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Titre du document / Document title

Regiospecific methylation of naringenin to ponciretin by soybean O-methyltransferase expressed in Escherichia coli

Auteur(s) / Author(s)

DAE HWAN KIM (1) ; KIM Bong-Gyu (1) ; LEE Youngshim (1) ; JI YOUNG RYU (2) ; LIM Yoongho (1) ; HUR Hor-Gil (2) ; AHN Joong-Hoon (1) ;

Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)

(1) Department of Molecular Biotechnology, Bio/Molecular Informatics Center, Konkuk University, 1 Hwayang-dong, Kwangjin-gu, Seoul 143-701, COREE, REPUBLIQUE DE
(2) Department of Environmental Science and Engineering, Gwangju Institute of Science and Technology, Gwangju, COREE, REPUBLIQUE DE

Résumé / Abstract

Flavonoids found in plants most likely undergo a variety of modification reactions such as hydroxylation, glycosylation, and/or methylation. Among these, O-methylation has an effect on the solubility and thus on the antimicrobial activity of the flavonoids. We analyzed the conversion of naringenin with a methyltransferase, SOMT-2, from Glycine max. SOMT-2 was expressed in Escherichia coli as a glutathion S-transferase fusion protein. E. coli harboring SOMT-2 was grown with daidzein, geninstein, apigenin, naringenin, and quercetin, respectively, and reaction products were analyzed with thin layer chromatography and HPLC. SOMT-2 could convert apigenin, daidzein, genistein, and quercetin into the corresponding 4'-O-methylated compounds such as acacetin, formononetin, biochanine A, and 4'-methylated quercetin whereas naringenin turned out to be the best substrate tested. SOMT-2 stoichiometically converted naringenin (4',5,7-trihyroxyflavanone) into a ponciretin (4'-methoxy-5,7-dihydroxyflavanone), whose structure was determined by NMR and LC/mass spectral analyses. Considering the reactions, SOMT-2 may have a regiospecific methylation activity, resulting in transforming 4'-hydroxyl group of flavonoids B-ring to 4'-methyl group.

Revue / Journal Title

Journal of biotechnology    ISSN  0168-1656   CODEN JBITD4 

Source / Source

2005, vol. 119, no2, pp. 155-162 [8 page(s) (article)] (17 ref.)

Langue / Language

Anglais

Editeur / Publisher

Elsevier, Amsterdam, PAYS-BAS  (1984) (Revue)

Mots-clés anglais / English Keywords

Spermatophyta

;

Angiospermae

;

Dicotyledones

;

Leguminosae

;

Bacteria

;

Enterobacteriaceae

;

Enzyme

;

Transferases

;

Biotransformation

;

Flavonoid

;

Glycine max

;

Escherichia coli

;

Methyltransferases

;

Soybean

;

Methylation

;

Regiospecificity

;

Mots-clés français / French Keywords

Spermatophyta

;

Angiospermae

;

Dicotyledones

;

Leguminosae

;

Bactérie

;

Enterobacteriaceae

;

Enzyme

;

Transferases

;

Biotransformation

;

Flavonoïde

;

Glycine max

;

Escherichia coli

;

Methyltransferases

;

Soja

;

Méthylation

;

Régiospécificité

;

Mots-clés espagnols / Spanish Keywords

Spermatophyta

;

Angiospermae

;

Dicotyledones

;

Leguminosae

;

Bacteria

;

Enterobacteriaceae

;

Enzima

;

Transferases

;

Biotransformación

;

Flavonoide

;

Glycine max

;

Escherichia coli

;

Methyltransferases

;

Soya

;

Metilación

;

Regiospecificidad

;

Mots-clés d'auteur / Author Keywords

O-Methyltransferase

;

Flavonoids

;

Biotransformation

;

Methylation

;

Localisation / Location

INIST-CNRS, Cote INIST : 20305, 35400013265369.0050

Nº notice refdoc (ud4) : 17084575



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