Isolation, structural elucidation, relative LC-MS response, and in vitro toxicity of novel azaspiracids from azadinium spinosum

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DOIResolve DOI: http://doi.org/10.1021/np500555k
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TypeArticle
Journal titleJournal of natural products
ISSN0163-3864
1520-6025
Volume77
Issue11
Pages24652474; # of pages: 10
AbstractWe identified three new azaspiracids (AZAs) with molecular weights of 715, 815, and 829 (AZA33 (3), AZA34 (4), and AZA35, respectively) in mussels, seawater, and Azadinium spinosum culture. Approximately 700 μg of 3 and 250 μg of 4 were isolated from a bulk culture of A. spinosum, and their structures determined by MS and NMR spectroscopy. These compounds differ significantly at the carboxyl end of the molecule from known AZA analogues and therefore provide valuable information on structure–activity relationships. Initial toxicological assessment was performed using an in vitro model system based on Jurkat T lymphocyte cytotoxicity, and the potencies of 3 and 4 were found to be 0.22- and 5.5-fold that of AZA1 (1), respectively. Thus, major changes in the carboxyl end of 1 resulted in significant changes in toxicity. In mussel extracts, 3 was detected at low levels, whereas 4 and AZA35 were detected only at extremely low levels or not at all. The structures of 3 and 4 are consistent with AZAs being biosynthetically assembled from the amino end.
Publication date
LanguageEnglish
AffiliationMeasurement Science and Standards; National Research Council Canada
Peer reviewedYes
NPARC number21274921
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Record identifier0826d1d5-8ccd-46cf-9361-5918d7b02826
Record created2015-04-29
Record modified2016-05-09
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