title: Identification and biosynthesis of a novel xanthomonadin-dialkylresorcinol-hybrid from Azoarcus sp. BH72.
abstract: A novel xanthomonadin-dialkylresorcinol hybrid named arcuflavin was identified in Azoarcus sp. BH72 by a combination of feeding experiments, HPLC-MS and MALDI-MS and gene clusters encoding the biosynthesis of this non-isoprenoid aryl-polyene containing pigment are reported. A chorismate-utilizing enzyme from the XanB2-type producing 3- and 4-hydroxybenzoic acid and an AMP-ligase encoded by these gene clusters were characterized, that might perform the first two steps of the polyene biosynthesis. Furthermore, a detailed analysis of the already known or novel biosynthesis gene clusters involved in the biosynthesis of polyene containing pigments like arcuflavin, flexirubin and xanthomonadin revealed the presence of similar gene clusters in a wide range of bacterial taxa, suggesting that polyene and polyene-dialkylresorcinol pigments are more widespread than previously realized.
authors.affiliation: Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Frankfurt am Main, Germany.
authors.forename: Tim A
authors.initials: TA
authors.lastname: Schöner
authors.affiliation: Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Frankfurt am Main, Germany.
authors.forename: Sebastian W
authors.initials: SW
authors.lastname: Fuchs
authors.affiliation: Lab of General Microbiology, University of Bremen, Bremen, Germany.
authors.forename: Barbara
authors.initials: B
authors.lastname: Reinhold-Hurek
authors.affiliation: Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Frankfurt am Main, Germany.
authors.forename: Helge B
authors.initials: HB
authors.lastname: Bode
mesh_terms: D000840:Anisoles / Q000737:chemistry / Q000378:metabolism*; D020627:Azoarcus / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D001688:Biological Products / Q000737:chemistry / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D023061:Gene Order; D016680:Genome, Bacterial; D015394:Molecular Structure; D005810:Multigene Family; D010860:Pigments, Biological / Q000235:genetics / Q000378:metabolism; D011090:Polyenes / Q000737:chemistry / Q000378:metabolism; D015203:Reproducibility of Results; D012118:Resorcinols / Q000737:chemistry / Q000378:metabolism*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000840:Anisoles; D001688:Biological Products; D010860:Pigments, Biological; D011090:Polyenes; D012118:Resorcinols; C108932:xanthomonadin I