New esters of okadaic acid in seawater and blue mussels (Mytilus edulis)

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 20, 2008, Pages 9628-9635

  Torgersen, Trine ^a   Miles, Christopher O ^a,b   Rundberger, Thomas ^a   Wilkins, Alistair L ^a,c  

^a NORWEGIAN VETERINARY INSTITUTE   (Norway)

^b RUAKURA RESEARCH CENTRE   (New Zealand)

^c UNIVERSITY OF WAIKATO   (New Zealand)

Author keywords

Algal toxin; Blue mussel; Dinophysis; Diol ester; DSP; Fatty acid esters; Hybrid ester; Mytilus edulis; Okadaic acid

Indexed keywords

ESTER; OKADAIC ACID; SEA WATER;

ALGA; ANIMAL; ARTICLE; BIVALVE; CHEMISTRY; METABOLISM;

ALGAE; ANIMALS; BIVALVIA; ESTERS; OKADAIC ACID; SEAWATER;

ALGAE; DINOPHYSIS; MYTILUS EDULIS;

EID: 55549105106     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8016749     Document Type: Article

References (29)

1. Lee, J.; Igarashi, T.; Fraga, S.; Dahl, E.; Hovgaard, P.; Yasumoto, T. Determination of diarrhetic shellfish toxins in various dinoflagellate species. J. Appl. Phycol. 1989, 1, 147-152.
2. Yasumoto, T.; Oshima, Y.; Sugawara, W.; Fukuyo, Y.; Oguri, H.; Igarashi, T.; Fujita, N. Identification of Dinophysis fortii as the causative organism of diarrhetic shellfish poisoning. Bull. Jpn. Soc. Sci. Fish. 1980, 46, 1405-1411.
3. Tachibana, K.; Scheuer, P. J.; Tsukitani, Y.; Kikuchi, H.; Van Engen, D.; Clardy, J.; Gopichand, Y.; Schmitz, F. J. Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria. J. Am. Chem. Soc. 1981, 103, 2469-2471.
4. Larsen, K.; Petersen, D.; Wilkins, A. L.; Samdal, I. A.; Sandvik, M.; Rundberget, T.; Goldstone, 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.
5. Murata, M.; Shimatani, M.; Sugitani, H.; Oshima, Y.; Yasumoto, T. Isolation and structure elucidation of the causative toxin of diarrhetic shellfish poisoning. Bull. Jpn. Soc. Sci. Fish. 1982, 43, 549-552.
6. Hu, T.; Doyle, J.; Jackson, D.; Marr, J. C.; Nixon, E.; Pleasance, S.; Quilliam, M. A.; Walter, J. A.; Wright, J. L. C. Isolation of a new diarrhetic shellfish poison from Irish mussles. J. Chem. Soc., Chem. Commun. 1992, 39-41.
7. Takai, A.; Murata, M.; Torigoe, K.; Isobe, M.; Mieskes, G.; Yasumoto, T. Inhibitory effect of okadaic acid derivatives on protein phosphatases. A study on structure-affinity relationship. Biochem. J. 1992, 284, 539-544.
8. Suganuma, M.; Fujiki, H.; Suguri, H.; Yoshizawa, S.; Hirota, M.; Nakayasu, M.; Ojika, M.; Wakamatsu, K.; Yamada, K.; Sugimura, T. Okadaic acid: an additional non-phorbol-12-tetradecanoate-13-acetate-type tumor promoter. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 1767-1771.
9. Fernández, 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.
10. Hu, T.; Marr, J. C.; deFreitas, A. S. W.; Quilliam, M. A.; Walter, J. A.; Wright, J. L. C. New diol esters isolated from cultures of the dinoflagellates Prorocentrum lima and Prorocentrum concavum. J. Nat. Prod. 1992, 55, 1631-1637.
11. 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 1994, 50, 9175-9180.
12. Suárez-Gómez, B.; Souto, M. L.; Cruz, P. G.; Fernández, J. J.; Norte, M. New targets in diarrhetic shellfish poisoning control. J. Nat. Prod. 2005, 68, 596-599.
13. Yasumoto, T.; Murata, M.; Lee, J.; Torigoe, K. Polyether toxins produced by dinoflagellates. In Mycotoxins and Phycotoxins '88; Natori, S., Hashimoto, K., Ueno, Y., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1989; pp 375-382.
14. 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.; 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.
15. Miles, C. O.; Wilkins, A. L.; Hawkes, A. D.; Jensen, D. J.; Cooney, J. M.; Larsen, K.; Petersen, D.; Rise, F.; Beuzenberg, V.; MacKenzie, A. L. Isolation and identification of a cis-C8-diol-ester of okadaic acid from Dinophysis acuta in New Zealand. Toxicon 2006, 48, 195-203.
16. 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.
17. 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.
18. 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.
19. Vale, P.; Sampayo, M. A. deM esters of okadaic acid and dinophysistoxin-2 in Portuguese bivalves related to human poisonings. Toxicon 1999, 37, 1109-1121.
20. Yasumoto, T.; Murata, M.; Oshima, Y.; Sano, M. Diarrhetic shellfish toxins. Tetrahedron 1985, 41, 1019-1025.
21. Torgersen, T.; Wilkins, A. L.; Rundberget, T.; Miles, C. O. Characterization of fatty acid esters of okadaic acid and related toxins in blue mussels (Mytilus edulis) from Norway. Rapid Commun. Mass Spectrom. 2008, 22, 1127-1136.
22. Vale, P. Detailed profiles of 7-O-acyl esters in plankton and shellfish from the Portuguese coast. J. Chromatogr., A 2006, 1128, 181-188.
23. Rundberget, T.; Sandvik, M.; Larsen, K.; Pizzaro, G. M.; Reguera, B.; Castberg, T.; Gaustad, E.; Loader, J. I.; Rise, F.; Wilkins, A. L.; Miles, C. O. Extraction of microlagal toxins by large-scale pumping of seawater in Spain and Norway, and isolation of okadaic acid and dinophysistoxin-2. Toxicon 2007, 50, 960-970.
24. Doucet, E.; Ross, N. N.; Quilliam, M. A. Enzymatic hydrolysis of esterified diarrhetic shellfish poisoning toxins and pectenotoxins. Anal. Bioanal. Chem. 2007, 389, 549-558.
25. 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.
26. King, I.; Childs, M. T.; Dorsett, C.; Ostrander, J. G.; Monsen, E. R. Shellfish: proximate composition, minerals, fatty acids and sterols. J. Am. Diet. Assoc. 1990, 90, 677-685.
27. 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.
28. Yanagi, T.; Murata, M.; Torigoe, K.; Yasumoto, T. Biological activities of semisynthetic analogs of dinophysistoxin-3, the major diarrhetic shellfish toxin. Agric. Biol. Chem. 1989, 53, 525-529.
29. Holmes, C. F. B.; Luu, H. A.; Carrier, F.; Schmitz, F. J. Inhibition of protein phosphatases-1 and -2A with acanthifolicin: comparison with diarrhetic shellfish toxins and identification of a region on okadaic acid important for inhibition. FEBS Lett. 1990, 270, 216-218.