Phenolic constituents from the aerial parts of Glycyrrhiza inflata and their antibacterial activities

J Asian Nat Prod Res. 2015;17(3):256-61. doi: 10.1080/10286020.2014.966095. Epub 2014 Oct 15.

Abstract

Chemical investigation on 90% ethanol extracts of the aerial parts of Glycyrrhiza inflata afforded two new phenolic constituents, 2-(3-methyl-2-butenyl)-3,5,4'-trihydroxy-bibenzyl (1) and (2S)-6-[(E)-3-hydroxymethyl-2-butenyl]-3',4',5,7-tetrahydroxy-dihydroflavanone (2) along with seven known dihydroflavanones (3-9). Compounds 1-9 were tested for their minimum inhibitory concentration (MIC) values of inhibiting Staphylococcus aureus and Staphylococcus epidermidis. Compound 1 showed moderate antibacterial activities against both S. aureus (MIC of 50.00 μg/ml) and S. epidermidis (MIC of 12.50 μg/ml). The analysis of structure-activity relationships revealed that the antibacterial activity of dihydroflavanones (2-9) was significantly affected by the position of prenyl group.

Keywords: Glycyrrhiza inflata; antibacterial activity; phenolic constituents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Bibenzyls
  • Flavanones
  • Glycyrrhiza / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Phenols / chemistry
  • Plant Components, Aerial / chemistry
  • Staphylococcus aureus / drug effects
  • Staphylococcus epidermidis / drug effects
  • Structure-Activity Relationship

Substances

  • (2S)-6-((E)-3-hydroxymethyl-2-butenyl)-3',4',5,7-tetrahydroxy-dihydroflavanone
  • 2-(3-methyl-2-butenyl)-3,5,4'-trihydroxy-bibenzyl
  • Anti-Bacterial Agents
  • Bibenzyls
  • Flavanones
  • Phenols