iso‐OPDA: An Early Precursor of cis‐Jasmone in Plants?
Identifieur interne : 001344 ( Istex/Corpus ); précédent : 001343; suivant : 001345iso‐OPDA: An Early Precursor of cis‐Jasmone in Plants?
Auteurs : Paulina D Browska ; Wilhelm BolandSource :
- ChemBioChem [ 1439-4227 ] ; 2007-12-17.
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- KwdEn :
Abstract
cis‐Jasmone is a highly appreciated fragrance and plant‐derived signal molecule that controls pollination, attracts parasitoids of attacking herbivores, and serves as an intra‐ and interspecific signal that controls gene expression. cis‐Jasmone is produced from linolenic acid along the jasmonic acid cascade. In addition to the conversion of jasmonic acid into cis‐jasmone, a novel pathway might exist that converts cis‐oxophytodienoic acid (OPDA), an early precursor of jasmonic acid, into iso‐OPDA. The planar iso‐OPDA is degraded by β‐oxidation to 3,7‐didehydrojasmonic acid, which yields cis‐jasmone by spontaneous decarboxylation. The degradation of iso‐OPDA to cis‐jasmone is demonstrated for many plant species and the yeast Saccharomyces cerevisiae.
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DOI: 10.1002/cbic.200700464
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ISTEX:53B0F2056B26C0B7AAB87A60C6B9561A7982B2A2Le document en format XML
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In addition to the conversion of jasmonic acid into cis‐jasmone, a novel pathway might exist that converts cis‐oxophytodienoic acid (OPDA), an early precursor of jasmonic acid, into iso‐OPDA. The planar iso‐OPDA is degraded by β‐oxidation to 3,7‐didehydrojasmonic acid, which yields cis‐jasmone by spontaneous decarboxylation. The degradation of iso‐OPDA to cis‐jasmone is demonstrated for many plant species and the yeast Saccharomyces cerevisiae.</div></front></TEI><istex><corpusName>wiley</corpusName><author><json:item><name>Paulina Dąbrowska Dipl.‐Chem.</name><affiliations><json:string>Max Planck Institute for Chemical Ecology, Hans‐Knöll‐Strasse 8, 07745 Jena, Germany, Fax: (+49) 3641‐571202</json:string></affiliations></json:item><json:item><name>Wilhelm Boland Prof. Dr.</name><affiliations><json:string>Max Planck Institute for Chemical Ecology, Hans‐Knöll‐Strasse 8, 07745 Jena, Germany, Fax: (+49) 3641‐571202</json:string><json:string>E-mail: Boland@ice.mpg.de</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>bioorganic chemistry</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>biosynthesis</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>cis‐jasmone</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>oxidation</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>oxylipins</value></json:item></subject><articleId><json:string>CBIC200700464</json:string></articleId><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><abstract>cis‐Jasmone is a highly appreciated fragrance and plant‐derived signal molecule that controls pollination, attracts parasitoids of attacking herbivores, and serves as an intra‐ and interspecific signal that controls gene expression. cis‐Jasmone is produced from linolenic acid along the jasmonic acid cascade. In addition to the conversion of jasmonic acid into cis‐jasmone, a novel pathway might exist that converts cis‐oxophytodienoic acid (OPDA), an early precursor of jasmonic acid, into iso‐OPDA. The planar iso‐OPDA is degraded by β‐oxidation to 3,7‐didehydrojasmonic acid, which yields cis‐jasmone by spontaneous decarboxylation. 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In addition to the conversion of jasmonic acid into cis‐jasmone, a novel pathway might exist that converts cis‐oxophytodienoic acid (OPDA), an early precursor of jasmonic acid, into iso‐OPDA. The planar iso‐OPDA is degraded by β‐oxidation to 3,7‐didehydrojasmonic acid, which yields cis‐jasmone by spontaneous decarboxylation. The degradation of iso‐OPDA to cis‐jasmone is demonstrated for many plant species and the yeast Saccharomyces cerevisiae.</p></abstract><abstract><p>The fragrance cis‐jasmone might be formed by a novel pathway from 12‐oxophytodienoic acid by isomerisation to iso‐oxophytodienoic acid (iso‐OPDA). 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KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2007-08-08"></event><event type="firstOnline" date="2007-11-21"></event><event type="publishedOnlineFinalForm" date="2007-12-05"></event><event type="publishedOnlineAcceptedOrEarlyUnpaginated" date="2007-11-21"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.4.4 mode:FullText source:FullText result:FullText" date="2011-02-01"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-08"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-15"></event></eventGroup><numberingGroup><numbering type="pageFirst">2281</numbering><numbering type="pageLast">2285</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:CBIC.CBIC200700464.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="4"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="33"></count></countGroup><titleGroup><title type="main" xml:lang="en"><i>iso</i>‐OPDA: An Early Precursor of <i>cis</i>‐Jasmone in Plants?</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Paulina</givenNames><familyName>Dąbrowska</familyName><degrees>Dipl.‐Chem.</degrees></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Wilhelm</givenNames><familyName>Boland</familyName><degrees>Prof. Dr.</degrees></personName><contactDetails><email>Boland@ice.mpg.de</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="aa" countryCode="DE" type="organization"><unparsedAffiliation>Max Planck Institute for Chemical Ecology, Hans‐Knöll‐Strasse 8, 07745 Jena, Germany, Fax: (+49) 3641‐571202</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">bioorganic chemistry</keyword><keyword xml:id="kwd2">biosynthesis</keyword><keyword xml:id="kwd3"><i>cis</i>‐jasmone</keyword><keyword xml:id="kwd4">oxidation</keyword><keyword xml:id="kwd5">oxylipins</keyword></keywordGroup><fundingInfo><fundingAgency>Max Planck Gesellschaft</fundingAgency></fundingInfo><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p><i>cis</i>‐Jasmone is a highly appreciated fragrance and plant‐derived signal molecule that controls pollination, attracts parasitoids of attacking herbivores, and serves as an intra‐ and interspecific signal that controls gene expression. <i>cis</i>‐Jasmone is produced from linolenic acid along the jasmonic acid cascade. In addition to the conversion of jasmonic acid into <i>cis</i>‐jasmone, a novel pathway might exist that converts <i>cis</i>‐oxophytodienoic acid (OPDA), an early precursor of jasmonic acid, into <i>iso</i>‐OPDA. The planar <i>iso</i>‐OPDA is degraded by β‐oxidation to 3,7‐didehydrojasmonic acid, which yields <i>cis</i>‐jasmone by spontaneous decarboxylation. The degradation of <i>iso</i>‐OPDA to <i>cis</i>‐jasmone is demonstrated for many plant species and the yeast <i>Saccharomyces cerevisiae.</i></p></abstract><abstract type="graphical" xml:lang="en"><p><b>The fragrance</b> <b><i>cis</i></b><b>‐jasmone</b> might be formed by a novel pathway from 12‐oxophytodienoic acid by isomerisation to <i>iso</i>‐oxophytodienoic acid (<i>iso</i>‐OPDA). 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In addition to the conversion of jasmonic acid into cis‐jasmone, a novel pathway might exist that converts cis‐oxophytodienoic acid (OPDA), an early precursor of jasmonic acid, into iso‐OPDA. The planar iso‐OPDA is degraded by β‐oxidation to 3,7‐didehydrojasmonic acid, which yields cis‐jasmone by spontaneous decarboxylation. The degradation of iso‐OPDA to cis‐jasmone is demonstrated for many plant species and the yeast Saccharomyces cerevisiae.</abstract><abstract>The fragrance cis‐jasmone might be formed by a novel pathway from 12‐oxophytodienoic acid by isomerisation to iso‐oxophytodienoic acid (iso‐OPDA). Three cycles of β‐oxidation and a final decarboxylation reaction yield cis‐jasmone in many plants, and even in the yeast Saccharomyces cerevisiae.</abstract><note type="funding">Max Planck Gesellschaft</note><subject lang="en"><genre>keywords</genre><topic>bioorganic chemistry</topic><topic>biosynthesis</topic><topic>cis‐jasmone</topic><topic>oxidation</topic><topic>oxylipins</topic></subject><relatedItem type="host"><titleInfo><title>ChemBioChem</title></titleInfo><titleInfo type="abbreviated"><title>ChemBioChem</title></titleInfo><genre type="journal">journal</genre><subject><genre>article-category</genre><topic>Full Paper</topic></subject><identifier type="ISSN">1439-4227</identifier><identifier type="eISSN">1439-7633</identifier><identifier type="DOI">10.1002/(ISSN)1439-7633</identifier><identifier type="PublisherID">CBIC</identifier><part><date>2007</date><detail type="volume"><caption>vol.</caption><number>8</number></detail><detail type="issue"><caption>no.</caption><number>18</number></detail><extent unit="pages"><start>2281</start><end>2285</end><total>5</total></extent></part></relatedItem><identifier type="istex">53B0F2056B26C0B7AAB87A60C6B9561A7982B2A2</identifier><identifier type="DOI">10.1002/cbic.200700464</identifier><identifier type="ArticleID">CBIC200700464</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2007 WILEY‐VCH Verlag GmbH & Co. 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