The oxidation of dehydroascorbic acid and 2,3-diketogulonate by distinct reactive oxygen species
Abstract
l-Ascorbate, dehydro-l-ascorbic acid (DHA), and 2,3-diketo-l-gulonate (DKG) can all quench reactive oxygen species (ROS) in plants and animals. The vitamin C oxidation products thereby formed are investigated here. DHA and DKG were incubated aerobically at pH 4.7 with peroxide (H2O2), ‘superoxide’ (a ~50:50 mixture of O2 and HO2), hydroxyl radicals (•OH, formed in Fenton mixtures), and illuminated riboflavin (generating singlet oxygen, 1O2). Products were monitored electrophoretically. DHA quenched H2O2 far more effectively than superoxide, but the main products in both cases were 4-O-oxalyl-l-threonate (4-OxT) and smaller amounts of 3-OxT and OxA + threonate. H2O2, but not superoxide, also yielded cyclic-OxT. Dilute Fenton mixture almost completely oxidised a 50-fold excess of DHA, indicating that it generated oxidant(s) greatly exceeding the theoretical •OH yield; it yielded oxalate, threonate, and OxT. 1O2 had no effect on DHA. DKG was oxidatively decarboxylated by H2O2, Fenton mixture, and 1O2, forming a newly characterised product, 2-oxo-l-threo-pentonate (OTP; ‘2-keto-l-xylonate’). Superoxide yielded negligible OTP. Prolonged H2O2 treatment oxidatively decarboxylated OTP to threonate. Oxidation of DKG by H2O2, Fenton mixture, or 1O2 also gave traces of 4-OxT but no detectable 3-OxT or cyclic-OxT. In conclusion, DHA and DKG yield different oxidation products when attacked by different ROS. DHA ismore »
- Authors:
-
[2]
- Univ. of Edinburgh, Scotland (United Kingdom). Inst. of Molecular Plant Sciences, Edinburgh Cell Wall Group; Univ. of Exeter (United Kingdom). Hatherly Labs., wildFIRE Lab.
- Univ. of Edinburgh, Scotland (United Kingdom). Inst. of Molecular Plant Sciences, Edinburgh Cell Wall Group
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC); U.K. Biotechnology and Biological Sciences Research Council (BBSRC)
- OSTI Identifier:
- 1658353
- Grant/Contract Number:
- AC02-05CH11231; BB/I015531/1
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Biochemical Journal
- Additional Journal Information:
- Journal Volume: 475; Journal Issue: 21; Journal ID: ISSN 0264-6021
- Publisher:
- Biochemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; ascorbic acid metabolism; dehydroascorbic acid; diketogulonate; reactive oxygen species; singlet oxygen; superoxide; agricultural & industrial bioscience; glycobiology; metabolism; plant biology
Citation Formats
Dewhirst, Rebecca A., and Fry, Stephen C. The oxidation of dehydroascorbic acid and 2,3-diketogulonate by distinct reactive oxygen species. United States: N. p., 2018.
Web. doi:10.1042/bcj20180688.
Dewhirst, Rebecca A., & Fry, Stephen C. The oxidation of dehydroascorbic acid and 2,3-diketogulonate by distinct reactive oxygen species. United States. https://doi.org/10.1042/bcj20180688
Dewhirst, Rebecca A., and Fry, Stephen C. Fri .
"The oxidation of dehydroascorbic acid and 2,3-diketogulonate by distinct reactive oxygen species". United States. https://doi.org/10.1042/bcj20180688. https://www.osti.gov/servlets/purl/1658353.
@article{osti_1658353,
title = {The oxidation of dehydroascorbic acid and 2,3-diketogulonate by distinct reactive oxygen species},
author = {Dewhirst, Rebecca A. and Fry, Stephen C.},
abstractNote = {l-Ascorbate, dehydro-l-ascorbic acid (DHA), and 2,3-diketo-l-gulonate (DKG) can all quench reactive oxygen species (ROS) in plants and animals. The vitamin C oxidation products thereby formed are investigated here. DHA and DKG were incubated aerobically at pH 4.7 with peroxide (H2O2), ‘superoxide’ (a ~50:50 mixture of O2 and HO2), hydroxyl radicals (•OH, formed in Fenton mixtures), and illuminated riboflavin (generating singlet oxygen, 1O2). Products were monitored electrophoretically. DHA quenched H2O2 far more effectively than superoxide, but the main products in both cases were 4-O-oxalyl-l-threonate (4-OxT) and smaller amounts of 3-OxT and OxA + threonate. H2O2, but not superoxide, also yielded cyclic-OxT. Dilute Fenton mixture almost completely oxidised a 50-fold excess of DHA, indicating that it generated oxidant(s) greatly exceeding the theoretical •OH yield; it yielded oxalate, threonate, and OxT. 1O2 had no effect on DHA. DKG was oxidatively decarboxylated by H2O2, Fenton mixture, and 1O2, forming a newly characterised product, 2-oxo-l-threo-pentonate (OTP; ‘2-keto-l-xylonate’). Superoxide yielded negligible OTP. Prolonged H2O2 treatment oxidatively decarboxylated OTP to threonate. Oxidation of DKG by H2O2, Fenton mixture, or 1O2 also gave traces of 4-OxT but no detectable 3-OxT or cyclic-OxT. In conclusion, DHA and DKG yield different oxidation products when attacked by different ROS. DHA is more readily oxidised by H2O2 and superoxide; DKG more readily by 1O2. The diverse products are potential signals, enabling organisms to respond appropriately to diverse stresses. Also, the reaction-product ‘fingerprints’ are analytically useful, indicating which ROS are acting in vivo.},
doi = {10.1042/bcj20180688},
journal = {Biochemical Journal},
number = 21,
volume = 475,
place = {United States},
year = {Fri Nov 09 00:00:00 EST 2018},
month = {Fri Nov 09 00:00:00 EST 2018}
}
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