Identification of Pinnatoxins and discovery of their fatty acid Ester Metabolites in mussels (Mytilus edulis) from Eastern Canada

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DOIResolve DOI: http://doi.org/10.1021/jf204824s
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TypeArticle
Journal titleJournal of Agricultural and Food Chemistry
Volume60
Issue6
Pages14371446; # of pages: 10
SubjectPinnatoxins; shellfish; Canada; fatty acids; esters; metabolites; LC-MS
AbstractPinnatoxins are a group of fast-acting cyclic imine toxins previously identified in shellfish from Asia, the southern Pacific, and northern Europe. In this work pinnatoxins were detected in mussels from locations across the eastern coast of Canada. Pinnatoxin G (6) was the major structural variant present, sometimes at levels >80 μg/kg, whereas much lower levels of pinnatoxin A (1) were detected in some samples. Increased concentrations were observed following base hydrolysis of extracts, leading to the discovery by LC-MS of a range of fatty acid esters of 6. Information on the structures of these acylated derivatives was provided through a series of mass spectrometric experiments, supported by partial synthesis, and it is proposed that the compounds are 28-O-acyl esters of 6. Although acyl esters of a range of other phycotoxins are known to form as metabolites in shellfish, this is the first report of their existence for this particular toxin class. The occurrence of pinnatoxins in North American shellfish further highlights the international distribution of these toxins.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Institute for Marine Biosciences
Peer reviewedYes
NRC number54087
NPARC number21268152
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Record identifiere326abc6-7773-4360-9cce-556de291efbc
Record created2013-05-10
Record modified2016-05-09
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