Altered regioselectivity of a poplar O-methyltransferase, POMT-7.
Identifieur interne : 003788 ( Main/Curation ); précédent : 003787; suivant : 003789Altered regioselectivity of a poplar O-methyltransferase, POMT-7.
Auteurs : Bong-Gyu Kim [Corée du Sud] ; Yoon Jung Lee ; Sunhee Lee ; Yoongho Lim ; Youhoon Cheong ; Joong-Hoon AhnSource :
- Journal of biotechnology [ 0168-1656 ] ; 2008.
Descripteurs français
- KwdFr :
- MESH :
- composition chimique : Lutéoline, Protein O-methyltransferase.
- génétique : Populus, Protein O-methyltransferase.
- métabolisme : Populus, Protein O-methyltransferase.
- Modèles moléculaires, Méthylation, Stéréoisomérie.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Luteolin, Protein O-Methyltransferase.
- genetics : Populus, Protein O-Methyltransferase.
- metabolism : Populus, Protein O-Methyltransferase.
- Methylation, Models, Molecular, Stereoisomerism.
Abstract
O-Methylated flavonoids are biosynthesized by regioselective flavonoid O-methyltransferases (OMTs), which may account for the limited number of naturally occurring flavonoids in nature. It was previously shown that poplar POMT-7 regioselectively methylates the 7-hydroxyl group of flavones, whereas rice ROMT-9 regioselectively methylates the 3'-hydroxyl group of the substrate. We co-expressed both OMT genes (POMT-7 and ROMT-9) in E. coli and carried out biotransformation experiments of some flavonoids with the transformed E. coli strain. Contrast to the predicted regioselectivity of both POMT-7 and ROMT-9, unexpected methylation reaction products, i.e. 3',4'-O-methylated flavonoids, in addition to the predicted ones, were obtained with luteolin (5,7,3',4'-tetrahydroxyflavone) and quercetin (3,5,7,3',4'-pentahydroxyflavone) as substrates. Reactions using the 3'-O-methyl derivative of luteolin and quercetin by POMT-7 revealed that the enzyme has altered its regioselectivity from the 7- to the 4'-hydroxyl groups. These results are discussed in terms of molecular modeling of POMT-7 in relation to its methyl donor.
DOI: 10.1016/j.jbiotec.2008.08.007
PubMed: 18817819
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last="Lim">Yoongho Lim</name></author><author><name sortKey="Cheong, Youhoon" sort="Cheong, Youhoon" uniqKey="Cheong Y" first="Youhoon" last="Cheong">Youhoon Cheong</name></author><author><name sortKey="Ahn, Joong Hoon" sort="Ahn, Joong Hoon" uniqKey="Ahn J" first="Joong-Hoon" last="Ahn">Joong-Hoon Ahn</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2008">2008</date><idno type="RBID">pubmed:18817819</idno><idno type="pmid">18817819</idno><idno type="doi">10.1016/j.jbiotec.2008.08.007</idno><idno type="wicri:Area/Main/Corpus">003788</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Corpus" wicri:corpus="PubMed">003788</idno><idno type="wicri:Area/Main/Curation">003788</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Curation">003788</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Altered regioselectivity of a poplar O-methyltransferase, POMT-7.</title><author><name sortKey="Kim, Bong Gyu" sort="Kim, Bong Gyu" uniqKey="Kim B" first="Bong-Gyu" last="Kim">Bong-Gyu Kim</name><affiliation wicri:level="1"><nlm:affiliation>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, Republic of Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul</wicri:regionArea></affiliation></author><author><name sortKey="Lee, Yoon Jung" sort="Lee, Yoon Jung" uniqKey="Lee Y" first="Yoon Jung" last="Lee">Yoon Jung Lee</name></author><author><name sortKey="Lee, Sunhee" sort="Lee, Sunhee" uniqKey="Lee S" first="Sunhee" last="Lee">Sunhee Lee</name></author><author><name sortKey="Lim, Yoongho" sort="Lim, Yoongho" uniqKey="Lim Y" first="Yoongho" last="Lim">Yoongho Lim</name></author><author><name sortKey="Cheong, Youhoon" sort="Cheong, Youhoon" uniqKey="Cheong Y" first="Youhoon" last="Cheong">Youhoon Cheong</name></author><author><name sortKey="Ahn, Joong Hoon" sort="Ahn, Joong Hoon" uniqKey="Ahn J" first="Joong-Hoon" last="Ahn">Joong-Hoon Ahn</name></author></analytic><series><title level="j">Journal of biotechnology</title><idno type="ISSN">0168-1656</idno><imprint><date when="2008" type="published">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Luteolin (chemistry)</term><term>Methylation (MeSH)</term><term>Models, Molecular (MeSH)</term><term>Populus (genetics)</term><term>Populus (metabolism)</term><term>Protein O-Methyltransferase (chemistry)</term><term>Protein O-Methyltransferase (genetics)</term><term>Protein O-Methyltransferase (metabolism)</term><term>Stereoisomerism (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Lutéoline (composition chimique)</term><term>Modèles moléculaires (MeSH)</term><term>Méthylation (MeSH)</term><term>Populus (génétique)</term><term>Populus (métabolisme)</term><term>Protein O-methyltransferase (composition chimique)</term><term>Protein O-methyltransferase (génétique)</term><term>Protein O-methyltransferase (métabolisme)</term><term>Stéréoisomérie (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Luteolin</term><term>Protein O-Methyltransferase</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Lutéoline</term><term>Protein O-methyltransferase</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Populus</term><term>Protein O-Methyltransferase</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Populus</term><term>Protein O-methyltransferase</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Populus</term><term>Protein O-Methyltransferase</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Populus</term><term>Protein O-methyltransferase</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Methylation</term><term>Models, Molecular</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Modèles moléculaires</term><term>Méthylation</term><term>Stéréoisomérie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">O-Methylated flavonoids are biosynthesized by regioselective flavonoid O-methyltransferases (OMTs), which may account for the limited number of naturally occurring flavonoids in nature. It was previously shown that poplar POMT-7 regioselectively methylates the 7-hydroxyl group of flavones, whereas rice ROMT-9 regioselectively methylates the 3'-hydroxyl group of the substrate. We co-expressed both OMT genes (POMT-7 and ROMT-9) in E. coli and carried out biotransformation experiments of some flavonoids with the transformed E. coli strain. Contrast to the predicted regioselectivity of both POMT-7 and ROMT-9, unexpected methylation reaction products, i.e. 3',4'-O-methylated flavonoids, in addition to the predicted ones, were obtained with luteolin (5,7,3',4'-tetrahydroxyflavone) and quercetin (3,5,7,3',4'-pentahydroxyflavone) as substrates. Reactions using the 3'-O-methyl derivative of luteolin and quercetin by POMT-7 revealed that the enzyme has altered its regioselectivity from the 7- to the 4'-hydroxyl groups. These results are discussed in terms of molecular modeling of POMT-7 in relation to its methyl donor.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">18817819</PMID><DateCompleted><Year>2009</Year><Month>03</Month><Day>19</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">0168-1656</ISSN><JournalIssue CitedMedium="Print"><Volume>138</Volume><Issue>3-4</Issue><PubDate><Year>2008</Year><Month>Nov</Month><Day>25</Day></PubDate></JournalIssue><Title>Journal of biotechnology</Title><ISOAbbreviation>J Biotechnol</ISOAbbreviation></Journal><ArticleTitle>Altered regioselectivity of a poplar O-methyltransferase, POMT-7.</ArticleTitle><Pagination><MedlinePgn>107-11</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.jbiotec.2008.08.007</ELocationID><Abstract><AbstractText>O-Methylated flavonoids are biosynthesized by regioselective flavonoid O-methyltransferases (OMTs), which may account for the limited number of naturally occurring flavonoids in nature. It was previously shown that poplar POMT-7 regioselectively methylates the 7-hydroxyl group of flavones, whereas rice ROMT-9 regioselectively methylates the 3'-hydroxyl group of the substrate. We co-expressed both OMT genes (POMT-7 and ROMT-9) in E. coli and carried out biotransformation experiments of some flavonoids with the transformed E. coli strain. Contrast to the predicted regioselectivity of both POMT-7 and ROMT-9, unexpected methylation reaction products, i.e. 3',4'-O-methylated flavonoids, in addition to the predicted ones, were obtained with luteolin (5,7,3',4'-tetrahydroxyflavone) and quercetin (3,5,7,3',4'-pentahydroxyflavone) as substrates. Reactions using the 3'-O-methyl derivative of luteolin and quercetin by POMT-7 revealed that the enzyme has altered its regioselectivity from the 7- to the 4'-hydroxyl groups. These results are discussed in terms of molecular modeling of POMT-7 in relation to its methyl donor.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Bong-Gyu</ForeName><Initials>BG</Initials><AffiliationInfo><Affiliation>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lee</LastName><ForeName>Yoon Jung</ForeName><Initials>YJ</Initials></Author><Author ValidYN="Y"><LastName>Lee</LastName><ForeName>Sunhee</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Lim</LastName><ForeName>Yoongho</ForeName><Initials>Y</Initials></Author><Author ValidYN="Y"><LastName>Cheong</LastName><ForeName>Youhoon</ForeName><Initials>Y</Initials></Author><Author ValidYN="Y"><LastName>Ahn</LastName><ForeName>Joong-Hoon</ForeName><Initials>JH</Initials></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>2008</Year><Month>09</Month><Day>04</Day></ArticleDate></Article><MedlineJournalInfo><Country>Netherlands</Country><MedlineTA>J Biotechnol</MedlineTA><NlmUniqueID>8411927</NlmUniqueID><ISSNLinking>0168-1656</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>EC 2.1.1.-</RegistryNumber><NameOfSubstance UI="D011497">Protein O-Methyltransferase</NameOfSubstance></Chemical><Chemical><RegistryNumber>KUX1ZNC9J2</RegistryNumber><NameOfSubstance UI="D047311">Luteolin</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D047311" MajorTopicYN="N">Luteolin</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008745" MajorTopicYN="N">Methylation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011497" MajorTopicYN="N">Protein O-Methyltransferase</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2008</Year><Month>04</Month><Day>24</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2008</Year><Month>08</Month><Day>13</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2008</Year><Month>08</Month><Day>20</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2008</Year><Month>9</Month><Day>27</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2009</Year><Month>3</Month><Day>20</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2008</Year><Month>9</Month><Day>27</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">18817819</ArticleId><ArticleId IdType="pii">S0168-1656(08)02343-2</ArticleId><ArticleId IdType="doi">10.1016/j.jbiotec.2008.08.007</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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