Goniomedines A and B: unprecedented bisindole alkaloids formed through fusion of two indole moieties via a dihydropyran unit

Org Lett. 2012 Aug 17;14(16):4162-5. doi: 10.1021/ol301832t. Epub 2012 Aug 6.

Abstract

Two novel bisindole alkaloids, goniomedines A (1) and B (2), possessing an unprecedented quebrachamine-pleioarpamine-type skeleton, in which indole moieties are fused via a dihydropyran unit, were isolated from the stem bark of Gonioma malagasy. The structures were elucidated by comprehensive analysis of MS and NMR spectroscopic data. Their absolute configurations were deduced following the comparison of experimental and theoretically calculated ECD spectra and through biogenetic considerations. Goniomedine B (2) exhibited moderate activity against Plasmodium falciparum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Apocynaceae / chemistry*
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects

Substances

  • Alkaloids
  • Indole Alkaloids
  • goniomedine A
  • goniomedine B
  • pleiocarpamine