Liquid chromatography–tandem mass spectrometry method for the detection of marine lipophilic toxins under alkaline conditions

Gerssen, Arjen; Mulder, Patrick P.J.; McElhinney, Mairead A.; Boer, Jacob de

doi:10.1016/j.chroma.2008.12.099

Cited by 155 publications

(103 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Similar chromatography for 3 was also observed using alkaline conditions on an analytical scale. 37 This is presumably related to the fact that both 3 and 6 lack a methyl group at the R 3 position (Figure 1), which somehow affects their chromatographic behavior. All fractions were collected based on UV detection at 210 nm to minimize contamination with nonazaspiracid analytes.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Improved Isolation Procedure for Azaspiracids from Shellfish, Structural Elucidation of Azaspiracid-6, and Stability Studies

Kilcoyne

Keogh

Clancy

et al. 2012

J. Agric. Food Chem.

View full text Add to dashboard Cite

Azaspiracids are a group of lipophilic polyether toxins produced by the small dinoflagellate Azadinium spinosum. They may accumulate in shellfish and can result in illnesses when consumed by humans. Research into analytical methods, chemistry, metabolism, and toxicology of azaspiracids has been severely constrained by the scarcity of high-purity azaspiracids. Consequently, since their discovery in 1995, considerable efforts have been made to develop methods for the isolation of azaspiracids in sufficient amounts and purities for toxicological studies, in addition to the preparation of standard reference materials. A seven-step procedure was improved for the isolation of azaspiracids-1−3 (1, 2, and 3) increasing recoveries 2-fold as compared to previous methods and leading to isolation of sufficiently purified azaspiracid-6 (6) for structural determination by NMR spectroscopy. The procedure, which involved a series of partitioning and column chromatography steps, was performed on 500 g of Mytilus edulis hepatopancreas tissue containing ∼14 mg of 1. Overall yields of 1 (52%), 2 (43%), 3 (43%), and 6 (38%) were good, and purities were confirmed by NMR spectroscopy. The structure of 6 was determined by one-and two-dimensional NMR spectroscopy and mass spectrometry. The stability of 6 relative to 1 was also assessed in three solvents in a short-term study that demonstrated the greatest stability in aqueous acetonitrile.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

Improved Isolation Procedure for Azaspiracids from Shellfish, Structural Elucidation of Azaspiracid-6, and Stability Studies

Kilcoyne

Keogh

Clancy

et al. 2012

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…The compounds were separated on an X-Bridge C8 column (2.1 mm Â 50 mm, 3.5 mm; Waters Corp.) at a flowrate of 500 mL/min, and an injection volume of 10 mL under alkaline conditions according to previously reported conditions (Gerssen et al, 2009;García-Altares et al, 2013). Briefly, mobile phase A consisted of 6.7 mM of ammonium hydroxide in ultrapure Milli-Q water.…”

Section: Lcems/ms Methods Bmentioning

confidence: 99%

Identification of gymnodimine D and presence of gymnodimine variants in the dinoflagellate Alexandrium ostenfeldii from the Baltic Sea

Harju

Koskela

Kremp

et al. 2016

Toxicon

View full text Add to dashboard Cite

a b s t r a c tGymnodimines are lipophilic toxins produced by the marine dinoflagellates Karenia selliformis and Alexandrium ostenfeldii. Currently four gymnodimine analogues are known and characterized. Here we describe a novel gymnodimine and a range of gymnodimine related compounds found in an A. ostenfeldii isolate from the northern Baltic Sea. Gymnodimine D (1) was extracted and purified from clonal cultures, and characterized by liquid chromatographyetandem mass spectrometry (LCeMS/MS), nuclear magnetic resonance (NMR) spectroscopy, and liquid chromatographyehigh resolution mass spectrometry (LC eHRMS) experiments. The structure of 1 is related to known gymnodimines (2e5) with a six-membered cyclic imine ring and several other fragments typical of gymnodimines. However, the carbon chain in the gymnodimine macrocyclic ring differs from the known gymnodimines in having two tetrahydrofuran rings in the macrocyclic ring.

show abstract

“…Separations of lipophilic toxins were performed by reverse-phase chromatography column XBridge C18 5 mm particle size, 3 mm diameter and 150 mm length (Waters, Dublin, Ireland), maintained at 40 C, with gradient elution using an alkaline (pH 11) mobile phase according to Gerssen et al (2009). Mobile phase A consisted of 6.7 mM of ammonia in ultrapure water.…”

Section: Shellfish Samplesmentioning

confidence: 99%

Amphidoma languida (Amphidomatacea, Dinophyceae) with a novel azaspiracid toxin profile identified as the cause of molluscan contamination at the Atlantic coast of southern Spain

Tillmann

Jaén²,

Fernandez³

et al. 2017

Harmful Algae

View full text Add to dashboard Cite

A B S T R A C TAzaspiracids (AZA) are a group of food poisoning phycotoxins that are known to accumulate in shellfish. They are produced by some species of the planktonic dinophycean taxon Amphidomataceae. Azaspiracids have been first discovered in Ireland but are now reported in shellfish from numerous global sites thus showing a wide distribution. In shellfish samples collected in 2009 near Huelva (Spain), AZA was also found along the Andalusian Atlantic coast for the first time. Analysis using LC-MS/MS revealed the presence of two different AZA analogues in different bivalve shellfish species (Chamelea gallina, Cerastoderma edule, Donax trunculus, and Solen vagina). In a number of samples, AZA levels exceeded the EU regulatory level of 160 mg AZA-1 eq. kg À1 (reaching maximum levels of >500 mg AZA-1 eq. kg À1 in Chamelea gallina and >250 mg AZA-1 eq. kg À1 in Donax trunculus) causing closures of some local shellfish production areas. One dinophyte strain established from the local plankton during the AZA contamination period and determined as Amphidoma languida was in fact toxigenic, and its AZA profile disclosed it as the causative species: it contained AZA-2 as the main compound and the new compound AZA-43 initially detected in the shellfish. AZA-43 had the same mass as AZA-3, but produced different collision induced dissociation (CID) spectra. High resolution mass spectrometric measurements indicated that there is an unsaturation in the H, I ring system of AZA-43 distinguishing it from the classical AZA such as AZA-1, -2, and -3. Furthermore, the Spanish strain was different from the previously reported AZA profile of the species that consist of AZA-38 and AZ-39. In molecular phylogenetics, the Andalusian strain formed a monophyletic group together with other strains of Am. languida, but ITS sequences data revealed surprisingly high intragenomic variability. The first Andalusian case of AZA contamination of shellfish above the EU regulatory limit reported here clearly revealed the risk of azaspiracid poisoning (AZP) for this area and also for the Atlantic coast of Iberia and North Africa. The present study underlines the need for continuous monitoring of AZA and the organisms producing such toxins.

show abstract

Liquid chromatography–tandem mass spectrometry method for the detection of marine lipophilic toxins under alkaline conditions

Cited by 155 publications

References 24 publications

Improved Isolation Procedure for Azaspiracids from Shellfish, Structural Elucidation of Azaspiracid-6, and Stability Studies

Improved Isolation Procedure for Azaspiracids from Shellfish, Structural Elucidation of Azaspiracid-6, and Stability Studies

Identification of gymnodimine D and presence of gymnodimine variants in the dinoflagellate Alexandrium ostenfeldii from the Baltic Sea

Amphidoma languida (Amphidomatacea, Dinophyceae) with a novel azaspiracid toxin profile identified as the cause of molluscan contamination at the Atlantic coast of southern Spain

Contact Info

Product

Resources

About