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

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DOIResolve DOI: http://doi.org/10.1021/np800066r
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TypeArticle
Journal titleJournal of Natural Products
ISSN0163-3864
1520-6025
Volume71
Issue9
Pages15181523
AbstractChemical 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
AffiliationNRC Institute for Marine Biosciences; National Research Council Canada
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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