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


Contact
Bernd.Krock [ at ] awi.de

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 nconfirmed in most cases. In the current study, fifteen among eighteen hypothetical benzoyl analogs were partially purified and identified from cultured isolates of G. 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.



Item Type
Article
Authors
Divisions
Primary Division
Programs
Primary Topic
Peer revision
ISI/Scopus peer-reviewed
Publication Status
Published
Eprint ID
45903
DOI 10.4172/2329-6836.1000275

Cite as
Duran, L. , Krock, B. , Cembella, A. , Peralta-Cruz, J. , Bustillos-Guzmán, J. J. and Band-Schmidt, C. J. (2017): Characterization of Benzoyl Saxitoxin Analogs from the Toxigenic Marine Dinoflagellate Gymnodinium catenatum by Hydrophilic Interaction Liquid Ion-Chromatography-Tandem Mass Spectrometry , Natural Products Chemistry & Research, 5 (4), p. 275 . doi: 10.4172/2329-6836.1000275


Download
[img]
Preview
PDF
Duranl_2017.pdf

Download (708kB) | Preview
Cite this document as:

Share


Citation

Research Platforms
N/A

Campaigns


Actions
Edit Item Edit Item