Spontaneous conversion of L-dehydroascorbic acid to L-ascorbic acid and L-erythroascorbic acid.
Dehydroascorbic acid, an oxidation product of ascorbic acid (vitamin C), spontaneously decomposed at neutral and higher pH levels to form three products that could be quantitated by HPLC-electrochemical analysis. One of the products was ascorbic acid, suggesting that dehydroascorbic acid was reduced to ascorbic acid without adding an exogenous reductant. The major newly produced compound was almost identical to ascorbic acid by UV spectroscopy, which therefore potentially interfered in the study of ascorbic acid metabolism. The ascorbic acid-like compound was isolated by reversed-phase HPLC and identified as L-erythroascorbic acid by mass spectrometry. Fe(II) and Cu(I) increased, whereas desferrioxamine, a potent iron chelator, inhibited L-erythroascorbic acid production. Phosphate, used as buffer, and cyanide greatly enhanced dehydroascorbic acid conversion to L-erythroascorbic acid. The identification of L-erythroascorbic acid and its quantitation by an electrochemical method provides a useful tool for future study of dehydroascorbic acid metabolism.
Jung
C H
CH
Department of Biochemistry, Michigan State University, East Lansing, Michigan, 48824, USA.
Wells
W W
WW
D001205:Ascorbic Acid / Q000737:chemistry* / Q000378:metabolism; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D003300:Copper / Q000737:chemistry; D003676:Deferoxamine / Q000737:chemistry; D003683:Dehydroascorbic Acid / Q000737:chemistry* / Q000378:metabolism; D004563:Electrochemistry; D008401:Gas Chromatography-Mass Spectrometry; D006863:Hydrogen-Ion Concentration; D066298:In Vitro Techniques; D007501:Iron / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet
D012996:Solutions; C005056:isoascorbic acid; D003300:Copper; D007501:Iron; D003676:Deferoxamine; D001205:Ascorbic Acid; D003683:Dehydroascorbic Acid