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

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

  • J Agric Food Chem. 2018 Jan 10;66(1):323-330. doi: 10.1021/acs.jafc.7b04418.
Patrícia Fontes Pinheiro,  Luciana Alves Parreira Menini,  Patrícia Campos Bernardes,  Sérgio Henriques Saraiva,  José Walkimar Mesquita Carneiro 1,  Adilson Vidal Costa,  Társila Rodrigues Arruda,  Mateus Ribeiro Lage 2,  Patrícia Martins Gonçalves,  Carolina de Oliveira Bernardes 3,  Elson Santiago Alvarenga 4,  Luciano Menini 5
Affiliations

Affiliations

  • 1 Department of Inorganic Chemistry, Federal Fluminense University Outeiro São Batista , CEP-24020-141 Niterói, Rio de Janeiro, Brazil.
  • 2 Federal University of Maranhão, Campus Rua José Leão, 484, Center , CEP-65800-000 Balsas, Maranhão, Brazil.
  • 3 Federal University of the Espírito Santo, Alto Universitário , 29500-000 Alegre, Espírito Santo, Brazil.
  • 4 Department of Chemistry, Federal University of Viçosa , Avenida Peter Henry Rolfs, s/n, 36570-900 Viçosa, Minas Gerais, Brazil.
  • 5 Laboratory of Applied Chemistry, Federal Institute of Education, Science, and Technology of Espírito Santo , Rodovia 482, Cachoeiro/Alegre, km 47 Distrito de Rive, 29500-000 Alegre, Espírito Santo, Brazil.
PMID: 29286652 DOI: 10.1021/acs.jafc.7b04418
Abstract

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.

Keywords

antimicrobial activity; chlorophenol; natural phenols; semisynthetic phenols.

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