Spirolide toxins

Cembella, A.D., Bauder, A.G., Lewis, N.L, and QuiUiam, M.A. Association of the gonyaulacoid dinoflagel-late Alexandrium ostenfeldii with spirolide toxins in size fractionated plankton, J. Plank. Res., 23, 1413-1419, 2001b. 

It is instructive to consider the geographical and population level differences in spirolide toxin profiles among cultured isolates and natural blooms of A. ostenfeldii. In general, typical spirolide profiles of this species from the northeast Atlantic region often contain primarily desmethyl C, didesmethyl C and 20-methyl G spirolides, but this is accompanied by considerable inter- and intrapopulation heterogeneity. The spirolide profile from plankton size fractions containing... 

Aasen, J.A.B. et al., Discovery of fatty acid ester metabohtes of spirolide toxins in mussels from Norway using liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 20(10), 1531-1537, 2006. 

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 Comm. Mass Spec. 20, 1531, 2006. Gonzalez A.V. et al. First evidence of spirolides in Spanish shellfish, Toxicon 48, 1068, 2006. Uemura D. et al. Pinnatoxin A a toxic amphoteric macrocycle from the Okinawan bivalve Pimm muricata, J. Am. Chem. Soc. 117, 1155, 1995. 

Okadaic acid (OA), dinophysistoxins (DTXs), pectenotoxins (PTXs), azaspiracids (AZAs) and spirolides Shellfish 9-2,012 ng/g (mainly OA group toxins) [204]... 

Biotoxins, mainly of the spirolide family, have been principally monitored in shellfish samples. Reported toxin levels vary from 2-585 ng/g [206] to 11-7,950 ng/g [205] in shellfish from France and Italy, respectively, whereas reported values for Spanish mussels were in the range of 13-20 ng/g [82]. This study employed the use of different MS modes of operation, enhanced MS (EMS) and MS3 experiments in order to confirm the first occurrence of spirolides in Spanish shellfish. Okadaic acids were the principal toxin contaminants found in shellfish samples from Galicia, Spain, with levels reaching 2,012 ng/g [204]. Putative palytoxin was for the first time detected in Italian waters at levels of 1,350 ng for plankton pellet) and 1,950 ng for butanol extract thus, it was suggested to be the causative agent responsible for the Genoa 2005 outbreak showing respiratory Ulness in people exposed to marine aerosols [31]. 

Brimble, M.A., and Furkert, D.P 2004. Synthesis of the l,6,8-trioxadispiro[4.1.5.2]tetradec-l 1-ene ring system present in the spirolide family of shellfish toxins and its conversion into a l,6,8-fi ioxadispiro[4.1.5.2]-tetradec-9-en-12-ol via base-induced rearrangement of an epoxide. Org Biomol Chem 2, 3573—3583. 

Cembella, A.D., Lewis, N.I., and Quilliam, M.A. 1999. Spirolide composition of micro-exfi acted pooled cells isolated from natural plankton assemblages and from cultiwes of file dinoflagellate Alexandrium ostenfeldii. Nat Toxins 7, 197—206. -------. 2000. The marine dinoflagellate Alexandrium ostenfeldii (Dinophyceae) as the causative organism of spirolide shellfish toxin. Phycologia 39, 61-1 A. 

Falk, M., Burton, I.W., Hu, T, Walter, J.A. and Wright, J.L.C., 2001. Assignment of the relative stereochemistry of the spirolides, macrocyclic toxins isolated from shellfish and from file cultured dmodigtWiXQ Alexandrium ostenfeldii. Tetrahedron 51, 8659-8665. 

Gill, S., Murphy, M., Clausen, I, 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... 

Wright, J.L.C., Curtis, J.M., Hu, X, and Walter, JA. 1997. The spirolides and prorocentrolide B new additions to a rapidly growing group of fast-acting toxins with a common pharmacophore. 8th Int Conf on Harmful Algae, Abstract p. 215. 

Amzil, Z., Royer, F., Sibat, M., Guimard, S., Neaud-Masson, N., and Chiantella, C. Lipophilic toxins in French shellfish first report of pectenotoxin-2, spirolide-C and their isomers by liquid chromatography/mass spectrometry, in Proceedings 12th International Conference on Flarmful Algae, Copenhagen, Denmark, September, 4—8 2006, abstract PO.05-05. 

FIGURE 26.2 Global distribution of spirolides in populations of the toxigenic dinoflagellate ostenfeldii and where the occurrence of these toxins in shellfish is proven or circumstantially associated with this dinoflagellate. 

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