Structures of Azaspiracid Analogs, Azaspiracid-4 and Azaspiracid-5, Causative Toxins of Azaspiracid Poisoning in Europe

  title={Structures of Azaspiracid Analogs, Azaspiracid-4 and Azaspiracid-5, Causative Toxins of Azaspiracid Poisoning in Europe},
  author={Katsuya Ofuji and Masayuki Satake and Terry Mcmahon and Kevin J. James and Hideo Naoki and Yasukatsu Oshima and Takeshi Yasumoto},
  journal={Bioscience, Biotechnology, and Biochemistry},
  pages={740 - 742}
Two new analogs of azaspiracid, azaspiracid-4 and azaspiracid-5, isolated from the mussel Mytilus edulis, involved in a newly emerged shellfish poisoning in Europe were determined to be 3-hydroxy-22-demethylazaspiracid and 23-hydroxy-22-demethylazaspiracid, respectively. 

Total synthesis and confirmation of the revised structures of azaspiracid-2 and azaspiracid-3.

The 39 steps: The recently proposed revised structures of azaspiracid-2 and -3 (see picture) have been confirmed through the total syntheses of the two compounds, representing a major improvement over the first-generation synthesis of azAspir acid-1 (50 steps).

Isolation of azaspiracid-2 from a marine sponge Echinoclathria sp. as a potent cytotoxin.

Effect of Dilution Rate on Azadinium spinosum and Azaspiracid (AZA) Production in Pilot Scale Photobioreactors for the Harvest of AZA1 and -2

Azadinium spinosum, a small dinoflagellate has recently been discovered and identified as the primary producer of azaspiracid-1 (AZA) and -2. Since AZA poisoning has been reported following

Structure Elucidation and in Vitro Toxicity of New Azaspiracids Isolated from the Marine Dinoflagellate Azadinium poporum

Two strains of Azadinium poporum, one from the Korean West coast and the other from the North Sea, were mass cultured for isolation of new azaspiracids and were found to be 6- and 3-fold less toxic than AZA-1.

Azaspiracid substituent at C1 is relevant to in vitro toxicity.

The azaspiracids are a group of marine toxins recently described that currently includes 20 analogues and the presence of a methyl moiety at C8 is irrelevant to AZA toxicity since AZA-1 andAZA-2 were equipotent regardless of the readout effect.

Synthetic study of azaspiracid-1: synthesis of the EFGHI-ring fragment.

A synthesis of the lower half C21-C40 fragment of the shellfish toxin, azaspiracid-1 was reported, which was synthesized by a coupling between the C28-C35 epoxide and the C36-C 40 dithioacetal anion, followed by the HI-ring spiroaminal formation.

Comparative effects of the marine algal toxins azaspiracid-1, -2, and -3 on Jurkat T lymphocyte cells.

The data support the growing body of evidence suggesting that natural analogues of AZA are highly potent and that they may have multiple molecular targets.



Multiple organ damage caused by a new toxin azaspiracid, isolated from mussels produced in Ireland.

Two analogs of azaspiracid isolated from mussels, Mytilus edulis, involved in human intoxication in Ireland.

Two new analogs of azaspiracid were isolated from mussels collected at Arranmore Island, Ireland in 1997 as additional causes of human intoxication by NMR and negative ion FAB CID MS/MS experiments.