Article

Journal of Chemical Ecology

, Volume 29, Issue 8, pp 1757-1770

First online:

Isolation, Characterization, and Quantitative Analysis of Microviridin J, a New Microcystis Metabolite Toxic to Daphnia

  • Thomas RohrlackAffiliated withFreshwater Biological Laboratory, University of Copenhagen Email author 
  • , Kirsten ChristoffersenAffiliated withFreshwater Biological Laboratory, University of Copenhagen
  • , Poul Erik HansenAffiliated withDepartment of Life Sciences and Chemistry, Roskilde University
  • , Wei ZhangAffiliated withDepartment of Life Sciences and Chemistry, Roskilde University
  • , Olaf CzarneckiAffiliated withGroup Ecophysiology, Department of Biology, Humboldt-University
  • , Manfred HenningAffiliated withGroup Ecophysiology, Department of Biology, Humboldt-University
  • , Jutta FastnerAffiliated withBiotechnology Center and Max Vollmer Institute, Technical University Berlin
  • , Marcel ErhardAffiliated withAnagnosTec GmbH, Im Biotechnologiepark TGZ II
  • , Brett A. NeilanAffiliated withSchool of Biotechnology and Biomolecular Sciences, University of New South Wales
    • , Melanie KaebernickAffiliated withGroup Genetics, Department of Biology, Humboldt-University

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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.

Microcystis cyanobacteria Daphnia microviridin NMR microcystin environmental toxins