Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency).
Identifieur interne : 003980 ( Main/Corpus ); précédent : 003979; suivant : 003981Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency).
Auteurs : John Ralph ; Hoon Kim ; Fachuang Lu ; John H. Grabber ; Jean-Charles Leplé ; Jimmy Berrio-Sierra ; Mohammad Mir Derikvand ; Lise Jouanin ; Wout Boerjan ; Catherine LapierreSource :
- The Plant journal : for cell and molecular biology [ 0960-7412 ] ; 2008.
English descriptors
- KwdEn :
- Aldehyde Oxidoreductases (deficiency), Aldehyde Oxidoreductases (metabolism), Biomarkers (chemistry), Biomarkers (metabolism), Coumaric Acids (chemistry), Coumaric Acids (metabolism), Guaiacol (analogs & derivatives), Guaiacol (chemistry), Guaiacol (metabolism), Lignin (chemistry), Lignin (metabolism), Magnoliopsida (metabolism), Molecular Structure (MeSH), Oxidation-Reduction (MeSH), Sulfides (chemistry), Sulfides (metabolism).
- MESH :
- chemical , analogs & derivatives : Guaiacol.
- chemical , chemistry : Biomarkers, Coumaric Acids, Guaiacol, Lignin, Sulfides.
- chemical , deficiency : Aldehyde Oxidoreductases.
- chemical , metabolism : Aldehyde Oxidoreductases, Biomarkers, Coumaric Acids, Guaiacol, Lignin, Sulfides.
- metabolism : Magnoliopsida.
- Molecular Structure, Oxidation-Reduction.
Abstract
A molecular marker compound, derived from lignin by the thioacidolysis degradative method, for structures produced when ferulic acid is incorporated into lignin in angiosperms (poplar, Arabidopsis, tobacco), has been structurally identified as 1,2,2-trithioethyl ethylguaiacol [1-(4-hydroxy-3-methoxyphenyl)-1,2,2-tris(ethylthio)ethane]. Its truncated side chain and distinctive oxidation state suggest that it derives from ferulic acid that has undergone bis-8-O-4 (cross) coupling during lignification, as validated by model studies. A diagnostic contour for such structures is found in two-dimensional (13)C-(1)H correlated (HSQC) NMR spectra of lignins isolated from cinnamoyl CoA reductase (CCR)-deficient poplar. As low levels of the marker are also released from normal (i.e. non-transgenic) plants in which ferulic acid may be present during lignification, notably in grasses, the marker is only an indicator for CCR deficiency in general, but is a reliable marker in woody angiosperms such as poplar. Its derivation, together with evidence for 4-O-etherified ferulic acid, strongly implies that ferulic acid is incorporated into angiosperm lignins. Its endwise radical coupling reactions suggest that ferulic acid should be considered an authentic lignin precursor. Moreover, ferulic acid incorporation provides a new mechanism for producing branch points in the polymer. The findings sharply contradict those reported in a recent study on CCR-deficient Arabidopsis.
DOI: 10.1111/j.1365-313X.2007.03345.x
PubMed: 18184422
Links to Exploration step
pubmed:18184422Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency).</title>
<author><name sortKey="Ralph, John" sort="Ralph, John" uniqKey="Ralph J" first="John" last="Ralph">John Ralph</name>
<affiliation><nlm:affiliation>US Dairy Forage Research Center, USDA-Agricultural Research Service, Madison, WI 53706, USA. john.ralph@ars.usda.gov</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Kim, Hoon" sort="Kim, Hoon" uniqKey="Kim H" first="Hoon" last="Kim">Hoon Kim</name>
</author>
<author><name sortKey="Lu, Fachuang" sort="Lu, Fachuang" uniqKey="Lu F" first="Fachuang" last="Lu">Fachuang Lu</name>
</author>
<author><name sortKey="Grabber, John H" sort="Grabber, John H" uniqKey="Grabber J" first="John H" last="Grabber">John H. Grabber</name>
</author>
<author><name sortKey="Leple, Jean Charles" sort="Leple, Jean Charles" uniqKey="Leple J" first="Jean-Charles" last="Leplé">Jean-Charles Leplé</name>
</author>
<author><name sortKey="Berrio Sierra, Jimmy" sort="Berrio Sierra, Jimmy" uniqKey="Berrio Sierra J" first="Jimmy" last="Berrio-Sierra">Jimmy Berrio-Sierra</name>
</author>
<author><name sortKey="Derikvand, Mohammad Mir" sort="Derikvand, Mohammad Mir" uniqKey="Derikvand M" first="Mohammad Mir" last="Derikvand">Mohammad Mir Derikvand</name>
</author>
<author><name sortKey="Jouanin, Lise" sort="Jouanin, Lise" uniqKey="Jouanin L" first="Lise" last="Jouanin">Lise Jouanin</name>
</author>
<author><name sortKey="Boerjan, Wout" sort="Boerjan, Wout" uniqKey="Boerjan W" first="Wout" last="Boerjan">Wout Boerjan</name>
</author>
<author><name sortKey="Lapierre, Catherine" sort="Lapierre, Catherine" uniqKey="Lapierre C" first="Catherine" last="Lapierre">Catherine Lapierre</name>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="2008">2008</date>
<idno type="RBID">pubmed:18184422</idno>
<idno type="pmid">18184422</idno>
<idno type="doi">10.1111/j.1365-313X.2007.03345.x</idno>
<idno type="wicri:Area/Main/Corpus">003980</idno>
<idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Corpus" wicri:corpus="PubMed">003980</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency).</title>
<author><name sortKey="Ralph, John" sort="Ralph, John" uniqKey="Ralph J" first="John" last="Ralph">John Ralph</name>
<affiliation><nlm:affiliation>US Dairy Forage Research Center, USDA-Agricultural Research Service, Madison, WI 53706, USA. john.ralph@ars.usda.gov</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Kim, Hoon" sort="Kim, Hoon" uniqKey="Kim H" first="Hoon" last="Kim">Hoon Kim</name>
</author>
<author><name sortKey="Lu, Fachuang" sort="Lu, Fachuang" uniqKey="Lu F" first="Fachuang" last="Lu">Fachuang Lu</name>
</author>
<author><name sortKey="Grabber, John H" sort="Grabber, John H" uniqKey="Grabber J" first="John H" last="Grabber">John H. Grabber</name>
</author>
<author><name sortKey="Leple, Jean Charles" sort="Leple, Jean Charles" uniqKey="Leple J" first="Jean-Charles" last="Leplé">Jean-Charles Leplé</name>
</author>
<author><name sortKey="Berrio Sierra, Jimmy" sort="Berrio Sierra, Jimmy" uniqKey="Berrio Sierra J" first="Jimmy" last="Berrio-Sierra">Jimmy Berrio-Sierra</name>
</author>
<author><name sortKey="Derikvand, Mohammad Mir" sort="Derikvand, Mohammad Mir" uniqKey="Derikvand M" first="Mohammad Mir" last="Derikvand">Mohammad Mir Derikvand</name>
</author>
<author><name sortKey="Jouanin, Lise" sort="Jouanin, Lise" uniqKey="Jouanin L" first="Lise" last="Jouanin">Lise Jouanin</name>
</author>
<author><name sortKey="Boerjan, Wout" sort="Boerjan, Wout" uniqKey="Boerjan W" first="Wout" last="Boerjan">Wout Boerjan</name>
</author>
<author><name sortKey="Lapierre, Catherine" sort="Lapierre, Catherine" uniqKey="Lapierre C" first="Catherine" last="Lapierre">Catherine Lapierre</name>
</author>
</analytic>
<series><title level="j">The Plant journal : for cell and molecular biology</title>
<idno type="ISSN">0960-7412</idno>
<imprint><date when="2008" type="published">2008</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aldehyde Oxidoreductases (deficiency)</term>
<term>Aldehyde Oxidoreductases (metabolism)</term>
<term>Biomarkers (chemistry)</term>
<term>Biomarkers (metabolism)</term>
<term>Coumaric Acids (chemistry)</term>
<term>Coumaric Acids (metabolism)</term>
<term>Guaiacol (analogs & derivatives)</term>
<term>Guaiacol (chemistry)</term>
<term>Guaiacol (metabolism)</term>
<term>Lignin (chemistry)</term>
<term>Lignin (metabolism)</term>
<term>Magnoliopsida (metabolism)</term>
<term>Molecular Structure (MeSH)</term>
<term>Oxidation-Reduction (MeSH)</term>
<term>Sulfides (chemistry)</term>
<term>Sulfides (metabolism)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Guaiacol</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Biomarkers</term>
<term>Coumaric Acids</term>
<term>Guaiacol</term>
<term>Lignin</term>
<term>Sulfides</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="deficiency" xml:lang="en"><term>Aldehyde Oxidoreductases</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Aldehyde Oxidoreductases</term>
<term>Biomarkers</term>
<term>Coumaric Acids</term>
<term>Guaiacol</term>
<term>Lignin</term>
<term>Sulfides</term>
</keywords>
<keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Magnoliopsida</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Molecular Structure</term>
<term>Oxidation-Reduction</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">A molecular marker compound, derived from lignin by the thioacidolysis degradative method, for structures produced when ferulic acid is incorporated into lignin in angiosperms (poplar, Arabidopsis, tobacco), has been structurally identified as 1,2,2-trithioethyl ethylguaiacol [1-(4-hydroxy-3-methoxyphenyl)-1,2,2-tris(ethylthio)ethane]. Its truncated side chain and distinctive oxidation state suggest that it derives from ferulic acid that has undergone bis-8-O-4 (cross) coupling during lignification, as validated by model studies. A diagnostic contour for such structures is found in two-dimensional (13)C-(1)H correlated (HSQC) NMR spectra of lignins isolated from cinnamoyl CoA reductase (CCR)-deficient poplar. As low levels of the marker are also released from normal (i.e. non-transgenic) plants in which ferulic acid may be present during lignification, notably in grasses, the marker is only an indicator for CCR deficiency in general, but is a reliable marker in woody angiosperms such as poplar. Its derivation, together with evidence for 4-O-etherified ferulic acid, strongly implies that ferulic acid is incorporated into angiosperm lignins. Its endwise radical coupling reactions suggest that ferulic acid should be considered an authentic lignin precursor. Moreover, ferulic acid incorporation provides a new mechanism for producing branch points in the polymer. The findings sharply contradict those reported in a recent study on CCR-deficient Arabidopsis.</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">18184422</PMID>
<DateCompleted><Year>2008</Year>
<Month>04</Month>
<Day>07</Day>
</DateCompleted>
<DateRevised><Year>2017</Year>
<Month>11</Month>
<Day>16</Day>
</DateRevised>
<Article PubModel="Print"><Journal><ISSN IssnType="Print">0960-7412</ISSN>
<JournalIssue CitedMedium="Print"><Volume>53</Volume>
<Issue>2</Issue>
<PubDate><Year>2008</Year>
<Month>Jan</Month>
</PubDate>
</JournalIssue>
<Title>The Plant journal : for cell and molecular biology</Title>
<ISOAbbreviation>Plant J</ISOAbbreviation>
</Journal>
<ArticleTitle>Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency).</ArticleTitle>
<Pagination><MedlinePgn>368-79</MedlinePgn>
</Pagination>
<ELocationID EIdType="doi" ValidYN="Y">10.1111/j.1365-313X.2007.03345.x</ELocationID>
<Abstract><AbstractText>A molecular marker compound, derived from lignin by the thioacidolysis degradative method, for structures produced when ferulic acid is incorporated into lignin in angiosperms (poplar, Arabidopsis, tobacco), has been structurally identified as 1,2,2-trithioethyl ethylguaiacol [1-(4-hydroxy-3-methoxyphenyl)-1,2,2-tris(ethylthio)ethane]. Its truncated side chain and distinctive oxidation state suggest that it derives from ferulic acid that has undergone bis-8-O-4 (cross) coupling during lignification, as validated by model studies. A diagnostic contour for such structures is found in two-dimensional (13)C-(1)H correlated (HSQC) NMR spectra of lignins isolated from cinnamoyl CoA reductase (CCR)-deficient poplar. As low levels of the marker are also released from normal (i.e. non-transgenic) plants in which ferulic acid may be present during lignification, notably in grasses, the marker is only an indicator for CCR deficiency in general, but is a reliable marker in woody angiosperms such as poplar. Its derivation, together with evidence for 4-O-etherified ferulic acid, strongly implies that ferulic acid is incorporated into angiosperm lignins. Its endwise radical coupling reactions suggest that ferulic acid should be considered an authentic lignin precursor. Moreover, ferulic acid incorporation provides a new mechanism for producing branch points in the polymer. The findings sharply contradict those reported in a recent study on CCR-deficient Arabidopsis.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Ralph</LastName>
<ForeName>John</ForeName>
<Initials>J</Initials>
<AffiliationInfo><Affiliation>US Dairy Forage Research Center, USDA-Agricultural Research Service, Madison, WI 53706, USA. john.ralph@ars.usda.gov</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Kim</LastName>
<ForeName>Hoon</ForeName>
<Initials>H</Initials>
</Author>
<Author ValidYN="Y"><LastName>Lu</LastName>
<ForeName>Fachuang</ForeName>
<Initials>F</Initials>
</Author>
<Author ValidYN="Y"><LastName>Grabber</LastName>
<ForeName>John H</ForeName>
<Initials>JH</Initials>
</Author>
<Author ValidYN="Y"><LastName>Leplé</LastName>
<ForeName>Jean-Charles</ForeName>
<Initials>JC</Initials>
</Author>
<Author ValidYN="Y"><LastName>Berrio-Sierra</LastName>
<ForeName>Jimmy</ForeName>
<Initials>J</Initials>
</Author>
<Author ValidYN="Y"><LastName>Derikvand</LastName>
<ForeName>Mohammad Mir</ForeName>
<Initials>MM</Initials>
</Author>
<Author ValidYN="Y"><LastName>Jouanin</LastName>
<ForeName>Lise</ForeName>
<Initials>L</Initials>
</Author>
<Author ValidYN="Y"><LastName>Boerjan</LastName>
<ForeName>Wout</ForeName>
<Initials>W</Initials>
</Author>
<Author ValidYN="Y"><LastName>Lapierre</LastName>
<ForeName>Catherine</ForeName>
<Initials>C</Initials>
</Author>
</AuthorList>
<Language>eng</Language>
<GrantList CompleteYN="Y"><Grant><GrantID>P41GM66326</GrantID>
<Acronym>GM</Acronym>
<Agency>NIGMS NIH HHS</Agency>
<Country>United States</Country>
</Grant>
<Grant><GrantID>P41RR02301</GrantID>
<Acronym>RR</Acronym>
<Agency>NCRR NIH HHS</Agency>
<Country>United States</Country>
</Grant>
<Grant><GrantID>RR02781</GrantID>
<Acronym>RR</Acronym>
<Agency>NCRR NIH HHS</Agency>
<Country>United States</Country>
</Grant>
<Grant><GrantID>RR08438</GrantID>
<Acronym>RR</Acronym>
<Agency>NCRR NIH HHS</Agency>
<Country>United States</Country>
</Grant>
</GrantList>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
<PublicationType UI="D052061">Research Support, N.I.H., Extramural</PublicationType>
<PublicationType UI="D013486">Research Support, U.S. Gov't, Non-P.H.S.</PublicationType>
</PublicationTypeList>
</Article>
<MedlineJournalInfo><Country>England</Country>
<MedlineTA>Plant J</MedlineTA>
<NlmUniqueID>9207397</NlmUniqueID>
<ISSNLinking>0960-7412</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="C527831">1,2,2-trithioeethyl ethylguaiacol</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D015415">Biomarkers</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D003373">Coumaric Acids</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D013440">Sulfides</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>6JKA7MAH9C</RegistryNumber>
<NameOfSubstance UI="D006139">Guaiacol</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>9005-53-2</RegistryNumber>
<NameOfSubstance UI="D008031">Lignin</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>AVM951ZWST</RegistryNumber>
<NameOfSubstance UI="C004999">ferulic acid</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>EC 1.2.-</RegistryNumber>
<NameOfSubstance UI="D000445">Aldehyde Oxidoreductases</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>EC 1.2.1.44</RegistryNumber>
<NameOfSubstance UI="C019904">cinnamoyl CoA reductase</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName UI="D000445" MajorTopicYN="N">Aldehyde Oxidoreductases</DescriptorName>
<QualifierName UI="Q000172" MajorTopicYN="N">deficiency</QualifierName>
<QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015415" MajorTopicYN="N">Biomarkers</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D003373" MajorTopicYN="N">Coumaric Acids</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006139" MajorTopicYN="N">Guaiacol</DescriptorName>
<QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008031" MajorTopicYN="N">Lignin</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D019684" MajorTopicYN="N">Magnoliopsida</DescriptorName>
<QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010084" MajorTopicYN="N">Oxidation-Reduction</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013440" MajorTopicYN="N">Sulfides</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName>
</MeshHeading>
</MeshHeadingList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2008</Year>
<Month>1</Month>
<Day>11</Day>
<Hour>9</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2008</Year>
<Month>4</Month>
<Day>9</Day>
<Hour>9</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2008</Year>
<Month>1</Month>
<Day>11</Day>
<Hour>9</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">18184422</ArticleId>
<ArticleId IdType="pii">TPJ3345</ArticleId>
<ArticleId IdType="doi">10.1111/j.1365-313X.2007.03345.x</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Bois/explor/PoplarV1/Data/Main/Corpus
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 003980 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Corpus/biblio.hfd -nk 003980 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Bois |area= PoplarV1 |flux= Main |étape= Corpus |type= RBID |clé= pubmed:18184422 |texte= Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency). }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Corpus/RBID.i -Sk "pubmed:18184422" \ | HfdSelect -Kh $EXPLOR_AREA/Data/Main/Corpus/biblio.hfd \ | NlmPubMed2Wicri -a PoplarV1
This area was generated with Dilib version V0.6.37. |