Planta Medica, Inhaltsverzeichnis Planta Med 2006; 72(10): 912-916DOI: 10.1055/s-2006-947190 Original Paper Pharmacology © Georg Thieme Verlag KG Stuttgart · New York Prenylated Xanthones as Potential Antiplasmodial Substances Wilawan Mahabusarakam1 , Kunnika Kuaha2 , Prapon Wilairat3 , Walter C. Taylor4 1Department of Chemistry, Prince of Songkla University, Hat Yai, Songkhla, Thailand 2Department of Immunology, Faculty of Associated Medical Sciences, Khon Kaen University, Khon Kaen, Thailand 3Department of Biochemistry, Faculty of Science, Mahidol University, Bangkok, Thailand 4School of Chemistry, University of Sydney, Sydney, NSW, Australia Artikel empfehlen Abstract Artikel einzeln kaufen Abstract Mangostin, the major xanthone of Garcinia mangostana, and a series of synthetic derivatives were investigated for their in vitro antiplasmodial activity against Plasmodium falciparum. Mangostin itself showed moderate activity, but prenylated xanthones containing alkylamino functional groups exhibited quite potent antiplasmodial activity. Some structure-activity relationships are proposed. Key words Mangostin - G. mangostana - Guttiferae - prenylated xanthones - antiplasmodial - Plasmodium falciparum Volltext Referenzen References 1 Guerin P, Olliaro J P, Nosten F, Druilhe P, Laxminarayan R, Binka F. et al . Malaria: current status of control, diagnosis, treatment, and a proposed agenda for research and development. Lancet Inf Dis. 2002; 2 564-73 2 Liu M, Wilairat P, Croft S L, Tan A LC, Go M L. Structure-activity relationships of antileishmanial and antimalarial chalcones. Bioorg Med Chem 2003: 2729-38 3 Iwasa K, Nishiyama Y, Ichimaru M, Moriyasu M, Kim H S, Wataya Y. et al . Structure-activity relationships of quaternary protoberberine alkaloids having an antimalarial activity. Eur J Med Chem. 1999; 34 1077-83 4 Campell W E, Gammon D W, Smith P, Abrahams M, Purves T D. Composition and antimalarial activity in vitro of the essential oil of Tetradenia riparia . Planta Med. 1997; 63 270-2 5 Murakami N, Mostaqul H M, Tamura S, Itakaki S, Horii T, Kobayashi M. New antimalarial flavonol glycoside from Hydrangeae dulcis folium. Bioorg Med Chem Lett. 2001; 11 2445-7 6 Likhitwitayawuid K, Chanmahasathien W, Ruangrungsi N, Krungkrai J. Xanthones with antimalarial activity from Garcinia dulcis . Planta Med. 1998; 64 281-2 7 Likhitwitayawuid K, Phadungcharoen T, Krungkrai J. Antimalarial xanthones from Garcinia cowa . Planta Med. 1998; 64 70-2 8 Isaka M, Jaturaput A, Rukseree K, Danwisetkanjana K, Tanticharoen M, Thebtaranonth Y. Phomoxanthones A and B, novel xanthone dimers from the endophytic fungus Phomopsis species. J Nat Prod. 2001; 64 1015-8 9 Ignatushchenko M V, Winter R W, Baechinger H P, Hinrichs D J, Riscoe M K. Xanthones as antimalarial agents: studies of a possible mode of action. FEBS Lett. 1997; 409 67-73 10 Kelly J X, Winter R, Peyton D H, Hinrichs D J, Riscoe M. Optimization of xanthones for antimalarial activity: the 3,6-bis-ω-diethylaminoalkoxyxanthone series. Antimicrob Agents Chemother. 2002; 46 144-50 11 Mahabusarakam W, Wiriyachitra P, Phongpaichit S. Antimicrobial activities of chemical constituents from Garcinia mangostana L. J Sci Soc Thailand. 1986; 12 239-42 12 Williams P, Ongsakul M, Proudfoot J, Croft K D, Beilin L. Mangostin inhibits the oxidative modification of human low density lipoprotein. Free Radic Res. 1995; 23 175-84 13 Gopalakrishnan C, Shankaranarayanan D, Kameswaran L, Nazimudeen S KPG. Effect of mangostin, a xanthone from Garcinia mangostana Linn. in immunopathological and inflammatory reactions. Indian J Exp Biol. 1980; 18 843-6 14 Vlietinck A J, De Bruyne T, Apers S, Pieters L A. Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection. Planta Med. 1998; 64 97-109 15 Riscoe M, Kelly J X, Winter R. Xanthones as antimalarial agents: discovery, mode of action and optimization. Curr Med Chem. 2005; 12 2539-49 16 Mahabusarakam W, Proudfoot J, Taylor W C, Croft K. Inhibition of lipoprotein oxidation by prenylated xanthones derived from mangostin. Free Radic Res. 2000; 33 643-59 17 Lu X Z, Hasmeda M, Mahabusarakam W, Ternai B, Ternai P C, Polya G M. Inhibition of eukaryote protein kinases and of a cyclic nucleotide-binding phosphatase by prenylated xanthones. Chem Biol Interact. 1998; 114 121-40 18 Desjardins R E, Canfield C J, Haynes J D, Chulay J C. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob Agents Chemother. 1979; 16 710-8 19 Thaithong S, Beale G H. Resistance of ten Thai isolates of Plasmodium falciparum to chloroquine and pyrimethamine by in vitro tests. Trans R Soc Trop Med Hyg. 1981; 75 271-3 20 Hay A E, Helesbeux J J, Duval O, Labaied M, Grellier P, Richomme P. Antimalarial xanthones from Calophyllum caledonicum and Garcinia vieillardii . Life Sci. 2004; 75 3077-85 21 Fotie J, Nkengfack A E, Rukunga G, Tolo F, Peter M G, Heydenreich M. In-vivo antimalarial activity of some oxygenated xanthones. Ann Trop Med Parasitol. 2003; 97 683-8 W. Mahabusarakam Department of Chemistry Prince of Songkla University Hat Yai Songkhla 90112 Thailand Telefon: +66-74-212-918 Fax: +66-74-212-918 eMail: wilawan.m@psu.ac.th