cDNA cloning and functional characterisation of CYP98A14 and NADPH:cytochrome P450 reductase from Coleus blumei involved in rosmarinic acid biosynthesis

Plant Molecular Biology

Volumn 69, Issue 3, 2009, Pages 239-253

  Eberle, David ^a   Ullmann, Pascaline ^b   Werck Reichhart, Danièle ^b   Petersen, Maike ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b INST DE BIOL MOLEC DES PLANTES   (France)

Author keywords

Coleus blumei (Lamiaceae); CYP98 family; Cytochrome P450; NADPH:cytochrome P450 reductase; Rosmarinic acid

Indexed keywords

CINNAMIC ACID DERIVATIVE; DEPSIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; ROSMARINIC ACID; VEGETABLE PROTEIN;

AMINO ACID SEQUENCE; ANGIOSPERM; ARTICLE; CHEMISTRY; CLASSIFICATION; ENZYMOLOGY; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; METHODOLOGY; MOLECULAR CLONING; MOLECULAR GENETICS; PHYLOGENY; SEQUENCE HOMOLOGY;

AMINO ACID SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CINNAMATES; CLONING, MOLECULAR; DEPSIDES; LAMIACEAE; MOLECULAR SEQUENCE DATA; NADPH-FERRIHEMOPROTEIN REDUCTASE; PHYLOGENY; PLANT PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID;

COLEUS; LAMIACEAE; MAGNOLIOPHYTA; SACCHAROMYCES CEREVISIAE; SOLENOSTEMON SCUTELLARIOIDES;

EID: 58549119938     PISSN: 01674412     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11103-008-9420-7     Document Type: Article

References (57)

1. N Abdulrazzak B Pollet J Ehlting 2006 A coumaroyl-3′-ester hydroxylase insertion mutant reveals the existence of nonredundant meta-hydroxylation pathways and essential roles for phenolic precursors in cell expansion and plant growth Plant Physiol 140 30 48 10.1104/pp.105.069690
2. AM Anterola JH Jeon LB Davin 2002 Transcriptional control of monolignol biosynthesis in Pinus taeda-factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism J Biol Chem 277 18272 18280 10.1074/jbc.M112051200
3. S Bak RA Kahn HL Nielsen 1998 Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin Plant Mol Biol 38 725 734 10.1023/A:1006064202774
4. I Benveniste A Lesot G Hasenfratz 1991 Multiple forms of NADPH-cytochrome P450 reductase in higher plants Biochem Biophys Res Commun 177 105 112 10.1016/0006-291X(91)91954-B
5. MM Bradford 1976 A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal Biochem 72 248 254 10.1016/0003-2697(76)90527-3
6. M Brosché C Fant SW Bergkvist 1999 Molecular markers for UV-B stress in plants: alteration of the expression of four classes of genes in Pisum sativum and the formation of high molecular mass RNA adducts Biochim Biophys Acta 1447 185 198
7. CA Cooper E Gasteiger NH Packer 2001 GlycoMod-A software tool for determining glycosylation compositions from mass spectrometric data Proteomics 1 340 349 10.1002/1615-9861(200102)1:2<340::AID-PROT340>3.0.CO;2-B
8. 5 is required for full activity of flavonoid 3′, 5′-hydroxylase, a cytochrome P450 involved in the formation of blue flowercolors Proc Natl Acad Sci USA 96 778 783 10.1073/pnas.96.2.778
9. J Ehlting B Hamberger R Million-Rousseau 2006 Cytochromes P450 in phenolic metabolism Phytochem Rev 5 239 270 10.1007/s11101-006-9025-1
10. BE Ellis GHN Towers 1970 Biogenesis of rosmarinic acid in Mentha Biochem J 118 291 297
11. J Felsenstein 1989 PHYLIP-Phylogeny Inference Package (Version 3.2) Cladistics 5 164 166
12. Forkmann G, Heller W (1999) Biosynthesis of flavonoids. In: Barton DHR, Nakanishi K, Meth-Coon O, Sankawa U (eds) Comprehensive natural products chemistry, polyketides and other secondary metabolites including fatty acids and their derivatives, 1st edn. Elsevier Science, Oxford, pp 713-748
13. R Franke JM Humphreys MR Hemm 2002 The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism Plant J 30 33 45 10.1046/j.1365-313X.2002.01266.x
14. DR Gang T Beuerle P Ullmann 2002 Differential production of meta hydroxylated phenylpropanoids in Sweet Basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases Plant Physiol 130 1536 1544 10.1104/pp.007146
15. G Giuliano GE Bartley PA Scolino 1993 Regulation of carotenoid biosynthesis during tomato development Plant Cell 5 379 387
16. BA Halkier 1996 Catalytic reactivities and structure/function relationships of cytochrome P450 enzymes Phytochem 43 1 21 10.1016/0031-9422(96) 00263-4
17. W Heller T Kühnl 1985 Elicitor induction of a microsomal 5-O-(4-coumaroyl) shikimate 3′-hydroxylase in parsley cell suspension cultures Arch Biochem Biophys 241 453 460 10.1016/0003-9861(85)90570-3
18. L Hoffmann S Maury F Martz 2003 Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism J Biol Chem 278 95 103 10.1074/jbc.M209362200
19. S Jennewein H Park JH DeJong 2005 Coexpression in yeast of Taxus cytochrome P450 reductase with cytochrome P450 oxygenases involved in taxol biosynthesis Biotechnol Bioeng 89 588 598 10.1002/bit.20390
20. DH Kim BG Kim HJ Lee 2005 Enhancement of isoflavone synthase activity by co-expression of P450 reductase from rice Biotechnol Lett 27 1291 1294 10.1007/s10529-005-0221-7
21. E Koopmann K Hahlbrock 1997 Differentially regulated NADPH:cytochrome P450 oxidoreductases in parsley Proc Natl Acad Sci USA 94 14954 14959 10.1073/pnas.94.26.14954
22. T Kühnl U Koch W Heller 1987 Chlorogenic acid biosynthesis: characterization of a light-induced microsomal 5-O-(4-coumaroyl)-d-quinate/ shikimate 3′-hydroxylase from carrot (Daucus carota L.) cell suspension cultures Arch Biochem Biophys 258 226 232 10.1016/0003-9861(87)90339-0
23. V Mahesh R Million-Rousseau P Ullmann 2007 Functional characterization of two p-coumaroyl ester 3′-hydroxylase genes from coffee tree: evidence of a candidate for chlorogenic acid biosynthesis Plant Mol Biol 64 145 159 10.1007/s11103-007-9141-3
24. M Matsuno A Nagatsu Y Ogihara 2002 CYP98A6 from Lithospermum erythrorhizon encodes 4-coumaroyl-4′-hydroxyphenyllactic acid 3-hydroxylase involved in rosmarinic acid biosynthesis FEBS Lett 514 219 224 10.1016/S0014-5793(02)02368-2
25. AH Meijer MI Lopes Cardoso JT Voskuilen 1993 Isolation and characterization of a cDNA clone from Catharanthus roseus encoding NADPH:cytochrome P-450 reductase, an enzyme essential for reactions catalysed by cytochrome P-450 monooxygenases in plants Plant J 4 47 60 10.1046/j.1365-313X. 1993.04010047.x
26. M Mizutani D Ohta 1998 Two isoforms of NADPH:cytochrome P450 reductase in Arabidopsis thaliana-Gene structure, heterologous expression in insect cells, and differential regulation Plant Physiol 116 357 367 10.1104/pp.116.1.357
27. M Mizutani D Ohta R Sato 1997 Isolation of a cDNA and a genomic clone encoding cinnamate 4-hydroxylase from Arabidopsis and its expression manner in planta Plant Physiol 113 755 763 10.1104/pp.113.3.755
28. M Morant A Hehn D Werck-Reichhart 2002 Conservation and diversity of gene families explored using the CODEHOP strategy in higher plants BMC Plant Biol 2 7 10.1186/1471-2229-2-7
29. M Morant GA Schoch P Ullmann 2007 Catalytic activity, duplication and evolution of the CYP98 cytochrome P450 family in wheat Plant Mol Biol 63 1 19 10.1007/s11103-006-9028-8
30. D Mumberg R Müller M Funk 1995 Yeast vectors for the controlled expression of heterologous proteins in different genetic backgrounds Gene 156 119 122 10.1016/0378-1119(95)00037-7
31. RB Nair Q Xia CJ Kartha 2002 Arabidopsis CYP98A3 mediating aromatic 3-hydroxylation. Developmental regulation of the gene, and expression in yeast Plant Physiol 130 210 220 10.1104/pp.008649
32. DR Nelson MA Schuler SM Paquette 2004 Comparative genomics of rice and Arabidopsis. Analysis of 727 cytochrome P450 genes and pseudogenes from a monocot and a dicot Plant Physiol 135 756 772 10.1104/pp.104.039826
33. R Niggeweg AJ Michael C Martin 2004 Engineering plants with increased levels of the antioxidant chlorogenic acid Nat Biotechnol 22 746 754 10.1038/nbt966
34. D Ohta M Mizutani 2004 Redundancy or flexibility: molecular diversity of the electron transfer components for P450 monooxygenases in higher plants Front Biosci 9 1587 1597 10.2741/1356
35. M Petersen 1997 Cytochrome P-450-dependent hydroxylation in the biosynthesis of rosmarinic acid in Coleus Phytochemistry 45 1165 1172 10.1016/S0031-9422(97)00135-0
36. M Petersen MSJ Simmonds 2003 Rosmarinic acid Phytochemistry 62 121 125 10.1016/S0031-9422(02)00513-7
37. M Petersen E Häusler B Karwatzki 1993 Proposed biosynthetic pathway for rosmarinic acid in cell cultures of Coleus blumei Benth Planta 189 10 14 10.1007/BF00201337
38. M Petersen D Van Der Straeten G Bauw 1995 Full-length cDNA clone from Coleus blumei (Z49150) with high similarity to cobalamine-independent methionine synthase Plant Physiol 109 338
39. Y Pi Z Liao Y Chai 2006 Molecular cloning and characterization of a novel stem-specific gene from Camptotheca acuminata J Biochem Mol Biol 39 68 75
40. D Pompon B Louerat A Bronine 1996 Yeast expression of animal and plant P450s in optimized redox environments Methods Enzymol 272 51 64 10.1016/S0076-6879(96)72008-6
41. 5 in cytochrome P450 reactions J Biochem Mol Toxicol 16 311 316 10.1002/jbt.10052
42. TD Porter 2004 Jud Coon: 35 years of P450 research, a synopsis of P450 history Drug Metab Dispos 32 1 6 10.1124/dmd.32.1.1
43. DK Ro J Ehlting CJ Douglas 2002 Cloning, functional expression, and subcellular localization of multiple NADPH-cytochrome P450 reductases from hybrid poplar Plant Physiol 130 1837 1851 10.1104/pp.008011
44. A Rosco HH Pauli W Priesner 1997 Cloning and heterologous expression of NADPH-cytochrome P450 reductases from the Papaveraceae Arch Biochem Biophys 348 369 377 10.1006/abbi.1997.0374
45. TM Rose ER Schultz JG Henikoff 1998 Consensus-degenerate hybrid oligonucleotide primers for amplification of distantly-related sequences Nucleic Acids Res 26 1628 1635 10.1093/nar/26.7.1628
46. G Schoch S Goepfert M Morant 2001 CYP98A3 from Arabidopsis thaliana is a 3′-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway J Biol Chem 276 36566 36574 10.1074/jbc.M104047200
47. G Schoch M Morant N Abdulrazzak 2006 The meta-hydroxylation step in the phenylpropanoid pathway: a new level of complexity in the pathway and its regulation Environ Chem Lett 4 127 136 10.1007/s10311-006-0062-1
48. MA Schuler 1996 Plant cytochrome P450 monooxygenases Crit Rev Plant Sci 15 235 284 10.1080/713608134
49. MA Schuler D Werck-Reichhart 2003 Functional genomics of P450s Annu Rev Plant Biol 54 629 667 10.1146/annurev.arplant.54.031902.134840
50. MS Shet K Sathasivan MA Arlotto 1993 Purification, characterization, and cDNA cloning of an NADPH-cytochrome P450 reductase from mung bean Proc Natl Acad Sci USA 90 2890 2894 10.1073/pnas.90.7.2890
51. B Siminszky FT Corbin ER Ward 1999 Expression of a soybean cytochrome P450 monooxygenase cDNA in yeast and tobacco enhances the metabolism of phenylurea herbicides Proc Natl Acad Sci USA 96 1750 1755 10.1073/pnas.96.4.1750
52. DL Simmons PA Lalley CB Kasper 1985 Chromosomal assignments of genes coding for components of the mixed-function oxidase system in mice. Genetic localization of the cytochrome P-450PCN and P-450 PB gene families and the NADPH-cytochrome P-450 oxidoreductase and epoxide hydratase genes J Biol Chem 260 515 521
53. P Urban D Werck-Reichhart HG Teutsch 1994 Characterization of recombinant plant cinnamate 4-hydroxylase produced in yeast. Kinetic and spectral properties of the major plant P450 of the phenylpropanoid pathway Eur J Biochem 222 843 850 10.1111/j.1432-1033.1994.tb18931.x
54. P Urban C Mignotte M Kazmeier 1997 Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-cytochrome P450 reductases with P450 CYP73A5 J Biol Chem 272 19176 19186 10.1074/jbc.272.31.19176
55. M Wang DL Roberts R Paschke 1997 Three-dimensional structure of NADPH-cytochrome P450 reductase: prototype for FMN- and FAD-containing enzymes Proc Natl Acad Sci USA 94 8411 8416 10.1073/pnas.94.16.8411
56. Werck-Reichhart D, Bak S, Paquette S (2002) Cytochromes P450. In: Somerville CR, Meyerowitz EM (eds) Arabidopsis book. American Society of Plant Biologists, Rockville
57. T Yamada H Imaishi A Oka 1998 Molecular cloning and expression in Saccharomyces cerevisiae of tobacco NADPH-cytochrome P450 oxidoreductase cDNA Biosci Biotechnol Biochem 62 1403 1411 10.1271/bbb.62.1403