Literature DB >> 12924931

Three novel hydroxybenzoate saxitoxin analogues isolated from the dinoflagellate Gymnodinium catenatum.

Andrew Negri1, David Stirling, Michael Quilliam, Susan Blackburn, Chris Bolch, Ian Burton, Geoff Eaglesham, Krista Thomas, John Walter, Rick Willis.   

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).

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Year:  2003        PMID: 12924931     DOI: 10.1021/tx034037j

Source DB:  PubMed          Journal:  Chem Res Toxicol        ISSN: 0893-228X            Impact factor:   3.739


  18 in total

Review 1.  On the chemistry, toxicology and genetics of the cyanobacterial toxins, microcystin, nodularin, saxitoxin and cylindrospermopsin.

Authors:  Leanne Pearson; Troco Mihali; Michelle Moffitt; Ralf Kellmann; Brett Neilan
Journal:  Mar Drugs       Date:  2010-05-10       Impact factor: 5.118

2.  Biosynthetic intermediate analysis and functional homology reveal a saxitoxin gene cluster in cyanobacteria.

Authors:  Ralf Kellmann; Troco Kaan Mihali; Young Jae Jeon; Russell Pickford; Francesco Pomati; Brett A Neilan
Journal:  Appl Environ Microbiol       Date:  2008-05-16       Impact factor: 4.792

3.  Accumulation, biotransformation, histopathology and paralysis in the Pacific calico scallop Argopecten ventricosus by the paralyzing toxins of the dinoflagellate Gymnodinium catenatum.

Authors:  Amada Y Escobedo-Lozano; Norma Estrada; Felipe Ascencio; Gerardo Contreras; Rosalba Alonso-Rodriguez
Journal:  Mar Drugs       Date:  2012-05-09       Impact factor: 6.085

Review 4.  Neurotoxic alkaloids: saxitoxin and its analogs.

Authors:  Maria Wiese; Paul M D'Agostino; Troco K Mihali; Michelle C Moffitt; Brett A Neilan
Journal:  Mar Drugs       Date:  2010-07-20       Impact factor: 5.118

5.  A putative gene cluster from a Lyngbya wollei bloom that encodes paralytic shellfish toxin biosynthesis.

Authors:  Troco K Mihali; Wayne W Carmichael; Brett A Neilan
Journal:  PLoS One       Date:  2011-02-10       Impact factor: 3.240

6.  Saxitoxin puffer fish poisoning in the United States, with the first report of Pyrodinium bahamense as the putative toxin source.

Authors:  Jan H Landsberg; Sherwood Hall; Jan N Johannessen; Kevin D White; Stephen M Conrad; Jay P Abbott; Leanne J Flewelling; R William Richardson; Robert W Dickey; Edward L E Jester; Stacey M Etheridge; Jonathan R Deeds; Frances M Van Dolah; Tod A Leighfield; Yinglin Zou; Clarke G Beaudry; Ronald A Benner; Patricia L Rogers; Paula S Scott; Kenji Kawabata; Jennifer L Wolny; Karen A Steidinger
Journal:  Environ Health Perspect       Date:  2006-10       Impact factor: 9.031

7.  Toxin profile of Gymnodinium catenatum (Dinophyceae) from the Portuguese coast, as determined by liquid chromatography tandem mass spectrometry.

Authors:  Pedro R Costa; Alison Robertson; Michael A Quilliam
Journal:  Mar Drugs       Date:  2015-04-13       Impact factor: 5.118

8.  Bacterial community affects toxin production by Gymnodinium catenatum.

Authors:  Maria E Albinsson; Andrew P Negri; Susan I Blackburn; Christopher J S Bolch
Journal:  PLoS One       Date:  2014-08-12       Impact factor: 3.240

9.  Docking Simulation of the Binding Interactions of Saxitoxin Analogs Produced by the Marine Dinoflagellate Gymnodinium catenatum to the Voltage-Gated Sodium Channel Nav1.4.

Authors:  Lorena M Durán-Riveroll; Allan D Cembella; Christine J Band-Schmidt; José J Bustillos-Guzmán; José Correa-Basurto
Journal:  Toxins (Basel)       Date:  2016-05-06       Impact factor: 4.546

10.  Characterisation of the paralytic shellfish toxin biosynthesis gene clusters in Anabaena circinalis AWQC131C and Aphanizomenon sp. NH-5.

Authors:  Troco K Mihali; Ralf Kellmann; Brett A Neilan
Journal:  BMC Biochem       Date:  2009-03-30       Impact factor: 4.059

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