Biochemistry of Azaspiracid Poisoning Toxins

Phycotoxins: Chemistry and Biochemistry

Volumn , Issue , 2007, Pages 311-318

  Vilariño, Natalia ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Azaspiracid poisoning syndrome; Azaspiracid poisoning toxins; Biochemistry; Shellfish; Toxic algal blooms

Indexed keywords

EID: 46349098039     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470277874.ch17     Document Type: Chapter

References (39)

1. Alfonso, A., Roman, Y., Vieytes, M.R., Ofuji, K., Satake, M., Yasumoto, T., and Botana, L.M. 2005. Azaspiracid-4 inhibits Ca21 entry by stored operated channels in human T lymphocytes. Biochem Pharmacol 69, 1627-1636.
2. Colman, J.R., Dechraoui, M.Y., Dickey, R.W., and Ramsdell, J.S. 2004. Characterization of the developmental toxicity of Caribbean ciguatoxins in finfish embryos. Toxicon 44, 59-66.
3. Colman, J.R., Twiner, M.J., Hess, P., McMahon, T., Satake, M., Yasumoto, T., Doucette, G.J., and Ramsdell, J.S. 2005. Teratogenic effects of azaspiracid-1 identified by microinjection of Japanese medaka (Oryzias latipes) embryos. Toxicon 45, 881-890.
4. EU. 2002. Commission decision 2002/225/EC of 15 March. 2002. laying down detailed rules for the implementation of council directive 91/492/EEC as regards the maximum levels and the methods of analysis of certain marine biotoxins in bivalve molluscs, echinoderms, tunicates and marine gastropods. OJ L75, 62-64.
5. EU/SANCO. 2001. Report of the meeting of the working group on toxicology of DSP and AZP 21 to 23rd May 2001, Brussels.
6. FAO. 2004. Food and nutrition paper on marine biotoxins.
7. Fujiki, H., Suganuma, M., Komori, A., Yatsunami, J., Okabe, S., Ohta, T., and Sueoka, E. 1994. A new tumor promotion pathway and its inhibitors. Cancer Detect Prev 18, 1-7.
8. Fujiki, H., Suganuma, M., Nishiwaki, S., Yoshizawa, S., Winyar, B., Sugimura, T., and Schmitz, F. J. 1990. A new pathway of tumor promotion by the okadaic acid class compounds. Adv Second Messenger Phosphoprotein Res 24, 340-344.
9. Furey, A., Moroney, C., Brana-Magdalena, A., Saez, M.J., Lehane, M., and James, K.J. 2003. Geographical, temporal, and species variation of the polyether toxins, azaspiracids, in shellfish. Environ Sci Technol 37, 3078-3084.
10. Hess, P., Nguyen, L., Aasen, J., Keogh, M., Kilcoyne, J., McCarron, P., and Aune, T. 2005. Tissue distribution, effects of cooking and parameters affecting the extraction of azaspiracids from mussels, Mytilus edulis, prior to analysis by liquid chromatography coupled to mass spectrometry. Toxicon 46, 62-71.
11. Ito, E., Satake, M., Ofuji, K., Higashi, M., Harigaya, K., McMahon, T., and Yasumoto, T. 2002. Chronic effects in mice caused by oral administration of sublethal doses of azaspiracid, a new marine toxin isolated from mussels. Toxicon 40, 193-203.
12. Ito, E., Satake, M., Ofuji, K., Kurita, N., McMahon, T., James, K., and Yasumoto, T. 2000. Multiple organ damage caused by a new toxin azaspiracid, isolated from mussels produced in Ireland. Toxicon 38, 917-930.
13. Ito, E., Terao, K., McMahon, T., Silke, J., and Yasumoto, T. 1998. Acute pathological changes in mice caused by crude extracts of novel toxins isolated from Irish mussels. Ed. Reguera, B., Blanco, J., Fernandez, M.L., and Wyatt, T. Santiago de Compostela, Spain: IOC of UNESCO and Xunta de Galicia, 588-589.
14. James, K.J., Fidalgo Saez, M.J., Furey, A., and Lehane, M. 2004. Azaspiracid poisoning, the food-borne illness associated with shellfish consumption. Food Addit Contam 21, 879-892.
15. James, K.J., Furey, A., Lehane, M., Ramstad, H., Aune, T., Hovgaard, P., Morris, S., Higman, W., Satake, M., and Yasumoto, T. 2002a. First evidence of an extensive northern European distribution of azaspiracid poisoning (AZP) toxins in shellfish. Toxicon 40, 909-915.
16. James, K.J., Furey, 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.
17. James, K.J., Lehane, M., Moroney, C., Fernandez-Puente, P., Satake, M., Yasumoto, T., and Furey, A. 2002b. Azaspiracid shellfish poisoning: unusual toxin dynamics in shellfish and the increased risk of acute human intoxications. Food Addit Contam 19, 555-561.
18. James, K.J., Moroney, C., Roden, C., Satake, M., Yasumoto, T., Lehane, M., and Furey, A. 2003a. Ubiquitous "benign" alga emerges as the cause of shellfish contamination responsible for the human toxic syndrome, azaspiracid poisoning. Toxicon 41, 145-151.
19. James, K.J., Sierra, M.D., Lehane, M., Brana Magdalena, A., and Furey, A. 2003b. Detection of five new hydroxyl analogues of azaspiracids in shellfish using multiple tandem mass spectrometry. Toxicon 41, 277-283.
20. Jeong, H.J., and Latz, M.I. 1994. Growth and grazing rates of the heterotrophic dinoflagellate, Protoperidinium, on red tide dinoflagellates. Mar Ecol Prog Ser 106, 173-185.
21. Kimm-Brinson, K.L., and Ramsdell, J.S. 2001. The red tide toxin, brevetoxin, induces embryo toxicity and developmental abnormalities. Environ Health Perspect 109, 377-381.
22. Latz, M.I., and Jeong, H.J. 1996. Effect of red tide dinoflagellate diet and cannibalism on the bioluminescence of the heterotrophic dinoflagellates Protoperidinium spp. Mar Ecol Prog Ser 132, 275-285.
23. Magdalena, A.B., Lehane, M., Krys, S., Fernandez, M.L., Furey, A., and James, K.J. 2003a. The first identification of azaspiracids in shellfish from France and Spain. Toxicon 42, 105-108.
24. Magdalena, A.B., Lehane, M., Moroney, C., Furey, A., and James, K.J. 2003b. Food safety implications of the distribution of azaspiracids in the tissue compartments of scallops (Pecten maximus). Food Addit Contam 20, 154-160.
25. McMahon, T., and Silke, J. 1996. Winter toxicity of unknown aetiology in mussels. Harmful Algae News 14, 2.
26. McMahon, T., and Silke, J. 1998. Re-occurrence of winter toxicity. Harmful Algae News 17, 12-16.
27. Nicolaou, K.C., Chen, D.Y., Li, Y., Qian, W., Ling, T., Vyskocil, S., Koftis, T.V., Govindasamy, M., and Uesaka, N. 2003a. Total synthesis of the proposed azaspiracid-1 structure, part 2: coupling of the C1-C20, C21-C27, and C28-C40 fragments and completion of the synthesis. Angew Chem Int Ed Engl 42, 3649-3653.
28. Nicolaou, K.C., Li, Y., Uesaka, N., Koftis, T.V., Vyskocil, S., Ling, T., Govindasamy, M., Qian, W., Bernal, F., and Chen, D.Y. 2003b. Total synthesis of the proposed azaspiracid-1 structure, part 1: construction of the enantiomerically pure C1-C20, C21-C27, and C28-C40 fragments. Angew Chem Int Ed Engl 42, 3643-3648.
29. Ofuji, K., Satake, M., McMahon, T., James, K.J., Naoki, H., Oshima, Y., and Yasumoto, T. 2001. Structures of azaspiracid analogs, azaspiracid-4 and azaspiracid-5, causative toxins of azaspiracid poisoning in Europe. Biosci Biotechnol Biochem 65, 740-742.
30. Ofuji, K., Satake, M., McMahon, T., Silke, J., James, K. J., Naoki, H., Oshima, Y., and Yasumoto, T. 1999a. Two analogs of azaspiracid isolated from mussels, Mytilus edulis, involved in human intoxication in Ireland. Nat Toxins 7, 99-102.
31. Ofuji, K., Satake, M., Oshima, Y., McMahon, T., James, K. J., and Yasumoto, T. 1999b. A sensitive and specific determination method for azaspiracids by liquid chromatography mass spectrometry. Nat Toxins 7, 247-250.
32. RASFF. 2005. Rapid Alert System for Food and Feed. Week 47, 2005.
33. Roman, Y., Alfonso, A., Louzao, M. C., de la Rosa, L.A., Leira, F., Vieites, J.M., Vieytes, M.R., Ofuji, K., Satake, M., Yasumoto, T., and Botana, L.M. 2002. Azaspiracid-1, a potent, nonapoptotic new phycotoxin with several cell targets. Cell Signal 14, 703-716.
34. Roman, Y., Alfonso, A., Vieytes, M.R., Ofuji, K., Satake, M., Yasumoto, T., and Botana, L.M. 2004. Effects of Azaspiracids 2 and 3 on intracellular cAMP, [Ca2+], and pH. Chem Res Toxicol 17, 1338-1349.
35. Satake, M., Ofuji, K., Naoki, H., James, K., Furey, A., McMahon, T., Silke, J., and Yasumoto, T. 1998a. Azaspiracid, a New Marine Toxin Having Unique Spiro Ring Assemblies, Isolated from Irish Mussels, Mytilus edulis. J Am Chem Soc 120.
36. Satake, M., Ofuji, K., James, K., Furey, A. and Yasumoto, T. 1998b. New toxic event caused by Irish mussels. Ed. Reguera, B., Blanco, J., Fernandez, M., and Wyatt, T. Xunta de Galicia and IOC of UNESCO, 468-469.
37. Twiner, M.J., Hess, P., Dechraoui, M.Y., McMahon, T., Samons, M.S., Satake, M., Yasumoto, T., Ramsdell, J.S., and Doucette, G.J. 2005. Cytotoxic and cytoskeletal effects of azaspiracid-1 on mammalian cell lines. Toxicon 45, 891-900.
38. Vilariño, N. Nicolaou, K.C., Frederick, M.O., Cagide, E., Ares, I.R., Louzao, M.C., Vieytes, M.R., and Botana, L.M. 2006. Cell growth inhibition and actin cytoskeleton disorganisation induced by azaspiracid-A. Structure-activities studies. Chem. Res. Toxicol 19, 1459-1466.
39. Volmer, D.A., Brombacher, S., and Whitehead, B. 2002. Studies on azaspiracid biotoxins. I. Ultrafast high-resolution liquid chromatography/mass spectrometry separations using monolithic columns. Rapid Commun Mass Spectrom 16, 2298-2305.