Production of 7-epi-pectenotoxin-2 seco acid and assessment of its acute toxicity to mice

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 4, 2006, Pages 1530-1534

  Miles, Christopher O ^a,b   Wilkins, Alistair L ^c   Munday, John S ^d   Munday, Rex ^a   Hawkes, Allan D ^a   Jensen, Dwayne J ^e   Cooney, Janine M ^e   Beuzenberg, Veronica ^f  

^a RUAKURA RESEARCH CENTRE   (New Zealand)

^b NORWEGIAN VETERINARY INSTITUTE   (Norway)

^c UNIVERSITY OF WAIKATO   (New Zealand)

^d MASSEY UNIVERSITY   (New Zealand)

^e THE NEW ZEALAND INSTITUTE FOR PLANT AND FOOD RESEARCH LIMITED   (New Zealand)

^f CAWTHRON INSTITUTE   (New Zealand)

Author keywords

Dinophysis; Mussel; Pectenotoxin; PTX 2 seco acid; Seco acid; Toxicology

Indexed keywords

FURAN DERIVATIVE; PECTENOTOXIN 2 SECO ACID; PECTENOTOXIN-2-SECO ACID; PYRAN DERIVATIVE;

ANIMAL; ARTICLE; BIVALVE; CHEMISTRY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; METABOLISM; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SHELLFISH;

ANIMALS; BIVALVIA; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; FURANS; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; PYRANS; SHELLFISH;

ANIMALIA; DINOPHYCEAE; DINOPHYSIS;

EID: 33644870057     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0523871     Document Type: Article

References (24)

1. James, K. J.; Bishop, A. G.; Draisci, R.; Palleschi, L.; Marchiafava, C.; Ferretti, E.; Satake, M.; Yasumoto, T. Liquid chromatographic methods for the isolation and identification of new pectenotoxin-2 analogues from marine phytoplankton and shellfish. J. Chromatogr. A 1999, 844, 53-65.
2. MacKenzie, L.; Holland, P.; McNabb, P.; Beuzenberg, V.; Selwood, A.; Suzuki, T. Complex toxin profiles in phytoplankton and Greenshell mussels (Perna canaliculus), revealed by LC-MS/MS analysis. Toxicon 2002, 40, 1321-1330.
3. Pavela-Vrancic, M.; 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.
4. Vale, P.; Sampayo, M. A. de M. Pectenotoxin-2 seco acid, 7-epi-pectenotoxin-2 seco acid and pectenotoxin-2 in shellfish and plankton from Portugal. Toxicon 2002, 40, 979-987.
5. Yasamoto, T.; Murata, M.; Lee, J.-S.; Torigoe, K. Polyether toxins produced by dinoflagellates. In Mycotoxins and Phycotoxins '88; Natori, S., Hashimoto, K., Ueno, Y., Eds.; Elsevier: Amsterdam, 1989; pp 375-382.
6. Daiguji, M.; Satake, M.; James, K. J.; Bishop, A.; MacKenzie, L.; Naoki, H.; Yasumoto, T. Structures of new pectenotoxin analogues, pectenotoxin-2 seco acid and 7-epi-pectenotoxin-2 seco acid, isolated from a dinoflagellate and greenshell mussels. Chem. Lett. 1998, 653-654.
7. Draisci, R.; Lucentini, L.; Giannetti, L.; Boria, P.; Poletti, R. First report of pectenotoxin-2 (PTX-2) in algae (Dinophysis fortii) related to seafood poisoning in Europe. Toxicon 1996, 34, 923-935.
8. Lee, J.-S.; 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.
9. Suzuki, T.; Mitsuya, T.; Matsubara, H.; Yamasaki, M. Determination of pectenotoxin-2 after solid-phase extraction from seawater and from the dinoflagellate Dinophysis fortii by liquid chromatography with electrospray mass spectrometry and ultraviolet detection. Evidence of oxidation of pectenotoxin-2 to pectenotoxin-6 in scallops. J. Chromatogr. A 1998, 815, 155-160.
10. Miles, C. O.; Wilkins, A. L.; Samdal, I. A.; Sandvik, M.; Petersen, D.; Quilliam, M. A.; Naustvoll, L. J.; Rundberget, T.; Torgersen, T.; Hovgaard, P.; Jensen, D. J.; Cooney, J. M. A novel pectenotoxin, PTX-12, in Dinophysis spp. and shellfish from Norway. Chem. Res. Toxicol. 2004, 17, 1423-1433.
11. Suzuki, T.; Beuzenberg, V.; Mackenzie, L.; Quilliam, M. A. Liquid chromatography-mass spectrometry of spiroketal stereo-isomers of pectenotoxins and the analysis of novel pectenotoxin isomers in the toxic dinoflagellate Dinophysis acuta from New Zealand. J. Chromatogr. A 2003, 992, 141-150.
12. Suzuki, T.; Beuzenberg, V.; Mackenzie, L.; Walter, J.; LeBlanc, P.; Mackinnon, S.; Miles, C. O.; Wilkins, A. L.; Munday, R.; Jensen, D. J.; Cooney, J. M.; Quilliam, M. A. Identification of pectenotoxin-11 as 34S- hydroxypectenotoxin-2, a new pectenotoxin analogue in the toxic dinoflagellate Dinophysis acuta from New Zealand. Chem. Res. Toxicol., in press.
13. 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.
14. Suzuki, T.; Mackenzie, L.; Stirling, D.; Adamson, J. Pectenotoxin-2 seco acid: A toxin converted from pectenotoxin-2 by the New Zealand Greenshell mussel, Perna canaliculus. Toxicon 2001, 39, 507-514.
15. Suzuki, T.; MacKenzie, L.; Stirling, D.; Adamson, J. Conversion of pectenotoxin-2 to pectenotoxin-2 seco acid in the New Zealand scallop, Pecten novaezelandiae. Fish Sci. 2001, 67, 506-510.
16. Ishige, M.; Satoh, N.; Yasumoto, T. Pathological studies on mice administered with the causative agent of diarrhetic shellfish poisoning (okadaic acid and pectenotoxin-2). Hokkaidoritsu Eisei Kenkyushoho 1988, 15-18.
17. Yasumoto, T.; Murata, M. Marine Toxins. Chem. Rev. 1993, 93, 1897-1909.
18. Terao, K.; Ito, E.; Yanagi, T.; Yasumoto, T. Histopathological studies on experimental marine toxin poisoning. I. Ultrastructural changes in the small intestine and liver of suckling mice induced by dinophysistoxin-1 and pectenotoxin-1. Toxicon 1986, 24, 1141-1151.
19. Burgess, V. A.; Seawright, A.; Eaglesham, G.; Shaw, G.; Moore, M. In The acute oral toxicity of the shellfish toxins pectenotoxin-2 seco acid and 7-epi-pectenotoxin-2 seco acid in mice. Poster presented at the 4th International Conference on Molluscan Shellfish Safety, Santiago de Compostela, Spain, 2002.
20. Burgess, V.; Shaw, G. Investigations into the toxicology of pectenenotoxin-2-seco acid and 7-epi pectenotoxin 2-seco acid to aid in a health risk assessment for the consumption of shellfish contaminated with these shellfish toxins in Australia; Report on Project No. 2001/258; National Research Centre for Environmental Toxicology: Archerfield, Queensland, Australia, 2003.
21. Burgess, V. A. Ph.D. Toxicology investigations with the pectenotoxin-2 seco acids. Thesis, Griffith University, Brisbane, Australia, 2003, p 283. Available at: http://www4.gu.edu.au:8080/adt-root/public/adt-QGU20030905.090222/ (accessed Jan 16, 2006).
22. Miles, C. O.; Wilkins, A. L.; Hawkes, A. D.; Selwood, A.; Jensen, D. J.; Aasen, J.; Munday, R.; Samdal, I. A.; Briggs, L. R.; Beuzenberg, V.; MacKenzie, A. L. Isolation of a 1,3-enone isomer of heptanor-41-oxoyessotoxin from Protoceratium reticulatum cultures. Toxicon 2004, 44, 325-336.
23. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy - High-Resolution Methods and Applications in Organic Chemistry and Biochemistry, 3rd ed.; VCH: Weinheim, Germany, 1990.
24. Report of the Joint FAO/IOC/WHO ad hoc Expert Consultation on Biotoxins in Bivalve Molluscs, Oslo, Norway, Sep 26-30, 2004 (advance prepublication copy); FAO/IOC/WHO: Oslo, Norway, 2005. Available at http://www.fao.org/es/ESN/ food/risk_biotoxin_en.stm (accessed Jan 16, 2006).