title: MK4588, a new antibiotic related to xanthocillin.
abstract: 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.
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Yokohama, Japan.
authors.forename: J
authors.initials: J
authors.lastname: Itoh
authors.forename: Y
authors.initials: Y
authors.lastname: Takeuchi
authors.forename: S
authors.initials: S
authors.lastname: Gomi
authors.forename: S
authors.initials: S
authors.lastname: Inouye
authors.forename: T
authors.initials: T
authors.lastname: Mikawa
authors.forename: N
authors.initials: N
authors.lastname: Yoshikawa
authors.forename: H
authors.initials: H
authors.lastname: Ohkishi
mesh_terms: 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
chemical_list: 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