Coumarin, anthroquinone and stilbene derivatives with anticholinesterase activity

Z Naturforsch C J Biosci. 2008 May-Jun;63(5-6):366-70. doi: 10.1515/znc-2008-5-610.

Abstract

Acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are the key enzymes in pathogenesis of Alzheimer's disease (AD), which is characterized by a deficit in central cholinergic transmission. In the current study, AChE and BChE inhibitory activities of seven coumarin derivatives [umbelliferone (1), 4-methylumbelliferone (2), 4-hydroxycoumarin (3), scopoletin (4), 8-methoxypsoralen (5), bergapten (6), and iso-bergapten (7)], a furanocoumarin mixture obtained from Heracleum crenatifolium Boiss. (Umbelliferae), as well as of two anthroquinone derivatives [rhein (8) and aloe-emodine (9)] and one stilbene, rhapontin (10), were tested by the spectrophotometric method of Ellman using an ELISA microplate-reader at 1 mg mL(-1). Among them, the furanocoumarin mixture [(68.8 +/- 0.76)%], bergapten [(62.4 +/- 0.74)%], aloe-emodine [(57.2 +/- 1.32)%], scopoletin [(53.1 +/- 0.83)%], and 4-methylumbelliferone [(62.3 +/- 1.03)%] showed over 50% inhibition against AchE, while umbelliferone [(54.3 +/- 0.23)%], 4-methylumbelliferone [(80.9 +/- 1.17)%], scopoletin [(73.5 +/- 1.01)%], 8-methoxypsoralen [(67.1 +/- 0.98)%], as well as the furanocoumarin mixture [(76.7 +/- 0.95)%] had a notable anti-BChE effect.

MeSH terms

  • 5-Methoxypsoralen
  • Anthraquinones / pharmacology*
  • Butyrylcholinesterase / metabolism
  • Cholinesterase Inhibitors / pharmacology*
  • Coumarins / pharmacology*
  • Furocoumarins / pharmacology
  • Ginkgo biloba
  • Heracleum / chemistry*
  • Methoxsalen / analogs & derivatives
  • Methoxsalen / pharmacology
  • Monoamine Oxidase Inhibitors / pharmacology
  • Scopoletin / pharmacology
  • Stilbenes / pharmacology

Substances

  • Anthraquinones
  • Cholinesterase Inhibitors
  • Coumarins
  • Furocoumarins
  • Monoamine Oxidase Inhibitors
  • Stilbenes
  • 5-Methoxypsoralen
  • Butyrylcholinesterase
  • rhapontin
  • Scopoletin
  • Methoxsalen