7-Desmethyl-microcystin-RR, a hepatotoxin from a waterbloom of Microcystis aeruginosa

Z Naturforsch C J Biosci. 1992 May-Jun;47(5-6):335-40. doi: 10.1515/znc-1992-0603.

Abstract

A peptide toxin was isolated from a waterbloom of Microcystis aeruginosa from Lake Frøylandsvatn in Norway. The isolation procedure included liquid and solid phase extraction and reversed phase high performance liquid chromatography. Amino acid analysis yielded D-glutamic acid, D-erythro-beta-methylaspartic acid and D-alanine in equimolar and L-arginine in twofold molar ratios. The presence of dehydroalanine was confirmed by hydrogenation and subsequent amino acid analysis with combined gas liquid chromatography/mass spectrometry. Investigation of the toxin with fast atom bombardment mass spectrometry showed a nominal relative molecular mass of 1023. 3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyl- 4,6-decadienoic acid (Adda) was identified by 1H NMR and 1H, 1H COSY spectroscopy. The structure of the toxin was elucidated as 7-desmethyl-microcystin-RR.

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Chromatography, Gas
  • Chromatography, High Pressure Liquid
  • Gas Chromatography-Mass Spectrometry
  • Liver / drug effects
  • Liver / pathology*
  • Magnetic Resonance Spectroscopy
  • Microcystins
  • Microcystis*
  • Molecular Sequence Data
  • Molecular Structure
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Toxins, Biological / isolation & purification*

Substances

  • Microcystins
  • Peptides, Cyclic
  • Toxins, Biological
  • 7-desmethylmicrocystin RR