Laccase-Catalyzed Heterocoupling of Dihydroquercetin and p-Aminobenzoic Acid: Effect of the Reaction Product on Cultured Cells

Biochemistry (Mosc). 2018 Aug;83(8):992-1001. doi: 10.1134/S0006297918080102.

Abstract

Derivatization of the natural flavonoid dihydroquercetin with p-aminobenzoic acid was carried out in an ethyl acetate/citric buffer biphasic system using laccase from the fungus Trametes hirsuta. The main reaction product yield was ~68 mol %. The product was characterized by 1H NMR, 13C NMR, and liquid chromatography-mass spectroscopy, and its structure was elucidated. The reaction product affected viability of cultured human rhabdomyosarcoma cells (RD cell line) in a dose-dependent manner and, therefore, can be of interest to pharmaceutical industry.

MeSH terms

  • 4-Aminobenzoic Acid / chemistry*
  • Acetates / chemistry
  • Biocatalysis*
  • Cell Line, Tumor
  • Citric Acid / chemistry
  • Humans
  • Laccase / metabolism*
  • Quercetin / analogs & derivatives*
  • Quercetin / chemistry
  • Trametes / enzymology

Substances

  • Acetates
  • Citric Acid
  • ethyl acetate
  • Quercetin
  • taxifolin
  • Laccase
  • 4-Aminobenzoic Acid