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DOI: 10.1055/s-2002-32893
Bioactive Sesquiterpene Lactones from Centaurea Species and their Cytotoxic/Cytostatic Activity Against Human Cell Lines in vitro
Publication History
Received: October 5, 2001
Accepted: January 20, 2002
Publication Date:
22 July 2002 (online)
Abstract
Sesquiterpene lactones isolated from the aerial parts of various species of the genus Centaurea were examined for their in vitro cytotoxic/cytostatic activity against five human cell lines (i. e., DLD1, SF268, MCF7, H460 and OVCAR3). Compounds 1 - 4 were isolated from C. zuccariniana, 5 and 6 from C. achaia, 7 from C. thessala ssp. drakiensis and compounds 8 and 9 from C. deusta. Compound 1, 8α-O-(3,4-dihydroxy-2-methylenebutanoyloxy)dehydromelitensine was found to be the most active, exhibited a considerable growth inhibiting activity against three of the cell lines tested, while compound 5 8α-O-(3-hydroxy-2-methylenepropanoyl)dehydromelitensin exhibited a growth inhibiting effect against most of the tested cell lines. A new eudesmanolide (8α-hydroxysonchucarpolide, 4) was isolated from C. zuccariniana and its structure was elucidated by spectroscopic methods.
- 1 Mabberlay D J. The Plant-Book. 2nd edition Cambridge University Press 1997: 440
- 2 Skaltsa H, Lazari D, Georgiadou E, Kakavas S, Constantinidis T h. Sesquiterpene lactones from Centaurea species: C. thessala ssp. drakiensis and C. attica ssp. attica . Planta Medica. 1999; 65 393
- 3 Skaltsa H, Lazari D, Garcia B, Pedro J, Sokovic M ., Constantinidis T h. Sesquiterpene lactones from Centaurea achaia, a Greek endemic species. Antifungal activity. Z. Naturforsch. C. 2000; 55c 534-9
- 4 Skaltsa H, Lazari D, Panagouleas C, Georgiadou E, Garcia B, Sokovic M. Sesquiterpene lactones from Centaurea thessala Hausskn. ssp. drakiensis (Freyn & Sint.) Georg. and Centaurea attica Nym. ssp. attica. Antifungal activity. Phytochemistry. 2000; 55 903-8
- 5 Karioti A, Skaltsa H, Lazari D, Sokovic M, Garcia B, Harvala C. Secondary metabolites from Centaurea deusta with antimicrobial activity. Z. Naturforsch. C 2001, in press
- 6 Rodriguez E, Towers G HN, Mitchell J C. Biological activities of sesquiterpene lactones. Phytochemistry. 1976; 15 1573-80
- 7 Kupchan S M, Eakin M A, Thomas A M. Structure cytotoxicity relationship among the sesquiterpene lactones. Journal of Medicinal Chemistry. 1971; 14 1147-52
-
8 Kupchan S M. Advances in the Chemistry of tumor-inhibitory natural products. Runeckles VD. (ed.)
In: Recent Advances in Phytochemistry . New York, London; Plenum Press 1975 IX: 167-88 - 9 Coll J C, Bowden B F. The application of vacuum liquid chromatography to the separation of terpene mixtures. Journal of Natural Products. 1986; 49 943-5
- 10 Jakupovic J, Jia Y, Pathack V P, Bohlmann F, King R M. Bisabolene derivatives and sequiterpene lactones from Centaurea species. Planta Medica. 1986; 5 399-401
- 11 Rustaiyan A, Niknejad A, Aynechi Y. Chemical constituents of Centaurea brugueriana . Planta Medica. 1982; 44 185-7
- 12 Bruno M, Herz W. Sesquiterpene lactones and flavones from Centaurea cineraria ssp. umbrosa.. Phytochemistry1988; 27 1873-5
- 13 Monks A, Scudiero D, Skehan P, Shomaker R, Paull K, Vistica D, Hose C. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer I.. 1991; 83 661-757
- 14 Mashadesh H, Hatziantoniou S, Demetzos C, Dimas K, Georgopoulos A, Rallis M. Encapsulation of vinblastine into new liposome formulations prepared from Triticum (wheat germ) lipids and its activity against human leukemic cell lines. Anticancer Research. 2000; 20 4385-90
Prof. Dr. Assist. H Skaltsa
University of Athens
School of Pharmacy
Division of Pharmacognosy
Panepistimiopolis
Zografou
GR-157 71 Athens
Greece
Email: skaltsa@pharm.uoa.gr
Fax: +30108613965
Phone: +30107274593