title: Volatile lactones from streptomycetes arise via the antimycin biosynthetic pathway.
abstract: The volatiles released by several streptomycetes were collected by using a closed-loop stripping apparatus (CLSA) and analysed by GC-MS. The obtained headspace extracts of various species contained blastmycinone, a known degradation product of the fungicidal antibiotic, antimycin A(3b), and several unknown derivatives. The suggested structures of these compounds, based on their mass spectra and GC retention indices, were confirmed by comparison to synthetic reference samples. Additional compounds found in the headspace extracts were butenolides formed from the blastmycinones by elimination of the carboxylic acid moiety. Analysis of a gene knockout mutant in the antimycin biosynthetic gene cluster demonstrated that all blastmycinones and butenolides are formed via the antimycin biosynthetic pathway. The structural variation of the blastmycinones identified here is much larger than within the known antimycins, thus suggesting that several antimycin derivatives remain to be discovered.
authors: Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
authors: Ramona
authors: R
authors: Riclea
authors: Bertrand
authors: B
authors: Aigle
authors: Pierre
authors: P
authors: Leblond
authors: Ilka
authors: I
authors: Schoenian
authors: Dieter
authors: D
authors: Spiteller
authors: Jeroen S
authors: JS
authors: Dickschat
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis; D000968:Antimycin A / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry / Q000378:metabolism; D053898:Biosynthetic Pathways; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013302:Streptomyces / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism
chemical_list: C416059:blastomycinone; C032456:antimycin; D000968:Antimycin A; C004511:butenolide; D015107:4-Butyrolactone