title: Identification of the actinorhodin monomer and its related compound from a deletion mutant of the actVA-ORF4 gene of Streptomyces coelicolor A3(2).
abstract: An oxygenated derivative of dihydrokalafungin (DHK) was isolated from a deletion mutant of the actVA-ORF4 gene involved in the biosynthesis of a dimeric benzoisochromanequinone (BIQ) antibiotic, actinorhodin (ACT), in Streptomyces coelicolor A3(2). Spectroscopic analysis elucidated its structure as 8-hydroxy-DHK, corresponding to the monomeric unit of ACT. Further metabolite analysis identified its related compound, clearly derived from the reduction of 8-hydroxy-DHK. The structures of these metabolites indicate the essential role of ActVA-ORF4 in ACT biosynthesis, specifically in dimerization of a BIQ intermediate via C-C bond formation.
authors: Research Institute of Pharmaceutical Sciences, Musashino University, Tokyo, Japan.
authors: Takaaki
authors: T
authors: Taguchi
authors: Takayuki
authors: T
authors: Ebihara
authors: Atsushi
authors: A
authors: Furukawa
authors: Yumiko
authors: Y
authors: Hidaka
authors: Ryuji
authors: R
authors: Ariga
authors: Susumu
authors: S
authors: Okamoto
authors: Koji
authors: K
authors: Ichinose
mesh_terms: D000880:Anthraquinones / Q000032:analysis / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000032:analysis / Q000096:biosynthesis*; D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D017353:Gene Deletion; D009682:Magnetic Resonance Spectroscopy; D009154:Mutation; D021241:Spectrometry, Mass, Electrospray Ionization; D048372:Streptomyces coelicolor / Q000378:metabolism*; D000095622:Benzoisochromanequinones
chemical_list: D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; C013390:actinorhodin; D000095622:Benzoisochromanequinones