Acetylenic acid analogues from the edible mushroom Chanterelle (Cantharellus cibarius) and their effects on the gene expression of peroxisome proliferator-activated receptor-gamma target genes

Bioorg Med Chem Lett. 2012 Mar 15;22(6):2347-9. doi: 10.1016/j.bmcl.2012.01.070. Epub 2012 Jan 28.

Abstract

A new acetylenic acid, (10E,14Z)-9-oxooctadeca-10,14-dien-12-ynoic acid (1), was isolated from the edible mushroom Chanterelle (Cantharellus cibarius), together with a known acetylenic acid, (10E,14Z)-9-hydroxyoctadeca-10,14-dien-12-ynoic acid (2) and their structures were determined through analysis of NMR and mass data. The new acetylenic acid (1) specifically activated peroxisome proliferator-activated receptor (PPAR)-γ with an EC(50) value of 1.88 μM as measured by a reporter gene assay. Expression of PPAR-γ target genes were significantly altered as well, supporting the hypothesis that compound 1 is a PPAR-γ potential agonist that regulates transcription of the PPAR-γ target genes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / chemistry*
  • Alkynes / chemistry*
  • Alkynes / isolation & purification
  • Alkynes / pharmacology
  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • CHO Cells
  • Chromans / pharmacology
  • Cricetinae
  • Dose-Response Relationship, Drug
  • Fatty Acids, Unsaturated / chemistry*
  • Fatty Acids, Unsaturated / isolation & purification
  • Fatty Acids, Unsaturated / pharmacology
  • Gene Expression
  • Genes, Reporter
  • Hep G2 Cells
  • Humans
  • Hypoglycemic Agents / chemistry*
  • Hypoglycemic Agents / isolation & purification
  • Hypoglycemic Agents / pharmacology
  • Luciferases / genetics
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • PPAR gamma / agonists*
  • PPAR gamma / genetics
  • PPAR gamma / metabolism
  • Thiazolidinediones / pharmacology
  • Transfection
  • Troglitazone

Substances

  • Alkynes
  • Antineoplastic Agents
  • Chromans
  • Fatty Acids, Unsaturated
  • Hypoglycemic Agents
  • PPAR gamma
  • Thiazolidinediones
  • 2-hexadecynoic acid
  • Luciferases
  • Troglitazone