Increase of rutin antioxidant activity by generating Maillard reaction products with lysine

Bioorg Med Chem Lett. 2016 Jun 1;26(11):2680-4. doi: 10.1016/j.bmcl.2016.04.008. Epub 2016 Apr 5.

Abstract

Rutin exists in medicinal herbs, fruits, vegetables, and a number of plant-derived sources. Dietary sources containing rutin are considered beneficial because of their potential protective roles in multiple diseases related to oxidative stresses. In the present study, the change and antioxidation activity of rutin in Maillard reaction with lysine through a heating process were investigated. There is release of glucose and rhamnose that interact with lysine to give Maillard reaction products (MRPs), while rutin is converted to less-polar quercetin and a small quantity of isoquercitrin. Because of their high cell-membrane permeability, the rutin-lysine MRPs increase the free radical-scavenging activity in HepG2 cells, showing cellular antioxidant activity against Cu(2+)-induced oxidative stress higher than that of rutin. Furthermore, the MRPs significantly increased the Cu/Zn SOD (superoxide dismutase) activity and Cu/Zn SOD gene expression of HepG2 cells, consequently enhancing antioxidation activity.

Keywords: Antioxidant; Lysine; Maillard reaction; Reactive oxygen species; Rutin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Cell Membrane Permeability / drug effects
  • Dose-Response Relationship, Drug
  • Hep G2 Cells
  • Humans
  • Lysine / chemistry
  • Lysine / pharmacology*
  • Maillard Reaction
  • Molecular Structure
  • Oxidative Stress / drug effects
  • Rutin / chemistry
  • Rutin / pharmacology*
  • Structure-Activity Relationship
  • Superoxide Dismutase / metabolism

Substances

  • Antioxidants
  • Rutin
  • Superoxide Dismutase
  • Lysine