Production, Stability, and Antioxidative and Antimicrobial Activities of Two l-Ascorbate Analogues from Phycomyces blakesleeanus: d-Erythroascorbate and d-Erythroascorbate Glucoside

d-Erythroascorbate (d-EAA), a five-carbon analogue of l-ascorbate (l-AA), and d-erythroascorbate monoglucoside (d-EAAG) are accumulated in Phycomyces blakesleeanus grown on glucose (99.5 and 1084 μg/g mycelial dry weight, respectively) and also excreted into the culture medium. Both compounds showed...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2010-10, Vol.58 (19), p.10631-10638
Main Authors: Gutierrez-Larrainzar, Marta, de Castro, Cristina, del Valle, Pilar, Rúa, Javier, García-Armesto, María Rosario, Busto, Félix, de Arriaga, Dolores
Format: Article
Language:English
Subjects:
animal pathogenic bacteria
Anti-Infective Agents - pharmacology
antimicrobial properties
antioxidant activity
Antioxidants - pharmacology
ascorbic acid
Ascorbic Acid - analogs & derivatives
Ascorbic Acid - biosynthesis
Ascorbic Acid - chemistry
Ascorbic Acid - pharmacology
Biological and medical sciences
biosynthesis
chemical composition
chemical structure
Culture Media
d-erythroascorbate
d-erythroascorbate monoglucoside
Drug Stability
Escherichia coli
food additives
Food Chemistry/Biochemistry
Food industries
Food microbiology
Fundamental and applied biological sciences. Psychology
glucose
glucosides
Glucosides - biosynthesis
Glucosides - chemistry
Glucosides - pharmacology
Glucosyltransferases - metabolism
mycelium
natural additives
Phycomyces - enzymology
Phycomyces - metabolism
Phycomyces blakesleeanus
spectral analysis
stereoisomers
ultraviolet-visible spectroscopy
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Summary:d-Erythroascorbate (d-EAA), a five-carbon analogue of l-ascorbate (l-AA), and d-erythroascorbate monoglucoside (d-EAAG) are accumulated in Phycomyces blakesleeanus grown on glucose (99.5 and 1084 μg/g mycelial dry weight, respectively) and also excreted into the culture medium. Both compounds showed UV spectral properties and ionization constants similar to those of l-AA. d-EAAG was much more stable to aerobic oxidation than d-EAA and l-AA at acidic pH. d-EAAG is synthesized from d-erythroascorbate by a mycelial glucosyltransferase activity that uses UDP-glucose as glucose substrate donor with K m = 2.5 mM and 41.3 μM for d-EAA. This glucosyltransferase activity was maximal in the stationary growth phase in parallel with maximal production of d-EAAG. The presence of d-arabinose or d-arabinono-1,4-lactone in the culture medium produces the maximal accumulation of d-EAA and d-EAAG (about 30- and 4-fold with respect to that obtained in glucose culture). Both compounds showed greater antioxidant activity than l-AA and other standard antioxidants, with a capacity similar to that of l-AA to inhibit the growth of Escherichia coli.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf102202e