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Structure elucidation, relative lc–ms response and in vitro toxicity of azaspiracids7–10isolated from mussels (mytilus edulis)

Kilcoyne, Jane
; 
Twiner, Michael J.
; 
McCarron, Pearse
; 
Crain, Sheila
; 
Giddings, Sabrina D.
; 
Foley, Barry
; 
Rise, Frode
; 
Hess, Philipp
; 
Wilkins, Alistair L.
; 
Miles, Christopher O.
Identifiers
http://hdl.handle.net/10379/12267
 https://doi.org/10.13025/27519
Publication Date
2015-05-27
Keywords
azaspiracid, structure confirmation, lc-ms molar response, nmr, mass spectrometry, purification, jurkat t, toxicity, azadinium-spinosum, c28-c40 fragments, mass-spectrometry, algal toxins, marine toxin, cell-lines, shellfish, analogs, mice, dinoflagellate
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Article
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Citation
Kilcoyne, Jane; Twiner, Michael J. McCarron, Pearse; Crain, Sheila; Giddings, Sabrina D.; Foley, Barry; Rise, Frode; Hess, Philipp; Wilkins, Alistair L.; Miles, Christopher O. (2015). Structure elucidation, relative lc–ms response and in vitro toxicity of azaspiracids7–10isolated from mussels (mytilus edulis). Journal of Agricultural and Food Chemistry 63 (20), 5083-5091
Abstract
Azaspiracids (AZAs) are marine biotoxins produced by dinoflagellates that can accumulate in shellfish, which if consumed can lead to poisoning events. AZA7-10, 7-10, were isolated from shellfish and their structures, previously proposed on the basis of only LC-MS/MS data, were confirmed by NMR spectroscopy. Purified AZA4-6, 4-6, and 7-10 were accurately quantitated by qNMR and used to assay cytotoxicity with Jurkat T lymphocyte cells for the first time. LC-MS(MS) molar response studies performed using isocratic and gradient elution in both selected ion monitoring and selected reaction monitoring modes showed that responses for the analogues ranged from 0.3 to 1.2 relative to AZA1, 1. All AZA analogues tested were cytotoxic to Jurkat T lymphocyte cells in a time- and concentration-dependent manner; however, there were distinct differences in their EC50 values, with the potencies for each analogue being: AZA6 > AZA8 > AZA1 > AZA4 approximate to AZA9 > AZA5 approximate to AZA10. This data contributes to the understanding of the structure-activity relationships of AZAs.
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Publisher
American Chemical Society (ACS)
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
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Externally hosted open access publications with University of Galway authors (2)