Cytisine-like alkaloids from Ormosia hosiei Hemsl. & E.H. Wilson

Phytochemistry. 2014 Nov:107:97-101. doi: 10.1016/j.phytochem.2014.07.022. Epub 2014 Aug 26.

Abstract

Four alkaloids named hosieines A-D were isolated from the root and stem of Ormosia hosiei. Their flat structures were established by mass spectrometry and by a combination of NMR experiments. These molecules probably share a common biosynthetic origin with the lupin alkaloids but they differ in the formation of the last ring, being here part of a rare 2-azabicyclo[3.2.1]octane system. Their absolute configuration was determined by X-ray crystallography using CuKα radiation. As has been described for cytisine, they display a remarkable affinity towards neuronal nicotinic acetylcholine α4β2 receptor.

Keywords: Cytisine; Fabaceae; Ormosia hosiei.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Azocines / chemistry
  • Azocines / isolation & purification
  • Azocines / pharmacology
  • Crystallography, X-Ray
  • Fabaceae / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Plant Stems / chemistry
  • Quinolizines / chemistry
  • Quinolizines / isolation & purification
  • Quinolizines / pharmacology
  • Receptors, Nicotinic / drug effects*

Substances

  • Alkaloids
  • Azocines
  • Quinolizines
  • Receptors, Nicotinic
  • nicotinic receptor alpha4beta2
  • cytisine