<tableCitation id="C6D00338FF8EBD475F55B938E48F193A" box="[567,649,1080,1099]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetBox="[85,1488,196,358]" captionTargetId="graphics-205@3.[777,818,259,286]" captionText="Table 1 NMR spectroscopic data of conoidecyclics A-C in CDCl a. 3" pageId="9" pageNumber="10">Table S1</tableCitation>
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) based upon TLC (8:2 v/v,
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<emphasis id="B926EA91FF8EBD475D92B955E6FD1919" bold="true" box="[240,251,1109,1128]" italics="true" pageId="9" pageNumber="10">n</emphasis>
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-hexane:EtOAc) and RP C
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<subScript id="17D634C6FF8EBD475C90B95BE4021918" attach="left" box="[498,516,1115,1129]" fontSize="6" pageId="9" pageNumber="10">18</subScript>
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-HPLC (MeOH/acetonitrile MeCN, 3:2 v/v) analysis, and those fractions (TC
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<subScript id="17D634C6FF8EBD475F41B977E42A19F4" attach="left" box="[547,556,1143,1157]" fontSize="6" pageId="9" pageNumber="10">1</subScript>
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-TC
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<subScript id="17D634C6FF8EBD475F2FB977E45019F4" attach="left" box="[589,598,1143,1157]" fontSize="6" pageId="9" pageNumber="10">5</subScript>
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) were assessed for their bioactivities. The fractions possessing potential bioactive properties were chosen for further purification. The fractions TC
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<subScript id="17D634C6FF8EBD475FF7B9AFE49819CC" attach="left" box="[661,670,1199,1213]" fontSize="6" pageId="9" pageNumber="10">3</subScript>
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(EtOAc:
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<emphasis id="B926EA91FF8EBD475F92B9A8E4FD19CA" bold="true" box="[752,763,1192,1211]" italics="true" pageId="9" pageNumber="10">n</emphasis>
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- hexane 2:3 v/v;
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<quantity id="4CAA9B66FF8EBD475D9FB9C4E73C19A6" box="[253,314,1220,1239]" metricMagnitude="-3" metricUnit="kg" metricValue="4.65" pageId="9" pageNumber="10" unit="g" value="4.65">4.65 g</quantity>
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, 15.5% yield) and TC
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<subScript id="17D634C6FF8EBD475F67B9CBE40819A8" attach="left" box="[517,526,1227,1241]" fontSize="6" pageId="9" pageNumber="10">4</subScript>
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(EtOAc:
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<emphasis id="B926EA91FF8EBD475F3FB9C4E46E19A6" bold="true" box="[605,616,1220,1239]" italics="true" pageId="9" pageNumber="10">n</emphasis>
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-hexane 7:3 v/v;
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<quantity id="4CAA9B66FF8EBD475D06B9E0E6A31982" box="[100,165,1248,1267]" metricMagnitude="-3" metricUnit="kg" metricValue="4.26" pageId="9" pageNumber="10" unit="g" value="4.26">4.26 g</quantity>
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, 14.2% yield) displayed greater attenuation potential against COX-2 and 5-LOX enzymes. The radical scavenging potential of TC
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<subScript id="17D634C6FF8EBD475FB3B803E4DC1860" attach="left" box="[721,730,1283,1297]" fontSize="6" pageId="9" pageNumber="10">3</subScript>
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||
and TC
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<subScript id="17D634C6FF8EBD475D1CB81FE681185C" attach="left" box="[126,135,1311,1325]" fontSize="6" pageId="9" pageNumber="10">4</subScript>
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against 1,1-diphenyl-2-picryl-hydrazil (DPPH) and 2, 2
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<superScript id="7C279BCBFF8EBD475FEAB814E48A1850" attach="none" box="[648,652,1300,1313]" fontSize="6" pageId="9" pageNumber="10">′</superScript>
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-azino-bis-3- ethylbenzothiozoline-6-sulfonic acid (ABTS
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<superScript id="7C279BCBFF8EBD475C9EB82EE40E184D" attach="left" box="[508,520,1326,1340]" fontSize="6" pageId="9" pageNumber="10">+</superScript>
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||
) were found to be greater compared to others (
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<tableCitation id="C6D00338FF8EBD475C49B84FE77B1812" box="[299,381,1359,1379]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetBox="[85,1488,196,358]" captionTargetId="graphics-205@3.[777,818,259,286]" captionText="Table 1 NMR spectroscopic data of conoidecyclics A-C in CDCl a. 3" pageId="9" pageNumber="10">Table S1</tableCitation>
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), and therefore, were selected for downstream purification. Likewise, the sub-fraction TC
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<subScript id="17D634C6FF8EBD475F29B873E45218F0" attach="left" box="[587,596,1395,1409]" fontSize="6" pageId="9" pageNumber="10">3</subScript>
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was subjected to fractionation on a silica gel (230–400 mesh) loaded glass column (
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<quantity id="4CAA9B66FF8EBD475FBEB887E68E18C7" metricMagnitude="-1" metricUnit="m" metricValue="4.5" pageId="9" pageNumber="10" unit="mm" value="450.0">450 mm</quantity>
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×
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<quantity id="4CAA9B66FF8EBD475DC7B8A3E6EC18C7" box="[165,234,1443,1462]" metricMagnitude="-2" metricUnit="m" metricValue="3.0" pageId="9" pageNumber="10" unit="mm" value="30.0">30 mm</quantity>
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). Step-wise gradient elution with
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<emphasis id="B926EA91FF8EBD475F44B8A3E43718C7" bold="true" box="[550,561,1443,1462]" italics="true" pageId="9" pageNumber="10">n</emphasis>
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-hexane-EtOAc (9:1 to 3:2, v/v) yielded twenty sub-fractions (20 mL/fraction), which were combined to four (TC
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<subScript id="17D634C6FF8EBD475C4EB8E2E7451881" attach="left" box="[300,323,1506,1520]" fontSize="6" pageId="9" pageNumber="10">3-1</subScript>
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-TC
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<subScript id="17D634C6FF8EBD475C06B8E2E77D1881" attach="right" box="[356,379,1506,1520]" fontSize="6" pageId="9" pageNumber="10">3-4</subScript>
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) after TLC (
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||
<emphasis id="B926EA91FF8EBD475C8EB8DBE7F1189F" bold="true" box="[492,503,1499,1518]" italics="true" pageId="9" pageNumber="10">n</emphasis>
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-hexane-EtOAc, 4:1 v/v) and RP-C
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<subScript id="17D634C6FF8EBD475DF0B8FEE6A21B7D" attach="left" box="[146,164,1534,1548]" fontSize="6" pageId="9" pageNumber="10">18</subScript>
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HPLC (MeOH–MeCN, 3:2 v/v) experiments. The fraction TC
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<subScript id="17D634C6FF8EBD475F89B8FEE5041B7D" attach="left" box="[747,770,1534,1548]" fontSize="6" pageId="9" pageNumber="10">3-4</subScript>
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(
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<quantity id="4CAA9B66FF8EBD475D09BB13E6AB1B57" box="[107,173,1555,1574]" metricMagnitude="-3" metricUnit="kg" metricValue="1.19" pageId="9" pageNumber="10" unit="g" value="1.19">1.19 g</quantity>
|
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, 3.96% yield) eluted at
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<emphasis id="B926EA91FF8EBD475CC2BB13E7AD1B57" bold="true" box="[416,427,1555,1574]" italics="true" pageId="9" pageNumber="10">n</emphasis>
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||
-hexane-EtOAc (6:4, v/v) displayed potential bioactivities (
|
||
<tableCitation id="C6D00338FF8EBD475C2ABB2EE7991B33" box="[328,415,1582,1602]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetBox="[85,1488,196,358]" captionTargetId="graphics-205@3.[777,818,259,286]" captionText="Table 1 NMR spectroscopic data of conoidecyclics A-C in CDCl a. 3" pageId="9" pageNumber="10">Table S1</tableCitation>
|
||
). Therefore, TC
|
||
<subScript id="17D634C6FF8EBD475F5FBB36E4531B35" attach="left" box="[573,597,1590,1604]" fontSize="6" pageId="9" pageNumber="10">3-4</subScript>
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||
was further subfractionated on fine silica gel (SP
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<subScript id="17D634C6FF8EBD475CCBBB52E7B41B11" attach="right" box="[425,434,1618,1632]" fontSize="6" pageId="9" pageNumber="10">1</subScript>
|
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–B
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<subScript id="17D634C6FF8EBD475CABBB52E7DB1B11" attach="left" box="[457,477,1618,1632]" fontSize="6" pageId="9" pageNumber="10">1A</subScript>
|
||
, 230–400 mesh,
|
||
<quantity id="4CAA9B66FF8EBD475FE4BB4AE4B51B2C" box="[646,691,1610,1629]" metricMagnitude="-2" metricUnit="kg" metricValue="1.2" pageId="9" pageNumber="10" unit="g" value="12.0">12 g</quantity>
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) loaded into a column connected to the flash chromatography system (SP
|
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<subScript id="17D634C6FF8EBD475FAABB6EE4D71B0D" attach="right" box="[712,721,1646,1660]" fontSize="6" pageId="9" pageNumber="10">1</subScript>
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–B
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<subScript id="17D634C6FF8EBD475F8ABB6EE4FA1B0D" attach="left" box="[744,764,1646,1660]" fontSize="6" pageId="9" pageNumber="10">1A</subScript>
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, Biotage,
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<collectingCountry id="F3457613FF8EBD475DDABB82E7041BE4" box="[184,258,1666,1685]" name="Sweden" pageId="9" pageNumber="10">Sweden</collectingCountry>
|
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) by increasing gradient of
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<emphasis id="B926EA91FF8EBD475F64BB82E4171BE4" bold="true" box="[518,529,1666,1685]" italics="true" pageId="9" pageNumber="10">n</emphasis>
|
||
-hexane/EtOAc/MeOH to acquire twelve sub-fractions (15 mL/fraction). The latter fractions were combined to three (TC
|
||
<subScript id="17D634C6FF8EBD475C55BBC1E75D1BBE" attach="left" box="[311,347,1729,1743]" fontSize="6" pageId="9" pageNumber="10">3-4-1</subScript>
|
||
-TC
|
||
<subScript id="17D634C6FF8EBD475C1EBBC1E7A71BBE" attach="left" box="[380,417,1729,1743]" fontSize="6" pageId="9" pageNumber="10">3-4-3</subScript>
|
||
) after TLC (
|
||
<emphasis id="B926EA91FF8EBD475F71BBBAE4181BBC" bold="true" box="[531,542,1722,1741]" italics="true" pageId="9" pageNumber="10">n</emphasis>
|
||
-hexane-EtOAc, 8:2 v/v) and RP-C
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<subScript id="17D634C6FF8EBD475DA2BBDDE6D41B9A" attach="left" box="[192,210,1757,1771]" fontSize="6" pageId="9" pageNumber="10">18</subScript>
|
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HPLC (MeOH/MeCN, 3:2 v/v). TC
|
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<subScript id="17D634C6FF8EBD475F53BBDDE4501B9A" attach="left" box="[561,598,1757,1771]" fontSize="6" pageId="9" pageNumber="10">3-4-1</subScript>
|
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(
|
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<quantity id="4CAA9B66FF8EBD475F0ABBD6E4B11B98" box="[616,695,1750,1769]" metricMagnitude="-4" metricUnit="kg" metricValue="7.68" pageId="9" pageNumber="10" unit="g" value="0.768">0.768 g</quantity>
|
||
, 2.56% yield) was purified on silica gel GF
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<subScript id="17D634C6FF8EBD475CD6BBF9E7C91A76" attach="left" box="[436,463,1785,1799]" fontSize="6" pageId="9" pageNumber="10">254</subScript>
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by
|
||
<emphasis id="B926EA91FF8EBD475C97BBF2E4061A74" bold="true" box="[501,512,1778,1797]" italics="true" pageId="9" pageNumber="10">n</emphasis>
|
||
-hexane: EtOAc (25:1, v/v) solvent system using the preparatory TLC (PTLC) system to yield conoidecyclic A (
|
||
<quantity id="4CAA9B66FF8EBD475D87BA29E7221A4C" box="[229,292,1833,1853]" metricMagnitude="-5" metricUnit="kg" metricValue="8.5" pageId="9" pageNumber="10" unit="mg" value="85.0">85 mg</quantity>
|
||
, 0.28%, based on dry weight) and conoidecyclic B (
|
||
<quantity id="4CAA9B66FF8EBD475D09BA46E6A91A28" box="[107,175,1862,1881]" metricMagnitude="-5" metricUnit="kg" metricValue="7.3" pageId="9" pageNumber="10" unit="mg" value="73.0">73 mg</quantity>
|
||
, 0.24%, based on dry weight), and their homogeneity was confirmed by TLC (EtOAc/
|
||
<emphasis id="B926EA91FF8EBD475C3FBA62E76E1A04" bold="true" box="[349,360,1890,1909]" italics="true" pageId="9" pageNumber="10">n</emphasis>
|
||
-hexane, 1:9 v/v) and RP-C
|
||
<subScript id="17D634C6FF8EBD475F01BA69E4731A06" attach="left" box="[611,629,1897,1911]" fontSize="6" pageId="9" pageNumber="10">18</subScript>
|
||
HPLC (MeOH/ MeCN, 3:2 v/v). The fraction TC
|
||
<subScript id="17D634C6FF8EBD475CC6BA84E7AB1AE3" attach="left" box="[420,429,1924,1938]" fontSize="6" pageId="9" pageNumber="10">4</subScript>
|
||
was subjected to flash chromatography on a silica gel column (230–400 mesh) with a gradient elution of
|
||
<emphasis id="B926EA91FF8EBD475E50BE59E53B1E1D" bold="true" box="[818,829,857,876]" italics="true" pageId="9" pageNumber="10">n</emphasis>
|
||
-hexane/EtOAc/MeOH to yield sixteen fractions (15 mL/fraction), which were combined into three (TC
|
||
<subScript id="17D634C6FF8EBD4759EDBE7CE2A01EFB" attach="right" box="[1167,1190,892,906]" fontSize="6" pageId="9" pageNumber="10">4-1</subScript>
|
||
-TC
|
||
<subScript id="17D634C6FF8EBD4759A4BE7CE2DB1EFB" attach="left" box="[1222,1245,892,906]" fontSize="6" pageId="9" pageNumber="10">4-3</subScript>
|
||
) after TLC (EtOAc-
|
||
<emphasis id="B926EA91FF8EBD4758F7BE75E3A61EF9" bold="true" box="[1429,1440,885,904]" italics="true" pageId="9" pageNumber="10">n</emphasis>
|
||
-hexane, 1:4 v/v). TC
|
||
<subScript id="17D634C6FF8EBD475EBABE98E5E91ED7" attach="left" box="[984,1007,920,934]" fontSize="6" pageId="9" pageNumber="10">4-2</subScript>
|
||
(
|
||
<quantity id="4CAA9B66FF8EBD475E9CBE91E2381ED5" box="[1022,1086,913,932]" metricMagnitude="-3" metricUnit="kg" metricValue="1.15" pageId="9" pageNumber="10" unit="g" value="1.15">1.15 g</quantity>
|
||
, 3.83% yield) displayed greater bioactive potential than other column sub-fractions (
|
||
<tableCitation id="C6D00338FF8EBD4759B1BEADE3211EB1" box="[1235,1319,941,960]" captionStart="Table 1" captionStartId="3.[100,150,150,166]" captionTargetBox="[85,1488,196,358]" captionTargetId="graphics-205@3.[777,818,259,286]" captionText="Table 1 NMR spectroscopic data of conoidecyclics A-C in CDCl a. 3" pageId="9" pageNumber="10">Table S1</tableCitation>
|
||
), and flash chromatographic separation using a gradient elution of
|
||
<emphasis id="B926EA91FF8EBD475857BEC9E3461EAD" bold="true" box="[1333,1344,969,988]" italics="true" pageId="9" pageNumber="10">n</emphasis>
|
||
-hexane/EtOAc yielded eleven fractions (13 mL/fraction), which were combined into three (TC
|
||
<subScript id="17D634C6FF8EBD475EEFB908E5B41967" attach="left" box="[909,946,1032,1046]" fontSize="6" pageId="9" pageNumber="10">4-2-1</subScript>
|
||
-TC
|
||
<subScript id="17D634C6FF8EBD475EB1B908E5FE1967" attach="right" box="[979,1016,1032,1046]" fontSize="6" pageId="9" pageNumber="10">4-2-3</subScript>
|
||
). The bioactive fraction TC
|
||
<subScript id="17D634C6FF8EBD475867B908E32C1967" attach="left" box="[1285,1322,1032,1046]" fontSize="6" pageId="9" pageNumber="10">4-2-3</subScript>
|
||
(
|
||
<quantity id="4CAA9B66FF8EBD47585BB901E3801965" box="[1337,1414,1025,1044]" metricMagnitude="-4" metricUnit="kg" metricValue="4.42" pageId="9" pageNumber="10" unit="g" value="0.442">0.442 g</quantity>
|
||
, 1.47% yield) was a mixture, and was further purified by PTLC (EtOAc:
|
||
<emphasis id="B926EA91FF8EBD4758F7B91DE3A61941" bold="true" box="[1429,1440,1053,1072]" italics="true" pageId="9" pageNumber="10">n</emphasis>
|
||
-hexane, 1:26, v/v) to obtain conoidecyclic C (
|
||
<quantity id="4CAA9B66FF8EBD4759A1B938E305193D" box="[1219,1283,1080,1100]" metricMagnitude="-5" metricUnit="kg" metricValue="6.5" pageId="9" pageNumber="10" unit="mg" value="65.0">65 mg</quantity>
|
||
, 0.22%, based on dry weight). The homogeneity of the latter was confirmed by RP-C
|
||
<subScript id="17D634C6FF8EBD4758EAB95BE39C1918" attach="both" box="[1416,1434,1115,1129]" fontSize="6" pageId="9" pageNumber="10">18</subScript>
|
||
HPLC (MeOH–MeCN 3:2, v/v) and TLC (EtOAc/
|
||
<emphasis id="B926EA91FF8EBD4759DFB970E2CE19F2" bold="true" box="[1213,1224,1136,1155]" italics="true" pageId="9" pageNumber="10">n</emphasis>
|
||
-hexane 1:4, v/v).
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |