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

Abstract

Despite the available data regarding antimicrobial activity of phenolic acids, studies dealing with the effects of their metabolites or derivatives are scarce. Therefore, the antimicrobial and demelanizing activities of Coprinopsis atramentaria extract, its organic acids, and methylated and glucuronated derivatives were evaluated. The antifungal activity was stronger than the antibacterial effects. In general, individual compounds (mostly organic acids) gave higher activity than the extract and even higher than the standards used in the assays. Methylated derivatives presented the highest demelanizing activity toward Aspergillus niger, A. fumigatus and Penicillium verrucosum var. cyclopium). The inclusion of methyl groups in the parental compound (CoAM1, CoAM2and CoAM3) strongly increased antibacterial and antifungal activities of CoA, while the inclusion of acetyl groups (CoAGP) increased the antifungal activity but the antibacterial properties were maintained. For HA and CA, the inclusion of methyl groups (HAM1, HAM2, HAM3 and CAM) increased the demelanizing activity, but decreased the antimicrobial properties. The present work contributes to the knowledge of the mechanisms involved in the antimicrobial properties of organic acids namely, phenolic acids, usually present in mushrooms. Organic acids, methylated and glucuronated derivatives could be used as antimicrobial agents.

Plant Phytochemicals in Food Preservation: Antifungal Bioactivity: A Review

“…2), shows antifungal activity against Aspergillus and Penicillium, with a remarkable demelanizing activity over Aspergillus niger, Aspergillus fumigatus, and Penicillium verrucosum var. cyclopium, an effect that is interesting as melanin is an important factor in fungal virulence (35).…”

An Apple Fruit Fermentation (AFF) Treatment Improves the Composition of the Rhizosphere Microbial Community and Growth of Strawberry (Fragaria × ananassa Duch ‘Benihoppe’) Seedlings

“…licheniformis in the fermentation process. Coprinus atramentarius , has been reported to secrete organic acids and other active substances that act as antibacterial agents [ 40 ]. In Camellia sinensis , adding B .…”

Natural Sources, Pharmacokinetics, Biological Activities and Health Benefits of Hydroxycinnamic Acids and Their Metabolites

“…On the other hand, there have not been many studies describing the antimicrobial properties of HCAs’ metabolites ( Table 1 ) up to date. Due to commercial unavailability, Heleno and coauthors synthesized protected forms of cinnamic and p -coumaric glucuronides and methylated metabolites to compare their antimicrobial activities with parent HCAs against many Gram-positive ( S. aureus , B. cereus , L. monocytogenes , M. flavus ), and Gram-negative bacteria ( P. aeruginosa , E. coli , S. typhimurium , E. cloacae ), and fungi [ 63 , 150 , 151 ]. Concerning the antibacterial activity, only the glucuronide protected form of p -coumaric acid retained antibacterial activity of the parent acid, whereas 2,3,4-tri-O-acetyl-1-cinnamoyl-D-glucuronic acid methyl ester showed lower activity than the parent compound.…”

“…On the other hand, the measurement of antifungal activity disclosed higher potency compared to the respective parent HCAs against the majority of the evaluated fungi. Similarly, methylated derivatives of p -coumaric acid exhibited mostly higher antibacterial and antifungal activities than p -coumaric acid itself [ 63 , 150 ].…”