Mutat Res. 2008 Feb 23. [Epub ahead of print]
4-Oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation:
Occurrence, detection and adduct formation.
Kasai H, Kawai K.
Department of Environmental Oncology, Institute of Industrial
Ecological Sciences, University of Occupational and Environmental
Health, 1-1 Iseigaoka, Yahatanishi-ku, Kitakyushu 807-8555, Japan.
The purpose of this review is to summarize our recent studies of a
novel mutagen, 4-oxo-2-hexenal. To identify the mutagens formed in a
model reaction of lipid peroxidation, linolenic acid methyl ester and
hemin were reacted with dG. 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. 4-OHE reacts with DNA to form dG, dC, and 5-methyl-dC(5-Me-
dC)-adducts (dG*, dC*, 5-Me-dC*) in vitro. After 4-OHE was orally
administered to mice, these adducts were detected in esophageal,
stomach and intestinal DNA by liquid chromatography coupled with
electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS). We
also confirmed the formation of 4-OHE during the heat processing of
edible vegetable oil, and during cooking. It was present at an
especially high concentration in broiled saury. 4-OHE is probably
generated by the oxidation of omega-3 fats. These results provide a
warning to humans, who may be exposed to this mutagen. Since 4-OHE
induces DNA adduct formation in experimental animal organs, further
studies on the carcinogenicity of 4-OHE and the detection of 4-OHE-DNA
adducts in human tissue will be required. |
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