Structural Assignment and Total Synthesis of Azaspiracid‐1

Azaspiracids (AZA) are polyether marine toxins that accumulate in various shellfish species and have been associated with severe gastrointestinal human intoxications since 1995. This toxin class has since been reported from several countries, including Morocco and much of western Europe. A regulatory limit of 160 µg AZA/kg whole shellfish flesh was established by the EU in order to protect human health; however, in some cases, AZA concentrations far exceed the action level. Herein we discuss recent advances on the chemistry of various AZA analogs, review the ecology of AZAs, including the putative progenitor algal species, collectively interpret the in vitro and in vivo data on the toxicology of AZAs relating to human health issues, and outline the European legislature associated with AZAs.

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“…1) 10, 11. A detailed review of the synthetic approach and structure revision has recently been published 12.…”

Section: Chemistry Of Azasmentioning

confidence: 99%

Azaspiracid Shellfish Poisoning: A Review on the Chemistry, Ecology, and Toxicology with an Emphasis on Human Health Impacts

et al. 2008

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“…A few years after this unattributed toxic incident, the first member of a novel group of marine biotoxins designated as ''azaspiracid'' (AZA) was isolated and characterized from shellfish (as AZA-1) (Satake et al, 1998) and later structurally revised Frederick et al, 2007). Following confirmation of AZA-1 as the cause of human poisoning, other cases of intoxication from consumption of mussels from Ireland, France and Italy were also unambiguously attributed to the AZP syndrome (James et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

Characterization of azaspiracids in plankton size-fractions and isolation of an azaspiracid-producing dinoflagellate from the North Sea

et al. 2009

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“…Yet subsequent chemical analysis of contaminated mussels found only insignificant levels of DSP toxins. The causative toxin was later isolated and structurally characterised from toxic mussels from Ireland (Satake et al, 1998), and later structurally revised Frederick et al, 2007), as a nitrogen-containing polyether with a unique spiral ring assembly, a cyclic amine, and a carboxylic acid. This novel marine biotoxin was named azaspiracid (AZA).…”

Section: Introductionmentioning

confidence: 99%

Azadinium spinosumgen. et sp. nov. (Dinophyceae) identified as a primary producer of azaspiracid toxins

Tillmann

Elbrächter

Krock

et al. 2009

European Journal of Phycology

252

218

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Azaspiracids (AZAs) are a group of lipophilic marine biotoxins associated with human incidents of shellfish poisoning. During a research cruise to the North Sea, we analysed size-fractionated plankton for AZA by mass spectrometry and successfully isolated an AZA-producing dinoflagellate from the east coast of Scotland. As shown previously, an axenic culture of this dinoflagellate produces AZA 1, AZA 2 and an isomer of AZA 2. Here we give a taxonomic description of this new taxon Azadinium spinosum gen. et sp. nov., as a de novo producer of AZAs. Azadinium spinosum is a small (12-16 mm length and 7-11 mm width) peridinin-containing photosynthetic dinoflagellate with a superficial resemblance under light microscopy to gymnodinioids, but with a thin theca. The large nucleus is spherical and located posteriorly, whereas the single chloroplast is parietal, lobed, and typically extends into both the epi-and hyposome. The Kofoidian thecal tabulation is APC, 4 0 , 3a, 6 00 , 6C, 5?S, 6 000 , 2 0000 . This plate pattern has an epithecal affinity to the Peridiniales and a hypothecal affinity to the Gonyaulacales, but is distinctly different from described dinoflagellate genera. The assignment of A. spinosum to the dinoflagellates is supported by molecular phylogenetic analysis of four genes, SSU rDNA, LSU rDNA (D1/D2 region), ITS and cytochrome oxidase (subunit 1) (COI). In agreement with the morphological description, phylogenetic analysis did not show any particularly close affiliation to the Peridiniales or Gonyaulacales, nor to any other dinoflagellate order represented in molecular databases. Consequently, we erected a new genus, Azadinium, for this taxon. However the ordinal affiliation of the genus is uncertain. This study represents the first description and confirmation of a new dinoflagellate species capable of producing AZA and is thus an important advance in surveillance programmes for toxigenic microalgae and toxins of human health significance.

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Structural Assignment and Total Synthesis of Azaspiracid‐1

Cited by 6 publications

References 15 publications

Azaspiracid Shellfish Poisoning: A Review on the Chemistry, Ecology, and Toxicology with an Emphasis on Human Health Impacts

Azaspiracid Shellfish Poisoning: A Review on the Chemistry, Ecology, and Toxicology with an Emphasis on Human Health Impacts

Characterization of azaspiracids in plankton size-fractions and isolation of an azaspiracid-producing dinoflagellate from the North Sea

Azadinium spinosumgen. et sp. nov. (Dinophyceae) identified as a primary producer of azaspiracid toxins

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