Cytotoxic and antibacterial compounds from <i>Schinus terebinthifolia</i> Raddi fruits

Chromatographic procedures of extracts of <i>Schinus terebinthifolia</i> Raddi fruits afforded <i>(Z)</i>-masticadienoic (<b>1</b>) and 3β-masticadienolic (<b>2</b>) acids, tetrahydroamentoflavone (<b>3</b>), and 4-<i>O</i>-methyl gallic acid (<b>4</b>). Addicionally, the derivative 6-oxo masticadienoic acid (<b>1a</b>) 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 <i>in vitro</i> cytotoxicity against the A549 human lung cancer cell line, as well as antimicrobial activity tests. Compounds <b>2</b> and <b>1a</b> 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 <i>Escherichia coli</i>, <i>Staphylococcus aureus</i>, and <i>Pseudomonas aeruginosa.</i> Except for 4-<i>O</i>-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.