Enzymatic hydrolysis of esterified diarrhetic shellfish poisoning toxins and pectenotoxins

Analytical and Bioanalytical Chemistry

Volumn 389, Issue 1, 2007, Pages 335-342

  Doucet, Erin ^a,b   Ross, Neil N ^a   Quilliam, Michael A ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b DALHOUSIE UNIVERSITY   (Canada)

Author keywords

Diarrhetic shellfish poisoning (DSP); Dinophysistoxins; Enzymatic hydrolysis; Esters; Liquid chromatography mass spectrometry; Okadaic acid; Pectenotoxins

Indexed keywords

DIARRHETIC SHELLFISH POISONING (DSP); DINOPHYSISTOXINS; ENZYMATIC HYDROLYSIS; OKADAIC ACID; PECTENOTOXINS;

ENZYME ACTIVITY; ESTERIFICATION; ESTERS; FISH; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

TOXIC MATERIALS;

ALKALI; DINOPHYSISTOXIN 3; ESTERASE; MARINE TOXIN; PYRAN DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ESTERIFICATION; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; SHELLFISH; SWINE;

ALKALIES; ANIMALS; CHROMATOGRAPHY, LIQUID; ESTERASES; ESTERIFICATION; HYDROLYSIS; LIPASE; MARINE TOXINS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PYRANS; SHELLFISH; SWINE;

SUS;

EID: 34548240088     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-007-1489-3     Document Type: Article

References (38)

1. Botana LM (2000) Seafood and freshwater toxins: pharmacology, physiology and detection. Marcel Dekker, New York
2. Yasumoto T, Murata M (1993) Marine toxins. Chem Rev 93:1897-1909
3. Yasumoto T, Murata M, Oshima Y, Sano M, Matsumoto GK, Clardy J (1985) Diarrhetic shellfish toxins. Tetrahedron 41:1019-1025
4. Hu T, Doyle J, Jackson D, Marr J, Nixon E, Pleasance S, Quilliam MA, Walter JA, Wright JLC (1992) Isolation of a new diarrhetic shellfish poison from Irish mussels. J Chem Soc Chem Commun 39-41
5. Bailojan C, Takai A (1988) Inhibitory effects of a marine sponge toxin, OA, on protein phosphatases. Biochem J 256:283-290
6. Cohen P, Holmes CFB, Tsukitani Y (1990) Okadaic acid: a new probe for the study of cellular regulation. Trends Biochem Sci 15:98-102
7. Mestrovic V, Pavela Vrancic A (2003) Inhibition of alkaline phosphatase activity by okadaic acid, a protein phosphatase inhibitor. Biochimie 85:647-650
8. Haystead TAJ, Sim ATR, Carling D, Honnor RC, Tsukitani Y, Cohen P, Hardie DG (1989) Effects of the tumor promoter okadaic acid on intracellular protein phosphorylation and metabolism. Nature 337:78-81
9. Fujiki H, Suganuma M (1993) Tumor promotion by inhibitors of protein phosphatases 1 and 2A: the okadaic acid class of compounds. Adv Cancer Res 61:143-194
10. Dahl E, Johannessen T (2001) Relationship between occurrence of Dinophysis species (Dinophyceae) and shellfish toxicity. Phycologia 40:223-227
11. Hu T, Marr J, de Freitas ASW, Quilliam MA, Walter JA, Wright JLC, Pleasance S (1992) New diol esters of okadaic acid isolated from cultures of the dinoflagellates Prorocentrum lima and Prorocentrum concavum. J Nat Prod 55:1631-1637
12. Pan Y, Cembella AD, Quilliam MA (1999) Cell cycle and toxin production in the benthic dinoflagellate Prorocentrum lima. Mar Biol 134:541-549
13. Quilliam MA, Hardstaff WR, Ishida N, McLachlan JL, Reeves AR, Ross NW, Windust AJ (1996) In: Yasumoto T, Oshima Y, Fukuyo Y (eds) Harmful and toxic algal blooms. Production of diarrhetic shellfish poisoning (DSP) toxins by Prorocentrum lima in culture and development of analytical methods. IOC/UNESCO, Paris, pp 289-292
14. Morono A, Arevalo F, Fernandez ML, Maneiro J, Pazos Y, Salgado C, Blanco J (2003) Accumulation and transformation of DSP toxins in mussels Mytilus galloprovincialis during a toxic episode caused by Dinophysis acuminata. Aquat Toxicol 62:269-280
15. Suzuki T, Mitsuya T (2001) Comparison of dinophysistoxin-1 and esterified dinophysistoxin-1 (dinophysistoxin-3) contents in the scallop Patinopecten yessoensis and the mussel Mytilus galloprovincialis. Toxicon 39:905-908
16. Vale P, Sampayo MAD (2002) 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 40:989-996
17. Castberg T, Torgersen T, Aasen J, Aune T, Naustvoll LJ (2004) Diarrhoetic shellfish poisoning toxins in Cancer pagurus Linnaeus 1758 (Brachyura, Cancridae) in Norwegian waters. Sarsia 89:311-317
18. Marr JC, Hu T, Pleasance S, Quilliam MA, Wright JLC (1992) Detection of new 7-O-acyl derivatives of diarrhetic shellfish poisoning toxins by liquid chromatography-mass spectrometry. Toxicon 30:1621-1630
19. Vale P, De Sampayo MA (2002) Esterification of DSP toxins by Portuguese bivalves from the northwest coast determined by LC-MS-a widespread phenomenon. Toxicon 40:33-42
20. Suzuki T, Ota H, Yamasaki M (1999) Direct evidence of transformation of dinophysistoxin-1 to 7-O-acyl-dinophysistoxin-1 (dinophysistoxin-3) in the scallop Patinopecten yessoensis. Toxicon 37:187-198
21. Hamano Y, Kinoshita Y, Yasumoto T (1986) Enteropathogenicity of diarrhetic shellfish toxins in intestinal models (studies on diarrhetic shellfish toxins I). J Food Hyg Soc Jpn 27:375-379
22. Yanagi T, Murata M, Torigoe K, Yasumoto T (1989) Biological activities of semisynthetic analogs of dinophysistoxin-3, the major diarrhetic shellfish toxin. Agric Biol Chem 53:525-529
23. Torgersen T, Aasen J, Aune T (2005) Diarrhetic shellfish poisoning by okadaic acid esters from brown crabs (Cancer pagurus) in Norway. Toxicon 46:572-578
24. Hu T, Curtis JM, Walter JA, Wright JLC (1995) Identification of DTX-4, a new water-soluble phosphatase inhibitor from the toxic dinoflagellate Prorocentrum lima. J Chem Soc Chem Commun 597-599
25. Hu T, Curtis JM, Walter JA, McLachlan JL, Wright JLC (1995) Two new water-soluble DSP toxin derivatives from Prorocentrum maculosum: possible storage and excretion products of the dinoflagellate. Tetrahedron Lett 36:9273-9276
26. Suzuki T, Beuzenberg V, Mackenzie L, Quilliam MA (2004) Discovery of okadaic acid esters in the toxic dinoflagellate dinophysis acuta from New Zealand using liquid chromatography tandem mass spectrometry. Rapid Comm Mass Spectrom 18:1131-1138
27. Needham J, Hu T, McLachlan JL, Walter JA, Wright JLC (1995) Biosynthetic studies of the DSP toxin DTX-4 and an okadaic acid diol ester. J Chem Soc Chem Commun 1623-1624
28. Suzuki T, Yoshizawa R, Kawamura T, Yamasaki M (1996) Interference of free fatty acids from the hepatopancreas of mussels with the mouse bioassay for shellfish toxins. Lipids 31:641-645
29. Fernández ML, Miguez A, Cacho E, Martinez A (1996) Detection of okadaic acid esters in the hexane extracts of Spanish mussels. Toxicon 34:381-387
30. Mountfort DO, Suzuki T, Truman P (2001) Protein phosphatase inhibition assay adapted for determination of total DSP in contaminated mussels. Toxicon 39:383-390
31. Gonzalez JC, Leira F, Fontal OI, Vieytes MR, Arevalo FF, Vieites JM, Bermudez Puente M, Muniz S, Salgado C, Yasumoto T, Botana LM (2002) 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 466:233-246
32. Lee JS, Yanagi T, Kenma R, Yasumoto T (1987) Fluorometric determination of diarrhetic shellfish toxins by high-performance liquid chromatography. Agric Biol Chem 51:877-881
33. Quilliam MA (1995) Analysis of diarrhetic shellfish poisoning toxins in shellfish tissue by liquid chromatography with fluorometric and mass spectrometric detection. J AOAC Int 78:555-570
34. Quilliam MA, Hess P, Dell'Aversano C (2001) In: deKoe WJ, Samson RA, van Egmond HP, Gilbert J, Sabino M (eds) Mycotoxins and phycotoxins in perspective at the turn of the century. Recent developments in the analysis of phycotoxins by liquid chromatography-mass spectrometry. WJ deKoe, Wageningen, The Netherlands, pp 383-391
35. Aasen JAB, Hardstaff W, Aune T, Quilliam MA (2006) Discovery of fatty acid ester metabolites of spirolide toxins in mussels from Norway using liquid chromatography/tandem mass spectrometry. Rapid Comm Mass Spectrom 20:1531-1537
36. Wilkins AL, Rehmann N, Torgersen T, Rundberget T, Keogh M, Petersen D, Hess P, Rise F, Miles CO (2006) Identification of fatty acid esters of pectenotoxin-2 seco acid in blue mussels (Mytilus edulis) from Ireland. J Agric Food Chem 54:5672-5678
37. Quilliam MA, Ross NW (1995) Analysis of diarrhetic shellfish poisoning toxins and metabolites in plankton and shellfish by ion-spray liquid chromatography-mass spectrometry. In: Snyder AP (ed) Biochemical and biotechnological applications of electrospray ionization mass spectrometry. American Chemical Society, Washington, DC, pp 351-364
38. Suzuki T, Mackenzie L, Stirling D, Adamson J (2001) Pectenotoxin-2 seco acid: a toxin converted from pectenotoxin-2 by the New Zealand greenshell mussel, Perna canaliculus. Toxicon 39:507-514