Separation of eicosapentaenoic acid and docosahexaenoic acid in fish oil by kinetic resolution using lipase

JAOCS, Journal of the American Oil Chemists' Society

Volumn 75, Issue 11, 1998, Pages 1551-1556

  Haraldsson, Gudmundur G ^a   Kristinsson, Björn ^a  

^a UNIVERSITY OF ICELAND   (Iceland)

Author keywords

DMA; EPA; Esterification; Ethanolysis; Fish oil; Kinetic resolution; Lipase; Lipozyme IM; n 3 fatty acids; Rhizomucor miehei lipase

Indexed keywords

CATALYST SELECTIVITY; ENZYME IMMOBILIZATION; ESTERIFICATION; ESTERS; ETHANOL; OILS AND FATS; REACTION KINETICS;

DOCOSAHEXANOIC ACID; EICOSAPENTANOIC ACID; LIPASE; LIPOZYME; TRANSESTERIFICATION;

FATTY ACIDS;

EID: 0032206184     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-998-0093-9     Document Type: Article

References (27)

1. Health Effects of Dietary Fatty Acids, edited by G.J. Nelson, American Oil Chemists' Society, Champaign, 1991, pp. 1-274.
2. Haraldsson, G.G., B. Kristinsson, R. Sigurdardottir, G.G. Gudmundsson, and H. Breivik, The Preparation of Concentrates of Eicosapentaenoic Acid and Docosahexaenoic Acid by LipaseCatalyzed Transesterification of Fish Oil with Ethanol, J. Am. Oil Chem. Soc. 74:1419-1424 (1997).
3. G.G. Haraldsson, The Application of Lipases for Modification of Fats and Oils, Including Marine Oils, in Advances in Fisheries Technology for Increased Profitability, edited by M.N. Voigt and R. Bhotta, Technomic Publishing Co., Inc., Lancaster, 1989, pp. 337-357.
4. Haraldsson, G.G., and B. Hjaltason, Using Biotechnology to Modify Marine Lipids, INFORM 3:626-629 (1992).
5. Hills, M.J., I. Kiewitt, and K. Mukherjee, Enzymatic Fractionation of Fatty Acids: Enrichment of γ-Linolenic Acid and Do-cosahexaenoic Acid by Selective Esterification Catalyzed by Lipases, J. Am. Oil Chem. Soc. 67:561-564 (1990).
6. Pedersen, S.B., and G. Hölmer, Studies of the Fatty Acid Specificity of the Lipase from Rhizomucor miehei Toward 20:17n-9, 20:5n-3, 22:1n-9 and 22:6n-3, Ibid. 72:239-243 (1995).
7. Pedersen, S.B., and G. Hölmer, Studies of the Fatty Acid Specificity of the Lipase from Rhizomucor miehei Toward 20:17n-9, 20:5n-3, 22:1n-9 and 22:6n-3, Ibid. 72:239-243 (1995).
8. Pedersen, S.B., and G. Hölmer, Studies of the Fatty Acid Specificity of the Lipase from Rhizomucor miehei Toward 20:17n-9, 20:5n-3, 22:1n-9 and 22:6n-3, Ibid. 72:239-243 (1995).
9. Pedersen, S.B., and G. Hölmer, Studies of the Fatty Acid Specificity of the Lipase from Rhizomucor miehei Toward 20:17n-9, 20:5n-3, 22:1n-9 and 22:6n-3, Ibid. 72:239-243 (1995).
10. Pedersen, S.B., and G. Hölmer, Studies of the Fatty Acid Specificity of the Lipase from Rhizomucor miehei Toward 20:17n-9, 20:5n-3, 22:1n-9 and 22:6n-3, Ibid. 72:239-243 (1995).
11. Langholz, P., P. Andersen, T. Forskov, and W. Schmidtsdorff, Application of a Specificity of Mucor miehei Lipase to Concentrate Docosahexaenoic Acid (DHA), Ibid. 66:1120-1123 (1989).
12. Takagi, T.J., Fractionation of Polyenoic Acids from Marine Lipids, Ibid. 66:488-489 (1989).
13. Shimada, Y., A. Sugihara, H. Nakano, T. Kuramoto, T. Nagao, M. Gemba, and Y. Tominaga, Purification of Docosahexaenoic Acid by Selective Esterification of Fatty Acids from Tuna Oil with Rhizopus delemar Lipase, Ibid. 74:97-101 (1997).
14. Shimada, Y., K. Maruyama, A. Sugihara, S. Moriyama, and Y. Tominaga, Purification of Docosahexaenoic Acid from Tuna Oil by a Two-Step Enzymatic Method: Hydrolysis and Selective Esterification, Ibid. 74:1441-1446 (1997).
15. Haraldsson, G.G., B.Ö. Gudmundsson, and Ö. Almarsson, The Synthesis of Homogeneous Triglycerides of Eicosapentaenoic Acid and Docosahexaenoic Acid by Lipase, Tetrahedron 51:941-952 (1995).
16. Maehr, H., G. Zenchoff, and D.L. Coffen, Enzymatic Enhancement of n-3 Fatty Acid Content in Fish Oils, J. Am. Oil Chem. Soc. 71:464-467 (1994).
17. Shimada, Y., K. Maruyama, M. Nakamura, S. Nakayama, A. Sugihara, and Y. Tominaga, Selective Hydrolysis of Polyunsaturated Fatty Acid-Containing Oil with Geotrichum candidum Lipase, Ibid. 72:1577-1581 (1995).
18. Shimada, Y., K. Maruyama, S. Okazaki, M. Nakamura, A. Sugihara, and Y. Tominaga, Enrichment of Polyunsaturated Fatty Acids with Geotrichum candidum Lipase, Ibid. 71:951-954 (1994).
19. Tanaka, Y., J. Hirano, and T. Funada, Concentration of Docosahexaenoic Acid in Glyceride by Hydrolysis of Fish Oil with Candida cylindracea Lipase, Ibid. 69:1210-1214 (1992).
20. McNeill, G.P., R.G. Ackman, and S.R. Moore, Lipase-Catalyzed Enrichment of Long-Chain Polyunsaturated Fatty Acids, Ibid. 73:1403-1407 (1996).
21. Moore, S.R., and G.P. McNeill, Production of Triglycerides Enriched in Long-Chain n-3 Polyunsaturated Fatty Acids from Fish Oil, Ibid. 73:1409-1414 (1996).
22. Sonnet, P.E., and J.A. Gazzillo, Evaluation of Lipase Selectivity for Hydrolysis, Ibid. 68:11-15 (1991).
23. Christie, W.W., The Positional Distributions of Fatty Acids in Triglycerides, in Analysis of Oils and Fats, edited by R.J. Hamilton and J.B. Rossell, Elsevier, London, 1986, pp. 313-339.
24. Haraldsson, G.G., and Ö. Almarsson, Studies on the Positional Specificity of Lipase from Mucor miehei During Interesterification Reactions of Cod Liver Oil with n-3 Polyunsaturated Fatty Acid and Ethyl Ester Concentrates, Acta Chem. Scand. 45:723-730 (1991).
25. Kagan, H.B., and J.C. Fiaud, Kinetic Resolution, in Topics in Stereochemistry, edited by E.L. Eliel and S.H. Wilen, Wiley-Interscience, New York, 1988, Vol. 18, pp. 249-330.
26. Haraldsson, G.G., The Preparation of Triglycerides Highly Enriched with n-3 Polyunsaturated Fatty Acids via Lipase Catalyzed Interesterification, in Proceedings of the 15th Scandinavian Symposium on Lipids, edited by V.K.S. Shukla and G. Hölmer, Lipidforum, 1989, pp. 245-248.
27. Enzymatic Reactions in Organic Media, edited by A.M.P. Koskinen and A.M. Klibanov, Blackie Academic and Professional, London, 1996, pp. 1-314.