Biosynthesis of L-ascorbic acid in plants: new pathways for an old antioxidant

Valpuesta, Victoriano; Botella, Miguel A.

doi:10.1016/j.tplants.2004.10.002

Cited by 275 publications

(194 citation statements)

References 36 publications

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“…Although very rare, L-lyxonic acid has also been identified as a vitamin C product (24); the rare sugar D-lyxose can be found in a modified form in a limited number of organisms (26). Among the compounds involved in the synthesis of vitamin C are L-gulose, L-gulonic acid, L-galactose, and L-galactonic acid (27). The lack of significant relative abundances of the L enantiomers of sugar acids (from interior meteorite samples), particularly L-arabinonic acid and L-threonic acid, suggests that the observed D EE are likely to be indigenous to the meteorites.…”

Section: Natural Occurrence Of Relevant Sugar Derivatives and Enantiomentioning

confidence: 99%

Enantiomer excesses of rare and common sugar derivatives in carbonaceous meteorites

Cooper

Rios

2016

Proc. Natl. Acad. Sci. U.S.A.

123

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Biological polymers such as nucleic acids and proteins are constructed of only one-the D or L-of the two possible nonsuperimposable mirror images (enantiomers) of selected organic compounds. However, before the advent of life, it is generally assumed that chemical reactions produced 50:50 (racemic) mixtures of enantiomers, as evidenced by common abiotic laboratory syntheses. Carbonaceous meteorites contain clues to prebiotic chemistry because they preserve a record of some of the Solar System's earliest (∼4.5 Gy) chemical and physical processes. In multiple carbonaceous meteorites, we show that both rare and common sugar monoacids (aldonic acids) contain significant excesses of the D enantiomer, whereas other (comparable) sugar acids and sugar alcohols are racemic. Although the proposed origins of such excesses are still tentative, the findings imply that meteoritic compounds and/or the processes that operated on meteoritic precursors may have played an ancient role in the enantiomer composition of life's carbohydrate-related biopolymers.carbonaceous meteorites | sugar acids | enantiomer excesses | aldonic acids | polyols T he organic phase of carbonaceous meteorites comprises an insoluble "macromolecular" material (1-3), a complex mixture of largely uncharacterized solvent-extractable compounds (4), as well as discrete (identified) soluble organic compounds such as amino acids (3, 5) nucleobases (6, 7), and sugar derivatives (8). Analyses of this prebiotic organic carbon have been important in understanding its early Solar System synthesis and history: Characteristics of the organic phase suggest that it consists of both products and survivors of interstellar/presolar grain irradiation (9) and subsequent encapsulation and aqueous reactions (10, 11) in asteroids "parent bodies."Several identified meteoritic organic compounds are chiral: They can exist as two nonsuperimposable mirror image compounds called enantiomers, commonly designated D and L. To date, most chiral meteoritic compounds are reported to be racemic mixtures, i.e., their D and L enantiomers are equal in abundance (3). Racemic compounds are expected in nature because typical abiotic synthetic processes are (historically) thought to occur in the absence of asymmetric influences. Racemic mixtures are equated with pristine/uncontaminated abiotic samples when discussing meteoritic compounds. However, some meteoritic amino acids that are rare on Earth, i.e., they are not constituents of proteins and therefore less likely to be contaminants, have been confirmed to contain L enantiomer excesses (EE) (3, 12, 13). The origins of such excesses are unknown.Sugars, aldehydes, or ketones that contain multiple carbon hydroxyl (carbon alcohol) groups, are also chiral and were likely necessary for the origin of life. In the majority of extant biological sugars and derivatives ("polyols"), the D enantiomers are significantly more abundant than the L enantiomers (we will note exceptions in Results and Natural Occurrence of Relevant Sugar Derivatives and Enantiomers)...

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Section: Natural Occurrence Of Relevant Sugar Derivatives and Enantiomentioning

confidence: 99%

Enantiomer excesses of rare and common sugar derivatives in carbonaceous meteorites

Cooper

Rios

2016

Proc. Natl. Acad. Sci. U.S.A.

123

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“…At least in one case, exogenously increasing the levels of the L-Galactono-1,4-lactone dehydrogenase intermediate can enhance oxidative stress tolerance (Zhao et al, 2005), and it has been suggested that the dehydrogenase may be an important control point in ascorbic acid synthesis (Valpuesta and Botella, 2004).…”

Section: Antioxidative and Detoxification Proteinsmentioning

confidence: 99%

Proteomic Study of Low-Temperature Responses in Strawberry Cultivars (Fragaria×ananassa) That Differ in Cold Tolerance

Koehler

Wilson²,

Goodpaster

et al. 2012

Plant Physiology

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To gain insight into the molecular basis contributing to overwintering hardiness, a comprehensive proteomic analysis comparing crowns of octoploid strawberry (Fragaria 3 ananassa) cultivars that differ in freezing tolerance was conducted. Four cultivars were examined for freeze tolerance and the most cold-tolerant cultivar ('Jonsok') and least-tolerant cultivar ('Frida') were compared with a goal to reveal how freezing tolerance is achieved in this distinctive overwintering structure and to identify potential cold-tolerance-associated biomarkers. Supported by univariate and multivariate analysis, a total of 63 spots from twodimensional electrophoresis analysis and 135 proteins from label-free quantitative proteomics were identified as significantly differentially expressed in crown tissue from the two strawberry cultivars exposed to 0-, 2-, and 42-d cold treatment. Proteins identified as cold-tolerance-associated included molecular chaperones, antioxidants/detoxifying enzymes, metabolic enzymes, pathogenesis-related proteins, and flavonoid pathway proteins. A number of proteins were newly identified as associated with cold tolerance. Distinctive mechanisms for cold tolerance were characterized for two cultivars. In particular, the 'Frida' cold response emphasized proteins specific to flavonoid biosynthesis, while the more freezing-tolerant 'Jonsok' had a more comprehensive suite of known stress-responsive proteins including those involved in antioxidation, detoxification, and disease resistance. The molecular basis for 'Jonsok'-enhanced cold tolerance can be explained by the constitutive level of a number of proteins that provide a physiological stress-tolerant poise. Strawberry (Fragaria 3 ananassa) cultivation predominates in regions with mild winters. In colder climates, overwintering hardiness is an essential trait for strawberry cultivation. Freezing injury of strawberry plants is one of the greatest factors in reducing crop yield and quality in temperate regions. Winter damage in Norway, for example, on average causes losses of 20%. Thus, production of cultivars with improved freezing hardiness is one of Norway's major objectives for their strawberry breeding programs. Improvement of cold hardiness is desirable for securing economic sustainability of the existing crops, and for expanding the growing regions of temperate fruit crops. Because strawberry is a representative species for the Rosaceae crops (e

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“…Wheeler et al ( 5 ) have proved that AsA is synthesized mainly from D -glucose via GDP-mannose, L -galactose, and L -galactono-1,4-lactone. Some novel shunts for AsA biosynthesis have also been reported recently ( 6 ). Higher plants use AsA as an electron donor for AsA peroxidase for scavenging of ROS ( 7 ), and this is quite distinct from the case in mammals, which use GSH for selenocysteine-containing glutathione peroxidase.…”

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confidence: 99%

Heterologous Expression of Dehydroascorbate Reductase from Rice and Its Application to Determination of Dehydroascorbate Concentrations

Amako

Ushimaru

Ishikawa

et al. 2006

J Nutr Sci Vitaminol

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SummaryWe constructed an expression vector for rice dehydroascorbate reductase (DHAR) (EC 1.8.5.4) with a polyhistidine tag at the amino terminus and introduced the vector into several strains of Escherichia coli . On conventional induction treatment with isopropylthiol-␤ -D -galactoside, E. coli harboring rice DHAR cDNA produced doublet polypeptides of about 27 kDa. Induction duration or growth temperature did not affect the ratio of these polypeptides. Only the larger polypeptide, corresponding to full-length recombinant DHAR, was produced in E. coli supplemented with tRNAs for several minor codons. Most of the enzymatic characteristics of the recombinant DHAR were similar to those of the native one, although the recombinant protein showed increased heat susceptibility. Using recombinant DHAR, we developed a method for simple and precise determination of dehydroascorbate concentrations in tissue extracts by spectrophotometry, and we successfully applied the method to several fruit juices and vegetables.

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Biosynthesis of L-ascorbic acid in plants: new pathways for an old antioxidant

Cited by 275 publications

References 36 publications

Enantiomer excesses of rare and common sugar derivatives in carbonaceous meteorites

Enantiomer excesses of rare and common sugar derivatives in carbonaceous meteorites

Proteomic Study of Low-Temperature Responses in Strawberry Cultivars (Fragaria×ananassa) That Differ in Cold Tolerance

Heterologous Expression of Dehydroascorbate Reductase from Rice and Its Application to Determination of Dehydroascorbate Concentrations

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