Cyclic imine toxins: Chemistry, biogeography, biosynthesis, and pharmacology

Seafood and Freshwater Toxins: Pharmacology, Physiology, and Detection, Second Edition

Volumn , Issue , 2008, Pages 561-580

  Cembella, Allan ^a   Krock, Bernd ^a  

^a ALFRED WEGENER INSTITUTE FOR POLAR AND MARINE RESEARCH   (Germany)

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EID: 76349096541     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (50)

1. Seki, T. et al. Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate, Gymnodinium sp, Tetrahedron Lett. 36(39), 7093-7096, 1995.
2. Uemura, D. et al. Pinnatoxin A: A toxic amphoteric macrocycle from the Okinawan bivalve Pinna muricata, J. Am. Chem. Soc. 117(3), 1155-1156, 1995.
3. Torigoe, K. et al. Prorocentrolide, a toxic nitrogenous macrocycle from a marine dinoflagellate, Prorocentrum lima, J. Am. Chem. Soc. 110(23), 7876-7877, 1988.
4. Hu, T. et al. Isolation and structure of prorocentrolide B, a fast-acting toxin from Prorocentrum macu-losum, J. Nat. Prod. 59(11), 1010-1014, 1996.
5. Takada, N. et al. Structural determination of pteriatoxins A, B and C, extremely potent toxins from the bivalve Pteria penguin, Tetrahedron Lett. 42(20), 3495-3497, 2001.
6. Hu, T. et al. Spirolides B and D, two novel macrocycles isolated from the digestive glands of shellfish, J. Chem. Soc. Chem. Commun. 2159-2161, 1995.
7. Lu, C.-K. et al. Spiro-prorocentrimine, a novel macrocyclic lactone from a benthic Prorocentrum spp. of Taiwan, Tetrahedron Lett. 42(9), 1713-1716, 2001.
8. Chou, T. et al. Isolation and structure of pinnatoxin D, a new shellfish poison from the Okinawan bivalve Pinna muricata, Tetrahedron Lett. 37(23), 4027-4030, 1996.
9. Takada, N. et al. Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata, Tetrahedron Lett. 42(20), 3491-3494, 2001.
10. Zheng, S.Z. et al. The isolation and bioactivities of pinnatoxin, Chin. J. Mar. Drugs. 33, 33-35, 1990.
11. MacPherson, G.R. et al. Studies of the biosynthesis of DTX-5a and DTX-5b by the dinoflagellate Prorocentrum maculosum: Regiospecificity of the putative Baeyer-Villigerase and insertion of a single amino acid in a polyketide chain, J. Org. Chem. 68(5), 1659-1664, 2003.
12. MacKinnon, S.L. et al. Biosynthesis of 13-desmethyl spirolide C by the dinoflagellate Alexandrium ostenfeldii, J. Org. Chem. 71(23), 8724-8731, 2006.
13. Mackenzie, L. et al. A Gymnodinium spp. bloom and the contamination of shellfish with lipid soluble toxins in New Zealand, January-April 1993, in Harmful Marine Algal Blooms, Lassus, P. Arzul, G. Erard, E. Gentien, P. and Marcaillou, C. eds. Lavoisier, Intercept Ltd. Nantes, France, 1993, pp. 795-800.
14. Miles, C.O. et al. Gymnodimine C, an isomer of gymnodimine B, from Karenia selliformis, J. Agric. Fd. Chem. 51(16), 4838-4840, 2003.
15. MacKenzie, L.A. et al. Gymnodimine contamination of shellfish in New Zealand, in Harmful and Toxic Algal Blooms, 7th International Conference on Toxic Phytoplankton, Yasumoto, T. Oshima, Y. and Fukuyo, Y. eds. IOC, UNESCO, Sendai, Japan, 1995, pp. 97-100.
16. Faust, M.A. Alternate asexual reproduction of Prorocentrum lima in culture, in Toxic Phytoplankton Blooms in the Sea, Smayda, T.J. and Shimizu, Y. eds. Elsevier, New York, 1993, pp. 115-119.
17. Gribble, K.E. et al. Distribution and toxicity of Alexandrium ostenfeldii (Dinophyceae) in the Gulf of Maine, USA, Deep Sea Res. Pt. II 52(19-21), 2745-2763, 2005.
18. Aasen, J.A.B. et al. Detection and identification of spirolides in Norwegian shellfish and plankton, Chem. Res. Toxicol. 18(3), 509-515, 2005.
19. Graham, J. et al. Identification and assessment of the toxicity burden of natural phytoplankton populations, in 6th International Conference of Molluscan Shellfish Safety, Blenheim, New Zealand, 2007.
20. Mallat, E. et al. First approach towards the implementation of passive sampling adsorption devices for the identification of lipophilic toxins in the shellfish monitoring program in the coastal embay-ments of the Ebro Delta, in 6th International Conference on Molluscan Shellfish Safety, Blenheim, New Zealand, 2007.
21. MacKenzie, L. et al. The resting cyst and toxicity of Alexandrium ostenfeldii (Dinophyceae) in New Zealand, Phycologia 35(2), 148-155, 1996.
22. Selwood, A. et al. Occurence of spirolides in New Zealand, in 6th International Conference on Molluscan Shellfish Safety, Blenheim, New Zealand, 2007.
23. Cembella, A.D. et al. Identifying the planktonic origin and distribution of spirolides in coastal Nora Scotian waters, in Harmful Algae, Reguera, B. Blanio, J. Fernandez, M.L. and Wyatt, T. eds. Xunta de Galicia and IOC/UNESCO, Santiago de Compostela, 1988, pp. 481-484.
24. Cembella, A.D. Lewis, N.I. and Quilliam, M.A. The marine dinoflagellate Alexandrium ostenfeldii (Dinophyceae) as the causative organism of spirolide shellfish toxins, Phycologia 39(1), 67-74, 2000.
25. Seki, T. et al. Gymnodimine, a novel toxic imine isolated from the Foveaux Strait oysters and Gymnodinium spp. in Harmful and Toxic Algal Blooms, 7th International Conference on Toxic Phytoplankton, Yasumoto, T. Oshima, Y. and Fukuyo, Y. eds. IOC, UNESCO, Sendai, Japan, 1995, pp. 495-498.
26. Miles, C.O. et al. New analogue of gymnodimine from a Gymnodinium species, J. Agric. Fd. Chem. 48(4), 1373-1376, 2000.
27. MacKinnon, S.L. et al. Spirolides isolated from Danish strains of the toxigenic dinoflagellate Alexandrium ostenfeldii, J. Nat. Prod. 69(7), 983-987, 2006.
28. Sleno, L. Windust, A.J. and Volmer, D.A. Structural study of spirolide marine toxins by mass spectrometry. Part I: Fragmentation pathways of 13-desmethyl spirolide C by collision-induced dissociation and infrared multiphon dissociation mass spectrometry, Anal. Bioanal. Chem. 378(4), 969-976, 2004.
29. Sleno, L. Chalmers, M.J. and Volmer, D.A. Structural study of spirolide marine toxins by mass spectrometry. Part II: Mass spectrometric characterization of unknown spirolides and related compounds in a cultured phytoplankton extract, Anal. Bioanal. Chem. 378(4), 977-986, 2004.
30. Ciminiello, P. et al. Toxin profile of Alexandrium ostenfeldii (Dinophyceae) from the Northern Adriatic Sea revealed by liquid chromatography-mass spectrometry, Toxicon 47(5), 597-604, 2006.
31. Hu, T. et al. Characterization of biologically inactive spirolides E and F: Identification of the spirolide pharmacophore, Tetrahedron Lett. 37(43), 7671-7674, 1996.
32. Cembella, A.D. et al. Association of the gonyaulacoid dinoflagellate Alexandrium ostenfeldii with spirolide toxins in size-fractionated plankton, J. Plankton Res. 23(12), 1413-1419, 2001.
33. Cembella, A.D. Lewis, N.I. and Quilliam, M.A. Spirolide composition of micro-extracted pooled cells isolated from natural plankton assemblages and from cultures of the dinoflagellate Alexandrium ostenfeldii, Nat. Toxins 7(5), 197-206, 1999.
34. Cembella, A.D. and Krock, B. Biogeography of spirolides in Alexandrium ostenfeldii from the North Atlantic—implications for shellfish toxicity and seafood safety, in 6th International Conference on Molluscan Shellfish Safety Blenheim, New Zealand, 2007.
35. Pigozzi, S. et al. First evidence of spirolide accumulation in Northwestern Adriatic Shellfish, in 9th International Conference on Harmful Algal Blooms, Copenhagen, Denmark, 2006.
36. Ruhl, A. et al. Determination of new algal neurotoxins (spirolides) near the Scottish east coast, in International Council for the Exploration of the Sea, Copenhagen Denmark, 2001.
37. Aasen, J.A.B. et al. Discovery of fatty acid ester metabolites of spirolide toxins in mussels from Norway using liquid chromatography/tandem mass spectrometry, Rapid Commun. Mass Spectrom. 20(10), 1531-1537, 2006.
38. Villar Gonzalez, A. et al. First evidence of spirolides in Spanish shellfish, Toxicon 48(8), 1068-1074, 2006.
39. Vershinin, A. et al. Phytoplankton composition of the Kandalaksha Gulf, Russian White Sea: Dinophysis and lipophilic toxins in the blue mussel (Mytilus edulis), Harmful Algae 5(5), 558-564, 2006.
40. Shimizu, Y. Chemistry and mechanism of action, in Seafood and Freshwater Toxins: Pharmacology, Physiology and Detection, Botana, L.M. ed. Marcel Dekker, New York, 2000, pp. 151-172.
41. Needham, J. et al. Biosynthetic studies of the DSP toxin DTX-4 and an okadaic acid diol ester. J. Chem. Soc. Chem. Comm. 1623-1624, 1995.
42. Kuramoto, M. Arimoto, H. and Uemura, D. Bioactive alkaloids from the sea: A review, Marine Drugs 2(1), 39-54, 2004.
43. Jaeckisch, N. et al. Genomic characterization of the spirolide-producing dinoflagellate Alexandrium ostenfeldii with special emphasis on PKS genes, in 12th International Conference on Harmful Algae, Copenhagen, Denmark, 2007.
44. John, U. et al. Novel insights into the evolution of polyketide synthases through phylogenomic analyses, Protist 2007, (in press).
45. Munday, R. et al. Acute toxicity of gymnodimine to mice, Toxicon 44(2), 173-178, 2004.
46. Stewart, M. et al. The absolute stereochemistry of the New Zealand shellfish toxin gymnodimine, Tetrahedron Lett. 38, 4889-4890, 1997.
47. Richard, D. et al. Investigations into the toxicology and pharmacology of spirolides, a novel group of shellfish toxins, in Harmful Algal Blooms 2000, Hallegraeff, G.M. Blackburn, S.I. Bolch, C.J.S. and Lewis, R.J. eds. IOC, UNESCO, Paris, 2001, pp. 383-386.
48. Gill, S. et al. Neural injury biomarkers of novel shellfish toxins. Spirolides: A pilot study using immunochemical and transcriptional analysis, Neurotoxicology 24(4-5), 593-604, 2003.
49. Pulido, O. et al. Toxicological neuropathy from domoic acid to spirolides—the Health Canada experience, Can. Tech. Rep. Fish. Aquat. Sci. 2386, 36-44, 2001.
50. Kantu, C.M. Pharmacological Studies on Bioactive Substances from Alexandrium ostenfeldii, MSc thesis, University of Bremen, 2006.