Cytotoxicity of Coprinopsis atramentaria extract, organic acids and their synthesized methylated and glucuronate derivatives

•Protected glucuronide derivatives of organic acids were synthesized.•The compounds revealed higher antimicrobial activity than commercial standards.•The compounds revealed higher antimicrobial activity than G. lucidum extract.•The extract was the only one with demelanizing activity against A. niger.•The compounds could be deprotected to obtain glucuronide metabolites.

Coprinopsis atramentaria is a wild edible mushroom whose methanolic extract revealed a marked antioxidant activity; p-hydroxybenzoic (HA), p-coumaric (CoA) and cinnamic (CA) acids were identified in the extract. In the present work, the cytotoxicity of C. atramentaria extract, previously identified organic acids and their synthesized derivatives (methylated compounds and protected glucuronides) was evaluated. Among all the tested cell lines (MCF-7-breast adenocarcinoma, NCI-H460-non-small cell lung carcinoma, HCT15-colon carcinoma, HeLa-cervical carcinoma and HepG2-hepatocellular carcinoma), the extract presented good activity for the first three cell lines mentioned; in most of the cases methylated and glucuronide derivatives showed a higher activity than the corresponding parental compounds. The substitution of the carboxylic group (in parental organic acids) for an ester (in methylated derivatives) increased the cytotoxicity for tumor cell lines. Acetylated glucuronide derivatives showed higher cytotoxicity when compared with the corresponding parental acids.