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Evidence-Based Complementary and Alternative Medicine
Volume 2013 (2013), Article ID 761323, 13 pages
http://dx.doi.org/10.1155/2013/761323
Research Article

Trans-β-Caryophyllene: An Effective Antileishmanial Compound Found in Commercial Copaiba Oil (Copaifera spp.)

1Laboratório de Imunobiologia das Leishmanioses, Instituto de Microbiologia Paulo de Góes, Universidade Federal do Rio de Janeiro, Avenida Carlos Chagas Filho 373, Bloco D, Sala D1-44, Ilha do Fundão, 21941-902 Rio de Janeiro, RJ, Brazil
2Faculdade de Farmácia, Centro de Ciências da Saúde, Bloco K, 2° Andar, Universidade Federal do Rio de Janeiro, Cidade Universitária, Ilha do Fundão, 21941-902 Rio de Janeiro, RJ, Brazil
3Departamento de Produtos Naturais, Instituto de Tecnologia em Fármacos, Fundação Oswaldo Cruz, Rua Sizenando Nabuco 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil

Received 11 March 2013; Accepted 1 June 2013

Academic Editor: Marco Leonti

Copyright © 2013 Deivid C. Soares et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

This study investigated the leishmanicidal activity against Leishmania amazonensis of four commercial oils from Copaifera spp. named as C1, C2, C3, and C4, the sesquiterpene and diterpene pools obtained from distilling C4, and isolated β-caryophyllene (CAR). Copaiba oils chemical compositions were analyzed by gas chromatography and correlated with biological activities. Diterpenes-rich oils C2 and C3 showed antipromastigote activity. Sesquiterpenes-rich C1 and C4, and isolated CAR presented a dose-dependent activity against intracellular amastigotes, with IC50s of 2.9 µg/mL, 2.3 µg/mL, and 1.3 µg/mL (6.4 µM), respectively. Based on the highest antiamastigote activity and the low toxicity to the host cells, C4 was steamdistillated to separate pools of sesquiterpenes and diterpenes. Both pools were less active against L. amazonensis and more toxic for the macrophages than the whole C4 oil. The leishmanicidal activity of C3 and C4 oils, as well as C4 fractions and CAR, appears to be independent of nitric oxide production by macrophages. This study pointed out β-caryophyllene as an effective antileishmanial compound and also to its role as potential chemical marker in copaiba oils or fractions derived thereof, aiming further development of this rainforest raw material for leishmaniasis therapy.