Immobilized lipase-catalyzed production of structured lipids with eicosapentaenoic acid at specific positions

  • Ki-Teak Lee
  • Casimir C. Akoh
Article

Abstract

Structured lipids (SL) were synthesized by the interesterification reaction between medium-chain triacylglycerols and eicosapentaenoic acid (EPA) ethyl ester. The products were partially purified, and the fatty acid at thesn-2 position was determined after pancreatic lipase-catalyzed hydrolysis. The effect of additives (water and glycerol) on the rate of reaction was also investigated. Mol% EPA incorporated into the triacylglycerols was increased by adding water when trilaurin and tricaprylin were the substrates and IM 60 was the biocatalyst. With SP 435, EPA incorporation was always less with additional water than without water. The addition of glycerol (0.005 g or 0.01 g) improved interesterification catalyzed by IM 60 to some degree, but an excess amount (0.02 g) inhibited the reaction. The reaction with glycerol showed no significant difference with SP 435. After scale-up and fractionation by column chromatography, we could recover approximately 0.3–0.4 g of product/g of reaction products. After hydrolysis by pancreatic lipase, we can conclude that IM 60 has a high specificity forsn-1,3 positions. With SP 435 lipase, 34.8–39.3 mol% of EPA was found at thesn-2 position of the recovered SL.

Key Words

Additives column chromatography eicosapentaenoic acid hydrolysis interesterification medium-chain triacylglycerols pancreatic lipase 

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References

  1. 1.
    Simopoulos, A.P., Omega-3 Fatty Acids in Health and Disease and in Growth and Development,Am. J. Clin. Nutr. 54:438–463 (1991).Google Scholar
  2. 2.
    Terano, T., J.A. Salmon, G.A. Higgs, and S. Moncada, Eicosapentaenoic Acid as a Modulator of Inflammation. Effect on Prostaglandin and Leukotriene Synthesis,Biochem. Pharmacol. 35:779–785 (1986).CrossRefGoogle Scholar
  3. 3.
    Haines, A.P., T.A.B. Sanders, J.D. Imeson, R.F. Mahler, J. Martin, M. Mistry, M. Vickers, and P.G. Wallance, Effects of a Fish Oil Supplement on Platelet Function, Haemostatic Variables and Albuminuria in Insulin-Dependent Diabetics,Thromb. Res. 43:643–655 (1986).CrossRefGoogle Scholar
  4. 4.
    Braden, L.M., and K.K. Carroll, Dietary Polyunsaturated Fat in Relation to Mammary Carcinogenesis in Rat,Lipids 21:285–288 (1986).CrossRefGoogle Scholar
  5. 5.
    Uauy-Dagach, R., and A. Valenzuela, Marine Oils as a Source of Omega-3 Fatty Acids in the Diet,Prog. Food Nutr. Sci. 16:199–243 (1992).Google Scholar
  6. 6.
    Sardesai, V.M.: Nutritional Role of Polyunsaturated Fatty Acids,J. Nutr. Biochem. 3:154–166 (1992).CrossRefGoogle Scholar
  7. 7.
    Bach, A.C., and V.K. Babayan, Medium-Chain Triglycerides: An Update,Am. J. Clin. Nutr. 36:950–961 (1982).Google Scholar
  8. 8.
    Cohen, L.A., D.O. Thompson, Y. Maeura, and J.H. Weisburger, Influence of Dietary Medium-Chain Triglycerides on the Development ofN-methylnitrosourea-Induced Rat Mammary Tumors,Cancer. Res. 44:5023–5028 (1984).Google Scholar
  9. 9.
    Brozozowski, A.M., Z.S. Derewenda, G.G. Donson, D.M. Lawson, J.P. Turkenburg, F. Bjorkling, B. Huge-Jenen, S.A. Patkar, and L. Thim, A Model for Interfacial Activation in Lipases from the Structure of a Fungal Lipase-Inhibitor Complex.Nature 351:491–494 (1991).CrossRefGoogle Scholar
  10. 10.
    Gupta, M.N., Enzyme Function in Organic Solvents,Eur. J. Biochem. 203:25–32 (1992).CrossRefGoogle Scholar
  11. 11.
    Triantafyllou, A., P. Adlercreutz, and B. Mattiasson, Influence of the Reaction Medium on Enzyme Activity in Bio-Organic Synthesis: Behavior of Lipase fromCandida rugosa in the Presence of Polar Additives,Biotechnol. Appl. Biochem. 17:167–179 (1993).Google Scholar
  12. 12.
    Luddy, F.E., R.A. Barford, S.F. Herb, P. Magidman, and R.W. Riemenschneider, Pancreatic Lipase Hydrolysis of Triglycerides by a Semimicro Technique,J. Am. Oil Chem. Soc. 41:693–696 (1963).Google Scholar
  13. 13.
    Huang, K.-H., and C.C. Akoh, Lipase-Catalyzed Incorporation of n-3 Polyunsaturated Fatty Acids into Vegetable Oils,J. Am. Oil Chem. Soc. 71:1277–1280 (1994).Google Scholar
  14. 14.
    Quinlan, P., and S. Moore, Modification of Triglycerides by Lipases: Process Technology and Its Application to the Production of Nutritionally Improved Fats,INFORM 4:580–585 (1993).Google Scholar
  15. 15.
    Jensen, G.L., N. McGarvey, R. Tarasezewski, S.K. Wixson, D.L. Seidner, T. Pai, Y.-Y. Yeh, T.W. Lee, and S.J. DeMichele, Lymphatic Absorption of Enterally Fed Structured Triacylglycerol vs. Physical Mix in a Canine Model,Am. J. Clin. Nutr. 60:518–524 (1994).Google Scholar

Copyright information

© AOCS Press 1996

Authors and Affiliations

  • Ki-Teak Lee
    • 1
  • Casimir C. Akoh
    • 1
  1. 1.Department of Food Science and TechnologyThe University of GeorgiaAthens

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