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一种新型维生素E衍生物2-(α-D-吡喃葡萄糖基)甲基-2,5,7,8-四甲基色满-6-醇的抗氧化活性

Antioxidant activity of a novel vitamin E derivative, 2-(alpha-D glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol.

作者信息

Murase H, Moon J H, Yamauchi R, Kato K, Kunieda T, Yoshikawa T, Terao J

机构信息

The United Graduate School of Agricultural Sciences, Gifu University, Japan.

出版信息

Free Radic Biol Med. 1998 Jan 15;24(2):217-25. doi: 10.1016/s0891-5849(97)00221-9.

DOI:10.1016/s0891-5849(97)00221-9
PMID:9433895
Abstract

A novel vitamin E derivative, 2-(alpha-D-glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol (TMG), has excellent water-solubility (> 1 x 10[3] mg/ml). The antioxidant activity of TMG was investigated. Kinetic studies of the inhibition of radical-chain reaction of methyl linoleate in solution demonstrated that the peroxyl radical-scavenging activity was not changed by the replacement of phytiyl side chain of vitamin E to glucosyl group. TMG acted as an effective inhibitor on lipid peroxidation of egg yolk phosphatidylcholine (PC)-liposomal suspension induced by a water-soluble and a lipid-soluble radical generator, 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH) and 2,2'-azobis(2,4-dimethylvaleronitrile) (AMVN). Its effectiveness was higher than that of ascorbic acid (AsA) when liposomal suspension was exposed to a lipid-soluble radical generator, AMVN. TMG also showed an excellent antioxidant activity on cupric ion-induced lipid peroxidation of PC-liposomal suspension, and suppressed the oxidation of rat brain homogenate which contained trace level of iron ion. On the other hand, AsA acted as a prooxidant on both the cupric ion-induced liposomal peroxidation and the oxidation of rat brain homogenate. When human plasma was exposed to either AAPH or AMVN, the accumulation of cholesteryl ester hydroperoxides was retarded by the addition of TMG.

摘要

一种新型维生素E衍生物,2-(α-D-吡喃葡萄糖基)甲基-2,5,7,8-四甲基色满-6-醇(TMG),具有优异的水溶性(>1×10³mg/ml)。对TMG的抗氧化活性进行了研究。溶液中亚油酸甲酯自由基链反应抑制的动力学研究表明,将维生素E的植基侧链替换为葡萄糖基不会改变过氧自由基清除活性。TMG对由水溶性和脂溶性自由基引发剂2,2'-偶氮二(2-脒基丙烷)二盐酸盐(AAPH)和2,2'-偶氮二(2,4-二甲基戊腈)(AMVN)诱导的蛋黄磷脂酰胆碱(PC)脂质体悬浮液的脂质过氧化起到有效抑制作用。当脂质体悬浮液暴露于脂溶性自由基引发剂AMVN时,其效果高于抗坏血酸(AsA)。TMG对铜离子诱导的PC脂质体悬浮液脂质过氧化也表现出优异的抗氧化活性,并抑制了含有痕量铁离子的大鼠脑匀浆的氧化。另一方面,AsA在铜离子诱导的脂质体过氧化和大鼠脑匀浆氧化中均起到促氧化剂的作用。当人血浆暴露于AAPH或AMVN时,添加TMG可延缓胆固醇酯氢过氧化物的积累。

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