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Identification of noveltrans isomers of 20∶5n−3 in liver lipids of rats fed a heated oil

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Lipids

Abstract

Trans polyunsaturated n−3 fatty acids are formed as a result of the heat treatment of vegetable oils. It was demonstrated previously that the 18∶3 Δ9cis, 12cis, 15trans containing acis Δ9 ethylenic bond was converted to a geometrical isomer of 20∶5n−3, the 20∶5 Δ5cis, 8cis, 11cis, 14cis, 17trans. In the present study, we have identified two new isomers of eicosapentaenoic acid, the Δ11 monotrans and the Δ11, 17 ditrans isomers in liver of rats fed a heated oil. These are formed as a result of the conversion of two of the main isomers of linolenic acid which are present in refined and frying oils, the 18∶3 Δ9trans, 12cis, 15cis and the 18∶3 Δ9trans, 12cis, 15trans.

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Abbreviations

DMOX:

dimethyl oxazoline derivatives

ECL:

equivalent chain length

EPA:

eicosapentaenoic acid

FAME:

fatty acid methyl esters

FTIR:

Fourier transform infrared

GLC:

gas-liquid chromatography

PUFA:

polyunsaturated fatty acids

References

  1. Ackman, R.G., Hooper, S.N., and Hooper, D.L. (1974) Linolenic Acid Artifact from the Deodorization of Oil,J. Am. Oil Chem. Soc. 51, 42–49.

    CAS  Google Scholar 

  2. Grandgirard, A., Sébédio, J.L., and Fleury J. (1984) Geometrical Isomerization of Linolenic Acid During Heat Treatment of Vegetable Oils,J. Am. Oil. Chem. Soc. 61, 1563–1568.

    CAS  Google Scholar 

  3. Sébédio, J.L., Grandgirard, A., and Prévost, J. (1988) Linoleic Acid Isomers in Heat Treated Sunflower Oils,J. Am. Oil Chem. Soc. 65, 365–366.

    Google Scholar 

  4. Wolff, R.L. (1992)Trans Polyunsaturated Fatty Acids in French Edible Rapeseed and Soybean Oils,J. Am. Oil Chem. Soc. 69 106–110.

    CAS  Google Scholar 

  5. Wolff, R.L., and Sébédio, J.L. (1991) Geometrical Isomers of Linolenic Acid in Low-Calorie Spreads Marketed in France,J. Am. Oil Chem. Soc. 68, 719–725.

    CAS  Google Scholar 

  6. Chardigny, J.M., Sébédio, J.L., and Berdeaux, O. (1995)Trans Polyunsaturated Fatty Acids: Occurrence and Nutritional Implication, inAdvances in Applied Lipid Research (Padley, F.B., ed.) Vol. 2, JAI Press, London, in press.

    Google Scholar 

  7. Wolff, R.L. (1995) Recent Applications of Capillary Gas Chromatography to Some Difficult Separations of Positional or Geometrical Isomers of Unsaturated Fatty Acids, inNew Trends in Lipid and Lipoprotein Analysis (Sébédio, J.L., and Perkins, E.G. eds.) pp. 147–180, AOCS Press, Champaign.

    Google Scholar 

  8. Chen, Z.Y., Pelletier, G., Hollywood, R., and Ratnayake, W.M.N. (1995)Trans Fatty Acid Isomers in Canadian Human Milk,Lipids 30, 15–21.

    PubMed  CAS  Google Scholar 

  9. Chardigny, J.M., Wolff, R.L., Mager, E., Sébédio, J.L., Martine, L., Juanéda, P., and Grandgirard, A. (1995)Trans Mono- and Polyunsaturated Fatty Acids in Human Milk,Eur. J. Clin. Nutr. 49, 523–531.

    PubMed  CAS  Google Scholar 

  10. Privett, O.S., Stearns, E.M., and Nickell, E.C. (1967) Metabolism of Geometric Isomers of Linoleic Acid in Rat,J. Nutr. 92, 302–310.

    Google Scholar 

  11. Beyers, E.C., and Emken, E.A. (1991) Metabolites ofcis-trans andtrans-cis Isomers of Linoleic Acid in Mice and Incorporation into Tissue Lipids,Biochim. Biophys. Acta 1082, 275–284.

    PubMed  CAS  Google Scholar 

  12. Grandgirard, A., Piconneaux, A., Sébédio, J.L., O'Keefe, S.F., Le Quéré, J.L., and Sémon, E. (1989) Occurrence of Geometrical Isomers of Eicosapentaenoic and Docosahexaenoic Acids in Liver Lipids of Rats Fed Heated Linseed Oil,Lipids 24, 799–804.

    PubMed  CAS  Google Scholar 

  13. Chardigny, J.M., Sébédio, J.L., Juanéda, P., Vatèle, J.M., and Grandgirard, A. (1993) Occurrence of n−3trans Polyunsaturated Fatty Acids in Human Platelets,Nutr. Res. 13, 1105–1111.

    Article  CAS  Google Scholar 

  14. O'Keefe, S.F., Lagarde, M., Grandgirard, A., and Sébédio, J.L. (1990)Trans Omega-3 Eicosapentaenoic and Docosahexaenoic Acids Exhibit Different Inhibitory Effects on Arachidonic Acid Metabolism in Human Platelets Compared to the Respectivecis Fatty Acids,J. Lipid Res. 31, 1241–1246.

    PubMed  Google Scholar 

  15. Chardigny, J.M., Sébédio, J.L., Juanéda, P., Vatèle, J.M., and Grandgirard, A. (1995) Effects oftrans n−3 Polyunsaturated Fatty Acids on Human Platelet Aggregation,Nutr. Res. 15, 1463–1471.

    Article  CAS  Google Scholar 

  16. Sébédio, J.L., and Chardigny, J.M. (1996) Physiological Effects oftrans and Cyclic Fatty Acids, inDeep Frying: Practices, Chemistry and Nutrition (Perkins, E.G., and Erickson, M., eds.), AOCS Press, Champaign, in press.

    Google Scholar 

  17. Ratnayake, W.N.M., Chen, Z.Y., Pelletier, G., and Weber, D. (1994) Occurrence of 5c, 8c, 11c, 14t-Eicosatetraenoic Acid and Other Unusual Polyunsaturated Fatty Acids in Rats Fed Partially Hydrogenated Canola Oil,Lipids 29, 707–714.

    PubMed  CAS  Google Scholar 

  18. Lemarchal, P., and Bornens, M. (1968) Désaturation de l'Acide Élaïdique par le Foie de Ratin vitro, Bull. Soc. Chim. Biol. 50, 195–217.

    PubMed  CAS  Google Scholar 

  19. Grandgirard, A., and Sébédio, J.L. (1989) Incorporation des Isomères Géométriques des Acides Eicosapentaènoique et Docosahéxaènoique dans les Tissus de Rats ayant Ingéré des Corps Gras Chauffés, inProceedings of the 1st EUROLIPID Congress, June 6–9, 1989 (Karleskind, A., ed.) pp. 792–799, Paris.

  20. Vatèle, J.M., Doan, H.D., Fenet, B., Chardigny, J.M., and Sébédio, J.L. (1996) Synthesis of methyl (5Z,8Z,11E,14Z,17E)- and (5Z,8Z,11E,14Z,17Z)-Eicosapentaenoate (EPA Δ11t and Δ11t, 17t),Chem. Phys. Lipids 75, in press.

  21. Folch, J., Lees, M., and Sloane-Stanley, G.M. (1957) A Simple Method for the Determination and Purification of Total Lipids from Animal Tissues,J. Biol. Chem. 226, 497–509.

    PubMed  CAS  Google Scholar 

  22. Morrison, W.R., and Smith, L.M. (1964) Preparation of Fatty Acid Methyl Esters and Dimethylacetals from Lipids with Boron-Fluoride Methanol,J. Lipid Res. 5, 600–608.

    PubMed  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  24. Piconneaux, A. (1987) Etude de la Désaturation et de l'Élongationin vivo d'Isomères Géométriques de l'Acide Linolénique, Ph.D. Thesis, University of Burgundy, pp. 134–147.

  25. Sébédio, J.L., Le Quéré, J.L., Sémon, E., Morin, O., Prévost, J., and Grandgirard, A. (1987) Heat Treatment of Vegetable Oils. II. GC-MS and GC FTIR Spectra of Some Isolated Cyclic Fatty Acid Monomers.J. Am. Oil Chem. Soc. 64, 1324–1333.

    Google Scholar 

  26. O'Keefe S.F., Gaskins-Wright, S., Wiley, V., and Chen, I.C. (1994) Levels oftrans Geometrical Isomers of Essential Fatty Acids in Some Unhydrogenated US Vegetable Oils,J. Food Lipid 1, 165–176.

    Google Scholar 

  27. Brenner, R.R. (1971) The Desaturation Step in the Animal Biosynthesis of Polyunsaturated Fatty Acids,Lipids 16, 920–926.

    Google Scholar 

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Chardigny, JM., Sébédio, JL., Grandgirard, A. et al. Identification of noveltrans isomers of 20∶5n−3 in liver lipids of rats fed a heated oil. Lipids 31, 165–168 (1996). https://doi.org/10.1007/BF02522616

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  • DOI: https://doi.org/10.1007/BF02522616

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