1354. Bostrycoidin

Nomenclature

CAS number: 4589-33-7
6,9-Dihydroxy-7-methoxy-3-methylbenz[g]isoquinoline-5,10-dione; 5,8-dihydroxy-6-methoxy-3-methyl-2-aza-9,10-anthraquinone.
C15H11NO5; mol wt 285.25.
C 63.16%, H 3.89%, N 4.91%, O 28.04%.

Description and references

Antibiotic substance produced by Fusarium bostrycoides: Hamilton et al., Antibiot. Chemother. 3, 853 (1953); Cajori et al., J. Biol. Chem. 208, 107 (1954). Structure: Arsenault, Tetrahedron Lett. 1965, 4033. Synthesis: D. W. Cameron et al., ibid. 21, 5089 (1980).

Chemical structure

Properties

Dark red crystals; mp 243-244°, changes to purple in alkaline medium, yellow in acid medium. Stable at room temp and withstands autoclaving. Insol in water; sol in abs ethanol and in 60% ethanol; moderately sol in dioxane, benzene, acetone, chloroform, carbon tetrachloride. Soluble in aq sodium carbonate solns. Partly sol in corn oil. Active in vitro against Mycobacterium tuberculosis. Serum seems to interfere.