Positional Isomers of Monohydroperoxides Produced during the Autoxidation of Methyl Ester and Triglycerides of Eicosapentaenoic Acid

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  • KAWATSU Tomoe
    Department of Applied Biological Chemistry, Faculty of Agriculture, Touhoku University
  • ENDO Yasushi
    Department of Applied Biological Chemistry, Faculty of Agriculture, Touhoku University
  • FUJIMOTO Kenshiro
    Department of Applied Biological Chemistry, Faculty of Agriculture, Touhoku University

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  • エイコサペンタエン酸のメチルエステル及びトリグリセリドの自動酸化で生成するモノヒドロペルオキシド位置異性体
  • エイコサペンタエンサン ノ メチルエステル オヨビ トリグリセリド ノ ジドウ

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Abstract

The methyl ester of eicosapentaenoic acid (EPA) and three triglycerides containing EPA (EEE, trieicosapentaenoylglycerol; EEP, 1, 2 (or 2, 3) -dieicosapentaenoyl-3 (or 1) -palm-itoylglycerol; EPP, 1, 2 (or 2, 3) -dipalmitoyl-3 (or 1) -eicosapentaenoylglycerol) were autoxidized and their monohydroperoxide (MHP) isomers were analyzed by normal phase high-performance liquid chromatography (HPLC). Eight MHP isomers (18-, 15-, 14-, 12-, 11-, 9-, 8-, 5-position) were found in the autoxidized methyl ester of EPA and the major component was 18-MHP. Although eihgt MHP isomers were detected during the autoxidation of EEE, EEP and EPP, 5-MHP was produced in only slight amount. The lipid structure is thus shown to be a determining factor of the composition of the MHP isomers of EPA.

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