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Three Novel Hydroxybenzoate Saxitoxin Analogues Isolated from the Dinoflagellate Gymnodinium catenatum

Citation

Negri, A and Stirling, D and Quilliam, M and Blackburn, S and Bolch, CJS and Burton, I and Eaglesham, G and Thomas, K and Walter, J and Willis, R, Three Novel Hydroxybenzoate Saxitoxin Analogues Isolated from the Dinoflagellate Gymnodinium catenatum, Chemical Research in Toxicology, 16, (8) pp. 1029-1033. ISSN 0893-228X (2003) [Refereed Article]

DOI: doi:10.1021/tx034037j

Abstract

In a recent survey of paralytic shellfish poisoning (PSP) toxins in Gymnodinium catenatum Graham extracts, using LC with postcolumn oxidation and fluorescence detection, three novel saxitoxin analogues were revealed in isolates from several locations, including Australian waters. We have named them as G. catenatum toxins, GC1,(1), GC2 (2), and GC3 (3). The compounds were isolated from a culture of the Australian strain-by LC-MS-guided fractionation employing a C18-silica column and hydrophilic interaction chromatography. The unusual structures of these novel compounds were characterized by low- and high-resolution MS, MS/MS, and NMR spectroscopy. GC3 (3) was found to be the 4-hydroxybenzoate ester derivative of decarbamoylsaxitoxin, while GC1 (1) and GC2 (2) are the epimeric 11-hydroxysulfate derivatives of GC3 (3).

Item Details

Item Type:Refereed Article
Research Division:Agricultural and Veterinary Sciences
Research Group:Fisheries Sciences
Research Field:Fish Pests and Diseases
Objective Division:Animal Production and Animal Primary Products
Objective Group:Fisheries - Aquaculture
Objective Field:Fisheries - Aquaculture not elsewhere classified
Author:Bolch, CJS (Dr Christopher Bolch)
ID Code:27558
Year Published:2003
Web of Science® Times Cited:73
Deposited By:TAFI - Aquaculture
Deposited On:2003-08-01
Last Modified:2004-03-29
Downloads:0

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