Isolation, characterization, and quantitative analysis of Microviridin J, a new Microcystis metabolite toxic to Daphnia

J Chem Ecol. 2003 Aug;29(8):1757-70. doi: 10.1023/a:1024889925732.

Abstract

This paper describes the purification and characterization of microviridin J. a newly discovered metabolite of Microcystis that causes a lethal molting disruption in Daphnia spp., upon ingestion of living cyanobacterial cells. Microviridin J consists of an acetylated chain of 13 amino acids arranged in three rings and two side chains. Unlike other known isoforms of microviridin, microviridin J contains arginine that imparts a unique solution conformation characterized by proximal hydrophobic interactions between Arg and other regions of the molecule. This eventually results in the formation and stabilization of an additional ring system. Microviridin J potently inhibits porcine trypsin, bovine chymotrypsin, and daphnid trypsin-like proteases. The activity against trypsin is most likely due to Arg and its distinctive conformational interactions. Overall, the data presented for microviridin J emphasize once again the ability of cyanobacteria to produce numerous and potent environmental toxins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bacterial Toxins / chemistry
  • Bacterial Toxins / isolation & purification*
  • Bacterial Toxins / toxicity*
  • Daphnia
  • Magnetic Resonance Spectroscopy
  • Microcystis / chemistry
  • Microcystis / pathogenicity*
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / toxicity*
  • Toxicity Tests

Substances

  • Bacterial Toxins
  • Peptides, Cyclic
  • microviridin J