246 lines
26 KiB
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246 lines
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<document id="C26214FB0B15AFE7C77B979E811A6DD3" 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="03CE8794BA55A746AE724C78FE493FDD" 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 R. Br." docType="treatment" docVersion="1" lastPageNumber="78" 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="77" updateTime="1705326194582" updateUser="juliana">
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<mods:titleInfo id="B31F08299FBA20D39AF8C0346F9EBF10">
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<mods:title id="30F82EAF1764A32C00D96BE63FAF4592">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="3454475C6A6D2E6BD34FA6DD3B2B7F3D">Deans, Bianca J.</mods:namePart>
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<mods:affiliation id="E1747CBDE2411AC95113B769F6748616">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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</mods:name>
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</mods:role>
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<mods:namePart id="BE1C6593F7C89F68FC01D13655B8B462">Tedone, Laura</mods:namePart>
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<mods:affiliation id="C1A375FD821EB30F56AC9396CF9BA193">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:role>
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<mods:namePart id="30A7BB5939BB38A385F224F6CED5FC83">Bissember, Alex C.</mods:namePart>
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<mods:affiliation id="50AB00B84056F0CF69904E3AA1EDF872">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:nameIdentifier id="4304BC4C1F11732B84F681E7F5EAF01D" type="email">alex.bissember@utas.edu.au</mods:nameIdentifier>
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</mods:role>
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<mods:namePart id="5C10EAB97AA434B07813ADBC5E6945AE">Smith, Jason A.</mods:namePart>
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<mods:affiliation id="F235914FB209C5AB32A8BE201320C8CC">School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia</mods:affiliation>
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<mods:typeOfResource id="F7E90653B2E3EB02645D87A838E84A46">text</mods:typeOfResource>
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<mods:title id="1B8C6B1A991CBA0E986F78F5C25CE19F">Phytochemistry</mods:title>
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</mods:titleInfo>
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<mods:part id="02EE68685CF5D4187FB3C47717EB37E6">
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<mods:date id="ED560FB57B39FED7C23C0D6CEDCA2E8E">2018</mods:date>
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<mods:number id="9153CCD5D5A2ACA23C7C3E6EBC9A9A5B">2018-09-30</mods:number>
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<mods:number id="2C1B8AB941C1ED2B48FB4EB1E04BE9EE">153</mods:number>
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<mods:start id="3D80C1683CC307FCF1E29ADA49597104">74</mods:start>
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<mods:end id="C634798198259119D563085BB56EE794">78</mods:end>
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<mods:url id="3EBBB08C33B27B63FF0A373F7BC29A96">http://dx.doi.org/10.1016/j.phytochem.2018.05.019</mods:url>
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</mods:location>
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<mods:classification id="E3F34C05C2D587FA7964CEE4953EEFA7">journal article</mods:classification>
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<mods:identifier id="FCAF92FC0D58CCC4338C5F975FAB0F3B" type="DOI">10.1016/j.phytochem.2018.05.019</mods:identifier>
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<mods:identifier id="7A835D3110C96F5F65578B6AD2E605E9" type="ISSN">1873-3700</mods:identifier>
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<mods:identifier id="ADEFCF7A9D587DA6ED58EB310D4CF424" type="Zenodo-Dep">10483773</mods:identifier>
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</mods:mods>
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<treatment id="03CE8794BA55A746AE724C78FE493FDD" LSID="urn:lsid:plazi:treatment:03CE8794BA55A746AE724C78FE493FDD" httpUri="http://treatment.plazi.org/id/03CE8794BA55A746AE724C78FE493FDD" lastPageId="4" lastPageNumber="78" pageId="3" pageNumber="77">
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<subSubSection id="C37D6509BA55A741AE724C78FBCD3F68" box="[818,1141,606,625]" pageId="3" pageNumber="77" type="nomenclature">
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<paragraph id="8BD83682BA55A741AE724C78FBCD3F68" blockId="3.[818,1141,606,625]" box="[818,1141,606,625]" pageId="3" pageNumber="77">
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<heading id="D09081EEBA55A741AE724C78FBCD3F68" bold="true" box="[818,1141,606,625]" fontSize="36" level="1" pageId="3" pageNumber="77" reason="1">
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<emphasis id="B913EA90BA55A741AE724C78FBCD3F68" bold="true" box="[818,1141,606,625]" italics="true" pageId="3" pageNumber="77">
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4.5. Extraction of
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<taxonomicName id="4C674D01BA55A741AE9B4C78FBCD3F68" ID-CoL="3VWYW" authority="R. Br." authorityName="R. Br." box="[987,1141,606,625]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="tinctoria">Lomatia tinctoria</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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</subSubSection>
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<subSubSection id="C37D6509BA55A741AE134CB0FBDC3B3C" pageId="3" pageNumber="77" type="description">
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<paragraph id="8BD83682BA55A741AE134CB0FAA5390A" blockId="3.[818,1488,662,1573]" pageId="3" pageNumber="77">
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<emphasis id="B913EA90BA55A741AE134CB0FBDA3FB0" bold="true" box="[851,1122,662,681]" pageId="3" pageNumber="77">Diethyl ether maceration.</emphasis>
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Fresh leaves including petiole of
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<taxonomicName id="4C674D01BA55A741A8FE4CB0FCC43FDD" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="tinctoria">
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<emphasis id="B913EA90BA55A741A8FE4CB0FCC43FDD" bold="true" italics="true" pageId="3" pageNumber="77">L. tinctoria</emphasis>
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</taxonomicName>
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(19.0 g) (extracted within 1 h of obtaining plant material to reduce the likelihood of decomposition) were cut at the petiole into ∼
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<quantity id="4C9F9B67BA55A741AE074CCFFC383FE5" box="[839,896,745,764]" metricMagnitude="-2" metricUnit="m" metricValue="2.5" pageId="3" pageNumber="77" unit="cm" value="2.5">2.5cm</quantity>
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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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<subScript id="17E334C7BA55A741A94F4D5BFBA03E93" attach="both" box="[1039,1048,893,906]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
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SO
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<subScript id="17E334C7BA55A741A9724D5BFB833E93" attach="left" box="[1074,1083,893,906]" fontSize="5" pageId="3" pageNumber="77">4</subScript>
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), filtered, and evaporated under reduced pressure to provide an orange residue (
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<quantity id="4C9F9B67BA55A741A9824DB7FAB53EBD" box="[1218,1293,913,932]" metricMagnitude="-4" metricUnit="kg" metricValue="2.07" pageId="3" pageNumber="77" unit="mg" value="207.0">207 mg</quantity>
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). This mixture was purified by automated flash chromatography to deliver juglone (
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<quantity id="4C9F9B67BA55A741AE794DEEFC3A3EC2" box="[825,898,968,987]" metricMagnitude="-4" metricUnit="kg" metricValue="1.1099999999999999" pageId="3" pageNumber="77" unit="mg" value="111.0">111 mg</quantity>
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, 0.58% w/w) as red/orange crystalline solid and a colorless semi-solid (
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<quantity id="4C9F9B67BA55A741AEDF4DC2FC643EEE" box="[927,988,996,1015]" metricMagnitude="-5" metricUnit="kg" metricValue="2.5" pageId="3" pageNumber="77" unit="mg" value="25.0">25 mg</quantity>
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, 0.13% w/w) containing nonacosane predominantly (as judged by GC-MS; see: Supporting Information).
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</paragraph>
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<paragraph id="8BD83682BA55A741AE134A3AFBAB385F" blockId="3.[818,1488,662,1573]" pageId="3" pageNumber="77">
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<emphasis id="B913EA90BA55A741AE134A3AFC203936" bold="true" box="[851,920,1052,1071]" pageId="3" pageNumber="77">PHWE.</emphasis>
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Immediately following the above-mentioned diethyl ether maceration, residual solvent was allowed to evaporate from the leaf material that remained (∼10 min). The ensuing
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<taxonomicName id="4C674D01BA55A741A8614A72FA30397E" box="[1313,1416,1108,1127]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="tinctoria">
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<emphasis id="B913EA90BA55A741A8614A72FA30397E" bold="true" box="[1313,1416,1108,1127]" italics="true" pageId="3" pageNumber="77">L. tinctoria</emphasis>
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</taxonomicName>
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leaves (
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<quantity id="4C9F9B67BA55A741AE794A56FCCC399A" box="[825,884,1136,1155]" metricMagnitude="-2" metricUnit="kg" metricValue="1.45" pageId="3" pageNumber="77" unit="g" value="14.5">14.5 g</quantity>
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) were then coarsely ground in a spice grinder, mixed with sand (
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<quantity id="4C9F9B67BA55A741AE794AAAFCEF3986" box="[825,855,1164,1183]" metricMagnitude="-3" metricUnit="kg" metricValue="2.0" pageId="3" pageNumber="77" unit="g" value="2.0">2 g</quantity>
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), and extracted using the identical PHWE method detailed previously. The ensuing extract was then concentrated under reduced pressure on a rotary evaporator (50 ̊C bath temperature) to remove EtOH. The ensuing aqueous extract was then extracted with EtOAc (3 × 60 mL), with the organic extracts combined, dried over Na
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<subScript id="17E334C7BA55A741A8DD4B22FA1E3808" attach="right" box="[1437,1446,1284,1297]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
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SO
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<subScript id="17E334C7BA55A741A8804B22FA713808" attach="left" box="[1472,1481,1284,1297]" fontSize="5" pageId="3" pageNumber="77">4</subScript>
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, filtered and evaporated under reduced pressured to provide a solid dark yellow residue (
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<quantity id="4C9F9B67BA55A741AE894B15FBB0385F" box="[969,1032,1331,1350]" metricMagnitude="-5" metricUnit="kg" metricValue="5.9" pageId="3" pageNumber="77" unit="mg" value="59.0">59 mg</quantity>
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).
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</paragraph>
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<paragraph id="8BD83682BA55A741AE134B69FBDC3B3C" blockId="3.[818,1488,662,1573]" pageId="3" pageNumber="77">
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A portion of the total 100 mL aqueous phase (30 mL) was evaporated to dryness (
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<quantity id="4C9F9B67BA55A741AE924B4DFBA23867" box="[978,1050,1387,1406]" metricMagnitude="-4" metricUnit="kg" metricValue="1.93" pageId="3" pageNumber="77" unit="mg" value="193.0">193 mg</quantity>
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) and dissolved in pyridine (1.5 mL) and cooled to 0 ̊C. Acetic anhydride (1.5 mL) was added dropwise and the magnetically stirred reaction mixture was maintained at room temperature. After 21 h, the mixture was concentrated under reduced pressure to afford a brown gum (
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<quantity id="4C9F9B67BA55A741AEBC4BFCFBFF38F4" box="[1020,1095,1498,1517]" metricMagnitude="-4" metricUnit="kg" metricValue="3.52" pageId="3" pageNumber="77" unit="mg" value="352.0">352 mg</quantity>
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). Purification by automated flash column chromatography (0
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<emphasis id="B913EA90BA55A741AEAD4BDEFBBA3B10" bold="true" box="[1005,1026,1528,1545]" italics="true" pageId="3" pageNumber="77">→</emphasis>
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100% EtOAc/hexanes; 10 min) provided α- and β- Glucose pentaacetate (
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<quantity id="4C9F9B67BA55A741A95B4834FBE13B3C" box="[1051,1113,1554,1573]" metricMagnitude="-5" metricUnit="kg" metricValue="9.1" pageId="3" pageNumber="77" unit="mg" value="91.0">91 mg</quantity>
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).
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</paragraph>
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</subSubSection>
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<subSubSection id="C37D6509BA55A746AE72486CFE493FDD" lastPageId="4" lastPageNumber="78" pageId="3" pageNumber="77" type="discussion">
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<paragraph id="8BD83682BA55A741AE72486CFA783B44" blockId="3.[818,1472,1610,1629]" box="[818,1472,1610,1629]" pageId="3" pageNumber="77">
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<emphasis id="B913EA90BA55A741AE72486CFA783B44" bold="true" box="[818,1472,1610,1629]" italics="true" pageId="3" pageNumber="77">
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4.6. Intraspecific studies of
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<taxonomicName id="4C674D01BA55A741A96D486CFB183B44" ID-CoL="3VWYS" box="[1069,1184,1610,1629]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="tasmanica">L. tasmanica</taxonomicName>
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,
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<taxonomicName id="4C674D01BA55A741A9ED486CFAB73B44" box="[1197,1295,1610,1629]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="tinctoria">L. tinctoria</taxonomicName>
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and
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<taxonomicName id="4C674D01BA55A741A87F486CFA783B44" box="[1343,1472,1610,1629]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="polymorpha">L. polymorpha</taxonomicName>
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</emphasis>
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</paragraph>
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<paragraph id="8BD83682BA55A746AE1348A4FEE93DD7" blockId="3.[818,1488,1666,1992]" lastBlockId="4.[100,771,155,708]" lastPageId="4" lastPageNumber="78" pageId="3" pageNumber="77">
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<emphasis id="B913EA90BA55A741AE1348A4FBE43B8C" bold="true" box="[851,1116,1666,1685]" pageId="3" pageNumber="77">Diethyl ether maceration.</emphasis>
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<specimenCount id="9D61FD0BBA55A741A92448A4FABB3B8C" box="[1124,1283,1666,1685]" count="3" pageId="3" pageNumber="77" type="generic">Three specimens</specimenCount>
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from each of the respective species were separately extracted (i.e., a total of nine extractions were performed). Fresh leaves including petiole of the
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<specimenCount id="9D61FD0BBA55A741A8C4489FFA683BD5" box="[1412,1488,1721,1740]" count="3" pageId="3" pageNumber="77" type="generic">
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three
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<taxonomicName id="4C674D01BA55A741A8FE489FFA683BD5" box="[1470,1488,1721,1740]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="tasmanica">
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<emphasis id="B913EA90BA55A741A8FE489FFA683BD5" bold="true" box="[1470,1488,1721,1740]" italics="true" pageId="3" pageNumber="77">L.</emphasis>
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</taxonomicName>
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</specimenCount>
|
|||
|
|
tasmanica specimens (A–C),
|
|||
|
|
<taxonomicName id="4C674D01BA55A741A90148F3FB1C3BF1" box="[1089,1188,1749,1768]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="tinctoria">
|
|||
|
|
<emphasis id="B913EA90BA55A741A90148F3FB1C3BF1" bold="true" box="[1089,1188,1749,1768]" italics="true" pageId="3" pageNumber="77">L. tinctoria</emphasis>
|
|||
|
|
</taxonomicName>
|
|||
|
|
(D–F) and
|
|||
|
|
<taxonomicName id="4C674D01BA55A741A85448F3FA2E3BF1" box="[1300,1430,1749,1768]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="3" pageNumber="77" phylum="Tracheophyta" rank="species" species="polymorpha">
|
|||
|
|
<emphasis id="B913EA90BA55A741A85448F3FA2E3BF1" bold="true" box="[1300,1430,1749,1768]" italics="true" pageId="3" pageNumber="77">L. polymorpha</emphasis>
|
|||
|
|
</taxonomicName>
|
|||
|
|
(G–I) (10.0 g each) were completely submerged in diethyl ether (125 mL) in a sealed vessel, without stirring at room temperature. After 5 h, the leaves were observed to darken, while the solutions displayed a vibrant orange color. The mixtures were filtered, dried (Na
|
|||
|
|
<subScript id="17E334C7BA55A741A9A2496BFB533A43" attach="both" box="[1250,1259,1869,1882]" fontSize="5" pageId="3" pageNumber="77">2</subScript>
|
|||
|
|
SO
|
|||
|
|
<subScript id="17E334C7BA55A741A846496BFAB73A43" attach="left" box="[1286,1295,1869,1882]" fontSize="5" pageId="3" pageNumber="77">4</subScript>
|
|||
|
|
), filtered, and concentrated under reduced pressure to provide orange residue (Specimen A,
|
|||
|
|
<quantity id="4C9F9B67BA55A741AE0B495BFC3F3A89" box="[843,903,1917,1936]" metricMagnitude="-5" metricUnit="kg" metricValue="6.4" pageId="3" pageNumber="77" unit="mg" value="64.0">64 mg</quantity>
|
|||
|
|
; Specimen B,
|
|||
|
|
<quantity id="4C9F9B67BA55A741A946495BFBFB3A89" box="[1030,1091,1917,1936]" metricMagnitude="-5" metricUnit="kg" metricValue="6.4" pageId="3" pageNumber="77" unit="mg" value="64.0">64 mg</quantity>
|
|||
|
|
; Specimen C,
|
|||
|
|
<quantity id="4C9F9B67BA55A741A982495BFB473A89" box="[1218,1279,1917,1936]" metricMagnitude="-5" metricUnit="kg" metricValue="9.6" pageId="3" pageNumber="77" unit="mg" value="96.0">96 mg</quantity>
|
|||
|
|
); (Specimen D,
|
|||
|
|
<quantity id="4C9F9B67BA55A741A8D0495BFA743A89" box="[1424,1484,1917,1936]" metricMagnitude="-5" metricUnit="kg" metricValue="6.5" pageId="3" pageNumber="77" unit="mg" value="65.0">65 mg</quantity>
|
|||
|
|
; Specimen E,
|
|||
|
|
<quantity id="4C9F9B67BA55A741AEE849BFFC5D3AB5" box="[936,997,1945,1964]" metricMagnitude="-5" metricUnit="kg" metricValue="6.4" pageId="3" pageNumber="77" unit="mg" value="64.0">64 mg</quantity>
|
|||
|
|
; Specimen F,
|
|||
|
|
<quantity id="4C9F9B67BA55A741A92349BFFB183AB5" box="[1123,1184,1945,1964]" metricMagnitude="-5" metricUnit="kg" metricValue="5.1" pageId="3" pageNumber="77" unit="mg" value="51.0">51 mg</quantity>
|
|||
|
|
); (Specimen G,
|
|||
|
|
<quantity id="4C9F9B67BA55A741A87049BFFAD53AB5" box="[1328,1389,1945,1964]" metricMagnitude="-5" metricUnit="kg" metricValue="8.5" pageId="3" pageNumber="77" unit="mg" value="85.0">85 mg</quantity>
|
|||
|
|
; Specimen H,
|
|||
|
|
<quantity id="4C9F9B67BA55A741AE0E4993FC323AD1" box="[846,906,1973,1992]" metricMagnitude="-5" metricUnit="kg" metricValue="8.4" pageId="3" pageNumber="77" unit="mg" value="84.0">84 mg</quantity>
|
|||
|
|
; Specimen I,
|
|||
|
|
<quantity id="4C9F9B67BA55A741A9484993FBFD3AD1" box="[1032,1093,1973,1992]" metricMagnitude="-5" metricUnit="kg" metricValue="6.8" pageId="3" pageNumber="77" unit="mg" value="68.0">68 mg</quantity>
|
|||
|
|
). The respective crude samples were then each analyzed by
|
|||
|
|
<superScript id="7C129BCABA52A746AC5F4EBDFE903DB1" attach="right" box="[287,296,155,168]" fontSize="5" pageId="4" pageNumber="78">1</superScript>
|
|||
|
|
H NMR spectroscopy (CDCl
|
|||
|
|
<subScript id="17E334C7BA52A746AF7D4E8EFDFE3DAC" attach="left" box="[573,582,168,181]" fontSize="5" pageId="4" pageNumber="78">3</subScript>
|
|||
|
|
) and GC-MS (see: Supporting Information).
|
|||
|
|
</paragraph>
|
|||
|
|
<paragraph id="8BD83682BA52A746ADC54EF1FE493FDD" blockId="4.[100,771,155,708]" pageId="4" pageNumber="78">
|
|||
|
|
<emphasis id="B913EA90BA52A746ADC54EF1FF733DF3" bold="true" box="[133,203,215,234]" pageId="4" pageNumber="78">PHWE.</emphasis>
|
|||
|
|
Immediately following the above-mentioned diethyl ether maceration, residual solvent was allowed to evaporate from the remaining leaf material (∼10 min). The ensuing leaves were then coarsely ground in a spice grinder: Specimen A (
|
|||
|
|
<quantity id="4C9F9B67BA52A746AF4B4F0DFD843C27" box="[523,572,299,318]" metricMagnitude="-3" metricUnit="kg" metricValue="7.6" pageId="4" pageNumber="78" unit="g" value="7.6">7.6 g</quantity>
|
|||
|
|
); Specimen B (
|
|||
|
|
<quantity id="4C9F9B67BA52A746AF8B4F0DFD433C27" box="[715,763,299,318]" metricMagnitude="-3" metricUnit="kg" metricValue="7.7" pageId="4" pageNumber="78" unit="g" value="7.7">7.7 g</quantity>
|
|||
|
|
) Specimen C (
|
|||
|
|
<quantity id="4C9F9B67BA52A746AD9E4F61FEB63C43" box="[222,270,327,346]" metricMagnitude="-3" metricUnit="kg" metricValue="7.5" pageId="4" pageNumber="78" unit="g" value="7.5">7.5 g</quantity>
|
|||
|
|
); Specimen D (
|
|||
|
|
<quantity id="4C9F9B67BA52A746ACDA4F61FE733C43" box="[410,459,327,346]" metricMagnitude="-3" metricUnit="kg" metricValue="7.9" pageId="4" pageNumber="78" unit="g" value="7.9">7.9 g</quantity>
|
|||
|
|
); Specimen E (
|
|||
|
|
<quantity id="4C9F9B67BA52A746AF154F61FD3D3C43" box="[597,645,327,346]" metricMagnitude="-3" metricUnit="kg" metricValue="7.8" pageId="4" pageNumber="78" unit="g" value="7.8">7.8 g</quantity>
|
|||
|
|
); Specimen F (
|
|||
|
|
<quantity id="4C9F9B67BA52A746AD2B4F45FF233C6F" box="[107,155,355,374]" metricMagnitude="-3" metricUnit="kg" metricValue="7.7" pageId="4" pageNumber="78" unit="g" value="7.7">7.7 g</quantity>
|
|||
|
|
); Specimen G (
|
|||
|
|
<quantity id="4C9F9B67BA52A746AC764F45FEDE3C6F" box="[310,358,355,374]" metricMagnitude="-3" metricUnit="kg" metricValue="8.5" pageId="4" pageNumber="78" unit="g" value="8.5">8.5 g</quantity>
|
|||
|
|
); Specimen H (
|
|||
|
|
<quantity id="4C9F9B67BA52A746AF424F45FD8A3C6F" box="[514,562,355,374]" metricMagnitude="-3" metricUnit="kg" metricValue="7.8" pageId="4" pageNumber="78" unit="g" value="7.8">7.8 g</quantity>
|
|||
|
|
); Specimen I (
|
|||
|
|
<quantity id="4C9F9B67BA52A746AF854F45FD4F3C6F" box="[709,759,355,374]" metricMagnitude="-3" metricUnit="kg" metricValue="7.7" pageId="4" pageNumber="78" unit="g" value="7.7">7.7 g</quantity>
|
|||
|
|
). Respective samples were mixed with sand (
|
|||
|
|
<quantity id="4C9F9B67BA52A746AF504F59FD963C8B" box="[528,558,383,402]" metricMagnitude="-3" metricUnit="kg" metricValue="2.0" pageId="4" pageNumber="78" unit="g" value="2.0">2 g</quantity>
|
|||
|
|
), and extracted using standard PHWE method described previously. The ensuing extract was then concentrated under reduced pressure to remove EtOH (50 ̊C bath temperature). The ensuing aqueous extracts were then extracted with EtOAc (3 × 30 mL), with the organic extracts combined, dried over Na
|
|||
|
|
<subScript id="17E334C7BA52A746AD3E4C34FF3F3F06" attach="both" box="[126,135,530,543]" fontSize="5" pageId="4" pageNumber="78">2</subScript>
|
|||
|
|
SO
|
|||
|
|
<subScript id="17E334C7BA52A746ADE24C34FF133F06" attach="left" box="[162,171,530,543]" fontSize="5" pageId="4" pageNumber="78">4</subScript>
|
|||
|
|
, filtered and evaporated under reduced pressured to provide solid dark green residues:
|
|||
|
|
<taxonomicName id="4C674D01BA52A746AC214C00FE6B3F20" box="[353,467,550,569]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="4" pageNumber="78" phylum="Tracheophyta" rank="species" species="tasmanica">
|
|||
|
|
<emphasis id="B913EA90BA52A746AC214C00FE6B3F20" bold="true" box="[353,467,550,569]" italics="true" pageId="4" pageNumber="78">L. tasmanica</emphasis>
|
|||
|
|
</taxonomicName>
|
|||
|
|
(Specimen A,
|
|||
|
|
<quantity id="4C9F9B67BA52A746AF214C00FD253F20" box="[609,669,550,569]" metricMagnitude="-5" metricUnit="kg" metricValue="2.6" pageId="4" pageNumber="78" unit="mg" value="26.0">26 mg</quantity>
|
|||
|
|
; Specimen B,
|
|||
|
|
<quantity id="4C9F9B67BA52A746ADC64C64FF7A3F4C" box="[134,194,578,597]" metricMagnitude="-5" metricUnit="kg" metricValue="3.2" pageId="4" pageNumber="78" unit="mg" value="32.0">32 mg</quantity>
|
|||
|
|
; Specimen C,
|
|||
|
|
<quantity id="4C9F9B67BA52A746AC1F4C64FE243F4C" box="[351,412,578,597]" metricMagnitude="-5" metricUnit="kg" metricValue="2.1" pageId="4" pageNumber="78" unit="mg" value="21.0">21 mg</quantity>
|
|||
|
|
);
|
|||
|
|
<taxonomicName id="4C674D01BA52A746ACF54C64FDA73F4C" box="[437,543,578,597]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="4" pageNumber="78" phylum="Tracheophyta" rank="species" species="tinctoria">
|
|||
|
|
<emphasis id="B913EA90BA52A746ACF54C64FDA73F4C" bold="true" box="[437,543,578,597]" italics="true" pageId="4" pageNumber="78">L. tinctoria</emphasis>
|
|||
|
|
</taxonomicName>
|
|||
|
|
(Specimen D,
|
|||
|
|
<quantity id="4C9F9B67BA52A746AF824C64FD473F4C" box="[706,767,578,597]" metricMagnitude="-5" metricUnit="kg" metricValue="1.1" pageId="4" pageNumber="78" unit="mg" value="11.0">11 mg</quantity>
|
|||
|
|
; Specimen E,
|
|||
|
|
<quantity id="4C9F9B67BA52A746ADA24C78FEA63F68" box="[226,286,606,625]" metricMagnitude="-5" metricUnit="kg" metricValue="2.4" pageId="4" pageNumber="78" unit="mg" value="24.0">24 mg</quantity>
|
|||
|
|
; Specimen F,
|
|||
|
|
<quantity id="4C9F9B67BA52A746ACE74C78FE5C3F68" box="[423,484,606,625]" metricMagnitude="-5" metricUnit="kg" metricValue="2.1" pageId="4" pageNumber="78" unit="mg" value="21.0">21 mg</quantity>
|
|||
|
|
);
|
|||
|
|
<taxonomicName id="4C674D01BA52A746ACB74C78FDC13F68" box="[503,633,606,625]" class="Magnoliopsida" family="Proteaceae" genus="Lomatia" kingdom="Plantae" order="Proteales" pageId="4" pageNumber="78" phylum="Tracheophyta" rank="species" species="polymorpha">
|
|||
|
|
<emphasis id="B913EA90BA52A746ACB74C78FDC13F68" bold="true" box="[503,633,606,625]" italics="true" pageId="4" pageNumber="78">L. polymorpha</emphasis>
|
|||
|
|
</taxonomicName>
|
|||
|
|
(Specimen G,
|
|||
|
|
<quantity id="4C9F9B67BA52A746AD244C5CFF193F94" box="[100,161,634,653]" metricMagnitude="-5" metricUnit="kg" metricValue="7.6" pageId="4" pageNumber="78" unit="mg" value="76.0">76 mg</quantity>
|
|||
|
|
; Specimen H,
|
|||
|
|
<quantity id="4C9F9B67BA52A746AC6C4C5CFED03F94" box="[300,360,634,653]" metricMagnitude="-5" metricUnit="kg" metricValue="2.1" pageId="4" pageNumber="78" unit="mg" value="21.0">21 mg</quantity>
|
|||
|
|
; Specimen I,
|
|||
|
|
<quantity id="4C9F9B67BA52A746ACAB4C5CFD903F94" box="[491,552,634,653]" metricMagnitude="-5" metricUnit="kg" metricValue="1.8" pageId="4" pageNumber="78" unit="mg" value="18.0">18 mg</quantity>
|
|||
|
|
). The respective crude samples were then each analyzed by
|
|||
|
|
<superScript id="7C129BCABA52A746ACFD4CB7FE7E3F87" attach="right" box="[445,454,657,670]" fontSize="5" pageId="4" pageNumber="78">1</superScript>
|
|||
|
|
H NMR spectroscopy (acetone-
|
|||
|
|
<emphasis id="B913EA90BA52A746AFA64CB0FD493FB0" bold="true" box="[742,753,662,681]" italics="true" pageId="4" pageNumber="78">d</emphasis>
|
|||
|
|
<subScript id="17E334C7BA52A746AFB14CB8FD423FB2" attach="left" box="[753,762,670,683]" fontSize="5" pageId="4" pageNumber="78">6</subScript>
|
|||
|
|
) and LC-MS (see: Supporting Information).
|
|||
|
|
</paragraph>
|
|||
|
|
</subSubSection>
|
|||
|
|
</treatment>
|
|||
|
|
</document>
|