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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>
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