2001
DOI: 10.1021/np000457m
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Hydroxylations and Methylations of Quercetin, Fisetin, and Catechin byStreptomycesgriseus

Abstract: Preparative-scale biotransformation of quercetin (1), fisetin (7), and (+)-catechin (12) with Streptomyces griseus (ATCC 13273) resulted in the isolation and characterization of nine known hydroxylated and/or methylated (2--6, 8, 9, 11, 13a) metabolites and two previously unknown (10 and 14) metabolites. S.griseus catalyzed aromatic hydroxylations of rings A and B of quercetin and fisetin. Mono- and dimethoxy ring-B metabolites were obtained with all three substrates. Methylation appeared to occur only when ca… Show more

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Cited by 52 publications
(40 citation statements)
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“…Of them, the 13 C NMR data of three derivatives were already published. 5,6,7 Because only the partial NMR data of others have been known, however, the complete assignments of their 1 H and 13 C NMR data are reported here. One of the 13 C NMR data published previously showed the incorrect 13 C NMR data, thus their corrected values were determined in this study.…”
mentioning
confidence: 99%
“…Of them, the 13 C NMR data of three derivatives were already published. 5,6,7 Because only the partial NMR data of others have been known, however, the complete assignments of their 1 H and 13 C NMR data are reported here. One of the 13 C NMR data published previously showed the incorrect 13 C NMR data, thus their corrected values were determined in this study.…”
mentioning
confidence: 99%
“…Flavones have also been implicated in various physiological activities, such as antioxidants, phytoestrogens in controlling breast cancer incidence, and osteogenesis, for example, and in chemotaxis of nitrogen-fixing bacteria (23,24,34). Considering this, there has been an increasing interest in the production of novel compounds from flavones using microbial reactions (25,26,37). Previously, biphenyl dioxygenase from P. pseudoalcaligenes KF707 was shown to produce cis-2Ј,3Ј-dihydrodiol on the B ring of flavone (33).…”
mentioning
confidence: 99%
“…Methylation reactions employing mesophilic microbes viz. Cunninghamella elegans, Streptomyces griseus, and Bruveria was reported by Park et al [19], Hosny et al [20], and Costa et al [21]. Biological activity studies of this metabolite are to be performed.…”
Section: Resultsmentioning
confidence: 94%