Recovery mechanism of the antioxidant activity from carnosic acid quinone, an oxidized sage and rosemary antioxidant

J Agric Food Chem. 2002 Oct 9;50(21):5863-9. doi: 10.1021/jf025605o.

Abstract

A solution of carnosic acid quinone, which is a radical chain-termination product having no antioxidant activity in the antioxidant reaction of carnosic acid, recovers potent antioxidant activity upon standing. The HPLC analysis of an aged solution of carnosic acid quinone revealed that several antioxidants are produced in the solution. From the time-course and quantitative analyses of the formation of the products and their structural analysis, an antioxidant mechanism from carnosic acid quinone is proposed that includes a redox reaction of carnosic acid quinone in addition to the isomerization to lactone derivatives. In the first stage of antioxidation, carnosic acid, the reduction product from carnosic acid quinone, contributes to the potent antioxidant activity of the solution. This proposed mechanism can explain one of the reasons for the strong antioxidant activity of the extract of the popular herbs sage and rosemary.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes
  • Acetonitriles
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Benzoquinones / chemistry*
  • Diterpenes / chemistry*
  • Diterpenes / pharmacology*
  • Isomerism
  • Lactones / chemistry
  • Methanol
  • Oxidation-Reduction
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology*
  • Rosmarinus / chemistry*
  • Salvia officinalis / chemistry*
  • Solutions

Substances

  • Abietanes
  • Acetonitriles
  • Antioxidants
  • Benzoquinones
  • Diterpenes
  • Lactones
  • Plant Extracts
  • Solutions
  • quinone
  • rosmanol
  • salvin
  • Methanol
  • acetonitrile