The toxin tetramine from the "edible" whelk Neptunea antiqua.
The chemical nature of extracts of the marine gastropod Neptunea antiqua collected in the North Sea has been investigated. Amino acid analysis and spectroscopical studies (FAB MS, 1H NMR, 13C NMR and IR) on fractions purified by Biogel P-2 and Amberlite IR 120 column chromatography allowed the identification of 19 components. It was established that the water-soluble toxin responsible for poisonings, following ingestion of this snail, is tetramine (the tetramethylammonium ion present as an unknown salt). Contrary to what occurs in other Neptunea species (N. arthritica and N. intersculpta), tetramine was found not only in the salivary gland, but also in the remaining part of the animal, albeit in smaller concentration. In the isolated guinea-pig ileum assay, synergistic effects with other main components present (betaine, homarine) could not be demonstrated. Choline esters, believed to act synergistically in other Neptunea species, were not detected in Neptunea antiqua.
Anthoni
U
U
Department of General and Organic Chemistry, H.C. Orsted Institute, Copenhagen, Denmark.
Bohlin
L
L
Larsen
C
C
Nielsen
P
P
Nielsen
N H
NH
Christophersen
C
C
D000818:Animals; D001952:Bridged-Ring Compounds / Q000032:analysis* / Q000633:toxicity; D005260:Female; D006168:Guinea Pigs; D006801:Humans; D007082:Ileum / Q000187:drug effects; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000032:analysis* / Q000633:toxicity; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D051381:Rats; D012469:Salivary Glands / Q000032:analysis; D012758:Shellfish / Q000032:analysis*; D014020:Tissue Extracts / Q000032:analysis / Q000633:toxicity
D001952:Bridged-Ring Compounds; D008387:Marine Toxins; D014020:Tissue Extracts; C010349:tetramethylenedisulfotetramine