Essential Oils and Hexane Extracts from Leaves and Fruits of Cistus monspeliensis. Cytotoxic Activity of ent-13-epi-Manoyl Oxide and its Isomers

Dimitra Angelopoulou; Costas Demetzos; Costas Dimas; Dimitrios Perdetzoglou; Anargyros Loukis

doi:10.1055/s-2001-11497

Planta Medica, Table of Contents

Planta Med 2001; 67(2): 168-171
DOI: 10.1055/s-2001-11497

Letter

Essential Oils and Hexane Extracts from Leaves and Fruits of Cistus monspeliensis. Cytotoxic Activity of ent-13-epi-Manoyl Oxide and its Isomers

Dimitra Angelopoulou¹ , Costas Demetzos^1,*, Costas Dimas² , Dimitrios Perdetzoglou¹ , Anargyros Loukis¹

¹ School of Pharmacy, Department of Pharmacognosy, University of Athens, Greece
² International Institute of Anticancer Research, Attiki, Greece

Abstract

Essential oils and hexane extracts from Cistus monspeliensis L. leaves and fruits were analysed by GC-MS. Manoyl oxide and its isomers, 3β-hydroxy-manoyl oxide, 3β-hydroxy-13-epi-manoyl oxide, as well as 3β-acetoxy-13-epi-manoyl oxide were detected for the first time in C. monspeliensis L. Ent-13-epi-manoyl oxide was isolated from the hexane extract of leaves and its structure was determined using spectroscopic methods. In vitro cytotoxic activity of ent-13-epi-manoyl oxide and mixtures of manoyl oxide isomers at 10^-4 M concentrations ranged from 11.1 to 32.2 % of the activity for a vinblastine control evaluated against nine leukemic cell lines. The results showed that the manoyl oxide isomer mixtures as well as ent-13-epi-manoyl oxide exhibited a slight growth inhibiting activity.

Full Text

References

1 Polunin O. Flowers of Europe a field guide. Oxford University Press 1969: 254
2 Demetzos C, Stahl B, Anastasaki T, Gazouli M, Tzouvelekis L, Rallis M. Chemical analysis and antimicrobial activity of the resin Ladano of its essential oil and of the isolated compounds. Planta Medica. 1999; 65 76-9
3 Anastasaki T, Demetzos C, Perdetzoglou D, Gazouli M, Loukis A, Harvala C. Analysis of labdane type diterpenes from Cistus creticus (subsp. creticus and subsp. eriocephalus), by GC and GC-MS. Planta Medica. 1999; 65 735-9
4 Adams R P. Identification of essential oil components by gas chromatography/mass spectrometry. Carol Stream, IL; Allured Publ. Corp. 1995
5 Uzman B G, Foley G E, Farber S, Lazarus H. Morphologic variationsin human leukemic lymphoblasts (ccrf-cem cells) after long term culture and exposure to chemotherapeutic agents. Cancer. 1966; 19 1725-42
6 Minowada M, Ohnuma T, Moore G E. Rosette-forming human lyphoid cells. I. Establishment and evidence for origin of thymus-derived lymphocytes. J. Natl. Cancer Inst.. 1972; 49 891-5
7 Gootenberg J E, Ruscetti F W, Mier J W, Gardar A, Gallo R C. Human cutaneous T cell lymphoma and leukemia cell lines produce and respond to T cell growth factor. J. of Exp. Med.. 1981; 154zz 1403-18
8 Rovera C, O'Brian T G, Schneider C, Newmann R, Kemslead J, Greaves M. Induction of differentiation in human promyelocytic leukemia cells by tumor promoters. Science. 1981; 204 868
9 Alder S, Ciampi A, McCullosh E A. A kinetic and clonal analysis of heterogeneity in k562 cells. J. of Cellular Physiology. 1984; 118 186-92
10 Fujimori A, Harker W G, Kohlhagen G, Hoki Y, Pommier Y. Mutation at the catalytic site of topoisomerase I in CEM/C2, a human leukemia cell line resistant to camptothecin. Cancer Res.. 1995; 55 1339-46
11 Harker W G, Slade D L, Dalton W S, Meltzer P S, Trent J M. Multidrug resistance in mitoxantrone-selected HL-60 leukemia cells in the absence of P-glycoprotein overexpression. Cancer Res.. 1989; 49 4542-9
12 Harker W G, Slade D L, Drake F H, Parr R L. Mitoxantrone resistance in HL-60 leukemia cells: reduced nuclear topoisomerase II catalytic activity and drug-induced DNA cleavage in association with reduced expression of the topoisomerase II beta isoform. Biochemistry. 1991; 30 9953-61
13 Dimas K, Kokkinopoulos D, Demetzos C, Vaos V, Marselos M, Malamas M, Tzavaras T. The effect of sclareol on growth and cell cycle progression of human leukemic cell lines. Leukemia Res.. 1999; 23 217-34
14 Monks A, Scudiero D, Skehan P, Shomaker R, Paull K, Vistica D et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. JNCI. 1991; 83 757-66
15 Mossman T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Imm. Meth.. 1983; 65 55-63
16 Denizot F, Lang R. Rapid colorimetric assay for cell growth and survival: Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Imm. Meth.. 1986; 89 271-7
17 Gülz P. The composition of terpene hydrocarbons in the ess. oil from leaves of four Cistus species. Z. Naturforsch. 1984; 39c 699-704
18 Torres M E, Velasco-Negueruela A, Perez-Alonso J M, Pinilla M G. Volatile constituents of two Salvia species grown wild in Spain. J. Ess. Oil Res.. 1997; 9 27-33
19 Roussis V, Tsoukatou M, Chinou I, Ortiz A. Composition and antibacterial activity of the essential oil of Helichrysum rupestre and H. ambiguum growing in the Balearic Island. Part III. Planta Medica. 1998; 64 675-6
20 Skaltsa H, Lazari D, Chinou I, Loukis A. Composition and antibacterial activity of the essential oils of Stachys candida and S. chrysantha from Southern Greece. Planta Medica. 1999; 65 393-4
21 Hodges R, Reed R I. The stereochemistry of manoyl oxide. Tetrahedron. 1960; 10 71-5
22 Kalpoutzakis E, Chinou I, Mitaku S, Skaltsounis A L, Harvala C. Antibacterial labdane type diterpenes from the resin Ladano of Cistus creticus subsp. creticus . Natural Product Letters. 1998; 11 173-9
23 Van den Dool H, Kratz P D. Generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatog.. 1963; 11 463-71

Ass. Prof. Dr. Costas Demetzos

School of Pharmacy

Department of Pharmacognosy

Panepistimiopolis Zografou 15771

Athens

Greece

Email: demetzos@galenos.pharm.uoa.gr

Fax: +30-1-7274596