Discovery of fatty acid ester metabolites of spirolide toxins in mussels from Norway using lipid chromotography-tandem mass spectrometry

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DOIResolve DOI: http://doi.org/10.1002/rcm.2501
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TypeArticle
Journal titleRapid Communications in Mass Spectrometry
ISSN1097-0231
Volume20
Issue10
Pages15311537; # of pages: 7
Subjectphytoplankton; Alexandrium ostenfeldii; toxins; shellfish; fatty acids; metabolites; bioassay; mass spectrometry
AbstractCultured mussels sampled in the spring of 2002 and 2003 from Skjer, a location in the Sognefjord, Norway, tested positive in the mouse bioassay for lipophilic toxins. In a previous report, it was established that a number of spirolides, cyclic imine toxins produced by the phytoplankton Alexandrium ostenfeldii, were present in the mussels and were responsible for the observed toxicity. The main toxin proved to be a new compound named 20-methyl spirolide G. In subsequent studies, a delayed onset of spirolide-like symptoms in the mouse bioassay exceeding the usual time limit of 20 min was observed in some samples, with symptoms and death appearing as long as 45-50 min after injection. It is well known that shellfish can extensively metabolize other toxins, such as okadaic acid and the dinophysistoxins, to fatty acid acyl esters and it is also known that a delayed onset of toxic symptoms with such metabolites can occur. Analyses performed with liquid chromatography/tandem mass spectrometry (LC/MS/MS) have revealed a complex mixture of esters of 20-methyl spirolide G in the contaminated mussels. Precursor ion scanning has delineated the range of fatty acid esters involved, while product ion scanning has provided information on structure. Identity was also supported through reaction of 20-methyl spirolide G with palmitic anhydride, which produced a derivative with a retention time and spectrum identical with one putative metabolite, 17-O-palmitoyl-20-methyl spirolide G.
Publication date
PublisherJohn Wiley & Sons, Inc.
Copyright noticeCopyright © 2006 John Wiley & Sons, Ltd.
LanguageEnglish
AffiliationNRC Institute for Marine Biosciences; National Research Council Canada
Peer reviewedYes
NRC number55503
1460
NPARC number3538358
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Record identifiera69c9d11-7e87-4721-beed-f2ed29b4c270
Record created2009-03-01
Record modified2016-05-09
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