Identification of fatty acid esters of pectenotoxin-2 seco acid in blue mussels (Mytilus edulis) from Ireland.
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.
Wilkins
Alistair L
AL
National Veterinary Institute, P.B. 8156 Dep., 0033 Oslo, Norway.
Rehmann
Nils
N
Torgersen
Trine
T
Rundberget
Thomas
T
Keogh
Myra
M
Petersen
Dirk
D
Hess
Philipp
P
Rise
Frode
F
Miles
Christopher O
CO
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000032:analysis*; D005227:Fatty Acids / Q000032:analysis*; D005663:Furans / Q000032:analysis* / Q000737:chemistry*; D007494:Ireland; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D049880:Mytilus edulis / Q000737:chemistry*; D011714:Pyrans / Q000032:analysis* / Q000737:chemistry*; D000095702:Polyether Toxins
D004952:Esters; D005227:Fatty Acids; D005663:Furans; D018942:Macrolides; D011714:Pyrans; C420916:pectenotoxin-2-seco acid; D000095702:Polyether Toxins