Oscillapeptin J, a new grazer toxin of the freshwater cyanobacterium Planktothrix rubescens

J Nat Prod. 2003 Mar;66(3):431-4. doi: 10.1021/np020397f.

Abstract

Oscillapeptin J (1), a new and highly potent crustacean grazer toxin, was isolated from the axenic cyanobacterium Planktothrix rubescens, which frequently forms blooms in freshwater lakes. Chemical and spectroscopic analyses, including high resolving MS and two-dimensional NMR, were used to elucidate the compound's structure as a depsiheptapeptide of the oscillapeptin type. Strict application of a bioassay-guided isolation procedure proved this compound to be one of the major causative agents (besides [d-Asp(3),(E)-Dhb(7)]microcystin-RR) of the acute grazer toxicity of P. rubescens from Lake Zürich. The LC(50) value of oscillapeptin J as determined for the freshwater crustacean Thamnocephalus platyurus was 15.6 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bacterial Toxins / chemistry
  • Bacterial Toxins / isolation & purification*
  • Bacterial Toxins / toxicity
  • Cyanobacteria / chemistry*
  • Decapoda / drug effects*
  • Germany
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / toxicity

Substances

  • Bacterial Toxins
  • Peptides, Cyclic
  • oscillapeptin J