210 lines
25 KiB
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210 lines
25 KiB
XML
<document id="25742725E09E646BA21CD6CB74A46A05" 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="03CE8794BA57A743AD244D53FA843F68" 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 tasmanica W. M. Curtis" 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="E404C78EBCF92C6FA13C5E916A418B7D">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="757A729F2A785B5DC14293D712CD261A">Deans, Bianca J.</mods:namePart>
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<mods:affiliation id="8A3B35C83359622BB8843E83AA89F634">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:namePart id="CDEB6426C2245F2DDA41F60A3F4C559C">Tedone, Laura</mods:namePart>
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<mods:affiliation id="CA3B89912BAC7F76A22D9DC21E1A07E8">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="B7B0E7A6976FE586092341FDA0DEEFC0">Bissember, Alex C.</mods:namePart>
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<mods:affiliation id="3514B1B31F38A9658ABD29B9CD2D2B5E">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:nameIdentifier id="E000DB374ADA3B81A0416BBB81758073" type="email">alex.bissember@utas.edu.au</mods:nameIdentifier>
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<mods:namePart id="07C045EA12200799338CCD5028392583">Smith, Jason A.</mods:namePart>
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<mods:affiliation id="9134101063B5105C6C08314646AF8E63">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:title id="5C78E550CE0A16B44D6936F1F5B8F0A4">Phytochemistry</mods:title>
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<mods:date id="5EABBCDD48E0CBA8A00FE3D36BF481B1">2018</mods:date>
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<mods:number id="4FAE279E5B61E64F4C90AB5D3FAA03AD">2018-09-30</mods:number>
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<mods:number id="34B068B44A831AE36952BB5EA441BA8C">153</mods:number>
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<mods:start id="30DF02DCBB6787A6E05A29F45F0CF39E">74</mods:start>
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<mods:url id="3B8545DC16B29AF9933462FF74B5E741">http://dx.doi.org/10.1016/j.phytochem.2018.05.019</mods:url>
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<mods:identifier id="0A0E9C74EE7A33872B47CF150EF595B6" type="DOI">10.1016/j.phytochem.2018.05.019</mods:identifier>
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<mods:identifier id="8B91B2D377A2D7EB16407BD41605CD1A" type="ISSN">1873-3700</mods:identifier>
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<treatment id="03CE8794BA57A743AD244D53FA843F68" LSID="urn:lsid:plazi:treatment:03CE8794BA57A743AD244D53FA843F68" httpUri="http://treatment.plazi.org/id/03CE8794BA57A743AD244D53FA843F68" lastPageNumber="75" pageId="1" pageNumber="75">
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<subSubSection id="C37D6509BA57A743AD244D53FE843E91" box="[100,316,885,904]" pageId="1" pageNumber="75" type="nomenclature">
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<paragraph id="8BD83682BA57A743AD244D53FE843E91" blockId="1.[100,316,885,904]" box="[100,316,885,904]" pageId="1" pageNumber="75">
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<heading id="D09081EEBA57A743AD244D53FE843E91" bold="true" box="[100,316,885,904]" fontSize="36" level="1" pageId="1" pageNumber="75" reason="1">
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<emphasis id="B913EA90BA57A743AD244D53FE843E91" bold="true" box="[100,316,885,904]" italics="true" pageId="1" pageNumber="75">
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2.1.
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<taxonomicName id="4C674D01BA57A743ADD24D53FE843E91" ID-CoL="3VWYS" authority="W. M. Curtis" authorityName="W. M. Curtis" box="[146,316,885,904]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tasmanica">Lomatia tasmanica</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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<subSubSection id="C37D6509BA57A743ADC54D8AFA843F68" pageId="1" pageNumber="75" type="description">
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<paragraph id="8BD83682BA57A743ADC54D8AFD943833" blockId="1.[100,771,940,1768]" pageId="1" pageNumber="75">
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Maceration of
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<taxonomicName id="4C674D01BA57A743AC554D8AFE323EA6" box="[277,394,940,959]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tasmanica">
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<emphasis id="B913EA90BA57A743AC554D8AFE323EA6" bold="true" box="[277,394,940,959]" italics="true" pageId="1" pageNumber="75">L. tasmanica</emphasis>
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</taxonomicName>
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provided the naphthoquinone juglone (
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<emphasis id="B913EA90BA57A743AD2C4DEEFFC03EC2" bold="true" box="[108,120,968,987]" pageId="1" pageNumber="75">1</emphasis>
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) (0.34% w/w) (
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<figureCitation id="135C2A07BA57A743AC564DEEFEF53EC2" box="[278,333,968,987]" captionStart="Fig" captionStartId="1.[197,227,1965,1982]" captionTargetBox="[188,682,1798,1943]" captionTargetId="graphics-1163@1.[318,520,1812,1916]" captionTargetPageId="1" captionText="Fig. 1. Juglone (1), lomatiol (2), and naphtharazin (3)." figureDoi="http://doi.org/10.5281/zenodo.10483777" httpUri="https://zenodo.org/record/10483777/files/figure.png" pageId="1" pageNumber="75">Fig. 1</figureCitation>
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). The
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<superScript id="7C129BCABA57A743ACCD4DE2FE2E3EC8" attach="right" box="[397,406,964,977]" fontSize="5" pageId="1" pageNumber="75">1</superScript>
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H and
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<superScript id="7C129BCABA57A743AC974DE2FE513EC8" attach="right" box="[471,489,964,977]" fontSize="5" pageId="1" pageNumber="75">13</superScript>
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C NMR spectroscopic and MS data (see: Supporting Information) were consistent with equivalent data previously reported in the literature (
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<bibRefCitation id="EFF64B73BA57A743AC874A26FD62390A" author="de Freitas Araujo, D. M. & Vieira, G. A. B. & de Mattos, M. C. & Lemos, T. L. G. & de Oliveira, M. & Melo, V. M. M. & de Gonzalo, G. & Gotor-Fernandez, V. & Gotor, V." box="[455,730,1024,1043]" pageId="1" pageNumber="75" pagination="279 - 283" refId="ref7081" refString="de Freitas Araujo, D. M., Vieira, G. A. B., de Mattos, M. C., Lemos, T. L. G., de Oliveira, M., da, C. F., Melo, V. M. M., de Gonzalo, G., Gotor-Fernandez, V., Gotor, V., 2009. Chemoenzymatic preparation of a biologically active naphthoquinone from Tabebuia impetiginosa using lipases or alcohol dehydrogenases. J. Mol. Catal. B Enzym. 63, 279 - 283." type="journal article" year="2009">de Freitas Araujo et al., 2009</bibRefCitation>
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). In addition, this extract also contained a chromatographically inseparable mixture of
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<emphasis id="B913EA90BA57A743AD8C4A1EFF6F3952" bold="true" box="[204,215,1080,1099]" italics="true" pageId="1" pageNumber="75">n</emphasis>
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-alkanes (0.30% w/w).
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<superScript id="7C129BCABA57A743ACF34A15FE043959" attach="right" box="[435,444,1075,1088]" fontSize="5" pageId="1" pageNumber="75">1</superScript>
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H NMR and GC-MS analysis of this mixture was consistent with nonacosane (C
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<subScript id="17E334C7BA57A743AF4B4A7AFDA53970" attach="both" box="[523,541,1116,1129]" fontSize="5" pageId="1" pageNumber="75">29</subScript>
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H
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<subScript id="17E334C7BA57A743AF6D4A7AFD873970" attach="left" box="[557,575,1116,1129]" fontSize="5" pageId="1" pageNumber="75">60</subScript>
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) as the major component and heptacosane (C
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<subScript id="17E334C7BA57A743AC3E4A5EFE28399C" attach="both" box="[382,400,1144,1157]" fontSize="5" pageId="1" pageNumber="75">27</subScript>
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H
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<subScript id="17E334C7BA57A743ACE04A5EFE0A399C" attach="left" box="[416,434,1144,1157]" fontSize="5" pageId="1" pageNumber="75">56</subScript>
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) as the minor component (see: Supporting Information) (
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<bibRefCitation id="EFF64B73BA57A743AC1E4AAAFDF73986" author="Lytovchenko, A. & Beleggia, R. & Schauer, N. & Isaacson, T. & Leuendorf, J. E. & Hellmann, H. & Rose, J. K. C. & Fernie, A. R." box="[350,591,1164,1183]" pageId="1" pageNumber="75" refId="ref7739" refString="Lytovchenko, A., Beleggia, R., Schauer, N., Isaacson, T., Leuendorf, J. E., Hellmann, H., Rose, J. K. C., Fernie, A. R., 2009. Application of GC-MS for the detection of lipophilic compounds in diverse plant tissues. Plant Meth. 5. http: // dx. doi. org / 10.1186 / 1746 - 4811 - 5 - 4." type="book" year="2009">Lytovchenko et al., 2009</bibRefCitation>
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). Neither of these long-chain alkanes has previously been reported from any
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<taxonomicName id="4C674D01BA57A743AFF94A8EFF1539CF" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="undetermined">
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<emphasis id="B913EA90BA57A743AFF94A8EFCB939A2" bold="true" box="[697,769,1192,1211]" italics="true" pageId="1" pageNumber="75">Lomatia</emphasis>
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species.
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</taxonomicName>
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This suggests that these hydrocarbons represent major components of the epicuticular wax coating of the characteristically robust
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<taxonomicName id="4C674D01BA57A743AD244ADDFF723817" box="[100,202,1275,1294]" class="Magnoliopsida" family="Proteaceae" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="family">Proteaceae</taxonomicName>
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leaves. The PHWE extract provided glucose as a mixture of α- and β- anomers (see: Supporting Information).
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</paragraph>
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<paragraph id="8BD83682BA57A743ADC54B15FB1B3DD7" blockId="1.[100,771,940,1768]" lastBlockId="1.[818,1487,159,625]" pageId="1" pageNumber="75">
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Juglone (
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<emphasis id="B913EA90BA57A743AD9F4B15FF53385F" bold="true" box="[223,235,1331,1350]" pageId="1" pageNumber="75">1</emphasis>
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), as well as other naphthoquinone pigments, have previously been isolated from numerous
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<taxonomicName id="4C674D01BA57A743AC9C4B69FDCB387B" box="[476,627,1359,1378]" pageId="1" pageNumber="75">
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<emphasis id="B913EA90BA57A743AC9C4B69FD9C387B" bold="true" box="[476,548,1359,1378]" italics="true" pageId="1" pageNumber="75">Lomatia</emphasis>
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species
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</taxonomicName>
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, including the Tasmanian endemic
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<taxonomicName id="4C674D01BA57A743AC654B4DFD2D3867" authority="(Moir and Thompson, 1973)" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" box="[293,661,1387,1406]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tinctoria">
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<emphasis id="B913EA90BA57A743AC654B4DFE3E3867" bold="true" box="[293,390,1387,1406]" italics="true" pageId="1" pageNumber="75">L. tinctoria</emphasis>
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(
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<bibRefCitation id="EFF64B73BA57A743ACD44B4DFD353867" author="Moir, M. & Thompson, R. H." box="[404,653,1387,1406]" 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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. A range of related naphthoquinones have been isolated from other
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<taxonomicName id="4C674D01BA57A743AF2C4BA1FD463883" box="[620,766,1415,1434]" pageId="1" pageNumber="75">
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<emphasis id="B913EA90BA57A743AF2C4BA1FD0C3883" bold="true" box="[620,692,1415,1434]" italics="true" pageId="1" pageNumber="75">Lomatia</emphasis>
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species
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</taxonomicName>
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, including: lomatiol (
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<emphasis id="B913EA90BA57A743AC674B85FE8B38AF" bold="true" box="[295,307,1443,1462]" pageId="1" pageNumber="75">2</emphasis>
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||
) (
|
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<figureCitation id="135C2A07BA57A743AC0A4B85FE3938AF" box="[330,385,1443,1462]" captionStart="Fig" captionStartId="1.[197,227,1965,1982]" captionTargetBox="[188,682,1798,1943]" captionTargetId="graphics-1163@1.[318,520,1812,1916]" captionTargetPageId="1" captionText="Fig. 1. Juglone (1), lomatiol (2), and naphtharazin (3)." figureDoi="http://doi.org/10.5281/zenodo.10483777" httpUri="https://zenodo.org/record/10483777/files/figure.png" pageId="1" pageNumber="75">Fig. 1</figureCitation>
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), which has been identified in the seeds of both endemic Tasmanian
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<taxonomicName id="4C674D01BA57A743ACC24B99FE5F38CB" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" box="[386,487,1471,1490]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tinctoria">
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<emphasis id="B913EA90BA57A743ACC24B99FE5F38CB" bold="true" box="[386,487,1471,1490]" italics="true" pageId="1" pageNumber="75">L. tinctoria</emphasis>
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</taxonomicName>
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and
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<taxonomicName id="4C674D01BA57A743AF5F4B99FF2438F4" authority="(Hooker, 1936)" baseAuthorityName="Hooker" baseAuthorityYear="1936" 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="B913EA90BA57A743AF5F4B99FD1C38CB" bold="true" box="[543,676,1471,1490]" italics="true" pageId="1" pageNumber="75">L. polymorpha</emphasis>
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(
|
||
<bibRefCitation id="EFF64B73BA57A743AFF74B99FF2C38F4" author="Hooker, S. C." pageId="1" pageNumber="75" pagination="1181 - 1190" refId="ref7187" refString="Hooker, S. C., 1936. Lomatiol. Part 11. Its occurrence, constitution, relation to and conversion into lapachol. Also a synthesis of lapachol. J. Am. Chem. Soc. 58, 1181 - 1190." type="journal article" year="1936">Hooker, 1936</bibRefCitation>
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)
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</taxonomicName>
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, and naphtharazin (
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<emphasis id="B913EA90BA57A743AC194BFCFEDD38F4" bold="true" box="[345,357,1498,1517]" pageId="1" pageNumber="75">3</emphasis>
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) from various species (
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||
<bibRefCitation id="EFF64B73BA57A743AF7F4BFCFF2C3B10" 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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||
). Perhaps the presence of a single naphthoquinone in
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<taxonomicName id="4C674D01BA57A743AFD14BD0FCBA3B10" box="[657,770,1526,1545]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tasmanica">
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<emphasis id="B913EA90BA57A743AFD14BD0FCBA3B10" bold="true" box="[657,770,1526,1545]" italics="true" pageId="1" pageNumber="75">L. tasmanica</emphasis>
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</taxonomicName>
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reflects the primitive and ancient position of
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<taxonomicName id="4C674D01BA57A743AF614834FD2D3B3C" box="[545,661,1554,1573]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tasmanica">
|
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<emphasis id="B913EA90BA57A743AF614834FD2D3B3C" bold="true" box="[545,661,1554,1573]" italics="true" pageId="1" pageNumber="75">L. tasmanica</emphasis>
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</taxonomicName>
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within the lineage, as an evolved trend of increased pigment composition complexity is observed within later descendants within the genus (
|
||
<bibRefCitation id="EFF64B73BA57A743AFEC486CFEBC3B60" 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>
|
||
). While it is possible that juglone
|
||
<emphasis id="B913EA90BA57A743AF104840FDE43B60" bold="true" box="[592,604,1638,1657]" pageId="1" pageNumber="75">1</emphasis>
|
||
can be produced during extraction from its glycoside 1,4,8-trihydroxynaphthalene-1-Oβ-
|
||
<subScript id="17E334C7BA57A743AD374884FF303BA8" attach="none" box="[119,136,1694,1713]" fontSize="6" pageId="1" pageNumber="75">D-</subScript>
|
||
glucose
|
||
<emphasis id="B913EA90BA57A743AD9748B8FF5B3BA8" bold="true" box="[215,227,1694,1713]" pageId="1" pageNumber="75">6</emphasis>
|
||
(
|
||
<bibRefCitation id="EFF64B73BA57A743ADB448B8FE093BA8" author="Duroux, L. & Delmotte, F. M. & Lancelin, J. - M. & Keravis, G. & Jay-Allemand, C." box="[244,433,1694,1713]" pageId="1" pageNumber="75" pagination="275 - 283" refId="ref6901" refString="Duroux, L., Delmotte, F. M., Lancelin, J. - M., Keravis, G., Jay-Allemand, C., 1998. Insight into naphthoquinone metabolism: a-glucosidase-catalysed hydrolysis of hydrojuglone a-D-glucopyranoside. Biochem. J. 333, 275 - 283." type="journal article" year="1998">Duroux et al., 1998</bibRefCitation>
|
||
), extraction of fresh leaves from a representative specimen of
|
||
<taxonomicName id="4C674D01BA57A743AC28489FFE623BD5" box="[360,474,1721,1740]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tasmanica">
|
||
<emphasis id="B913EA90BA57A743AC28489FFE623BD5" bold="true" box="[360,474,1721,1740]" italics="true" pageId="1" pageNumber="75">L. tasmanica</emphasis>
|
||
</taxonomicName>
|
||
with diethyl ether for 5 min in an oxygen-free atmosphere did not detect the presence of glycoside
|
||
<emphasis id="B913EA90BA57A743AFAF48F3FD433BF1" bold="true" box="[751,763,1749,1768]" pageId="1" pageNumber="75">6</emphasis>
|
||
. This indicates that naphthoquinone
|
||
<emphasis id="B913EA90BA57A743A9CC4EB9FB203DAB" bold="true" box="[1164,1176,159,178]" pageId="1" pageNumber="75">1</emphasis>
|
||
is not an artefact of extraction/ isolation and is a true natural product.
|
||
</paragraph>
|
||
<paragraph id="8BD83682BA57A743AE134EF1FA843F68" blockId="1.[818,1487,159,625]" pageId="1" pageNumber="75">
|
||
Juglone (
|
||
<emphasis id="B913EA90BA57A743AEF64EF1FC7A3DF3" bold="true" box="[950,962,215,234]" pageId="1" pageNumber="75">1</emphasis>
|
||
), like many naphthoquinones, exhibits antifungal (
|
||
<bibRefCitation id="EFF64B73BA57A743AE7A4ED5FC403C1F" author="Meazza, G. & Dayan, F. E. & Wedge, D. E." box="[826,1016,243,262]" pageId="1" pageNumber="75" pagination="3824 - 3828" refId="ref7827" refString="Meazza, G., Dayan, F. E., Wedge, D. E., 2003. Activity of quinones on Colletotrichum species. J. Agric. Food Chem. 51, 3824 - 3828." type="journal article" year="2003">Meazza et al., 2003</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="EFF64B73BA57A743A9474ED5FB533C1F" author="Wianowska, D. & Garbaczewska, S. & Cieniecka-Roslonkiewicz, A. & Dawidowicz, A. L. & Jankowska, A." box="[1031,1259,243,262]" pageId="1" pageNumber="75" pagination="263 - 267" refId="ref8247" refString="Wianowska, D., Garbaczewska, S., Cieniecka-Roslonkiewicz, A., Dawidowicz, A. L., Jankowska, A., 2016. Comparison of antifungal activity of extracts from different Juglans regia cultivars and juglone. Microb. Pathog. 100, 263 - 267." type="journal article" year="2016">Wianowska et al., 2016</bibRefCitation>
|
||
), antimycobacterial activity (
|
||
<bibRefCitation id="EFF64B73BA57A743AE324F29FBA93C3B" author="Tran, T. & Saheba, E. & Arcerio, A. V. & Chavez, V. & Li, Q. & Martinez, L. E. & Primm, T. P." box="[882,1041,271,290]" pageId="1" pageNumber="75" pagination="4809 - 4813" refId="ref8187" refString="Tran, T., Saheba, E., Arcerio, A. V., Chavez, V., Li, Q., Martinez, L. E., Primm, T. P., 2004. Quinones as antimycobacterial agents. Bioorg. Med. Chem. 12, 4809 - 4813." type="journal article" year="2004">Tran et al., 2004</bibRefCitation>
|
||
), and is a reported antifeedant towards insects (
|
||
<bibRefCitation id="EFF64B73BA57A743AE7A4F0DFC4C3C27" author="Akhtar, Y. & Isman, M. B. & Niehaus, L. A. & Lee, C. - H. & Lee, H. - S." box="[826,1012,299,318]" pageId="1" pageNumber="75" pagination="8 - 14" refId="ref6167" refString="Akhtar, Y., Isman, M. B., Niehaus, L. A., Lee, C. - H., Lee, H. - S., 2012. Antifeedant and toxic effects of naturally occurring and synthetic quinones to the cabbage looper, Trichoplusia ni. Crop Protect. 31, 8 - 14." type="journal article" year="2012">Akhtar et al., 2012</bibRefCitation>
|
||
). In addition, juglone is reported to affect plant development, including the promotion of cell division, cell elongation and root formation (
|
||
<bibRefCitation id="EFF64B73BA57A743AEBC4F45FABD3C6F" author="Compton, M. E. & Preece, J. E." box="[1020,1285,355,374]" pageId="1" pageNumber="75" pagination="160 - 163" refId="ref6514" refString="Compton, M. E., Preece, J. E., 1988. Effects of phenolic compounds on tobacco callus and blackberry shoot cultures. J. Am. Soc. Hort. Sci. 113, 160 - 163." type="journal article" year="1988">Compton and Preece, 1988</bibRefCitation>
|
||
). Naphthoquinone
|
||
<emphasis id="B913EA90BA57A743A8834F45FA773C6F" bold="true" box="[1475,1487,355,374]" pageId="1" pageNumber="75">1</emphasis>
|
||
also has reported allelopathic activity and toxicity towards plants, with its bioactivity as a phytotoxin first reported in 1928 (
|
||
<bibRefCitation id="EFF64B73BA57A743A8794FBCFA133CB4" author="Davis, E. F." box="[1337,1451,410,429]" pageId="1" pageNumber="75" pagination="620 - 621" refId="ref6587" refString="Davis, E. F., 1928. The toxic principle of Juglans nigra as identified with synthetic juglone, and its toxic effects on tomato and alfalfa plants. Am. J. Bot. 15, 620 - 621." type="journal article" year="1928">Davis, 1928</bibRefCitation>
|
||
). It has been reported that plants may release juglone to stunt the growth of competing plants found in close proximity; and may serve to provide a chemical ecological advantage (eg.
|
||
<bibRefCitation id="EFF64B73BA57A743A9CC4FC8FA843F18" author="Topal, S. & Kocacalistan, I. & Arslan, O. & Tel, A. Z." box="[1164,1340,494,513]" pageId="1" pageNumber="75" pagination="259 - 269" refId="ref8148" refString="Topal, S., Kocacalistan, I., Arslan, O., Tel, A. Z., 2006. Herbicidal effects of juglone as an allelochemical. Phyton 46, 259 - 269." type="journal article" year="2006">Topal et al., 2006</bibRefCitation>
|
||
). The reported bioactivity of juglone may provide some insight into the chemical ecological defenses that
|
||
<taxonomicName id="4C674D01BA57A743A9664C00FB243F20" box="[1062,1180,550,569]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tasmanica">
|
||
<emphasis id="B913EA90BA57A743A9664C00FB243F20" bold="true" box="[1062,1180,550,569]" italics="true" pageId="1" pageNumber="75">L. tasmanica</emphasis>
|
||
</taxonomicName>
|
||
may have developed (perhaps against fungus), as well as interactions and environmental pressures that
|
||
<taxonomicName id="4C674D01BA57A743AE1E4C78FC683F68" box="[862,976,606,625]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tasmanica">
|
||
<emphasis id="B913EA90BA57A743AE1E4C78FC683F68" bold="true" box="[862,976,606,625]" italics="true" pageId="1" pageNumber="75">L. tasmanica</emphasis>
|
||
</taxonomicName>
|
||
may have been exposed to over time.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |