Planta Med 2006; 72(3): 270-272
DOI: 10.1055/s-2005-916179
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Minor Alkaloids From Guatteria dumetorum with Antileishmanial Activity

Jhonny Edmith Correa1 , Carlos Hernán Ríos1 , Amparo del Rosario Castillo2 , Luz I. Romero2 , Eduardo Ortega-Barría2 , Phyllis D. Coley3 , 4 , Thomas A. Kursar3 , 4 , Maria Verónica Heller4 , William H. Gerwick5 , Luis Cubilla Rios1
  • 1Laboratorio de Bioorgánica Tropical, Universidad de Panamá, República de Panamá
  • 2Instituto de Investigaciones Científicas Avanzadas y Servicios de Alta Tecnología, República de Panamá
  • 3Department of Biology, University of Utah, XXX, Utah, USA
  • 4Instituto Smithsonian de Investigaciones Tropicales, República de Panamá
  • 5College of Pharmacy, Oregon State University, Corvallis, Oregon, USA
Further Information

Publication History

Received: May 14, 2005

Accepted: July 22, 2005

Publication Date:
05 December 2005 (online)

Abstract

Nine known alkaloids [(+)-isodomesticine (1), (+)-norisodomesticine (2), (+)-nantenine (3), (+)-neolitsine (4), (+)-lirioferine (5), (+)-N-methyllaurotetanine (6), (+)-norlirioferine (7), (+)-isoboldine (8) and (+)-reticuline (9)] were isolated from young leaves of Guatteria dumetorum. Their structures were confirmed by NMR, mass and UV spectral analysis and by comparison to literature data. The growth inhibitory activity of each alkaloid was determined against the parasite Leishmania mexicana. Compounds 1 - 4 all showed significant activity whereby potency increased when a methylenedioxy functionality was present, especially at the 1,2-positions.

References

  • 1 Montenegro H, Gutiérrez M, Romero L I, Ortega-Barría , Capson T L, Cubilla L. Aporphine alkaloids from Guatteria spp. with leishmanicidal activity.  Planta Med. 2003;  69 677-9
  • 2 Berman J. Recent developments in leishmaniasis: epidemiology, diagnosis, and treatment.  Curr Infect Dis Rep. 2005;  7 33-8
  • 3 Li D, Zhao B, Sim S P, Li T K, Liu A, Liu L F. et al . 2,3-Dimethoxybenzo[i]phenanthridines: topoisomerase I-targeting anticancer agents.  Bioorg Med Chem. 2003;  11 521-8
  • 4 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
  • 5 Werbovetz A, Bhattacharjee K, Brendle J, Scovil P. Analysis of stereoelectronic properties of camptothecin analogues in relation to biological activity.  Bioorg Med Chem. 2000;  8 1741-7
  • 6 Guinaudeau H, Leboeuf M, Cave A. Aporphine alkaloids.  J Nat Prod. 1975;  38 275-335
  • 7 Hocquemiller R, Cave A, Raharisololalao A. Alcaloides de Xylopya buxifolia et de Xylopia danguyella .  J Nat Prod. 1981;  44 551-6
  • 8 Chen C L, Chang H M, Cowling E, Huang C Y, Gates R. Aporphine alkaloids and lignans formed in response to injury of sapwood in Liriodendron tulipifera .  Phytochemistry. 1976;  15 1161-7
  • 9 Castro O, López J, Vergara A. Aporphine alkaloids from Phoebe pittieri .  Phytochemistry. 1985;  24 203-4
  • 10 Gellert E, Summons R E. Alkaloids of the genus Cinnamomum. II. Alkaloids of the bark of Cinnamomum sp. T.G.H. 13 077.  Aust J Chem. 1970;  23 2095-9
  • 11 Williams C, Espinosa O A, Montenegro H, Cubilla L, Capson T L, Ortega-Barría E. et al . Hydrosoluble formazan XTT: its application to natural products drug discovery for Leishmania .  J Microbiol Methods. 2003;  55 813-6
  • 12 Golenser J, Frankenburg S, Enrenfreund T, Domb A J. Efficacious treatment of experimental leishmaniasis with amphotericin B-arabinogalactan water-soluble derivatives.  Antimicrob Agents Chemother. 1999;  43 2209-14
  • 13 Shin I S, Tanifuji H, Arata Y, Morizawa Y, Nakayama T, Wataya Y. 3′-Deoxy-3′-fluoroinosine as a potent antileishmanial agent. The metabolism and selective cytotoxic effect of 3′-deoxy-3′-fluoroinosine against Leishmania tropica and L. donovani in vitro and in vivo .  Parasitol Res. 1995;  81 622-6
  • 14 Sahpaz S, Bories C, Loiseau P M, Cortes D, Hocquemiller R, Laurens A. et al . Cytotoxic and antiparasitic activity from Annona senegalensis seeds.  Planta Med. 1994;  60 538-40

Dr. Luis Cubilla Rios

Departamento de Química Orgánica

Apdo. 0824 - 10 835

Universidad de Panamá

Panama City

Republic of Panamá

Phone: +507-6681-5371

Fax: +507-264-4450

Email: lucr@ancon. up.ac.pa