Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum1
Identifieur interne : 000402 ( Ncbi/Merge ); précédent : 000401; suivant : 000403Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum1
Auteurs : Limei Chang ; Jillian M. Hagel ; Peter J. FacchiniSource :
- Plant Physiology [ 0032-0889 ] ; 2015.
Abstract
A subset of multifunctional O-methyltransferases is involved in the formation of the tetra-O-methylated benzylisoquinoline alkaloid glaucine.
Url:
DOI: 10.1104/pp.15.01240
PubMed: 26297140
PubMed Central: 4587479
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Isolation and Characterization of <italic>O</italic>
-methyltransferases Involved in the Biosynthesis of Glaucine in <italic>Glaucium flavum</italic>
<xref ref-type="fn" rid="fn1"><sup>1</sup>
</xref>
</title>
<author><name sortKey="Chang, Limei" sort="Chang, Limei" uniqKey="Chang L" first="Limei" last="Chang">Limei Chang</name>
</author>
<author><name sortKey="Hagel, Jillian M" sort="Hagel, Jillian M" uniqKey="Hagel J" first="Jillian M." last="Hagel">Jillian M. Hagel</name>
</author>
<author><name sortKey="Facchini, Peter J" sort="Facchini, Peter J" uniqKey="Facchini P" first="Peter J." last="Facchini">Peter J. Facchini</name>
</author>
</titleStmt>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Isolation and Characterization of <italic>O</italic>
-methyltransferases Involved in the Biosynthesis of Glaucine in <italic>Glaucium flavum</italic>
<xref ref-type="fn" rid="fn1"><sup>1</sup>
</xref>
</title>
<author><name sortKey="Chang, Limei" sort="Chang, Limei" uniqKey="Chang L" first="Limei" last="Chang">Limei Chang</name>
</author>
<author><name sortKey="Hagel, Jillian M" sort="Hagel, Jillian M" uniqKey="Hagel J" first="Jillian M." last="Hagel">Jillian M. Hagel</name>
</author>
<author><name sortKey="Facchini, Peter J" sort="Facchini, Peter J" uniqKey="Facchini P" first="Peter J." last="Facchini">Peter J. Facchini</name>
</author>
</analytic>
<series><title level="j">Plant Physiology</title>
<idno type="ISSN">0032-0889</idno>
<idno type="eISSN">1532-2548</idno>
<imprint><date when="2015">2015</date>
</imprint>
</series>
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<front><div type="abstract" xml:lang="en"><p>A subset of multifunctional O-methyltransferases is involved in the formation of the tetra-O-methylated benzylisoquinoline alkaloid glaucine.</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">Plant Physiol</journal-id>
<journal-id journal-id-type="iso-abbrev">Plant Physiol</journal-id>
<journal-id journal-id-type="hwp">plantphysiol</journal-id>
<journal-id journal-id-type="publisher-id">aspb</journal-id>
<journal-title-group><journal-title>Plant Physiology</journal-title>
</journal-title-group>
<issn pub-type="ppub">0032-0889</issn>
<issn pub-type="epub">1532-2548</issn>
<publisher><publisher-name>American Society of Plant Biologists</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">26297140</article-id>
<article-id pub-id-type="pmc">4587479</article-id>
<article-id pub-id-type="publisher-id">PP201501240</article-id>
<article-id pub-id-type="doi">10.1104/pp.15.01240</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Articles</subject>
<subj-group subj-group-type="heading"><subject>Biochemistry and Metabolism</subject>
</subj-group>
</subj-group>
</article-categories>
<title-group><article-title>Isolation and Characterization of <italic>O</italic>
-methyltransferases Involved in the Biosynthesis of Glaucine in <italic>Glaucium flavum</italic>
<xref ref-type="fn" rid="fn1"><sup>1</sup>
</xref>
</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Chang</surname>
<given-names>Limei</given-names>
</name>
</contrib>
<contrib contrib-type="author"><name><surname>Hagel</surname>
<given-names>Jillian M.</given-names>
</name>
</contrib>
<contrib contrib-type="author"><name><surname>Facchini</surname>
<given-names>Peter J.</given-names>
</name>
<xref ref-type="corresp" rid="cor1">*</xref>
</contrib>
<aff id="aff1">Department of Biological Sciences, University of Calgary, Calgary, Alberta T2N 1N4, Canada</aff>
</contrib-group>
<author-notes><fn><p><ext-link ext-link-type="uri" xlink:href="http://www.plantphysiol.org/cgi/doi/10.1104/pp.15.01240">www.plantphysiol.org/cgi/doi/10.1104/pp.15.01240</ext-link>
</p>
</fn>
<corresp id="cor1"><label>*</label>
Address correspondence to <email>pfacchin@ucalgary.ca</email>
.</corresp>
<fn id="afn1"><p>The author responsible for distribution of materials integral to the findings presented in this article in accordance with the policy described in the Instructions for Authors (<ext-link ext-link-type="uri" xlink:href="http://www.plantphysiol.org">www.plantphysiol.org</ext-link>
) is: Peter J. Facchini (<email>pfacchin@ucalgary.ca</email>
).</p>
</fn>
<fn id="afn2"><p>L.C. conducted most of the experiments and cowrote the article; J.M.H. performed the mass spectrometry analysis; P.J.F. conceived and supervised the research and cowrote the article.</p>
</fn>
</author-notes>
<pmc-comment>Fake ppub date generated by PMC from publisher
pub-date/@pub-type='epub-ppub' </pmc-comment>
<pub-date pub-type="ppub"><month>10</month>
<year>2015</year>
</pub-date>
<pub-date pub-type="epub"><day>21</day>
<month>8</month>
<year>2015</year>
</pub-date>
<volume>169</volume>
<issue>2</issue>
<fpage>1127</fpage>
<lpage>1140</lpage>
<history><date date-type="received"><day>06</day>
<month>8</month>
<year>2015</year>
</date>
<date date-type="accepted"><day>20</day>
<month>8</month>
<year>2015</year>
</date>
</history>
<permissions><copyright-statement>© 2015 American Society of Plant Biologists. All Rights Reserved.</copyright-statement>
<copyright-year>2015</copyright-year>
</permissions>
<self-uri xlink:role="icon" xlink:href="PP_PP201501240_ic1.gif"></self-uri>
<abstract abstract-type="precis"><p>A subset of multifunctional O-methyltransferases is involved in the formation of the tetra-O-methylated benzylisoquinoline alkaloid glaucine.</p>
</abstract>
<abstract><p>Transcriptome resources for the medicinal plant <italic>Glaucium flavum</italic>
were searched for orthologs showing identity with characterized <italic>O</italic>
-methyltransferases (OMTs) involved in benzylisoquinoline alkaloid biosynthesis. Seven recombinant proteins were functionally tested using the signature alkaloid substrates for six OMTs: norlaudanosoline 6-OMT, 6-<italic>O</italic>
-methyllaudanosoline 4′-OMT, reticuline 7-OMT, norreticuline 7-OMT, scoulerine 9-OMT, and tetrahydrocolumbamine OMT. A notable alkaloid in yellow horned poppy (<italic>G. flavum</italic>
[GFL]) is the aporphine alkaloid glaucine, which displays C8-C6′ coupling and four <italic>O</italic>
-methyl groups at C6, C7, C3′, and C4′ as numbered on the 1-benzylisoquinoline scaffold. Three recombinant enzymes accepted 1-benzylisoquinolines with differential substrate and regiospecificity. GFLOMT2 displayed the highest amino acid sequence identity with norlaudanosoline 6-OMT, showed a preference for the 6-<italic>O</italic>
-methylation of norlaudanosoline, and <italic>O</italic>
-methylated the 3′ and 4′ hydroxyl groups of certain alkaloids. GFLOMT1 showed the highest sequence identity with 6-<italic>O</italic>
-methyllaudanosoline 4′OMT and catalyzed the 6-<italic>O</italic>
-methylation of norlaudanosoline, but more efficiently 4′-<italic>O</italic>
-methylated the GFLOMT2 reaction product 6-<italic>O</italic>
-methylnorlaudanosoline and its <italic>N</italic>
-methylated derivative 6-<italic>O</italic>
-methyllaudanosoline. GFLOMT1 also effectively 3′-<italic>O</italic>
-methylated both reticuline and norreticuline. GFLOMT6 was most similar to scoulerine 9-OMT and efficiently catalyzed both 3′- and 7′-<italic>O</italic>
-methylations of several 1-benzylisoquinolines, with a preference for <italic>N</italic>
-methylated substrates. All active enzymes accepted scoulerine and tetrahydrocolumbamine. Exogenous norlaudanosoline was converted to tetra-<italic>O</italic>
-methylated laudanosine using combinations of <italic>Escherichia coli</italic>
producing (1) GFLOMT1, (2) either GFLOMT2 or GFLOMT6, and (3) coclaurine <italic>N</italic>
-methyltransferase from <italic>Coptis japonica</italic>
. Expression profiles of <italic>GFLOMT1</italic>
, <italic>GFLOMT2</italic>
, and <italic>GFLOMT6</italic>
in different plant organs were in agreement with the <italic>O</italic>
-methylation patterns of alkaloids in <italic>G. flavum</italic>
determined by high-resolution, Fourier-transform mass spectrometry.</p>
</abstract>
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<notes><glossary><title>Glossary</title>
<def-list><def-item><term id="term1">BIA</term>
<def id="def1"><p>benzylisoquinoline alkaloid</p>
</def>
</def-item>
<def-item><term id="term2">SAM</term>
<def id="def2"><p><italic>S</italic>
-adenosyl-<sc>l</sc>
-Met</p>
</def>
</def-item>
<def-item><term id="term3">cDNA</term>
<def id="def3"><p>complementary DNA</p>
</def>
</def-item>
<def-item><term id="term4">LC</term>
<def id="def4"><p>liquid chromatography</p>
</def>
</def-item>
<def-item><term id="term5">MS/MS</term>
<def id="def5"><p>tandem mass spectrometry</p>
</def>
</def-item>
<def-item><term id="term6">CID</term>
<def id="def6"><p>collision-induced dissociation</p>
</def>
</def-item>
<def-item><term id="term7"><italic>m</italic>
/<italic>z</italic>
</term>
<def id="def7"><p>mass-to-charge ratio</p>
</def>
</def-item>
<def-item><term id="term8">FTMS</term>
<def id="def8"><p>Fourier-transform mass spectrometry</p>
</def>
</def-item>
<def-item><term id="term9">IPTG</term>
<def id="def9"><p>isopropyl β-<sc>d</sc>
-thiogalactopyranoside</p>
</def>
</def-item>
</def-list>
</glossary>
</notes>
</front>
</pmc>
<affiliations><list></list>
<tree><noCountry><name sortKey="Chang, Limei" sort="Chang, Limei" uniqKey="Chang L" first="Limei" last="Chang">Limei Chang</name>
<name sortKey="Facchini, Peter J" sort="Facchini, Peter J" uniqKey="Facchini P" first="Peter J." last="Facchini">Peter J. Facchini</name>
<name sortKey="Hagel, Jillian M" sort="Hagel, Jillian M" uniqKey="Hagel J" first="Jillian M." last="Hagel">Jillian M. Hagel</name>
</noCountry>
</tree>
</affiliations>
</record>
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