Antillatoxin B, a neurotoxic lipopeptide from the marine cyanobacterium Lyngbya majuscula

J Nat Prod. 2001 Jul;64(7):983-5. doi: 10.1021/np010107f.

Abstract

Bioassay-guided fractionation of organic extracts from two Lyngbya majuscula collections led to the isolation of a new secondary metabolite, antillatoxin B, an unusual N-methyl homophenylalanine analogue of the potent neurotoxin antillatoxin. Its structure was deduced from 2D NMR and data comparisons with antillatoxin. Antillatoxin B exhibited significant sodium channel-activating (EC(50) = 1.77 microM) and ichthyotoxic (LC(50) = 1 microM) properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Cyanobacteria / chemistry*
  • Goldfish
  • Lipopeptides
  • Lipoproteins / chemistry
  • Lipoproteins / isolation & purification*
  • Lipoproteins / pharmacology
  • Lyngbya Toxins / chemistry
  • Lyngbya Toxins / isolation & purification*
  • Lyngbya Toxins / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Neuroblastoma
  • Peptides, Cyclic*
  • Sodium Channels / drug effects
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Lipopeptides
  • Lipoproteins
  • Lyngbya Toxins
  • Peptides, Cyclic
  • Sodium Channels
  • antillatoxin
  • antillatoxin B