8-hydroxydihydrochelerythrine and 8-hydroxydihydrosanguinarine with a potent acetylcholinesterase inhibitory activity from Chelidonium majus L

Biol Pharm Bull. 2006 Nov;29(11):2317-20. doi: 10.1248/bpb.29.2317.

Abstract

Ethanol extract of the aerial portion of Chelidonium majus L. inhibited acetylcholinesterase (AChE) activity without a significant inhibition of butyrylcholinesterase (BuChE). Using mass spectrometry and NMR studies, three active constituents were isolated and identified: 8-hydroxydihydrochelerythrine (1), 8-hydroxydihydrosanguinarine (2), and berberine (3). Compounds 1-3 showed potent inhibitory activity against AChE, with IC50 (microM) values of 0.61-1.85. Compound 1 exhibited competitive and selective inhibition for AChE.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism
  • Berberine / chemistry
  • Berberine / isolation & purification
  • Berberine / pharmacology
  • Butyrylcholinesterase / metabolism
  • Chelidonium / chemistry*
  • Chloroform / chemistry
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology*
  • Chromatography / methods
  • Dose-Response Relationship, Drug
  • Ethanol / chemistry
  • Herbal Medicine
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification
  • Heterocyclic Compounds, 4 or More Rings / pharmacology*
  • Methanol / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular / methods
  • Plant Components, Aerial / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Polycyclic Compounds / chemistry
  • Polycyclic Compounds / isolation & purification
  • Polycyclic Compounds / pharmacology

Substances

  • 8-hydroxydihydrochelerythrine
  • 8-hydroxydihydrosanguinarine
  • Cholinesterase Inhibitors
  • Heterocyclic Compounds, 4 or More Rings
  • Plant Extracts
  • Polycyclic Compounds
  • Berberine
  • Ethanol
  • Chloroform
  • Acetylcholinesterase
  • Butyrylcholinesterase
  • Methanol