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Planta Med 2011; 77(10): 999-1004
DOI: 10.1055/s-0030-1270713
Biological and Pharmacological Activity
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Inhibition of Stromelysin-1 by Caffeic Acid Derivatives from a Propolis Sample from Algeria

Narimane Segueni1 , 3 , Abdulmagid Alabdul Magid2 , Martine Decarme1 , Salah Rhouati3 , Mesbah Lahouel4 , Frank Antonicelli1 , Catherine Lavaud2 , William Hornebeck1
  • 1Unité Medyc, Université de Reims Champagne Ardennes, UFR de Médecine, Reims, France
  • 2Laboratoire de Pharmacognosie, Université de Reims Champagne Ardennes, Institut de Chimie Moléculaire de Reims, Reims, France
  • 3Laboratoire des Produits Naturels d'Origine Végétale et de Synthèse Organique, Université Mentouri, Département de Chimie, Constantine, Algérie
  • 4Laboratoire de Phytopharmacologie, Université de Jijel, Département de Biologie, Jijel, Algérie
Further Information

Publication History

received July 7, 2010 revised Dec. 16, 2010

accepted Dec. 28, 2010

Publication Date:
08 February 2011 (online)

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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 (B3) of the investigated propolis sample was found to potently inhibit MMP-3 activity (IC50 = 0.15 ± 0.03 µg/mL), with no or only weak activity on other MMPs. This fraction also inhibited plasmin amidolytic activity (IC50 = 0.05 µg/mL) and impeded plasmin-mediated proMMP-3 activation. B3 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 (IC50 = 6.3 × 10−7 M). In addition, both caffeic acid and (+)-chicoric acid methyl ester present in fraction B3 significantly inhibited UVA-mediated MMP-3 upregulation by fibroblasts.

Key words

propolis - matrix metalloproteinase (MMP) - MMP‐3 inhibitors - plasmin - caffeic acid - chicoric acid

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Prof. Catherine Lavaud

Laboratoire de Pharmacognosie
Université de Reims Champagne Ardennes
Institut de Chimie Moléculaire de Reims
UMR 6229 CNRS

Bâtiment 18, BP 1039

51687 Reims Cedex 2

France

Phone: +33 3 26 91 35 48

Fax: +33 3 26 91 31 66

Email: catherine.lavaud@univ-reims.fr

    www.thieme-connect.de/ejournals/toc/plantamedica