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 : 003894 ( Main/Exploration ); précédent : 003893; suivant : 003895Identification 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 [États-Unis] ; 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.
Descripteurs français
- KwdFr :
- Acides coumariques (composition chimique), Acides coumariques (métabolisme), Aldehyde oxidoreductases (déficit), Aldehyde oxidoreductases (métabolisme), Guaïacol (analogues et dérivés), Guaïacol (composition chimique), Guaïacol (métabolisme), Lignine (composition chimique), Lignine (métabolisme), Magnoliopsida (métabolisme), Marqueurs biologiques (composition chimique), Marqueurs biologiques (métabolisme), Oxydoréduction (MeSH), Structure moléculaire (MeSH), Sulfures (composition chimique), Sulfures (métabolisme).
- MESH :
- analogues et dérivés : Guaïacol.
- composition chimique : Acides coumariques, Guaïacol, Lignine, Marqueurs biologiques, Sulfures.
- déficit : Aldehyde oxidoreductases.
- métabolisme : Acides coumariques, Aldehyde oxidoreductases, Guaïacol, Lignine, Magnoliopsida, Marqueurs biologiques, Sulfures.
- Oxydoréduction, Structure moléculaire.
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
Affiliations:
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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="KwdFr" xml:lang="fr"><term>Acides coumariques (composition chimique)</term><term>Acides coumariques (métabolisme)</term><term>Aldehyde oxidoreductases (déficit)</term><term>Aldehyde oxidoreductases (métabolisme)</term><term>Guaïacol (analogues et dérivés)</term><term>Guaïacol (composition chimique)</term><term>Guaïacol (métabolisme)</term><term>Lignine (composition chimique)</term><term>Lignine (métabolisme)</term><term>Magnoliopsida (métabolisme)</term><term>Marqueurs biologiques (composition chimique)</term><term>Marqueurs biologiques (métabolisme)</term><term>Oxydoréduction (MeSH)</term><term>Structure moléculaire (MeSH)</term><term>Sulfures (composition chimique)</term><term>Sulfures (métabolisme)</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="analogues et dérivés" xml:lang="fr"><term>Guaïacol</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Acides coumariques</term><term>Guaïacol</term><term>Lignine</term><term>Marqueurs biologiques</term><term>Sulfures</term></keywords><keywords scheme="MESH" qualifier="déficit" xml:lang="fr"><term>Aldehyde oxidoreductases</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Magnoliopsida</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Acides coumariques</term><term>Aldehyde oxidoreductases</term><term>Guaïacol</term><term>Lignine</term><term>Magnoliopsida</term><term>Marqueurs biologiques</term><term>Sulfures</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Molecular Structure</term><term>Oxidation-Reduction</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Oxydoréduction</term><term>Structure moléculaire</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><affiliations><list><country><li>États-Unis</li></country><region><li>Wisconsin</li></region></list><tree><noCountry><name sortKey="Berrio Sierra, Jimmy" sort="Berrio Sierra, Jimmy" uniqKey="Berrio Sierra J" first="Jimmy" last="Berrio-Sierra">Jimmy Berrio-Sierra</name><name sortKey="Boerjan, Wout" sort="Boerjan, Wout" uniqKey="Boerjan W" first="Wout" last="Boerjan">Wout Boerjan</name><name sortKey="Derikvand, Mohammad Mir" sort="Derikvand, Mohammad Mir" uniqKey="Derikvand M" first="Mohammad Mir" last="Derikvand">Mohammad Mir Derikvand</name><name sortKey="Grabber, John H" sort="Grabber, John H" uniqKey="Grabber J" first="John H" last="Grabber">John H. Grabber</name><name sortKey="Jouanin, Lise" sort="Jouanin, Lise" uniqKey="Jouanin L" first="Lise" last="Jouanin">Lise Jouanin</name><name sortKey="Kim, Hoon" sort="Kim, Hoon" uniqKey="Kim H" first="Hoon" last="Kim">Hoon Kim</name><name sortKey="Lapierre, Catherine" sort="Lapierre, Catherine" uniqKey="Lapierre C" first="Catherine" last="Lapierre">Catherine Lapierre</name><name sortKey="Leple, Jean Charles" sort="Leple, Jean Charles" uniqKey="Leple J" first="Jean-Charles" last="Leplé">Jean-Charles Leplé</name><name sortKey="Lu, Fachuang" sort="Lu, Fachuang" uniqKey="Lu F" first="Fachuang" last="Lu">Fachuang Lu</name></noCountry><country name="États-Unis"><region name="Wisconsin"><name sortKey="Ralph, John" sort="Ralph, John" uniqKey="Ralph J" first="John" last="Ralph">John Ralph</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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