Skip to main content

Formation of genotoxic dicarbonyl compounds in dietary oils upon oxidation

Lipids volume 39, Article number: 481 (2004) Cite this article

Abstract

Dietary oils—tuna, salmon, cod liver, soybean, olive, and corn oils—were treated with accelerated storage conditions (60°C for 3 and 7 d) and a cooking condition (200°C for 1 h). Genotoxic malonaldehyde (MA), glyoxal, and methylglyoxal formed in the oils were analyzed by GC. Salmon oil produced the greatest amount of MA (1070±77.0 ppm of oil) when it was heated at 60°C for 7 d. The highest formation of glyoxal was obtained from salmon oil heated at 60°C for 3 d. More glyoxal was found from salmon and cod liver oils when they were heated for 3 d (12.8±1.10 and 7.07±0.19 ppm, respectively) than for 7d (6.70±0.08 and 5.94±0.38 ppm, respectively), suggesting that glyoxal underwent secondary reactions during a prolonged time. The amount of methyglyoxal formed ranged from 2.03±0.13 (cod liver oil) to 2.89±0.11 ppm (tuna oil) in the fish oils heated at 60°C for 7 d. Among vegetable oils, only olive oil yielded methylglyoxal (0.61±0.03 ppm) under accelerated storage conditions. When oils were treated under cooking conditions, the aldehydes formed were comparable to those formed under accelerated storage conditions. Fish oils produced more MA, glyoxal, and methylglyoxal than did vegetable oils because the fish oils contained higher levels of long-chain PUFA, such as EPA and DHA, than did the vegetable oils. A statistically significant correlation (P<0.05) between the α-tocopherol content and the oxidation parameters was obtained from only MA and fish oils heated at 60°C for 3 d.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

Price includes VAT (USA)
Tax calculation will be finalised during checkout.

Abbreviations

MA:

malonaldehyde

1-MP:

1-methylpyrazole

NPD:

nitrogen phosphorus detector

ROS:

reactive oxygen species

SPE:

solid-phase extraction

References

  1. Yoshikawa, T. (1985) Diseases, in Peroxide Lipid in Biological Systems (Uchiyama, M., Matsuo, M., and Sagai, M., eds.), pp. 289–313, Japan Scientific Society Press, Tokyo.

    Google Scholar 

  2. St. Angelo, A.J. (1996) Lipid Oxidation in Foods, Crit. Rev. Food Sci. Nutr. 36, 175–224.

    PubMed  CAS  Google Scholar 

  3. Vercelotti, J.R., St. Angelo, A.J., and Spanier, A.M. (1992) Lipid Oxidation in Foods: An Overview in Lipid Oxidation in Foods (St. Angelo, A.J., ed.), pp. 1–11, American Chemical Society Symposium Series 500, American Chemical Society, Washington, DC.

    Google Scholar 

  4. Kubow, S. (1990) Toxicity of Dietary Lipid Peroxidation Products, Trends Food Sci. Technol. 1, 67–71.

    CAS  Article  Google Scholar 

  5. Ohta, S. (1985) Toxicity of Oxidized Oils and Fats, Shoku no Kagaku 91, 43–48.

    CAS  Google Scholar 

  6. Edem, D.O. (2002) Palm Oil. Biochemical, Physiological, Nutritional, Hematological and Toxicological Aspects: A Review, Plant Foods Hum. Nutr. 57, 319–341.

    PubMed  CAS  Article  Google Scholar 

  7. Oarada, M., Miyazawa, T., Fujimoto, K., Ito, E., Terao, K., and Kaneda, T. (1988) Degeneration of Lymphoid Tissues in Mice with the Oral Intake of Low Molecular Weight Compounds Formed During Oil Autoxidation, Agric. Biol. Chem. 52, 2101–2102.

    CAS  Google Scholar 

  8. Isong, E.U., Ebong, P.E., Ifon, E.T., Umoh, I.B., and Eka, O.U. (1997) Thermoxidized Palm Oil Induces Reproductive Toxicity in Healthy and Malnourished Rats, Plant Foods Hum. Nutr. 51, 159–166.

    PubMed  CAS  Article  Google Scholar 

  9. Frankel, E.N., and Neff, W.E. (1983) Formation of Malonaldehyde from Lipid Oxidation Products, Biochim. Biophys. Acta 754, 264–270.

    CAS  Google Scholar 

  10. Yin, D., and Brunk, U.T. (1995) Carbonyl Toxification Hypothesis of Biological Aging, in Molecular Basis of Aging (Macieira-Coehl, A., ed.), pp. 421–436, CRC, Boca Raton, FL.

    Google Scholar 

  11. Okado-Matsumoto, A., and Fridovich, I. (2000) The Role of α,β-Dicarbonyl Compounds in the Toxicity of Short Chain Sugars, J. Biol. Chem. 275, 34853–34857.

    PubMed  CAS  Article  Google Scholar 

  12. Siu, G.M., Draper, H.H., and Valli, V.E. (1983) Oral Toxicity of Malonaldehyde: A 90-Day Study on Mice, J. Toxicol. Environ. Health 11, 105–119.

    PubMed  CAS  Google Scholar 

  13. Kalapos, M.P. (1999) Methylglyoxal in Living Organisms. Chemistry, Biochemistry, Toxicology and Biological Implications, Toxicol. Lett. 110, 145–175.

    PubMed  CAS  Article  Google Scholar 

  14. Bird, R.P., Draper, H.H., and Valli, V.E.O. (1982) Toxicological Evaluation of Malonaldehyde: A 12-Month Study of Mice, J. Toxicol. Environ. Health 10, 897–905.

    PubMed  CAS  Article  Google Scholar 

  15. Baskaran, S., and Balasubramanian, K.A. (1990) Toxicity of Methylglyoxal Towards Rat Enterocytes and Colonocytes, Biochem. Int. 21, 165–174.

    PubMed  CAS  Google Scholar 

  16. Takahashi, M., Okamiya, H., Furukawa, F., Toyoda, K., Sato, H., Imaida, K., and Hayashi, Y. (1989) Effect of Glyoxal and Methyl Glyoxal Administration on Gastric Carcinogenesis in Wistar Rats After Initiation with N-Methyl-N′-nitro-N-nitrosoguanidine, Carcinogenesis, 10, 1925–1927.

    PubMed  CAS  Google Scholar 

  17. Niyati-Shirkhodaee, F., and Shibamoto, T. (1993) Gas Chromatographic Analysis of Glyoxal and Methylglyoxal Formed from Lipids and Related Compounds upon Ultraviolet Irradiation, J. Agric. Food Chem. 41, 227–230.

    CAS  Article  Google Scholar 

  18. Eder, K., Keller, U., Hirche, F., and Brandsch, C. (2003) Thermally Oxidized Dietary Fats Increase the Susceptibility of Rat LDL to Lipid Peroxidation but Not Their Uptake by Macrophages, J. Nutr. 133, 2830–2837.

    PubMed  CAS  Google Scholar 

  19. Umano, K., Dennis, K.J., and Shibamoto, T. (1988) Analysis of Free Malondialdehyde in Photoirradiated Corn Oil and Beef Fat via a Pyrazole Derivative, Lipids 23, 811–814.

    PubMed  CAS  Google Scholar 

  20. Dennis, K.J., and Shibamoto, T. (1990) Gas Chromatographic Analysis of Reactive Carbonyl Compounds Formed from Lipids upon UV Irradiation, Lipids, 25, 460–464.

    PubMed  CAS  Google Scholar 

  21. Tamura, H., and Shibamoto, T. (1991) Gas Chromatographic Analysis of Malonaldehyde and 4-Hydroxy-2-(E)-nonenal Produced from Arachidonic Acid and Linoleic Acid in a Lipid Peroxidation Model System, Lipids 26, 170–173.

    PubMed  CAS  Google Scholar 

  22. Miyake, T., and Shibamoto, T. (1998) Inhibition of Malonaldehyde and Acetaldehyde Formation from Blood Plasma Oxidation by Naturally Occurring Antioxidants, J. Agric. Food Chem. 46, 3694–3697.

    CAS  Article  Google Scholar 

  23. Ichinose, T., Miller, M.G., and Shibamoto, T. (1989) Gas Chromatographic Analysis of Free and Bound Malonaldehyde in Rat Liver Homogenates, Lipids 24, 895–898.

    PubMed  CAS  Google Scholar 

  24. Wootton, M., Edwards, R.A., Faraji-Haremi, R., and Johnson, A.T. (1976) Effect of Accelerated Storage Conditions on the Chemical Composition and Properties of Australian Honeys. 1. Color, Acidity and Total Nitrogen Content, J. Apicul. Res. 15, 23–28.

    CAS  Google Scholar 

  25. Wootton, M., Edwards, R.A., Faraji-Haremi, R., and Williams, P.J. (1978) Effect of Accelerated Storage Conditions on the Chemical Composition and Properties of Australian Honeys. 3. Changes in Volatile Components, J. Apicul. Res. 17, 167–172.

    CAS  Google Scholar 

  26. Hawrysh, A.J., Shand, P.J., Tokarska, B., and Lin, C. (1988) Effects of Tertiary Butylhydroquinone on the Stability of Canola Oil. I. Accelerated Storage, Can. Inst. Food Sci. Technol. J. 21, 549–554.

    CAS  Google Scholar 

  27. Stapelfeldt, H., Nielsen, B.R., and Skibsted, L.H. (1997) Effect of Heat Treatment, Water Activity and Storage Temperature on the Oxidative Stability of Whole Milk Powder, Int. Dairy J. 7, 331–339.

    CAS  Article  Google Scholar 

  28. Ogata, J., Hagiwara, Y., Hagiwara, H., and Shibamoto, T. (1996) Inhibition of Malonaldehyde Formation by Antioxidants from ω-3 Polyunsaturated Fatty Acids, J. Am. Oil Chem. Soc. 73, 653–656.

    CAS  Google Scholar 

  29. Lee, K.-G., Mitchell, A.E., and Shibamoto, T. (2000) Determination of Antioxidant Properties of Aroma Extracts from Various Beans, J. Agric. Food Chem. 48, 4817–4820.

    PubMed  CAS  Article  Google Scholar 

  30. Lee, K.-G., and Shibamoto, T. (2002) Determination of Antioxidant Potential of Volatile Extracts Isolated from Various Herbs and Spices, J. Agric. Food Chem. 50, 4947–4952.

    PubMed  CAS  Article  Google Scholar 

  31. Yanishilieva, N.V., and Marinova, E.M. (2001) Stabilization of Edible Oils with Natural Antioxidants, Eur. J. Lipid Sci. Technol. 103, 752–767.

    Article  Google Scholar 

  32. Kishida, E., Oribe, M., and Kojo, S. (1990) Relationship Among Malondialdehyde, TBA-Reactive Substances, and Tocopherols in the Oxidation of Rapeseed Oil, J. Nutr. Sci. Vitaminol. 35, 619–623.

    Google Scholar 

  33. Quiles, J.L., Ramirez-Tortosa, M.C., Gomez, J.A., Huertas, J.R., and Mataix, J. (2002) Role of Vitamin E and Phenolic Compounds in the Antioxidant Capacity, Measured by ESR, of Virgin Olive, Olive and Sunflower Oils After Frying, Food Chem. 76, 461–468.

    CAS  Article  Google Scholar 

  34. Moree-Testa, P., and Saint-Jalm, Y. (1981) Determination of α-Dicarbonyl Compounds in Cigarette Smoke, J. Chromatogr. 217, 197–208.

    CAS  Article  Google Scholar 

  35. Nishiyama, T., Hagiwara, Y., Hagiwara, H., and Shibamoto, T. (1994) Formation and Inhibition of Genotoxic Glyoxal and Malonaldehyde from Phospholipids and Fish Liver Oil upon Lipid Peroxidation, J. Agric. Food Chem. 42, 1728–1731.

    CAS  Article  Google Scholar 

  36. Pryor, W.A., Stanley, J.P., and Blair, E. (1976) Autoxidation of Polyunsaturated Fatty Acids: II. A Suggested Mechanism for the Formation of TBA-Reactive Materials from Prostaglandin-like Endoperoxides, Lipids 11, 370–379.

    PubMed  CAS  Google Scholar 

  37. Tamura, H., Kitta, K., and Shibamoto, T. (1991) Formation of Reactive Aldehydes from Fatty Acids in a Fe2+/H2O2 Oxidation System, J. Agric. Food Chem. 39, 439–442.

    CAS  Article  Google Scholar 

  38. Frankel, E.N. (1993) Formation of Headspace Volatiles by Thermal Decomposition of Oxidized Fish Oils vs. Oxidized Vegetable Oils, J. Am. Oil Chem. Soc. 70, 767–772.

    CAS  Google Scholar 

  39. Esterbauer, H. (1982) Aldehydic Products of Lipid Peroxidation, in Free Radicals, Lipid Peroxidation, Cancer (McBrien, D.C.H., and Slater, T.F., eds.), pp. 101–128, Academic Press, London.

    Google Scholar 

  40. Neff, W.E., Selke, E., Mounts, T.L., Rinsch, W., Frankel, E.N., and Zeitoun, M. (1992) Effect of Triacylglycerol Composition and Structures on Oxidative Stability of Oils from Selected Soybean Germplasm, J. Am. Oil. Chem. Soc. 69, 111–118.

    CAS  Google Scholar 

  41. Gunstone, F.D., Harwood, J.L., and Padley, F.B. (1986) The Lipid Handbook, Chapman & Hall, New York.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Environmental Toxicology, University of California-Davis, One Shields Ave., 95616, Davis, CA

    Kazutoshi Fujioka & Takayuki Shibamoto

Authors
  1. Kazutoshi Fujioka
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Takayuki Shibamoto
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Takayuki Shibamoto.

About this article

Cite this article

Fujioka, K., Shibamoto, T. Formation of genotoxic dicarbonyl compounds in dietary oils upon oxidation. Lipids 39, 481 (2004). https://doi.org/10.1007/s11745-004-1254-y

Download citation

  • Received:

  • Accepted:

  • DOI: https://doi.org/10.1007/s11745-004-1254-y

Keywords

  • Methylglyoxal
  • Glyoxal
  • Quinoxaline
  • Sodium Thiosulfate Solution
  • Nitrogen Phosphorus Detector