Abstract
Three commercially available immobilized lipases, Novozym 435 from Candida antarctica, Lipozyme IM from Rhizomucor miehei, and Lipase PS-C from Pseudomonas cepacia, were used as biocatalysts for the interesterification of conjugated linoleic acid (CLA) ethyl ester and tricaprylin. The reactions were carried out in hexane, and the products were analyzed by gas-liquid chromatography. The effects of molar ratio, enzyme load, incubation time, and temperature on CLA incorporation were investigated. Novozym 435, as compared to Lipozyme IM and Lipase PC-C, showed the highest degree of CLA incorporation into tricaprylin. By hydrolysis with pancreatic lipase, it was found that Lipozyme IM and Lipase PS-C exhibited high selectivity for the sn-1,3 position of the triacylglycerol early in the interesterification, with small extents of incorporation of CLA into the sn-2 position, probably due to acyl migration, at later reaction times. A small extent of sn-1,3 selectivity during interesterification by Novozym 435 was observed.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Ha, Y.L., N.K. Grimm, and M.W. Pariza, Anticarcinogens from Fried Ground Beef: Heated-Altered Derivatives of Linoleic Acid, Carcinogenesis 8:1881–1887 (1987).
Werner, S.A., L.O. Luedecke, and T.D. Shultz, Determination of Conjugated Linoleic Acid Content and Isomer Distribution in Three Cheddar-Type Cheeses: Effects of Cheese Cultures, Processing, and Aging, J. Agric. Food Chem. 40:1817–1821 (1992).
Shantha, N.C., E.A. Decker, and Z. Ustunol, Conjugated Linoleic Acid Concentration in Processed Cheese, J. Am. Oil Chem. Soc. 69:425–428 (1992).
Lin, H., T.D. Boylston, M.J. Chang, L.O. Luedecke, and T.D. Shultz, Survey of the Conjugated Linoleic Acid Content of Dairy Products, J. Dairy Sci. 78:2358–2365 (1995).
McGuire, M.K., Y. Park, R.A. Behre, L.Y. Harrison T.D. Shulz, and M.A. McGuire, Conjugated Linoleic Acid Concentrations of Human Milk and Infant Formula, Nutr. Res. 17:1277–1283 (1997).
Chin, S.F., J.M. Storkson, K.J. Albright, M.E. Cook, and M.W. Pariza, Dietary Sources of Conjugated Dienoic Isomers of Linoleic Acid, a Newly Recognized Class of Anticarcinogens, J. Food Comp. Anal. 5:185–197 (1992).
Dugan, M.E.R., J.L. Aalhus, A.L. Schaefer, and J.K.G. Kramer, The Effect of Conjugated Linoleic Acid on Fat to Lean Repartitioning and Feed Conversion in Pigs, Can. J. Anim. Sci. 77: 723–725 (1997).
Chin, S.F., J.M. Storkson, K.J. Albright, M.E. Cook, and M.W. Pariza, Conjugated Linoleic Acid Is a Growth Factor for Rats as Shown by Enhanced Weight Gain and Improved Feed Efficiency, J. Nutr. 124:2344–2349 (1994).
Cook, M.E., C.C. Miller, Y. Park, and M.W. Pariza, Immune Modulation by Altered Nutrition Metabolism: Nutritional Control of Immune-Induced Growth Depression, Poult. Sci. 72:1301–1305 (1993).
Nicolosi, R.J., E.J. Rogers, D. Kritchevsky, J.A. Scimeca, and P.J. Huth, Dietary Conjugated Linoleic Acid Reduces Plasma Lipoproteins and Early Aortic Atherosclerosis in Hypercholesterolemic Hamsters, Artery 22:266–277 (1997).
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).
Lee, K.N., D. Kritchevsky, and M.W. Pariza, Conjugated Linoleic Acid and Atherosclerosis in Rabbits, Atherosclerosis 108:19–25 (1994).
Bach, A.C., and V.K. Babayan, Medium-Chain Triglycerides: An Update, Am. J. Clin. Nutr. 36:950–961 (1982).
Cohen, L.A., D.O. Thompson, Y. Maeura, and J.H. Weisburger, Influence of Dietary Medium-Chain Triglycerides on the Development of N-Methylnitrosourea-Induced Rat Mammary Tumors, Cancer Res. 44:5023–5028 (1984).
Bray, G.A., M. Lee, and T.L. Bray, Weight Gain of Rats Fed Medium-Chain Triglycerides Is Less Than Rats Fed Long-Chain Triglycerides, Int. J. Obesity 4:27–32 (1980).
Babayan, V.K., Medium Chain Triglycerides, in Dietary Fat Requirements in Health and Development, edited by J. Beare-Rogers, American Oil Chemists' Society, Champaign, 1988, pp. 73–86.
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).
Akoh, C.C., and R.V. Sista, Enzymatic Modification of Borage Oil: Incorporation of Eicosapentaenoic Acid, J. Food Lipids 2:231–238 (1995).
Ray, S., and D.K. Bhattacharyya, Comparative Nutritional Study of Enzymatically and Chemically Interesterified Palm Oil Products, J. Am. Oil Chem. Soc. 72:327–330 (1995).
Luddy, F.E., R.A. Barford, S.F. Herb, P. Magidman, and R.W. Riemenschneider, Pancreatic Lipase Hydrolysis of Triglycerides by Semimicro Technique, ——Ibid. 51:693–696 (1964).
Whittaker, J.R., Principles of Enzymology for the Food Sciences, Marcel Dekker, New York, pp. 31–42 (1972).
Jandacek, R.J., J.A. Whiteside, B.N. Holcombe, R.A. Volpenhein, and J.D. Taulbee, The Rapid Hydrolysis and Efficient Absorption of Triglycerides with Octanoic Acid in the 1 and 3 Position and Long Chain Fatty Acid in the 2-Position, Am. J. Clin. Nutr. 45:940–945 (1987).
Miura, S., A. Ogawa, and H. Konishi, A Rapid Method for Enzymatic Synthesis and Purification of the Structured Triacylglycerol, 1,3-Dilauroyl-2-oleoyl-glycerol, J. Am. Oil Chem. Soc. 76:927–931 (1999).
Xu X., S. Balchen, C.-E. Høy, and J. Adler-Nissen, Pilot Batch Production of Specific-Structured Lipids by Lipase-Catalyzed Interesterification: Preliminary Study on Incorporation and Acyl Migration, ——Ibid. 75:301–308 (1998).
Lee, K.T., and T.A. Foglia, Synthesis, Purification, and Characterization of Structured Lipids Produced from Chicken Fat, ——Ibid. 77:1027–1034 (2000).
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Kim, IH., Yoon, CS., Cho, SH. et al. Lipase-catalyzed incorporation of conjugated linoleic acid into tricaprylin. J Amer Oil Chem Soc 78, 547–551 (2001). https://doi.org/10.1007/s11746-001-0301-4
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11746-001-0301-4