Description and references

Polyene antibiotic complex containing at least eight pentaene compounds, which has been resolved into three pure components, filipin II, III (major), and IV, which differ in the number of hydroxyl groups present (8, 9, 9, resp.) and filipin I, a mixture of at least 5 components. Described as a single entity in the earlier literature. Initial isolation from Streptomyces filipenensis in Philippine soil: Whitfield et al., J. Am. Chem. Soc. 77, 4799 (1955). Early structural work: Dhar et al., Proc. Chem. Soc. London 1960, 310; Djerassi et al., Tetrahedron Lett. 1961, 383; Golding, Rickards, ibid. 1964, 2615; Dhar et al., J. Chem. Soc. 1964, 842; Ceder, Ryhage, Acta Chem. Scand. 18, 588 (1964). Separation of filipin complex into components: Bergy, Eble, J. Antibiot. 23, 414 (1970); see also Rickards et al., ibid. 603. Mechanism of action: R. W. Holz in Antibiotics vol. 5, pt. 2, F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 313-340. Filipin also interacts specifically with 3β-hydroxysterols (e.g. cholesterol): P. M. Elias et al., J. Histochem. Cytochem. 27, 1247 (1979); see also N. J. Severs, H. J. Simons, Nature 303, 637 (1983).

Properties

Derivative