Identification of fatty acid esters of pectenotoxin-2 seco acid in blue mussels (Mytilus edulis) from Ireland

J Agric Food Chem. 2006 Jul 26;54(15):5672-8. doi: 10.1021/jf060396j.

Abstract

Pectenotoxins from marine dinoflagellates of the genus Dinophysis are rapidly hydrolyzed by many shellfish to give pectenotoxin-2 seco acid, which isomerizes to 7-epi-pectenotoxin-2 seco acid. Three series of fatty acid esters of pectenotoxin-2 seco acid (PTX-2 seco acid) and 7-epi-PTX-2 seco acid were detected by LC-MS analysis of extracts from blue mussels (Mytilus edulis) from Ireland. The locations of the fatty acid ester linkages were identified by a combination of LC-MSn in positive- and negative-ion modes, LC-MS analysis of the products from reaction of the esters with sodium periodate, and NMR analysis of purified samples of the two most abundant ester derivatives. The 37-O-acyl esters of PTX-2 seco acid were the most abundant, followed by the corresponding 11-O-acyl esters, accompanied by low levels of the 33-O-acyl esters. The most abundant fatty acid esters in the fractionated sample were, in order, the 16:0, 22:6, 14:0, 16:1, 18:4, and 20:5 fatty acids, although a wide array of other PTX-2 seco acid fatty acid esters were also present at low levels.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Esters / analysis*
  • Fatty Acids / analysis*
  • Furans / analysis*
  • Furans / chemistry*
  • Ireland
  • Macrolides
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mytilus edulis / chemistry*
  • Pyrans / analysis*
  • Pyrans / chemistry*

Substances

  • Esters
  • Fatty Acids
  • Furans
  • Macrolides
  • Pyrans
  • pectenotoxin-2-seco acid