Open AccessThree Novel Hydroxybenzoate Saxitoxin Analogues Isolated from the Dinoflagellate Gymnodinium catenatum
Author(s) -
Andrew P. Negri,
David Stirling,
Michael A. Quilliam,
Susan I. Blackburn,
Chris J S Bolch,
Ian W. Burton,
Geoff Eaglesham,
Krista Thomas,
John A. Walter,
Rick Willis
Publication year - 2003
Publication title -
chemical research in toxicology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.031
H-Index - 156
eISSN - 1520-5010
pISSN - 0893-228X
DOI - 10.1021/tx034037j
Subject(s) - saxitoxin , dinoflagellate , chromatography , gymnodinium , chemistry , fractionation , toxin , biology , botany , organic chemistry , biochemistry , phytoplankton , nutrient
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).
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