Studies on the Chemical Constituents and Anti-inflammatory Activities from the Stem Wood of Zanthoxylum avicennae

• Main Authors: Tzu-Ying Wang, 王姿穎
• Other Authors: Jih-Jung Chen
• Format: Others
• Language: zh-TW
• Published: 2008
• Online Access: http://ndltd.ncl.edu.tw/handle/24661628096882334312

碩士 === 大仁科技大學 === 製藥科技研究所 === 96 === Zanthoxylum avicennae (Lam.) DC. (Rutaceae) is an evergreen shrub distributed in Vietnam, Philippines, southern China, and Taiwan. In our studies on the anti-inflammatory constituents of Formosan plants, many species have been screened for in vitro anti-inflammatory activity, and Z. avicennae has been found to be one of the active species. In our search for compounds with anti-inflammatory activities, 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), (7′S,8′S)-nocomtal (4), a new coumarinolignan, (7′S,8′S)-4′-O-methylcleo- miscosin D (5), two new lignan derivatives, (+)-9′-O-(Z)-feruloyl-5,5′-dimethoxylariciresinol (6), (+)-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) and 19 known compounds (9–27) have been isolated and identified from the stem wood of Z. avicennae. Nineteen known compounds include a coumarinolignan, cleomiscosin D (9), six coumarins, aesculetin dimethyl ether (10), scopoletin (11), 6,7,8-trimethoxycoumarin (12), luvangetin (13), avicennol (14), and avicennol methyl ether (15), four furoquinolines, γ-fagarine (16), dictamnine (17),skimmianine (18), and robustine (19), a furo-4-quinolone, isodictamnine(20), two 2-quinolones, 4-methoxy-1-methyl-2-quinolone (21) and edulitine (22), two phenylpropenoids, integrifoliolin (23) and methyl (E)-4-(3′-methyl-2′-enyloxy)cinnamate (24), a lignan, (–)-syringaresinol(25), a benzenoid, syringaldehyde (26), and a steroid, β-sitosterol (27).The structures of all isolates were determined through spectral analyses and comparison of their physical and spectral data with literatures. Among the isolated compounds, (7′S,8′S)-4′-O-methylcleomiscosin D (5), cleomiscosin D (9), skimmianine (18), robustine (19), and integrifoliolin (23) exhibited inhibition (IC50 ≤ 18.19 M) of superoxide anion generation by human neutrophils in response to formyl-L- methionyl-L-leuckyl-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 M.