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Lipase-assisted concentration of n-3 polyunsaturated fatty acids in acylglycerols from marine oils

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Journal of the American Oil Chemists’ Society

Abstract

Preparation of n-3 polyunsaturated fatty acid (PUFA) concentrates from seal blubber oil (SBO) and menhaden oil (MHO) in the form of acylglycerols was carried out by hydrolysis with a number of commercial microbial lipases. The lipases tested were Aspergillus niger, Candida cylindracea (CC), Chromobacterium viscosum, Geotrichum candidum, Mucor miehei, Pseudomonas sp., Rhizopus oryzae, and Rhizopus niveus. After lipase-assisted hydrolysis of oils, free fatty acids were removed, and fatty acid composition of the mixture containing mono-, di-, and triacylglycerols was determined. All lipases were effective in increasing the n-3 PUFA content of the remaining acylglycerols of both SBO and MHO. The highest concentration of n-3 PUFA was provided by CC lipase; 43.5% in SBO [9.75% eicosapentaenoic acid (EPA), 8.61% docosapentaenoic acid (DPA), and 24.0% docosahexaenoic acid (DHA)] and 44.1% in MHO (18.5% EPA, 3.62% DPA, and 17.3% DHA) after 40 h of hydrolysis. Thus, CC lipase appears to be most suitable for preparation of n-3 PUFA in the acylglycerol form from marine oils.

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References

  1. Bang, H.O., J. Dyerberg, and N. Hjorne, The Composition of Food Consumed by Greenland Eskimos, Acta. Med. Scand. 200:59–73 (1976).

    Google Scholar 

  2. Dyerberg, J., Linolinate-Derived Polyunsaturated Fatty Acids and Prevention of Atherosclerosis, J. Nutr. Rev. 44:125–134 (1986).

    Article  CAS  Google Scholar 

  3. Simopoulos, A.P., Omega-3 Fatty Acids in Health and Disease and Growth and Development, Am. J. Clin. Nutr. 54:438–463 (1991).

    CAS  Google Scholar 

  4. Kinsella, J.E., Food Components with Potential Therapeutic Benefits: The n-3 Polyunsaturated Fatty Acids of Fish Oils, Food Technol. 40: 89–97 (1986).

    CAS  Google Scholar 

  5. Singh, G., and R.K. Chandra, Biochemical and Cellular Effects of Fish Oils, Prog. Food Nutr. Sci. 12:371–419 (1988).

    CAS  Google Scholar 

  6. Branden, L.M., and K.K. Carroll, Dietary Polyunsaturated Fats in Relation to Mammary Carcinogenesis in Rats, Lipids 21:285–288 (1986).

    Article  Google Scholar 

  7. Hanazaki, T., A. Hirai, T. Terano, J. Sajiki, S. Kondo, T. Fujita, Y. Tamura, and A. Kumagai, Effects of Orally Administrated Ethyl Ester of Eicosapentaenoic Acid on Pig-Like Substance Production by Rat Aorta, Prostaglandins 23:557–567 (1982).

    Article  Google Scholar 

  8. El-Boustani, S., C. Colette, L. Monnier, B. Descomps, C.A. Panlet, and F. Mendey, Enternal Absorption in Man of Eicosapentaenoic Acid in Different Chemical Forms, Lipids 22:711–714 (1987).

    Article  CAS  Google Scholar 

  9. Lawson, L.D., and B.G. Hughes, Human Absorption of Fish Oil Fatty Acids as Triacylglycerols, Free Fatty Acids or Ethyl Esters, Biochem. Biophys. Res. Comm. 152:328–335 (1988).

    Article  CAS  Google Scholar 

  10. Yang, L.Y., A. Kuksis, and J.J. Myher, Lumenal Hydrolysis of Menhaden and Rapeseed Oil and Their Fatty Acid Methyl and Ethyl Esters in the Rats, Biochem. Cell Biol. 67:192–204 (1989).

    Article  CAS  Google Scholar 

  11. Haraldsson, G.G., and P.A. Hoskuldsson, The Preparation of Triglycerides Highly Enriched with ω3 Polyunsaturated Fatty Acids via Lipase Catalysed Interesterification, Tetrahed. Lett. 30:1671–1674 (1989).

    Article  CAS  Google Scholar 

  12. Tanaka, Y., J. Hirano, and T. Funada, Concentration of Docosahexaenoic Acid in Glyceride by Hydrolysis of Fish Oil with Candida cylindracea Lipase, J. Am. Oil Chem. Soc. 69:1210–1214 (1992).

    Article  CAS  Google Scholar 

  13. Hoshino, T., T. Yamane, and S. Shimuzu, Selective Hydrolysis of Fish Oil by Lipase to Concentrate ω3 Polyunsaturated Fatty Acids, Agric. Biol. Chem. 54:1459–1467 (1990).

    CAS  Google Scholar 

  14. Shimada, Y., K. Maruyama, S. Okazaki, M. Nakamura, A. Sugihara, and Y. Tominaga, Enrichment of Polyunsaturated Fatty Acids with Geotrichum candidum Lipase, J. Am. Oil. Chem. Soc. 71:951–954 (1994).

    Article  CAS  Google Scholar 

  15. Yadwad, V.B., O.P. Ward, and L.C. Noronha, Application of Lipase to Concentrate the Docosahexaenoic Acid (DHA) Fraction of Fish Oil, Biotech. Bioeng. 38:956–959 (1991).

    Article  CAS  Google Scholar 

  16. Maehr, H., G. Zenchoff, and D.L. Coffen, Enzymic Enhancement of n-3 Fatty acid Content in Fish Oils, J. Am. Oil Chem. Soc. 71:463–467 (1994).

    Article  CAS  Google Scholar 

  17. Bottino, N.R., G.A. Vandenburg, and R. Reiser, Resistance of Certain Long-Chain Polyunsaturated Fatty Acids of Marine Oils to Pancreatic Lipase Hydrolysis, Lipids 2:489–493 (1967).

    Article  CAS  Google Scholar 

  18. Shahidi, F., and U.N. Wanasundara, Oxidative Stability of Encapsulated Seal Blubber Oil, in Flavor Technology, Physical Chemistry, Modification and Process, edited by C.-T. Ho, C.-T. Tan, and C.-H. Tong, ACS Symposium Series No. 610, American Chemical Society, Washington DC, 1995, pp. 139–151.

    Google Scholar 

  19. Wanasundara, U.N., and F. Shahidi, Stabilization of Seal Blubber and Menhaden Oils with Green Tea Catechins, J. Am. Oil Chem. Soc. 73:1183–1190 (1996).

    Article  CAS  Google Scholar 

  20. Wanasundara, U.N., Marine Oils, Stabilization, Structural Characterization and Omega-3 Fatty Acid Concentration, Ph.D. thesis, Memorial University of Newfoundland, St. John’s, Canada, 1996.

    Google Scholar 

  21. Official Methods and Recommended Practices of the American Oil Chemists’ Society, 4th edn., edited by D. Firestone, American Oil Chemists’ Society, Champaign, 1990.

    Google Scholar 

  22. Shahidi, F., U.N. Wanasundara, and N. Brunet, Oxidative Stability of Oil from Blubber of Harp Seal (Phoca groenlandica) as Assessed by NMR and Standard Procedures, Food Res. Inter. 27:555–562 (1994).

    Article  CAS  Google Scholar 

  23. Kotting, J., and H. Elbe, Lipases and Phospholipases in Organic Synthesis, in Lipases, edited by P. Woolley and S.B. Petersen, Cambridge University Press, Cambridge, 1994, pp. 289–313.

    Google Scholar 

  24. Wanasundara, U.N., and F. Shahidi, Positional Distribution of Fatty Acids in Triacylglycerols of Seal Blubber Oil, J. Food Lipids 4:51–64 (1997).

    Article  CAS  Google Scholar 

  25. Lie, O., and G. Lambertsen, Fatty Acid Specificity of Candida cylindracea Lipase, Fette Seifen Anstrichm. 88:365–368 (1986).

    Article  CAS  Google Scholar 

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Correspondence to Fereidoon Shahidi.

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Wanasundara, U.N., Shahidi, F. Lipase-assisted concentration of n-3 polyunsaturated fatty acids in acylglycerols from marine oils. J Am Oil Chem Soc 75, 945–951 (1998). https://doi.org/10.1007/s11746-998-0271-9

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  • DOI: https://doi.org/10.1007/s11746-998-0271-9

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