|
Adams PD, Afonine PV, Bunkoczi G, Chen VB, Davis IW, Echols N, Headd JJ, Hung LW, Kapral GJ, Grosse-Kunstleve RW, McCoy AJ, Moriarty NW, Oeffner R, Read RJ, Richardson DC, Richardson JS, Terwilliger TC, Zwart PH (2010) PHENIX: a comprehensive Python-based system for macromolecular structure solution. Acta Crystallogr D Biol Crystallogr 66 (Pt 2):213-221. Afonine PV, Grosse-Kunstleve RW, Echols N, Headd JJ, Moriarty NW, Mustyakimov M, Terwilliger TC, Urzhumtsev A, Zwart PH, Adams PD (2012) Towards automated crystallographic structure refinement with phenix.refine. cta Crystallogr D Biol Crystallogr 68 (Pt 4):352-367. Afonine PV, Moriarty NW, Mustyakimov M, Sobolev OV, Terwilliger TC, Turk D, Urzhumtsev A, Adams PD (2015) FEM: feature-enhanced map. Acta Crystallogr D Biol Crystallogr 71 (Pt 3):646-666. Babos M, Halasz K, Zagyva T, Zold-Balogh A, Szego D, Bratek Z (2011) Preliminary notes on dual relevance of ITS sequences and pigments in Hygrocybe taxonomy. Persoonia 26:99-107. Brockington SF, Walker RH, Glover BJ, Soltis PS, Soltis DE (2011) Complex pigment evolution in the Caryophyllales. New Phytol 190 (4):854-864 Canovas FG, Garcia-Carmona F, Sanchez JV, Pastor JL, Teruel JA (1982) The role of pH in the melanin biosynthesis pathway. J Biol Chem 257 (15):8738-8744 Christinet L, Burdet FRX, Zaiko M, Hinz U, Zryd JP (2004) Characterization and functional identification of a novel plant 4,5-extradiol dioxygenase involved in betalain pigment biosynthesis in Portulaca grandiflora. Plant Physiol 134 (1):265-274. Dunwell JM, Culham A, Carter CE, Sosa-Aguirre CR, Goodenough PW (2001) Evolution of functional diversity in the cupin superfamily. Trends in Biochem Sci 26 (12):740-746. Eltis LD, Bolin JT (1996) Evolutionary relationships among extradiol dioxygenases. J Bacteriol 178 (20):5930-5937. Emsley P, Cowtan K (2004) Coot: model-building tools for molecular graphics. Acta Crystallogr D Biol Crystallogr 60 (Pt 12 Pt 1):2126-2132. Gandia-Herrero F (2005) Betaxanthins as Substrates for Tyrosinase. An Approach to the Role of Tyrosinase in the Biosynthetic Pathway of Betalains. Plant Physiol 138 (1):421-432. Gandía-Herrero F, Escribano J, García-Carmona F (2007) Characterization of the Activity of Tyrosinase on Betanidin. J Agric Food Chem 55 (4):1546-1551. Gandia-Herrero F, Escribano J, Garcia-Carmona F (2010) Structural implications on color, fluorescence, and antiradical activity in betalains. Planta 232 (2):449-460. Gandia-Herrero F, Escribano J, Garcia-Carmona F (2012) Purification and antiradical properties of the structural unit of betalains. J Nat Prod 75 (6):1030-1036. Gandia-Herrero F, Garcia-Carmona F (2012) Characterization of recombinant Beta vulgaris 4,5-DOPA-extradiol-dioxygenase active in the biosynthesis of betalains. Planta 236 (1):91-100. Gandia-Herrero F, Garcia-Carmona F (2013) Biosynthesis of betalains: yellow and violet plant pigments. Trends Plant Sci 18 (6):334-343. Gandia-Herrero F, Garcia-Carmona F (2014) Escherichia coli protein YgiD produces the structural unit of plant pigments betalains: characterization of a prokaryotic enzyme with DOPA-extradiol-dioxygenase activity. Appl Microbiol Biotechnol 98 (3):1165-1174. Gandia-Herrero F, Garcia-Carmona F, Escribano J (2005) Botany: floral fluorescence effect. Nature 437 (7057):334. Girod P-A, Zryd J-P (1991) Biogenesis of betalains: Purification and partial characterization of dopa 4,5-dioxygenase from Amanita muscaria. Phytochemistry 30 (1):169-174. Godoy-Alcántar C, Yatsimirsky AK, Lehn JM (2005) Structure-stability correlations for imine formation in aqueous solution. J Phys Org Chem 18 (10):979-985. Green BR, Durnford DG (1996) The Chlorophyll-Carotenoid Proteins of Oxygenic Photosynthesis. Annu Rev Plant Physiol Plant Mol Biol 47:685-714. Groce SL, Lipscomb JD (2003) Conversion of extradiol aromatic ring-cleaving homoprotocatechuate 2,3-dioxygenase into an intradiol cleaving enzyme. J Am Chem Soc 125 (39):11780-11781. Guengerich FP (2001) Common and Uncommon Cytochrome P450 Reactions Related to Metabolism and Chemical Toxicity. Chem Res Toxicol 14 (6):611-650. Hans J, Brandt W, Vogt T (2004) Site-directed mutagenesis and protein 3D-homology modelling suggest a catalytic mechanism for UDP-glucose-dependent betanidin 5-O-glucosyltransferase from Dorotheanthus bellidiformis. Plant J 39 (3):319-333. Hatlestad GJ, Sunnadeniya RM, Akhavan NA, Gonzalez A, Goldman IL, McGrath JM, Lloyd AM (2012) The beet R locus encodes a new cytochrome P450 required for red betalain production. Nat Genet 44 (7):816-820. Hinz UG, Fivaz J, Girod PA, Zyrd JP (1997) The gene coding for the DOPA dioxygenase involved in betalain biosynthesis in Amanita muscaria and its regulation. Mol Gen Genet 256 (1):1-6 Holm L, Rosenstrom P (2010) Dali server: conservation mapping in 3D. Nucleic Acids Res 38 (Web Server issue):W545-549. Jouanneau Y (2010) Oxidative Inactivation of Ring-Cleavage Extradiol Dioxygenases: Mechanism and Ferredoxin-Mediated Reactivation.1071-1079. Kishima Y, Suiko M, Adachi T (1991) Betalain Pigmentation in Petal of Portulaca is Preceded by a Dramatic Tyrosine Accumulation. J Plant Physiol 137 (4):505-506. Koehntop KD, Emerson JP, Que L, Jr. (2005) The 2-His-1-carboxylate facial triad: a versatile platform for dioxygen activation by mononuclear non-heme iron(II) enzymes. J Biol Inorg Chem 10 (2):87-93. Kovaleva EG, Lipscomb JD (2007) Crystal structures of Fe2+ dioxygenase superoxo, alkylperoxo, and bound product intermediates. Science 316 (5823):453-457. Land EJ, Riley PA (2000) Spontaneous Redox Reactions of Dopaquinone and the Balance between the Eumelanic and Phaeomelanic Pathways. Pigment Cell Res 13 (4):273-277. Laskowski RA, Rullmannn JA, MacArthur MW, Kaptein R, Thornton JM (1996) AQUA and PROCHECK-NMR: programs for checking the quality of protein structures solved by NMR. J Biomol NMR 8 (4):477-486 Lechner JF, Wang LS, Rocha CM, Larue B, Henry C, McIntyre CM, Riedl KM, Schwartz SJ, Stoner GD (2010) Drinking water with red beetroot food color antagonizes esophageal carcinogenesis in N-nitrosomethylbenzylamine-treated rats. J Med Food 13 (3):733-739. Li J, Christensen BM (1993) Identification of Products and Intermediates During L-Dopa Oxidation to Dopachrome Using High Pressure Liquid Chromatography with Electrochemical Detection. J Liq Chromatogr 16 (5):1117-1133. Lin G, Reid G, Bugg TD (2001) Extradiol oxidative cleavage of catechols by ferrous and ferric complexes of 1,4,7-triazacyclononane: insight into the mechanism of the extradiol catechol dioxygenases. J Am Chem Soc 123 (21):5030-5039 Lu X, Wang Y, Zhang Z (2009) Radioprotective activity of betalains from red beets in mice exposed to gamma irradiation. Eur J Pharmacol 615 (1-3):223-227. McCoy AJ, Grosse-Kunstleve RW, Adams PD, Winn MD, Storoni LC, Read RJ (2007) Phaser crystallographic software. J Appl Crystallogr 40 (Pt 4):658-674. Mueller LA, Hinz U, Zryd JP (1997) The formation of betalamic acid and muscaflavin by recombinant dopa-dioxygenase from Amanita. Phytochemistry 44 (4):567-569. Nambara E, Marion-Poll A (2005) Abscisic acid biosynthesis and catabolism. Annu Rev Plant Biol 56:165-185. Niyogi KK (2000) Safety valves for photosynthesis. Curr Opin Plant Biol 3 (6):455-460 Riley PA (2000) Tyrosinase Kinetics: A Semi-quantitative Model of the Mechanism of Oxidation of Monohydric and Dihydric Phenolic Substrates. J Theor Biol 203 (1):1-12. Sasaki N (2005) Isolation and Characterization of cDNAs Encoding an Enzyme with Glucosyltransferase Activity for cyclo-DOPA from Four O''clocks and Feather Cockscombs. Plant Cell Physiol 46 (4):666-670. Sasaki N, Abe Y, Goda Y, Adachi T, Kasahara K, Ozeki Y (2009) Detection of DOPA 4,5-dioxygenase (DOD) activity using recombinant protein prepared from Escherichia coli cells harboring cDNA encoding DOD from Mirabilis jalapa. Plant Cell Physiol 50 (5):1012-1016. Schliemann W, Kobayashi N, Strack D (1999) The Decisive Step in Betaxanthin Biosynthesis Is a Spontaneous Reaction1. Plant Physiol 119 (4):1217-1232. Schliemann W, Steiner U, Strack D (1998) Betanidin formation from dihydroxyphenylalanine in a model assay system. Phytochemistry 49 (6):1593-1598 Sekiguchi H, Ozeki Y, Sasaki N (2010) In vitro synthesis of betaxanthins using recombinant DOPA 4,5-dioxygenase and evaluation of their radical-scavenging activities. J Agric Food Chem 58 (23):12504-12509. Shimada S, Otsuki H, Sakuta M (2007) Transcriptional control of anthocyanin biosynthetic genes in the Caryophyllales. J Exp Bot 58 (5):957-967. Shu L, Chiou YM, Orville AM, Miller MA, Lipscomb JD, Que L, Jr. (1995) X-ray absorption spectroscopic studies of the Fe(II) active site of catechol 2,3-dioxygenase. Implications for the extradiol cleavage mechanism. Biochemistry 34 (20):6649-6659 Sreekanth D, Arunasree MK, Roy KR, Chandramohan Reddy T, Reddy GV, Reddanna P (2007) Betanin a betacyanin pigment purified from fruits of Opuntia ficus-indica induces apoptosis in human chronic myeloid leukemia Cell line-K562. Phytomedicine 14 (11):739-746. Stintzing F, Schliemann W (2007) Pigments of fly agaric (Amanita muscaria). Z Naturforsch C 62 (11-12):779-785 Stintzing FC, Schieber A, Carle R (2002) Betacyanins in fruits from red-purple pitaya, Hylocereus polyrhizus (Weber) Britton & Rose. Food Chem 77 (1):101-106. Strack D, Vogt T, Schliemann W (2003) Recent advances in betalain research. Phytochemistry 62 (3):247-269. Sugimoto K, Senda M, Kasai D, Fukuda M, Masai E, Senda T (2014) Molecular mechanism of strict substrate specificity of an extradiol dioxygenase, DesB, derived from Sphingobium sp. SYK-6. PLoS One 9 (3):e92249. Sugimoto K, Senda T, Aoshima H, Masai E, Fukuda M, Mitsui Y (1999) Crystal structure of an aromatic ring opening dioxygenase LigAB, a protocatechuate 4,5-dioxygenase, under aerobic conditions. Structure 7 (8):953-965 Tanaka Y, Sasaki N, Ohmiya A (2008) Biosynthesis of plant pigments: anthocyanins, betalains and carotenoids. Plant J 54 (4):733-749. Toivonen PMA, Brummell DA (2008) Biochemical bases of appearance and texture changes in fresh-cut fruit and vegetables. Postharvest Biol Technol 48 (1):1-14. Trezzini GF, Zrÿb JP (1991) Characterization of some natural and semi-synthetic betaxanthins. Phytochemistry 30 (6):1901-1903. Vaillancourt FH, Barbosa CJ, Spiro TG, Bolin JT, Blades MW, Turner RF, Eltis LD (2002) Definitive evidence for monoanionic binding of 2,3-dihydroxybiphenyl to 2,3-dihydroxybiphenyl 1,2-dioxygenase from UV resonance Raman spectroscopy, UV/Vis absorption spectroscopy, and crystallography. J Am Chem Soc 124 (11):2485-2496 Vaillancourt FH, Bolin JT, Eltis LD (2006) The ins and outs of ring-cleaving dioxygenases. Crit Rev Biochem Mol Biol 41 (4):241-267. Wyler H, Chiovini J (1968) Die Synthese von Cyclodopa (Leukodopachrom). Helvetica Chimica Acta 51 (6):1476-1494.
|