Polyhydroxylated amide analogs of yessotoxin from Protoceratium reticulatum

Toxicon

Volumn 45, Issue 1, 2005, Pages 61-71

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

^a RUAKURA RESEARCH CENTRE   (New Zealand)

^b NORWEGIAN VETERINARY INSTITUTE   (Norway)

^c UNIVERSITY OF WAIKATO   (New Zealand)

^d CAWTHRON INSTITUTE   (New Zealand)

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

Author keywords

Protoceratium reticulatum; Yessotoxin

Indexed keywords

41 A HOMOYESSOTOXIN; 9 METHYL 41 A HOMOYESSOTOXIN; TOXIN; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DINOFLAGELLATE; FEMALE; HYDROXYLATION; ISOLATION PROCEDURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTOCERATIUM RETICULATUM; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; ETHERS, CYCLIC; FEMALE; MICE; MOLECULAR STRUCTURE; MOLLUSK VENOMS; OXOCINS;

PROTOCERATIUM RETICULATUM;

EID: 9744246051     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2004.09.011     Document Type: Article

References (28)

1. T. Aune, R. Sorby, T. Yasumoto, H. Ramstad, and T. Landsverk Comparison of oral and intraperitoneal toxicity of yessotoxin towards mice Toxicon 40 2002 77 82
2. Briggs, L.R., Miles, C.O., Garthwaite, I., Ross, K.M., Towers, N.R., Samdal, I.A., Aasen, J., Torgersen, T., Petersen, D., 2002. Immunoassays for analysis of yessotoxins, Tenth International Conference on Harmful Algal Blooms, St Pete Beach, FL, USA, p. 37.
3. P. Ciminiello, E. Fattorusso, M. Forino, S. Magno, R. Poletti, and R. Viviani Isolation of adriatoxin, a new analogue of yessotoxin from mussels of the Adriatic Sea Tetrahedron Lett. 39 1998 8897 8900
4. P. Ciminiello, E. Fattorusso, M. Forino, R. Poletti, and R. Viviani Structure determination of carboxyhomoyessotoxin, a new yessotoxin analogue isolated from Adriatic mussels Chem. Res. Toxicol. 13 2000 770 774
5. P. Ciminiello, E. Fattorusso, M. Forino, R. Poletti, and R. Viviani A new analogue of yessotoxin, carboxyyessotoxin, isolated from Adriatic sea mussels Eur. J. Org. Chem. 2000 2000 291 295
6. J.M. Cooney, D.J. Jensen, and C.O. Miles Ion-trap LC-MS as a tool for structural characterisation of marine algal toxins P. Holland L. Rhodes L. Brown HABTech 2003 Cawthron Report No. 906 2003 Cawthron Institute Nelson, New Zealand 59 64
7. M. Daiguji, M. Satake, H. Ramstad, T. Aune, H. Naoki, and T. Yasumoto Structure and fluorometric HPLC determination of 1-desulfoyessotoxin, a new yessotoxin analog isolated from mussels from Norway Nat. Toxins 6 1998 235 239
8. R. Draisci, E. Ferretti, L. Palleschi, C. Marchiafava, R. Poletti, A. Milandri, A. Ceredi, and M. Pompei High levels of yessotoxin in mussels and presence of yessotoxin and homoyessotoxin in dinoflagellates of the Adriatic Sea Toxicon 37 1999 1187 1193
9. European Union Commission decision of 15 March 2002 laying down detailed rules for the implementation of Council Directive 91/492/EEC as regards the maximum permitted levels and the methods for analysis of certain marine biotoxins in bivalve molluscs, echinoderms, tunicates and marine gastropods (2002/225/EC) Off. J. Eur. Communities L 75/62 2002
10. T. Hu, J.M. Curtis, J.A. Walter, J.L. McLachlan, and J.L.C. Wright Two new water-soluble DSP toxin derivatives from the dinoflagellate Prorocentrum maculosum: possible storage and excretion products Tetrahedron Lett. 36 1995 9273 9276
11. L.M. Jackman, and S. Sternhill Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry 1969 Pergamon press Oxford
12. G.R. Macpherson, I.W. Burton, P. LeBlanc, J.A. Walter, and J.L.C. Wright 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 2003 1659 1664
13. C.O. Miles, A.L. Wilkins, A.D. Hawkes, A. Selwood, D.J. Jensen, J. Aasen, R. Munday, I.A. Samdal, L.R. Briggs, V. Beuzenberg, A.L. MacKenzie, and P.T. Holland Isolation of a 1,3-enone isomer of heptanor-41-oxoyessotoxin from Protoceratium reticulatum cultures Toxicon 44 2004 325 336
14. Miles, C.O., Wilkins, A.L., Samdal, I.A., Briggs, L.R., Aasen, J., Cooney, J.M., Jensen, D.J., Hawkes, A.D., Holland, P.T., Petersen, D., Quilliam, M.A., Selwood, A., MacKenzie, A.L., Beuzenberg, V., Munday, R., 2004b. Protoceratium reticulatum produces numerous yessotoxin analogues, Fifth International Conference on Molluscan Shellfish Safety, Galway, Ireland, pp. 44.
15. M. Murata, M. Kumagai, J.S. Lee, and T. Yasumoto Isolation and structure of yessotoxin, a novel polyether compound implicated in diarrhetic shellfish poisoning Tetrahedron Lett. 28 1987 5869 5872
16. H. Ogino, M. Kumagai, and T. Yasumoto Toxicologic evaluation of yessotoxin Nat. Toxins 5 1997 255 259
17. B. Paz, P. Riobó, M. Luisa Fernández, S. Fraga, and J.M. Franco Production and release of yessotoxins by the dinoflagellates Protoceratium reticulatum and Lingulodinium polyedrum in culture Toxicon 44 2004 251 258
18. I.A. Samdal, L.J. Naustvoll, C.D. Olseng, L.R. Briggs, and C.O. Miles Use of ELISA to identify Protoceratium reticulatum as a source of yessotoxin in Norway Toxicon 44 2004 75 82
19. M. Satake Biosynthesis of the marine polyether toxin, yessotoxin Tennen Yuki Kagoubutsu Toronkai Yoshishu 42 2000 259 264
20. M. Satake, K. Terasawa, Y. Kadowaki, and T. Yasumoto Relative configuration of yessotoxin and isolation of two new analogs from toxic scallops Tetrahedron Lett. 37 1996 5955 5958
21. M. Satake, L. MacKenzie, and T. Yasumoto Identification of Protoceratium reticulatum as the biogenetic origin of yessotoxin Nat. Toxins 5 1997 164 167
22. M. Satake, A. Tubaro, J.-S. Lee, and T. Yasumoto Two new analogs of yessotoxin, homoyessotoxin and 45-hydroxyhomoyessotoxin, isolated from mussels of the Adriatic Sea Nat. Toxins 5 1997 107 110
23. M. Satake, T. Ichimura, K. Sekiguchi, S. Yoshimatsu, and Y. Oshima Confirmation of yessotoxin and 45,46,47-trinoryessotoxin production by Protoceratium reticulatum collected in Japan Nat. Toxins 7 1999 147 150
24. Satake, M., Eiki, K., Oshima, Y., Mitsuya, T., Sekiguchi, K., Koike, K., Ogata, T., 2002. Yessotoxin production by Protoceratium reticulatum in Japan and structures of its new analogs, Tenth International Conference on Harmful Algae, St Pete Beach, Fl, USA.
25. K. Terao, E. Ito, M. Oarada, M. Murata, and T. Yasumoto Histopathological studies on experimental marine toxin poisoning - 5. The effects in mice of yessotoxin isolated from Patinopecten yessoensis and of a desulfated derivative Toxicon 28 1990 1095 1104
26. A. Tubaro, S. Sosa, M. Carbonatto, G. Altinier, F. Vita, M. Melato, M. Satake, and T. Yasumoto Oral and intraperitoneal acute toxicity studies of yessotoxin and homoyessotoxins in mice Toxicon 41 2003 783 792
27. G. Wang, and R.I. Hollingsworth Direct conversion of (S)-3-hydroxy- γ-butyrolactone to chiral three-carbon building blocks J. Org. Chem. 64 1999 1036 1038
28. G. Wang, and R.I. Hollingsworth A simple three-step method for preparing homochiral 5-trityloxymethyl-2-oxazolidinones from optically active 3-hydroxy-γ-butyrolactones Tetrahedron: Asymmetry 11 2000 4429 4432