Studies on the chemical constituents of rutaceous plants. LIX. The chemical constituents of Xanthoxylum nitidum (Roxb.) D.C. (Fagara nitida Roxb.) (1) Examination of the alkaloidal fraction of the bark

Abstract

Chemical constituents in the alkaloidal fraction of the bark of Formosan X. nitidum (ROXB.) D.C. (F. nitida ROXB.) (Japanese name : Teriha-Zansho), Rutaceae, which was collected in the area of Ping-Tung Hsien, were examined. Twelve alkaloids [nitidine (1), oxynitidine (2), 6-methoxy-5, 7-dihydrochelerythrine (4), oxychelerythrine (6), des-N-methyl-chelerythrine (7), chelerythrine (14), arnottianamide (24), liriodenine (25), bocconoline (26), decarine (27), integriamide (28), and isoarnottianamide (13)] and three lignans [l-asarinin (20), l-sesamin (21), and l-syringaresinol (29)], a coumarin, aesculetin dimethyl ether (22), together with β-sitosterol (23) were isolated. Other than the above seventeen known compounds a new phenolic benzo [c] phenanthridone alkaloid designated as oxyterihanine (30a) was also isolated as a minor component. While the past three groups reported that nitidine (1) was a sole quaternary benzo-[c] phenanthridine alkaloid in the same plants collected in the areas of Hong-Kong and of China mainland (Gauanx and Gauantung), in our case, chelerythrine (14) was isolated as a major component. Nitidine (1) was isolated from the plant collected at March as a second component, but chelecythrine (14) was essentially a sole benzo [c] phenanthridine alkaloid in the case of the plant collected at July and at September. The seasonal variation of the contents of the quaternary benzo [c] phenanthridine alkaloids is discussed.