Potential defense-related prenylated isoflavones in lactofen-induced soybean.
Identifieur interne : 001678 ( Main/Exploration ); précédent : 001677; suivant : 001679Potential defense-related prenylated isoflavones in lactofen-induced soybean.
Auteurs : Jiye Cheng [États-Unis] ; Chunhua Yuan [États-Unis] ; Terrence L. Graham [États-Unis]Source :
- Phytochemistry [ 1873-3700 ] ; 2011.
Descripteurs français
- KwdFr :
- Chromatographie en phase liquide (MeSH), Herbicides (pharmacologie), Isoflavones (composition chimique), Isoflavones (isolement et purification), Métabolome (MeSH), Prénylation (MeSH), Soja (composition chimique), Spectrométrie de masse (MeSH), Structure moléculaire (MeSH), Éthers de polyhalogénophényle (pharmacologie).
- MESH :
- composition chimique : Isoflavones, Soja.
- isolement et purification : Isoflavones.
- pharmacologie : Herbicides, Éthers de polyhalogénophényle.
- Chromatographie en phase liquide, Métabolome, Prénylation, Spectrométrie de masse, Structure moléculaire.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Isoflavones.
- chemical , isolation & purification : Isoflavones.
- chemical , pharmacology : Halogenated Diphenyl Ethers, Herbicides.
- chemistry : Soybeans.
- Chromatography, Liquid, Mass Spectrometry, Metabolome, Molecular Structure, Prenylation.
Abstract
An integrated LC-MS and NMR metabolomic study was conducted to investigate metabolites whose formation was induced by lactofen (1), a soybean (Glycine max L.) disease resistance-inducing herbicide. First, LC-MS analyses of control and lactofen (1)-induced soybean extracts were performed. The LC-MS raw data were then processed by a custom designed bioinformatics program to detect the induced metabolites so formed. Finally, structures of unknown induced metabolites were determined on the basis of their 1D and 2D NMR spectroscopic data. Structure of two previously unreported compounds, 7,8-dihydroxy-4'-methoxy-3'-prenylisoflavone (2) and 7-hydroxy-4',8-dimethoxy-3'-prenylisoflavone (3) were elucidated together with four known prenylated compounds, 3'-prenyldaidzein (4), 8-prenyldaidzein (5), 3'-prenylgenistein (6), and 4-prenylcoumestrol (7). Compounds (2-6) are reported for the first time in soybean, as are the (13)C chemical shift assignments for compound (7). Formation of these six prenylated compounds was also induced by the primary defense glucan elicitor from the cell wall of the pathogen Phytophthora sojae (Kauf. and Gerde.), further suggesting a potential role in soybean defense. These results highlight the metabolic flexibility within soybean secondary product pathways and suggest that prenylation may be associated with defense responses. Moreover, this study demonstrates a promising future approach using metabolomics on elicitor-induced plants for discovery of unknown compounds even in relatively well studied plants.
DOI: 10.1016/j.phytochem.2011.03.010
PubMed: 21477824
Affiliations:
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Graham</name><affiliation wicri:level="2"><nlm:affiliation>Department of Plant Pathology, The Ohio State University, Columbus, OH 43210, United States.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Plant Pathology, The Ohio State University, Columbus, OH 43210</wicri:regionArea><placeName><region type="state">Ohio</region></placeName></affiliation></author></analytic><series><title level="j">Phytochemistry</title><idno type="eISSN">1873-3700</idno><imprint><date when="2011" type="published">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Chromatography, Liquid (MeSH)</term><term>Halogenated Diphenyl Ethers (pharmacology)</term><term>Herbicides (pharmacology)</term><term>Isoflavones (chemistry)</term><term>Isoflavones (isolation & purification)</term><term>Mass Spectrometry (MeSH)</term><term>Metabolome (MeSH)</term><term>Molecular Structure (MeSH)</term><term>Prenylation (MeSH)</term><term>Soybeans (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Chromatographie en phase liquide (MeSH)</term><term>Herbicides (pharmacologie)</term><term>Isoflavones (composition chimique)</term><term>Isoflavones (isolement et purification)</term><term>Métabolome (MeSH)</term><term>Prénylation (MeSH)</term><term>Soja (composition chimique)</term><term>Spectrométrie de masse (MeSH)</term><term>Structure moléculaire (MeSH)</term><term>Éthers de polyhalogénophényle (pharmacologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Isoflavones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Isoflavones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Halogenated Diphenyl Ethers</term><term>Herbicides</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Soybeans</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Isoflavones</term><term>Soja</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Isoflavones</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Herbicides</term><term>Éthers de polyhalogénophényle</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Chromatography, Liquid</term><term>Mass Spectrometry</term><term>Metabolome</term><term>Molecular Structure</term><term>Prenylation</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Chromatographie en phase liquide</term><term>Métabolome</term><term>Prénylation</term><term>Spectrométrie de masse</term><term>Structure moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">An integrated LC-MS and NMR metabolomic study was conducted to investigate metabolites whose formation was induced by lactofen (1), a soybean (Glycine max L.) disease resistance-inducing herbicide. First, LC-MS analyses of control and lactofen (1)-induced soybean extracts were performed. The LC-MS raw data were then processed by a custom designed bioinformatics program to detect the induced metabolites so formed. Finally, structures of unknown induced metabolites were determined on the basis of their 1D and 2D NMR spectroscopic data. Structure of two previously unreported compounds, 7,8-dihydroxy-4'-methoxy-3'-prenylisoflavone (2) and 7-hydroxy-4',8-dimethoxy-3'-prenylisoflavone (3) were elucidated together with four known prenylated compounds, 3'-prenyldaidzein (4), 8-prenyldaidzein (5), 3'-prenylgenistein (6), and 4-prenylcoumestrol (7). Compounds (2-6) are reported for the first time in soybean, as are the (13)C chemical shift assignments for compound (7). Formation of these six prenylated compounds was also induced by the primary defense glucan elicitor from the cell wall of the pathogen Phytophthora sojae (Kauf. and Gerde.), further suggesting a potential role in soybean defense. These results highlight the metabolic flexibility within soybean secondary product pathways and suggest that prenylation may be associated with defense responses. Moreover, this study demonstrates a promising future approach using metabolomics on elicitor-induced plants for discovery of unknown compounds even in relatively well studied plants. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">21477824</PMID><DateCompleted><Year>2015</Year><Month>04</Month><Day>07</Day></DateCompleted><DateRevised><Year>2017</Year><Month>11</Month><Day>16</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1873-3700</ISSN><JournalIssue CitedMedium="Internet"><Volume>72</Volume><Issue>9</Issue><PubDate><Year>2011</Year><Month>Jun</Month></PubDate></JournalIssue><Title>Phytochemistry</Title><ISOAbbreviation>Phytochemistry</ISOAbbreviation></Journal><ArticleTitle>Potential defense-related prenylated isoflavones in lactofen-induced soybean.</ArticleTitle><Pagination><MedlinePgn>875-81</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.phytochem.2011.03.010</ELocationID><Abstract><AbstractText>An integrated LC-MS and NMR metabolomic study was conducted to investigate metabolites whose formation was induced by lactofen (1), a soybean (Glycine max L.) disease resistance-inducing herbicide. First, LC-MS analyses of control and lactofen (1)-induced soybean extracts were performed. The LC-MS raw data were then processed by a custom designed bioinformatics program to detect the induced metabolites so formed. Finally, structures of unknown induced metabolites were determined on the basis of their 1D and 2D NMR spectroscopic data. Structure of two previously unreported compounds, 7,8-dihydroxy-4'-methoxy-3'-prenylisoflavone (2) and 7-hydroxy-4',8-dimethoxy-3'-prenylisoflavone (3) were elucidated together with four known prenylated compounds, 3'-prenyldaidzein (4), 8-prenyldaidzein (5), 3'-prenylgenistein (6), and 4-prenylcoumestrol (7). Compounds (2-6) are reported for the first time in soybean, as are the (13)C chemical shift assignments for compound (7). Formation of these six prenylated compounds was also induced by the primary defense glucan elicitor from the cell wall of the pathogen Phytophthora sojae (Kauf. and Gerde.), further suggesting a potential role in soybean defense. These results highlight the metabolic flexibility within soybean secondary product pathways and suggest that prenylation may be associated with defense responses. Moreover, this study demonstrates a promising future approach using metabolomics on elicitor-induced plants for discovery of unknown compounds even in relatively well studied plants. </AbstractText><CopyrightInformation>Copyright © 2011 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Cheng</LastName><ForeName>Jiye</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Department of Plant Pathology, The Ohio State University, Columbus, OH 43210, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Yuan</LastName><ForeName>Chunhua</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Campus Chemical Instrument Center, The Ohio State University, Columbus, OH 43210, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Graham</LastName><ForeName>Terrence L</ForeName><Initials>TL</Initials><AffiliationInfo><Affiliation>Department of Plant Pathology, The Ohio State University, Columbus, OH 43210, United States.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2011</Year><Month>04</Month><Day>07</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Phytochemistry</MedlineTA><NlmUniqueID>0151434</NlmUniqueID><ISSNLinking>0031-9422</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D055768">Halogenated Diphenyl Ethers</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D006540">Herbicides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007529">Isoflavones</NameOfSubstance></Chemical><Chemical><RegistryNumber>L44N8UV47O</RegistryNumber><NameOfSubstance UI="C055370">lactofen</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D002853" MajorTopicYN="N">Chromatography, Liquid</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D055768" MajorTopicYN="N">Halogenated Diphenyl Ethers</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006540" MajorTopicYN="N">Herbicides</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D007529" MajorTopicYN="N">Isoflavones</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013058" MajorTopicYN="N">Mass Spectrometry</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D055442" MajorTopicYN="N">Metabolome</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D054876" MajorTopicYN="N">Prenylation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013025" MajorTopicYN="N">Soybeans</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2010</Year><Month>08</Month><Day>05</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2011</Year><Month>01</Month><Day>24</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2011</Year><Month>03</Month><Day>10</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2011</Year><Month>4</Month><Day>12</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2011</Year><Month>4</Month><Day>12</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>4</Month><Day>8</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">21477824</ArticleId><ArticleId IdType="pii">S0031-9422(11)00145-2</ArticleId><ArticleId IdType="doi">10.1016/j.phytochem.2011.03.010</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>États-Unis</li></country><region><li>Ohio</li></region></list><tree><country name="États-Unis"><region name="Ohio"><name sortKey="Cheng, Jiye" sort="Cheng, Jiye" uniqKey="Cheng J" first="Jiye" last="Cheng">Jiye Cheng</name></region><name sortKey="Graham, Terrence L" sort="Graham, Terrence L" uniqKey="Graham T" first="Terrence L" last="Graham">Terrence L. Graham</name><name sortKey="Yuan, Chunhua" sort="Yuan, Chunhua" uniqKey="Yuan C" first="Chunhua" last="Yuan">Chunhua Yuan</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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