메뉴 건너뛰기




Volumn 71, Issue 3, 2007, Pages 754-760

2-O-α-D-glucopyranosyl-L-ascorbic acid scavenges 1,1-diphenyl-2- picrylhydrazyl radicals via a covalent adduct formation

Author keywords

1,1 diphenyl 2 picrylhydrazyl radical; 2 O D glucopyranosyl L ascorbic acid; Covalent adduct formation; Radical scavenging mechanism; Reaction stoichiometry

Indexed keywords

1,1-DIPHENYL-2-PICRYLHYDRAZYL RADICAL; 2-O-Α-D-GLUCOPYRANOSYL-L-ASCORBIC ACID; COVALENT ADDUCT FORMATION; RADICAL-SCAVENGING MECHANISM; REACTION STOICHIOMETRY;

EID: 33947576052     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.60602     Document Type: Article
Times cited : (17)

References (26)
  • 1
    • 0025349048 scopus 로고
    • Formation of a stable L-ascorbic acid α-glucoside by mammalian α-glucosidase-catalyzed trans-glucosylation
    • 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 trans-glucosylation. Biochim. Biophys. Acta, 1035, 44-50 (1990).
    • (1990) Biochim. Biophys. Acta , vol.1035 , pp. 44-50
    • Yamamoto, I.1    Muto, N.2    Nagata, E.3    Nakamura, T.4    Suzuki, Y.5
  • 2
    • 0025633123 scopus 로고    scopus 로고
    • 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 glucoside α-glucosidases: its improved stability and structure determination. Chem. Pharm. Bull., 38, 3020-3023 (1990).
    • 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 glucoside α-glucosidases: its improved stability and structure determination. Chem. Pharm. Bull., 38, 3020-3023 (1990).
  • 3
    • 0000040234 scopus 로고
    • Synthesis of 2-O-α-D-glucopyranosyl L-ascorbic acid by cyclomaltodextrin glucanotransferase from Bacillus stearothermophilus
    • 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).
    • (1991) Agric. Biol. Chem , vol.55 , pp. 1751-1756
    • Aga, H.1    Yoneyama, M.2    Sakai, S.3    Yamamoto, I.4
  • 4
    • 0027110858 scopus 로고
    • The crystal structure and physicochemical properties of L-ascorbic acid 2-glucoside
    • 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).
    • (1992) Carbohydr. Res , vol.232 , pp. 197-205
    • Mandai, T.1    Yoneyama, M.2    Sakai, S.3    Muto, N.4    Yamamoto, I.5
  • 5
    • 0025611002 scopus 로고
    • Antiscorbutic activity of L-ascorbic acid 2-glucoside and its availability as a vitamin C supplement in normal rats and guinea pigs
    • 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).
    • (1990) J. Pharmacobio-Dyn , vol.13 , pp. 688-695
    • Yamamoto, I.1    Suga, S.2    Mitoh, Y.3    Tanaka, M.4    Muto, N.5
  • 7
    • 0026525023 scopus 로고
    • Collagen synthesis in human skin fibroblasts is stimulated by a stable form of ascorbate, 2-O-α-D-glucopyranosyl-L-ascorbic acid
    • 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).
    • (1992) J. Nutr , vol.122 , pp. 871-877
    • Yamamoto, I.1    Muto, N.2    Murakami, K.3    Akiyama, J.4
  • 8
    • 0031827156 scopus 로고    scopus 로고
    • 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
    • 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).
    • (1998) J. Nutr. Sci. Vitaminol , vol.44 , pp. 345-359
    • Kumano, Y.1    Sakamoto, T.2    Egawa, M.3    Iwai, I.4    Tanaka, M.5    Yamamoto, I.6
  • 9
    • 0031858945 scopus 로고    scopus 로고
    • Enhancing effect of 2-O-α-D-glucopyranosyl-L- ascorbic acid, a stable ascorbic acid derivative, on collagen synthesis
    • 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).
    • (1998) Biol. Pharm. Bull , vol.21 , pp. 662-666
    • Kumano, Y.1    Sakamoto, T.2    Egawa, M.3    Tanaka, M.4    Yamamoto, I.5
  • 11
    • 33645539270 scopus 로고
    • 2-O-Octadecylascorbic acid with no vitamin C activity in ODS-od/od rats
    • Horio, F., Kobayashi, T., and Yoshida, A., 2-O-Octadecylascorbic acid with no vitamin C activity in ODS-od/od rats. Agric. Biol. Chem., 55, 1429-1430 (1991).
    • (1991) Agric. Biol. Chem , vol.55 , pp. 1429-1430
    • Horio, F.1    Kobayashi, T.2    Yoshida, A.3
  • 12
    • 0034985238 scopus 로고    scopus 로고
    • Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2G
    • 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).
    • (2001) Chem. Pharm. Bull , vol.49 , pp. 642-644
    • Fujinami, Y.1    Tai, A.2    Yamamoto, I.3
  • 13
    • 0042796062 scopus 로고    scopus 로고
    • Long-term radical scavenging activity of AA-2G and 6-Acyl-AA-2G against 1,1-diphenyl-2-picrylhydrazyl
    • 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).
    • (2002) Biol. Pharm. Bull , vol.25 , pp. 1503-1505
    • Takebayashi, J.1    Tai, A.2    Yamamoto, I.3
  • 14
    • 1642427823 scopus 로고    scopus 로고
    • pH-dependent long-term radical scavenging activity of AA-2G and 6-Octa-AA-2G against 2,20-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation
    • Takebayashi, J., Tai, A., and Yamamoto, I., pH-dependent long-term radical scavenging activity of AA-2G and 6-Octa-AA-2G against 2,20-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation. Biol. Pharm. Bull., 26, 1368-1370 (2003).
    • (2003) Biol. Pharm. Bull , vol.26 , pp. 1368-1370
    • Takebayashi, J.1    Tai, A.2    Yamamoto, I.3
  • 15
    • 33645541662 scopus 로고    scopus 로고
    • 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
    • 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).
    • (2006) Biol. Pharm. Bull , vol.29 , pp. 766-771
    • Takebayashi, J.1    Tai, A.2    Gohda, E.3    Yamamoto, I.4
  • 16
    • 0034132309 scopus 로고    scopus 로고
    • Studies on the 1,1-diphenyl-2-picrylhydrazyl radical scavenging mechanism for a 2-pyrone compound
    • Abe, N., Nemoto, A., Tsuchiya, Y., Hojo, H., and Hirota, A., Studies on the 1,1-diphenyl-2-picrylhydrazyl radical scavenging mechanism for a 2-pyrone compound. Biosci. Biotechnol. Biochem., 64, 306-313 (2000).
    • (2000) Biosci. Biotechnol. Biochem , vol.64 , pp. 306-313
    • Abe, N.1    Nemoto, A.2    Tsuchiya, Y.3    Hojo, H.4    Hirota, A.5
  • 17
    • 0000907157 scopus 로고    scopus 로고
    • Isolation of a 2-pyrone compound as an antioxidant from a fungus and its new reaction product with 1,1-diphenyl-2-picrylhydrazyl radical
    • Hirota, A., Nemoto, A., Tsuchiya, Y., Hojo, H., and Abe, N., Isolation of a 2-pyrone compound as an antioxidant from a fungus and its new reaction product with 1,1-diphenyl-2-picrylhydrazyl radical. Biosci. Biotechnol. Biochem., 63, 418-420 (1999).
    • (1999) Biosci. Biotechnol. Biochem , vol.63 , pp. 418-420
    • Hirota, A.1    Nemoto, A.2    Tsuchiya, Y.3    Hojo, H.4    Abe, N.5
  • 18
    • 0035799725 scopus 로고    scopus 로고
    • Unusually large numbers of electrons for the oxidation of polyphenolic antioxidants
    • Hotta, H., Sakamoto, H., Nagano, S., Osakai, T., and Tsujino, Y., Unusually large numbers of electrons for the oxidation of polyphenolic antioxidants. Biochim. Biophys. Acta, 1526, 159-167 (2001).
    • (2001) Biochim. Biophys. Acta , vol.1526 , pp. 159-167
    • Hotta, H.1    Sakamoto, H.2    Nagano, S.3    Osakai, T.4    Tsujino, Y.5
  • 19
    • 0037104669 scopus 로고    scopus 로고
    • Higher radical scavenging activities of polyphenolic antioxidants can be ascribed to chemical reactions following their oxidation
    • Hotta, H., Nagano, S., Ueda, M., Tsujino, Y., Koyama, J., and Osakai, T., Higher radical scavenging activities of polyphenolic antioxidants can be ascribed to chemical reactions following their oxidation. Biochim. Biophys. Acta, 1572, 123-132 (2002).
    • (2002) Biochim. Biophys. Acta , vol.1572 , pp. 123-132
    • Hotta, H.1    Nagano, S.2    Ueda, M.3    Tsujino, Y.4    Koyama, J.5    Osakai, T.6
  • 20
    • 0037122702 scopus 로고    scopus 로고
    • Synthesis and characterization of a series of novel monoacylated ascorbic acid derivatives, 6-O-acyl-2-O-α-D-glucopyranosyl- L-ascorbic acids, as skin antioxidants
    • Yamamoto, I., Tai, A., Fujinami, Y., Sasaki, K., and Okazaki, S., Synthesis and characterization of a series of novel monoacylated ascorbic acid derivatives, 6-O-acyl-2-O-α-D-glucopyranosyl- L-ascorbic acids, as skin antioxidants. J. Med. Chem., 45, 462-468 (2002).
    • (2002) J. Med. Chem , vol.45 , pp. 462-468
    • Yamamoto, I.1    Tai, A.2    Fujinami, Y.3    Sasaki, K.4    Okazaki, S.5
  • 21
    • 0021362463 scopus 로고
    • β-Carotene: An unusual type of lipid antioxidant
    • Burton, G. W., and Ingold, K. U., β-Carotene: an unusual type of lipid antioxidant. Science, 224, 569-573 (1984).
    • (1984) Science , vol.224 , pp. 569-573
    • Burton, G.W.1    Ingold, K.U.2
  • 23
    • 0023923325 scopus 로고
    • Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids
    • Kato, K., Terao, S., Shimamoto, N., and Hirata, M., Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids. J. Med. Chem., 31, 793-798 (1988).
    • (1988) J. Med. Chem , vol.31 , pp. 793-798
    • Kato, K.1    Terao, S.2    Shimamoto, N.3    Hirata, M.4
  • 24
    • 0034058793 scopus 로고    scopus 로고
    • Ascorbic acid 2-glucoside prevents sinusoidal endothelial cell apoptosis in supercooled preserved grafts in rat liver transplantation
    • Matsukawa, H., Yagi, T., Matsuda, H., Kawahara, H., Yamamoto, I., Matsuoka, J., and Tanaka, N., Ascorbic acid 2-glucoside prevents sinusoidal endothelial cell apoptosis in supercooled preserved grafts in rat liver transplantation. Transplant. Proc., 32, 313-317 (2000).
    • (2000) Transplant. Proc , vol.32 , pp. 313-317
    • Matsukawa, H.1    Yagi, T.2    Matsuda, H.3    Kawahara, H.4    Yamamoto, I.5    Matsuoka, J.6    Tanaka, N.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.