Enzymatic synthesis of novel quercetin sialyllactoside derivatives

Nat Prod Res. 2019 Jul;33(13):1944-1952. doi: 10.1080/14786419.2018.1481842. Epub 2018 Jun 6.

Abstract

Quercetin and its derivatives are important flavonols that show diverse biological activity, such as antioxidant, anticarcinogenic, anti-inflammatory, and antiviral activities. Adding different substituents to quercetin may change the biochemical activity and bioavailability of molecules, when compared to the aglycone. Here, we have synthesised two novel derivatives of quercetin, quercetin-3-O-β-d-glucopyranosyl, 4''-O-d-galactopyranosyl 3'''-O-α-N-acetyl neuraminic acid i.e. 3'-sialyllactosyl quercetin (3'SL-Q) and quercetin-3-O-β-d-glucopyranosyl, 4''-O-β-d-galactopyranosyl 6'''-O-α-N-acetyl neuraminic acid i.e. 6'-sialyllactosyl quercetin (6'SL-Q) with the use of glycosyltransferases and sialyltransferases enzymes. These derivatives of quercetin were characterised by high-resolution quadrupole-time-of-flight electrospray ionisation mass spectrometry (HR-QTOF-ESI/MS) and 1H and 13C nuclear magnetic resonance (NMR) analyses.

Keywords: Quercetin derivatives; galactosylation; sialylation.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Chemistry Techniques, Synthetic
  • Drug Screening Assays, Antitumor
  • Glycosyltransferases / chemistry
  • Glycosyltransferases / metabolism
  • Hep G2 Cells
  • Humans
  • Lactose / analogs & derivatives*
  • Lactose / chemical synthesis
  • Lactose / chemistry
  • Lactose / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Quercetin / analogs & derivatives*
  • Quercetin / chemical synthesis
  • Quercetin / chemistry*
  • Quercetin / pharmacology
  • Sialic Acids / chemical synthesis
  • Sialic Acids / chemistry*
  • Sialic Acids / pharmacology
  • Sialyltransferases / chemistry
  • Sialyltransferases / metabolism
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Antineoplastic Agents, Phytogenic
  • Sialic Acids
  • isoquercitrin
  • N-acetylneuraminoyllactose
  • Quercetin
  • Glycosyltransferases
  • Sialyltransferases
  • Lactose