Journal of Agricultural and Food Chemistry 2010-10-13

Production, stability, and antioxidative and antimicrobial activities of two L-ascorbate analogues from phycomyces blakesleeanus: D-erythroascorbate and D-erythroascorbate glucoside.

Marta Gutierrez-Larrainzar, Cristina de Castro, Pilar del Valle, Javier Rúa, María Rosario García-Armesto, Félix Busto, Dolores de Arriaga

Index: J. Agric. Food Chem. 58(19) , 10631-8, (2010)

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Abstract

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.