Identification and Semi-Synthesis of 3- O-Protocatechuoylceanothic Acid, a Novel and Natural GPR120 Agonist †

Molecules. 2019 Sep 26;24(19):3487. doi: 10.3390/molecules24193487.

Abstract

The identification and three step synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist, is described. This ceanothane-type triterpenoid was identified from the components of Ziziphus jujuba roots and was found to be a new GPR120 agonist with a novel structure. We synthetically converted ceanothic acid, which does not have GPR120 agonist activity, into 3-O-protocatechuoylceanothic acid in three steps. In addition, we present the corrected NMR spectrum of 3-O-protocatechuoylceanothic acid based on our synthesis.

Keywords: 3-O-protocatechuoylceanothic acid; G protein-coupled receptor; GPR120; agonist; semi-synthesis.

MeSH terms

  • Animals
  • CHO Cells
  • Chemistry Techniques, Synthetic
  • Cricetulus
  • Humans
  • Ligands
  • Molecular Structure
  • Receptors, G-Protein-Coupled / agonists
  • Receptors, G-Protein-Coupled / chemistry*
  • Recombinant Proteins
  • Structure-Activity Relationship
  • Triterpenes / chemical synthesis*
  • Triterpenes / pharmacology*

Substances

  • FFAR4 protein, human
  • Ligands
  • Receptors, G-Protein-Coupled
  • Recombinant Proteins
  • Triterpenes