The preparation of certified calibration solutions for azaspiracid-1, -2, and -3, potent marine biotoxins found in shellfish

Perez, Ruth A; Rehmann, Nils; Crain, Sheila; LeBlanc, Patricia; Craft, Cheryl; MacKinnon, Shawna L.; Reeves, Kelley; Burton, Ian W.; Walter, John A.; Heß, Philipp; Quilliam, Michael A.; Melanson, Jeremy E.

doi:10.1007/s00216-010-4161-2

Cited by 39 publications

(41 citation statements)

References 26 publications

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“…The use of ethanol as an extraction solvent for the purification of azaspiracids has previously been reported. 33 Small scale tests with methanol and ethanol as extraction solvents showed that both solvents were equivalent in terms of extraction efficiency. Ethanol was chosen as the extraction solvent primarily to minimize the formation of side products, which can be significant when methanol is used as an extractant.…”

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.

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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.

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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.

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“…As such, many of the previous SAR studies have been confined to the study of AZA1 and its synthetic fragments (43,44); however, purified AZA2 and AZA3 have recently become available commercially (45).…”

Section: Acs Paragon Plus Environment Chemical Research Inmentioning

confidence: 99%

Comparative Effects of the Marine Algal Toxins Azaspiracid-1, -2, and -3 on Jurkat T Lymphocyte Cells

Twiner

El-Ladki

Kilcoyne

et al. 2012

Chem. Res. Toxicol.

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“…The aliquot had been set aside after NMR-characterization of the whole lot and was stored in methanol at −80 °C, a condition under which no degradation of AZA1 was observed during a 12-month stability study (Perez et al, 2010). The isolation procedure has been briefly described by Ronzitti et al (2007).…”

Section: Methodsmentioning

confidence: 99%

Combined oral toxicity of azaspiracid-1 and yessotoxin in female NMRI mice

Aasen

Espenes

Miles

et al. 2011

Toxicon

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For many years, the presence of yessotoxins (YTXs) in shellfish has contributed to the outcome of the traditional mouse bioassay and has on many occasions caused closure of shellfisheries. Since YTXs do not appear to cause diarrhoea in man and exert low oral toxicity in animal experiments, it has been suggested that they should be removed from regulation.Before doing so, it is important to determine whether the oral toxicity of YTXs is enhanced when present together with shellfish toxins known to cause damage to the gastrointestinal tract. Consequently, mice were given high doses of YTX, at 1 or 5 mg/kg body weight, either alone or together with azaspiracid-1 (AZA1) at 200 µg/kg. The latter has been shown to induce damage to the small intestine at this level. The combined exposure caused no clinical effects, and no pathological changes were observed in internal organs. These results correspond well with the very low levels of YTX detected in internal organs by means of LC-MS/MS and ELISA after dosing. Indeed, the very low absorption of YTX when given alone remained largely unchanged when YTX was administered in combination with AZA1. Thus, the oral toxicity of YTX is not enhanced in the presence of sub-lethal levels of AZA1.3

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The preparation of certified calibration solutions for azaspiracid-1, -2, and -3, potent marine biotoxins found in shellfish

Cited by 39 publications

References 26 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

Comparative Effects of the Marine Algal Toxins Azaspiracid-1, -2, and -3 on Jurkat T Lymphocyte Cells

Combined oral toxicity of azaspiracid-1 and yessotoxin in female NMRI mice

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