title: Studies on the preparation of bioactive lignans by oxidative coupling reaction. II. Oxidative coupling reaction of methyl(E)-3-(4,5-dihydroxy-2-methoxyphenyl)propenoate and lipid peroxidation inhibitory effects of the produced lignans.
abstract: 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.
authors.affiliation: New Drug Research Laboratories, Kanebo Co., Ltd., Osaka, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Maeda
authors.lastname: Masuda
authors.forename: T
authors.initials: T
authors.lastname: Tokoroyama
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D001205:Ascorbic Acid / Q000494:pharmacology; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D002396:Catechols / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D015227:Lipid Peroxidation / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D010084:Oxidation-Reduction; D051381:Rats; D017208:Rats, Wistar
chemical_list: D000975:Antioxidants; D002396:Catechols; C092640:methyl-3-(4,5-dihydroxy-2-methoxyphenyl)propenoate; D001205:Ascorbic Acid