Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate, Gymnodinium sp.

Seki, Tetsuya; Satake, Masayuki; MacKenzie, Lincoln; Kaspar, Heinrich F.; Yasumoto, Takeshi

doi:10.1016/0040-4039(95)01434-j

Cited by 283 publications

(260 citation statements)

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“…In addition, more connectivities were seen because of higher sample concentration. The observed 1 H and 13 C ppm values were similar to the values measured for the corresponding functional groups of gymnodimine A (2) (Seki et al, 1995) and 12-methylgymnodimine (5) (Van Wagoner et al, 2011). The comparison of the chemical shifts for 1, 2, and 5 is presented in the supporting information (Table S1).…”

Section: Nmr Analysessupporting

confidence: 52%

“…1) are cyclic imines produced by two species of marine planktonic dinoflagellates, Karenia selliformis and Alexandrium ostenfeldii. Gymnodimine A (2) was found first in New Zealand oysters in 1994 (Seki et al, 1995;Stewart et al, 1997), and since then, it has been detected in several other locations around the world, and supposedly produced by K. selliformis. The hydroxylated analogues, gymnodimine B (3) and C (4), have also been isolated from K. selliformis (Miles et al, 2000(Miles et al, , 2003.…”

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

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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: Nmr Analysessupporting

confidence: 52%

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

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“…[10] and associated with amnesic shellfish poisoning (ASP) in humans, was found at all stations over a wide concentration range from 0.5 to 12,800 ng per plankton net tow (approximately 2500 L of seawater filtered). The macrocyclic imine gymnodimine and related analogues, which occur primarily in temperate waters around New Zealand [11] but also the Mediterranean [12], in association with the dinoflagellate Karenia brevesulcata, were not detected. The related group of macrocyclic imine toxins known as spirolides and originating from the dinoflagellate Alexandrium ostenfeldii was detected at some stations.…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2008

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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.

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“…1 and 2). There are, however, other toxins associated with HAB species such as superoxide and (or) hydroxyl radicals (Oda et al 1992;Tanaka et al 1992), lipoteichoic acids with hemagglutinin activity (Ahmed et al 1995), and pentacyclic derivatives with a fused azine (Seki et al 1995). Other toxic effects of HAB algae have been documented but the toxins remain to be elucidated (e.g.…”

Section: Toxin Overviewmentioning

confidence: 99%

Marine algal toxins: Biochemistry, genetics, and molecular biology

Plumley

1997

Limnology & Oceanography

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Toxic compounds are frequently, but not universally, associated with alg,al blooms. Several dinoflagellate and diatom species are capable of toxin synthesis. Some bacteria are also capable of synthesizing at least one family of "algal" toxins. Previous work on algal toxins can be broadly grouped in four categories: observations on the variability in toxin production by single species or among strains of a species, frequently as a function of environmental growth conditions; isotope feeding studies to reveal the identity of the substrates that are precursors to the toxin compounds; the genetics of toxin production; and the pharmacological aspects of toxins. Information gleaned from these studies provides a firm foundation for launching more contemporaneous research efforts to understand the biochemistry and molecular biology of toxins. The goals are to develop an understanding of the machinery (i.e. the enzymes and the genes that encode them) required to synthesize toxins, to understand how this machinery is regulated by environmental conditions, and gain insights as to how the tox n biosynthetic genes evolved and(or) have been spread through the marine community.The production of toxic compounds is a common, but not universal, characteristic of harmful algal blooms (HABs). Surprisingly, only a few HAB toxins have been characterized and these are synthesized by only a limited number of algal species (Steidinger 1993). Toxigenic algae may, however, exert an inordinately large adverse impact on other members of the community because toxins can flow through aquatic food chains in a manner analogous to the movement of carbon or energy (Smayda 1992). Toxigenic algae thus may have significant impacts on ecosystem processes as toxins affect viability, growth, fecundity, and recruitment of a wide range of organisms.This manuscript is concerned with the biochemistry and genetics of toxin production by HAB species. Most information is for marine toxins as these have been better documented than the freshwater toxins. Saxitoxins, the causative agent of paralytic shellfish poisoning, are used as a model throughout this review as they are the best characterized marine toxin in terms of biochemistry and genetics. The physiology and ecology of the organisms that synthesize saxitoxins are also better documented than for other HAB species; this information permits a more robust interpretation of biochemical and genetic data for the saxitoxins than for other HAB toxins. Inauspiciously, very little is known about the molecular biology of HAB toxins, making this topic difficult to review. The goal in writing the molecular section was to interpret the biochemical, genetic, and physiological data in a context that would encourage and arouse others to Acknowledgments

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Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate, Gymnodinium sp.

Cited by 283 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

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

Marine algal toxins: Biochemistry, genetics, and molecular biology

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