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

@article{Ofuji2001StructuresOA,
  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},
  year={2001},
  volume={65},
  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.
TLDR
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.
  • R. Ueoka, A. Ito, +6 authors S. Matsunaga
  • Biology, Medicine
    Toxicon : official journal of the International Society on Toxinology
  • 2009
TLDR
A combination of HPLC using ODS, GS320, and Phenylhexyl stationary phases permitted the purification without using acid or inorganic additives in the mobile phase of Azaspiracid-2 to exhibit potent cytotoxicity against P388 cells.
Structure toxicity relationships of synthetic azaspiracid-1 and analogs in mice
TLDR
The lack of toxicity exhibited by the severely truncated azaspiracid-1 analogs implies that the entire or at least a major part of the structure of AZA-1 is required for biological activity.
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
TLDR
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.
TLDR
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.
TLDR
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.
Detection of five new hydroxyl analogues of azaspiracids in shellfish using multiple tandem mass spectrometry.
TLDR
Five new azaspiracids, AZA7-AZA11, have been found in mussels (Mytilus edulis), one of which is a positional isomer of AZA1 and four of the new compounds are isomers with a mass of 857.5 amu.
Comparative effects of the marine algal toxins azaspiracid-1, -2, and -3 on Jurkat T lymphocyte cells.
TLDR
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.
Facile biomimetic syntheses of the azaspiracid spiroaminal
Abstract The azaspiracid natural products display a common spiroaminal-containing terminal domain that has inspired the development of two new methods for spiroaminal syntheses—a Staudinger
...
1
2
3
4
5
...

References

SHOWING 1-3 OF 3 REFERENCES
Two analogs of azaspiracid isolated from mussels, Mytilus edulis, involved in human intoxication in Ireland.
TLDR
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.
Multiple organ damage caused by a new toxin azaspiracid, isolated from mussels produced in Ireland.
  • E. Ito, M. Satake, +4 authors T. Yasumoto
  • Biology, Medicine
    Toxicon : official journal of the International Society on Toxinology
  • 2000
TLDR
In vivo studies with mice revealed that the causative agent, azaspiracid, caused necrosis in the lamina propria of the small intestine and in lymphoid tissues such as thymus, spleen and the Peyer's patches.