FN Archimer Export Format PT J TI Identification of 21,22-Dehydroazaspiracids in Mussels ( Mytilus edulis ) and in Vitro Toxicity of Azaspiracid-26 BT AF KILCOYNE, Jane MCCARRON, Pearse TWINER, Michael J. RISE, Frode HESS, Philipp WILKINS, Alistair L. MILES, Christopher O. AS 1:1;2:2;3:3;4:4;5:5;6:6;7:2,6; FF 1:;2:;3:;4:;5:PDG-ODE-DYNECO-PHYC;6:;7:; C1 Marine Inst, Oranmore H91 R673, Galway, Ireland. Natl Res Council Canada, Measurement Sci & Stand, Halifax, NS B3H 3Z1, Canada. Wayne State Univ, Detroit Receiving Hosp, Dept Emergency Med, Detroit, MI 48202 USA. Univ Oslo, Dept Chem, N-0315 Oslo, Norway. Ifremer, Lab Phycotoxines, Rue Ile Yeu, F-44311 Nantes, France. Norwegian Vet Inst, POB 750 Sentrum, N-0106 Oslo, Norway. C2 MARINE INST, IRELAND NATL RES COUNCIL CANADA, CANADA UNIV WAYNE STATE, USA UNIV OSLO, NORWAY IFREMER, FRANCE NORWEGIAN VET INST, NORWAY SI NANTES SE PDG-ODE-DYNECO-PHYC IN WOS Ifremer jusqu'en 2018 copubli-europe copubli-int-hors-europe IF 4.257 TC 21 UR https://archimer.ifremer.fr/doc/00428/54001/55286.pdf LA English DT Article AB 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). PY 2018 PD APR SO Journal Of Natural Products SN 0163-3864 PU Amer Chemical Soc VL 81 IS 4 UT 000431165100019 BP 885 EP 893 DI 10.1021/acs.jnatprod.7b00973 ID 54001 ER EF