title: 4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation, causes DNA adduct formation in mouse organs.
abstract: To identify mutagens formed in a model reaction of lipid peroxidation, linolenic acid methyl ester and hemin were reacted with dG. As a result, a 4-oxo-2-hexenal-dG adduct (dG*) was identified in the model reaction mixture. The 4-oxo-2-hexenal (4-OHE) showed mutagenic activity in the Salmonella typhimurium strains TA100 and TA104. After 4-OHE was orally administered to mice, dG, 4-OHE-dC- and 4-OHE-5-methyl-dC adducts were detected in esophageal, stomach and intestinal DNA. In the vapor phase released from the methyl linolenate-hemin model system, and in the smoke released during the broiling of fish, 4-OHE was detected by GCMS. The 4-OHE seems to be produced by the auto-oxidation of omega-3 polyunsaturated fatty acids. These results provide a warning to workers dealing with omega-3 fats, who may be exposed to this volatile mutagen.
authors.affiliation: Department of Environmental Oncology, Institute of Industrial Ecological Sciences University of Occupational and Environmental Health, 1-1 Iseigaoka, Yahatanishi-ku, Kitakyushu 807-8555, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Kasai
authors.forename: Muneyuki
authors.initials: M
authors.lastname: Maekawa
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Kawai
authors.forename: Kenji
authors.initials: K
authors.lastname: Hachisuka
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Hikaru
authors.initials: H
authors.lastname: Nakamura
authors.forename: Ryuichi
authors.initials: R
authors.lastname: Sawa
authors.forename: Saburo
authors.initials: S
authors.lastname: Matsui
authors.forename: Tomonari
authors.initials: T
authors.lastname: Matsuda
mesh_terms: D000395:Air Pollutants, Occupational / Q000633:toxicity; D000447:Aldehydes / Q000633:toxicity*; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003296:Cooking; D018736:DNA Adducts; D004249:DNA Damage; D019652:Extraction and Processing Industry; D015525:Fatty Acids, Omega-3 / Q000737:chemistry / Q000378:metabolism*; D043371:Fatty Acids, Omega-6 / Q000737:chemistry / Q000378:metabolism*; D019649:Food Industry; D015227:Lipid Peroxidation; D051379:Mice; D009152:Mutagenicity Tests; D009153:Mutagens; D016273:Occupational Exposure; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics
chemical_list: C506591:4-oxo-(E)-2-hexenal; D000395:Air Pollutants, Occupational; D000447:Aldehydes; D018736:DNA Adducts; D015525:Fatty Acids, Omega-3; D043371:Fatty Acids, Omega-6; D009153:Mutagens