Inhibition of stromelysin-1 by caffeic acid derivatives from a propolis sample from Algeria

Planta Med. 2011 Jul;77(10):999-1004. doi: 10.1055/s-0030-1270713. Epub 2011 Feb 8.

Abstract

Stromelysin-1 (matrix metalloproteinase-3: MMP-3) occupies a central position in collagenolytic and elastolytic cascades, leading to cutaneous intrinsic and extrinsic aging. We screened extracts of a propolis sample from Algeria with the aim to isolate compounds able to selectively inhibit this enzyme. A butanolic extract (B (3)) of the investigated propolis sample was found to potently inhibit MMP-3 activity (IC (50) = 0.15 ± 0.03 µg/mL), with no or only weak activity on other MMPs. This fraction also inhibited plasmin amidolytic activity (IC (50) = 0.05 µg/mL) and impeded plasmin-mediated proMMP-3 activation. B (3) was fractionated by HPLC, and one compound, characterized by NMR and mass spectroscopy and not previously identified in propolis, i.e., (+)-chicoric acid, displayed potent IN VITRO MMP-3 inhibitory activity (IC (50) = 6.3 × 10 (-7) M). In addition, both caffeic acid and (+)-chicoric acid methyl ester present in fraction B (3) significantly inhibited UVA-mediated MMP-3 upregulation by fibroblasts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adult
  • Algeria
  • Butanols / chemistry
  • Caffeic Acids / chemistry
  • Caffeic Acids / pharmacology*
  • Cells, Cultured
  • Chromatography, High Pressure Liquid
  • Complex Mixtures / chemistry
  • Drug Evaluation, Preclinical
  • Enzyme Activation / drug effects
  • Fibrinolysin / antagonists & inhibitors
  • Fibrinolysin / pharmacology
  • Fibroblasts / drug effects
  • Fibroblasts / enzymology
  • Fibroblasts / radiation effects
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Matrix Metalloproteinase 3
  • Matrix Metalloproteinase Inhibitors*
  • Middle Aged
  • Phenols / pharmacology
  • Propolis / chemistry*
  • Protease Inhibitors / pharmacology*
  • Succinates / chemistry
  • Succinates / pharmacology
  • Ultraviolet Rays
  • Young Adult

Substances

  • Butanols
  • Caffeic Acids
  • Complex Mixtures
  • Matrix Metalloproteinase Inhibitors
  • Phenols
  • Protease Inhibitors
  • Succinates
  • Propolis
  • Fibrinolysin
  • MMP3 protein, human
  • Matrix Metalloproteinase 3
  • chicoric acid
  • caffeic acid
  • caftaric acid