Molecular cloning and biochemical characterization of three Concord grape (Vitis labrusca) flavonol 7-O-glucosyltransferases

Planta

Volumn 234, Issue 6, 2011, Pages 1201-1214

  Hall, Dawn ^a,b   Kim, Kyung Hee ^a   De Luca, Vincenzo ^a  

^a BROCK UNIVERSITY   (Canada)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Concord grape; Detoxification mechanism; Flavonol; Glucosyltransferase; Xenobiotic

Indexed keywords

2,4,5 TRICHLOROPHENOL; 2,4,5-TRICHLOROPHENOL; ANTHOCYANIN; CHLOROPHENOL; FLAVONOL DERIVATIVE; GLUCOSYLTRANSFERASE; HYBRID PROTEIN; VEGETABLE PROTEIN;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; FLOWER; FRUIT; GENE EXPRESSION REGULATION; GENETICS; KINETICS; METABOLISM; MOLECULAR CLONING; NUCLEOTIDE SEQUENCE; PHYLOGENY; PLANT GENOME; PLANT LEAF; SEQUENCE ALIGNMENT; TRANSGENIC PLANT; VITIS;

ANTHOCYANINS; BASE SEQUENCE; CHLOROPHENOLS; CLONING, MOLECULAR; FLAVONOLS; FLOWERS; FRUIT; GENE EXPRESSION REGULATION, PLANT; GENOME, PLANT; GLUCOSYLTRANSFERASES; KINETICS; PHYLOGENY; PLANT LEAVES; PLANT PROTEINS; PLANTS, GENETICALLY MODIFIED; RECOMBINANT FUSION PROTEINS; SEQUENCE ALIGNMENT; SUBSTRATE SPECIFICITY; VITIS;

VITACEAE; VITIS LABRUSCA;

EID: 81955163004     PISSN: 00320935     EISSN: 14322048     Source Type: Journal    
DOI: 10.1007/s00425-011-1474-0     Document Type: Article

References (50)

1. Ali A, Strommer J (2003) A simple extraction and chromatographic system for the simultaneous analysis of anthocyanins and stilbenes of Vitis species. J Agric Food Chem 51: 7246-7251.
2. Amico V, Chillemi R, Mangiafico S, Spatafora C, Tringali C (2008) Polyphenol-enriched fractions from Sicilian grape pomace: HPLC-DAD analysis and antioxidant activity. Bioresource Technol 99: 5960-5966.
3. Bowles D (2002) A multigene family of glycosyltransferases in a model plant, Arabidopsis thaliana. Biochem Soc Trans 30: 301-306.
4. Brazier-Hicks M, Edwards LA, Edwards R (2007) Selection of plants for roles in phytoremediation: the importance of glucosylation. Plant Biotechnol J 5: 627-635.
5. Caputi L, Lim E, Bowles D (2008) Discovery of new biocatalysts for the glucosylation of terpenoid scaffolds. Chem Eur J 14: 6656-6662.
6. Cascado CG, Heredia A (1999) Structure and dynamics of reconstituted cuticular waxes of grape berry cuticle (Vitis vinifera L.). J Exp Bot 50: 175-182.
7. Castillo-Muñoz N, Gómez-Alonso S, García-Romero E, Hermosín-Gutiérrez I (2007) Flavonol profiles of Vitis vinifera red grapes and their single cultivar wines. J Agric Food Chem 55: 992-1002.
8. Castillo-Muñoz N, Gómez-Alonso S, García-Romero E, Gómez V, Velders A, Hermosín-Gutiérrez I (2009) Flavonol 3-O-glycosides series of Vitis vinifera cv. Petit Verdot red wine grapes. J Agr Food Chem 57: 209-219.
9. Dong X (2004) NPR1, all things considered. Curr Opin Plant Biol 7: 547-552.
10. Fischer T, Gosch C, Pfeiffer J, Halbwirth H, Halle C, Stich K, Forkmann G (2007) Flavonoid genes of pear (Pyrus communis). Trees 21: 521-529.
11. Ford CM, Boss PK, Høj PB (1998) Cloning and characterization of Vitis vinifera UDP-Glucose: flavonoid 3-O-glucosyltransferase, 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.
12. Hall D, De Luca V (2007) Mesocarp localization of a bi-functional resveratrol/hydroxycinnamic acid glucosyltransferase of Concord grape (Vitis labrusca). Plant J 49: 579-591.
13. Harborne JB (1967) Comparative biochemistry of the flavonoids. Academic Press, London.
14. Hirotani M, Kuroda R, Suzuki H, Yoshikawa T (2000) Cloning and expression of UDP-glucose: flavonoid 7-O-glucosyltransferase from hairy root cultures of Scutellaria baicalensis. Planta 210: 1006-1013.
15. Hou B, Lim E, Higgins G, Bowles D (2004) N-Glucosylation of cytokinins by glucosyltransferases of Arabidopsis thaliana. J Biol Chem 279: 47822-47832.
16. Huntley A (2007) Grape flavonoids and menopausal health. Menopause Int 13: 165-169.
17. Imanishi S, Hashizume K, Kojima H, Ichihara A, Nakamura K (1998) An mRNA of tobacco cell, which is rapidly inducible by methyl jasmonate in the presence of cycloheximide, codes for a putative glycosyltransferases. Plant Cell Physiol 39: 202-211.
18. Imayama T, Yoshihara N, Fukuchi-Mizutani M, Tanaka Y, Ino I, Yabuya T (2004) Isolation and characterization of a cDNA clone of UDP-glucose: anthocyanin 5-O-glucosyltransferase in Iris hollandica. Plant Sci 167: 1243-1248.
19. Jánváry L, Hoffmann T, Pfeiffer J, Hausmann L, Töpfer R, Fischer T, Schwab W (2009) A double mutation in the anthocyanin 5-O-glucosyltranferase gene disrupts enzymatic activity in Vitis vinifera L. J Agr Food Chem 57: 3512-3518.
20. Jones P, Vogt T (2001) Glycosyltransferases in secondary plant metabolism: tranquilizers and stimulant controllers. Planta 213: 164-174.
21. Jones P, Møller B, Høj P (1999) The UDP-glucose: p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. J Biol Chem 274: 35483-35491.
22. Jones P, Meßner B, Nakajima JI, Schäffner AR, Saito K (2003) UGT73C6 and UGT78D1, glycosyltransferases involved in flavonol glycoside biosynthesis in Arabidopsis thaliana. J Biol Chem 278: 43910-43918.
23. Jurd L (1962) Spectral properties of flavonoid compounds. In: Geissmann TA (ed) The chemistry of flavonoid compounds. Pergamon Press Inc, Oxford, pp 107-155.
24. Kramer CM, Prata RTN, Willits MG, De Luca V, Steffens JC, Graser G (2003) Cloning and regiospecificity studies of two flavonoid glucosyltransferases from Allium cepa. Phytochemistry 64: 1069-1076.
25. Langcake P, Pryce RJ (1977) A new class of phytoalexins from grapevine. Experientia 33: 151-152.
26. Leifert W, Abeywardena M (2008) Cardioprotective actions of grape polyphenols. Nutr Res 28: 729-737.
27. Li Y, Baldauf S, Lim EK, Bowles DJ (2001) Phylogenetic analysis of the UDP-glycosyltransferase multigene family of Arabidopsis thaliana. J Biol Chem 276: 4338-4343.
28. Lim E, Doucet CJ, Li Y, Elias L, Worrall D, Spencer SP, Ross J, Bowles DJ (2002) The activity of Arabidopsis glycosyltransferases toward salicylic acid, 4-hydroxybenzoic acid and other benzoates. J Biol Chem 277: 586-592.
29. Lim E, Baldauf S, Li Y, Elias L, Worrall D, Spencer SP, Jackson RG, Taguchi G, Ross J, Bowles DJ (2003) Evolution of substrate recognition across a multigene family of glycosyltransferases in Arabidopsis. Glycobiology 13: 139-145.
30. Lim E, Doucet C, Hou B, Jackson R, Abrams S, Bowles D (2005) Resolution of (+)-abscisic acid using an Arabidopsis glucosyltransferase. Tetrahedron Assymetr 16: 143-147.
31. Loutre C, Dixon DP, Brazier M, Slater M, Cole DJ, Edwards R (2003) Isolation of a glucosyltransferase from Arabidopsis thaliana active in the metabolism of the persistent pollutant 3, 4-dichloroaniline. Plant J 34: 485-493.
32. Meßner B, Thulke O, Schäffner AR (2003) Arabidopsis glucosyltransferases with activities toward both endogenous and xenobiotic substrates. Planta 217: 138-146.
33. Moore MO, Giannasi DE (1994) Foliar flavonoids of eastern North American Vitis (Vitaceae) north of Mexico. Plant Syst Evol 193: 21-36.
34. Muñoz-Espada A, Wood K, Bordelon B, Watkins B (2004) Anthocyanin quantification and radical scavenging capacity of Concord, Norton, and Marechal Foch grapes and wines. J Agr Food Chem 52: 6779-6786.
35. Nagashima S, Tomo S, Orihara Y, Yoshikawa T (2004) Cloning and characterization of glucosyltransferase cDNA from Eucalyptus perriniana cultured cells. Plant Biotech 21: 343-348.
36. Noguchi A, Saito A, Homma Y, Nakao M, Sasaki N, Nishino T, Takahashi S, Nakayama T (2007) A UDP-glucose: isoflavone 7-O-glucosyltransferase from the roots of soybean (Glycine max) seedlings. J Biol Chem 282: 23581-23590.
37. Ogata J, Kanno Y, Itoh Y, Tsugawa H, Suzuki M (2005) Plant biochemistry: anthocyanin biosynthesis in roses. Nature 435: 757-758.
38. Ono E, Homma Y, Horikawa M, Kunikane-Doi S, Imai H, Takahashi S, Kawai Y, Ishiguro M, Fukui Y, Nakayama T (2010) Functional differentiation of the glycosyltransferases that contribute to the chemical diversity of bioactive flavonol glycosides in grapevines (Vitis vinifera). Plant Cell 22: 2856-2871.
39. Park HJ, Cha HC (2003) Flavonoids from leaves and exocarps of the grape Kyoho. Korean J Biol Sci 7: 327-330.
40. Polásková P, Herszage J, Ebeler S (2008) Wine flavor: chemistry in a glass. Chem Soc Rev 37: 2478-2489.
41. Schneider E, von der Heydt H, Esperester A (2008) Evaluation of polyphenol composition in red leaves from different varieties of Vitis vinifera. Plant Med 74: 565-572.
42. Taguchi G, Ubukata T, Nobuaki H, Yamamoto H, Okazaki M (2003) Cloning and characterization of a glucosyltransferase that reacts on the 7-hydroxyl group of flavonol and the 3-hydroxyl group of coumarin from tobacco cells. Arch Biochem Biophys 420: 95-102.
43. Tian L, Blount JW, Dixon RA (2006) Phenylpropanoid glycosyltransferases from osage orange (Maclura pomifera) fruit. FEBS Lett 580: 6915-6920.
44. Tohge T, Nishiyama Y, Hirai MY, Yano M, Nakajima J, Awazuhara M, Inoue E, Takahashi H, Goodenow DB, Kitayama M, Noji M, Yamazaki M, Saito K (2005) Functional genomics by integrated analysis of metabolome and transcriptome of Arabidopsis plants over-expressing an MYB transcription factor. Plant J 42: 218-235.
45. Vogt T, Jones P (2000) Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci 5: 380-388.
46. Vogt T, Zimmermann E, Grimm R, Meyer M, Strack D (1997) Are the characteristics of betanidin glucosyltransferases from cell-suspension cultures of Dorotheanthus bellidiformis indicative of their phylogenetic relationship with flavonoid glucosyltransferase? Planta 203: 349-361.
47. Vogt T, Grimm R, Strack D (1999) Cloning and expression of a cDNA encoding betanidin 5-O-glucosyltransferase, a betanidin- and flavonoid-specific enzyme with high homology to inducible glucosyltransferases from the Solanaceae. Plant J 19: 509-519.
48. Willits MG, Giovanni M, Prata RTN, Kramer CM, De Luca V, Steffens JC, Graser G (2004) Bio-fermentation of modified flavonoids: an example of in vivo diversification of secondary metabolites. Phytochemistry 65: 31-41.
49. Wu X, Prior RL (2005) Systematic identification and characterization of anthocyanins by HPLC-ESI-MS/MS in common foods in the United States: fruits and berries. J Agric Food Chem 53: 2589-2599.
50. Yamazaki M, Yamagishi E, Gong Z, Fukuchi-Mizutani M, Fukui Y, Tanaka Y, Kusumi T, Yamaguchi M, Saito K (2002) Two flavonoid glucosyltransferases from Petunia hybrida: molecular cloning, biochemical properties and developmentally regulated expression. Plant Mol Biol 48: 401-411.