Dinoflagellate polyether within the yessotoxin, pectenotoxin and okadaic acid toxin groups: Characterization, analysis and human health implications

Toxicon

Volumn 56, Issue 2, 2010, Pages 191-217

  Dominguez, Humberto J ^a   Paz, Beatriz ^b,c   Daranas, Antonio H ^a   Norte, Manuel ^a   Franco, José M ^b,c   Fernández, José J ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b INSTITUTO DE INVESTIGACIONES MARINAS   (Spain)

^c Instituto Español de Oceanografía   (Spain)

Author keywords

Diarrhetic Shellfish Poisoning (DSP); Dinophysistoxins (DTXs); Okadaic acid (OA); Pectenotoxins (PTXs); Yessotoxins (YTXs)

Indexed keywords

DINOPHYSISTOXIN 1; MARINE TOXIN; OKADAIC ACID; PECTENOTOXIN; POLYETHER; UNCLASSIFIED DRUG; YESSOTOXIN;

ARTICLE; BIOASSAY; BIVALVE; CAPILLARY ELECTROPHORESIS; CARDIOTOXICITY; CHEMICAL STRUCTURE; DIARRHEA; DINOFLAGELLATE; DISEASE SEVERITY; FOOD CONTAMINATION; FOOD CONTROL; FOOD INTAKE; FOOD POISONING; GASTROINTESTINAL DISEASE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIQUID CHROMATOGRAPHY; LIVER NECROSIS; NONHUMAN; PRIORITY JOURNAL; PUBLIC HEALTH; RADIOIMMUNOASSAY; RISK ASSESSMENT; SHELLFISH POISONING; TOXIN ANALYSIS;

ANIMALS; DINOFLAGELLIDA; HUMANS; LIVER; MICE; MOLECULAR STRUCTURE; MYOCARDIUM; NECROSIS; OKADAIC ACID; OXOCINS; PYRANS; RATS; SHELLFISH; SHELLFISH POISONING; TOXICITY TESTS;

BIVALVIA; DINOPHYCEAE; MUS;

EID: 77953286814     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2009.11.005     Document Type: Article

References (262)

1. Aasen J., Samdal I.A., Miles C.O., Dahl E., Briggs L.R., Aune T. Yessotoxins in Norwegian blue mussels (Mytilus edulis): uptake from Protoceratium reticulatum, metabolism and depuration. Toxicon 2005, 45:265-272.
2. Aasen J., Hardstaff W.R., Aune T., Quilliam M.A. Discovery of fatty acid ester metabolites of spirolide toxins in mussels from Norway using liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2006, 20:1531-1537.
3. Alfonso A., de la Rosa L.A., Vieytes M.R., Yasumoto T., Botana L.M. Yessotoxin, a novel phycotoxin, activates phosphodiesterase activity. Effect of yessotoxin on cAMP levels in human lymphocytes. Biochem. Pharmacol. 2003, 65:193-208.
4. 2+ entry by stored operated channels in human T Iymphocytes. Biochem. Pharmacol. 2005, 69:1543-1680.
5. Alfonso A., Vieytes M.R., Ofuji K., Satake M., Nicolaou K.C., Frederick M.O., Botana L.M. Azaspiracids modulate intracellular pH levels in human lymphocytes. Biochem. Biophys. Res. Commun. 2006, 346:1091-1099.
6. Allingham J.S., Miles C.O., Rayment I. A structural basis for regulation of actin polymerization by pectenotoxins. J. Mol. Biol. 2007, 371:959-970.
7. Armstrong M., Kudela R. Evaluation of California isolates of Lingulodinium poliedrum for the production of yessotoxin. Afr. J. Mar. Sci. 2006, 25:399-401.
8. Amzil Z., Pouchus Y.F., Le Boterf J., Roussakis C., Verbist J.F., Marcaillou-LeBaut C., Masselin P. Short-time cytotoxicity of mussel extracts: a new bioassay for okadaic acid detection. Toxicon 1992, 30:1419-1425.
9. Aonuma S., Ushijima T., Nakayasu M., Shima H., Sugimura T., Nagao M. Mutation induction by okadaic acid, a protein phosphatase inhibitor, in CHL cells, but not in S. typhimurium. Mutat. Res. 1991, 250:375-381.
10. Ares I.R., Louzao M.C., Vieytes M.R., Yasumoto T., Botana L.M. Actin cytoskeleton of rabbit intestinal cells is a target for potent marine phycotoxins. J. Exp. Biol. 2005, 208:4345-4354.
11. Ares I.R., Louzao M.C., Espiña B., Vieytes M.R., Miles C.O., Yasumoto T., Botana L.M. Lactone ring of Pectenotoxins: a key factor for their activity on cytoskeletal dynamics. Cell. Physiol. Biochem. 2007, 19:263-292.
12. Aune T., Yasumoto T., Engeland E. Light and scanning electron microscopic studies on effects of marine algal toxins toward freshly prepared hepatocytes. J. Toxicol. Environ. Health 1991, 34:1-9.
13. Aune T., Yndestad M. Diarrhetic shellfish poisoning. Algal Toxins in Seafood and Drinking Water 1993, 87-104. Academic Press, London. L.A. Falconer (Ed.).
14. Aune T., Sorby R., Yasumoto T., Ramstad H., Landsverk T. Comparison of oral and intraperitoneal toxicity of yessotoxin towards mice. Toxicon 2002, 40:77-82.
15. Aune T., Larsen S., Aasen J.A.B., Rehmann N., Satake M., Hess P. Relative toxicity of dinophysistoxin-2 (DTX-2) compared with okadaic acid, based on acute intraperitoneal toxicity in mice. Toxicon 2007, 49:1-7.
16. Aune T., Aasen J.A.B., Miles C.O., Larsen S. Effect of mouse strain and gender on LD50 of yessotoxin. Toxicon 2008, 52:535-540.
17. Berven G., Sætre F., Halvorsen K., Seglen P.O. Effects of the diarrhetic shellfish toxin, okadaic acid, on cytoskeletal elements, viability and functionality of rat liver and intestinal cells. Toxicon 2001, 39:349-362.
18. Bialojan C., Takai A. Inhibitory effect of a marine-sponge toxin, okadaic acid, on protein phosphatases. Biochem. J. 1988, 256:2283-2290.
19. Bianchi C., Fato R., Angelin A., Trombetti F., Ventrella V., Borgatti A.R., Fattorusso E., Ciminiello P., Bernardi P., Lenaz G., Parenti C.G. Yessotoxin, a shellfish biotoxin, is a potent inducer of the permeability transition in isolated mitochondria and intact cells. Biochim. Biophys. Acta 2004, 1656:139-147.
20. Blanco J., Moroño A., Fernández M.L. Toxic episodes in shellfish, produced by lipophilic phycotoxins: an overview. Revista Galega de Recursos Mariños Monografías 2005, 1:1-70.
21. Bouaïcha N., Hennion M.C., Sandra P. Determination of okadaic acid by micellar electrokinetic chromatography with ultraviolet detection. Toxicon 1997, 35:273-281.
22. Bouaïcha N., Maatouk I., Vincent G., Levi Y. A colorimetric and fluorometric microplate assay for the detection of microcystin-LR in drinking water without preconcentration. Food Chem. Toxicol. 2002, 40:1677-1683.
23. Briggs L.R., Garthwaite L.L., Miles C.O., Garthwaite T., Ross K.M., Towers N.R., Quilliam M.A. The newest ELISA-pectenotoxin. Marine Biotoxin Science Workshop No. 14. MAF, W., New Zealand 2000, 71-75.
24. Briggs L.R. Immunoassay development for shellfish toxins. Frac. HABTech03 Workshop (Cawthron Report No. 906), Nelson, 3 2003, P. Holland, L. Rhodes, L. Brown (Eds.).
25. Briggs L.R., Miles C.O., Fitzgerald J.M., Ross K.M., Garthwaite I., Towers N.R. Enzyme-linked immunosorbent assay for the detection of yessotoxin and its analogues. J. Agric. Food Chem. 2004, 52:5836-5842.
26. Burgess V., Shaw G. Pectenotoxins-an issue for public health: a review of their comparative toxicology and metabolism. Environ. Int. 2001, 27:275-283.
27. Callegari F., Sosa S., Ferrari S., Soranzo M.R., Pierotti S., Yasumoto T., Tubaro A., Rossini G.P. Oral administration of yessotoxin stabilizes E-cadherin in mouse colon. Toxicology 2006, 227:145-155.
28. Callegari F., Rossini G.P. Yessotoxin inhibits the complete degradation of E-cadherin. Toxicology 2008, 244:133-144.
29. Carmody E.P., James K.J., Kelly S.S. Diarrhetic shellfish poisoning: evaluation of enzyme-linked immunosorbent assays methods for dinophysistoxin-2 determination. J. AOAC Int. 1995, 78:1403-1408.
30. Carvalho P.S., Catia R., Moukha S., Matias W.G., Creppy E.E. Comparative study of domoic acid and okadaic acid induced-chromosomal abnormalities in the CACO-2 cell line. Int. J. Environ. Res. Public Health 2006, 3:4-10.
31. CEN Foodstuffs-Determination of Okadaic Acid and Dinophysistoxin in Mussels-HPLC Method with Solid Phase Extraction Clean-up after Derivatization and Fluorimetric Detection 2004, European Standardization Committee (CEN), Brussels, Belgium, Standard 14524.
32. Chae H.D., Choi T.S., Kim B.M., Jung J.H., Bang Y.J., Shin D.Y. Oocyte-based screening of cytokinesis inhibitors and identification of pectenotoxin-2 that induces Bim/Bax-mediated apoptosis in p53-deficient tumors. Oncogene 2005, 24:4813-4829.
33. Chae H.D., Kim B.M., Yun U.J., Shin D.Y. Deregulation of Cdk2 causes Bim-mediated apoptosis in p53-deficient tumors following actin damage. Oncogene 2008, 27:4115-4121.
34. Ciminiello P., Fattorusso E., Forino M., Magno S., Poletti R., Satake M., Viviani R., Yasumoto T. Yessotoxin in mussels of the northern Adriatic Sea. Toxicon 1997, 35:177-183.
35. Ciminiello P., Fattorusso E., Forino M., Magno S., Poletti R., Viviani R. Isolation of adriatoxin, a new analogue of yessotoxin from mussels of the Adriatic Sea. Tetrahedron Lett. 1998, 39:8897-8900.
36. Ciminiello P., Fattorusso E., Forino M., Poletti R., Viviani R. A new analogue of yessotoxin, carboxyyessotoxin, isolated from Adriatic Sea mussels. Eur. J. Organic. Chem. 2000, 291-295.
37. Ciminiello P., Fattorusso E., Forino M., Poletti R., Viviani R. Structure determination of carboxyhomoyessotoxin, a new yessotoxin analogue isolated from adriatic mussels. Chem. Res. Toxicol. 2000, 13:770-774.
38. Ciminiello P., Fattorusso E., Forino M., Poletti R. 42,43,44,45,46,47,55-Heptanor-41-oxohomoyessotoxin, a new biotoxin from mussels of the northern Adriatic sea. Chem. Res. Toxicol. 2001, 14:596-599.
39. Ciminiello P., Dell-Aversano C., Fattorusso E., Forino M., Magno S., Poletti R. The detection and identification of 42,43,44,45,46,47,55-heptanor-41-oxoyessotoxin, a new marine toxin from Adriatic shellfish, by liquid chromatography-mass spectrometry. Chem. Res. Toxicol. 2002, 15:979-984.
40. Ciminiello P., Dell-Aversano C., Fattorusso E., Forino M., Magno S., Poletti R. Direct detection of yessotoxin and its analogues by liquid chromatography coupled with electrospray ion trap mass spectrometry. J. Chromatogr. A 2002, 968:61-69.
41. Ciminiello P., Dell-Aversano C., Fattorusso E., Forino M., Magno S., Guerrini F., Pistocchi R., Boni L. Complex yessotoxins profile in Protoceratium reticulatum from north-western Adriatic Sea revealed by LC-MS analysis. Toxicon 2003, 42:7-14.
42. Ciminiello P., Dell-Aversano C., Fattorusso E., Forino M., Grauso L., Magno S., Poletti R., Tartaglione L. Desulfoyessotoxins from Adriatic Mussels: a new problem for seafood safety control. Chem. Res. Toxicol. 2007, 20:95-98.
43. Cohen P. The structure and regulation of protein-phosphatases. Annu. Rev. Biochem. 1989, 58:453-508.
44. Cohen P., Holmes C.F.B., Tsukitani Y. Okadaic acid: a new probe for the study of cellular regulation. Trends Biochem. Sci. 1990, 15:98-102.
45. Cordier S., Monfort C., Miossec L., Richardson S., Belin C. Ecological analysis of digestive cancer mortality related to contamination by diarrhetic shellfish poisoning toxins along the coasts of France. Environ. Res. 2000, 84:145-150.
46. Creppy E.E., Traore A., Baudrimont I., Cascante M., Carratu M.R. Recent advances in the study of epigenetic effects induced by the phycotoxin okadaic acid. Toxicology 2002, 181-182:433-439.
47. CRL-MB, 2007. Standard operating procedure for detection of okadaic acid, dinophysistoxins and pectenotoxins by mouse bioassay. Working group CRLMB/NRL. Version 4.0, April 2007. Community Reference Laboratory for Marine Biotoxins (CRL-MB). URL: https://www.aesa.msc.es/crlmb/web/CRLMB.jsp.
48. Cruz P.G., Daranas A.H., Fernández J.J., Souto M.L., Norte M. DTX-5c, a new OA sulphate ester derivative from cultures of Prorocentrum belizeanum. Toxicon 2006, 47:920-924.
49. Cruz P.G., Daranas A.H., Fernández J.J., Norte M. 19- epi-Okadaic acid, a novel protein phosphatase inhibitor whit enhanced selectiviy. Org. Lett. 2007, 9:3045-3048.
50. Cruz P.G., Fernández J.J., Norte M., Daranas A.H. Belizeanic acid: a potent protein phosphatase 1 inhibitor belonging to the okadaic acid class, whit an unusual skeloton. Chem. Eur. J. 2008, 14:6948-6956.
51. Daiguji M., Satake M., James K.J., Bishop A., MacKenzie L., Naoki H., Yasumoto T. Structures of new pectenotoxin analogs, pectenotoxin-2 seco acid and 7-epi-pectenotoxin-2 seco acid, isolated from a dinoflagellate and greenshell mussels. Chemistry Lett. 1998, 7:653-654.
52. Daiguji M., Satake M., Ramstad H., Aune T., Naoki H., Yasumoto T. Structure and fluorometric HPLC determination of 1-desulfoyessotoxin, a new yessotoxin analog isolated from mussels from Norway. Nat. Toxins 1998, 6:235-239.
53. Daranas H.A., Norte M., Fernandez J.J. Toxic marine microalgae. Toxicon 2001, 39:1101-1132.
54. Daranas A.H., Cruz P.G., Creus A.H., Norte M., Fernández J.J. Self-association of okadaic acid as a pathway to the cell. Org. Lett. 2007, 9:4191-4194.
55. De la Rosa L.A., Alfonso A., Vilariño N., Vieytes M.R., Botana L.M. Modulation of cytosolic calcium levels of human lymphocytes by yessotoxin, a novel marine phycotoxin. Biochem. Pharmacol 2001, 61:827-833.
56. 2+ channel blockers and kinases. Cell. Signal 2001, 12:711-716.
57. De la Iglesia P., Gago-Martinez A., Yasumoto T. Advanced studies for the application of high performance capillary electrophoresis for the analysis of yessotoxin and 45-hydroxyyessotoxin. J. Chromatogr. A 2007, 1156:160-166.
58. Díaz Sierra M., Furey A., Lehane M., Braña A., James K.J. Detection of six new azaspiracids in shellfish using liquid chromatography with multiple tandem mass spectrometry. Harmful Algae 2002, Florida Fish and Wildlife Conservation Commission 2004, 204-206. Florida Institute of Oceanography and Intergovernmental Oceanographic Commission of UNESCO, St. Petersburg, Florida, USA. K.A. Steidinger, J.H. Landsberg, C.R. Tomas, G.A. Vargo (Eds.).
59. Diogène G., Fessard V., Ammar M., Dubreuil A., Puiseux-Dao S. Evaluation of cytotoxic responses to a maitotoxin extract and okadaic acid. Harmful Marine Algal Blooms, Lavoisier 1995, 285-290. Intercept Ltd., London, New York. P. Lassus, G. Arzul, E. Erard-Le Denn, P. Gentien, C. Marcaillou-Le Baut (Eds.).
60. Døskeland, S.O., Serres, M.H., Fladmark, K.E., 2000. Assay for phosphatase-targeting toxins, PCT Gazette, 18 May 2000, Patent Application PCT/BG99/03756, International. Publication Number: WO 00/28325.
61. Doucet E., Ross N.N., Quilliam M.A. Enzymatic hydrolysis of esterified diarrhetic shellfish poisoning toxins and pectenotoxins. Anal. Bioanal. Chem. 2007, 389:335-342.
62. Draisci R., Lucentini L., Giannetti L., Boria P., Poletti R. First report of pectenotoxin-2 (PTX-2) in algae (Dinophysis fortii) related to seafood poisoning in Europe. Toxicon 1996, 34:923-935.
63. Draisci R., Giannetti L., Lucentini L., Ferretti E., Palleschi L., Marchiafava C. Direct identification of yessotoxin in shellfish by liquid chromatography coupled with mass spectrometry and tandem mass spectrometry. Rapid Commun. Mass Spectrom. 1998, 12:1291-1296.
64. Draisci R., Palleschi L., Giannetti L., Lucentini L., James K.J., Bishop A.G., Satake M., Yasumoto T. New approach to the direct detection of known and new diarrhoeic shellfish toxins in mussels and phytoplankton by liquid chromatography-mass spectrometry. J. Chromatogr. A 1999, 847:213-221.
65. EC Commission Decision 2002/225/EC of 15 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. Off. J. Eur. Commun. March 2002, 62.
66. EC, 2004. Regulation N° 853/2004 of the European Parlamient and of the Council of 29 April 2004, laying down specific hygiene rules for food of animal origin. L 226, p. 22.
67. EC Commission Regulation N° 2074/2005 of 5 December 2005, laying down implementing measures for certain products under Regulation (EC) N° 853/2004 of the European Parliament and of the Council and for the organisation of official controls under Regulation (EC) N° 854/2004 of the European Parliament and of the Council and Regulation (EC) N° 882/2004 of the European Parliament and of the Council, derogating from Regulation (EC) N° 852/2004 of the European Parliament and of the Council and amending Regulations (EC) N° 853/2004 and (EC) N° 854/2004. Off. J. Eur. Union 2005, L 338:27.
68. Edebo L., Lange S., Li X.P., Allenmark S. Toxic mussels and okadaic acid induce rapid hypersecretion in the rat small intestine. APMIS 1988, 96:1029-1035.
69. EFSA Opinion of the Scientific Panel on Contaminants in the Food chain on a request from the European Commission on marine biotoxins in shellfish-okadaic acid and analogues. EFSA J. 2008, 589:1-62.
70. EU/SANCO, 2001. Report of the meeting of the working group on toxicology of DSP and AZP. European Union/Directorate General for Health and Consumer Affairs (EU/SANCO). 21 to 23rd, May 2001, Brussels.
71. FAO Marine Biotoxins 2004, vol. 80. Food and Agriculture Organization of the United Nations (FAO), Food and Nutrition, Food and Agriculture Organization, Rome, Italy, pp. 53.
72. FAO/IOC/WHO, 2004. Report of the Joint Food and Agriculture Organization of the United Nations/Intergovernmental Oceanographic Commission of UNESCO/World Health Organization (FAO/IOC/WHO) ad hoc Expert Consultation on Biotoxins in Bivalve Molluscs. Oslo, Norway, September 26-30. URL:. ftp://ftp.fao.org/es/esn/food/biotoxin_report_en.pdf.
73. Feng G., Ohmori Y., Chang P.L. Production of chemokine CXCL1/KC by okadaic acid through the nuclear factor-kB pathway. Carcinogenesis 2006, 27:43-52.
74. Fernández M.L., Míguez A., Cacho E., Martínez A. Detection of okadaic acid esters in the hexane extracts of Spanish mussels. Toxicon 1996, 34:381-387.
75. Fernandez J.J., Candenas M.L., Souto M.L., Trujillo M.M., Norte M. Okadaic acid, useful tools for studying cellular processes. Curr. Med. Chem. 2002, 9:229-262.
76. Fernández M.L., Míguez A., Cacho E., Martínez A., Diogéne J., Yasumoto T. Bioensayos con mamíferos y ensayos bioquímicos y celulares para la detección de Ficotoxinas. Floraciones Algales Nocivas en el Cono Sur Americano 2002, 77-120. Instituto Español de Oceanografía. E.A. Sar, M.E. Ferrario, B. Reguera (Eds.).
77. Fernandez J.J., Suárez-Gómez B., Souto M.L., Norte M. Identification of new okadaic acid derivatives from laboratory cultures of Prorocentrum lima. J. Nat. Prod. 2003, 66:1294-1296.
78. Fernández M.L., Reguera B., González-Gil S., Míguez A. Pectenotoxin-2 in single-cell isolates of Dinophysis caudata and Dinophysis acuta from the Galician Rías (NW Spain). Toxicon 2006, 48:477-490.
79. Ferrari S., Ciminiello P., Dell-Aversano C., Forino M., Malaguti C., Tubaro A., Poletti R., Yasumoto T., Fattorusso E., Rossini G.P. Structure-Activity relationships of yessotoxins in cultured cells. Chem. Res. Toxicol. 2004, 17:1251-1257.
80. Fessard V., Grosse Y., Pfohl L.A., Puiseux D.S. Okadaic acid treatment induces DNA adduct formation in BHK21 C13 fibroblasts and HESV keratinocytes. Mutat. Res. 1996, 361:133-141.
81. Finch S.C., Wilkins A.L., Hawkes A.D., Jensen D.J., MacKenzie L., Beuzenberg V., Quilliam M.A., Olseng C.D., Samdal I.A., Aasen J.A.G., Selwood A.I., Cooney J.M., Sandvik M., Miles C.O. Isolation and identification of (44- R, S)-44,55-dihydroxyyessotoxin from Protoceratium reticulatum, and its occurrence in extracts of shellfish from New Zealand, Norway and Canada. Toxicon 2005, 46:160-170.
82. Fladmark K.E., Serres M.H., Larsen N.L., Yasumoto T., Aune T., Døskeland S.O. Sensitive detection of apoptogenic toxins in suspension cultures of rat and salmon hepatocytes. Toxicon 1998, 36:1101-1114.
83. Fontal O.I., Vieytes M.R., Baptista de Sousa J.M.V., Louzao M.C., Botana A.M. A fluorescent microplate assay for Microcystin-LR. Anal. Biochem. 1999, 269:289-296.
84. Franchini A., Marchesini E., Poletti R., Ottaviani E. Acute toxic effect of the algal yessotoxin on Purkinje cells from the cerebellum of Swiss CD1 mice. Toxicon 2004, 43:347-352.
85. Franchini A., Marchesini E., Poletti R., Ottaviani E. Lethal and sub-lethal yessotoxin dose induced morpho-functional alterations in intraperitoneal injected Swiss CD1 mice. Toxicon 2004, 44:83-90.
86. Franchini A., Marchesini E., Poletti R., Ottaviani E. Swiss mice CD1 fed on mussels contaminated by okadaic acid and yessotoxins: effects on thymus and spleen. Eur. J. Histochem. 2005, 49:179-188.
87. Fujiki H., Suganuma M., Suguri H., Yoshizawa S., Takagi K., Uda N., Wakamatsu K., Yamada K., Murata M., Yasumoto T., Sugimura T. Diarrhetic shellfish toxins, DTX-1, is a potent tumor promoter on mouse skin. Jpn J. Cancer Res. 1988, 79:1089-1093.
88. Fujiki H., Suganuma M. Tumor promotion by inhibitors of protein phosphatases 1 and 2A: the okadaic acid class of compounds. Adv. Cancer Res. 1993, 61:143-194.
89. Fujiki H., Suganuma M. Unique features of the okadaic acid activity class of tumor promoters. J. Carcer Res. Clin. Oncol. 1999, 125:150-155.
90. Fux E., McMillan D., Bire R., Hess P. Development of an ultra-performance liquid chromatography mass spectrometry method for the detection of lipophilic marine toxins. J. Chromatogr. A 2007, 1157:273-280.
91. García C., Pereira P., Valle L., Lagos N. Quantitation of diarrhetic shellfish poisoning toxins in Chilean Mussel using pyrenyldiazomethane as fluorescent labeling reagent. Biol. Res. 2003, 36:171-183.
92. Garthwaite I. Keeping shellfish safe to eat: a brief review of shellfish toxins, and methods for their detection. Trends Food Sci. Technol. 2000, 11:235-244.
93. González J.C., Leira F., Fontal O.I., Vieytes M.R., Arévalo F.F., Vieites J.M., Bermúdez de la Puente M., Muñiz S., Salgado C., Yasumoto T., Botana L.M. Inter-laboratory validation of the fluorescent protein phosphatase inhibition assay to determine diarrhetic shellfish toxins: intercomparison with liquid chromatography and mouse bioassay. Anal. Chim. Acta 2002, 466:233-246.
94. Goto H., Igarashi T., Yamamoto M., Yasuda M., Sekiguchi R., Watai M., Tanno K., Yasumoto T. Quantitative determination of marine toxins associated with diarrhetic shellfish poisoning by liquid chromatography coupled with mass spectrometry. J. Chromatogr. A 2001, 907:181-189.
95. Hallegraeff G.M., Anderson D.M., Cembella A.D. Manual on Harmful Marine Microalgae, IOC Manuals and Guides 1995, vol. 33. IOC of UNESCO, Paris, pp. 551.
96. Hamano Y., Kinoshita Y., Yasumoto T. Enteropathogenity of diarrhetic shellfish toxins in intestinal models. J. Food Hyg. Soc. Jpn. 1986, 27:375-379.
97. Hescheler J., Mieske G., Rüegg J.C., Takai A., Trautwein W. Effects of a protein phosphatase inhibitor, okadaic acid, on membrane currents of isolated guinea-pig cardiac myocytes. Pflügers Arch. 1988, 412:248-252.
98. Holmes C.F.B. Liquid chromatography-linked protein phosphatase bioassay; a highly sensitive marine bioscreen for okadaic acid and related diarrhetic shellfish toxins. Toxicon 1991, 29:469-477.
99. Holmes M.J., Lewis R.J., Jones A., Wong Hoy A.W. Cooliatoxin, the first toxin from Coolia monotis (Dinophyceae). Nat. Toxins 1995, 3:355-362.
100. Honkanen R.E., Mowdy D.E., Dickey R.W. Detection of DSP-toxins, okadaic acid, and dinophysistoxin-1 in shellfish by serine/threonine protein phosphatase assay. J. AOAC Int. 1996, 79:1336-1343.
101. Hori M., Matsuura Y., Yoshimoto R., Ozaki H.Y.T., Karaki H. Actin depolymerizing action by marine toxin, pectenotoxin-2. Nipp. Yakuri. Zass. 1999, 114:225-229.
102. Hosokawa M., Tsukada H., Saitou T., Kodama M., Onomura M., Nakamura H., Fukuda K., Seino Y. Effects of okadaic acid on rat colon. Dig. Dis. Sci. 1998, 43:2526-2535.
103. Hu T., Doyle J., Jackson D.M., Marr J., Nixon E., Pleasance S., Quilliam M.A., Walter J.A., Wright J.L.C. Isolation of a new diarrhetic shellfish poison from Irish mussels. J. Chem. Soc., Chem. Commun. 1992, 1:39-44.
104. Hu T., Marr J., De Freitas A.S.W., Quilliam M.A., Walter J.A., Wright J.L.C., Pleasance S. New diol esters isolated from cultures of the dinoflagellates Prorocentrum lima and Prorocentrum concavum. J. Nat. Prod. 1992, 55:1631-1637.
105. Hu T., Marr J., Defreitas A.S.W., Quilliam M.A., Walter J.A., Wright J.L.C. New diol ester (of okadaic acid) isolated from cultures of Prorocentrum lima and Prorocentrum concavum. J. Nat. Prod. 1992, 55:1631-1637.
106. Hu T., Curtis J.M., Walter J.A., McLachlan J.L., Wright J.L.C. Two new water-soluble DSP toxin derivatives from the dinoflagellate Prorocentrum maculosum: possible storage and excretion products. Tetrahedron Lett. 1995, 36:9273-9276.
107. Huang J.M.C., Wu C.H. Mechanism of the toxic action of T17 brevetoxin from Ptychodiscus brevis on nerve membranes. Toxic Dinoflagellates 1985, 351-356. Elsevier, New York. D.M. Anderson, A.W. White, D.G. Baden (Eds.).
108. Huynh C., Pinelli E., Puiseux-Dao S., Boulekbache H., Pfohl-Leszkowicz A. Okadaic acid and DNA adduct formation. Harmful Algae, Xunta de Galicia and Intergovernmental Oceanographic Commission of UNESCO, Santiago de Compostela 1998, 581-583. B. Reguera, J. Blanco, M.L. Fernández, T. Wyatt (Eds.).
109. Ikehara T., Shinjo F., Ikehara S., Imamura S., Yasumoto T. Baculovirus expression, purification, and characterization of human protein phosphatase 2A catalytic subunit α and β. Protein Expr. Purif. 2006, 45:150-156.
110. Imai I., Sugioka H., Nishitani G., Mitsuya T., Hamano Y. Monitoring of DSP toxins in small-sized plankton fraction of seawater collected in Mutsu Bay, Japan, by ELISA method: relation with toxin contamination of scallop. Mar. Pollut. Bull. 2003, 47:114-117.
111. Ishige, M., Satoh, N., Yasumoto, T., 1988. Pathological studies on the mice administered with the causative agent of diarrhetic shellfish poisoning (okadaic acid and pectenotoxin-2). Report from the Hokkaido Institute of Health vol. 38, pp. 15-19.
112. Isobe M., Sugiyama Y., Ito T., Ohtani I.I., Toya Y., Nishigohri Y., Takai A. New analysis method for protein phosphatase type 2A inhibitors using the firefly bioluminescence system. Biosci. Biotechnol. Biochem. 1995, 59:2235-2238.
113. Ito E., Terao K. Injury and recovery process of intestine caused by okadaic acid and related compounds. Nat. Toxins 1994, 2:371-377.
114. Ito E., Yasumoto T., Takai A., Imanishi S., Harada K. Investigation of the distribution and excretion of okadaic acid in mice using immunostaining method. Toxicon 2002, 40:159-165.
115. Ito, E., Speijers, G., Fessard, V., Le Hégarat, L., Yasumoto, T., 2004. Draft to the Joint Food and Agriculture Organization of the United Nations/Intergovernmental Oceanographic Commission of UNESCO/World Health Organization (FAO/IOC/WHO) ad hoc Expert Consultation on Biotoxins in Bivalve Molluscs, Oslo, Norway.
116. Ito, E., 2006. Verification of diarrhetic activities of PTX-2 and okadaic acid in vivo, 12th International Conference on Harmful Algae, 2006, Abstract PO 08-01, pp. 198.
117. Ito E., Suzuki T., Oshima Y., Yasumoto T. Studies of diarrhetic activity on pectenotoxin-6 in the mouse and rat. Toxicon 2008, 51:707-716.
118. 3+ chelates as non-radioisotopic tracers. J. Immunol. Methods 1986, 87:13-20.
119. James K., Bishop A.G., Gillman M., Kelly S.S., Roden C., Draisci R., Lucentini L., Giannetti L., Boria P. Liquid chromatography with fluorimetric, mass spectrometric and tandem mass spectrometric detection for the investigation of the seafood-toxin-producing phytoplankton, Dinophysis acuta. J. Chromatogr. A 1997, 777:213-221.
120. James K.J., Bishop A.G., Draisci R., Palleschi L., Marchiafava C., Ferretti E., Satake M., Yasumoto T. Liquid chromatographic methods for the isolation and identification of new pectenotoxin-2 analogues from marine phytoplankton and shellfish. J. Chromatogr. A 1999, 844:53-65.
121. Jung J.H., Sim C.J., Lee C.O. Cytotoxic compounds from a two-sponge association. J. Nat. Prod. 1995, 58:1722-1726.
122. Kat M. Diarrhetic mussel poisoning in the Netherlands related to the dinoflagellate Dinophysis acuminata. Antonie van Leeuwenhoek 1983, 49:417-427.
123. Kat M. Dinophysis acuminata blooms, the distinct cause of Dutch mussel poisoning. Toxic Dinoflagellates 1985, 73-77. Elsevier, New York. D.M. Anderson, A.W. White, D.G. Baden (Eds.).
124. Kleivdal, H., Briggs, L., Miles, C.O., 2005. Development and validation of YTX ELISA-a rappid assay for the determination of yessotoxin in shellfish and environmental samples, Marine and Freshwater Toxins Analysis, First Joint Symposium and AOAC Task Force Meeting, Baiona, Spain, pp. 53.
125. Konishi M., Yang X., Li B., Fairchild C.R., Shimizu Y. Highly cytotoxic metabolites from the culture supernatant of the temperate dinoflagellate Protoceratium cf. reticulatum. J. Nat. Prod. 2004, 67:1309-1313.
126. Larsen K., Petersen D., Wilkins A.L., Samdal I.A., Sandvik M., Rundberget T., Golstone D., Arcus V., Hovgaard P., Rise F., Rehmann N., Hess P., Miles C.O. Clarification of the C-35 stereochemistries of dinophysistoxin-1 and dinophysistoxin-2 and its consequences for binding to protein phosphatase. Chem. Res. Toxicol. 2007, 20:868-875.
127. Lawrence J.E., Bauder A.G., Quilliam M.A., Cembella A.D. Prorocentrum lima: a putative link to diarrhetic shellfish poisoning in Nova Scotia, Canada. Harmful Algae, Xunta de Galicia and IOC of UNESCO, Santiago de Compostela 1998, 78-79. B. Reguera, J. Blanco, M.L. Fernández, T. Wyatt (Eds.).
128. Laycock M.V., Jellett J.F., Easy D.J., Donovan M.A. First report of a new rapid assay for diarrhetic shellfish poisoning toxins. Harmful Algae 2006, 5:74-78.
129. Le Hégarat L., Peuch L., Fessard V., Poul J.M., Dragacci S. Aneugenic potential of okadaic acid revealed by the micronucleus assay combined with the FISH technique in CHO-K1 cells. Mutagenesis 2003, 18:293-298.
130. Le Hégarat L., Nesslany F., Mourot A., Marzin D., Fessard V. Lack of DNA damage induction by okadaic acid, a marine toxin, in the CHO-Hprt and the in vitro UDS assays. Mutat. Res. 2004, 564:139-147.
131. Le Hégarat L., Orsiere T., Botta A., Fessard V. Okadaic acid: Chromosomal nondisjunction analysis in human lymphocytes and study of aneugenic pathway in CHO-K1 cells. Mutat. Res. 2005, 578:53-63.
132. Le Hégarat L., Jacquin A.G., Bazin E., Fessard V. Genotoxicity of the marine toxin okadaic acid in human Caco-2 cells and in mice gut cells. Environ. Toxicol. 2006, 21:55-64.
133. Lee J.S., Yanagi T., Kenma R., Yasumoto T. Fluorometric determination of diarrhetic shellfish toxins by high-performance liquid chomatography. Agric. Biol. Chem. 1987, 51:877-881.
134. Lee J.S., Igarashi T., Fraga S., Dahl E., Hovgaard P., Yasumoto T. Determination of diarrhetic shellfish toxins in various dinoflagellate species. J. App. Phycol. 1989, 1:147-152.
135. Lee J.S., Murata M., Yasumoto T. Analytical methods for the determination of diarrhetic shellfish toxins. Mycotoxins and Phycotoxins'88 1989, 327-334. Elsevier Science, Tokyo. S. Natori, K. Hashimoto, Y. Ueno (Eds.).
136. Leira F., Alvarez C., Vieites J.M., Vieytes M.R., Botana L.M. Characterization of distinct apoptotic changes induced by okadaic acid and yessotoxin in the BE(2)-M17 neuroblastoma cell line. Toxicol. in vitro 2002, 16:23-31.
137. Leira F., Cabado A., Vieytes M.R., Roman Y., Alfonso A., Botana L.M., Yasumoto T., Malaguti C., Rossini G.P. Characterization of F-actin depolymerization as a major toxic event induced by pectenotoxin-6 in neuroblastoma cells. Biochem. Pharmacol. 2002, 63:1979-1988.
138. Levine L., Fujiki H., Yamada K., Ojika M., Gjika H.B., Van Vanakis H. Production of antibodies and development of a radioimmunoassay for okadaic acid. Toxicon 1988, 26:1123-1128.
139. Loader J.I., Hawkes A.D., Beuzenberg V., Jensen D.J., Cooney J.M., Wilkins A.L., Fitzgerald J.M., Briggs L.R., Miles C.O. Convenient large-scale purification of yessotoxin from Protoceratium reticulatum culture and Isolation of a novel furanoyessotoxin. J. Agric. Food Chem. 2007, 55:11093-11100.
140. MacKenzie L., Suzuki T., Adamson J. Elimination and differential transformation of yessotoxin by the greenshell mussel Perna canaliculus and the blue mussel Mytilus gallopovincialis. Harmful Algal Blooms 2000, IOC of UNESCO 2001, 371-374. G.M. Hallegraeff, S.I. Blackburn, C.J. Bolch, R.J. Lewis (Eds.).
141. MacKenzie L., Holland P., McNabb P., Beuzenberg V., Selwood A., Suzuki T. Complex toxin profiles in phytoplankton and Greenshell mussels (Perna canaliculus), revealed by LC-MS/MS analysis. Toxicon 2002, 40:1321-1330.
142. MacKenzie A.L., Beuzenberg V., Holland P., McKabb P., Suzuki T., Selwood A. Pectenotoxin and okadaic acid-based toxin profiles in Dinophysis acuta and Dinophysis acuminata from New Zealand. Harmful Algae 2005, 4:75-85.
143. MacKenzie L., Beuzenberg V., Holland P., McNabb P., Suzuki T., Selwood A. Pectenotoxin and okadaic acid-based toxin profiles in Dinophysis acuta and Dinophysis acuminata from New Zealand. Harmful Algae 2005, 4:75-85.
144. Malagoli D., Casarini L., Ottaviani E. Algal toxin yessotoxin signalling pathways involve immunocyte mussel calcium channels. Cell Biol. Int. 2006, 30:721-726.
145. Malagoli D., Marchesini E., Ottaviani E. Lysosomes as the target of yessotoxin in invertebrate and vertebrate cell lines. Toxicol. Lett. 2006, 167:75-83.
146. Malagoli D., Ottaviani E. Yessotoxin affects fMLP-induced cell shape changes in Mytilus galloprovincialis immunocytes. Cell Biol. Int. 2004, 28:57-61.
147. Malaguti C., Ciminiello P., Fattorusso E., Rossini G.P. Caspase activation and death induced by yessotoxin in HeLa cells. Toxicol. in Vitro 2002, 16:357-363.
148. Marr J.C., Hu T., Pleasance S., Quilliam M.A., Wright J.L.C. Detection of new 7- O-acyl derivatives of diarrhetic shellfish poisoning toxins by liquid chromatography-mass spectrometry. Toxicon 1992, 30:1621-1630.
149. Matias W.G., Traore A., Creppy E.E. Variations in the distribution of okadaic acid in organs and biological fluids of mice related to diarrhoeic syndrome. Hum. Exp. Toxicol. 1999, 18:345-350.
150. McCarron P., Emteborg H., Hess P. Freeze-drying for the stabilisation of shellfish toxins in mussel tissue (Mytilus edulis) reference materials. Anal. Bioanal. Chem. 2007, 387:2475-2486.
151. McNabb P., Selwood A.I., Holland P.T. Multi-residue method for determination of algal toxins in shellfish: Single laboratory validation and inter-laboratory study. J. AOAC Int. 2005, 88(3):761-772.
152. Miles C.O., Wilkins A.L., Hawkes A.D., Selwood A., Jensen D.J., Aasen J., Munday R., Samdal I.A., Briggs L.R., Beuzenberg V., MacKenzie A.L. Isolation of a 1,3-enone isomer of heptanor-41-oxoyessotoxin from Protoceratium reticulatum cultures. Toxicon 2004, 44:325-336.
153. Miles C.O., Wilkins A.L., Jensen D.J., Cooney J.M., Quilliam M.A., Aasen J., MacKenzie A.L. Isolation of 41a-homoyessotoxin and the identification of 9-Methyl-41a-homoyessotoxin and Nor-ring-A-yessotoxin from Protoceratium reticulatum. Chem. Res. Toxicol. 2004, 17:1414-1422.
154. Miles C.O., Wilkins A.L., Munday R., Dines M.H., Hawkes A.D., Briggs L.R., Sandvik M., Jensen D.J., Cooney J.M., Holland P.T., Quilliam M.A., MacKenzie A.L., Beuzenberg V. Isolation of pectenotoxin-2 from Dinophysis acuta and its conversion to pectenotoxin-2 seco acid, and preliminary assessment of their acute toxicities. Toxicon 2004, 43:1-9.
155. Miles C.O., Wilkins A.L., Samdal I.A., Sandvik M., Petersen D., Quilliam M.A., Naustvoll L.J., Jensen D.J., Cooney J.M. A novel pectenotoxin, PTX-12, in Dinophysis spp. and shellfish from Norway. Chem. Res. Toxicol. 2004, 17:1423-1433.
156. Miles C.O., Samdal I.A., Aasen J.A.G., Jensen D.J., Quilliam M.A., Petersen D., Briggs L.R., Wilkins A.L., Rise F., Cooney J.M., MacKenzie L. Evidence for numerous analogs of yessotoxin in Protoceratium reticulatum. Harmful Algae 2005, 4:1075-1091.
157. Miles C.O., Wilkins A.L., Hawkes A.D., Selwood A., Jensen D.J., Munday R., Cooney J.M., Beuzenberg V. Polyhydroxilated amide analogs of yessotoxin from Protoceratium reticulatum. Toxicon 2005, 45:61-71.
158. Miles C.O., Wilkins A.L., Allan D.H., Selwood A.I., Jensen D.J., Cooney J.M., Beuzenberg V., MacKenzie A.L. Identification of 45-hydroxy-46,47-dinoryessotoxin, 44-oxo-45,46,47-trinoryessotoxin, and 9-methyl-42,43,44,45,46,47,55-heptanor-38-en-41-oxoyessotoxin, and partial characterization of some minor yessotoxins, from Protoceratium reticulatum. Toxicon 2006, 47:229-240.
159. Miles C.O., Wilkins A.L., Hawkes A.D., Jensen D.J., Selwood A.I., Beuzenberg V., MacKenzie A.L., Cooney J.M., Holland P.T. Isolation and identification of pectenotoxins-13 and -14 from Dinophysis acuta in New Zealand. Toxicon 2006, 48:152-159.
160. Miles C.O., Wilkins A.L., Selwood A.I., Hawkes A.D., Jensen D.J., Cooney J.M., Beuzenberg V., MacKenzie A.L. Isolation of yessotoxin 32-O-[ß-l-arabinofuranosyl-(5'-1')-ß-l-arabinofuranoside] from Protoceratium reticulatum. Toxicon 2006, 47:510-516.
161. 2/M arrest, endoreduplication, and apoptosis by actin depolymerization agent pectenotoxin-2 in human leukemia cells, involving activation of ERK and JNK. Biochem. Pharmacol. 2008, 76:312-321.
162. Morohashi A., Satake M., Murata K., Naoki H., Kaspar H.F., Yasumoto T. Brevetoxin B3, a new brevetoxin analog isolated from the greenshell mussel Perna canaliculus involved in neurotoxic shellfish poisoning in New Zealand. Tetrahedron Lett. 1995, 36:8995-8998.
163. Mountfort D.O., Suzuki T., Truman P. Protein phosphatase inhibition assay adapted for determination of total DSP in contaminated mussels. Toxicon 2001, 39:383-390.
164. Murakami Y., Oshima Y., Yasumoto T. Identifcation of okadaic acid as a toxic component of a marine dinofagellate Prorocentrum lima. Bull. Japan Soc. Sci. Fish 1982, 48:69-72.
165. Murata M., Shimatani M., Sugitani H., Oshima Y., Yasumoto T. Isolation and structural elucidation of the causative toxin of diarrhetic shellfish poisoning. Bull. Jpn Soc. Sci. Fish 1982, 48:549-552.
166. Murata M., Sano M., Iwashita T., Naoki H., Yasumoto T. The structure of pectenotoxin-3, a new constituent of diarrhetic shellfish toxins. Agri. Biol. Chem. 1986, 50:2693-2695.
167. Murata M., Masanori K., Lee J.S., Yasumoto T. Isolation and structure of yessotoxin, a novel polyether compound implicated in diarrhetic shellfish poisoning. Tetrahedron Lett. 1987, 28:5869-5872.
168. Nogueiras M.J., Gago-Martinez A., Paniello A.I., Twohig M., James K., Lawrence J.F. Comparison of different fluorometric HPLC method for analysis of acidic polyether toxins in marine phytoplankton. Anal. Bioanal. Chem. 2003, 377:1202-1206.
169. Norte M., Padilla A., Fernández J.J., Souto M.L. Structural determination and biosynthetic origin of two ester derivatives of okadaic acid isolated from Prorocentrum lima. Tetrahedron Lett. 1994, 50:9175-9180.
170. Ofuji K., Satake M., McMahon T., Silke J., James K.J., Naoki H., Oshima Y., Yasumoto T. Two analogs of azaspiracid isolated from mussels, Mytilus edulis, involved in human intoxication in Ireland. Nat. Toxins 1999, 7:99-102.
171. Ogino H., Kumagai M., Yasumoto T. Toxicologic evaluation of yessotoxin. Nat. Toxins 1997, 5:255-259.
172. Pavela-Vrancic M., Mestrovic V., Marasovi I., Gillman M., Furey A., James K. The occurrence of 7-epi-pectenotoxin-2 seco acid in the coastal waters of the central Adriatic (Kastela Bay). Toxicon 2001, 39:771-779.
173. Paz B., Riobó P., Fernández M.L., Fraga S., Franco J.M. Production and release of yessotoxins by the dinoflagellates Protoceratium reticulatum and Lingulodinium polyedrum in culture. Toxicon 2004, 44:251-258.
174. Paz B., Riobó P., Souto M.L., Gil L.V., Norte M., Fernandez J.J., Franco J.M. Detection and identification of glycoyessotoxin A in a culture of the dinoflagellate Protoceratium reticulatum. Toxicon 2006, 48:611-619.
175. Paz B., Daranas A.H., Cruz P.G., Franco J.M., Pizarro G., Souto M.L., Norte M., Fernández J.J. Characterisation of okadaic acid related toxins by liquid chromatography coupled with mass spectrometry. Toxicon 2007, 50:225-235.
176. Paz B., Riobó P., Ramilo I., Franco J.M. Yessotoxins profile in strains of Protoceratium reticulatum from Spain and USA. Toxicon 2007, 50:1-17.
177. Paz B., Daranas A.H., Cruz P.G., Franco J.M., Norte M., Fernández J.J. Identification of 19- epi-okadaic acid, a new diarrhetic shellfish poisoning toxin, by liquid chromatography with mass spectrometry detection. Mar. Drugs 2008, 6:489-495.
178. Paz B., Daranas A.H., Norte M., Riobó P., Franco J.M., Fernández J.J. Yessotoxin, a group of marine polyether toxins: an overview. Mar. Drugs 2008, 6:73-102.
179. Pazos M.J., Alfonso A., Vieytes M.R., Yasumoto T., Vieites J.M., Botana L.M. Resonant mirror biosensor detection method based on yessotoxin-phosphodiesterase interactions. Anal. Biochem. 2004, 335:112-118.
180. Pazos M.J., Alfonso A., Vieytes M.R., Yasumoto T., Botana L.M. Kinetic analysis of the interaction between yessotoxin and analogues and immobilized phosphodiesterases using a resonant mirror optical biosensor. Chem. Res. Toxicol. 2005, 18:1155-1160.
181. Pazos M.J., Alfonso A., Vieytes M.R., Yasumoto T., Botana L.M. Study of the interaction between different phosphodiesterases and yessotoxin using a resonant mirror biosensor. Chem. Res. Toxicol. 2006, 19:794-800.
182. Pérez-Gómez A., Novelli A., Ferrero-Gutiérrez A., Franco J.M., Paz B., Fernández-Sánchez M.T. Potent neurotoxic action of the shellfish biotoxin yessotoxin on cultured cerebellar neurons. Toxicol. Sci. 2006, 90:168-177.
183. Pierotti S., Albano C., Milandri A., Callegari F., Poletti R., Rossini G.P. A slot blot procedure for the measurement of yessotoxins by a functional assay. Toxicon 2007, 49:36-45.
184. Pierotti S., Malaguti C., Milandri A., Poletti R., Rossini G.P. Functional assay to measure yessotoxins in contaminated mussel samples. Anal. Biochem. 2003, 312:208-216.
185. Quilliam M.A. Analysis of diarrhetic shellfish poisoning toxins in shellfish tissue by liquid chromatography with fluorometric and mass spectrometric detection. J. AOAC Int. 1995, 78:555-570.
186. Ramstad H., Larsen S., Aune T. Repeatability and validity of a fluorimetric HPLC method in the quantification of yessotoxin in blue mussels (Mytilus edulis) related to the mouse bioassay. Toxicon 2001, 39:1393-1397.
187. Rhodes L., McNabb P., de Salas M., Briggs L., Beuzenberg V., Gladstone M. Yessotoxin production by Gonyaulax spinifera. Harmful Algae 2006, 5:148-155.
188. Riobó P., Paz B., Franco J.M., Vázquez J.A., Murado M.A., Cacho E. Mouse bioassay for palytoxin. Specific symptoms and dose-response against dose-death time relationships. Food Chem. Toxicol. 2008, 46:2639-2647.
189. Ronzitti G., Callegari F., Malaguti C., Rossini G.P. Selective disruption of the E-cadherin-catenin system by an algal toxin. Br. J. Cancer 2004, 90:1100-1107.
190. Ronzitti G., Rossini G.P. Yessotoxin induces the accumulation of altered E-cadherin dimers that are not part of adhesive structures in intact cells. Toxicology 2008, 244:145-156.
191. Samdal I.A., Naustvoll L.J., Olseng C.D., Briggs L.R., Miles C.O. Use of ELISA to identify Protoceratium reticulatum as a source of yessotoxin in Norway. Toxicon 2004, 44:75-82.
192. Samdal, I.A., 2005. Yessotoxins in algae and mussels -Studies on its sources, disposition, and levels, Norwegian School of Veterinary Science, PhD Thesis, Oslo, pp. 53.
193. Samdal I.A., Aasen J.A.G., Briggs L.R., Dahl E., Miles C.O. Comparison of ELISA and LC-MS analyses for yessotoxins in blue mussels (Mytilus edulis). Toxicon 2005, 46:7-15.
194. Sasaki K., Satake M., Yasumoto T. Identification of the absolute configuration of pectenotoxin-6, a polyether macrolide compound, by NMR spectroscopic method using a chiral anisotropic reagent, phenylglycine methyl ester. Biosci. Biotechnol. Biochem. 1997, 61:1783-1785.
195. Sasaki K., Wright J.L.C., Yasumoto T. The identification and characterization of pectenotoxin PTX4 and PTX7 as spiroketal stereoisomers of two previously reported pectenotoxins. J. Org. Chem. 1998, 63:2475-2480.
196. Satake M., Terasawa K., Kadowaki Y., Yasumoto T. Relative configuration of YTX and isolation of two new analogs from toxic scallops. Tetrahedron Lett. 1996, 37:5955-5958.
197. Satake M., MacKenzie L., Yasumoto T. Identification of Protoceratium reticulatum as the biogenetic origin of yessotoxin. Nat. Toxins 1997, 5:164-167.
198. Satake M., Tubaro A., Lee J.S., Yasumoto T. Two new analogs of yessotoxin, homoyessotoxin and 45-hydroxyhomoyessotoxin, isolated from mussels of the Adriatic Sea. Nat. Toxins 1997, 5:107-110.
199. Satake M., Ichimura T., Sekiguchi K., Yoshimatsu S., Oshima Y. Confirmation of yessotoxin and 45,46,47-trinoryessotoxin production by Protoceratium reticulatum collected in Japan. Nat. Toxins 1999, 7:147-150.
200. Satake M., Eiki K., Ichimura T., Ota S., Sekiguchi K., Oshima Y. Structure of 45,46,47-trinorhomoyessotoxin, a new yessotoxin analog, from Protoceratium reticulatum which represents the first detection of a homoyessotoxin analog in Japan. Harmful Algae 2006, 5:731-735.
201. Schmitz F.J., Prasad R.S., Gopichand Y., Hossain M.B., Van der Helm D., Schmidt P. Acanthifolicin, a new episulfide-containing polyether carboxylic acid from extracts of the marine sponge Pandaros acanthifolium. J. Am. Chem. Soc. 1981, 103:2467-2469.
202. Serres M.H., Fladmark K.E., Doskeland S.O. An ultrasensitive competitive binding assay for the detection of toxins affecting protein phosphatases. Toxicon 2000, 38:347-360.
203. Shewstowsky W.S., Quilliam M.A., Sikorski H.M. An idyotipic -anti idyotipic competitive immunoassay for quantitation of okadaic acid. Toxicon 1992, 30:1441-1448.
204. Simon J.F., Vernoux J.P. Highly sensitive assay of okadaic acid using proteinphosphatase and paranitrophenyl phosphate. Natural Toxins 1994, 2:293-301.
205. Souto M.L., Fernandez J.J., Franco J.M., Paz B., Gil L.V., Norte M. Glycoyessotoxin A, a new yessotoxin derivate from cultures of Protoceratium reticulatum. J. Nat. Prod. 2005, 68:420-422.
206. Spector I., Braet F., Shochet N.R., Bubb M.R. New anti-actin drugs in the study of the organization and function of the actin cytoskeleton. Microsc. Res. Technol. 1999, 47:18-37.
207. Stobo L.A., Lewis J., Quilliam M.A., Hardstaff W.R., Gallacher S., Webster L., Smith E., McKenzie M. Detection of yessotoxin in UK and Canadian isolates of phytoplankton and optimization and validation of LC-MS methods. 8th Canadian Workshop on Harmful Marine Algae 2003, 8-14. Gulf Fisheries Centre, Moncton, New Brunswick, Canada. S. Bates (Ed.).
208. Stobo L.A., Lacaze J.P., Scott A.C., Gallacher S., Smith E.A., Quilliam M.A. Liquid chromatography with mass spectrometry-detection of lipophilic shellfish toxins. J. AOAC Int. 2005, 88:1371-1382.
209. Suárez-Gómez B., Souto M.L., Norte M., Fernández J.J. Isolation and structural determination of DTX-6, a new okadaic acid derivative. J. Nat. Prod. 2001, 64:1363-1364.
210. Suárez-Gómez B., Souto M.L., Cruz P.G., Fernández J.J., Norte M. New target in diarrhetic shelfish poisoning control. J. Nat. Prod. 2005, 68:596-599.
211. Suárez-Korsnes M., Hetland D.L., Espenes A., Aune T. Induction of apoptosis by YTX in myoblast cell lines via mitochondrial signalling transduction pathway. Toxicol. in Vitro 2006, 20:1419-1426.
212. Suárez-Korsnes M., Hetland D.L., Espenes A., Tranulis M.A., Aune T. Apoptotic events induced by yessotoxin in myoblast cell lines from rat and mouse. Toxicol. in Vitro 2006, 20:1077-1087.
213. Suárez-Korsnes M., Hetland D.L., Espenes A., Aune T. Cleavage of tensin during cytoskeleton disruption in YTX-induced apoptosis. Toxicol. in Vitro 2007, 21:9-15.
214. Suganuma M., Tatematsu M., Yatsunami J., Yoshizawa S., Okabe S., Uemura D., Fujiki H. An alternative theory of tissue specificity by tumor promotion of okadaic acid in glandular stomach of SD rats. Carcinogenesis 1992, 13:1841-1845.
215. Suganuma M., Fujiki H., Suguri H., Yoshizawa S., Hirota M., Nakayasu M., Ojika M., Wakamatsu K., Yamada K., Sugimura T. Okadaic acid: an additional nonphorbol-12-tetradecanoate 13-acetate-type tumor promoter. Proc. Natl. Acad. Sci. U.S.A. 1988, 85:1768-1771.
216. Suganuma M., Okabe S., Marino M.W., Sakai A., Sueoka E., Fujiki H. Essential role of Tumor Necrosis Factor α (TNF-α) in tumor promotion as revealed by TNF-α-deficient mice. Cancer Res. 1999, 59:4516-4518.
217. Suzuki T., Mitsuya T., Imai M., Yamasaki M. DSP toxin contents in Dinophysis fortii and scallops collected at Mutsu Bay, Japan. J. App. Phycol. 1997, 8:509-515.
218. Suzuki T., Ota H., Yamasaki M. Direct evidence of transformation of dinophysistoxin-1 to 7- O-acyl-dinophysistoxin-1 (dinophysistoxin-3) in the scallop Patinopecten yessoensis. Toxicon 1999, 37:187-198.
219. Suzuki T., Yasumoto T. Liquid chromatography-electrospray ionization mass spectrometry of the diarrhetic shellfish-poisoning toxins okadaic acid, dinophysistoxin-1 and pectenotoxin-6 in bivalves. J. Chromatogr. A 2000, 874:199-206.
220. Suzuki T., Mackenzie L., Stirling D., Adamson J. Conversion of pectenotoxin-2 to pectenotoxin-2 seco acid in the New Zealand scallop, Pecten novaezelandiae. Fish. Sci. 2001, 67:506-510.
221. Suzuki T., MacKenzie L., Stirling D., Adamson J. Pectenotoxin-2 seco acid: a toxin converted from pectenotoxin-2 by the New Zealand Greenshell mussel, Perna canaliculus. Toxicon 2001, 39:507-514.
222. Suzuki T., Beuzenberg V., Mackenzie L., Quilliam M.A. Liquid chromatography-mass spectrometry of spiroketal stereoisomers of pectenotoxins and the analysis of novel pectenotoxin isomers in the toxic dinoflagellate Dinophysis acuta from New Zealand. J. Chromatogr. A 2003, 992:141-150.
223. Suzuki T., Beuzenberg V., MacKenzie L., Quilliam M.A. Discovery of okadaic acid esters in the toxic dinoflagellate Dinophysis acuta from New Zealand using liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2004, 18:1131-1138.
224. Suzuki T., Jin T., Shirota Y., Mitsuya T., Okomura Y., Kamiyama T. Quantification of lipophilic toxins associated with diarrhetic shellfish poisoning in Japanese bivalves by liquid chromatography-mass spectrometry and comparison with mouse bioassay. Fish. Sci. 2005, 71:1370-1378.
225. Suzuki T., Walter J.A., LeBlanc P., MacKinnon S., Miles C.O., Wilkins A.L., Munday R., Beuzenberg V., MacKenzie A.L., Jensen D.J., Cooney J.M., Quilliam M.A. Identification of pectenotoxin-11 as 34 S-hydroxypectenotoxin-2, a new pectenotoxin analogue in the toxic dinoflagellate Dinophysis acuta from New Zealand. Chem. Res. Toxicol. 2006, 19:310-318.
226. Tachibana K., Scheuer P., Tsukitani Y., Kikuchi H., Enden V., Clardy J., Gopichand Y., Schmitz F. Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria. J. Am. Chem. Soc. 1981, 103:2469-2471.
227. Takai A., Mieskes G. Inhibitory effect of okadaic acid on the p-nitrophenyl phosphate phosphatase activity of protein phosphatases. Biochem. J. 1991, 275:233-239.
228. Ten-Hage L., Delaunay N., Pichon V., Couté A., Puiseux-Dao S., Turquet J. Okadaic acid production from the marine benthic dinoflagellate Prorocentrum arenarium Faust (Dinophyceae) isolated from Europa Island coral reef ecosystem (SW Indian Ocean). Toxicon 2000, 38:1043-1054.
229. Terao K., Ito E., Yanagi T., Yasumoto T. Histopathological studies on experimental marine toxin poisoning. I. Ultrastructural changes in the small intestine and liver of suckling mice induced by dinophysistoxin-1 and pectenotoxin-1. Toxicon 1986, 24:1141-1151.
230. Terao K., Ito E., Oarada M., Murata M., Yasumoto T. Histopatological studies on experimental marine toxin poisoning-5. The effects in mice of yessotoxin isolated from Patinopecten yessoensis and of a desulfated derivate. Toxicon 1990, 28:1095-1104.
231. Terao K., Ito E., Ohkusu M., Yasumoto T. A comparative study of the effects of DSP-toxins on mice and rats. Toxic Phytoplankton Blooms in the Sea 1993, 581-586. Elsevier, Amsterdam. T.J. Smayda, Y. Shimizu (Eds.).
232. Tohda H., Nagao M., Sugimura T., Oikawa A. Okadaic acid, a protein phosphatase inhibitor, induces sister-chromatid exchanges depending on the presence of bromodeoxyuridine. Mutat. Res. 1993, 289:275-280.
233. Tripuraneni J., Koutsouris A., Pestic L., De Lanerolle P., Hecht G. The toxin of diarrhetic shellfish poisoning, okadaic acid, increases intestinal epithelial paracellular permeability. Gastroenterology 1997, 112:100-108.
234. Tubaro A., Florio C., Luxich E., Sosa S., Della Loggia R., Yasumoto T. A protein phosphatase 2A inhibition assay for a fast and sensitive assessment of okadaic acid contamination in mussels. Toxicon 1996, 34:743-752.
235. Tubaro A., Florio C., Luxich E., Vertua R., Della Loggia R., Yasumoto T. Suitability of the MTT-based cytotoxicity assay to detect okadaic acid contamination of mussels. Toxicon 1996, 34:965-974.
236. Tubaro A., Sidari L., Della-Loggia R., Yasumoto T. Occurrence of yessotoxin-like toxins in phytoplankton and mussels from northern Adriatic Sea. Harmful Algae, Xunta de Galicia and IOC of UNESCO 1998, 470-472. B. Reguera, J. Blanco, M.L. Fenández, T. Wyatt (Eds.).
237. Tubaro A., Sosa S., Carbonatto M., Altinier G., Vita F., Melato M., Satake M., Yasumoto T. Oral and intraperitoneal acute toxicity studies of yessotoxin and homoyessotoxins in mice. Toxicon 2003, 41:783-792.
238. Tubaro A., Sosa S., Altinier G., Soranzo M.R., Satake M., Loggia R.D., Yasumoto T. Short-term oral toxicity of homoyessotoxins, yessotoxin and okadaic acid in mice. Toxicon 2004, 43:439-445.
239. Tubaro A., Giangaspero A., Ardizzone M., Soranzo M.R., Vita F., Yasumoto T., Maucher J.M., Ramsdell J.S., Sosa S. Ultrastructural damage to heart tissue from repeated oral exposure to yessotoxin resolves in 3 months. Toxicon 2008, 51:1225-1235.
240. Usagawa T., Nishimura M., Itoh Y., Uda T., Yasumoto T. Preparation of monoclonal antibodies against okadaic acid prepared from the sponge Halichondria okadai. Toxicon 1989, 27:1323-1330.
241. Vale P., Sampayo M.A. First confirmation of human diarrhoeic poisonings by okadaic acid esters after ingestion of razor clams (Solen marginatus) and green crabs (Carcinus maenas) in Aveiro lagoon, Portugal and detection of okadaic acid esters in phytoplankton. Toxicon 2002, 40:989-996.
242. Vale P., Sampayo M.A. Pectenotoxin-2 seco acid, 7-epi-pectenotoxin-2 seco acid and pectenotoxin-2 in shellfish and plankton from Portugal. Toxicon 2002, 40:979-987.
243. Vale P., Bire R., Hess P. Confirmation by LC-MS/MS of azaspiracids in shellfish from the Portuguese north-western coast. Toxicon 2008, 51:1449-1456.
244. Van Apeldoorn, M.E., 1998. Diarrhoeic shellfish poisoning: A review. RIVM/CSR Report 05722A00.
245. Van den Heuvel J.P. Xenobiotic receptor systems. Introduction and overview. Comprehensive Toxicology 2002, vol. XIV:646. Elsevier Science BV, Amsterdam. J.P. Vanden Heuvel, G.H. Perdew, W.B. Mattes, W.F. Greenlee (Eds.).
246. Van der Hoeven, F.A., 2007. Het bepalen van de toxicitite its graad van diarrhetic shellfish poison (DSP) met behulp van de rattentest. Draft CKP protocol 1.22. Centrum Kleine Proefdieren, Wageningen, the Netherlands.
247. Van Egmond H.P., Aune T., Lassus P., Speijers G., Waldock M. Paralytic and diarrhoeic shellfish poisons: occurrence in Europe, toxicity, analysis and regulation. J. Nat. Toxins 1993, 2:41-83.
248. Vernoux J.P., Le Baut C., Masselin P., Marais C., Baron B., Choumiloff R., Proniewski F., Nizard G., Bohec M. The use of Daphnia magna for detection of okadaic acidin mussel extracts. Food Add. Cont. 1993, 10:603-608.
249. Vieytes M.R., Fontal O.I., Leira Sanmartin F., Baptista de Sousa J.M.V., Botana L.M. A fluorescent microplate assay for diarrheic shellfish toxins. Anal. Biochem. 1997, 248:258-264.
250. Vilarino N., Nicolaou K.C., Frederick M.O., Cagide E., Ares I.M., Louzao M.C., Vieytes M.R., Botana L.M. Cell growth inhibition and actin cytoskeleton disorganization induced by azaspiracid-l structure-activity studies. Chem. Res. Toxicol. 2006, 19:1459.
251. Wilkins A.L., Rehmann N., Torgersen T., Rundberget T., Keogh M., Petersen D., Hess P., Rise F., Miles C.O. Identification of fatty acid esters of pectenotoxin-2 seco acid in Blue mussels (Mytilus edulis) from Ireland. J. Agric. Food Chem. 2006, 54:5672-5678.
252. Wright J.L.C. Dealing with seafood toxins: present approaches and future options. Food Res. Int. 1995, 28:347-358.
253. Yasumoto T., Oshima Y., Yamaguchi M. Occurrence of a new type of shellfish poisoning in the Tohoku district. Bull. Jpn. Soc. Sci. Fish 1978, 44:1249-1255.
254. Yasumoto T., Sugawara W., Fukuyo Y., Oguri H., Igarashi T., Fujita N. Identification of Dinophysis fortii as the causative organism of diarrhetic shellfish poisoning in the Tohoku district. Bull. Jpn Soc. Sci. Fish 1980, 46:1405-1411.
255. Yasumoto T., Murata M., Oshima Y., Sano M., Matsumoto G.K., Clardy J. Diarrhetic shellfish toxins. Tetrahedron 1985, 41:1019-1025.
256. Yasumoto Y., Seino N., Murakami Y., Murata M. Toxins produced by benthic dinoflagellates. Biol. Bull. 1987, 172:128-131.
257. Yasumoto T., Murata M., Lee J.S., Torigoe K. Polyether Toxins Produced by Dinoflagellates 1989, Elsevier, Amsterdam, pp. 375-382.
258. Yasumoto T., Murata M. Polyeter toxin involved in seafood poisoning. ACS Symposium Series 1990, 120-132. American Chemical Society, Washington DC. S. Hall, G.R. Strichartz (Eds.).
259. Yasumoto T., Murata A. Marine toxins. Chem. Rev. 1993, 93:1897-1909.
260. Yasumoto T., Fukui M., Sasaki K., Sugiyama K. Determinations of marine toxins in foods. J. AOAC Int. 1995, 78:574-582.
261. Yasumoto T., Takizawa A. Fluorometric measurement of yessotoxins in shellfish by high-pressure liquid chromatography. Biosci. Biotechnol. Biochem. 1997, 61:1775-1777.
262. Zhou Z.H., Komiyama M., Terao K., Shimada Y. Effects of pectenotoxin-1 on liver cells In Vitro. Nat. Toxins 1994, 2:132-135.