471 lines
41 KiB
XML
471 lines
41 KiB
XML
<document id="14B5564F6E34550BD5AD895CDAFBD70A" ID-DOI="10.1016/j.phytochem.2018.06.008" ID-ISSN="1873-3700" ID-Zenodo-Dep="10484041" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="juliana" IM.materialsCitations_approvedBy="juliana" IM.metadata_approvedBy="juliana" IM.tables_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1704938836113" checkinUser="felipe" docAuthor="Milutinović, Violeta, Niketić, Marjan, Krunić, Aleksej, Nikolić, Dejan, Petković, Miloš, Ušjak, Ljuboš & Petrović, Silvana" docDate="2018" docId="90640E19FFD28D4AFFA687D5FD6742B1" docLanguage="en" docName="Phytochemistry.154.19-30.pdf" docOrigin="Phytochemistry 154" docSource="http://dx.doi.org/10.1016/j.phytochem.2018.06.008" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Hieracium calophyllum subsp. flowering" docType="treatment" docVersion="3" lastPageNumber="29" masterDocId="6C5D7661FFDB8D40FFC2840EFFA6401D" masterDocTitle="Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance" masterLastPageNumber="30" masterPageNumber="19" pageNumber="28" updateTime="1705328458641" updateUser="juliana">
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<mods:title id="8E24F4D1251E359A2CB2D76B5A8E6C50">Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance</mods:title>
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<mods:namePart id="0B1ADD81762F1DB98C0D90CAECCCBFE1">Milutinović, Violeta</mods:namePart>
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<mods:affiliation id="FB91919BAB4EFA71C9DFEA7C15ABD5ED">Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="2CAA58BFC2A23246A712CD2F9F37E767">Niketić, Marjan</mods:namePart>
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<mods:affiliation id="659B8ACF99B2DBEEF34993395F0542ED">Natural History Museum, Njegoševa 51, 11000 Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="884E3DE6303D0DB118C6154EF5BD3763">Krunić, Aleksej</mods:namePart>
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<mods:affiliation id="711D7F7FE5487F7909E6AF8E627DDCB2">Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL 60612, USA</mods:affiliation>
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<mods:name id="86EB6A6D3A93738F1519B790CDF88DA2" type="personal">
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<mods:namePart id="1F4D97B3E37523FD27BD28C26F83949B">Nikolić, Dejan</mods:namePart>
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<mods:affiliation id="50BA6474AF8B7DA3ADEAEB2EF1F4C929">Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL 60612, USA</mods:affiliation>
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</mods:name>
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<mods:namePart id="313B056C8005854AD0E3DBFCCADD5D37">Petković, Miloš</mods:namePart>
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<mods:affiliation id="AE80EC4CB147EF66A6F935852C40C8E9">Department of Organic Chemistry, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="3B379E6F95BC983979E1E4AD86FC30B8">Ušjak, Ljuboš</mods:namePart>
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<mods:affiliation id="52135AA3D661736092BB634F328A1C75">Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="FDBFF639EB93C4004C6675BEADC04935">Petrović, Silvana</mods:namePart>
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<mods:affiliation id="4DA7923499D2C2BE5C96A7D8F4EA5167">Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia</mods:affiliation>
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<mods:nameIdentifier id="9269529F08800FDE32EB312C03806C3E" type="email">silvana.petrovic@pharmacy.bg.ac.rs</mods:nameIdentifier>
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<mods:typeOfResource id="26880745A9CD95E34102B31A97275D54">text</mods:typeOfResource>
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<mods:title id="D4164103635052C81D949920B56A11A2">Phytochemistry</mods:title>
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<mods:part id="FE63259870BD3F86DEC56000F407F2FE">
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<mods:date id="104492FF3A323FB4A2C16D98D555B1DC">2018</mods:date>
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<mods:number id="02479283D16B5A98E58312BA71A3EE6A">2018-10-31</mods:number>
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<mods:number id="71A9621EB802952C3C7E28CE45AFD0BF">154</mods:number>
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<mods:start id="D3159249EF834884275F29BDC50E92D6">19</mods:start>
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<mods:end id="E86D35D1CA75C7198F5C4AD55C09261A">30</mods:end>
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<mods:url id="0242DFC07AFD58ED035E7472191D060A">http://dx.doi.org/10.1016/j.phytochem.2018.06.008</mods:url>
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<mods:classification id="3CDB0DAEEDF00FFB406A417EBD4B1DEF">journal article</mods:classification>
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<mods:identifier id="5DA6CBF3BD67F017F10EB58B21D668E3" type="DOI">10.1016/j.phytochem.2018.06.008</mods:identifier>
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<mods:identifier id="7F894C7132B0362636436E119DC952A9" type="ISSN">1873-3700</mods:identifier>
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<mods:identifier id="D2160357CFFEDA49C35F99A9DEDB4A7B" type="Zenodo-Dep">10484041</mods:identifier>
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</mods:mods>
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<treatment id="90640E19FFD28D4AFFA687D5FD6742B1" LSID="urn:lsid:plazi:treatment:90640E19FFD28D4AFFA687D5FD6742B1" httpUri="http://treatment.plazi.org/id/90640E19FFD28D4AFFA687D5FD6742B1" lastPageId="10" lastPageNumber="29" pageId="9" pageNumber="28">
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<subSubSection id="50D7EC84FFD28D49FFA687D5FF4B4417" pageId="9" pageNumber="28" type="nomenclature">
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<paragraph id="1872BF0FFFD28D49FFA687D5FF4B4417" blockId="9.[100,763,987,1034]" pageId="9" pageNumber="28">
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<emphasis id="2AB9631DFFD28D49FFA687D5FF4B4417" bold="true" italics="true" pageId="9" pageNumber="28">
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<heading id="433A0863FFD28D49FFA687D5FD5D43F3" bold="true" box="[100,763,987,1006]" centered="true" fontSize="36" level="1" pageId="9" pageNumber="28" reason="1">
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4.3. Preparation of MeOH extract of
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<taxonomicName id="DFCDC48CFFD28D49FE7A87D5FDE743F3" ID-CoL="3LM4Y" authority="R. Uechtr." box="[440,577,987,1006]" class="Magnoliopsida" family="Asteraceae" genus="Hieracium" kingdom="Plantae" order="Asterales" pageId="9" pageNumber="28" phylum="Tracheophyta" rank="species" species="calophyllum">H. calophyllum</taxonomicName>
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flowering heads and
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</heading>
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<heading id="433A0863FFD28D49FFA687F9FF4B4417" box="[100,237,1015,1034]" fontSize="8" level="3" pageId="9" pageNumber="28" reason="8">isolation of SLs</heading>
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</emphasis>
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</paragraph>
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</subSubSection>
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<subSubSection id="50D7EC84FFD28D4AFF478021FD6742B1" lastPageId="10" lastPageNumber="29" pageId="9" pageNumber="28" type="description">
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<paragraph id="1872BF0FFFD28D49FF478021FB1944AC" blockId="9.[100,771,1070,1982]" lastBlockId="9.[818,1487,987,1201]" pageId="9" pageNumber="28">
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Dried and powdered flowering heads of
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<taxonomicName id="DFCDC48CFFD28D49FDC78021FD29445F" box="[517,655,1071,1090]" class="Magnoliopsida" family="Asteraceae" genus="Hieracium" kingdom="Plantae" order="Asterales" pageId="9" pageNumber="28" phylum="Tracheophyta" rank="species" species="calophyllum">
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<emphasis id="2AB9631DFFD28D49FDC78021FDB2445F" bold="true" box="[517,532,1071,1090]" italics="true" pageId="9" pageNumber="28">H</emphasis>
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.
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<emphasis id="2AB9631DFFD28D49FDE38021FD29445F" bold="true" box="[545,655,1071,1090]" italics="true" pageId="9" pageNumber="28">calophyllum</emphasis>
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</taxonomicName>
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||
(
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<quantity id="DF3512EAFFD28D49FD5F8021FD60445F" box="[669,710,1071,1090]" metricMagnitude="-2" metricUnit="kg" metricValue="1.3" pageId="9" pageNumber="28" unit="g" value="13.0">13 g</quantity>
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) were macerated with
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||
<collectingCountry id="60DAFF9FFFD28D49FEC28044FEBB4440" box="[256,285,1098,1117]" name="Switzerland" pageId="9" pageNumber="28">CH</collectingCountry>
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<subScript id="8449BD4AFFD28D49FEDC805DFE81447D" attach="right" box="[286,295,1107,1120]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
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Cl
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||
<subScript id="8449BD4AFFD28D49FEF9805DFEE2447D" attach="left" box="[315,324,1107,1120]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
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||
(1:15 w/v) at room temperature for 48 h. The extract was filtered, and the residual material dried at room temperature and re-extracted with MeOH (1:15 w/v) by bimaceration procedure (2 × 48 h). Combined MeOH extracts were evaporated under reduced pressure using a rotary evaporator (Büchi Rotavapor R- II, Flawil,
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<collectingCountry id="60DAFF9FFFD28D49FF0980D8FEE744F4" box="[203,321,1238,1257]" name="Switzerland" pageId="9" pageNumber="28">Switzerland</collectingCountry>
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). The thus obtained dried MeOH extract (
|
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<quantity id="DF3512EAFFD28D49FD1C80D8FD5C44F4" box="[734,762,1238,1257]" metricMagnitude="-3" metricUnit="kg" metricValue="3.0" pageId="9" pageNumber="28" unit="g" value="3.0">3 g</quantity>
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) was then suspended in H
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<subScript id="8449BD4AFFD28D49FEAB80F4FED4451A" attach="both" box="[361,370,1274,1287]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
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O (300 ml), extracted successively with
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<collectingCountry id="60DAFF9FFFD28D49FFA68100FF27453C" box="[100,129,1294,1313]" name="Switzerland" pageId="9" pageNumber="28">CH</collectingCountry>
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||
<subScript id="8449BD4AFFD28D49FF408118FF2D453E" attach="right" box="[130,139,1302,1315]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
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Cl
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<subScript id="8449BD4AFFD28D49FF5D8118FF0E453E" attach="left" box="[159,168,1302,1315]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
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(300 ml), EtOAc (600 ml) and
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<emphasis id="2AB9631DFFD28D49FE2F8100FE5E453C" bold="true" box="[493,504,1294,1313]" italics="true" pageId="9" pageNumber="28">n</emphasis>
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-BuOH (600 ml), and then lyophilised. The thus obtained dry residue (
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<quantity id="DF3512EAFFD28D49FDD28124FDE64520" box="[528,576,1322,1341]" metricMagnitude="-4" metricUnit="kg" metricValue="5.0" pageId="9" pageNumber="28" unit="g" value="0.5">0.5 g</quantity>
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) was redissolved in H
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<subScript id="8449BD4AFFD28D49FFB68140FFDB4546" attach="both" box="[116,125,1358,1371]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
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O (
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<quantity id="DF3512EAFFD28D49FF598148FF6A4544" box="[155,204,1350,1369]" metricMagnitude="-6" metricUnit="kg" metricValue="8.0" pageId="9" pageNumber="28" unit="mg" value="8.0">8 mg</quantity>
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/ml) and subjected to preparative HPLC with MS detection, on an Agilent LC/MS System, equipped with Zorbax SB-C
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<subScript id="8449BD4AFFD28D49FD628164FD14456A" attach="left" box="[672,690,1386,1399]" fontSize="5" pageId="9" pageNumber="28">18</subScript>
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column (250 ×
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<quantity id="DF3512EAFFD28D49FF6D8173FF5F458D" box="[175,249,1405,1424]" metricMagnitude="-3" metricUnit="m" metricValue="9.4" pageId="9" pageNumber="28" unit="mm" value="9.4">9.4 mm</quantity>
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; 5 μm particle size). SLs were eluted using 0.1% (v/v) HCO
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<subScript id="8449BD4AFFD28D49FF5081ACFF3D45B2" attach="right" box="[146,155,1442,1455]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
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H/H
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<subScript id="8449BD4AFFD28D49FF0781ACFF6845B2" attach="both" box="[197,206,1442,1455]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
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O (mobile phase A) and MeOH (mobile phase B), and selected gradient program: 10–20% B (5 min), 20–30% B (5 min), isocratic 30% B (3 min), 30-20% B (7 min), 20–50% B (4 min), 50–90% B (6 min), with the total run time of 30 min, post run time of 5 min, flow rate of 2 ml/min, and the injection volume (
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<subScript id="8449BD4AFFD28D49FDD18207FD914603" attach="right" box="[531,567,1545,1566]" fontSize="5" pageId="9" pageNumber="28">Vinj</subScript>
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) of 100 μl. DAD was operating at
|
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<quantity id="DF3512EAFFD28D49FF23822BFE8C4625" box="[225,298,1573,1592]" metricMagnitude="-7" metricUnit="m" metricValue="2.1" pageId="9" pageNumber="28" unit="nm" value="210.0">210 nm</quantity>
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,
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<quantity id="DF3512EAFFD28D49FEF7822BFED94625" box="[309,383,1573,1592]" metricMagnitude="-7" metricUnit="m" metricValue="2.54" pageId="9" pageNumber="28" unit="nm" value="254.0">254 nm</quantity>
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,
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||
<quantity id="DF3512EAFFD28D49FE4B822BFE764625" box="[393,464,1573,1592]" metricMagnitude="-7" metricUnit="m" metricValue="3.2" pageId="9" pageNumber="28" unit="nm" value="320.0">320 nm</quantity>
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and
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<quantity id="DF3512EAFFD28D49FDC0822BFDEF4625" box="[514,585,1573,1592]" metricMagnitude="-7" metricUnit="m" metricValue="3.5" pageId="9" pageNumber="28" unit="nm" value="350.0">350 nm</quantity>
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wavelengths. MSD was recording in the positive ion and full-scan mode in the range of
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<emphasis id="2AB9631DFFD28D49FD25824FFFCB4672" bold="true" italics="true" pageId="9" pageNumber="28">m/ z</emphasis>
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80–700 to acquire Total Ion Chromatogram (TIC). Optimized ion source parameters were as follows: fragmentor voltage of 200 V, nebulising drying gas flow of 9 L/min at 350 ̊C, nebulizer pressure of 40 psi and capillary voltage of 3000 V. Splitter was set at 1000:1. Time-based fractionation afforded eleven fractions, F 1–11, which were collected during 0.5 min (F 1–3), 1 min (F 4–6, 9), or 3 min (F 7, 8, 10, 11). Fraction F 4 (
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||
<subScript id="8449BD4AFFD28D49FE8E830AFEF84704" attach="left" box="[332,350,1796,1817]" fontSize="5" pageId="9" pageNumber="28">tR</subScript>
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||
= 14.32 min) afforded compound
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||
<emphasis id="2AB9631DFFD28D49FD69830AFD11470A" bold="true" box="[683,695,1796,1815]" pageId="9" pageNumber="28">1</emphasis>
|
||
(
|
||
<quantity id="DF3512EAFFD28D49FD05830AFD51470A" box="[711,759,1796,1815]" metricMagnitude="-6" metricUnit="kg" metricValue="1.0" pageId="9" pageNumber="28" unit="mg" value="1.0">1 mg</quantity>
|
||
), F 6 (
|
||
<subScript id="8449BD4AFFD28D49FF5F832EFF094728" attach="left" box="[157,175,1824,1845]" fontSize="5" pageId="9" pageNumber="28">tR</subScript>
|
||
= 15.55 min) compound
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||
<emphasis id="2AB9631DFFD28D49FE76832EFE66472E" bold="true" box="[436,448,1824,1843]" pageId="9" pageNumber="28">2</emphasis>
|
||
(
|
||
<quantity id="DF3512EAFFD28D49FE16832EFDBF472E" box="[468,537,1824,1843]" metricMagnitude="-6" metricUnit="kg" metricValue="1.5" pageId="9" pageNumber="28" unit="mg" value="1.5">1.5 mg</quantity>
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||
), F 7 (
|
||
<subScript id="8449BD4AFFD28D49FDAB832EFDDD4728" attach="left" box="[617,635,1824,1845]" fontSize="5" pageId="9" pageNumber="28">tR</subScript>
|
||
= 16.72 min) compound
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||
<emphasis id="2AB9631DFFD28D49FF118332FF794752" bold="true" box="[211,223,1852,1871]" pageId="9" pageNumber="28">3</emphasis>
|
||
(
|
||
<quantity id="DF3512EAFFD28D49FF308332FE844752" box="[242,290,1852,1871]" metricMagnitude="-6" metricUnit="kg" metricValue="3.0" pageId="9" pageNumber="28" unit="mg" value="3.0">3 mg</quantity>
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||
) and F 9 (
|
||
<subScript id="8449BD4AFFD28D49FE568332FE00474C" attach="left" box="[404,422,1852,1873]" fontSize="5" pageId="9" pageNumber="28">tR</subScript>
|
||
= 31.25 min) compound
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||
<emphasis id="2AB9631DFFD28D49FD658332FD154752" bold="true" box="[679,691,1852,1871]" pageId="9" pageNumber="28">4</emphasis>
|
||
(
|
||
<quantity id="DF3512EAFFD28D49FD078332FD5E4752" box="[709,760,1852,1871]" metricMagnitude="-6" metricUnit="kg" metricValue="5.0" pageId="9" pageNumber="28" unit="mg" value="5.0">5 mg</quantity>
|
||
). Compounds
|
||
<emphasis id="2AB9631DFFD28D49FF188356FF404776" bold="true" box="[218,230,1880,1899]" pageId="9" pageNumber="28">2</emphasis>
|
||
and
|
||
<emphasis id="2AB9631DFFD28D49FED78356FE874776" bold="true" box="[277,289,1880,1899]" pageId="9" pageNumber="28">3</emphasis>
|
||
gradually decomposed upon one-week standing in D
|
||
<subScript id="8449BD4AFFD28D49FFB18372FFDA4794" attach="both" box="[115,124,1916,1929]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
|
||
O solution at temperature above 303 K. The mixture of
|
||
<emphasis id="2AB9631DFFD28D49FD6B837DFD13479B" bold="true" box="[681,693,1907,1926]" pageId="9" pageNumber="28">2</emphasis>
|
||
and its degradation products was further separated on Zorbax SB-C
|
||
<subScript id="8449BD4AFFD28D49FD608396FD1247B8" attach="left" box="[674,692,1944,1957]" fontSize="5" pageId="9" pageNumber="28">18</subScript>
|
||
column (50 ×
|
||
<quantity id="DF3512EAFFD28D49FF6183A5FF4A47A3" box="[163,236,1963,1982]" metricMagnitude="-3" metricUnit="m" metricValue="9.4" pageId="9" pageNumber="28" unit="mm" value="9.4">9.4 mm</quantity>
|
||
; 5 μm particle size) affording
|
||
<emphasis id="2AB9631DFFD28D49FDE883A5FDE447A3" bold="true" box="[554,578,1963,1982]" pageId="9" pageNumber="28">2a</emphasis>
|
||
(
|
||
<quantity id="DF3512EAFFD28D49FD9483A5FD3A47A3" box="[598,668,1963,1982]" metricMagnitude="-7" metricUnit="kg" metricValue="5.0" pageId="9" pageNumber="28" unit="mg" value="0.5">0.5 mg</quantity>
|
||
). For this purpose, mobile phases: 0.1% (v/v) HCO
|
||
<subScript id="8449BD4AFFD28D49FB0387EDFB6C43ED" attach="both" box="[1217,1226,995,1008]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
|
||
H/H
|
||
<subScript id="8449BD4AFFD28D49FB3787EDFB5843ED" attach="right" box="[1269,1278,995,1008]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
|
||
O (A) and MeOH (B), and fast gradient program: 20–30% B (5 min), 50–90% B (6 min), 90- 20% B (3 min), with the total run time of 15 min, flow rate of 2 ml/ min, and
|
||
<subScript id="8449BD4AFFD28D49FC4F8021FC084459" attach="left" box="[909,942,1071,1092]" fontSize="5" pageId="9" pageNumber="28">Vinj</subScript>
|
||
of 60 μl were used. The mixture of
|
||
<emphasis id="2AB9631DFFD28D49FAC18021FAA9445F" bold="true" box="[1283,1295,1071,1090]" pageId="9" pageNumber="28">3</emphasis>
|
||
and its degradation products was fractioned using the same column, mobile phases, flow rate and
|
||
<subScript id="8449BD4AFFD28D49FC4B8068FC0C4461" attach="left" box="[905,938,1126,1148]" fontSize="5" pageId="9" pageNumber="28">Vinj</subScript>
|
||
, with slightly different gradient program, i.e. 20–30% B (5 min), 30-20% B (5 min), 50–90% B (2 min), 90-20% B (1 min), and the total run time of 14 min, affording
|
||
<emphasis id="2AB9631DFFD28D49FB6F8090FB1F44AC" bold="true" box="[1197,1209,1182,1201]" pageId="9" pageNumber="28">4</emphasis>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD28D49FCF080D6FAF2451A" blockId="9.[818,1487,1240,1427]" pageId="9" pageNumber="28">
|
||
<heading id="433A0863FFD28D49FCF080D6FAF2451A" centered="true" fontSize="8" level="3" pageId="9" pageNumber="28" reason="8">
|
||
<emphasis id="2AB9631DFFD28D49FCF080D6FAF2451A" italics="true" pageId="9" pageNumber="28">
|
||
<emphasis id="2AB9631DFFD28D49FCF080D6FBE944F6" bold="true" box="[818,1103,1240,1259]" italics="true" pageId="9" pageNumber="28">4.3.1. Calophyllamine B (1, 3</emphasis>
|
||
β
|
||
<emphasis id="2AB9631DFFD28D49FB9880D6FBCF44F6" bold="true" box="[1114,1129,1240,1259]" italics="true" pageId="9" pageNumber="28">-(</emphasis>
|
||
β
|
||
<emphasis id="2AB9631DFFD28D49FBB780D6FAE544F6" bold="true" box="[1141,1347,1240,1259]" italics="true" pageId="9" pageNumber="28">-glucopyranosyl)-oxy-8</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD28D49FA8C80D6FA1A44F6" bold="true" box="[1358,1468,1240,1259]" italics="true" pageId="9" pageNumber="28">-hydroxy-13</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD28D49FA0A80D6FBCD451A" bold="true" italics="true" pageId="9" pageNumber="28">- (N-prolyl)-eudesma-1,4(15)-dien-5</emphasis>
|
||
α,
|
||
<emphasis id="2AB9631DFFD28D49FBBF80FAFB2F451A" bold="true" box="[1149,1161,1268,1287]" italics="true" pageId="9" pageNumber="28">6</emphasis>
|
||
β,
|
||
<emphasis id="2AB9631DFFD28D49FB5880FAFB00451A" bold="true" box="[1178,1190,1268,1287]" italics="true" pageId="9" pageNumber="28">7</emphasis>
|
||
α,
|
||
<emphasis id="2AB9631DFFD28D49FB7580FAFB69451A" bold="true" box="[1207,1231,1268,1287]" italics="true" pageId="9" pageNumber="28">11</emphasis>
|
||
β
|
||
<emphasis id="2AB9631DFFD28D49FB1880FAFAF2451A" bold="true" box="[1242,1364,1268,1287]" italics="true" pageId="9" pageNumber="28">H-12,6-olide)</emphasis>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD28D49FC91811EFB6E458E" blockId="9.[818,1487,1240,1427]" pageId="9" pageNumber="28">
|
||
White solid [
|
||
<emphasis id="2AB9631DFFD28D49FC11811EFC79453E" box="[979,991,1296,1315]" italics="true" pageId="9" pageNumber="28">α</emphasis>
|
||
]
|
||
<subScript id="8449BD4AFFD28D49FC2A8116FC554538" attach="left" box="[1000,1011,1304,1317]" fontSize="5" pageId="9" pageNumber="28">D</subScript>
|
||
+106 (
|
||
<emphasis id="2AB9631DFFD28D49FB85811EFBF6453E" bold="true" box="[1095,1104,1296,1315]" italics="true" pageId="9" pageNumber="28">c</emphasis>
|
||
0.5, H
|
||
<subScript id="8449BD4AFFD28D49FB548116FB394538" attach="both" box="[1174,1183,1304,1317]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
|
||
O).
|
||
<superScript id="EFB81247FFD28D49FB048105FB694505" attach="right" box="[1222,1231,1291,1304]" fontSize="5" pageId="9" pageNumber="28">1</superScript>
|
||
H,
|
||
<superScript id="EFB81247FFD28D49FB2C8105FAA64505" attach="right" box="[1262,1280,1291,1304]" fontSize="5" pageId="9" pageNumber="28">13</superScript>
|
||
C, DEPT, HMBC, and NOESY spectroscopic data are presented in
|
||
<tableCitation id="554F8AB4FFD28D49FB388122FAEE4522" box="[1274,1352,1324,1343]" captionStart="Table 2" captionStartId="3.[99,149,551,568]" captionTargetBox="[115,1924,612,1497]" captionTargetPageId="3" captionText="Table 2 1 H, 13 C, DEPT, HMBC, and NOESY/ROESY data of compounds 1, 2 and 3 in D O." pageId="9" pageNumber="28">Table 2</tableCitation>
|
||
. HRMS
|
||
<emphasis id="2AB9631DFFD28D49FA678122FA6C4522" bold="true" box="[1445,1482,1324,1343]" italics="true" pageId="9" pageNumber="28">m/z</emphasis>
|
||
: 540.2456 [M + H]
|
||
<superScript id="EFB81247FFD28D49FC31814DFBA5454D" attach="left" box="[1011,1027,1347,1360]" fontSize="5" pageId="9" pageNumber="28">+</superScript>
|
||
(calcd 540.2439 for [M + H]
|
||
<superScript id="EFB81247FFD28D49FAF7814DFAE3454D" attach="left" box="[1333,1349,1347,1360]" fontSize="5" pageId="9" pageNumber="28">+</superScript>
|
||
C
|
||
<subScript id="8449BD4AFFD28D49FA9F815EFAC94540" attach="right" box="[1373,1391,1360,1373]" fontSize="5" pageId="9" pageNumber="28">26</subScript>
|
||
H
|
||
<subScript id="8449BD4AFFD28D49FABC815EFA364540" attach="both" box="[1406,1424,1360,1373]" fontSize="5" pageId="9" pageNumber="28">38</subScript>
|
||
NO
|
||
<subScript id="8449BD4AFFD28D49FA6D815EFA674540" attach="left" box="[1455,1473,1360,1373]" fontSize="5" pageId="9" pageNumber="28">11</subScript>
|
||
), qTOF-MS/MS (15 eV)
|
||
<emphasis id="2AB9631DFFD28D49FBC6816AFB8E456A" bold="true" box="[1028,1064,1380,1399]" italics="true" pageId="9" pageNumber="28">m/z</emphasis>
|
||
(rel. int.): 540.2456 (100), 494.2445 (22), 316.2084 (3), 128.0718 (4), 100.0759 (4).
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD28D49FCF081B4FB7245F4" blockId="9.[818,1487,1466,1624]" pageId="9" pageNumber="28">
|
||
<heading id="433A0863FFD28D49FCF081B4FB7245F4" centered="true" fontSize="8" level="3" pageId="9" pageNumber="28" reason="8">
|
||
<emphasis id="2AB9631DFFD28D49FCF081B4FB7245F4" italics="true" pageId="9" pageNumber="28">
|
||
<emphasis id="2AB9631DFFD28D49FCF081B4FBDA45D0" bold="true" box="[818,1148,1466,1485]" italics="true" pageId="9" pageNumber="28">4.3.2. Calophyllamine A (2, 3</emphasis>
|
||
β,
|
||
<emphasis id="2AB9631DFFD28D49FB4E81B4FB3E45D0" bold="true" box="[1164,1176,1466,1485]" italics="true" pageId="9" pageNumber="28">8</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD28D49FB6781B4FA8245D0" bold="true" box="[1189,1316,1466,1485]" italics="true" pageId="9" pageNumber="28">-dihydroxy-13</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD28D49FAF281B4FC4A45F4" bold="true" italics="true" pageId="9" pageNumber="28">-(N-prolyl)-guaia- 4(15),10(14)-dien-5</emphasis>
|
||
α,
|
||
<emphasis id="2AB9631DFFD28D49FC3F81D8FBAF45F4" bold="true" box="[1021,1033,1494,1513]" italics="true" pageId="9" pageNumber="28">6</emphasis>
|
||
β,
|
||
<emphasis id="2AB9631DFFD28D49FBD881D8FB8045F4" bold="true" box="[1050,1062,1494,1513]" italics="true" pageId="9" pageNumber="28">7</emphasis>
|
||
α,
|
||
<emphasis id="2AB9631DFFD28D49FBFA81D8FBF645F4" bold="true" box="[1080,1104,1494,1513]" italics="true" pageId="9" pageNumber="28">11</emphasis>
|
||
β
|
||
<emphasis id="2AB9631DFFD28D49FB9981D8FB7245F4" bold="true" box="[1115,1236,1494,1513]" italics="true" pageId="9" pageNumber="28">H-12,6-olide)</emphasis>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD28D49FC9181FCFA874645" blockId="9.[818,1487,1466,1624]" pageId="9" pageNumber="28">
|
||
White solid.
|
||
<superScript id="EFB81247FFD28D49FC1181E3FC7A45E7" attach="right" box="[979,988,1517,1530]" fontSize="5" pageId="9" pageNumber="28">1</superScript>
|
||
H,
|
||
<superScript id="EFB81247FFD28D49FC3E81E3FBA845E7" attach="right" box="[1020,1038,1517,1530]" fontSize="5" pageId="9" pageNumber="28">13</superScript>
|
||
C, HMBC, ROESY spectroscopic data are presented in
|
||
<tableCitation id="554F8AB4FFD28D49FC4E8203FC77463D" box="[908,977,1549,1568]" captionStart="Table 2" captionStartId="3.[99,149,551,568]" captionTargetBox="[115,1924,612,1497]" captionTargetPageId="3" captionText="Table 2 1 H, 13 C, DEPT, HMBC, and NOESY/ROESY data of compounds 1, 2 and 3 in D O." pageId="9" pageNumber="28">Table 2</tableCitation>
|
||
. HRMS
|
||
<emphasis id="2AB9631DFFD28D49FBDF8203FBE4463D" bold="true" box="[1053,1090,1549,1568]" italics="true" pageId="9" pageNumber="28">m/z</emphasis>
|
||
: 378.1916 [M + H]
|
||
<superScript id="EFB81247FFD28D49FAC38207FAB7460B" attach="left" box="[1281,1297,1545,1558]" fontSize="5" pageId="9" pageNumber="28">+</superScript>
|
||
(calcd 378.1911 for [M+H]
|
||
<superScript id="EFB81247FFD28D49FCB9822BFC2D462F" attach="left" box="[891,907,1573,1586]" fontSize="5" pageId="9" pageNumber="28">+</superScript>
|
||
C
|
||
<subScript id="8449BD4AFFD28D49FC63823CFC154622" attach="right" box="[929,947,1586,1599]" fontSize="5" pageId="9" pageNumber="28">20</subScript>
|
||
H
|
||
<subScript id="8449BD4AFFD28D49FC01823CFC734622" attach="both" box="[963,981,1586,1599]" fontSize="5" pageId="9" pageNumber="28">28</subScript>
|
||
NO
|
||
<subScript id="8449BD4AFFD28D49FC31823CFC5A4622" attach="left" box="[1011,1020,1586,1599]" fontSize="5" pageId="9" pageNumber="28">6</subScript>
|
||
), qTOF-MS/MS (15 eV)
|
||
<emphasis id="2AB9631DFFD28D49FB268227FAAE4621" bold="true" box="[1252,1288,1577,1596]" italics="true" pageId="9" pageNumber="28">m/z</emphasis>
|
||
(rel. int.): 378.1892 (100), 332.1865 (22), 128.0710 (10), 100.0729 (4).
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD28D49FCF08271FACB46B3" blockId="9.[818,1487,1663,1878]" pageId="9" pageNumber="28">
|
||
<heading id="433A0863FFD28D49FCF08271FACB46B3" centered="true" fontSize="8" level="3" pageId="9" pageNumber="28" reason="8">
|
||
<emphasis id="2AB9631DFFD28D49FCF08271FACB46B3" italics="true" pageId="9" pageNumber="28">
|
||
<emphasis id="2AB9631DFFD28D49FCF08271FBE9468F" bold="true" box="[818,1103,1663,1682]" italics="true" pageId="9" pageNumber="28">4.3.3. 8-Epiixerisamine A (3, 3</emphasis>
|
||
β
|
||
<emphasis id="2AB9631DFFD28D49FB988271FBCF468F" bold="true" box="[1114,1129,1663,1682]" italics="true" pageId="9" pageNumber="28">-(</emphasis>
|
||
β
|
||
<emphasis id="2AB9631DFFD28D49FBB78271FAE5468F" bold="true" box="[1141,1347,1663,1682]" italics="true" pageId="9" pageNumber="28">-glucopyranosyl)-oxy-8</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD28D49FA8C8271FA1A468F" bold="true" box="[1358,1468,1663,1682]" italics="true" pageId="9" pageNumber="28">-hydroxy-13</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD28D49FA0A8271FB2246B3" bold="true" italics="true" pageId="9" pageNumber="28">- (N-prolyl)-guaia-4(15),10(14)-dien-5</emphasis>
|
||
α,
|
||
<emphasis id="2AB9631DFFD28D49FB548295FB0446B3" bold="true" box="[1174,1186,1691,1710]" italics="true" pageId="9" pageNumber="28">6</emphasis>
|
||
β,
|
||
<emphasis id="2AB9631DFFD28D49FB718295FB1946B3" bold="true" box="[1203,1215,1691,1710]" italics="true" pageId="9" pageNumber="28">7</emphasis>
|
||
α,
|
||
<emphasis id="2AB9631DFFD28D49FB128295FB4E46B3" bold="true" box="[1232,1256,1691,1710]" italics="true" pageId="9" pageNumber="28">11</emphasis>
|
||
β
|
||
<emphasis id="2AB9631DFFD28D49FB368295FACB46B3" bold="true" box="[1268,1389,1691,1710]" italics="true" pageId="9" pageNumber="28">H-12,6-olide)</emphasis>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD28D49FC9182B9FC4C474B" blockId="9.[818,1487,1663,1878]" pageId="9" pageNumber="28">
|
||
White solid [
|
||
<emphasis id="2AB9631DFFD28D49FC1782B9FC4746D7" box="[981,993,1719,1738]" italics="true" pageId="9" pageNumber="28">α</emphasis>
|
||
]
|
||
<subScript id="8449BD4AFFD28D49FC2B82B1FC5246D1" attach="left" box="[1001,1012,1727,1740]" fontSize="5" pageId="9" pageNumber="28">D</subScript>
|
||
−3.6 (
|
||
<emphasis id="2AB9631DFFD28D49FB8182B9FBEA46D7" bold="true" box="[1091,1100,1719,1738]" italics="true" pageId="9" pageNumber="28">c</emphasis>
|
||
1.2, H
|
||
<subScript id="8449BD4AFFD28D49FB5682B1FB3B46D1" attach="both" box="[1172,1181,1727,1740]" fontSize="5" pageId="9" pageNumber="28">2</subScript>
|
||
O).
|
||
<superScript id="EFB81247FFD28D49FB0682BCFB6B46A2" attach="right" box="[1220,1229,1714,1727]" fontSize="5" pageId="9" pageNumber="28">1</superScript>
|
||
H,
|
||
<superScript id="EFB81247FFD28D49FB2F82BCFB5946A2" attach="right" box="[1261,1279,1714,1727]" fontSize="5" pageId="9" pageNumber="28">13</superScript>
|
||
C, DEPT, ROESY and HMBC spectroscopic data are presented in
|
||
<tableCitation id="554F8AB4FFD28D49FB3A82DDFAE046FB" box="[1272,1350,1747,1766]" captionStart="Table 2" captionStartId="3.[99,149,551,568]" captionTargetBox="[115,1924,612,1497]" captionTargetPageId="3" captionText="Table 2 1 H, 13 C, DEPT, HMBC, and NOESY/ROESY data of compounds 1, 2 and 3 in D O." pageId="9" pageNumber="28">Table 2</tableCitation>
|
||
. HRMS
|
||
<emphasis id="2AB9631DFFD28D49FA6782DDFA6C46FB" bold="true" box="[1445,1482,1747,1766]" italics="true" pageId="9" pageNumber="28">m/z</emphasis>
|
||
: 540.2456 [M + H]
|
||
<superScript id="EFB81247FFD28D49FC3182E4FBA546EA" attach="left" box="[1011,1027,1770,1783]" fontSize="5" pageId="9" pageNumber="28">+</superScript>
|
||
(calcd 540.2439 for [M + H]
|
||
<superScript id="EFB81247FFD28D49FAF782E4FAE346EA" attach="left" box="[1333,1349,1770,1783]" fontSize="5" pageId="9" pageNumber="28">+</superScript>
|
||
C
|
||
<subScript id="8449BD4AFFD28D49FA9F82F9FAC94719" attach="right" box="[1373,1391,1783,1796]" fontSize="5" pageId="9" pageNumber="28">26</subScript>
|
||
H
|
||
<subScript id="8449BD4AFFD28D49FABC82F9FA364719" attach="both" box="[1406,1424,1783,1796]" fontSize="5" pageId="9" pageNumber="28">38</subScript>
|
||
NO
|
||
<subScript id="8449BD4AFFD28D49FA6D82F9FA674719" attach="left" box="[1455,1473,1783,1796]" fontSize="5" pageId="9" pageNumber="28">11</subScript>
|
||
), qTOF-MS/MS (15 eV)
|
||
<emphasis id="2AB9631DFFD28D49FBC78305FB8C4703" bold="true" box="[1029,1066,1803,1822]" italics="true" pageId="9" pageNumber="28">m/z</emphasis>
|
||
(rel. int.): 540.2456 (100), 494.2414 (9), 378.1885 (22), 360.1806 (5), 332.1909 (5), 316.1909 (3), 128.0734 (10), 100.0886 (6).
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD28D49FCF08373FB4047B1" blockId="9.[818,1488,1917,1994]" pageId="9" pageNumber="28">
|
||
<heading id="433A0863FFD28D49FCF08373FB4047B1" centered="true" fontSize="8" level="3" pageId="9" pageNumber="28" reason="8">
|
||
<emphasis id="2AB9631DFFD28D49FCF08373FB4047B1" italics="true" pageId="9" pageNumber="28">
|
||
<emphasis id="2AB9631DFFD28D49FCF08373FB8B478D" bold="true" box="[818,1069,1917,1936]" italics="true" pageId="9" pageNumber="28">4.3.4. Crepiside E (4, 3</emphasis>
|
||
β
|
||
<emphasis id="2AB9631DFFD28D49FBFA8373FBE1478D" bold="true" box="[1080,1095,1917,1936]" italics="true" pageId="9" pageNumber="28">-(</emphasis>
|
||
β
|
||
<emphasis id="2AB9631DFFD28D49FB908373FA93478D" bold="true" box="[1106,1333,1917,1936]" italics="true" pageId="9" pageNumber="28">-D-glucopyranosyl)-oxy-8</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD28D49FA838373FB9047B1" bold="true" italics="true" pageId="9" pageNumber="28">-hydroxy-guaia- 4(15),10(14),11(13)-trien-5</emphasis>
|
||
α,
|
||
<emphasis id="2AB9631DFFD28D49FB8A8397FBF247B1" bold="true" box="[1096,1108,1945,1964]" italics="true" pageId="9" pageNumber="28">6</emphasis>
|
||
β,
|
||
<emphasis id="2AB9631DFFD28D49FBA78397FBD747B1" bold="true" box="[1125,1137,1945,1964]" italics="true" pageId="9" pageNumber="28">7</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD28D49FBBF8397FB4047B1" bold="true" box="[1149,1254,1945,1964]" italics="true" pageId="9" pageNumber="28">-12,6-olide)</emphasis>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD28D49FC9183BBFA7647D5" blockId="9.[818,1488,1917,1994]" box="[851,1488,1968,1994]" pageId="9" pageNumber="28">
|
||
Brownish gum. [
|
||
<emphasis id="2AB9631DFFD28D49FC3383BAFC5B47DA" box="[1009,1021,1972,1991]" italics="true" pageId="9" pageNumber="28">α</emphasis>
|
||
]
|
||
<subScript id="8449BD4AFFD28D49FBC483B3FBB747D7" attach="left" box="[1030,1041,1981,1994]" fontSize="5" pageId="9" pageNumber="28">D</subScript>
|
||
+24.3 (c 1.2, MeOH).
|
||
<superScript id="EFB81247FFD28D49FB3083BEFB5D47A0" attach="right" box="[1266,1275,1968,1981]" fontSize="5" pageId="9" pageNumber="28">1</superScript>
|
||
H,
|
||
<superScript id="EFB81247FFD28D49FAD583BEFA8F47A0" attach="right" box="[1303,1321,1968,1981]" fontSize="5" pageId="9" pageNumber="28">13</superScript>
|
||
C, COSY, NOESY,
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD18D4AFFA68491FE184123" blockId="10.[100,770,159,318]" pageId="10" pageNumber="29">
|
||
TOCSY, HMBC spectroscopic data are presented in
|
||
<tableCitation id="554F8AB4FFD18D4AFD858491FD3F40AF" box="[583,665,159,178]" captionStart="Table 1" captionStartId="1.[100,150,1075,1092]" captionTargetPageId="1" captionText="Table 1 List of the investigated Hieracium species with infrageneric classification." pageId="10" pageNumber="29">Table S1</tableCitation>
|
||
. HRMS
|
||
<emphasis id="2AB9631DFFD18D4AFD258491FFCB40D3" bold="true" italics="true" pageId="10" pageNumber="29">m/ z</emphasis>
|
||
: 447.1645 [M + Na]
|
||
<superScript id="EFB81247FFD18D4AFEFA84B9FEEE40D9" attach="left" box="[312,328,183,196]" fontSize="5" pageId="10" pageNumber="29">+</superScript>
|
||
(calcd 447.1625 for [M + Na]
|
||
<superScript id="EFB81247FFD18D4AFDA984B9FDDD40D9" attach="left" box="[619,635,183,196]" fontSize="5" pageId="10" pageNumber="29">+</superScript>
|
||
C
|
||
<subScript id="8449BD4AFFD18D4AFD4C84CAFD0640CC" attach="right" box="[654,672,196,209]" fontSize="5" pageId="10" pageNumber="29">21</subScript>
|
||
H
|
||
<subScript id="8449BD4AFFD18D4AFD6D84CAFD6740CC" attach="both" box="[687,705,196,209]" fontSize="5" pageId="10" pageNumber="29">28</subScript>
|
||
O
|
||
<subScript id="8449BD4AFFD18D4AFD1384CAFD7C40CC" attach="right" box="[721,730,196,209]" fontSize="5" pageId="10" pageNumber="29">9</subScript>
|
||
Na), qTOF-MS/MS (25 eV)
|
||
<emphasis id="2AB9631DFFD18D4AFEFA84D9FEFB40F7" bold="true" box="[312,349,215,234]" italics="true" pageId="10" pageNumber="29">m/z</emphasis>
|
||
(rel. int.): 263.1304 (29); 245.1204 (16); 227.1058 (100); 217.1268 (57); 209.1308 (14); 201.1261 (14); 199.1140 (62); 183.1078 (11); 181.104 (72); 175.0810 (5); 171.1170 (55); 143.0926 (12); 131.0869 (19).
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD18D4AFFA68568FE314188" blockId="10.[100,770,358,684]" pageId="10" pageNumber="29">
|
||
<heading id="433A0863FFD18D4AFFA68568FE314188" centered="true" fontSize="8" level="3" pageId="10" pageNumber="29" reason="8">
|
||
<emphasis id="2AB9631DFFD18D4AFFA68568FE314188" italics="true" pageId="10" pageNumber="29">
|
||
<emphasis id="2AB9631DFFD18D4AFFA68568FE1E4164" bold="true" box="[100,440,358,377]" italics="true" pageId="10" pageNumber="29">4.3.5. Desacylcynaropicrin (2a, 3</emphasis>
|
||
β,
|
||
<emphasis id="2AB9631DFFD18D4AFE0B8568FE734164" bold="true" box="[457,469,358,377]" italics="true" pageId="10" pageNumber="29">8</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD18D4AFE238568FF414188" bold="true" italics="true" pageId="10" pageNumber="29">-dihydroxy-guaia-4(15),10(14), 11(13)-trien-5</emphasis>
|
||
α,
|
||
<emphasis id="2AB9631DFFD18D4AFF3A858CFEA24188" bold="true" box="[248,260,386,405]" italics="true" pageId="10" pageNumber="29">6</emphasis>
|
||
β,
|
||
<emphasis id="2AB9631DFFD18D4AFED7858CFE874188" bold="true" box="[277,289,386,405]" italics="true" pageId="10" pageNumber="29">7</emphasis>
|
||
α
|
||
<emphasis id="2AB9631DFFD18D4AFEEF858CFE314188" bold="true" box="[301,407,386,405]" italics="true" pageId="10" pageNumber="29">-12,6-olide)</emphasis>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="1872BF0FFFD18D4AFF478590FD6742B1" blockId="10.[100,770,358,684]" pageId="10" pageNumber="29">
|
||
White solid, [
|
||
<emphasis id="2AB9631DFFD18D4AFEC98590FEB141AC" box="[267,279,414,433]" italics="true" pageId="10" pageNumber="29">α</emphasis>
|
||
]
|
||
<subScript id="8449BD4AFFD18D4AFEE285A9FE8D41A9" attach="left" box="[288,299,423,436]" fontSize="5" pageId="10" pageNumber="29">D</subScript>
|
||
= +34 (
|
||
<emphasis id="2AB9631DFFD18D4AFE528590FE3F41AC" bold="true" box="[400,409,414,433]" italics="true" pageId="10" pageNumber="29">c</emphasis>
|
||
0.5, H
|
||
<subScript id="8449BD4AFFD18D4AFE1D85A9FE4E41A9" attach="both" box="[479,488,423,436]" fontSize="5" pageId="10" pageNumber="29">2</subScript>
|
||
O).
|
||
<superScript id="EFB81247FFD18D4AFDCD8594FDBE41BA" attach="right" box="[527,536,410,423]" fontSize="5" pageId="10" pageNumber="29">1</superScript>
|
||
H NMR (500 MHz, D
|
||
<subScript id="8449BD4AFFD18D4AFD2185A9FD4A41A9" attach="both" box="[739,748,423,436]" fontSize="5" pageId="10" pageNumber="29">2</subScript>
|
||
O, TMS):
|
||
<emphasis id="2AB9631DFFD18D4AFF6185B4FF0841D0" box="[163,174,442,461]" italics="true" pageId="10" pageNumber="29">δ</emphasis>
|
||
<subScript id="8449BD4AFFD18D4AFF6F85CCFF1F41D2" attach="left" box="[173,185,450,463]" fontSize="5" pageId="10" pageNumber="29">H</subScript>
|
||
6.25 (d,
|
||
<emphasis id="2AB9631DFFD18D4AFECD85B4FEBF41D0" bold="true" box="[271,281,442,461]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 3.4 Hz, H-13b); 6.16 (d,
|
||
<emphasis id="2AB9631DFFD18D4AFDDE85B4FD8041D0" bold="true" box="[540,550,442,461]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 3.0 Hz, H-13a); 5.45 (s, H-15b); 5.34 (s, H-15a); 5.16 (s, H-14b); 5.04 (s, H-14a); 4.64 (t,
|
||
<emphasis id="2AB9631DFFD18D4AFFA685FCFFC84218" bold="true" box="[100,110,498,517]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 6.2 Hz, H-3); 4.36 (t,
|
||
<emphasis id="2AB9631DFFD18D4AFE9185FCFEFB4218" bold="true" box="[339,349,498,517]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 9.8 Hz, H-6); 4.06 (dd,
|
||
<emphasis id="2AB9631DFFD18D4AFD9185FCFDFB4218" bold="true" box="[595,605,498,517]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 7.6, 4.7 Hz, H- 8); 3.06 (m, H-1); 2.99 (q,
|
||
<emphasis id="2AB9631DFFD18D4AFEAB8600FED5423C" bold="true" box="[361,371,526,545]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 9.9 Hz, H-5); 3.00 (t,
|
||
<emphasis id="2AB9631DFFD18D4AFDA28600FDCC423C" bold="true" box="[608,618,526,545]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 9.8 Hz, H-7); 2.72 (dd,
|
||
<emphasis id="2AB9631DFFD18D4AFF048624FF764220" bold="true" box="[198,208,554,573]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 13.6, 4.9 Hz, H-9β); 2.33 (dd,
|
||
<emphasis id="2AB9631DFFD18D4AFDDB8624FD854220" bold="true" box="[537,547,554,573]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 14.6, 3.8 Hz, H-9α); 2.22 (td,
|
||
<emphasis id="2AB9631DFFD18D4AFF7E8648FF604244" bold="true" box="[188,198,582,601]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 13.5, 7.0 Hz, H-2β); 1.76 (td,
|
||
<emphasis id="2AB9631DFFD18D4AFE3C8648FDAE4244" bold="true" box="[510,520,582,601]" italics="true" pageId="10" pageNumber="29">J</emphasis>
|
||
= 11.9, 9.2 Hz, H-2α).
|
||
<superScript id="EFB81247FFD18D4AFD21864FFD534253" attach="right" box="[739,757,577,590]" fontSize="5" pageId="10" pageNumber="29">13</superScript>
|
||
C NMR (125 MHz, D
|
||
<subScript id="8449BD4AFFD18D4AFEDE8664FE83426A" attach="both" box="[284,293,618,631]" fontSize="5" pageId="10" pageNumber="29">2</subScript>
|
||
O):
|
||
<emphasis id="2AB9631DFFD18D4AFE8C866FFEFF4269" box="[334,345,609,628]" italics="true" pageId="10" pageNumber="29">δ</emphasis>
|
||
<subScript id="8449BD4AFFD18D4AFE9A8664FEC4426A" attach="left" box="[344,354,618,631]" fontSize="5" pageId="10" pageNumber="29">C</subScript>
|
||
173.0 (C-12); 151.6 (C-4); 141.6 (C-10); 123.7 (C-13); 116.8 (C-14); 112.4 (C-15); 79.6 (C-6); 72.6 (C-3); 71.2 (C-8); 50.1 (C-7); 49.3 (C-5); 44.7 (C-1); 40.2 (C-9); 37.6 (C-2).
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |