메뉴 건너뛰기




Volumn 744, Issue , 2015, Pages 147-156

Synthesis and biological evaluation of a novel baicalein glycoside as an anti-inflammatory agent

Author keywords

Amylosucrase; Anti inflammation; Baicalein; Glycoside; Nrf2; Transglycosylation

Indexed keywords

BAICALEIN; REACTIVE OXYGEN METABOLITE; TRANSCRIPTION FACTOR NRF2; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; FLAVANONE DERIVATIVE; GLYCOSIDE; LIPOPOLYSACCHARIDE; NFE2L2 PROTEIN, MOUSE; NITRIC OXIDE;

EID: 84918814162     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2014.10.013     Document Type: Article
Times cited : (46)

References (41)
  • 1
    • 70349205883 scopus 로고    scopus 로고
    • Inclusion complex of butachlor with β-cyclodextrin: Characterization, solubility, and speciation-dependent adsorption
    • H. Bian, J. Chen, X. Cai, P. Liu, H. Liu, X. Qiao, and L. Huang Inclusion complex of butachlor with β-cyclodextrin: characterization, solubility, and speciation-dependent adsorption J. Agric. Food Chem. 57 2009 7453 7458
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 7453-7458
    • Bian, H.1    Chen, J.2    Cai, X.3    Liu, P.4    Liu, H.5    Qiao, X.6    Huang, L.7
  • 3
    • 84863449358 scopus 로고    scopus 로고
    • Separation of quercetins biological activity from its oxidative property through bioisosteric replacement of the catecholic hydroxyl groups with fluorine atoms
    • S.Y. Cho, M.K. Kim, H. Mok, H. Choo, and Y.J. Chong Separation of quercetins biological activity from its oxidative property through bioisosteric replacement of the catecholic hydroxyl groups with fluorine atoms J. Agric. Food Chem. 60 2012 6499 6506
    • (2012) J. Agric. Food Chem. , vol.60 , pp. 6499-6506
    • Cho, S.Y.1    Kim, M.K.2    Mok, H.3    Choo, H.4    Chong, Y.J.5
  • 6
    • 0033136878 scopus 로고    scopus 로고
    • Stroke therapy in traditional Chinese medicine (TCM): Prospects for drug discovery and development
    • X. Gong, and N.J. Sucher Stroke therapy in traditional Chinese medicine (TCM): prospects for drug discovery and development Trends Pharmacol. Sci. 20 1999 191 196
    • (1999) Trends Pharmacol. Sci. , vol.20 , pp. 191-196
    • Gong, X.1    Sucher, N.J.2
  • 7
    • 84874860234 scopus 로고    scopus 로고
    • Molecular effects of baicalein in Hct116 cells and Caenorhabditis elegans: Activation of the Nrf2 signaling pathway and prolongation of lifespan
    • S. Havermann, R. Rohrig, Y. Chovolou, H.U. Humpf, and W.J. Wätjen Molecular effects of baicalein in Hct116 cells and Caenorhabditis elegans: activation of the Nrf2 signaling pathway and prolongation of lifespan J. Agric. Food Chem. 61 2013 2158 2164
    • (2013) J. Agric. Food Chem. , vol.61 , pp. 2158-2164
    • Havermann, S.1    Rohrig, R.2    Chovolou, Y.3    Humpf, H.U.4    Wätjen, W.J.5
  • 12
    • 0033800922 scopus 로고    scopus 로고
    • Regulation of genes encoding NAD(P)H:quinone oxidoreductases
    • A.K. Jaiswal Regulation of genes encoding NAD(P)H:quinone oxidoreductases Free Radic. Biol. Med. 29 2000 254 262
    • (2000) Free Radic. Biol. Med. , vol.29 , pp. 254-262
    • Jaiswal, A.K.1
  • 13
    • 57249097185 scopus 로고    scopus 로고
    • Conversion of puerarin into its 7-O-glycoside derivatives by Microbacterium oxydans (CGMCC 1788) to improve its water solubility and pharmacokinetic properties
    • J.R. Jiang, S. Yuan, J.F. Ding, S.C. Zhu, H.D. Xu, T. Chen, X.D. Cong, W.P. Xu, H. Ye, and Y.J. Dai Conversion of puerarin into its 7-O-glycoside derivatives by Microbacterium oxydans (CGMCC 1788) to improve its water solubility and pharmacokinetic properties Appl. Microbiol. Biotechnol. 81 2008 647 657
    • (2008) Appl. Microbiol. Biotechnol. , vol.81 , pp. 647-657
    • Jiang, J.R.1    Yuan, S.2    Ding, J.F.3    Zhu, S.C.4    Xu, H.D.5    Chen, T.6    Cong, X.D.7    Xu, W.P.8    Ye, H.9    Dai, Y.J.10
  • 15
    • 68949186622 scopus 로고    scopus 로고
    • Enzymatic synthesis of salicin glycosides through transglycosylation catalyzed by amylosucrases from Deinococcus geothermalis and Neisseria polysaccharea
    • J.H. Jung, D.H. Seo, S.J. Ha, M.C. Song, J. Cha, S.H. Yoo, T.J. Kim, N.I. Baek, M.Y. Baik, and C.S. Park Enzymatic synthesis of salicin glycosides through transglycosylation catalyzed by amylosucrases from Deinococcus geothermalis and Neisseria polysaccharea Carbohydr. Res. 344 2009 1612 1619
    • (2009) Carbohydr. Res. , vol.344 , pp. 1612-1619
    • Jung, J.H.1    Seo, D.H.2    Ha, S.J.3    Song, M.C.4    Cha, J.5    Yoo, S.H.6    Kim, T.J.7    Baek, N.I.8    Baik, M.Y.9    Park, C.S.10
  • 16
    • 70350345820 scopus 로고    scopus 로고
    • Anti-inflammatory effects of Scutellaria baicalensis extract via suppression of immune modulators and MAP kinase signaling molecules
    • E.H. Kim, B. Shim, S. Kang, G. Jeong, J.S. Lee, Y.B. Yu, and M. Chun Anti-inflammatory effects of Scutellaria baicalensis extract via suppression of immune modulators and MAP kinase signaling molecules J. Ethnopharmacol. 126 2009 320 331
    • (2009) J. Ethnopharmacol. , vol.126 , pp. 320-331
    • Kim, E.H.1    Shim, B.2    Kang, S.3    Jeong, G.4    Lee, J.S.5    Yu, Y.B.6    Chun, M.7
  • 17
    • 78650321830 scopus 로고    scopus 로고
    • Enhanced stability and intracellular accumulation of quercetin by protection of the chemically or metabolically susceptible hydroxyl groups with a pivaloxymethyl (POM) promoiety
    • M.K. Kim, K.S. Park, C. Lee, H.R. Park, H. Choo, and Y. Chong Enhanced stability and intracellular accumulation of quercetin by protection of the chemically or metabolically susceptible hydroxyl groups with a pivaloxymethyl (POM) promoiety J. Med. Chem. 53 2010 8597 8607
    • (2010) J. Med. Chem. , vol.53 , pp. 8597-8607
    • Kim, M.K.1    Park, K.S.2    Lee, C.3    Park, H.R.4    Choo, H.5    Chong, Y.6
  • 18
    • 58949103807 scopus 로고    scopus 로고
    • In vitro solubility, stability and permeability of novel quercetin-amino acid conjugates
    • N.K. Kim, K.S. Park, W.S. Yeo, H. Choo, and Y. Chong In vitro solubility, stability and permeability of novel quercetin-amino acid conjugates Bioorg. Med. Chem. 17 2009 1164 1171
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 1164-1171
    • Kim, N.K.1    Park, K.S.2    Yeo, W.S.3    Choo, H.4    Chong, Y.5
  • 20
    • 0021228426 scopus 로고
    • Studies on Scutellariae radix. VII. Anti-arthritic and anti-inflammatory actions of methanolic extract and flavonoid components from Scutellariae radix
    • M. Kubo, H. Matsuda, M. Tanaka, Y. Kimura, H. Okuda, M. Higashino, T. Tani, K. Namba, and S. Arichi Studies on Scutellariae radix. VII. Anti-arthritic and anti-inflammatory actions of methanolic extract and flavonoid components from Scutellariae radix Chem. Pharm. Bull. 32 1984 2724 2729
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 2724-2729
    • Kubo, M.1    Matsuda, H.2    Tanaka, M.3    Kimura, Y.4    Okuda, H.5    Higashino, M.6    Tani, T.7    Namba, K.8    Arichi, S.9
  • 21
    • 33846684768 scopus 로고    scopus 로고
    • Scutellaria baicalensis, a herbal medicine: Anti-proliferative and apoptotic activity against acute lymphocytic leukemia, lymphoma and myeloma cell lines
    • T. Kumagai, C.I. Müller, J.C. Desmond, Y. Imai, D. Heber, and H.P. Koeffler Scutellaria baicalensis, a herbal medicine: anti-proliferative and apoptotic activity against acute lymphocytic leukemia, lymphoma and myeloma cell lines Leuk. Res. 31 2007 523 530
    • (2007) Leuk. Res. , vol.31 , pp. 523-530
    • Kumagai, T.1    Müller, C.I.2    Desmond, J.C.3    Imai, Y.4    Heber, D.5    Koeffler, H.P.6
  • 23
    • 8844249354 scopus 로고    scopus 로고
    • Separation methods used for Scutellaria baicalensis active components
    • H.B. Li, Y. Jiang, and F.J. Chen Separation methods used for Scutellaria baicalensis active components J. Chromatogr. B 812 2004 277 290
    • (2004) J. Chromatogr. B , vol.812 , pp. 277-290
    • Li, H.B.1    Jiang, Y.2    Chen, F.J.3
  • 24
    • 0029704787 scopus 로고    scopus 로고
    • The anti-inflammatory activity of Scutellaria rivularis extracts and its active components, baicalin, baicalein and wogonin
    • C.C. Lin, and D.E. Shieh The anti-inflammatory activity of Scutellaria rivularis extracts and its active components, baicalin, baicalein and wogonin Am. J. Chin. Med. 24 1996 31 36
    • (1996) Am. J. Chin. Med. , vol.24 , pp. 31-36
    • Lin, C.C.1    Shieh, D.E.2
  • 25
    • 55549086179 scopus 로고    scopus 로고
    • Effect of bakumijiogan, an herbal formula in traditional Chinese medicine, on atopic dermatitis-like skin lesions induced by mite antigen in NC/Jic mice
    • T. Makino, M. Hamanaka, H. Yamashita, and H. Mizukami Effect of bakumijiogan, an herbal formula in traditional Chinese medicine, on atopic dermatitis-like skin lesions induced by mite antigen in NC/Jic mice Biol. Pharm. Bull. 31 2008 2108 2113
    • (2008) Biol. Pharm. Bull. , vol.31 , pp. 2108-2113
    • Makino, T.1    Hamanaka, M.2    Yamashita, H.3    Mizukami, H.4
  • 26
    • 0027325255 scopus 로고
    • Nitric oxide synthase structure and mechanism
    • M.A. Marletta Nitric oxide synthase structure and mechanism J. Biol. Chem. 268 1993 12231 12234
    • (1993) J. Biol. Chem. , vol.268 , pp. 12231-12234
    • Marletta, M.A.1
  • 28
    • 33644872994 scopus 로고    scopus 로고
    • Synthesis, structure analyses, and characterization of novel epigallocatechin gallate (EGCG) glycosides using the glucansucrase from Leuconostoc mesenteroides B-1299CB
    • Y.H. Moon, J.H. Lee, J.S. Ahn, S.H. Nam, D.K. Oh, D.H. Park, H.J. Chung, S. Kang, D.F. Day, and D.J. Kim Synthesis, structure analyses, and characterization of novel epigallocatechin gallate (EGCG) glycosides using the glucansucrase from Leuconostoc mesenteroides B-1299CB J. Agric. Food Chem. 54 2006 1230 1237
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 1230-1237
    • Moon, Y.H.1    Lee, J.H.2    Ahn, J.S.3    Nam, S.H.4    Oh, D.K.5    Park, D.H.6    Chung, H.J.7    Kang, S.8    Day, D.F.9    Kim, D.J.10
  • 29
    • 3242736468 scopus 로고    scopus 로고
    • β-Cyclodextrin as a suitable solubilizing agent for in situ absorption study of poorly water-soluble drugs
    • M. Oda, H. Saitoh, M. Kobayashi, and B. Aungst β-Cyclodextrin as a suitable solubilizing agent for in situ absorption study of poorly water-soluble drugs Int. J. Pharm. 280 2004 95 102
    • (2004) Int. J. Pharm. , vol.280 , pp. 95-102
    • Oda, M.1    Saitoh, H.2    Kobayashi, M.3    Aungst, B.4
  • 31
    • 84865438089 scopus 로고    scopus 로고
    • Enzymatic synthesis of piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii DSM 6725
    • H. Park, J. Kim, K.H. Choi, S. Hwang, S.J. Yang, N.I. Baek, and J. Cha Enzymatic synthesis of piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii DSM 6725 J. Agric. Food Chem. 60 2012 8183 8189
    • (2012) J. Agric. Food Chem. , vol.60 , pp. 8183-8189
    • Park, H.1    Kim, J.2    Choi, K.H.3    Hwang, S.4    Yang, S.J.5    Baek, N.I.6    Cha, J.7
  • 32
    • 0041825750 scopus 로고    scopus 로고
    • Glycosylation of resveratrol protects it from enzymic oxidation
    • G. Regev-Shoshani, O. Shoseyov, I. Bilkis, and Z. Kerem Glycosylation of resveratrol protects it from enzymic oxidation Biochem. J. 374 2003 157 163
    • (2003) Biochem. J. , vol.374 , pp. 157-163
    • Regev-Shoshani, G.1    Shoseyov, O.2    Bilkis, I.3    Kerem, Z.4
  • 33
    • 0020429373 scopus 로고
    • Selective inhibition of platelet lipoxygenase by baicalein
    • K. Sekiya, and H. Okuda Selective inhibition of platelet lipoxygenase by baicalein Biochem. Biophys. Res. Commun. 105 1982 1090 1095
    • (1982) Biochem. Biophys. Res. Commun. , vol.105 , pp. 1090-1095
    • Sekiya, K.1    Okuda, H.2
  • 34
    • 33750613056 scopus 로고    scopus 로고
    • Two-site substrate recognition model for the Keap1-Nrf2 system: A hinge and latch mechanism
    • K.I. Tong, A. Kobayashi, F. Katsuoka, and M. Yamamoto Two-site substrate recognition model for the Keap1-Nrf2 system: a hinge and latch mechanism Biol. Chem. 387 2006 1311 1320
    • (2006) Biol. Chem. , vol.387 , pp. 1311-1320
    • Tong, K.I.1    Kobayashi, A.2    Katsuoka, F.3    Yamamoto, M.4
  • 35
    • 0033022302 scopus 로고    scopus 로고
    • Inhibitory effects of baicalein and wogonin on lipopolysaccharide-induced nitric oxide production in macrophages
    • I. Wakabayashi Inhibitory effects of baicalein and wogonin on lipopolysaccharide-induced nitric oxide production in macrophages Pharmacol. Toxicol. 84 1999 288 291
    • (1999) Pharmacol. Toxicol. , vol.84 , pp. 288-291
    • Wakabayashi, I.1
  • 36
    • 34548267589 scopus 로고    scopus 로고
    • Improving metabolic stability of cancer chemoprotective polyphenols
    • T. Walle, X. Wen, and U.K. Walle Improving metabolic stability of cancer chemoprotective polyphenols Expert Opin. Drug Metab. Toxicol. 3 2007 379 388
    • (2007) Expert Opin. Drug Metab. Toxicol. , vol.3 , pp. 379-388
    • Walle, T.1    Wen, X.2    Walle, U.K.3
  • 38
    • 23944446872 scopus 로고    scopus 로고
    • Stability of baicalin in biological fluids in vitro
    • J. Xing, X. Chen, and D.J. Zhong Stability of baicalin in biological fluids in vitro J. Pharm. Biomed. Anal. 39 2005 593 600
    • (2005) J. Pharm. Biomed. Anal. , vol.39 , pp. 593-600
    • Xing, J.1    Chen, X.2    Zhong, D.J.3
  • 39
    • 3843058752 scopus 로고    scopus 로고
    • Antioxidant activity of glycosylated vitamin P and its suppressive effect on oxidative stress in hyperlipidemic mice
    • M. Yamada, H. Mitsuzumi, Y. Tsuzaki, Y. Miwa, H. Chaen, and I.J. Yamamoto Antioxidant activity of glycosylated vitamin P and its suppressive effect on oxidative stress in hyperlipidemic mice Jpn. Soc. Nutr. Food Sci. 56 2003 355 363
    • (2003) Jpn. Soc. Nutr. Food Sci. , vol.56 , pp. 355-363
    • Yamada, M.1    Mitsuzumi, H.2    Tsuzaki, Y.3    Miwa, Y.4    Chaen, H.5    Yamamoto, I.J.6
  • 41
    • 80055021869 scopus 로고    scopus 로고
    • Enhancing effect of hydroxypropyl-β-cyclodextrin on the intestinal absorption process of genipin
    • Y. Zhang, F.C. Meng, Y.L. Cui, and Y.F. Song Enhancing effect of hydroxypropyl-β-cyclodextrin on the intestinal absorption process of genipin J. Agric. Food Chem. 59 2011 10919 10926
    • (2011) J. Agric. Food Chem. , vol.59 , pp. 10919-10926
    • Zhang, Y.1    Meng, F.C.2    Cui, Y.L.3    Song, Y.F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.