Isolation of 41a-homoyessotoxin and the identification of 9-methyl-41a-homoyessotoxin and nor-ring A-yessotoxin from Protoceratium reticulatum

Chem Res Toxicol. 2004 Nov;17(11):1414-22. doi: 10.1021/tx049832r.

Abstract

41a-homoyessotoxin (1), a new analogue of yessotoxin (7), was isolated from extracts of Protoceratium reticulatum grown in culture. In addition, 9-methyl-41a-homoyessotoxin (2) and a nor-ring A-yessotoxin (3) were identified as the major components of a mixed fraction. The structural information was initially obtained from LC-UV and LC-MS3 chromatograms, with subsequent definitive structure determination by NMR, LC-MS/MS, and high-resolution MS. Full 1H and indirectly detected 13C NMR assignments for all but two carbon atoms were obtained from ca. 100 microg of 1. Full 1H NMR assignments for 2 and 3 and identification of three new heptanor-41-oxo-analogues of 3 (4-6) during LC-MS3 analysis of a fraction containing 1-3 and 7 are also reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chemical Fractionation
  • Dinoflagellida / chemistry
  • Dinoflagellida / metabolism*
  • Ethers, Cyclic / chemistry*
  • Ethers, Cyclic / isolation & purification*
  • Molecular Structure
  • Mollusk Venoms / chemistry*
  • Oxocins / chemistry*
  • Oxocins / isolation & purification*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • 41a-homoyessotoxin
  • Ethers, Cyclic
  • Mollusk Venoms
  • Oxocins
  • yessotoxin