Galloylquinic acid derivatives from Copaifera langsdorffii leaves display gastroprotective activity

Chem Biol Interact. 2017 Jan 5:261:145-155. doi: 10.1016/j.cbi.2016.11.028. Epub 2016 Nov 25.

Abstract

Nine new methylated galloylquinic acids were isolated from an aqueous fraction of Copaifera langsdorffii (Fabaceae-Caesalpinioideae) leaf hydroalcoholic extract (3-8, 11, 12, and 14), along with three known methylated galloylquinic acids (1, 2, and 15) and four galloylquinic acids (9, 10, 13, and 16). These compounds were characterized by nuclear magnetic resonance spectroscopy and mass spectrometry. They were further tested in a gastroprotection assay (Ethanol-HCl induced ulcer model in mice), in which all of them significantly reduced the total lesion area, and increased the cure ratio in comparison with pantoprazole. Also, the tested compounds displayed cytotoxicity against gastric adenocarcinoma cells.

Keywords: Adenocarcinoma; Copaiba; Galloylquinic acid; Gastroprotection; Phenol; Ulcer.

MeSH terms

  • 2-Pyridinylmethylsulfinylbenzimidazoles / pharmacology
  • Administration, Oral
  • Animals
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cell Death / drug effects
  • Chemical Fractionation
  • Chromatography, High Pressure Liquid
  • Fabaceae / chemistry*
  • Flow Cytometry
  • Gallic Acid / administration & dosage
  • Gallic Acid / pharmacology
  • Gastric Mucosa / drug effects*
  • Inhibitory Concentration 50
  • Male
  • Mice, Inbred BALB C
  • Pantoprazole
  • Plant Leaves / chemistry*
  • Protective Agents / administration & dosage
  • Protective Agents / pharmacology*
  • Proton Magnetic Resonance Spectroscopy
  • Quinic Acid / administration & dosage
  • Quinic Acid / chemistry
  • Quinic Acid / isolation & purification
  • Quinic Acid / pharmacology*

Substances

  • 2-Pyridinylmethylsulfinylbenzimidazoles
  • Protective Agents
  • Quinic Acid
  • Gallic Acid
  • Pantoprazole