title: New aminocoumarin antibiotics from a cloQ-defective mutant of the clorobiocin producer Streptomyces roseochromogenes DS12.976.
abstract: Three new antibiotics, vanillobiocin, isovanillobiocin and declovanillobiocin, were isolated from the culture broth of a cloQ-defective mutant of the clorobiocin producer Streptomyces roseochromogenes, which is blocked in the biosynthesis of the prenylated 4-hydroxybenzoic acid moiety of clorobiocin. Spectroscopic analysis showed that the isolated compounds were similar to clorobiocin, but contained vanillic acid as the acyl component instead of the prenylated 4-hydroxybenzoic acid present in clorobiocin. Isovanillobiocin differs from vanillobiocin by the position of the pyrrole unit attached to the sugar moiety of the antibiotic. Declovanillobiocin lacks the chlorine atom at the aminocoumarin ring. All three compounds had lower antibiotic activity against Bacillus subtilis than clorobiocin.
authors.affiliation: Pharmazeutische Biologie, Pharmazeutisches Institut, Eberhard-Karls-Universität Tübingen Auf der Morgenstelle 8, 72076 Tübingen, Germany.
authors.forename: Anja
authors.initials: A
authors.lastname: Freitag
authors.forename: Ute
authors.initials: U
authors.lastname: Galm
authors.forename: Shu-Ming
authors.initials: SM
authors.lastname: Li
authors.forename: Lutz
authors.initials: L
authors.lastname: Heide
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D005285:Fermentation; D008826:Microbial Sensitivity Tests; D009675:Novobiocin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D013302:Streptomyces; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D009675:Novobiocin; C006260:clorobiocin