Novel Amino Acid Metabolite Produced by Streptomyces sp.: I. Taxonomy, Isolation, and Structural Elucidation

• Published in: Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 1997, Vol.61 (6), p.1007-1010
• Main Authors: Tajika, Tatsuharu, Bando, Isao, Furuta, Takaki, Moriya, Noriko, Koshino, Hiroyuki, Uramoto, Masakazu
• Format: Article
• Language: English
• Subjects: Absorption; amino acid; Amino Acids - classification; Amino Acids - isolation & purification; Amino Acids - metabolism; Amino Acids - pharmacology; Antibiotics (antibacterial agents, antifungal agents); Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; Applied microbiology; Arginine - analogs & derivatives; Arginine - chemistry; arginine analogue; Biological and medical sciences; Biotechnology; Chromatography, High Pressure Liquid; Culture Media; Fundamental and applied biological sciences. Psychology; Imidazoles - chemistry; Imidazoles - isolation & purification; Imidazoles - metabolism; Imidazoles - pharmacology; imidazoline derivative; Ion Exchange Resins - chemistry; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Microbiology; Microscopy, Electron, Scanning; Ornithine - analogs & derivatives; Ornithine - chemistry; Ornithine - isolation & purification; Ornithine - metabolism; Ornithine - pharmacology; Pyruvaldehyde - chemistry; Spectrometry, Mass, Fast Atom Bombardment; Streptomyces; Streptomyces - classification; Streptomyces - metabolism; Streptomyces - ultrastructure
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.61.1007

A strain of streptomycete isolated from a soil sample was found to produce a novel amino acid metabolite. The compound was purified from the culture fluid by column chromatography, using cation exchange resin, a synthetic adsorbent, and finally by preparative HPLC with a reverse-phase column. The structure of the compound was established as N δ -(5-methyl-4-oxo-2-imidazolin-2-yl)-L-ornithine on the basis of an analysis of the spectral data and chemical degradation. This was confirmed by comparing the NMR spectrum of the metabolite with that of the compound synthesized by treating methylglyoxal and N α -acetyl-L-arginine. The substance did not show any antimicrobial activity against bacteria, fungi and yeasts by the agar plate method, but exhibited a weak preventive effect on cucumber powdery mildew disease in a pot test.