Antiparasitic activities of acridone alkaloids from Swinglea glutinosa (Bl.) Merr.

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Abstract

Onze alcalóides acridônicos isolados de Swinglea glutinosa (Bl.) Merr. foram avaliados para suas atividades in vitro contra linhagens de Plasmodium falciparum sensíveis a cloroquina 3D7, Trypanosoma brucei rhodesiense STIB9000 e Leishmania donovani L82. Ensaios com células KB foram também executados com o objetivo de se determinar o grau de toxicidade das substâncias ativas contra os parasitas. Nove dos compostos apresentaram IC50 entre 0,3 e 11,6 μM contra P. falciparum. Em contraste, um pequeno número de compostos mostrou atividade significativa contra T. brucei rhodesiense e nenhum apresentou atividade contra L. donovani. Entre os alcalóides três tiveram IC50 < 1,0 μM contra P. falciparum, enquanto que contra T. b. rhodesiense cinco mostraram IC50 < 10 μM. A caracterização dos alcalóides, 1,3,5-triidróxi-4-metóxi-10-metil-2,8-bis(3-metilbut-2-enil)acridin-9(10H)-ona (1), 2,3-diidro-4,9-diidróxi-2-(2-hidróxipropan-2-il)-11-metóxi-10-metilfuro[3,2-b]acridin-5(10H)-ona (2) e 3,4-diidro-3,5,8-triidróxi-6-metóxi-2,2,7-trimetil-2H-pirano[2,3-a]acridin-12(7H)-ona (3), é aqui discutida. Discute-se também a relação estrutura-atividade para todos os compostos ensaiados. O isolamento e dados espectrais para os alcalóides 1-3 estão sendo aqui descritos pela primeira vez, embora em trabalho anterior tenham sido relatadas as suas atividades citotóxicas. Eleven acridone alkaloids isolated from Swinglea glutinosa (Bl.) Merr. were examined for in vitro activity against chloroquine-sensitive Plasmodium falciparum 3D7, Trypanosoma brucei rhodesiense STIB900 and Leishmania donovani L82. An assay with KB cells was developed in order to compare in vitro toxicity of alkaloids with the selective action on the parasites. Nine of the compounds had IC50 values ranging from 0.3 to 11.6 μM against P. falciparum. In contrast, a small number of compounds showed significant activity against T. brucei rhodesiense and none had activity against L. donovani. Among the alkaloids three had IC50 < 1.0 μM against P. falciparum, whereas against T. b. rhodesiense five had IC50 < 10 μM. The characterization of the acridone alkaloids, 1,3,5-trihydroxy-4-methoxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9(10H)-one (1), 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-methoxy-10-methylfuro[3,2-b]acridin-5(10H)-one (2) and 3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2H-pyrano[2,3-a]acridin-12(7H)-one (3), is discussed, as well as the structure-activity relationship of all compounds assayed. Isolation and spectral data of alkaloids 1-3 are described for the first time although their citotoxicities to cancer cells have been described before. © 2009 Sociedade Brasileira de Química.

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dos Santos, D. A. P., Vieira, P. C., da Silva, M. F. das G. F., Fernandes, J. B., Rattray, L., & Croft, S. L. (2009). Antiparasitic activities of acridone alkaloids from Swinglea glutinosa (Bl.) Merr. Journal of the Brazilian Chemical Society, 20(4), 644–651. https://doi.org/10.1590/s0103-50532009000400008

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