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Synthesis, antioxidant and antimicrobial evaluation of simple aromatic esters of ferulic acid

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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 (IC50 of 0.19, 0.27 and 0.20 mM, respectively) was found to be twice as active as α-tocopherol (IC50 = 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.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330, Etiler, Ankara, Turkey

    Burcu Çaliskan Ergün & Erden Banoglu

  2. Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Ankara University, 06100, Tandogan, Ankara, Turkey

    Tülay Çoban

  3. Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Gazi University, 06330, Etiler, Ankara, Turkey

    Fatma Kaynak Onurdag

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  1. Burcu Çaliskan Ergün
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  2. Tülay Çoban
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  4. Erden Banoglu
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Correspondence to Erden Banoglu.

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Ergün, B.Ç., Çoban, T., Onurdag, F.K. et al. Synthesis, antioxidant and antimicrobial evaluation of simple aromatic esters of ferulic acid. Arch. Pharm. Res. 34, 1251–1261 (2011). https://doi.org/10.1007/s12272-011-0803-y

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  • DOI: https://doi.org/10.1007/s12272-011-0803-y

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