A class of plant glycosyltransferases involved in cellular homeostatis

EMBO Journal

Volumn 23, Issue 15, 2004, Pages 2915-2922

  Lim, Eng Kiat ^a   Bowles, Dianna J ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Biocatalysis; Cellular homeostasis; Detoxification; Glycosyltransferases; Regioselective glucosylation

Indexed keywords

AUXIN; BILE ACID; CYTOKININ; ENZYME; FLAVONOID; GLYCOSYLTRANSFERASE; HERBICIDE; MAMMALIAN ENZYME; NONSTEROID ANTIINFLAMMATORY AGENT; PESTICIDE; PLANT ENZYME; RETINOID; SMALL MOLECULE TRANSPORT AGENT; STEROID; THYROID HORMONE; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE GLUCOSE; URIDINE DIPHOSPHATE GLUCURONIC ACID; VEGETABLE PROTEIN; XENOBIOTIC AGENT;

BIOTRANSFORMATION; CELL HOMEOSTASIS; CELL METABOLISM; CELLULAR DISTRIBUTION; CONSENSUS SEQUENCE; DETOXIFICATION; DIETARY METABOLITE; DRUG ACTIVITY; ENZYME GLYCOSYLATION; ENZYME SUBSTRATE COMPLEX; HOMEOSTASIS; MAMMAL; METABOLITE; PLANT; PRIORITY JOURNAL; PROTEIN EXPRESSION; REGULATORY MECHANISM; REVIEW;

GENE EXPRESSION REGULATION, PLANT; GLYCOSYLATION; GLYCOSYLTRANSFERASES; HOMEOSTASIS; PLANTS;

MAMMALIA;

EID: 4143071626     PISSN: 02614189     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.emboj.7600295     Document Type: Review

References (77)

1. Aherne SA, O'Brien NM (2002) Dietary flavonols: chemistry, food content, and metabolism. Nutrition 18: 75-81
2. Arend J, Warzecha H, Hefner T, Stockigt J (2001) Utilizing genetically engineered bacteria to produce plant-specific glucosides. Biotechnol Bioeng 76: 126-131
3. Bock KW (2003) Vertebrate UDP-glucuronosyltransferases: functional and evolutionary aspects. Biochem Pharmacol 66: 691-696
4. Bosio A, Binczek E, Lebeau MM, Fernald AA, Stoffel W (1996) The human gene CGT encoding the UDP-galactose ceramide galactosyl transferase (cerebroside synthase): cloning, characterization, and assignment to human chromosome 4, band q26. Genomics 34: 69-75
5. Bouktaib M, Atmani A, Rolando C (2002) Regio- and stereoselective synthesis of the major metabolite of quercetin, quercetin-3-O-β-D- glucuronide. Tetrahedron Lett 43: 6263-6266
6. Bourne Y, Henrissat B (2001) Glycoside hydrolases and glycosyltransferases: families and functional modules. Curr Opin Struct Biol 11: 593-600
7. Campbell JA, Davies GJ, Bulone V, Henrissat B (1997) A classification of nucleotide-diphospho-sugar glycosyltransferases based on amino acid sequence similarities. Biochem J 326: 929-942
8. Chong J, Baltz R, Schmitt C, Beffa R, Fritig B, Saindrenan P (2002) Downregulation of a pathogen-responsive tobacco UDP-Glc:phenylpropanoid glucosyltransferase reduces scopoletin glucoside accumulation, enhances oxidative stress, and weakens virus resistance. Plant Cell 14: 1093-1107
9. Coleman JOD, Blake-Kalff MMA, Davies TGE (1997) Detoxification of xenobiotics by plants: chemical modification and vacuolar compartmentation. Trends Plant Sci 2: 144-151
10. Coutinho PM, Deleury E, Davies GJ, Henrissat B (2003) An evolving hierarchical family classification for glycosyltransferases. J Mol Biol 328: 307-317
11. Fukuchi-Mizutani M, Okuhara H, Fukui Y, Nakao M, Katsumoto Y, Yonekura-Sakakibara K, Kusumi T, Hase T, Tanaka Y (2003) Biochemical and molecular characterization of a novel UDP-glucose:anthoyanin 3′-O-glucosyltransferase, a key enzyme for blue anthocyanin biosynthesis, from gentian. Plant Physiol 132: 1652-1663
12. Gong Q-H, Cho JW, Huang T, Potter C, Gholam N, Basu NK, Kubota S, Carvalho S, Pennington MW, Owens IS, Popescu NC (2001) Thirteen UDPglucuronosyltransferase genes are encoded at the human UGT1 gene complex locus. Pharmacogenetics 11: 357-368
13. Hansen KS, Kristensen C, Tattersall DB, Jones PR, Olsen CE, Bak S, Møller BL (2003) The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolour. Phytochemistry 64: 143-151
14. Heidlas JE, Lees WJ, Whitesides GM (1992) Practical enzyme-based syntheses of uridine 57prime;-diphosphogalactose and uridine 5′-diphospho-N-acetylgalactosamine on a gram scale. J Org Chem 57: 152-157
15. Hirschberg CB, Robbins PW, Abeijon C (1998) Transporters of nucleotide sugar, ATP, and nucleotide sulfate in the endoplasmic reticulum and Golgi apparatus. Annu Rev Biochem 67: 49-69
16. Hoffmeister D, Wilkinson B, Foster G, Sidebottom PJ, Ichinose K, Bechtold A (2002) Engineered urdamycin glycosyltransferases are broadened and altered in substrate specificity. Chem Biol 9: 287-295
17. Hösel W (1981) Glycosylation and glycosidases. In The Biochemistry of Plant, Stumpf PK, Conn EE (eds) pp 725-753. New York: Acedemic Press
18. Hu Y, Walker S (2002) Remarkable structural similarities between diverse glycosyltransferases. Chem Biol 9: 1287-1296
19. Hughes J, Hughes MA (1994) Multiple secondary plant product UDP-glucose glucosyltransferase genes expressed in cassava (Manihot esculenta Crantz) cotyledons. DNA Sequence 5: 41-49
20. Hundle BS, O'Brien DA, Alberti M, Beyer P, Hearst JE (1992) Functional expression of zeaxanthin glucosyltransferase from Erwinia herbicola and a proposed uridine-diphosphate binding site. Proc Natl Acad Sci USA 89: 9321-9325
21. Ichikawa Y, Lin YC, Dumas DP, Shen GJ, Garcia-Junceda E, Willams MA, Bayer R, Ketcham C, Walker LE, Paulson JC, Wong CH (1992) Chemical-enzymatic synthesis and conformational analysis of sialyl Lewis x and derivatives. J Am Chem Soc 114: 9283-9298
22. Ikan R (1999) Naturally Occurring Glycosides. Chichester (UK): Wiley
23. Jackson RG, Kowalczyk M, Li Y, Higgins G, Ross J, Sandberg G, Bowles DJ (2002) Over-expression of an Arabidopsis gene encoding a glucosyltransferase of indole-3-acetic acid: phenotypic characterisation of transgenic lines. Plant J 32: 573-583
24. Jackson RG, Lim E-K, Li Y, Kowalczyk M, Sandberg G, Hoggett J, Ashford DA, Bowles DJ (2001) Identification and biochemical characterisation of an Arabidopsis indole-3-acetic acid glucosyltransferase. J Biol Chem 276: 4350-4356
25. Jones P, Messner B, Nakajima J-I, Schaffner A, Saito K (2003) UGT73C6 and UGT78D1-glycosyltransferases involved in flavonol glycoside biosynthesis in Arabidopsis thaliana. J Biol Chem 278: 43910-43918
26. Jones P, Vogt T (2001) Glycosyltransferases in secondary plant metabolism: tranquilizers and stimulant controllers. Planta 213: 164-174
27. King CD, Rios GR, Green MD, Tephly TR (2000) UDP- glucuronosyltransferases. Curr Drug Metab 1: 143-161
28. Kleczkowski K, Schell F (1995) Phytohormone conjugates: nature and function. Crit Rev Plant Sci 14: 283-298
29. Klein M, Weissenböck G, Dufaud A, Gaillard C, Kreuz K, Martinoia E (1996) Different energization mechanisms drive the vacuolar uptake of a flavonoid glucoside and a herbicide glucoside. J Biol Chem 271: 29666-29671
30. Kolter T, Sandhoff K (1999) Sphingolipids-their metabolic pathways and the pathobiochemistry of neurodegenerative diseases. Angew Chem Int Ed 38: 1532-1568
31. König J, Nies AT, Cui Y, Leier I, Keppler D (1999) Conjugate export pumps of the multidrug resistance protein (MRP) family: localization, substrate specificity, and MRP2-mediated drug resistance. Biochem Biophys Acta 1461: 377-394
32. 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
33. Kruh GD, Belinsky MG (2003) The MRP family of drug efflux pumps. Oncogene 22: 7537-7552
34. Li M, Han X, Yu B (2002) Synthesis of quercetin 3-O-(2″-galloyl)- α-L-arabinopyranoside. Tetrahedron Lett 43: 9467-9470
35. Li Y, Baldauf S, Lim E-K, Bowles DJ (2001) Phylogenetic analysis of the UDP-glycosyltransferase multigene family of Arabidopsis thaliana. J Biol Chem 276: 4338-4343
36. Lim E-K, Ashford DA, Hou B, Jackson RG, Bowles DJ (2004) Arabidopsis glycosyltransferases as biocatalysts in fermentation for regioselective synthesis of diverse quercetin glucosides. Biotech Bioeng, (in press)
37. Lim E-K, Baldauf S, Li Y, Elias L, Worrall D, Spencer SP, Jackson RG, Taguchi G, Ross J, Bowles DJ (2003a) Evolution of substrate recognition across a multigene family of glycosyltransferases in Arabidopsis. Glycobiology 13: 139-145
38. Lim E-K, Doucet CJ, Elias L, Worrall D, Li Y, Ross J, Bowles DJ (2002) Activity of the group 1 glycosyltransferases of Arabidopsis towards salicylic acid, para-hydroxybenzoic acid and other benzoates. J Biol Chem 277: 586-592
39. Lim E-K, Higgins GS, Li Y, Bowles DJ (2003b) Regioselectivity of glucosylation of caffeic acid by a UDP-glucose:glucosyltransferase is maintained in planta. Biochem J 373: 987-992
40. Lim E-K, Li Y, Parr A, Jackson R, Ashford DA, Bowles DJ (2001) Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis. J Biol Chem 276: 4344-4349
41. 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
42. Mackenzie PI, Owen IS, Burchell B, Bock KW, Bairoch A, Bélanger A, Fournel-Gigleux S, Green M, Hum DW, Iyanagi T, Lancet D, Louisot P, Magdalou J, Chowdhury JR, Ritter JK, Schachter H, Tephly TR, Tipton KF, Nebert DW (1997) The UDP glycosyltransferases gene superfamily: recommended nomenclature update based on evolutionary divergence. Pharmacogenetics 7: 255-269
43. Marillia EF, MacPherson JM, Tsang EWT, van Audenhove K, Keller WA, GrootWassink JWD (2001) Molecular cloning of a Brassica napus thiohydroximate S-glucosyltransferase gene and its expression in Escherichia coli. Physiol Plant 113: 176-184
44. Martin RC, Mok DWS, Smets R, van Onckelen HA, Mok MC (2001a) Development of transgenic tobacco harbouring a zeatin O-glucosyltransferase gene from Phaseolus. In vitro Cell Dev Biol Plant 37: 354-360
45. Martin RC, Mok MC, Habben JE, Mok DWS (2001b) A maize cytokinin gene encoding an O-glucosyltransferase specific to cis-zeatin. Proc Natl Acad Sci USA 98: 5922-5926
46. Martin RC, Mok MC, Mok DWS (1999) A gene encoding the cytokinin enzyme zeatin O-xylosyltransferase of Phaseolus vulgaris. Plant Physiol 120: 553-557
47. Martinoia E, Klein M, Geisler M, Bovet L, Forestier C, Kolukisaoglu Ü, Müller-Röber B, Schulz B (2002) Multifunctionality of plant ABC transporters-more than just detoxifiers. Planta 214: 345-355
48. Meßner B, Thulke O, Schäffner AR (2003) Arabidopsis glucosyltransferases with activities toward both endogenous and xenobiotic substrates. Planta 217: 138-146
49. Miller KD, Guyon V, Evans JNS, Shuttleworth WA, Taylor LP (1999) 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
50. Miners JO, Smith PA, Sorich MJ, Mckinnon RA, Mackenzie PI (2004) Predicting human drug glucuronidation parameters: application of in vitro and in silico modelling approaches. Annu Rev Pharmacol Toxicol 44: 1-25
51. Mulichak AM, Losey HC, Lu W, Wawrzak Z, Walsh CT, Garavito RM (2003) Structure of the TDP-epi-vancosaminyltransferase GtfA from the chloroeremomycin biosynthetic pathway. Proc Natl Acad Sci USA 100: 9238-9243
52. Mulichak AM, Losey HC, Walsh CT, Garavito RM (2001) Structure of the UDP-glucosyltransferase GtfB that modifies the heptapeptide aglycone in the biosynthesis of vancomycin group antibiotics. Structure 9: 547-557
53. Nagashima S, Inagaki R, Kubo A, Hirotani M, Yoshikawa T (2004) cDNA cloning and expression of isoflavonoid-specific glucosyltransferase from Glycynhiza echinata cell-suspension cultures. Planta 218: 456-459
54. Paquette S, Møller BL, Bak S (2003) On the origin of family 1 plant glycosyltransferases. Phytochemistry 62: 399-413.
55. Pillot T, Ouzzine M, Fournel-Gigleux S, Lafaurie C, Tebbi D, Treat S, Radominska A, Lester R, Siest G, Magdalou J (1993) Determination of the human liver UDP-glucuronosyltransferase 2B4 domains involved in the binding of UDP-glucuronic acid using photoaffinity labeling of fusion proteins. Biochem Biophys Res Commun 197: 785-791
56. Poppenberger B, Berthiller F, Lucyshyn D, Sieberer T, Schuhmacher R, Krska R, Kuchler K, Glössl J, Luschnig C, Adam G (2003) Detoxification of the Fusarium mycotoxin deoxynivalenol by a UDP-glucosyltransferase from Arabidopsis thaliana. J Biol Chem 278: 47905-47914
57. Quiel JA, Bender J (2003) Glucose conjugation of anthranilate by the Arabidopsis UGT74F2 glucosyltransferase is required for tryptophan mutant blue fluorescence. J Biol Chem 278: 6275-6281
58. Radominska-Pandya A, Czernik PJ, Little JM, Battaglia E, Mackenzie PI (1999) Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev 31: 817-899
59. Rea PA, Li Z-S, Lu Y-P, Drozdowicz YM (1998) From vacuole GS-X pumps to multispecific ABC transporters. Annu Rev Plant Physiol Plant MolBiol 49: 727-760
60. Ross J, Li Y, Lim E-K, Bowles DJ (2001) Higher plant glycosyltransferases. Genome Biol 2: 3004.1-3004.6
61. Ross P, Mayer R, Benziman M (1991) Cellulose biosynthesis and function in bacteria. Microbiol Rev 55: 35-58
62. Sandermann H, Pflugmacher S (1998) Taxonomic distribution of plant glucosyltransferases acting on xenobiotics. Photochemistry 49: 507-511
63. Sprong H, Kruithof B, Leijendekker R, Slot JW, van Meer G, van der Sluijs P (1998) UDP-galactose:ceramide galactosyltransferase is a class I integral membrane protein of the endoplasmic reticulum. J Biol Chem 273: 25880-25888
64. Taguchi G, Ubukata T, Hayashida N, Yamamoto H, Okazaki M (2003) Cloning and characterization of a glucosyltransferase that reacts on 7-hydroxyl group of flavonol and 3-hydroxyl group of coumarin from tobacco cells. Arch Biochem Biophys 420: 95-102
65. Taguchi G, Yazawa T, Hayashida N, Okazaki M (2001) Molecular cloning and heterologous expression of novel glucosyltransferases from tobacco cultured cells that have broad substrate specificity and are induced by salicylic acid and auxin. Eur J Biochem 268: 1-10
66. Tarbouriech N, Charnock SJ, Davies GJ (2001) Three-dimensional structures of the Mn and Mg dTDP complexes of the family GT-2 glycosyltransferase SpsA: a comparison with related NDP-sugar glycosyltransferases. J Mol Biol 314: 655-661
67. Tukey RH, Strassburg CP (2000) Human UDP-glucuronosyltransferases: metabolism, expression and disease. Annu Rev Pharmacol Toxicol 40: 581-616
68. Ünligil UM, Rini JM (2000) Glycosyltransferase structure and mechanism. Curr Opin Struct Biol 10: 510-517
69. Veach YK, Martin RC, Mok DWS, Malbeck J, Vankova R, Mok MC (2003) O-glucosylation of cis-zeatin in maize. Characterization of genes, enzymes, and endogenous cytokinins. Plant Physiol 131: 1374-1380
70. Vogt T (2002) Substrate specificity and sequence analysis define a polyphyletic origin of betanidin 5- and 6-O-glucosyltransferase from Dorotheanthus bellidiformis. Planta 214: 492-495
71. Vogt T, Jones P (2000) Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci 5: 380-386
72. von Rad U, Hüttl R, Lottspeich F, Gierl A, Frey M (2001) Two glucosyltransferases are involved in detoxification of benzoxazinoids in maize. Plant J 28: 633-642
73. Willits MG, Giovanni M, Prata RTN, Kramer CM, Luca VD, Steffens JC, Graser G (2004) Bio-fermentation of modified flavonoids: an example of in vivo diversification of secondary metabolites. Phytochemistry 65: 31-41
74. Winkel-Shirley B (1999) Evidence for enzyme complexes in the phenylpropanoid and flavonoid pathways. Physiol Plant 107: 142-149
75. Wong CH, Wang R, Ichikawa Y (1992) Regeneration of sugar nucleotide for enzymatic oligosaccharide synthesis: use of Gal-1-phosphate uridyltransferase in the regeneration of UDP-galactose, UDP-2-deoxygalactose, and UDP-galactosamine. J Org Chem 57: 4343-4344
76. Yamazaki M, Yamagishi E, Gong ZZ, 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
77. Zhang Z, Kochhar S, Grigorov M (2003) Exploring the sequence-structure protein landscape in the glycosyltransferase family. Protein Sci 12: 2291-2302