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In previous papers1,2) we described the derivation of new macrolide antibiotics using the technique of hybrid biosynthesis. In a series of further trials, we obtained two new compounds by incubating a daunomycin producer Streptomyces sp. KA-464 in the presence of cerulenin with the 16-membered lactone protylonolide, which is a precursor of tylosin biosynthesis and possesses a structure corresponding to the aglycone moiety. This paper describes the isolation and structures of a new macrolide aglycone and a macrolide antibiotic. Streptomyces sp. strain KA-464 (KCC U-0202) was cultured in a daunomycin production medium (4% glucose, 1.5% dried yeast, 0.2 NaCI, 0.1% KH2PO4i 0.1% CaCO3, 0.01 MgSO4.7H20, 0.001 % FeSO4.7H20, 0.001 ZnSO4.7H2O, 0.001 % CuSO4.5H20, pH 7.0). To the culture medium 801&g/ml of cerulenine was added initially and at a 24-hour interval to prevent the de novo synthesis of the aglycone moiety, the daunomycinones. After 72 hours of cultivation, 100 ,ug/ml of protylonolide was added and the cultivation was continued for a further 48 hours. The cultured broth (5 liters) was centrifuged to separate cells. The cells were extracted with one liter of acetone, and the extract was concentrated in vacuo. The residue was combined with the supernatant, which was then extracted with ethyl acetate. The combined organic extracts were evaporated to dryness.

Hybrid biosynthesis of a new macrolide antibiotic by a daunomycin-producing microorganism.