Teleocidins
Title: Teleocidins
CAS Registry Number: 78474-55-2
Literature References: Indole alkaloid tumor promoters isolated from the mycelia of Streptomyces. Consists of teleocidin A (two isomers) and, the major component, teleocidin B (four isomers). The mixture is known as telocidin; the name is derived from its toxicity to fish (Teleostei). Isoln: M. Takashima, H. Sakai, Bull. Agric. Chem. Soc. Jpn. 24, 647 (1960). Resolution into A and B and their isomers: H. Fujiki, T. Sugimura, Cancer Surv. 2, 539 (1983). Structure: S. Sakai et al., Chem. Pharm. Bull. 32, 354 (1984). Abs config: Y. Endo et al., ibid. 358. Structure determn of B isomers: Y. Hitotsuyanagi et al., ibid. 4233. Structure-activity study: T. Kawai et al., J. Med. Chem. 35, 2248 (1992). Tumor promotion: H. Fujiki et al., Biochem. Biophys. Res. Commun. 90, 976 (1979); eidem, Carcinogenesis 3, 895 (1982). Review: H. Fujiki, T. Sugimura, Adv. Cancer Res. 49, 233-264 (1987).
Properties: White-crystal like powder, dec >61°. Easily sol in methanol, ethanol, ether, acetone, ethyl-acetate, benzene, chloroform, carbon tetrachloride; slightly sol in petroleum-ether, petroleum-benzine, ligroin. Almost insol in water, %5 HCl and 5% NaOH solution. LD50 orally in mice: 2 mg/kg (Takashima).
Toxicity data: LD50 orally in mice: 2 mg/kg (Takashima)
 
Derivative Type: Teleocidin B4
CAS Registry Number: 11032-05-6
CAS Name: (4S,7S,10R,13R)-13-Ethenyl-1,3,4,5,7,8,10,11,12,13-decahydro-4-(hydroxymethyl)-8,10,13-trimethyl-7,10-bis(1-methylethyl)-6H-benzo[g][1,4]diazonino[7,6,5-cd]indol-6-one
Additional Names: olivoretin D
Molecular Formula: C28H41N3O2
Molecular Weight: 451.64
Percent Composition: C 74.46%, H 9.15%, N 9.30%, O 7.09%
 
Derivative Type: Dihydroteleocidin B
Literature References: Structure: H. Harada et al., Bull. Chem. Soc. Jpn. 39, 1773 (1966). Tumor promoting activity: H. Fujiki et al., Proc. Natl. Acad. Sci. USA 78, 3872 (1981).
 
Use: use: Tumor promoting agent.

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