Skip to main content
Log in

Analysis of conjugated linoleic acid isomers and content in french cheeses

  • Published:
Journal of the American Oil Chemists' Society

Abstract

Conjugated linoleic acid (CLA) occurs in food as a result of microbial enzymatic reactions, free radical-type oxidation, and heat treatment. CLA is found in animal products, such as meat and dairy products, especially in cheeses. The CLA composition of 12 different French cheeses was determined by a combination of different analytical methods: reversed-phase high-performance liquid chromatography (RP-HPLC), gas chromatography-mass spectrometry (GC-MS), GC-Fourier transform infrared (GC-FTIR), and silver nitrate thin-layer chromatography (AgNO3-TLC). New isomers (Δ8,10- and Δ11,13-octadecadienoic acids with all possible cis and trans configurations) that co-eluted with previously identified isomers (Δ9c,11t-; Δ9t,11c-; Δ10c,12t-; Δ10t,12c-; Δ11c,13c-; Δ9c,11c-; Δ10c,12c-; Δ9t,11t-; Δ10t12t-octadecadienoic acids) were detected. Δ9c,11t-Octadecadienoic acid was the major CLA isomer in these cheeses. All isomers were present in each product, whatever the production process. However, CLA content in the cheeses varied from 5.3 to 15.80 mg/g of cheese fat, which depended primarily on the origin of the milk (season, geography) and somewhat on the production process.

This is a preview of subscription content, log in via an institution to check access.

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Ha, Y.L., N.K. Grimm, and M.W. Pariza, Anticarcinogens from Fried Ground Beef: Heat-Altered Derivatives of Linoleic Acid, Carcinogenesis 8:1881–1887 (1987).

    Article  PubMed  CAS  Google Scholar 

  2. Cawood, P., D.G. Wickens, S.A. Iversen, J.M. Braganza, and T.C Dormandy, The Nature of Diene Conjugation in Human Serum, Bile and Duodenal Juice, Fed. Eur. Biol. Soc. 59:280–283 (1983).

    Google Scholar 

  3. Gurr, I.G., Isomeric fatty acids, Biochem. Soc. Trans. 15:336–338 (1987).

    PubMed  CAS  Google Scholar 

  4. Viviani, R., Metabolism of Long Chain Fatty Acids in the Rumen, Adv. Lipid Res. 8:267–346 (1970).

    PubMed  CAS  Google Scholar 

  5. Ha, Y.L., N.K. Grimm, and M.W. Pariza, Newly Recognized Anticarcinogenic Fatty Acids: Identification and Quantification in Natural and Processed Cheeses, J. Agric. Food Chem. 37:75–81 (1989).

    Article  CAS  Google Scholar 

  6. Pariza, M.W., L.J. Loretz, J.M. Storkson, and N.C. Holland, Mutagens and Modulator of Mutagenesis in Fried Ground Beef, Cancer Res. 43 (Suppl):2444s (1983).

  7. Ip, C., J.A. Scimeca, and H.J. Thompson, Conjugated Linoleic Acid. A Powerful Anticarcinogen from Animal Fat Sources, Cancer Suppl. 74:1050–1054 (1994).

    CAS  Google Scholar 

  8. 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).

    PubMed  CAS  Google Scholar 

  9. Schonberg, S., and H.E. Krokan, The Inhibitory Effect of Conjugated Dienoic Derivatives of Linoleic Acid on the Growth of Human Tumor Cell Lines Is Part Due to Increased Lipid Peroxidation, Anticancer Res. 15:1241–1246 (1995).

    PubMed  CAS  Google Scholar 

  10. Nicolosi, R.J., K.V. Courtemanche, L. Laitinien, J.A. Scimeca, and P.J. Huth, Effect of Feeding Diets Enriched in Conjugated Linoleic Acid on Lipoproteins and Aortic Atherogenesis in Hamsters, Circulation 88:Suppl. 2458 (1993).

    Google Scholar 

  11. Lee, K.N., D. Kritchevsky, and M.W. Pariza, Conjugated Linoleic Acid and Atherosclerosis in Rabbits, Atherosclerosis 108:19–25 (1994).

    Article  PubMed  CAS  Google Scholar 

  12. Lin, H., T.D. Boylston, M.J. Chang, L.O. Luedecke, and T.D. Shultz, Survey of the Conjugated Linoleic Acid Contents of Dairy Products, J. Dairy Sci. 78:2358–2365 (1994).

    Google Scholar 

  13. Wolff, R.L., and A.F.M. Castera-Rossignol, Mise au point et évaluation d’une méthode d’extraction de la matière grasse de fromage de type Emmental, Rev. Fr. Corps Gras 3:123–132 (1987).

    Google Scholar 

  14. Maniongui, C., J. Gresti, M. Bugaut, S. Gauthier, and J. Bézard, Determination of Bovine Butterfat Triglycerides by Reversed-Phase Liquid Chromatography and Gas Chromatography, J. Chromatogr. 543:81–103 (1991).

    Article  PubMed  CAS  Google Scholar 

  15. Sébédio, J.L., and R.G. Ackman, Some Minor Fatty Acids of Rapeseed Oils, J. Am. Oil Chem. Soc. 56:15–21 (1979).

    Google Scholar 

  16. Sébédio, J.L., and R.G. Ackman, Calculation of GLC Retention Data for Some Accessible C20 Isomeric cis-Unsaturated Fatty Acids, Chromatogr. Sci. 20:231–234 (1982).

    Google Scholar 

  17. Fay, L., and U. Richly, Location of Double Bonds in Polyunsaturated Acids by Gas Chromatography-Mass Spectrometry After 4,4-Dimethyloxazoline Derivatization, J. Chromatogr. 541:89–98 (1991).

    Article  CAS  Google Scholar 

  18. Spitzer, V., F. Marx, and K. Pfeilsticker, Electron Impact Mass Spectra of the Oxazoline Derivatives of Some Conjugated Diene and Triene C18 Fatty Acids, J. Am. Oil Chem. Soc. 71:873–876 (1994).

    Article  CAS  Google Scholar 

  19. Zhang, J.Y., Q.T. Yu, and Z.H. Huang, Chemical Modification in Mass Spectrometry. IV—2-Alkenyl-4,4-dimethyloxazolines as Derivatives for the Double Bond Location of Long-Chain Olefinic Acids, Biomed. Environ. Mass Spectrom. 15:33–44 (1988).

    Article  CAS  Google Scholar 

  20. Berdeaux, O., W.W. Christie, F.D. Gunstone, and J.L. Sébédio, Large-Scale Synthesis of Methyl cis-9,trans-11-Octadecadienoate from Methyl Ricinoleate, J. Am. Oil Chem. Soc. 74:1011–1015 (1997).

    Article  CAS  Google Scholar 

  21. Polan, C.E., J.J. McNeill, and S.B Tove, Biohydrogenation of Unsaturated Fatty Acids by the Rumen Bacteria, J. Bacteriol. 88:1056 (1964).

    PubMed  CAS  Google Scholar 

  22. Kepler, C.R., and S.B. Tove, Biohydrogenation of Unsaturated Fatty Acids. III Purification and Properties of a Linoleate Δ12-cis, Δ11-trans-Isomerase from Butyrivibrio fibrisolvens, J. Biol. Chem. 242:5686–5692 (1967).

    PubMed  CAS  Google Scholar 

  23. Dobson, G., and W.W. Christie, Structural Analysis of Fatty Acids by Mass Spectrometry of Picolinyl Esters and Dimethyloxazoline Derivatives, Trends Anal. Chem. 15:130–137 (1996).

    CAS  Google Scholar 

  24. Hopkins, C.Y., Fatty Acids with Conjugated Unsaturation, in Topics in Lipid Chemistry, edited by F.D. Gunstone, Elek Books, London, 1972, Vol. 3, pp. 37–85.

    Google Scholar 

  25. Chin, S.F., J.M. Storkson, Y.L. Ha, and M.W. Pariza, Dietary Sources of Conjugated Dienoic Acid Isomers of Linoleic Acid, A Newly Recognized Class of Anticarcinogens, J. Food Comp. Anal. 5:185–197 (1992).

    Article  CAS  Google Scholar 

  26. Jiang, J., L. Bjoerck, R. Fonden, and M. Emanuelson, Occurrence of Conjugated cis-9,trans-11-Octadecadienoic Acid in Bovine Milk: Effects of Feed and Dietary Regimen, J. Dairy Sci. 79:438–445 (1996).

    Article  PubMed  CAS  Google Scholar 

  27. Ward, P.F.V., T.W. Scott, and R.M.C. Dawson, The Hydrogenation of Unsaturated Fatty Acids by the Rumen Bacteria, Biochem. J. 92:60 (1994).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to J. C. Martin.

About this article

Cite this article

Lavillonnière, F., Martin, J.C., Bougnoux, P. et al. Analysis of conjugated linoleic acid isomers and content in french cheeses. J Amer Oil Chem Soc 75, 343–352 (1998). https://doi.org/10.1007/s11746-998-0051-6

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-998-0051-6

Key Words

Navigation