Maeda S, Tokoroyama T
New Drug Research Laboratories, Kanebo Co., Ltd., Osaka, Japan.
Chem Pharm Bull (Tokyo). 1994 Dec;42(12):2506-13. doi: 10.1248/cpb.42.2506.
The oxidative coupling reaction of methyl (E)-3-4(4,5-dihydroxy-2-methoxyphenyl)propenoate (10), obtainable from esculetin, has been studied using silver oxide and potassium hexacyanoferrate(III). The products were separated, after acetylation, by silica gel column chromatography. 1-Aryl-1,2-dihydronaphthalene derivative 12 was obtained as a major product, accompanied by the benzo[kl]xanthene derivative 13. In the oxidation with silver oxide, a benzodioxane compound 14a was produced additionally in a minor amount. Thus, the course of the reaction differed notably from those of ferulic or caffeic acid derivatives. The compounds 11, 12, 13 and 14a were tested for their inhibitory effects on lipid peroxidation in rat brain homogenate and rat liver microsomes. They showed activities more effective than that of idebenone in rat brain homogenate, and were found to be more potent than benzofuran lignans 4 and 5, and much more potent than (+/-)-alpha-tocopherol in rat liver microsomes.
已使用氧化银和铁氰化钾（III）研究了可从七叶亭制得的（E）-3-4（4,5-二羟基-2-甲氧基苯基）丙酸甲酯（10）的氧化偶联反应。乙酰化后，产物通过硅胶柱色谱法分离。得到1-芳基-1,2-二氢萘衍生物12作为主要产物，并伴有苯并[k,l]呫吨衍生物13。在用氧化银氧化时，还少量生成了苯并二恶烷化合物14a。因此，该反应过程与阿魏酸或咖啡酸衍生物的反应过程明显不同。测试了化合物11、12、13和14a对大鼠脑匀浆和大鼠肝微粒体脂质过氧化的抑制作用。它们在大鼠脑匀浆中显示出比艾地苯醌更有效的活性，并且发现在大鼠肝微粒体中比苯并呋喃木脂素4和5更有效，比（±）-α-生育酚更有效得多。
