We examined the antioxidant activities of various tocopherols (Toc) and their models under as nearly physiological conditions as possible, using egg lecithin liposomes as models of biomembranes. Toc can be exert the antioxidative effects without being oxidized when sufficient Toc to inhibit lipid peroxidation completely were incorporated in the liposome membranes, but when less quantities of Toc were incorporated, they were decomposed with increase in lipid peroxide formation. Cholesterol did not act as an antioxidant, even when incorporated in large amount into the liposome membranes, but it increased the antioxidative efficiency of α-Toc. The activities of Toc on ascorbic acid-Fe^<2+>-induced lipid peroxidation increased in order α-Toc>β-Toc>γ-Toc>δ-Toc>tocol, in agreement with their known order of biological vitamin E potencies. α-Toc model, in which the isoprenoid chain of α-Toc replaced by propionic acid, showed less activity. One molecule each of α-, β-, γ-, δ-Toc and tocol were calculated to be able to protect 220, 120, 100, 30 and 20 molecules, respectively, of polyunsaturated fatty acids. The ratio of α-Toc to polyunsaturated fatty acid moieties corresponds to that of membranes in highly oxygenated tissues such as heart and lung. The possible mechanism of the high efficient inhibitory effects of the Toc on ascorbic acid-Fe^<2+>-induced lipid peroxidation in liposome membranes is discussed.
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