Domoic acids

The synthesis of kalnlc acid, acromehc acid, and related compounds such as domoic acid has been the subject of considerable investigation A simple and direct toiue to neurophysi-ologically active kalnlc acid analogs has been reported, as shovm in Scheme 10 31 ... 

Hardstafe WR, Jamieson WD, Milley JE, Quilliam MA, Sim PG (1990) Reference materials for domoic acid, a marine neurotoxin. Fresenius J Anal Chem 338 520-525. 

Although isolated in 1959 (125) from the now rare red alga Chondria armata Okamura (Rhodomelaceae), domoic acid (77) was given a tentative structure... 

Daigo K (1959) Constituents of Chondria armata. IV. Determination of domoic acid. Yakuga Zasshi 79 360-364... 

Alfonso M, Duran R, Campos F, Perez-Vences D, Faro LR, et al. 2003. Mechanisms underlying domoic acid-induced dopamine release from striatum an in vivo microdialysis study. Neurochem Res 28(10) 1487-1493. 

Okadaic acid Dinophysistoxins (>6) Domoic acid (3) Azaspiracid (5) Ciguatoxin (>10) Maitotoxin Scaritoxin... 

ASP is caused by eating shellfish contaminated with one or more of three domoic acid derivatives, which are excitatory neurotoxic amino acids (Baden and Trainer, 1993). Domoic acid is produced by the diatom Nitzchia pungens and accumulates in mussels, specifically Mytilus edulis (Baden and Trainer, 1993). Domoic acid is similar in structure to the excitatory dicarboxylic amino acid, kainic acid, and has an antagonistic effect at the glutamate receptor. Both... 

The first cases of ASP were identified after an outbreak associated with eating cultivated mussels harvested from Prince Edward Island, Canada (Perl et ah, 1990 Todd, 1990b). Domoic acid also has been implicated in the deaths of marine mammals along the U.S. Pacific coast (Scholin et ah, 2000), and human diseases from eating shellfish contaminated with domoic acid have been anecdotally reported in the U.S. Pacific Northwest. 

Toxin (primary or class of toxins) Saxitoxin Brevetoxin Okadaic acid, dinophysistoxin Domoic acid, kainic acid Azaspiracid Ciguatoxin... 

Kawatsu, K., Hamano, Y. and Noguchi, T., Production and characterization of a monoclonal antibody against domoic acid and its application to enz5mie... 

Perl, T.M., et al.. An outbreak of toxic encephalopathy caused by eating mussels contaminated with domoic acid, N. Engl. J. Med., 322, 25, 1775, 1990. 

Shinozaki, Y. and Ishida, M., Inhibition of quisqualate responses by domoic acid or kainic acid in crayfish opener muscle. Brain Res., 109, 435, 1976. 

Takeuchi, H., et al., Elfects of alpha-kainic acid, domoic acid and their derivatives on a molluscan giant neuron sensitive to beta-hydroxy-L-glutamic acid, Eur. J. Pharmacol, 102, 2, 325, 1984. 

Tor, E.R., Puschner, B. and Whitehead, W.E., Rapid determination of domoic acid in serum and urine by liquid chromatography-electrospray tandem mass spectrometry, J. Agric. Food Chem., 51, 7, 1791, 2003. 

For example, some compounds will dissolve in water and others in fat (called a lipid). One of their 20 questions was, "Does the poisoning agent dissolve in water or fat To get an answer, they shook one mussel sample with a mixture of water and another mussel sample with a mixture of fat and injected the water and fat parts into different mice.The part of the mussel that dissolved in the water still caused the mice to scratch themselves, but the part that dissolved in fat didn t. So they knew they were looking for a chemical that dissolves in water. They divided the mussel over and over using many different methods, including chromatography, which is similar to the project at the end of this chapter. Finally, after four days of continuous work, the scientists had separated out of the mixture a pure substance that was the toxic compound.They compared all of its properties to compounds they already knew about and found a match a neurotoxic compound called "domoic acid. ... 

Now that we know exactly what caused the problem, seafood can be checked for domoic acid to make sure there are no more poisonings. 

Mestel, Rosie. Hitch s birds deranged by dodgy anchovies (toxicity of domoic acid in Alfred Hitchcock s seabirds). New Scientist 147.nl987 Quly 22,1995) 6(1). Expanded Academic HSHR Thomson Gale. EIN Remote Access. 29 Mar. 2007. 

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