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 μM) 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 μM.