138. Actinobolin
Nomenclature
Description and references
Antibiotic produced by Streptomyces griseoviridus var atrofaciens; (+)-form is naturally occurring. Isoln and characterization: T. H. Haskell, Q. R. Bartz, Antibiot. Annu. 1958-1959, 505; T. H. Haskell et al., US 3043830 (1962 to Parke, Davis). Structural studies: Struck et al., Tetrahedron Lett. 1967, 1589; Munk et al., J. Am. Chem. Soc. 89, 4158 (1967). Structure: eidem, ibid. 90, 1087 (1968). Absolute configuration and chemistry: Antosz et al., ibid. 92, 4933 (1970). Crystal structure: J. B. Wetherington, J. W. Moncrief, Acta Crystallogr. B31, 501 (1975). Total synthesis: M. Yoshioka et al., J. Am. Chem. Soc. 106, 1133 (1984); eidem, Heterocycles 21, 151 (1984); R. S. Garigipati et al., J. Am. Chem. Soc. 107, 7790 (1985). Antibacterial activity and toxicity: R. F. Pittillo et al., Antibiot. Annu. 1958-1959, 497. Series of articles on antineoplastic activity: ibid. 515-532. Inhibition of protein synthesis: D. Smithers et al., Mol. Pharmacol. 5, 433 (1969). Experimental use as cariostat: D. E. Hunt et al., J. Dent. Res. 50, 371 (1971). Reduction of periodontal syndrome in mice, rats: J. H. Shaw, J. K. Ivimey, Arch. Oral Biol. 18, 357 (1973).
