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Volumn 16, Issue 1, 2016, Pages

Molecular cloning and characterization of a flavonoid-O-methyltransferase with broad substrate specificity and regioselectivity from Citrus depressa

Author keywords

Citrus depressa; Flavonoid; Nobiletin; O methyltransferase; S adenosyl l methionine dependent

Indexed keywords

FLAVONOID; METHYLTRANSFERASE; PLANT PROTEIN; RECOMBINANT PROTEIN;

EID: 84983336049     PISSN: None     EISSN: 14712229     Source Type: Journal    
DOI: 10.1186/s12870-016-0870-9     Document Type: Article
Times cited : (58)

References (43)
  • 1
    • 34347353371 scopus 로고    scopus 로고
    • A Journey of Twenty-Five Years through the Ecological Biochemistry of Flavonoids
    • Tahara S. A Journey of Twenty-Five Years through the Ecological Biochemistry of Flavonoids. Biosci Biotechnol Biochem. 2007;71(6):1387-404.
    • (2007) Biosci Biotechnol Biochem , vol.71 , Issue.6 , pp. 1387-1404
    • Tahara, S.1
  • 2
    • 0028155769 scopus 로고
    • The flavonoid biosynthetic pathway in plants: Function and evolution
    • Koes RE, Quattrocchio F, Mol JNM. The flavonoid biosynthetic pathway in plants: Function and evolution. Bio Essays. 1994;16(2):123-32.
    • (1994) Bio Essays , vol.16 , Issue.2 , pp. 123-132
    • Koes, R.E.1    Quattrocchio, F.2    Mol, J.N.M.3
  • 3
    • 0036011081 scopus 로고    scopus 로고
    • Biosynthesis of flavonoids and effects of stress
    • Winkel-Shirley B. Biosynthesis of flavonoids and effects of stress. Curr Opin Plant Biol. 2002;5(3):218-23.
    • (2002) Curr Opin Plant Biol , vol.5 , Issue.3 , pp. 218-223
    • Winkel-Shirley, B.1
  • 4
    • 0029867672 scopus 로고    scopus 로고
    • Flavonoids-Chemistry, metabolism, cardioprotective effects, and dietary sources
    • Cook NC, Samman S. Flavonoids-Chemistry, metabolism, cardioprotective effects, and dietary sources. J Nutr Biochem. 1996;7(2):66-76.
    • (1996) J Nutr Biochem , vol.7 , Issue.2 , pp. 66-76
    • Cook, N.C.1    Samman, S.2
  • 5
    • 0032400815 scopus 로고    scopus 로고
    • Flavonoids: Dietary occurrence and biochemical activity
    • Peterson JMS, Dwyer J, Dsc RD. Flavonoids: Dietary occurrence and biochemical activity. Nutr Res. 1998;18(12):1995-2018.
    • (1998) Nutr Res , vol.18 , Issue.12 , pp. 1995-2018
    • Peterson, J.M.S.1    Dwyer, J.2    Dsc, R.D.3
  • 6
    • 0142245411 scopus 로고    scopus 로고
    • Flavonoid function and activity to plants and other organisms
    • Iwashina T. Flavonoid function and activity to plants and other organisms. Biol Sci Space. 2003;17(1):24-44.
    • (2003) Biol Sci Space , vol.17 , Issue.1 , pp. 24-44
    • Iwashina, T.1
  • 7
    • 33746496150 scopus 로고    scopus 로고
    • Significance of flavonoids in plant resistance: a review
    • Treutter D. Significance of flavonoids in plant resistance: a review. Environ Chem Lett. 2006;4:147-57.
    • (2006) Environ Chem Lett , vol.4 , pp. 147-157
    • Treutter, D.1
  • 8
    • 64849085940 scopus 로고    scopus 로고
    • Antifeedant activity of ethanolic extract from Flourensia oolepis and isolation of pinocembrin as its active principle compound
    • Napal GND, Aarpinella MC, Palacios SM. Antifeedant activity of ethanolic extract from Flourensia oolepis and isolation of pinocembrin as its active principle compound. Bioresour Technol. 2009;100(14):36693673.
    • (2009) Bioresour Technol , vol.100 , Issue.14 , pp. 36693673
    • Napal, G.N.D.1    Aarpinella, M.C.2    Palacios, S.M.3
  • 9
    • 18044382563 scopus 로고    scopus 로고
    • Flavonoids as developmental regulators
    • Taylor LP, Grotewold E. Flavonoids as developmental regulators. Curr Opin Plant Biol. 2005;8(3):317-23.
    • (2005) Curr Opin Plant Biol , vol.8 , Issue.3 , pp. 317-323
    • Taylor, L.P.1    Grotewold, E.2
  • 10
    • 33750610365 scopus 로고    scopus 로고
    • Flavonoids with anti-Helicobacter pylori activity from Cistus laurifolius leaves
    • Ustün O, Ozçelik B, Akyön Y, Abbasoglu U, Yesilada E. Flavonoids with anti-Helicobacter pylori activity from Cistus laurifolius leaves. J Ethnopharmacol. 2006;108(3):457-61.
    • (2006) J Ethnopharmacol , vol.108 , Issue.3 , pp. 457-461
    • Ustün, O.1    Ozçelik, B.2    Akyön, Y.3    Abbasoglu, U.4    Yesilada, E.5
  • 11
    • 0022517588 scopus 로고
    • 3-methylquercetin is a potent and selective inhibitor of poliovirus RNA synthesis
    • Castrillo J, Berghe DV, Carrasco L. 3-methylquercetin is a potent and selective inhibitor of poliovirus RNA synthesis. Virology. 1986;152(1):219-27.
    • (1986) Virology , vol.152 , Issue.1 , pp. 219-227
    • Castrillo, J.1    Berghe, D.V.2    Carrasco, L.3
  • 12
    • 0036173982 scopus 로고    scopus 로고
    • Inhibition of Activator Protein-1 Binding Activity and Phosphatidylinositol 3-Kinase Pathway by Nobiletin, a Polymethoxy Flavonoid, Results in Augmentation of Tissue Inhibitor of Metalloproteinases-1 Production and Suppression of Production of Matrix Metalloproteinases-1 and -9 in Human Fibrosarcoma HT-1080 Cells
    • Sato T, Koike L, Miyata Y, Hirata M, Mimaki Y, Sashida Y, Yano M, Ito A. Inhibition of Activator Protein-1 Binding Activity and Phosphatidylinositol 3-Kinase Pathway by Nobiletin, a Polymethoxy Flavonoid, Results in Augmentation of Tissue Inhibitor of Metalloproteinases-1 Production and Suppression of Production of Matrix Metalloproteinases-1 and -9 in Human Fibrosarcoma HT-1080 Cells. Cancer Res. 2002;62(4):1025-9.
    • (2002) Cancer Res , vol.62 , Issue.4 , pp. 1025-1029
    • Sato, T.1    Koike, L.2    Miyata, Y.3    Hirata, M.4    Mimaki, Y.5    Sashida, Y.6    Yano, M.7    Ito, A.8
  • 13
    • 4344618973 scopus 로고    scopus 로고
    • Anti-tumour effects of nobiletin, a citrus flavonoid, on gastric cancer include: antiproliferative effects, induction of apoptosis and cell cycle deregulation
    • Yoshimizu N, Otani Y, Saikawa Y, Kubota T, Yoshida M, Furukawa T, Kumai K, Kameyama K, Fujii M, Yano M, et al. Anti-tumour effects of nobiletin, a citrus flavonoid, on gastric cancer include: antiproliferative effects, induction of apoptosis and cell cycle deregulation. Aliment Pharmacol Ther. 2004;20:95-101.
    • (2004) Aliment Pharmacol Ther , vol.20 , pp. 95-101
    • Yoshimizu, N.1    Otani, Y.2    Saikawa, Y.3    Kubota, T.4    Yoshida, M.5    Furukawa, T.6    Kumai, K.7    Kameyama, K.8    Fujii, M.9    Yano, M.10
  • 14
    • 84865414853 scopus 로고    scopus 로고
    • Polymethoxy Flavonoids, Nobiletin and Tangeretin, Prevent Lipopolysaccharide-Induced Inflammatory Bone Loss in an Experimental Model for Periodontitis
    • Tominari T, Hirata M, Matsumoto C, Inada M, Miyaura C. Polymethoxy Flavonoids, Nobiletin and Tangeretin, Prevent Lipopolysaccharide-Induced Inflammatory Bone Loss in an Experimental Model for Periodontitis. J Pharmacol Sci. 2012;119(4):390-4.
    • (2012) J Pharmacol Sci , vol.119 , Issue.4 , pp. 390-394
    • Tominari, T.1    Hirata, M.2    Matsumoto, C.3    Inada, M.4    Miyaura, C.5
  • 15
    • 84911481118 scopus 로고    scopus 로고
    • Bioavailability of ctrus polymethoxylated flavones and their biological role in metabolic syndorome and hyperlipidemia
    • In: Noreddin A, editors. Intech
    • Evans M, Sharma P, Guthrie N. Bioavailability of ctrus polymethoxylated flavones and their biological role in metabolic syndorome and hyperlipidemia. In: Noreddin A, editors. Readings in advanced pharmacokinetics - Theory, methods and applications. Intech; 2012. p. 267-84. http://www.intechopen.com/books/readings-in-advanced-pharmacokinetics-theory-methods-and-applications.
    • (2012) Readings in advanced pharmacokinetics - Theory, methods and applications , pp. 267-284
    • Evans, M.1    Sharma, P.2    Guthrie, N.3
  • 16
    • 33745769794 scopus 로고    scopus 로고
    • Citrus polymethoxylated flavones improve lipid and glucose homeostasis and modulate adipocytokines in fructose-induced insulin resistant hamsters
    • Li RW, Theriault AG, Au K, Douglas TD, Casaschi A, Kurowska EM, Mukherjee R. Citrus polymethoxylated flavones improve lipid and glucose homeostasis and modulate adipocytokines in fructose-induced insulin resistant hamsters. Life Sci. 2006;79(4):365-73.
    • (2006) Life Sci , vol.79 , Issue.4 , pp. 365-373
    • Li, R.W.1    Theriault, A.G.2    Au, K.3    Douglas, T.D.4    Casaschi, A.5    Kurowska, E.M.6    Mukherjee, R.7
  • 18
    • 84879369568 scopus 로고    scopus 로고
    • Identification through high-throughput screening of 4'-methoxyflavone and 3',4'-dimethoxyflavone as novel neuroprotective inhibitors of parthanatos
    • Fatokun AA, Liu JO, Dawson VL, Dawson TM. Identification through high-throughput screening of 4'-methoxyflavone and 3',4'-dimethoxyflavone as novel neuroprotective inhibitors of parthanatos. Br J Pharmacol. 2013;169(6):1263-78.
    • (2013) Br J Pharmacol , vol.169 , Issue.6 , pp. 1263-1278
    • Fatokun, A.A.1    Liu, J.O.2    Dawson, V.L.3    Dawson, T.M.4
  • 20
    • 40949149451 scopus 로고    scopus 로고
    • Interactive effects of polymethoxy flavones from Citrus on cell growth inhibition in human neuroblastoma SH-SY5Y cells
    • Akao Y, Itoh T, Ohguchi K, Iinuma M, Nozawa Y. Interactive effects of polymethoxy flavones from Citrus on cell growth inhibition in human neuroblastoma SH-SY5Y cells. Bioorg Med Chem. 2008;16(6):2803-10.
    • (2008) Bioorg Med Chem , vol.16 , Issue.6 , pp. 2803-2810
    • Akao, Y.1    Itoh, T.2    Ohguchi, K.3    Iinuma, M.4    Nozawa, Y.5
  • 21
    • 47849089229 scopus 로고    scopus 로고
    • Citrus nobiletin suppresses bone loss in ovariectomized ddY mice and collagen-induced arthritis in DBA/1 J mice: Possible involvement of receptor activator of NF-kappaB ligand (RANKL)-induced osteoclastogenesis regulation
    • Murakami A, Song M, Katsumata S-I, Uehara M, Suzuki K, Ohigashi H. Citrus nobiletin suppresses bone loss in ovariectomized ddY mice and collagen-induced arthritis in DBA/1 J mice: Possible involvement of receptor activator of NF-kappaB ligand (RANKL)-induced osteoclastogenesis regulation. Biofactors. 2007;30(3):179-92.
    • (2007) Biofactors , vol.30 , Issue.3 , pp. 179-192
    • Murakami, A.1    Song, M.2    Katsumata, S.-I.3    Uehara, M.4    Suzuki, K.5    Ohigashi, H.6
  • 22
    • 0032126760 scopus 로고    scopus 로고
    • Conserved sequence motifs in plant S-adenosyl-L-methionine-dependent methyltransferase
    • Joshi CP, Chiang VL. Conserved sequence motifs in plant S-adenosyl-L-methionine-dependent methyltransferase. Plant Mol Biol. 1998;37:663-74.
    • (1998) Plant Mol Biol , vol.37 , pp. 663-674
    • Joshi, C.P.1    Chiang, V.L.2
  • 23
    • 0034711291 scopus 로고    scopus 로고
    • Modifications in Lignin and Accumulation of Phenolic Glucosides in Poplar Xylem upon Down-regulation of Caffeoyl-Coenzyme A O-Methyltransferase, an Enzyme Involved in Lignin Biosynthesis
    • Meyermans H, Morreel K, Lapierre C, Pollet B, De Bruyn A, Busson R, Herdewijn P, Devreese B, Van Beeumen J, Marita JM, et al. Modifications in Lignin and Accumulation of Phenolic Glucosides in Poplar Xylem upon Down-regulation of Caffeoyl-Coenzyme A O-Methyltransferase, an Enzyme Involved in Lignin Biosynthesis. J Biol Chem. 2000;275(47):36899-909.
    • (2000) J Biol Chem , vol.275 , Issue.47 , pp. 36899-36909
    • Meyermans, H.1    Morreel, K.2    Lapierre, C.3    Pollet, B.4    Bruyn, A.5    Busson, R.6    Herdewijn, P.7    Devreese, B.8    Beeumen, J.9    Marita, J.M.10
  • 24
    • 0033783438 scopus 로고    scopus 로고
    • Essential Role of Caffeoyl Coenzyme A O-Methyltransferase in Lignin Biosynthesis in Woody Poplar Plants
    • Zhong R, Morrison WH, Himmelsbach DS, Poole FL, Ye Z-H. Essential Role of Caffeoyl Coenzyme A O-Methyltransferase in Lignin Biosynthesis in Woody Poplar Plants. Plant Physiol. 2000;124(2):563-78.
    • (2000) Plant Physiol , vol.124 , Issue.2 , pp. 563-578
    • Zhong, R.1    Morrison, W.H.2    Himmelsbach, D.S.3    Poole, F.L.4    Ye, Z.-H.5
  • 25
  • 26
    • 0742325335 scopus 로고
    • O-methylation of flavonoids by cell-free extracts of calamondin orange
    • Brunet G, Ibrahim RK. O-methylation of flavonoids by cell-free extracts of calamondin orange. Phytochemistry. 1980;19(5):741-6.
    • (1980) Phytochemistry , vol.19 , Issue.5 , pp. 741-746
    • Brunet, G.1    Ibrahim, R.K.2
  • 27
    • 84945581505 scopus 로고    scopus 로고
    • Systematic analysis of O-methyltransferase gene family and identification of potential members involved in the formation of O-methylated flavonoids in Citrus
    • Liu X, Luo Y, Wu H, Xi W, Yu J, Zhang Q, Zhou Z. Systematic analysis of O-methyltransferase gene family and identification of potential members involved in the formation of O-methylated flavonoids in Citrus. Gene. 2016;575(2, Part 2):458-72.
    • (2016) Gene , vol.575 , Issue.2 , pp. 458-472
    • Liu, X.1    Luo, Y.2    Wu, H.3    Xi, W.4    Yu, J.5    Zhang, Q.6    Zhou, Z.7
  • 28
    • 2142647808 scopus 로고    scopus 로고
    • Flavonoid methylation: a novel 4'-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases
    • Schroder G, Wehinger E, Lukacin R, Wellmann F, Seefelder W, Schwab W, Schroder J. Flavonoid methylation: a novel 4'-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases. Phytochemistry. 2004;65(8):1085-94.
    • (2004) Phytochemistry , vol.65 , Issue.8 , pp. 1085-1094
    • Schroder, G.1    Wehinger, E.2    Lukacin, R.3    Wellmann, F.4    Seefelder, W.5    Schwab, W.6    Schroder, J.7
  • 29
    • 0031882371 scopus 로고    scopus 로고
    • Plant O-methyltransferase: molecular analysis, common signature and classification
    • Ibrahim RK, Bruneau A, Bantignies B. Plant O-methyltransferase: molecular analysis, common signature and classification. Plant Mol Biol. 1998;36:1-10.
    • (1998) Plant Mol Biol , vol.36 , pp. 1-10
    • Ibrahim, R.K.1    Bruneau, A.2    Bantignies, B.3
  • 30
    • 77957371299 scopus 로고    scopus 로고
    • Plant Flavonoid O-Methyltransferases: Substrate Specificity and Application
    • Kim B-G, Sung SH, Chong Y, Lim Y, Ahn J-H. Plant Flavonoid O-Methyltransferases: Substrate Specificity and Application. J Plant Biol. 2010;53(5):321-9.
    • (2010) J Plant Biol , vol.53 , Issue.5 , pp. 321-329
    • Kim, B.-G.1    Sung, S.H.2    Chong, Y.3    Lim, Y.4    Ahn, J.-H.5
  • 31
    • 0035983842 scopus 로고    scopus 로고
    • Structural Basis for the Modulation of Lignin Monomer Methylation by Caffeic Acid/5-Hydroxyferulic Acid 3/5-O-Methyltransferase
    • Zubieta C, Kota P, Ferrer J-L, Dixon RA, Noel JP. Structural Basis for the Modulation of Lignin Monomer Methylation by Caffeic Acid/5-Hydroxyferulic Acid 3/5-O-Methyltransferase. Plant Cell. 2002;14(6):1265-77.
    • (2002) Plant Cell , vol.14 , Issue.6 , pp. 1265-1277
    • Zubieta, C.1    Kota, P.2    Ferrer, J.-L.3    Dixon, R.A.4    Noel, J.P.5
  • 32
    • 0035119588 scopus 로고    scopus 로고
    • Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferase
    • Zubieta C, He XZ, Dixon RA, Noel JP. Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferase. Nat Struct Mol Biol. 2001;8:271-9.
    • (2001) Nat Struct Mol Biol , vol.8 , pp. 271-279
    • Zubieta, C.1    He, X.Z.2    Dixon, R.A.3    Noel, J.P.4
  • 33
    • 0038118144 scopus 로고    scopus 로고
    • A flavonol O-methyltransferase from Catharanthus roseus performing two sequential methylations
    • Cacace S, Schröder G, Wehinger E, Strack D, Schmidt J, Schröder J. A flavonol O-methyltransferase from Catharanthus roseus performing two sequential methylations. Phytochemistry. 2003;62(2):127-37.
    • (2003) Phytochemistry , vol.62 , Issue.2 , pp. 127-137
    • Cacace, S.1    Schröder, G.2    Wehinger, E.3    Strack, D.4    Schmidt, J.5    Schröder, J.6
  • 35
    • 84867132244 scopus 로고    scopus 로고
    • A Set of Regioselective O-Methyltransferases Gives Rise to the Complex Pattern of Methoxylated Flavones in Sweet Basil
    • Berim A, Hyatt DC, Gang DR. A Set of Regioselective O-Methyltransferases Gives Rise to the Complex Pattern of Methoxylated Flavones in Sweet Basil. Plant Physiol. 2012;160(2):1052-69.
    • (2012) Plant Physiol , vol.160 , Issue.2 , pp. 1052-1069
    • Berim, A.1    Hyatt, D.C.2    Gang, D.R.3
  • 36
    • 0742287178 scopus 로고    scopus 로고
    • Bio-fermentation of modified flavonoids: an example of in vivo diversification of secondary metabolites
    • Willits MG, Giovanni M, Prata RT, Kramer CM, De Luca V, Steffens JC, Graser G. Bio-fermentation of modified flavonoids: an example of in vivo diversification of secondary metabolites. Phytochemistry. 2004;65(1):31-41.
    • (2004) Phytochemistry , vol.65 , Issue.1 , pp. 31-41
    • Willits, M.G.1    Giovanni, M.2    Prata, R.T.3    Kramer, C.M.4    Luca, V.5    Steffens, J.C.6    Graser, G.7
  • 37
    • 78651507123 scopus 로고    scopus 로고
    • Engineering of flavonoid O-methyltransferase for a novel regioselectivity
    • Joe EJ, Kim BG, An BC, Chong Y, Ahn JH. Engineering of flavonoid O-methyltransferase for a novel regioselectivity. Mol Cells. 2010;30(2):137-41.
    • (2010) Mol Cells , vol.30 , Issue.2 , pp. 137-141
    • Joe, E.J.1    Kim, B.G.2    An, B.C.3    Chong, Y.4    Ahn, J.H.5
  • 38
    • 0033178672 scopus 로고    scopus 로고
    • Identification of specific residues involved in substrate discrimination in two plant O-methyltransferases
    • Wang J, Pichersky E. Identification of specific residues involved in substrate discrimination in two plant O-methyltransferases. Arch Biochem Biophys. 1999;368(1):172-80.
    • (1999) Arch Biochem Biophys , vol.368 , Issue.1 , pp. 172-180
    • Wang, J.1    Pichersky, E.2
  • 39
    • 77955709841 scopus 로고    scopus 로고
    • Two O-methyltransferase involved in the biosynthesis of methoxypyrazines: grape-derived aroma compounds important to wine flavour
    • Dunlevy JD, Sool KL, Perkins MV, Dennis EG, Keyzers RA, Kalua CM, Boss PK. Two O-methyltransferase involved in the biosynthesis of methoxypyrazines: grape-derived aroma compounds important to wine flavour. Plant Mol Biol. 2010;74:77-89.
    • (2010) Plant Mol Biol , vol.74 , pp. 77-89
    • Dunlevy, J.D.1    Sool, K.L.2    Perkins, M.V.3    Dennis, E.G.4    Keyzers, R.A.5    Kalua, C.M.6    Boss, P.K.7
  • 40
    • 0033083604 scopus 로고    scopus 로고
    • Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis
    • Frick S, Kutchan TM. Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis. Plant J. 1999;17(4):329-39.
    • (1999) Plant J , vol.17 , Issue.4 , pp. 329-339
    • Frick, S.1    Kutchan, T.M.2
  • 41
    • 84871913034 scopus 로고    scopus 로고
    • Molecular cloning: a laboratory manua
    • 3rd ed. Cold Spring Harbor: Cold Spring Harbor Laboratory Press
    • Green MR, Sambrook J. Molecular cloning: a laboratory manua. 3rd ed. Cold Spring Harbor: Cold Spring Harbor Laboratory Press; 2001.
    • (2001)
    • Green, M.R.1    Sambrook, J.2
  • 43
    • 0028949381 scopus 로고
    • Thermal asymmetric interlaced PCR: automatable amplification and sequencing of insert end fragments from P1 and YAC clones for chromosome walking
    • Liu YG, Whittier RF. Thermal asymmetric interlaced PCR: automatable amplification and sequencing of insert end fragments from P1 and YAC clones for chromosome walking. Genomics. 1995;25(3):674-81.
    • (1995) Genomics , vol.25 , Issue.3 , pp. 674-681
    • Liu, Y.G.1    Whittier, R.F.2


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