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<document id="691603F85408E645E7CA1A955FDF559E" 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. &amp; Smith, Jason A." docDate="2018" docId="03CE8794BA57A740AE724BA8FE473986" 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 tinctoria" docType="treatment" docVersion="1" lastPageNumber="76" 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="BF141A7D14AD01882009FCB1061FD340">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="471F5E83801D8F621CB089DE3EAFDF2A">Deans, Bianca J.</mods:namePart>
<mods:affiliation id="FB3B03F2612D2A6CC703E21B60F9D8B0">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:namePart id="E6C3B46C0C5166AC0630BC90C87A3771">Tedone, Laura</mods:namePart>
<mods:affiliation id="DFFF0E2A21514116FB86DD4275A37E8B">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia &amp; Australian Centre for Research on Separation Science (ACROSS), University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:namePart id="7F1A72ED026CB5F08E9CFC1846898A9E">Bissember, Alex C.</mods:namePart>
<mods:affiliation id="0EA37DC6B76FA062969FB6A52DD7B9A8">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:namePart id="8DF14ED096555B36F8A51D3659AD008A">Smith, Jason A.</mods:namePart>
<mods:affiliation id="8F625DA3EC4FC8F87E7E371E631509D3">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:title id="5DF2161CBC55FE7DF0C02E2522AC8FC9">Phytochemistry</mods:title>
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<mods:date id="D0CB2D0A4E834AE0B5417A6C2B42476A">2018</mods:date>
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<treatment id="03CE8794BA57A740AE724BA8FE473986" LSID="urn:lsid:plazi:treatment:03CE8794BA57A740AE724BA8FE473986" httpUri="http://treatment.plazi.org/id/03CE8794BA57A740AE724BA8FE473986" lastPageId="2" lastPageNumber="76" pageId="1" pageNumber="75">
<subSubSection id="C37D6509BA57A743AE724BA8FC4138B8" box="[818,1017,1422,1441]" pageId="1" pageNumber="75" type="nomenclature">
<paragraph id="8BD83682BA57A743AE724BA8FC4138B8" blockId="1.[818,1017,1422,1441]" box="[818,1017,1422,1441]" pageId="1" pageNumber="75">
<heading id="D09081EEBA57A743AE724BA8FC4138B8" bold="true" box="[818,1017,1422,1441]" fontSize="36" level="1" pageId="1" pageNumber="75" reason="1">
<emphasis id="B913EA90BA57A743AE724BA8FC4138B8" bold="true" box="[818,1017,1422,1441]" italics="true" pageId="1" pageNumber="75">
2.3.
<taxonomicName id="4C674D01BA57A743AE204BA8FC4138B8" ID-CoL="3VWYW" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" box="[864,1017,1422,1441]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tinctoria">Lomatia tinctoria</taxonomicName>
</emphasis>
</heading>
</paragraph>
</subSubSection>
<subSubSection id="C37D6509BA57A740AE134BE0FF6F3F94" lastPageId="2" lastPageNumber="76" pageId="1" pageNumber="75" type="description">
<paragraph id="8BD83682BA57A740AE134BE0FDDC3C8B" blockId="1.[818,1487,1478,1580]" lastBlockId="2.[100,770,159,653]" lastPageId="2" lastPageNumber="76" pageId="1" pageNumber="75">
Maceration of
<taxonomicName id="4C674D01BA57A743AEA24BE0FBFE38C0" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" box="[994,1094,1478,1497]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="1" pageNumber="75" phylum="Tracheophyta" rank="species" species="tinctoria">
<emphasis id="B913EA90BA57A743AEA24BE0FBFE38C0" bold="true" box="[994,1094,1478,1497]" italics="true" pageId="1" pageNumber="75">L. tinctoria</emphasis>
</taxonomicName>
provided juglone (
<emphasis id="B913EA90BA57A743A8444BE0FAA838C0" bold="true" box="[1284,1296,1478,1497]" pageId="1" pageNumber="75">1</emphasis>
) (0.58% w/w) and nonacosane (C
<subScript id="17E334C7BA57A743AEFC4BCCFC7638EE" attach="both" box="[956,974,1514,1527]" fontSize="5" pageId="1" pageNumber="75">29</subScript>
H
<subScript id="17E334C7BA57A743AE9E4BCCFC4838EE" attach="left" box="[990,1008,1514,1527]" fontSize="5" pageId="1" pageNumber="75">60</subScript>
) (0.13% w/w), as supported by
<superScript id="7C129BCABA57A743A86A4BFBFA8B38F3" attach="right" box="[1322,1331,1501,1514]" fontSize="5" pageId="1" pageNumber="75">1</superScript>
H NMR and GC-MS data (see: Supporting Information) (
<bibRefCitation id="EFF64B73BA57A743A9ED4BDBFA203B09" author="Lytovchenko, A. &amp; Beleggia, R. &amp; Schauer, N. &amp; Isaacson, T. &amp; Leuendorf, J. E. &amp; Hellmann, H. &amp; Rose, J. K. C. &amp; Fernie, A. R." box="[1197,1432,1533,1552]" 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>
). GC-MS analysis of the crude diethyl ether extract also indicated the presence of heptacosane in small quantities (see: Supporting Information). The PHWE extract provided glucose as a mixture of α- and β- anomers. Juglone has been previously isolated from the seeds, wood and bark of
<taxonomicName id="4C674D01BA54A740AD944ED5FE8C3C1F" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" box="[212,308,243,262]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tinctoria">
<emphasis id="B913EA90BA54A740AD944ED5FE8C3C1F" bold="true" box="[212,308,243,262]" italics="true" pageId="2" pageNumber="76">L. tinctoria</emphasis>
</taxonomicName>
, however, the leaves were not investigated (
<bibRefCitation id="EFF64B73BA54A740AF954ED5FE973C3B" author="Moir, M. &amp; Thompson, R. H." pageId="2" pageNumber="76" 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>
). Notably, juglone (
<emphasis id="B913EA90BA54A740ACB34F29FE473C3B" bold="true" box="[499,511,271,290]" pageId="2" pageNumber="76">1</emphasis>
) was the
<emphasis id="B913EA90BA54A740AF214F29FD3F3C3B" bold="true" box="[609,647,271,290]" italics="true" pageId="2" pageNumber="76">only</emphasis>
naphthoquinone pigment isolated from both
<taxonomicName id="4C674D01BA54A740ACED4F0DFDA93C27" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" box="[429,529,299,318]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tinctoria">
<emphasis id="B913EA90BA54A740ACED4F0DFDA93C27" bold="true" box="[429,529,299,318]" italics="true" pageId="2" pageNumber="76">L. tinctoria</emphasis>
</taxonomicName>
and
<taxonomicName id="4C674D01BA54A740AF064F0DFD703C27" baseAuthorityName="Hooker" baseAuthorityYear="1936" box="[582,712,299,318]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="polymorpha">
<emphasis id="B913EA90BA54A740AF064F0DFD703C27" bold="true" box="[582,712,299,318]" italics="true" pageId="2" pageNumber="76">L. polymorpha</emphasis>
</taxonomicName>
(vide supra). Moreover, lomatiol (
<emphasis id="B913EA90BA54A740AC394F61FE3D3C43" bold="true" box="[377,389,327,346]" pageId="2" pageNumber="76">2</emphasis>
) was not isolated from either of these plants, despite previously being reported in the seeds of both species albeit only using qualitative methods (
<bibRefCitation id="EFF64B73BA54A740AC954F59FDEF3C8B" author="Hooker, S. C." box="[469,599,383,402]" pageId="2" pageNumber="76" 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>
).
</paragraph>
<caption id="DF18660ABA57A743AE72495CFCC33AA7" ID-DOI="http://doi.org/10.5281/zenodo.10483775" ID-Zenodo-Dep="10483775" httpUri="https://zenodo.org/record/10483775/files/figure.png" pageId="1" pageNumber="75" startId="1.[818,848,1914,1931]" targetBox="[850,1454,1610,1892]" targetPageId="1" targetType="figure">
<paragraph id="8BD83682BA57A743AE72495CFCC33AA7" blockId="1.[818,1487,1914,1982]" pageId="1" pageNumber="75">
<emphasis id="B913EA90BA57A743AE72495CFCD53A92" bold="true" box="[818,877,1914,1931]" pageId="1" pageNumber="75">Fig. 2.</emphasis>
Dihydroquercetin 3-
<emphasis id="B913EA90BA57A743A960495CFB963A92" bold="true" box="[1056,1070,1914,1931]" italics="true" pageId="1" pageNumber="75">O</emphasis>
-β- D-xyloside (
<emphasis id="B913EA90BA57A743A9ED495CFB003A92" bold="true" box="[1197,1208,1914,1931]" pageId="1" pageNumber="75">4</emphasis>
), quercetin 3-
<emphasis id="B913EA90BA57A743A875495CFAFB3A92" bold="true" box="[1333,1347,1914,1931]" italics="true" pageId="1" pageNumber="75">O</emphasis>
-β- D- glucose (
<emphasis id="B913EA90BA57A743A8F7495CFA7A3A92" bold="true" box="[1463,1474,1914,1931]" pageId="1" pageNumber="75">5</emphasis>
), 1,4,8-trihydroxynaphthalene-1-
<emphasis id="B913EA90BA57A743A97C49B2FBF23ABC" bold="true" box="[1084,1098,1940,1957]" italics="true" pageId="1" pageNumber="75">O</emphasis>
-β- D- glucose (
<emphasis id="B913EA90BA57A743A98549B2FB683ABC" bold="true" box="[1221,1232,1940,1957]" pageId="1" pageNumber="75">6</emphasis>
), and 4-
<emphasis id="B913EA90BA57A743A85C49B2FA803ABC" bold="true" box="[1308,1336,1940,1957]" italics="true" pageId="1" pageNumber="75">O -p</emphasis>
-coumaroyl-D- glucose (
<emphasis id="B913EA90BA57A743AE23498BFCD63AA7" bold="true" box="[867,878,1965,1982]" pageId="1" pageNumber="75">7</emphasis>
).
</paragraph>
</caption>
<caption id="DF18660ABA57A743AD85498BFD193AA7" ID-DOI="http://doi.org/10.5281/zenodo.10483777" ID-Zenodo-Dep="10483777" box="[197,673,1965,1982]" httpUri="https://zenodo.org/record/10483777/files/figure.png" pageId="1" pageNumber="75" startId="1.[197,227,1965,1982]" targetBox="[188,682,1798,1943]" targetPageId="1" targetType="figure">
<paragraph id="8BD83682BA57A743AD85498BFD193AA7" blockId="1.[197,673,1965,1982]" box="[197,673,1965,1982]" pageId="1" pageNumber="75">
<emphasis id="B913EA90BA57A743AD85498BFF463AA7" bold="true" box="[197,254,1965,1982]" pageId="1" pageNumber="75">Fig. 1.</emphasis>
Juglone (
<emphasis id="B913EA90BA57A743AC15498BFED83AA7" bold="true" box="[341,352,1965,1982]" pageId="1" pageNumber="75">1</emphasis>
), lomatiol (
<emphasis id="B913EA90BA57A743AC87498BFE6A3AA7" bold="true" box="[455,466,1965,1982]" pageId="1" pageNumber="75">2</emphasis>
), and naphtharazin (
<emphasis id="B913EA90BA57A743AFC9498BFD2C3AA7" bold="true" box="[649,660,1965,1982]" pageId="1" pageNumber="75">3</emphasis>
).
</paragraph>
</caption>
<paragraph id="8BD83682BA54A740ADC54FBCFF6F3F94" blockId="2.[100,770,159,653]" pageId="2" pageNumber="76">
These data indicate that, although all three species contained heptacosane and nonacosane, there are some differences in the chemical profiles of the respective leaf waxes associated with different species of
<taxonomicName id="4C674D01BA54A740AD244FC8FF143F18" box="[100,172,494,513]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="genus">
<emphasis id="B913EA90BA54A740AD244FC8FF143F18" bold="true" box="[100,172,494,513]" italics="true" pageId="2" pageNumber="76">Lomatia</emphasis>
</taxonomicName>
. Also, these non-polar molecules possibly reflect the epicuticular morphology of each species.
<taxonomicName id="4C674D01BA54A740ACF54C2CFD903F04" box="[437,552,522,541]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tasmanica">
<emphasis id="B913EA90BA54A740ACF54C2CFD903F04" bold="true" box="[437,552,522,541]" italics="true" pageId="2" pageNumber="76">L. tasmanica</emphasis>
</taxonomicName>
, which ostensibly features the thickest leaf epicuticular layer and provided the highest yields of non-polar components while
<taxonomicName id="4C674D01BA54A740ACEA4C64FD883F4C" baseAuthorityName="Hooker" baseAuthorityYear="1936" box="[426,560,578,597]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="polymorpha">
<emphasis id="B913EA90BA54A740ACEA4C64FD883F4C" bold="true" box="[426,560,578,597]" italics="true" pageId="2" pageNumber="76">L. polymorpha</emphasis>
</taxonomicName>
, which contains the thinnest surface coating, provided the lowest yields of these non-polar compounds.
</paragraph>
</subSubSection>
<subSubSection id="C37D6509BA54A740AD244C97FE473986" pageId="2" pageNumber="76" type="discussion">
<paragraph id="8BD83682BA54A740AD244C97FCB93FDD" blockId="2.[100,769,689,708]" box="[100,769,689,708]" pageId="2" pageNumber="76">
<emphasis id="B913EA90BA54A740AD244C97FCB93FDD" bold="true" box="[100,769,689,708]" italics="true" pageId="2" pageNumber="76">
2.4. Intraspecific variation of
<taxonomicName id="4C674D01BA54A740AC334C97FE5D3FDD" ID-CoL="3VWYS" box="[371,485,689,708]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tasmanica">L. tasmanica</taxonomicName>
,
<taxonomicName id="4C674D01BA54A740ACB14C97FDEA3FDD" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" box="[497,594,689,708]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tinctoria">L. tinctoria</taxonomicName>
and
<taxonomicName id="4C674D01BA54A740AFC14C97FCB93FDD" baseAuthorityName="Hooker" baseAuthorityYear="1936" box="[641,769,689,708]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="polymorpha">L. polymorpha</taxonomicName>
</emphasis>
</paragraph>
<paragraph id="8BD83682BA54A740ADC54CCFFE473986" blockId="2.[100,770,745,1183]" pageId="2" pageNumber="76">
Intraspecific variation between all three species was also investigated.
<specimenCount id="9D61FD0BBA54A740AD904D23FED53E01" box="[208,365,773,792]" count="3" pageId="2" pageNumber="76" type="generic">Three specimens</specimenCount>
from each species
<taxonomicName id="4C674D01BA54A740AF614D23FD2B3E01" box="[545,659,773,792]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tasmanica">
<emphasis id="B913EA90BA54A740AF614D23FD2B3E01" bold="true" box="[545,659,773,792]" italics="true" pageId="2" pageNumber="76">L. tasmanica</emphasis>
</taxonomicName>
(specimens AC),
<taxonomicName id="4C674D01BA54A740ADE04D07FEBB3E2D" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" box="[160,259,801,820]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tinctoria">
<emphasis id="B913EA90BA54A740ADE04D07FEBB3E2D" bold="true" box="[160,259,801,820]" italics="true" pageId="2" pageNumber="76">L. tinctoria</emphasis>
</taxonomicName>
(specimens DF), and
<taxonomicName id="4C674D01BA54A740ACA04D07FDD93E2D" baseAuthorityName="Hooker" baseAuthorityYear="1936" box="[480,609,801,820]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="polymorpha">
<emphasis id="B913EA90BA54A740ACA04D07FDD93E2D" bold="true" box="[480,609,801,820]" italics="true" pageId="2" pageNumber="76">L. polymorpha</emphasis>
</taxonomicName>
(specimens GI) were collected from their respective populations. Each specimen was subject to the aforementioned two complementary extraction procedures. Analysis of the three individual specimens from the three respective species indicated consistency in phytochemical profiles within each of the species sampled (as judged by GC-MS, LC-MS and
<superScript id="7C129BCABA54A740AFF34D8EFD043EAC" attach="right" box="[691,700,936,949]" fontSize="5" pageId="2" pageNumber="76">1</superScript>
H NMR spectroscopic analysis; see: Supporting Information). This tentatively suggests limited intraspecific variation within the respective endemic Tasmanian populations of each of species. Notably, analysis of the crude PHWE extracts of all leaf specimens (AI) were consistent with the presence of both juglone (
<emphasis id="B913EA90BA54A740AC3C4A1EFE303952" bold="true" box="[380,392,1080,1099]" pageId="2" pageNumber="76">1</emphasis>
) and its parent glycoside
<emphasis id="B913EA90BA54A740AF3A4A1EFD3E3952" bold="true" box="[634,646,1080,1099]" pageId="2" pageNumber="76">6</emphasis>
as judged by LCMS (see: Supporting Information). It is likely that because glycoside
<emphasis id="B913EA90BA54A740AD244A56FFC8399A" bold="true" box="[100,112,1136,1155]" pageId="2" pageNumber="76">6</emphasis>
is only present in trace amounts in both
<taxonomicName id="4C674D01BA54A740ACAF4A56FDE7399A" box="[495,607,1136,1155]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tasmanica">
<emphasis id="B913EA90BA54A740ACAF4A56FDE7399A" bold="true" box="[495,607,1136,1155]" italics="true" pageId="2" pageNumber="76">L. tasmanica</emphasis>
</taxonomicName>
and
<taxonomicName id="4C674D01BA54A740AFCE4A56FD56399A" baseAuthorityName="Moir and Thompson" baseAuthorityYear="1973" box="[654,750,1136,1155]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tinctoria">
<emphasis id="B913EA90BA54A740AFCE4A56FD56399A" bold="true" box="[654,750,1136,1155]" italics="true" pageId="2" pageNumber="76">L. tinctoria</emphasis>
</taxonomicName>
it was not isolated via flash chromatography.
</paragraph>
</subSubSection>
</treatment>
</document>