Journal
FEBS LETTERS
Volume 555, Issue 3, Pages 601-605Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/S0014-5793(03)01358-9
Keywords
antioxidant pharmacophore; folic acid; tetrahydrofolate; 5-methyltetrahydrofolate; 4-hydroxy-2,5,6-triaminopyrimidine
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The presumed protective effect of folic acid on the pathogenesis of cardiovascular, hematological and neurological diseases and cancer has been associated with the antioxidant activity of folic acid. Peroxynitrite (PON) scavenging activity and inhibition of lipid peroxidation (LPO) of the physiological forms of folate and of structurally related compounds were tested. It was found that the fully reduced forms of folate, i.e. tetrahydrofolate (THF) and 5-methyltetrahydrofolate (5-MTHF), had the most prominent antioxidant activity. It appeared that their protection against LPO is less pronounced than their PON scavenging activity. The antioxidant activity of these forms of folic acid resides in the pterin core, the antioxidant pharmacophore is 4-hydroxy-2,5,6-triaminopyrimidine. It is suggested that an electron donating effect of the 5-amino group is of major importance for the antioxidant activity of 4-hydroxy-2,5,6-triaminopyrimidine. A similar electron donating effect is probably important for the antioxidant activity of THF and 5-MTHF. (C) 2003 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.
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