Dehydroascorbic Acid

Tolbert, Bert M.; Ward, J.

doi:10.1021/ba-1982-0200.ch005

Cited by 72 publications

(34 citation statements)

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“…1e). The formation of this requires the presence of the C6 hydroxyl group (12). The overall geometry of this molecule and the presence of multiple hydroxyl groups has suggested a similarity of this structure to that of glucose (24).…”

Section: -Bromo-6-deoxy-l-ascorbic Acidmentioning

confidence: 94%

“…On the other hand, the oxidized form of ascorbic acid (DHA) has been shown to exist in solution as hydrates and can also form a cyclic hemiketal (Fig. 1e) (12). This latter structure cannot be formed in the absence of the 6-hydroxyl group.…”

Section: Characterization Of 6-halo-ascorbic Acid Analogs and Halodehmentioning

confidence: 99%

“…Our rationale for using 6-halo-ascorbic acid analogs was based in part on their structures obtained from 13 C NMR (12). The reduced forms of the 6-halo ascorbic acid analogs are structurally similar to ascorbic acid, and we predicted that they would be transported by SVCT1 and SVCT2.…”

Section: -Bromo-6-deoxy-l-ascorbic Acidmentioning

confidence: 99%

“…Second, the products of oxidation of 6-halo-6-deoxy-L-ascorbic acids, the 6-halo-dehydroascorbic acids, cannot cyclize, in contrast to DHA, which exists in solution predominantly as a bicyclic hemiketal (see Fig. 1e) (12). Unfortunately, the properties of the 6-halo-ascorbates themselves have been only partially described (11).…”

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confidence: 99%

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6-Bromo-6-deoxy-l-ascorbic Acid

Corpe

Lee

Kwon

et al. 2005

Journal of Biological Chemistry

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Vitamin C intracellular accumulation is mediated by Na؉ -dependent vitamin C transporters SVCT1 and -2 and dehydroascorbic acid transporters GLUT1 and -3. It is unclear which pathways dominate in vivo. As a new step to resolve this issue, we identified and tested 6-bromo-6-deoxy-L-ascorbic acid as a specific candidate for SVCTs. In high performance liquid chromatography and electron paramagnetic resonance analyses, the reduced compounds ascorbic acid and 6-bromo-6-deoxy-L-ascorbic acid were similar. The oxidized products 6-bromo-6-deoxy dehydroascorbic acid (BrDHA) and dehydroascorbic acid (DHA) had comparable stabilities, based on reduction recoveries. Upon expression of GLUT1 or GLUT3 in Xenopus oocytes, BrDHA was neither transported nor bound, in contrast to robust transport of DHA. The findings were not explained by differences in the oocyte reduction of DHA and BrDHA because lysed oocytes reduced both compounds equally. Further, there was no transport of the reduced compound, 6-bromo-6-deoxy-L-ascorbic acid, by GLUT1 or GLUT3. As a prerequisite for investigating 6-bromo-6-deoxy-L-ascorbic acid transported by SVCTs, SVCT2 transport activity in oocytes was enhanced 14-fold by construction and use of a vector that added a fixed poly(A) tail to the 3 end of cRNA. For SVCT1 and SVCT2 expressed in oocytes, similar K m and V max values were observed for ascorbic acid and 6-bromo-6-deoxy-Lascorbic acid. In human fibroblasts, predicted to have SVCT-mediated ascorbate accumulation, K m and V max values were again comparable for ascorbic acid and 6-bromo-6-deoxy-L-ascorbic acid. Using activated human neutrophils, predicted to have ascorbate accumulation mediated predominantly by DHA and GLUT transporters, 6-bromo-6-deoxy-L-ascorbic acid accumulation was <1% of accumulation when compared with ascorbic acid. We conclude that 6-bromo-6-deoxy-L-ascorbic acid is the first transport substrate identified as completely specific for SVCTs, but not GLUTs, and provide a new strategy to determine the contribution of each pathway to ascorbate accumulation.

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Section: -Bromo-6-deoxy-l-ascorbic Acidmentioning

confidence: 94%

Section: Characterization Of 6-halo-ascorbic Acid Analogs and Halodehmentioning

confidence: 99%

Section: -Bromo-6-deoxy-l-ascorbic Acidmentioning

confidence: 99%

mentioning

confidence: 99%

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6-Bromo-6-deoxy-l-ascorbic Acid

Corpe

Lee

Kwon

et al. 2005

Journal of Biological Chemistry

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“…Subsequent sections highlight the neurobehavioral link between striatal AA release and glutamate uptake and their disruption in HD. Numerous sources provide detailed information on AA biochemistry (13,121), the molecular genetics of HD (29,75,111,117), and corticostriatal involvement in behavioral control (68,86).…”

Section: Antioxidants and Redox Signalingmentioning

confidence: 99%

Dysregulation of Corticostriatal Ascorbate Release and Glutamate Uptake in Transgenic Models of Huntington's Disease

Rebec

2013

Antioxidants & Redox Signaling

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Significance: Dysregulation of cortical and striatal neuronal processing plays a critical role in Huntington's disease (HD), a dominantly inherited condition that includes a progressive deterioration of cognitive and motor control. Growing evidence indicates that ascorbate (AA), an antioxidant vitamin, is released into striatal extracellular fluid when glutamate is cleared after its release from cortical afferents. Both AA release and glutamate uptake are impaired in the striatum of transgenic mouse models of HD owing to a downregulation of glutamate transporter 1 (GLT1), the protein primarily found on astrocytes and responsible for removing most extracellular glutamate. Improved understanding of an AA-glutamate interaction could lead to new therapeutic strategies for HD. Recent Advances: Increased expression of GLT1 following treatment with ceftriaxone, a beta-lactam antibiotic, increases striatal glutamate uptake and AA release and also improves the HD behavioral phenotype. In fact, treatment with AA alone restores striatal extracellular AA to wild-type levels in HD mice and not only improves behavior but also improves the firing pattern of neurons in HD striatum. Critical Issues: Although evidence is growing for an AA-glutamate interaction, several key issues require clarification: the site of action of AA on striatal neurons; the precise role of GLT1 in striatal AA release; and the mechanism by which HD interferes with this role. Future Directions: Further assessment of how the HD mutation alters corticostriatal signaling is an important next step. A critical focus is the role of astrocytes, which express GLT1 and may be the primary source of extracellular AA.

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Partition of vitamin C activity in commercial citrus products

Lee¹,

Coates²

1999

Nahrung

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Dehydroascorbic Acid

Cited by 72 publications

References 0 publications

6-Bromo-6-deoxy-l-ascorbic Acid

6-Bromo-6-deoxy-l-ascorbic Acid

Dysregulation of Corticostriatal Ascorbate Release and Glutamate Uptake in Transgenic Models of Huntington's Disease

Partition of vitamin C activity in commercial citrus products

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