Modulation of arachidonic acid metabolism by phenols: relation to their structure and antioxidant/prooxidant properties

Free Radic Biol Med. 1999 Jan;26(1-2):193-201. doi: 10.1016/s0891-5849(98)00179-8.


The effects of substituted catechols (3-methylcatechol, 4-methylcatechol, 4-nitrocatechol, and guaiacol) and trihydroxybenzenes (pyrogallol, propyl gallate, 1,2,4-trihydroxybenzene, and 1,3,5-trihydroxybenzene) on the synthesis of prostaglandin (PG)E2 and leukotriene (LT)B4 were tested in human A23187-stimulated polymorphonuclear leukocytes. The effects were related to their peroxyl-radical-scavenging (antioxidant), superoxide-scavenging (antioxidant), and superoxide-generating (prooxidant) properties. In general, compounds with hydroxyl groups in the ortho position increased PGE2/LTB4 ratio, and compounds with hydroxyl groups in the meta position decreased PGE2/LTB4 ratio. Catechols, which have hydroxyl groups in the ortho position, were the most potent peroxyl radical and superoxide anion scavengers. Trihydroxybenzenes (pyrogallol, 1,2,4-trihydroxybenzene, and 1,3,5-trihydroxybenzene) generated superoxide, whereas dihydroxybenzenes did not. Thus, the positions and number of hydroxyl groups seem to be the most important properties determining the action of phenolic compounds on PGE2/LTB4 ratio and their antioxidant/prooxidant activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry*
  • Antioxidants / pharmacology*
  • Arachidonic Acid / metabolism*
  • Calcimycin / pharmacology
  • Catechols / chemistry
  • Catechols / pharmacology
  • Dinoprostone / metabolism
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology
  • Humans
  • In Vitro Techniques
  • Ionophores / pharmacology
  • Leukotriene B4 / metabolism
  • Neutrophils / drug effects
  • Neutrophils / metabolism
  • Oxidants / chemistry*
  • Oxidants / pharmacology*
  • Peroxides / metabolism
  • Phenols / chemistry*
  • Phenols / pharmacology*
  • Structure-Activity Relationship
  • Superoxides / metabolism


  • Antioxidants
  • Catechols
  • Free Radical Scavengers
  • Ionophores
  • Oxidants
  • Peroxides
  • Phenols
  • Superoxides
  • Leukotriene B4
  • Arachidonic Acid
  • perhydroxyl radical
  • Calcimycin
  • Dinoprostone