Synthesis of flavonol 3-O-glycoside by UGT78D1

Glycoconjugate Journal

Volumn 29, Issue 5-6, 2012, Pages 425-432

  Ren, Guangxiang ^a   Hou, Jingli ^a   Fang, Qinghong ^a   Sun, Hong ^a   Liu, Xiaoyan ^a   Zhang, Lianwen ^a   Wang, Peng George ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Flavonol; Substrate specificity.; UDPglucose.; UGT78D1

Indexed keywords

3 HYDROXYFLAVONE; 6 HYDROXYFLAVANONE; 6 HYDROXYFLAVONE; 7 HYDROXYFLAVANONE; AMPELOPSIN; APIGENIN; ASTRAGALIN; BAICALEIN; CHRYSIN; DAIDZEIN; DIHYDROQUERCEIN; FISETIN; FLAVANOID; FLAVONOL 3 O GLYCOSIDE; FLAVONOL DERIVATIVE; GALANGIN; GENISTEIN; GLYCOSYLTRANSFERASE; HESPERETIN; ISORHAMNETIN; KAEMPFEROL; LUTEOLIN; MORIN; MYRICETIN; NARINGENIN; QUERCETIN; SCUTELLARIN; TAXIFOLIOL; UGT78D1; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEOTIDE SEQUENCE; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ANTIOXIDANTS; FLAVONOIDS; GLYCOSIDES; GLYCOSYLATION; GLYCOSYLTRANSFERASES; KAEMPFEROLS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PLANT PROTEINS; QUERCETIN; URIDINE DIPHOSPHATE GLUCOSE;

EID: 84865735755     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-012-9410-5     Document Type: Article

References (24)

1. Dixon, R.A., Steele, C.L.: Flavonoids and isoflavonoids - A gold mine for metabolic engineering. Trends Plant Sci. 4, 394-400 (1999
2. Dixon, R.A.: Natural products and disease resistance. Nature 411, 843-847 (2001
3. Ross, J.A., Kasum, C.M.: Dietary flavonoids: Bioavailability, metabolic effects, and safety. Annu. Rev. Nutr. 22, 19-34 (2002 (Pubitemid 35221452)
4. Halliwell, B., Rafter, J., Jenner, A.: Health promotion by flavonoids, tocopherols, tocotrienols, and other phenols: Direct or indirect effects? Antioxidant or not? Am. J. Clin. Nutr. 81, 268S-276S (2005
5. Nicolle, E., Souard, F., Faure, P., Boumendjel, A.: Flavonoids as promising lead compounds in type 2 diabetes mellitus: Molecules of interest and structure-activity relationship. Curr. Med. Chem. 18, 2661-2672 (2011
6. Jones, P., Messner, B., Nakajima, J.-I., Schäffner, A.R., Saito, K.: UGT73C6 and UGT78D1, glycosyltransferase involved in flavonol glycoside biosynthesis in Arabidopsis thliana. J. Biol. Chem. 278(45), 43910-43918 (2003 (Pubitemid 37377130)
7. Tamara, P.K., John, M.P.: Natural product polyphenols of relevance to human health. Pharm. Biol. 42(Suppl), 46-63 (2004
8. Scalbert, A., Johnson, I.T., Saltmarsh, M.: Polyphenols: Antioxidants and beyond. Am. J. Clin. Nutr. 81, 215-217 (2005
9. Manach, C.,Williamson, G., Moland, C., Scalbert, A., Rémé sy, C.: Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr. 81, 230-242 (2005
10. Williamson, G., Manach, C.: Bioavailability and bioefficacy of polyphenols in humans. II. Review of 97 intervention studies. Am. J. Clin. Nutr. 81, 243-255 (2005
11. Jones, P., Vogt, T.: Glycosyltransferases in secondary plant metablolism: Tranquilizers and stimulant controllers. Planta 213, 164-174 (2001 (Pubitemid 32623572)
12. Vogt, T., Jones, P.: Glycosyltransferases in plant natural product synthesis: Characterization of a supergene family. Trends Plant Sci. 5, 380-386 (2000
13. Li, Y., Baldauf, S., Lim, E.-K., Bowles, D.J.: Phylogenetic analysis of UDP-glycosyltransferases multigene family of Arabidopsis thaliana. J. Biol. Chem. 276, 4338-4343 (2001
14. Paquette, S., Moller, B.L., Bak, S.: On the origin of family 1 plant glycosyltransferases. Phytochem. 62, 399-413 (2003 (Pubitemid 36168942)
15. Simkhada, D., Lee, H.C., Sohng, J.K.: Genetic engineering approach for the production of rhamnosyl and allosyl flavonoids from Escherichia coli. Biotechnol. Bioeng. 107, 154- 162 (2010
16. Choi, S.H., Ryu, M., Yoon, Y.J., Kim, D.-M., Lee, E.Y.: Glycosylation of various flavonoids by recombinant oleandomycin glycosyltransferase from Streptomyces antibioticus in batch and repeated batch modes. Biotechnol. Lett. 34, 499- 505 (2012
17. Lim, E.K., Doucet, C.J., Elias, L., Worrall, D., Li, Y., Ross, J., Bowles, D.J.: Activity of the group 1 glycosyltransferases of Arabidopsis towards salicylic acid, para-hydroxybenzoic acid and other benzoates. J. Biol. Chem. 277, 586-592 (2002 (Pubitemid 34952095)
18. Lim, E.-K., Ashford, D.A., Hou, B., Jackson, R.G., Bowles, D.J.: Arabidopsis Glycosyltransferases as biocatalysts in fermentation for regioselective synthesis of diverse quercetin glucosides. Biotech. Bioeng. 87, 623-631 (2004 (Pubitemid 39295407)
19. Ford, C.M., Boss, P.K., Høj, P.B.: Cloning and characterization of Vitis vinifera UDP-glucose: Flavonoid 3-O-glucosyltransferases, a homologue of the enzyme encoded by the maize Bronze-1 locus that may primarily serve to glucosylate anthocyanidins in vivo. J. Biol. Chem. 273, 9224-9233 (1998 (Pubitemid 28176214)
20. Kramer, C.M., Prata, R.T.N.,Willits,M.G., De Luca, V., Steffens, J.C., Graser, G.: Cloning and regiospecificity studies of two flavonoid glucosyltransferases from Allium cepa. Phytochemistry 64, 1069- 1076 (2003 (Pubitemid 37295329)
21. Miller, K.D.,Guyon,V., Evans, J.N.S., Shuttleworth,W.A., Taylor, L.P.: Purification, cloning, and heterologous expression of a catalytically efficient flavonol 3-O-galactosyltransferase expressed in the male gametophyte of Petunia hybrida. J. Biol. Chem. 274, 34011-34019 (1999 (Pubitemid 129511733)
22. Willits, M.G., Giovanni, M., Prata, R.T.N., Kramer, C.M., Luca, V.D., Steffens, J.C., Graser, G.: Bio-fermentation of modified flavonoids: An example of in vivo diversification of secondary metabolites. Phytochemistry 65, 31-41 (2004 (Pubitemid 38155890)
23. Castillo-Muñoz, N., Gómez-Alonso, S., García-Romero, E., Gómez, M.V., Velders, A.H., Hermosín-Gutiérrez, I.: Flavonol 3-Glycosides series of vitis 1 vinifera cv. petit verdot red wine grapes. J. Agric. Food Chem. 57, 209-219 (2009
24. Agrawal, P.K.: Carbon-13 NMR of flavonoids. Elsevier Science, New York (1989)