Formation of thomasidioic acid from dehydrosinapinic acid dilactone under neutral conditions, and a remaining inhibitory activity against peroxynitrite-mediated protein nitration.
Dehydrosinapinic acid dilactone (1) was converted to thomasidioic acid (3) and (E,E)-2,3-bis(3,5-dimethoxy-4-hydroxybenzylidene)succinic acid (4) via an alpha,beta-unsaturated gamma-lactone type dimer (2) in phosphate buffer (pH 7.4). A study of the reaction mechanism was accomplished by observing the reaction of methyl ester of 2. The lignans (3, 4) were also prevented the peroxynitrite-mediated protein nitration.
Niwa
Toshio
T
Department of Research and Development, San-ei Sucrochemical Co., Ltd., 24-5 Kitahama-machi, Chita, 478-8503, Aichi, Japan. toshio-niwa@sanei.toki.co.jp
Doi
Umeyuki
U
Osawa
Toshihiko
T
D001565:Benzoates / Q000138:chemical synthesis*; D001713:Biphenyl Compounds / Q000138:chemical synthesis*; D003373:Coumaric Acids / Q000737:chemistry / Q000494:pharmacology*; D019281:Dimerization; D006863:Hydrogen-Ion Concentration; D007783:Lactones / Q000737:chemistry; D017705:Lignans / Q000494:pharmacology; D016877:Oxidants / Q000737:chemistry*; D030421:Peroxynitrous Acid / Q000737:chemistry*; D011506:Proteins / Q000187:drug effects / Q000378:metabolism
D001565:Benzoates; D001713:Biphenyl Compounds; D003373:Coumaric Acids; D007783:Lactones; D017705:Lignans; D016877:Oxidants; D011506:Proteins; C475898:thomasidioic acid; D030421:Peroxynitrous Acid; C073734:sinapinic acid