3-amino-1-4-dimethyl-5h-pyrido(4-3-b)indole and daidzein

The antimutagenic activity of four isoflavones isolated from soybean miso toward three kinds of mutagens, AF-2, MNNG, and Trp-P-1, was evaluated by the Ames test. 8-Hydroxyisoflavones had greater suppressive potency than that of daidzein, and 6-hydroxydaidzein had almost the same activity as daidzein. These results indicated the number of hydroxy and methoxy groups and the position of these functional groups were important for antimutagenic activity.

Topics: Antimutagenic Agents; Carbolines; Drug Antagonism; Free Radical Scavengers; Furylfuramide; Glycine max; Isoflavones; Methylnitronitrosoguanidine; Mutagens; Salmonella typhimurium; Structure-Activity Relationship

Two isoflavones, daidzein (1) and genistein (2), were isolated from soybean hypocotyls. Daidzein and genistein showed a suppressive effect on umu gene expression of the SOS response in Salmonellatyphimurium TA1535/pSK1002 against the mutagen 3-amino-1, 4-dimethyl-5H-pyrido[4,3b]indole (Trp-P-1), which requires liver metabolizing enzymes. Compound 1 suppressed 73% of the SOS-inducing activity at concentrations <0.74 micromol/mL, and the ID(50) value was 0.37 micromol/mL. Compound 2 suppressed 95% of the SOS-inducing activity at concentrations <0.74 micromol/mL, and the ID(50) value was 0.17 micromol/mL. Compounds 1 and 2 were also assayed with the mutagen 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide) and activated Trp-P-1. In addition to the antimutagenic activities of daidzein and genistein against Trp-P-1, frylfuramide and activated Trp-P-1 were assayed by an Ames test using S. typhimurium TA100.

Topics: Antimutagenic Agents; Carbolines; Genistein; Glycine max; Hypocotyl; Isoflavones; Mutagenicity Tests; Mutagens; Salmonella typhimurium; Seeds; SOS Response, Genetics