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Semisynthetic Phenol Derivatives Obtained from Natural Phenols: Antimicrobial Activity and Molecular Properties

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journal contribution
posted on 29.12.2017, 21:04 by Patrícia Fontes Pinheiro, Luciana Alves Parreira Menini, Patrícia Campos Bernardes, Sérgio Henriques Saraiva, José Walkimar Mesquita Carneiro, Adilson Vidal Costa, Társila Rodrigues Arruda, Mateus Ribeiro Lage, Patrícia Martins Gonçalves, Carolina de Oliveira Bernardes, Elson Santiago Alvarenga, Luciano Menini
Semisynthetic phenol derivatives were obtained from the natural phenols: thymol, carvacrol, eugenol, and guaiacol through catalytic oxychlorination, Williamson synthesis, and aromatic Claisen rearrangement. The compounds characterization was carried out by 1H NMR, 13C NMR, and mass spectrometry. The natural phenols and their semisynthetic derivatives were tested for their antimicrobial activity against the bacteria: Staphylococcus aureus, Escherichia coli, Listeria innocua, Pseudomonas aeruginosa, Salmonella enterica Typhimurium, Salmonella enterica ssp. enterica, and Bacillus cereus. Minimum inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) values were determined using concentrations from 220 to 3.44 μg mL–1. Most of the tested compounds presented MIC values ≤220 μg mL–1 for all the bacteria used in the assays. The molecular properties of the compounds were computed with the PM6 method. Through principle components analysis, the natural phenols and their semisynthetic derivatives with higher antimicrobial potential were grouped.