Alistonitrine A, a caged monoterpene indole alkaloid from Alstonia scholaris

Org Lett. 2014 Feb 21;16(4):1080-3. doi: 10.1021/ol403625g. Epub 2014 Feb 3.

Abstract

Alistonitrine A, a new monoterpene indole alkaloid incorporating a third nitrogen atom, was isolated from the leaves of Alstonia scholaris and found to possess an unprecedented caged skeleton with a unique 6/5/6/5/5/6 ring system. Its structure and absolute configuration were established by extensive spectroscopic analyses and electron circular dichroism calculations. A plausible biogenetic pathway has been proposed for the biosynthesis of alistonitrine A from picrinine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alstonia / chemistry*
  • Indole Alkaloids / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Secologanin Tryptamine Alkaloids / chemistry*
  • Secologanin Tryptamine Alkaloids / isolation & purification*

Substances

  • Indole Alkaloids
  • Secologanin Tryptamine Alkaloids
  • alistonitrine A
  • picrinine