Increased Excretion of Dehydroascorbic and Diketogulonic Acids in Urine of Rats after Standardized Temperature Shock

Monier, Mary Mills; Weiss, Roslyn J.

doi:10.3181/00379727-84-20550

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“…Here we have characterised five non-redox products of DKG catabolism formed at room temperature in aqueous, slightly sub-pH7 solutions mimicking the plant apoplast (Green & Fry, 2005) and certain animal fluids such as urine, in which DKG is found (Monier & Weiss, 1953;Koshiishi et al, 1998). Two of these products (two epimers of 2-carboxy-L-threopentonolactone; CPLs) appear to be new compounds, whose production in vivo may offer analytically informative clues as to the redox state of the cellular compartments in which they occur as well as 'informing' the organism of non-oxidative, non-acidic conditions.…”

Section: Introductionmentioning

confidence: 99%

Characterisation of the non-oxidative degradation pathway of dehydroascorbic acid in slightly acidic aqueous solution

Dewhirst¹,

Murray²,

Mackay³

et al. 2020

Archives of Biochemistry and Biophysics

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Although L-ascorbate (vitamin C) is an important biological antioxidant, its degradation pathways in vivo remain incompletely characterised. Ascorbate is oxidised to dehydroascorbic acid, which can be either hydrolysed to diketogulonate (DKG) or further oxidised. DKG can be further degraded, oxidatively or non-oxidatively. Here we characterise DKG products formed non-enzymically and non-oxidatively at 20°C and at a slightly acidic pH typical of the plant apoplast.High-voltage electrophoresis revealed at least five products, including two novel CPLs (epimers of 2-carboxy-L-threo-pentonolactone), which slowly interconverted with CPA (2carboxy-L-threo-pentonate). One of the two CPLs has an exceptionally low pKa. The CPL structures were supported by MS [(C6H7O7) -] and by 1 H and 13 C NMR spectroscopy.Xylonate and its lactone also appeared.Experiments with [1-14 C]DKG showed that all five products (including the 5-carbon xylonate and its lactone) retained DKG's carbon-1; therefore, most xylonate arose by decarboxylation of CPLs or CPA, one of whose -COOH groups originates from C-2 or C-3 of DKG after a 'benzilic acid rearrangement'. Since CPLs appeared before CPA, a DKG lactone is probably the main species undergoing this rearrangement.CPA and CPL also form non-enzymically in vivo, where they may be useful to researchers as 'fingerprints', or to organisms as 'signals', indicating a non-oxidative, slightly acidic biological compartment.

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Section: Introductionmentioning

confidence: 99%