Identification and biosynthesis of a novel xanthomonadin-dialkylresorcinol-hybrid from Azoarcus sp. BH72

PLoS One. 2014 Mar 11;9(3):e90922. doi: 10.1371/journal.pone.0090922. eCollection 2014.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anisoles / chemistry
  • Anisoles / metabolism*
  • Azoarcus / chemistry
  • Azoarcus / genetics
  • Azoarcus / metabolism*
  • Biological Products / chemistry
  • Biological Products / metabolism*
  • Gas Chromatography-Mass Spectrometry
  • Gene Order
  • Genome, Bacterial
  • Molecular Structure
  • Multigene Family
  • Pigments, Biological / genetics
  • Pigments, Biological / metabolism
  • Polyenes / chemistry
  • Polyenes / metabolism
  • Reproducibility of Results
  • Resorcinols / chemistry
  • Resorcinols / metabolism*
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Anisoles
  • Biological Products
  • Pigments, Biological
  • Polyenes
  • Resorcinols
  • xanthomonadin I

Grant support

Work in the Bode lab was funded by the Deutsche Forschungsgemeinschaft (DFG). The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.