Gymnodimine C, an Isomer of Gymnodimine B, from <i>Karenia selliformis</i>

Miles, Christopher O.; Wilkins, Alistair L.; Stirling, David; MacKenzie, A. Lincoln

doi:10.1021/jf030101r

Cited by 102 publications

(93 citation statements)

References 4 publications

(9 reference statements)

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“…Accurate masses (Table 3) of 1 and the minor gymnodimine were consistent with the molecular formula for gymnodimine B/C, C 32 H 45 O 5 N (with 11 rings or double bond equivalents), previously isolated from K. selliformis (Miles et al, 2000(Miles et al, , 2003. However, the mass spectrometric fragmentation patterns differed from those expected for gymnodimine B/C based on reports from literature (Ben Naila et al, 2012).…”

Section: Resultssupporting

confidence: 80%

“…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. 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.…”

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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Section: Resultssupporting

confidence: 80%

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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“…New gymnodimine isomers, gymnodimine B and C, were isolated from Karenia selliformis (Fig. 4) (Miles et al, 2000(Miles et al, ,2003. The absolute configuration of gambieric acid from Gambierdiscus toxicus was determined by a combination of Mosher analysis, NMR, and chiral HPLC (Morohashi et al, 2000).…”

Section: F Othermentioning

confidence: 99%

The Biosynthesis of Polyketide Metabolites by Dinoflagellates

Rein

Snyder

2006

Advances in Applied Microbiology Volume 59

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“…1) have been identified from contaminated shellfish or from extracts of the dinoflagellate Karenia selliformis (12)(13)(14)(15). Similar to spirolides, gymnodimines contain a spirocyclic imine but, in contrast to spirolides, they bear a trisubstituted tetrahydrofuran embedded within a 16-membered macrocycle.…”

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confidence: 99%

Structural determinants in phycotoxins and AChBP conferring high affinity binding and nicotinic AChR antagonism

Bourne

Radić

Aráoz

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

147

194

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Spirolide and gymnodimine macrocyclic imine phycotoxins belong to an emerging class of chemical agents associated with marine algal blooms and shellfish toxicity. Analysis of 13-desmethyl spirolide C and gymnodimine A by binding and voltage-clamp recordings on muscle-type α1 2 βγδ and neuronal α3β2 and α4β2 nicotinic acetylcholine receptors reveals subnanomolar affinities, potent antagonism, and limited subtype selectivity. Their binding to acetylcholine-binding proteins (AChBP), as soluble receptor surrogates, exhibits picomolar affinities governed by diffusion-limited association and slow dissociation, accounting for apparent irreversibility. Crystal structures of the phycotoxins bound to Aplysia-AChBP (≈2.4Å) show toxins neatly imbedded within the nest of aromatic side chains contributed by loops C and F on opposing faces of the subunit interface, and which in physiological conditions accommodates acetylcholine. The structures also point to three major features: (i) the sequence-conserved loop C envelops the bound toxins to maximize surface complementarity; (ii) hydrogen bonding of the protonated imine nitrogen in the toxins with the carbonyl oxygen of loop C Trp147 tethers the toxin core centered within the pocket; and (iii) the spirolide bisspiroacetal or gymnodimine tetrahydrofuran and their common cyclohexene-butyrolactone further anchor the toxins in apical and membrane directions, along the subunit interface. In contrast, the sequence-variable loop F only sparingly contributes contact points to preserve the broad receptor subtype recognition unique to phycotoxins compared with other nicotinic antagonists. These data offer unique means for detecting spiroimine toxins in shellfish and identify distinctive ligands, functional determinants and binding regions for the design of new drugs able to target several receptor subtypes with high affinity.acetylcholine binding protein | marine phycotoxins | nicotinic acetylcholine receptor | pharmacological and structural analyses | seafood poisoning

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Gymnodimine C, an Isomer of Gymnodimine B, from Karenia selliformis

Cited by 102 publications

References 4 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

The Biosynthesis of Polyketide Metabolites by Dinoflagellates

Structural determinants in phycotoxins and AChBP conferring high affinity binding and nicotinic AChR antagonism

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