Neolignans, a Coumarinolignan, Lignan Derivatives, and a Chromene: Anti-inflammatory Constituents from Zanthoxylum avicennae

Abstract

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.