Characterization of spirolides A, C, and 13-desmethyl C, new marine toxins isolated from toxic plankton and contaminated shellfish

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DOIResolve DOI: http://doi.org/10.1021/np000416q
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TypeArticle
Journal titleJournal of Natural Products
ISSN0163-3864
1520-6025
Volume64
Issue3
Pages308312
AbstractThree additional marine toxins, spirolides A (1), C (3), and 13-desmethyl-C (7), were isolated from contaminated scallops and phytoplankton collections obtained from a Nova Scotian aquaculture site, as well as from batch cultures of the dinoflagellate Alexandrium ostenfeldii obtained as a single-cell isolate from these phytoplankton assemblages. The structures of these new spirolide derivatives, characterized by mass spectrometry and NMR, indicate a close relationship with spirolides B (2) and D (4) isolated previously from contaminated shellfish in the same area. All of these compounds display “fast-acting” toxicity in the traditional bioassay used for monitoring shellfish, and this is related to the presence of a cyclic imine function in all these compounds. Those spirolides containing a vicinal dimethyl group in the seven-membered ring are resistant to oxalic acid hydrolysis, whereas those that do not are readily hydrolyzed. These observations suggest that the extra methyl group on the seven-membered imine ring of 3, 4, and 7 appears to block the process of imine hydrolysis perhaps by stereochemical interference.
Publication date
LanguageEnglish
AffiliationNRC Institute for Marine Biosciences; National Research Council Canada
Peer reviewedYes
NPARC number23001024
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Record identifierb9134016-0ad1-4ff4-8ac0-6016d70b776d
Record created2016-11-29
Record modified2016-11-29
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