Aryl Polyenes, a Highly Abundant Class of Bacterial Natural Products, Are Functionally Related to Antioxidative Carotenoids

Chembiochem. 2016 Feb 2;17(3):247-53. doi: 10.1002/cbic.201500474. Epub 2016 Jan 5.


Bacterial pigments of the aryl polyene type are structurally similar to the well-known carotenoids with respect to their polyene systems. Their biosynthetic gene cluster is widespread in taxonomically distant bacteria, and four classes of such pigments have been found. Here we report the structure elucidation of the aryl polyene/dialkylresorcinol hybrid pigments of Variovorax paradoxus B4 by HPLC-UV-MS, MALDI-MS and NMR. Furthermore, we show for the first time that this pigment class protects the bacterium from reactive oxygen species, similarly to what is known for carotenoids. An analysis of the distribution of biosynthetic genes for aryl polyenes and carotenoids in bacterial genomes is presented; it shows a complementary distribution of these protective pigments in bacteria.

Keywords: antioxidants; aryl polyenes; carotenoids; dialkylresorcinols; dyes/pigments; natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / metabolism*
  • Bacterial Proteins / classification
  • Bacterial Proteins / genetics
  • Bacterial Proteins / metabolism
  • Biological Products / chemistry
  • Biological Products / metabolism*
  • Carotenoids / chemistry
  • Carotenoids / metabolism*
  • Chromatography, High Pressure Liquid
  • Comamonadaceae / genetics
  • Comamonadaceae / metabolism*
  • Genome, Bacterial
  • Multigene Family
  • Mutagenesis
  • Phylogeny
  • Polyenes / chemistry
  • Polyenes / metabolism*
  • Reactive Oxygen Species / metabolism
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization


  • Antioxidants
  • Bacterial Proteins
  • Biological Products
  • Polyenes
  • Reactive Oxygen Species
  • Carotenoids