Traditionally used medicinal plants against uncomplicated urinary tract infections: Hexadecyl coumaric acid ester from the rhizomes of Agropyron repens (L.) P. Beauv. with antiadhesive activity against uropathogenic E. coli

Fitoterapia. 2017 Mar:117:22-27. doi: 10.1016/j.fitote.2016.12.010. Epub 2016 Dec 29.

Abstract

The rhizomes from Agropyron repens are traditionally used for the treatment of uncomplicated urinary tract infections. Extracts prepared with solvents of different polarity did not show any cytotoxic effects against different strains of uropathogenic E. coli (UPEC) and human T24 bladder cells under in vitro conditions. Significant antiadhesive activity against the bacterial attachment to human T24 bladder cells was found for an acetone extract (AAE) at concentrations >250μg/mL. More hydrophilic extracts did not influence the bacterial attachment to the eukaryotic host cells. Bioassay guided fractionation of AAE led to the identification of (E)-hexadecyl-3-(4-hydroxyphenyl)-acrylate (hexadecyl-coumaric acid ester) 1 as the compound responsible for inhibiting the UPEC adhesion to T24 bladder cells. 1 reduced the bacterial invasion into the bladder cells as shown by a specific invasion assay. Additionally, 1 was obtained by chemical synthesis, and also the synthetic structural analogs 2 and 3 were tested for their potential antiadhesive activity, indicating that a shorter alkyl chain at the ester function as well as the lack of hydroxylation of the phenyl moiety will abolish the antiadhesive activity.

Keywords: Adhesion; Agropyron repens; Bladder cells; Coumaric acid ester; Uropathogenic E. coli.

MeSH terms

  • Agropyron / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Bacterial Adhesion / drug effects*
  • Cell Line
  • Coumaric Acids / isolation & purification
  • Coumaric Acids / pharmacology*
  • Epithelial Cells / drug effects
  • Esters / isolation & purification
  • Esters / pharmacology*
  • Humans
  • Plant Extracts / chemistry
  • Plants, Medicinal / chemistry
  • Rhizome / chemistry
  • Urinary Bladder / cytology
  • Urinary Tract Infections / drug therapy
  • Urinary Tract Infections / microbiology
  • Uropathogenic Escherichia coli / drug effects*

Substances

  • Anti-Bacterial Agents
  • Coumaric Acids
  • Esters
  • Plant Extracts