title: Formation of an activated N-nitroso compound in nitrite-treated fava beans (Vicia faba).
abstract: Fava beans are prominent in the diet of the Colombian population at high gastric cancer risk. Upon nitrite treatment under simulated gastric conditions, a potent mutagen was formed as detected by a forward mutation assay using Salmonella typhimurium TM677 without microsomal activation. The promutagen was partially purified by preparative t.l.c. and normal phase h.p.l.c. of the acetone-soluble portion of a dried aqueous extract. The nitrosated promutagen fully accounted for the mutagenicity observed with whole fava beans. One gram of fresh fava beans yielded approximately 0.35 nmol of mutagen. Mutagenicity data indicated that this mutagen was more potent than N-methyl-N'-nitro-N-nitrosoguanidine. The characteristics of the mutagen were typical of an activated N-nitroso compound, that is a compound in which the N-nitroso moiety is attached to an activating group, such as a carbonyl group. Irradiation of the mutagen yielded a Griess positive reaction. By reverse-phase h.p.l.c. photohydrolysis, a single peak could be ascribed to the mutagen. Its stability varied as a function of pH, being most unstable under alkaline conditions. Cysteine and phosphate concentration had no effect on its rate of decomposition, thereby strongly suggesting that the mutagen is an N-nitrosourea. The results obtained in this study support the hypothesis of carcinogenesis via the intragastric production of activated N-nitroso compounds.
mesh_terms: D007887:Fabaceae / Q000378:metabolism*; D006868:Hydrolysis; D009152:Mutagenicity Tests; D009153:Mutagens / Q000032:analysis / Q000378:metabolism; D009573:Nitrites / Q000494:pharmacology*; D009602:Nitrosamines / Q000378:metabolism*; D010777:Photochemistry; D010946:Plants, Medicinal
chemical_list: D009153:Mutagens; D009573:Nitrites; D009602:Nitrosamines