Flavonoids from Brickellia glutinosa

Journal of Natural Products
1984.0

Abstract

In a continuation of a phytochemical investigation of the genus Brickellia (Tribe Eupatorieae, Subtribe Alomiinae, Family Compositae) (1-6), we now report the isolation and characterization of eleven flavonoids from Brickellia glutinosa A. Gray e.g., 5,7,3'-trihydroxy-3, 6, 4'-trimethoxy-7-O-P-D-glucosylflavone ( centaurein) (7), 5,7,4 ' -trihydroxy-3, 6, 3'- trimethoxyflavone- 4' sulfate (jaceidin-4'-sulfate) (8),5,7,3', 4'-tetrahydroxy-3, 6-dimethoxy-7 -0- P-D-glucosylflavone (quercetagetin-3,6 dimethylether-7-0-P-D-glucoside) (9), 5, 7, 3',4'-tetrahydroxy-3-methoxyflavone (quercetin-3-methylether), 3,5,7, 3',4 '-pentahydroxyflavone (quercetin), 5, 3', 4'-trihydroxy-3, 6, 7-trimethoxyflavone (quercetagetin-3,6,7-trimethylether) (lo), 5,3',4'-trihydroxy-3,7-dimethoxyflavone (quercetin-3,7-dimethylether) (1 l), 3,5,3',4'-tetrahydroxy-6, 7-dimethoxyflavone (eupatolitin) (lo), 5, 3'-dihydroxy-6, 7, 2', 4', 5'-pentamethoxyflavone (brickellin) (lo), 5,7 dihydroxy-3, 6, 3', 4'-ttetramethoxyflavone (quercetagetin-3, 6, 3', 4'-tetramethylether) (lo), 5,4'-dihydroxy-3,6,7-trimethoxyflavone (penduletin) (12), and the aldose reductase (AR) inhibitory activity of five of these flavonoids.Many flavonoids have been established as effective inhibitors of AR, the enzyme that converts D-glucose and D- galactose to sorbitol. This inhibitory activity is of importance as this property imparts potential therapeutic value to flavonoids in the treatment of diabetic and galactosemic cataract (13).The previous chemotaxonomic work on Brickellia indicated that this genus produced flavonoids which, based on established structure-activity relationships, would be potent inhibitors of AR ( 14). Additionally, the flavonoid pattern of these Brickellia species and related members of the Alomiinae is proving to be useful in assessing the generic alignments in the tribe (15).

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