Oxidation of synthetic triacylglycerols containing eicosapentaenoic and docosahexaenoic acids: Effect of oxidation system and triacylglycerol structure
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Thirteen synthetic triacylglycerols (TAG) containing eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA) were oxidized in the presence of 2,2′-azobis(2,4-dimethyl-valeronitrile) (AMVN) and 2,2′-azobis(2-amidinopropane)dihydrochloride (AAPH) as aqueous and nonaqueous radical initiators to investigate the influence of TAG structure and oxidation system on the oxidative stability of TAG that contain highly unsaturated fatty acids (HUFA). A 2:1 (mol/mol) mixture of trieicosapentaenoylglycerol and tripalmitoylglycerol was most susceptible to the AMVN-initiated oxidation among three types of TAG that contained EPA and palmitic acid (2:1, mol/mol). Compared with 1,2 (or 2,3)-dieicosapentaenoyl-3(or 1)-palmitoylglycerol (EEP) and 1,3-dieicosapentaenoyl-2-palmitoylglycerol (EPE), the oxidative rate of EEP was somewhat higher. A similar result was obtained for DHA-containing TAG. The oxidative rate of TAG that contained EPA and palmitic acid (1:2, mol/mol) showed a positive correlation with the amount of EPA in a single TAG molecule. Moreover, in the nonaqueous system, the oxidative rate of EPA-containing TAG was affected by unsaturation and carbon chainlength of constituent fatty acids. In the AAPH-initiated oxidation in the aqueous system, the oxidative rate of TAG with EPA and palmitic acid was higher with the increased quantity of EPA in a single TAG molecule. Also, constituent fatty acids modified the oxidative rate of EPA-containing TAG in an aqueous system. The glycerol position of EPA and DHA also affected the oxidative rate of the TAG. EPA and DHA located at the 1,2 (or 2,3)-position of glycerol were more oxidizable than those at the 1,3-position during AAPH-initiated oxidation. Thus, 1,2(or2,3)-dipalmitoyl-3(or 1)-eicosapentaenoylglycerol was oxidized faster than 1,3-dipalmitoyl-2-eicosapentaenoylglycerol. These observations suggest that the oxidative stability of TAG that contain HUFA could be modulated by the oxidation system and TAG structure.
- Kaneda, T., Toxicity of Autoxidized Oils, in Sea Foods in Nutrition, edited by S. Konosu, Koseisha Koseikaku, Tokyo, 1984, pp. 70–83.
- Kaneda, T., and T. Miyazawa, Lipid Peroxides and Nutrition, World Rev. Nutr. Diet. 50:186–214 (1987).
- Oarada, M., and T. Miyazawa, The Effect of Rancid Oils on Lymphoid Tissues, Yukagaku 39:373–379 (1990).
- Raghuveer, K.G., and E.G. Hammond, The Influence of Glyceride Structure on the Rate of Autoxidation, J. Am. Oil Chem. Soc. 44:239–243 (1967). CrossRef
- Lau, F.Y., E.G. Hammond, and P.F. Ross, Effect of Randomization on the Oxidation of Corn Oil, Ibid.:407–411 (1982). CrossRef
- Wada, S., and C. Koizumi, Influence of the Position of Unsaturated Fatty Acid Esterified Glycerol on the Oxidation Rate of Triglyceride, Ibid.:1105–1109 (1983).
- Park, D.K., J. Terao, and S. Matsushita, Influence of Interesterification on the Autoxidative Stability of Vegetable Oils, Agric. Biol. Chem. 47:121–123 (1983).
- Park, D.K., J. Terao, and S. Matsushita, Influence of Triglyceride Molecular Species on Autoxidation, Ibid.:2243–2249 (1983).
- Park, D.K., J. Terao, and S. Matsushita, Influence of the Positions of Unsaturated Acyl Groups in Glycerides on Autoxidation, Ibid.:2251–2255 (1983).
- Tautorus, C.L., and A.R. McCurdy, Effect of Randomization on Oxidative Stability of Vegetable Oils at Two Different Temperatures, J. Am. Oil Chem. Soc. 67:525–530 (1990). CrossRef
- Neff, W.E., E. Selke, T.L. Mounts, W.M. Rinsch, E.N. Frankel, and M.A.M. Zeitoun, Effect of Triacylglycerol Composition and Structures on Oxidative Stability of Oils from Selected Soybean Germplasm, Ibid.:111–118 (1992). CrossRef
- Yoon, H.S., T. Ohshima, and C. Koizumi, Susceptibilities of Different Molecular Species of Soybean Oil Triglycerides to Non-Catalyzed and Fe2+-Catalyzed Oxidations, Nippon Shokuhin Kogyo Gakkaishi 40:123–132 (1993).
- Neff, W.E., T.L. Mounts, W.M. Rinsch, H. Konishi, and M.A. El-Agaimy, Oxidative Stability of Purified Canola Oil Triacylglycerols with Altered Fatty Acid Compositions as Affected by Triacylglycerol Composition and Structure, J. Am. Oil Chem. Soc. 71:1101–1109 (1994). CrossRef
- Kimoto, H., Y. Endo, and K. Fujimoto, Influence of Interesterification on the Oxidative Stability of Marine Oil Triacylglycerols, Ibid.:469–473 (1994). CrossRef
- Endo, Y., S. Hoshizaki, and K. Fujimoto, Autoxidation of Synthetic Isomers of Triacylglycerol Containing Eicosapentaenoic Acid, Ibid.:543–548 (1997). CrossRef
- Awl, R.A., E.N. Frankel, and D. Weisleder, Synthesis and Characterization of Triacylglycerols Containing Linoleate and Linolenate, Lipids 24:866–982 (1989). CrossRef
- Endo, Y., T. Chiba, and K. Fujimoto, Oxidative and Hydrolytic Stability of Synthetic Diacyl Glyceryl Ether, Biosci. Biotech. Biochem. 60:216–219 (1996).
- Miyashita, K., E.N. Frankel, W.E. Neff, and R.A. Awl, Autoxidation of Polyunsaturated Triacylglycerols. III. Synthetic Triacylglycerols Containing Linoleate and Linolenate, Lipids 25:48–53 (1990). CrossRef
- Frankel, E.N., E. Selke, W.E. Neff, and K. Miyashita, Autoxidation of Polyunsaturated Triacylglycerols. IV. Volatile Decomposition Products from Triacylglycerols Containing Linoleate and Linolenate, Ibid.:442–446 (1992). CrossRef
- Endo, Y., H. Kimoto, and K. Fujimoto, Retarded Autoxidation of Sardine Oil with Oleate, Biosci. Biotech. Biochem. 57:2202–2204 (1993). CrossRef
- Miyashita, K., E. Nara, and T. Ota, Oxidative Stability of Free Fatty Acid Mixtures from Soybean, Linseed, and Sardine Oils in an Aqueous Solution, Fisheries Sci. 60:315–318 (1994).
- Miyashita, K., M. Hirano, E. Nara, and T. Ota, Oxidative Stability of Triglycerides from Orbital Fat of Tuna and Soybean Oil in an Emulsion, Ibid.:273–275 (1995).
- Oxidation of synthetic triacylglycerols containing eicosapentaenoic and docosahexaenoic acids: Effect of oxidation system and triacylglycerol structure
Journal of the American Oil Chemists' Society
Volume 74, Issue 9 , pp 1041-1045
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- Docosahexaenoic acid
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