FN Archimer Export Format
PT J
TI Isolation, Structure Elucidation, Relative LC-MS Response, and in Vitro Toxicity of Azaspiracids from the Dinoflagellate Azadinium spinosum
BT 
AF KILCOYNE, Jane
   NULTY, Ciara
   JAUFFRAIS, Thierry
   MCCARRON, Pearse
   HERVE, Fabienne
   FOLEY, Barry
   RISE, Frode
   CRAIN, Sheila
   WILKINS, Alistair L.
   TWINER, Michael J.
   HESS, Philipp
   MILES, Christopher O.
AS 1:1,2;2:1;3:3,4;4:5;5:3;6:2;7:6;8:5;9:7;10:8;11:3;12:7,9;
FF 1:;2:;3:;4:;5:PDG-ODE-LITTORAL-PHYC;6:;7:;8:;9:;10:;11:PDG-ODE-LITTORAL-PHYC;12:;
C1 Inst Marine, Galway, Ireland.
   Dublin Inst Technol, Sch Chem & Pharmaceut Sci, Dublin 8, Ireland.
   IFREMER, Lab Phycotoxines, F-44311 Nantes, France.
   Univ Nantes, Fac Sci & Tech, Mer Mol Sante EA2160, F-44322 Nantes, France.
   Natl Res Council Canada, Halifax, NS B3H 3Z1, Canada.
   Univ Oslo, Dept Chem, N-0315 Oslo, Norway.
   Norwegian Vet Inst, N-0106 Oslo, Norway.
   Univ Michigan, Dept Nat Sci, Dearborn, MI 48128 USA.
   Univ Oslo, Sch Pharm, Dept Pharmaceut Chem, N-0316 Oslo, Norway.
C2 MARINE INST GALWAY, IRELAND
   DUBLIN INST TECHNOL, IRELAND
   IFREMER, FRANCE
   UNIV NANTES, FRANCE
   NATL RES COUNCIL CANADA, CANADA
   UNIV OSLO, NORWAY
   NORWEGIAN VET INST, NORWAY
   UNIV MICHIGAN, USA
   UNIV OSLO, NORWAY
SI NANTES
SE PDG-ODE-LITTORAL-PHYC
IN WOS Ifremer jusqu'en 2018
   copubli-france
   copubli-europe
   copubli-univ-france
   copubli-int-hors-europe
IF 3.798
TC 39
UR https://archimer.ifremer.fr/doc/00245/35606/34414.pdf
LA English
DT Article
AB We 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 mu g of 3 and 250 mu g 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. 
PY 2014
PD NOV
SO Journal Of Natural Products
SN 0163-3864
PU Amer Chemical Soc
VL 77
IS 11
UT 000345472100020
BP 2465
EP 2474
DI 10.1021/np500555k
ID 35606
ER

EF