Characterization of multiple isolates from an Alexandrium ostenfeldii bloom in The Netherlands

Waal, Dedmer B. Van de; Tillmann, Urban; Martens, Helge; Krock, Bernd; Scheppingen, Yvonne van; John, Uwe

doi:10.1016/j.hal.2015.08.002

Cited by 64 publications

(72 citation statements)

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“…Two of the gymnodimines of the Dutch A. ostenfeldii (GYM A and 12-Me-GYM A) have been described in the previous analysis of the same population [32]. However, our in-depth analysis revealed the presence of two additional gymnodimines so far unreported.…”

Section: Discussionsupporting

confidence: 46%

Toxin Variability Estimations of 68 Alexandrium ostenfeldii (Dinophyceae) Strains from The Netherlands Reveal a Novel Abundant Gymnodimine

et al. 2017

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Alexandrium ostenfeldii is a toxic dinoflagellate that has recently bloomed in Ouwerkerkse Kreek, The Netherlands, and which is able to cause a serious threat to shellfish consumers and aquacultures. We used a large set of 68 strains to the aim of fully characterizing the toxin profiles of the Dutch A. ostenfeldii in consideration of recent reports of novel toxins. Alexandrium ostenfeldii is known as a causative species of paralytic shellfish poisoning, and consistently in the Dutch population we determined the presence of several paralytic shellfish toxins (PST) including saxitoxin (STX), GTX2/3 (gonyautoxins), B1 and C1/C2. We also examined the production of spiroimine toxins by the Dutch A. ostenfeldii strains. An extensive liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis revealed a high intraspecific variability of spirolides (SPX) and gymnodimines (GYM). Spirolides included 13-desMethyl-spirolide C generally as the major compound and several other mostly unknown SPX-like compounds that were detected and characterized. Besides spirolides, the presence of gymnodimine A and 12-Methyl-gymnodimine A was confirmed, together with two new gymnodimines. One of these was tentatively identified as an analogue of gymnodimine D and was the most abundant gymnodimine (calculated cell quota up to 274 pg cell−1, expressed as GYM A equivalents). Our multi-clonal approach adds new analogues to the increasing number of compounds in these toxin classes and revealed a high strain variability in cell quota and in toxin profile of toxic compounds within a single population.

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Section: Discussionsupporting

confidence: 46%

Toxin Variability Estimations of 68 Alexandrium ostenfeldii (Dinophyceae) Strains from The Netherlands Reveal a Novel Abundant Gymnodimine

et al. 2017

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“…The genetic basis for cyclic imine production is presently not very well understood. Previously it was found that A. ostenfeldii isolates from U.S East Coast estuaries and brackish coastal waters in the Netherlands produce both PSP toxins and cyclic imines, spirolides as well as various gymnodimines (Van Wagoner et al, 2011;Van de Waal et al, 2015). The respective isolates are phylogenetically closely related to A. ostenfeldii populations from the Baltic Sea , which motivated us to search for gymnodimines in Baltic A. ostenfeldii cultures.…”

Section: Resultsmentioning

confidence: 99%

“…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). Besides 12-methylgymnodimine isolated from an A. ostenfeldii strain from the U.S. East Coast, gymnodimine A and 12-methylgymnodimine have been found together with spirolides in isolates from a recent bloom of A. ostenfeldii in the Netherlands ( Van de Waal et al, 2015). Moreover, novel fatty acid ester metabolites of gymnodimine A (de la and several unknown gymnodimine-like compounds (McCarron et al, 2014) have been detected in shellfish by liquid chromatographyemass spectrometry (LCeMS).…”

Section: Introductionmentioning

confidence: 99%

“…Several unknown analogues have also been described together with known spirolides (Sleno et al, 2004;Almandoz et al, 2014;Tillmann et al, 2014;Rundberget et al, 2011). Certain A. ostenfeldii isolates may produce both spirolides and gymnodimines (Van Wagoner et al, 2011;Van de Waal et al, 2015). Due to their structural similarity, a possible explanation may be a common biosynthetic pathway.…”

Section: Introductionmentioning

confidence: 99%

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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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“…Furthermore, there was no clear link between the distribution of likely toxigenic source organisms and the macrocyclic imine toxin SPX-1, elsewhere attributed to Alexandrium ostenfeldii (Cembella et al, 1999(Cembella et al, , 2000. This apparent lack of coherence between the presence of the toxin and the associated taxon also applied to GYM, usually produced by Karenia selliformis (Medhioub et al, 2009;Miles et al, 2003), or in brackish water by A. ostenfeldii (Harju et al, 2016;Van de Waal et al, 2015;Van Wagoner et al, 2011). High amounts of these toxins (Table 2) were detected in only one sample, and this simultaneous presence may indicate A. ostenfeldii as producer species of both toxins (Harju et al, 2016;Van de Waal et al, 2015;Van Wagoner et al, 2011).…”

Section: Discussionmentioning

confidence: 99%

Toxigenic algae and associated phycotoxins in two coastal embayments in the Ebro Delta (NW Mediterranean)

et al. 2016

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Characterization of multiple isolates from an Alexandrium ostenfeldii bloom in The Netherlands

Cited by 64 publications

References 53 publications

Toxin Variability Estimations of 68 Alexandrium ostenfeldii (Dinophyceae) Strains from The Netherlands Reveal a Novel Abundant Gymnodimine

Toxin Variability Estimations of 68 Alexandrium ostenfeldii (Dinophyceae) Strains from The Netherlands Reveal a Novel Abundant Gymnodimine

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

Toxigenic algae and associated phycotoxins in two coastal embayments in the Ebro Delta (NW Mediterranean)

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