Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters

• Published in: Food and chemical toxicology Vol. 58; pp. 95 - 100
• Main Authors: Heleno, Sandrina A., Ferreira, Isabel C.F.R., Esteves, Ana P., Ćirić, Ana, Glamočlija, Jasmina, Martins, Anabela, Soković, Marina, Queiroz, Maria João R.P.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01-08-2013; Elsevier
• Subjects: Acetylated glucuronides; Acetylation; acids; anti-infective agents; Anti-Infective Agents - pharmacology; anti-infective properties; Antimicrobial activity; Aspergillus niger; Benzoates - chemistry; Benzoates - pharmacology; Biological and medical sciences; Chemical synthesis; Cinnamates - chemistry; Cinnamates - pharmacology; Cinnamic acid; Esters; Ganoderma lucidum; Glucuronides - chemistry; humans; Magnetic Resonance Spectroscopy; Medical sciences; medicinal fungi; Melanins - metabolism; metabolism; metabolites; mushrooms; p-Hydroxybenzoic acid; Plant Extracts - pharmacology; Reishi - chemistry; Spectrometry, Mass, Electrospray Ionization; Toxicology; Ganoderma lucidum; Acetylated glucuronides; Antimicrobial activity; p-Hydroxybenzoic acid; Chemical synthesis; Cinnamic acid; Phenolic acid; Activity; Extract; Antimicrobial agent; Glucuroconjugate; Basidiomycota; Fungi; Ester; Antibacterial agent; Ganoderma
• ISSN: 0278-6915; 1873-6351
• DOI: 10.1016/j.fct.2013.04.025

•Protected glucuronide derivatives of p-hydroxybenzoic and cinnamic 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 acetylated glucuronide derivatives could be deprotected to obtain glucuronide metabolites.
Mushroom extracts or isolated compounds may be useful in the search of new potent antimicrobial agents. Herein, it is described the synthesis of protected (acetylated) glucuronide derivatives of p-hydroxybenzoic and cinnamic acids, two compounds identified in the medicinal mushroom Ganoderma lucidum. Their antimicrobial and demelanizing activities were evaluated and compared to the parent acids and G. lucidum extract. p-Hydroxybenzoic and cinnamic acids, as also their protected glucuronide derivatives revealed high antimicrobial (antibacterial and antifungal) activity, even better than the one showed by commercial standards. Despite the variation in the order of parent acids and the protected glucuronide derivatives, their antimicrobial activity was always higher than the one revealed by the extract. Nevertheless, the extract was the only one with demelanizing activity against Aspergillus niger. The acetylated glucuronide derivatives could be deprotected to obtain glucuronide metabolites, which circulate in the human organism as products of the metabolism of the parent compounds.