title: Synthesis, antioxidant and antimicrobial evaluation of simple aromatic esters of ferulic acid.
abstract: Aromatic ester derivatives of ferulic acid where the phenolic hydroxyl is free (6a-d) or acetylated (5a-d) were evaluated for their antioxidant and antimicrobial properties. The superoxide radical scavenging capacity of compounds 5d and 6d-e (IC(50) of 0.19, 0.27 and 0.20 mM, respectively) was found to be twice as active as α-tocopherol (IC(50) = 0.51 mM). DPPH radical scavenging capacity was moderate and only found in compounds bearing free phenolic hydroxyl groups (6a-e). With regard to antimicrobial properties, compounds 6b and 6c displayed significant activity against Enterococcus faecalis (MICs = 16 μg/mL) and vancomycin-resistant E. faecalis (MIC for 6b, 32 and for 6c, 16 μg/mL). Compound 6c also demonstrated prominent activity against planktonic Staphylococcus aureus with a MIC value of <8 μg/mL and it inhibited bacterial biofilm formation by S. aureus with a MBEC value of <8 μg/mL, which was 64 and 128 times more potent than ofloxacin and vancomycin, respectively.
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330 Etiler, Ankara, Turkey.
authors: Burcu Caliskan
authors: BC
authors: Ergün
authors: Tülay
authors: T
authors: Coban
authors: Fatma Kaynak
authors: FK
authors: Onurdag
authors: Erden
authors: E
authors: Banoglu
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018441:Biofilms / Q000187:drug effects; D001713:Biphenyl Compounds / Q000378:metabolism; D002176:Candida albicans / Q000187:drug effects; D003373:Coumaric Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013293:Enterococcus faecalis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D004952:Esters; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D007711:Klebsiella pneumoniae / Q000187:drug effects; D015227:Lipid Peroxidation; D008826:Microbial Sensitivity Tests; D010851:Picrates / Q000378:metabolism; D013211:Staphylococcus aureus / Q000187:drug effects; D013481:Superoxides / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D003373:Coumaric Acids; D004952:Esters; D016166:Free Radical Scavengers; D010851:Picrates; D013481:Superoxides; C004999:ferulic acid; C004931:1,1-diphenyl-2-picrylhydrazyl