Analogues of perillaketone as highly potent agonists of TRPA1 channel

Food Chem. 2013 Dec 1;141(3):2044-51. doi: 10.1016/j.foodchem.2013.05.063. Epub 2013 May 24.

Abstract

Transient receptor potential (TRP) channels represent interesting molecular target structures involved in a number of different physiological and pathophysiological systems. In particular, TRPA1 channel is involved in nociception and in sensory perception of many pungent chemesthetic compounds, which are widespread in spices and food plants, including Perilla frutescens. A natural compound from P. frutescens (isoegomaketone) and 16 synthetic derivatives of perillaketone have been prepared and tested in vitro on rTRPA1 expressed in HEK293 cells and their potency, efficacy and desensibilisation activity measured. Most derivatives proved to be high potency agonists of TRPA1, with a potency higher than most natural agonists reported in the literature. These furylketones derivatives, represent a new class of chemical structures active on TRPA1 with many potential applications in the agrifood and pharmaceutical industry.

Keywords: Chemesthesis; Perilla frutescens; Perillaketone; TRPA1 ion channels; Transient receptor potential.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • HEK293 Cells
  • Humans
  • Kinetics
  • Molecular Structure
  • Monoterpenes / chemical synthesis
  • Monoterpenes / chemistry*
  • Perilla / chemistry*
  • Plant Extracts / chemical synthesis
  • Plant Extracts / chemistry*
  • Rats
  • Transient Receptor Potential Channels / agonists*
  • Transient Receptor Potential Channels / chemistry

Substances

  • Monoterpenes
  • Plant Extracts
  • Transient Receptor Potential Channels
  • perilla ketone