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

Juha Alanko, Asko Riutta, Päivi Holm, I. Muchá, Heikki Vapaatalo, Timo Metsä-Ketelä

Research output: Article

93 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)193-201
Number of pages9
JournalFree Radical Biology and Medicine
Volume26
Issue number1-2
DOIs
Publication statusPublished - jan. 1999

Fingerprint

Leukotriene B4
Phenols
Dinoprostone
Arachidonic Acid
Metabolism
Superoxides
Hydroxyl Radical
Antioxidants
Catechols
Modulation
Pyrogallol
Scavenging
Propyl Gallate
Guaiacol
Calcimycin
Neutrophils
hydroxyhydroquinone
perhydroxyl radical

ASJC Scopus subject areas

  • Medicine(all)
  • Toxicology
  • Clinical Biochemistry

Cite this

Modulation of arachidonic acid metabolism by phenols : Relation to their structure and antioxidant/prooxidant properties. / Alanko, Juha; Riutta, Asko; Holm, Päivi; Muchá, I.; Vapaatalo, Heikki; Metsä-Ketelä, Timo.

In: Free Radical Biology and Medicine, Vol. 26, No. 1-2, 01.1999, p. 193-201.

Research output: Article

Alanko, Juha ; Riutta, Asko ; Holm, Päivi ; Muchá, I. ; Vapaatalo, Heikki ; Metsä-Ketelä, Timo. / Modulation of arachidonic acid metabolism by phenols : Relation to their structure and antioxidant/prooxidant properties. In: Free Radical Biology and Medicine. 1999 ; Vol. 26, No. 1-2. pp. 193-201.
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