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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">The Roles of a Flavone-6-Hydroxylase and 7-<italic>O</italic>-Demethylation in the Flavone Biosynthetic Network of Sweet Basil<xref ref-type="fn" rid="FN1">*</xref><xref ref-type="fn" rid="FN2"><sup><inline-graphic xlink:href="sbox.jpg"></inline-graphic></sup></xref></title><author><name sortKey="Berim, Anna" sort="Berim, Anna" uniqKey="Berim A" first="Anna" last="Berim">Anna Berim</name><affiliation><nlm:aff id="aff1">From the Institute of Biological Chemistry Washington State University, Pullman, Washington 99164-6340</nlm:aff></affiliation></author><author><name sortKey="Gang, David R" sort="Gang, David R" uniqKey="Gang D" first="David R." last="Gang">David R. Gang</name><affiliation><nlm:aff id="aff1">From the Institute of Biological Chemistry Washington State University, Pullman, Washington 99164-6340</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">23184958</idno><idno type="pmc">3548489</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3548489</idno><idno type="RBID">PMC:3548489</idno><idno type="doi">10.1074/jbc.M112.420448</idno><date when="2012">2012</date><idno type="wicri:Area/Pmc/Corpus">000C62</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">The Roles of a Flavone-6-Hydroxylase and 7-<italic>O</italic>-Demethylation in the Flavone Biosynthetic Network of Sweet Basil<xref ref-type="fn" rid="FN1">*</xref><xref ref-type="fn" rid="FN2"><sup><inline-graphic xlink:href="sbox.jpg"></inline-graphic></sup></xref></title><author><name sortKey="Berim, Anna" sort="Berim, Anna" uniqKey="Berim A" first="Anna" last="Berim">Anna Berim</name><affiliation><nlm:aff id="aff1">From the Institute of Biological Chemistry Washington State University, Pullman, Washington 99164-6340</nlm:aff></affiliation></author><author><name sortKey="Gang, David R" sort="Gang, David R" uniqKey="Gang D" first="David R." last="Gang">David R. Gang</name><affiliation><nlm:aff id="aff1">From the Institute of Biological Chemistry Washington State University, Pullman, Washington 99164-6340</nlm:aff></affiliation></author></analytic><series><title level="j">The Journal of Biological Chemistry</title><idno type="ISSN">0021-9258</idno><idno type="eISSN">1083-351X</idno><imprint><date when="2012">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p><bold>Background:</bold> Late steps of lipophilic flavone biosynthesis in mints are unknown.</p><p><bold>Results:</bold> CYP82D monooxygenases catalyze 6-hydroxylation of 7-<italic>O</italic>-methylated precursor, whose 7-methyl group is subsequently removed by demethylation in basil but not in peppermint.</p><p><bold>Conclusion:</bold> Flavone biosynthesis in basil involves an unusual loop.</p><p><bold>Significance:</bold> Novel mechanisms elucidated in basil suggest a new hypothesis for similar metabolic networks in other plants.</p></div></front></TEI><pmc article-type="research-article"><pmc-comment>The publisher of this article does not allow downloading of the full text in XML form.</pmc-comment>
<front><journal-meta><journal-id journal-id-type="nlm-ta">J Biol Chem</journal-id><journal-id journal-id-type="iso-abbrev">J. Biol. Chem</journal-id><journal-id journal-id-type="hwp">jbc</journal-id><journal-id journal-id-type="pmc">jbc</journal-id><journal-id journal-id-type="publisher-id">JBC</journal-id><journal-title-group><journal-title>The Journal of Biological Chemistry</journal-title></journal-title-group><issn pub-type="ppub">0021-9258</issn><issn pub-type="epub">1083-351X</issn><publisher><publisher-name>American Society for Biochemistry and Molecular Biology</publisher-name><publisher-loc>9650 Rockville Pike, Bethesda, MD 20814, U.S.A.</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">23184958</article-id><article-id pub-id-type="pmc">3548489</article-id><article-id pub-id-type="publisher-id">M112.420448</article-id><article-id pub-id-type="doi">10.1074/jbc.M112.420448</article-id><article-categories><subj-group subj-group-type="heading"><subject>Metabolism</subject></subj-group></article-categories><title-group><article-title>The Roles of a Flavone-6-Hydroxylase and 7-<italic>O</italic>-Demethylation in the Flavone Biosynthetic Network of Sweet Basil<xref ref-type="fn" rid="FN1">*</xref><xref ref-type="fn" rid="FN2"><sup><inline-graphic xlink:href="sbox.jpg"></inline-graphic></sup></xref></article-title><alt-title alt-title-type="short">Flavone-6-Hydroxylase and 7-Demethylase in Basil</alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Berim</surname><given-names>Anna</given-names></name><xref ref-type="aff" rid="aff1"></xref></contrib><contrib contrib-type="author"><name><surname>Gang</surname><given-names>David R.</given-names></name><xref ref-type="aff" rid="aff1"></xref><xref ref-type="corresp" rid="cor1"><sup>1</sup></xref></contrib><aff id="aff1">From the Institute of Biological Chemistry Washington State University, Pullman, Washington 99164-6340</aff></contrib-group><author-notes><corresp id="cor1"><label>1</label> To whom correspondence should be addressed. Tel.: <phone>509-335-0550</phone>; Fax: <fax>509-335-7643</fax>; E-mail: <email>gangd@wsu.edu</email>.</corresp></author-notes><pub-date pub-type="ppub"><day>18</day><month>1</month><year>2013</year></pub-date><pub-date pub-type="epub"><day>26</day><month>11</month><year>2012</year></pub-date><volume>288</volume><issue>3</issue><fpage>1795</fpage><lpage>1805</lpage><history><date date-type="received"><day>27</day><month>9</month><year>2012</year></date><date date-type="rev-recd"><day>14</day><month>11</month><year>2012</year></date></history><permissions><copyright-statement>© 2013 by The American Society for Biochemistry and Molecular Biology, Inc.</copyright-statement><copyright-year>2013</copyright-year></permissions><self-uri xlink:title="pdf" xlink:type="simple" xlink:href="zbc00313001795.pdf"></self-uri><abstract abstract-type="teaser"><p><bold>Background:</bold> Late steps of lipophilic flavone biosynthesis in mints are unknown.</p><p><bold>Results:</bold> CYP82D monooxygenases catalyze 6-hydroxylation of 7-<italic>O</italic>-methylated precursor, whose 7-methyl group is subsequently removed by demethylation in basil but not in peppermint.</p><p><bold>Conclusion:</bold> Flavone biosynthesis in basil involves an unusual loop.</p><p><bold>Significance:</bold> Novel mechanisms elucidated in basil suggest a new hypothesis for similar metabolic networks in other plants.</p></abstract><abstract><p>Lipophilic flavonoids found in the Lamiaceae exhibit unusual 6- and 8-hydroxylations whose enzymatic basis is unknown. We show that crude protein extracts from peltate trichomes of sweet basil (<italic>Ocimum basilicum</italic> L.) cultivars readily hydroxylate position 6 of 7-<italic>O</italic>-methylated apigenin but not apigenin itself. The responsible protein was identified as a P450 monooxygenase from the CYP82 family, a family not previously reported to be involved in flavonoid metabolism. This enzyme prefers flavones but also accepts flavanones <italic>in vitro</italic> and requires a 5-hydroxyl in addition to a 7-methoxyl residue on the substrate. A peppermint (<italic>Mentha</italic> × <italic>piperita</italic> L.) homolog displayed identical substrate requirements, suggesting that early 7-<italic>O</italic>-methylation of flavones might be common in the Lamiaceae. This hypothesis is further substantiated by the pioneering discovery of 2-oxoglutarate-dependent flavone demethylase activity in basil, which explains the accumulation of 7-<italic>O</italic>-demethylated flavone nevadensin.</p></abstract><kwd-group><kwd>Cytochrome P450</kwd><kwd>Dioxygenase</kwd><kwd>Hydroxylase</kwd><kwd>Metabolism</kwd><kwd>Secondary Metabolism</kwd><kwd>O-Demethylation</kwd><kwd>Basil</kwd><kwd>Lipophilic Flavones</kwd></kwd-group></article-meta></front></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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