Subscribe to RSS
DOI: 10.1055/s-2003-818005
© Georg Thieme Verlag Stuttgart · New York
allo-Aromadendrane- and Picrotoxane-Type Sesquiterpenes from Dendrobium moniliforme
Publication History
Received: April 22, 2003
Accepted: September 29, 2003
Publication Date:
29 January 2004 (online)
![](https://www.thieme-connect.de/media/plantamedica/200312/lookinside/thumbnails/10.1055-s-2003-818005-1.jpg)
Abstract
Eight sesquiterpenes, four stilbene derivatives along with two lignans have been isolated from lipophilic fraction of stems of Dendrobium moniliforme (Orchidaceae). Among the eight sesquiterpenes, one allo-aromadendrane-type and four picrotoxane-type sesquiterpenes were identified to be new compounds, and α-dihydropicrotoxinin was isolated as a new natural product. Their structures were established on the basis of spectroscopic analysis.
Key words
Dendrobium moniliforme - Orchidaceae - sesquiterpene - dendrobiumanes A - E - allo-aromadendrane - picrotoxane
References
-
1 Jiangsu New Medical C ollege, Dictionary of Chinese herb m edicines. Shanghai; Shanghai Scientific and Technologic Press 1986: pp. 586-90
- 2 Kierkegaard P, Pilotti A M. Studies on Orchidaceae alkaloids XX. The constitution and relative configuration of crepidine, an alkaloid from Dendrobium crepidatum Lindl. Acta Chem Scand. 1970; 24 3757-9
- 3 Zhao W M, Ye Q H, Tan X J, Jiang H L, Li X Y, Chen K X, Kinghorn A D. Three new sesquiterpene glycosides from Dendrobium nobile with immunomodulatory activity. J Nat Prod. 2001; 64 1196-200
- 4 Zhao Y L, Wang S L, Li X Y. Studies on the polysaccharides of Dendrobium aphyllum . Acta Bot Yunnan. 1994; 16 392-6
- 5 Lee Y H, Park J D, Baek N I, Kim S I, Ahn B Z. In vitro and in vivo antitumoral phenanthrenes from the aerial parts of Dendrobium nobile . Planta Med. 1995; 61 178-80
- 6 Fan C Q, Wang W, Wang Y P, Qin G W, Zhao W M. Chemical constituents from Dendrobium densiflorum . Phytochemistry. 2001; 57 1255-8
- 7 Lin T H, Chang S J, Chen C C, Wang J P, Tsao L T. Two phenanthraquinones from Dendrobium moniliforme . J Nat Prod. 2001; 64 1084-6
- 8 Lin T H, Chang S J, Chen C C. Constituents from the stems of Dendrobium moniliforme . Chin Pharm J. 2000; 52 251-9
- 9 Zhao C S, Liu Q F, Halaweish F, Shao B P, Ye Y Q, Zhao W M. Copacamphane, picrotoxane, and alloaromadendrane sesquiterpene glycosides and phenolic glycosides from Dendrobium moniliforme . J Nat Prod. 2003; 66 1140-3
- 10 Mercer D, Robertson A. Picrotoxin. Part II. picrotone and picrotonol. J Chem Soc 1936: 288-94
- 11 Miyazawa M, Uemura T, Kameoka H. Biotransformation of sesquiterpenoids, (+)-aromadendrene and (-)-alloaromadendrene by Glomerella cingulata . Phytochemistry. 1995; 40 793-6
- 12 Miyashita M, Suzuki T, Yoshikoshi A. Stereoselective total synthesis of (-)-picrotoxinin and (-)-picrotin. J Am Chem Soc. 1989; 111 3728-34
- 13 Shimizu M, Shogawa H, Hayashi T, Arisawa M, Suzuki S, Yoshizaki M, Morita N, Ferro E, Basualdo I, Berganza L H. Anti-inflammatory constituents of topically applied crude drugs. III. Constituents and anti-inflammatory effect of Paraguayan crude drug ”Tamandá cuná” (Catasetum barbatum Lindle). Chem Pharm Bull. 1988; 36 4447-52
- 14 Majumder P L, Guha S, Sen S. Bibenzyl derivatives from the orchid Dendrobium amoenum . Phytochemistry. 1999; 52 1365-9
- 15 Juneja R K, Sharma S C, Tandon J S. Two substituted bibenzyls and dihydrophenanthrene from Cymbidium aloifolium . Phytochemistry. 1987; 26 1123-5
- 16 Lee T T, Rock G L, Stoessl A. Effects of orchinol and related phenanthrenes on the enzymic degradation of indole-3-acetic acid. Phytochemistry. 1978; 17 1721-6
- 17 Kobayashi H, Karasawa H, Miyase T, Fukushima S. Studies on the constituents of Cistanchis herba. V. Isolation and structures of two new phenylpropanoid glycosides, cistanosides E and F. Chem Pharm Bull. 1985; 33 1452-7
- 18 Weinges K. Die Lignane des Überwallungsharzes der Fichte. Tetrahedron Lett 1960: 1-2
- 19 Greca M D, Ferrara M, Fiorentino A, Monaco P, Previtera L. Antialgal compounds from Zantedeschia aethiopica . Phytochemistry. 1998; 49 1299-304
- 20 Tane P, Ayafor J F, Farrugia L J, Connolly J D, Rycroft D S, Tillequin F. Picrotoximaesin, a novel picrotoxane sesquiterpenoid from the berries of Maesobotrya floribunda . Nat Prod Lett. 1996; 9 39-45
Dr. Jieping Zhu
Institut de Chimie des Substances Naturelles
CNRS
91198 Gif-sur-Yvette Cedex
France
Fax: +33-1-6907-7247
Email: zhu@icsn.cnrs-gif.fr