Abstract
Effects of water content, reaction time, and their relationships in the production of two types of specific-structured lipids (sn-MLM- and sn-LML-types: L-long chain fatty acids; M-medium chain fatty acids) by lipase-catalyzed interesterification in a solvent-free system were studied. The biocatalyst used was Lipozyme IM (commercial immobilized lipase). The substrates used for sn-MLM-type were fish oil and capric acid, and medium chain triacylglycerols and sunflower free fatty acids for sn-LML-type. The observed incorporation with the time course agrees well with the Michaelis-Menten equation, while the acyl migration is proportional to time within the range of 20 mol% acyl migration (MLM-type: M f =0.2225 T, R2=0.98; LML-type: M f =0.5618 T, R2=0.99). As water content (wt%, on the enzyme basis) increased from 3.0 to 11.6% for MLM-type and from 3.0 to 7.2% for LML-type in the solvent-free systems, the incorporation rates in the first 5 h increased from 3.34 to 10.30%/h, and from 7.29 to 11.12%/h, respectively. However, the acyl migration rates also increased from 0.22 to 1.12%/h and from 0.56 to 1.37%/h, respectively. Different effects in the production of two totally position-opposed lipids can be observed. Presumably these are caused by the different chain length of the fatty acids. The relationships between reaction time and water content are inverse and give a quantitative prediction of incorporation and acyl migration in selected reaction conditions and vice versa. The acyl migration can not be totally avoided in present systems, but can be reduced to a relatively low level. Acyl migration during the downstream processing has also been observed and other factors influencing the acyl migration are briefly discussed.
Similar content being viewed by others
References
Akoh, C.C., Structured Lipids—Enzymatic Approaches, INFORM 6:1055–1061 (1995).
Macrae, A.R., Tailored Triacylglycerols and Esters, Biochem. Soc. Transact. 17:1146–1148 (1989).
Eigtved, P., Enzymes and Lipid Modification, in Advances in Applied Lipid Research, edited by Fred B. Padley, JAI Press Ltd., London, Vol. 1, 1992.
Akoh, C.C., Enzymatic Modification of Lipids, in Food Lipids and Health, edited by Richard E. McDonald and David B. Min, Marcel Dekker, Inc., New York, 1996.
Ramamurthi, S., and A.R. McCurdy, Interesterification—Current Status and Future Prospects, in Development and Processing of Vegetable Oils for Human Nutrition, edited by Roman Przybylski and Bruce E. McDonald, AOCS Press, Champaign, 1996.
Huyghebaert, A., D. Verhaeghe, and H. De Moor, Fat Products Using Chemical and Enzymatic Interesterification, in Fats in Food Products, edited by D.P.J. Moran and K.K. Rajah, Blackie Academic & Professional, London, 1994.
Bjorkling, F., S.E. Godtfredsen, and O. Kirk, The Future Impact of Industrial Lipases, Trends in Biotech. 9:360–363 (1991).
Chistensen, M.S., A. Mullertz, and C.-E. Høy, Absorption of Triglycerides with Defined or Random Structure by Rats with Biliary and Pancreatic Diversion, Lipids 30:521–525 (1995).
Jensen, M.M., M.S. Chistensen, and C.-E. Høy, Intestinal Absorption of Octanoic, Decanoic and Linoleic Acids: Effects of Triacylglycerol Structure, Ann. Nutr. Metab. 38:104–116 (1995).
Andersen, P.S., Structured Triglycerides in the Prevention of Coronary Heart Disease, Ph.D. Thesis, Technical University of Denmark, 1995.
Chistensen, M.S., C.-E. Høy, C.C. Becker, and T.G. Redgrave, Intestinal Absorption and Lymphatic Transport of Eicosapentaenoic (EPA), Docosahexaenoic (DHA), and Decanoic Acids: Dependence on Intramolecular Triacylglycerol Structure, Am. J. Clin. Nutr. 61:56–61 (1995).
Seto, A., and O. Yamada, Fats and Oils Having Superior Digestibility and Absorptivity, European Patent Specification 0 265 699 B1 (1987).
Chistensen, T.C., and G. Hølmer, Lipase Catalyzed Acyl-Exchange Reactions of Butter Oil: Synthesis of a Human Milk Fat Substitute for Infant Formulas, Milchwissenschaft 48:543–548 (1993).
Lee, K.-T., and C.C. Akoh, Immobilized Lipase-Catalyzed Production of Structured Lipids with Eicosapentaenioc Acid at Specific Positions, J. Am. Oil Chem. Soc. 73:611–615 (1996).
Huang, K.-H., and C.C. Akoh, Enzymatic Synthesis of Structured Lipids: Transesterification of Triolein and Caprylic Acid Ethyl Ester, Ibid.:245–250 (1996).
Shikura, A., K. Fujimoto, T. Suzuki, and K. Arai, Improved Lipase-Catalyzed Incorporation of Long-Chain Fatty Acids into Medium-Chain Triglycerides Assisted by Supercritical Carbon Dioxide Extraction, Ibid.:961–967 (1994).
Shieh, C.-J., C.C. Akoh, and P.E. Koehler, Four-Factor Response Surface Optimization of the Enzymatic Modification of Triolein to Structured Lipids, Ibid.:619–623 (1995).
Huang, K.-H., and C.C. Akoh, Optimization and Scale-Up of Enzymatic Synthesis of Structured Lipids Using RSM, J. of Food Sci. 61:137–141 (1996).
Shimada, Y., A. Sugihara, K. Maruyama, T. Nagao, S. Nakayama, H. Nakano, and Y. Tominaga, Production of Structured Lipids Containing Docosahexaenoic and Caprylic Acids Using Immobilized Rhizopus delemar Lipase, J. Ferment. Bioeng. 81:299–303 (1996).
Becker, C.C., A. Rosenquist, and G. Hølmer, Regiospecific Analysis of Triacylglycerols Using Allyl Magnesium Bromide, Lipids 28:147–149 (1993).
Official Methods and Recommended Practices of the American Oil Chemists’ Society, 4th edn., AOCS Press, 1993, Methods Ca 5a and Cd 8.
Macrae, A.R., Interesterification of Fats and Oils, in Biocatalysts in Organic Syntheses, edited by J. Tramper, H.C. van der Plas, and P. Linko, Elsevier Sci. Pub., Amsterdam, 1985.
Miller, D.A., J.M. Prausnitz, and H.W. Blach, Kinetics of Lipase-Catalyzed Interesterification of Triglycerides in Cyclohexane, Enzyme Microb. Technol. 13:98–103 (1991).
Bloomer, S., P. Adlercreutz, and B. Mattiasson, Triglyceride Interesterification by Lipases. 2. Reaction Parameters for the Reduction of Trisaturate Impurities and Diglycerides in Batch Reactions, Biocatalysis 5:145–162 (1991).
Bloomer, S., P. Adlercreutz, and B. Mattiasson, Kilogram-Scale Ester Synthesis of Acyl Donor and Use in Lipase-Catalyzed Interesterifications, J. Am. Oil Chem. Soc. 69:966–973 (1992).
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Xu, X., Balchen, S., Høy, C.E. et al. Pilot batch production of specific-structured lipids by lipase-catalyzed interesterification: Preliminary study on incorporation and acyl migration. J Amer Oil Chem Soc 75, 301–308 (1998). https://doi.org/10.1007/s11746-998-0045-4
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11746-998-0045-4