Subscribe to RSS
DOI: 10.1055/s-2008-1074544
© Georg Thieme Verlag KG Stuttgart · New York
Cytotoxicity of Prenylated Xanthones and Other Constituents from the Wood of Garcinia merguensis
Publication History
Received: January 17, 2008
Revised: March 26, 2008
Accepted: April 20, 2008
Publication Date:
03 June 2008 (online)
![](https://www.thieme-connect.de/media/plantamedica/200808/lookinside/thumbnails/10.1055-s-2008-1074544-1.jpg)
Abstract
One new prenylated xanthone 5-farnesyltoxyloxanthone B (4), three known xanthones α-mangostin (1), rubraxanthone (2) and isocowanol (3) as well as (2E,6E,10E)-4β-hydroxy-3-methyl-5β-(3,7,11,15-tetramethylhexadeca-2,6,10-tetraenyl)-cyclohex-2-en-1-one (5) and 3,3′,4-O-trimethylellagic acid were isolated from the wood of Garcinia merguensis Wight. The cytotoxic activities of compounds 1 – 5 were evaluated against the MCF-7, MDA-MB-231, NCI-H-460 and SF-268 cell lines with rubraxanthone 2 and 5 exhibiting the highest activity at 9.0 and 12.1 μM, respectively, against MCF-7 cells.
Key words
Garcinia merguensis - Guttiferae - xanthones - 5-farnesyltoxyloxanthone - cytotoxic activity
References
- 1 Nguyen L -HD, Vo H T, Pham H D, Connolly J D, Harrison L J. Xanthones from the bark of Garcinia merguensis. . Phytochemistry. 2003; 63 467-70
- 2 Wahyuni F S, Byrne L T, Dachriyanus , Dianita R, Jubahar J, Lajis N H. et al . A new ring reduced tetraprenyltoluquinone and a prenylated xanthone from Garcinia cowa. . Aust J Chem. 2004; 57 223-6
- 3 Rukachaisirikul V, Naklue W, Phongpaichit S, Towatana N H, Maneenoon K. Phloroglucinols, depsidones and xanthones from the twigs of Garcinia parvifolia. . Tetrahedron. 2006; 62 8578-85
- 4 Khac D D, Tran-Van S, Campos A M, Lallemand J -Y, Fetizon M. Ellagic compounds from Diplopanax stachyanthus. . Phytochemistry. 1990; 29 251-6
- 5 Sen A K, Sarkar K K, Mazumber P C, Banerji N, Uusori R, Hase T. The structures of garcinones A, B and C: three new xanthones from Garcinia mangostana. . Phytochemistry. 1982; 21 1747-50
- 6 Wan A SC. High resolution NMR studies of mangostin. Planta Med. 1973; 24 297-300
- 7 Ampofo S A, Waterman P G. Xanthones from three Garcinia species. Phytochemistry. 1986; 25 2351-5
- 8 Lee H -H, Ng S. 13C NMR spectra of 1,3,6-trihydroxy-7-methoxy-8-(3,7-dimethyl-2,6-octadienyl)-xanthone and its dimethyl derivative. Phytochemistry. 1982; 21 2151-4
- 9 Ito C, Itoigawa M, Takakura T, Ruangrungsi N, Enjo F, Takuda H. et al . Chemical constituents of Garcinia fusca: Structure elucidation of eight new xanthones and their cancer preventive activity. J Nat Prod. 2003; 66 200-5
- 10 Ee G CL, Lim C K, Rahmat A. Structure activity relationship of xanthones from Mesua daphnifolia and Garcinia nitiola towards human estrogen negative breast cancer cell line. Nat Prod Sci 2005; 11 : 220 – 4 [Chem Abstr. 2006; 144 266 592]
- 11 Ee G CL, Izzadin S A, Rahmani M, Sukari M A, Lee H . α-Mangostin and rubraxanthone, two potential lead compounds for anti-cancer activity against CEM-SS cell line. Nat Prod Sci 2006; 12 : 138 – 43 [Chem Abst. 2007; 146 9688]
- 12 Azebaze A GB, Meyer M, Valentin A, Nguemfo E L, Fomum Z T, Nkengfack A F. Prenylated xanthone derivatives with antiplasmodial activity from Allenblackia monticola Staner LC. Chem Pharm Bull. 2006; 54 111-3
- 13 Kardono L BS, Hanafi M, Sherley G, Kosela S, Harrison L J. Bioactive constituents of Garcinia porrecta and G. parvifolia grown in Indonesia. Pakistan J Biol Sci 2006; 9 : 483 – 6 [Chem Abstr. 2007; 46 224 703]
- 14 Pedro M, Cerqueira F, Sousa M E, Nascimento M SJ, Pinto M. Xanthones as inhibitors of growth of human cancer cell lines and their effects on the proliferation of human lymphocytes in vitro. . Bioorg Med Chem. 2002; 10 3725-30
- 15 Castanheiro R AP, Pinto M MM, Silva A MS, Cravo S MM, Gales L, Damas A . et al . Dihydroxyxanthones prenylated derivatives: Synthesis, structure elucidation and growth inhibitory activity on human tumor cell lines with improvement of selectivity for MCF-7. Bioorg Med Chem. 2007; 15 6080-8
- 16 Monks A, Scudiero D, Skehan P, Shoemaker 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. J Natl Cancer. Inst1991; 83 757-66
- 17 Skehan P, Storeng R, Scudiero D, Monks A, MacMahon J, Vistica D. et al . New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst. 1985; 82 1107-12
- 18 Vieira L MM, Kijjoa A, Wilairat R, Nascimento M SJ, Gales L, Damas A M. et al . Bioactive friedolanostanes and 11 (10→8)-abeolanostanes from the bark of Garcinia speciosa. . J Nat Prod 2004; 67 : 2043 – 47; corr ibid. 2005; 68 969
Prof. Werner Herz
Department of Chemistry and Biochemistry
718 Dittmer Bldg.
Tallahassee
Florida 32306–4390
USA
Phone: +1/850/644/2774
Fax: +1/850/644/8281
Email: jdulin@chem.fsu.edu