Autoxidation of synthetic isomers of triacylglycerol containing eicosapentaenoic acid |
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Authors: | Yasushi Endo Sanae Hoshizaki Kenshiro Fujimoto |
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Affiliation: | (1) Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba, 981 Sendai, Japan |
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Abstract: | 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. |
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Keywords: | Autoxidation eicosapentaenoic acid hydroperoxide oxidative stability triacylglycerol triacylglycerol structure |
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