Design, Synthesis and Evaluation of Novel Radical-Scavenging Antioxidant against Lipid Peroxidation.

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  • NOGUCHI Noriko
    Research Center for Advanced Science and Technology, University of Tokyo

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  • 新規抗酸化物質の設計・合成とその活性評価
  • シンキ コウ サンカ ブッシツ ノ セッケイ ゴウセイ ト ソノ カッセイ ヒ

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Abstract

With increasing evidence which shows the involvement of oxygen radicals in a variety of pathological events, cancer and aging, the role of antioxidants has received much attention. In order to develop a novel potent radical-scavenging antioxidant, the ideal structure of phenolic compound was designed considering the factors that determine antioxidant potency. 2, 3-Dihydro-5-hydroxy-2, 2-dipentyl-4, 6-di-t-butylbenzofuran (BO-653) was thus synthesized and its antioxidant activity was evaluated against lipid peroxidations in vitro. The electron spin resonance study showed that the phenoxyl radical derived from BO-653 was more resonance-stabilized than α-tocopheroxyl radical and BO-653 reduced α-tocopheroxyl radical rapidly. Although the chemical reactivity of BO-653 toward peroxyl radical was smaller than that of α-tocopherol, its antioxidant potency against lipid peroxidation in phosphatidylcholine liposomal membranes an low density lipoprotein (LDL) was superior to that of α-tocopherol. Ascorbic acid reduced the phenoxyl radical derived from BO-653 in the homogeneous solution, but it did not spare BO-653 in the oxidation of liposomal membranes or LDL. It was concluded that BO-653 is a potent novel radical-scavenging antioxidant.

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