Estudo químico e biológico de Cordia trichotoma (Vell) Arrab. ex Steud

Abstract

This work describes the phytochemical reinvestigation of Cordia trichotoma (Vell.) Arrab. ex Steud, belonging to the Boraginaceae family. Studies report pharmacological and/or biological activities, such as bactericidal, antifungal, larvicidal against Aedes aegypti and anti-inflammatory, for some species of the genus Cordia. Thus, this study aimed to contribute to the phytochemical knowledge of C. trichotoma, through the isolation and structural characterization of the secondary metabolites of the species. The chemical investigation of the hexane (CTCH) and ethanolic extracts of the heartwood (CTCE) resulted in the isolation of a new sesquiterpene 8,11-epoxy-cadi-3-9-ene (CT6), together with seven sesquiterpenes already described in the literature, -cadinol (CT1); 1,,trihydroxyeudesmane (CT2); 1,,trihydroxyeudesmane (CT3); 1,,,tetrahydroxyeudesmane (CT4); 1,,-trihydroxyoppositane (CT5), 15-oxo--cadinol (CT7), and canangaterpene III (CT8). In addition, they include two phenylpropanoids, 3-(2',4',5'-trimethoxyphenyl)-propanoic acid (CT9) and methyl 3-(2',4',5'-trimethoxyphenyl)-propanoate (CT10). The sesquiterpenes CT4, CT7 and CT8 are being described for the first time in the genus Cordia. The structures of the isolated compounds were characterized through analysis of 1D (1H, 13C and DEPT) and 2D (COSY, HMQC and HMBC) NMR data and comparison with data described in the literature. The acetylcholinesterase inhibitory activity of CTCH, CTCE, hexane fraction of the liquid-liquid partition of ethanolic heartwood extract (CTCEH), dichloromethane fraction of the liquid-liquid partition of ethanolic heartwood extract (CTCED), the ethyl acetate fraction of the liquid-liquid partition of the ethanolic heartwood extract (CTCEA), together with the isolated compounds CT1, CT2, CT3, CT4, CT5 and CT6 were evaluated and among CTCH, CTCE, CTCEH, CTCED and CTCEA showed satisfactory results. The extracts in hexane and ethanol (CTCH and CTCE) were evaluated for cytotoxicity on the human tumor lines HCT 116 (colorectal carcinoma), NCI-H1299 (non-small cell lung cancer) and K562 (chronic myeloid leukemia) and larvicidal activity against Aedes aegypti, in both, only the hexane heartwood extract (CTCH) exhibited low cytotoxic potential in human tumor lines and strong potential as a natural larvicidal agent.