Investigations into the toxicology of spirolides, a group of marine phycotoxins

Toxins

Volumn 4, Issue 1, 2012, Pages 1-14

  Munday, Rex ^a   Quilliam, Michael A ^b   LeBlanc, Patricia ^b   Lewis, Nancy ^b   Gallant, Pamela ^b   Sperker, Sandra A ^b   Stephen Ewart, H ^b,c   MacKinnon, Shawna L ^b  

^a RUAKURA RESEARCH CENTRE   (New Zealand)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^c Novaceutics Consulting   (Canada)

Author keywords

Acute toxicity; Alexandrium ostenfeldii; Marine phycotoxin; Seafood poisoning; Spirolides

Indexed keywords

13 DESMETHYL SPIROLIDE C; 20 METHYL SPIROLIDE G; MARINE TOXIN; SPIROLIDE; SPIROLIDE A; SPIROLIDE B; SPIROLIDE C; UNCLASSIFIED DRUG;

ACUTE TOXICITY; ALEXANDRIUM OSTENFELDII; ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CELL DIFFERENTIATION; CELL VIABILITY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYTOTOXICITY TEST; DINOFLAGELLATE; FEMALE; IN VITRO STUDY; INTRACELLULAR SIGNALING; LD 50; MAMMAL CELL; MOUSE; NONHUMAN; TOXIN ANALYSIS;

ANIMALS; CELL LINE; FEMALE; HUMANS; LETHAL DOSE 50; MARINE TOXINS; MICE; RISK ASSESSMENT; SPIRO COMPOUNDS;

ALEXANDRIUM OSTENFELDII; DINOPHYCEAE; MAMMALIA; MUS;

EID: 84856240092     PISSN: None     EISSN: 20726651     Source Type: Journal    
DOI: 10.3390/toxins4010001     Document Type: Article

References (32)

1. 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.
2. Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S.; Chen, H. Pinnatoxin A: A toxic amphoteric macrocycle from the Okinawan bivalve Pinna muricata. J. Am. Chem. Soc. 1995, 117, 1155-1156.
3. Takada, N.; Umemura, N.; Suenaga, K.; Chou, T.; Nagatsu, S.; Haino, T.; Yamada, K.; Uemura, D. Pinnatoxins B and C, the most toxic components in the pinnatoxins series from the Okinawan bivalve Pinna muricata. Tetrahedron Lett. 2001, 42, 3491-3494.
4. Lu, C.-K.; Lee, G.-H.; Huang, R.; Chou, H.-N. Spiro-prorocentrimine, a novel macrocyclic lactone from a benthic Prorocentrum sp. of Taiwan. Tetrahedron Lett. 2000, 42, 1713-1716.
5. Seki, T.; Satake, M.; MacKenzie, L.; Kasper, H.F.; Yasumoto, T. Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate, Gymnodinium sp. Tetrahedron Lett. 1995, 36, 7093-7096.
6. Cembella, A.D.; Lewis, N.I.; Quilliam, M.A. Spirolide composition in micro-extracted pooled cells isolated from natural plankton assemblages and from cultures of the dinoflagellate Alexandrium ostenfeldii. Nat. Toxins 1999, 7, 197-206.
7. Cembella, A.D.; Lewis, N.I.; Quilliam, M.A. The marine dinoflagellate Alexandrium ostenfeldii (Dinophyceae) as the causative organism of spirolide shellfish toxins. Phycologica 2000, 39, 67-74.
8. Hansen, P.J.; Cembella, A.D.; Moestrup, O. The marine dinoflagellate Alexandrium ostenfeldii: Paralytic shellfish toxin concentration, composition, and toxicity to a tintinnid ciliate. J. Phycol. 1992, 28, 597-603.
9. Hu, T.; Curtis, J.M.; Walter, J.A.; Wright, J.L.C. Characterization of biologically inactive spirolides E and F: Identification of the spirolide pharmacophore. Tetrahedron Lett. 1996, 37, 7671-7674.
10. Richard, D.; Arsenault, E.; Cembella, A.; Quilliam, M. Investigations into the Toxicology and Pharmacology of Spirolides, a Novel Group of Shellfish Toxins. In Proceedings of the 9th International Conference on Harmful Microalgae, Hobart, Australia, 6-11 February 2001; Hallegraeff, G.M., Blackburn, S.I., Bolch, C.J., Lewis, R.J., Eds.; pp. 383-386.
11. Bourne, Y.; Radic, Z.; Araoz, R.; Talley, T.T.; Benoit, E.; Servent, D.; Taylor, P.; Molgo, J.; Marchot, P. Structural determinants in phycotoxins and AChBP conferring high affinity binding and nicotinic AChR antagonism. Proc. Natl. Acad. Sci. USA 2010, 107, 6076-6081.
12. Wandscheer, C.B.; Vilarino, N.; Espina, B.; Louzao, M.C.; Botana, L.M. Human muscarinic acetylcholine receptors are a target of the marine toxin 13-desmethyl C spirolide. Chem. Res. Toxicol. 2010, 23, 1753-1761.
13. Fritz, L.; Triemer, R.E. Preliminary Studies of Cell Wall Formation in Temporary Cysts of Gonyaulax tamarensis. In Toxic Dinoflagellates; Anderson, D.M., White, A.W., Baden, D.G., Eds.; Elsevier-North Holland: New York, NY, USA, 1985; pp. 117-120.
14. Hu, T.; Burton, I.W.; Cembella, A.D.; Curtis, J.M.; Quilliam, M.A.; Walter, J.A.; Wright, J.L.C. Characterization of spirolides A, C and 13-desmethyl C, New marine toxins isolated from toxic plankton and contaminated shellfish. J. Nat. Prod. 2001, 64, 308-312.
15. Aasen, J.; MacKinnon, S.L.; LeBlanc, P.; Walter, W.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.
16. Roach, J.S.; LeBlanc, P.; Lewis, N.I.; Munday, R.; Quilliam, M.A.; MacKinnon, S.L. Characterization of a dispiroketal spirolide subclass from Alexandrium ostenfeldii. J. Nat. Prod. 2009, 72, 1237-1240.
17. OECD. OECD guideline for testing of chemicals 425. Acute oral toxicity-up and down procedure, Organisation for Economic Co-operation and Development, Paris, 2001. Available online: http://www.epa.gov/oppfead1/harmonization/docs/E425guideline.pdf (accessed on 29 December 2011).
18. EPA User documentation for the AOT425StatPgm program prepared for the US Environmental Protection Agency by Westat, May 2001; updated by USEPA September 2002. Available online: http://www.oecd.org/dataoecd/19/57/1839830.pdf (accessed on 29 December 2011).
19. Munday, R.; Towers, N.R.; Mackenzie, L.; Beuzenberg, V.; Holland, P.T.; Miles, C.O. Acute toxicity of gymnodimine to mice. Toxicon 2004, 44, 173-178.
20. Aune, T.; Sørby, R.; Yasumoto, T.; Ramstad, H.; Landsverk, T. Comparison of oral and intraperitoneal toxicity of yessotoxin towards mice. Toxicon 2002, 40, 77-82.
21. Harada, T.; Oshima, Y.; Yasumoto, T. Assessment of potential activation of gonyautoxin V in the stomach of mice and rats. Toxicon 1984, 22, 476-478.
22. Munday, R. Toxicological requirements for risk assessment of shellfish contaminants: A review. Afr. J. Mar. Sci. 2006, 28, 447-449.
23. Dashiell, O.L.; Kennedy, G.L. The effects of fasting on the acute oral toxicity of nine chemicals in the rat. J. Appl. Toxicol. 1984, 4, 320-325.
24. Kast, A.; Nishikawa, J. The effect of fasting on oral acute toxicity of drugs in rats and mice. Lab. Anim. 1981, 15, 359-364.
25. Massey, R.M.; McElligott, T.E.; Racz, W.J. Acetaminophen toxicity in fed and fasted mice. Can. J. Physiol. Pharmacol. 1982, 60, 399-404.
26. Strubelt, O.; Dost-Kempf, E.; Siegers, C.-P.; Younes, M.; Völpel, M.; Preuss, U.; Dreckmann, J.G. The influence of fasting on the susceptibility of mice to hepatotoxic injury. Toxicol. Appl. Pharmacol. 1981, 60, 66-77.
27. Chavanet, P.; Joly, V.; Rigaud, D.; Bolard, J.; Carbon, C.; Yeni, P. Influence of diet on experimental toxicity of amphotericin B deoxycholate. Antimicrob. Agents Chemother. 1994, 38, 963-968.
28. Price, V.F.; Miller, M.G.; Jollow, D.J. Mechanisms of fasting-induced potentiation of acetaminophen hepatotoxicity in the rat. Biochem. Pharmacol. 1987, 36, 427-433.
29. Mantle, P.G. Risk assessment and the importance of ochratoxins. Int. Biodeterior. Biodegrad. 2002, 50, 143-146.
30. Munday, R. Toxicology of Cyclic Imines: Gymnodimine, Spirolides, Pinnatoxins, Pteriatoxins, Prorocentrolide, Spiro-Procentrimine and Symbioimines. In Seafood and Freshwater Toxins, Pharmacology, Physiology and Detection, 2nd ed.; Botana, L.M., Ed.; Taylor & Francis Ltd.: New York, NY, USA, 2008; pp. 581-594.
31. Otero, P.; Alfonso, A.; Rodriguez, P.; Rubiolo, J.A.; Cifuentes, J.M.; Bermudez, R.; Vieytes, M.R.; Botana, L.M. Pharmacokinetic and toxicological data of spirolides after oral and intraperitoneal administration. Food Chem. Toxicol. 2011, doi:10.1016/j.fct.2011.10.062, in press.
32. Munday, R.; Aune, T.; Rossini, G.P. Toxicology of the Yessotoxins. In Seafood and Freshwater Toxins, Pharmacology, Physiology and Detection, 2nd ed.; Botana, L.M., Ed.; Taylor & Francis Ltd.: New York, NY, USA, 2008; pp. 329-339.