Azaspiracid shellfish poisoning

James, K.J, Lehane, M., Moroney, C., Eernandez-Puente, P, Satake, M., Yasumoto, T, and Eurey, A. 2002b. Azaspiracid shellfish poisoning unusual toxin dynamics in shellfish and the increased risk of acute human intoxications. FoodAddit Contam 19, 555-561. 

Azaspiracids [azaspiracid-1 (18)] are another class of highly unusual polyketide polyethers originally isolated from Irish mussels that caused azaspiracid shellfish poisoning (5). They are produced by the dinoflagellate Protoperidinium crassipes. A similar class of polyether toxins named pinnatoxins [pinnatoxin A (19)] were reported from the bivalve Pinna pectinata a closely related species P. attenuata is known to cause food poisoning in China. Pinnatoxins are likely of dinoflagellate origin and activate Ca channels (15). 

Commonly used synonyms for these sources and types of toxicity include azaspiracid shellfish poisoning (AZP) caused by five azaspiracid analogs ... 

Azaspiracid shellfish poisoning (AZP). Food and Agriculture Organization site about azaspiradds. Forms Chapter 6 of a comprehensive document on marine biotoxins. http //en.wikipedia.org/wild/Bivalvia Bivalvia. 

Twiner, M.J., Rehmann, N., Hess, P., and Doucette, G.J. (2008) Azaspiracid shellfish poisoning A review on the chemistry, ecology, and toxicology with an emphasis on human health impacts. Mar. Drugs, 6, 39-72. 

AZP, the most-recently characterized marine seafood poisoning, is associated with eating shellfish contaminated with azaspiracids. The first human intoxications attributed to AZP occurred in the Netherlands, and the symptoms included those similar to DSP (i.e., nausea, vomiting, severe diarrhea, and stomach cramps). However, although chemical analyses did not identify significant levels of the diarrhetic shellfish poisons, they identified a new class of toxins (James et ah, 2003a). 

In 1995, a report of human illness with diarrhetic shellfish poisoning (DSP)-like symptoms in the Netherlands was eventually found to result from the consumption of poisoned mussels (Mytilus edulis) harvested from Killary Harbour, Ireland (McMahon 1996). Yasumoto, Satake, and co-workers eventually isolated and proposed a stracture for the causative agent of this condition azaspiracid-1 (la. Fig. 16.1). The unique polyether stracture of azaspiracid-1 (la) is characterized by several spiro-cyclic systems, including an azaspiro ring fused to a 2,9-dioxabicyclo[3.3.1]nonane system and a terminal carboxylic acid. In total, there are nine rings and twenty stereogenic centers within the structure proposed by Yasumoto and co-workers in 1998 (Satake 1998). This stracture was based primarily on NMR spectroscopic data and did not include absolute stereochemistry, nor did it specify relative stereochemistry between the ABCDE and FGHI domains. 

The clinical symptoms caused by azaspiracid poisoning in humans are similar to diarrhetic shellfish poisoning and to bacterial enterotoxin poisoning. Because of the similarity of the gastrointestinal symptoms induced by this new toxin and the well characterized DSP (diarrheic shellfish poisoning) toxins in humans, azaspiracids have been classified at times in the diarrheic toxin group. However, when the chemical stmcture of this new toxin was identified as a completely different molecule from DSP toxins, this toxic syndrome was named azaspiracid poisoning (AZP). 

Azaspiracid (AZA) poisoning has been reported in five countries, all of them in the European Union and all from consumption of mussels cultivated in Ireland. The first outbreak occurred in Netherlands in November 1995 with eight people affected. The symptoms were similar to those of DSP, but the concentration of the major DSP toxins were very low [60]. No known organisms producing DSP toxins were observed in water samples collected at that time. In addition, a slowly progressing paralysis was observed in the mouse assay using mussel extracts. These neurotoxic symptoms were quite different from typical DSP toxicity. Subsequently, AZA was identified, and the new toxic syndrome was called AZA shellfish poisoning. 

Azaspiracid poisoning (AZP) is the most recently discovered of the toxic syndromes from shellfish consumption. The symptoms of acute AZP intoxication closely resembles those associated with diarrhetic shellfish poisoning (DSP), and include diarrhea, vomiting, and headache and the first confirmed incident was in 1995 (Netherlands), following the consumption of mussels (Mytilus edulis) that were cultivated in Ireland (Satake et al., 1998). Since these symptoms are similar to bacterial enterotoxin poisoning, and analytical methods for the detection of these toxins have only been developed in recent years, it is probable that there have been many unreported cases of this poisoning. The first azaspiracid to be identified was AZAl (Figure 35.1, = H R = CH3),... 

DSP Diarrhetic shellfish poison OA Okadaic acid DTXs Dinophysistoxins PTXs Pectenotoxins YTXs Yessotoxins and AZAs Azaspiracids. 

B. Diarrhetic shellfish poisoning is caused by several identified toxins, all of which appear to be produced by marine dinoflagellates. Suspected toxins include okadaic acid, dinophysistoxins, and azaspiracid. 

B. Diarrhetic shellfish poisoning causes nausea, vomiting, stomach cramps, and severe diarrhea. In animal studies, azaspiracid toxin caused damage to the liver, spleen, and small intestine. 

Structure, nomenclature and occurrence The group of marine toxins known as azaspiracids (AZA) was only recently discovered to be the cause of shellfish poisoning in humans. Their source is the algae of the genus Protoperidinium. Azaspiracids are a group of polyethers (such as okadaic acid), but they contain a nitrogen heterocyclic amine piperidine (10-246). About 20 different derivatives have... 

James, K.J., et al.. First evidence of an extensive northern European distribution of azaspiracid poisoning (AZP) toxins in shellfish, Toxicon, 40, 7, 909, 2002. 

James, K.J., et al.. Ubiquitous benign alga emerges as the cause of shellfish contamination responsible for the human toxic syndrome, azaspiracid poisoning, Toxicon, 41, 2, 145, 2003a. 

James, K.J., Fidalgo Saez, M.J., Furey, A., and Lehane, M. 2004. Azaspiracid poisoning, the food-borne illness associated with shellfish consumption. Food Additives and Contaminants 21, 879-892. 

Azaspiracid poisoning symptoms in humans include nausea, vomiting, diarrhea, stomach cramps, and headache. The symptoms appear 3 to 18 hours after eating contaminated shellfish, and the recovery is complete within 2 to 5 days (James et al. 2004 McMahon et al. 1996). 

James, K.J., Eurey, A., Lehane, M., Ramstad, H., Aune, T, Hovgaard P., Morris, S., Higman, W., Satake, M., andYasumoto, T. 2002a. Eirst evidence of an extensive northern European distribution of azaspiracid poisoning (AZP) toxins in shellfish. Toxicon 40, 909-915. 

James, K. J, Eurey, A., Satake, M., and Yasumoto, T. 2000. Azaspiracid Poisoning (AZP) A new shellfish toxic syndrome in Europe. Abstract for the 9th International Conference on Algal Blooms, Tasmania, Australia. 

Azaspiracid (AZA-1) and related compounds were involved in a nnmber of recent hnman intoxifications, cansing DSP-like symptoms. The toxic syndrome is called azaspiracid poisoning (AZP). The LC-MS analysis of AZA-1 was reported by Draisci et al. [125]. Isocratic elntion with 85% acetonitrile in 0.03% aqneons TFA from a 1.0-imn-ID Cig colnnm at 30 pl/min was performed. [M+H] was observed at m/z 842. In MS-MS, three snbsequent water losses were observed, next to several other minor fragments. The irrstrumental detection limit was 20 pg, which is cortsiderably better than the conventional mottse bioassay (2.8 pg). Lehane et al. [126] reported the analysis of AZA-1 and fom related compounds in shellfish down to 0.05 pg/ml. The same group compared various SPE methods [127]. They developed a CRM procedtrre with an ion-trap irrstrument for the determination of... 

The first human acute intoxications attributed to newly described azaspiracid poisoning (AZP) occurred in the Netherlands after consumption of contaminated shellfish. The symptoms were similar to the nausea, vomiting, severe diarrhea, and stomach cramps of DSP. AZP in humans has been reported throughout Europe since 1995, and azaspiracids have been found in shellfish harvested in Spain, France, and northern Europe. 

The azaspiracids (AZAs) are a new group of toxins identified in 1995 during an outbreak in the Netherlands, when symptoms of DSP poisoning were observed, but with very low concentration of OA and DTX in shellfish [60]. After purification, it was possible to identify this family of new toxins called azaspiracids [61]. 

KJ James, MJ Hidalgo Saez, Eurey A, M Lehane. Azaspiracid poisoning, the food-home illness associated with shellfish consumption. FoodAddit. Contam. 21 879-892, 2004. 

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