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Journal of the American Oil Chemists' Society

, Volume 75, Issue 2, pp 261–267 | Cite as

Conjugated linoleic acid and oxidative stress

  • Sebastiano BanniEmail author
  • Elisabetta Angioni
  • Maria Stefania Contini
  • Gianfranca Carta
  • Viviana Casu
  • Giorgio Amedeo Iengo
  • Maria Paola Melis
  • Monica Deiana
  • Maria Assunta Dessì
  • Francesco P. Corongiu
Article

Abstract

At the present time, conjugated linoleic acid (CLA) is the subject of a growing number of studies since it has been demonstrated to possess anticarcinogenic and antiatherogenic activities in experimental animal models and to increase in some pathological states in humans. In both situations, CLA has been claimed to be involved in oxidative stress, as an antioxidant in the first case and as a primary product of a free-radical attack on polyunsaturated fatty acids (PUFA) in the other. The controversial results are due mostly to a lack of a suitable methodology because the presence of conjugated dienes (CD) in lipid moiety has been taken for years as evidence of lipid peroxidation due to the occurrence of this structure in fatty acid hydroperoxides. We have recently developed a new methodology that consists of the extraction of fatty acids, including CD fatty acid hydroperoxides, by mild saponification and their separation and identification by high-performance liquid chromatography with diode array detector. Fatty acid analyses of liver homogenate, oxidized in vitro either with Fe-ADP or t-butyl hydroperoxide (t-ButylHP), of lamb and rats fed CLA at levels known to prevent carcinogenesis, showed that CLA and its metabolites steadily decreased during oxidative stress and that they are more prone to oxidation than their corresponding methylene-interrupted fatty acids. No significant antioxidant effect of CLA was detected in any model tested. However, CD fatty acid hydroperoxides increased in the t-ButylHP model but not in the Fe-ADP model, owing probably to the degradation of CD fatty acid hydroperoxides induced by this oxidative agent. In conclusion, CLA and its metabolites seem to behave, under oxidative stress, as regular PUFA. Thus, it is highly unlikely that the peculiar effects of CLA are directly related to interference in lipoperoxidative processes.

Key words

Conjugated dienes conjugated linoleic acid diode array detector HPLC hydroperoxides oxidative stress second derivative UV spectrophotometry 

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References

  1. 1.
    Corongiu, F.P., and S. Banni, Detection of Conjugated Dienes by Second Derivative Ultraviolet Spectrophotometry, Meth. Enzymol. 233:303–310 (1994).PubMedGoogle Scholar
  2. 2.
    Glende, E.A., and R.O. Recknagel, Spectrophotometric Detection of Lipid-Conjugated Dienes, in In Vitro Toxicity Indicators, edited by C.A. Tyson and J.M. Frazier, Academic Press, San Diego, 1994, pp. 400–406.Google Scholar
  3. 3.
    Porter, N.A., L.S. Lehman, and D.G. Wujek, Oxidation Mechanisms of Polyunsaturated Fatty Acids, in Oxygen Radicals in Chemistry and Biology, Walter De Gruyter & Co. Berlin, 1984, pp. 235–247.Google Scholar
  4. 4.
    Banni, S., R.W. Evans, M.G. Salgo, F.P. Corongiu, and B. Lombardi, Conjugated Diene and Trans Fatty Acids in Tissue Lipids of Rats Fed an Hepatocarcinogenic Choline-Devoid Diet, Carcinogenesis 11:2053–2057 (1990).PubMedCrossRefGoogle Scholar
  5. 5.
    Banni, S., B.W. Day, R.W. Evans, F.P. Corongiu, and B. Lombardi, Liquid Chromatography Mass Spectrometric Analysis of Conjugated Diene Fatty Acids in a Partially Hydrogenated Fat, J. Am. Oil Chem. Soc. 71:1321–1325 (1994).CrossRefGoogle Scholar
  6. 6.
    Kepler, R.C., P.W. Tucker, and S.B. Tove, Biohydrogenation of Unsaturated Fatty Acids. IV. Substrate Specificity and Inhibition of Linoleate 12-cis,11-trans Isomerase from Butyrivibrio fibrisolvens, J. Biol. Chem. 245:3612 (1970).PubMedGoogle Scholar
  7. 7.
    Fogerty, A.C., G.L. Ford, and D. Svoronos, Octadeca-9,11-dienoic Acid in Foodstuffs and in the Lipids of Human Blood and Breast Milk, Nutr. Rep. Int. 38:937–944 (1995).Google Scholar
  8. 8.
    Banni, S., G. Carta, M.S. Contini, E. Angioni, M. Deiana, M.A. Dessì, M.P. Melis, and F.P. Corongiu, Characterization of Conjugated Diene Fatty Acids in Milk, Dairy Products, and Lamb Tissues, J. Nutr. Biochem. 7:150–155 (1996).CrossRefGoogle Scholar
  9. 9.
    Banni, S., B.W. Day, R.W. Evans, F.P. Corongiu, and B. Lombardi, Detection of Conjugated Diene Isomers of Linoleic Acid in Liver Lipids of Rats Fed a Choline-Devoid Diet Indicates That the Diet Does Not Cause Lipoperoxidation, Ibid.:281–289 (1995).CrossRefGoogle Scholar
  10. 10.
    Ha, Y.L., J. Storkson, and M.W. Pariza, Inhibition of Benzo(a)pyrene-Induced Mouse Forestomach Neoplasia by Conjugated Dienoic Derivatives of Linoleic Acid, Cancer Res. 50:1097–1101 (1990).PubMedGoogle Scholar
  11. 11.
    Ip, C., M. Singh, H.J. Thompson, and J.A. Scimeca, Conjugated Linoleic Acid Suppresses Mammary Carcinogenesis and Proliferative Activity of the Mammary Gland in the Rat, Ibid.:1212–1215 (1994).PubMedGoogle Scholar
  12. 12.
    Liew, C., H.A.J. Schut, S.F. Chin, M.W. Pariza, and R.H. Dashwood, Protection of Conjugated Linoleic Acids Against 2-Amino-3-methylimidazo[4,5-f]quinoline-Induced Colon Carcinogenesis in the F344 Rat: A Study of Inhibitory Mechanisms, Carcinogenesis 16:3037–3043 (1995).PubMedCrossRefGoogle Scholar
  13. 13.
    Lee, K.N., D. Kritchevsky, and M.W. Pariza, Conjugated Linoleic Acid and Atherosclerosis in Rabbits, Atherosclerosis 108:19–25 (1994).PubMedCrossRefGoogle Scholar
  14. 14.
    Dormandy, T.L., and D.G. Wickens, The Experimental and Clinical Pathology of Diene Conjugation, Chem. Phys. Lipids 45:353–364 (1987).PubMedCrossRefGoogle Scholar
  15. 15.
    Banni, S., L. Lucchi, A. Baraldi, B. Botti, G. Cappelli, F.P. Corongiu, M.A. Dessì, A. Tomasi, and E. Lusvarghi, No Direct Evidence of Increased Lipid Peroxidation in Hemodialysed Patients, Nephron 72:177–183 (1996).PubMedCrossRefGoogle Scholar
  16. 16.
    Thompson, S., and M.T. Smith, Measurements of Diene Conjugated from Linoleic Acid in Plasma by High-Performance Liquid Chromatography: A Questionable Noninvasive Assay of Free Radical Activity? Chem. Biol. Interact. 55:357–366 (1985).PubMedCrossRefGoogle Scholar
  17. 17.
    Halliwell, B., and S. Chirico, Lipid Peroxidation: Its Mechanism, Measurement, and Significance, Am. J. Clin. Nutr. 57:715S-725S (1993).PubMedGoogle Scholar
  18. 18.
    Ip, C., S.F. Chin, J.A. Scimeca, and M.W. Pariza, Mammary Cancer Prevention by Conjugated Dienoic Derivative of Linoleic Acid, Cancer Res. 51:6118–6124 (1991).PubMedGoogle Scholar
  19. 19.
    Van Den Berg, J.J.M., N.E. Cook, and D.L. Tribble, Reinvestigation of the Antioxidant Properties of Conjugated Linoleic Acid, Lipids 30:599–605 (1995).PubMedCrossRefGoogle Scholar
  20. 20.
    Banni, S., M.S. Contini, E. Angioni, M. Deiana, M.A. Dessì, M.P. Melis, G. Carta, and F.P. Corongiu, A Novel Approach to Study Linoleic Acid Autoxidation: Importance of Simultaneous Detection of the Substrate and Its Derivative Oxidation Products, Free Radical Res. 25:43–53 (1996).Google Scholar
  21. 21.
    Banni, S., R.W. Evans, M.G. Salgo, F.P. Corongiu, and B. Lombardi, Conjugated Diene and Trans Fatty Acids in a Choline-Devoid Diet Hepatocarcinogenic in the Rat, Carcinogenesis 11:2047–2051 (1990).PubMedCrossRefGoogle Scholar
  22. 22.
    Folch, J., M. Lees, and G.H. Sloane-Stanley, A Simple Method for the Isolation and Purification of Total Lipids from Animal Tissues, J. Biol. Chem. 226:497–509 (1957).PubMedGoogle Scholar
  23. 23.
    Chiang, S.D., C.F. Gessert, and O.H. Lowry, Colorimetric Determination of Extracted Lipids. An Adaptation for Microgram Amounts of Lipids Obtained from Cerumen, Curr. List Med. Lit. Res. Rep. 33:56–113 (1957).Google Scholar
  24. 24.
    Halliwell, B., and J.M.C. Gutteridge, Free Radicals in Biology and Medicine, 2nd edn., Clarendon Press, Oxford, 1989.Google Scholar
  25. 25.
    Tomasi, A., S. Banni, A. Bini, B. Botti, M.A. Dessì, and A. Iannone, A Critical Overview on Spin Trapping, Salicylate Oxidation, and Conjugated Dienes Determination as Probes for the Detection of Free Radical Reactions In Vivo, in Free Radicals in the Environment, Medicine and Toxicology, edited by H. Nohl, H. Esterbauer, and C. Rice-Evans, Richelieu Press, London, 1994, pp. 265–286.Google Scholar
  26. 26.
    Banni, S., E. Angioni, G. Carta, V. Casu, M. Deiana, M.A. Dessì, L. Lucchi, M.P. Melis, A. Rosa, S. Scrugli, D. Sicbaldi, E. Solla, and F.P. Corongiu, Metabolism of Conjugated Linoleic Acid in Pathological States, 88th AOCS Annual Meeting (Abstract), 1997.Google Scholar
  27. 27.
    Nugteren, D.H., Inhibition of Prostaglandin Biosynthesis by 8cis, 12trans, 14cis-Eicosatrienoic Acid and 5cis, 8cis, 12trans, 14cis-Eicosatetraenoic Acid, Biochim. Biophys. Acta 121:171–176 (1970).Google Scholar

Copyright information

© AOCS Press 1998

Authors and Affiliations

  • Sebastiano Banni
    • 1
    Email author
  • Elisabetta Angioni
    • 1
  • Maria Stefania Contini
    • 1
  • Gianfranca Carta
    • 1
  • Viviana Casu
    • 1
  • Giorgio Amedeo Iengo
    • 1
  • Maria Paola Melis
    • 1
  • Monica Deiana
    • 1
  • Maria Assunta Dessì
    • 1
  • Francesco P. Corongiu
    • 1
  1. 1.Dipartimento di Biologia Sperimentale, Sezione Patologia SperimentaleUniversita’ degli Studi di Cagliari, Cittadella UniversitariaMonserrato (Cagliari)Italy

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