Report on the first detection of pectenotoxin-2, spirolide-A and their derivatives in French shellfish

Marine Drugs

Volumn 5, Issue 4, 2007, Pages 168-179

  Amzil, Zouher ^a   Sibat, Manoella ^a   Royer, Florence ^a   Masson, Nadine ^a   Abadie, Eric ^a  

^a IFREMER   (France)

Author keywords

DSP toxins; LC MS analysis; Pectenotoxins; Spirolides

Indexed keywords

AZASPIRACID; DINOPHYSISTOXIN; GYMNODIMINE DERIVATIVE; OKADOIC ACID; PECTENOTOXIN 2; SPIROLIDE A; TOXIN; UNCLASSIFIED DRUG; YESSOTOXIN;

ARTICLE; BIOASSAY; CONTROLLED STUDY; ELECTROSPRAY; FRANCE; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PHYTOPLANKTON; SHELLFISH; SHELLFISH POISONING;

ALGAE;

EID: 37749020553     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md504168     Document Type: Article

References (35)

1. Murata, M.; Shimatani, M.; Sugitani, H.; Oshima, Y.; Yasumoto, T. Isolation and structural elucidation of the causative toxin of diarrhetic shellfish poisoning. Bull. Jap. Soc. Fish. 1982, 48, 549-552.
2. Kumagai, M.; Yanagi, T.; Murata, M.; Yasumoto, T.; Kat, M.; Lassus, P.; Rodriguez-Vasquez, J.A. Okadaic acid as causative toxin of diarrhetic shellfish poisoning in Europe. Agric. Biol. Chem.1986, 50, 2853-2857.
3. Hu, T.; Doyle, J.; Jackson, D.; Marr, J.; Nixon, E.; Pleasance, S.; Quilliam, M.A.; Walter, J.A.; Writh, J.L.C. Isolation of a new diarrhetic shellfish poison from Irish mussels. Chem. Commun. 1992, 39-41.
4. 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.
5. Vale, P.; Antonia, M.; Sampayo, M. Esters of okadaic acid related to human poisonings. Toxicon 1999, 37, 1109-1121.
6. 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.
7. Yasumoto, T.; Murata, M.; Oshima, Y.; Sano, M.; Matsumoto, G.K.; Clardy, J. Diarrhetic shellfish toxins. Tetrahedron 1985, 41, 1019-1025.
8. Murata, M.; Kumagai, M.; Lee, J.S.; Yasumoto, T. Isolation and structure of yessotoxin, a polyether compound implicated in diarrhetic shellfish poisoning. Tetrahedron Lett. 1987, 28, 5869-5872.
9. Satake, M.; Mackenzie, L.; Yasumoto, T. Identification of Protoceratium reticulatum as the biogenetic origin of yessotoxin. Natural Toxins 1997, 5, 164-167.
10. Ofuji, K.; Satake, M.; McMahon, T.; James, K.J.; Naoki, H.; Oshima, Y.; Yasumoto, T. Two analogs of azaspiracids isolated from mussels, Mytilus edulis, involved in human intoxication in Ireland. Natural Toxins 1999, 7, 99-102.
11. James, K.J.; Furey, A.; Lehane, M.; Ramstad, H.; Aune, T.; Hovgaard, P.; Morris, S.; Higman, W.; Satake, M.; Yasumoto, T. First evidence of an extensive northern European distribution of azaspiracid poisoning (AZP) toxins in shellfish. Toxicon 2002, 40, 909-915.
12. Yasumoto, T.; Murata, M.; Oshima, Y.; Matsumoto, G.K.; Clardy, J. Diarrhetic Shellfish Poisoning. In: Sea Food Toxins; Ragelis, E.P. (ed.); ACS Symposium Series: A.C.S.: Washington, DC, 1984; vol. 262, pp. 208-214.
13. Hu, T.; Curtis, J.M.; Oshima, Y.; Quilliam, M.A.; Walter, J.A.; Watson-Wright, W.M.; Wright, J.L.C. Spirolides B and D, two novel macrocycles isolated from the digestive glands of shellfish. J. Chem. Soc., Chem. Commun. 1995, 2159-2161.
14. Cembella, A.D.; Quilliam, M.A.; Lewis, N.I.; Bauder, A.G.; Wright J.L.C. Identifying the plankton origin and distribution of spirolides in coastal Nova Scotian waters. In Harmful Algae; Reguera B.; Blanco J.; Fernandez M.L.; Wyatt T. (Eds); Xunta de Galicia and Intergovernmental Oceanographic Commission of UNESCO, 1998; pp. 481-484.
15. Cembella, A.D.; Lewis, N.I.; Quilliam, M.A. The marine dinoflagellate Alexandrium ostenfeldii (Dinophyceae) as the causative organism of spirolides shellfish toxins, Phycologia 2000, 39, 67-74.
16. Aasen, J.; Mackinnon, S.L.; Le Blanc, P.; Walter, J.A.; Hovgaard, P.; Aune, T.; Quilliam, M.A. Detection and identification of spirolides in Norwegian shellfish and plankton. Chem. Res. Toxicol. 2005, 18, 509-515.
17. Villar Gonzalez, A.; Rodriguez-Valasco, M.L.; Ben-Gigirey, B.; Botana, L.M. First evidence of spirolides in Spanish shellfish. Toxicon 2006, 48, 1068-1074.
18. Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Magno, S.; Tartaglione, L.; Cangini, M.; Pompei, M.; Guerrini, F.; Boni, L.; Pistochi, R. Toxin profile of Alexandrium ostenfeldii (Dinophyceae) from the Northern Adriatic sea revealed by liquid chromatography-mass spectrometry. Toxicon 2006, 47, 597-604.
19. MacKenzie, L.; Haywood, A.; Adamson, J.; Truman, P.; Till, D.; Deki, T.; Satake, M.; Yasumoto, T. Gymnodimine contamination of shellfish in New Zealand, In Harmful and toxic algal blooms; Yasumoto, T.; Oshima, Y.; Fukuyo, Y. (eds),; IOC of UNESCO Publish.: Paris, 1996; pp. 97-100.
20. McKenzie, L.; Beuzenberg, V.; McNabb, P. Production of gymnodimine by Karenia selliformis. (Haywood et al).; In: Harmful Algae 2002. Steidinger, K.A.; Landsberg, C.R.; Vargo, G.A (eds); Florida Fish and Wildlife Conservation Commission, Florida Institute of Aceanography, and IOC of UNESCO Publish: Paris; 2004; pp. 160-162.
21. Biré, R.; Krys, S.; Frémy, J.M.; Dragacci, S.; Stirling, D.; Kharrat, R. First evidence on occurrence of gymnodimine in clams from Tunisia, J. Nat. Toxins 2002, 11, 269-275.
22. Lassus, P.; Bardouil, M.; Berthome, J.P.; Maggi, P.; Truquet, P.; Le Dean, L. Seasonal occurrence of Dinophysis sp. along the French coast between 1983 and 1987. Aquat. Living Ressour 1988, 1, 155-164.
23. Lassus, P.; LeDoux, M.; Bardouil, M.; Bohec, M.; Erard-LeDenn, E. Kinetics of Alexandrium minitum Halim toxin accumulation in mussels and clams. Natural Toxins 1994, 2, 329-333.
24. Masselin, P.; Lassus, P.; Bardouil, M.. High performance liquid chromatography analysis of diarrhoeic toxins in Dinophysis spp. from the French coast. J. Appl. Phycol. 1992, 4, 385-389.
25. Masselin, P.; Amzil, Z.; Abadie, E.; Nézan, E.; Le Bec, C.; Chiantella, C.; Truquet, P. Paralytic shellfish poisoning on the French Mediterranean coast in the autumn 1998: Alexandrium tamarense complex (Dinophyceae) as causative agent. In Harmful Algal Blooms. Hallegraeff, G.M.; Blackburn, S.I.; Bolch, C.J.; Lewis R.J. (eds); JOC of UNESCO Publish.: Paris, 2001; pp., 407-410.
26. Amzil, Z.; Fresnel, J.; Le Gal, D.; Billard C. Domoic acid accumulation in french shellfish in relation to toxic species of Pseudo-nitzschia multiseries and P. pseudodelicatissima. Toxicon 2001, 39, 1245-1251,
27. Amzil, Z.; Mathias, A. First report on detection of okadaic acid 7-O-acyl-ester derivatives (DTX-3) in French shellfish. In Molluscan Shellfish Safety. Henshilwood, K.; Deegan, B.; McMahon, T.; Cusak, C.; Keaveney, S.; Silke, J.; O' Cinneide, M.; Lyons, D.; Hess P. (eds); The Marine Institute, Rinville, Oranmore, Galway, Ireland, 2006; pp. 150-161.
28. Quilliam, M. A.; Hess, P.; Dell'Aversano, C. Recent developments in the analysis of phycotoxins by liquid chromatography-mass spectrometry. In: Mycotoxins and Phycotoxins in Perspective at the Turn of the Millenium; De Koe, W.J.; Sampson, R.A.; Van Egmond, H.P.; Gilbert J.; Sabino, M. (eds.).; DeKoe W.J., Wageningen, The Netherlands, 2001; pp. 383-391.
29. Mondeguer, F.; Genin, E.; Mestre, G.; Nsengiyumva, C. Validation of an automated procedure of solid phase extraction of mussels digestive glands for identification and quantification of Dinophysistoxins in LC/ESI/MS2 by quadruple ion trap. In Molluscan Shellfish Safety. Henshilwood, K.; Deegan, B.; McMahon, T.; Cusak, C.; Keaveney, S.; Silke, J.; O' Cinneide, M.; Lyons, D.; Hess P. (eds); The Marine Institute, Rinville, Oranmore, Galway, Ireland, 2006; pp. 94-99.
30. 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.; Quilliam, M.A.; MacKenzie, A.L.; Beuzenberg, V.; Towers, N.R. 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.
31. Suzuki, T.; MacKenzie, L.; Stirling, D.; Adamson, J. Pectenotoxin-2 seco acid: a toxin converted from pectenotoxin-2 by the New Zealand Greenshell mussel, Pena canaliculus. Toxicon 2001, 39, 207-514.
32. McKenzie, 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.
33. Vrancic, M.P.; Mestrovic, V.; Marasovic, I.; Gillman, M.; Furey, A.; James K.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.
34. Vale, P.; De 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, 972-987.
35. Blanco, J.; Alvarez, G.; Uribe, E. Identification of pectenotoxins in plankton, filter feeders, and isolated cells of a Dinophysis acuminata with an atypical toxin profile, from Chile. Toxicon 2007, 49, 710-716.