Metabolic products of microorganisms. 246. 2880-II, a metabolite related to ferulic acid from Streptomyces griseoflavus.

The Journal of Antibiotics
1988.0

Abstract

By chemical screening methods we detected in the mycelium of Streptomyces griseoflavus (strain Tii 2880) the colabomycin-complex and a second compound called 2880-ll. 2880-ll was separated from crude extracts by silica gel chromatography and further purified by repeated chromatography on Sephadex LH-20 yielding a yellow amorphous powder. Its physico-chemical properties (MP 272°C; IR, UV, electron impact mass spectra, ¹H NMR, ¹³C NMR) were characterized. Structural elucidation via nuclear Overhauser enhancement difference experiments and spectral analyses revealed 2880-ll as (E)-N-(3-hydroxy-1-oxocyclopent-2-en-2-yl)-3-(4-hydroxy-3-methoxyphenyl)propenamide. Biosynthetically, it could be derived from ferulic acid and 2-amino-3-hydroxycyclopent-2-enone. In disc-diffusion assays against Gram-positive and Gram-negative bacteria, yeasts and fungi, 2880-ll showed no significant inhibitory activity up to 1 mg/ml.

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