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.
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.
Maeda
S
S
New Drug Research Laboratories, Kanebo Co. Ltd., Osaka, Japan.
Masuda
H
H
Tokoroyama
T
T
D000818:Animals; D001923:Brain Chemistry / Q000187:drug effects; D002396:Catechols / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D015227:Lipid Peroxidation / Q000187:drug effects*; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D010084:Oxidation-Reduction; D051381:Rats; D014810:Vitamin E / Q000494:pharmacology
D002396:Catechols; C096565:methyl-3-(4,5-dihydroxy-2--methoxyphenyl)-2-butenoate; D014810:Vitamin E