MK4588, a new antibiotic related to xanthocillin.
A new antibiotic, MK4588, structurally related to xanthocillin, was isolated from the culture broth of Leptosphaeria sp. L-179. Antibiotic MK4588 exhibited inhibitory activity against a limited range of Gram-positive and Gram-negative bacteria. The antibiotic was degraded by alkali to a more active product. The structures of MK4588 and the degradation product were determined to be (1R*,6S*,7S*)-7-(Z)-(1-isocyano-2-(4-methoxyphenyl]ethenyl-1-hydro xy-7- isocyanobicyclo[4,2,0]oct-2-en-4-one and (Z)-2,3-diisocyano-1-(4-methoxyphenyl)buta-1,3-diene, respectively, by NMR spectral analyses coupled with X-ray crystallographic analysis of MK4588.
Itoh
J
J
Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Yokohama, Japan.
Takeuchi
Y
Y
Gomi
S
S
Inouye
S
S
Mikawa
T
T
Yoshikawa
N
N
Ohkishi
H
H
D000900:Anti-Bacterial Agents / Q000032:analysis* / Q000096:biosynthesis / Q000302:isolation & purification / Q000494:pharmacology; D001203:Ascomycota / Q000145:classification / Q000378:metabolism*; D001419:Bacteria / Q000187:drug effects*; D001643:Bridged Bicyclo Compounds / Q000032:analysis / Q000302:isolation & purification / Q000494:pharmacology; D002070:Butadienes / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology; D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D005285:Fermentation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014961:X-Ray Diffraction
D000900:Anti-Bacterial Agents; D001643:Bridged Bicyclo Compounds; D002070:Butadienes; C064638:7-(1-isocyano-2-(4-methoxyphenyl))ethenyl-1-hydroxy-7-isocyanobicyclo(4,2,0)oct-2-en-4-one; C064639:2,3-diisocyano-1-(4-methoxyphenyl)buta-1,3-diene