Description and references

Powerful neurotoxin produced by the dinoflagellates Gonyaulax catenella, or G. tamarensis, the consumption of which causes the California sea mussel Mytilus californianus, the Alaskan butterclam Saxidomus giganteus and the scallop to become poisonous: Sommer et al., Arch. Pathol. 24, 537, 560 (1937); Schantz et al., Can. J. Chem. 39, 2117 (1961); Ghazarossian et al., Biochem. Biophys. Res. Commun. 59, 1219 (1974). These poisonous shellfish have been connected to instances of toxic “red-tides” where the high concentrations of algae discoloring the water were of the Gonyaulax genus. Isoln and partial characterization: Schantz et al., J. Am. Chem. Soc. 79, 5230 (1957); Mold et al., ibid. 5235. Purifn and biochemical data: Schantz et al., Biochemistry 5, 1191 (1966); Schantz, Ann. N.Y. Acad. Sci. 90, 843 (1960). pKa values: R. S. Rogers, H. Rapoport, J. Am. Chem. Soc. 102, 7335 (1980). Toxicity: G. S. Wiberg, N. R. Stephenson, Toxicol. Appl. Pharmacol. 2, 607 (1960). Structural studies: Schuett, Rapoport, J. Am. Chem. Soc. 84, 2266 (1962); Wong et al., ibid. 93, 4633, 7344 (1971). Revised structure: Schantz et al., ibid. 97, 1238 (1975); Bordner et al., ibid. 97, 6008 (1975). Pharmacology including study of sodium transport inhibition: Cheymol et al., Arch. Int. Pharmacodyn. Ther. 174, 393 (1968); Evans, Br. Med. Bull. 25, 263 (1969). Stereospecific total synthesis of dl-saxitoxin: H. Tanino et al., J. Am. Chem. Soc. 99, 2818 (1977); Y. Kishi, Heterocycles 14, 1477 (1980). Reviews: Kao, Pharmacol. Rev. 18, 997 (1966); Kao, Fed. Proc. 31, 1117 (1972); Narahashi, ibid. 1124, Evans, Int. Rev. Neurobiol. 15, 83 (1972); Y. Shimizu in Progress in the Chemistry of Natural Products vol. 45, W. Herz et al., Eds. (Springer-Verlag, New York, 1984) pp 239-246. See also Brevetoxins.

Derivative