Molecular cloning and characterization of a flavonoid-O-methyltransferase with broad substrate specificity and regioselectivity from Citrus depressa
Identifieur interne : 000122 ( Main/Exploration ); précédent : 000121; suivant : 000123Molecular cloning and characterization of a flavonoid-O-methyltransferase with broad substrate specificity and regioselectivity from Citrus depressa
Auteurs : Nobuya Itoh ; Chisa Iwata ; Hiroshi TodaSource :
- BMC Plant Biology [ 1471-2229 ] ; 2016.
Abstract
Flavonoids are secondary metabolites that play significant roles in plant cells. In particular, polymethoxy flavonoids (PMFs), including nobiletin, have been reported to exhibit various health-supporting properties such as anticancer, anti-inflammatory, and anti-pathogenic properties. However, it is difficult to utilize PMFs for medicinal and dietary use because plant cells contain small amounts of these compounds. Biosynthesis of PMFs in plant cells is carried out by the methylation of hydroxyl groups of flavonoids by
In this study, we isolated five genes encoding FOMT (
Five FOMT genes were isolated from
The online version of this article (doi:10.1186/s12870-016-0870-9) contains supplementary material, which is available to authorized users.
Url:
DOI: 10.1186/s12870-016-0870-9
PubMed: 27549218
PubMed Central: 4994406
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Molecular cloning and characterization of a flavonoid-<italic>O</italic>-methyltransferase with broad substrate specificity and regioselectivity from <italic>Citrus depressa</italic></title><author><name sortKey="Itoh, Nobuya" sort="Itoh, Nobuya" uniqKey="Itoh N" first="Nobuya" last="Itoh">Nobuya Itoh</name><affiliation><nlm:aff id="Aff1">Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398 Japan</nlm:aff><wicri:noCountry code="subfield">Toyama 939-0398 Japan</wicri:noCountry></affiliation></author><author><name sortKey="Iwata, Chisa" sort="Iwata, Chisa" uniqKey="Iwata C" first="Chisa" last="Iwata">Chisa Iwata</name><affiliation><nlm:aff id="Aff1">Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398 Japan</nlm:aff><wicri:noCountry code="subfield">Toyama 939-0398 Japan</wicri:noCountry></affiliation></author><author><name sortKey="Toda, Hiroshi" sort="Toda, Hiroshi" uniqKey="Toda H" first="Hiroshi" last="Toda">Hiroshi Toda</name><affiliation><nlm:aff id="Aff1">Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398 Japan</nlm:aff><wicri:noCountry code="subfield">Toyama 939-0398 Japan</wicri:noCountry></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">27549218</idno><idno type="pmc">4994406</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4994406</idno><idno type="RBID">PMC:4994406</idno><idno type="doi">10.1186/s12870-016-0870-9</idno><date when="2016">2016</date><idno type="wicri:Area/Pmc/Corpus">000648</idno><idno type="wicri:Area/Pmc/Curation">000647</idno><idno type="wicri:Area/Pmc/Checkpoint">000101</idno><idno type="wicri:Area/Ncbi/Merge">002153</idno><idno type="wicri:Area/Ncbi/Curation">002153</idno><idno type="wicri:Area/Ncbi/Checkpoint">002153</idno><idno type="wicri:Area/Main/Merge">000122</idno><idno type="wicri:Area/Main/Curation">000122</idno><idno type="wicri:Area/Main/Exploration">000122</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Molecular cloning and characterization of a flavonoid-<italic>O</italic>-methyltransferase with broad substrate specificity and regioselectivity from <italic>Citrus depressa</italic></title><author><name sortKey="Itoh, Nobuya" sort="Itoh, Nobuya" uniqKey="Itoh N" first="Nobuya" last="Itoh">Nobuya Itoh</name><affiliation><nlm:aff id="Aff1">Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398 Japan</nlm:aff><wicri:noCountry code="subfield">Toyama 939-0398 Japan</wicri:noCountry></affiliation></author><author><name sortKey="Iwata, Chisa" sort="Iwata, Chisa" uniqKey="Iwata C" first="Chisa" last="Iwata">Chisa Iwata</name><affiliation><nlm:aff id="Aff1">Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398 Japan</nlm:aff><wicri:noCountry code="subfield">Toyama 939-0398 Japan</wicri:noCountry></affiliation></author><author><name sortKey="Toda, Hiroshi" sort="Toda, Hiroshi" uniqKey="Toda H" first="Hiroshi" last="Toda">Hiroshi Toda</name><affiliation><nlm:aff id="Aff1">Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398 Japan</nlm:aff><wicri:noCountry code="subfield">Toyama 939-0398 Japan</wicri:noCountry></affiliation></author></analytic><series><title level="j">BMC Plant Biology</title><idno type="eISSN">1471-2229</idno><imprint><date when="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><sec><title>Background</title><p>Flavonoids are secondary metabolites that play significant roles in plant cells. In particular, polymethoxy flavonoids (PMFs), including nobiletin, have been reported to exhibit various health-supporting properties such as anticancer, anti-inflammatory, and anti-pathogenic properties. However, it is difficult to utilize PMFs for medicinal and dietary use because plant cells contain small amounts of these compounds. Biosynthesis of PMFs in plant cells is carried out by the methylation of hydroxyl groups of flavonoids by <italic>O</italic>-methyltransferases (FOMT), and many kinds of FOMTs with different levels of substrate specificity and regioselectivity are cooperatively involved in this biosynthesis.</p></sec><sec><title>Results</title><p>In this study, we isolated five genes encoding FOMT (<italic>CdFOMT1</italic>, <italic>3</italic>, <italic>4</italic>, <italic>5</italic>, and <italic>6</italic>) from <italic>Citrus depressa</italic>, which is known to accumulate nobiletin in the peels of its fruits. The genes encoded Mg<sup>2+</sup>-independent <italic>O</italic>-methyltransferases and showed high amino acid sequence similarity (60–95 %) with higher plant flavonoid <italic>O</italic>-methyltransferases. One of these genes is <italic>CdFOMT5</italic>, which was successfully expressed as a soluble homodimer enzyme in <italic>Escherichia coli</italic>. The molecular mass of the recombinant <italic>CdFOMT5</italic> subunit was 42.0 kDa including a 6× histidine tag. The enzyme exhibited <italic>O</italic>-methyltransferase activity for quercetin, naringenin, (-)-epicatechin, and equol using <italic>S</italic>-adenosyl-<sc>l</sc>-methionine (SAM) as a methyl donor, and its optimal pH and temperature were pH 7.0 and 45 °C, respectively. The recombinant CdFOMT5 demonstrated methylation activity for the 3-, 5-, 6-, and 7-hydroxyl groups of flavones, and 3,3′,5,7-tetra-<italic>O</italic>-methylated quercetin was synthesized from quercetin as a final product of the whole cell reaction system. Thus, CdFOMT5 is a <italic>O</italic>-methyltransferase possessing a broad range of substrate specificity and regioselectivity for flavonoids.</p></sec><sec><title>Conclusions</title><p>Five FOMT genes were isolated from <italic>C. depressa</italic>, and their nucleotide sequences were determined. CdFOMT5 was successfully expressed in <italic>E. coli</italic> cells, and the enzymatic properties of the recombinant protein were characterized. Recombinant CdFOMT5 indicated <italic>O</italic>-methyltransferase activity for many flavonoids and a broad regioselectivity for quercetin as a substrate. Whole-cell biocatalysis using CdFOMT5 expressed in <italic>E. coli</italic> cells was performed using quercetin as a substrate, and 3,3′,5,7-tetramethylated quercetin was obtained as the final product.</p></sec><sec><title>Electronic supplementary material</title><p>The online version of this article (doi:10.1186/s12870-016-0870-9) contains supplementary material, which is available to authorized users.</p></sec></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Tahara, S" uniqKey="Tahara S">S Tahara</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Koes, Re" uniqKey="Koes R">RE Koes</name></author><author><name sortKey="Quattrocchio, F" uniqKey="Quattrocchio F">F Quattrocchio</name></author><author><name sortKey="Mol, Jnm" uniqKey="Mol J">JNM Mol</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Winkel Shirley, B" uniqKey="Winkel Shirley B">B 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sortKey="Keyzers, Ra" uniqKey="Keyzers R">RA Keyzers</name></author><author><name sortKey="Kalua, Cm" uniqKey="Kalua C">CM Kalua</name></author><author><name sortKey="Boss, Pk" uniqKey="Boss P">PK Boss</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Frick, S" uniqKey="Frick S">S Frick</name></author><author><name sortKey="Kutchan, Tm" uniqKey="Kutchan T">TM Kutchan</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Green, Mr" uniqKey="Green M">MR Green</name></author><author><name sortKey="Sambrook, J" uniqKey="Sambrook J">J Sambrook</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Dellaporta, Sl" uniqKey="Dellaporta S">SL Dellaporta</name></author><author><name sortKey="Wood, J" uniqKey="Wood J">J Wood</name></author><author><name sortKey="Hicks, Jb" uniqKey="Hicks J">JB Hicks</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Liu, Yg" uniqKey="Liu Y">YG Liu</name></author><author><name sortKey="Whittier, Rf" uniqKey="Whittier R">RF Whittier</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list></list><tree><noCountry><name sortKey="Itoh, Nobuya" sort="Itoh, Nobuya" uniqKey="Itoh N" first="Nobuya" last="Itoh">Nobuya Itoh</name><name sortKey="Iwata, Chisa" sort="Iwata, Chisa" uniqKey="Iwata C" first="Chisa" last="Iwata">Chisa Iwata</name><name sortKey="Toda, Hiroshi" sort="Toda, Hiroshi" uniqKey="Toda H" first="Hiroshi" last="Toda">Hiroshi Toda</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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