Formation of direct-acting genotoxic substances in nitrosated smoked fish and meat products: identification of simple phenolic precursors and phenyldiazonium ions as reactive products.
Epidemiological studies have associated the consumption of smoked fish and meat products with an increased risk of stomach cancer. Therefore, the reaction of such smoked foods with nitrite under acidic conditions was investigated and was shown to produce potent direct-acting genotoxic substances as detected by the SOS Chromotest. Similar genotoxic activity was observed in nitrosated samples of wood-smoke condensates. Simple phenolic compounds such as phenol, 3-methoxycatechol, catechol and vanillin were identified as the precursors of the genotoxic substances. These phenolic compounds also exhibited direct-acting genotoxicity after nitrosation. The major genotoxic substances formed after nitrosation of phenol were isolated and identified as 4- and 2-hydroxyphenyldiazonium ions. Nitrosation of various wood-smoke condensates was found to generate the same type of diazonium compounds, which in part account for the genotoxicity of nitrosated smoked foods.
Ohshima
H
H
International Agency for Research on Cancer, Lyon, France.
Friesen
M
M
Malaveille
C
C
Brouet
I
I
Hautefeuille
A
A
Bartsch
H
H
D000818:Animals; D002645:Chickens; D003979:Diazonium Compounds / Q000302:isolation & purification* / Q000633:toxicity; D005396:Fish Products / Q000032:analysis* / Q000633:toxicity; D005399:Fishes; D008401:Gas Chromatography-Mass Spectrometry; D008460:Meat / Q000032:analysis / Q000633:toxicity; D008461:Meat Products / Q000032:analysis* / Q000633:toxicity; D009152:Mutagenicity Tests; D009603:Nitroso Compounds / Q000633:toxicity*; D010636:Phenols / Q000302:isolation & purification* / Q000633:toxicity; D012474:Salmon; D013552:Swine
D003979:Diazonium Compounds; D009603:Nitroso Compounds; D010636:Phenols; C035176:benzenediazonium