692 lines
71 KiB
XML
692 lines
71 KiB
XML
<document id="A59C0FF8DFC0272503C79C25EF90D55B" ID-DOI="10.1016/j.phytochem.2020.112533" ID-ISSN="1873-3700" ID-Zenodo-Dep="8292672" IM.bibliography_approvedBy="julia" IM.illustrations_approvedBy="julia" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="julia" IM.taxonomicNames_approvedBy="julia" IM.treatments_approvedBy="julia" checkinTime="1693249889966" checkinUser="felipe" docAuthor="Mukhtarova, Lucia S., Lantsova, Natalia V., Khairutdinov, Bulat I. & Grechkin, Alexander N." docDate="2020" docId="24402D474367FFEF087E916AFB66F923" docLanguage="en" docName="Phytochemistry.180.112533.pdf" docOrigin="Phytochemistry (112533) 180" docSource="http://dx.doi.org/10.1016/j.phytochem.2020.112533" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Physcomitrella patens subsp. gametophores Bruch & Schimp." docType="treatment" docVersion="3" lastPageNumber="3" masterDocId="D879553F4366FFED081A933FFF9DFFDA" masterDocTitle="Lipoxygenase pathway in model bryophytes: 12 - oxo- 9 (13), 15 - phytodienoic acid is a predominant oxylipin in Physcomitrella patens" masterLastPageNumber="7" masterPageNumber="1" pageNumber="2" updateTime="1693406579488" updateUser="julia">
|
||
<mods:mods id="EA8B3BF6BF65C06EB063FCECC1349C85" xmlns:mods="http://www.loc.gov/mods/v3">
|
||
<mods:titleInfo id="0607DABDCAC64E0EDF532E1C544C67F2">
|
||
<mods:title id="B7039107646D9E8E8488B53B6FC81731">Lipoxygenase pathway in model bryophytes: 12 - oxo- 9 (13), 15 - phytodienoic acid is a predominant oxylipin in Physcomitrella patens</mods:title>
|
||
</mods:titleInfo>
|
||
<mods:name id="7068C32607392845E3F2FC2274B71D83" type="personal">
|
||
<mods:role id="465BA7BB4F67656342107A5593D6648F">
|
||
<mods:roleTerm id="1B7B28C22A353083ACBE59CBB9B1FF36">Author</mods:roleTerm>
|
||
</mods:role>
|
||
<mods:namePart id="5A3A8979BA21FDD188A03B306C5FFF38">Mukhtarova, Lucia S.</mods:namePart>
|
||
</mods:name>
|
||
<mods:name id="28C25CC689E2840715816719663EAB8F" type="personal">
|
||
<mods:role id="AFF65523FCA0C7D22A8C4A9D113068AD">
|
||
<mods:roleTerm id="C07BDC54860E836101529750262CDF06">Author</mods:roleTerm>
|
||
</mods:role>
|
||
<mods:namePart id="DAE92E41195E933204DEBFA49D484F8C">Lantsova, Natalia V.</mods:namePart>
|
||
</mods:name>
|
||
<mods:name id="6283E7D66A486861405BD217CA739111" type="personal">
|
||
<mods:role id="8C1F97C50F877FFF370FE6BAFB82E4B0">
|
||
<mods:roleTerm id="6D16E46D52888647A5B46BFB2C64AAA5">Author</mods:roleTerm>
|
||
</mods:role>
|
||
<mods:namePart id="686A47677C401BACEB59A0C16E7F044F">Khairutdinov, Bulat I.</mods:namePart>
|
||
</mods:name>
|
||
<mods:name id="1A78346DBB4E291C9E72733670989B29" type="personal">
|
||
<mods:role id="CDDFBE8E53EC4FEC20B3CCE12CD51806">
|
||
<mods:roleTerm id="768073FBA64E494ADAD20DD8229F50DB">Author</mods:roleTerm>
|
||
</mods:role>
|
||
<mods:namePart id="29AE35D0BC78F83A276D1A39AA89D6D9">Grechkin, Alexander N.</mods:namePart>
|
||
</mods:name>
|
||
<mods:typeOfResource id="0D0446AE7C9F885EDA86E638E27A59AF">text</mods:typeOfResource>
|
||
<mods:relatedItem id="BF67A80551AB3320C174DE5C68C2482B" type="host">
|
||
<mods:titleInfo id="52322357176A2C046D2BE2C69CD4319B">
|
||
<mods:title id="029C09F05C7CC4251738CDA564CBAEA3">Phytochemistry</mods:title>
|
||
</mods:titleInfo>
|
||
<mods:part id="05C0CAC798210C3477E2A6228701035D">
|
||
<mods:date id="E3EDFB7CC6621B77F236B2657F4D400D">2020</mods:date>
|
||
<mods:detail id="120F56C0F939A997910A949557BE60B0" type="series">
|
||
<mods:title id="B2737F89D1BAD84AEE257FDA74DACF2C">112533</mods:title>
|
||
</mods:detail>
|
||
<mods:detail id="A8210DE78066E11B43225BD375BEB6FA" type="pubDate">
|
||
<mods:number id="72928752E01DDAE591C75E0340B0CC7B">2020-12-31</mods:number>
|
||
</mods:detail>
|
||
<mods:detail id="998469D57B5EF1BE07CC3A1C14ED8567" type="volume">
|
||
<mods:number id="CB2E5E64CFCB3B6980638B4402CB42EB">180</mods:number>
|
||
</mods:detail>
|
||
<mods:extent id="3116FC3AF01EC98D4BF481A37B849981" unit="page">
|
||
<mods:start id="EA444428B90CBA4634DC30DEC232B58C">1</mods:start>
|
||
<mods:end id="0BAC200F29B4CED30E201557E7D9D736">7</mods:end>
|
||
</mods:extent>
|
||
</mods:part>
|
||
</mods:relatedItem>
|
||
<mods:location id="01E7C00714A27F6BF7708740A48A0332">
|
||
<mods:url id="B1ABA3E44A8A9A86E7DBDBF7CFF55151">http://dx.doi.org/10.1016/j.phytochem.2020.112533</mods:url>
|
||
</mods:location>
|
||
<mods:classification id="3EA07D1A94333D24FF19E72173F5B509">journal article</mods:classification>
|
||
<mods:identifier id="F26FDA3A4D3D58DB934C667E73F2B76B" type="DOI">10.1016/j.phytochem.2020.112533</mods:identifier>
|
||
<mods:identifier id="5834BA7535C10BAFEF95A4798C275D1C" type="ISSN">1873-3700</mods:identifier>
|
||
<mods:identifier id="42ADBCF81CEDC5153DED46E0FC165E4F" type="Zenodo-Dep">8292672</mods:identifier>
|
||
</mods:mods>
|
||
<treatment id="24402D474367FFEF087E916AFB66F923" LSID="urn:lsid:plazi:treatment:24402D474367FFEF087E916AFB66F923" httpUri="http://treatment.plazi.org/id/24402D474367FFEF087E916AFB66F923" lastPageId="2" lastPageNumber="3" pageId="1" pageNumber="2">
|
||
<subSubSection id="E4F3CFDA4367FFEC087E916AFE47FDB2" box="[100,474,597,616]" pageId="1" pageNumber="2" type="nomenclature">
|
||
<paragraph id="AC569C514367FFEC087E916AFE47FDB2" blockId="1.[100,474,597,616]" box="[100,474,597,616]" pageId="1" pageNumber="2">
|
||
<heading id="F71E2B3D4367FFEC087E916AFE47FDB2" bold="true" box="[100,474,597,616]" fontSize="36" level="1" pageId="1" pageNumber="2" reason="1">
|
||
<emphasis id="9E9D40434367FFEC087E916AFE47FDB2" bold="true" box="[100,474,597,616]" italics="true" pageId="1" pageNumber="2">
|
||
2.1. Oxylipins of
|
||
<taxonomicName id="6BE9E7D24367FFEC0912916AFEC4FDB2" authority="(Hedw.) Bruch & Schimp." authorityName="Bruch & Schimp." baseAuthorityName="Hedw." box="[264,345,597,616]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="1" pageNumber="2" phylum="Bryophyta" rank="subSpecies" species="patens" subSpecies="gametophores">P. patens</taxonomicName>
|
||
gametophores
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
</subSubSection>
|
||
<subSubSection id="E4F3CFDA4367FFEF089E91B2FB66F923" lastPageId="2" lastPageNumber="3" pageId="1" pageNumber="2" type="description">
|
||
<paragraph id="AC569C514367FFEC089E91B2FC9EFD7A" blockId="1.[100,771,653,700]" box="[132,771,653,672]" pageId="1" pageNumber="2">
|
||
The oxylipin profile of
|
||
<taxonomicName id="6BE9E7D24367FFEC094C91B2FE39FD7A" box="[342,420,653,672]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="1" pageNumber="6" phylum="Bryophyta" rank="subSpecies" species="patens" subSpecies="gametophores">
|
||
<emphasis id="9E9D40434367FFEC094C91B2FE39FD7A" bold="true" box="[342,420,653,672]" italics="true" pageId="1" pageNumber="2">P. patens</emphasis>
|
||
</taxonomicName>
|
||
gametophores is presented in
|
||
<figureCitation id="34D280D44367FFEC0AA091B2FD62FD7A" box="[698,767,653,672]" captionStart="Fig" captionStartId="1.[100,130,1913,1930]" captionTargetBox="[303,1286,742,1884]" captionTargetId="figure-438@1.[301,1287,741,1886]" captionTargetPageId="1" captionText="Fig. 1. The GC-MS oxylipin profiles of P. patens (A, B) and M. polymorpha (C, D). A and C, the profiles of endogenous oxylipins (Me/TMSi), the mixed ion current chromatograms (m/z 149, 177, 210, 225, 238, 278, 306, 308, 311). B and D, profiles of oxylipins (Me/TMSi) biosynthesized upon the in vitro preincubations of P. patens and M. polymorpha with α linolenic acid. The experimental details are described under “Experimental”." figureDoi="http://doi.org/10.5281/zenodo.8292674" httpUri="https://zenodo.org/record/8292674/files/figure.png" pageId="1" pageNumber="2">Fig. 1A</figureCitation>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="AC569C514367FFEC087E9196FB87FE64" blockId="1.[100,771,653,700]" lastBlockId="1.[818,1487,148,697]" pageId="1" pageNumber="2">
|
||
The predominant endogenous oxylipin was product
|
||
<emphasis id="9E9D40434367FFEC0A479196FDF4FD66" bold="true" box="[605,617,681,700]" pageId="1" pageNumber="2">1</emphasis>
|
||
(retention time 16.2 min, equivalent chain length (ECL) 20.61). For further characterization of the lipoxygenase pathway in
|
||
<taxonomicName id="6BE9E7D24367FFEC0CB6938FFB60FF19" box="[1196,1277,176,195]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="1" pageNumber="2" phylum="Bryophyta" rank="species" species="patens">
|
||
<emphasis id="9E9D40434367FFEC0CB6938FFB60FF19" bold="true" box="[1196,1277,176,195]" italics="true" pageId="1" pageNumber="2">P. patens</emphasis>
|
||
</taxonomicName>
|
||
and structural identification of product
|
||
<emphasis id="9E9D40434367FFEC0BF093F4FC6BFF04" bold="true" box="[1002,1014,203,222]" pageId="1" pageNumber="2">1</emphasis>
|
||
, the homogenate of gametophores was incubated with α linolenic acid. The GC-MS chromatogram of products (Me/ TMSi) of α linolenate conversion is presented in
|
||
<figureCitation id="34D280D44367FFEC0D0B923CFAC5FECD" box="[1297,1368,259,279]" captionStart="Fig" captionStartId="1.[100,130,1913,1930]" captionTargetBox="[303,1286,742,1884]" captionTargetId="figure-438@1.[301,1287,741,1886]" captionTargetPageId="1" captionText="Fig. 1. The GC-MS oxylipin profiles of P. patens (A, B) and M. polymorpha (C, D). A and C, the profiles of endogenous oxylipins (Me/TMSi), the mixed ion current chromatograms (m/z 149, 177, 210, 225, 238, 278, 306, 308, 311). B and D, profiles of oxylipins (Me/TMSi) biosynthesized upon the in vitro preincubations of P. patens and M. polymorpha with α linolenic acid. The experimental details are described under “Experimental”." figureDoi="http://doi.org/10.5281/zenodo.8292674" httpUri="https://zenodo.org/record/8292674/files/figure.png" pageId="1" pageNumber="2">Fig. 1B</figureCitation>
|
||
. The second product (by abundance) was the peak of 13-hydroxy-9,11,15-octadecatrienoic acid (Me/TMSi). Minorities were represented by peaks of
|
||
<emphasis id="9E9D40434367FFEC0D899204FA37FE94" bold="true" box="[1427,1450,315,334]" italics="true" pageId="1" pageNumber="2">cis</emphasis>
|
||
-12- OPDA (Me) and α ketol, 12-oxo-13-hydroxy-9,15-octadecadienoic acid (Me/TMSi), as seen from
|
||
<figureCitation id="34D280D44367FFEC0C31924CFBEEFE5C" box="[1067,1139,371,390]" captionStart="Fig" captionStartId="1.[100,130,1913,1930]" captionTargetBox="[303,1286,742,1884]" captionTargetId="figure-438@1.[301,1287,741,1886]" captionTargetPageId="1" captionText="Fig. 1. The GC-MS oxylipin profiles of P. patens (A, B) and M. polymorpha (C, D). A and C, the profiles of endogenous oxylipins (Me/TMSi), the mixed ion current chromatograms (m/z 149, 177, 210, 225, 238, 278, 306, 308, 311). B and D, profiles of oxylipins (Me/TMSi) biosynthesized upon the in vitro preincubations of P. patens and M. polymorpha with α linolenic acid. The experimental details are described under “Experimental”." figureDoi="http://doi.org/10.5281/zenodo.8292674" httpUri="https://zenodo.org/record/8292674/files/figure.png" pageId="1" pageNumber="2">Fig. 1B</figureCitation>
|
||
. The mass spectrum of
|
||
<emphasis id="9E9D40434367FFEC0D40924CFAECFE5C" bold="true" box="[1370,1393,371,390]" italics="true" pageId="1" pageNumber="2">cis</emphasis>
|
||
-12-OPDA (Me) and the corresponding mass fragmentation scheme are presented in Supplementary
|
||
<figureCitation id="34D280D44367FFEC0BC59294FB89FE64" box="[991,1044,427,446]" captionStart="Fig" captionStartId="1.[100,130,1913,1930]" captionTargetBox="[303,1286,742,1884]" captionTargetId="figure-438@1.[301,1287,741,1886]" captionTargetPageId="1" captionText="Fig. 1. The GC-MS oxylipin profiles of P. patens (A, B) and M. polymorpha (C, D). A and C, the profiles of endogenous oxylipins (Me/TMSi), the mixed ion current chromatograms (m/z 149, 177, 210, 225, 238, 278, 306, 308, 311). B and D, profiles of oxylipins (Me/TMSi) biosynthesized upon the in vitro preincubations of P. patens and M. polymorpha with α linolenic acid. The experimental details are described under “Experimental”." figureDoi="http://doi.org/10.5281/zenodo.8292674" httpUri="https://zenodo.org/record/8292674/files/figure.png" pageId="1" pageNumber="2">Fig. 1</figureCitation>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="AC569C514367FFEF0B4B92F8FC9FFDF7" blockId="1.[818,1487,148,697]" lastBlockId="2.[100,770,148,1004]" lastPageId="2" lastPageNumber="3" pageId="1" pageNumber="2">
|
||
The mass spectrum of predominant product
|
||
<emphasis id="9E9D40434367FFEC0CED92F9FA9EFE03" bold="true" box="[1271,1283,454,473]" pageId="1" pageNumber="2">1</emphasis>
|
||
possessed M
|
||
<superScript id="5B9C31194367FFEC0D6492FEFA10FE15" attach="left" box="[1406,1421,449,463]" fontSize="6" pageId="1" pageNumber="2">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434367FFEC0DB192F9FA52FE03" bold="true" box="[1451,1487,454,473]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
306 (16%), [M – MeO]
|
||
<superScript id="5B9C31194367FFEC0C1F92E2FB89FE31" attach="right" box="[1029,1044,477,491]" fontSize="6" pageId="1" pageNumber="2">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434367FFEC0C3792DDFBCFFE2F" bold="true" box="[1069,1106,482,501]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
275 (12),
|
||
<emphasis id="9E9D40434367FFEC0CAB92DDFB4BFE2F" bold="true" box="[1201,1238,482,501]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
217 (14), [M – C1/C6]
|
||
<superScript id="5B9C31194367FFEC0DB692E2FA26FE31" attach="right" box="[1452,1467,477,491]" fontSize="6" pageId="1" pageNumber="2">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434367FFEC0B2892C1FCCBFDCB" bold="true" box="[818,854,510,529]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
177 (78), [M – C1/C8]
|
||
<superScript id="5B9C31194367FFEC0C3192C6FBA7FDDD" attach="right" box="[1067,1082,505,519]" fontSize="6" pageId="1" pageNumber="2">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434367FFEC0C4992C1FBEAFDCB" bold="true" box="[1107,1143,510,529]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
149 (100),
|
||
<emphasis id="9E9D40434367FFEC0CF992C1FA9AFDCB" bold="true" box="[1251,1287,510,529]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
135 (38), and
|
||
<emphasis id="9E9D40434367FFEC0D9492C1FA2EFDCB" bold="true" box="[1422,1459,510,529]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
91 (65). The spectrum matched that of
|
||
<emphasis id="9E9D40434367FFEC0C939125FB3CFDF7" bold="true" box="[1161,1185,538,557]" italics="true" pageId="1" pageNumber="2">iso</emphasis>
|
||
-12-OPDA, i.e. 12-oxo-9(13),15- phytodienoic acid (Me) (
|
||
<bibRefCitation id="C878E1A04367FFEC0C329109FB4DFD93" author="Vick, B. A. & Zimmerman, D. C. & Weisleder, D." box="[1064,1232,566,586]" pageId="1" pageNumber="2" pagination="734 - 740" refId="ref9877" 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 converted compound
|
||
<emphasis id="9E9D40434367FFEC0C1E916DFB8DFDBF" bold="true" box="[1028,1040,594,613]" pageId="1" pageNumber="2">1</emphasis>
|
||
(Me) to product, whose mass spectrum (Supplementary
|
||
<figureCitation id="34D280D44367FFEC0BB89151FC4BFD5B" box="[930,982,622,641]" captionStart="Fig" captionStartId="3.[305,335,1206,1223]" captionTargetBox="[303,1286,149,1178]" captionTargetId="figure-622@3.[301,1287,148,1179]" captionTargetPageId="3" captionText="Fig. 2. The electron impact mass spectra and fragmentation schemes (insets) for products 1 (A), 2 (B), and 3 (C)." figureDoi="http://doi.org/10.5281/zenodo.8292676" httpUri="https://zenodo.org/record/8292676/files/figure.png" pageId="1" pageNumber="2">Fig. 2</figureCitation>
|
||
) possessed M
|
||
<superScript id="5B9C31194367FFEC0C4F9157FBF9FDAC" attach="both" box="[1109,1124,616,630]" fontSize="6" pageId="1" pageNumber="2">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434367FFEC0C649151FB3FFD5B" bold="true" box="[1150,1186,622,641]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
310 (0.1%), [M – MeO]
|
||
<superScript id="5B9C31194367FFEC0D989157FA0CFDAC" attach="right" box="[1410,1425,616,630]" fontSize="6" pageId="1" pageNumber="2">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434367FFEC0DB19151FA52FD5B" bold="true" box="[1451,1487,622,641]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
279 (1%), [M – C14/C18 +H]
|
||
<superScript id="5B9C31194367FFEC0C5291BBFBCAFD48" attach="right" box="[1096,1111,644,658]" fontSize="6" pageId="1" pageNumber="2">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434367FFEC0C7591B5FB09FD47" bold="true" box="[1135,1172,650,669]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
240 (4), [M – C1/C8]
|
||
<superScript id="5B9C31194367FFEC0D4191BBFAF7FD48" attach="right" box="[1371,1386,644,658]" fontSize="6" pageId="1" pageNumber="2">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434367FFEC0D9991B5FA3AFD47" bold="true" box="[1411,1447,650,669]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
153 (15), and
|
||
<emphasis id="9E9D40434367FFEC0B889199FC2AFD63" bold="true" box="[914,951,678,697]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
83 (100). These spectral patterns fully corresponded to that of the cyclopentanone 12-oxophytonoic acid (Me), which is also formed upon the hydrogenation of 12-OPDA (
|
||
<bibRefCitation id="C878E1A04364FFEF0A11938FFD51FF19" author="Grechkin, A. N. & Chechetkin, I. R. & Mukhtarova, L. S. & Hamberg, M." box="[523,716,176,195]" pageId="2" pageNumber="3" pagination="87 - 99" refId="ref7828" refString="Grechkin, A. N., Chechetkin, I. R., Mukhtarova, L. S., Hamberg, M., 2002. Role of structure and pH in cyclization of allene oxide fatty acids: implications for the reaction mechanism. Chem. Phys. Lipids 120, 87 - 99." type="journal article" year="2002">Grechkin et al., 2002</bibRefCitation>
|
||
). The sequential NaBH
|
||
<subScript id="306D9E144364FFEF08E593ECFE95FF3B" attach="left" box="[255,264,211,225]" fontSize="6" pageId="2" pageNumber="3">4</subScript>
|
||
reduction, methylation, hydrogenation over PtO
|
||
<subScript id="306D9E144364FFEF0AD693ECFD48FF3B" attach="right" box="[716,725,211,225]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
, and trimethylsilylation converted compound
|
||
<emphasis id="9E9D40434364FFEF09F093D8FE6BFF20" bold="true" box="[490,502,231,250]" pageId="2" pageNumber="3">1</emphasis>
|
||
to products, appearing as a group of three closely eluting peaks during the GC-MS analysis and having the identical mass spectral patterns (Supplementary
|
||
<figureCitation id="34D280D44364FFEF0A8A9220FD59FEE8" box="[656,708,287,306]" captionStart="Fig" captionStartId="4.[251,281,1012,1029]" captionTargetBox="[340,1247,150,982]" captionTargetId="figure-703@4.[338,1249,148,984]" captionTargetPageId="4" captionText="Fig. 3. The proposed pathways of biosynthesis of major cyclopentenones in P. patens and M. polymorpha. β oxn, β oxidation." figureDoi="http://doi.org/10.5281/zenodo.8292678" httpUri="https://zenodo.org/record/8292678/files/figure.png" pageId="2" pageNumber="3">Fig. 3</figureCitation>
|
||
): [M – Me]
|
||
<superScript id="5B9C31194364FFEF08909209FF04FE9E" attach="left" box="[138,153,310,324]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF08AF9204FF47FE94" bold="true" box="[181,218,315,334]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
369 (4%), [M – Me – MeO]
|
||
<superScript id="5B9C31194364FFEF09F89209FE6CFE9E" attach="left" box="[482,497,310,324]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0A179204FDAFFE94" bold="true" box="[525,562,315,334]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
337 (3),
|
||
<emphasis id="9E9D40434364FFEF0A919204FD2DFE94" bold="true" box="[651,688,315,334]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
224 (3),
|
||
<emphasis id="9E9D40434364FFEF087E9268FF14FEB0" bold="true" box="[100,137,343,362]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
159 (6), [
|
||
<collectingCountry id="D4FEDCC14364FFEF08F39268FE97FEB0" box="[233,266,343,362]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
<subScript id="306D9E144364FFEF09109261FE8EFEB6" attach="left" box="[266,275,350,364]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
––
|
||
<collectingCountry id="D4FEDCC14364FFEF093D9268FED9FEB0" box="[295,324,343,362]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
–
|
||
<collectingCountry id="D4FEDCC14364FFEF09559268FEF1FEB0" box="[335,364,343,362]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
––O
|
||
<superScript id="5B9C31194364FFEF098A926EFE01FE85" attach="left" box="[400,412,337,351]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
–SiMe
|
||
<subScript id="306D9E144364FFEF09CC9261FE42FEB6" attach="left" box="[470,479,350,364]" fontSize="6" pageId="2" pageNumber="3">3</subScript>
|
||
] at
|
||
<emphasis id="9E9D40434364FFEF0A129268FDB0FEB0" bold="true" box="[520,557,343,362]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
129 (100), [SiMe
|
||
<subScript id="306D9E144364FFEF0ACD9261FD7DFEB6" attach="right" box="[727,736,350,364]" fontSize="6" pageId="2" pageNumber="3">3</subScript>
|
||
] at
|
||
<emphasis id="9E9D40434364FFEF087E924CFF14FE5C" bold="true" box="[100,137,371,390]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
73 (70). The spectral patterns matched that of cyclopentanol 12-hydroxyphytonoic acid (Me/TMSi) (
|
||
<bibRefCitation id="C878E1A04364FFEF09EA92B0FD52FE78" author="Grechkin, A. N. & Chechetkin, I. R. & Mukhtarova, L. S. & Hamberg, M." box="[496,719,399,418]" pageId="2" pageNumber="3" pagination="87 - 99" refId="ref7828" refString="Grechkin, A. N., Chechetkin, I. R., Mukhtarova, L. S., Hamberg, M., 2002. Role of structure and pH in cyclization of allene oxide fatty acids: implications for the reaction mechanism. Chem. Phys. Lipids 120, 87 - 99." type="journal article" year="2002">Grechkin et al., 2002</bibRefCitation>
|
||
). Its appearance as a few peaks is explained by the formation of enantiomers and geometric isomers of cyclopentanol. Overall, the described data are fully consistent with the identification of compound
|
||
<emphasis id="9E9D40434364FFEF0A5492DDFDC7FE2F" bold="true" box="[590,602,482,501]" pageId="2" pageNumber="3">1</emphasis>
|
||
as the Me ester of 12-oxo-9(13),15-phytodienoic acid (
|
||
<emphasis id="9E9D40434364FFEF09A592C1FE4AFDCB" bold="true" box="[447,471,510,529]" italics="true" pageId="2" pageNumber="3">iso</emphasis>
|
||
-12-OPDA). For final structural approval, compound
|
||
<emphasis id="9E9D40434364FFEF09379125FEA4FDF7" bold="true" box="[301,313,538,557]" pageId="2" pageNumber="3">1</emphasis>
|
||
was purified, and the NMR data were recorded.
|
||
</paragraph>
|
||
<caption id="F896CCD94367FFEC087E9446FBB2F867" ID-DOI="http://doi.org/10.5281/zenodo.8292674" ID-Zenodo-Dep="8292674" httpUri="https://zenodo.org/record/8292674/files/figure.png" pageId="1" pageNumber="2" startId="1.[100,130,1913,1930]" targetBox="[303,1286,742,1884]" targetPageId="1" targetType="figure">
|
||
<paragraph id="AC569C514367FFEC087E9446FBB2F867" blockId="1.[100,1487,1913,1982]" pageId="1" pageNumber="2">
|
||
<emphasis id="9E9D40434367FFEC087E9446FF00F850" bold="true" box="[100,157,1913,1930]" pageId="1" pageNumber="2">Fig. 1.</emphasis>
|
||
The GC-MS oxylipin profiles of
|
||
<taxonomicName id="6BE9E7D24367FFEC09AF9445FE63F850" box="[437,510,1914,1930]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="1" pageNumber="2" phylum="Bryophyta" rank="species" species="patens">
|
||
<emphasis id="9E9D40434367FFEC09AF9445FE63F850" bold="true" box="[437,510,1914,1930]" italics="true" pageId="1" pageNumber="2">P. patens</emphasis>
|
||
</taxonomicName>
|
||
(A, B) and
|
||
<taxonomicName id="6BE9E7D24367FFEC0A789445FD40F850" box="[610,733,1913,1930]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="1" pageNumber="2" phylum="Marchantiophyta" rank="species" species="polymorpha">
|
||
<emphasis id="9E9D40434367FFEC0A789445FD40F850" bold="true" box="[610,733,1913,1930]" italics="true" pageId="1" pageNumber="2">M. polymorpha</emphasis>
|
||
</taxonomicName>
|
||
(C, D). A and C, the profiles of endogenous oxylipins (Me/TMSi), the mixed ion current chromatograms (
|
||
<emphasis id="9E9D40434367FFEC08EC94ACFE8AF87E" bold="true" box="[246,279,1939,1956]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
|
||
149, 177, 210, 225, 238, 278, 306, 308, 311). B and D, profiles of oxylipins (Me/TMSi) biosynthesized upon the
|
||
<emphasis id="9E9D40434367FFEC0CE294ACFAAFF87E" bold="true" box="[1272,1330,1939,1956]" italics="true" pageId="1" pageNumber="2">in vitro</emphasis>
|
||
preincubations of
|
||
<taxonomicName id="6BE9E7D24367FFEC087E9493FF33F866" box="[100,174,1964,1980]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="1" pageNumber="2" phylum="Bryophyta" rank="species" species="patens">
|
||
<emphasis id="9E9D40434367FFEC087E9493FF33F866" bold="true" box="[100,174,1964,1980]" italics="true" pageId="1" pageNumber="2">P. patens</emphasis>
|
||
</taxonomicName>
|
||
and
|
||
<taxonomicName id="6BE9E7D24367FFEC08C09493FEC8F867" box="[218,341,1964,1981]" class="Marchantiopsida" family="Marchantiaceae" genus="Marchantia" kingdom="Plantae" order="Marchantiales" pageId="1" pageNumber="2" phylum="Marchantiophyta" rank="species" species="polymorpha">
|
||
<emphasis id="9E9D40434367FFEC08C09493FEC8F867" bold="true" box="[218,341,1964,1981]" italics="true" pageId="1" pageNumber="2">M. polymorpha</emphasis>
|
||
</taxonomicName>
|
||
with α linolenic acid. The experimental details are described under “Experimental”.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="AC569C514364FFEF089E9109FDF9FC0A" blockId="2.[100,770,148,1004]" pageId="2" pageNumber="3">
|
||
The NMR spectral data for compound
|
||
<emphasis id="9E9D40434364FFEF09FE9109FE6DFD93" bold="true" box="[484,496,566,585]" pageId="2" pageNumber="3">1</emphasis>
|
||
are presented in
|
||
<tableCitation id="E16BA9EA4364FFEF0A959109FD49FD93" box="[655,724,566,585]" captionStart="Table 1" captionStartId="2.[100,150,1072,1088]" captionTargetPageId="2" captionText="Table 1 The NMR spectral data (1 H-NMR, 1 H– 1 H–COSY, 1 H– 1H-TOCSY, 1 H– 13C-HSQC and 1H–13C-HMBC) for compound 1 Me ester. 600 MHz, [2H]benzene, 303 K. 6" pageId="2" pageNumber="3">Table 1</tableCitation>
|
||
. The attribution of signals of protons at C2/C8 and C14/C18 was confirmed by the
|
||
<superScript id="5B9C31194364FFEF08BE9157FF30FDAC" attach="right" box="[164,173,616,630]" fontSize="6" pageId="2" pageNumber="3">1</superScript>
|
||
H–
|
||
<superScript id="5B9C31194364FFEF08DD9157FF4DFDAC" attach="right" box="[199,208,616,630]" fontSize="6" pageId="2" pageNumber="3">1</superScript>
|
||
H–COSY correlations. The
|
||
<superScript id="5B9C31194364FFEF09D39157FE4FFDAC" attach="right" box="[457,466,616,630]" fontSize="6" pageId="2" pageNumber="3">1</superScript>
|
||
H-NMR spectrum possessed only two olefinic protons H15 and H16. At the same time, the
|
||
<superScript id="5B9C31194364FFEF0A9291BBFD07FD48" attach="right" box="[648,666,644,658]" fontSize="6" pageId="2" pageNumber="3">13</superScript>
|
||
C chemical shifts (
|
||
<tableCitation id="E16BA9EA4364FFEF08B29199FF6EFD63" box="[168,243,678,697]" captionStart="Table 1" captionStartId="2.[100,150,1072,1088]" captionTargetPageId="2" captionText="Table 1 The NMR spectral data (1 H-NMR, 1 H– 1 H–COSY, 1 H– 1H-TOCSY, 1 H– 13C-HSQC and 1H–13C-HMBC) for compound 1 Me ester. 600 MHz, [2H]benzene, 303 K. 6" pageId="2" pageNumber="3">Table 1</tableCitation>
|
||
) estimated from the HSQC and HMBC spectral data, demonstrated the presence of double bond between C9 and C13, the cyclopentenone carbons bearing the side chains. Position of C9 and C13 towards the neighbouring functional groups (particularly, H8 and H14) is unequivocally confirmed by the heteronuclear multiple bond correlations (
|
||
<superScript id="5B9C31194364FFEF08A39014FF5FFCE3" attach="right" box="[185,194,811,825]" fontSize="6" pageId="2" pageNumber="3">1</superScript>
|
||
H,
|
||
<superScript id="5B9C31194364FFEF08C29014FF77FCE3" attach="right" box="[216,234,811,825]" fontSize="6" pageId="2" pageNumber="3">13</superScript>
|
||
C-HMBC data,
|
||
<tableCitation id="E16BA9EA4364FFEF099F900EFE4EFC9E" box="[389,467,817,836]" captionStart="Table 1" captionStartId="2.[100,150,1072,1088]" captionTargetPageId="2" captionText="Table 1 The NMR spectral data (1 H-NMR, 1 H– 1 H–COSY, 1 H– 1H-TOCSY, 1 H– 13C-HSQC and 1H–13C-HMBC) for compound 1 Me ester. 600 MHz, [2H]benzene, 303 K. 6" pageId="2" pageNumber="3">Table 1</tableCitation>
|
||
). Other chemical shifts were unambiguously attributed thanks the
|
||
<superScript id="5B9C31194364FFEF09D59078FE45FC8F" attach="right" box="[463,472,839,853]" fontSize="6" pageId="2" pageNumber="3">1</superScript>
|
||
H–
|
||
<superScript id="5B9C31194364FFEF09E99078FE61FC8F" attach="right" box="[499,508,839,853]" fontSize="6" pageId="2" pageNumber="3">1</superScript>
|
||
H–COSY, HSQC and HMBC spectra, for instance, the homonuclear and heteronuclear multiple bond correlations (estimated from the HMBC spectral data). To summarize, the data fully confirmed the identification of compound
|
||
<emphasis id="9E9D40434364FFEF0A9A909EFD11FC6E" bold="true" box="[640,652,929,948]" pageId="2" pageNumber="3">1</emphasis>
|
||
as 12-oxo-9 (13),15-phytodienoic acid (Me), i.e., the
|
||
<emphasis id="9E9D40434364FFEF09FC9082FE63FC0A" bold="true" box="[486,510,957,976]" italics="true" pageId="2" pageNumber="3">iso</emphasis>
|
||
-12-OPDA.
|
||
</paragraph>
|
||
<paragraph id="AC569C514364FFEF089E90E6FBC9FD47" blockId="2.[100,770,148,1004]" lastBlockId="2.[818,1490,148,1785]" pageId="2" pageNumber="3">
|
||
The less abundant product
|
||
<emphasis id="9E9D40434364FFEF099F90E7FE0CFC31" bold="true" box="[389,401,984,1003]" pageId="2" pageNumber="3">2</emphasis>
|
||
, possessing similar product patterns to those of compound
|
||
<emphasis id="9E9D40434364FFEF0BE993ABFC62FF7D" bold="true" box="[1011,1023,148,167]" pageId="2" pageNumber="3">1</emphasis>
|
||
, had shorter retention time (13.2 min) and the equivalent chain length (ECL) 18.53. The mass spectrum of product
|
||
<emphasis id="9E9D40434364FFEF0DD9938FFA52FF19" bold="true" box="[1475,1487,176,195]" pageId="2" pageNumber="3">2</emphasis>
|
||
(
|
||
<figureCitation id="34D280D44364FFEF0B2093F4FCE1FF05" box="[826,892,203,223]" captionStart="Fig" captionStartId="3.[305,335,1206,1223]" captionTargetBox="[303,1286,149,1178]" captionTargetId="figure-622@3.[301,1287,148,1179]" captionTargetPageId="3" captionText="Fig. 2. The electron impact mass spectra and fragmentation schemes (insets) for products 1 (A), 2 (B), and 3 (C)." figureDoi="http://doi.org/10.5281/zenodo.8292676" httpUri="https://zenodo.org/record/8292676/files/figure.png" pageId="2" pageNumber="3">Fig. 2B</figureCitation>
|
||
) possessed M
|
||
<superScript id="5B9C31194364FFEF0BE393F9FB95FF0E" attach="left" box="[1017,1032,198,212]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0C3893F4FBDBFF04" bold="true" box="[1058,1094,203,222]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
278 (25%), [M – Et]
|
||
<superScript id="5B9C31194364FFEF0D1C93F9FA88FF0E" attach="right" box="[1286,1301,198,212]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0D3493F4FACEFF04" bold="true" box="[1326,1363,203,222]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
249 (10), [M – MeO]
|
||
<superScript id="5B9C31194364FFEF0B6D93DDFC1BFF2A" attach="left" box="[887,902,226,240]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0BBA93D8FC58FF20" bold="true" box="[928,965,231,250]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
247 (5), [M – C1/C4]
|
||
<superScript id="5B9C31194364FFEF0C8B93DDFB3DFF2A" attach="left" box="[1169,1184,226,240]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0CA093D8FB42FF20" bold="true" box="[1210,1247,231,250]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
177 (100), [M – C1/C6]
|
||
<superScript id="5B9C31194364FFEF0DD993DDFA4FFF2A" attach="none" box="[1475,1490,226,240]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0B53923CFCF0FECC" bold="true" box="[841,877,259,278]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
149 (97),
|
||
<emphasis id="9E9D40434364FFEF0BD7923CFC6FFECC" bold="true" box="[973,1010,259,278]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
135 (36),
|
||
<emphasis id="9E9D40434364FFEF0C48923CFBEAFECC" bold="true" box="[1106,1143,259,278]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
122 (40),
|
||
<emphasis id="9E9D40434364FFEF0CCD923CFB66FECC" bold="true" box="[1239,1275,259,278]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
105 (34),
|
||
<emphasis id="9E9D40434364FFEF0D41923CFA1DFECC" bold="true" box="[1371,1408,259,278]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
91 (77),
|
||
<emphasis id="9E9D40434364FFEF0B289220FCCBFEE8" bold="true" box="[818,854,287,306]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
79 (79), and
|
||
<emphasis id="9E9D40434364FFEF0BC09220FC62FEE8" bold="true" box="[986,1023,287,306]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
67 (41). The spectral patterns of product
|
||
<emphasis id="9E9D40434364FFEF0D8A9220FA01FEE8" bold="true" box="[1424,1436,287,306]" pageId="2" pageNumber="3">2</emphasis>
|
||
indicated the structure of 2,3-dinor analogue of compound
|
||
<emphasis id="9E9D40434364FFEF0D2D9204FADEFE94" bold="true" box="[1335,1347,315,334]" pageId="2" pageNumber="3">1</emphasis>
|
||
, i.e. 2,3-dinor-12-oxo-9(13)-PDA (Me) (dinor-
|
||
<emphasis id="9E9D40434364FFEF0C799268FBE6FEB0" bold="true" box="[1123,1147,343,362]" italics="true" pageId="2" pageNumber="3">iso</emphasis>
|
||
-12-OPDA). The sequential NaBH
|
||
<subScript id="306D9E144364FFEF0DDC9261FA52FEB6" attach="left" box="[1478,1487,350,364]" fontSize="6" pageId="2" pageNumber="3">4</subScript>
|
||
reduction, methylation, hydrogenation over PtO
|
||
<subScript id="306D9E144364FFEF0CE49245FA9AFE52" attach="left" box="[1278,1287,378,392]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
, and trimethylsilylation turned product
|
||
<emphasis id="9E9D40434364FFEF0BE892B0FC63FE78" bold="true" box="[1010,1022,399,418]" pageId="2" pageNumber="3">2</emphasis>
|
||
to compound
|
||
<emphasis id="9E9D40434364FFEF0C9292B0FB3DFE78" bold="true" box="[1160,1184,399,418]" pageId="2" pageNumber="3">2a</emphasis>
|
||
, whose mass spectrum (Supplementary Fig. 4) possessed [M – Me]
|
||
<superScript id="5B9C31194364FFEF0C60929AFB14FE69" attach="right" box="[1146,1161,421,435]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0CB89294FB5BFE64" bold="true" box="[1186,1222,427,446]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
341 (7%), [M – Me – MeO]
|
||
<superScript id="5B9C31194364FFEF0DD9929AFA4FFE69" attach="none" box="[1475,1490,421,435]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0B5392F9FCF3FE03" bold="true" box="[841,878,454,473]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
309 (1), [M – TMSiOH]
|
||
<superScript id="5B9C31194364FFEF0C5592FEFBC3FE15" attach="left" box="[1103,1118,449,463]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0C6392F9FB03FE03" bold="true" box="[1145,1182,454,473]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
266 (5),
|
||
<emphasis id="9E9D40434364FFEF0CEE92F9FA84FE03" bold="true" box="[1268,1305,454,473]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
234 (4%),
|
||
<emphasis id="9E9D40434364FFEF0D9B92F9FA3BFE03" bold="true" box="[1409,1446,454,473]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
164 (7), [
|
||
<collectingCountry id="D4FEDCC14364FFEF0B7B92DCFC1FFE2C" box="[865,898,483,502]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
<subScript id="306D9E144364FFEF0B9892D5FC16FE22" attach="left" box="[898,907,490,504]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
––
|
||
<collectingCountry id="D4FEDCC14364FFEF0B8592DCFC21FE2C" box="[927,956,483,502]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
–
|
||
<collectingCountry id="D4FEDCC14364FFEF0BDD92DCFC79FE2C" box="[967,996,483,502]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
––O
|
||
<superScript id="5B9C31194364FFEF0C1292E2FB89FE31" attach="left" box="[1032,1044,477,491]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
–SiMe
|
||
<subScript id="306D9E144364FFEF0C5492D5FBCAFE22" attach="left" box="[1102,1111,490,504]" fontSize="6" pageId="2" pageNumber="3">3</subScript>
|
||
] at
|
||
<emphasis id="9E9D40434364FFEF0C9992DDFB3AFE2F" bold="true" box="[1155,1191,482,501]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
129 (100), [SiMe
|
||
<subScript id="306D9E144364FFEF0D4C92D5FAC2FE22" attach="right" box="[1366,1375,490,504]" fontSize="6" pageId="2" pageNumber="3">3</subScript>
|
||
] at
|
||
<emphasis id="9E9D40434364FFEF0D9092DDFA32FE2F" bold="true" box="[1418,1455,482,501]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
73 (60). Fragment
|
||
<collectingCountry id="D4FEDCC14364FFEF0BD092C1FC7AFDCB" box="[970,999,510,529]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
<subScript id="306D9E144364FFEF0BFD9139FC6DFDCE" attach="left" box="[999,1008,518,532]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
––
|
||
<collectingCountry id="D4FEDCC14364FFEF0C1F92C1FBBFFDCB" box="[1029,1058,510,529]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
–
|
||
<collectingCountry id="D4FEDCC14364FFEF0C3792C1FBD7FDCB" box="[1069,1098,510,529]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
––O
|
||
<superScript id="5B9C31194364FFEF0C7492C6FBE7FDDD" attach="right" box="[1134,1146,505,519]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
–SiMe
|
||
<subScript id="306D9E144364FFEF0CA99139FB21FDCE" attach="left" box="[1203,1212,518,532]" fontSize="6" pageId="2" pageNumber="3">3</subScript>
|
||
representing a base peak at
|
||
<emphasis id="9E9D40434364FFEF0B289125FCCBFDF7" bold="true" box="[818,854,538,557]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
129 is distinguishing for TMSi-cyclopentanol structures. Overall, the described mass spectral data allow ascribing the structures of 1- hydroxy-2-(2’(Z)-pentenyl)-cyclopentane-3-hexanoic acid (Me/TMSi) and 2,3-dinor-12-oxo-9(13)-PDA (Me) (dinor-
|
||
<emphasis id="9E9D40434364FFEF0CEE9151FA91FD5B" bold="true" box="[1268,1292,622,641]" italics="true" pageId="2" pageNumber="3">iso</emphasis>
|
||
-12-OPDA) to compounds
|
||
<emphasis id="9E9D40434364FFEF0B6691B5FC09FD47" bold="true" box="[892,916,650,669]" pageId="2" pageNumber="3">2a</emphasis>
|
||
and
|
||
<emphasis id="9E9D40434364FFEF0BDE91B5FC4DFD47" bold="true" box="[964,976,650,669]" pageId="2" pageNumber="3">2</emphasis>
|
||
, respectively.
|
||
</paragraph>
|
||
<paragraph id="AC569C514364FFEF0B4B9199FC01FA38" blockId="2.[818,1490,148,1785]" pageId="2" pageNumber="3">
|
||
The hydroxy fatty acids have also been detected in
|
||
<taxonomicName id="6BE9E7D24364FFEF0D509199FA00FD63" box="[1354,1437,678,697]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="2" pageNumber="3" phylum="Bryophyta" rank="species" species="patens">
|
||
<emphasis id="9E9D40434364FFEF0D509199FA00FD63" bold="true" box="[1354,1437,678,697]" italics="true" pageId="2" pageNumber="3">P. patens</emphasis>
|
||
</taxonomicName>
|
||
. The hydroxy acids 13-hydroxy-9,11,15-octadecatrienoic (13-HOT) and 13- hydroxy-9,11-octadecadienoic acids (13-HOD) (Me/TMSi) derived from the 13-lipoxygenase activity were detected (their spectral data are not presented). Upon the sequential reduction with sodium borohydride, hydrogenation over PtO
|
||
<subScript id="306D9E144364FFEF0C0D9007FBBDFC9C" attach="left" box="[1047,1056,824,838]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
, methylation with diazomethane, and trimethylsilylation these products turned to the 13-hydroxystearic acid (Me/ TMSi), thus confirming the identification of 13-HOT and 13-HOD. Besides, there was a minor product, eluting close before the methyl stearate, whose mass spectrum possessed [M – Me]
|
||
<superScript id="5B9C31194364FFEF0CFB90A4FB6DFC73" attach="right" box="[1249,1264,923,937]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0D13909EFAB0FC6E" bold="true" box="[1289,1325,929,948]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
337 (0.6%), [M – MeO]
|
||
<superScript id="5B9C31194364FFEF0B7D9088FCEBFC1F" attach="left" box="[871,886,951,965]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0B8B9082FC2BFC0A" bold="true" box="[913,950,957,976]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
321 (0.4%), [M – MeCH
|
||
<subScript id="306D9E144364FFEF0C8790FBFB3BFC08" attach="both" box="[1181,1190,964,978]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
<collectingCountry id="D4FEDCC14364FFEF0CBC9082FB5EFC0A" box="[1190,1219,957,976]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
––CHCH
|
||
<subScript id="306D9E144364FFEF0D0890FBFA86FC08" attach="right" box="[1298,1307,964,978]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
]
|
||
<superScript id="5B9C31194364FFEF0D3E9088FAAEFC1F" attach="left" box="[1316,1331,951,965]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0D579082FAEFFC0A" bold="true" box="[1357,1394,957,976]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
283 (62), [M – (
|
||
<collectingCountry id="D4FEDCC14364FFEF0B7090E6FC14FC36" box="[874,905,985,1004]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
<subScript id="306D9E144364FFEF0B9390DFFC0FFC34" attach="left" box="[905,914,992,1006]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
)
|
||
<subScript id="306D9E144364FFEF0B8090DFFC3EFC34" attach="right" box="[922,931,992,1006]" fontSize="6" pageId="2" pageNumber="3">5</subScript>
|
||
COOMe]
|
||
<superScript id="5B9C31194364FFEF0BEF90ECFB99FC3B" attach="left" box="[1013,1028,979,993]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0C0590E6FBD9FC36" bold="true" box="[1055,1092,985,1004]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
223 (1),
|
||
<emphasis id="9E9D40434364FFEF0C8190E6FB5DFC36" bold="true" box="[1179,1216,985,1004]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
161 (23),
|
||
<emphasis id="9E9D40434364FFEF0D3990E6FAD5FC36" bold="true" box="[1315,1352,985,1004]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
133 (48),
|
||
<emphasis id="9E9D40434364FFEF0DB190E6FA52FC36" bold="true" box="[1451,1487,985,1004]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
119 (26),
|
||
<emphasis id="9E9D40434364FFEF0B8E90CBFC25FBDD" bold="true" box="[916,952,1012,1031]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
105 (15),
|
||
<emphasis id="9E9D40434364FFEF0C3890CBFBDAFBDD" bold="true" box="[1058,1095,1012,1031]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
91 (24), [SiMe
|
||
<subScript id="306D9E144364FFEF0CC790C3FB7BFBD0" attach="right" box="[1245,1254,1020,1034]" fontSize="6" pageId="2" pageNumber="3">3</subScript>
|
||
]
|
||
<superScript id="5B9C31194364FFEF0CF590D0FB63FC27" attach="left" box="[1263,1278,1007,1021]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0D0790CBFADFFBDD" bold="true" box="[1309,1346,1012,1031]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
73 (100). The main characteristic fragment at
|
||
<emphasis id="9E9D40434364FFEF0C7A972FFB18FBF9" bold="true" box="[1120,1157,1040,1059]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
283 allowed the preliminary identification of the product as the 11-hydroxy-7,9,13-hexadecatrienoic acid (11-HHT, Me/TMSi). For further structural confirmation, the product was subjected to the sequential reduction with sodium borohydride, hydrogenation over PtO
|
||
<subScript id="306D9E144364FFEF0C0D97B8FBBDFB4F" attach="left" box="[1047,1056,1159,1173]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
, methylation with diazomethane, and trimethylsilylation. The mass spectrum of the resulting saturated analogue possessed [M – Me]
|
||
<superScript id="5B9C31194364FFEF0BFC978DFC68FB1A" attach="right" box="[998,1013,1202,1216]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0C149787FBAEFB11" bold="true" box="[1038,1075,1208,1227]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
343 (0.3%), [M – MeO]
|
||
<superScript id="5B9C31194364FFEF0D0A978DFA82FB1A" attach="right" box="[1296,1311,1202,1216]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0D2D9787FAC1FB11" bold="true" box="[1335,1372,1208,1227]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
327 (0.4%), [M – Me – MeO]
|
||
<superScript id="5B9C31194364FFEF0BD197F1FC47FB06" attach="left" box="[971,986,1230,1244]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0BEE97ECFB84FB3C" bold="true" box="[1012,1049,1235,1254]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
311 (3%), [M – Pe]
|
||
<superScript id="5B9C31194364FFEF0CC897F1FB7CFB06" attach="right" box="[1234,1249,1230,1244]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0CE197ECFABDFB3C" bold="true" box="[1275,1312,1235,1254]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
287 (21),
|
||
<emphasis id="9E9D40434364FFEF0D9B97ECFA3BFB3C" bold="true" box="[1409,1446,1235,1254]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
258 (6), [M – (
|
||
<collectingCountry id="D4FEDCC14364FFEF0B8F97CFFC29FAD9" box="[917,948,1264,1283]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
<subScript id="306D9E144364FFEF0BAE97C8FC20FADF" attach="left" box="[948,957,1271,1285]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
)
|
||
<subScript id="306D9E144364FFEF0BDF97C8FC53FADF" attach="right" box="[965,974,1271,1285]" fontSize="6" pageId="2" pageNumber="3">9</subScript>
|
||
COOMe]
|
||
<superScript id="5B9C31194364FFEF0C3A97D5FBB2FB22" attach="left" box="[1056,1071,1258,1272]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0C5797D0FBECFAD8" bold="true" box="[1101,1137,1263,1282]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
173 (62),
|
||
<emphasis id="9E9D40434364FFEF0CC297D0FB61FAD8" bold="true" box="[1240,1276,1263,1282]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
159 (6),
|
||
<emphasis id="9E9D40434364FFEF0D4D97D0FAE1FAD8" bold="true" box="[1367,1404,1263,1282]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
129 (6), [
|
||
<collectingCountry id="D4FEDCC14364FFEF0B2D9634FCC5FAC4" box="[823,856,1291,1310]" name="Switzerland" pageId="2" pageNumber="3">CH</collectingCountry>
|
||
<subScript id="306D9E144364FFEF0B42962CFCFCFAFB" attach="left" box="[856,865,1299,1313]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
––O
|
||
<superScript id="5B9C31194364FFEF0B9F9639FC0CFACE" attach="left" box="[901,913,1286,1300]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
–SiMe
|
||
<subScript id="306D9E144364FFEF0BD0962CFC4EFAFB" attach="left" box="[970,979,1299,1313]" fontSize="6" pageId="2" pageNumber="3">3</subScript>
|
||
] at
|
||
<emphasis id="9E9D40434364FFEF0BE59634FBB9FAC4" bold="true" box="[1023,1060,1291,1310]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
103 (12),
|
||
<emphasis id="9E9D40434364FFEF0C949634FB2EFAC4" bold="true" box="[1166,1203,1291,1310]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
75 (41), [SiMe
|
||
<subScript id="306D9E144364FFEF0D53962CFACFFAFB" attach="left" box="[1353,1362,1299,1313]" fontSize="6" pageId="2" pageNumber="3">3</subScript>
|
||
]
|
||
<superScript id="5B9C31194364FFEF0D419639FAF7FACE" attach="left" box="[1371,1386,1286,1300]" fontSize="6" pageId="2" pageNumber="3">+</superScript>
|
||
at
|
||
<emphasis id="9E9D40434364FFEF0D909634FA32FAC4" bold="true" box="[1418,1455,1291,1310]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
|
||
73 (100). The fragmentation patterns matched that for 11-hydroxypalmitic acid (Me/TMSi) (
|
||
<bibRefCitation id="C878E1A04364FFEF0BC2967CFB05FA8C" author="Osipova, E. V. & Lantsova, N. V. & Chechetkin, I. R. & Mukhitova, F. K. & Hamberg, M. & Grechkin, A. N." box="[984,1176,1347,1367]" pageId="2" pageNumber="3" pagination="708 - 716" refId="ref9001" refString="Osipova, E. V., Lantsova, N. V., Chechetkin, I. R., Mukhitova, F. K., Hamberg, M., Grechkin, A. N., 2010. Hexadecanoid pathway in plants: lipoxygenase dioxygenation of (7 Z, 10 Z, 13 Z) - hexadecatrienoic acid. Biochemistry (Moscow) 75, 708 - 716." type="journal article" year="2010">Osipova et al., 2010</bibRefCitation>
|
||
), thus confirming the identification of the unreduced product as the 11-HHT (Me/TMSi). The ratio of 11-HHT to 13-HOT was ca. 1:10, as estimated by integration of the total ion current chromatograms. The hydroxy derivatives of arachidonic and eicosapentaenoic acids were present only at trace levels (results not presented).
|
||
</paragraph>
|
||
<caption id="F896CCD94364FFEF087E970FFDF2FBAF" pageId="2" pageNumber="3" startId="2.[100,150,1072,1088]" targetBox="[116,754,1156,1917]" targetIsTable="true" targetPageId="2" targetType="table">
|
||
<paragraph id="AC569C514364FFEF087E970FFF3AFB9B" blockId="2.[100,769,1072,1141]" box="[100,167,1072,1089]" pageId="2" pageNumber="3">
|
||
<emphasis id="9E9D40434364FFEF087E970FFF3AFB9B" bold="true" box="[100,167,1072,1089]" pageId="2" pageNumber="3">Table 1</emphasis>
|
||
</paragraph>
|
||
<paragraph id="AC569C514364FFEF087E9776FC9CFBA9" blockId="2.[100,769,1072,1141]" pageId="2" pageNumber="3">
|
||
The NMR spectral data (
|
||
<superScript id="5B9C31194364FFEF0923977BFEDCFB8A" attach="right" box="[313,321,1092,1104]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H-NMR,
|
||
<superScript id="5B9C31194364FFEF0997977BFE08FB8A" attach="right" box="[397,405,1092,1104]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H–
|
||
<superScript id="5B9C31194364FFEF09B7977BFE28FB8A" attach="right" box="[429,437,1092,1104]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H–COSY,
|
||
<superScript id="5B9C31194364FFEF0A13977BFD8CFB8A" attach="right" box="[521,529,1092,1104]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H–
|
||
<superScript id="5B9C31194364FFEF0A33977BFDACFB8A" attach="right" box="[553,561,1092,1104]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H-TOCSY,
|
||
<superScript id="5B9C31194364FFEF0A97977BFD08FB8A" attach="right" box="[653,661,1092,1104]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H–
|
||
<superScript id="5B9C31194364FFEF0AB7977BFD20FB8A" attach="right" box="[685,701,1092,1104]" fontSize="5" pageId="2" pageNumber="3">13</superScript>
|
||
C-HSQC and
|
||
<superScript id="5B9C31194364FFEF08939761FF0CFBB0" attach="right" box="[137,145,1118,1130]" fontSize="5" pageId="2" pageNumber="3">1</superScript>
|
||
H–
|
||
<superScript id="5B9C31194364FFEF08B39761FF24FBB0" attach="right" box="[169,185,1118,1130]" fontSize="5" pageId="2" pageNumber="3">13</superScript>
|
||
C-HMBC) for compound
|
||
<emphasis id="9E9D40434364FFEF0996975CFE0AFBAE" bold="true" box="[396,407,1123,1140]" pageId="2" pageNumber="3">1</emphasis>
|
||
Me ester. 600 MHz, [
|
||
<superScript id="5B9C31194364FFEF0A4B9761FDC4FBB0" attach="right" box="[593,601,1118,1130]" fontSize="5" pageId="2" pageNumber="3">2</superScript>
|
||
H]benzene, 303 K.
|
||
</paragraph>
|
||
<paragraph id="AC569C514364FFEF0A7D9756FDF2FBAF" blockId="2.[100,769,1072,1141]" box="[615,623,1129,1141]" pageId="2" pageNumber="3">
|
||
<subScript id="306D9E144364FFEF0A7D9756FDF2FBAF" attach="left" box="[615,623,1129,1141]" fontSize="5" pageId="2" pageNumber="3">6</subScript>
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="AC569C514364FFEF086E97B7FDE4F8A7" pageId="2" pageNumber="3">
|
||
<table id="DEE96EF143640012086E97BBFD6FF8A7" box="[116,754,1156,1917]" gridcols="4" gridrows="33" pageId="2" pageNumber="3">
|
||
<tr id="12D99E1343640012086E97BBFD6FFB4C" box="[116,754,1156,1174]" gridrow="0" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E97BBFF2CFB4C" box="[116,177,1156,1174]" gridcol="0" gridrow="0" pageId="2" pageNumber="3">Position</th>
|
||
<th id="5108F76F4364001208C597BBFEC0FB4C" box="[223,349,1156,1174]" gridcol="1" gridrow="0" pageId="2" pageNumber="3">13C chemical</th>
|
||
<th id="5108F76F43640012096497BBFDBCFB4C" box="[382,545,1156,1174]" gridcol="2" gridrow="0" pageId="2" pageNumber="3">1H chemical shifts</th>
|
||
<th id="5108F76F436400120A5E97BBFD6FFB4C" box="[580,754,1156,1174]" gridcol="3" gridrow="0" pageId="2" pageNumber="3">Homonuclear and</th>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E97A1FD6FFB76" box="[116,754,1182,1196]" gridrow="1" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E97A1FF2CFB76" box="[116,177,1182,1196]" gridcol="0" gridrow="1" pageId="2" pageNumber="3">number</th>
|
||
<td id="5108F76F4364001208C597A1FEC0FB76" box="[223,349,1182,1196]" gridcol="1" gridrow="1" pageId="2" pageNumber="3">shifts (ppm);</td>
|
||
<td id="5108F76F43640012096497A1FDBCFB76" box="[382,545,1182,1196]" gridcol="2" gridrow="1" pageId="2" pageNumber="3">(ppm); multiplicity;</td>
|
||
<td id="5108F76F436400120A5E97A1FD6FFB76" box="[580,754,1182,1196]" gridcol="3" gridrow="1" pageId="2" pageNumber="3">heteronuclear multiple</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E978AFD6FFB1E" box="[116,754,1205,1220]" gridrow="2" pageId="2" pageNumber="3" rowspan-0="1">
|
||
<td id="5108F76F4364001208C5978AFEC0FB1E" box="[223,349,1205,1220]" gridcol="1" gridrow="2" pageId="2" pageNumber="3">functional group</td>
|
||
<td id="5108F76F436400120964978AFDBCFB1E" box="[382,545,1205,1220]" gridcol="2" gridrow="2" pageId="2" pageNumber="3">coupling constant</td>
|
||
<td id="5108F76F436400120A5E978AFD6FFB1E" box="[580,754,1205,1220]" gridcol="3" gridrow="2" pageId="2" pageNumber="3">bond correlations</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E97F3FD6FFB00" box="[116,754,1228,1242]" gridrow="3" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-3="1">
|
||
<td id="5108F76F43640012096497F3FDBCFB00" box="[382,545,1228,1242]" gridcol="2" gridrow="3" pageId="2" pageNumber="3">(Hz)</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E97D0FD6FFB27" box="[116,754,1263,1277]" gridrow="4" pageId="2" pageNumber="3" rowspan-2="1">
|
||
<th id="5108F76F43640012086E97D0FF2CFB27" box="[116,177,1263,1277]" gridcol="0" gridrow="4" pageId="2" pageNumber="3">1</th>
|
||
<td id="5108F76F4364001208C597D0FEC0FB27" box="[223,349,1263,1277]" gridcol="1" gridrow="4" pageId="2" pageNumber="3">173.59; COOMe</td>
|
||
<td id="5108F76F436400120A5E97D0FD6FFB27" box="[580,754,1263,1277]" gridcol="3" gridrow="4" pageId="2" pageNumber="3">H2; H3</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9639FD6FFACC" box="[116,754,1286,1302]" gridrow="5" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E9639FF2CFACC" box="[116,177,1286,1302]" gridcol="0" gridrow="5" pageId="2" pageNumber="3">2</th>
|
||
<td id="5108F76F4364001208C59639FEC0FACC" box="[223,349,1286,1302]" gridcol="1" gridrow="5" pageId="2" pageNumber="3">34.03; CH2</td>
|
||
<td id="5108F76F4364001209649639FDBCFACC" box="[382,545,1286,1302]" gridcol="2" gridrow="5" pageId="2" pageNumber="3">2.13, t, 7.4 (H3)</td>
|
||
<td id="5108F76F436400120A5E9639FD6FFACC" box="[580,754,1286,1302]" gridcol="3" gridrow="5" pageId="2" pageNumber="3">C1; C3; C4; H3; H4</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9622FD6FFAF7" box="[116,754,1309,1325]" gridrow="6" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E9622FF2CFAF7" box="[116,177,1309,1325]" gridcol="0" gridrow="6" pageId="2" pageNumber="3">3</th>
|
||
<td id="5108F76F4364001208C59622FEC0FAF7" box="[223,349,1309,1325]" gridcol="1" gridrow="6" pageId="2" pageNumber="3">25.21; CH2</td>
|
||
<td id="5108F76F4364001209649622FDBCFAF7" box="[382,545,1309,1325]" gridcol="2" gridrow="6" pageId="2" pageNumber="3">1.55, tt, 7.4 (H5)</td>
|
||
<td id="5108F76F436400120A5E9622FD6FFAF7" box="[580,754,1309,1325]" gridcol="3" gridrow="6" pageId="2" pageNumber="3">C1; C2; C4; H4; H5</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E960BFD6FFA9E" box="[116,754,1332,1348]" gridrow="7" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E960BFF2CFA9E" box="[116,177,1332,1348]" gridcol="0" gridrow="7" pageId="2" pageNumber="3">4</th>
|
||
<td id="5108F76F4364001208C5960BFEC0FA9E" box="[223,349,1332,1348]" gridcol="1" gridrow="7" pageId="2" pageNumber="3">29.33; CH2</td>
|
||
<td id="5108F76F436400120964960BFDBCFA9E" box="[382,545,1332,1348]" gridcol="2" gridrow="7" pageId="2" pageNumber="3">1.15, m</td>
|
||
<td id="5108F76F436400120A5E960BFD6FFA9E" box="[580,754,1332,1348]" gridcol="3" gridrow="7" pageId="2" pageNumber="3">C2; C3</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9675FD6FFA81" box="[116,754,1354,1371]" gridrow="8" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E9675FF2CFA81" box="[116,177,1354,1371]" gridcol="0" gridrow="8" pageId="2" pageNumber="3">5</th>
|
||
<td id="5108F76F4364001208C59675FEC0FA81" box="[223,349,1354,1371]" gridcol="1" gridrow="8" pageId="2" pageNumber="3">29.36; CH2</td>
|
||
<td id="5108F76F4364001209649675FDBCFA81" box="[382,545,1354,1371]" gridcol="2" gridrow="8" pageId="2" pageNumber="3">1.11, m</td>
|
||
<td id="5108F76F436400120A5E9675FD6FFA81" box="[580,754,1354,1371]" gridcol="3" gridrow="8" pageId="2" pageNumber="3">C3</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E965EFD6FFAA8" box="[116,754,1377,1394]" gridrow="9" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E965EFF2CFAA8" box="[116,177,1377,1394]" gridcol="0" gridrow="9" pageId="2" pageNumber="3">6</th>
|
||
<td id="5108F76F4364001208C5965EFEC0FAA8" box="[223,349,1377,1394]" gridcol="1" gridrow="9" pageId="2" pageNumber="3">29.82; CH2</td>
|
||
<td id="5108F76F436400120964965EFDBCFAA8" box="[382,545,1377,1394]" gridcol="2" gridrow="9" pageId="2" pageNumber="3">1.08, m</td>
|
||
<td id="5108F76F436400120A5E965EFD6FFAA8" box="[580,754,1377,1394]" gridcol="3" gridrow="9" pageId="2" pageNumber="3">C7</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9647FD6FFA53" box="[116,754,1400,1417]" gridrow="10" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E9647FF2CFA53" box="[116,177,1400,1417]" gridcol="0" gridrow="10" pageId="2" pageNumber="3">7</th>
|
||
<td id="5108F76F4364001208C59647FEC0FA53" box="[223,349,1400,1417]" gridcol="1" gridrow="10" pageId="2" pageNumber="3">27.48; CH2</td>
|
||
<td id="5108F76F4364001209649647FDBCFA53" box="[382,545,1400,1417]" gridcol="2" gridrow="10" pageId="2" pageNumber="3">1.19, m</td>
|
||
<td id="5108F76F436400120A5E9647FD6FFA53" box="[580,754,1400,1417]" gridcol="3" gridrow="10" pageId="2" pageNumber="3">C8; C9</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E96B0FD6FFA7A" box="[116,754,1423,1440]" gridrow="11" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E96B0FF2CFA7A" box="[116,177,1423,1440]" gridcol="0" gridrow="11" pageId="2" pageNumber="3">8</th>
|
||
<td id="5108F76F4364001208C596B0FEC0FA7A" box="[223,349,1423,1440]" gridcol="1" gridrow="11" pageId="2" pageNumber="3">31.26; CH2</td>
|
||
<td id="5108F76F43640012096496B0FDBCFA7A" box="[382,545,1423,1440]" gridcol="2" gridrow="11" pageId="2" pageNumber="3">2.07, t, 7.8 (H7)</td>
|
||
<td id="5108F76F436400120A5E96B0FD6FFA7A" box="[580,754,1423,1440]" gridcol="3" gridrow="11" pageId="2" pageNumber="3">C6; C7; C9; C10; C12;</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9699FD6FFA6E" box="[116,754,1446,1460]" gridrow="12" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-2="1">
|
||
<td id="5108F76F436400120A5E9699FD6FFA6E" box="[580,754,1446,1460]" gridcol="3" gridrow="12" pageId="2" pageNumber="3">C13; H6; H7; H10</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9682FD6FFA11" box="[116,754,1469,1483]" gridrow="13" pageId="2" pageNumber="3" rowspan-2="1">
|
||
<th id="5108F76F43640012086E9682FF2CFA11" box="[116,177,1469,1483]" gridcol="0" gridrow="13" pageId="2" pageNumber="3">9</th>
|
||
<td id="5108F76F4364001208C59682FEC0FA11" box="[223,349,1469,1483]" gridcol="1" gridrow="13" pageId="2" pageNumber="3">171.85; C</td>
|
||
<td id="5108F76F436400120A5E9682FD6FFA11" box="[580,754,1469,1483]" gridcol="3" gridrow="13" pageId="2" pageNumber="3">C12; C13; C14; C15;</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E96EBFD6FFA38" box="[116,754,1492,1506]" gridrow="14" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-2="1">
|
||
<td id="5108F76F436400120A5E96EBFD6FFA38" box="[580,754,1492,1506]" gridcol="3" gridrow="14" pageId="2" pageNumber="3">C16; H7; H8; H10; H11</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E96D4FD6FFA21" box="[116,754,1515,1531]" gridrow="15" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E96D4FF2CFA21" box="[116,177,1515,1531]" gridcol="0" gridrow="15" pageId="2" pageNumber="3">10</th>
|
||
<td id="5108F76F4364001208C596D4FEC0FA21" box="[223,349,1515,1531]" gridcol="1" gridrow="15" pageId="2" pageNumber="3">28.99; CH2</td>
|
||
<td id="5108F76F43640012096496D4FDBCFA21" box="[382,545,1515,1531]" gridcol="2" gridrow="15" pageId="2" pageNumber="3">1.88, m</td>
|
||
<td id="5108F76F436400120A5E96D4FD6FFA21" box="[580,754,1515,1531]" gridcol="3" gridrow="15" pageId="2" pageNumber="3">C9; C11; C12; C13;</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E953EFD6FF9D5" box="[116,754,1537,1551]" gridrow="16" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-2="1">
|
||
<td id="5108F76F436400120A5E953EFD6FF9D5" box="[580,754,1537,1551]" gridcol="3" gridrow="16" pageId="2" pageNumber="3">C15; H8; H14; H15</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9527FD6FF9F3" box="[116,754,1560,1577]" gridrow="17" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E9527FF2CF9F3" box="[116,177,1560,1577]" gridcol="0" gridrow="17" pageId="2" pageNumber="3">11</th>
|
||
<td id="5108F76F4364001208C59527FEC0F9F3" box="[223,349,1560,1577]" gridcol="1" gridrow="17" pageId="2" pageNumber="3">34.18; CH2</td>
|
||
<td id="5108F76F4364001209649527FDBCF9F3" box="[382,545,1560,1577]" gridcol="2" gridrow="17" pageId="2" pageNumber="3">2.03, m</td>
|
||
<td id="5108F76F436400120A5E9527FD6FF9F3" box="[580,754,1560,1577]" gridcol="3" gridrow="17" pageId="2" pageNumber="3">C9; C10; C12; H14;</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9510FD6FF9E7" box="[116,754,1583,1597]" gridrow="18" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-2="1">
|
||
<td id="5108F76F436400120A5E9510FD6FF9E7" box="[580,754,1583,1597]" gridcol="3" gridrow="18" pageId="2" pageNumber="3">H15</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9579FD6FF98E" box="[116,754,1606,1620]" gridrow="19" pageId="2" pageNumber="3" rowspan-2="1">
|
||
<th id="5108F76F43640012086E9579FF2CF98E" box="[116,177,1606,1620]" gridcol="0" gridrow="19" pageId="2" pageNumber="3">12</th>
|
||
<td id="5108F76F4364001208C59579FEC0F98E" box="[223,349,1606,1620]" gridcol="1" gridrow="19" pageId="2" pageNumber="3">207.28; CO</td>
|
||
<td id="5108F76F436400120A5E9579FD6FF98E" box="[580,754,1606,1620]" gridcol="3" gridrow="19" pageId="2" pageNumber="3">H10; H11; H14</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9562FD6FF9B1" box="[116,754,1629,1643]" gridrow="20" pageId="2" pageNumber="3" rowspan-2="1">
|
||
<th id="5108F76F43640012086E9562FF2CF9B1" box="[116,177,1629,1643]" gridcol="0" gridrow="20" pageId="2" pageNumber="3">13</th>
|
||
<td id="5108F76F4364001208C59562FEC0F9B1" box="[223,349,1629,1643]" gridcol="1" gridrow="20" pageId="2" pageNumber="3">139.70; C</td>
|
||
<td id="5108F76F436400120A5E9562FD6FF9B1" box="[580,754,1629,1643]" gridcol="3" gridrow="20" pageId="2" pageNumber="3">H10; H11; H14</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E954BFD6FF95E" box="[116,754,1652,1668]" gridrow="21" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E954BFF2CF95E" box="[116,177,1652,1668]" gridcol="0" gridrow="21" pageId="2" pageNumber="3">14</th>
|
||
<td id="5108F76F4364001208C5954BFEC0F95E" box="[223,349,1652,1668]" gridcol="1" gridrow="21" pageId="2" pageNumber="3">21.85; CH2</td>
|
||
<td id="5108F76F436400120964954BFDBCF95E" box="[382,545,1652,1668]" gridcol="2" gridrow="21" pageId="2" pageNumber="3">3.06, d, 7.2 (H15)</td>
|
||
<td id="5108F76F436400120A5E954BFD6FF95E" box="[580,754,1652,1668]" gridcol="3" gridrow="21" pageId="2" pageNumber="3">C9; C12; C13; C15;</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E95B5FD6FF943" box="[116,754,1674,1689]" gridrow="22" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-2="1">
|
||
<td id="5108F76F436400120A5E95B5FD6FF943" box="[580,754,1674,1689]" gridcol="3" gridrow="22" pageId="2" pageNumber="3">C16; H10; H11; H15;</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E959EFD6FF975" box="[116,754,1697,1711]" gridrow="23" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-2="1">
|
||
<td id="5108F76F436400120A5E959EFD6FF975" box="[580,754,1697,1711]" gridcol="3" gridrow="23" pageId="2" pageNumber="3">H16; H17; H18</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9587FD6FF91C" box="[116,754,1720,1734]" gridrow="24" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E9587FF2CF91C" box="[116,177,1720,1734]" gridcol="0" gridrow="24" pageId="2" pageNumber="3">15</th>
|
||
<td id="5108F76F4364001208C59587FEC0F91C" box="[223,349,1720,1734]" gridcol="1" gridrow="24" pageId="2" pageNumber="3">126.15; CH</td>
|
||
<td id="5108F76F4364001209649587FDBCF91C" box="[382,545,1720,1734]" gridcol="2" gridrow="24" pageId="2" pageNumber="3">5.48, dtt, 10.7 (H16),</td>
|
||
<td id="5108F76F436400120A5E9587FD6FF91C" box="[580,754,1720,1734]" gridcol="3" gridrow="24" pageId="2" pageNumber="3">C14; H10; H11; H14;</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E95F0FD6FF907" box="[116,754,1743,1757]" gridrow="25" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1">
|
||
<td id="5108F76F43640012096495F0FDBCF907" box="[382,545,1743,1757]" gridcol="2" gridrow="25" pageId="2" pageNumber="3">1.4 (H17)</td>
|
||
<td id="5108F76F436400120A5E95F0FD6FF907" box="[580,754,1743,1757]" gridcol="3" gridrow="25" pageId="2" pageNumber="3">H17; H18</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E95D9FD6FF92E" box="[116,754,1766,1780]" gridrow="26" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E95D9FF2CF92E" box="[116,177,1766,1780]" gridcol="0" gridrow="26" pageId="2" pageNumber="3">16</th>
|
||
<td id="5108F76F4364001208C595D9FEC0F92E" box="[223,349,1766,1780]" gridcol="1" gridrow="26" pageId="2" pageNumber="3">132.29; CH</td>
|
||
<td id="5108F76F43640012096495D9FDBCF92E" box="[382,545,1766,1780]" gridcol="2" gridrow="26" pageId="2" pageNumber="3">5.42, dtt, 7.0 (H17),</td>
|
||
<td id="5108F76F436400120A5E95D9FD6FF92E" box="[580,754,1766,1780]" gridcol="3" gridrow="26" pageId="2" pageNumber="3">H14; H17; H18</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E95C2FD6FF8D1" box="[116,754,1789,1803]" gridrow="27" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-3="1">
|
||
<td id="5108F76F43640012096495C2FDBCF8D1" box="[382,545,1789,1803]" gridcol="2" gridrow="27" pageId="2" pageNumber="3">1.5 (H14)</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E942CFD6FF8FE" box="[116,754,1811,1828]" gridrow="28" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E942CFF2CF8FE" box="[116,177,1811,1828]" gridcol="0" gridrow="28" pageId="2" pageNumber="3">17</th>
|
||
<td id="5108F76F4364001208C5942CFEC0F8FE" box="[223,349,1811,1828]" gridcol="1" gridrow="28" pageId="2" pageNumber="3">21.07; CH2</td>
|
||
<td id="5108F76F436400120964942CFDBCF8FE" box="[382,545,1811,1828]" gridcol="2" gridrow="28" pageId="2" pageNumber="3">2.21, dq, 7.5 (H18)</td>
|
||
<td id="5108F76F436400120A5E942CFD6FF8FE" box="[580,754,1811,1828]" gridcol="3" gridrow="28" pageId="2" pageNumber="3">C15; C16; C18; H14;</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9415FD6FF8E2" box="[116,754,1834,1848]" gridrow="29" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-2="1">
|
||
<td id="5108F76F436400120A5E9415FD6FF8E2" box="[580,754,1834,1848]" gridcol="3" gridrow="29" pageId="2" pageNumber="3">H15; H16; H18</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E947EFD6FF888" box="[116,754,1857,1874]" gridrow="30" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E947EFF2CF888" box="[116,177,1857,1874]" gridcol="0" gridrow="30" pageId="2" pageNumber="3">18</th>
|
||
<td id="5108F76F4364001208C5947EFEC0F888" box="[223,349,1857,1874]" gridcol="1" gridrow="30" pageId="2" pageNumber="3">14.44; CH3</td>
|
||
<td id="5108F76F436400120964947EFDBCF888" box="[382,545,1857,1874]" gridcol="2" gridrow="30" pageId="2" pageNumber="3">0.98, t</td>
|
||
<td id="5108F76F436400120A5E947EFD6FF888" box="[580,754,1857,1874]" gridcol="3" gridrow="30" pageId="2" pageNumber="3">C16; C17; H14; H15;</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9467FD6FF8BC" box="[116,754,1880,1894]" gridrow="31" pageId="2" pageNumber="3" rowspan-0="1" rowspan-1="1" rowspan-2="1">
|
||
<td id="5108F76F436400120A5E9467FD6FF8BC" box="[580,754,1880,1894]" gridcol="3" gridrow="31" pageId="2" pageNumber="3">H16; H17</td>
|
||
</tr>
|
||
<tr id="12D99E1343640012086E9450FD6FF8A7" box="[116,754,1903,1917]" gridrow="32" pageId="2" pageNumber="3">
|
||
<th id="5108F76F43640012086E9450FF2CF8A7" box="[116,177,1903,1917]" gridcol="0" gridrow="32" pageId="2" pageNumber="3">(1)</th>
|
||
<td id="5108F76F4364001208C59450FEC0F8A7" box="[223,349,1903,1917]" gridcol="1" gridrow="32" pageId="2" pageNumber="3">51.02; COOMe</td>
|
||
<td id="5108F76F4364001209649450FDBCF8A7" box="[382,545,1903,1917]" gridcol="2" gridrow="32" pageId="2" pageNumber="3">3.37; s</td>
|
||
<td id="5108F76F436400120A5E9450FD6FF8A7" box="[580,754,1903,1917]" gridcol="3" gridrow="32" pageId="2" pageNumber="3">C1, H2</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="AC569C514364FFEF0B4B96D5FB66F923" blockId="2.[818,1490,148,1785]" pageId="2" pageNumber="3">
|
||
The following minor oxylipins were detected (by order of elution) except the products mentioned above. First, dodecane-1,12-dioic acid (Me). Second, 12-hydroxydodecanoic acid (Me/TMSi). Both compounds were detected upon the NaBH
|
||
<subScript id="306D9E144364FFEF0C53957AFBCFF989" attach="left" box="[1097,1106,1605,1619]" fontSize="6" pageId="2" pageNumber="3">4</subScript>
|
||
reduction of products and their catalytic hydrogenation over PtO
|
||
<subScript id="306D9E144364FFEF0C08955EFB86F9B5" attach="left" box="[1042,1051,1633,1647]" fontSize="6" pageId="2" pageNumber="3">2</subScript>
|
||
. Besides, the 9-oxononanoic acid (Me), azelaic acid (Me), (2
|
||
<emphasis id="9E9D40434364FFEF0BAA9549FC21F953" bold="true" box="[944,956,1654,1673]" italics="true" pageId="2" pageNumber="3">E</emphasis>
|
||
)-4-hydroxy-2-nonenoic acid (Me/TMSi) were detected. All these products are biosynthesized via the HPL pathway, occurring in
|
||
<taxonomicName id="6BE9E7D24364FFEF0B289591FBD1F91B" authority="(Stumpe et al., 2006)" baseAuthorityName="Stumpe" baseAuthorityYear="2006" box="[818,1100,1710,1729]" class="Bryopsida" family="Funariaceae" genus="Physcomitrella" kingdom="Plantae" order="Funariales" pageId="2" pageNumber="3" phylum="Bryophyta" rank="species" species="patens">
|
||
<emphasis id="9E9D40434364FFEF0B289591FC1CF91B" bold="true" box="[818,897,1710,1729]" italics="true" pageId="2" pageNumber="3">P. patens</emphasis>
|
||
(
|
||
<bibRefCitation id="C878E1A04364FFEF0B949591FBDFF91B" author="Stumpe, M. & Bode, J. & Wichard, T. & Schaaf, A. & Frank, W. & Frank, M. & Reski, R. & Pohnert, G. & Feussner, I." box="[910,1090,1710,1729]" pageId="2" pageNumber="3" pagination="301 - 312" refId="ref9702" refString="Stumpe, M., Bode, J., Gobel ¨, C., Wichard, T., Schaaf, A., Frank, W., Frank, M., Reski, R., Pohnert, G., Feussner, I., 2006. Biosynthesis of C 9 - aldehydes in the moss Physcomitrella patens. Biochim. Biophys. Acta 1761, 301 - 312." type="journal article" year="2006">Stumpe et al., 2006</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
. The spectra of mentioned chain cleavage products (not shown) match those for the same non-volatile HPL products published before (
|
||
<bibRefCitation id="C878E1A04364FFEF0C1395D9FB73F923" author="Mukhtarova, L. S. & Mukhitova, F. K. & Gogolev, Y. V. & Grechkin, A. N." box="[1033,1262,1766,1785]" pageId="2" pageNumber="3" pagination="356 - 364" refId="ref8620" 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>
|
||
).
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |