6999. Palytoxin
Nomenclature
Description and references
Potent toxin isolated from zoanthid coral of the genus Palythoa that is the most poisonous non-proteinaceous substance known. Isoln from “Limu-make-o-Hana”, the Hawaiian name for the highly toxic coelenterate Palythoa toxica: R. E. Moore, P. J. Scheuer, Science 172, 495 (1971). Structure: R. E. Moore, G. Bartolini, J. Am. Chem. Soc. 103, 2491 (1981). Structure of palytoxin from P. tuberculosa of Okinawa (differs from palytoxin from P. toxica at two positions): D. Uemura et al., Tetrahedron Lett. 22, 2781 (1981). Proposed absolute configuration of 60 of the 64 chiral centers: R. E. Moore et al., J. Am. Chem. Soc. 104, 3776 (1982). Structure and stereochemistry: J. K. Cha et al., ibid. 7369. Discussion of the structural elucidation, see Y. Shimizu, Nature 302, 212 (1983); review: R. E. Moore, Prog. Chem. Org. Nat. Prod. 48, 82-202 (1985). Synthetic studies: Y. Kishi, Chem. Scr. 27, 573 (1987). Pharmacological study: P. N. Kaul et al., Proc. West. Pharmacol. Soc. 17, 294 (1974). Mechanism of action and treatment of palytoxin poisoning: J. A. Vick et al., Toxicol. Appl. Pharmacol. 34, 214 (1975). Mode of contractile action on vascular smooth muscle: K. Ito et al., Eur. J. Pharmacol. 46, 9 (1977). Depolarizing action on frog spinal cord: Y. Kudo, S. Shibata, Br. J. Pharmacol. 71, 575 (1980). Toxicology and toxicity studies: J. S. Wiles et al., Toxicon 12, 427 (1974); K. Ito et al., Arch. Int. Pharmacodyn. Ther. 258, 146 (1982). Brief review of biology: P. J. Scheuer, Acc. Chem. Res. 10, 33-39 (1977). Review of synthetic studies and conformational analysis: Y. Kishi, Pure Appl. Chem. 61, 313-324 (1989).
