Irbic acid, a dicaffeoylquinic acid derivative from Centella asiatica cell cultures

Fitoterapia. 2011 Oct;82(7):950-4. doi: 10.1016/j.fitote.2011.05.008. Epub 2011 May 23.

Abstract

3,5-O-dicaffeoyl-4-O-malonilquinic acid (1) (irbic acid) has been isolated for the first time from cell cultures of Centella asiatica and till now it has never been reported to be present in the intact plant. Evidence of its structure was obtained by spectroscopic analyses (MS/NMR). Besides 1, cell cultures produce also the known 3,5-O-dicaffeoylquinic acid, chlorogenic acid, and the triferulic acid 2 (4-O-8'/4'-O-8″-didehydrotriferulic acid). Biological activities were evaluated for compound 1, which showed to have a strong radical scavenging capacity, together with a high inhibitory activity on collagenase. This suggests a possible utilization of this substance as a topical agent to reduce the skin ageing process.

MeSH terms

  • Cell Culture Techniques
  • Centella / chemistry*
  • Collagenases / drug effects*
  • Collagenases / metabolism
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / isolation & purification
  • Free Radical Scavengers / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Quinic Acid / analogs & derivatives*
  • Quinic Acid / chemistry
  • Quinic Acid / isolation & purification
  • Quinic Acid / pharmacology

Substances

  • 3,5-O-dicaffeoyl-4-O-malonilquinic acid
  • Enzyme Inhibitors
  • Free Radical Scavengers
  • Plant Extracts
  • Quinic Acid
  • Collagenases