treatments-xml/data/03/FB/87/03FB8795FF8EBD475D06BE59E37419F2.xml

<document id="E8B8CCAC95E49EE1AE181527A5B26186" ID-CLB-Dataset="264237" ID-DOI="10.1016/j.phytochem.2021.112909" ID-GBIF-Dataset="8fb5ad8b-262f-4221-b858-8817e02af56a" 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="diego" IM.treatments_approvedBy="diego" checkinTime="1692305013203" checkinUser="felipe" docAuthor="Chakraborty, Kajal &amp; 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:F36D69FC8B198FBE91029DF9C24697D3.6:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="6" docTitle="Turbinaria conoides Kutzing" docType="treatment" docVersion="9" 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="1738923367832" updateUser="diego">
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<mods:title id="FD2FDC5DF3B5FA6A193FE6C2483893C6">Conoidecyclics A-C from marine macroalga Turbinaria conoides: Newly described natural macrolides with prospective bioactive properties</mods:title>
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<mods:namePart id="C922C39E3071A15B99B1A1E06BE86EB4">Chakraborty, Kajal</mods:namePart>
<mods:affiliation id="680038CDD4DC716357CCD08DFB8F4C9F">* &amp; Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P. B. No. 1603, Cochin, Kerala State, &amp; *</mods:affiliation>
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<mods:title id="A9F1D6E6F7A3DDBE233C83EBA73934B7">Phytochemistry</mods:title>
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<treatment id="03FB8795FF8EBD475D06BE59E37419F2" ID-DOI="http://doi.org/10.5281/zenodo.8269120" ID-GBIF-Taxon="212447660" ID-Zenodo-Dep="8269120" LSID="urn:lsid:plazi:treatment:03FB8795FF8EBD475D06BE59E37419F2" httpUri="http://treatment.plazi.org/id/03FB8795FF8EBD475D06BE59E37419F2" lastPageNumber="10" pageId="9" pageNumber="10" scope_family="Sargassaceae">
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<emphasis id="B926EA91FF8EBD475D06BE59E4C01E1D" bold="true" box="[100,710,857,876]" italics="true" pageId="9" pageNumber="10">
4.3. Chromatographic purification of organic extract of 
<taxonomicName id="4C524D00FF8EBD475F02BE59E4C01E1D" authority="(J. Agardh) Kutzing" authorityName="Kutzing" baseAuthorityName="J. Agardh" box="[608,710,857,876]" class="Phaeophyceae" family="Sargassaceae" genus="Turbinaria" kingdom="Chromista" order="Fucales" pageId="9" pageNumber="10" phylum="Gyrista" rank="species" species="conoides">T. conoides</taxonomicName>
</emphasis>
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The solvent extract of 
<taxonomicName id="4C524D00FF8EBD475C11BE91E7D91ED5" box="[371,479,913,932]" class="Phaeophyceae" family="Sargassaceae" genus="Turbinaria" kingdom="Chromista" order="Fucales" pageId="9" pageNumber="10" phylum="Gyrista" rank="species" species="conoides">
<emphasis id="B926EA91FF8EBD475C11BE91E7D91ED5" bold="true" box="[371,479,913,932]" italics="true" pageId="9" pageNumber="10">T. conoides</emphasis>
</taxonomicName>
(
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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="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>
) with silica gel (60–120 mesh, 
<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>
). The elution was initiated with less polar solvent (
<emphasis id="B926EA91FF8EBD475C28B901E7531965" bold="true" box="[330,341,1025,1044]" italics="true" pageId="9" pageNumber="10">n</emphasis>
-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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through TC 
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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" httpUri="http://table.plazi.org/id/DF2D660BFF84BD4D5D06BD96E43D1DB2" pageId="9" pageNumber="10" tableUuid="DF2D660BFF84BD4D5D06BD96E43D1DB2">Table S1</tableCitation>
) based upon TLC (8:2 v/v, 
<emphasis id="B926EA91FF8EBD475D92B955E6FD1919" bold="true" box="[240,251,1109,1128]" italics="true" pageId="9" pageNumber="10">n</emphasis>
-hexane:EtOAc) and RP C 
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-HPLC (MeOH/acetonitrile MeCN, 3:2 v/v) analysis, and those fractions (TC 
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-TC 
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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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(EtOAc: 
<emphasis id="B926EA91FF8EBD475F92B9A8E4FD19CA" bold="true" box="[752,763,1192,1211]" italics="true" pageId="9" pageNumber="10">n</emphasis>
- hexane 2:3 v/v; 
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, 15.5% yield) and TC 
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(EtOAc: 
<emphasis id="B926EA91FF8EBD475F3FB9C4E46E19A6" bold="true" box="[605,616,1220,1239]" italics="true" pageId="9" pageNumber="10">n</emphasis>
-hexane 7:3 v/v; 
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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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and TC 
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against 1,1-diphenyl-2-picryl-hydrazil (DPPH) and 2, 2 
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-azino-bis-3- ethylbenzothiozoline-6-sulfonic acid (ABTS 
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) were found to be greater compared to others (
<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" httpUri="http://table.plazi.org/id/DF2D660BFF84BD4D5D06BD96E43D1DB2" pageId="9" pageNumber="10" tableUuid="DF2D660BFF84BD4D5D06BD96E43D1DB2">Table S1</tableCitation>
), and therefore, were selected for downstream purification. Likewise, the sub-fraction TC 
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was subjected to fractionation on a silica gel (230–400 mesh) loaded glass column (
<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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). Step-wise gradient elution with 
<emphasis id="B926EA91FF8EBD475F44B8A3E43718C7" bold="true" box="[550,561,1443,1462]" italics="true" pageId="9" pageNumber="10">n</emphasis>
-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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-TC 
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) after TLC (
<emphasis id="B926EA91FF8EBD475C8EB8DBE7F1189F" bold="true" box="[492,503,1499,1518]" italics="true" pageId="9" pageNumber="10">n</emphasis>
-hexane-EtOAc, 4:1 v/v) and RP-C 
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HPLC (MeOH–MeCN, 3:2 v/v) experiments. The fraction TC 
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(
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, 3.96% yield) eluted at 
<emphasis id="B926EA91FF8EBD475CC2BB13E7AD1B57" bold="true" box="[416,427,1555,1574]" italics="true" pageId="9" pageNumber="10">n</emphasis>
-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" httpUri="http://table.plazi.org/id/DF2D660BFF84BD4D5D06BD96E43D1DB2" pageId="9" pageNumber="10" tableUuid="DF2D660BFF84BD4D5D06BD96E43D1DB2">Table S1</tableCitation>
). Therefore, TC 
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was further subfractionated on fine silica gel (SP 
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–B 
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, 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>
) loaded into a column connected to the flash chromatography system (SP 
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–B 
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, Biotage, 
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) by increasing gradient of 
<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 
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-TC 
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) 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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HPLC (MeOH/MeCN, 3:2 v/v). TC 
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(
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, 2.56% yield) was purified on silica gel GF 
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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 (
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, 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 
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HPLC (MeOH/ MeCN, 3:2 v/v). The fraction TC 
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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 
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) 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 
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(
<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" httpUri="http://table.plazi.org/id/DF2D660BFF84BD4D5D06BD96E43D1DB2" pageId="9" pageNumber="10" tableUuid="DF2D660BFF84BD4D5D06BD96E43D1DB2">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 
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(
<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 
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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>