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In vitro desaturation or elongation of monotrans isomers of linoleic acid by rat liver microsomes

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Abstract

Several nutritional studies have shown the in vivo conversion of the 9c,12t-18:2 and 9t,12c-18:2 into long chain polyunsaturated fatty acids (PUFA) containing 20 carbons (geometrical isomers of eicosadienoic and eicosatetraenoic acids). In the present work, some in vitro studies were carried out in order to have precise information on the conversion of these two isomers.

In a first set of experiments, studies were focused on the in vitro Δ6 desaturation, the first regulatory step of the biosynthesis of n-6 long chain PUFA, from 9c,12c-18:2. Rat liver microsomes were prepared and incubated under desaturation conditions with [1-14C]-9c,12c-18:2 in presence of unlabelled 9c,12t-, 9t,12c- or 9t,12t-18:2. The data show that each trans isomer induced a decrease of the Δ6 desaturation of the [1-14C]-9c,12c-18:2, but the 9c,12t-18:2 was the most potent inhibitor (up to 63%). Rat liver microsomes were also incubated with [1-14C]-9c,12c-18:2, [1-14C]-9c,12t-18:2 or [1-14C]-9t,12c-18:2 under desaturation conditions. The results indicated that 18:2 Δ9c,12t is a much better substrate for desaturase than 9t,12c-18:2. Moreover, the conversion levels of [1-14C]-9c,12t-18:2 was similar to what was observed for its all cis homologue, at low substrate concentration only. In a second set of experiments, in vitro elongation studies of each mono-trans 18:2 isomers and 9c,12c-18:2 were carried out. For that purpose, rat liver microsomes were incubated with [1-14C]-9c,12c-18:2, [1-14C]-9c,12t-18:2 or [1-14C]-9t,12c-18:2 under elongation conditions. The data show that [1-14C]-9t,12c-18:2 is better elongated than 9c,12c-18:2 while the amount of product formed from [1-14C]-9c,12t-18:2 was lower than was produced from the 9c,12c-18:2.

Thus, the desaturation enzymes presented a higher affinity for the 9c,12t-18:2 whereas the elongation enzyme presented a higher affinity for the 9t,12c-18:2.

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References

  1. Sébédio JL, Grandgirard A, Prévost J: Linoleic acid isomers in heat treated sunflower oils. J Am Oil Chem Soc 65: 362-366, 1988

    Google Scholar 

  2. O'Keefe SF, Gaskins-Wright S, Willey V, Chen-Chen I: Level of trans geometrical isomers of essential fatty acids in some unhydrogenated U.S. vegetable oils. J Food Lipids 1: 165-176, 1994

    Google Scholar 

  3. Chardigny JM, Sébédio JL, Berdeaux O: Trans polyunsaturated fatty acids: Occurence and nutritional implication. In: FB Padley (ed). Advances in Applied Lipid Research. JAI Press, London Vol II, 1996, pp 1–33

    Google Scholar 

  4. Privett OS, Stearns EM, Nickell EC: Metabolism of the geometrical isomers of linoleic acid in the rat. J Nutr 92: 303–310, 1967

    Google Scholar 

  5. Anderson RL, Fullner CS, Hollenbach EJ: Effect of trans isomers of linoleic acid on the metabolism of linoleic acid in rat. J Nutr 105: 393–400, 1975

    Google Scholar 

  6. Beyers EC, Emken EA: Metabolites of cis, trans, and trans, cis isomers of linoleic acid in mice and incorporation into tissue lipids. Biochim Biophys Acta 1082: 275–284, 1991

    Google Scholar 

  7. Ratnayake WMN, Chen RY, Pelletier G, Weber D: Occurrence of 5c,8c,11c,15t eicosatetraenoic acid and other unusual polyunsaturated fatty acids in rats fed partially hydrogenated canola oil. Lipids 22: 707–714, 1994

    Google Scholar 

  8. Berdeaux O, Sébédio JL, Chardigny JM, Mairot T, Blond JP, Vatèle JM, Noël JP: Effect of trans n-6 fatty acids on the fatty acid profile of tissues and microsomal metabolism in the rat. Grasas Aceit 47: 86–99, 1996

    Google Scholar 

  9. Brenner RR: The desaturation step in animal biosynthesis of polyunsaturated fatty acids. Lipids 6: 567–571, 1971

    Google Scholar 

  10. Cook HW, Emken EA. Geometric and positional fatty acid isomers interact differently with desaturation and elongation of linoleic acid in cultured glioma cells. Cell Biol 68: 653–660, 1990

    Google Scholar 

  11. Marcel YL, Christiansen K, Holman RT: The preferred metabolic pathway from linoleic acid to arachidonic acid in vivo. Biochim Biophys Acta 164: 25–34, 1968

    Google Scholar 

  12. Berdeaux O, Vatèle JM, Eynard T, Nour M, Poullain D, Noël JP, Sébédio JL: Synthesis of (9Z,12E)-and (9E,12Z)-[1-14C] linoleic acid and (5Z,8Z,11Z,14E)-[1-14C] arachidonic acid. Chem Phys Lipids 78: 71–80, 1995

    Google Scholar 

  13. Snyder JM, Scholfield CR: Cis-trans isomerization of unsaturated fatty acids with p-toluenesulfinic acid. J Am Chem Soc 59: 462–470, 1982

    Google Scholar 

  14. Morris LJ: Separation of lipids by silver ion chromatography. J Lipid Res 7: 717–732, 1966

    Google Scholar 

  15. Hill EE, Husband DR, Lands WEM: The selective incorporation of 14C-glycerol into different species of phosphatidic acid, phosphatidyl-ethanolamine, and phosphatidylcholine. J Biol Chem 243: 4440–4451, 1968

    Google Scholar 

  16. Grandgirard A, Piconneaux A, Sébédio JL, O'Keefe SF, Sémon E, Le Quéré JL: Occurrence of geometrical isomers of eicosapentaenoic and docosahexenoic acids in liver lipids of rats fed heated linseed oil. Lipids 24: 799–804, 1989

    Google Scholar 

  17. Blond JP, Bézard J: Δ5-desaturation of dihomogammalinolenic acid (20:3 n-6) into arachidonic acid (20:4 n-6) by rat liver microsomes and incorporation of fatty acid in microsome phospholipids. Biochim Biophys Acta 1084: 255–260, 1991

    Google Scholar 

  18. Layne E: Spectrophotometric and turbidimetric methods for measuring proteins. In: Methods in Enzymology, Academic Press, New York 3, 1957, pp 447–454

    Google Scholar 

  19. Cao J, Blond JP, Bézard J: Inhibition of fatty acid Δ6-and Δ5-desaturation by cyclopropene fatty acids in rat liver microsomes. Biochim Biophys Acta 1210: 27–34, 1993

    Google Scholar 

  20. Chardigny JM, Blond JP, Bretillon L, Mager E, Poullain D, Martine L, Vatèle JM, Noël JP, Sébédio JL: Conversion of 18:3 Δ9cis, 12cis, 15trans in rat liver microsomes. Lipids 32: 731–735, 1997

    Google Scholar 

  21. Mohrhauer H, Christiansen K, Gan MV, Deubic M, Holman RT: Chain elongation of linoleic acid and its inhibition by other fatty acids in vitro. J Biol Chem 242: 4507–4514, 1967

    Google Scholar 

  22. Morrison WL, Smith LM: Preparation of fatty acids methyl esters and dimethylacetals from lipids with boron fluoride-methanol. J Chromatogr 5: 600–608, 1964

    Google Scholar 

  23. Narce M Gresti J, Bézard J: A method for evaluating the bioconversion of radioactive polyunsaturated fatty acids by reversedphase liquid chromatography. J Chromatogr 448: 249–264, 1988

    Google Scholar 

  24. Mohrhauer H, Holman R: The effect of dose level of essential fatty acids upon fatty acid composition of the rat liver. J Lipid Res 4: 151–159, 1963

    Google Scholar 

  25. Bézard J, Blond JP, Bernard A, Clouet P: The metabolism and availability of essential fatty acids in animal and human tissues. Reprod Nutr Dev 34: 539–568, 1994

    Google Scholar 

  26. Sébédio JL: Classical chemical techniques for fatty acid analysis. In: JL Sébédio, EG Perkins (eds). New Trends in Lipid and Lipoprotein Analysis. AOCS, Champaign, 1994, pp 277–289

    Google Scholar 

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Berdeaux, O., Blond, J., Brétillon, L. et al. In vitro desaturation or elongation of monotrans isomers of linoleic acid by rat liver microsomes. Mol Cell Biochem 185, 17–25 (1998). https://doi.org/10.1023/A:1006859616647

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