Estudo químico e avaliação do potencial efeito biológico das folhas e flores de Hymenaea stigonocarpa Mart. ex Hayne (Fabaceae)

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Universidade Federal de Goiás


The Brazilian Savannah is rich in plant species, and that is why it is promising to study natural products (NPs) which can act as sources for the development of new drugs, such as chemotherapeutic and chemopreventive agents, and inhibitors of enzymes such as cathepsins, which are lysosomal proteases with beneficial functions but are also involved in pathological processes (cancer, arthritis, osteoporosis, immune disorders and viral infections). Although these enzymes have been studied as targets for drug development, few inhibitors based on NPs have been described in the literature. In this work the chemical-biological study of Hymenaea stigonocarpa was carried out in the search for potential secondary metabolites capable of inhibiting the activity of cathepsins K, L and V as well as the viability of tumor cells S-180 and Ehrlich. By means of chromatographic techniques, 5 substances were isolated from the leaf extract, which have not been previously reported to H. stigonocarpa: labd-7,13-dien-15-oic acid (I), labd-7-en-15-oic acid (II), ent-Δ13,14-labd-8-β-ol-15-oic acid (III), 4’,5,7-trihydroxy-3’,5-dimethoxyflavone (IV) and p-hydroxybenzoic acid (V), along with one substance obtained from the flower extract, which has not been described in the literature: 18-hydroxy-ent-halima-1(10),13-E-dien-15-oic acid (VI). Therefore, this study has contributed to enrich the knowledge of NPs produced by this species. The diterpenoids I and III were assayed for their cytotoxic potential, showing unsatisfactory IC50 values. However, studies have shown that labdane and halimane diterpenoids possess potent cytotoxic effect and that substance IV, isolated in this work, can be considered to have pronounced anticancer activity, making this species promising in the search for compounds capable of inhibiting tumor cells viability. Compounds I, III, III* (methyl ester of III), IV, V and VI were tested against cathepsins K, L and V. The most significant results were observed for compounds I, IV, V and VI against cathepsin V; I and V against the cathepsin L and I against cathepsin K. The inhibitory potency values of these compounds were determined and the most significant results were observed for compound IV (IC50 = 2.9 and 36.9 mM) against cathepsins V and L, respectively. Literature data have reported significant inhibitory activities for flavonoids against cathepsin K, indicating, together with the results obtained in this work, the need for further studies of H. stigonocarpa in the search for cysteine proteases inhibitors.



Cerrado, Hymenaea stigonocarpa, Produtos naturais, Atividade biológica, Natural products, Biological activity


MONTEIRO, A. F. Estudo químico e avaliação do potencial efeito biológico das folhas e flores de Hymenaea stigonocarpa Mart. ex Hayne (Fabaceae). 2014. 157 f. Dissertação (Mestrado em Química) - Universidade Federal de Goiás, Catalão, 2014.