Autoxidation of synthetic isomers of triacylglycerol containing eicosapentaenoic acid
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Several triacylglycerols (TAG) that contained eicosapentaenoic acid (EPA) were chemically synthesized and stored at 25°C to assess the influence of TAG structure on oxidative stability and formation of oxidation products. Oxidative stability was evaluated by oxygen consumption during storage of the TAG. Autoxidation products of TAG were analyzed by high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS). Results showed that a 2:1 (mole/mole) mixture of trieicosapentaenoylglycerol (EEE) and tripalmitoylglycerol (PPP) was most susceptible to autoxidation. The oxidative stability of TAG that contained EPA and palmitic acid was negatively correlated with the moles of EPA in a single TAG molecule. When TAG with one EPA and two other fatty acids were oxidized, chainlength of constituent fatty acids hardly affected the oxidative stability of EPA-containing TAG molecules, except for stearic acid. HPLC and LC-MS analyses showed that monohydroperoxides were major oxidation products regardless of type of TAG. Bis- and tris-hydroperoxides were formed during autoxidation of EEE and dieicos-apentaenoylpalmitoylglycerol. Monohydroperoxy epidioxides were found in all autoxidized TAG. These observations suggested that TAG structure affected the oxidation of TAG with highly unsaturated fatty acids.
- 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).
- Tautorus, C.L., and A.R. McCurdy, Effect of Randomization on Oxidative Stability of Vegetable Oils at Two Different Temperatures, Ibid.:525–530 (1990). CrossRef
- Neff, W.E., E. Selke, T.L. Mounts, W.W. Rinsch, E.N. Frankel, and M.A.M. Zeitoun, Effect of Triacylglycerol Composition and Structures on Oxidative Stability of Oils from Selected Soybean Germplasm,: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 Affected by Triacylglycerol Composition and Structure, J. Am. Oil Chem. Soc. 71:1101–1109 (1994). CrossRef
- Endo, Y., H. Kimoto, and K. Fujimoto, Retarded Autoxidation of Sardine Oil with Oleate, Biosci. Biotech. Biochem. 57:2202–2204 (1993). CrossRef
- Kimoto, H., Y. Endo, and K. Fujimoto, Influence of Interesterification on the Oxidative Stability of Marine Oil Triacylglycerols, J. Am. Oil Chem. Soc. 71:469–473 (1994). CrossRef
- Awl, R.A., E.N. Frankel, and D. Weisleder, Synthesis and Characterization of Triacylglycerols Containing Linoleate and Linolenate, Lipids 24:866–872 (1989). 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
- Miyashita, K., E.N. Frankel, W.E. Neff, and R.A. Awl, Autoxidation of Polyunsaturated Triacylglycerols. III. Synthetic Triacylglycerols Containing Linoleate and Linolenate, Ibid.:48–53 (1990). CrossRef
- 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).
- Yamauchi, R., T. Yamada, K. Kato, and Y. Ueno, Monohydroperoxides Formed by Autoxidation and Photosensitized Oxidation of Methyl Eicosapentaenoate, Ibid.:2897–2902 (1983).
- Yamauchi, R., T. Yamada, K. Kato, and Y. Ueno, Autoxidation and Photosensitized Oxidation of Methyl Eicosapentaenoate: Secondary Oxidation Products, Ibid.:2077–2082 (1985).
- Frankel, E.N., Review, Recent Advances in Lipid Oxidation, J. Sci. Food Agric. 54:495–511 (1991). CrossRef
- Autoxidation of synthetic isomers of triacylglycerol containing eicosapentaenoic acid
Journal of the American Oil Chemists' Society
Volume 74, Issue 5 , pp 543-548
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- eicosapentaenoic acid
- oxidative stability
- triacylglycerol structure
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