In vitro gastrointestinal absorption of red wine anthocyanins - Impact of structural complexity and phase II metabolization

Food Chem. 2020 Jul 1:317:126398. doi: 10.1016/j.foodchem.2020.126398. Epub 2020 Feb 11.

Abstract

Malvidin-3-O-glucoside, malvidin-3,5-O-diglucoside, malvidin-3-O-(6-O-coumaroyl)-glucoside-5-O-glucoside from Chinese Vitis davidii red wine were used to investigate the role of glucoside, diglucoside and coumaroylated glucoside moieties on their transport efficiency through MKN-28 gastric and Caco-2 intestinal cells. Due to the already described conversion of 3-O-glucosylated anthocyanins into 3-O-glucuronidated, the 3-O-glucuronidated metabolite of malvidin-3-O-glucoside was also tested. The antiproliferative activity was higher for the glucuronidated metabolite in both cell lines. All anthocyanins were transported through MKN-28 gastric cells and Caco-2 intestinal cells with transport efficiencies ranging from 4% to 9% in MKN-28 and from 3% to 5% in Caco-2. No significant differences on transport efficiencies were observed at 180 min among the different anthocyanins in MKN-28. The transport efficiency of malvidin-3-O-glucuronide at 180 min was about 3-4% in Caco-2 and MKN-28 cells. Computational studies were performed to evaluate the interaction between anthocyanins and glucose gastric transporters GLUT1 and GLUT3, which supported the experimental findings.

Keywords: Absorption; Anthocyanins; Bioavailability; Caco-2; MKN-28; Metabolization.

MeSH terms

  • Anthocyanins / analysis
  • Anthocyanins / chemistry
  • Anthocyanins / pharmacokinetics*
  • Caco-2 Cells
  • Cell Survival / drug effects
  • Glucose Transporter Type 1 / chemistry
  • Glucose Transporter Type 1 / metabolism
  • Glucose Transporter Type 3 / chemistry
  • Glucose Transporter Type 3 / metabolism
  • Glucosides / analysis
  • Glucosides / chemistry
  • Glucosides / pharmacokinetics
  • Humans
  • Inactivation, Metabolic
  • Intestinal Absorption
  • Molecular Docking Simulation
  • Vitis / chemistry*
  • Wine*

Substances

  • Anthocyanins
  • Glucose Transporter Type 1
  • Glucose Transporter Type 3
  • Glucosides
  • SLC2A1 protein, human
  • SLC2A3 protein, human
  • malvidin-3-glucoside