Spiroimine shellfish poisoning (SSP) and the spirolide family of shellfish toxins: Isolation, structure, biological activity and synthesis

Guéret, Stéphanie M.; Brimble, Margaret A.

doi:10.1039/c005400n

Cited by 68 publications

(55 citation statements)

References 80 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…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). Compared to other cyclic imines, such as the structurally related pinnatoxins (Araoz et al, 2011) and spirolides (Gueret and Brimble, 2010), knowledge on gymnodimines is still limited. Gymnodimine A is a fast-acting toxin with high intraperitoneal toxicity in mice (LD 50 of 80e96 mg/kg) (Kharrat et al, 2008;Munday et al, 2004) and similar bioactivities have been reported from other cyclic imines (Munday, 2008).…”

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

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: 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

“…Other positions where structural variability was observed for spirolides C and D are 13 and 19 on the spiroketal ring system, with the presence or absence of methyl substituents, and 27, where hydroxy and keto substituents were evidenced in some cases. The second spirolide group contains the biologically inactive spirolides E and F, which present the same chemical features as spirolides A and B, respectively, except for the cyclic imine that becomes an acyclic aminoketone (reviewed by Guéret and Brimble 2010). These structural changes suggest that they are probably shellfish metabolites of spirolides A and B.…”

Section: Spirolides Chemical Characteristics Of Spirolide Toxinsmentioning

confidence: 95%

Spirolides and Cyclic Imines: Toxicological Profile

Molgó

Benoit

Aráoz

et al. 2016

Marine and Freshwater Toxins

View full text Add to dashboard Cite

“…Studies directed at the total synthesis of pinnatoxins 68 and spirolides 69,70 have been reviewed previously. The aim of this section will be to provide a broader overview of the total synthesis efforts and an analysis of the most recent progress in the field.…”

Section: Synthetic Chemistry and Chemical Stability Of CI Toxinsmentioning

confidence: 99%

Synthesis and biology of cyclic imine toxins, an emerging class of potent, globally distributed marine toxins

et al. 2015

View full text Add to dashboard Cite

From a small group of exotic compounds isolated only two decades ago, Cyclic Imine (CI) toxins have become a major class of marine toxins with global distribution. Their distinct chemical structure, biological mechanism of action, and intricate chemistry ensures that CI toxins will continue to be the subject of fascinating fundamental studies in the broad fields of chemistry, chemical biology, and toxicology. The worldwide occurrence of potent CI toxins in marine environments, their accumulation in shellfish, and chemical stability are important considerations in assessing risk factors for human health. This review article aims to provide an account of chemistry, biology, and toxicology of CI toxins from their discovery to the present day.

show abstract

Spiroimine shellfish poisoning (SSP) and the spirolide family of shellfish toxins: Isolation, structure, biological activity and synthesis

Cited by 68 publications

References 80 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

Spirolides and Cyclic Imines: Toxicological Profile

Synthesis and biology of cyclic imine toxins, an emerging class of potent, globally distributed marine toxins

Contact Info

Product

Resources

About