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

被引：60

作者：

Gueret, Stephanie M. ^{[1
]}

Brimble, Margaret A. ^{[1
]}

机构：

[1] Univ Auckland, Dept Chem, Auckland 1023, New Zealand

来源：

NATURAL PRODUCT REPORTS | 2010年 / 27卷 / 09期

关键词：

DINOFLAGELLATE ALEXANDRIUM-OSTENFELDII; HARMFUL ALGAL BLOOMS; LIQUID-CHROMATOGRAPHY; PRECHROMATOGRAPHIC OXIDATION; QUANTITATIVE-DETERMINATION; MARINE TOXINS; PART I; DINOPHYCEAE; TOXICITY; GYMNODINIUM;

D O I：

10.1039/c005400n

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Spirolides are metabolites of the dinoflagellates Alexandrium ostenfeldii and Alexandrium peruvianum. Spirolides (A-D) were isolated from the digestive glands of contaminated mussels ( Mytilus edulis), scallops (Placopecten magellanicus) and toxic plankton from the east coast of Nova Scotia in Canada. Fourteen members of the spirolide family of marine biotoxins have since been identified from around the world. The relative stereochemistry of these compounds was established via molecular modelling and NMR studies. Related marine toxins containing a spiroimine unit have been classified as fast-acting toxins and the spirolides also target muscarinic and nicotinic acetylcholine receptors and are weak activators of L-type transmembrane Ca2+ channels. The spirolides are macrocycles that are comprised of two parts: a bis-spiroacetal moiety and an unusual 6,7-bicyclic spiroimine.

引用

页码：1350 / 1366

页数：17

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