Planta Med 2008; 74(8): 864-866
DOI: 10.1055/s-2008-1074544
Natural Products Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxicity of Prenylated Xanthones and Other Constituents from the Wood of Garcinia merguensis

Anake Kijjoa1 , 2 , Maria Jose Gonzalez3 , 4 , Madalena M. Pinto3 , 4 , Maria São José Nascimento3 , 5 , Nair Campos2 , Ing-On Mondranondra6 , Artur M.S. Silva7 , Graham Eaton8 , Werner Herz9
  • 1ICBAS – Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, Porto, Portugal
  • 2Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Porto, Portugal
  • 3Centro de Estudo de Química Orgânica, Fitoquímica e Farmacologia, Universidade do Porto, Porto, Portugal
  • 4Serviço de Química Orgânica, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal
  • 5Serviço de Microbiologia, Faculdade de Farmacia, Universidade do Porto, Porto, Portugal
  • 6Department of Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand
  • 7Departamento de Química, Universidade de Aveiro, Aveiro, Portugal
  • 8Department of Chemistry, University of Leicester, Leicester, England
  • 9Department of Chemistry and Biochemistry, The Florida State University, Tallahassee, Florida, USA
Further Information

Publication History

Received: January 17, 2008 Revised: March 26, 2008

Accepted: April 20, 2008

Publication Date:
03 June 2008 (online)

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.

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

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