389 lines
41 KiB
XML
389 lines
41 KiB
XML
<document id="588B2CF7D1AA1641471898082A89E1A3" ID-DOI="10.1016/j.phytochem.2015.08.003" ID-ISSN="1873-3700" ID-Zenodo-Dep="10489001" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="jonas" IM.materialsCitations_approvedBy="jonas" IM.metadata_approvedBy="felipe" IM.taxonomicNames_approvedBy="jonas" IM.treatments_approvedBy="jonas" checkinTime="1704956715174" checkinUser="felipe" docAuthor="Ogorodnikova, Anna V., Mukhitova, Fakhima K. & Grechkin, Alexander N." docDate="2015" docId="03ED841CFFF3FFD4FFFCFCEE6856F93B" docLanguage="en" docName="Phytochemistry.118.42-50.pdf" docOrigin="Phytochemistry 118" docSource="http://dx.doi.org/10.5281/zenodo.8250065" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Selaginella martensii Spring" docType="treatment" docVersion="1" lastPageNumber="44" masterDocId="FFD4FC64FFF2FFD6FF8EFF9B6C30FFDF" masterDocTitle="Oxylipins in the spikemoss Selaginella martensii: Detection of divinyl ethers, 12 - oxophytodienoic acid and related cyclopentenones" masterLastPageNumber="50" masterPageNumber="42" pageNumber="43" updateTime="1705622638938" updateUser="jonas">
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<mods:mods id="0F06B2598F0F8C45849B702384B7EDC1" xmlns:mods="http://www.loc.gov/mods/v3">
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<mods:titleInfo id="B40306BFBC2EAEA5970541DBD25BC80A">
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<mods:title id="B13CC866BA71F93F014AA493B5E05771">Oxylipins in the spikemoss Selaginella martensii: Detection of divinyl ethers, 12 - oxophytodienoic acid and related cyclopentenones</mods:title>
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<mods:name id="756F5AE3E146CFF60EF3029A487C8BE6" type="personal">
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<mods:role id="2A6F91E352321812CF86C7EDB30D181D">
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<mods:roleTerm id="50DF63452B9B045501F7299A3177F8A9">Author</mods:roleTerm>
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<mods:namePart id="FB866AE685683D2D35324CCA3BC2CF61">Ogorodnikova, Anna V.</mods:namePart>
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</mods:name>
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<mods:name id="0C332DD724DF83D54ED7ABC1F67D238E" type="personal">
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<mods:role id="449055E95F5D4C49DDAA5650FA20885E">
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<mods:roleTerm id="357891A835C68F54195D12A0F77D8488">Author</mods:roleTerm>
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</mods:role>
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<mods:namePart id="179A60424CDD433035B5723DBD6FD731">Mukhitova, Fakhima K.</mods:namePart>
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</mods:name>
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<mods:name id="6082D3F608D87E6EBB28A6C4AA5D5F7A" type="personal">
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<mods:role id="77534100BCDA461FEB7C40B5A2447D3A">
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<mods:roleTerm id="44CDE224912F6D85D5080A3338523AD3">Author</mods:roleTerm>
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</mods:role>
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<mods:namePart id="7A69B7457D78BAAF9B8BDEBBD952F137">Grechkin, Alexander N.</mods:namePart>
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</mods:name>
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<mods:typeOfResource id="54A245B27616B8D8A9DCB8256A66606C">text</mods:typeOfResource>
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<mods:titleInfo id="A67E371EE489B1B32BF21EF1F615A5C9">
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<mods:title id="07226385A24385A1D58127BD2CC93C66">Phytochemistry</mods:title>
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</mods:titleInfo>
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<mods:part id="49C074BC07A03AB065F049277B1CF8A4">
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<mods:date id="975B2D8A65AE70983F66455A4D5FCE92">2015</mods:date>
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<mods:detail id="5F9CC289A8D8380C28394AE5C3606CD2" type="pubDate">
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<mods:number id="30427E07A90DE24508A40FAC3CA33FAC">2015-08-12</mods:number>
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</mods:detail>
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<mods:detail id="914937E8B944011223DCE85C15FFC879" type="volume">
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<mods:number id="FC21CE76D1FC2766B5E8AE01CC589EFF">118</mods:number>
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</mods:detail>
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<mods:extent id="BC80C056C49C3F99DC072A8AAE88CB9B" unit="page">
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<mods:start id="09AA22F2FFCCF9DBF17B5431C6A76A49">42</mods:start>
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<mods:end id="EF35741A8F38EA9316FED72AA94CAFF6">50</mods:end>
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</mods:extent>
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</mods:part>
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<mods:location id="ACAF30BC2B4F6DA06F524C0D67697CA0">
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<mods:url id="0B99ADDA5FEA48B8B78E00D6F5E29E33">http://dx.doi.org/10.5281/zenodo.8250065</mods:url>
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</mods:location>
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<mods:classification id="CBAB6C310B00546146316978FC13C92E">journal article</mods:classification>
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<mods:identifier id="AD5D0231B6BB283B2813245B20C11571" type="DOI">10.1016/j.phytochem.2015.08.003</mods:identifier>
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<mods:identifier id="D307C3389C9DE49806C5FE3A9B4B7EC9" type="ISSN">1873-3700</mods:identifier>
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<mods:identifier id="293D7E367192B899BFF388460506821E" type="Zenodo-Dep">10489001</mods:identifier>
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</mods:mods>
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<treatment id="03ED841CFFF3FFD4FFFCFCEE6856F93B" LSID="urn:lsid:plazi:treatment:03ED841CFFF3FFD4FFFCFCEE6856F93B" httpUri="http://treatment.plazi.org/id/03ED841CFFF3FFD4FFFCFCEE6856F93B" lastPageId="2" lastPageNumber="44" pageId="1" pageNumber="43">
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<subSubSection id="C35E6681FFF3FFD7FFFCFCEE6DE9FC56" box="[114,473,885,905]" pageId="1" pageNumber="43" type="nomenclature">
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<paragraph id="8BFB350AFFF3FFD7FFFCFCEE6DE9FC56" blockId="1.[114,473,885,905]" box="[114,473,885,905]" pageId="1" pageNumber="43">
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<heading id="D0B38266FFF3FFD7FFFCFCEE6DE9FC56" box="[114,473,885,905]" fontSize="36" level="2" pageId="1" pageNumber="43" reason="3">
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<emphasis id="B930E918FFF3FFD7FFFCFCEE6DE9FC56" box="[114,473,885,905]" italics="true" pageId="1" pageNumber="43">
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2.1. Profiling of
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<taxonomicName id="4C444E89FFF3FFD7FE85FCEE6D4DFC56" ID-CoL="4WC3B" authority="Spring" authorityName="Spring" box="[267,381,885,905]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="1" pageNumber="43" phylum="Tracheophyta" rank="species" species="martensii">S. martensii</taxonomicName>
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oxylipins
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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="C35E6681FFF3FFD4FF1FFC356856F93B" lastPageId="2" lastPageNumber="44" pageId="1" pageNumber="43" type="biology_ecology">
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<paragraph id="8BFB350AFFF3FFD7FF1FFC3569EDFA4A" blockId="1.[113,783,941,1157]" lastBlockId="1.[831,1501,880,2015]" pageId="1" pageNumber="43">
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The aerial parts of
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<taxonomicName id="4C444E89FFF3FFD7FED5FC366DE0FC1E" box="[347,464,941,961]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="1" pageNumber="43" phylum="Tracheophyta" rank="species" species="martensii">
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<emphasis id="B930E918FFF3FFD7FED5FC366DE0FC1E" box="[347,464,941,961]" italics="true" pageId="1" pageNumber="43">S. martensii</emphasis>
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</taxonomicName>
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plants possessed the complex oxylipins patterns. The structural formulae of two major oxylipins groups, namely the divinyl ethers and cyclopentenones, are presented in
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<figureCitation id="137F298FFFF3FFD7FF5DFB996D22FBCA" box="[211,274,1026,1045]" captionStart="Fig" captionStartId="1.[119,145,1999,2013]" captionTargetBox="[127,769,1214,1970]" captionTargetId="figure-823@1.[126,770,1213,1970]" captionTargetPageId="1" captionText="Fig. 1. The structural formulae of divinyl ether oxylipins detected in S. martensii." figureDoi="http://doi.org/10.5281/zenodo.10489007" httpUri="https://zenodo.org/record/10489007/files/figure.png" pageId="1" pageNumber="43">Figs. 1</figureCitation>
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and
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<figureCitation id="137F298FFFF3FFD7FECCFB996D7FFBCA" box="[322,335,1026,1045]" captionStart="Fig" captionStartId="1.[831,857,763,777]" captionTargetBox="[998,1336,182,733]" captionTargetId="figure-841@1.[995,1337,181,734]" captionTargetPageId="1" captionText="Fig. 2. The structural formulae of cyclopentenone oxylipins detected in S.martensii. Products 4 and 8 were racemates composed of depicted structured and their mirror enantiomers." figureDoi="http://doi.org/10.5281/zenodo.10489003" httpUri="https://zenodo.org/record/10489003/files/figure.png" pageId="1" pageNumber="43">2</figureCitation>
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, respectively. Oxylipins were extracted from
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<taxonomicName id="4C444E89FFF3FFD7FFFFFB866CD2FBEE" box="[113,226,1053,1073]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="1" pageNumber="43" phylum="Tracheophyta" rank="species" species="martensii">
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<emphasis id="B930E918FFF3FFD7FFFFFB866CD2FBEE" box="[113,226,1053,1073]" italics="true" pageId="1" pageNumber="43">S. martensii</emphasis>
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</taxonomicName>
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tissues, methylated, and trimethylsilylated. The resulting oxylipin derivatives were subjected to the GC–MS analyses. The observed total ion current (TIC) oxylipin profile is presented in
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<figureCitation id="137F298FFFF3FFD7FFFFFBE96C8CFB5A" box="[113,188,1138,1157]" captionStart="Fig" captionStartId="2.[87,113,745,759]" captionTargetBox="[360,1192,182,714]" captionTargetId="figure-302@2.[359,1193,181,715]" captionTargetPageId="2" captionText="Fig. 3. The GC–MS profiling of oxylipins (Me/TMSi) from the aerial parts of S. martensii plants. (A) The total ion current (TIC) chromatogram. (B) Selected ion chromatograms (SIC) at m/z 308 (upper chromatogram) and m/z 306 (lower chromatogram)." figureDoi="http://doi.org/10.5281/zenodo.10489009" httpUri="https://zenodo.org/record/10489009/files/figure.png" pageId="1" pageNumber="43">
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Fig. 3
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<taxonomicName id="4C444E89FFF3FFD7FF25FBE96C8CFB5A" baseAuthorityName="Heylaerts" baseAuthorityYear="1891" box="[171,188,1138,1157]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="1" pageNumber="43" phylum="Tracheophyta" rank="species" species="major">A</taxonomicName>
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</figureCitation>
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. Major oxylipins
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<emphasis id="B930E918FFF3FFD7FEFBFBEA6DACFB5B" bold="true" box="[373,412,1137,1157]" pageId="1" pageNumber="43">1–3</emphasis>
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and
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<emphasis id="B930E918FFF3FFD7FE58FBEA6DCCFB5B" bold="true" box="[470,508,1137,1157]" pageId="1" pageNumber="43">4–9</emphasis>
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possessed M
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<superScript id="7C319842FFF3FFD7FD07FBF56EA2FBA5" attach="left" box="[649,658,1134,1146]" fontSize="5" pageId="1" pageNumber="43">+</superScript>
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at
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<emphasis id="B930E918FFF3FFD7FD34FBEA6EFDFB5A" box="[698,717,1137,1157]" italics="true" pageId="1" pageNumber="43">m</emphasis>
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/
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<emphasis id="B930E918FFF3FFD7FD5BFBEA6EEFFB5A" box="[725,735,1137,1157]" italics="true" pageId="1" pageNumber="43">z</emphasis>
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308 and 306, respectively (
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<figureCitation id="137F298FFFF3FFD7FBA7FCEB685FFC5C" box="[1065,1135,880,899]" captionStart="Fig" captionStartId="2.[87,113,745,759]" captionTargetBox="[360,1192,182,714]" captionTargetId="figure-302@2.[359,1193,181,715]" captionTargetPageId="2" captionText="Fig. 3. The GC–MS profiling of oxylipins (Me/TMSi) from the aerial parts of S. martensii plants. (A) The total ion current (TIC) chromatogram. (B) Selected ion chromatograms (SIC) at m/z 308 (upper chromatogram) and m/z 306 (lower chromatogram)." figureDoi="http://doi.org/10.5281/zenodo.10489009" httpUri="https://zenodo.org/record/10489009/files/figure.png" pageId="1" pageNumber="43">Fig. 3B</figureCitation>
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) in their mass spectra. Products
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<emphasis id="B930E918FFF3FFD7FA4DFCEB6F7CFC41" bold="true" pageId="1" pageNumber="43">1– 3</emphasis>
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had nearly identical mass spectra, see the spectrum of compound
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<emphasis id="B930E918FFF3FFD7FCB1FC3C6F7CFC65" bold="true" box="[831,844,935,954]" pageId="1" pageNumber="43">2</emphasis>
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(
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<figureCitation id="137F298FFFF3FFD7FCD0FC3C6F99FC64" box="[862,937,935,955]" captionStart="Fig" captionStartId="2.[366,392,1523,1537]" captionTargetBox="[360,1190,855,1492]" captionTargetId="figure-348@2.[359,1191,855,1493]" captionTargetPageId="2" captionText="Fig. 4. The electron impact mass spectra and fragmentation schemes of divinyl ethers 2 (a) and 7 (b)." figureDoi="http://doi.org/10.5281/zenodo.10489011" httpUri="https://zenodo.org/record/10489011/files/figure.png" pageId="1" pageNumber="43">Fig. 4A</figureCitation>
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) as an example. These spectra fully corresponded to those of etheroleic acid (Me ester) and its geometric isomers (
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<bibRefCitation id="EFD548FBFFF3FFD7FCC9FC446811FC2D" author="Grechkin, A. N. & Fazliev, F. N. & Mukhtarova, L. S." box="[839,1057,991,1011]" pageId="1" pageNumber="43" pagination="159 - 162" refId="ref6361" refString="Grechkin, A. N., Fazliev, F. N., Mukhtarova, L. S., 1995. The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: detection of the novel divinyl ether oxylipins. FEBS Lett. 371, 159 - 162." type="journal article" year="1995">Grechkin et al., 1995</bibRefCitation>
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,
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<bibRefCitation id="EFD548FBFFF3FFD7FBA1FC446852FC2D" author="Grechkin, A. N. & Ilyasov, A. V. & Hamberg, M." box="[1071,1122,991,1010]" pageId="1" pageNumber="43" pagination="137 - 142" refId="ref6414" refString="Grechkin, A. N., Ilyasov, A. V., Hamberg, M., 1997. On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs. Eur. J. Biochem. 245, 137 - 142." type="journal article" year="1997">1997</bibRefCitation>
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and
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<bibRefCitation id="EFD548FBFFF3FFD7FB17FC446907FC2D" author="Hamberg, M." box="[1177,1335,991,1010]" pageId="1" pageNumber="43" pagination="1061 - 1071" refId="ref6462" refString="Hamberg, M., 1998. A pathway for biosynthesis of divinyl ether fatty acids in green leaves. Lipids 33, 1061 - 1071." type="journal article" year="1998">Hamberg, 1998</bibRefCitation>
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). Oxylipins
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<emphasis id="B930E918FFF3FFD7FA38FC4469ECFC2D" bold="true" box="[1462,1500,991,1011]" pageId="1" pageNumber="43">5–7</emphasis>
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(M
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<superScript id="7C319842FFF3FFD7FCD5FC6C6F54FBDC" attach="left" box="[859,868,1015,1027]" fontSize="5" pageId="1" pageNumber="43">+</superScript>
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at
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<emphasis id="B930E918FFF3FFD7FC05FC616FAEFBD1" box="[907,926,1018,1038]" italics="true" pageId="1" pageNumber="43">m</emphasis>
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/
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<emphasis id="B930E918FFF3FFD7FC2BFC616F9FFBD1" box="[933,943,1018,1038]" italics="true" pageId="1" pageNumber="43">z</emphasis>
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306) also exhibited the identical mass spectral data. The spectrum of product
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<emphasis id="B930E918FFF3FFD7FBCDFB8C6860FBF5" bold="true" box="[1091,1104,1047,1066]" pageId="1" pageNumber="43">7</emphasis>
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is illustrated in
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<figureCitation id="137F298FFFF3FFD7FB74FB8C6970FBF5" box="[1274,1344,1047,1066]" captionStart="Fig" captionStartId="2.[366,392,1523,1537]" captionTargetBox="[360,1190,855,1492]" captionTargetId="figure-348@2.[359,1191,855,1493]" captionTargetPageId="2" captionText="Fig. 4. The electron impact mass spectra and fragmentation schemes of divinyl ethers 2 (a) and 7 (b)." figureDoi="http://doi.org/10.5281/zenodo.10489011" httpUri="https://zenodo.org/record/10489011/files/figure.png" pageId="1" pageNumber="43">Fig. 4B</figureCitation>
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. The spectra of products
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<emphasis id="B930E918FFF3FFD7FC2FFBA86FF8FB99" bold="true" box="[929,968,1075,1094]" pageId="1" pageNumber="43">5–7</emphasis>
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matched those of etherolenic acid (Me ester) and its geometric isomers (
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<bibRefCitation id="EFD548FBFFF3FFD7FBB5FBD46912FBBD" author="Grechkin, A. N. & Fazliev, F. N. & Mukhtarova, L. S." box="[1083,1314,1103,1122]" pageId="1" pageNumber="43" pagination="159 - 162" refId="ref6361" refString="Grechkin, A. N., Fazliev, F. N., Mukhtarova, L. S., 1995. The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: detection of the novel divinyl ether oxylipins. FEBS Lett. 371, 159 - 162." type="journal article" year="1995">Grechkin et al., 1995</bibRefCitation>
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,
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<bibRefCitation id="EFD548FBFFF3FFD7FABDFBD4695AFBBD" author="Grechkin, A. N. & Ilyasov, A. V. & Hamberg, M." box="[1331,1386,1103,1122]" pageId="1" pageNumber="43" pagination="137 - 142" refId="ref6414" refString="Grechkin, A. N., Ilyasov, A. V., Hamberg, M., 1997. On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs. Eur. J. Biochem. 245, 137 - 142." type="journal article" year="1997">1997</bibRefCitation>
|
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;
|
||
<bibRefCitation id="EFD548FBFFF3FFD7FAF5FBD46F42FBA1" author="Hamberg, M." pageId="1" pageNumber="43" pagination="1061 - 1071" refId="ref6462" refString="Hamberg, M., 1998. A pathway for biosynthesis of divinyl ether fatty acids in green leaves. Lipids 33, 1061 - 1071." type="journal article" year="1998">Hamberg, 1998</bibRefCitation>
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). The equivalent chain length (ECL) values 19.03, 19.56 and 19.80 (respectively) of peaks
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<emphasis id="B930E918FFF3FFD7FBE5FB1D6848FB46" bold="true" box="[1131,1144,1158,1177]" pageId="1" pageNumber="43">1</emphasis>
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,
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<emphasis id="B930E918FFF3FFD7FB0AFB1D68A1FB46" bold="true" box="[1156,1169,1158,1177]" pageId="1" pageNumber="43">2</emphasis>
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||
and
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<emphasis id="B930E918FFF3FFD7FB4BFB1D68E2FB46" bold="true" box="[1221,1234,1158,1177]" pageId="1" pageNumber="43">3</emphasis>
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were ca. 0.20 bigger than those of (ω5
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<emphasis id="B930E918FFF3FFD7FC46FB3A6FE3FB6A" box="[968,979,1185,1205]" italics="true" pageId="1" pageNumber="43">Z</emphasis>
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||
)-etheroleic, etheroleic and (11
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<emphasis id="B930E918FFF3FFD7FA92FB3A6918FB6A" box="[1308,1320,1185,1205]" italics="true" pageId="1" pageNumber="43">Z</emphasis>
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)-etheroleic acids (Me esters) (
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<bibRefCitation id="EFD548FBFFF3FFD7FC30FB256869FB0D" author="Hamberg, M." box="[958,1113,1214,1234]" pageId="1" pageNumber="43" pagination="1061 - 1071" refId="ref6462" refString="Hamberg, M., 1998. A pathway for biosynthesis of divinyl ether fatty acids in green leaves. Lipids 33, 1061 - 1071." type="journal article" year="1998">Hamberg, 1998</bibRefCitation>
|
||
,
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<bibRefCitation id="EFD548FBFFF3FFD7FBEDFB2468A5FB0D" author="Hamberg, M." box="[1123,1173,1215,1234]" pageId="1" pageNumber="43" pagination="565 - 569" refId="ref6513" refString="Hamberg, M., 2004. Isolation and structures of two divinyl ether fatty acids from Clematis vitalba. Lipids 39, 565 - 569." type="journal article" year="2004">2004</bibRefCitation>
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), measured on a methylsiloxane GLC column. Peak
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<emphasis id="B930E918FFF3FFD7FB8DFB416820FB32" bold="true" box="[1027,1040,1242,1261]" pageId="1" pageNumber="43">7</emphasis>
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corresponded to (11
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<emphasis id="B930E918FFF3FFD7FB64FB4268C6FB32" box="[1258,1270,1241,1261]" italics="true" pageId="1" pageNumber="43">Z</emphasis>
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)-etherolenic acid (Me ester), ECL value 20.22. Etherolenic and (ω5
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<emphasis id="B930E918FFF3FFD7FA97FB6E6915FAD6" box="[1305,1317,1269,1289]" italics="true" pageId="1" pageNumber="43">Z</emphasis>
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)-etherolenic acid Me esters (
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<emphasis id="B930E918FFF3FFD7FC23FA896F8AFAFA" bold="true" box="[941,954,1298,1317]" pageId="1" pageNumber="43">5</emphasis>
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and
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||
<emphasis id="B930E918FFF3FFD7FC64FA896FC7FAFA" bold="true" box="[1002,1015,1298,1317]" pageId="1" pageNumber="43">6</emphasis>
|
||
) appeared as a single peak on 5% phenylmethylsiloxane columns (ECL 20.05). For final structural identification, the individual divinyl ethers were separated at micro-preparative scale and purified by HPLC. Then the NMR spectral data were recorded for each of isomers
|
||
<emphasis id="B930E918FFF3FFD7FB86FA1A681EFA4B" bold="true" box="[1032,1070,1409,1429]" pageId="1" pageNumber="43">1–3</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF3FFD7FBECFA1968B8FA4A" bold="true" box="[1122,1160,1410,1429]" pageId="1" pageNumber="43">5–7</emphasis>
|
||
. These data are presented below.
|
||
</paragraph>
|
||
<paragraph id="8BFB350AFFF3FFD7FCD0FA056FC5F801" blockId="1.[831,1501,880,2015]" pageId="1" pageNumber="43">
|
||
Mass spectra of products
|
||
<emphasis id="B930E918FFF3FFD7FBE7FA066846FA6F" bold="true" box="[1129,1142,1437,1456]" pageId="1" pageNumber="43">4</emphasis>
|
||
,
|
||
<emphasis id="B930E918FFF3FFD7FB0AFA0668A1FA6F" bold="true" box="[1156,1169,1437,1456]" pageId="1" pageNumber="43">8</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF3FFD7FB46FA0668E5FA6F" bold="true" box="[1224,1237,1437,1456]" pageId="1" pageNumber="43">9</emphasis>
|
||
also exhibited M
|
||
<superScript id="7C319842FFF3FFD7FA04FA0169A3FA79" attach="left" box="[1418,1427,1434,1446]" fontSize="5" pageId="1" pageNumber="43">+</superScript>
|
||
at
|
||
<emphasis id="B930E918FFF3FFD7FA36FA0669FBFA6E" box="[1464,1483,1437,1457]" italics="true" pageId="1" pageNumber="43">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF3FFD7FA5CFA0669ECFA6E" box="[1490,1500,1437,1457]" italics="true" pageId="1" pageNumber="43">z</emphasis>
|
||
306. Products
|
||
<emphasis id="B930E918FFF3FFD7FC5EFA226FEDFA13" bold="true" box="[976,989,1465,1484]" pageId="1" pageNumber="43">4</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF3FFD7FB9FFA22682EFA13" bold="true" box="[1041,1054,1465,1484]" pageId="1" pageNumber="43">8</emphasis>
|
||
have nearly identical spectral patterns. The mass spectrum of compound
|
||
<emphasis id="B930E918FFF3FFD7FBE1FA4E684CFA37" bold="true" box="[1135,1148,1493,1512]" pageId="1" pageNumber="43">8</emphasis>
|
||
is presented in
|
||
<figureCitation id="137F298FFFF3FFD7FAADFA4E695BFA36" box="[1315,1387,1493,1513]" captionStart="Fig" captionStartId="3.[113,139,1072,1086]" captionTargetBox="[387,1219,182,1041]" captionTargetId="figure-207@3.[386,1220,181,1042]" captionTargetPageId="3" captionText="Fig. 5. The electron impact mass spectra and fragmentation schemes (insets) of cyclopentenone oxylipins detected in S. martensii. a, b and c, spectra of products 8, 9 and 10, respectively." figureDoi="http://doi.org/10.5281/zenodo.10489013" httpUri="https://zenodo.org/record/10489013/files/figure.png" pageId="1" pageNumber="43">Fig. 5A</figureCitation>
|
||
. This spectrum matches that of
|
||
<emphasis id="B930E918FFF3FFD7FBABFA6B680EF9DB" box="[1061,1086,1520,1540]" italics="true" pageId="1" pageNumber="43">cis</emphasis>
|
||
-12-oxo-10,15(
|
||
<emphasis id="B930E918FFF3FFD7FB58FA6B68D1F9DB" box="[1238,1249,1520,1540]" italics="true" pageId="1" pageNumber="43">Z</emphasis>
|
||
)-phytodienoic acid (12- oxo-PDA) Me ester (
|
||
<bibRefCitation id="EFD548FBFFF3FFD7FB87F99668DCF9FF" author="Chechetkin, I. R. & Blufard, A. & Hamberg, M. & Grechkin, A. N." box="[1033,1260,1549,1569]" pageId="1" pageNumber="43" pagination="2008 - 2015" refId="ref6018" refString="Chechetkin, I. R., Blufard, A., Hamberg, M., Grechkin, A. N., 2008. A lipoxygenasedivinyl ether synthase pathway in flax (Linum usitatissimum L.) leaves. Phytochemistry 69, 2008 - 2015." type="journal article" year="2008">Chechetkin et al., 2008</bibRefCitation>
|
||
). Both the mass spectra and the retention times of products
|
||
<emphasis id="B930E918FFF3FFD7FB25F9B26888F9E3" bold="true" box="[1195,1208,1577,1596]" pageId="1" pageNumber="43">4</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF3FFD7FB67F9B268C6F9E3" bold="true" box="[1257,1270,1577,1596]" pageId="1" pageNumber="43">8</emphasis>
|
||
corresponded to those of
|
||
<emphasis id="B930E918FFF3FFD7FCD7F9DF6FBAF987" box="[857,906,1604,1624]" italics="true" pageId="1" pageNumber="43">trans</emphasis>
|
||
-12-oxo-PDA and
|
||
<emphasis id="B930E918FFF3FFD7FBB1F9DF6868F987" box="[1087,1112,1604,1624]" italics="true" pageId="1" pageNumber="43">cis</emphasis>
|
||
-12-oxo-PDA (Me esters), respectively. Compound
|
||
<emphasis id="B930E918FFF3FFD7FC3DF9FA6FF0F9AB" bold="true" box="[947,960,1633,1652]" pageId="1" pageNumber="43">9</emphasis>
|
||
possessed the distinct, recognizable mass fragmentation patterns (
|
||
<figureCitation id="137F298FFFF3FFD7FC43F9E66820F94F" box="[973,1040,1661,1680]" captionStart="Fig" captionStartId="3.[113,139,1072,1086]" captionTargetBox="[387,1219,182,1041]" captionTargetId="figure-207@3.[386,1220,181,1042]" captionTargetPageId="3" captionText="Fig. 5. The electron impact mass spectra and fragmentation schemes (insets) of cyclopentenone oxylipins detected in S. martensii. a, b and c, spectra of products 8, 9 and 10, respectively." figureDoi="http://doi.org/10.5281/zenodo.10489013" httpUri="https://zenodo.org/record/10489013/files/figure.png" pageId="1" pageNumber="43">Fig. 5B</figureCitation>
|
||
) of 12-oxo-9(13),15(
|
||
<emphasis id="B930E918FFF3FFD7FB6FF9E768DDF94F" box="[1249,1261,1660,1680]" italics="true" pageId="1" pageNumber="43">Z</emphasis>
|
||
)-phytodienoic acid (Me ester) (
|
||
<bibRefCitation id="EFD548FBFFF3FFD7FC08F9026817F973" author="Vick, B. A. & Zimmerman, D. C. & Weisleder, D." box="[902,1063,1689,1708]" pageId="1" pageNumber="43" pagination="734 - 740" refId="ref7767" refString="Vick, B. A., Zimmerman, D. C., Weisleder, D., 1979. Thermal alteration of a cyclic fatty acid produced by a flaxseed extract. Lipids 14, 734 - 740." type="journal article" year="1979">Vick et al., 1979</bibRefCitation>
|
||
). Catalytic hydrogenation turned product
|
||
<emphasis id="B930E918FFF3FFD7FA41F90269ECF973" bold="true" box="[1487,1500,1689,1708]" pageId="1" pageNumber="43">9</emphasis>
|
||
to a nearly equimolar mixture of
|
||
<emphasis id="B930E918FFF3FFD7FB1BF92868F6F918" box="[1173,1222,1715,1735]" italics="true" pageId="1" pageNumber="43">trans</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF3FFD7FB75F9286924F918" box="[1275,1300,1715,1735]" italics="true" pageId="1" pageNumber="43">cis</emphasis>
|
||
isomers of 12-oxophytonoic acid (Me). Their mass spectra exhibited M
|
||
<superScript id="7C319842FFF3FFD7FAD0F9566957F906" attach="left" box="[1374,1383,1741,1753]" fontSize="5" pageId="1" pageNumber="43">+</superScript>
|
||
at
|
||
<emphasis id="B930E918FFF3FFD7FA04F95469ADF93C" box="[1418,1437,1743,1763]" italics="true" pageId="1" pageNumber="43">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF3FFD7FA2BF954699FF93C" box="[1445,1455,1743,1763]" italics="true" pageId="1" pageNumber="43">z</emphasis>
|
||
310 (0.1%), [M
|
||
<superScript id="7C319842FFF3FFD7FC2AF9726F9DF92A" attach="left" box="[932,941,1769,1781]" fontSize="5" pageId="1" pageNumber="43">+</superScript>
|
||
<emphasis id="B930E918FFF3FFD7FC23F9776F8EF920" box="[941,958,1772,1791]" italics="true" pageId="1" pageNumber="43">—</emphasis>
|
||
MeO] at
|
||
<emphasis id="B930E918FFF3FFD7FB97F970681CF920" box="[1049,1068,1771,1791]" italics="true" pageId="1" pageNumber="43">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF3FFD7FBBAF970680EF920" box="[1076,1086,1771,1791]" italics="true" pageId="1" pageNumber="43">z</emphasis>
|
||
279 (1%), [M
|
||
<superScript id="7C319842FFF3FFD7FB46F97268E1F92A" attach="left" box="[1224,1233,1769,1781]" fontSize="5" pageId="1" pageNumber="43">+</superScript>
|
||
<emphasis id="B930E918FFF3FFD7FB5FF97768D2F920" box="[1233,1250,1772,1791]" italics="true" pageId="1" pageNumber="43">—</emphasis>
|
||
Me(
|
||
<collectingCountry id="F353759AFFF3FFD7FA89F9776917F920" box="[1287,1319,1772,1791]" name="Switzerland" pageId="1" pageNumber="43">CH</collectingCountry>
|
||
<subScript id="17C0374FFFF3FFD7FAA9F96E6900F8DE" attach="left" box="[1319,1328,1781,1793]" fontSize="5" pageId="1" pageNumber="43">2</subScript>
|
||
)
|
||
<subScript id="17C0374FFFF3FFD7FAB6F96E6971F8DE" attach="none" box="[1336,1345,1781,1793]" fontSize="5" pageId="1" pageNumber="43">4</subScript>
|
||
+H] at
|
||
<emphasis id="B930E918FFF3FFD7FA04F97069ADF920" box="[1418,1437,1771,1791]" italics="true" pageId="1" pageNumber="43">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF3FFD7FA2AF970699EF920" box="[1444,1454,1771,1791]" italics="true" pageId="1" pageNumber="43">z</emphasis>
|
||
240 (4%), [M
|
||
<superScript id="7C319842FFF3FFD7FC1AF89F6FADF8CF" attach="left" box="[916,925,1796,1808]" fontSize="5" pageId="1" pageNumber="43">+</superScript>
|
||
<emphasis id="B930E918FFF3FFD7FC12F8936F9DF8C4" box="[924,941,1800,1819]" italics="true" pageId="1" pageNumber="43">—</emphasis>
|
||
(
|
||
<collectingCountry id="F353759AFFF3FFD7FC3DF8936FE3F8C4" box="[947,979,1800,1819]" name="Switzerland" pageId="1" pageNumber="43">CH</collectingCountry>
|
||
<subScript id="17C0374FFFF3FFD7FC5DF88A6FECF8C2" attach="left" box="[979,988,1809,1821]" fontSize="5" pageId="1" pageNumber="43">2</subScript>
|
||
)
|
||
<subScript id="17C0374FFFF3FFD7FC6AF88A6FDDF8C2" attach="right" box="[996,1005,1809,1821]" fontSize="5" pageId="1" pageNumber="43">7</subScript>
|
||
COOMe] at
|
||
<emphasis id="B930E918FFF3FFD7FBE9F89C684AF8C4" box="[1127,1146,1799,1819]" italics="true" pageId="1" pageNumber="43">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF3FFD7FB0CF89C68BCF8C4" box="[1154,1164,1799,1819]" italics="true" pageId="1" pageNumber="43">z</emphasis>
|
||
153 (14%), 83 (100%). Similarly, the hydrogenation turned compounds
|
||
<emphasis id="B930E918FFF3FFD7FB48F8BF68E3F8E8" bold="true" box="[1222,1235,1828,1847]" pageId="1" pageNumber="43">4</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF3FFD7FA8BF8BF6922F8E8" bold="true" box="[1285,1298,1828,1847]" pageId="1" pageNumber="43">8</emphasis>
|
||
to
|
||
<emphasis id="B930E918FFF3FFD7FABDF8B86954F8E8" box="[1331,1380,1827,1847]" italics="true" pageId="1" pageNumber="43">trans</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF3FFD7FA19F8B86980F8E8" box="[1431,1456,1827,1847]" italics="true" pageId="1" pageNumber="43">cis</emphasis>
|
||
isomers of 12-oxophytonoic acid (Me), respectively. The obtained results allowed us to assign the structures of Me esters of
|
||
<emphasis id="B930E918FFF3FFD7FA2CF8C069E3F8B0" box="[1442,1491,1883,1903]" italics="true" pageId="1" pageNumber="43">trans</emphasis>
|
||
- 12-oxo-PDA,
|
||
<emphasis id="B930E918FFF3FFD7FC47F8EC6FD2F854" box="[969,994,1911,1931]" italics="true" pageId="1" pageNumber="43">cis</emphasis>
|
||
-12-oxo-PDA and 12-oxo-9(13)-PDA to products
|
||
<emphasis id="B930E918FFF3FFD7FCB1F8086F7CF879" bold="true" box="[831,844,1939,1958]" pageId="1" pageNumber="43">4</emphasis>
|
||
,
|
||
<emphasis id="B930E918FFF3FFD7FCD6F8086F55F879" bold="true" box="[856,869,1939,1958]" pageId="1" pageNumber="43">8</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF3FFD7FC17F8086F96F879" bold="true" box="[921,934,1939,1958]" pageId="1" pageNumber="43">9</emphasis>
|
||
, respectively. Steric analysis of purified
|
||
<emphasis id="B930E918FFF3FFD7FACFF808696AF878" box="[1345,1370,1939,1959]" italics="true" pageId="1" pageNumber="43">cis</emphasis>
|
||
-12-oxo-PDA (
|
||
<emphasis id="B930E918FFF3FFD7FCC9F8346F64F81D" bold="true" box="[839,852,1967,1986]" pageId="1" pageNumber="43">8</emphasis>
|
||
, Me ester) revealed that it was composed of 45% (
|
||
<emphasis id="B930E918FFF3FFD7FAD4F8346957F81C" box="[1370,1383,1967,1987]" italics="true" pageId="1" pageNumber="43">R</emphasis>
|
||
,
|
||
<emphasis id="B930E918FFF3FFD7FAE2F8346949F81C" box="[1388,1401,1967,1987]" italics="true" pageId="1" pageNumber="43">R</emphasis>
|
||
) and 55% (
|
||
<emphasis id="B930E918FFF3FFD7FCC9F8516F62F801" box="[839,850,1994,2014]" italics="true" pageId="1" pageNumber="43">S</emphasis>
|
||
,
|
||
<emphasis id="B930E918FFF3FFD7FCD8F8516F51F801" box="[854,865,1994,2014]" italics="true" pageId="1" pageNumber="43">S</emphasis>
|
||
) enantiomers.
|
||
</paragraph>
|
||
<caption id="DF3B6582FFF3FFD7FFF9F8546F39F802" ID-DOI="http://doi.org/10.5281/zenodo.10489007" ID-Zenodo-Dep="10489007" box="[119,777,1998,2013]" httpUri="https://zenodo.org/record/10489007/files/figure.png" pageId="1" pageNumber="43" startId="1.[119,145,1999,2013]" targetBox="[127,769,1214,1970]" targetPageId="1" targetType="figure">
|
||
<paragraph id="8BFB350AFFF3FFD7FFF9F8546F39F802" blockId="1.[119,777,1998,2013]" box="[119,777,1998,2013]" pageId="1" pageNumber="43">
|
||
<emphasis id="B930E918FFF3FFD7FFF9F8546C99F802" bold="true" box="[119,169,1999,2013]" pageId="1" pageNumber="43">Fig. 1.</emphasis>
|
||
The structural formulae of divinyl ether oxylipins detected in
|
||
<taxonomicName id="4C444E89FFF3FFD7FD24F8556F36F802" box="[682,774,1998,2013]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="1" pageNumber="43" phylum="Tracheophyta" rank="species" species="martensii">
|
||
<emphasis id="B930E918FFF3FFD7FD24F8556F36F802" box="[682,774,1998,2013]" italics="true" pageId="1" pageNumber="43">S. martensii</emphasis>
|
||
</taxonomicName>
|
||
.
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="DF3B6582FFF0FFD4FFD9FD726EF6FCD1" ID-DOI="http://doi.org/10.5281/zenodo.10489009" ID-Zenodo-Dep="10489009" httpUri="https://zenodo.org/record/10489009/files/figure.png" pageId="2" pageNumber="44" startId="2.[87,113,745,759]" targetBox="[360,1192,182,714]" targetPageId="2" targetType="figure">
|
||
<paragraph id="8BFB350AFFF0FFD4FFD9FD726EF6FCD1" blockId="2.[87,1474,744,782]" pageId="2" pageNumber="44">
|
||
<emphasis id="B930E918FFF0FFD4FFD9FD726CB8FD28" bold="true" box="[87,136,745,759]" pageId="2" pageNumber="44">Fig. 3.</emphasis>
|
||
The GC–MS profiling of oxylipins (Me/TMSi) from the aerial parts of
|
||
<taxonomicName id="4C444E89FFF0FFD4FD3BFD736F20FD28" box="[693,784,744,759]" class="Lycopodiopsida" family="Selaginellaceae" genus="Selaginella" kingdom="Plantae" order="Selaginellales" pageId="2" pageNumber="44" phylum="Tracheophyta" rank="species" species="martensii">
|
||
<emphasis id="B930E918FFF0FFD4FD3BFD736F20FD28" box="[693,784,744,759]" italics="true" pageId="2" pageNumber="44">S. martensii</emphasis>
|
||
</taxonomicName>
|
||
plants. (A) The total ion current (TIC) chromatogram. (B) Selected ion chromatograms (SIC) at
|
||
<emphasis id="B930E918FFF0FFD4FF16FD646C97FCD1" box="[152,167,767,782]" italics="true" pageId="2" pageNumber="44">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF0FFD4FF23FD646C85FCD1" box="[173,181,767,782]" italics="true" pageId="2" pageNumber="44">z</emphasis>
|
||
308 (upper chromatogram) and
|
||
<emphasis id="B930E918FFF0FFD4FE4CFD646DE1FCD1" box="[450,465,767,782]" italics="true" pageId="2" pageNumber="44">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF0FFD4FE59FD646DEFFCD1" box="[471,479,767,782]" italics="true" pageId="2" pageNumber="44">z</emphasis>
|
||
306 (lower chromatogram).
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="DF3B6582FFF0FFD4FEE0FA68689CF9DE" ID-DOI="http://doi.org/10.5281/zenodo.10489011" ID-Zenodo-Dep="10489011" box="[366,1196,1523,1537]" httpUri="https://zenodo.org/record/10489011/files/figure.png" pageId="2" pageNumber="44" startId="2.[366,392,1523,1537]" targetBox="[360,1190,855,1492]" targetPageId="2" targetType="figure">
|
||
<paragraph id="8BFB350AFFF0FFD4FEE0FA68689CF9DE" blockId="2.[366,1196,1523,1537]" box="[366,1196,1523,1537]" pageId="2" pageNumber="44">
|
||
<emphasis id="B930E918FFF0FFD4FEE0FA686D90F9DE" bold="true" box="[366,416,1523,1537]" pageId="2" pageNumber="44">Fig. 4.</emphasis>
|
||
The electron impact mass spectra and fragmentation schemes of divinyl ethers
|
||
<emphasis id="B930E918FFF0FFD4FBBFFA68680BF9DE" bold="true" box="[1073,1083,1523,1537]" pageId="2" pageNumber="44">2</emphasis>
|
||
(a) and
|
||
<emphasis id="B930E918FFF0FFD4FB0EFA6868BAF9DE" bold="true" box="[1152,1162,1523,1537]" pageId="2" pageNumber="44">7</emphasis>
|
||
(b).
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8BFB350AFFF0FFD4FFF8F9DE6EA8F854" blockId="2.[87,757,1605,2015]" pageId="2" pageNumber="44">
|
||
Peak of one more related minor product
|
||
<emphasis id="B930E918FFF0FFD4FD9CF9DE6E1BF987" bold="true" box="[530,555,1605,1624]" pageId="2" pageNumber="44">10</emphasis>
|
||
eluted shortly after the methyl stearate (not illustrated). Despite its relative minority, it is of substantial interest. Its mass spectrum is presented in
|
||
<figureCitation id="137F298FFFF0FFD4FFD9F9026CAFF973" box="[87,159,1689,1708]" captionStart="Fig" captionStartId="3.[113,139,1072,1086]" captionTargetBox="[387,1219,182,1041]" captionTargetId="figure-207@3.[386,1220,181,1042]" captionTargetPageId="3" captionText="Fig. 5. The electron impact mass spectra and fragmentation schemes (insets) of cyclopentenone oxylipins detected in S. martensii. a, b and c, spectra of products 8, 9 and 10, respectively." figureDoi="http://doi.org/10.5281/zenodo.10489013" httpUri="https://zenodo.org/record/10489013/files/figure.png" pageId="2" pageNumber="44">Fig. 5C</figureCitation>
|
||
. It possessed M
|
||
<superScript id="7C319842FFF0FFD4FECFF90E6D7AF97E" attach="left" box="[321,330,1685,1697]" fontSize="5" pageId="2" pageNumber="44">+</superScript>
|
||
at
|
||
<emphasis id="B930E918FFF0FFD4FEE3F9036DB0F973" box="[365,384,1688,1708]" italics="true" pageId="2" pageNumber="44">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF0FFD4FE09F9036DA1F973" box="[391,401,1688,1708]" italics="true" pageId="2" pageNumber="44">z</emphasis>
|
||
278 and characteristic fragmentation patterns shown in the scheme (
|
||
<figureCitation id="137F298FFFF0FFD4FE54F92F6E23F918" box="[474,531,1716,1735]" captionStart="Fig" captionStartId="3.[113,139,1072,1086]" captionTargetBox="[387,1219,182,1041]" captionTargetId="figure-207@3.[386,1220,181,1042]" captionTargetPageId="3" captionText="Fig. 5. The electron impact mass spectra and fragmentation schemes (insets) of cyclopentenone oxylipins detected in S. martensii. a, b and c, spectra of products 8, 9 and 10, respectively." figureDoi="http://doi.org/10.5281/zenodo.10489013" httpUri="https://zenodo.org/record/10489013/files/figure.png" pageId="2" pageNumber="44">Fig. 5</figureCitation>
|
||
, inset). Product
|
||
<emphasis id="B930E918FFF0FFD4FD4FF92F6EEAF918" bold="true" box="[705,730,1716,1735]" pageId="2" pageNumber="44">10</emphasis>
|
||
is the
|
||
<emphasis id="B930E918FFF0FFD4FFF1F9546CA8F93C" box="[127,152,1743,1763]" italics="true" pageId="2" pageNumber="44">cis</emphasis>
|
||
-2,3-dinor-12-oxo-PDA, a lower homologue of compound
|
||
<emphasis id="B930E918FFF0FFD4FD66F94B6EC5F93C" bold="true" box="[744,757,1744,1763]" pageId="2" pageNumber="44">8</emphasis>
|
||
(
|
||
<bibRefCitation id="EFD548FBFFF0FFD4FFD1F9776D12F920" author="Weber, H. & Vick, B. A. & Farmer, E. E." box="[95,290,1772,1792]" pageId="2" pageNumber="44" pagination="10473 - 10478" refId="ref7808" refString="Weber, H., Vick, B. A., Farmer, E. E., 1997. Dinor-oxo-phytodienoic acid: a new hexadecanoid signal in the jasmonate family. Proc. Natl. Acad. Sci. U. S. A. 94, 10473 - 10478." type="journal article" year="1997">Weber et al., 1997</bibRefCitation>
|
||
). Catalytic hydrogenation turned product
|
||
<emphasis id="B930E918FFF0FFD4FD55F9776EC4F920" bold="true" box="[731,756,1772,1791]" pageId="2" pageNumber="44">10</emphasis>
|
||
to nearly equimolar mixture of
|
||
<emphasis id="B930E918FFF0FFD4FE17F89C6DFAF8C4" box="[409,458,1799,1819]" italics="true" pageId="2" pageNumber="44">trans</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF0FFD4FE70F89C6E27F8C4" box="[510,535,1799,1819]" italics="true" pageId="2" pageNumber="44">cis</emphasis>
|
||
isomers of 2,3-dinor-12-oxophytonoic acid (Me). Their mass spectra exhibited [M
|
||
<superScript id="7C319842FFF0FFD4FFFAF8A76C4DF897" attach="left" box="[116,125,1852,1864]" fontSize="5" pageId="2" pageNumber="44">+</superScript>
|
||
<emphasis id="B930E918FFF0FFD4FFF2F8DB6CBDF88C" box="[124,141,1856,1875]" italics="true" pageId="2" pageNumber="44">—</emphasis>
|
||
MeO] at
|
||
<emphasis id="B930E918FFF0FFD4FF62F8A46CCFF88C" box="[236,255,1855,1875]" italics="true" pageId="2" pageNumber="44">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF0FFD4FE89F8A46D21F88C" box="[263,273,1855,1875]" italics="true" pageId="2" pageNumber="44">z</emphasis>
|
||
279 (1%), [M
|
||
<superScript id="7C319842FFF0FFD4FE2FF8A76D9AF897" attach="left" box="[417,426,1852,1864]" fontSize="5" pageId="2" pageNumber="44">+</superScript>
|
||
<emphasis id="B930E918FFF0FFD4FE24F8DB6D8BF88C" box="[426,443,1856,1875]" italics="true" pageId="2" pageNumber="44">—</emphasis>
|
||
Me(
|
||
<collectingCountry id="F353759AFFF0FFD4FE6EF8DB6E30F88C" box="[480,512,1856,1875]" name="Switzerland" pageId="2" pageNumber="44">CH</collectingCountry>
|
||
<subScript id="17C0374FFFF0FFD4FD8EF8D26E39F88A" attach="left" box="[512,521,1865,1877]" fontSize="5" pageId="2" pageNumber="44">2</subScript>
|
||
)
|
||
<subScript id="17C0374FFFF0FFD4FD9FF8D26E2AF88A" attach="none" box="[529,538,1865,1877]" fontSize="5" pageId="2" pageNumber="44">4</subScript>
|
||
+H] at
|
||
<emphasis id="B930E918FFF0FFD4FDE9F8A46E4AF88C" box="[615,634,1855,1875]" italics="true" pageId="2" pageNumber="44">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF0FFD4FD0FF8A46EBBF88C" box="[641,651,1855,1875]" italics="true" pageId="2" pageNumber="44">z</emphasis>
|
||
212 (7%), [M
|
||
<superScript id="7C319842FFF0FFD4FFFAF8C36C4DF8BB" attach="left" box="[116,125,1880,1892]" fontSize="5" pageId="2" pageNumber="44">+</superScript>
|
||
<emphasis id="B930E918FFF0FFD4FFF2F8C76CBDF8B0" box="[124,141,1884,1903]" italics="true" pageId="2" pageNumber="44">—</emphasis>
|
||
(
|
||
<collectingCountry id="F353759AFFF0FFD4FF1DF8C76C83F8B0" box="[147,179,1884,1903]" name="Switzerland" pageId="2" pageNumber="44">CH</collectingCountry>
|
||
<subScript id="17C0374FFFF0FFD4FF3DF8FE6C8CF8AE" attach="left" box="[179,188,1893,1905]" fontSize="5" pageId="2" pageNumber="44">2</subScript>
|
||
)
|
||
<subScript id="17C0374FFFF0FFD4FF4AF8FE6CFDF8AE" attach="right" box="[196,205,1893,1905]" fontSize="5" pageId="2" pageNumber="44">7</subScript>
|
||
COOMe] at
|
||
<emphasis id="B930E918FFF0FFD4FEC6F8C06D6BF8B0" box="[328,347,1883,1903]" italics="true" pageId="2" pageNumber="44">m</emphasis>
|
||
/
|
||
<emphasis id="B930E918FFF0FFD4FEEDF8C06D5DF8B0" box="[355,365,1883,1903]" italics="true" pageId="2" pageNumber="44">z</emphasis>
|
||
153 (15%), 83 (100%). The
|
||
<emphasis id="B930E918FFF0FFD4FD1EF8C06E99F8B0" box="[656,681,1883,1903]" italics="true" pageId="2" pageNumber="44">cis</emphasis>
|
||
-2,3-dinor-12-oxophytonoic acid (Me) had the ECL value 18.22.
|
||
</paragraph>
|
||
<paragraph id="8BFB350AFFF0FFD4FFF8F80F6856F93B" blockId="2.[87,757,1605,2015]" lastBlockId="2.[805,1475,1605,1764]" pageId="2" pageNumber="44">
|
||
Along with the above mentioned DES and AOS products, some minor oxylipins have been detected. These are 9-oxononanoic acid, azelaic acid and (3
|
||
<emphasis id="B930E918FFF0FFD4FEA6F8516D04F801" box="[296,308,1994,2014]" italics="true" pageId="2" pageNumber="44">Z</emphasis>
|
||
)-traumatic acid. Their physical data (not presented) were identical to those described in our recent paper (
|
||
<bibRefCitation id="EFD548FBFFF0FFD4FCA3F9FA6814F9AB" author="Mukhtarova, L. S. & Mukhitova, F. K. & Gogolev, Y. V. & Grechkin, A. N." box="[813,1060,1633,1652]" pageId="2" pageNumber="44" pagination="356 - 364" refId="ref6937" refString="Mukhtarova, L. S., Mukhitova, F. K., Gogolev, Y. V., Grechkin, A. N., 2011. Hydroperoxide lyase cascade in pea seedlings: non-volatile oxylipins and their age and stress dependent alterations. Phytochemistry 72, 356 - 364." type="journal article" year="2011">Mukhtarova et al., 2011</bibRefCitation>
|
||
). Appearance of these chain fragmentation products is apparently related to the HPL activity. Besides, the Oi- ketol, 12-oxo-13-hydroxy-9,15-octadecadienoic acid (Me/ TMS) was detected. However, it was much less abundant than the cyclopentenones
|
||
<emphasis id="B930E918FFF0FFD4FC72F94B6839F93C" bold="true" box="[1020,1033,1744,1763]" pageId="2" pageNumber="44">4</emphasis>
|
||
,
|
||
<emphasis id="B930E918FFF0FFD4FB9BF94B6812F93C" bold="true" box="[1045,1058,1744,1763]" pageId="2" pageNumber="44">8</emphasis>
|
||
and
|
||
<emphasis id="B930E918FFF0FFD4FBDBF94B6852F93C" bold="true" box="[1109,1122,1744,1763]" pageId="2" pageNumber="44">9</emphasis>
|
||
.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |