Identification of 21,22-Dehydroazaspiracids in Mussels ( Mytilus edulis ) and in Vitro Toxicity of Azaspiracid-26

Type Article
Date 2018-04
Language English
Author(s) Kilcoyne Jane1, McCarron Pearse2, Twiner Michael J.3, Rise Frode4, Hess PhilippORCID5, Wilkins Alistair L.6, Miles Christopher O.2, 6
Affiliation(s) 1 : Marine Inst, Oranmore H91 R673, Galway, Ireland.
2 : Natl Res Council Canada, Measurement Sci & Stand, Halifax, NS B3H 3Z1, Canada.
3 : Wayne State Univ, Detroit Receiving Hosp, Dept Emergency Med, Detroit, MI 48202 USA.
4 : Univ Oslo, Dept Chem, N-0315 Oslo, Norway.
5 : Ifremer, Lab Phycotoxines, Rue Ile Yeu, F-44311 Nantes, France.
6 : Norwegian Vet Inst, POB 750 Sentrum, N-0106 Oslo, Norway.
Source Journal Of Natural Products (0163-3864) (Amer Chemical Soc), 2018-04 , Vol. 81 , N. 4 , P. 885-893
DOI 10.1021/acs.jnatprod.7b00973
WOS© Times Cited 6
Abstract

Azaspiracids (AZAs) are marine biotoxins produced by the genera Azadinium and Amphidoma, pelagic marine dinoflagellates that may accumulate in shellfish resulting in human illness following consumption. The complexity of these toxins has been well documented, with more than 40 structural variants reported that are produced by dinoflagellates, result from metabolism in shellfish, or are extraction artifacts. Approximately 34 μg of a new AZA with MW 823 Da (AZA26 (3)) was isolated from blue mussels (Mytilus edulis), and its structure determined by MS and NMR spectroscopy. AZA26, possibly a bioconversion product of AZA5, lacked the C-20–C-21 diol present in all AZAs reported thus far and had a 21,22-olefin and a keto group at C-23. Toxicological assessment of 3 using an in vitro model system based on Jurkat T lymphocyte cells showed the potency to be ∼30-fold lower than that of AZA1. The corresponding 21,22-dehydro-23-oxo-analogue of AZA10 (AZA28) and 21,22-dehydro analogues of AZA3, -4, -5, -6, -9, and -10 (AZA25, -48 (4), -60, -27, -49, and -61, respectively) were also identified by HRMS/MS, periodate cleavage reactivity, conversion from known analogues, and NMR (for 4 that was present in a partially purified sample of AZA7).

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Kilcoyne Jane, McCarron Pearse, Twiner Michael J., Rise Frode, Hess Philipp, Wilkins Alistair L., Miles Christopher O. (2018). Identification of 21,22-Dehydroazaspiracids in Mussels ( Mytilus edulis ) and in Vitro Toxicity of Azaspiracid-26. Journal Of Natural Products, 81(4), 885-893. Publisher's official version : https://doi.org/10.1021/acs.jnatprod.7b00973 , Open Access version : https://archimer.ifremer.fr/doc/00428/54001/