Neolignans, a coumarinolignan, lignan derivatives, and a chromene:: Anti-inflammatory constituents from Zanthoxylum avicennae

Eight new compounds, including four new neolignans, (7'S,8'S)-bilagrewin (1), (7'S,8'S)-5-demethoxybilagrewin (2), (7'S,8'S)-5-O-demethyl-4'-O-methylbilagrewin (3), and (7'S,8'S)-nocomtal (4), a new coumarinolignan, (7'S,8'S)-4'-O-methylcleomiscosin D (5), two new lignan derivatives, (+)-9'-O-(Z)-feruloyl-5,5'-dimethoxylariciresinol (6) and (+)-9'-O-(E)-feruloyl-5,5'-dimethoxylariciresinol (7), and a new chromene, (E)-3-(2,2-dimethyl-2H-chromen-6-yl)prop-2-enal (8), have been isolated from the stem wood of Zanthoxylum avicennae, together with 18 known compounds (9-26). The structures of these new compounds were determined through spectroscopic and MS analyses. (7'S,8'S)-4'-O-Methylcleomiscosin D (5), cleomiscosin D (9), skimmianine (18), robustine (19), and integrifoliolin (23) exhibited inhibition (IC50 <= 18.19 mu M) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (FMLP/CB). In addition, skimmianine (18) inhibited FMLP/CB-induced elastase release with an IC50 value of 19.15 0.66 mu M.