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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Dioxygenases Catalyze <italic>O-</italic>Demethylation and <italic>O,O</italic>-Demethylenation with Widespread Roles in Benzylisoquinoline Alkaloid Metabolism in Opium Poppy<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="Farrow, Scott C" sort="Farrow, Scott C" uniqKey="Farrow S" first="Scott C." last="Farrow">Scott C. Farrow</name><affiliation><nlm:aff id="aff1">From the Department of Biological Sciences, University of Calgary, Calgary, Alberta T2N 1N4, Canada</nlm:aff></affiliation></author><author><name sortKey="Facchini, Peter J" sort="Facchini, Peter J" uniqKey="Facchini P" first="Peter J." last="Facchini">Peter J. Facchini</name><affiliation><nlm:aff id="aff1">From the Department of Biological Sciences, University of Calgary, Calgary, Alberta T2N 1N4, Canada</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">23928311</idno><idno type="pmc">3789997</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3789997</idno><idno type="RBID">PMC:3789997</idno><idno type="doi">10.1074/jbc.M113.488585</idno><date when="2013">2013</date><idno type="wicri:Area/Pmc/Corpus">000C63</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Dioxygenases Catalyze <italic>O-</italic>Demethylation and <italic>O,O</italic>-Demethylenation with Widespread Roles in Benzylisoquinoline Alkaloid Metabolism in Opium Poppy<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="Farrow, Scott C" sort="Farrow, Scott C" uniqKey="Farrow S" first="Scott C." last="Farrow">Scott C. Farrow</name><affiliation><nlm:aff id="aff1">From the Department of Biological Sciences, University of Calgary, Calgary, Alberta T2N 1N4, Canada</nlm:aff></affiliation></author><author><name sortKey="Facchini, Peter J" sort="Facchini, Peter J" uniqKey="Facchini P" first="Peter J." last="Facchini">Peter J. Facchini</name><affiliation><nlm:aff id="aff1">From the Department of Biological Sciences, University of Calgary, Calgary, Alberta T2N 1N4, Canada</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="2013">2013</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p><bold>Background:</bold> Thebaine 6-<italic>O</italic>-demethylase (T6ODM) and codeine <italic>O</italic>-demethylase (CODM) catalyze late steps of morphine biosynthesis in opium poppy.</p><p><bold>Results:</bold> New dealkylation reactions, including <italic>O,O</italic>-demethylenation, have been detected for T6ODM, CODM, and other 2-oxoglutarate/Fe(II)-dependent dioxygenases (ODDs). Virus-induced gene silencing supports physiological functions.</p><p><bold>Conclusion:</bold> Certain ODDs are multifunctional dealkylating enzymes with widespread roles in benzylisoquinoline alkaloid metabolism.</p><p><bold>Significance:</bold> Enzymes responsible for <italic>O</italic>-demethylation and <italic>O,O</italic>-demethylenation in plant alkaloid biosynthesis have been discovered.</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">23928311</article-id><article-id pub-id-type="pmc">3789997</article-id><article-id pub-id-type="publisher-id">M113.488585</article-id><article-id pub-id-type="doi">10.1074/jbc.M113.488585</article-id><article-categories><subj-group subj-group-type="heading"><subject>Plant Biology</subject></subj-group></article-categories><title-group><article-title>Dioxygenases Catalyze <italic>O-</italic>Demethylation and <italic>O,O</italic>-Demethylenation with Widespread Roles in Benzylisoquinoline Alkaloid Metabolism in Opium Poppy<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">Alkaloid O-Demethylation and O,O-Demethylenation</alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Farrow</surname><given-names>Scott C.</given-names></name><xref ref-type="aff" rid="aff1"></xref><xref ref-type="author-notes" rid="FN3"><sup>1</sup></xref></contrib><contrib contrib-type="author"><name><surname>Facchini</surname><given-names>Peter J.</given-names></name><xref ref-type="aff" rid="aff1"></xref><xref ref-type="corresp" rid="cor1"><sup>2</sup></xref></contrib><aff id="aff1">From the Department of Biological Sciences, University of Calgary, Calgary, Alberta T2N 1N4, Canada</aff></contrib-group><author-notes><corresp id="cor1"><label>2</label> Holds the Canada Research Chair in Plant Metabolic Processes Biotechnology. To whom correspondence should be addressed. Tel.: <phone>403-220-7651</phone>; E-mail: <email>pfacchin@ucalgary.ca</email>.</corresp><fn fn-type="other" id="FN3"><label>1</label><p>Recipient of scholarships from the Natural Sciences and Engineering Research Council of Canada and Alberta Innovates Technology Futures.</p></fn></author-notes><pub-date pub-type="ppub"><day>4</day><month>10</month><year>2013</year></pub-date><pub-date pub-type="epub"><day>8</day><month>8</month><year>2013</year></pub-date><volume>288</volume><issue>40</issue><fpage>28997</fpage><lpage>29012</lpage><history><date date-type="received"><day>24</day><month>5</month><year>2013</year></date><date date-type="rev-recd"><day>29</day><month>7</month><year>2013</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="zbc04013028997.pdf"></self-uri><abstract abstract-type="teaser"><p><bold>Background:</bold> Thebaine 6-<italic>O</italic>-demethylase (T6ODM) and codeine <italic>O</italic>-demethylase (CODM) catalyze late steps of morphine biosynthesis in opium poppy.</p><p><bold>Results:</bold> New dealkylation reactions, including <italic>O,O</italic>-demethylenation, have been detected for T6ODM, CODM, and other 2-oxoglutarate/Fe(II)-dependent dioxygenases (ODDs). Virus-induced gene silencing supports physiological functions.</p><p><bold>Conclusion:</bold> Certain ODDs are multifunctional dealkylating enzymes with widespread roles in benzylisoquinoline alkaloid metabolism.</p><p><bold>Significance:</bold> Enzymes responsible for <italic>O</italic>-demethylation and <italic>O,O</italic>-demethylenation in plant alkaloid biosynthesis have been discovered.</p></abstract><abstract><p>In opium poppy, the antepenultimate and final steps in morphine biosynthesis are catalyzed by the 2-oxoglutarate/Fe(II)-dependent dioxygenases, thebaine 6-<italic>O-</italic>demethylase (T6ODM) and codeine <italic>O-</italic>demethylase (CODM). Further investigation into the biochemical functions of CODM and T6ODM revealed extensive and unexpected roles for such enzymes in the metabolism of protopine, benzo[<italic>c</italic>]phenanthridine, and rhoeadine alkaloids. When assayed with a wide range of benzylisoquinoline alkaloids, CODM, T6ODM, and the functionally unassigned paralog DIOX2, renamed protopine <italic>O</italic>-dealkylase, showed novel and efficient dealkylation activities, including regio- and substrate-specific <italic>O</italic>-demethylation and <italic>O,O</italic>-demethylenation. Enzymes catalyzing <italic>O,O</italic>-demethylenation, which cleave a methylenedioxy bridge leaving two hydroxyl groups, have previously not been reported in plants. Similar cleavage of methylenedioxy bridges on substituted amphetamines is catalyzed by heme-dependent cytochromes P450 in mammals. Preferred substrates for <italic>O,O</italic>-demethylenation by CODM and protopine <italic>O</italic>-dealkylase were protopine alkaloids that serve as intermediates in the biosynthesis of benzo[<italic>c</italic>]phenanthridine and rhoeadine derivatives. Virus-induced gene silencing used to suppress the abundance of <italic>CODM</italic> and/or <italic>T6ODM</italic> transcripts indicated a direct physiological role for these enzymes in the metabolism of protopine alkaloids, and they revealed their indirect involvement in the formation of the antimicrobial benzo[<italic>c</italic>]phenanthridine sanguinarine and certain rhoeadine alkaloids in opium poppy.</p></abstract><kwd-group><kwd>Dioxygenase</kwd><kwd>Gene Silencing</kwd><kwd>Mass Spectrometry (MS)</kwd><kwd>Metabolic Regulation</kwd><kwd>Plant Biochemistry</kwd><kwd>Plant Physiology</kwd><kwd>Secondary Metabolism</kwd></kwd-group></article-meta></front></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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