Characterization of the radical-scavenging reaction of 2-O-substituted ascorbic acid derivatives, AA-2G, AA-2P, and AA-2S: a kinetic and stoichiometric study.
The aim of this study was to characterize the antioxidant activity of three ascorbic acid (AA) derivatives O-substituted at the C-2 position of AA: ascorbic acid 2-glucoside (AA-2G), ascorbic acid 2-phosphate (AA-2P), and ascorbic acid 2-sulfate (AA-2S). The radical-scavenging activities of these AA derivatives and some common low molecular-weight antioxidants such as uric acid or glutathione against 1,1-diphenyl-picrylhydrazyl (DPPH) radical, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS+), or galvinoxyl radical were kinetically and stoichiometrically evaluated under pH-controlled conditions. Those AA derivatives slowly and continuously reacted with DPPH radical and ABTS+, but not with galvinoxyl radical. They effectively reacted with DPPH radical under acidic conditions and with ABTS+ under neutral conditions. In contrast, AA immediately quenched all species of radicals tested at all pH values investigated. The reactivity of Trolox, a water-soluble vitamin E analogue, was comparable to that of AA in terms of kinetics and stoichiometrics. Uric acid and glutathione exhibited long-lasting radical-scavenging activity against these radicals under certain pH conditions. The radical-scavenging profiles of AA derivatives were closer to those of uric acid and glutathione rather than to that of AA. The number of radicals scavenged by one molecule of AA derivatives, uric acid, or glutathione was equal to or greater than that by AA or Trolox under the appropriate conditions. These data suggest the potential usage of AA derivatives as radical scavengers.
Takebayashi
Jun
J
Department of Immunochemistry, Faculty of Pharmaceutical Sciences, Okayama University, Japan.
Tai
Akihiro
A
Gohda
Eiichi
E
Yamamoto
Itaru
I
D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000494:pharmacology*; D001559:Benzhydryl Compounds / Q000737:chemistry; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D002839:Chromans / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000494:pharmacology*; D005978:Glutathione / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D010851:Picrates / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry; D014527:Uric Acid / Q000494:pharmacology
D001559:Benzhydryl Compounds; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D002839:Chromans; D016166:Free Radical Scavengers; D010851:Picrates; D013451:Sulfonic Acids; D014527:Uric Acid; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D005978:Glutathione; D001205:Ascorbic Acid; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid; C020338:galvinoxyl