Development of quantitative NMR method with internal standard for the standard solutions of paralytic shellfish toxins and characterisation of gonyautoxin-5 and gonyautoxin-6

Toxicon

Volumn 56, Issue 4, 2010, Pages 589-595

  Watanabe, Ryuichi ^a   Suzuki, Toshiyuki ^a   Oshima, Yasukatsu ^b  

^a FISHERIES RESEARCH AGENCY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

Gonyautoxin 5; Gonyautoxin 6; Internal standard; Paralytic shellfish toxins; Quantitative NMR

Indexed keywords

GONYAUTOXIN; GONYAUTOXIN 5; GONYAUTOXIN 6; SAXITOXIN; SHELLFISH TOXIN; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG;

ACCURACY; ANIMAL EXPERIMENT; ARTICLE; BIOASSAY; CONTROLLED STUDY; ISOLATION PROCEDURE; MALE; MOUSE; MUSSEL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROCESS DEVELOPMENT; PROCESS OPTIMIZATION; QUANTITATIVE ANALYSIS; RELAXATION TIME; REPRODUCIBILITY; STANDARDIZATION; STRUCTURE ANALYSIS; TOXICITY TESTING; TOXIN ANALYSIS; TOXIN STRUCTURE;

DINOPHYCEAE; GYMNODINIUM CATENATUM; MUS;

EID: 77954952013     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2010.06.002     Document Type: Article

References (34)

1. Anderson D.M., Sullivan J.J., Reguera B. Paralytic shellfish poisoning in northwest Spain: the toxicity of the dinoflagellate Gymnodinium catenatum. Toxicon 1989, 27:665-674.
2. AOAC official method 959.08 Paralytic shellfish poison. Biological method. Final action. Official Methods of Analysis-AOAC-Fourteenth Edition 1995, 21-22. Association of Official Analytical Chemists, Arlington, (Chapter 35). S. Williams (Ed.).
3. Arakawa O., Nishio S., Noguchi T., Shida Y., Onoue Y. A new saxitoxin analogue from a xanthid crab Atergatis floridus. Toxicon 1995, 33:1577-1584.
4. Aversano C.D., Hess P., Quilliam M.A. Hydrophilic interaction liquid chromatography-mass spectrometry for the analysis of paralytic shellfish poisoning (PSP) toxins. J. Chromatogr. A. 2005, 1081:190-201.
5. Ben-Gigirey B., Rodríguez-Velasco M.L., Villar-González A., Botana L.M. Influence of the sample toxic profile on the suitability of a high performance liquid chromatography method for official paralytic shellfish toxins control. J. Chromatogr. A. 2007, 1140:78-87.
6. 1H NMR with external standards: use in preparation of calibration solutions for algal toxins and other natural products. Anal. Chem. 2005, 77:3123-3131.
7. 1H NMR quantification in very dilute toxin solutions: application to anatoxin-a analysis. Toxicon 2005, 46:236-240.
8. Fleming J.J., Du Bois J. A synthesis of (+)-Saxitoxin. J. Am. Chem. Soc. 2006, 128:3926-3927.
9. Genenah A.A., Shimizu Y. Specific toxicity of paralytic shellfish poisons. J. Agric. Food Chem. 1981, 29:1289-1291.
10. Harada T., Oshima Y., Yasumoto T. Structures of two paralytic shellfish toxins, Gonyautoxins V and VI, isolated from a tropical dinoflagellate, Pyrodinium bahamense var. compressa. Agric. Biol. Chem. 1982, 46:1861-1864.
11. Holzgrabe U., Deubner R., Schollmayer C., Waibel B. Quantitative NMR spectroscopy - application in drug analysis. J. Pharm. Biomed. Anal. 2005, 38:806-812.
12. Kodama M., Ogata T., Sakamoto S., Sato S., Honda T., Miwatani T. Production of paralytic shellfish toxins by a bacterium Moraxella sp. isolated from Protogonyaulax tamarensis. Toxicon 1990, 28:707-714.
13. Larive C.K., Jayawickrama D., Orfi L. Quantitative analysis of peptides with NMR spectroscopy. Appl. Spectrosc. 1997, 51:1531-1536.
14. Laycock M.V., Thibault P., Ayer S.W., Walter J.A. Isolation and purification procedures for the preparation of paralytic shellfish poisoning toxin standards. Nat. Toxins 1994, 2:175-183.
15. Lawrence J.F., Niedzwiadek B. Quantitative determination of paralytic shellfish poisoning toxins in shellfish using prechromatographic oxidation and liquid chromatography with fluorescence detection. J. AOAC Int. 2001, 84:1099-1108.
16. Lawrence J.F., Niedzwiadek B., Menard C. Quantitative determination of paralytic shellfish poisoning toxins in shellfish using prechromatographic oxidation and liquid chromatography with fluorescence detection: interlaboratory study. J. AOAC Int. 2004, 87:83-100.
17. Lin H.P., Cho Y., Yashiro H., Yamada T., Oshima Y. Purification and characterization of paralytic shellfish toxin transforming enzyme from Mactra chinensis. Toxicon 2004, 44:657-668.
18. Miyamura K., Matsuyama Y., Oh S.J. Occurrence of the toxic dinoflagellate Gymnodinium catenatum, toxin contents of suspended matter and prediction of PSP outbreak in the scallop Chlamys noblis in Inokushi bay, Oita prefecture. Nippon Suisan Gakk. 2007, 73:34-42.
19. Molica R., Onodera H., Garciá C., Rivas M., Andrinolo D., Nascimento S., Meguro H., Oshima Y., Azevedo S., Lagos N. Toxins in the freshwater cyanobacterium Cylindrospermopsis raciborskii (Cyanophycaea) isolated from Tabocas reservoir in Caruaru, Brazil, including demonstration of a new saxitoxin analogue. Phycologia 2002, 41:606-611.
20. Negri A., Stirling D., Quilliam M., Blackburn S., Bolch C., Burton I., Eaglesham G., Thomas K., Walter J., Willis R. Three novel hydroxybenzoate saxitoxin analogues isolated from the dinoflagellate Gymnodinium catenatum. Chem. Res. Toxicol. 2003, 16:1029-1033.
21. Onodera H., Satake M., Oshima Y., Yasumoto T., Carmichael W.W. New saxitoxin analogues from the freshwater filamentous cyanobacterium Lyngbya wollei. Nat. Toxins 1997, 5:146-151.
22. Oshima Y., Hasegawa M., Yasumoto T., Hallegraeff G., Blackburn S. Dinoflagellate Gymnodinium catenatum as the source of paralytic shellfish toxins in Tasmanian shellfish. Toxicon 1987, 25:1105-1111.
23. Oshima Y., Blackburn S.I., Hallegraeff G.M. Comparative study on paralytic shellfish toxin profiles of the dinoflagellate Gymnodinium catenatum from three different countries. Mar. Biol. 1993, 116:471-476.
24. Oshima Y. Chemical and enzymatic transformation of paralytic shellfish toxins in marine organisms. Harmful Marine Algal Blooms 1995, 475-480. Lavoisier/Intercept, Paris. P. Lassus, G. Arzul, E. Erard, P. Gentien, C. Marcaillou (Eds.).
25. Oshima Y. Post-column derivatization HPLC methods for paralytic shellfish poisons. Manual on Harmful Marine Microalgae 1995, 81-84. UNESCO. G.M. Hallegraeff, D.M. Anderson, A.D. Cembella (Eds.).
26. Pauli G.F. qNMR - a versatile concept for the validation of natural product reference compounds. Phytochem. Anal. 2001, 12:28-42.
27. 1H NMR: development and potential of a method for natural products analysis. J. Nat. Prod. 2005, 68:133-149.
28. Pomati F., Sacchi S., Rossetti C., Giovannardi S., Onodera H., Oshima Y., Neilan B.A. The freshwater cyanobacterium Planktothrix sp. FP1: molecular identification and detection of paralytic shellfish poisoning toxins. J. Phycol. 2000, 36:553-562.
29. Rizzo V., Pinciroli V. Quantitative NMR in synthetic and combinatorial chemistry. J. Pharm. Biomed. Anal. 2005, 38:851-857.
30. Sato S., Sakai R., Kodama M. Identification of thioether intermediates in the reductive transformation of gonyautoxins into saxitoxins by thiols. Bioorg. Med. Chem. Lett. 2000, 10:1787-1789.
31. Shimizu Y., Alam M., Oshima Y., Fallon W.E. Presence of four toxins in red tide infested clams and cultured Gonyaulax tamarensis cells. Biochem. Biophys. Res. Commun. 1975, 66:731-737.
32. Sullivan J.J. High-performance liquid chromatographic method applied to paralytic shellfish poisoning research. Marine Toxins-origin, Structure and Molecular Pharmacology 1990, 66-77. The American Chemical Society, Washington. S. Hall, G. Strichartz (Eds.).
33. Sullivan J.J., Iwaoka W.T., Liston J. Enzymatic transformation of PSP toxins in the littleneck clam (Protothaca staminea). Biochem. Biophys. Res. Commun. 1983, 144:465-472.
34. Watanabe R., Samusawa-Saito R., Oshima Y. Development of saxitoxin-conjugated affinity gels. Bioconjug. Chem. 2006, 17:459-465.