Identification of Fatty Acid Esters of Pectenotoxin-2 Seco Acid in Blue Mussels (<i>Mytilus edulis</i>) from Ireland

Wilkins, Alistair L.; Rehmann, Nils; Torgersen, Trine; Rundberget, Thomas; Keogh, Myra; Petersen, Dirk; Heß, Philipp; Rise, Frode; Miles, Christopher O.

doi:10.1021/jf060396j

Cited by 66 publications

(43 citation statements)

References 26 publications

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“…This species has recently been reported to produce PTX-2 in northwest Spain (Fernandez et al, 2006). The less toxic form (PTX-2SA) is a metabolite of PTX-2 and not known to be produced by phytoplankton directly (Miles et al, 2004;Wilkins et al, 2006). The presence of PTX-2SA in the phytoplankton samples analysed in this study may have resulted from the breakdown of PTX-2 after either being released into the water column or after the cells have died during the sampling or transportation processes, hence the observed significant relationship may not be relevant in this case.…”

Section: Discussionmentioning

confidence: 81%

Occurrence and seasonal variations of algal toxins in water, phytoplankton and shellfish from North Stradbroke Island, Queensland, Australia

Takahashi

Qian

Eaglesham

et al. 2007

Marine Environmental Research

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A number of marine microalgae are known to produce toxins that can accumulate in shellfish and when eaten, lead to toxic and potentially fatal reactions in humans. This paper reports on the occurrence and seasonal variations of algal toxins in the waters, phytoplankton and shellfish of Southeast Queensland, Australia. These algal toxins include okadaic acid (OA), domoic acid (DA), gymnodimine (GD), pectenotoxin-2 (PTX-2) and pectenotoxin-2-seco acid (PTX-2-SA), which were detected in the sampled shellfish and phytoplankton, via HPLC-MS/MS. Dissolved OA, PTX-2 and GD were also detected in the samples collected from the water column. This was the first occasion that DA and GD have been reported in shellfish, phytoplankton and the water column in Queensland waters. Phytoplankton tows contained both the toxic Dinophysis and Pseudo-nitzschia algae species, and are suspected of being the most likely producers of the OA, PTX-2s and DA found in shellfish of this area. The number of cells, however, did not correlate with the amount of toxins present in either shellfish or phytoplankton. This indicates that toxin production by algae varies with time and the species present and that number of cells alone cannot be used as an indicator for the presence of toxins. The presence of OA and PTX-2s were more frequently seen in the summer, while DA and GD were detected throughout the year and without any obvious seasonal patterns.

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Section: Discussionmentioning

confidence: 81%

Occurrence and seasonal variations of algal toxins in water, phytoplankton and shellfish from North Stradbroke Island, Queensland, Australia

Takahashi

Qian

Eaglesham

et al. 2007

Marine Environmental Research

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“…The accumulation of the parent toxins avoiding bio-transformation that occur in shellfish such as the esterification of okadaic acid into 7-O-acyl Okadaic ester (Suzuki et al, 1999), the conversion of PTX2 into PTX2 seco-acid (Suzuki et al, 2001;Miles et al, 2004) and PTX2 seco-acid ester derivatives (Wilkins et al, 2006). Similarly, the oxidation of YTX into 45-hydroxy-YTX and carboxy-YTX can be avoided, thereby reducing the number of analytes to be considered in the analytical procedure.…”

Section: Discussionmentioning

confidence: 99%

Field and mesocosm trials on passive sampling for the study of adsorption and desorption behaviour of lipophilic toxins with a focus on OA and DTX1

et al. 2008

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Abstract:It has been demonstrated that polymeric resins can be used as receiving phase in passive samplers designed for the detection of lipophilic marine toxins at sea and was referred to as solid phase adsorption toxin tracking (SPATT). The present study describes the uptake and desorption behaviour of the lipophilic marine toxins okadaic acid (OA) and dinophysistoxin-1 (DTX1) from Prorocentrum lima cultures by five styrene-divinylbenzene based polymeric resins Sepabeads ® SP850, Sepabeads ® SP825L, Amberlite ® XAD4, Dowex ® Optipore ® L-493 and Diaion ® HP-20. All resins accumulated OA and DTX1 from the P. lima culture with differences in adsorption rate and equilibrium rate. Following statistical evaluation, HP-20, SP850 and SP825L demonstrated similar adsorption rates. However, possibly due to its larger pore size, the HP-20 did not seem to reach equilibrium within 72 h exposure as opposed to the SP850 and SP825L. This was confirmed when the resins were immersed at sea for 1 week on the West Coast of Ireland. Furthermore, this work also presents a simple and efficient extraction method suitable to SPATT samplers exposed to artificial or natural culture media.

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“…The presence of 7-O-acyl derivates of okadaic acid and dinophysistoxins has been well documented, 20−23 and similar acyl esters of pectenotoxins, 24 brevetoxins, 25 and spirolides 26 have been reported. Because pinnatoxins also contain hydroxyl groups that could be acylated, it seems possible that similar metabolites of these compounds would occur.…”

Section: ■ Introductionmentioning

confidence: 99%

Identification of Pinnatoxins and Discovery of Their Fatty Acid Ester Metabolites in Mussels (Mytilus edulis) from Eastern Canada

McCarron

Rourke

Hardstaff

et al. 2012

J. Agric. Food Chem.

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Pinnatoxins are a group of fast-acting cyclic imine toxins previously identified in shellfish from Asia, the southern Pacific, and northern Europe. In this work pinnatoxins were detected in mussels from locations across the eastern coast of Canada. Pinnatoxin G (6) was the major structural variant present, sometimes at levels >80 μg/kg, whereas much lower levels of pinnatoxin A (1) were detected in some samples. Increased concentrations were observed following base hydrolysis of extracts, leading to the discovery by LC-MS of a range of fatty acid esters of 6. Information on the structures of these acylated derivatives was provided through a series of mass spectrometric experiments, supported by partial synthesis, and it is proposed that the compounds are 28-O-acyl esters of 6. Although acyl esters of a range of other phycotoxins are known to form as metabolites in shellfish, this is the first report of their existence for this particular toxin class. The occurrence of pinnatoxins in North American shellfish further highlights the international distribution of these toxins.

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Identification of Fatty Acid Esters of Pectenotoxin-2 Seco Acid in Blue Mussels (Mytilus edulis) from Ireland

Cited by 66 publications

References 26 publications

Occurrence and seasonal variations of algal toxins in water, phytoplankton and shellfish from North Stradbroke Island, Queensland, Australia

Occurrence and seasonal variations of algal toxins in water, phytoplankton and shellfish from North Stradbroke Island, Queensland, Australia

Field and mesocosm trials on passive sampling for the study of adsorption and desorption behaviour of lipophilic toxins with a focus on OA and DTX1

Identification of Pinnatoxins and Discovery of Their Fatty Acid Ester Metabolites in Mussels (Mytilus edulis) from Eastern Canada

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