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<document id="228D50A7B7137357854172AA1F6A8D5E" 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="03CE8794BA54A741AE724B15FD883E01" 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="77" masterDocId="FFF7FFECBA56A742AD404E26FFB83D19" masterDocTitle="Phytochemical profile of the rare, ancient clone Lomatia tasmanica and comparison to other endemic Tasmanian species L. tinctoria and L. polymorpha" masterLastPageNumber="78" masterPageNumber="74" pageNumber="76" updateTime="1705326194582" updateUser="juliana">
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<mods:title id="E1460174DF0AD461ADFB12F49FEDD732">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="6F04CBC13146D26AB14C0CFAEC37D1A8">Deans, Bianca J.</mods:namePart>
<mods:affiliation id="275E79FF1565DFEEA6AD80633D122EE3">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:namePart id="3C7A438C6B2315F37AECEE856E2C83F5">Tedone, Laura</mods:namePart>
<mods:affiliation id="EDE0B76D6F74ED00A8DEBB269398F999">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="5058645F24A5B35D80AC03FE624CE061">Bissember, Alex C.</mods:namePart>
<mods:affiliation id="307CEEB0AD568528C3F4520EBB0CF36A">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
<mods:nameIdentifier id="132960B5A1A2769ED07726F06EC1813F" type="email">alex.bissember@utas.edu.au</mods:nameIdentifier>
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<mods:namePart id="844AE07EA9412911BA4001C8B5A36C04">Smith, Jason A.</mods:namePart>
<mods:affiliation id="4D93EF1AA9324C899C209BEFF8DE825D">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<treatment id="03CE8794BA54A741AE724B15FD883E01" LSID="urn:lsid:plazi:treatment:03CE8794BA54A741AE724B15FD883E01" httpUri="http://treatment.plazi.org/id/03CE8794BA54A741AE724B15FD883E01" lastPageId="3" lastPageNumber="77" pageId="2" pageNumber="76">
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<paragraph id="8BD83682BA54A740AE724B15FB3D385F" blockId="2.[818,1157,1331,1350]" box="[818,1157,1331,1350]" pageId="2" pageNumber="76">
<heading id="D09081EEBA54A740AE724B15FB3D385F" bold="true" box="[818,1157,1331,1350]" fontSize="36" level="1" pageId="2" pageNumber="76" reason="1">
<emphasis id="B913EA90BA54A740AE724B15FB3D385F" bold="true" box="[818,1157,1331,1350]" italics="true" pageId="2" pageNumber="76">
4.3. Extraction of
<taxonomicName id="4C674D01BA54A740AE9B4B15FB3D385F" ID-CoL="3VWYS" authority="W. M. Curtis" authorityName="W. M. Curtis" box="[987,1157,1331,1350]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tasmanica">Lomatia tasmanica</taxonomicName>
</emphasis>
</heading>
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<paragraph id="8BD83682BA54A740AE134B4DFA703A1D" blockId="2.[818,1488,1387,1992]" pageId="2" pageNumber="76">
<emphasis id="B913EA90BA54A740AE134B4DFBDA3867" bold="true" box="[851,1122,1387,1406]" pageId="2" pageNumber="76">Diethyl ether maceration.</emphasis>
Fresh leaves including petiole of
<taxonomicName id="4C674D01BA54A740A8FE4B4DFC343883" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tasmanica">
<emphasis id="B913EA90BA54A740A8FE4B4DFC343883" bold="true" italics="true" pageId="2" pageNumber="76">L. tasmanica</emphasis>
</taxonomicName>
(
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) (extracted within 1 h of obtaining plant material to reduce the likelihood of decomposition) were cut at the petiole into
<quantity id="4C9F9B67BA54A740AE074B98FC3D38C8" box="[839,901,1470,1489]" metricMagnitude="-2" metricUnit="m" metricValue="2.5" pageId="2" pageNumber="76" unit="cm" value="2.5">2.5 cm</quantity>
pieces (to form an even layer of material in the extraction vessel). The plant material was then completely submerged in diethyl ether (250 mL) and the vessel was sealed and maintained at room temperature. After 5 h, the leaves were observed to change to a black color, while the solution displayed a vibrant orange color. The mixture was filtered, dried (Na
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SO
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), filtered, and evaporated under reduced pressure to provide an orange residue (
<quantity id="4C9F9B67BA54A740A9834840FAB53B60" box="[1219,1293,1638,1657]" metricMagnitude="-4" metricUnit="kg" metricValue="1.93" pageId="2" pageNumber="76" unit="mg" value="193.0">193 mg</quantity>
). This mixture was purified by automated flash chromatography (0 30
<emphasis id="B913EA90BA54A740A84A48A2FAA73B8C" bold="true" box="[1290,1311,1668,1685]" italics="true" pageId="2" pageNumber="76"></emphasis>
% hexanes/EtOAc) to deliver juglone (
<quantity id="4C9F9B67BA54A740AEA848B8FB9D3BA8" box="[1000,1061,1694,1713]" metricMagnitude="-5" metricUnit="kg" metricValue="6.0" pageId="2" pageNumber="76" unit="mg" value="60.0">60 mg</quantity>
, 0.34% w/w) as red/orange crystalline solid (NMR spectroscopic data is provided in the Supporting Information) and a colorless semi-solid (
<quantity id="4C9F9B67BA54A740A96F48F3FBD43BF1" box="[1071,1132,1749,1768]" metricMagnitude="-5" metricUnit="kg" metricValue="5.3" pageId="2" pageNumber="76" unit="mg" value="53.0">53 mg</quantity>
, 0.30% w/w) containing a mixture of nonacosane (major component) and heptacosane (minor component).
</paragraph>
<paragraph id="8BD83682BA54A740AE13492BFABE3A6D" blockId="2.[818,1488,1387,1992]" pageId="2" pageNumber="76">
<emphasis id="B913EA90BA54A740AE13492BFC753A39" bold="true" box="[851,973,1805,1824]" pageId="2" pageNumber="76">Nonacosane</emphasis>
. (
<bibRefCitation id="EFF64B73BA54A740AEA3492BFB6C3A39" 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="[995,1236,1805,1824]" pageId="2" pageNumber="76" 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>
). EI-MS (
<emphasis id="B913EA90BA54A740A872492BFAFA3A39" bold="true" box="[1330,1346,1805,1824]" italics="true" pageId="2" pageNumber="76">m</emphasis>
/
<emphasis id="B913EA90BA54A740A80D492BFAEE3A39" bold="true" box="[1357,1366,1805,1824]" italics="true" pageId="2" pageNumber="76">z</emphasis>
): 408.
<emphasis id="B913EA90BA54A740A8E0492BFC323A25" bold="true" pageId="2" pageNumber="76">Heptacosane</emphasis>
. (
<bibRefCitation id="EFF64B73BA54A740AEDD490FFB3C3A25" 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="[925,1156,1833,1852]" pageId="2" pageNumber="76" 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>
). EI-MS (
<emphasis id="B913EA90BA54A740A99C490FFB543A25" bold="true" box="[1244,1260,1833,1852]" italics="true" pageId="2" pageNumber="76">m</emphasis>
/
<emphasis id="B913EA90BA54A740A9B7490FFAB83A25" bold="true" box="[1271,1280,1833,1852]" italics="true" pageId="2" pageNumber="76">z</emphasis>
): 380. See Supporting Information for
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H NMR spectrum and the GC chromatogram of the mixture containing nonacosane and heptacosane.
</paragraph>
<paragraph id="8BD83682BA54A741AE13495BFE493F18" blockId="2.[818,1488,1387,1992]" lastBlockId="3.[100,771,159,792]" lastPageId="3" lastPageNumber="77" pageId="2" pageNumber="76">
<emphasis id="B913EA90BA54A740AE13495BFC2A3A89" bold="true" box="[851,914,1917,1936]" pageId="2" pageNumber="76">PHWE</emphasis>
. Immediately following the above-mentioned diethyl ether maceration, residual solvent was allowed to evaporate from the leaf material that remained (10 min). The ensuing
<taxonomicName id="4C674D01BA54A740A8554993FA333AD1" box="[1301,1419,1973,1992]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="2" pageNumber="76" phylum="Tracheophyta" rank="species" species="tasmanica">
<emphasis id="B913EA90BA54A740A8554993FA333AD1" bold="true" box="[1301,1419,1973,1992]" italics="true" pageId="2" pageNumber="76">L. tasmanica</emphasis>
</taxonomicName>
leaves (
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) were then coarsely ground in a spice grinder, mixed with sand (
<quantity id="4C9F9B67BA55A741AD2C4E9DFF313DD7" box="[108,137,187,206]" metricMagnitude="-3" metricUnit="kg" metricValue="2.0" pageId="3" pageNumber="77" unit="g" value="2.0">2 g</quantity>
), placed into the portafilter (sample compartment) of an espresso machine and extracted using 35% v/v EtOH/H
<subScript id="17E334C7BA55A741AF764EF9FD873DF5" attach="both" box="[566,575,223,236]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
O (200 mL of a hot solution). The ensuing extract was then concentrated under reduced pressure on a rotary evaporator to dryness (50 ̊C bath temperature) to provide a brown residue (
<quantity id="4C9F9B67BA55A741AC174F0DFE2D3C27" box="[343,405,299,318]" metricMagnitude="-3" metricUnit="kg" metricValue="1.2" pageId="3" pageNumber="77" unit="g" value="1.2">1.20 g</quantity>
). The crude extract was adsorbed onto a 1:1 mixture of silica gel and Celite and fractionated by automated flash column chromatography (0
<emphasis id="B913EA90BA55A741ACE54F42FE023C6C" bold="true" box="[421,442,356,373]" italics="true" pageId="3" pageNumber="77"></emphasis>
40% MeOH/EtOAc; 18 min). This resulted in a combined fraction predominantly containing the two saccharides (
<quantity id="4C9F9B67BA55A741AD9D4FBCFE9E3CB4" box="[221,294,410,429]" metricMagnitude="-4" metricUnit="kg" metricValue="5.39" pageId="3" pageNumber="77" unit="mg" value="539.0">539 mg</quantity>
) as judged by
<superScript id="7C129BCABA55A741ACF14FB0FE023CBA" attach="right" box="[433,442,406,419]" fontSize="5" pageId="3" pageNumber="77">1</superScript>
H and
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C NMR spectroscopy. Due to difficulties isolating these compounds by flash column chromatography, this mixture was reacted with acetic anhydride to enable purification as described immediately below.
</paragraph>
<paragraph id="8BD83682BA55A741ADC54C2CFD883E01" blockId="3.[100,771,159,792]" pageId="3" pageNumber="77">
<emphasis id="B913EA90BA55A741ADC54C2CFD343F04" bold="true" box="[133,652,522,541]" pageId="3" pageNumber="77">Peracetylation of saccharides obtained from PHWE.</emphasis>
A portion of the mixture (
<quantity id="4C9F9B67BA55A741ADA34C00FE963F20" box="[227,302,550,569]" metricMagnitude="-4" metricUnit="kg" metricValue="2.06" pageId="3" pageNumber="77" unit="mg" value="206.0">206 mg</quantity>
), obtained as described immediately above, was dissolved in pyridine (1.5 mL), cooled to 0 ̊C. Acetic anhydride (1.5 mL) was added dropwise and the reaction mixture magnetically stirred at room temperature. After 21 h, the reaction mixture was concentrated under reduced pressure to afford a brown gum (
<quantity id="4C9F9B67BA55A741AFED4CB0FD403FB0" box="[685,760,662,681]" metricMagnitude="-4" metricUnit="kg" metricValue="4.4" pageId="3" pageNumber="77" unit="mg" value="440.0">440 mg</quantity>
). Purification by automated flash column chromatography (0
<emphasis id="B913EA90BA55A741AFF24C95FD7F3FDD" bold="true" box="[690,711,691,708]" italics="true" pageId="3" pageNumber="77"></emphasis>
100% EtOAc/hexanes; 10 min) provided an inseparable mixture of α- and β- glucose pentaacetate (
<quantity id="4C9F9B67BA55A741AC7C4CCFFEC03FE5" box="[316,376,745,764]" metricMagnitude="-5" metricUnit="kg" metricValue="8.5" pageId="3" pageNumber="77" unit="mg" value="85.0">85 mg</quantity>
) as a colorless film (NMR spectroscopic data is provided in the Supporting Information).
</paragraph>
</subSubSection>
</treatment>
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