Metabolic products of microorganisms. 222 .BETA.-Oxotryptamine derivatives isolated from Streptomyces ramulosus.

The Journal of Antibiotics
1983.0

Abstract

Besides acetomycin, Streptomyces ramulosus Tu 34 produces several other metabolites which were extracted from the culture broth with 1-butanol at pH 8 and separated on silica gel. In chemical screening, two compounds, 34-M and 34-N, were identified as β-oxotryptamine derivatives. 34-N was purified via Sephadex LH-20 chromatography and identified as N-acetyl-β-oxotryptamine (1). 34-M was purified through silica gel chromatography and crystallization, and identified as N-acetyl-α-hydroxy-β-oxotryptamine (2). Their structures were elucidated by physicochemical data (melting point, optical rotation, molecular formula, IR, UV, EI-MS), ¹H and ¹³C NMR spectra, and derivative preparation (diacetate 3 and dimethyl acetal 4). The metabolites 1 and 2 indicate that S. ramulosus produces enzymes capable of oxidizing tryptophan or tryptamine derivatives in the side chain. The existence of 1 supports the hypothesis that N-acyl-β-oxotryptamines might be bioconverted to indolyloxazoles, common metabolites of Streptomyces. Neither 1 nor 2 exhibited antibacterial or antifungal activity.

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