title: Mechanism(s) involved in meat mutagen formation and inhibition.
abstract: The Maillard reaction, which involves Amadori rearrangement as a key step, also results in sugar fragmentation and free radical formation. The imidazoquinoline meat mutagens (2-amino-3-methylimidazo[4,5-f]-quinoline, or IQ, and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline, or MeIQ) are formed from a reaction mixture containing alkylpyridine free radicals and creatinine. The imidazoquinoxaline meat mutagens (2-amino-3,4-dimethylimidazo[4,5-f]-quinoxaline, or MeIQx, and 2-amino-3,4,8-trimethylimidazo[4,5-f]-quinoxaline, or 4,8-DiMeIQx) may be produced by reacting a mixture containing dialkylpyrazine free radicals and creatinine. Two different pathways for free radical formation are proposed. One involves bimolecular ring formation from the enaminol form of the glycoaldehyde alkylimine and is followed by oxidative formation of the free radical. The other pathway involves formation of N,N1-dialkylpyrazinium ions from glyoxal monoalkylimine followed by reduction to produce the free radicals. The respective intermediates (glycoaldehyde alkylimine and glyoxal monoalkylamine) are formed by reacting glycoaldehyde and glyoxal with amino compounds. The glycoaldehyde system reacts faster and produces more free radicals than the glyoxal system. The reactions help to explain the formation of imidazoquinoxaline meat mutagens and their predominance in fried fish and why these mutagens are present in larger quantities in fried ground beef than the imidazoquinoline-type meat mutagens. These two pathways may not be the only mechanisms involved in formation of meat mutagens, but other free radical reactions may also contribute to meat mutagenicity and are mentioned briefly.(ABSTRACT TRUNCATED AT 250 WORDS)
authors.affiliation: Department of Food Science and Human Nutrition, Michigan State University, East Lansing 48824.
authors.forename: A M
authors.initials: AM
authors.lastname: Pearson
authors.forename: C
authors.initials: C
authors.lastname: Chen
authors.forename: J I
authors.initials: JI
authors.lastname: Gray
authors.forename: S D
authors.initials: SD
authors.lastname: Aust
mesh_terms: D000818:Animals; D002084:Butylated Hydroxytoluene / Q000494:pharmacology; D005609:Free Radicals / Q000378:metabolism; D015416:Maillard Reaction; D008460:Meat / Q000009:adverse effects*; D008956:Models, Chemical; D015394:Molecular Structure; D009153:Mutagens / Q000737:chemistry / Q000378:metabolism*; D009573:Nitrites / Q000494:pharmacology; D011804:Quinolines / Q000737:chemistry / Q000378:metabolism; D011810:Quinoxalines / Q000737:chemistry / Q000378:metabolism; D014810:Vitamin E / Q000494:pharmacology
chemical_list: D005609:Free Radicals; D009153:Mutagens; D009573:Nitrites; D011804:Quinolines; D011810:Quinoxalines; D014810:Vitamin E; D002084:Butylated Hydroxytoluene