2-O-β-D-Glucopyranosyl-L-ascorbic acid

2-O-α-D-Glucopyranosyl-L-ascorbic acid (AA-2G) is a glucosylated derivative of L-ascorbic acid that has antioxidant and radioprotective activities.^1,2,3 It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals in a cell-free assay (EC₅₀ = 61 μM in 60% ethanol).¹ AA-2G (5 mM) inhibits γ-radiation-induced cell death in CHO-10B2 and radiosensitive xrs5 cells, as well as UVC- or broadband UVB-induced cell death in CHO-10B2 and UV-sensitive UV135 cells.² It is hydrolyzed to ascorbic acid by α-glucosidase and increases serum levels of ascorbic acid in rats and guinea pigs when administered orally at doses of 19.2 and 96 mg/animal, respectively.³ AA-2G (19.2 mg/animal per day) reverses weight loss and inhibits subcutaneous hemorrhage in guinea pigs fed a vitamin C-deficient diet.

1.Fujinami, Y., Tai, A., and Yamamoto, I.Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2GChem. Pharm. Bull. (Tokyo)49(5):642-644(2001) 2.Maeda, J., Allum, A.J., Mussallem, J.T., et al.Ascorbic acid 2-glucoside pretreatment protects cells from ionizing radiation, UVC, and short wavelength of UVBGenes (Basel)11(3)238(2020) 3.Yamamoto, I., Suga, S., Mitoh, Y., et al.Antiscorbutic activity of ?-ascorbic acid 2-glucoside and its availability as a vitamin C supplement in normal rats and guinea pigsJ. Pharmacobiodyn13(11)688-695(1990)