Stability of mutagenic nitrosated products of indole compounds occurring in vegetables.

Levels of indolylglucosinolates in Brassica vegetables correlated significantly with the amounts of N-nitroso compounds formed in these vegetables after nitrite treatment. Nitrosation of indole-3-carbinol, indole-3-acetonitrile and indole, hydrolysis products of an indolylglucosinolate, resulted in formation of nitrosated products, which were directly mutagenic to Salmonella typhimurium TA100. The nitrosated products were unstable at pH 2 but stable at pH 8. Experiments to elucidate the mechanisms behind these differences in stability showed an equilibrium between the nitrosated indole compound and the free compound plus nitrite.