Antioxidant properties of 2-O-β-D-glucopyranosyl-L-ascorbic acid

Bioscience, Biotechnology and Biochemistry

Volumn 72, Issue 6, 2008, Pages 1558-1563

  Takebayashi, Jun ^a   Yagi, Yasuyuki ^b   Ishii, Rie ^c   Abe, Shigeki ^c   Yamada, Kazuhiko ^a   Tai, Akihiro ^c,d  

^a NATIONAL INSTITUTE OF HEALTH AND NUTRITION   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^c OKAYAMA UNIVERSITY   (Japan)

^d PREFECTURAL UNIVERSITY OF HIROSHIMA   (Japan)

Author keywords

2 O D glucopyranosyl L ascorbic acid; Antioxidant activity; In vitro radical scavenging assay; Moderate and long lasting radical scavenging reaction; Stable vitamin C derivative

Indexed keywords

ORGANIC ACIDS;

ANTI-OXIDANT PROPERTIES; ANTIOXIDANT ACTIVITIES; ASCORBIC ACID (ASC); IN-VITRO; L ASCORBIC ACID; RADICAL CATION (RC); SULFONIC ACID (SFA);

KETONES;

2 O (BETA D GLUCOPYRANOSYL)ASCORBIC ACID; 2,2' AZINO DI (3 ETHYLBENZOTHIAZOLINE) 6 SULFONIC ACID; 2,2' AZOBIS(2 AMIDINOPROPANE); 2,2'-AZINO-DI-(3-ETHYLBENZOTHIAZOLINE)-6-SULFONIC ACID; 2,2'-AZOBIS(2-AMIDINOPROPANE); 2-O-(BETA-D-GLUCOPYRANOSYL)ASCORBIC ACID; AMIDINE; ANTIOXIDANT; ASCORBIC ACID; BENZOTHIAZOLE DERIVATIVE; DRUG DERIVATIVE; SULFONIC ACID DERIVATIVE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ERYTHROCYTE; HEMOLYSIS; PH; SHEEP;

AMIDINES; ANIMALS; ANTIOXIDANTS; ASCORBIC ACID; BENZOTHIAZOLES; ERYTHROCYTES; HEMOLYSIS; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; SHEEP; SULFONIC ACIDS;

EID: 45849110979     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.80063     Document Type: Article

References (25)

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).