These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


PUBMED FOR HANDHELDS

Search MEDLINE/PubMed


  • Title: Anti-tyrosinase, antioxidant, and antibacterial activities of novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans.
    Author: Xia L, Idhayadhulla A, Lee YR, Wee YJ, Kim SH.
    Journal: Eur J Med Chem; 2014 Oct 30; 86():605-12. PubMed ID: 25218909.
    Abstract:
    Novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans (7a-k) were synthesized using ceric ammonium nitrate (CAN)-catalyzed formal [3 + 2] cycloaddition. Synthesized compounds were evaluated for their tyrosinase inhibitory, antioxidant, and antibacterial activities. A modified spectrophotometric method using l-DOPA as substrate was used to determine tyrosinase inhibitory activities, and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay was used to evaluate antioxidant properties. Antibacterial activities against gram-negative Escherichia coli (KCTC-1924) and gram-positive Staphylococcus aureus (KCTC-1916) were evaluated using the disc diffusion technique. Of the synthesized compounds, 7b with a 4-acetyl and an electron-enriched dihydronaphthofuran ring showed the highest tyrosinase-inhibition activity (IC50 = 8.91 μg/mL), which was comparable with that of standard kojic acid (IC50 = 10.16 μg/mL), potent antioxidant activity (IC50 = 3.33 μg/mL), which was comparable with that of BHT (IC50 = 34.67 μg/mL), and excellent antibacterial activities (MICs: 0.50 μg/mL against E. coli and S. aureus strains). A mechanistic analysis of 7b demonstrated that its tyrosinase inhibitory activity was reversible and competitive. Compounds 7c and 7d showed potent antioxidant activities (IC50: 6.30 and 5.01 μg/mL), and compound 7d also exhibited potent inhibitory activity against E. coli with a MIC of 0.5 μg/mL. Furthermore, compounds 7a, 7e, 7f, and 7i showed potent antibacterial activities against S. aureus with MICs of 0.5 μg/mL, which was comparable to that of ampicillin (MIC = 0.5 μg/mL).
    [Abstract] [Full Text] [Related] [New Search]