4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation, causes DNA adduct formation in mouse organs

Ind Health. 2005 Oct;43(4):699-701. doi: 10.2486/indhealth.43.699.

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.

MeSH terms

  • Air Pollutants, Occupational / toxicity
  • Aldehydes / toxicity*
  • Animals
  • Chromatography, High Pressure Liquid
  • Cooking
  • DNA Adducts*
  • DNA Damage
  • Extraction and Processing Industry
  • Fatty Acids, Omega-3 / chemistry
  • Fatty Acids, Omega-3 / metabolism*
  • Fatty Acids, Omega-6 / chemistry
  • Fatty Acids, Omega-6 / metabolism*
  • Food Industry
  • Lipid Peroxidation*
  • Mice
  • Mutagenicity Tests
  • Mutagens*
  • Occupational Exposure
  • Salmonella typhimurium / drug effects
  • Salmonella typhimurium / genetics

Substances

  • 4-oxo-(E)-2-hexenal
  • Air Pollutants, Occupational
  • Aldehydes
  • DNA Adducts
  • Fatty Acids, Omega-3
  • Fatty Acids, Omega-6
  • Mutagens