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Antimicrobial Agents and Chemotherapy, May 1999, p. 1234-1241, Vol. 43, No. 5
0066-4804/99/$04.00+0
Copyright © 1999, American Society for Microbiology. All rights reserved.

Selective Effect of 2',6'-Dihydroxy-4'-Methoxychalcone Isolated from Piper aduncum on Leishmania amazonensis

Eduardo Caio Torres-Santos,1 Davyson Lima Moreira,2 Maria Auxiliadora C. Kaplan,2 Maria Nazareth Meirelles,3 and Bartira Rossi-Bergmann1,*

Instituto de Biofisica Carlos Chagas Filho1 and Núcleo de Pesquisa de Produtos Naturais,2 Universidade Federal do Rio de Janeiro, and Laboratório de Ultraestrutura Celular, Instituto Oswaldo Cruz, FIOCRUZ,3 Rio de Janeiro, Brazil

Received 16 July 1998/Returned for modification 30 September 1998/Accepted 8 March 1999

2',6'-Dihydroxy-4'-methoxychalcone (DMC) was purified from the dichloromethane extract of Piper aduncum inflorescences. DMC showed significant activity in vitro against promastigotes and intracellular amastigotes of Leishmania amazonensis, with 50% effective doses of 0.5 and 24 µg/ml, respectively. Its inhibitory effect on amastigotes is apparently a direct effect on the parasites and is not due to activation of the nitrogen oxidative metabolism of macrophages, since the production of nitric oxide by both unstimulated and recombinant gamma interferon-stimulated macrophages was decreased rather than increased with DMC. The phagocytic activity of macrophages was functioning normally even with DMC concentrations as high as 80 µg/ml, as seen by electron microscopy and by the uptake of fluorescein isothiocyanate-labeled beads. Ultrastructural studies also showed that in the presence of DMC the mitochondria of promastigotes were enlarged and disorganized. Despite destruction of intracellular amastigotes, no disarrangement of macrophage organelles were observed, even at 80 µg of DMC/ml. These observations suggest that DMC is selectively toxic to the parasites. Its simple structure may well enable it to serve as a new lead compound for the synthesis of novel antileishmanial drugs.

* Corresponding author. Mailing address: Instituto de Biofisica Carlos Chagas Filho, Universidade Federal do Rio de Janeiro, 21.949-900 Rio de Janeiro, RJ, Brazil. Phone: 55 (21) 260 6963. Fax: 55 (21) 2808193. E-mail: bbergman{at}ibccf.biof.ufrj.br.

Antimicrobial Agents and Chemotherapy, May 1999, p. 1234-1241, Vol. 43, No. 5
0066-4804/99/$04.00+0
Copyright © 1999, American Society for Microbiology. All rights reserved.


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