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  3. 4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation: occurrence, detection and adduct formation

4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation: occurrence, detection and adduct formation

  • Mutat Res. 2008 Jul-Aug;659(1-2):56-9. doi: 10.1016/j.mrrev.2008.02.003.
Hiroshi Kasai 1,  Kazuaki Kawai
Affiliations

Affiliation

  • 1 Department of Environmental Oncology, Institute of Industrial Ecological Sciences, University of Occupational and Environmental Health, 1-1 Iseigaoka, Yahatanishi-ku, Kitakyushu 807-8555, Japan. h-kasai@med.uoeh-u.ac.jp
PMID: 18406660 DOI: 10.1016/j.mrrev.2008.02.003
Abstract

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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