Malonylniphimycin: Macrolide Antibiotic from Streptomyces hygroscopicus B-7: Physico-chemical Properties and Structure Elucidation.

The Journal of Antibiotics
1997.0

Abstract

In the course of our screening program for active substances of microbial origin, an antifungal antibiotic complex was isolated from the culture broth of a strain of Streptomyces hygroscopicus B-7 and designated AK-B7. It is a complex of non-polyenic antifungal antibiotics. In the previous paper, taxonomy of the producing organism S. hygroscopicus B-7 and biological activity of the antibiotic complex were presented. In this report we describe the production, isolation, physico-chemical properties and the structure elucidation of the non-polyenic antibiotic AK-B7-3 (malonylniphimycin) through the use of two-dimensional NMR techniques. Malonylniphimycin was isolated as a colorless powder with melting point of 114-116°C, optically active with [α]₅₅⁰ value of +36.5° (c=0.5, MeOH), soluble in lower alcohols, dimethylsulfoxide, N,N-dimethylformamide but insoluble in ethyl acetate, chloroform and water, giving positive reactions to potassium permanganate, 3% vanillin-sulphuric acid solution, Dragendorf and Sakaguchi test. Its UV spectrum in MeOH showed absorption maximum at 232nm (ε 2200). Structural analysis via 2D NMR (¹H COSY, ¹H-¹³C COSY) revealed two malonyl residues at C-23 and C-19. Malonylniphimycin possesses biological activity against Gram-positive bacteria, fungi and yeasts, but lower activity than niphimycin A.

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