Subincanadines A-C, novel quaternary indole alkaloids from Aspidosperma subincanum

J Org Chem. 2002 Sep 6;67(18):6449-55. doi: 10.1021/jo025854b.

Abstract

Three novel quaternary indole alkaloids with an unprecedented 1-azoniatricyclo[4.3.3.0(1,5)]undecane moiety, subincanadines A-C (1-3), as well as two new indole alkaloids with a 1-azabicyclo[5.2.2]undecane moiety, subincanadines D (4) and E (5), and a new indole alkaloid with a 1-azabicyclo[4.3.1]decane moiety, subincanadine F (6), have been isolated from the barks of Aspidosperma subincanum Mart, and the structures of 1-6 and the stereochemistry of 1-3 were elucidated by spectroscopic data and chemical means.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspidosperma / chemistry*
  • Brazil
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Inhibitory Concentration 50
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxidation-Reduction
  • Plant Bark / chemistry
  • Plants, Medicinal / chemistry*

Substances

  • Indole Alkaloids
  • subincanadine A
  • subincanadine B
  • subincanadine C