Novel amino acid metabolite produced by Streptomyces sp.: I. Taxonomy, isolation, and structural elucidation.
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 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(delta)-(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(alpha)-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 mildew disease in a pot test.
Tajika
T
T
Faculty of Agriculture, Tamagawa University, Tokyo, Japan.
Bando
I
I
Furuta
T
T
Moriya
N
N
Koshino
H
H
Uramoto
M
M
D000042:Absorption; D000596:Amino Acids / Q000145:classification / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D001120:Arginine / Q000031:analogs & derivatives / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003470:Culture Media; D007093:Imidazoles / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology; D007475:Ion Exchange Resins / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008855:Microscopy, Electron, Scanning; D009952:Ornithine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology; D011765:Pyruvaldehyde / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013302:Streptomyces / Q000145:classification / Q000378:metabolism* / Q000648:ultrastructure
D000596:Amino Acids; D003470:Culture Media; D007093:Imidazoles; D007475:Ion Exchange Resins; C107968:N(delta)-(5-methyl-4-oxo-2-imidazolin-2-yl)ornithine; D011765:Pyruvaldehyde; D001120:Arginine; D009952:Ornithine; C000015:N-acetyl-L-arginine