Arabidopsis thaliana β-glucosidase BGLU15 attacks flavonol 3-O-β-glucoside-7-O-α-rhamnosides

Agati, 2012, Flavonoids as antioxidants in plants: location and functional significance, Plant Sci., 196, 67, 10.1016/j.plantsci.2012.07.014 Ahn, 2010, Scopolin-hydrolyzing β-glucosidases in roots of Arabidopsis, Plant Cell Physiol., 51, 132, 10.1093/pcp/pcp174 Andersson, 2009, Myrosinases from root and leaves of Arabidopsis thaliana have different catalytic properties, Phytochemistry, 70, 1345, 10.1016/j.phytochem.2009.07.036 Andréasson, 2001, Different myrosinase and idioblast distribution in Arabidopsis and Brassica napus, Plant Physiol., 127, 1750, 10.1104/pp.010334 Arnau, 2006, Current strategies for the use of affinity tags and tag removal for the purification of recombinant proteins, Protein Expr. Purif., 48, 1, 10.1016/j.pep.2005.12.002 Barrett, 1995, The crystal structure of a cyanogenic β-glucosidase from white clover, a family 1 glycosyl hydrolase, Structure, 3, 951, 10.1016/S0969-2126(01)00229-5 Baumgertel, 2003, Purification and characterization of a flavonol 3-O-β-heterodisaccharidase from the dried herb of Fagopyrum esculentum Moench, Phytochemistry, 64, 411, 10.1016/S0031-9422(03)00418-7 Borderies, 2003, Proteomics of loosely bound cell wall proteins of Arabidopsis thaliana cell suspension cultures: a critical analysis, Electrophoresis, 24, 3421, 10.1002/elps.200305608 Bozzo, 2006, Differential synthesis of phosphate-starvation inducible purple acid phosphatase isozymes in tomato (Lycopersicon esculentum) suspension cells and seedlings, Plant Cell Environ., 29, 303, 10.1111/j.1365-3040.2005.01422.x Bradford, 1976, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein–dye binding, Anal. Biochem., 72, 248, 10.1016/0003-2697(76)90527-3 Buer, 2010, Flavonoids: new roles for old molecules, J. Integr. Plant Biol., 52, 98, 10.1111/j.1744-7909.2010.00905.x Chapelle, 2012, Impact of the absence of stem-specific β-glucosidases on lignin and monolignols, Plant Physiol., 160, 1204, 10.1104/pp.112.203364 Coronado, 1995, Alfalfa root flavonoid production is nitrogen regulated, Plant Physiol., 108, 533, 10.1104/pp.108.2.533 Dharmawardhana, 1999, cDNA cloning and heterologous expression of coniferin β-glucosidase, Plant Mol. Biol., 40, 365, 10.1023/A:1006226931512 DuPont, 2000, Effect of variety, processing, and storage on the flavonoid glycoside content and composition of lettuce and endive, J. Agric. Food Chem., 48, 3957, 10.1021/jf0002387 Escamilla-Treviño, 2006, Arabidopsis thaliana β-glucosidases BGLU45 and BGLU46 hydrolyse monolignol glucosides, Phytochemistry, 67, 1651, 10.1016/j.phytochem.2006.05.022 Gerasimenko, 2002, Heterologous expression of a Rauvolfia cDNA encoding strictosidine glucosidase, a biosynthetic key to over 2000 monoterpenoid indole alkaloids, Eur. J. Biochem., 269, 2204, 10.1046/j.1432-1033.2002.02878.x Gosch, 2010, Phloridzin: biosynthesis, distribution and physiological relevance in plants, Phytochemistry, 71, 838, 10.1016/j.phytochem.2010.03.003 Harborne, 2000, Advances in flavonoid research since 1992, Phytochemistry, 55, 481, 10.1016/S0031-9422(00)00235-1 Himeno, 2013, Identification of rice β-glucosidase with high hydrolytic activity towards salicylic acid β-d-glucoside, Biosci. Biotechnol. Biochem., 77, 934, 10.1271/bbb.120889 Hösel, 1975, β-Glucosidases from Cicer arietinum L. Purification and properties of isoflavone-7-O-glucoside specific β-glucosidases, Eur. J. Biochem., 57, 607, 10.1111/j.1432-1033.1975.tb02336.x Inoue, 1996, Purification and characterization of furostanol glycoside 26-O-β-glucosidase from Costus speciosus rhizomes, FEBS Lett., 378, 157, 10.1016/0014-5793(95)01447-0 Ishiguro, 1991, A flavanonol rhamnoside from Hypericum japonicum, Phytochemistry, 30, 3152, 10.1016/S0031-9422(00)98277-3 Jones, 2003, UGT73C6 and UGT78D1, glycosyltransferases involved in flavonol glycoside biosynthesis in Arabidopsis thaliana, J. Biol. Chem., 278, 43910, 10.1074/jbc.M303523200 Ketudat Cairns, 2010, Glucosidases, Cell. Mol. Life Sci., 67, 3389, 10.1007/s00018-010-0399-2 Kim, 2014, Chemically induced conditional rescue of the Reduced Epidermal Fluorescence8 mutant of Arabidopsis reveals rapid restoration of growth and selective turnover of secondary metabolite pools, Plant Physiol., 164, 584, 10.1104/pp.113.229393 Laemmli, 1970, Cleavage of structural proteins during the assembly of the head of bacteriophage T4, Nature, 227, 680, 10.1038/227680a0 Larbat, 2012, Influence of repeated short-term nitrogen limitation on leaf phenolics metabolism in tomato, Phytochemistry, 77, 119, 10.1016/j.phytochem.2012.02.004 Larkin, 2007, Clustal W and Clustal X version 2.0, Bioinformatics, 23, 2947, 10.1093/bioinformatics/btm404 Lea, 2007, Nitrogen deficiency enhances expression of specific MYB and bHLH transcription factors and accumulation of end products in the flavonoid pathway, Planta, 225, 1245, 10.1007/s00425-006-0414-x Lee, 2006, Activation of glucosidase via stress-induced polymerization rapidly increases active pools of abscisic acid, Cell, 126, 1109, 10.1016/j.cell.2006.07.034 Lillo, 2008, Nutrient depletion as a key factor for manipulating gene expression and product formation in different branches of the flavonoid pathway, Plant Cell Environ., 31, 587, 10.1111/j.1365-3040.2007.01748.x Livak, 2001, Analysis of relative gene expression data using real-time quantitative PCR and the 2−ΔΔCT method, Methods, 25, 402, 10.1006/meth.2001.1262 Løvdal, 2010, Synergistic effects of nitrogen depletion, temperature, and light on the content of phenolic compounds and gene expression in leaves of tomato, Phytochemistry, 2010, 605, 10.1016/j.phytochem.2009.12.014 Manzanares, 2007, α-l-Rhamnosidases: old and new insights, 117 Marais, 2006, The stereochemistry of flavonoids, 1 Mizutani, 2002, Cloning of β-primeverosidase from tea leaves, a key enzyme in tea aroma formation, Plant Physiol., 130, 2164, 10.1104/pp.102.011023 Morant, 2008, β-Glucosidases as detonators of plant chemical defense, Phytochemistry, 69, 1795, 10.1016/j.phytochem.2008.03.006 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 Nakabayashi, 2014, Enhancement of oxidative and drought tolerance in Arabidopsis by overaccumulation of antioxidant flavonoids, Plant J., 77, 367, 10.1111/tpj.12388 Naoumkina, 2007, Different mechanisms for phytoalexin induction by pathogen and wound signals in Medicago truncatula, Proc. Natl. Acad. Sci. USA, 104, 17909, 10.1073/pnas.0708697104 Nomura, 2008, The new β-d-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha, J. Biol. Chem., 283, 34650, 10.1074/jbc.M806953200 Olsen, 2009, Temperature and nitrogen effects on regulators and products of the flavonoid pathway: experimental and kinetic model studies, Plant Cell Environ., 32, 286, 10.1111/j.1365-3040.2008.01920.x Opassiri, 2006, Analysis of rice glycosyl hydrolase family 1 and expression of Os4bglu12 β-glucosidase, BMC Plant Biol., 6, 33, 10.1186/1471-2229-6-33 Roepke, 2013, Biocatalytic synthesis of quercetin 3-O-glucoside-7-O-rhamnoside by metabolic engineering of Escherichia coli, ChemBioChem, 14, 2418, 10.1002/cbic.201300474 Saito, 2013, The flavonoid biosynthetic pathway in Arabidopsis: structural and genetic diversity, Plant Physiol. Biochem., 72, 21, 10.1016/j.plaphy.2013.02.001 Sambrook, 1989 Srisomsap, 1996, Isolation and characterization of an enzyme with β-d-glucosidase/β-d-fucosidase activities from Dalbergia cochinchinensis Pierre, J. Biochem., 119, 585, 10.1093/oxfordjournals.jbchem.a021282 Stewart, 2001, The effect of nitrogen and phosphorus deficiency on flavonol accumulation in plant tissues, Plant Cell Environ., 24, 1189, 10.1046/j.1365-3040.2001.00768.x Suzuki, 2005, Effect of UV-B radiation, cold and dessication stress on rutin concentration and rutin glucosidase activity in tartary buckwheat (Fagopyrum tataricum) leaves, Plant Sci., 168, 1303, 10.1016/j.plantsci.2005.01.007 Suzuki, 2006, An isoflavone conjugate-hydrolyzing β-glucosidase from the roots of soybean (Glycine max) seedlings. Purification, gene cloning, phylogenetics, and cellular localization, J. Biol. Chem., 281, 30251, 10.1074/jbc.M605726200 Svasti, 1999, Dalcochinin-8′-O-β-d-glucoside and its β-glucosidase enzyme from Dalbergia cochinchinensis, Phytochemistry, 50, 739, 10.1016/S0031-9422(98)00552-4 Takahama, 2000, Deglucosidation of quercetin glucosides to the aglycone and formation of antifungal agents by peroxidase-dependent oxidation of quercetin on browning of onion scales, Plant Cell Physiol., 41, 1021, 10.1093/pcp/pcd025 Tamura, 2013, MEGA6: molecular evolutionary genetics analysis version 6.0, Mol. Biol. Evol., 30, 2725, 10.1093/molbev/mst197 Toghe, 2005, Functional genomics by integrated analysis of metabolome and transcriptome of Arabidopsis plants over-expressing an MYB transcription factor, Plant J., 42, 218, 10.1111/j.1365-313X.2005.02371.x Tranchimand, 2010, The rutin catabolic pathway with special emphasis on quercetinase, Biodegradation, 21, 833, 10.1007/s10532-010-9359-7 Wang, 2013, Plant cell wall lignification and monolignol metabolism, Front. Plant Sci., 4, 00220, 10.3389/fpls.2013.00220 Warzecha, 2000, Molecular cloning and functional bacterial expression of a plant glucosidase specifically involved in alkaloid biosynthesis, Phytochemistry, 54, 657, 10.1016/S0031-9422(00)00175-8 Xu, 2004, Functional genomic analysis of Arabidopsis thaliana glycoside hydrolase family 1, Plant Mol. Biol., 55, 343, 10.1007/s11103-004-0790-1 Xu, 2012, A vacuolar β-glucosidase homolog that possesses glucose-conjugated abscisic acid hydrolyzing activity plays an important role in osmotic stress responses in Arabidopsis, Plant Cell, 24, 2184, 10.1105/tpc.112.095935 Yin, 2014, Kaempferol 3-O-rhamnoside-7-O-rhamnoside is an endogenous flavonol inhibitor of polar auxin transport in Arabidopsis shoots, New Phytol., 201, 466, 10.1111/nph.12558 Yonekura-Sakaibara, 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, 10.1074/jbc.M611498200 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 Zarei, 2011, Two GCC boxes and AP2/ERF-domain transcription factor ORA59 in jasmonate/ethylene-mediated activation of the PDF1.2 promoter in Arabidopsis, Plant Mol. Biol., 75, 321, 10.1007/s11103-010-9728-y Zhao, 2010, The ‘ins’ and ‘outs’ of flavonoid transport, Trends Plant Sci., 15, 72, 10.1016/j.tplants.2009.11.006 Zhou, 2012, Properties of β-thioglucoside hydrolases (TGG1 and TGG2) from leaves of Arabidopsis thaliana, Plant Sci., 191–192, 82, 10.1016/j.plantsci.2012.02.004