Artículos de revistas
The Stemona Alkaloids
Registro en:
0120405407; 9780120405404
Alkaloids: Chemistry And Biology. , v. 62, n. , p. 77 - 173, 2005.
10994831
10.1016/S1099-4831(05)62002-0
2-s2.0-33645222093
Autor
Pilli R.A.
Rosso G.B.
De Oliveira M.D.C.F.
Institución
Resumen
The Stemonaceae (order Dioscoreales) is a small, monocotyledonous family with three small genera: Croomia (Southeastern North America and Japan), Stemona (Southeast Asia through Malaysia to North Australia), and Stichoneuron (Southeast Asia, including the Malay Peninsula) (1). Herbal extracts from various plants belonging to the Stemonaceae family have been used for the treatment of respiratory diseases and as antihelmintics in China and other East Asian countries for thousands of years. Amongst them, three species of the Stemona genus (S. tuberosa, S. japonica, and S. sessilifolia), which comprises about 25 species and represents the largest genus of the Stemonaceae family, have been officially listed in the 2000 Edition of the Chinese Pharmacopoeia as antitussive traditional Chinese medicinal herbs (2). Since the roots of several species are widely used as insecticides and for medicinal purposes, they are sold in local markets and herb shops. As an example, the dried roots of S. japonica, S. sessilifolia, or S. tuberosa (known as "Bai Bu" in traditional Chinese medicine, "Bach Bo" in Vietnam, or "Non Tai Yak" and "Pong Mot Ngam" in Thailand) contain several alkaloids, such as tuberostemonine, stenine, isostemonamine, stemonine, and protostemonine, and are used to suppress excitation of the respiratory center and inhibit the coughing reflex (3-5). The active principles are claimed to exert antituberculous, antibacterial, antifungal, and antihelminthic effects. "Bai Bu" displays a pesticide effect against Pediculus capitus, and the alcohol based extract is used as an insecticide and household spraying agent (6). However, because of the similarity of the fleshy tuberous roots, the same vernacular names are often used for different species, and even for representatives from other plant families. Caution is therefore recommended in order to properly classify plant material for studies or practical applications in agriculture and medicine (3-5). Despite their long history in traditional medicine, phytochemical studies on the Stemonaceae family have been limited to 14 species. Notwithstanding, these studies have provided structurally unique alkaloids which have sparked interest regarding their chemical and biological properties. Most of the Stemona alkaloids are structurally characterized by the presence of a pyrrolo[1,2-a]azepine (also known as perhydroazaazulene or 4-azaazulene) or, as revealed recently, a pyrido[1,2-a]azepine nucleus (Fig. 1). The Stemona alkaloids represent a class of polycyclic alkaloids with relatively complex structures which emerged from the structural elucidation of its first representative, tuberostemonine (Fig. 2) in the 1960s (7). Götz and Strunz reviewed this class of alkaloids in 1975 covering the structural elucidation of tuberostemonine, stenine, oxotuberostemonine, stemonine, protostemonine, stemofoline, and tuberostemonine A (7). Additionally, the physical data of 11 representatives of this family possessing unknown structures were also described. The field was reviewed again in 2000 covering literature data up to 1998 (8). The pyrrolo[1,2-a]azepine ring system is also present in alkaloid 275A which has been isolated from the skin of a Colombian poison frog, Dendrobates lehmanni (9). A limited number of Stemona alkaloids either lack or have a hidden pyrrolo[1,2-a]azepine architecture which can only be revealed on cleavage or formation of C-C bonds. This review focuses on the structural classification, isolation and structural elucidation, biological activity, and total synthesis of the Stemona alkaloids reported so far in the literature. Although dihydrophenanthrenes and stilbenoids, particularly several phenylbenzofurans, have been isolated from Stemona species (S. collinsae and Stemona cf. pierrei) and are of interest in their own right, these compounds are not included in the present review (10,11). © 2005 Elsevier Inc. All rights reserved. 62
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