New alkaloid, benzenoid, and anti-inflammatory constituents from Zanthoxylum ailanthoides

Zanthoxylum ailanthoides Sieb. & Zucc. (Rutaceae) is a medium-to-large-sized tree distributed in Japan, Korea, China, Philippines, and Taiwan [1]. Its leaves are used as folk medicine to treat common cold in Taiwan [2]. Lignans, coumarins, quinolines, flavonoids, benzo[c]phenanthridines, and triterpenoids are the major constituents of this plant. Investigation on EtOAc-soluble fraction of the stem bark of Zanthoxylum ailanthoides has led to the isolation of a new alkaloid, N-(4-methoxyphenethyl)-2-(4-methoxyphenyl)-N,N-dimethylethanamine (1) and a new benzenoid, (–)-4-(4′-hydroxy-3′-methylbutoxy)benzaldehyde (2), together with seventeen known compounds, including a terpenoid, β-amyrin (3), two benzo[c]phenanthridines, norchelerythrine (4) and decarine (5), three lignans, (+)-episesamin (6), (–)-hinokinin (7), and evofolin-B (8), four coumarins, bergapten (9), 6,7,8-trimethoxycoumarin (10), aesculetin dimethyl ether (11), and xanthyletin (12), six benzenoids, methyl (E)-p-hydroxycinnamate (13), methyl (Z)-p-hydroxycinnamate (14), methyl 4-hydroxybenzoate (15), methyl 4-p-hydroxydihyhydrocinnamate (16), (+)-4′-(4′′-hydroxy-3′′-methylbutyloxy)-3-phenylpropenol (17), and syringaldehyde (18), and a furoquinoline, γ-fagarine(19). The structures of the two new compounds were determined through spectroscopic and MS analyses. The structural elucidation of 1 and 2 and the anti-inflammatory activity of the isolates are described.

Acknowledgements: This work was supported by grant from the National Science Council of the Republic of China.

References: 1. Chang, C.E., Hartley T.G. (1993) Rutaceae in Flora of Taiwan, 2nd edn. Editorial Committee of the Flora of Taiwan, Taipei,

Taiwan, Vol. 3: pp 510–544

2. Gan, W. S. (1970) Manual of Medicinal Plants in Taiwan, National Research Institute of Chinese Medicine, Taiwan, Vol. II: p 375.