The flavonoid biosynthetic pathway in Arabidopsis: Structural and genetic diversity

Haslam, 1993

Halliwell, 2005, Health promotion by flavonoids, tocopherols, tocotrienols, and other phenols: direct or indirect effects? Antioxidant or not?, The American Journal of Clinical Nutrition, 81, 268S, 10.1093/ajcn/81.1.268S

Wang, 2009, Dietary intake of selected flavonols, flavones, and flavonoid-rich foods and risk of cancer in middle-aged and older women, The American Journal of Clinical Nutrition, 89, 905, 10.3945/ajcn.2008.26913

Jan, 2010, Dietary flavonoid quercetin and associated health benefits—An overview, Food Reviews International, 26, 302, 10.1080/87559129.2010.484285

Bino, 2004, Potential of metabolomics as a functional genomics tool, Trends in Plant Science, 9, 418, 10.1016/j.tplants.2004.07.004

Saito, 2010, Metabolomics for functional genomics, systems biology, and biotechnology, Annual Review of Plant Biology, 61, 463, 10.1146/annurev.arplant.043008.092035

Winkel-Shirley, 2001, Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology, Plant Physiology, 126, 485, 10.1104/pp.126.2.485

Grotewold, 2006, The genetics and biochemistry of floral pigments, Annual Review of Plant Biology, 57, 761, 10.1146/annurev.arplant.57.032905.105248

Davies, 2006, Molecular biology and biotechnology of flavonoid biosynthesis, 143

Lepiniec, 2006, Genetics and biochemistry of seed flavonoids, Annual Review of Plant Biology, 57, 405, 10.1146/annurev.arplant.57.032905.105252

Farag, 2007, Metabolic profiling and systematic identification of flavonoids and isoflavonoids in roots and cell suspension cultures of Medicago truncatula using HPLC-UV-ESI-MS and GC-MS, Phytochemistry, 68, 342, 10.1016/j.phytochem.2006.10.023

Suzuki, 2008, Metabolic profiling of flavonoids in Lotus japonicus using liquid chromatography Fourier transform ion cyclotron resonance mass spectrometry, Phytochemistry, 69, 99, 10.1016/j.phytochem.2007.06.017

Hosseinian, 2008, Measurement of anthocyanins and other phytochemicals in purple wheat, Food Chemistry, 109, 916, 10.1016/j.foodchem.2007.12.083

Horai, 2010, MassBank: a public repository for sharing mass spectral data for life sciences, Journal of Mass Spectrometry, 45, 703, 10.1002/jms.1777

Matsuda, 2009, MS/MS spectral tag-based annotation of non-targeted profile of plant secondary metabolites, Plant Journal, 57, 555, 10.1111/j.1365-313X.2008.03705.x

Sawada, 2012, RIKEN tandem mass spectral database (ReSpect) for phytochemicals: a plant-specific MS/MS-based data resource and database, Phytochemistry, 82, 38, 10.1016/j.phytochem.2012.07.007

Graham, 1998, Flavonoid and flavonol glycoside metabolism in Arabidopsis, Plant Physiology and Biochemistry, 36, 135, 10.1016/S0981-9428(98)80098-3

Veit, 1999, Major flavonoids from Arabidopsis thaliana leaves, Journal of Natural Products, 62, 1301, 10.1021/np990080o

Bloor, 2002, The structure of the major anthocyanin in Arabidopsis thaliana, Phytochemistry, 59, 343, 10.1016/S0031-9422(01)00460-5

Tohge, 2005, Functional genomics by integrated analysis of metabolome and transcriptome of Arabidopsis plants over-expressing an MYB transcription factor, Plant Journal, 42, 218, 10.1111/j.1365-313X.2005.02371.x

Kerhoas, 2006, Structural characterization of the major flavonoid glycosides from Arabidopsis thaliana seeds, Journal of Agricultural and Food Chemistry, 54, 6603, 10.1021/jf061043n

Routaboul, 2006, Flavonoid diversity and biosynthesis in seed of Arabidopsis thaliana, Planta, 224, 96, 10.1007/s00425-005-0197-5

Stobiecki, 2006, Profiling of phenolic glycosidic conjugates in leaves of Arabidopsis thaliana using LC/MS, Metabolomics, 2, 197, 10.1007/s11306-006-0031-5

Tohge, 2007, Phytochemical genomics in Arabidopsis thaliana: a case study for functional identification of flavonoid biosynthesis genes, Pure and Applied Chemistry, 79, 811, 10.1351/pac200779040811

Yonekura-Sakakibara, 2008, Comprehensive flavonol profiling and transcriptome coexpression analysis leading to decoding gene-metabolite correlations in Arabidopsis, Plant Cell, 20, 2160, 10.1105/tpc.108.058040

Nakabayashi, 2009, Metabolomics-oriented isolation and structure elucidation of 37 compounds including two anthocyanins from Arabidopsis thaliana, Phytochemistry, 70, 1017, 10.1016/j.phytochem.2009.03.021

Tohge, 2009, Web-based resources for mass-spectrometry-based metabolomics: a user's guide, Phytochemistry, 70, 450, 10.1016/j.phytochem.2009.02.004

Matsuda, 2010, AtMetExpress development: a phytochemical atlas of Arabidopsis development, Plant Physiology, 152, 566, 10.1104/pp.109.148031

Vallabhaneni, 2012, Characterization of flavonol glycosides in individual Arabidopsis root tips by flow injection electrospray mass spectrometry, Phytochemistry, 73, 114, 10.1016/j.phytochem.2011.09.013

Rowan, 2009, Environmental regulation of leaf colour in red 35S: PAP1 Arabidopsis thaliana, New Phytologist, 182, 102, 10.1111/j.1469-8137.2008.02737.x

Stracke, 2010, Analysis of production of flavonol glycosides-dependent flavonol glycoside accumulation in Arabidopsis thaliana plants reveals MYB11-, MYB12-and MYB111-independent flavonol glycoside accumulation, New Phytologist, 188, 985, 10.1111/j.1469-8137.2010.03421.x

Kitamura, 2010, Metabolic profiling and cytological analysis of proanthocyanidins in immature seeds of Arabidopsis thaliana flavonoid accumulation mutants, Plant Journal, 62, 549, 10.1111/j.1365-313X.2010.04174.x

Tanner, 2003, Proanthocyanidin biosynthesis in plants – purification of legume leucoanthocyanidin reductase and molecular cloning of its cDNA, Journal of Biological Chemistry, 278, 31647, 10.1074/jbc.M302783200

Xie, 2005, Proanthocyanidin biosynthesis – still more questions than answers?, Phytochemistry, 66, 2127, 10.1016/j.phytochem.2005.01.008

Pang, 2007, Early steps in proanthocyanidin biosynthesis in the model legume Medicago truncatula, Plant Physiology, 145, 601, 10.1104/pp.107.107326

Pollastri, 2011, Flavonols: old compounds for old roles, Annals of Botany, 108, 1225, 10.1093/aob/mcr234

Dixon, 1995, Stress-induced phenylpropanoid metabolism, Plant Cell, 7, 1085, 10.2307/3870059

Winkel-Shirley, 2002, Molecular genetics and control of anthocyanin expression, 75, 10.1016/S0065-2296(02)37044-7

Taylor, 2005, Flavonoids as developmental regulators, Current Opinion in Plant Biology, 8, 317, 10.1016/j.pbi.2005.03.005

Roberts, 2006, Seduced by the dark side: integrating molecular and ecological perspectives on the influence of light on plant defence against pests and pathogens, New Phytologist, 170, 677, 10.1111/j.1469-8137.2006.01707.x

Falcone Ferreyra, 2012, Flavonoids: biosynthesis, biological functions, and biotechnological applications, Frontiers in Plant Science, 3, 1, 10.3389/fpls.2012.00222

Teng, 2005, Sucrose-specific induction of anthocyanin biosynthesis in Arabidopsis requires the MYB75/PAP1 gene, Plant Physiology, 139, 1840, 10.1104/pp.105.066688

Diaz, 2006, Leaf yellowing and anthocyanin accumulation are two genetically independent strategies in response to nitrogen limitation in Arabidopsis thaliana, Plant and Cell Physiology, 47, 74, 10.1093/pcp/pci225

Korn, 2010, Predicting Arabidopsis freezing tolerance and heterosis in freezing tolerance from metabolite composition, Molecular Plant, 3, 224, 10.1093/mp/ssp105

Korn, 2008, Heterosis in the freezing tolerance, and sugar and flavonoid contents of crosses between Arabidopsis thaliana accessions of widely varying freezing tolerance, Plant Cell and Environment, 31, 813, 10.1111/j.1365-3040.2008.01800.x

Matsuda, 2011, Mass spectra-based framework for automated structural elucidation of metabolome data to explore phytochemical diversity, Frontiers in Plant Science, 2, 40, 10.3389/fpls.2011.00040

Martens, 2003, Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley, FEBS Letters, 544, 93, 10.1016/S0014-5793(03)00479-4

Caputi, 2011, A genome-wide phylogenetic reconstruction of family 1 UDP-glycosyltransferases revealed the expansion of the family during the adaptation of plants to life on land, Plant Journal, 69, 1030, 10.1111/j.1365-313X.2011.04853.x

Bredebach, 2011, Three 2-oxoglutarate-dependent dioxygenase activities of Equisetum arvense L. forming flavone and flavonol from (2S)-naringenin, Phytochemistry, 72, 557, 10.1016/j.phytochem.2011.01.036

T. Tohge, M. Watanabe, R. Hoefgen, A.R. Fernie, The evolution of phenylpropanoid metabolism in the green lineage, Critical Reviews in Biochemistry and Molecular biology, in press.

Turnbull, 2004, Mechanistic studies on three 2-oxoglutarate-dependent oxygenases of flavonoid biosynthesis: anthocyanidin synthase, flavonol synthase, and flavanone 3β-hydroxylase, Journal of Biological Chemistry, 279, 1206, 10.1074/jbc.M309228200

Yonekura-Sakakibara, 2011, An evolutionary view of functional diversity in family 1 glycosyltransferases, Plant Journal, 66, 182, 10.1111/j.1365-313X.2011.04493.x

Keurentjes, 2006, The genetics of plant metabolism, Nature Genetics, 38, 842, 10.1038/ng1815

Tohge, 2010, Combining genetic diversity, informatics and metabolomics to facilitate annotation of plant gene function, Nature Protocols, 5, 1210, 10.1038/nprot.2010.82

Routaboul, 2012, Metabolite profiling and quantitative genetics of natural variation for flavonoids in Arabidopsis, Journal of Experimental Botany, 63, 3749, 10.1093/jxb/ers067

Fraser, 2011, The phenylpropanoid pathway in Arabidopsis, The Arabidopsis Book, e0152, 10.1199/tab.0152

Maeda, 2012, The shikimate pathway and aromatic amino acid biosynthesis in plants, Annual Review of Plant Biology, 63, 73, 10.1146/annurev-arplant-042811-105439

Ohl, 1990, Functional properties of a phenylalanine ammonia-lyase promoter from Arabidopsis, Plant Cell, 2, 837

Shufflebottom, 1993, Transcription of two members of a gene family encoding phenylalanine ammonia-lyase leads to remarkably different cell specificities and induction patterns, Plant Journal, 3, 835, 10.1111/j.1365-313X.1993.00835.x

Rohde, 2004, Molecular phenotyping of the pal1 and pal2 mutants of Arabidopsis thaliana reveals far-reaching consequences on phenylpropanoid, amino acid, and carbohydrate metabolism, Plant Cell, 16, 2749, 10.1105/tpc.104.023705

Raes, 2003, Genome-wide characterization of the lignification toolbox in Arabidopsis, Plant Physiology, 133, 1051, 10.1104/pp.103.026484

Cochrane, 2004, The Arabidopsis phenylalanine ammonia lyase gene family: kinetic characterization of the four PAL isoforms, Phytochemistry, 65, 1557, 10.1016/j.phytochem.2004.05.006

Huang, 2010, Functional analysis of the Arabidopsis PAL gene family in plant growth, development, and response to environmental stress, Plant Physiology, 153, 1526, 10.1104/pp.110.157370

Mizutani, 1997, Isolation of a cDNA and a genomic clone encoding cinnamate 4-hydroxylase from Arabidopsis and its expression manner in planta, Plant Physiology, 113, 755, 10.1104/pp.113.3.755

Werck-Reichhart, 2002

Schilmiller, 2009, Mutations in the cinnamate 4-hydroxylase gene impact metabolism, growth and development in Arabidopsis, Plant Journal, 60, 771, 10.1111/j.1365-313X.2009.03996.x

Ehlting, 1999, Three 4-coumarate: coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms, Plant Journal, 19, 9, 10.1046/j.1365-313X.1999.00491.x

Hamberger, 2004, The 4-coumarate: CoA ligase gene family in Arabidopsis thaliana comprises one rare, sinapate-activating and three commonly occurring isoenzymes, Proceedings of the National Academy of Sciences of the United States of America, 101, 2209, 10.1073/pnas.0307307101

Nikolau, 2003, Plant biotin-containing carboxylases, Archives of Biochemistry and Biophysics, 414, 211, 10.1016/S0003-9861(03)00156-5

Alban, 2000, Biotin metabolism in plants, Annual Review of Plant Physiology and Plant Molecular Biology, 51, 17, 10.1146/annurev.arplant.51.1.17

Sasaki, 2004, Plant acetyl-CoA carboxylase: structure, biosynthesis, regulation, and gene manipulation for plant breeding, Bioscience, Biotechnology, and Biochemistry, 68, 1175, 10.1271/bbb.68.1175

Li, 2011, Reverse-genetic analysis of the two biotin-containing subunit genes of the heteromeric acetyl-coenzyme A carboxylase in Arabidopsis indicates a unidirectional functional redundancy, Plant Physiology, 155, 293, 10.1104/pp.110.165910

Roesler, 1994, Structure and expression of an Arabidopsis acetyl-coenzyme A carboxylase gene, Plant Physiology, 105, 611, 10.1104/pp.105.2.611

Yanai, 1995, Genomic organization of 251 kDa acetyl-CoA carboxylase genes in Arabidopsis: tandem gene duplication has made two differentially expressed isozymes, Plant and Cell Physiology, 36, 779, 10.1093/oxfordjournals.pcp.a078822

Babiychuk, 2011, Plastid gene expression and plant development require a plastidic protein of the mitochondrial transcription termination factor family, Proceedings of the National Academy of Sciences of the United States of America, 108, 6674, 10.1073/pnas.1103442108

Puyaubert, 2008, Dual targeting of Arabidopsis holocarboxylase synthetase1: a small upstream open reading frame regulates translation initiation and protein targeting, Plant Physiology, 146, 478, 10.1104/pp.107.111534

Fatland, 2005, Reverse genetic characterization of cytosolic acetyl-CoA generation by ATP-citrate lyase in Arabidopsis, Plant Cell, 17, 182, 10.1105/tpc.104.026211

Baud, 2004, gurke and pasticcino3 mutants affected in embryo development are impaired in acetyl-CoA carboxylase, EMBO Reports, 5, 515, 10.1038/sj.embor.7400124

Amid, 2012, The sensitive to freezing3 mutation of Arabidopsis thaliana is a cold-sensitive allele of homomeric acetyl-CoA carboxylase that results in cold-induced cuticle deficiencies, Journal of Experimental Botany, 63, 5289, 10.1093/jxb/ers191

Lu, 2011, The glossyhead1 allele of ACC1 reveals a principal role for multidomain acetyl-coenzyme A carboxylase in the biosynthesis of cuticular waxes by Arabidopsis, Plant Physiology, 157, 1079, 10.1104/pp.111.185132

White, 1998, Physiological and biochemical consequences of down regulation, using antisense, of the high molecular weight form of acetyl CoA carboxylase in Brassica napus, 63

Baud, 2003, Multifunctional acetyl-CoA carboxylase 1 is essential for very long chain fatty acid elongation and embryo development in Arabidopsis, Plant Journal, 33, 75, 10.1046/j.1365-313X.2003.016010.x

Ebel, 1977, Enzymes of flavone and flavonol-glycoside biosynthesis. Coordinated and selective induction in cell-suspension cultures of Petroselinum hortense, European Journal of Biochemistry, 75, 201, 10.1111/j.1432-1033.1977.tb11518.x

Shorrosh, 1994, Molecular cloning, characterization, and elicitation of acetyl-CoA carboxylase from alfalfa, Proceedings of the National Academy of Sciences of the United States of America, 91, 4323, 10.1073/pnas.91.10.4323

Kusano, 2011, Metabolomics reveals comprehensive reprogramming involving two independent metabolic responses of Arabidopsis to UV-B light, Plant Journal, 67, 354, 10.1111/j.1365-313X.2011.04599.x

Konishi, 1996, Induction of cytosolic acetyl-coenzyme A carboxylase in pea leaves by ultraviolet-B irradiation, Plant and Cell Physiology, 37, 1197, 10.1093/oxfordjournals.pcp.a029073

Austin, 2003, The chalcone synthase superfamily of type III polyketide synthases, Natural Product Reports, 20, 79, 10.1039/b100917f

Shirley, 1995, Analysis of Arabidopsis mutants deficient in flavonoid biosynthesis, Plant Journal, 8, 659, 10.1046/j.1365-313X.1995.08050659.x

Kim, 2010, LAP6/POLYKETIDE SYNTHASE A and LAP5/POLYKETIDE SYNTHASE B encode hydroxyalkyl alpha-pyrone synthases required for pollen development and sporopollenin biosynthesis in Arabidopsis thaliana, Plant Cell, 22, 4045, 10.1105/tpc.110.080028

Dobritsa, 2010, LAP5 and LAP6 encode anther-specific proteins with similarity to chalcone synthase essential for pollen exine development in Arabidopsis, Plant Physiology, 153, 937, 10.1104/pp.110.157446

Ngaki, 2012, Evolution of the chalcone-isomerase fold from fatty-acid binding to stereospecific catalysis, Nature, 485, 530, 10.1038/nature11009

Pelletier, 1996, Analysis of flavanone 3-hydroxylase in Arabidopsis seedlings – coordinate regulation with chalcone synthase and chalcone isomerase, Plant Physiology, 111, 339, 10.1104/pp.111.1.339

Owens, 2008, Biochemical and genetic characterization of Arabidopsis flavanone 3β-hydroxylase, Plant Physiology and Biochemistry, 46, 833, 10.1016/j.plaphy.2008.06.004

Schoenbohm, 2000, Identification of the Arabidopsis thaliana flavonoid 3′-hydroxylase gene and functional expression of the encoded P450 enzyme, Biological Chemistry, 381, 749, 10.1515/BC.2000.095

Pelletier, 1997, Characterization of flavonol synthase and leucoanthocyanidin dioxygenase genes in Arabidopsis – further evidence for differential regulation of ‘early’ and ‘late’ genes, Plant Physiology, 113, 1437, 10.1104/pp.113.4.1437

Prescott, 2002, In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana, Phytochemistry, 60, 589, 10.1016/S0031-9422(02)00155-3

Wisman, 1998, Knock-out mutants from an En-1 mutagenized Arabidopsis thaliana population generate phenylpropanoid biosynthesis phenotypes, Proceedings of the National Academy of Sciences of the United States of America, 95, 12432, 10.1073/pnas.95.21.12432

Owens, 2008, Functional analysis of a predicted flavonol synthase gene family in Arabidopsis, Plant Physiology, 147, 1046, 10.1104/pp.108.117457

Stracke, 2009, Metabolomic and genetic analyses of flavonol synthesis in <i>Arabidopsis thaliana support the in vivo involvement of leucoanthocyanidin dioxygenase, Planta, 229, 427, 10.1007/s00425-008-0841-y

Preuß, 2009, Arabidopsis thaliana expresses a second functional flavonol synthase, FEBS Letters, 583, 1981, 10.1016/j.febslet.2009.05.006

Shirley, 1992, Effects of ionizing-radiation on a plant genome – analysis of 2 Arabidopsis transparent-testa mutations, Plant Cell, 4, 333

Bowerman, 2012, Analysis of T-DNA alleles of flavonoid biosynthesis genes in Arabidopsis ecotype Columbia, BMC Research Notes, 5, 485, 10.1186/1756-0500-5-485

Abrahams, 2003, The Arabidopsis TDS4 gene encodes leucoanthocyanidin dioxygenase (LDOX) and is essential for proanthocyanidin synthesis and vacuole development, Plant Journal, 35, 624, 10.1046/j.1365-313X.2003.01834.x

Nakajima, 2001, Reaction mechanism from leucoanthocyanidin to anthocyanidin 3-glucoside, a key reaction for coloring in anthocyanin biosynthesis, Journal of Biological Chemistry, 276, 25797, 10.1074/jbc.M100744200

Welford, 2001, Evidence for oxidation at C-3 of the flavonoid C-ring during anthocyanin biosynthesis, Chemical Communications (Cambridge), 1828, 10.1039/b105576n

Saito, 1999, Direct evidence for anthocyanidin synthase as a 2-oxoglutarate-dependent oxygenase: molecular cloning and functional expression of cDNA from a red forma of Perilla frutescens, Plant Journal, 17, 181, 10.1046/j.1365-313X.1999.00365.x

Martens, 2010, Multifunctional flavonoid dioxygenases: flavonol and anthocyanin biosynthesis in Arabidopsis thaliana L, Phytochemistry, 71, 1040, 10.1016/j.phytochem.2010.04.016

Nakajima, 2006, Mechanistic study on the oxidation of anthocyanidin synthase by quantum mechanical calculation, Journal of Biological Chemistry, 281, 21387, 10.1074/jbc.M600303200

Devic, 1999, The BANYULS gene encodes a DFR-like protein and is a marker of early seed coat development, Plant Journal, 19, 387, 10.1046/j.1365-313X.1999.00529.x

Xie, 2004, Anthocyanidin reductases from Medicago truncatula and Arabidopsis thaliana, Archives of Biochemistry and Biophysics, 422, 91, 10.1016/j.abb.2003.12.011

Xie, 2003, Role of anthocyanidin reductase, encoded by BANYULS in plant flavonoid biosynthesis, Science, 299, 396, 10.1126/science.1078540

Bogs, 2005, Proanthocyanidin synthesis and expression of genes encoding leucoanthocyanidin reductase and anthocyanidin reductase in developing grape berries and grapevine leaves, Plant Physiology, 139, 652, 10.1104/pp.105.064238

Yuan, 2012, Molecular cloning and characterization of PtrLAR3, a gene encoding leucoanthocyanidin reductase from Populus trichocarpa, and its constitutive expression enhances fungal resistance in transgenic plants, Journal of Experimental Botany, 63, 2513, 10.1093/jxb/err425

Pourcel, 2005, TRANSPARENT TESTA10 encodes a laccase-like enzyme involved in oxidative polymerization of flavonoids in Arabidopsis seed coat, Plant Cell, 17, 2966, 10.1105/tpc.105.035154

Pourcel, 2007, Flavonoid oxidation in plants: from biochemical properties to physiological functions, Trends in Plant Science, 12, 29, 10.1016/j.tplants.2006.11.006

Li, 2001, Phylogenetic analysis of the UDP-glycosyltransferase multigene family of Arabidopsis thaliana, Journal of Biological Chemistry, 276, 4338, 10.1074/jbc.M007447200

D'Auria, 2005, The secondary metabolism of Arabidopsis thaliana: growing like a weed, Current Opinion in Plant Biology, 8, 308, 10.1016/j.pbi.2005.03.012

Jones, 2003, UGT73C6 and UGT78D1, glycosyltransferases involved in flavonol glycoside biosynthesis in Arabidopsis thaliana, Journal of Biological Chemistry, 278, 43910, 10.1074/jbc.M303523200

Yonekura-Sakakibara, 2007, Identification of a flavonol 7-O-rhamnosyltransferase gene determining flavonoid pattern in Arabidopsis by transcriptome coexpression analysis and reverse genetics, Journal of Biological Chemistry, 282, 14932, 10.1074/jbc.M611498200

Yonekura-Sakakibara, 2012, Two glycosyltransferases involved in anthocyanin modification delineated by transcriptome independent component analysis in Arabidopsis thaliana, Plant Journal, 69, 154, 10.1111/j.1365-313X.2011.04779.x

Matsuba, 2010, A novel glucosylation reaction on anthocyanins catalyzed by acyl-glucose-dependent glucosyltransferase in the petals of carnation and delphinium, Plant Cell, 22, 3374, 10.1105/tpc.110.077487

Miyahara, 2012, Isolation of an acyl-glucose-dependent anthocyanin 7-O-glucosyltransferase from the monocot Agapanthus africanus, Journal of Plant Physiology, 169, 1321, 10.1016/j.jplph.2012.05.004

T. Miyahara, R. Sakiyama, Y. Ozeki, N. Sasaki, Acyl-glucose-dependent glucosyltransferase catalyzes the final step of anthocyanin formation in Arabidopsis, Journal of Plant Physiology, in press.

Yonekura-Sakakibara, 2008, Modification and stabilization of anthocyanins, 169

D'Auria, 2007, Identification and characterization of the BAHD acyltransferase malonyl CoA: anthocyanidin 5-O-glucoside-6′-O-malonyltransferase (At5MAT) in Arabidopsis thaliana, FEBS Letters, 581, 872, 10.1016/j.febslet.2007.01.060

Muzac, 2000, Functional expression of an Arabidopsis cDNA clone encoding a flavonol 3′-O-methyltransferase and characterization of the gene product, Archives of Biochemistry and Biophysics, 375, 385, 10.1006/abbi.1999.1681

Goujon, 2003, A new Arabidopsis thaliana mutant deficient in the expression of O-methyltransferase impacts lignins and sinapoyl esters, Plant Molecular Biology, 51, 973, 10.1023/A:1023022825098

St-Pierre, 2000, Chapter nine evolution of acyltransferase genes: origin and diversification fo the BAHD superfamily of acyltransferases involved in secondary metabolism, 285, 10.1016/S0079-9920(00)80010-6

Milkowski, 2004, Serine carboxypeptidase-like acyltransferases, Phytochemistry, 65, 517, 10.1016/j.phytochem.2003.12.018

Luo, 2007, Convergent evolution in the BAHD family of acyl transferases: identification and characterization of anthocyanin acyl transferases from Arabidopsis thaliana, Plant Journal, 50, 678, 10.1111/j.1365-313X.2007.03079.x

Fraser, 2007, Related Arabidopsis serine carboxypeptidase-like sinapoylglucose acyltransferases display distinct but overlapping substrate specificities, Plant Physiology, 144, 1986, 10.1104/pp.107.098970

Kubo, 2007, Anthocyaninless1 gene of Arabidopsis thaliana encodes a UDP-glucose:flavonoid-3-O-glucosyltransferase, Journal of Plant Research, 120, 445, 10.1007/s10265-006-0067-7

Yamazaki, 2002, Two flavonoid glucosyltransferases from Petunia hybrida: molecular cloning, biochemical properties and developmentally regulated expression, Plant Molecular Biology, 48, 401, 10.1023/A:1014043214943

Yamazaki, 1999, Molecular cloning and biochemical characterization of a novel anthocyanin 5-O-glucosyltransferase by mRNA differential display for plant forms regarding anthocyanin, Journal of Biological Chemistry, 274, 7405, 10.1074/jbc.274.11.7405

Lim, 2001, Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis, Journal of Biological Chemistry, 276, 4344, 10.1074/jbc.M007263200

Morita, 2005, Plant Journal, 42, 353, 10.1111/j.1365-313X.2005.02383.x

Sawada, 2005, UDP-glucuronic acid:anthocyanin glucuronosyltransferase from red daisy (Bellis perennis) flowers. Enzymology and phylogenetics of a novel glucuronosyltransferase involved in flower pigment biosynthesis, Journal of Biological Chemistry, 280, 899, 10.1074/jbc.M410537200

Usadel, 2004, RHM2 is involved in mucilage pectin synthesis and is required for the development of the seed coat in Arabidopsis, Plant Physiology, 134, 286, 10.1104/pp.103.034314

Western, 2004, MUCILAGE-MODIFIED4 encodes a putative pectin biosynthetic enzyme developmentally regulated by APETALA2, TRANSPARENT TESTA GLABRA1, and GLABRA2 in the Arabidopsis seed coat, Plant Physiology, 134, 296, 10.1104/pp.103.035519

Oka, 2007, Functional analysis of Arabidopsis thaliana RHM2/MUM4, a multidomain protein involved in UDP-D-glucose to UDP-L-rhamnose conversion, Journal of Biological Chemistry, 282, 5389, 10.1074/jbc.M610196200

Shikazono, 2001, Rearrangements of the DNA in carbon ion-induced mutants of Arabidopsis thaliana, Genetics, 157, 379, 10.1093/genetics/157.1.379

Kitamura, 2004, TRANSPARENT TESTA 19 is involved in the accumulation of both anthocyanins and proanthocyanidins in Arabidopsis, Plant Journal, 37, 104, 10.1046/j.1365-313X.2003.01943.x

Zhao, 2010, The mysteries of proanthocyanidin transport and polymerization, Plant Physiology, 153, 437, 10.1104/pp.110.155432

Debeaujon, 2001, The TRANSPARENT TESTA12 gene of Arabidopsis encodes a multidrug secondary transporter-like protein required for flavonoid sequestration in vacuoles of the seed coat endothelium, Plant Cell, 13, 853, 10.1105/tpc.13.4.853

Marinova, 2007, The Arabidopsis MATE transporter TT12 acts as a vacuolar flavonoid/H+-antiporter active in proanthocyanidin-accumulating cells of the seed coat, Plant Cell, 19, 2023, 10.1105/tpc.106.046029

Thompson, 2010, An Arabidopsis flavonoid transporter is required for anther dehiscence and pollen development, Journal of Experimental Botany, 61, 439, 10.1093/jxb/erp312

Marrs, 1995, A glutathione-s-transferase involved in vacuolar transfer encoded by the maize gene bronze-2, Nature, 375, 397, 10.1038/375397a0

Wangwattana, 2008, Characterization of PAP1-upregulated Glutathione S-transferase genes in Arabidopsis thaliana, Plant Biotechnology, 25, 191, 10.5511/plantbiotechnology.25.191

Alfenito, 1998, Functional complementation of anthocyanin sequestration in the vacuole by widely divergent glutathione S-transferases, Plant Cell, 10, 1135, 10.1105/tpc.10.7.1135

Loyall, 2000, Glutathione and a UV light-induced glutathione S-transferase are involved in signaling to chalcone synthase in cell cultures, Plant Cell, 12, 1939

Mueller, 2000, AN9, a petunia glutathione S-transferase required for anthocyanin sequestration, is a flavonoid-binding protein, Plant Physiology, 123, 1561, 10.1104/pp.123.4.1561

Kitamura, 2012, Molecular characterization of an anthocyanin-related glutathione S-transferase gene in cyclamen, Journal of Plant Physiology, 169, 636, 10.1016/j.jplph.2011.12.011

Kitamura, 2008, Transport of flavonoids, 123

Smith, 2003, Arabidopsis AtGSTF2 is regulated by ethylene and auxin, and encodes a glutathione S-transferase that interacts with flavonoids, Plant Journal, 36, 433, 10.1046/j.1365-313X.2003.01890.x

Zhao, 2009, MATE transporters facilitate vacuolar uptake of epicatechin 3′-O-Glucoside for proanthocyanidin biosynthesis in Medicago truncatula and Arabidopsis, Plant Cell, 21, 2323, 10.1105/tpc.109.067819

Sun, 2012, Arabidopsis TT19 functions as a carrier to transport anthocyanin from the cytosol to tonoplasts, Molecular Plant, 5, 387, 10.1093/mp/ssr110

Baxter, 2005, A plasma membrane H+-ATPase is required for the formation of proanthocyanidins in the seed coat endothelium of Arabidopsis thaliana, Proceedings of the National Academy of Sciences of the United States of America, 102, 2649, 10.1073/pnas.0406377102

Yonekura-Sakakibara, 2013, Transcriptome data modeling toward plant metabolic engineering, Current Opinion in Biotechnology, 10.1016/j.copbio.2012.10.018

R.A. Dixon, C. Liu, J.H. Jun, Metabolic engineering of anthocyanins and condensed tannins in plants, Current Opinion in Biotechnology, in press.

A. Bar-Even, D. Salah Tawfik, Engineering specialized metabolic pathways-is there a room for enzyme improvements?, Current Opinion in Biotechnology, in press.

Yamazaki, 2011, Molecular genetic study on the anthocyanin chemotypes of Perilla frutescens var. crispa, Natural Product Communications, 6, 423, 10.1177/1934578X1100600322

Saito, 2002, Biochemistry and molecular biology of the late-stage of biosynthesis of anthocyanin: lessons from Perilla frutescens as a model plant, New Phytologist, 155, 9, 10.1046/j.1469-8137.2002.00440.x

Yonekura-Sakakibara, 2009, Functional genomics for plant natural product biosynthesis, Natural Product Reports, 26, 1466, 10.1039/b817077k

Yonekura-Sakakibara, 2006, Review: genetically modified plants for the promotion of human health, Biotechnology Letters, 28, 1983, 10.1007/s10529-006-9194-4

Butelli, 2008, Enrichment of tomato fruit with health-promoting anthocyanins by expression of select transcription factors, Nature Biotechnology, 26, 1301, 10.1038/nbt.1506

R. Nakabayashi, K. Saito, Metabolomics for unknown plant metabolites, Analytical and Bioanalytical Chemistry, in press.

Oikawa, 2012, Metabolite analyses of single cells, Plant Journal, 70, 30, 10.1111/j.1365-313X.2012.04967.x

De Luca, 2012, Mining the biodiversity of plants: a revolution in the making, Science, 336, 1658, 10.1126/science.1217410