Palytoxins: Biological and chemical determination

Toxicon

Volumn 57, Issue 3, 2011, Pages 368-375

  Riobó, Pilar ^a   Franco, José M ^a  

^a INSTITUTO DE INVESTIGACIONES MARINAS   (Spain)

Author keywords

Cell cultures; Fluorescence detection (FLD); Haemolytic assay; Immunoassays; Liquid chromatography (LC); Matrix; Mouse bioassay (MBA); Ostreopsis; Palytoxin (PLTX); Ultraviolet detection (UV)

Indexed keywords

ALCOHOL; MARINE TOXIN; METHANOL; OSTREOGRYCIN; PALYTOXIN; PALYTOXIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; CYTOTOXICITY TEST; FLUORESCENCE ANALYSIS; HEMOLYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROPHOBICITY; IMMUNOASSAY; LD 50; LIPOPHILICITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; TOXIN ANALYSIS; TOXIN STRUCTURE;

ACRYLAMIDES; ANIMALS; BIOLOGICAL ASSAY; CHEMICAL FRACTIONATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, LIQUID; DINOFLAGELLIDA; ELECTROPHORESIS, CAPILLARY; HEMOLYSIS; IMMUNOASSAY; MARINE TOXINS; MASS SPECTROMETRY; MICE; MOLECULAR STRUCTURE; TOXICITY TESTS;

DINOPHYCEAE; OSTREOPSIS; PALYTHOA;

EID: 79952317801     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2010.09.012     Document Type: Article

References (90)

1. Alcala A.C., Alcala L.C., Garth J.S., Yasumura D., Yasumoto T. Human fatality due to ingestion of the crab Demania reynaudii that contained a palytoxin-like toxin. Toxicon 1988, 26(1):105-107.
2. Aligizaki K., Katikou P., Nikolaidis G., Panou A. First episode of shellfish contamination by palytoxin-like compounds from Ostreopsis species (Aegean sea, Greece). Toxicon 2008, 51:418-427.
3. Artigas P., Gadsby D.C. Na+/K+-pump ligands modulate gating of palytoxin-induced ion channels. PNAS 2003, 100(2):501-505.
4. Artigas P., Gadsby D.C. Ouabain affinity determining residues lie close to the Na/K pump ion pathway. PNAS 2006, 103(33):12613-12618.
5. Attaway, D.H, L.S. Ciereszko., 1974. Isolation and partial characterization of Caribbean palytoxin. Proceedings of Second International Coral Reef Symposium I, Great Barrier Reef Comunity, Brisbane.
6. Ballantine D.L., Tosteson C.G., Bardales A.T. Population dynamics and toxicity of natural populations of benthic dinoflagellates in southwestern Puerto Rico. Journal of Experimental Marine Biology and Ecology 1988, 119:201-212.
7. Bellocci M., Ronzitti G., Milandri A., Melchiorre N., Grillo C., Poletti R., Yasumoto T., Rossini G.P. A cytolytic assay for the measurement of palytoxin based on a cultured monolayer cell line. Analytical Biochemistry 2008, 374(1):48-55.
8. Beress L., Zwick J., Kolkenbrock H.J., Kaul P.N., Wasserrmann O. A method for the isolation of the Caribbean palytoxin (C-PTX) from the coelenterate (zoanthid) Palythoa caribaeorum. Toxicon 1983, 21:285-290.
9. Bignami G.S. A rapid and sensitive hemolysis neutralization assay for palytoxin. Toxicon 1993, 31(6):817-820.
10. Bignami G.S., Raybould T.J.G., Sachinvala N.D., Grothaus P.G., Simpson S.B., Lazo C.B., Byrnes J.B., Moore R.E., Vann D.C. Monoclonal antibody-based enzyme-linked immunoassays for the measurement of palytoxin in biological samples. Toxicon 1992, 30:687-700.
11. Bottalico, A., Milella, P., Felicini, G.P., 2002. Fioritura di Ostreopsis spl (Dynophyta) nel porto di Otranto. Abstract Book of the Riunione Scientifica Annuale del Gruppo di lavoro per l'Algologia. Chioggia (VE), Italy, 8-9 November, Società Botanica Italiana, 21.
12. Cañete E., Diogène J. Comparative study of the use of neuroblastoma cells (Neuro-2a) and neuroblastoma × glioma hybrid cells (NG108-15) for the toxic effect quantification of marine toxins. Toxicon 2008, 52(4):541-550.
13. Cha J.K., Christ W.J., Finan J.M., Fujioka H., Kishi Y., Klein L.L., Ko S.S., Leder J., McWhorter W.W., Pfaff P., Yonaga M., Uemura D., Hirata Y. Stereochemistry of palytoxin. 4. Complete structure. Journal of the American Chemical Society 1982, 104:7369-7371.
14. Ciminiello P., Dell'Aversano C., Fattorusso E., Forino M., Magno G.S., Tartaglione L., Grillo C., Melchiorre N. The Genoa 2005 outbreak. Determination of putative palytoxin in Mediterranean Ostreopsis ovata by a new liquid chromatography tandem mass spectrometry method. Analytical Chemistry 2006, 78(17):6153-6159.
15. Ciminiello P., Dell-Aversano C., Fattorusso E., Forino M., Tartaglione L., Grillo C., Melchiorre N. Putative palytoxin and its new analogue, ovatoxin-a, in Ostreopsis ovata collected along the Ligurian coasts during the 2006 toxic outbreak. Journal of American Society for Mass Spectrometry 2008, 19:111-120.
16. Ciminiello P., Dell'Aversano C., Dello Iacovo E., Fattorusso E., Forino M., Grauso L., Tartaglione L., Florio C., Lorenzon P., De Bortoli M., Tubaro A., Poli M., Bignami G. Stereostructure and biological activity of 42-Hydroxy-palytoxin: a new palytoxin analogue from Hawaiian Palythoa subspecies. Chemical Research in Toxicology 2009, 22:1851-1859.
17. Deeds J.R., Schwartz M.D. Human risk associated with palytoxin exposure. Toxicon 2010, 56:150-162.
18. Espiña B., Cagide E., Louzao M.C., Fernández M.M., Vieites M.R., Katikou P., Villar A., Jaen D., Maman L., Botana L.M. Specific and dynamic detection of palytoxins by in vitro microplate assay with human neuroblastoma cells. Bioscience Reports 2009, 29(1):13-23.
19. Fraga, S., Riobó P., Diogene J., Paz B., Franco J.M., 2004. Toxic and potentially toxic benthic dinoflagellates observed in Macaronesia (NE Atlantic archipelagos). XIth International Conference on Harmful Algae, Cape Town (South Africa).
20. Frolova G.M., Kuznetsova T.A., MikhaÄlov V.V., Eliakov G.B. Immunoenzyme method for detecting microbial producers of palytoxin. Bioorganicheskaia Khimiia 2000, 26(4):315-320.
21. Frolova G.M., Kuznetsova T.A., Mikhailov V.V., Elyakov G.B. An enzyme linked immunosorbent assay for detecting palytoxin-producing bacteria. Russian Journal of Bioorganic Chemistry 2000, 26(4):285-289.
22. Fukui M., Murata M., Inoue A., Gawel M., Yasumoto T. Ocurrence of palytoxin in the Trigger fish Melichtys vidua. Toxicon 1987, 25:1121-1124.
23. Fusetani N., Sato S., Hashimoto K. Occurrence of water soluble toxin in a parrotfish Ypsiscarus oviforns which is probably responsible for parrotfish liver poisoning. Toxicon 1985, 23:105-112.
24. Garet E., Cabado A.G., Vieites J.M., González-Fernández A. Rapid isolation of single-chain antibodies by phage display technology directed against one of the most potent marine toxins: palytoxin. Toxicon 2010, 55:1519-1526.
25. Gleibs S., Mebs D. Distribution and sequestration of palytoxin in coral reef animals. Toxicon 1999, 37:1521-1527.
26. Gleibs S., Mebs D., Werding B. Studies on the origin and distribution of palytoxin in a Caribbean coral reef. Toxicon 1995, 33(11):1531-1537.
27. Gonzáles R.B., Alcala A.C. Fatalities from crab poisoning on Negros Island, Philippines. Toxicon 1977, 15:169-170.
28. Granéli, E., Ferreira C.E.L., Yasumoto T., Rodrigues E., Neves M.H.B., 2002. Sea urchins poisoning by the benthic dinoflagellate Ostreopsis ovata on the Brazilian coast. Book of abstracts Xth International Conference on Harmful algae (Florida).
29. Guerrini F., Pezzolesi L., Feller A., Riccardi M., Ciminiello P., Dell'Aversano C., Tartaglione L., Iacovo E.D., Fattorusso E., Forino M., Pistocchi R. Comparative growth and toxin profile of cultured Ostreopsis ovata from the Tyrrhenian and Adriatic Seas. Toxicon 2010, 55(2-3):211-220.
30. Habermann E. Palytoxin acts through Na+, K+-ATPase. Toxicon 1989, 27:1171-1187.
31. Habermann E., Chhatwal G.S. Ouabain inhibits the increase due to Palytoxin of cation permeability of erythrocytes. Naunyn-Schmiedeberg's Archives of Pharmacology 1982, 319:101-107.
32. Habermann E., Ahnert-Hilger G., Chhatwal G.S., Beress L. Delayed haemolytic action of palytoxin. Biochemica et Biophysica Acta 1981, 649:481-486.
33. Hashimoto Y., Fusetani N., Kimura S. Aluterin: a toxin of Filefish, Alutera scripta, probably originated from a zoantharian, Palythoa tuberculosa. Bulletin of the Japanese Society of Scientific Fisheries 1969, 35:1086.
34. Hirata, Y., D. Uemura and Y. Ohizumi; 1988. Chemistry and pharmacology of palytoxin. Handbook of natural toxins. M. Dekker. New York. vol.3, Marine toxins and venoms: 241-258.
35. Hoffmann K., Hermanns-Clausen M., Buhl C., Büchler M.W., P.Schemmer, Mebs D., Kauferstein S. A case of palytoxin poisoning due to contact with zoanthid corals through a skin injury. Toxicon 2008, 51:1535-1537.
36. Inuzuka T., Uemura D., Arimoto H. The conformational features of palytoxin in aqueous solution. Tetrahedron 2008, 64(33):7718-7723.
37. Kimura S., Hashimoto K. Purification of the toxin in a zoanthid Palythoa tuberculosa. Publications of the Seto Marine Biological Laboratory 1973, 20:713-718.
38. Kodama A.M., Hokama Y., Yasumoto T., Fukui M., Manea S.J., Sutherland N. Clinical and laboratory findings implicating palytoxin as cause of ciguatera poisoning due to Decapterus macrosoma (mackerel). Toxicon 1989, 27:1051-1053.
39. Lau C.O., Khoo H.E., Yuen R., Wan M., Tan C.H. Isolation of a novel fluorescent toxin from the coral reef crab, Lophozozymus pictor. Toxicon 1993, 31:1341-1345.
40. Lau C.O., Tan C.H., Khoo H.E., Yuen R., Lewis R.J., Corpuz G.P., Bignami G.S. Lophozozymus pictor toxin: a fluorescent structural isomer of palytoxin. Toxicon 1995, 33(10):1373-1377.
41. Ledreux A., Krys S., Bernard C. Suitability of the Neuro-2a cell line for the detection of palytoxin and analogues (neurotoxic phycotoxins). Toxicon 2009, 53(2):300-308.
42. Lenoir S., Ten-Hage L., Turquet J., Quod J.P., Bernard C., Hennion M.C. First evidence of palytoxin analogues from an Ostreopsis mascarenensis (Dinophyceae) benthic bloom in southwestern Indian Ocean. Journal of Phycology 2004, 40:1042-1051.
43. Levine L., Fujiki H., Gjika H.B., Van Vunakis H. A radioimmunoassay for palytoxin. Toxicon 1988, 26:1115-1121.
44. Mahnir V.M., Kozlovskaja E.J. Isolation of palytoxin from the sea anemone Radianthus macrodactylus. Bioorganic Chemistry 1992, 18:751-752.
45. Majlesi N., Su M.K., Chang G.M., Lee D.C., Greller H.A. A case of inhalational exposure to palytoxin. Clinical Toxicology 2008, 46:637.
46. Mereish K.A., Morris S., McCullers G., Taylor T.J., Bunner D.L. Analysis of palytoxin by liquid chromatography and capillary electrophoresis. Journal of Liquid Chromatography 1991, 14(5):1025-1031.
47. Moore R.E. Structure of palytoxin. Fortschritte der Chemie Organischer Naturst 1985, 48:81-202.
48. Moore R.E., Bartolini G. Structure of palytoxin. Journal of American Chemical Society 1981, 103:2491-2494.
49. Moore R.E., Scheuer P.J. Palytoxin: a new marine toxin from a coelenterate. Science 1971, 172:495-498.
50. Morton, S. L., K. S. Sifleet, L. L. Smith and M. L. Parsons. Morphology and ecology of a new species of Ostreopsis (Dinophyceae), O. tholus sp. nov., isolated from Hilo, Hawaii, USA. in preparation.
51. Nakajima I., Oshima Y., Yasumoto T. Toxicity of benthic dinoflagellates in Okinawa. Bulletin of the Japanese Society of Scientific Fisheries 1981, 47(8):1029-1033.
52. Noguchi T., Hwang D., Arakawa O., Daigo K., Sato S., Ozaki H., Kwoi N., Ito M., Hashimoto K. Palytoxin as the causative agent in the parrotfish poisoning. Progress in Venom and toxin research 1987, 325-335. National University of Singapore, Kent Ridge, Singapore. P.G. A, C.K. Tan (Eds.).
53. Okano H., Masuoka H., Kamei S., Seko T., Koyabu S., Tsunemoto K., Tamiya T., Ueda K., Nakazawa S., Sugawa M., Suzuki H., Watanabe M., Yatani R., Nakano T. Rhabdomyolysis and myocardial damage induced by palytoxin, a toxin of blue humphead parrotfish. Internal Medicine 1998, 37:330-333.
54. Oku N., Sata N.U., Matsunaga S., Uchida H., Fusetani N. Identification of palytoxin as a principle which causes morphological changes in rat 3Y1 cells in the zoanthid Palythoa aff. margaritae. Toxicon 2004, 43(1):21-25.
55. Onuma Y., Satake M., Ukena T., Roux J., Chanteau S., Rasolofonirina N., Ratsimaloto N., Naoki H., Yasumoto T. Identification of putative palytoxin as the cause of clupeotoxism. Toxicon 1999, 37(1):55-65.
56. Pearce I., Marshall J.A., Hallegraeff G.M. Toxic epiphytic dinoflagellates from East Coast Tasmania, Australia. Harmful Algal blooms 2000 2001, 54-57. Intergovernmental Oceanographic Commision of UNESCO, Tasmania. G.M. Hallegraeff, S.I. Blackburn, C.J. Bolch, R.J. Lewis (Eds.).
57. Penna A., Vila M., Fraga S., Giacobbe M.G., Andreoni F., Riobó P., Vernesi C. Characterization of Ostreopsis and Coolia (Dinophyceae) isolates in the Western Mediterranean Sea based on morphology, toxicity and internal transcribed spacer 5.8s rDNA sequences. Journal of Phycology 2005, 41:212-245.
58. Quod J.P. Ostreopsis mascarenensis sp. nov. (Dinophyceae), dinoflagellé toxique associé à la ciguatera dans l'océan Indien. Cryptogamie, Algol 1994, 15(4):243-251.
59. Rhodes L., Adamson J., Suzuki T., Briggs L., Garthwaite I. Toxic marine epiphytic dinoflagellates, Ostreopsis siamensis and Coolia monotis (Dinophyceae), in New Zealand. New Zealand Journal of Marine and Freshwater Research 2000, 34:371-383.
60. Rhodes L., Towers N., Briggs L., Munday R., Adamson J. Uptake of palytoxin-like compounds by shellfish fed Ostreopsis siamensis (Dinophyceae). New Zealand Journal of Marine and Freshwater Research 2002, 36:631-636.
61. Riobó P., Paz B., Fernández M.L., Fraga S., Franco J.M. Lipophylic toxins of different strains of Ostreopsidaceae and Gonyaulaceae. Harmful Algae 2002. Proceedings of the Xth International Conference on harmful Algae 2004, 119-121. Florida fish and Wildlife Conservation Commission and Intergovernamental Oceanographic Commission of UNESCO, Florida. K.A. Steidinger, J.H. Landsberg, C.R. Thomas, G.A. Vargo (Eds.).
62. Riobó, P., Paz B., Fraga S., Franco J.M., 2004b. A new method for the analysis of Palytoxin with liquid chromatography coupled to fluorescence detection and MS, comparison with hemolytic assay of Palytoxin in benthic dinoflagellates Ostreopsis spp. XIth International Conference on Harmful Algae, Cape Town (South Africa).
63. Riobó P., Paz B., Franco J.M. Analysis of palytoxin-like in Ostreopsis cultures by liquid chromatography with precolumn derivatization and fluorescence detection. Analytica Chimica Acta 2006, 566:217-223.
64. Riobó P., Paz B., Franco J.M., Vázquez J., Murado M.A. Proposal for a simple and sensitive haemolytic assay for palytoxin. Toxicological dynamics, kinetics, ouabain inhibition and thermal stability. Harmful Algae 2008, 7:415-429.
65. Riobó P., Paz B., Franco J.M., Vázquez J.A., Murado M.A., Cacho E. Mouse bioassay for Palitoxin. Dose-response and dose-death time relationships. Food and chemical toxicology 2007.
66. Sala G.L., Bellocci M., Rossini G.P. The cytotoxic pathway triggered by palytoxin involves a change in the cellular pool of stress response proteins. Chemical Research in Toxicology 2009, 22:2009-2016.
67. Sansoni G., Borghini B., Camici G., Casotti M., Righini P., Rustighi C. Fioriture algali di Ostreopsis ovata (Gonyaulacales: Dinophyceae): un problema emergente. Biologia Ambientale 2003, 17(1):17-23.
68. Seemann P., Gernert C., Schmitt S., Mebs D., Hentschel U. Detection of hemolytic bacteria from Palythoa caribaeorum (Cnidaria, Zoantharia) using a novel palytoxin-screening assay. Antonie Van Leeuwenhoek 2009, 96(4):405-411.
69. Simoni F., Gaddi A., Di Paolo C., Lepri L. Harmful epiphytic dinoflagellates on Tyrrhenian Sea. Harmful Algae News 2003, 24:13-14.
70. Simoni F., Di Paolo C., Gori L., Lepri L. Further investigation on blooms of Ostreopsis ovata, Coolia monotis, Prorocentrum lima, on the macroalgae of artificial and natural reefs in the Northern Tyrrhenian Sea. Harmful Algae News 2004, 26:5-7.
71. Tan C.H., Lau C.O. Chemisty and Detection of Palytoxin. Seafood and Freshwater Toxins: pharmacology, physiology and Detection 2000, 533-548. Marcel Dekker, New York. L.M. Botana (Ed.).
72. Taniyama S., Arakawa O., Terada M., Nishio S., Takatani T., Mahmud Y., Noguchi T. Ostreopsis sp., a possible origin of palytoxin (PTX) in parrotfish Scarus ovifrons. Toxicon 2003, 42:29-33.
73. Taniyama S., Mahmud Y., Terada M., Takatani T. Occurrence of a food poisoning incident by palytoxin form a serranid Epinephelus sp. in Japan. Journal of Natural Toxins 2002, 11(4):277-282.
74. Taniyama S., Mahmud Y., Tanu M.B., Takatani T., Arakawa O., Noguchi T. Delayed haemolytic activity by the freshwater puffer Tetradon sp. toxin. Toxicon 2001, 39:725-727.
75. Teh Y.F., Gardiner J.E. Partial purification of Lophozozymus pictor toxin. Toxicon 1974, 12:603-610.
76. Tognetto L., Bellato S., Moro I., Andreoli C. Occurrence of Ostreopsis ovata (Dinophyceae) in the Tyrrhenian Sea during summer 1994. Botanica Marina 1995, 38:291-295.
77. Turquet J., Lenoir S., Quod J.P., Ten-Hage L., Hennion M.C. Toxicity and toxin profiles of a bloom of Ostreopsis mascarenensis, Dinophyceae, from the SW Indian Ocean. Harmful Algae 2002. Proceedings of the Xth International Conference on Harmful Algae 2003, Florida Fish and Wildlife Conservation Commission and Intergovernamental Oceanographic Commission of UNESCO, Florida. K.A. Steidinger, J.H. Landsberg, C.R. Thomas, G.A. Vargo (Eds.).
78. Uemura D. Bioactive Polyethers. Bioorganic Marine Chemistry 1991, 4:1-27. Springer-Verlag, Berlin Heidelberg. P.J. Scheuer (Ed.).
79. Uemura D. Bioorganic studies on marine natural products, diverse chemical structures and bioactivities. The Chemical Record 2006, 6:235-248.
80. Uemura D., Ueda K., Hirata Y., Iwashita T., Naoki H. Further studies on palytoxin II. Structure of palytoxin. Tetrahedron Letters 1985, 22:1007-1017.
81. Ukena T., Satake M., Usami M., Oshima Y., Naoki H., Fujita T., Kan Y., Yasumoto T. Structure elucidation of Ostreocin D, a Palytoxin analog isolated from the Dinoflagellate Ostreopsis siamensis. Bioscience, Biotechnology, and Biochemistry 2001, 65(11):2585-2588.
82. Ukena T., Satake M., Usami M., Oshima Y., Fujita T., Naoki H., Yasumoto T. Structural confirmation of ostreocin-D by application of negative-ion fast-atom bombardment collision-induced dissociation tandem mass spectrometric methods. Rapid Communications in Mass Spectrometry 2002, 16:2387-2393.
83. Usami M., Satake M., Ishida S., Inoue A., Kan Y., Yasumoto T. Palytoxin analogs from the dinoflagellate Ostreopsis siamensis. Journal of the American Chemical Society 1995, 117(19):5389-5390.
84. Vila M., Garcés E., Masó M. Potentially toxic epiphytic dinoflagellates assemblages on macroalgae in the NW Mediterranean. Aquatic Microbial Ecology 2001, 26:51-60.
85. Walsh G.E., Bowers R.L. A review of Hawaiian zoanthids with descriptions of three new species. Zoological Journal of the Linnean Society 1971, 50:161-180.
86. Wiles J.S., Vick J.A., Christensen M.K. Toxicological evaluation of palytoxin in several animal species. Toxicon 1974, 12:427.
87. Yasumoto T., Oshima Y., Yamaguchi M. Occurrence of a new type of shellfish poisoning in the Tohoku district. Bulletin of the Japanese Society of Scientific Fisheries 1978, 44:1249-1255.
88. Yasumoto T., Yasumura D., Ohizumi Y., Takahashi M., Alcala A.C., Alcala L.C. Palytoxin in two species of xanthid crab from the Philippines. Agricultural and Biological Chemistry 1986, 50:163-167.
89. Yasumoto T., Seino N., Murakami Y., Murata M. Toxins produced by benthic dinoflagellates. Biological Bulletin 1987, 172:128-131.
90. Zingone A., Siano R., D'Alelio D., Sarno D. Potentially toxic and harmful microalgae from coastal waters of the Campania region (Tyrrhenian Sea, Mediterranean Sea). Harmful Algae 2006, 5:321-337.