Goitrin--a nitrosatable constitutent of plant foodstuffs.
N-nitrosamides are known as direct-acting carcinogens at the site of their formation; they do not need any metabolic activation in vivo. The conditions leading to their formation in the stomach, and also their genotoxicity, have been thoroughly studied with some model compounds. Several reports link this type of compound to the induction of gastric cancer in human. However, only limited data are presently available about possible precursors of N-nitrosamides in foods. In the present study we found that goitrin --a naturally occurring compound in cruciferous vegetables and rape--could be easily nitrosated by treatment with nitrite under stomach conditions, yielding with loss of sulfur the N-nitroso- oxazolidone 4 (fig.). This product has a mutagenicity pattern and potency similar to that of N-nitroso-N-methyl-N'- nitroguanidine (MNNG) in the Ames Salmonella/mammalian microsome test.
D001711:Biotransformation; D001937:Brassica / Q000032:analysis; D009152:Mutagenicity Tests; D009603:Nitroso Compounds / Q000378:metabolism*; D010080:Oxazoles / Q000378:metabolism*; D023303:Oxazolidinones
D009603:Nitroso Compounds; D010080:Oxazoles; D023303:Oxazolidinones; C004333:goitrin