Norditerpenoid Alkaloids from the Processed Tubers of Aconitum carmichaeli

Sang Hee Shim, Ju Sun Kim, Sam Sik Kang
2003 Chemical and pharmaceutical bulletin  
The aconite root is an indispensable and common drug in Chinese traditional medicine. The processed lateral root of Aconitum carmichaeli DEBEAUX (Ranunculaceae), now officially listed as "Prepared Aconite" in the Korean Pharmacopoeia, seventh edition, is used as an analgesic and anesthetic agent in the treatment of neuralgic and rheumatic conditions. 1) The aconite plants are known to contain a number of norditerpenoid and diterpenoid alkaloids. 2-8) During our work on diterpenoid alkaloids
more » ... enoid alkaloids from Aconitum plants, we isolated four new norditerpenoid alkaloids (3-5, 8) and five known ones (1, 2, 6, 7, 9) from the processed tubers of A. carmichaeli. 9) The structures were determined by detailed NMR analyses including 1 H-1 H correlation spectroscopy (COSY), heteronuclear multiple-quantum coherence (HMQC), and heteronuclear multiple-bond connectivity (HMBC) techniques. In this paper, we report on the isolation and structural elucidation of these compounds. Results and Discussion Compound 3 was isolated as an amorphous powder. The electron impact (EI) and positive FAB-MS showed a molecular ion [M] ϩ at m/z 567 and a quasimolecular ion [MϩH] ϩ at m/z 568, respectively. The high-resolution (HR) EI-MS showed a molecular ion peak [M] ϩ at m/z 567.3273 corresponding to the molecular formula C 33 H 45 NO 7 . The spectral data of 3 are quite similar to those of 14-O-acetylneoline (2). Comparison of the 1 H-and 13 C-NMR spectra of 3 with that of 14-O-acetylneoline (2) 11) clearly indicated the new alkaloid to be a neoline derivative possessing a cinnamoyl group [d H 6.42 (1H, d, Jϭ16.2 Hz), m), m), 7.68 (1H, d, Jϭ16.2
doi:10.1248/cpb.51.999 pmid:12913245 fatcat:v24on4xw7zeqnesrzool33mk5q