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

Volumn 56, Issue 8, 2010, Pages 1327-1333

  Ciminiello, Patrizia ^a   Dell'Aversano, Carmela ^a   Iacovo, Emma Dello ^a   Fattorusso, Ernesto ^a   Forino, Martino ^a   Grauso, Laura ^a   Tartaglione, Luciana ^a   Guerrini, Franca ^b   Pezzolesi, Laura ^b   Pistocchi, Rossella ^b  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Adriatic Sea; Alexandrium ostenfeldii; LC MS; NMR; Spirolide

Indexed keywords

27 HYDROXY 13 DESMETHYLSPIROLIDE C; 27 OXO 13,19 DIDESMETHYLSPIROLIDE C; MARINE TOXIN; UNCLASSIFIED DRUG;

ALEXANDRIUM OSTENFELDII; ANIMAL EXPERIMENT; ARTICLE; DINOFLAGELLATE; FEMALE; MASS SPECTROMETRY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; TOXICITY TESTING; TOXIN ANALYSIS; TOXIN STRUCTURE;

ANIMALS; DINOFLAGELLIDA; MARINE TOXINS; MICE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SPIRO COMPOUNDS; TOXICITY TESTS;

ALEXANDRIUM OSTENFELDII; DINOPHYCEAE;

EID: 77958485849     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2010.07.016     Document Type: Article

References (16)

1. Balech E., Tangen K. Morphology and taxonomy of toxic species in the Tamarensis group (Dinophyceae): Alexandrium excavatum (Braarud) comb. nov. and Alexandrium ostenfeldii (Paulsen) comb. nov. Sarsia 1985, 70:333-343.
2. Cembella A.D., Lewis N.I., Quilliam M.A. Spirolide composition of micro-extracted pooled cells isolated from natural plankton assemblages and from cultures of dinoflagellate Alexandrium ostenfeldii. Nat. Toxins 1999, 7:197-206.
3. Cembella A.D., Quilliam M.A., Lewis N.I. The marine dinoflagellate Alexandrium ostenfeldii (Dinophyceae) as the causative organism of spirolide shellfish toxins. Phycologia 2000, 39:67-74.
4. Ciminiello P., Dell'Aversano C., Fattorusso E., Magno S., Tartaglione L., Cangini M., Pompei M., Guerrini F., Boni L., Pistocchi R. Toxin profile of Alexandrium ostenfeldii (Dinophyceae) from the northern Adriatic Sea revealed by liquid chromatography-mass spectrometry. Toxicon 2006, 47:597-604.
5. Ciminiello P., Dell'Aversano C., Fattorusso E., Forino M., Grauso L., Tartaglione L., Guerrini F., Pistocchi R. Spirolide toxin profile of Adriatic Alexandrium ostenfeldii cultures and structure elucidation of 27-hydroxy-13,19-didesmethyl spirolide C. J. Nat. Prod. 2007, 70:1878-1883.
6. Ciminiello P., Catalanotti B., Dell'Aversano C., Fattorusso C., Fattorusso E., Forino M., Grauso L., Leo A., Tartaglione L. Full relative stereochemistry assignment and conformational analysis of 13,19-didesmethyl spirolide C. via NMR- and molecular modeling-based techniques. A step towards understanding spirolide's mechanism of action. Org. Biomol. Chem. 2009, 7:3613-3880.
7. Ciminiello P., Dell'Aversano C., Fattorusso E., Forino M., Tartaglione L., Boschetti L., Rubini S., Cangini M., Pigozzi S., Poletti R. Complex toxin profile of Mytilus galloprovincialis from the Adriatic Sea revealed by LC-MS. Toxicon 2010, 55:280-288.
8. Guillard R.R.L. Culture of Phytoplankton for Feeding Marine Invertebrates. Culture of Marine Invertebrates Animals 1975, 26-60. Plenum Press, New York. W.L. Smith, M.H. Chanley (Eds.).
9. Hoshaw R.W., Rosowski J.R. Culture Methods and Growth Measurements. Handbook of Phycological Methods 1973, 53-67. Cambridge University Press, New York. J.R. Stein (Ed.).
10. 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, 20:2159-2161.
11. 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.
12. Mackenzie L., White D., Oshima Y., Kapa J. The resting cyst of Alexandrium ostenfeldii (Dinophyceae) in New Zealand. Phycologia 1996, 35:148-155.
13. MacKinnon S.L., Walter J.A., Quilliam M.A., Cembella A.D., LeBlanc P., Burton I.W., Hardstaff W.R., Lewis N.I. Spirolides isolated from Danish strains of the toxigenic dinoflagellate Alexandrium ostenfeldii. J. Nat. Prod. 2006, 69:983-987.
14. Richard D., Arsenault E., Cembella A.D., Quilliam M.A. Investigations into the Toxicology and Pharmacology of Spirolides, a Novel Group of Shellfish Toxins. Intergovernmental Oceanographic Commission of UNESCO 2001, 383-386. Harmful Algal Blooms 2000, Paris. G.M. Hallegraeff, S.I. Blackburn, C.J. Bolch, R.J. Lewis (Eds.).
15. Sleno L., Chalmers M.J., 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. 2004, 378:977-986.
16. Utermöhl H. Zur Vervollkommnung der quantitativen Phyto-plankton-Methodik. Mitt. Int. Verein. Limnol. 1958, 9:1-38.