Mutagenicity and cytotoxicity of nitropyrrole compounds derived from the reaction of 2-acetylpyrrole with nitrite

Article abstract of DOI:10.1016/0278-6915(94)90161-9

2-Acetylpyrrole (AP) is a product of model browning systems, and has been isolted as a major flavour component of many foods. Reaction of AP with nitrite produces two N-nitropyrrole compounds, 1-nitro-2-acetyl-pyrrole (NAP) and 1,3,5-trinitro-2-acetylpyrrole (TNAP), the chemical structures of which have been confirmed by spectral studies, including UV mass, nuclear magnetic resonance, infra-red and elemental analysis (EA). NAP and TNAP are moderately mutagenic to the Salmonella strains TA98 and TA100 in the absence of a mammalian activation system and are markedly cytotoxic to mouse C3H10T1/2 cells. These results suggest that the formation of direct-acting mutagens of nitro-derivatives may take place in nitrite-containing food or in vivo by nitrosation following ingestion of AP.