Journal of the American Oil Chemists' Society

, Volume 78, Issue 1, pp 25–30 | Cite as

Characterization and oxidative stability of enzymatically produced fish and canola oil-based structured lipids

Article

Abstract

Two-kilogram quantities of structured lipids (SL) of menhaden fish and canola oils containing caprylic acids (8∶0) were produced in a laboratory-scale packed-bed bioreactor by acidolysis catalyzed by an immobilized lipase, Lipozyme IM, from Rhizomucor miehei. SL were characterized and their oxidative stabilities investigated. The SL contained 29.5% 8∶0 for fish oil and 40.15 for canola oil. Polyunsaturated fatty acids (PUFA) of fish oil remained unchanged after the modification while PUFA of canola oil were reduced from 29.6 to 21.2%. Monoenes, especially 18∶1n−9, were completely replaced by 8∶0 in fish oil and reduced from 61.9 to 34.7% in canola oil. Downstream processing of enzymatically produced SL led to loss in natural total tocopherol contents of the fish and canola oils. The effects of antioxidants such as α-tocopherol (TOC), tert-butylhydroxyquinone (TBHQ), and combinations thereof on the oxidative stability of SL were investigated. SL were analyzed for oxidative stability index, peroxide value, conjugated diene content, free fatty acid content, iodine value, saponification number, and thiobarbituric acid value. Iodine value of unmodified fish oil (154.71) was reduced to 144.10 and that of canola oil (114.49) to 97.27 after modification. The SN increased from 183.72 to 242.63 for fish oil and from 172.50 to 227.90 for canola oil. TBHQ exhibited better antioxidant effects than TOC. A combination of TBHQ/TOC also proved to be an effective antioxidant for SL. We suggest the addition of antioxidants to enzymatically produced and purified SL.

Key words

Antioxidants canola conjugated diene menhaden monoenes oxidative stability polyunsaturated fatty acids structured lipids thiobarbituric acid 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Willis, W.M., R.W. Lencky, and A.G. Marangoni, Lipid Modification Strategies in the Production of Nutritionally Functional Fats and Oils, Crit. Rev. Food Sci. Nutr. 38:1–36 (1998).CrossRefGoogle Scholar
  2. 2.
    Kennedy, J.P., Structured Lipids: Fats of the Future, Food Technol. 45:76–83 (1991).Google Scholar
  3. 3.
    Holmes, M.D., D.J. Hunter, G.A. Colditz, M.J. Stampfer, and S.E. Hankinson, Association of Dietary Intake of Fat and Fatty Acids with Risk of Breast Cancer, JAMA 281:914–920 (1999).CrossRefGoogle Scholar
  4. 4.
    Akoh, C.C., Structured Lipids-Enzymatic Approach, Inform 6:1055–1061 (1995).Google Scholar
  5. 5.
    Opstvedt, J., N. Urdahl, and J. Pettersen, Fish Oil—An Old Fat Source with New Possibilities, in Edible Fats and Oils Processing: Basic Principles and Modern Practices, edited by D.R. Erickson, American Oil Chemists' Society, Champaign, 1990, pp. 250–259.Google Scholar
  6. 6.
    Vinter, H., Production of High Quality Fish Oil, in Fish Oils: Technology, Nutrition and Marketing, edited by R.J. Hamilton and R.D. Rice, P.J. Barnes and Associates High Wycombe, 1995, pp. 27–33.Google Scholar
  7. 7.
    Forsyth, J.S., Lipids and Infant Formulas, Nutr. Res. Rev. 11:255–278 (1998).CrossRefGoogle Scholar
  8. 8.
    Chapman, K.W., I. Sagi, J.M. Regenstein, T. Bimbo, J.B. Crowther, and C.E. Stauffer, Oxidative Stability of Hydrogenated Menhaden Oil Shortening Blends in Cookies, Crackers, and Snacks, J. Am. Oil Chem. Soc. 73:167–172 (1996).CrossRefGoogle Scholar
  9. 9.
    Kolanowski, W. F. Swiderski, and S. Berger, Possibilities of Fish Oil Application for Food Products Enrichment with n−3 PUFA, Int. J. Food Sci. Nutr. 50:39–49 (1999)CrossRefGoogle Scholar
  10. 10.
    Lee, K.-T., C.C. Akoh, and D.L. Dawe, Effects of Structured Lipid Containing Omega-3 and Medium Chain Fatty Acids on Serum Lipids and Immunological Variables in Mice, J. Nutr. Biochem. 23:187–208 (1999).Google Scholar
  11. 11.
    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).Google Scholar
  12. 12.
    Willis, W.M., and A.G. Marangoni, Enzymatic Interesterification, in Food Lipids: Chemistry, Nutrition, and Biotechnology, edited by C.C. Akoh and D.B. Min, Marcel Dekker Inc, New York, 1998, pp. 665–698.Google Scholar
  13. 13.
    Moussata, C.O., and C.C. Akoh, Influence of Lipase-Catalyzed Interesterification on the Oxidative Stability of Melon Seed Oil Triacylglycerols, J. Am. Oil. Chem. Soc. 75:1155–1158 (1998).Google Scholar
  14. 14.
    Mu, H., X. Hu, and C.-E. Høy, Production of Specific-Structured Triacylglycerols by Lipase-Catalyzed Interesterification in a Laboratory-Scale Continuous Reactor, ——Ibid. 75:1187–1193 (1998).Google Scholar
  15. 15.
    Official Methods and Recommended Practices of the American Oil Chemists' Society, edited by D. Firestone, Champaign, Official Methods Ca 5a-40, TI 1a-64, Cd 1b-87, Cd 8-53, Cd 12-b, and Ti la-64Google Scholar
  16. 16.
    Nakayama, R., Y. Tamura, H. Kikuzaki, and N. Nakatani, Antioxidant Effect of the Constituents of Susabinori (Porphyra yezoensis), J. Am. Oil Chem. Soc. 76:649–653 (1999).Google Scholar
  17. 17.
    Chase, G.W., C.C. Akoh, and R.R. Eitenmiller, Analysis of Tocopherols in Vegetable Oils by High-Performance Liquid Chromatography: Comparison of Fluorescence and Evaporative Light-Scattering Detection, ——Ibid. 71:877–880 (1994).Google Scholar
  18. 18.
    SAS Institute Inc., SAS User's Guide: Basic, Version 5 edn., SAS Institute Inc, Cary, 1996.Google Scholar
  19. 19.
    Moussata, C.O., and C.C. Akoh, Lipase-Catalyzed Incorporation of Oleic Acid into Melon Seed Oil, J. Am. Oil Chem. Soc. 74:177–179 (1997).Google Scholar
  20. 20.
    Rossell, J.B., Classical Analysis of Oils and Fats, in Analysis of Oils and Fats, edited by R.J. Hamilton and R.B. Rossell (Elsevier Applied Science Publishers, New York, 1986, p. 12.Google Scholar
  21. 21.
    Williams, K.A., Marine Animal and Fish Oils, in Oils, Fats, and Fatty Foods: Their Practical Examination, 4th edition, edited by K.A. Williams, American Elsevier Publishing Company, New York, 1966, pp. 241–251.Google Scholar
  22. 22.
    Lee, K.T., and C.C. Akoh, Characterization of Enzymatically Synthesized Structured Lipids Containing Eicosapentaenoic, Docosahexaenoic, and Caprylic Acids, J. Am. Oil Chem. Soc. 75:495–499 (1998)Google Scholar
  23. 23.
    Akoh, C.C., Oxidative Stability of Fat Substitutes and Vegetable Oils by the Oxidative Stability Index Method, J. Am. Oil Chem. Soc. 71:211–215 (1994).Google Scholar
  24. 24.
    Jennings, B.H., and C.C. Akoh, Enzymatic Modification of Triacylglycerols of High Eicosapentaenoic and Docosahexaenoic Acids Content to Produce Structured Lipids, ——Ibid. 76:1133–1137 (1999).Google Scholar
  25. 25.
    Hopia, A., S.-W. Huang, and E.N. Frankel, Effect of α-Tocopherol and Trolox on the Decomposition of Methyl Linoleate Hydroperoxides, Lipids 31:357–365 (1996).CrossRefGoogle Scholar

Copyright information

© AOCS Press 2001

Authors and Affiliations

  1. 1.Department of Food Science & TechnologyThe University of GeorgiaAthens

Personalised recommendations