Four anti-protozoal and anti-bacterial compounds from Tapirira guianensis

Four cyclic alkyl polyol derivatives have been isolated from a CH 2Cl 2 extract of Tapirira guianensis bark. Their anti-leishmanial, anti-plasmodial, anti-bacterial and anti-fungal activities were evaluated in vitro. Tapirira guianensis is a common tree used in traditional medicine in French Guiana against several infectious diseases (malaria, leishmaniasis, bacteria, etc.). The bioassay-guided purification of CH 2Cl 2 bark extract led to the isolation of four cyclic alkyl polyol derivatives: 4,6,2′-trihydroxy-6-[10′(Z)-heptadecenyl]-1-cyclohexen-2-one (1a), 1,4,6-trihydroxy-1,2′-epoxy-6-[10′( Z)-heptadecenyl]-2-cyclohexene (1b), 1,4,5,2′-tetrahydroxy-1-[10′(Z)-heptadecenyl]-2-cyclohexene (2), and 1,3,4,6-tetrahydroxy-1,2′-epoxy-6-[10′( Z)-heptadecenyl]-cyclohexane (3). The structures were established on the basis of 1D and 2D NMR analyses. The anti-leishmanial, anti-plasmodial, anti-bacterial (on Staphylococcus aureus, Staphylococcus epidermidis and Escherichia coli), and anti-fungal (on Candida albicans) activities of the extracts and of these original compounds were evaluated. Two showed medicinal interest supporting the traditional uses of the plant. The structures were established through spectral analyses of the isolates and their derivatives.