Scavenging Ability of Homogentisic Acid and Ergosterol toward Free Radicals Derived from Ethanol Consumption

J Phys Chem B. 2018 Aug 2;122(30):7514-7521. doi: 10.1021/acs.jpcb.8b04619. Epub 2018 Jul 20.

Abstract

Acute, or chronic, ethanol consumption leads to the formation of free radicals in the liver, which is related to hepatic damage. Among these radicals 1-hydroxyethyl, CH(OH)CH3, is the most abundant one. Thus, efficient CH(OH)CH3 scavengers are likely candidates to offer liver protection after ethanol consumption. In the present work ergosterol and homogentisic acid (HGA), which are found in edible mushrooms, were investigated as potential candidates to that purpose. The investigation was carried out following the QM-ORSA protocol, and using the density functional theory (DFT). The overall rate constants calculated for the CH(OH)CH3 radical scavenging activity of ergosterol in lipid and ethanol media are 1.34 × 107 and 1.86 × 107 M-1 s-1, respectively. For homogentisic acid the overall rate constant in lipid, ethanol and aqueous media are 4.33 × 108, 2.74 × 106, and 3.62 × 107 M-1 s-1, respectively. Accordingly, both compounds are predicted to efficiently scavenge the CH(OH)CH3 radical. Thus, the results from this investigation support the antioxidant capability of edible mushrooms, their potential beneficial effects against ethanol hepatotoxicity, and the nutraceuticals properties of ergosterol and homogentisic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / chemistry
  • Agaricales / metabolism
  • Ergosterol / chemistry*
  • Ethanol / chemistry*
  • Free Radical Scavengers / chemistry*
  • Homogentisic Acid / chemistry*
  • Hydroxyl Radical / chemistry*
  • Quantum Theory
  • Thermodynamics

Substances

  • Free Radical Scavengers
  • Hydroxyl Radical
  • Ethanol
  • Homogentisic Acid
  • Ergosterol