- 1) Englard, S., and Seifter, S., The biochemical functions of ascorbic acid. Annu. Rev. Nutr., 6, 365–406 (1986).
- 2) Naidu, K. A., Vitamin C in human health and disease is still a mystery? An overview. Nutr. J., 2, 7 (2003).
- 3) Bendich, A., Machlin, L. J., Scandurra, O., Burton, G. W., and Wayner, D. D. M., The antioxidant role of vitamin C. Adv. Free Radic. Biol. Med., 2, 419–444 (1986).
- 4) Yamamoto, I., Muto, N., Nagata, E., Nakamura, T., and Suzuki, Y., Formation of a stable L-ascorbic acid α-glucoside by mammalian α-glucosidase-catalyzed transglucosylation. Biochim. Biophys. Acta, 1035, 44–50 (1990).
- 5) Yamamoto, I., Muto, N., Murakami, K., Suga, S., and Yamaguchi, H., L-Ascorbic acid α-glucoside formed by regioselective transglucosylation with rat intestinal and rice seed α-glucosidases: its improved stability and structure determination. Chem. Pharm. Bull., 38, 3020–3023 (1990).
- 6) Aga, H., Yoneyama, M., Sakai, S., and Yamamoto, I., Synthesis of 2-O-α-D-glucopyranosyl L-ascorbic acid by cyclomaltodextrin glucanotransferase from Bacillus stearothermophilus. Agric. Biol. Chem., 55, 1751–1756 (1991).
- 7) Mandai, T., Yoneyama, M., Sakai, S., Muto, N., and Yamamoto, I., The crystal structure and physicochemical properties of L-ascorbic acid 2-glucoside. Carbohydr. Res., 232, 197–205 (1992).
- 8) Yamamoto, I., Suga, S., Mitoh, Y., Tanaka, M., and Muto, N., Antiscorbutic activity of L-ascorbic acid 2-glucoside and its availability as a vitamin C supplement in normal rats and guinea pigs. J. Pharmacobio-Dyn., 13, 688–695 (1990).
- 9) Wakamiya, H., Suzuki, E., Yamamoto, I., Akiba, M., Otsuka, M., and Arakawa, N., Vitamin C activity of 2-O-α-D-glucopyranosyl-L-ascorbic acid in guinea pigs. J. Nutr. Sci. Vitaminol., 38, 235–245 (1992).
- 10) Yamamoto, I., Muto, N., Murakami, K., and Akiyama, J., Collagen synthesis in human skin fibroblasts is stimulated by a stable form of ascorbate, 2-O-α-D-glucopyranosyl-L-ascorbic acid. J. Nutr., 122, 871–877 (1992).
- 11) Kumano, Y., Sakamoto, T., Egawa, M., Iwai, I., Tanaka, M., and Yamamoto, I., In vitro and in vivo prolonged biological activities of novel vitamin C derivative, 2-O-α-D-glucopyranosyl-L-ascorbic acid (AA-2G), in cosmetic fields. J. Nutr. Sci. Vitaminol., 44, 345–359 (1998).
- 12) Kumano, Y., Sakamoto, T., Egawa, M., Tanaka, M., and Yamamoto, I., Enhancing effect of 2-O-α-D-glucopyranosyl-L-ascorbic acid, a stable ascorbic acid derivative, on collagen synthesis. Biol. Pharm. Bull., 21, 662–666 (1998).
- 13) 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-2G. Chem. Pharm. Bull., 49, 642–644 (2001).
- 14) Takebayashi, J., Tai, A., and Yamamoto, I., Long-term radical scavenging activity of AA-2G and 6-Acyl-AA-2G against 1,1-diphenyl-2-picrylhydrazyl. Biol. Pharm. Bull., 25, 1503–1505 (2002).
- 15) Takebayashi, J., Tai, A., Gohda, E., and Yamamoto, I., Characterization of the radical-scavenging reaction of 2-O-substituted ascorbic acid derivatives, AA-2G, AA-2P, and AA-2S: a kinetic and stoichiometric study. Biol. Pharm. Bull., 29, 766–771 (2006).
- 16) Takebayashi, J., Asano, R., Nakae, Y., Saito, M., Gohda, E., Yamamoto, I., and Tai, A., 2-O-α-D-glucopyranosyl-L-ascorbic acid scavenges 1,1-diphenyl-2-picrylhydrazyl radicals via a covalent adduct formation. Biosci. Biotechnol. Biochem., 71, 754–760 (2007).
- 17) Takebayashi, J., Tai, A., and Yamamoto, I., pH-dependent long-term radical scavenging activity of AA-2G and 6-Octa-AA-2G against 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation. Biol. Pharm. Bull., 26, 1368–1370 (2003).
- 18) Takebayashi, J., Kaji, H., Ichiyama, K., Makino, K., Gohda, E., Yamamoto, I., and Tai, A., Inhibition of free radical-induced erythrocyte hemolysis by 2-O-substituted ascorbic acid derivatives. Free Radic. Biol. Med., 43, 1156–1164 (2007).
- 19) Toyoda-Ono, Y., Maeda, M., Nakao, M., Yoshimura, M., Sugiura-Tomimori, N., and Fukami, H., 2-O-(β-D-Glucopyranosyl)ascorbic acid, a novel ascorbic acid analogue isolated from Lycium fruit. J. Agric. Food Chem., 52, 2092–2096 (2004).
- 20) Toyada-Ono, Y., Maeda, M., Nakao, M., Yoshimura, M., Sugiura-Tomimori, N., Fukami, H., Nishioka, H., Miyashita, Y., and Kojo, S., A novel vitamin C analog, 2-O-(β-D-Glucopyranosyl)ascorbic acid: examination of enzymatic synthesis and biological activity. J. Biosci. Bioeng., 99, 361–365 (2005).
- 21) Gillespie, K., Chae, J. M., and Ainsworth, E. A., Rapid measurement of total antioxidant capacity in plants. Nat. Protoc., 2, 867–870 (2007).
- 22) Prior, R. L., Wu, X., and Schaich, K., Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. J. Agric. Food Chem., 53, 4290–4302 (2005).
- 23) Niki, E., Komuro, E., Takahashi, M., Urano, S., Ito, E., and Terao, K., Oxidative hemolysis of erythrocytes and its inhibition by free radical scavengers. J. Biol. Chem., 263, 19809–19814 (1988).
- 24) Sato, Y., Kamo, S., Takahashi, T., and Suzuki, Y., Mechanism of free radical-induced hemolysis of human erythrocytes: hemolysis by water-soluble radical initiator. Biochemistry, 34, 8940–8949 (1995).
- 25) Masatsuji-Kato, E., Tsuzuki, T., and Kobayashi, S., Reduction of UVB/A-generated free radicals by sodium L-ascorbyl-2-phosphate in cultured mouse skin. J. Health Sci., 51, 122–129 (2005).
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Antioxidant Properties of 2-O-β-D-Glucopyranosyl-L-ascorbic Acid
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