Cyclic imines: Chemistry and mechanism of action: A review

Chemical Research in Toxicology

Volumn 24, Issue 11, 2011, Pages 1817-1829

  Otero, Alberto ^a   Chapela, María José ^a   Atanassova, Miroslava ^a   Vieites, Juan M ^a   Cabado, Ana G ^a  

^a ANFACO CECOPESCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GYMNODIMINE; GYMNODIMINE A; GYMNODIMINE B; IMINE; MARINE TOXIN; PINNATOXIN; PINNATOXIN A; PINNATOXIN B; PINNATOXIN C; PINNATOXIN D; PINNATOXIN E; PINNATOXIN F; PROROCENTROLIDE; PTERIATOXIN; PTERIATOXIN A; PTERIATOXIN B; SPIRIPROROCENTRIMINE; SPIROLIDE; UNCLASSIFIED DRUG;

ACUTE TOXICITY; BIOASSAY; CALCIUM SIGNALING; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; DINOFLAGELLATE; ENANTIOSELECTIVITY; HIPPOCAMPUS; HUMAN; INTERNALIZATION; KARENIA SELLIFORMIS; MINIATURE ENDPLATE POTENTIAL; MUSCLE TWITCH; MUSSEL; NEUROMUSCULAR BLOCKING; NEUROMUSCULAR TRANSMISSION; NEUROTOXICITY; NONHUMAN; OYSTER; PARALYSIS; PHARMACOPHORE; POSTSYNAPTIC MEMBRANE; REVIEW; SCALLOP; STEREOCHEMISTRY; TOXIN ANALYSIS; TOXIN STRUCTURE; TOXIN SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; BINDING SITES; BIOLOGICAL ASSAY; CELL SURVIVAL; FOOD CONTAMINATION; HETEROCYCLIC COMPOUNDS, 3-RING; HUMANS; HYDROCARBONS, CYCLIC; IMINES; INJECTIONS, INTRAPERITONEAL; MARINE TOXINS; MICE; MICROALGAE; MUSCARINIC ANTAGONISTS; NICOTINIC ANTAGONISTS; PROTEIN BINDING; PYRANS; RECEPTORS, MUSCARINIC; RECEPTORS, NICOTINIC; SHELLFISH; SHELLFISH POISONING; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

MUS; RODENTIA;

EID: 81755182702     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200182m     Document Type: Review

References (62)

1. Krock, B., Tillmann, U., John, U., and Cembella, A. (2008) LC-MS-MS aboard ship: tandem mass spectrometry in the search for phycotoxins and novel toxigenic plankton from the North Sea Anal. Bioanal. Chem. 392, 797-803
2. EFSA (2010) EFSA report on data collection: future directions. EFSA J. 1533, 1-53.
3. Tindall, D. R., Dickey, R. W., Carlson, R. D., and Moreygaines, G. (1984) Ciguatoxigenic dinoflagellates from the Caribbean sea ACS Symp. Ser. 262, 225-240
4. Ciminiello, P., DellAversano, C., Fattorusso, E., Forino, M., Tartaglione, L., Boschetti, L., Rubini, S., Cangini, M., Pigozzi, S., and Poletti, R. (2010) Complex toxin profile of Mytilus galloprovincialis from the Adriatic sea revealed by LC-MS Toxicon 55, 280-288
5. Munday, R., Holland, P. T., McNabb, P., Selwood, A. I., and Rhodes, L. L. (2008) Comparative toxicity to mice of domoic acid and isodomoic acids A, B and C Toxicon 52, 954-956
6. Richard, D., Arsenaulf, E., Cembella, A., and Quilliam, M. (2001) Investigations into the Toxicology and Pharmacology of Spirolides, a Novel Group of Shellfish Toxins, in Harmful Algal Blooms 2000: Proceedings of the Ninth International Conference on Harmful Algal Blooms (Hallegraeff, G. M., Blackburn, S. I., Bolch, C. J., and Lewis, R. J., Eds.) pp 383-390, Intergovernmental Oceanographic Commission of UNESCO, Paris, France.
7. Molgo, J. (2008) Multiple events triggered by the use of botulinum neurotoxins at the vertebrate neuromuscular junction Toxicon 51, 45
8. Kharrat, R., Servent, D., Girard, E., Ouanounou, G., Amar, M., Marrouchi, R., Benoit, E., and Molgó, J. (2008) The marine phycotoxin gymnodimine targets muscular and neuronal nicotinic acetylcholine receptor subtypes with high affinity J. Neurochem. 107, 952-963
9. Miles, C. O., Rundberget, T., Sandvik, M., Aasen, J., and Selwood, A. (2010) The presence of pinnatoxins in Norwegian mussels Natl. Vet. Inst. Rep. Ser. 07b, 1-9
10. Yang, J., Cohn, S. T., and Romo, D. (2000) Studies toward (-)-gymnodimine: Concise routes to the spirocyclic and tetrahydrofuran moieties Org. Lett. 2, 763-766
11. Seki, T., Satake, M., Mackenzie, L., Kaspar, H. F., and Yasumoto, T. (1995) Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate, Gymnodinium sp Tetrahedron Lett. 36, 7093-7096
12. Stewart, M., Blunt, J. W., Munro, M. H., Robinson, W. T., and Hannah, D. J. (1997) The absolute stereochemistry of the New Zealand shellfish toxin gymnodimine Tetrahedron Lett. 38, 4889-4890 (Pubitemid 27277989)
13. Bire, R., Krys, S., Fremy, J. M., Dragacci, S., Stirling, D., and Kharrat, R. (2002) First evidence on occurrence of gymnodimine in clams from Tunisia J. Nat. Toxins 11, 269-275 (Pubitemid 36029231)
14. Miles, C. O., Wilkins, A. L., Stirling, D. J., and MacKenzie, A. L. (2000) New analogue of gymnodimine from a Gymnodinium species J. Agric. Food Chem. 48, 1373-1376 (Pubitemid 30243713)
15. Miles, C. O., Wilkins, A. L., Stirling, D. J., and MacKenzie, A. L. (2003) Gymnodimine C, an isomer of gymnodimine B, from Karenia selliformis J. Agric. Food Chem. 51, 4838-4840
16. Marrouchi, R., Dziri, F., Belayouni, N., Hamza, A., Benoit, E., Molgo, J., and Kharrat, R. (2009) Quantitative determination of gymnodimine-A by high performance liquid chromatography in contaminated clams from Tunisia coastline Marine Biotechnol. 12, 579-585
17. Mountfort, D., Beuzenberg, V., MacKenzie, L., and Rhodes, L. (2006) Enhancement of growth and gymnodimine production by the marine dinoflagellate, Karenia selliformis Harmful Algae 5, 658-664 (Pubitemid 44666554)
18. Dragunow, M., Trzoss, M., Brimble, M. A., Cameron, R., Beuzenberg, V., Holland, P., and Mountfort, D. (2005) Investigations into the cellular actions of the shellfish toxin gymnodimine and analogues Environ. Toxicol. Pharmacol. 20, 305-312 (Pubitemid 41058785)
19. White, J. D., Quaranta, L., and Wang, G. Q. (2007) Studies on the synthesis of (-)-gymnodimine. Subunit synthesis and coupling J. Org. Chem. 72, 1717-1728 (Pubitemid 46355470)
20. Kong, K., Romo, D., and Lee, C. (2009) Enantioselective total synthesis (-)-gymnodimine employing a of the marine toxin barbier-type macrocyclization Angew. Chem., Int. Ed. 48, 7402-7405
21. Ciminiello, P., DellAversano, C., Fattorusso, E., Magno, S., Tartaglione, L., Cangini, M., Pompei, M., Guerrini, F., Boni, L., and Pistocchi, R. (2006) Toxin profile of Alexandrium ostenfeldii (Dinophyceae) from the Northern Adriatic Sea revealed by liquid chromatography-mass spectrometry Toxicon 47, 597-604
22. Ciminiello, P., DellAversano, C., Dello Iacovo, E., Fattorusso, E., Forino, M., Grauso, L., Tartaglione, L., Guerrini, F., Pezzolesi, L., and Pistocchi, R. (2010) Characterization of 27-hydroxy-13-desmethyl spirolide C and 27-oxo-13,19-didesmethyl spirolide C. Further insights into the complex Adriatic Alexandrium ostenfeldii toxin profile Toxicon 56, 1327-1333
23. González, A. V., Rodríguez-Velasco, M. L., Ben-Gigirey, B., and Botana, L. M. (2006) First evidence of spirolides in Spanish shellfish Toxicon 48, 1068-1074 (Pubitemid 44737890)
24. Amzil, Z., Sibat, M., Royer, F., Masson, N., and Abadie, E. (2007) Report on the first detection of pectenotoxin-2, spirolide-A and their derivatives in French shellfish Marine Drugs 5, 168-179
25. Touzet, N., Franco, J. M., and Raine, R. (2008) Morphogenetic diversity and biotoxin composition of Alexandrium (Dinophyceae) in Irish coastal waters Harmful Algae 7, 782-797
26. Alvarez, G., Uribe, E., Avalos, P., Marino, C., and Blanco, J. (2010) First identification of azaspiracid and spirolides in Mesodesma donacium and Mulinia edulis from Northern Chile Toxicon 55, 638-641
27. Gueret, S. M. and Brimble, M. A. (2010) Spiroimine shellfish poisoning (SSP) and the spirolide family of shellfish toxins: isolation, structure, biological activity and synthesis Nat. Prod. Rep. 27, 1350-1366
28. Hu, T. M., Curtis, J. M., Oshima, Y., Quilliam, M. A., Walter, J. A., Watsonwright, W. M., and Wright, J. L. C. (1995) Spirolide-B and spirolide-D, 2 novel macrocycles isolated from the digestive glands of shellfish J. Chem. Soc., Chem. Commun. 2159-2161
29. Hu, T. M., Curtis, J. M., Walter, J. A., and Wright, J. L. C. (1996) Characterization of biologically inactive spirolides E and F: Identification of the spirolide pharmacophore Tetrahedron Lett. 37, 7671-7674 (Pubitemid 26344437)
30. Ishihara, J., Ishizaka, T., Suzuki, T., and Hatakeyama, S. (2004) Enantio- and stereocontrolled formation of the bisspiroacetal core of spirolide B Tetrahedron Lett. 45, 7855-7858 (Pubitemid 39302534)
31. Brimble, M. A. and Trzoss, M. (2004) A double alkylation-ring closing metathesis approach to spiroimines Tetrahedron 60, 5613-5622 (Pubitemid 38759341)
32. Meilert, K. and Brimble, M. A. (2005) Synthesis of the bis-spiroacetal moiety of spirolides B and D Org. Lett. 7, 3497-3500 (Pubitemid 41186815)
33. Stivala, C. E. and Zakarian, A. (2009) Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment Org. Lett. 11, 839-842
34. Gueret, S. M., Furkert, D. P., and Brimble, M. A. (2010) Synthesis of a functionalized 7,6-bicyclic spiroimine ring fragment of the spirolides Org. Lett. 12, 5226-5229
35. Otero, P., Alfonso, A., Vieytes, M. R., Cabado, A. G., Vieites, J. M., and Botana, L. M. (2010) Effects of environmental regimens on the toxin profile of Alexandrium ostenfeldii Environ. Toxicol. Chem. 29, 301-310
36. Zheng, S. Z., Huang, F. L., Chen, S. C., Tan, X. F., Zuo, J. B., Peng, J., and Xie, R. W. (1990) The isolation and bioactivities of pinnatoxin (in Chinese) Chinese J. Marine Drugs 33, 33-35
37. Uemura, D., Chou, T., Haino, T., Nagatsu, A., Fukuzawa, S., Zheng, S. Z., and Chen, H. S. (1995) Pinnatoxin-a: a toxic amphoteric macrocycle from the okinawan bivalve Pinna-muricata J. Am. Chem. Soc. 117, 1155-1156
38. Chou, T., Kamo, O., and Uemura, D. (1996) Relative stereochemistry of pinnatoxin A, a potent shellfish poison from Pinna muricata Tetrahedron Lett. 37, 4023-4026 (Pubitemid 26202915)
39. Chou, T., Haino, T., Kuramoto, M., and Uemura, D. (1996) Isolation and structure of pinnatoxin D, a new shellfish poison from the Okinawan bivalve Pinna muricata Tetrahedron Lett. 37, 4027-4030 (Pubitemid 26182904)
40. Kuramoto, M., Chou, T., and Uemura, D. (1999) Structures and functions of marine bioactive alkaloids J. Synth. Org. Chem. Jpn 57, 105-115 (Pubitemid 129699861)
41. Takada, N., Umemura, N., Suenaga, K., and Uemura, D. (2001) Structural determination of pteriatoxins A, B and C, extremely potent toxins from the bivalve Pteria penguin Tetrahedron Lett. 42, 3495-3497 (Pubitemid 32385747)
42. Suthers, B. D., Jacobs, M. F., and Kitching, W. (1998) Synthesis and NMR profiling of dioxabicyclo[3.2.1] octanes related to pinnatoxin D. Confirmation of the relative stereochemistry about rings E and F Tetrahedron Lett. 39, 2621-2624 (Pubitemid 28183934)
43. Selwood, A. I., Miles, C. O., Wilkins, A. L., van Ginkel, R., Munday, R., Rise, F., and McNabb, P. (2010) Isolation, structural determination and acute toxicity of pinnatoxins E, F and G J. Agric. Food Chem. 58, 6532-6542
44. Beaumont, S., Ilardi, E. A., Tappin, N. D. C., and Zakarian, A. (2010) Marine toxins with spiroimine rings: total synthesis of pinnatoxin A Eur. J. Org. Chem. 5743-5765
45. Kuramoto, M., Arimoto, H., and Uemura, D. (2004) Bioactive alkaloids from the sea: a review Marine Drugs 2, 39-54
46. Rhodes, L., Smith, K., Selwood, A., McNabb, P., van Ginkel, R., Holland, P., and Munday, R. (2010) Production of pinnatoxins by a peridinoid dinoflagellate isolated from Northland, New Zealand Harmful Algae 9, 384-389
47. Uemura, D. (2006) Bioorganic studies on marine natural products: Diverse chemical structures and bioactivities Chem. Rec. 6, 235-248
48. McCauley, J. A., Nagasawa, K., Lander, P. A., Mischke, S. G., Semones, M. A., and Kishi, Y. (1998) Total synthesis of pinnatoxin A J. Am. Chem. Soc. 120, 7647-7648 (Pubitemid 28383432)
49. Sugimoto, T., Ishihara, J., and Murai, A. (1999) Synthesis of the B,C,D,E,F-ring fragment of pinnatoxins Synlett 541-544 (Pubitemid 29225710)
50. Nakamura, S., Kikuchi, F., and Hashimoto, S. (2008) Stereoselective synthesis of a C1-C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence Tetrahedron-Asymmetry 19, 1059-1067
51. Trost, B. M. and Toste, F. D. (1999) Ruthenium-catalyzed cycloisomerization of 1,6-enynes initiated by C-H activation J. Am. Chem. Soc. 121, 9728-9729 (Pubitemid 29498499)
52. Trost, B. M. and Toste, F. D. (2000) Ruthenium-catalyzed cycloisomerizations of 1,6- and 1,7-enynes J. Am. Chem. Soc. 122, 714-715
53. Trost, B. M. and Toste, F. D. (2002) Mechanistic dichotomy in CpRu(CH3CN)(3)PF6 catalyzed enyne cycloisomerizations J. Am. Chem. Soc. 124, 5025-5036 (Pubitemid 34495895)
54. Stivala, C. E. and Zakarian, A. (2008) Total synthesis of (+)-pinnatoxin A J. Am. Chem. Soc. 130, 3774-3776 (Pubitemid 351429841)
55. Matsuura, F., Peters, R., Anada, M., Harried, S. S., Hao, J. L., and Kishi, Y. (2006) Unified total synthesis of pteriatoxins and their diastereomers J. Am. Chem. Soc. 128, 7463-7465 (Pubitemid 43877519)
56. Hao, J. L., Matsuura, F., Kishi, Y., Kita, M., Uemura, D., Asai, N., and Iwashita, T. (2006) Stereochemistry of pteriatoxins A, B, and C J. Am. Chem. Soc. 128, 7742-7743 (Pubitemid 43945709)
57. Torigoe, K., Murata, M., and Yasumoto, T. (1988) Prorocentrolide, a toxic nitrogenous macrocycle from a marine dinoflagellate, Prorocentrum lima J. Am. Chem. Soc. 110, 7876-7877
58. Hu, T. M., deFreitas, A. S. W., Curtis, J. M., Oshima, Y., Walter, J. A., and Wright, J. L. C. (1996) Isolation and structure of prorocentrolide B, a fast-acting toxin from Prorocentrum maculosum J. Nat. Prod. 59, 1010-1014 (Pubitemid 26408647)
59. Lu, C.-K., Lee, G.-H., Huang, R., and Chou, H.-N. (2001) Spiro-prorocentrimine, a novel macrocyclic lactone from a benthic Prorocentrum sp. of Taiwan Tetrahedron Lett. 42, 1713-1716 (Pubitemid 32467535)
60. Gill, S., Murphy, M., Clausen, J., Richard, D., Quilliam, M., MacKinnon, S., LaBlanc, P., Mueller, R., and Pulido, O. (2003) Neural injury biomarkers of novel shellfish toxins, spirolides: A pilot study using immunochemical and transcriptional analysis NeuroToxicology 24, 593-604 (Pubitemid 36994230)
61. Bourne, Y., Radic, Z., Aráoz, R., Talley, T. T., Benoit, E., Servent, D., Taylor, P., Molgó, J., and Marchot, P. (2010) Structural determinants in phycotoxins and AChBP conferring high affinity binding and nicotinic AChR antagonism Proc. Natl. Acad. Sci. U.S.A. 107, 6076-6081
62. Wandscheer, C. B., Vilarinífo, N., Espinífa, B., Louzao, M. C., and Botana, L. M. (2010) Human muscarinic acetylcholine receptors are a target of the marine toxin 13-desmethyl C spirolide Chem. Res. Toxicol. 23, 1753-1761