Identification of 45-hydroxy-46,47-dinoryessotoxin, 44-oxo-45,46,47-trinoryessotoxin, and 9-methyl-42,43,44,45,46,47,55-heptanor-38-en-41-oxoyessotoxin, and partial characterization of some minor yessotoxins, from Protoceratium reticulatum

Toxicon. 2006 Feb;47(2):229-40. doi: 10.1016/j.toxicon.2005.11.001. Epub 2005 Dec 20.

Abstract

Preparative HPLC purification of a side-fraction obtained during purification of 44,55-dihydroxyyessotoxin (6) afforded fractions containing previously unidentified yessotoxin analogues. Careful analysis of these fractions by HPLC-UV, LC-MS3, and NMR spectroscopy, revealed the identities of some of these analogues as 45-hydroxy-46,47-dinoryessotoxin (1), 44-oxo-45,46,47-trinoryessotoxin (2) and 9-methyl-42,43,44,45,46,47,55-heptanor-38-en-41-oxoyessotoxin (5). Numerous other analogues were present but could only be characterized by HPLC-UV and LC-MS3 due to their low abundance. The HPLC-UV and LC-MS3 data confirm the presence of large numbers of yessotoxin analogues, some of which may be oxidative degradation products, in extracts of Protoceratium reticulatum. Compound-1 is the first 46,47-dinoryessotoxin to be identified.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dinoflagellida / chemistry*
  • Ethers, Cyclic / chemistry*
  • Ethers, Cyclic / isolation & purification*
  • Molecular Structure
  • Mollusk Venoms
  • Oxocins / chemistry*
  • Oxocins / isolation & purification*

Substances

  • Ethers, Cyclic
  • Mollusk Venoms
  • Oxocins
  • yessotoxin