Catechin derivatives from Parapiptadenia rigida with in vitro wound-healing properties

J Nat Prod. 2010 Dec 27;73(12):2035-41. doi: 10.1021/np100523s. Epub 2010 Nov 16.

Abstract

Analysis of the ethanolic extract of the bark from Parapiptadenia rigida resulted in the isolation of the new catechin derivatives 4',3''-di-O-methylapocynin-D (10), 4',3''-di-O-methylapocynin-B (11), epigallocatechin-3-O-ferulate (8), and 4'-O-methylepigallocatechin-3-O-ferulate (9) and the catechins 4'-O-methylepigallocatechin-3-O-gallate (6) and 4'-O-methylepicatechin-3-O-gallate (7). These compounds, isolated for the first time from a natural source, are accompanied by the five known catechins 4'-O-methylgallocatechin (1), 4'-O-methylepigallocatechin (2), 3'-O-methylepicatechin (3), epigallocatechin-3-O-gallate (4), and epicatechin-3-O-gallate (5). Compounds 5 and 7 displayed promising wound-healing effects in a scratch assay. Some of the catechin derivatives showed inhibitory effects on NF-κB DNA binding and p38α MAPK activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Brazil
  • Catechin / analogs & derivatives*
  • Catechin / chemistry
  • Catechin / pharmacology*
  • DNA / metabolism
  • Fabaceae / chemistry*
  • Mice
  • Mitogen-Activated Protein Kinase 14 / antagonists & inhibitors*
  • Molecular Structure*
  • NF-kappa B / antagonists & inhibitors
  • NF-kappa B / metabolism
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry
  • Swiss 3T3 Cells
  • Wound Healing / drug effects*

Substances

  • 3'-O-methylepicatechin
  • 4'-O-methylepigallocatechin
  • NF-kappa B
  • Catechin
  • DNA
  • epicatechin gallate
  • epigallocatechin gallate
  • Mitogen-Activated Protein Kinase 14
  • gallocatechol