Characterization of an isoflavonoid-specific prenyltransferase from Lupinus albus

Plant Physiology

Volumn 159, Issue 1, 2012, Pages 70-80

  Shen, Guoan ^a   Huhman, David ^a   Lei, Zhentian ^a   Snyder, John ^a   Sumner, Lloyd W ^a   Dixon, Richard A ^a  

^a PLANT BIOLOGY DIVISION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LUPINUS ALBUS; MEDICAGO TRUNCATULA;

EID: 84860583374     PISSN: 00320889     EISSN: 15322548     Source Type: Journal    
DOI: 10.1104/pp.112.195271     Document Type: Article

References (45)

1. Akashi T, Sasaki K, Aoki T, Ayabe S, Yazaki K (2009) Molecular cloning and characterization of a cDNA for pterocarpan 4-dimethylallyltransferase catalyzing the key prenylation step in the biosynthesis of glyceollin, a soybean phytoalexin. Plant Physiol 149: 683-693
2. Bednarek P, Franski R, Kerhoas L, Einhorn J, Wojtaszek P, Stobiecki M (2001) Profiling changes in metabolism of isoflavonoids and their conjugates in Lupinus albus treated with biotic elicitor. Phytochemistry 56: 77-85
3. Biggs DR, Welle R, Grisebach H (1990) Intracellular localization of prenyltransferases of isoflavonoid phytoalexin biosynthesis in bean and soybean. Planta 181: 244-248
4. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254
5. Esnault R, Buffard D, Breda C, Sallaud C, el Turk J, Kondorosi A (1993) Pathological and molecular characterizations of alfalfa interactions with compatible and incompatible bacteria, Xanthomonas campestris pv. alfalfae and Pseudomonas syringae pv. pisi. Mol Plant Microbe Interact 6: 655-664
6. Farag MA, Huhman DV, Lei Z, Sumner LW (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: 342-354
7. Ferro M, Salvi D, Riviere-Rolland H, Vermat T, Seigneurin-Berny D, Grunwald D, Garin J, Joyard J, Rolland N (2002) Integral membrane proteins of the chloroplast envelope: identification and subcellular localization of new transporters. Proc Natl Acad Sci USA 99: 11487-11492
8. Gagnon H, Ibrahim RK (1997) Effects of various elicitors on the accumulation and secretion of isoflavonoids in white lupin. Phytochemistry 44: 1463-1467
9. 14C]L-phenylalanine and their release into the culture medium. Plant Physiol 100: 76-79
10. Gamborg OL, Miller RA, Ojima K (1968) Nutrient requirements of suspension cultures of soybean root cells. Exp Cell Res 50: 151-158
11. Gilbert GA, Knight JD, Vance CP, Allan DL (2000) Proteoid root development of phosphorus deficient lupin is mimicked by auxin and phosphonate. Ann Bot (Lond) 85: 921-928
12. Harborne JB, Ingham JL, King L, Payne M (1976) The isopentenyl isoflavone luteone as a pre-infectional antifungal agent in the genus Lupinus. Phytochemistry 15: 1485-1487
13. Hatano T, Shintani Y, Aga Y, Shiota S, Tsuchiya T, Yoshida T (2000) Phenolic constituents of licorice. VIII. Structures of glicophenone and glicoisoflavanone, and effects of licorice phenolics on methicillin-resistant Staphylococcus aureus. Chem Pharm Bull (Tokyo) 48: 1286-1292
14. Hostettmann K, Marston A, Wolfender J-L (2005) Strategy in the search for new lead compounds and drugs from plants. CHIMIA Int J Chem 59: 291-294
15. Ingham J, Tahara S, Harborne J (1983) Fungitoxic isoflavones from Lupinus albus and other Lupinus species. Z Naturforsch C 38C: 194-200
16. Ingham JL (1990) Systematic aspects of phytoalexin formation within tribe Phaseoleae of the Leguminosae (subfamily Papilionoideae). Biochem Syst Ecol 18: 329-343
17. Johnson JF, Vance CP, Allan DL (1996) Phosphorus deficiency in Lupinus albus: altered lateral root development and enhanced expression of phosphoenolpyruvate carboxylase. Plant Physiol 112: 31-41
18. Karimi M, Inzé D, Depicker A (2002) Gateway vectors for Agrobacteriummediated plant transformation. Trends Plant Sci 7: 193-195
19. Katagiri Y, Ibrahim RK, Tahara S (2000) HPLC analysis of white lupin isoflavonoids. Biosci Biotechnol Biochem 64: 1118-1125
20. Keller RK, Thompson R (1993) Rapid synthesis of isoprenoid diphosphates and their isolation in one step using either thin layer or flash chromatography. J Chromatogr A 645: 161-167
21. Koeduka T, Shitan N, Kumano T, Sasaki K, Sugiyama A, Linley P, Kawasaki T, Ezura H, Kuzuyama T, Yazaki K (2011) Production of prenylated flavonoids in tomato fruits expressing a prenyltransferase gene from Streptomyces coelicolor A3(2). Plant Biol (Stuttg) 13: 411-415
22. Laflamme P, Khouri H, Gulick P, Ibrahim R (1993) Enzymatic prenylation of isoflavones in white lupin. Phytochemistry 34: 147-151
23. Limpens E, Ramos J, Franken C, Raz V, Compaan B, Franssen H, Bisseling T, Geurts R (2004) RNA interference in Agrobacterium rhizogenes-transformed roots of Arabidopsis and Medicago truncatula. J Exp Bot 55: 983-992
24. Liu CJ, Dixon RA (2001) Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents the formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis. Plant Cell 13: 2643-2658
25. Liu CJ, Huhman D, Sumner LW, Dixon RA (2003) Regiospecific hydroxylation of isoflavones by cytochrome p450 81E enzymes from Medicago truncatula. Plant J 36: 471-484
26. Máximo P, Lourenço A, Feio SS, Roseiro JC (2002) Flavonoids from Ulex airensis and Ulex europaeus ssp. europaeus. J Nat Prod 65: 175-178
27. Pang Y, Peel GJ, Sharma SB, Tang Y, Dixon RA (2008) A transcript profiling approach reveals an epicatechin-specific glucosyltransferase expressed in the seed coat of Medicago truncatula. Proc Natl Acad Sci USA 105: 14210-14215
28. Pang Y, Peel GJ, Wright E, Wang Z, Dixon RA (2007) Early steps in proanthocyanidin biosynthesis in the model legume Medicago truncatula. Plant Physiol 145: 601-615
29. Pennypacker BW, Knievel DP, Leath KT, Pell EJ, Hill RRJ (1990) Analysis of photosynthesis in resistant and susceptible alfalfa clones infected with Verticillium albo-atrum. Phytopathology 80: 1300-1306
30. Pompon D, Louerat B, Bronine A, Urban P (1996) Yeast expression of animal and plant P450s in optimized redox environments. Methods Enzymol 272: 51-64
31. Porto MDM, Grau CR, de Zoeten GA, Gaard G (1988) Histopathology of Colletotrichum trifolii on alfalfa. Phytopathology 78: 345-349
32. Queiroz EF, Wolfender JL, Atindehou KK, Traore D, Hostettmann K (2002) On-line identification of the antifungal constituents of Erythrina vogelii by liquid chromatography with tandem mass spectrometry, ultraviolet absorbance detection and nuclear magnetic resonance spectrometry combined with liquid chromatographic micro-fractionation. J Chromatogr A 974: 123-134
33. Sasaki K, Mito K, Ohara K, Yamamoto H, Yazaki K (2008) Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens. Plant Physiol 146: 1075-1084
34. Sasaki K, Tsurumaru Y, Yamamoto H, Yazaki K (2011) Molecular characterization of a membrane-bound prenyltransferase specific for isoflavone from Sophora flavescens. J Biol Chem 286: 24125-24134
35. Schröder G, Zähringer U, Heller W, Ebel J, Grisebach H (1979) Biosynthesis of antifungal isoflavonoids in Lupinus albus: enzymatic prenylation of genistein and 29-hydroxygenistein. Arch Biochem Biophys 194: 635-636
36. Shibuya Y, Sugimura Y, Tahara S, Mizutani J (1992) Accumulation of isoflavones in lupin seedlings treated with copper chloride. Biosci Biotechnol Biochem 56: 690-691
37. Sugiyama A, Linley PJ, Sasaki K, Kumano T, Yamamoto H, Shitan N, Ohara K, Takanashi K, Harada E, Hasegawa H, et al (2011) Metabolic engineering for the production of prenylated polyphenols in transgenic legume plants using bacterial and plant prenyltransferases. Metab Eng 13: 629-637
38. Tahara S, Ibrahim RK (1995) Prenylated isoflavonoids: an update. Phytochemistry 38: 1073-1094
39. Tahara S, Ingham JL, Nakahara S, Mizutani J, Harborne JB (1984) Fungitoxic dihydrofuranoisoflavones and related compounds in white lupin, Lupinus albus. Phytochemistry 23: 1889-1900
40. Tahara S, Orihara S, Ingham JL, Mizutani J (1989) Seventeen isoflavonoids from Lupinus albus roots. Phytochemistry 28: 901-911
41. Tamura K, Dudley J, Nei M, Kumar S (2007) MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) software version 4.0. Mol Biol Evol 24: 1596-1599
42. Thompson JD, Gibson TJ, Plewniak F, Jeanmougin F, Higgins DG (1997) The CLUSTAL_X Windows interface: flexible strategies for multiple sequence alignment aided by quality analysis tools. Nucleic Acids Res 25: 4876-4882
43. Tian L, Peel GJ, Lei Z, Aziz N, Dai X, He J, Watson B, Zhao PX, Sumner LW, Dixon RA (2009) Transcript and proteomic analysis of developing white lupin (Lupinus albus L.) roots. BMC Plant Biol 9: 1
44. Venkatesh TV, Karunanandaa B, Free DL, Rottnek JM, Baszis SR, Valentin HE (2006) Identification and characterization of an Arabidopsis homogentisate phytyltransferase paralog. Planta 223: 1134-1144
45. Yazaki K, Kunihisa M, Fujisaki T, Sato F (2002) Geranyl diphosphate: 4-hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon: cloning and characterization of a key enzyme in shikonin biosynthesis. J Biol Chem 277: 6240-6246