Complex profiles of hydrophobic paralytic shellfish poisoning compounds in Gymnodinium catenatum identified by liquid chromatography with fluorescence detection and mass spectrometry

Vale, Paulo

doi:10.1016/j.chroma.2008.04.073

Cited by 56 publications

(48 citation statements)

References 16 publications

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“…Chemical structure of saxitoxin and analogs produced by Gymnodinium catenatum. Structures marked with ( * ) were not fully characterized by NMR in previous studies but their probable structures were inferred based upon mass spectrometry [20]. According to our findings based upon mass spectrometry and NMR, we propose 3,4-dihydroxybenzoyl instead of 2,4-dihydroxybenzoyl for the GCa benzoyl analog series.…”

Section: Introductionmentioning

confidence: 95%

“…Nevertheless, we considered that the molecules with the sulfate group in α-position were the first to elute, as mentioned by Diener [25] and Dell' Aversano [26]. In such cases, structural identification must be supported by NMR, or at least by analysis of the molecular fragments obtained by tandem mass spectrometry, such as those reported by Vale [20]. …”

Section: Polarity Of Gc Toxins and Chromatographic Aspects Of Retentimentioning

confidence: 99%

“…Furthermore, in our earlier work and in previous studies of GCtoxins in unfractionated matrices (e.g., Vale [20]), 2 g C-18 silica cartridges were used for clean-up, typically yielding a 2:1 ratio of solid phase: sample volume. Although it is difficult to compare the amount of target analytes for purification in various fractions, the fractionation scheme whereby a relatively high amount (1.3 g) of crude extract was applied to 100 g C-18 silica column may have caused less specific separation and even breakthrough of toxin components due to excessive loading.…”

Section: Fractionationmentioning

confidence: 99%

“…A better grouping would be simply based upon structural consideration of their respective side chains, i.e., as carbamoyl, decarbamoyl, sulfocarbamoyl, or benzoyl analogs. The latter group can be further sub-divided into parahydroxybenzoyl, di-hydroxybenzoyl and sulfo-benzoyl analogs [20] ( Figure 1). …”

Section: Polarity Of Gc Toxins and Chromatographic Aspects Of Retentimentioning

confidence: 99%

“…[dcGTXs], and N-sulfocarbamoyl B and C toxins, versus so-called "hydrophobic" (e.g., benzoyl or GC) analogs [16,[19][20][21][22] (Figure 1). Identification of benzoyl analogs has been hampered mainly by the lack of analytical standards [20,21,23], but probable structures for some analogs have been proposed based upon mass spectrometric analysis [20].…”

Section: Introductionmentioning

confidence: 99%

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

Duran¹,

Krock²,

Cembella³

et al. 2017

Nat Prod Chem Res

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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 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 1 H-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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Section: Introductionmentioning

confidence: 95%

Section: Polarity Of Gc Toxins and Chromatographic Aspects Of Retentimentioning

confidence: 99%

Section: Fractionationmentioning

confidence: 99%

Section: Polarity Of Gc Toxins and Chromatographic Aspects Of Retentimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Duran¹,

Krock²,

Cembella³

et al. 2017

Nat Prod Chem Res

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Measurement of Algal Toxins in the Environment

Botana

Louzao

Alfonso

et al. 2009

Encyclopedia of Analytical Chemistry

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Algal toxins are important from an analytical point of view because they need to be constantly scrutinized owing to the danger they pose to consumers when they concentrate in filter‐feeding shellfish or in drinking water and fish. Their chemical diversity is very large, with each group having many analogs. Each group has different pharmacological activities, although not all the mechanisms of action are understood. The main marine toxin groups are as follows: saxitoxin and analogs, okadaic acid and dinophysistoxins, azaspiracids, yessotoxins, pectenotoxins, cyclic imines, domoic acid, ciguatoxins, brevetoxins, palytoxin, gambierol, and polycavernoside. The main cyanobacterial toxins considered are hepatotoxins such as microcystins, nodularin, and cylindrospermopsin. The research concerning marine toxins is underdeveloped owing to a historic scarcity of standards. This has delayed not only the progress in their pharmacology but also the development of methods for detection and measurement. In the current situation, the mouse bioassay is the most common method being used to measure them. New methods are rapidly emerging as future solutions: (i) functional and nonanalytical methods, which provide information on their toxicity and quantify the toxin group (cell assays, receptor assays, biosensor assays), (ii) biochemical methods that do not provide information on toxicity (antibody‐based methods), and (iii) analytical methods, which identify the species in each toxin group, and can quantify those for which standards are available. The main drawback of these methods is the lack of toxicity equivalent factors, which allow the conversion of toxin amounts to toxic values of a reference toxin. None of these methods has been validated, and therefore much remains to be done in the field.

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Chemistry and analysis of PSP toxins

Botana

López

2015

Phycotoxins

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Complex profiles of hydrophobic paralytic shellfish poisoning compounds in Gymnodinium catenatum identified by liquid chromatography with fluorescence detection and mass spectrometry

Cited by 56 publications

References 16 publications

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

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

Measurement of Algal Toxins in the Environment

Chemistry and analysis of PSP toxins

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