Abstract
Among more than 100 rice uridine diphosphate glycosyltransferases (UGTs), OsUGT-3 was selected as a candidate for producing flavonoid O-diglycosyltransferases based on phylogenetic analysis and molecular docking. This gene was functionally expressed in Escherichia coli. Analysis of kaempferol, luteolin, quercetin, and tricin reaction products using liquid chromatography-mass spectrometry revealed that these were diglucosylated. The glucosylation positions of kaempferol, which was the best substrate, were determined to be the 3- and 7-hydroxyl groups. This is the first flavonoid O-diglucosyltransferase described from rice.
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Fischbach MA, Lin H, Liu DR, Walsh CT (2005) In vitro characterization of IroB, a pathogen-associated C-glycosyltransferase. Proc Natl Acad Sci U S A 102:571–576
Gachon CMM, Langlois-Meurinne M, Saindrenan P (2005) Plant secondary metabolism glycosyltransferases: the emerging functional analysis. Trends Plant Sci 11:542–549
Hong BS, Kim JH, Kim NY, Kim BG, Chong Y, Ahn J-H (2007) Characterization of uridine-diphosphate dependent flavonoid glucosyltransferase from Oryza sativa. J Biochem Mol Biol 40:870–874
Jones P, Vogt T (2001) Glycosyltransferase in secondary plant metabolism: tranquilizers and stimulant controllers. Planta 213:164–174
Jones P, Messner B, Nakajima JI, Schäffner A, Satito K (2003) UGT73C6 and UGT78D1-glycosyltransferases involved in flavonol glycoside biosynthesis in Arabidopsis thaliana. J Biol Chem 278:43910–43918
Kim BG, Kim JH, Min SY, Shin KH, Kim JH, Kim HI, Ryu SN, Ahn J-H (2007) Anthocyanin content in rice is related to expression level of anthocyanin biosynthetic genes. J Plant Biol 50:156–160
Kim JH, Cheon YM, Kim BG, Ahn J-H (2008a) Analysis of flavonoids and characterization of the OsFNS gene involved in flavone biosynthesis in rice. J Plant Biol 51:97–101
Kim BG, Kim JH, Kim J, Lee C, Ahn J-H (2008b) Accumulation of flavonols by ultraviolet-B is related to induction of flavanone 3-β-hydroxylase and flavonol synthase in soybean. Mol Cell 25:247–252
Ko JH, Kim BG, Hur H-G, Lim Y, Ahn J-H (2006) Molecular cloning, expression and characterization of a glycosyltransferase from rice. Plant Cell Rep 25:741–746
Ko JH, Kim BG, Kim JH, Kim H, Lim CE, Lim J, Lee C, Lim Y, Ahn J-H (2008) Four glucosyltransferases from rice: cDNA cloning, expression, and characterization. J Plant Physiol 165:435–444
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
Kubo A, Arai Y, Nagashima S, Yoshikawa T (2004) Alteration of sugar donor specificities of plant glycosyltransferases by a single point mutation. Arch Biochem Biophys 429:198–203
Liang D, Qiao J (2007) Phylogenetic analysis of antibiotic glycosyltransferases. J Mol Evol 64:342–353
Lillo C, Lea US, Ruoff P (2008) Nutrient deletion as a key factor for manipulating gene expression and product formation in different branches of the flavonoid pathway. Plant Cell Environ 31:587–601
Lim E-K, Bowles DJ (2004) A class of plant glycosyltransferases involved in cellular homeostasis. EMBO J 23:2915–2922
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 Bioengr 87:623–631
Mackenzie PI, Owens IS, Burchell B, Bock KW, Bairoch A et al (1997) The UDP glycosyltransferase gene superfamily: Recommended nomenclature update based on evolutionary divergence. Pharmacogenetics 7:255–269
Markham KR, Tannera GJ, Caasi-Lit M, Whitecross MI, Nayudu M, Mitchell KA (1998) Possible protective role for 3′,4′-dihydroxyflavones induced by enhanced UV-B in a UV-tolerant rice cultivar. Phytochemistry 49:1913–1919
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 hybrid. J Biol Chem 274:34011–34019
Offen W, Martinez-Fleites C, Yang M, Lim E-K, Davis BG, Tarling CA, Ford CM, Bowles DJ, Davies GJ (2006) Structure of a flavonoid glucosyltransferase reveals the basis for plant natural product modification. EMBO J 25:1396–1405
Park SH, Kim BG, Lee SH, Lim Y, Cheong Y, Ahn J-H (2007) Molecular modeling and site directed mutagenesis of the O-methyltransferase, SOMT-9, reveals amino acids important for its reaction and regioselectivity. Bull Kor Chem Soc 28:2248–2252
Shao HS, He X, Achnine L, Blount JW, Dixon RA, Wang X (2005) Crystal structures of a multifunctional triterpene/flavonoid glycosyltransferase from Medicago truncatula. Plant Cell 17:3141–3154
Tahara S (2007) A journey of twenty-five years through the ecological biochemistry of flavonoids. Biosci Biotechnol Biochem 71:1387–1404
Torson JS, Hosted TJ Jr, Jiang JQ, Buggubs JB, Ahlert J (2001) Nature’s carbohydrate chemists: the enzymatic glycosylation of bioactive bacterial metabolites. Curr Org Chem 5:139–167
Vogt T, Zimmermann E, Grimm R, Meyer M, Stack D (1997) Are the characteristics of betanidin glucosyltransferases from cell suspension cultures of Dorotheanthus bellidiformis indicative of their phylogenetic relationship with flavonoid glucosyltransferases? Planta 203:349–361
Williams CA (2006) Flavone and flavonol O-glycosides. In: Andersen ØM, Markham KR (eds) Flavonoids; chemistry, biochemistry and application. CRC Press, Boca Raton, FL, USA, pp 749–856
Yonekura-Sakakibara K, Tohge T, Niida R, Saito K (2007) Identification of a flavonol 7-O-rhamnosyltransferase gene determining flavonoid pattern in Arabidopsis by transcriptome coexpression analysis and reverse genetics. J Biol Chem 282:14932–14941
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This work was supported by a Korea Research Foundation grant funded by the Korean Government (MOEHRD) (KRF-2005-214-00029).
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Kim, BG., Kim, N.Y., Kim, J.H. et al. Flavonoid O-Diglucosyltransferase from Rice: Molecular Cloning and Characterization. J. Plant Biol. 52, 41–48 (2009). https://doi.org/10.1007/s12374-008-9002-x
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DOI: https://doi.org/10.1007/s12374-008-9002-x