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Modification of menhaden oil by enzymatic acidolysis to produce structured lipids: Optimization by response surface design in a packed bed reactor

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Journal of the American Oil Chemists' Society

Abstract

Structured lipids from menhaden oil were produced by enzymatic acidolysis in a packed bed reactor. Response surface methodology was applied to optimize the reaction. Lipozyme IM from Rhizomucor miehei lipase was the biocatalyst, and caprylic acid was the acyl donor. Parameters such as residence time, substrate molar ratio, and reaction temperature were included for the optimization. High incorporation of acyl donor and retention of high levels of eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids in the original menhaden oil were obtained. Good quadratic models were obtained for the incorporation of caprylic acid and for the content of EPA plus DHA retained, by multiple regression with backward elimination. The coefficients of determination (R 2) for the two models were 0.91 and 0.87, respectively. The regression probabilities (P) were below 0.003 for both models. Also, the predicted values from the two models had linear relationships with the observed responses. All parameters studied had positive effects on the incorporation of caprylic acid, but only residence time and substrate molar ratio had negative effects on the content of EPA plus DHA retained. The optimal conditions generated from models were temperature =65°C, substrate molar ratio=4–5, and residence time=180–220 min. Incorporated caprylic acid did not replace DHA, but the content of EPA decreased somewhat with an increase in caprylic acid incorporation.

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References

  1. Kinsella, J.E., Seafoods and Fish Oil in Human Health and Disease, Marcel Dekker, New York, 1987, pp. 41–164.

    Google Scholar 

  2. Fish Oils in Nutrition, edited by M.E. Stansby, Van Nostrand Reinhold, New York, 1990, pp. 268–308.

    Google Scholar 

  3. Connor, S.L., and W.E. Connor, Are Fish Oils Beneficial in the Prevention and Treatment of Coronary Artery Disease? Am. J. Clin. Nutr. 66:S1020-S1031 (1997).

    Google Scholar 

  4. Høy, C.-E., M.S. Christensen, T. Redgrave, and P. Tso, Metabolism of Specific Structured Triacylglycerols, in Structural Modified Food Fats: Synthesis, Biochemistry, and Use, edited by A.B. Christophe, AOCS Press, Champaign, 1998, pp. 160–169.

    Google Scholar 

  5. Phan, C.T., B.-C. Mortimer, and T.G. Redgrave, Lipid Structures and the Intravenous Metabolism of Triglyceride-Rich Lipoproteins and Emulsions,, pp. 207–228.

    Google Scholar 

  6. Xu, X., C.-E. Høy, S. Balchen, and J. Adler-Nissen, Specific-Structured Lipids: Nutritional Perspectives and Production Potentials, in Proceedings of International Symposium on the Approaches to Functional Cereals and Oils, CCOA, Beijing, 1997, pp. 806–813.

  7. Akoh, C.C., Structured Lipids, in Food Lipids: Chemistry, Nutrition, and Biotechnology, edited by C.C. Akoh, and D.B. Min, Marcel Dekker, New York, 1998, pp. 699–727.

    Google Scholar 

  8. Christensen, 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).

    CAS  Google Scholar 

  9. Jensen, M.M., M.S. Christensen, and C.-E. Høy, Intestinal Absorption of Octanoic, Decanoic and Linoleic Acids: Effects of Triacylglycerol Structure, Ann. Nutr. Metab. 38:104–116 (1995).

    Article  Google Scholar 

  10. Christensen, 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).

    CAS  Google Scholar 

  11. Christensen, M.M., S.P. Lund, L. Simonsen, U. Haas, S.E. Simonsen, and C.-E. Høy, Dietary Structured Triacylglycerols Containing Docosahexaenoic Acid Given from Birth Affect Visual and Auditory Performance and Tissue Fatty Acid Profiles of Rats, J. Nutr. 128:1011–1017 (1998).

    CAS  Google Scholar 

  12. Christensen, M.M., and C.-E. Høy, Early Dietary Intervention with Structured Triacylglycerols Containing Docosahexaenoic Acid. Effect on Brain, Liver, and Adipose Tissue Lipids, Lipids 32:185–191 (1997).

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

  14. Pedersen, S.B., and G. Hølmer, Studies of the Fatty Acid Specificity of the Lipase from Rhizomucor miehei Toward 20∶1n−9, 20∶5n−3, 22∶1n−9 and 22∶6n−3, J. Am. Oil Chem. Soc. 72:239–243 (1995).

    CAS  Google Scholar 

  15. Haraldsson, G.G., and B. Kristinsson, Separation of Eicosapentaenoic Acid and Docosahexaenoic Acid in Fish Oil by Kinetic Resolution Using Lipase, 75:1551–1556 (1998).

    CAS  Google Scholar 

  16. Petersen, R.G., Design and Analysis of Experiments, Marcel Dekker, New York, 1985.

    Google Scholar 

  17. Xu, X., S. Balchen, C.-E. Høy, and J. Adler-Nissen, Production of Specific-Structured Lipids by Enzymatic Interesterification in a Pilot Continuous Enzyme Bed Reactor, J. Am. Oil Chem. Soc. 75:1573–1579 (1998).

    CAS  Google Scholar 

  18. Mu, H., X. Xu, and C.-E. Høy, Production of Specific-Structured Triacylglycerols by Lipase-Catalyzed Interesterification in a Laboratory Scale Continuous Reactor, 75:1187–1193 (1998).

    CAS  Google Scholar 

  19. Fomuso, L.B., and C.C. Akoh, Enzymatic Modification of Triolein: Incorporation of Caproic and Butyric Acids to Produce Reduced-Calorie Structured Lipids, 74:269–272 (1997).

    CAS  Google Scholar 

  20. Christie, W.W., Gas Chromatography and Lipids: A Practical Guide, The Oily Press Ltd., London, 1989, p. 72.

    Google Scholar 

  21. Becker, C.C., A. Rosenquist, and G. Hølmer, Regiospecific Analysis of Triacylglycerols Using Allyl Magnesium Bromide, Lipids 28:147–149 (1993).

    Google Scholar 

  22. Xu, X., H. Mu, C.-E. Høy, and J. Adler-Nissen, Production of Specifically Structured Lipids by Enzymatic Interesterification in a Pilot Enzyme Bed Reactor: Process Optimization by Response Surface Methodology, Fett/Lipid 101:158–164 (1999).

    Article  Google Scholar 

  23. Posorske, L.H., G.K. LeFebvre, C.A. Miller, T.T. Hansen, and B.L. Glenvig, Process Considerations of Continuous Fat Modification with an Immobilized Lipase, J. Am. Oil Chem. Soc. 65:922–926 (1988).

    CAS  Google Scholar 

  24. Hansen, T.T., and P. Eigtved, A New Immobilized Lipase for Interesterification and Ester Synthesis, in Proceedings: World Conference on Emerging Technologies in the Fats and Oils Industry, edited by A.R. Baldwin, American Oil Chemists’ Society, Champaign, 1986, pp. 365–369.

    Google Scholar 

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Correspondence to Casimir C. Akoh.

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Xu, X., Fomuso, L.B. & Akoh, C.C. Modification of menhaden oil by enzymatic acidolysis to produce structured lipids: Optimization by response surface design in a packed bed reactor. J Amer Oil Chem Soc 77, 171–176 (2000). https://doi.org/10.1007/s11746-000-0027-3

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  • DOI: https://doi.org/10.1007/s11746-000-0027-3

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