The oxidation of dehydroascorbic acid and 2,3-diketogulonate by distinct reactive oxygen species

Dewhirst, Rebecca A.; Fry, Stephen C.

doi:10.1042/bcj20180688

Title: The oxidation of dehydroascorbic acid and 2,3-diketogulonate by distinct reactive oxygen species

Journal Article · 09 November 2018 · Biochemical Journal

DOI: https://doi.org/10.1042/bcj20180688 · OSTI ID:1658353

Dewhirst, Rebecca A. ^[1];

^[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

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.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: U.K. Biotechnology and Biological Sciences Research Council (BBSRC); USDOE Office of Science (SC)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1658353

Journal Information:: Biochemical Journal, Journal Name: Biochemical Journal Journal Issue: 21 Vol. 475; ISSN 0264-6021

Publisher:: Biochemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
59 BASIC BIOLOGICAL SCIENCES
agricultural & industrial bioscience
ascorbic acid metabolism
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diketogulonate
glycobiology
metabolism
plant biology
reactive oxygen species
singlet oxygen
superoxide

Title: The oxidation of dehydroascorbic acid and 2,3-diketogulonate by distinct reactive oxygen species

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