메뉴 건너뛰기




Volumn 211, Issue , 2015, Pages 103-106

Biotransformation of phloretin by amylosucrase yields three novel dihydrochalcone glucosides

Author keywords

Amylosucrase; Chalcone; Glycosylation; Non Leloir glycosyltransferase; Phloretin

Indexed keywords

BIOACTIVITY;

EID: 84938575284     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2015.07.002     Document Type: Article
Times cited : (26)

References (42)
  • 1
    • 0032864542 scopus 로고    scopus 로고
    • Phlorizin, a competitive inhibitor of glucose transport, facilitates memory storage in mice
    • Boccia M.M., Kopf S.R., Baratti C.M. Phlorizin, a competitive inhibitor of glucose transport, facilitates memory storage in mice. Neurobiol. Learn. Mem. 1999, 71:104-112.
    • (1999) Neurobiol. Learn. Mem. , vol.71 , pp. 104-112
    • Boccia, M.M.1    Kopf, S.R.2    Baratti, C.M.3
  • 3
    • 77954242599 scopus 로고    scopus 로고
    • SGLT2 inhibition-a novel strategy for diabetes treatment
    • Chao E.C., Henry R.R. SGLT2 inhibition-a novel strategy for diabetes treatment. Nat. Rev. Drug Discov. 2010, 7:551-559.
    • (2010) Nat. Rev. Drug Discov. , vol.7 , pp. 551-559
    • Chao, E.C.1    Henry, R.R.2
  • 7
    • 84918183836 scopus 로고
    • Synthesis of two dihydrochalcone glucosides from Malus trilobata and Malus sieboldii arborescens
    • Farkas L., Nogradi M., Major A. Synthesis of two dihydrochalcone glucosides from Malus trilobata and Malus sieboldii arborescens. Chem. Ber. 1965, 98:2926-2929.
    • (1965) Chem. Ber. , vol.98 , pp. 2926-2929
    • Farkas, L.1    Nogradi, M.2    Major, A.3
  • 8
    • 51349123565 scopus 로고    scopus 로고
    • Novel glycosylated carboranylquinazolines for boron neutron capture therapy of tumors: synthesis, characterization, and in vitro toxicity studies
    • Genady A.R., El-Zaria M.E. Novel glycosylated carboranylquinazolines for boron neutron capture therapy of tumors: synthesis, characterization, and in vitro toxicity studies. Appl. Organometal. Chem. 2008, 22:227-232.
    • (2008) Appl. Organometal. Chem. , vol.22 , pp. 227-232
    • Genady, A.R.1    El-Zaria, M.E.2
  • 9
    • 77349113758 scopus 로고    scopus 로고
    • Cloning and heterologous expression of glycosyltransferases from Malus x domestica and Pyrus communis, which convert phloretin to phloretin 2'-O-glucoside (phloridzin)
    • Gosch C., Halbwirth H., Schneider B., Hölscher H., Stich K. Cloning and heterologous expression of glycosyltransferases from Malus x domestica and Pyrus communis, which convert phloretin to phloretin 2'-O-glucoside (phloridzin). Plant Sci. 2010, 178:299-306.
    • (2010) Plant Sci. , vol.178 , pp. 299-306
    • Gosch, C.1    Halbwirth, H.2    Schneider, B.3    Hölscher, H.4    Stich, K.5
  • 10
    • 58549111373 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors
    • Gupte A., Buolamwini J.K. Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors. Bioorg. Med. Chem. Lett. 2009, 19:917-921.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 917-921
    • Gupte, A.1    Buolamwini, J.K.2
  • 11
    • 0042302049 scopus 로고
    • Synthesis of a polysaccharide of the starch-glycogen class from sucrose by a cell-free, bacterial enzyme system (amylosucrase)
    • Hehre E.J., Hamilton D.M., Carlson A.S. Synthesis of a polysaccharide of the starch-glycogen class from sucrose by a cell-free, bacterial enzyme system (amylosucrase). J. Biol. Chem. 1949, 177:267-279.
    • (1949) J. Biol. Chem. , vol.177 , pp. 267-279
    • Hehre, E.J.1    Hamilton, D.M.2    Carlson, A.S.3
  • 12
    • 0028892526 scopus 로고
    • Structural analysis by NMR of antitumor drug-DNA complexes: 9-aminoanthracycline (SM-5887)
    • Igarashi J.-E., Sunagawa M. Structural analysis by NMR of antitumor drug-DNA complexes: 9-aminoanthracycline (SM-5887). Bioorg. Med. Chem. Lett. 1995, 5:2923-2928.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2923-2928
    • Igarashi, J.-E.1    Sunagawa, M.2
  • 13
    • 84923423739 scopus 로고    scopus 로고
    • Production of C-glucosides of flavonoids and related compounds by Escherichia coli expressing buckwheat C-glucosyltransferase
    • Ito T., Fujimoto S., Shimosaka M., Taguchi G. Production of C-glucosides of flavonoids and related compounds by Escherichia coli expressing buckwheat C-glucosyltransferase. Plant Biotechnol. 2014, 31:519-524.
    • (2014) Plant Biotechnol. , vol.31 , pp. 519-524
    • Ito, T.1    Fujimoto, S.2    Shimosaka, M.3    Taguchi, G.4
  • 14
    • 84938659424 scopus 로고
    • Glucosides of chalcones and hydrochalcones
    • Jorio M.A. Glucosides of chalcones and hydrochalcones. Ann. Chim. -Rome 1959, 49:1929-1940.
    • (1959) Ann. Chim. -Rome , vol.49 , pp. 1929-1940
    • Jorio, M.A.1
  • 15
    • 68949186622 scopus 로고    scopus 로고
    • Enzymatic synthesis of salicin glycosides through transglycosylation catalyzed by amylosucrases from Deinococcus geothermalis and Neisseria polysaccharea
    • Jung J.-H., Seo D.-H., Ha S.-J., Song M.-C., Cha J., Yoo S.-H., Kim T.-J., Baek N.-I., Baik M.-Y., Park C.-S. Enzymatic synthesis of salicin glycosides through transglycosylation catalyzed by amylosucrases from Deinococcus geothermalis and Neisseria polysaccharea. Carbohydr. Res. 2009, 344:1612-1619.
    • (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
    • 0016616213 scopus 로고
    • Synthesis and tastes of some flavanone- and dihydrochalcone glycosides
    • Kamiya S., Esaki S., Konishi F. Synthesis and tastes of some flavanone- and dihydrochalcone glycosides. Agr. Biol. Chem. 1975, 39:1757-1762.
    • (1975) Agr. Biol. Chem. , vol.39 , pp. 1757-1762
    • Kamiya, S.1    Esaki, S.2    Konishi, F.3
  • 18
    • 0030993973 scopus 로고    scopus 로고
    • Identification and quantification of major polyphenols in apple pomace
    • Lu Y., Foo L.Y. Identification and quantification of major polyphenols in apple pomace. Food Chem. 1997, 59:187-194.
    • (1997) Food Chem. , vol.59 , pp. 187-194
    • Lu, Y.1    Foo, L.Y.2
  • 19
    • 0017670531 scopus 로고
    • Purification and substrate specificity of brewer's yeast α-glucosidase
    • Matsusaka K., Chiba S., Shimomura T. Purification and substrate specificity of brewer's yeast α-glucosidase. Agric. Biol. Chem. 1977, 41:1917-1923.
    • (1977) Agric. Biol. Chem. , vol.41 , pp. 1917-1923
    • Matsusaka, K.1    Chiba, S.2    Shimomura, T.3
  • 20
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays
    • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65:55-63.
    • (1983) J. Immunol. Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 21
    • 0034054933 scopus 로고    scopus 로고
    • Bioavailabilities of quercetin-3-glucoside and quercetin-4'-glucoside do not differ in humans
    • Olthof M.R., Hollman P.C., Vree T.B., Katan M.B. Bioavailabilities of quercetin-3-glucoside and quercetin-4'-glucoside do not differ in humans. J. Nutr. 2000, 130:1200-1203.
    • (2000) J. Nutr. , vol.130 , pp. 1200-1203
    • Olthof, M.R.1    Hollman, P.C.2    Vree, T.B.3    Katan, M.B.4
  • 24
    • 84871171739 scopus 로고    scopus 로고
    • Bioconversion of piceid to piceid glucoside using amylosucrase from Alteromonas macleodii deep ecotype
    • Park H., Kim J., Park J.-H., Baek N.-I., Park C.-S., Lee H.-S., Cha J. Bioconversion of piceid to piceid glucoside using amylosucrase from Alteromonas macleodii deep ecotype. J. Microbiol. Biotechnol. 2012, 22:1698-1704.
    • (2012) J. Microbiol. Biotechnol. , vol.22 , pp. 1698-1704
    • Park, H.1    Kim, J.2    Park, J.-H.3    Baek, N.-I.4    Park, C.-S.5    Lee, H.-S.6    Cha, J.7
  • 27
    • 0036306766 scopus 로고    scopus 로고
    • The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids
    • Rezk B.M., Haenen G.R.M.M., van der Vijgh W.J.F., Bast A. The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem. Biophys. Res. Commun. 2002, 295:9-13.
    • (2002) Biochem. Biophys. Res. Commun. , vol.295 , pp. 9-13
    • Rezk, B.M.1    Haenen, G.R.M.M.2    van der Vijgh, W.J.F.3    Bast, A.4
  • 29
    • 3042728752 scopus 로고    scopus 로고
    • Metabolic modifications of birch leaf phenolics by an herbivorous insect: detoxification of flavonoid aglycones via glycosylation
    • Salminen J.P., Lahtinen M., Lempa K., Kapari L., Haukioja E., Pihlaja K. Metabolic modifications of birch leaf phenolics by an herbivorous insect: detoxification of flavonoid aglycones via glycosylation. Z. Naturforsch. C 2004, 59:437-444.
    • (2004) Z. Naturforsch. C , vol.59 , pp. 437-444
    • Salminen, J.P.1    Lahtinen, M.2    Lempa, K.3    Kapari, L.4    Haukioja, E.5    Pihlaja, K.6
  • 30
    • 33646152732 scopus 로고    scopus 로고
    • Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin, and apigenin bis-C-β-α--glucosides
    • Sato S., Akiya T., Nishizawa H., Suzuki T. Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin, and apigenin bis-C-β-α--glucosides. Carbohydr. Res. 2006, 341:964-970.
    • (2006) Carbohydr. Res. , vol.341 , pp. 964-970
    • Sato, S.1    Akiya, T.2    Nishizawa, H.3    Suzuki, T.4
  • 31
    • 72949120604 scopus 로고    scopus 로고
    • Generation of amylosucrase variants that terminate catalysis of acceptor elongation at the di- or trisaccharide stage
    • Schneider J., Fricke C., Overwin H., Hofmann B., Hofer B. Generation of amylosucrase variants that terminate catalysis of acceptor elongation at the di- or trisaccharide stage. Appl. Environ. Microbiol. 2009, 75:7453-7460.
    • (2009) Appl. Environ. Microbiol. , vol.75 , pp. 7453-7460
    • Schneider, J.1    Fricke, C.2    Overwin, H.3    Hofmann, B.4    Hofer, B.5
  • 32
    • 79952572881 scopus 로고    scopus 로고
    • High level expression of a recombinant amylosucrase gene and selected properties of the enzyme
    • 2011
    • Schneider J., Fricke C., Overwin H., Hofer B. High level expression of a recombinant amylosucrase gene and selected properties of the enzyme. Appl. Microbiol. Biotechnol. 2010, 89:1821-1829. 2011.
    • (2010) Appl. Microbiol. Biotechnol. , vol.89 , pp. 1821-1829
    • Schneider, J.1    Fricke, C.2    Overwin, H.3    Hofer, B.4
  • 33
    • 84938659425 scopus 로고    scopus 로고
    • Scifinder database: . http://www.cas.org/products/scifinder.
  • 34
    • 68249090990 scopus 로고    scopus 로고
    • Highly selective biotransformation of arbutin to arbutin-α-glucoside using amylosucrase from Deinococcus geothermalis DSM 11300
    • Seo D.-H., Jung J.-H., Ha S.-J., Song M.-C., Cha J., Yoo S.-H., Kim T.-J., Baek N.-I., Park C.-S. Highly selective biotransformation of arbutin to arbutin-α-glucoside using amylosucrase from Deinococcus geothermalis DSM 11300. J. Mol. Catal. B-Enzym. 2009, 60:113-118.
    • (2009) J. Mol. Catal. B-Enzym. , vol.60 , pp. 113-118
    • Seo, D.-H.1    Jung, J.-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    Park, C.-S.9
  • 36
    • 58749092120 scopus 로고    scopus 로고
    • Cloning, purification and characterisation of brassinin glucosyltransferase, a phytoalexin-detoxifying enzyme from the plant pathogen Sclerotinia sclerotiorum
    • Sexton A.C., Minic Z., Cozijnsen A.J., Pedras M.S., Howlett B.J. Cloning, purification and characterisation of brassinin glucosyltransferase, a phytoalexin-detoxifying enzyme from the plant pathogen Sclerotinia sclerotiorum. Fungal Genet. Biol 2009, 46:201-209.
    • (2009) Fungal Genet. Biol , vol.46 , pp. 201-209
    • Sexton, A.C.1    Minic, Z.2    Cozijnsen, A.J.3    Pedras, M.S.4    Howlett, B.J.5
  • 38
    • 0345544222 scopus 로고
    • Stereochemistry of enzyme, substrate, and products during β-amylase action
    • Thoma J.A., Koshland D.E. Stereochemistry of enzyme, substrate, and products during β-amylase action. J. Biol. Chem. 1960, 235:2511-2517.
    • (1960) J. Biol. Chem. , vol.235 , pp. 2511-2517
    • Thoma, J.A.1    Koshland, D.E.2
  • 39
    • 0141594732 scopus 로고    scopus 로고
    • Polyphenolic profiles in eight apple cultivars using high-performance liquid chromatography (HPLC)
    • Tsao R., Yang R., Young J.C., Zhu H. Polyphenolic profiles in eight apple cultivars using high-performance liquid chromatography (HPLC). J. Agric. Food Chem. 2003, 51:6347-6353.
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 6347-6353
    • Tsao, R.1    Yang, R.2    Young, J.C.3    Zhu, H.4
  • 40
    • 33644827448 scopus 로고    scopus 로고
    • Apple flavonoids inhibit growth of HT29 human colon cancer cells and modulate expression of genes involved in the biotransformation of xenobiotics
    • Veeriah S., Kautenburger T., Habermann N., Sauer J., Dietrich H., Will F., Pool-Zobel B.L. Apple flavonoids inhibit growth of HT29 human colon cancer cells and modulate expression of genes involved in the biotransformation of xenobiotics. Mol. Carcinog. 2006, 45:164-174.
    • (2006) Mol. Carcinog. , vol.45 , pp. 164-174
    • Veeriah, S.1    Kautenburger, T.2    Habermann, N.3    Sauer, J.4    Dietrich, H.5    Will, F.6    Pool-Zobel, B.L.7
  • 41
    • 0031127564 scopus 로고    scopus 로고
    • The role of carbohydrates in biologically active natural products
    • Weymouth-Wilson A.C. The role of carbohydrates in biologically active natural products. Nat. Prod. Rep. 1997, 14:99-110.
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 99-110
    • Weymouth-Wilson, A.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.