Efficiency of trapping methylglyoxal by phenols and phenolic acids

J Food Sci. 2011 Apr;76(3):H90-6. doi: 10.1111/j.1750-3841.2011.02067.x. Epub 2011 Mar 16.

Abstract

The carbonyl stress that leads to the formation of advanced glycation end products (AGEs) has drawn much attention recently because of its micro- and macrovascular implications. During monitoring of methylglyoxal (MG), the efficiency of phenolics to directly trap MG can be demonstrated. Twenty compounds consisting of a single benzene ring structure with the addition of at least one hydroxyl group were allowed to react with MG at 37 °C for 1 h under physiological conditions in pH 7.4 phosphate buffer solution. Compounds composed of a benzene structure with a mono-hydroxyl substitute cannot react with MG. Among benzenediols and di-hydroxyl benzoic acids, only hydroquinone reacted with MG and showed a 13% decrease in MG. Nevertheless, high reactivity was shown for 3 benzenetriols. The percentages of MG remaining were 45%, 51%, and 36% for pyrogallol, 1,2,4-trihydroxybenzene, and 1,3,5-trihydroxybenzene, respectively. When a carboxyl group is added to the benzenetriols, steric hindrance and carbon electron charges on benzene ring are the influential factors in reactivity. Using computational chemistry calculations, a carbon electron charge of -0.24 was the minimum value for high reactivity.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Discovery*
  • Flavonoids / chemistry*
  • Free Radical Scavengers / chemistry*
  • Glycation End Products, Advanced / antagonists & inhibitors
  • Hydroquinones / chemistry
  • Hydroxybenzoates / chemistry*
  • Phenols / chemistry*
  • Polyphenols
  • Pyruvaldehyde / analogs & derivatives
  • Pyruvaldehyde / chemistry*
  • Structure-Activity Relationship

Substances

  • Flavonoids
  • Free Radical Scavengers
  • Glycation End Products, Advanced
  • Hydroquinones
  • Hydroxybenzoates
  • Phenols
  • Polyphenols
  • Pyruvaldehyde
  • phenolic acid
  • hydroquinone