Chemoenzymatic reduction of citreorosein and its implications on aloe-emodin and rugulosin C (bio)synthesis

Org Biomol Chem. 2019 Oct 14;17(38):8711-8715. doi: 10.1039/c9ob01690b. Epub 2019 Sep 24.

Abstract

A chemoenzymatic reduction of citreorosein by the NADPH-dependent polyhydroxyanthracene reductase from Cochliobolus lunatus or MdpC from Aspergillus nidulans in the presence of Na2S2O4 gave access to putative biosynthetic intermediates, (R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracene-1(2H)-one and its oxidized form, (R)-3,4-dihydrocitreorosein. Herein, we discuss the implications of these results towards the (bio)synthesis of aloe-emodin and (+)-rugulosin C in fungi.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / metabolism*
  • Ascomycota / enzymology
  • Fungal Proteins / chemistry
  • Fungal Proteins / metabolism*
  • Molecular Structure
  • Oxidation-Reduction
  • Oxidoreductases Acting on CH-CH Group Donors / chemistry
  • Oxidoreductases Acting on CH-CH Group Donors / metabolism*

Substances

  • Anthraquinones
  • Fungal Proteins
  • rugulosin C
  • tetrahydroxynaphthalene reductase
  • Oxidoreductases Acting on CH-CH Group Donors
  • citreorosein