Enzymatic activity of cell-free extracts from Burkholderia oxyphila OX-01 bio-converts (+)-catechin and (-)-epicatechin to (+)-taxifolin

Biosci Biotechnol Biochem. 2016 Dec;80(12):2473-2479. doi: 10.1080/09168451.2016.1220822. Epub 2016 Aug 17.

Abstract

This study characterized the enzymatic ability of a cell-free extract from an acidophilic (+)-catechin degrader Burkholderia oxyphila (OX-01). The crude OX-01 extracts were able to transform (+)-catechin and (-)-epicatechin into (+)-taxifolin via a leucocyanidin intermediate in a two-step oxidation. Enzymatic oxidation at the C-4 position was carried out anaerobically using H2O as an oxygen donor. The C-4 oxidation occurred only in the presence of the 2R-catechin stereoisomer, with the C-3 stereoisomer not affecting the reaction. These results suggest that the OX-01 may have evolved to target both (+)-catechin and (-)-epicatechin, which are major structural units in plants.

Keywords: (+)-catechin; (+)-taxifolin; (−)-epicatechin; burkholderia; enzymatic reaction.

MeSH terms

  • Biotransformation
  • Burkholderia / enzymology*
  • Catechin / chemistry*
  • Catechin / metabolism*
  • Oxygen / metabolism
  • Quercetin / analogs & derivatives*
  • Quercetin / chemistry
  • Quercetin / metabolism
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Catechin
  • Quercetin
  • taxifolin
  • Oxygen