Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus

被引:53
作者
Hosny, M [1 ]
Dhar, K [1 ]
Rosazza, JPN [1 ]
机构
[1] Univ Iowa, Coll Pharm, Div Med & Nat Prod Chem, Ctr Biocatalysis & Bioproc, Iowa City, IA 52242 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2001年 / 64卷 / 04期
关键词
D O I
10.1021/np000457m
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
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 catechol functional groups were present. Metabolite structures were established by FABMS, EIMS, and 1D and 2D NMR analysis.
引用
收藏
页码:462 / 465
页数:4
相关论文
共 48 条
[1]   MICROBIOLOGICAL TRANSFORMATION OF (+/-)-FLAVANONE AND (+/-)-ISOFLAVANONE [J].
ABDELRAHIM, I ;
ABULHAJJ, YJ .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (03) :644-656
[2]   IMPORTANCE OF OXYGEN FUNCTIONS IN THE BIOLOGICAL HYDROXYLATION OF FLAVONOIDS BY ABSIDIA-BLACKESLEEANA [J].
ABULHAJJ, YJ ;
GHAFFARI, MA ;
MEHROTRA, S .
XENOBIOTICA, 1991, 21 (09) :1171-1177
[3]   Bioavailability and metabolism of the flavonol quercetin in the pig [J].
Ader, P ;
Wessmann, A ;
Wolffram, S .
FREE RADICAL BIOLOGY AND MEDICINE, 2000, 28 (07) :1056-1067
[4]  
Agrawal P.K., 1989, Carbon-13 NMR of Flavonoids
[5]   O-(DIHYDROBENZOFURANYL)-DIBENZO-ALPHA-PYRONES FROM U UMTIZA-LISTERANA [J].
BURGER, APN ;
BRANDT, EV ;
ROUX, DG .
PHYTOCHEMISTRY, 1983, 22 (12) :2813-2817
[6]   Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships [J].
Cao, GH ;
Sofic, E ;
Prior, RL .
FREE RADICAL BIOLOGY AND MEDICINE, 1997, 22 (05) :749-760
[7]   IDENTIFICATION OF PRODUCTS PRODUCED BY ANAEROBIC DEGRADATION OF NARINGIN BY BUTYRIVIBRIO SP C3 [J].
CHENG, KJ ;
KRISHNAMURTY, HG ;
JONES, GA ;
SIMPSON, FJ .
CANADIAN JOURNAL OF MICROBIOLOGY, 1971, 17 (01) :129-+
[8]   SCAVENGER AND ANTIOXIDANT PROPERTIES OF 10 SYNTHETIC FLAVONES [J].
COTELLE, N ;
BERNIER, JL ;
HENICHART, JP ;
CATTEAU, JP ;
GAYDOU, E ;
WALLET, JC .
FREE RADICAL BIOLOGY AND MEDICINE, 1992, 13 (03) :211-219
[9]   ISOLATION AND STUDIES OF THE MUTAGENIC ACTIVITY IN THE AMES TEST OF FLAVONOIDS NATURALLY-OCCURRING IN MEDICAL HERBS [J].
CZECZOT, H ;
TUDEK, B ;
KUSZTELAK, J ;
SZYMCZYK, T ;
DOBROWOLSKA, B ;
GLINKOWSKA, G ;
MALINOWSKI, J ;
STRZELECKA, H .
MUTATION RESEARCH, 1990, 240 (03) :209-216
[10]   STUDIES ON FLAVONOID METABOLISM - METABOLISM OF (+)-[14C]CATECHIN IN RAT AND GUINEA PIG [J].
DAS, NP ;
GRIFFITHS, LA .
BIOCHEMICAL JOURNAL, 1969, 115 (04) :831-+