Hapalindole-related alkaloids from the cultured cyanobacterium Fischerella ambigua

Phytochemistry. 2010 Dec;71(17-18):2116-23. doi: 10.1016/j.phytochem.2010.09.004. Epub 2010 Oct 19.

Abstract

Four hapalindole-related alkaloids, namely fischambiguines A and B, ambiguine P, ambiguine Q nitrile as well as ambiguine G nitrile were identified from the cultured cyanobacterium Fischerella ambigua (UTEX 1903). The structures were determined by spectroscopic analysis including MS, 1D and 2D NMR and X-ray crystallography. The alkaloids possessed fused pentacyclic and hexacyclic carbon skeletons. Fischambiguine B displayed a strong inhibitory activity against Mycobacterium tuberculosis with an MIC value of 2 μM, with no detectable cytotoxicity in a Vero cell line.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Bacillus anthracis / drug effects
  • Candida albicans / drug effects
  • Chlorocebus aethiops
  • Crystallography, X-Ray
  • Cyanobacteria / chemistry*
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects
  • Nuclear Magnetic Resonance, Biomolecular
  • Staphylococcus aureus / drug effects
  • Vero Cells

Substances

  • Indole Alkaloids
  • ambiguine G