Estudo dos metabólitos secundários e atividade antifúngica em resíduos madeireiros de Hymenaea courbaril L.

Abstract

Brazil has an extensive forest area, with a diversity of tree species. There are reports of several chemical studies in order to identify substances with economic and biological potential in the different vegetative parts, such as leaves, bark, fruit, resin and seeds, however most of the explored species do not have chemical studies of the secondary metabolites. found in wood. Among the plant families is Fabaceae, which is the third largest family of angiosperms, chemically characterized by compounds such as alkaloids, lignans, terpenes, among others. The species selected for this work was Hymenaea courbaril L. in order to evaluate the chemical constituents of wood residues (heartwood) and to search for biological activity of the isolated substances. The phytochemical study used column chromatographic techniques (silica gel and sephadex LH-20 stationary phases), in a thin and preparative layer, using the nuclear magnetic resonance spectroscopic technique (one- and two-dimensional) and low resolution mass spectrumetry. With the fractionation of the hexane extract, the purification of the eperúic acid diterpene (1) was obtained, which constitutes about 8% of this extract. Fractionation with the methanolic extract led to the isolation of diterpene (1) and its methyl ester (2), the triterpenes oleanolic acid (3) and hederagenin (10), the derivatives of resorcinol metoxikermadecine H (4) and kermadecine H (5), and the flavonoids quercetin (6), fisetinediol (7), liquerythigenin (8), and 3-methoxy-5,7,3',5'-tetrahydroxiflavanone (9). Since the substances metoxikermadecine H and 3-methoxy-5,7,3',5'-tetrahydroxyflavane are unprecedented in the literature. Considering the need for new antifungal agents of natural origin and the biological potential of the classes of flavonoids, terpenes and resorcinol derivatives, an antifungal test was carried out with substances 1, 2, 4, 5, 6 and 9 isolated from wood residues against Candida albicans (ATCC 60193) and Cryptococcus gattii (CFP 61), where kermadecine H (5) stood out among the tested substances.