Antioxidative Activities of Cysteine Derivatives and Cysteine-containing Dipeptides and Their Synergism with Antioxidants in the Autoxidation of Linoleic Acid

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  • リノール酸の自動酸化におけるシステインおよびシステイン含有ジペプチド誘導体の抗酸化作用と抗酸化剤に対する相乗効果

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Antioxidative and synergistic activities of 14 cysteine derivatives and 10 dipeptide derivatives with the sequences Cys (R)-Ser and Ser-Cys (R) were investigated, using an autoxidative system of linoleic acid, and the following results were obtained : 1) None of the tested compounds showed any marked antioxidative activity against autoxidation of linoleic acid. 2) In general, S-alkylcysteines were synergistically effective with both dl-α-tocopherol and dibutylhydroxytoluene (BHT). On the other hand, cysteine markedly increased POV of the system in the presence of BHT, while it showed synergistic activity toward α-tocopherol. 3) Blocking of the amino group of cysteine and S-alkylcysteines caused the loss of their synergistic activities, while blocking of the carboxyl group gave products with proxidative activity in the presence of antioxidants. 4) Both Cys (Bzl)-Ser and Ser-Cys (Bzl) showed synergistic effect nearly equal to their constituent amino acids. In analogy with S-alkylcysteins, blocking of the terminal groups, especially the carboxyl group, caused appreciable loss in the synergistic activities of the dipeptides, and a potent proxidative activity was observed with some blocked peptides including Ser-Cys (Bzl)-OBzl, BOC-Ser-Cys (Bzl)-OBzl, and Z-Cys (Bzl)-Ser-OMe. These results suggested that the synergistic action of cysteine derivatives and cysteine-containing peptides might be caused by cooperative action of blocked SH group and free NH2 and COOH groups.

Journal

  • Eisei kagaku

    Eisei kagaku 26 (1), 1-7, 1980

    The Pharmaceutical Society of Japan

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