157 lines
16 KiB
XML
157 lines
16 KiB
XML
<document id="1B9164504D2016C18C28C1A0021F8388" 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="03CE8794BA57A743AE724CBFFA09387C" 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" docType="treatment" docVersion="4" lastPageNumber="75" 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="75" updateTime="1705326194582" updateUser="juliana">
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<mods:title id="217F1C6E1816FF00023250130144182A">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="D62D6189D844DE40FB4BABA751B22389">Deans, Bianca J.</mods:namePart>
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<mods:affiliation id="B6E34B92C2551774ABD3E01C85A3FCE6">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:namePart id="AB805512C5E0D1B2A68B59A2E49C68B6">Tedone, Laura</mods:namePart>
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<mods:affiliation id="B7E1EB0BE305E6154002A8897DF65874">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="A8BBBAECE925CA0E29F94A0A68A7C194">Bissember, Alex C.</mods:namePart>
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<mods:affiliation id="F8C170CF868CA03D905ACCF74FD4D951">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:nameIdentifier id="524BF4372F972032434885C8D0B337CB" type="email">alex.bissember@utas.edu.au</mods:nameIdentifier>
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<mods:namePart id="016BE3AF118E623C672D2B811D25F3EF">Smith, Jason A.</mods:namePart>
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<mods:affiliation id="39C52715C74DC0846494CD84B73252EF">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:title id="8D1501F2F4F2B2CD5C3765385E924176">Phytochemistry</mods:title>
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<mods:part id="0B9A990681B2E45D570BB6500B8C3093">
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<mods:date id="663D251F5892E61D004AE86ACBD4A9C0">2018</mods:date>
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<mods:number id="CCC167F385C2E6B94B4B1EDA3B01BCF3">2018-09-30</mods:number>
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<mods:number id="4D6F015A0C40D260CDF8E2CF4F2C3C86">153</mods:number>
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<mods:identifier id="FE43A61FC1024CE8C663AAE794657037" type="DOI">10.1016/j.phytochem.2018.05.019</mods:identifier>
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<mods:identifier id="F29DEFF91BB18824A03FE60F60DB2214" type="ISSN">1873-3700</mods:identifier>
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<treatment id="03CE8794BA57A743AE724CBFFA09387C" LSID="urn:lsid:plazi:treatment:03CE8794BA57A743AE724CBFFA09387C" httpUri="http://treatment.plazi.org/id/03CE8794BA57A743AE724CBFFA09387C" lastPageNumber="75" pageId="1" pageNumber="75">
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<subSubSection id="C37D6509BA57A743AE724CBFFBA03FB5" box="[818,1048,665,684]" pageId="1" pageNumber="75" type="nomenclature">
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<paragraph id="8BD83682BA57A743AE724CBFFBA03FB5" blockId="1.[818,1048,665,684]" box="[818,1048,665,684]" pageId="1" pageNumber="75">
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<heading id="D09081EEBA57A743AE724CBFFBA03FB5" bold="true" box="[818,1048,665,684]" fontSize="36" level="1" pageId="1" pageNumber="75" reason="1">
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<emphasis id="B913EA90BA57A743AE724CBFFBA03FB5" bold="true" box="[818,1048,665,684]" italics="true" pageId="1" pageNumber="75">
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2.2.
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<taxonomicName id="4C674D01BA57A743AE204CBFFBA03FB5" ID-CoL="3VWY6" baseAuthorityName="Hooker" baseAuthorityYear="1936" box="[864,1048,665,684]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="polymorpha">Lomatia polymorpha</taxonomicName>
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</emphasis>
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</heading>
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<subSubSection id="C37D6509BA57A743AE134CF7FA09387C" pageId="1" pageNumber="75" type="description">
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<paragraph id="8BD83682BA57A743AE134CF7FC4E3EE2" blockId="1.[818,1488,721,1381]" pageId="1" pageNumber="75">
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Maceration of
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<taxonomicName id="4C674D01BA57A743AE9A4CF7FBE13FFD" baseAuthorityName="Hooker" baseAuthorityYear="1936" box="[986,1113,721,740]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="polymorpha">
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<emphasis id="B913EA90BA57A743AE9A4CF7FBE13FFD" bold="true" box="[986,1113,721,740]" italics="true" pageId="1" pageNumber="75">L. polymorpha</emphasis>
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</taxonomicName>
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provided juglone (
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<emphasis id="B913EA90BA57A743A84A4CF7FAAE3FFD" bold="true" box="[1290,1302,721,740]" pageId="1" pageNumber="75">1</emphasis>
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) (0.32% w/w), and a mixture of three aliphatic
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<emphasis id="B913EA90BA57A743A9194CCBFBDC3E19" bold="true" box="[1113,1124,749,768]" italics="true" pageId="1" pageNumber="75">n</emphasis>
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-alcohols (0.07% w/w), which were identified as tetracosanol (C
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<subScript id="17E334C7BA57A743A97D4D37FBF73E07" attach="both" box="[1085,1103,785,798]" fontSize="5" pageId="1" pageNumber="75">24</subScript>
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H
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<subScript id="17E334C7BA57A743A91E4D37FBC83E07" attach="both" box="[1118,1136,785,798]" fontSize="5" pageId="1" pageNumber="75">50</subScript>
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O), hexacosanol (C
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<subScript id="17E334C7BA57A743A8644D37FA8E3E07" attach="both" box="[1316,1334,785,798]" fontSize="5" pageId="1" pageNumber="75">26</subScript>
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H
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<subScript id="17E334C7BA57A743A8064D37FAE03E07" attach="both" box="[1350,1368,785,798]" fontSize="5" pageId="1" pageNumber="75">54</subScript>
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O) and octacosanol (C
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<subScript id="17E334C7BA57A743AED84D0BFC123E23" attach="both" box="[920,938,813,826]" fontSize="5" pageId="1" pageNumber="75">28</subScript>
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H
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<subScript id="17E334C7BA57A743AEFA4D0BFC743E23" attach="both" box="[954,972,813,826]" fontSize="5" pageId="1" pageNumber="75">58</subScript>
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O) in addition to heptacosane and nonacosane. The respective GC-MS and retention data were consistent with the equivalent data in National Institute of Standards and Technology (NIST) reference libraries (see: Supporting Information). GC-MS analysis of the purified fraction also indicated the presence of 1-pentacosanol, 1-heptacosanol, and 1-nonacosanol in small quantities (see: Supporting Information). Notably, this represents the first isolation of
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<emphasis id="B913EA90BA57A743A8304DEAFAC33EC6" bold="true" box="[1392,1403,972,991]" italics="true" pageId="1" pageNumber="75">n</emphasis>
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-alcohols from
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<taxonomicName id="4C674D01BA57A743AE264DCEFC163EE2" box="[870,942,1000,1019]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="genus">
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<emphasis id="B913EA90BA57A743AE264DCEFC163EE2" bold="true" box="[870,942,1000,1019]" italics="true" pageId="1" pageNumber="75">Lomatia</emphasis>
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</taxonomicName>
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leaves.
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</paragraph>
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<paragraph id="8BD83682BA57A743AE134A22FA09387C" blockId="1.[818,1488,721,1381]" pageId="1" pageNumber="75">
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The PHWE extract provided dihydroquercetin 3-
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<emphasis id="B913EA90BA57A743A8604A22FA97390E" bold="true" box="[1312,1327,1028,1047]" italics="true" pageId="1" pageNumber="75">O</emphasis>
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-β- D-xyloside (
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<emphasis id="B913EA90BA57A743A8FB4A22FA7F390E" bold="true" box="[1467,1479,1028,1047]" pageId="1" pageNumber="75">4</emphasis>
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) (0.22% w/w), quercetin 3-
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<emphasis id="B913EA90BA57A743A9794A06FBF0392A" bold="true" box="[1081,1096,1056,1075]" italics="true" pageId="1" pageNumber="75">O</emphasis>
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-β-
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<subScript id="17E334C7BA57A743A9224A02FBCA392A" attach="none" box="[1122,1138,1056,1075]" fontSize="6" pageId="1" pageNumber="75">D-</subScript>
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glucose (
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<emphasis id="B913EA90BA57A743A98B4A06FB6F392A" bold="true" box="[1227,1239,1056,1075]" pageId="1" pageNumber="75">5</emphasis>
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) (0.14% w/w), 1,4,8-trihydroxynaphthalene 1-
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<emphasis id="B913EA90BA57A743A9544A1DFB9B3957" bold="true" box="[1044,1059,1083,1102]" italics="true" pageId="1" pageNumber="75">O</emphasis>
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-β-
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<subScript id="17E334C7BA57A743A97D4A66FBF53957" attach="none" box="[1085,1101,1083,1102]" fontSize="6" pageId="1" pageNumber="75">D-</subScript>
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glucose (
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<emphasis id="B913EA90BA57A743A9EA4A1DFB0E3957" bold="true" box="[1194,1206,1083,1102]" pageId="1" pageNumber="75">6</emphasis>
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) (0.04% w/w), and 4-
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<emphasis id="B913EA90BA57A743A8E84A1DFA703957" bold="true" box="[1448,1480,1083,1102]" italics="true" pageId="1" pageNumber="75">O -p</emphasis>
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-
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<subScript id="17E334C7BA57A743AE724A71FC153973" attach="left" box="[818,941,1111,1130]" fontSize="6" pageId="1" pageNumber="75">coumaroyl-D-</subScript>
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glucose (
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<emphasis id="B913EA90BA57A743A9414A71FBB53973" bold="true" box="[1025,1037,1111,1130]" pageId="1" pageNumber="75">7</emphasis>
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) as a mixture of diastereoisomers, (0.03% w/w) (
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<figureCitation id="135C2A07BA57A743AE7A4A55FCD7399F" box="[826,879,1139,1158]" captionStart="Fig" captionStartId="1.[818,848,1914,1931]" captionTargetBox="[850,1454,1610,1892]" captionTargetPageId="1" captionText="Fig. 2. Dihydroquercetin 3-O-β-D-xyloside (4), quercetin 3-O-β-D-glucose (5), 1,4,8-trihydroxynaphthalene-1-O-β-D- glucose (6), and 4-O-p-coumaroyl-D-glucose (7)." figureDoi="http://doi.org/10.5281/zenodo.10483775" httpUri="https://zenodo.org/record/10483775/files/figure.png" pageId="1" pageNumber="75">Fig. 2</figureCitation>
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). The respective
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<superScript id="7C129BCABA57A743A9514A49FBA23965" attach="right" box="[1041,1050,1135,1148]" fontSize="5" pageId="1" pageNumber="75">1</superScript>
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H and
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<superScript id="7C129BCABA57A743A9194A49FBD33965" attach="right" box="[1113,1131,1135,1148]" fontSize="5" pageId="1" pageNumber="75">13</superScript>
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C NMR spectroscopic and MS data for compounds
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<emphasis id="B913EA90BA57A743AEE74AA9FC7239BB" bold="true" box="[935,970,1167,1186]" pageId="1" pageNumber="75">4–6</emphasis>
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were consistent with equivalent data previously reported in the literature (see: Supporting Information) (
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<bibRefCitation id="EFF64B73BA57A743A87E4A8DFBB639C3" author="Baderschneider, B. & Winterhalter, P." pageId="1" pageNumber="75" pagination="2788 - 2798" refId="ref6231" refString="Baderschneider, B., Winterhalter, P., 2001. Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from riesling wine and screening for antioxidant activity. J. Agric. Food Chem. 49, 2788 - 2798." type="journal article" year="2001">Baderschneider and Winterhalter, 2001</bibRefCitation>
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;
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<bibRefCitation id="EFF64B73BA57A743A9594AE1FB5339C3" author="Fernandez, J. & Reyes, R. & Ponce, H. & Oropeza, M. & VanCalsteren, M. - R. & Jankowski, C. & Campos, M. G." box="[1049,1259,1223,1242]" pageId="1" pageNumber="75" pagination="108 - 115" refId="ref7010" refString="Fernandez, J., Reyes, R., Ponce, H., Oropeza, M., VanCalsteren, M. - R., Jankowski, C., Campos, M. G., 2005. Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D 4 - induced contraction in Guinea-pig airways. Eur. J. Pharmacol. 522, 108 - 115." type="journal article" year="2005">Fernandez et al., 2005</bibRefCitation>
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;
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<bibRefCitation id="EFF64B73BA57A743A9B74AE1FAED39C3" author="Son, J. - K." box="[1271,1365,1223,1242]" pageId="1" pageNumber="75" pagination="203 - 205" refId="ref8108" refString="Son, J. - K., 1995. Isolation and structure determination of a new tetralone glucoside from the roots of Juglans mandshurica. Arch Pharm. Res. (Seoul) 18, 203 - 205." type="journal article" year="1995">Son, 1995</bibRefCitation>
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). Flavonoids have previously been isolated from
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<taxonomicName id="4C674D01BA57A743A9D44AC5FCD4380B" authority="(Moir and Thompson, 1973)" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="dentata">
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<emphasis id="B913EA90BA57A743A9D44AC5FB4939EF" bold="true" box="[1172,1265,1251,1270]" italics="true" pageId="1" pageNumber="75">L. dentata</emphasis>
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(
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<bibRefCitation id="EFF64B73BA57A743A8434AC5FCDA380B" author="Moir, M. & Thompson, R. H." pageId="1" pageNumber="75" pagination="1351 - 1353" refId="ref7896" refString="Moir, M., Thompson, R. H., 1973. Naphthaquinones in Lomatia species. Phytochemistry 12, 1351 - 1353." type="journal article" year="1973">Moir and Thompson, 1973</bibRefCitation>
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)
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</taxonomicName>
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. The NMR spectroscopic data and MS data for ester
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<emphasis id="B913EA90BA57A743A8274AD9FACB380B" bold="true" box="[1383,1395,1279,1298]" pageId="1" pageNumber="75">7</emphasis>
|
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was consistent with the proposed structure (see: Supporting Information). However, only limited NMR spectroscopic data has been reported for this known compound (
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<bibRefCitation id="EFF64B73BA57A743A9544B74FB6C387C" author="Birkofer, L. & Kaiser, C. & Hillges, B. & Barbara & Becker, F." box="[1044,1236,1362,1381]" pageId="1" pageNumber="75" pagination="196 - 202" refId="ref6320" refString="Birkofer, L., Kaiser, C., Hillges, B., Barbara, Becker, F., 1969. Sugar esters. V. NMR spectroscopic studies of O-acylglycoses. Justus Liebigs Ann. Chem. 725, 196 - 202." type="journal article" year="1969">Birkofer et al., 1969</bibRefCitation>
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;
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<bibRefCitation id="EFF64B73BA57A743A9A14B74FA1B387C" author="Kuraishi, T. & Kimura, T. & Murakami, T. & Sakai, Y. & Chen, C. - M." box="[1249,1443,1362,1381]" pageId="1" pageNumber="75" pagination="1998 - 2000" refId="ref7482" refString="Kuraishi, T., Kimura, T., Murakami, T., Sakai, Y., Chen, C. - M., 1984. Chemical and chemotaxonomic studies of pterophytes. XLVIII. Sugar ester from Plagiogyria euphlebia (Kunze) Mett. and Microlepia speluncae L. Chem. Pharm. Bull. 32, 1998 - 2000." type="journal article" year="1984">Kuraishi et al., 1984</bibRefCitation>
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).
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</paragraph>
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</subSubSection>
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</treatment>
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</document> |