Polyhydroxylated amide analogs of yessotoxin from Protoceratium reticulatum

Toxicon. 2005 Jan;45(1):61-71. doi: 10.1016/j.toxicon.2004.09.011.

Abstract

Two analogs of yessotoxin were isolated from extracts of a culture of Protoceratium reticulatum. The structures of the analogs were identified as trihydroxylated amides of 41a-homoyessotoxin (1) and 9-methyl-41a-homoyessotoxin (2) by one- and two-dimensional 1H and 13C NMR spectroscopy and LC-MS3 analyses. Structures were further confirmed by micro-scale chemical conversions combined with LC-MS3 analyses. No toxic effects were recorded in mice injected intraperitoneally with 2 at a dose of 5000 microg/kg.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

  • 41a-homoyessotoxin
  • 9-methyl-41a-homoyessotoxin
  • Ethers, Cyclic
  • Mollusk Venoms
  • Oxocins