Free radical scavenging behavior of folic acid: evidence for possible antioxidant activity.
The free radical scavenging properties and possible antioxidant activity of folic acid are reported. Pulse radiolysis technique is employed to study the one-electron oxidation of folic acid in homogeneous aqueous solution. The radicals used for this study are CCl(3)O(2)(*), N(3)(*), SO(4)(*-), Br(2)(*-), *OH, and O(*-). All these radicals react with folic acid under ambient condition at an almost diffusion-controlled rate producing two types of transients. The first transient absorption maximum is around 430 nm, which decays, and a simultaneous growth at around 390 nm is observed. Considering the chemical structure of folic acid, the absorption maximum at 430 nm has been assigned to a phenoxyl radical. The latter one is proposed to be a delocalized molecular radical. A permanent product has been observed in the oxidation of folic acid with CCl(3)O(2)(*) and N(3)(*) radicals, with a broad absorption band around 370-400 nm. The bimolecular rate constants for all the radical-induced oxidation reactions of folic acid have been measured. Folic acid is seen to scavenge these radicals very efficiently. In the reaction of thiyl radicals with folic acid, it has been observed that folic acid can not only scavenge thiyl radicals but can also repair these thiols at physiological pH. While carrying out the lipid peroxidation study, in spite of the fact that folic acid is considerably soluble in water, we observed a significant inhibition property in microsomal lipid peroxidation. A suitable mechanism for oxidation of folic acid and repair of thiyl radicals by folic acid has been proposed.
Joshi
R
R
Radiation Chemistry and Chemical Dynamics Division, Bhabha Atomic Research Centre, Mumbai, India.
Adhikari
S
S
Patro
B S
BS
Chattopadhyay
S
S
Mukherjee
T
T
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D001386:Azides / Q000378:metabolism; D004058:Diffusion; D005492:Folic Acid / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000494:pharmacology*; D005609:Free Radicals / Q000378:metabolism; D017665:Hydroxyl Radical; D015227:Lipid Peroxidation / Q000187:drug effects; D008862:Microsomes, Liver / Q000187:drug effects; D010084:Oxidation-Reduction; D010545:Peroxides; D011675:Pulse Radiolysis; D051381:Rats; D017208:Rats, Wistar; D013438:Sulfhydryl Compounds / Q000378:metabolism
D000975:Antioxidants; D001386:Azides; D016166:Free Radical Scavengers; D005609:Free Radicals; D010545:Peroxides; D013438:Sulfhydryl Compounds; C049375:perhydroxyl radical; D017665:Hydroxyl Radical; D005492:Folic Acid