Isolation, characterization and acetylcholinesterase inhibitory activity of alkaloids from roots of Stemona sessilifolia

Fitoterapia. 2013 Sep:89:257-64. doi: 10.1016/j.fitote.2013.06.010. Epub 2013 Jun 27.

Abstract

Two new alkaloids, named stenine A (1) and stenine B (2), along with the known compounds neostenine (3), stenine (4) and neotuberostemonine (5), were isolated from the roots of Stemona sessilifolia. Their structures were elucidated by 1D- and 2D-NMR spectra and X-ray single-crystal diffraction experiment. Anti-acetylcholinesterase (AChE) activity of compounds 1-5 were also tested. Compounds 2 and 4 showed significant anti-acetylcholinesterase activities, with IC50 values of 2.1±0.2 μM and 19.8±2.5 μM, resp. The mode of AChE inhibition by Compound 2 (the most potential AChE inhibitor) was reversible and competitive. In addition, molecular modeling was performed to explore the binding mode of compound 2 with AChE.

Keywords: Acetylcholinesterase inhibitors; Alkaloids; Alzheimer's disease; Stemona sessilifolia.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism*
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology*
  • Inhibitory Concentration 50
  • Models, Molecular
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Roots / chemistry
  • Stemonaceae / chemistry*

Substances

  • Alkaloids
  • Cholinesterase Inhibitors
  • Plant Extracts
  • stenine
  • Acetylcholinesterase