piperidines and epiderstatin

The structure of a novel antibiotic, epiderstatin, was determined as 4-[3-((Z)-3,5-dimethyl-2-oxopiperidin-6-ylidene)-2-oxopropyl]-2, 6-piperidinedione by spectroscopic analyses of 1H NMR, 13C NMR, 1H-1H correlation spectroscopy (COSY), 13C-1H COSY, heteronuclear multiple bond correlation spectroscopy, UV and IR spectra. The antibiotic belongs to the glutarimide antibiotics, however, the characteristic feature of epiderstatin is that it has a piperidone ring instead of a cyclohexanone ring.

Topics: Antibiotics, Antineoplastic; Epidermal Growth Factor; Magnetic Resonance Spectroscopy; Methylation; Molecular Structure; Piperidines; Piperidones; Pyridones; Spectrophotometry, Ultraviolet; Spectrum Analysis

Inhibitors of mitogenic activity induced by epidermal growth factor (EGF) were screened from culture broths of soil microorganisms. A strain of actinomycetes has been found to produce a new glutarimide antibiotic named epiderstatin which inhibits the incorporation of [3H]thymidine into quiescent animal cells stimulated by EGF. Taxonomic studies have revealed that the producing strain belongs to a subspecies of Streptomyces pulveraceus, thus the name, Streptomyces pulveraceus subsp. epiderstagenes was given to this strain. The molecular formula (C15H20N2O4) and UV profile (lambda max 295 nm) of the antibiotic are distinct from other known antibiotics. It inhibited the incorporation of [3H]thymidine into quiescent cells stronger than into growing cells.

Topics: Animals; Antibiotics, Antineoplastic; Cells, Cultured; Chromatography, Gel; Chromatography, High Pressure Liquid; Epidermal Growth Factor; Fermentation; Magnetic Resonance Spectroscopy; Microscopy, Electron, Scanning; Piperidines; Piperidones; Pyridones; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Spores, Bacterial; Streptomyces