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 α,β-unsaturated γ-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.