title: Ralfuranone Is Produced by an Alternative Aryl-Substituted γ-Lactone Biosynthetic Route in Ralstonia solanacearum.
abstract: The aryl-substituted γ-lactones ralfuranones A and B were isolated after feeding L-[1-(13)C]-phenylalanine to a liquid culture of the plant pathogenic bacterium Ralstonia solanacearum. (13)C NMR analysis demonstrated specific enrichment of the label at position 2 of the γ-lactone. This labeling pattern is consistent with a biosynthetic mechanism that includes direct cyclization of two monomeric phenylpyruvate precursors into an α,β-substituted lactone, but incompatible with a terphenylquinone intermediate. As the latter was shown as an intermediate in allantofuranone biosynthesis, we conclude that aryl-substituted γ-lactones can be assembled via divergent biosynthetic routes.
authors.affiliation: Department of Pharmaceutical Microbiology at the Hans-Knöll-Institute, Friedrich-Schiller-Universität , Beutenbergstrasse 11a, 07745 Jena, Germany.
authors.forename: Julia
authors.initials: J
authors.lastname: Pauly
authors.affiliation: Leibniz Institute for Natural Product Research and Infection Biology, Hans-Knöll-Institute , Beutenbergstrasse 11a, 07745 Jena, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Nett
authors.affiliation: Department of Pharmaceutical Microbiology at the Hans-Knöll-Institute, Friedrich-Schiller-Universität , Beutenbergstrasse 11a, 07745 Jena, Germany.
authors.forename: Dirk
authors.initials: D
authors.lastname: Hoffmeister
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000378:metabolism; D003500:Cyclization; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007783:Lactones / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D043368:Ralstonia solanacearum / Q000737:chemistry*
chemical_list: D005663:Furans; D007783:Lactones; C544237:allantofuranone; C000602065:ralfuranone A; C000602066:ralfuranone B; D015107:4-Butyrolactone