Characterization of Spirolides A, C, and 13-Desmethyl C, New Marine Toxins Isolated from Toxic Plankton and Contaminated Shellfish

Hu, Tingmo; Burton, Ian W.; Cembella, Allan; Curtis, Jonathan M.; Quilliam, Michael A.; Walter, John A.; Wright, Jeffrey L. C.

doi:10.1021/np000416q

Cited by 175 publications

(174 citation statements)

References 8 publications

Supporting

Mentioning

169

Contrasting

Order By: Relevance

“…Four pairs of compounds differing with two mass units (m/z 508/510, 524/526, m/z 540/542, and 582/584) were observed, which could indicate the butenolide double bond variation of the analogues, which is typical for spirolides (Fig. S32) (Hu et al, 2001). Moreover, six sodium adducts were detected with the same retention time as measured for [MþH] þ .…”

Section: Other Gymnodimine Analoguesmentioning

confidence: 66%

“…The causative organism of spirolide production was identified as A. ostenfeldii isolated in Nova Scotia, Canada and Limfjord, Denmark (Cembella et al, 2000). Spirolides A, C, and 13-desmethylspirolide C were isolated from A. ostenfeldii cultures (Nova Scotia, Canada) and their structures were determined (Hu et al, 2001). Subsequently, various spirolide analogues have been isolated and structurally characterized from A. ostenfeldii (Aasen et al, 2005;MacKinnon et al, 2006a;Roach et al, 2009;Ciminiello et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

Section: Other Gymnodimine Analoguesmentioning

confidence: 66%

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

Toxicon

View full text Add to dashboard Cite

show abstract

“…The related group of macrocyclic imine toxins known as spirolides and originating from the dinoflagellate Alexandrium ostenfeldii was detected at some stations. Cultured isolates of A. ostenfeldii may produces a diversity of spirolides [13,14], but only 20-methylspirolide G and to a lesser extent 13-desmethylspirolide C were found in the North Sea field plankton samples. Somewhat surprisingly, spirolides A, B, C, D, and G were completely absent.…”

Section: Resultsmentioning

confidence: 96%

LC-MS-MS aboard ship: tandem mass spectrometry in the search for phycotoxins and novel toxigenic plankton from the North Sea

et al. 2008

View full text Add to dashboard Cite

Phycotoxins produced by various species of toxigenic microalgae occurring in the plankton are a global threat to the security of seafood resources and the health of humans and coastal marine ecosystems. This has necessitated the development and application of advanced methods in liquid chromatography coupled to mass spectrometry (LC-MS) for monitoring of these compounds, particularly in plankton and shellfish. Most such chemical analyses are conducted in land-based laboratories on stored samples, and thus much information on the near real-time biogeographical distribution and dynamics of phycotoxins in the plankton is unavailable. To resolve this problem, we conducted shipboard analysis of a broad spectrum of phycotoxins collected directly from the water column on an oceanographic cruise along the North Sea coast of Scotland, Norway, and Denmark. We equipped the ship with a triple-quadrupole linear ion-trap hybrid LC-MS-MS system for detection and quantitative analysis of toxins, such as domoic acid, gymnodimine, spirolides, dinophysistoxins, okadaic acid, pectenotoxins, yessotoxins, and azaspiracids (AZAs). We focused particular attention on the detection of AZAs, a group of potent nitrogenous polyether toxins, because the culprit species associated with the occurrence of these toxins in shellfish has been controversial. Marine toxins were analyzed directly from size-fractionated plankton net tows (20 μm mesh size) and Niskin bottle samples from discrete depths, after rapid methanolic extraction but without any further clean-up. Almost all expected phycotoxins were detected in North Sea plankton samples, with domoic acid and 20-methylspirolide G being most abundant. Although AZA was the least abundant of these toxins, the high sensitivity of the LC-MS-MS enabled detailed quantification, indicating that the highest amounts of AZA-1 were present in the southern Skagerrak in the 3-20 μm sizefraction. The direct on-board toxin measurements enabled isolation of plankton from stations with high AZA-1 levels and from the most suspicious size-fraction, i.e. most likely to contain the AZA-producer. A large number (>100) of crude cultures were established by serial dilution and later screened for the presence of AZAs after several weeks growth. From one crude culture containing AZA, a small dinoflagellate was subsequently isolated and brought into pure culture. We have thus proved that even sophisticated mass spectrometers can be operated in ship laboratories without any limitation caused by vibrations of the ship's engine or by wave movement during heavy seas at wind forces up to nine Beaufort. On-board LC-MS-MS is a valuable method for near real-time analysis of phycotoxins in plankton for studies on bloom dynamics and the fate of toxins in the food web, and for characterization and isolation of putatively toxigenic organisms.

show abstract

“…The causative organism of spirolide toxicity in shellfish was recently identified as A. ostenfeldii (Paulsen) Balech & Tangen (Cembella et al, 2000), and certain isolates of this species can produce a wide diversity of spirolides in unialgal batch culture (Hu et al, 2001). The association of spirolides with A. ostenfeldil is important, given that this species is broadly distributed, particularly in north temperate latitudes.…”

Section: Introductionmentioning

confidence: 99%

Discrimination of the toxigenic dinoflagellatesAlexandrium tamarenseandA. ostenfeldiiin co-occurring natural populations from Scottish coastal waters

John

Cembella

Hummert³

et al. 2003

European Journal of Phycology

119

View full text Add to dashboard Cite

Blooms of the toxic dinoflagellate Alexandrium tamarense (Lebour) Balech, a known producer of potent neurotoxins associated with paralytic shellfish poisoning (PSP), are common annual events along the Scottish east coast. The cooccurrence of a second Alexandrium species, A. ostenfeldii (Paulsen) Balech & Tangen is reported in this study from waters of the Scottish east coast. The latter species has been suspected to be an alternative source of PSP toxins in northern Europe. Recent identification of toxic macrocyclic imines known as spirolides in A. ostenfeldii indicates a potential new challenge for monitoring toxic Alexandrium species and their respective toxins in natural populations. In mixed phytoplankton assemblages, A/exandrium species are difficult to discriminate accurately by convention~llight microscopy.Species-specific rRNA probes based upon 18S and 28S ribosomal DNA sequences were developed for A. ostenfeldii and tested by dot-blot and fluorescence in situ hybridization (FISH) techniques. Hybridization patterns of A. ostenfeldii probes for cultured A/exandrium isolates, and cells from field populations from the Scottish east coast, were compared with those of rONA probes fOf A. tamarense and a universal dinoflagellate probe. A/exandrium cell numbers in field samples determined by whole-cell in situ hybridization were much lower than those determined by optical microscopy with the Utermohl-~ethod involving sedimentation chambers, but the results were highly correlated (e.g. r 2 =0.94; n =6 for A. tamarense).Determination of spirolides and PSP toxins by instrumental analysis on board ship demonstrated the presence of both toxin groups in plankton assemblages collected from surface waters near the Orkney Islands, and confirmed the association of A. ostenfeldii with spirolides in northern Europe. These results show that rRNA probes for A. tamarense and A. ostenfe/dii are useful, albeit only semi-quantitative, tools to detect and discriminate these species in field studies.

show abstract

Characterization of Spirolides A, C, and 13-Desmethyl C, New Marine Toxins Isolated from Toxic Plankton and Contaminated Shellfish

Cited by 175 publications

References 8 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

LC-MS-MS aboard ship: tandem mass spectrometry in the search for phycotoxins and novel toxigenic plankton from the North Sea

Discrimination of the toxigenic dinoflagellatesAlexandrium tamarenseandA. ostenfeldiiin co-occurring natural populations from Scottish coastal waters

Contact Info

Product

Resources

About