Alkaloids and Chemical Diversity of Stemona tuberosa

Abstract

Phytochemical investigation of the chemical components of Stemona tuberosa led to the isolation of two new alkaloids named tuberostemonine K (1) and tuberospironine (2), together with the known tuberostemonine (3). The new structures of 1 and 2 were elucidated through extensive spectroscopic analyses, while the molecular structure of 3 was confirmed by X-ray analysis. A gradient reversed-phase HPLC-ELSD method was established for the investigation of the chemical diversity of S. tuberosa from 13 localities, and four types of chemical variation featured by the major components 3, neotuberostemonine (4), croomine (5), and stemoninine (6), respectively, were observed.

Quality evaluation of Radix Stemonae through simultaneous quantification of bioactive alkaloids by high‐performance liquid chromatography coupled with diode array and evaporative light scattering detectors

“…The voucher specimens were deposited at the Herbarium of the Department of Biology and the Museum of the Institute of Chinese Medicine, CUHK. Croomine (1), protostemonine (2), stemoninine (3), maistemonine (4), neotuberostemonine (5) and tuberostemonine (6) were previously isolated in our laboratory from different provenances of S. tuberosa and S. japonica, and their structures were confirmed by IR, 1 H-and 13 C-NMR, MS and X-ray diffraction analysis (Jiang et al, 2002(Jiang et al, , 2006aZhou et al, 2006), or by comparison with literature data (Götz and Strunz, 1973;Ye et al, 1994a,c;Fig. 1).…”

“…For example, didehydrostemofoline, a protostemonine-type alkaloid from S. collinsa, was found to have high insect toxicity with an LC 50 value as low as 0.8 ppm, which was significantly more potent than that of the well-known natural insecticide azadirachtin with an LC 50 8.2 ppm (Brem et al, 2002). Our laboratory has investigated the chemistry and antitussive activities of Stemona alkaloids (Chun et al, 2003;Jiang et al, 2002Jiang et al, , 2006aXu et al, 2006;Xu, 2006;Zhou et al, 2006), and discovered four chemical types of variations of S. tuberosa, characterized by croomine, stemoninine, neotuberostemonine, or tuberostemonine (Jiang et al, 2006a). Furthermore, the total alkaloid compositions of these four chemotypes of S. tuberosa were found to exhibit different degrees of antitussive properties in the citric acid-induced guinea-pig cough model .…”

“…As significant variations of chemistry and pharmacology were found in Stemona species, especially in S. tuberosa (Jiang et al, 2006a;Xu, 2006;Xu et al, 2006), quality control is a very important issue to ensure the safety and consistent efficacy of Radix Stemonae. Recently a qualitative HPLC-MS method has been developed to differentiate three Stemona species documented in the Chinese Pharmacopoeia (Zhou et al, 2006), but relatively high cost and complex sample preparation hinder its routine use.…”

Development and validation of a high‐performance liquid chromatographic method for the determination of stemoninine in rat plasma after administration of Stemona tuberosa extracts

“…Pharmacological effects of Stemonae Radix are antitussive, antituberculous, antibacterial, antifungal and antihelminthic (Greger, 2006;Jiang et al, 2006;Pilli et al, 2005). The most effective ingredients of the genus Stemonae are alkaloids, such as stemoninine, stemoninoamide, bisdehydrostemoninine, neotuberostemonine, neostenine, tuberostemonine and tuberostemonine H, which exhibited strong antitussive activity in the citric acid-induced guinea pig cough model (Chung et al, 2003;Lin et al, 2006Lin et al, , 2008Zhou et al, 2009).…”

Nonaqueous capillary electrophoresis‐electrospray ionization‐ion trap‐mass spectrometry analysis of pyrrolo‐ and pyrido[1,2‐a]azepine alkaloids in Stemona

“…Several representatives of this genus comprising about 31 species have been used in Chinese and Japanese medicine particularly for the treatment of respiratory diseases and against enteric helminths or ectoparasites on human and cattle since ancient times [4][5][6][7][8].…”