Absorption of 3(2H)-furanones by human intestinal epithelial Caco-2 cells

J Agric Food Chem. 2009 May 13;57(9):3949-54. doi: 10.1021/jf9001704.

Abstract

A number of 3(2H)-furanones are synthesized by fruits and have been found in cooked foodstuffs, where they impart flavor and odor because of their low perception thresholds. They show genotoxic properties in model studies but are also ranked among the antioxidants and anticarcinogens. This study examined the efficiency of intestinal absorption and metabolic conversion of 3(2H)-furanones by using Caco-2 cell monolayers as an intestinal epithelial cell model. The permeability of each agent was measured in both the apical to basal and basal to apical directions. 2,5-Dimethyl-4-methoxy-3(2H)-furanone (DMMF) showed the highest absorption rate in all experiments, while similar amounts of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF), 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF), and 4-hydroxy-5-methyl-3(2H)-furanone (HMF) were taken up. HDMF-glucoside was almost not absorbed but was hydrolyzed to a small extent. The transport of 3(2H)-furanones could not be saturated even at levels of 500 microM and occurred in both directions. Because the uptake was only slightly reduced by apical hyperosmolarity, passive diffusion by paracellular transport is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • 4-Butyrolactone / metabolism
  • Biological Transport
  • Caco-2 Cells
  • Diffusion
  • Epithelium / metabolism
  • Furans / metabolism*
  • Glucosides / chemical synthesis
  • Glucosides / metabolism
  • Humans
  • Hydrolysis
  • Intestinal Absorption*
  • Kinetics
  • Osmolar Concentration

Substances

  • Furans
  • Glucosides
  • 4-methoxy-2,5-dimethyl-3(2H)-furanone
  • furaneol
  • 4-Butyrolactone