alexa Characterization of Benzoyl Saxitoxin Analogs from the Toxigenic Marine Dinoflagellate Gymnodinium catenatum by Hydrophilic Interaction Liquid Ion-Chromatography-Tandem Mass Spectrometry
ISSN: 2329-6836

Natural Products Chemistry & Research
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Research Article

Characterization of Benzoyl Saxitoxin Analogs from the Toxigenic Marine Dinoflagellate Gymnodinium catenatum by Hydrophilic Interaction Liquid Ion-Chromatography-Tandem Mass Spectrometry

Durán-Riveroll ML1*, Bernd Krock2, Allan Cembella2, Javier Peralta Cruz3, Bustillos Guzmán JJ4 and Band Schmidt CJ5

1Academic Unit of Ecology and Aquatic Biodiversity, Institute of Marine Sciences and Limnology, National Autonomous University of Mexico, Mexico

2Helmholtz Center for Polar and Marine Research, Alfred Wegener Institute, Bremerhaven 27570, Germany

3National School of Biological Sciences-National Polytechnic Institute, Mexico City 11340, Mexico

4Center for Biological Research of the Northwest, La Paz, B.C.S. 23096, Mexico

5Interdisciplinary Center of Marine Sciences-National Polytechnic Institute, La Paz, B.C.S. 23000, Mexico

*Corresponding Author:
Durán-Riveroll ML
Academic Unit of Ecology and Aquatic Biodiversity, Institute of Marine Sciences and Limnology
National Autonomous University of Mexico, Mexico City 04510, Mexico
Tel: +52(55)5623-0222/44639
E-mail: [email protected]

Received Date: June 02, 2017; Accepted Date: June 12, 2017; Published Date: September 10, 2017

Citation: Duran-Riveroll ML, Krock B, Cembella A, Cruz JP, Guzmán JJB, et al. (2017) Characterization of Benzoyl Saxitoxin Analogs from the Toxigenic Marine Dinoflagellate Gymnodinium catenatum by Hydrophilic Interaction Liquid Ion-Chromatography-Tandem Mass Spectrometry. Nat Prod Chem Res 5:275. doi: 10.4172/2329-6836.1000275

Copyright: © 2017 Durán-Riveroll ML, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

 

Abstract

The chain-forming marine dinoflagellate Gymnodinium catenatum Graham has a remarkable capacity to produce a wide array of neurotoxic alkaloids associated with paralytic shellfish poisoning (PSP). More than a decade ago, a completely new group of benzoyl saxitoxin analogs produced exclusively by this species was discovered, but the exact structural assignments and diversity among global population has remained elusive and unconfirmed in most cases. In the current study, fifteen among eighteen hypothetical benzoyl analogs were partially purified and identified from cultured isolates of Gymnodinium catenatum from the Pacific coast of Mexico. Combined serial application of flash chromatography, preparative liquid chromatography and tandem mass spectrometry (LC-MS/MS) in multiple steps yielded a richness of benzoyl analogs that has not been reported nor confirmed before. Two sub-fractions were analyzed by 1H-NMR; results from one fraction showed a probable AMX pattern for three protons, consistent with the presence of a 3,4-dihydroxylated benzoyl ring. These findings could be interpreted to correct the 2,4- dihydroxylated structure previously proposed for the GCa benzoyl analog series. The revised and enhanced structural information on proposed benzoyl derivatives is necessary to provide further insights into biogeographical diversity of these potentially potent toxins produced by marine dinoflagellates and their role in seafood safety.

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