Cytotoxic and antibacterial compounds from Schinus terebinthifolia Raddi fruits.

Abstract

Chromatographic procedures of extracts of Schinus terebinthifolia Raddi fruits afforded (Z)-masticadienoic (1) and 3β-masticadienolic (2) acids, tetrahydroamentoflavone (3), and 4-O-methyl gallic acid (4). Addicionally, the derivative 6-oxo masticadienoic acid (1a) was prepared by an allylic oxidation. The chemical structures of obtained compounds were elucidated by spectrometric data analyses. Furthermore, both the semi-synthetic derivative and the metabolites were subjected to in vitro cytotoxicity against the A549 human lung cancer cell line, as well as antimicrobial activity tests. Compounds 2 and 1a exhibited cytotoxicity towards A549 cells with IC50 values of 20.13 and 6.11 µM, respectively. In the tests against pathogens, the CHCl₃ and EtOAc soluble fractions of MeOH extract along with the pure compounds, exhibited antibacterial activity against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. Except for 4-O-methyl gallic acid, the other pure compounds showed inhibitory microbial activities with MIC values ranging from 0.25 μg/mL to 25 μg/mL doses.