Isolation and structure elucidation of new and unusual saxitoxin analogues from mussels

From National Research Council Canada

DOIResolve DOI: http://doi.org/10.1021/np800066r
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Name affiliation
  1. National Research Council Canada. NRC Institute for Marine Biosciences
TypeArticle
Journal titleJournal of Natural Products
ISSN0163-3864
1520-6025
Volume71
Issue9
Pages1518–1523
Abstract
Chemical analyses of plankton and highly toxic mussel samples collected in eastern Canada during an intense bloom of the dinoflagellate Alexandrium tamarense established the presence of a complex mixture of paralytic shellfish poisoning (PSP) toxins. Application of a newly developed technique, hydrophilic interaction liquid chromatography-mass spectrometry, confirmed the identities of the known toxins and revealed the presence in the mussels of five saxitoxin analogues (M1-M5) that were not present in the plankton. Four of these compounds were isolated and their structures established by tandem mass spectrometry, 1D- and 2D-NMR spectroscopy, and chemical interconversion experiments. One of these was found to be 11beta-hydroxysaxitoxin (M2), while the other three were found to be new saxitoxin analogues, namely, 11beta-hydroxy-N-sulfocarbamoylsaxitoxin (M1), 11,11-dihydroxy-N-sulfocarbamoylsaxitoxin (M3), and 11,11-dihydroxysaxitoxin (M4). Compound M5 remains unidentified because of insufficient material for characterization.
Publication date
LanguageEnglish
Peer reviewedYes
IdentifierNRC-IMB-1710
NRC number42748
NPARC number3538296
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Record identifierc2b17b9e-a593-4f1f-b7ef-357624795c8f
Record created2009-03-01
Record modified2016-12-09
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