Biotransformation of two furanocoumarins by the fungi species Aspergillus sp. PTCC 5266 and Aspergillus niger PTCC 5010

Nat Prod Res. 2019 Mar;33(6):835-842. doi: 10.1080/14786419.2017.1413563. Epub 2018 Feb 22.

Abstract

The microbial transformations of peucedanin and oreoselon by the fungi Aspergillus niger and Aspergillus sp. were investigated for the first time. Incubation of peucedanin with A. niger yielded a new hydroxylated metabolite with high yield (56%), which was characterized as 2-(1-hydroxypropan-2-yl)-3-methoxy-7H-furo[3,2-g]chromen-7-one. Oreoselon was converted to a new reduced metabolite methyl 3-(2,3-dihydro-6-hydroxy-2-isopropyl-3-oxobenzofuran-5-yl)propanoate in biotransformation by Aspergillus sp. The structures of the metabolites were determined by spectroscopic methods including IR, EI-MS, 1H NMR, 13C NMR, and elemental analysis.

Keywords: Biotransformation; fungi; furanocoumarins; oreoselon; peucedanin.

MeSH terms

  • Aspergillus / metabolism*
  • Aspergillus niger / metabolism*
  • Biotransformation*
  • Coumarins
  • Furocoumarins / metabolism*
  • Hydroxylation
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Coumarins
  • Furocoumarins
  • peucedanin
  • oreoselone