Planta Med 2011; 77(4): 377-379
DOI: 10.1055/s-0030-1250384
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Antiplasmodial Constituents from the Fruit Pericarp of Pentadesma butyracea

Bruno Ndjakou Lenta1 , Louis Marie Kamdem2 , Silvère Ngouela2 , Ferdinand Tantangmo2 , Krishna Prasad Devkota3 , Fabrice Fekam Boyom4 , Philip John Rosenthal5 , Etienne Tsamo2
  • 1Department of Chemistry, Higher Teachers' Training College, University of Yaoundé 1, Yaoundé, Cameroon
  • 2Department of Organic Chemistry, Faculty of Science, TWAS Research Unit, University of Yaoundé 1, Yaoundé, Cameroon
  • 3Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Bielefeld, Germany
  • 4Department of Biochemistry, University of Yaoundé 1, Faculty of Science, Yaoundé, Cameroon
  • 5Division of Infectious Diseases, Department of Medicine, University of California, San Francisco, San Francisco, CA, USA
Further Information

Publication History

received March 22, 2010 revised September 1, 2010

accepted September 3, 2010

Publication Date:
06 October 2010 (online)

Abstract

Bioassay-guided fractionation of the fruit pericarp of Pentadesma butyracea, using the antiplasmodial test, led to the isolation of a new xanthone, named pentadexanthone (1), together with six known compounds: cratoxylone (2), α-mangostin (3), 1,3,5-trihydroxy-2-methoxyxanthone (4), garcinone E (5), (−)-epicathechin (6), and lupeol (7). The structure of 1 was elucidated by spectroscopic data analysis. An antiplasmodial assay was performed with the isolates, in which compounds 13 and 5 exhibited potent activity in vitro against Plasmodium falciparum chloroquine-resistant strain W2, with IC50 values below 3 µM.

References

  • 1 Tchobo F, Natta A, Barea B, Barouh N, Piombo G, Pina M, Soumanou M, Sohounhloue D. Characterization of Pentadesma butyracea sabine butters of different production regions in Benin.  J Am Oil Chem Soc. 2007;  84 755-760
  • 2 Sinsin B, Sinadouwirou T A. Socio-economic utilization of Pentadesma butyraceae sabine and its substainability in gallery forest of Benin.  Cah Agric. 2003;  12 75-79
  • 3 Wabo H K, Kikuchi H, Katou Y, Tane P, Oshima Y. Xanthones and a benzophenone from the roots of Pentadesma butyracea and their antiproliferative activity.  Phytochem Lett. 2010;  3 104-107
  • 4 Zelefack F, Guilet D, Fabre N, Bayet C, Chevalley S, Ngouela S, Lenta B N, Valentin A, Tsamo E, Dijoux-Franca M G. Cytotoxic and antiplasmodial xanthones from Pentadesma butyracea.  J Nat Prod. 2009;  72 954-957
  • 5 Shin-ichiro S, Makiko K, Hiromitsu T, Norio A, Nantarit C, Maitree S. The structure of garcinone E.  Chem Pharm Bull. 1993;  41 958-960
  • 6 Bennett G J, Harrison L J, Sia G L, Sim K Y. Triterpenoids, tocotrienols and xanthones from the bark of Cratoxyllum cochinchense.  Phytochemistry. 1993;  32 1245-1251
  • 7 Ly D H, Poul E H, Ole V, Fritz D, Hung D P, Lien-Hoa D N. Cytotoxic geranylated xanthones and O-alkylated derivatives of α-mangostin.  Chem Pharm Bull. 2009;  57 830-834
  • 8 Tosa H, Iinuma M, Tanaka T, Nozaki H, Ikeda S, Ttsutsui K, Tsu-tsui K, Yamada M, Fujimori S. Inhibitory activity of xanthone derivatives isolated from some guttiferaeous plants against DNA topoisomerases I and II.  Chem Pharm Bull. 1997;  45 418-420
  • 9 Ngouela S, Zelefack F, Lenta B N, Ngouamegne E T, Tchamo D N, Tsamo E, Connolly J D. Xanthones and other constituents of Allanblackia monticola.  Nat Prod Res. 2005;  19 685-688
  • 10 Mahato B S, Kundu A P. 13C NMR spectra of pentacyclic triterpenoids-A compilation and some salient features.  Phytochemistry. 1994;  37 1517-1575
  • 11 Hay A E, Hélesbeux J J, Duval O, Labaïed M, Grellier P, Richomme P. Antimalarial xanthones from Calophyllum caledonicum and Garcinia vieillardii.  Life Sci. 2004;  75 3077-3085
  • 12 Ziegler H L, Stærk D, Christensen J, Hviid L, Hägerstrand H, Jaroszewski J W. In vitro Plasmodium falciparum drug sensitivity assay: inhibition of parasite growth by incorporation of stomatocytogenic amphiphiles into the erythrocyte membrane.  Antimicrob Agents Chemother. 2002;  46 1441-1446
  • 13 Ngouela S, Lenta B N, Noungoue D T, Ngoupayo J, Fekam F B, Tsamo E, Gut J, Rosenthal P J, Connolly J D. Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn f.  Phytochemistry. 2006;  67 302-306
  • 14 Suksamrarn S, Komutiban O, Ratananukul P, Chimnoi N, Lartpornmatulee N, Suksamrarn A. Cytotoxic prenylated xanthones from the young fruit of Garcinia mangostana.  Chem Pharm Bull. 2006;  54 301-305
  • 15 Jung H A, Su B N, Keller W J, Mehta R G, Kinghorn A D. Antioxidant xanthones from the pericarp of Garcinia mangostana (Mangosteen).  J Agric Food Chem. 2006;  54 2077-2082
  • 16 Cedillo-Rivera R, Ramírez A, Muñoz O. A rapid colorimetric assay with the tetrazolium salt MMT and phenazine methosulfate (PMS) for viability of Entamoeba histolytica.  Arch Med Res. 1992;  23 59-61
  • 17 Singh A, Rosenthal P J. Comparison of efficacies of cysteine protease inhibitors against five strains of Plasmodium falciparum.  Antimicrob Agents Chemother. 2001;  45 949-951
  • 18 Lambros C, Vanderberg J P. Synchronization of Plasmodium falciparum erythrocytic stages in culture.  J Parasitol. 1979;  65 418-420

Dr. Bruno Ndjakou Lenta

Department of Chemistry
Higher Teachers' Training College
University of Yaoundé 1

P. O. Box 47

237 Yaoundé

Cameroon

Phone: +23 7 75 09 75 61

Email: lentabruno@yahoo.fr

>