Title: Lophotoxin
CAS Registry Number: 78697-56-0
CAS Name: (1R,2S,4S,10R,12R,14R,15R)-2-(Acetyloxy)-12-methyl-4-(1-methylethenyl)-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-diene-7-carboxaldehyde
Additional Names: LTX
Molecular Formula: C22H24O8
Molecular Weight: 416.42
Percent Composition: C 63.45%, H 5.81%, O 30.74%
Literature References: A novel neuromuscular toxin isolated from several spp of Pacific gorgonians (sea fans and whips) of the genus Lophogorgia. Although it belongs to the cembrene class of diterpenoids, the ability of LTX to cause irreversible postsynaptic blockade at the neuromuscular junction resembles the mode of action of the protein snake venom a-bungarotoxin (cf. bungarotoxins). Isoln and structure: W. Fenical et al., Science 212, 1512 (1981). Molecular mode of action: J. R. Smythies, Med. Hypotheses 7, 1457 (1981), C.A. 96, 137527 (1982). Toxicity study: P. Culver, R. S. Jacobs, Toxicon 19, 825 (1981). Description of the cytotoxic, ichthytoxic, and antibacterial activity of alcoholic extracts of gorgonians: R. S. Jacobs et al., Fed. Proc. 40, 26 (1981); V. J. Paul, W. Fenical, J. Org. Chem. 45, 3401 (1981).
Properties: White needles, mp 164-166°. [a]D27 +14.2° (c = 1.7 in chloroform). LD50 in mice (mg/kg): 8.9 s.c. (Culver, Jacobs).
Melting point: mp 164-166°
Optical Rotation: [a]D27 +14.2° (c = 1.7 in chloroform)
Toxicity data: LD50 in mice (mg/kg): 8.9 s.c. (Culver, Jacobs) |