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DOI: 10.1055/s-0029-1240727
© Georg Thieme Verlag KG Stuttgart · New York
Triterpene Saponins from Cyclamen trocopteranthum
Publication History
received June 30, 2009
revised September 10, 2009
accepted November 30, 2009
Publication Date:
12 January 2010 (online)

Abstract
Two new triterpene saponins (1–2) together with three known saponins, deglucocyclamin I (3), cyclamin (4), and mirabilin (5), were isolated from the tubers of Cyclamen trocopteranthum. They were elucidated as 3β-O-{4-O-[3-hydroxyl-3-methylglutaryl]-β-D-xylopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 4)-[β-D-glucopyranosyl-(1 → 2)]-α-L-arabinopyranosyl}-16α-hydroxy-13β,28-epoxy-oleanan-30-al (1) and 3β-O-{4-O-[3-hydroxyl-3-methylglutaryl]-β-D-xylopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1 → 4)-[β-D-glucopyranosyl-(1 → 2)]-α-L-arabinopyranosyl}-16α-hydroxy-20,30-lactone-olean-12-ene (2). Their structures were characterized mainly by a combination of 1D- and 2D‐NMR techniques (1H-1H COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectroscopy. Saponins 1, 3, and 4 showed a weak cytotoxic activity when tested against HT-29 and HCT 116 tumor colon cancer cells.
Key words
Cyclamen trocopteranthum - Primulaceae - triterpene saponin - dicrotalic acid
References
- 1 Güner A, Özhatay N, Ekim T, Baser K H C. Flora of Turkey and the East Aegean Islands, Vol. 11. Edinburgh; Edinburgh University Press 2000: 128-135
- 2 Reznicek G, Jurenitsch J, Robien W, Kubelka W. Saponins in Cyclamen species: configuration of cyclamiretin C and structure of isocyclamin. Phytochemistry. 1989; 28 825-828
- 3 Caliş I, Satana M E, Yürüker A, Kelican P, Demirdamar R, Alaçam R, Tanker N, Rüegger H, Sticher O. Triterpene saponins from Cyclamen mirabile and their biological activities. J Nat Prod. 1997; 60 315-318
- 4 Caliş I, Yürüker A, Tanker N, Wright A D, Sticher O. Triterpene saponins from Cyclamen coum var. coum. Planta Med. 1997; 63 166-170
- 5 Yayli N, Baltaci C, Zengin A, Kuçukislamoglu M, Genç H. A triterpenoid saponin from Cyclamen coum. Phytochemistry. 1998; 48 881-884
- 6 Yayli N, Baltaci C, Zengin A, Küçükislamoğlu M, Genç H, Küçük M. Pentacyclic triterpenoid saponin from Cyclamen coum. Planta Med. 1998; 64 382-384
- 7 Kartal M, Mitaine-Offer A C, Abu-Asaker M, Miyamoto T, Calis I, Wagner H, Lacaille-Dubois M A. Two new triterpene saponins from Eryngium campestre. Chem Pharm Bull. 2005; 53 1318-1320
-
8 Lacaille-Dubois M A.
Bioactive saponins with cancer related and immunomodulatory activity: recent developments. Atta-Ur-Rahman Studies in natural products chemistry series, Vol. 32. Amsterdam, The Netherlands; Elsevier Science 2005: 209-246 - 9 Ma L, Gu Y C, Luo J G, Wang J S, Huang X F, Kong L Y. Triterpenoid saponins from Dianthus versicolor. J Nat Prod. 2009; 72 640-644
- 10 Yun Y S, Shimizu K, Morita H, Takeya K, Itokawa H, Shirita O. Triterpenoid saponin from Vaccaria segetalis. Phytochemistry. 1997; 47 143-144
- 11 Plaza A, Cinco M, Tubaro A, Pizza C, Piacente S. New triterpene glycosides from the stems of Anomospermum grandifolium. J Nat Prod. 2003; 66 1606-1610
- 12 Kirmizibekmez H, Bassarello C, Piacente S, Pizza C, Calis I. Triterpene saponins from Calendula arvensis. Z Naturforsch. 2006; 61b 1170-1173
- 13 Carmichael J, De Graff W G, Gazdar A F, Minna J D, Mitchell J B. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res. 1987; 47 936-942
- 14 Haddad M, Miyamoto T, Laurens V, Lacaille-Dubois M A. Two new biologically active triterpenoidal saponins acylated with salicylic acid from Albizia adianthifolia. J Nat Prod. 2003; 66 372-377
Prof. Marie-Aleth Lacaille-Dubois
Laboratoire de Pharmacognosie
UMIB UPRES EA 3660
Faculté de Pharmacie
Université de Bourgogne
7, Bd Jeanne d'Arc, B. P. 87 900
21079 Dijon Cedex
France
Phone: + 33 3 80 39 32 29
Fax: + 33 3 80 39 33 00
Email: m-a.lacaille-dubois@u-bourgogne.fr