Spirolide

Spirolide biotoxins 13-desMeC SPX, 13,19-didesMeC SPX, 27-OH-13,19-didesMeC SPX, YTX, homoYTX, CarboxyYTX, CarboxyhomoYTX, 45-OHYTX, 45-OhhomoYTX, PTX-2sa Shellfish 11-7,950 ng/g [205]... 

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]. 

The silyl-Prins reaction between (Z)-4-trimethylsilyl-3-buten-l-ol 255 and aldehydes under mild Lewis acid conditions exclusively provides 2,6-ry -disubstituted 3,6-dihydropyrans 256 (Equation 115) <2002TL7055, 2003JOC7880>. A silyl-Prins reaction is also used to construct a 3,6-dihydropyran intermediate during a synthesis of the bis-spiroacetal moiety of the spirolides B and D in this instance a masked bromoaldehyde 257 is used as the cyclization partner (Equation 116) <2005OL3497>. 

Spirolides Muscarinic and/or Nicotinic Acetyichoiine Receptor Ligands ... 

Pulido 2001), appeared not to be involved since there were no transcriptional differences between controls and spirolide-treated animals (Gill et al. 2003). It is clear that further studies are needed to define the molecular targets for this growing number of phycotoxins. 

Aasen, J., MacKinnon, S.L., LeBlanc, R, Walter, J. A., Hovgaard, R, Aune, T, and Quilliam M.A., 2005. Detection and identification of spirolides in Norwegian shellfish and plankton. Chem Res Toxicol 18, 509-515. 

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., Bauder, A.G., Lewis, N.I., and Quilliam, M.A. 2001. Population dynamics and spirolide composition of file toxigenic 6mod. igQ dXQ Alexandrium ostenfeldii in coastal emba>ments of Nova Scotia. In Harmful Algal Blooms 2000, ed. Hallegraeff, G.M., Blackburn, S.I., Bolch, C.J., and Lewis, R.J. Intergovernmental Oceanographic Commission of UNESCO, 173-176. 

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. 

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