Isolation of a 1,3-enone isomer of heptanor-41-oxoyessotoxin from Protoceratium reticulatum cultures

Toxicon. 2004 Sep 1;44(3):325-36. doi: 10.1016/j.toxicon.2004.06.011.

Abstract

The 1,3-enone isomer (1) of heptanor-41-oxoyessotoxin (2) was isolated from extracts of Protoceratium reticulatum during large-scale production of yessotoxin (4). We found that 2 readily isomerizes to 1 in the presence of dilute ammonia and present evidence for the existence of 40-epi-2 (3) that also isomerizes to 1. 1-3 were detected by LC-MS methods both in extracts of P. reticulatum cultures and in mussels contaminated with yessotoxins. The isomerization of 2 and 3 into 1 occurs so readily that purification on basic alumina needs to be conducted carefully. No toxic effects were recorded in mice injected intraperitoneally with 1 at a dose of 5,000 microg/kg.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ammonia / metabolism
  • Animals
  • Biological Assay
  • Bivalvia / metabolism*
  • Chromatography, High Pressure Liquid
  • Chromatography, Liquid
  • Dinoflagellida / metabolism*
  • Environmental Monitoring
  • Ethers, Cyclic / chemistry*
  • Ethers, Cyclic / isolation & purification*
  • Ethers, Cyclic / toxicity
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Models, Molecular
  • New Zealand
  • Norway
  • Toxicity Tests, Acute

Substances

  • 42,43,44,45,46,47,55-heptanor-41-oxohomoyessotoxin
  • Ethers, Cyclic
  • Ammonia