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

Abstract

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, it was evaluated the cytotoxicity of C. atramentaria extract, previously identified organic acids and their synthesized derivatives (methylated compounds and protected glucuronides). 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.

The contribution of phenolic acids to the anti-inflammatory activity of mushrooms: Screening in phenolic extracts, individual parent molecules and synthesized glucuronated and methylated derivatives

“…Piazzon et al (2012), as well as our research group (Heleno et al, 2013a(Heleno et al, , 2014a, described the chemical or enzymatic synthesis of glucuronated, sulphated and methylated derivatives of several phenolic acids, obtaining structures similar to those formed in vivo after phenolic acid metabolism (Figure 6-8). (Heleno et al, 2013a); ii) Methylation of CA.…”

“…All the glucuronated, methylated and sulphated compounds mentioned above, and the respective parental phenolic acids, were studied for their bioactivities namely, antioxidant (Piazzon et al, 2012), antimicrobial (Heleno et al, 2013a(Heleno et al, , 2014a and antitumor (Heleno et al, 2014a) properties, in order to compare the biological activities of the parental compounds before and after in vivo metabolism. Oludemi Taofiq Ayodele…”

Comparative bioactive properties of Coprinopsis atramentaria extract, organic acids and synthesized derivatives

“…Furthermore, methylated and glucuronated derivatives of the mentioned compounds were synthetized and their bioactivities were evaluated and compared with those of the parental molecules and extract. In almost all of the cases the glucuronated and methylated derivatives increased the bioactivities of the parental compounds, revealing stronger properties than the extract, the parental compounds and, in the case of antimicrobial properties, even than the standards used [3]. This report allows the comparison between parental compounds and meta bolite derivatives.…”

Coprinopsis atramentaria extract, its organic acids, and synthesized glucuronated and methylated derivatives as antibacterial and antifungal agents

“…Methylated and glucuronated derivatives ( Figure 1) were synthesized and completely characterized as described previously by the authors, 10 and used in the antimicrobial assays.…”

“…Redhead, Vilgalys & Moncalvo, is a wild edible mushroom previously characterized by us for its nutritional composition, and its methanolic extract showed antioxidant 9 and antitumor activities. 10 p-Hydroxybenzoic (4.71 mg/100 g dry weight), p-coumaric (0.82 mg/100 g) and cinnamic (1.70 mg/100 g) acids were identified in the mentioned extract. Nonetheless, the mentioned compounds are rapidly metabolized in the human organism.…”