Antimicrobial O-Alkyl Derivatives of Naringenin and Their Oximes Against Multidrug-Resistant Bacteria

Molecules. 2020 Aug 10;25(16):3642. doi: 10.3390/molecules25163642.

Abstract

New antimicrobial agents are needed to address infections caused by multidrug-resistant bacteria. Here, we are reporting novel O-alkyl derivatives of naringenin and their oximes, including novel compounds with a naringenin core and O-hexyl chains, showing activity against clinical strains of clarithromycin-resistant Helicobacter pylori, vancomycin-resistant Enterococcus faecalis, methicillin-resistant Staphylococcus aureus, and beta-lactam-resistant Acinetobacter baumannii and Klebsiella pneumoniae. The minimum inhibitory concentrations (MICs), which provide a quantitative measure of antimicrobial activity, were in the low microgram range for the selected compounds. Checkerboard assays for the most active compounds in combination with antibiotics revealed interactions that varied from synergistic to neutral.

Keywords: O-alkyl derivative of naringenin; multidrug-resistant pathogens; naringenin; oxime.

MeSH terms

  • Acinetobacter baumannii / drug effects
  • Acinetobacter baumannii / isolation & purification
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Drug Resistance, Multiple, Bacterial / drug effects*
  • Flavanones / chemical synthesis
  • Flavanones / chemistry*
  • Flavanones / pharmacology
  • Helicobacter pylori / drug effects
  • Helicobacter pylori / isolation & purification
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Oximes / chemistry*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Flavanones
  • Oximes
  • naringenin