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通过氧化偶联反应制备生物活性木脂素的研究。VI. (E)-3-(4,5-二羟基-2-甲氧基苯基)-2-丁烯酸甲酯的氧化及所生成的咖啡醌的脂质过氧化抑制作用

Studies on the preparation of bioactive lignans by oxidative coupling reaction. VI. Oxidation of methyl (E)-3-(4,5-dihydroxy-2-methoxyphenyl)-2-butenoate and lipid peroxidation-inhibitory effects of the produced caffeoquinone.

作者信息

Maeda S, Masuda H, Tokoroyama T

机构信息

New Drug Research Laboratories, Kanebo Co. Ltd., Osaka, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1995 Sep;43(9):1588-91. doi: 10.1248/cpb.43.1588.

DOI:10.1248/cpb.43.1588
PMID:7586086
Abstract

Oxidation of hydroxy-alpha-methylcinnamate 5 derived from 4-methylesculetin afforded the alpha-methylcaffeoquinone derivative 7 without formation of the oxidative coupling product. The reaction of the alpha-methylferulate derivative 13 afforded a complex mixture of products. Thus, the hydroxy-alpha-methylcinnamates seem not to be suitable substrates for oxidative coupling. Compound 7 was tested for inhibitory effect on lipid peroxidation. It showed more potent activity than idebenone in rat brain homogenate, and was much more potent than (+/-)-alpha-tocopherol in rat liver microsomes.

摘要

源自4-甲基七叶亭的羟基-α-甲基肉桂酸酯5的氧化反应生成了α-甲基咖啡醌衍生物7,且未形成氧化偶联产物。α-甲基阿魏酸酯衍生物13的反应生成了复杂的产物混合物。因此,羟基-α-甲基肉桂酸酯似乎不是氧化偶联的合适底物。对化合物7进行了脂质过氧化抑制作用测试。在大鼠脑匀浆中,它显示出比艾地苯醌更强的活性,在大鼠肝微粒体中比(±)-α-生育酚活性更强得多。

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