Comparative evaluation of two structurally related flavonoids, isoliquiritigenin and liquiritigenin, for their oral infection therapeutic potential

J Nat Prod. 2011 Sep 23;74(9):1862-7. doi: 10.1021/np200174h. Epub 2011 Aug 25.

Abstract

Isoliquiritigenin (1) and liquiritigenin (2) are structurally related flavonoids found in a variety of plants. The purpose of this study was to perform a comparative analysis of biological properties of these compounds in regard to their therapeutic potential for oral infections. Compound 1 demonstrated significant antibacterial activity against three major periodontopathogens, Porphyromonas gingivalis, Fusobacterium nucleatum, and Prevotella intermedia. In contrast, 2 exerted less pronounced effects on the above bacterial species. Neither compound was effective against cariogenic bacteria (Streptococcus mutans and Streptococcus sobrinus). Furthermore, 1 exhibited a stronger inhibitory activity than 2 toward P. gingivalis collagenase and human matrix metalloproteinase 9. Finally, the capacity of 1 to attenuate the inflammatory response of macrophages induced by Aggregatibacter actinomycetemcomitans lipopolysaccharide (LPS) was much higher when compared to 2. The activation of transcriptional factors nuclear factor-κB (NF-κB) p65 and activator protein-1 (AP-1) associated with the LPS-induced inflammatory response in macrophages was inhibited strongly by 1, but less affected by 2.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Chalcones
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Flavanones / chemistry
  • Flavanones / isolation & purification*
  • Flavanones / pharmacology*
  • Fusobacterium nucleatum / drug effects
  • Humans
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Matrix Metalloproteinase Inhibitors
  • Molecular Structure
  • NF-kappa B / drug effects
  • Nuclear Magnetic Resonance, Biomolecular
  • Porphyromonas gingivalis / drug effects
  • Transcription Factor AP-1 / drug effects
  • Transcription Factor RelA

Substances

  • Anti-Bacterial Agents
  • Chalcones
  • Drugs, Chinese Herbal
  • Flavanones
  • Lipopolysaccharides
  • Matrix Metalloproteinase Inhibitors
  • NF-kappa B
  • Transcription Factor AP-1
  • Transcription Factor RelA
  • isoliquiritigenin
  • liquiritigenin