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Three Novel Hydroxybenzoate Saxitoxin Analogues Isolated from the Dinoflagellate Gymnodinium catenatum

journal contribution
posted on 2023-05-16, 14:28 authored by Negri, A, Stirling, D, Quilliam, M, Blackburn, S, Christopher BolchChristopher Bolch, Burton, I, Eaglesham, G, Thomas, K, Walter, J, Willis, R
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).

History

Publication title

Chemical Research in Toxicology

Volume

16

Issue

8

Pagination

1029-1033

ISSN

0893-228X

Department/School

Institute for Marine and Antarctic Studies

Publisher

American Chemical Society

Place of publication

Washington, USA

Repository Status

  • Restricted

Socio-economic Objectives

Fisheries - aquaculture not elsewhere classified

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