Survey of historical New Zealand shellfish samples for accumulation of gymnodimine

Stirling, David

doi:10.1080/00288330.2001.9517047

Cited by 51 publications

(40 citation statements)

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“…The hydroxylated analogues, gymnodimine B (3) and C (4), have also been isolated from K. selliformis (Miles et al, 2000(Miles et al, , 2003. These gymnodimines can be present in filter-feeding shellfish throughout the year, and have been detected in large quantities in coastal waters of New Zealand (Stirling, 2001) and Tunisia (Bire et al, 2002;Ben Naila et al, 2012) after prolonged blooms of K. selliformis. Recently, 12-methylgymnodimine (5) was isolated from A. ostenfeldii originating from estuaries at the U.S. East Coast, which was the first report of gymnodimines in Alexandrium or any other dinoflagellate species besides K. selliformis (Van Wagoner et al, 2011).…”

Section: Introductionmentioning

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

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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.

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Section: Introductionmentioning

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

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“…Currently, LC-MS/MS methods are considered the methods of choice for cyclic imines analysis in shellfish (EFSA 2010). Several publications have reported LC-MS/MS methods for SPXs, GYMs, PnTXs and PtTXs (Cembella et al 1999, Takada et al 2001a, 2001b, Stirling 2001, Biré et al 2002, Aasen et al 2005, Ciminiello et al 2006, Villar Gonzalez et al 2006, Fux et al 2007, Gerssen et al 2009a, 2009b, Seiwood et al 2010). These methods are based on reversed-phase LC coupled with electrospray ionization MS used in either the selected ion monitoring (SIM) or the selected reaction monitoring (SRM) modes (EFSA 2010).…”

Section: Liquid Chromatography With Tandem Mass Spectrometry Detectiomentioning

confidence: 99%

“…Incidents involving non-specific symptoms including gastric distress and tachycardia, such as the one recorded in Nova Scotia, Canada, raise reasonable suspicions, but they cannot be attributed to the consumption of SPX-containing shellfish, because similar episodes in the area took place at times when MBA results indicated absence of SPXs (Richard et al 2001). In New Zealand, which was the first country to detect the presence of GYMs in shellfish, the regulatory authorities decided that GYM-contaminated shellfish do not pose a human intoxication risk, as, according to their epidemiological data, no illnesses after shellfish consumption had been observed during the contamination incident (Mackenzie et al 1996, Stirling 2001. Moreover, in Rangaunu Harbour, New Zealand, where PnTXs had been detected in oysters at considerable concentrations, no adverse effects to consumers' health have been noticed (Munday et al 2004).…”

Section: Toxicity Of Cyclic Iminesmentioning

confidence: 99%

Cyclic imines, as emerging marine toxins: Chemical properties, distribution, toxicological aspects and detection methods

Chatzianastasiou¹,

Katikou²,

Zacharaki³

et al. 2017

J Hellenic Vet Med Soc

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Shellfish and, specifically, bivalve molluscs are a food commodity of great nterest for both commercial and public health reasons. They consume microalgae from surrounding waters, which are generally beneficial for aquaculture, but they comprise certain toxin-producing species. These species produce marine toxins which, via the filter-feeding mechanism of bivalve molluscs, accumulate in their tissues. This accumulation is more intense andmore dangerous for public health during the so-called periods of Harmful Algal Blooms (HABs) when the microalgal population grows. According to their chemical structure, marine toxins are classified into 8 groups, one of which is the cyclic imines. These lipophilic toxins were accidentally discovered during routine bioassays for the detection of other lipophilic marine toxins due to the induction of neurological symptoms and acute death in mice. They include the following subgroups: Spirolides (SPX), gymnodimines (GYM), pinnatoxins (PnTX), pteriatoxins (PtTX), prorocentrolides and spiro-prorocentrimines. The European Union (EU) is more concerned about the first three subgroups, because, in contrast with the latter three, they have already been detected in Europe or there is strong evidence supporting their presence. Spirolides are produced by the dmof\a.ge\\ate Alexandrìum ostenfeldii/peruvianum, gymnodimines by the dinoflagellate Karenia selliformis and pinnatoxins by a peridinoid dinoflagellate recently described in the new genus Vulcanodinium spp.. Although there is insufficient information regarding the geographical distribution of cyclic imines, the fact that they have been detected on multiple occasions in European waters, in combination with their aforementioned acute toxicity in mice after intraperitoneal injection, has established them, at least within the EU, as a topic of profound scientific research. In spite of their acute toxicity in mice, no incident of human intoxication has been attributed to cyclic imines. Presently, the EU has neither set any Maximum Permissible Limits for the concentration of cyclic imines in shellfish nor appointed any reference method for their detection and quantification. Currently, the methods applied are biological, biochemical and chemical. The biological method is a bioassay, which is conducted via the intraperitoneal injection of mice with an extract containing the compound under examination and it detects total toxicity. This properly is essential for the detection of unknown toxins, but the use of laboratory animals raises serious ethical concerns and animal welfare issues. The biochemical method is based on competition between cyclic imines and a fluorescently labelled compound for binding to receptors of the electric ray Torpedo marmorata. Finally, in respect of chemical methods, liquid chromatography with tandem mass spectrometry detection (LC-MS/MS) is the most significant method because it is fast, of high repeatability and specificity.

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“…However, lC-MS/MS methods are presently refined that allow highly sensitive detection of GYM, Pntx, Pttx, and SPx (Aasen et al, 2005a;Alvarez et al, 2010;Bire et al, 2002;Cembella et al, 1999;Ciminiello et al, 2006;Fux et al, 2007;Gerssen et al, 2009a,b;MacKenzie et al, 2002;Quilliam et al, 2001;Stirling, 2001;takada et al, 2001a,b;Villar Gonzalez et al, 2006;Miles et al, 2010).…”

Section: Symptomsmentioning

confidence: 99%

A roadmap for hazard monitoring and risk assessment of marine biotoxins on the basis of chemical and biological test systems

Daneshian

2013

ALTEX

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Summary Aquatic food accounts for over 40% of global animal food products, and the potential contamination with toxins of algal origin -marine biotoxins -poses a health threat for consumers. The gold standards to assess toxins in aquatic food have traditionally been in vivo methodssingle marine biotoxins or combinations of marine biotoxins and intoxication symptomatology as well as monitoring the "success" of controls implemented during fishery and aquaculture production, processing, and retailing. For this reason, a workshop was organized in ermatingen, Switzerland by the Center for Alternatives to Animal testing -europe (CAAteurope) within the framework of the transatlantic think tank for toxicology (t 4 ).In contrast to other food products where hygiene and potential contamination with microbes or mold toxins is the prime issue, the emphasis in aquatic products (shellfish and finfish) is, beyond viral and bacterial contaminations, primarily placed on potential contamination with marine biotoxins owing to the numerous and recurring human intoxications.The gold standards to assess toxins in aquatic food have traditionally been in vivo methods, i.e., the mouse and the rat bioassays. Besides the ethical issues of in vivo bioassays there are specific difficulties, e.g., different exposure route (i.p. versus oral), low inter-species comparability, high intra-species variability, and questionable extrapolation of quantitative risk to humans, thus highlighting the need for the development of more reliable detection and quantification methods. Based on this reasoning, the european Food Safety Authority (eFSA) advocates the use of an analytical method, i.e., LC-MS (Liquid Chromatography coupled Mass Spectrometry), as a substitute for in vivo bioassays for almost all classes of marine toxins. However, although lC-MS is a very sensitive method that has the advantages of being able to detect multiple toxins in a single analysis and being good for confirming the identity of toxins, the quality of quantitative analysis is dependent on the availability of calibration standards. While many new toxin structural analogues have been detected and identified using LC-MS, this technique -as with most other methods -is not good at detecting new toxin types. When new toxin analogues are detected but accurate standards are not yet available, only an approximate quantitation is possible using estimated response factors.For the purpose of risk assessment of food, however, it is imperative to focus on the possible adverse effects, independent of whether they stem from one toxin or a combination of toxins. As toxicity is defined by functional and structural changes of biological systems, the development of a human-relevant in vitro system for appropriate risk assessment of marine biotoxins in seafood stands to reason. Moreover, poor correlation of human intoxications, of acute symptomatology and long-term adverse effects, and of predictive in vitro, in vivo, and analytical detection methodologies of marine biotoxins stems not least from a...

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Survey of historical New Zealand shellfish samples for accumulation of gymnodimine

Cited by 51 publications

References 5 publications

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

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

Cyclic imines, as emerging marine toxins: Chemical properties, distribution, toxicological aspects and detection methods

A roadmap for hazard monitoring and risk assessment of marine biotoxins on the basis of chemical and biological test systems

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