Characterization of New Glycosides from the Fermentation Broths of Streptomyces hygroscopicus

From the ¹ From the Department of Biological Sciences, Purdue University, West Lafayette, Indiana 47906

Four new glycosides, hygromycin C, and Compounds D, E, and F, isolated from the fermentation broths of Streptomyces hygroscopicus, have been partially characterized. Adsorption spectra in the infrared and ultraviolet regions and isolation of components after acid and basic hydrolysis indicated that the glycosides have a similar aglycon, composed of 3,4-dihydroxy--methylcinnamic acid or an isomer of this compound and neoinosamine-2, linked via an amide bond. An unusual feature was the dioxymethylene bridge previously reported to exist on the inosamine portion of hygromycin A, evidence for which was obtained for hygromycin C but not for Compounds D, E, or F. The carbohydrate component of Compound F was identified as D-glucose, and that of hygromycin C as L-fucose. The carbohydrate component of Compounds D and E was determined to be a 5-keto-6-deoxyarabohexose; it was not determined if this was the D or L form. A number of free phenolic compounds were found in the ether-soluble extract of acidified broths and two of these were identified as p-hydroxybenzoic acid and 3,4-dihydroxy--methylcinnamic acid.

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