l-Theanine Inhibits (-)-Epigallocatechin-3-gallate Oxidation via Chelating Copper

J Agric Food Chem. 2022 Jun 29;70(25):7751-7761. doi: 10.1021/acs.jafc.2c01379. Epub 2022 Jun 13.

Abstract

Our recent study showed that glutamate can inhibit dopamine oxidation via chelating copper. l-Theanine is an amino acid analogue of glutamate, whereas tea (-)-epigallocatechin-3-gallate (EGCG) is similar to dopamine in avidly undergoing oxidation. We thus hypothesized that l-theanine could also restrain EGCG oxidation via chelating copper. The current study scrutinized influences of l-theanine on EGCG oxidation in vitro and in vivo. The in vitro results showed that l-theanine and copper formed an l-theanine-copper complex with impaired redox activity of copper. Accordingly, l-theanine effectively suppressed copper-facilitated EGCG oxidation, hydroxyl radical production, and DNA damage; inhibited EGCG autoxidation which in essence involves catalysis of transition metals such as copper; and reduced EGCG oxidation-associated formation of a quinone adduct with proteins known as quinoproteins. Consistently, l-theanine significantly increased hepatic EGCG levels and reduced hepatic quinoprotein levels and liver injury in mice treated with EGCG. These lines of evidence together suggest that tea l-theanine can protect against tea catechin oxidation.

Keywords: (−)-epigallocatechin-3-gallate; copper; l-theanine; oxidation; quinoprotein.

MeSH terms

  • Animals
  • Catechin* / analogs & derivatives
  • Catechin* / chemistry
  • Chelating Agents / pharmacology
  • Copper / metabolism
  • Dopamine
  • Glutamates / metabolism
  • Mice
  • Oxidation-Reduction
  • Tea / chemistry

Substances

  • Chelating Agents
  • Glutamates
  • Tea
  • Copper
  • theanine
  • Catechin
  • epigallocatechin gallate
  • Dopamine