385 lines
49 KiB
XML
385 lines
49 KiB
XML
<document id="BAB2040E56F90063B148738D66FC1323" ID-DOI="10.1016/j.phytochem.2021.112800" ID-ISSN="1873-3700" ID-Zenodo-Dep="8259223" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="jonas" IM.materialsCitations_approvedBy="jonas" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="jonas" IM.taxonomicNames_approvedBy="jonas" IM.treatments_approvedBy="jonas" checkinTime="1692308231745" checkinUser="felipe" docAuthor="King, Douglas I., Hamid, Kaiser, Tran, Van H., Duke, Rujee K. & Duke, Colin C." docDate="2021" docId="233B3318FFFE0265FFC0FF7160B7AF04" docLanguage="en" docName="Phytochemistry.188.112800.pdf" docOrigin="Phytochemistry (112800) 188" docSource="http://dx.doi.org/10.1016/j.phytochem.2021.112800" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Lepidosperma viscidum R. Br." docType="treatment" docVersion="3" lastPageNumber="6" masterDocId="DF024B60FFFB0260FFA4FFE5635EAC64" masterDocTitle="Kangaroo Island propolis types originating from two Lepidosperma species and Dodonaea humilis" masterLastPageNumber="11" masterPageNumber="1" pageNumber="6" updateTime="1692629521602" updateUser="jonas">
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<mods:title id="6831FC55CA2F5BA4295DB4AAD1515966">Kangaroo Island propolis types originating from two Lepidosperma species and Dodonaea humilis</mods:title>
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<mods:namePart id="4572A283A3B70D558DD094A865077917">King, Douglas I.</mods:namePart>
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<mods:affiliation id="1FB00B47B5C01E94C856E4BE650A1F4C">* & Sydney Pharmacy School, Faculty of Medicine and Health, The University of Sydney, New South Wales, Australia</mods:affiliation>
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<mods:namePart id="4402A7AF98DE1E68B4E5C1550AB5A95A">Hamid, Kaiser</mods:namePart>
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<mods:namePart id="D2019F98F60987A180E89E3EEA3710D8">Tran, Van H.</mods:namePart>
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<mods:namePart id="9D7986151B6FD66D8D7532C1E745880D">Duke, Rujee K.</mods:namePart>
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<mods:namePart id="BE02A7A891145B68AAD71473FFA91764">Duke, Colin C.</mods:namePart>
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<mods:title id="BFAEB20B05CCF173625CD1A5C66496E4">Phytochemistry</mods:title>
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<mods:date id="5B26CAAA73F5638AFB0C632E8EF9F7A0">2021</mods:date>
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<mods:title id="14BE08F7E546A891912A88CE17D0ECA9">112800</mods:title>
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<mods:number id="99A65344A5AE9B2FC9C5935259736AA9">2021-08-31</mods:number>
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<mods:identifier id="CA4E32A67E1185A1F3DE8598CE894D87" type="DOI">10.1016/j.phytochem.2021.112800</mods:identifier>
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<treatment id="233B3318FFFE0265FFC0FF7160B7AF04" LSID="urn:lsid:plazi:treatment:233B3318FFFE0265FFC0FF7160B7AF04" httpUri="http://treatment.plazi.org/id/233B3318FFFE0265FFC0FF7160B7AF04" lastPageNumber="6" pageId="5" pageNumber="6">
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<subSubSection id="E388D185FFFE0265FFC0FF7161CFACC2" box="[100,657,147,167]" pageId="5" pageNumber="6" type="nomenclature">
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<paragraph id="AB2D820EFFFE0265FFC0FF7161CFACC2" blockId="5.[100,657,147,167]" box="[100,657,147,167]" pageId="5" pageNumber="6">
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<heading id="F0653562FFFE0265FFC0FF7161CFACC2" bold="true" box="[100,657,147,167]" fontSize="36" level="1" pageId="5" pageNumber="6" reason="1">
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<emphasis id="99E65E1CFFFE0265FFC0FF7161CFACC2" bold="true" box="[100,657,147,167]" italics="true" pageId="5" pageNumber="6">
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2.3.
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<collectionCode id="CD831ACBFFFE0265FF31FF7163FEACC3" box="[149,160,148,167]" country="USA" lsid="urn:lsid:biocol.org:col:15707" name="Field Museum of Natural History, Botany Department" pageId="5" pageNumber="6" type="Herbarium">F</collectionCode>
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<typeStatus id="74293CACFFFE0265FF03FF716392ACC3" box="[167,204,148,167]" pageId="5" pageNumber="6">type</typeStatus>
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propolis and its botanical source from
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<taxonomicName id="6C92F98DFFFE0265FD88FF7161CFACC2" ID-CoL="3TDJ3" authority="R. Br." authorityName="R. Br." box="[556,657,147,167]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="viscidum">L. viscidum</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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<subSubSection id="E388D185FFFE0265FF20FF2960B7AF04" pageId="5" pageNumber="6" type="biology_ecology">
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<paragraph id="AB2D820EFFFE0265FF20FF296387AEB0" blockId="5.[100,771,203,1534]" pageId="5" pageNumber="6">
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A plant source foraged by honey bees to produce propolis on Kangaroo Island was found to be the resinous exudate of
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<taxonomicName id="6C92F98DFFFE0265FDC3FF02605DAC9F" box="[615,771,231,251]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="undetermined">
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<emphasis id="99E65E1CFFFE0265FDC3FF0261BEAC9E" bold="true" box="[615,736,231,250]" italics="true" pageId="5" pageNumber="6">Lepidosperma</emphasis>
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sp.
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</taxonomicName>
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Montebello (
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<bibRefCitation id="CF03FFFFFFFE0265FF7AFEE662DCAD72" author="Duke, C. C. & Tran, V. H. & Duke, R. K. & Abu-Mellal, A. & Plunkett, G. T. & King, D. I. & Hamid, K. & Wilson, K. L. & Barrett, R. L. & Bruhl, J. J." box="[222,386,259,279]" pageId="5" pageNumber="6" pagination="87 - 97" refId="ref11052" refString="Duke, C. C., Tran, V. H., Duke, R. K., Abu-Mellal, A., Plunkett, G. T., King, D. I., Hamid, K., Wilson, K. L., Barrett, R. L., Bruhl, J. J., 2017. A sedge plant as the source of Kangaroo Island propolis rich in prenylated p-coumarate ester and stilbenes. Phytochemistry 134, 87 - 97. https: // doi. org / 10.1016 / j. phytochem. 2016.11.005." type="journal article" year="2017">Duke et al., 2017</bibRefCitation>
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||
). The resinous exudates from other species of
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<taxonomicName id="6C92F98DFFFE0265FF07FEFA6242AD56" box="[163,284,287,306]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="genus">
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<emphasis id="99E65E1CFFFE0265FF07FEFA6242AD56" bold="true" box="[163,284,287,306]" italics="true" pageId="5" pageNumber="6">Lepidosperma</emphasis>
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</taxonomicName>
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||
genus collected on KI and south-east
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<collectingRegion id="69564CECFFFE0265FDD6FEFA605CAD56" box="[626,770,287,306]" country="Australia" name="South Australia" pageId="5" pageNumber="6">South Australia</collectingRegion>
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were compared by TLC and
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<superScript id="5CE72F46FFFE0265FED4FED06227AD27" attach="right" box="[368,377,309,323]" fontSize="6" pageId="5" pageNumber="6">1</superScript>
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H NMR analysis with propolis samples. A close match was found for both TLC (Supplementary data,
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<figureCitation id="33A99E8BFFFE0265FD34FEB2618EAD0E" box="[656,720,343,362]" captionStart="Fig" captionStartId="4.[161,191,1650,1667]" captionTargetBox="[302,1286,149,1622]" captionTargetId="figure-214@4.[301,1287,148,1623]" captionTargetPageId="4" captionText="Fig. 3. 1H NMR spectra of Lepidosperma sp Flinder Chase resin (A), plant resin from bee legs (B) and freshly deposited propolis from bee hives (C)." figureDoi="http://doi.org/10.5281/zenodo.8259229" httpUri="https://zenodo.org/record/8259229/files/figure.png" pageId="5" pageNumber="6">Fig. 3S</figureCitation>
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) and
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<superScript id="5CE72F46FFFE0265FFC0FE886333AD1F" attach="right" box="[100,109,365,379]" fontSize="6" pageId="5" pageNumber="6">1</superScript>
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H NMR spectra profiles (
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<figureCitation id="33A99E8BFFFE0265FEF6FE9662D8ADE2" box="[338,390,371,390]" captionStart="Fig" captionStartId="6.[326,356,940,957]" captionTargetBox="[226,1361,149,912]" captionTargetId="figure-552@6.[225,1362,148,913]" captionTargetPageId="6" captionText="Fig. 5. 1H NMR spectra of Lepidosperma viscidum resin (A) and freshly deposited propolis from bee hives (B)." figureDoi="http://doi.org/10.5281/zenodo.8259233" httpUri="https://zenodo.org/record/8259233/files/figure.png" pageId="5" pageNumber="6">Fig. 5</figureCitation>
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) between resin from
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<taxonomicName id="6C92F98DFFFE0265FDEFFE9661F0ADE1" box="[587,686,370,390]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="viscidum">
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<emphasis id="99E65E1CFFFE0265FDEFFE9661F0ADE1" bold="true" box="[587,686,370,390]" italics="true" pageId="5" pageNumber="6">L. viscidum</emphasis>
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</taxonomicName>
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(
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<figureCitation id="33A99E8BFFFE0265FD1FFE9661A5ADE2" box="[699,763,371,390]" captionStart="Fig" captionStartId="5.[100,130,1939,1956]" captionTargetBox="[254,617,1584,1909]" captionTargetId="figure-1366@5.[252,618,1582,1911]" captionTargetPageId="5" captionText="Fig. 4. Known prenylated stilbenes found in propolis and plant source resin in this study." figureDoi="http://doi.org/10.5281/zenodo.8259231" httpUri="https://zenodo.org/record/8259231/files/figure.png" pageId="5" pageNumber="6">Fig. 4S</figureCitation>
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) and propolis samples rich in
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<superScript id="5CE72F46FFFE0265FE21FE6C62D0ADF3" attach="right" box="[389,398,393,407]" fontSize="6" pageId="5" pageNumber="6">1</superScript>
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H NMR signals characteristic of flavanones, designated as F
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<typeStatus id="74293CACFFFE0265FEE1FE4E6230ADDA" box="[325,366,427,446]" pageId="5" pageNumber="6">type</typeStatus>
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propolis. F
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<typeStatus id="74293CACFFFE0265FE41FE4E6150ADDA" box="[485,526,427,446]" pageId="5" pageNumber="6">type</typeStatus>
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propolis is relatively uncommon on KI (18 out of 2602 samples) and relatively common in south-east
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<collectingRegion id="69564CECFFFE0265FF6AFE07623DAD91" box="[206,355,482,501]" country="Australia" name="South Australia" pageId="5" pageNumber="6">South Australia</collectingRegion>
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(4 out of 11 samples). This frequency of appearance is consistent with the uncommon occurrence of
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<taxonomicName id="6C92F98DFFFE0265FD39FE1A605CAE75" box="[669,770,510,530]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="viscidum">
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<emphasis id="99E65E1CFFFE0265FD39FE1A605CAE75" bold="true" box="[669,770,510,530]" italics="true" pageId="5" pageNumber="6">L. viscidum</emphasis>
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</taxonomicName>
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on KI and its common occurrence in the areas in
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<collectingRegion id="69564CECFFFE0265FD98FDFF6190AE49" box="[572,718,538,557]" country="Australia" name="South Australia" pageId="5" pageNumber="6">South Australia</collectingRegion>
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from where F-type propolis samples were collected.
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<taxonomicName id="6C92F98DFFFE0265FD84FDD361DAAE2D" box="[544,644,566,585]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="viscidum">
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<emphasis id="99E65E1CFFFE0265FD84FDD361DAAE2D" bold="true" box="[544,644,566,585]" italics="true" pageId="5" pageNumber="6">L. viscidum</emphasis>
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</taxonomicName>
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resinous leaf and leaf base ethanol extract from Seal Bay, KI, was fractionated by normal-phase short column vacuum chromatography and fractions of sufficient purity were characterised by
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<superScript id="5CE72F46FFFE0265FE40FD6162B3AEF6" attach="right" box="[484,493,644,658]" fontSize="6" pageId="5" pageNumber="6">1</superScript>
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H and
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<superScript id="5CE72F46FFFE0265FD96FD61611AAEF6" attach="right" box="[562,580,644,658]" fontSize="6" pageId="5" pageNumber="6">13</superScript>
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C NMR spectra and mass spectrometry resulting in the identification of five compounds
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||
<emphasis id="99E65E1CFFFE0265FD7CFD4361BAAEDD" bold="true" box="[728,740,678,697]" pageId="5" pageNumber="6">4</emphasis>
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||
,
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||
<emphasis id="99E65E1CFFFE0265FD4BFD4361A5AEDD" bold="true" box="[751,763,678,697]" pageId="5" pageNumber="6">5</emphasis>
|
||
,
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<emphasis id="99E65E1CFFFE0265FFC0FD24632EAEB0" bold="true" box="[100,112,705,724]" pageId="5" pageNumber="6">8</emphasis>
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||
,
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<emphasis id="99E65E1CFFFE0265FFD9FD2463D7AEB0" bold="true" box="[125,137,705,724]" pageId="5" pageNumber="6">9</emphasis>
|
||
and
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||
<emphasis id="99E65E1CFFFE0265FF1DFD246387AEB0" bold="true" box="[185,217,705,724]" pageId="5" pageNumber="6">10.</emphasis>
|
||
</paragraph>
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||
<paragraph id="AB2D820EFFFE0265FF20FD3863EBA83F" blockId="5.[100,771,203,1534]" pageId="5" pageNumber="6">
|
||
Chemistry of
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||
<taxonomicName id="6C92F98DFFFE0265FEA2FD3B6232AE94" box="[262,364,733,753]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="viscidum">
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<emphasis id="99E65E1CFFFE0265FEA2FD3B6232AE94" bold="true" box="[262,364,733,753]" italics="true" pageId="5" pageNumber="6">L. viscidum</emphasis>
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||
</taxonomicName>
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resin is markedly different from that previously observed in another propolis resin sourced from
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<taxonomicName id="6C92F98DFFFE0265FD2CFD1C605FAF68" box="[648,769,761,780]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="genus">
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||
<emphasis id="99E65E1CFFFE0265FD2CFD1C605FAF68" bold="true" box="[648,769,761,780]" italics="true" pageId="5" pageNumber="6">Lepidosperma</emphasis>
|
||
</taxonomicName>
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||
genus on Kangaroo Island (
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||
<bibRefCitation id="CF03FFFFFFFE0265FECCFCF06152AF4C" author="Duke, C. C. & Tran, V. H. & Duke, R. K. & Abu-Mellal, A. & Plunkett, G. T. & King, D. I. & Hamid, K. & Wilson, K. L. & Barrett, R. L. & Bruhl, J. J." box="[360,524,789,809]" pageId="5" pageNumber="6" pagination="87 - 97" refId="ref11052" refString="Duke, C. C., Tran, V. H., Duke, R. K., Abu-Mellal, A., Plunkett, G. T., King, D. I., Hamid, K., Wilson, K. L., Barrett, R. L., Bruhl, J. J., 2017. A sedge plant as the source of Kangaroo Island propolis rich in prenylated p-coumarate ester and stilbenes. Phytochemistry 134, 87 - 97. https: // doi. org / 10.1016 / j. phytochem. 2016.11.005." type="journal article" year="2017">Duke et al., 2017</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="CF03FFFFFFFE0265FDBDFCF061AAAF4C" author="Abu-Mellal, A. & Koolaji, N. & Duke, R. K. & Tran, V. H. & Duke, C. C." box="[537,756,789,809]" pageId="5" pageNumber="6" pagination="251 - 259" refId="ref10292" refString="Abu-Mellal, A., Koolaji, N., Duke, R. K., Tran, V. H., Duke, C. C., 2012. Prenylated cinnamate and stilbenes from Kangaroo Island propolis and their antioxidant activity. Phytochemistry 77, 251 - 259. https: // doi. org / 10.1016 / j. phytochem. 2012.01.012." type="journal article" year="2012">Abu-Mellal et al., 2012</bibRefCitation>
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||
). This propolis
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||
<typeStatus id="74293CACFFFE0265FF41FCD76250AF21" box="[229,270,818,837]" pageId="5" pageNumber="6">type</typeStatus>
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||
has resin sourced from
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<taxonomicName id="6C92F98DFFFE0265FE55FCD461D2AF21" box="[497,652,817,837]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="undetermined">
|
||
<emphasis id="99E65E1CFFFE0265FE55FCD46134AF20" bold="true" box="[497,618,817,836]" italics="true" pageId="5" pageNumber="6">Lepidosperma</emphasis>
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||
sp.
|
||
</taxonomicName>
|
||
Montebello, with chemistry extensively investigated (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FE4EFCA861D3AF04" author="Duke, C. C. & Tran, V. H. & Duke, R. K. & Abu-Mellal, A. & Plunkett, G. T. & King, D. I. & Hamid, K. & Wilson, K. L. & Barrett, R. L. & Bruhl, J. J." box="[490,653,845,864]" pageId="5" pageNumber="6" pagination="87 - 97" refId="ref11052" refString="Duke, C. C., Tran, V. H., Duke, R. K., Abu-Mellal, A., Plunkett, G. T., King, D. I., Hamid, K., Wilson, K. L., Barrett, R. L., Bruhl, J. J., 2017. A sedge plant as the source of Kangaroo Island propolis rich in prenylated p-coumarate ester and stilbenes. Phytochemistry 134, 87 - 97. https: // doi. org / 10.1016 / j. phytochem. 2016.11.005." type="journal article" year="2017">Duke et al., 2017</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="CF03FFFFFFFE0265FD3EFCA8638AAF18" author="Abu-Mellal, A. & Koolaji, N. & Duke, R. K. & Tran, V. H. & Duke, C. C." pageId="5" pageNumber="6" pagination="251 - 259" refId="ref10292" refString="Abu-Mellal, A., Koolaji, N., Duke, R. K., Tran, V. H., Duke, C. C., 2012. Prenylated cinnamate and stilbenes from Kangaroo Island propolis and their antioxidant activity. Phytochemistry 77, 251 - 259. https: // doi. org / 10.1016 / j. phytochem. 2012.01.012." type="journal article" year="2012">Abu-Mellal et al., 2012</bibRefCitation>
|
||
). The compounds isolated from resins of that species are predominantly C- and O-prenylated hydroxystilbenes or derivatives thereof, many with piceatannol as base structure. By comparison,
|
||
<taxonomicName id="6C92F98DFFFE0265FFC0FC586399AFAB" box="[100,199,956,976]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="viscidum">
|
||
<emphasis id="99E65E1CFFFE0265FFC0FC586399AFAB" bold="true" box="[100,199,956,976]" italics="true" pageId="5" pageNumber="6">L. viscidum</emphasis>
|
||
</taxonomicName>
|
||
resin appears to be predominantly 6- or 8-methyl or dimethyl polyhydroxyflavanones
|
||
<emphasis id="99E65E1CFFFE0265FEE0FC3D620EAF8F" bold="true" box="[324,336,984,1003]" pageId="5" pageNumber="6">8</emphasis>
|
||
,
|
||
<emphasis id="99E65E1CFFFE0265FEFFFC3D6239AF8F" bold="true" box="[347,359,984,1003]" pageId="5" pageNumber="6">9</emphasis>
|
||
and
|
||
<emphasis id="99E65E1CFFFE0265FE30FC3D62F3AF8F" bold="true" box="[404,429,984,1003]" pageId="5" pageNumber="6">10</emphasis>
|
||
(
|
||
<figureCitation id="33A99E8BFFFE0265FE1EFC3C62B3AF88" box="[442,493,985,1004]" captionStart="Fig" captionStartId="6.[100,130,1411,1428]" captionTargetBox="[108,766,1015,1382]" captionTargetId="figure-575@6.[106,767,1014,1383]" captionTargetPageId="6" captionText="Fig. 6. Known flavanones found in propolis and plant source resins in this study." figureDoi="http://doi.org/10.5281/zenodo.8259235" httpUri="https://zenodo.org/record/8259235/files/figure.png" pageId="5" pageNumber="6">Fig. 6</figureCitation>
|
||
);
|
||
<superScript id="5CE72F46FFFE0265FDA4FC366157AF85" attach="right" box="[512,521,979,993]" fontSize="6" pageId="5" pageNumber="6">1</superScript>
|
||
H NMR spectra of less pure fractions also suggests the presence of some O-methylated flavanones. Notably, prenylation appears to be less common in
|
||
<taxonomicName id="6C92F98DFFFE0265FDC7FBF46195A847" box="[611,715,1040,1060]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="viscidum">
|
||
<emphasis id="99E65E1CFFFE0265FDC7FBF46195A847" bold="true" box="[611,715,1040,1060]" italics="true" pageId="5" pageNumber="6">L. viscidum</emphasis>
|
||
</taxonomicName>
|
||
resin compounds, with the exception of the two dihydrochalcones,
|
||
<emphasis id="99E65E1CFFFE0265FD16FBC961E0A85B" bold="true" box="[690,702,1068,1087]" pageId="5" pageNumber="6">4</emphasis>
|
||
and
|
||
<emphasis id="99E65E1CFFFE0265FD4BFBC961A5A85B" bold="true" box="[751,763,1068,1087]" pageId="5" pageNumber="6">5</emphasis>
|
||
, isolated.
|
||
</paragraph>
|
||
<paragraph id="AB2D820EFFFE0265FF20FB816711AD2A" blockId="5.[100,771,203,1534]" lastBlockId="5.[818,1488,148,864]" pageId="5" pageNumber="6">
|
||
Compounds similar to
|
||
<emphasis id="99E65E1CFFFE0265FEC7FB816231A813" bold="true" box="[355,367,1124,1143]" pageId="5" pageNumber="6">4</emphasis>
|
||
and
|
||
<emphasis id="99E65E1CFFFE0265FE01FB8162EFA813" bold="true" box="[421,433,1124,1143]" pageId="5" pageNumber="6">5</emphasis>
|
||
without the 4-hydroxyprenyl substituent, 4,2
|
||
<superScript id="5CE72F46FFFE0265FF70FB986387A8EE" attach="none" box="[212,217,1149,1162]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
,4
|
||
<superScript id="5CE72F46FFFE0265FF48FB9863AFA8EE" attach="none" box="[236,241,1149,1162]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-trihydroxydihydrochalcone (davidigenin) (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FD2DFB6563CAA8CB" author="Jensen, S. R. & Nielsen, B. J. & Norn, V." pageId="5" pageNumber="6" pagination="2036 - 2038" refId="ref11718" refString="Jensen, S. R., Nielsen, B. J., Norn, V., 1977. Dihydrochalcones from Viburnum davidii and V. lantanoides. Phytochemistry 16, 2036 - 2038. https: // doi. org / 10.1016 / 0031 - 9422 (77) 80128 - 3." type="journal article" year="1977">Jensen et al., 1977</bibRefCitation>
|
||
) and 4,2
|
||
<superScript id="5CE72F46FFFE0265FF4FFB7C63AEA8C2" attach="none" box="[235,240,1177,1190]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-dihydroxy-4
|
||
<superScript id="5CE72F46FFFE0265FECEFB7C6231A8C2" attach="none" box="[362,367,1177,1190]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-methoxydihydrochalcone (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FDD0FB79620EA8AF" author="Kostrzewa-Suslow, E. & Janeczko, T." pageId="5" pageNumber="6" pagination="14810 - 14820" refId="ref11852" refString="Kostrzewa-Suslow, E., Janeczko, T., 2012. Microbial transformations of 7 - methoxyflavanone. Molecules 17 (12), 14810 - 14820. https: // doi. org / 10.3390 / molecules 171214810." type="journal article" year="2012">Kostrzewa-Susłow and Janeczko, 2012</bibRefCitation>
|
||
) have
|
||
<superScript id="5CE72F46FFFE0265FE32FB5762C1A8A4" attach="right" box="[406,415,1202,1216]" fontSize="6" pageId="5" pageNumber="6">1</superScript>
|
||
H and
|
||
<superScript id="5CE72F46FFFE0265FE47FB5762ABA8A4" attach="right" box="[483,501,1202,1216]" fontSize="6" pageId="5" pageNumber="6">13</superScript>
|
||
C NMR spectral results that show good partial concordance with
|
||
<emphasis id="99E65E1CFFFE0265FE18FB366296A882" bold="true" box="[444,456,1235,1254]" pageId="5" pageNumber="6">4</emphasis>
|
||
and
|
||
<emphasis id="99E65E1CFFFE0265FE51FB31615FA883" bold="true" box="[501,513,1236,1255]" pageId="5" pageNumber="6">5</emphasis>
|
||
. The most similar structure to
|
||
<emphasis id="99E65E1CFFFE0265FFD9FB1563D7A967" bold="true" box="[125,137,1264,1283]" pageId="5" pageNumber="6">5</emphasis>
|
||
reported was 3
|
||
<superScript id="5CE72F46FFFE0265FEBFFB09627EA89D" attach="none" box="[283,288,1260,1273]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-prenyl-4,2
|
||
<superScript id="5CE72F46FFFE0265FE2CFB0962D3A89D" attach="none" box="[392,397,1260,1273]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-dihydroxy-4
|
||
<superScript id="5CE72F46FFFE0265FDA3FB096152A89D" attach="none" box="[519,524,1260,1273]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-methoxydihydrochalcone (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FFC8FAEE621CA97A" author="Awouafack, M. D. & Kusari, S. & Ngamga, D. & Tane, P. & Spiteller, M." box="[108,322,1291,1311]" pageId="5" pageNumber="6" pagination="640 - 643" refId="ref10534" refString="Awouafack, M. D., Kusari, S., Lamsh ¨ oft, M., Ngamga, D., Tane, P., Spiteller, M., 2010. Semi-synthesis of dihydrochalcone derivatives and their in vitro antimicrobial activities. Planta Med. 76 (6), 640 - 643. https: // doi. org / 10.1055 / s- 0029 - 1240619." type="journal article" year="2010">Awouafack et al., 2010</bibRefCitation>
|
||
). The stereoisomer identified in
|
||
<emphasis id="99E65E1CFFFE0265FDD5FAEE6123A97A" bold="true" box="[625,637,1291,1310]" pageId="5" pageNumber="6">4</emphasis>
|
||
and
|
||
<emphasis id="99E65E1CFFFE0265FD0EFAEE61E8A97A" bold="true" box="[682,694,1291,1310]" pageId="5" pageNumber="6">5</emphasis>
|
||
was the
|
||
<emphasis id="99E65E1CFFFE0265FFC0FACD632EA95F" bold="true" box="[100,112,1320,1339]" italics="true" pageId="5" pageNumber="6">E</emphasis>
|
||
configuration. This configuration is reported to be predominant in terminally-hydroxylated prenyl groups in natural products (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FD2BFAA163CAA916" author="Erasto, P. & Bojase-Moleta, G. & Majinda, R. R." pageId="5" pageNumber="6" pagination="875 - 880" refId="ref11304" refString="Erasto, P., Bojase-Moleta, G., Majinda, R. R., 2004. Antimicrobial and antioxidant flavonoids from the root wood of Bolusanthus speciosus. Phytochemistry 65, 875 - 880. https: // doi. org / 10.1016 / j. phytochem. 2004.02.011." type="journal article" year="2004">Erasto et al., 2004</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="CF03FFFFFFFE0265FF06FA856201A916" author="Nguyen, N. T. & Nguyen, M. H. K. & Nguyen, H. X. & Bui, N. K. N. & Nguyen, M. T. T." box="[162,351,1375,1395]" pageId="5" pageNumber="6" pagination="1951 - 1955" refId="ref12833" refString="Nguyen, N. T., Nguyen, M. H. K., Nguyen, H. X., Bui, N. K. N., Nguyen, M. T. T., 2012. Tyrosinase inhibitors from the wood of Artocarpus heterophyllus. J. Nat. Prod. 75 (11), 1951 - 1955. https: // doi. org / 10.1021 / np 300576 w." type="journal article" year="2012">Nguyen et al., 2012</bibRefCitation>
|
||
). Compounds
|
||
<emphasis id="99E65E1CFFFE0265FE4FFABA62A9A916" bold="true" box="[491,503,1375,1394]" pageId="5" pageNumber="6">4</emphasis>
|
||
and
|
||
<emphasis id="99E65E1CFFFE0265FD8EFABA6168A916" bold="true" box="[554,566,1375,1394]" pageId="5" pageNumber="6">5</emphasis>
|
||
are previously undescribed: a number of 3
|
||
<superScript id="5CE72F46FFFE0265FE9EFA9D6261A9E1" attach="none" box="[314,319,1400,1413]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-prenyl hydroxydihydrochalcones have been reported from natural sources but no 5
|
||
<superScript id="5CE72F46FFFE0265FE72FA716285A9C5" attach="none" box="[470,475,1428,1441]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-prenylated structures to date. These 3
|
||
<superScript id="5CE72F46FFFE0265FF10FA5563E7A9D9" attach="none" box="[180,185,1456,1469]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-prenyl hydroxydihydrochalcones have been isolated from genera
|
||
<taxonomicName id="6C92F98DFFFE0265FF0FFA2B63A9A985" box="[171,247,1486,1505]" class="Magnoliopsida" family="Apiaceae" genus="Angelica" kingdom="Plantae" order="Apiales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="99E65E1CFFFE0265FF0FFA2B63A9A985" bold="true" box="[171,247,1486,1505]" italics="true" pageId="5" pageNumber="6">Angelica</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<taxonomicName id="6C92F98DFFFE0265FEA1FA2A6200A986" box="[261,350,1487,1506]" class="Magnoliopsida" family="Apiaceae" kingdom="Plantae" order="Apiales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Apiaceae</taxonomicName>
|
||
) (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FED0FA2A6146A986" author="Luo, L. & Wang, R. & Wang, X. & Ma, Z. & Li, N." box="[372,536,1487,1506]" pageId="5" pageNumber="6" pagination="992 - 998" refId="ref12380" refString="Luo, L., Wang, R., Wang, X., Ma, Z., Li, N., 2012 a. Compounds from Angelica keiskei with NQO 1 induction, DPPH scavenging and α- glucosidase inhibitory activities. Food Chem. 131 (3), 992 - 998. https: // doi. org / 10.1016 / j. foodchem. 2011.09.099." type="journal article" year="2012">Luo et al., 2012a</bibRefCitation>
|
||
),
|
||
<taxonomicName id="6C92F98DFFFE0265FD8AFA2A61D1A986" box="[558,655,1487,1506]" class="Magnoliopsida" family="Moraceae" genus="Artocarpus" kingdom="Plantae" order="Rosales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="99E65E1CFFFE0265FD8AFA2A61D1A986" bold="true" box="[558,655,1487,1506]" italics="true" pageId="5" pageNumber="6">Artocarpus</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<taxonomicName id="6C92F98DFFFE0265FD39FA2A61A5A986" box="[669,763,1487,1506]" class="Magnoliopsida" family="Moraceae" kingdom="Plantae" order="Rosales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Moraceae</taxonomicName>
|
||
) (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FFC8FA0F627EA99A" author="Jamil, S. & Sirat, H. M. & Jantan, I. & Aimi, N. & Kitajima, M." box="[108,288,1514,1534]" pageId="5" pageNumber="6" pagination="321 - 324" refId="ref11645" refString="Jamil, S., Sirat, H. M., Jantan, I., Aimi, N., Kitajima, M., 2008. A new prenylated dihydrochalcone from the leaves of Artocarpus lowii. J. Nat. Med. 62 (3), 321 - 324. https: // doi. org / 10.1007 / s 11418 - 008 - 0226 - 3." type="journal article" year="2008">Jamil et al., 2008</bibRefCitation>
|
||
),
|
||
<taxonomicName id="6C92F98DFFFE0265FE9DFA0E6225A99A" box="[313,379,1515,1534]" class="Magnoliopsida" family="Plantaginaceae" genus="Bacopa" kingdom="Plantae" order="Lamiales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="99E65E1CFFFE0265FE9DFA0E6225A99A" bold="true" box="[313,379,1515,1534]" italics="true" pageId="5" pageNumber="6">Bacopa</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<taxonomicName id="6C92F98DFFFE0265FE28FA0F6143A999" box="[396,541,1514,1533]" class="Magnoliopsida" family="Plantaginaceae" kingdom="Plantae" order="Lamiales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Plantaginaceae</taxonomicName>
|
||
) (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FD92FA0F61AAA99A" author="Suresh, A. & Sheela, X. Q. R. & Kanmani, R. & Mani, C. & Easwaran, L. & Stanley, A. L. & Ramani, V. A." box="[566,756,1514,1534]" pageId="5" pageNumber="6" pagination="965 - 970" refId="ref13143" refString="Suresh, A., Sheela, X. Q. R., Kanmani, R., Mani, C., Easwaran, L., Stanley, A. L., Ramani, V. A., 2010. Isolation and identification of a chalcone from Baccopa monnieri [sic]. Asian J. Chem. 22 (2), 965 - 970." type="journal article" year="2010">Suresh et al., 2010</bibRefCitation>
|
||
),
|
||
<taxonomicName id="6C92F98DFFFE0265FC96FF7160FDACC3" box="[818,931,148,167]" class="Magnoliopsida" family="Moraceae" genus="Broussonetia" kingdom="Plantae" order="Rosales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="99E65E1CFFFE0265FC96FF7160FDACC3" bold="true" box="[818,931,148,167]" italics="true" pageId="5" pageNumber="6">Broussonetia</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<taxonomicName id="6C92F98DFFFE0265FC13FF71674BACC3" box="[951,1045,148,167]" class="Magnoliopsida" family="Moraceae" kingdom="Plantae" order="Rosales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Moraceae</taxonomicName>
|
||
) (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FB97FF7167B3ACC3" author="Luo, L. & Shen, L. & Sun, F. & Dai, Y. & Zheng, H. & Ma, Z. & Xu, Y. & Guo, Z." box="[1075,1261,148,167]" pageId="5" pageNumber="6" pagination="230 - 235" refId="ref12452" refString="Luo, L., Shen, L., Sun, F., Dai, Y., Zheng, H., Ma, Z., Xu, Y., Guo, Z., 2012 b. Screening for aromatase ligands in the extract of Broussonetia papyrifera using high performance liquid chromatography and ESI-mass spectrometry. Anal. Methods 4 (1), 230 - 235. https: // doi. org / 10.1039 / c 1 ay 05659 j." type="journal article" year="2012">Luo et al., 2012b</bibRefCitation>
|
||
),
|
||
<taxonomicName id="6C92F98DFFFE0265FAADFF716604ACC3" box="[1289,1370,148,167]" class="Magnoliopsida" family="Fabaceae" genus="Eriosema" kingdom="Plantae" order="Fabales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="99E65E1CFFFE0265FAADFF716604ACC3" bold="true" box="[1289,1370,148,167]" italics="true" pageId="5" pageNumber="6">Eriosema</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<taxonomicName id="6C92F98DFFFE0265FACBFF716697ACC3" box="[1391,1481,148,167]" class="Magnoliopsida" family="Fabaceae" kingdom="Plantae" order="Fabales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Fabaceae</taxonomicName>
|
||
) (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FC9EFF556742ACA7" author="Awouafack, M. D. & Kouam, S. F. & Hussain, H. & Ngamga, D. & Tane, P. & Schulz, B. & Green, I. & Krohn, K." box="[826,1052,176,195]" pageId="5" pageNumber="6" pagination="50 - 54" refId="ref10455" refString="Awouafack, M. D., Kouam, S. F., Hussain, H., Ngamga, D., Tane, P., Schulz, B., Green, I., Krohn, K., 2008. Antimicrobial prenylated dihydrochalcones from Eriosema glomerata. Planta Med. 74 (1), 50 - 54. https: // doi. org / 10.1055 / s- 2007 - 993782." type="journal article" year="2008">Awouafack et al., 2008</bibRefCitation>
|
||
,
|
||
<bibRefCitation id="CF03FFFFFFFE0265FB8FFF556705ACA7" author="Awouafack, M. D. & Kusari, S. & Ngamga, D. & Tane, P. & Spiteller, M." box="[1067,1115,176,195]" pageId="5" pageNumber="6" pagination="640 - 643" refId="ref10534" refString="Awouafack, M. D., Kusari, S., Lamsh ¨ oft, M., Ngamga, D., Tane, P., Spiteller, M., 2010. Semi-synthesis of dihydrochalcone derivatives and their in vitro antimicrobial activities. Planta Med. 76 (6), 640 - 643. https: // doi. org / 10.1055 / s- 0029 - 1240619." type="journal article" year="2010">2010</bibRefCitation>
|
||
) and
|
||
<taxonomicName id="6C92F98DFFFE0265FB33FF4A664FACA6" box="[1175,1297,175,194]" class="Magnoliopsida" family="Fabaceae" genus="Lonchocarpus" kingdom="Plantae" order="Fabales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="99E65E1CFFFE0265FB33FF4A664FACA6" bold="true" box="[1175,1297,175,194]" italics="true" pageId="5" pageNumber="6">Lonchocarpus</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<taxonomicName id="6C92F98DFFFE0265FA85FF556625ACA7" box="[1313,1403,176,195]" class="Magnoliopsida" family="Fabaceae" kingdom="Plantae" order="Fabales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Fabaceae</taxonomicName>
|
||
) (Borges-Arg´aez et al., 2009), none of these genera being closely related to the
|
||
<taxonomicName id="6C92F98DFFFE0265FC96FF0D60FFAC9F" authorityName="de Jussieu" authorityYear="1789" box="[818,929,232,251]" class="Liliopsida" family="Cyperaceae" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Cyperaceae</taxonomicName>
|
||
. Limited information on biological activity of these compounds exists, but one is a reported strong free radical scavenger by the DPPH assay (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FC0FFEFA6715AD56" author="Jamil, S. & Sirat, H. M. & Jantan, I. & Aimi, N. & Kitajima, M." box="[939,1099,287,307]" pageId="5" pageNumber="6" pagination="321 - 324" refId="ref11645" refString="Jamil, S., Sirat, H. M., Jantan, I., Aimi, N., Kitajima, M., 2008. A new prenylated dihydrochalcone from the leaves of Artocarpus lowii. J. Nat. Med. 62 (3), 321 - 324. https: // doi. org / 10.1007 / s 11418 - 008 - 0226 - 3." type="journal article" year="2008">Jamil et al., 2008</bibRefCitation>
|
||
) and another has been observed to inhibit aromatase (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FC05FEDE671FAD2A" author="Luo, L. & Shen, L. & Sun, F. & Dai, Y. & Zheng, H. & Ma, Z. & Xu, Y. & Guo, Z." box="[929,1089,315,334]" pageId="5" pageNumber="6" pagination="230 - 235" refId="ref12452" refString="Luo, L., Shen, L., Sun, F., Dai, Y., Zheng, H., Ma, Z., Xu, Y., Guo, Z., 2012 b. Screening for aromatase ligands in the extract of Broussonetia papyrifera using high performance liquid chromatography and ESI-mass spectrometry. Anal. Methods 4 (1), 230 - 235. https: // doi. org / 10.1039 / c 1 ay 05659 j." type="journal article" year="2012">Luo et al., 2012b</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="AB2D820EFFFE0265FCF5FEB260B7AF04" blockId="5.[818,1488,148,864]" pageId="5" pageNumber="6">
|
||
The molecular weight of compounds identified as 5,7,4
|
||
<superScript id="5CE72F46FFFE0265FAFDFEB16600AD05" attach="none" box="[1369,1374,340,353]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-trihydroxy- 6,8-dimethylflavanone (farrerol) (
|
||
<emphasis id="99E65E1CFFFE0265FBD8FE9667D6ADE2" bold="true" box="[1148,1160,371,390]" pageId="5" pageNumber="6">8</emphasis>
|
||
), 5,7,3
|
||
<superScript id="5CE72F46FFFE0265FB75FE956788AD19" attach="none" box="[1233,1238,368,381]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
,5
|
||
<superScript id="5CE72F46FFFE0265FB4CFE9567B3AD19" attach="none" box="[1256,1261,368,381]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-tetrahydroxy-6,8-dimethylflavanone (
|
||
<emphasis id="99E65E1CFFFE0265FC63FE6A608DADC6" bold="true" box="[967,979,399,418]" pageId="5" pageNumber="6">9</emphasis>
|
||
) and 5,7,3
|
||
<superScript id="5CE72F46FFFE0265FBE2FE696715ADFD" attach="none" box="[1094,1099,396,409]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
,5
|
||
<superScript id="5CE72F46FFFE0265FBF9FE69673CADFD" attach="none" box="[1117,1122,396,409]" fontSize="6" pageId="5" pageNumber="6">′</superScript>
|
||
-tetrahydroxy-6-methylflavanone (
|
||
<emphasis id="99E65E1CFFFE0265FA0AFE6A6699ADC6" bold="true" box="[1454,1479,399,418]" pageId="5" pageNumber="6">10</emphasis>
|
||
) was determined by mass spectrometry. Close matches with literature
|
||
<superScript id="5CE72F46FFFE0265FA14FE40669CADD7" attach="right" box="[1456,1474,421,435]" fontSize="6" pageId="5" pageNumber="6">13</superScript>
|
||
C NMR and
|
||
<superScript id="5CE72F46FFFE0265FC32FE2460C1ADAB" attach="right" box="[918,927,449,463]" fontSize="6" pageId="5" pageNumber="6">1</superScript>
|
||
H NMR spectra enabled identification of the structures of these known compounds: farrelol (
|
||
<emphasis id="99E65E1CFFFE0265FB25FE0767D3AD91" bold="true" box="[1153,1165,482,501]" pageId="5" pageNumber="6">8</emphasis>
|
||
) (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FB02FE076664AD91" author="Lai, Y. & Zeng, H. & He, M. & Qian, H. & Wu, Z. & Luo, Z. & Xue, Y. & Yao, G. & Zhang, Y." box="[1190,1338,482,502]" pageId="5" pageNumber="6" pagination="237 - 243" refId="ref12141" refString="Lai, Y., Zeng, H., He, M., Qian, H., Wu, Z., Luo, Z., Xue, Y., Yao, G., Zhang, Y., 2016. 6, 8 - Di-C-methyl-flavonoids with neuroprotective activities from Rhododendron fortunei. Fitoterapia 112, 237 - 243. https: // doi. org / 10.1016 / j. fitote. 2016.06.008." type="journal article" year="2016">Lai et al., 2016</bibRefCitation>
|
||
);
|
||
<emphasis id="99E65E1CFFFE0265FAF4FE076602AD91" bold="true" box="[1360,1372,482,501]" pageId="5" pageNumber="6">9</emphasis>
|
||
(
|
||
<bibRefCitation id="CF03FFFFFFFE0265FAC9FE06603CAE75" author="Lou, X. - W. & Lin, Q. - H. & Zhang, G. - Y. & Liu, W. - Y. & Feng, F. & Qu, W." pageId="5" pageNumber="6" pagination="628 - 633" refId="ref12288" refString="Lou, X. - W., Lin, Q. - H., Zhang, G. - Y., Liu, W. - Y., Feng, F., Qu, W., 2015. Identification and characterization of three new flavonoids from Rhododendron dauricum. Chin. J. Nat. Med. 13 (8), 628 - 633. https: // doi. org / 10.1016 / S 1875 - 5364 (15) 30059 - 5." type="journal article" year="2015">Lou et al., 2015</bibRefCitation>
|
||
);
|
||
<emphasis id="99E65E1CFFFE0265FCD3FE1B60CEAE75" bold="true" box="[887,912,510,529]" pageId="5" pageNumber="6">10</emphasis>
|
||
(
|
||
<bibRefCitation id="CF03FFFFFFFE0265FC3BFE1B6779AE75" author="Yi, J. - H. & Zhang, G. - L. & Li, B. - G." box="[927,1063,510,530]" pageId="5" pageNumber="6" pagination="352 - 354" refId="ref13420" refString="Yi, J. - H., Zhang, G. - L., Li, B. - G., 2002. R Kfflsmraeffiw [Studies on the chemical constituents of Pseudotsuga sinensis]. Acta Pharm. Sin. 37 (5), 352 - 354." type="journal article" year="2002">Yi et al., 2002</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="CF03FFFFFFFE0265FB90FE1B67BCAE75" author="Zhang, Y. & Yan, G. & Sun, C. & Li, H. & Fu, Y. & Xu, W." box="[1076,1250,510,530]" pageId="5" pageNumber="6" refId="ref13473" refString="Zhang, Y., Yan, G., Sun, C., Li, H., Fu, Y., Xu, W., 2018. Apoptosis effects of dihydrokaempferol isolated from Bauhinia championii on synoviocytes. Evid. base Compl. Alternative Med. 2018 https: // doi. org / 10.1155 / 2018 / 9806160. Article ID 9806160, 10 pages." type="book" year="2018">Zhang et al., 2018</bibRefCitation>
|
||
). Farrerol (
|
||
<emphasis id="99E65E1CFFFE0265FAF6FE1B6600AE75" bold="true" box="[1362,1374,510,529]" pageId="5" pageNumber="6">8</emphasis>
|
||
) has a long history in the literature and has been isolated from plants from a widespread number of genera (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FBF8FDD367B3AE2D" author="Lai, Y. & Zeng, H. & He, M. & Qian, H. & Wu, Z. & Luo, Z. & Xue, Y. & Yao, G. & Zhang, Y." box="[1116,1261,566,586]" pageId="5" pageNumber="6" pagination="237 - 243" refId="ref12141" refString="Lai, Y., Zeng, H., He, M., Qian, H., Wu, Z., Luo, Z., Xue, Y., Yao, G., Zhang, Y., 2016. 6, 8 - Di-C-methyl-flavonoids with neuroprotective activities from Rhododendron fortunei. Fitoterapia 112, 237 - 243. https: // doi. org / 10.1016 / j. fitote. 2016.06.008." type="journal article" year="2016">Lai et al., 2016</bibRefCitation>
|
||
). Compound
|
||
<emphasis id="99E65E1CFFFE0265FACBFDD36625AE2D" bold="true" box="[1391,1403,566,585]" pageId="5" pageNumber="6">9</emphasis>
|
||
has previously been isolated from
|
||
<taxonomicName id="6C92F98DFFFE0265FB9DFDB76649AE01" box="[1081,1303,594,613]" class="Magnoliopsida" family="Ericaceae" genus="Rhododendron" kingdom="Plantae" order="Ericales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="dauricum">
|
||
<emphasis id="99E65E1CFFFE0265FB9DFDB76649AE01" bold="true" box="[1081,1303,594,613]" italics="true" pageId="5" pageNumber="6">Rhododendron dauricum</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<taxonomicName id="6C92F98DFFFE0265FA82FDB766DDAE01" box="[1318,1411,594,613]" class="Magnoliopsida" family="Ericaceae" kingdom="Plantae" order="Ericales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Ericaceae</taxonomicName>
|
||
) (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FA3DFDB760C5AEE5" author="Wang, L. & Zhu, X. & Lou, X. & Zheng, F. & Feng, Y. & Liu, W. & Feng, F. & Xie, N." pageId="5" pageNumber="6" pagination="3161 - 3169" refId="ref13326" refString="Wang, L., Zhu, X., Lou, X., Zheng, F., Feng, Y., Liu, W., Feng, F., Xie, N., 2015. Systematic characterization and simultaneous quantification of the multiple components of Rhododendron dauricum based on high-performance liquid chromatography with quadrupole time-of-flight tandem mass spectrometry. J. Separ. Sci. 38 (18), 3161 - 3169. https: // doi. org / 10.1002 / jssc. 201500553." type="journal article" year="2015">Wang et al., 2015</bibRefCitation>
|
||
) as per farrerol, and
|
||
<emphasis id="99E65E1CFFFE0265FBC4FD8B6727AEE5" bold="true" box="[1120,1145,622,641]" pageId="5" pageNumber="6">10</emphasis>
|
||
from the conifer
|
||
<taxonomicName id="6C92F98DFFFE0265FABFFD8B6691AEE5" box="[1307,1487,622,641]" class="Pinopsida" family="Pinaceae" genus="Pseudotsuga" kingdom="Plantae" order="Pinales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="sinensis">
|
||
<emphasis id="99E65E1CFFFE0265FABFFD8B6691AEE5" bold="true" box="[1307,1487,622,641]" italics="true" pageId="5" pageNumber="6">Pseudotsuga sinensis</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<taxonomicName id="6C92F98DFFFE0265FC9CFD6F60D1AEF9" box="[824,911,650,669]" class="Pinopsida" family="Pinaceae" kingdom="Plantae" order="Pinales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Pinaceae</taxonomicName>
|
||
) (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FC05FD6F677CAEF9" author="Yi, J. - H. & Zhang, G. - L. & Li, B. - G." box="[929,1058,650,669]" pageId="5" pageNumber="6" pagination="352 - 354" refId="ref13420" refString="Yi, J. - H., Zhang, G. - L., Li, B. - G., 2002. R Kfflsmraeffiw [Studies on the chemical constituents of Pseudotsuga sinensis]. Acta Pharm. Sin. 37 (5), 352 - 354." type="journal article" year="2002">Yi et al., 2002</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="CF03FFFFFFFE0265FB89FD6F678AAEF9" author="Zhang, Y. & Yan, G. & Sun, C. & Li, H. & Fu, Y. & Xu, W." box="[1069,1236,650,669]" pageId="5" pageNumber="6" refId="ref13473" refString="Zhang, Y., Yan, G., Sun, C., Li, H., Fu, Y., Xu, W., 2018. Apoptosis effects of dihydrokaempferol isolated from Bauhinia championii on synoviocytes. Evid. base Compl. Alternative Med. 2018 https: // doi. org / 10.1155 / 2018 / 9806160. Article ID 9806160, 10 pages." type="book" year="2018">Zhang et al., 2018</bibRefCitation>
|
||
). Neither species belong to families closely related to the
|
||
<taxonomicName id="6C92F98DFFFE0265FBF6FD43679FAEDD" authorityName="de Jussieu" authorityYear="1789" box="[1106,1217,678,697]" class="Liliopsida" family="Cyperaceae" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="family">Cyperaceae</taxonomicName>
|
||
. No reports of biological activity for these compounds were found (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FB19FD276632AEB0" author="Wang, L. & Zhu, X. & Lou, X. & Zheng, F. & Feng, Y. & Liu, W. & Feng, F. & Xie, N." box="[1213,1388,705,725]" pageId="5" pageNumber="6" pagination="3161 - 3169" refId="ref13326" refString="Wang, L., Zhu, X., Lou, X., Zheng, F., Feng, Y., Liu, W., Feng, F., Xie, N., 2015. Systematic characterization and simultaneous quantification of the multiple components of Rhododendron dauricum based on high-performance liquid chromatography with quadrupole time-of-flight tandem mass spectrometry. J. Separ. Sci. 38 (18), 3161 - 3169. https: // doi. org / 10.1002 / jssc. 201500553." type="journal article" year="2015">Wang et al., 2015</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="CF03FFFFFFFE0265FADFFD24603CAE95" author="Yi, J. - H. & Zhang, G. - L. & Li, B. - G." pageId="5" pageNumber="6" pagination="352 - 354" refId="ref13420" refString="Yi, J. - H., Zhang, G. - L., Li, B. - G., 2002. R Kfflsmraeffiw [Studies on the chemical constituents of Pseudotsuga sinensis]. Acta Pharm. Sin. 37 (5), 352 - 354." type="journal article" year="2002">Yi et al., 2002</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="CF03FFFFFFFE0265FCC8FD38674AAE95" author="Zhang, Y. & Yan, G. & Sun, C. & Li, H. & Fu, Y. & Xu, W." box="[876,1044,733,753]" pageId="5" pageNumber="6" refId="ref13473" refString="Zhang, Y., Yan, G., Sun, C., Li, H., Fu, Y., Xu, W., 2018. Apoptosis effects of dihydrokaempferol isolated from Bauhinia championii on synoviocytes. Evid. base Compl. Alternative Med. 2018 https: // doi. org / 10.1155 / 2018 / 9806160. Article ID 9806160, 10 pages." type="book" year="2018">Zhang et al., 2018</bibRefCitation>
|
||
). F
|
||
<typeStatus id="74293CACFFFE0265FB93FD3B673EAE95" box="[1079,1120,734,753]" pageId="5" pageNumber="6">type</typeStatus>
|
||
propolis and its resin source
|
||
<taxonomicName id="6C92F98DFFFE0265FAC8FD3B6691AE94" box="[1388,1487,733,753]" class="Liliopsida" family="Cyperaceae" genus="Lepidosperma" kingdom="Plantae" order="Poales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="viscidum">
|
||
<emphasis id="99E65E1CFFFE0265FAC8FD3B6691AE94" bold="true" box="[1388,1487,733,753]" italics="true" pageId="5" pageNumber="6">L. viscidum</emphasis>
|
||
</taxonomicName>
|
||
are a promising source of a diverse range of flavanones of potentially useful biological activity, and of farrerol, a compound of intense pharmaceutical interest (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FC58FCD467C5AF20" author="Dai, F. & Gao, L. & Zhao, Y. & Wang, C. & Xie, S." box="[1020,1179,817,837]" pageId="5" pageNumber="6" pagination="686 - 693" refId="ref10848" refString="Dai, F., Gao, L., Zhao, Y., Wang, C., Xie, S., 2016. Farrerol inhibited angiogenesis through Akt / mTOR, Erk and Jak 2 / Stat 3 signal pathway. Phytomedicine 23, 686 - 693. https: // doi. org / 10.1016 / j. phymed. 2016.03.008." type="journal article" year="2016">Dai et al., 2016</bibRefCitation>
|
||
) and long-term traditional use (
|
||
<bibRefCitation id="CF03FFFFFFFE0265FC9EFCA86085AF04" author="Chen, J. & Wang, G. - Y. & Shi, Y. - P." box="[826,987,845,864]" pageId="5" pageNumber="6" pagination="341 - 354" refId="ref10779" refString="Chen, J., Wang, G. - Y., Shi, Y. - P., 2009. Method development and validation for simultaneous HPLC analysis of six active components of the Chinese medicine Qin- Bao-Hong antitussive tablet. Acta Chromatogr. 21 (2), 341 - 354. https: // doi. org / 10.1556 / AChrom. 21.2009.2.12." type="journal article" year="2009">Chen et al., 2009</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |