243 lines
23 KiB
XML
243 lines
23 KiB
XML
<document id="87F415008E11061C13D43F08AD824A3B" ID-DOI="10.1016/j.phytochem.2018.05.019" ID-ISSN="1873-3700" ID-Zenodo-Dep="10483773" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="felipe" IM.materialsCitations_approvedBy="juliana" IM.metadata_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1704937347236" checkinUser="felipe" docAuthor="Deans, Bianca J., Tedone, Laura, Bissember, Alex C. & Smith, Jason A." docDate="2018" docId="03CE8794BA55A741AD244D1BFAE93F20" docLanguage="en" docName="Phytochemistry.153.74-78.pdf" docOrigin="Phytochemistry 153" docSource="http://dx.doi.org/10.1016/j.phytochem.2018.05.019" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Lomatia polymorpha R. Br" docType="treatment" docVersion="3" lastPageNumber="77" masterDocId="FFF7FFECBA56A742AD404E26FFB83D19" masterDocTitle="Phytochemical profile of the rare, ancient clone Lomatia tasmanica and comparison to other endemic Tasmanian species L. tinctoria and L. polymorpha" masterLastPageNumber="78" masterPageNumber="74" pageNumber="77" updateTime="1705326194582" updateUser="juliana">
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<mods:titleInfo id="0B19C160DA438C9179FDB5ABBF254285">
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<mods:title id="000B5D516F02BAD2AE8ECBCCD673B6B3">Phytochemical profile of the rare, ancient clone Lomatia tasmanica and comparison to other endemic Tasmanian species L. tinctoria and L. polymorpha</mods:title>
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<mods:namePart id="A95F3DC67F4C38AA51869766D16157F5">Deans, Bianca J.</mods:namePart>
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<mods:affiliation id="79662D4889C3B20DB13C264A0C3085FA">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:namePart id="848F28C411E94B4B639F0F3DA686D37C">Tedone, Laura</mods:namePart>
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<mods:affiliation id="6F885028F5404D48FFD5D52F9E455721">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia & Australian Centre for Research on Separation Science (ACROSS), University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:namePart id="D61D92EBF9748F165DB5A10BD6FB3B4B">Bissember, Alex C.</mods:namePart>
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<mods:affiliation id="10E853CFC9CB80D0B811B2D06AD37D29">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:nameIdentifier id="A35E91C06BA5E1BDDF76EFAD7F798364" type="email">alex.bissember@utas.edu.au</mods:nameIdentifier>
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<mods:namePart id="2AE4970EF05EBD833413C2DFF6ED6C73">Smith, Jason A.</mods:namePart>
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<mods:affiliation id="CEC572E7477456AC3430E59F6A4FAE08">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:title id="6E006316F4845B18EDA3FC6261AA042E">Phytochemistry</mods:title>
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<mods:date id="D0BB9EC15D1FA0AF38EA1F5E8366CF0B">2018</mods:date>
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<mods:number id="BCC79F47402336BF9B340AFECF552B39">2018-09-30</mods:number>
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<mods:number id="2441EADF6374DA0FF36DC542381EEAD4">153</mods:number>
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<mods:identifier id="DDAECD56C51AA55ABD5358CE78EADA16" type="ISSN">1873-3700</mods:identifier>
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<treatment id="03CE8794BA55A741AD244D1BFAE93F20" LSID="urn:lsid:plazi:treatment:03CE8794BA55A741AD244D1BFAE93F20" httpUri="http://treatment.plazi.org/id/03CE8794BA55A741AD244D1BFAE93F20" lastPageNumber="77" pageId="3" pageNumber="77">
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<subSubSection id="C37D6509BA55A741AD244D1BFE7F3E49" box="[100,455,829,848]" pageId="3" pageNumber="77" type="nomenclature">
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<paragraph id="8BD83682BA55A741AD244D1BFE7F3E49" blockId="3.[100,455,829,848]" box="[100,455,829,848]" pageId="3" pageNumber="77">
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<heading id="D09081EEBA55A741AD244D1BFE7F3E49" bold="true" box="[100,455,829,848]" fontSize="36" level="1" pageId="3" pageNumber="77" reason="1">
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<emphasis id="B913EA90BA55A741AD244D1BFE7F3E49" bold="true" box="[100,455,829,848]" italics="true" pageId="3" pageNumber="77">
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4.4. Extraction of
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<taxonomicName id="4C674D01BA55A741AC4E4D1BFE7F3E49" ID-CoL="3VWY6" authority="(Labill.) R. Br" authorityName="R. Br" baseAuthorityName="Labill." box="[270,455,829,848]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="polymorpha">Lomatia polymorpha</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="C37D6509BA55A741ADC54D53FAE93F20" pageId="3" pageNumber="77" type="description">
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<paragraph id="8BD83682BA55A741ADC54D53FDC739CF" blockId="3.[100,771,885,1992]" pageId="3" pageNumber="77">
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<emphasis id="B913EA90BA55A741ADC54D53FE2C3E91" bold="true" box="[133,404,885,904]" pageId="3" pageNumber="77">Diethyl ether maceration.</emphasis>
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Fresh leaves including petiole of
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<taxonomicName id="4C674D01BA55A741AFB14D53FF753EBD" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="polymorpha">
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<emphasis id="B913EA90BA55A741AFB14D53FF753EBD" bold="true" italics="true" pageId="3" pageNumber="77">L. polymorpha</emphasis>
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</taxonomicName>
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(
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<quantity id="4C9F9B67BA55A741AD9E4DB7FEA13EBD" box="[222,281,913,932]" metricMagnitude="-2" metricUnit="kg" metricValue="1.83" pageId="3" pageNumber="77" unit="g" value="18.3">18.3 g</quantity>
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) were removed from the stems (to form an even layer of material in the extraction vessel). The plant material was then completely submerged in diethyl ether (250 mL) and the vessel was sealed and maintained at room temperature. After 5 h, the leaves were observed to change to a darker green/black color, while the solution displayed a vibrant yellow color. The mixture was filtered, dried (Na
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<subScript id="17E334C7BA55A741ADC64A66FF373954" attach="both" box="[134,143,1088,1101]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
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SO
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<subScript id="17E334C7BA55A741ADEA4A66FF0B3954" attach="left" box="[170,179,1088,1101]" fontSize="5" pageId="3" pageNumber="77">4</subScript>
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), filtered, and evaporated under reduced pressure to provide an orange residue (
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<quantity id="4C9F9B67BA55A741AC604A72FED2397E" box="[288,362,1108,1127]" metricMagnitude="-4" metricUnit="kg" metricValue="1.49" pageId="3" pageNumber="77" unit="mg" value="149.0">149 mg</quantity>
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). This mixture was purified by automated flash chromatography to deliver juglone (
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<quantity id="4C9F9B67BA55A741ACB54A56FD8A399A" box="[501,562,1136,1155]" metricMagnitude="-5" metricUnit="kg" metricValue="6.0" pageId="3" pageNumber="77" unit="mg" value="60.0">60 mg</quantity>
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, 0.32% w/w) as red/ orange crystalline solid and a colorless semi-solid (
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<quantity id="4C9F9B67BA55A741AF054AAAFD3A3986" box="[581,642,1164,1183]" metricMagnitude="-5" metricUnit="kg" metricValue="1.3" pageId="3" pageNumber="77" unit="mg" value="13.0">13 mg</quantity>
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, 0.07% w/w) containing a mixture of the three
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<emphasis id="B913EA90BA55A741ACE34A8EFE1639A2" bold="true" box="[419,430,1192,1211]" italics="true" pageId="3" pageNumber="77">n</emphasis>
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-alcohols tetracosan-1-ol (C
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<subScript id="17E334C7BA55A741AFF14A96FD7B39A4" attach="both" box="[689,707,1200,1213]" fontSize="5" pageId="3" pageNumber="77">24</subScript>
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H
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<subScript id="17E334C7BA55A741AF924A96FD5C39A4" attach="both" box="[722,740,1200,1213]" fontSize="5" pageId="3" pageNumber="77">50</subScript>
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||
O), hexacosan-1-ol (C
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||
<subScript id="17E334C7BA55A741AC4D4AEAFEA739C0" attach="both" box="[269,287,1228,1241]" fontSize="5" pageId="3" pageNumber="77">26</subScript>
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H
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<subScript id="17E334C7BA55A741AC6F4AEAFEF939C0" attach="both" box="[303,321,1228,1241]" fontSize="5" pageId="3" pageNumber="77">54</subScript>
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O) and octacosan-1-ol (C
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||
<subScript id="17E334C7BA55A741AF6E4AEAFDF839C0" attach="both" box="[558,576,1228,1241]" fontSize="5" pageId="3" pageNumber="77">28</subScript>
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H
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||
<subScript id="17E334C7BA55A741AF0F4AEAFDD939C0" attach="both" box="[591,609,1228,1241]" fontSize="5" pageId="3" pageNumber="77">58</subScript>
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O).
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</paragraph>
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||
<paragraph id="8BD83682BA55A741ADC54AF9FDEE387B" blockId="3.[100,771,885,1992]" pageId="3" pageNumber="77">
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||
<emphasis id="B913EA90BA55A741ADC54AF9FE9039EB" bold="true" box="[133,296,1247,1266]" pageId="3" pageNumber="77">Tetracosan-1-ol.</emphasis>
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EIC (
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<emphasis id="B913EA90BA55A741AC264AF9FECE39EB" bold="true" box="[358,374,1247,1266]" italics="true" pageId="3" pageNumber="77">m</emphasis>
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/
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<emphasis id="B913EA90BA55A741ACC04AF9FE3139EB" bold="true" box="[384,393,1247,1266]" italics="true" pageId="3" pageNumber="77">z</emphasis>
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||
): 336 [M–18]
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||
<superScript id="7C129BCABA55A741AF574AFDFD9F39F1" attach="none" box="[535,551,1243,1256]" fontSize="5" pageId="3" pageNumber="77">+</superScript>
|
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.
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<emphasis id="B913EA90BA55A741AF774AF9FD6939EB" bold="true" box="[567,721,1247,1266]" pageId="3" pageNumber="77">Hexacosan-1-ol</emphasis>
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. EIC (
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<emphasis id="B913EA90BA55A741AD2C4ADDFFC43817" bold="true" box="[108,124,1275,1294]" italics="true" pageId="3" pageNumber="77">m</emphasis>
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/
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||
<emphasis id="B913EA90BA55A741ADC74ADDFF283817" bold="true" box="[135,144,1275,1294]" italics="true" pageId="3" pageNumber="77">z</emphasis>
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): 364 [M–18]
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<superScript id="7C129BCABA55A741AC594AD1FE91381D" attach="none" box="[281,297,1271,1284]" fontSize="5" pageId="3" pageNumber="77">+</superScript>
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, 336.
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<emphasis id="B913EA90BA55A741AC294ADDFDBD3817" bold="true" box="[361,517,1275,1294]" pageId="3" pageNumber="77">Octacosan-1-ol.</emphasis>
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EIC (
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<emphasis id="B913EA90BA55A741AF7F4ADDFDF73817" bold="true" box="[575,591,1275,1294]" italics="true" pageId="3" pageNumber="77">m</emphasis>
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/
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<emphasis id="B913EA90BA55A741AF1A4ADDFDDB3817" bold="true" box="[602,611,1275,1294]" italics="true" pageId="3" pageNumber="77">z</emphasis>
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): 392 [M–18]
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<superScript id="7C129BCABA55A741AFAC4AD1FD44381D" attach="none" box="[748,764,1271,1284]" fontSize="5" pageId="3" pageNumber="77">+</superScript>
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, 364, 336. See Supporting Information for the
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<superScript id="7C129BCABA55A741AF4D4B34FDAE3806" attach="right" box="[525,534,1298,1311]" fontSize="5" pageId="3" pageNumber="77">1</superScript>
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H NMR spectrum, as well as GC-MS data (retention time, LRI, TIC, and EIC for selected diagnostic ions) of the mixture containing the three
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<emphasis id="B913EA90BA55A741ACB04B69FE43387B" bold="true" box="[496,507,1359,1378]" italics="true" pageId="3" pageNumber="77">n</emphasis>
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-alcohols.
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</paragraph>
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<paragraph id="8BD83682BA55A741ADC54B4DFC103DF3" blockId="3.[100,771,885,1992]" lastBlockId="3.[818,1488,159,569]" pageId="3" pageNumber="77">
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<emphasis id="B913EA90BA55A741ADC54B4DFF733867" bold="true" box="[133,203,1387,1406]" pageId="3" pageNumber="77">PHWE.</emphasis>
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Immediately following the above-mentioned diethyl ether maceration, residual solvent was allowed to evaporate from the leaf material that remained (∼10 min). The ensuing
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<taxonomicName id="4C674D01BA55A741AF7D4B85FD0738AF" box="[573,703,1443,1462]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="polymorpha">
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<emphasis id="B913EA90BA55A741AF7D4B85FD0738AF" bold="true" box="[573,703,1443,1462]" italics="true" pageId="3" pageNumber="77">L. polymorpha</emphasis>
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||
</taxonomicName>
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||
leaves (
|
||
<quantity id="4C9F9B67BA55A741AD2B4B99FF1E38CB" box="[107,166,1471,1490]" metricMagnitude="-2" metricUnit="kg" metricValue="1.45" pageId="3" pageNumber="77" unit="g" value="14.5">14.5 g</quantity>
|
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) were then coarsely ground in a spice grinder, mixed with sand (
|
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<quantity id="4C9F9B67BA55A741AD2B4BFCFF3138F4" box="[107,137,1498,1517]" metricMagnitude="-3" metricUnit="kg" metricValue="2.0" pageId="3" pageNumber="77" unit="g" value="2.0">2 g</quantity>
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||
), and extracted using the identical espresso PHWE method detailed previously. The ensuing extract was then concentrated under reduced pressure on a rotary evaporator (50 ̊C bath temperature) to remove EtOH. The extract was then extracted with EtOAc (3 × 60 mL), with the organic extracts combined, dried over Na
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||
<subScript id="17E334C7BA55A741ACAC4874FE4D3B46" attach="both" box="[492,501,1618,1631]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
|
||
SO
|
||
<subScript id="17E334C7BA55A741AF4F4874FDA03B46" attach="left" box="[527,536,1618,1631]" fontSize="5" pageId="3" pageNumber="77">4</subScript>
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||
, filtered and evaporated under reduced pressured to provide a solid dark green residue (
|
||
<quantity id="4C9F9B67BA55A741AD2B48A4FF0D3B8C" box="[107,181,1666,1685]" metricMagnitude="-4" metricUnit="kg" metricValue="1.49" pageId="3" pageNumber="77" unit="mg" value="149.0">149 mg</quantity>
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||
). This residue was purified by flash chromatography (0
|
||
<emphasis id="B913EA90BA55A741AFFE48A2FD6B3B8C" bold="true" box="[702,723,1668,1685]" italics="true" pageId="3" pageNumber="77">→</emphasis>
|
||
30%
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||
<collectingCountry id="F3707612BA55A741AD2448B8FF393BA8" box="[100,129,1694,1713]" name="Switzerland" pageId="3" pageNumber="77">CH</collectingCountry>
|
||
<subScript id="17E334C7BA55A741ADC14880FF323BAA" attach="both" box="[129,138,1702,1715]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
|
||
Cl
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||
<subScript id="17E334C7BA55A741ADDE4880FF1F3BAA" attach="left" box="[158,167,1702,1715]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
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||
/MeOH; 11 min) to afford dihydroquercetin 3-
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<emphasis id="B913EA90BA55A741AF3648B8FD3D3BA8" bold="true" box="[630,645,1694,1713]" italics="true" pageId="3" pageNumber="77">O</emphasis>
|
||
-β- D-xyloside (
|
||
<emphasis id="B913EA90BA55A741AD2C489FFFC03BD5" bold="true" box="[108,120,1721,1740]" pageId="3" pageNumber="77">4</emphasis>
|
||
) as a dark yellow film (
|
||
<quantity id="4C9F9B67BA55A741AC16489FFE2A3BD5" box="[342,402,1721,1740]" metricMagnitude="-5" metricUnit="kg" metricValue="2.1" pageId="3" pageNumber="77" unit="mg" value="21.0">21 mg</quantity>
|
||
) and quercetin 3-
|
||
<emphasis id="B913EA90BA55A741AF77489FFDFE3BD5" bold="true" box="[567,582,1721,1740]" italics="true" pageId="3" pageNumber="77">O</emphasis>
|
||
-β-
|
||
<subScript id="17E334C7BA55A741AF204898FDC83BD5" attach="none" box="[608,624,1721,1740]" fontSize="6" pageId="3" pageNumber="77">D-</subScript>
|
||
glucose (
|
||
<emphasis id="B913EA90BA55A741AF84489FFD683BD5" bold="true" box="[708,720,1721,1740]" pageId="3" pageNumber="77">5</emphasis>
|
||
) as a yellow solid (
|
||
<quantity id="4C9F9B67BA55A741ADA948F3FE9D3BF1" box="[233,293,1749,1768]" metricMagnitude="-5" metricUnit="kg" metricValue="1.7" pageId="3" pageNumber="77" unit="mg" value="17.0">17 mg</quantity>
|
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) and A fraction of co-eluted compounds (
|
||
<quantity id="4C9F9B67BA55A741AFFF48F3FD443BF1" box="[703,764,1749,1768]" metricMagnitude="-5" metricUnit="kg" metricValue="6.0" pageId="3" pageNumber="77" unit="mg" value="60.0">60 mg</quantity>
|
||
) was purified further by flash chromatography (20% MeOH/
|
||
<collectingCountry id="F3707612BA55A741AFD748D7FD0E3A1D" box="[663,694,1777,1796]" name="Switzerland" pageId="3" pageNumber="77">CH</collectingCountry>
|
||
<subScript id="17E334C7BA55A741AFF548DCFD063A1E" attach="both" box="[693,702,1786,1799]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
|
||
Cl
|
||
<subScript id="17E334C7BA55A741AF9248DCFD633A1E" attach="left" box="[722,731,1786,1799]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
|
||
), to also afford dihydroquercetin 3-
|
||
<emphasis id="B913EA90BA55A741ACCA492BFE213A39" bold="true" box="[394,409,1805,1824]" italics="true" pageId="3" pageNumber="77">O</emphasis>
|
||
-β- D-xyloside (
|
||
<emphasis id="B913EA90BA55A741AF64492BFD883A39" bold="true" box="[548,560,1805,1824]" pageId="3" pageNumber="77">4</emphasis>
|
||
) (
|
||
<quantity id="4C9F9B67BA55A741AF06492BFD3B3A39" box="[582,643,1805,1824]" metricMagnitude="-5" metricUnit="kg" metricValue="1.1" pageId="3" pageNumber="77" unit="mg" value="11.0">11 mg</quantity>
|
||
, overall yield 0.22% w/w). Fractions which contained a mixture of quercetin 3-
|
||
<emphasis id="B913EA90BA55A741AF88490FFD6F3A25" bold="true" box="[712,727,1833,1852]" italics="true" pageId="3" pageNumber="77">O</emphasis>
|
||
-β- D- glucose (
|
||
<emphasis id="B913EA90BA55A741ADFD4963FF713A41" bold="true" box="[189,201,1861,1880]" pageId="3" pageNumber="77">5</emphasis>
|
||
) with two minor components were combined and subsequently purified by automated reverse phase chromatography (0
|
||
<emphasis id="B913EA90BA55A741AFA84945FD453A6D" bold="true" box="[744,765,1891,1908]" italics="true" pageId="3" pageNumber="77">→</emphasis>
|
||
50% MeCN/H
|
||
<subScript id="17E334C7BA55A741ADA849A3FF493A8B" attach="both" box="[232,241,1925,1938]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
|
||
O; 13 min), to also provide quercetin 3-
|
||
<emphasis id="B913EA90BA55A741AF20495BFDD73A89" bold="true" box="[608,623,1917,1936]" italics="true" pageId="3" pageNumber="77">O</emphasis>
|
||
-β- D- glucose (
|
||
<emphasis id="B913EA90BA55A741AFAD495BFD413A89" bold="true" box="[749,761,1917,1936]" pageId="3" pageNumber="77">5</emphasis>
|
||
) (
|
||
<quantity id="4C9F9B67BA55A741AD2C49BFFF243AB5" box="[108,156,1945,1964]" metricMagnitude="-6" metricUnit="kg" metricValue="3.0" pageId="3" pageNumber="77" unit="mg" value="3.0">3 mg</quantity>
|
||
, overall yield 0.14% w/w), 1,4,8-trihydroxynaphthalene-1-
|
||
<emphasis id="B913EA90BA55A741AF8849BFFD6F3AB5" bold="true" box="[712,727,1945,1964]" italics="true" pageId="3" pageNumber="77">O</emphasis>
|
||
-β-
|
||
<subScript id="17E334C7BA55A741AFB149BBFCBA3AB5" attach="none" box="[753,770,1945,1964]" fontSize="6" pageId="3" pageNumber="77">D-</subScript>
|
||
glucose (
|
||
<emphasis id="B913EA90BA55A741ADF94993FF7D3AD1" bold="true" box="[185,197,1973,1992]" pageId="3" pageNumber="77">6</emphasis>
|
||
) (
|
||
<quantity id="4C9F9B67BA55A741AD9B4993FEB43AD1" box="[219,268,1973,1992]" metricMagnitude="-6" metricUnit="kg" metricValue="6.0" pageId="3" pageNumber="77" unit="mg" value="6.0">6 mg</quantity>
|
||
, 0.04% w/w) as a clear film, and 4-
|
||
<emphasis id="B913EA90BA55A741AF1F4993FDC73AD1" bold="true" box="[607,639,1973,1992]" italics="true" pageId="3" pageNumber="77">O -p</emphasis>
|
||
-
|
||
<subScript id="17E334C7BA55A741AFC54993FCBA3AD1" attach="right" box="[645,770,1973,1992]" fontSize="6" pageId="3" pageNumber="77">coumaroyl-D-</subScript>
|
||
glucose (
|
||
<emphasis id="B913EA90BA55A741AEC84EB9FC2C3DAB" bold="true" box="[904,916,159,178]" pageId="3" pageNumber="77">7</emphasis>
|
||
) (
|
||
<quantity id="4C9F9B67BA55A741AEED4EB9FC653DAB" box="[941,989,159,178]" metricMagnitude="-6" metricUnit="kg" metricValue="5.0" pageId="3" pageNumber="77" unit="mg" value="5.0">5 mg</quantity>
|
||
, 0.03% w/w) as a pale yellow solid. NMR spectroscopic data for compounds
|
||
<emphasis id="B913EA90BA55A741A91E4E9DFB393DD7" bold="true" box="[1118,1153,187,206]" pageId="3" pageNumber="77">4–7</emphasis>
|
||
is provided in the Supporting Information.
|
||
</paragraph>
|
||
<paragraph id="8BD83682BA55A741AE134ED5FAE93F20" blockId="3.[818,1488,159,569]" pageId="3" pageNumber="77">
|
||
<emphasis id="B913EA90BA55A741AE134ED5FAD73C1F" bold="true" box="[851,1391,243,262]" pageId="3" pageNumber="77">Peracetylation of saccharides obtained from PHWE.</emphasis>
|
||
The aqueous phase from the above-mentioned EtOAc extraction step, was evaporated and a portion of the crude residue (
|
||
<quantity id="4C9F9B67BA55A741A9AE4F0DFA803C27" box="[1262,1336,299,318]" metricMagnitude="-4" metricUnit="kg" metricValue="1.76" pageId="3" pageNumber="77" unit="mg" value="176.0">176 mg</quantity>
|
||
), thus obtained, was dissolved in pyridine (1.5 mL) and cooled to 0 ̊C. Acetic anhydride (1.5 mL) was then added dropwise to this mixture and the magnetically stirred mixture maintained at room temperature. After 21 h, the mixture was concentrated under reduced pressure to afford a brown gum (
|
||
<quantity id="4C9F9B67BA55A741AE784F90FC3B3CD0" box="[824,899,438,457]" metricMagnitude="-4" metricUnit="kg" metricValue="2.42" pageId="3" pageNumber="77" unit="mg" value="242.0">242 mg</quantity>
|
||
), which was loaded onto a silica plug (50% EtOAc/hexanes elution), to remove
|
||
<collectingCountry id="F3707612BA55A741AEAC4FF4FBB13CFC" box="[1004,1033,466,485]" name="Switzerland" pageId="3" pageNumber="77">CH</collectingCountry>
|
||
<subScript id="17E334C7BA55A741A9494FFDFBAA3CF1" attach="both" box="[1033,1042,475,488]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
|
||
Cl
|
||
<subScript id="17E334C7BA55A741A9664FFDFB973CF1" attach="left" box="[1062,1071,475,488]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
|
||
-insoluble by-products. This provided a light brown mixture of non-polar components (
|
||
<quantity id="4C9F9B67BA55A741A9894FC8FABF3F18" box="[1225,1287,494,513]" metricMagnitude="-5" metricUnit="kg" metricValue="7.0" pageId="3" pageNumber="77" unit="mg" value="70.0">70 mg</quantity>
|
||
). Purification by automated flash column chromatography (0
|
||
<emphasis id="B913EA90BA55A741A99B4C2AFB483F04" bold="true" box="[1243,1264,524,541]" italics="true" pageId="3" pageNumber="77">→</emphasis>
|
||
100% EtOAc/hexanes; 10 min) provided α- and β- glucose pentaacetate (
|
||
<quantity id="4C9F9B67BA55A741A8484C00FAFD3F20" box="[1288,1349,550,569]" metricMagnitude="-5" metricUnit="kg" metricValue="1.6" pageId="3" pageNumber="77" unit="mg" value="16.0">16 mg</quantity>
|
||
).
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |