Mutagenicity and cytotoxicity of nitropyrrole compounds derived from the reaction of 2-acetyl pyrrole with nitrite.
2-Acetylpyrrole (AP) is a product of model browning systems, and has been isolated 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.
Wang
C J
CJ
Institute of Biochemistry, Chung Shan Medical and Dental College, Taichung, Taiwan, Republic of China.
Lin
Y L
YL
Lin
J K
JK
D000818:Animals; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects*; D003114:Colony-Forming Units Assay; D066298:In Vitro Techniques; D008297:Male; D009152:Mutagenicity Tests; D009153:Mutagens / Q000633:toxicity*; D011758:Pyrroles / Q000138:chemical synthesis / Q000633:toxicity*; D051381:Rats; D017207:Rats, Sprague-Dawley; D012486:Salmonella typhimurium / Q000187:drug effects
C089524:1,3,5-trinitro-2-acetylpyrrole; C089525:1-nitro-2-acetylpyrrole; D009153:Mutagens; D011758:Pyrroles