Koniamborine, the first pyrano[3,2-b]indole alkaloid and other secondary metabolites from Boronella koniambiensis

J Nat Prod. 2005 Jul;68(7):1083-6. doi: 10.1021/np050013w.

Abstract

Two new alkaloids, (-)-cis-1,2-dihydroxy-1,2-dihydromedicosmine (3) and koniamborine (4), have been isolated from Boronella koniambiensis aerial parts. Their structures have been established from NMR and mass data. Koniamborine is a novel type of alkaloid, which derives from the pyrano[3,2-b]indole basic skeleton, described for the first time from nature. 6-Methoxy-1-methylisatin, also present in the plant material, can be considered biogenetically as a degradation product of the fused pyrone ring of 4.

MeSH terms

  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification*
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / isolation & purification*
  • Molecular Structure
  • New Caledonia
  • Rutaceae / chemistry*

Substances

  • 1,2-dihydroxy-1,2-dihydromedicosmine
  • Heterocyclic Compounds, 4 or More Rings
  • Indole Alkaloids
  • koniamborine