Molecular cloning of two genes encoding cinnamate 4-hydroxylase (C4H) from oilseed rape (Brassica napus)

Journal of Biochemistry and Molecular Biology

Volumn 40, Issue 2, 2007, Pages 247-260

  Chen, An He ^a,b   Chai, You Rong ^a   Li, Jia Na ^a   Chen, Li ^a  

^a SOUTHWEST UNIVERSITY   (China)

^b CHONGQING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Cinnamate 4 hydroxylase; Cloning; Expression; Oilseed rape (Brassica napus)

Indexed keywords

ARABIDOPSIS; ARABIDOPSIS THALIANA; BRASSICA NAPUS; BRASSICACEAE;

EID: 34047173037     PISSN: 12258687     EISSN: 02191024     Source Type: Journal    
DOI: 10.5483/bmbrep.2007.40.2.247     Document Type: Article

References (54)

1. Anterola, A. M. and Lewis, N. G. (2002) Trends in lignin modification: a comprehensive analysis of the effects of genetic manipulations/mutations on lignification and vascular integrity. Phytochemistry 61, 221-294.
2. Barber, M. S. and Mitchell, H. J. (1997) Regulation of phenylpropanoid metabolism in relation to lignin biosynthesis in plants. Int. Rev. Cytol. 172, 243-293.
3. Bell-Lelong, D. A., Cusumano, J. C., Meyer, K. and Chapple, C. (1997) Cinnamate-4-hydroxylase expression in Arabidopsis (Regulation in response to development and the environment). Plant Physiol. 113, 729-738.
4. Benavente-Garcia, O., Castillo, J., Marin, F. R., Ortuno, A. and Del Rio, J. A. (1997) Uses and properties of Citrus flavonoids. J. Agric. Food Chem. 45, 4505-4515.
5. Bendtsen, J. D., Nielsen, H., von Heijne, G. and Brunak, S. (2004) Improved prediction of signal peptides: SignalP 3.0. J. Mol. Biol. 340, 783-795.
6. Betz, C., McCollum, T. G. and Mayer, R. T. (2001) Differential expression of two cinnamate 4-hydroxylase genes in 'Valencia' orange (Citrus sinensis Osbeck). Plant Mol. Biol. 46, 741-748.
7. Blom, N., Sicheritz-Ponten, T., Gupta, R., Gammeltoft, S. and Brunak, S. (2004) Prediction of post-translational glycosylation and phosphorylation of proteins from the amino acid sequence. Proteomics 4, 1633-1649.
8. Cavell, A., Lydiate, D., Parkin, I., Dean, C. and Trick, M. (1998) Collinearity between a 30-centimorgan segment in Arabidopsis thaliana chromosome 4 and duplicated regions within the Brassica napus genome. Genome 41, 62-69.
9. Chapple, C. (1998) Molecular-genetic analysis of plant cytochrome P450-dependent monooxygenases. Annu. Rev. Plant Physiol. Plant Mol. Biol. 49, 311-343.
10. Damert, A., Leibiger, B. and Leibiger, I. B. (1996) Dual function of the intron of the rat insulin I gene in regulation of gene expression. Diabetologia 39, 1165-1172.
11. Debeaujon, I., Nesi, N., Perez, P., Devic, M., Grandjean, O., Caboche, M. and Lepiniec, L., (2003) Proanthocyanidin-accumulating cells in Arabidopsis testa: regulation of differentiation and role in seed development. Plant Cell 15, 2514-2531.
12. Di Carlo, G., Mascolo, N., Izzo, A. A. and Capasso, F. (1999) Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci. 65, 337-353.
13. Dixon, R. A. and Paiva, N. L. (1995) Stress-induced phenylpropanoid metabolism. Plant Cell 7, 1085-1097.
14. Dixon, R. A. and Steele, C. L. (1999) Flavonoids and isoflavonoids - a gold mine for metabolic engineering. Trends Plant Sci. 4, 394-400.
15. Dixon, R. A., Lamb, C. J., Masoud, S., Sewalt, V. J. H. and Paiva, N. L. (1996) Metabolic engineering: prospects for crop improvement through the genetic manipulation of phenylpropanoid biosynthesis and defense responses - a review. Gene 179, 61-71.
16. Fahrendorf, T. and Dixon, R, A. (1993) Molecular cloning of the elicitor-inducible cinnamic acid 4-hydroxylase cytochrome P450 from alfalfa. Arch. Biochem. Biophys. 305, 509-515.
17. Fourmann, M., Barret, P., Froger, N., Baron, C., Charlot, F., Delourme, R. and Brunel, D. (2002) From Arabidopsis thaliana to Brassica napus: development of amplified consensus genetic markers (ACGM) for construction of a gene map. Theor. Appl. Genet. 105, 1196-1206.
18. Frank, M. R., Deyneka, J. M. and Schuler, M. A. (1996) Cloning of wound-induced cytochrome P450 monooxygenases expressed in pea. Plant Physiol. 110, 1035-1046.
19. Gabriac, B., Werck-Reichhart, D., Teutsch, H. and Durst, F. (1991) Purification and immunocharacterization of a plant cytochrome P450: the cinnamic acid 4-hydroxylase. Arch. Biochem. Biophys. 288, 302-309.
20. Geourjon, C. and Deléage, G. (1995) SOPMA: Significant improvement in protein secondary structure prediction by consensus prediction from multiple alignments. Cabios 11, 681-684.
21. Guex, N. and Peitsch, M. C. (1997) SWISS-MODEL and the Swiss-PdbViewer: An environment for comparative protein modeling. Electrophoresis 18, 2714-2723.
22. Harakava, R. (2005) Genes encoding enzymes of the lignin biosynthesis pathway in Eucalyptus. Genet. Mol. Biol. 28, 601-607.
23. Harborne, J. B. and Williams, C. A. (2000) Advances in flavonoid research since 1992. Phytochemistry 55, 481-504.
24. Hasemann, C. A., Kurumbail, R. G., Boddupalli, S. S., Peterson, J. A. and Deisenhofer, J. (1995) Structure and function of cytochromes P450: a comparative analysis of three crystal structures. Structure 3, 41-62.
25. Heneen, W. K. and Brismar, K. (2001) Maternal and embryonal control of seed colour by different Brassica alboglabra chromosomes. Plant Breed. 120, 325-329.
26. Hofmann, K. and Stoffel, W. (1993) TMbase - A database of membrane spanning proteins segments. Biol. Chem. Hoppe-Seyler 374, 166.
27. Jaakola, L., Pirttilä, A. M., Halonen, M. and Hohtola, A. (2001) Isolation of high quality RNA from bilberry (Vaccinium myrtillus L.) fruit. Mol. Biotechnol. 19, 201-203.
28. Koopman, E., Logemann, E. and Hahlbrock, K. (1999) Regulation and functional expression of cinnamate 4-hydroxylase from parsley. Plant Physiol. 119, 49-55.
29. Le Marchand, L. (2002) Cancer preventive effects of flavonoids: a review. Biomed. Pharmacother. 56, 296-301.
30. Lukens, L., Quijada, P., Udall, J., Pires, J. C., Schranz, M. E. and Osborn, T. C. (2004) Genome redundancy and plasticity within ancient and recent Brassica crop species. Biol. J. Linnean Soc. 82, 665-674.
31. Lysak, M. A., Berr, A., Pecinka, A., Schmidt, R., McBreen, K. and Schubert, I. (2006) Mechanisms of chromosome number reduction in Arabidopsis thaliana and related Brassicaceae species. Proc. Natl. Acad. Sci. USA 103, 5224-5229.
32. Lysak, M. A., Koch, M. A., Pecinka, A. and Schubert, I. (2005) Chromosome triplication found across the tribe Brassiceae. Genome Res. 15, 516-525.
33. Madera, M., Vogel, C., Kummerfeld, S. K., Chothia, C. and Gough, J. (2004) The SUPERFAMILY database in 2004: additions and improvements. Nucleic Acids Res. 32, 235-239.
34. Manthey, J. A., Guthrie, N. and Grohmann, K. (2001) Biological properties of citrus flavonoids pertaining to cancer and inflammation. Curr. Med. Chem. 8, 135-153.
35. Marchler-Bauer, A. and Bryant, S. H. (2004) CD-Search: protein domain annotations on the fly. Nucleic Acids Res. 32, 327-331.
36. Mitaku, S., Hirokawa, T. and Tsuji, T. (2002) Amphiphilicity index of polar amino acids as an aid in the characterization of amino acid preference at membrane-water interfaces. Bioinformatics 18, 608-616.
37. Mizutani, M., Ohta, D. and Sato, R. (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.
38. Mizutani, M., Ward, E., DiMaio, J., Ohta, D., Ryals, J. and Sato, R. (1993) Molecular cloning and sequencing of a cDNA encoding mung bean cytochrome P450 (P450C4H) possessing cinnamate 4-hydroxylase activity. Biochem. Biophys. Res. Comm. 190, 875-880.
39. Nedelkina, S., Jupe, S. C., Blee, K. A., Schalk, M., Werck-Reichhart, D. and Bolwell, G. P. (1999) Novel characteristics and regulation of a divergent cinnamate 4-hydroxylase (CYP73A15) from French bean: engineering expression in yeast. Plant Mol. Biol. 39, 1079-1090.
40. Nelson, D. R., Schuler, M. A., Paquette, S. M., Werck-Reichhart, D. and Bak, S. (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.
41. Petersen Brown, R., Berenbaum, M. R. and Schuler, M. A. (2004) Transcription of a lepidopteran cytochrome P450 promoter is modulated by multiple elements in its 5′ UTR and repressed by 20-hydroxyecdysone. Insect Mol. Biol. 13, 337-347.
42. Rechards, E. J. (1995) Preparation and analysis of DNA; in Short Protocol in Molecular Biology, Ausubel, F. M., Brent, R., Kingston, R. E., Moore, D. D., Seidman, J. G., Smith, J. A. and Struhl, K. (eds.), pp. 36-38, John Wiley and Sons, New York, USA.
43. Rupasinghe, S., Baudry, J. and Schuler, M. A. (2003) Common active site architecture and binding strategy of four phenylpropanoid P450s from Arabidopsis thaliana as revealed by molecular modeling. Protein Eng. 16, 721-731.
44. Russell, D. W. (1971) The metabolism of aromatic compounds in higher plants. Properties of cinnamic acid 4-hydroxylase of pea seedlings and some aspects of its metabolic and developmental control. J. Biol. Chem. 246, 3870-3778.
45. Sambrook, J. and Russell, D. W. (2001) Molecular Cloning: A Laboratory Manual, 3rd ed. Cold Spring Harbor Laboratory Press, New York, USA.
46. Schmidt, R., Acarkan, A., Boivin, K. (2001) Comparative structural genomics in the Brassicaceae family. Plant Physiol. Biochem. 39, 253-262.
47. Schoch, G. A., Attias, R., Le Ret, M. and Werck-Reichhart, D. (2003) Key substrate recognition residues in the active site of a plant cytochrome P450, CYP73A1. Homology guided site-directed mutagenesis. Eur. J. Biochem. 270, 3684-3695.
48. Seidman, C. E., Struhl, K. and Sheen, J. (1995) Escherichia coli, plasmids, and bacteriophages; in Short Protocols in Molecular Biology, Ausubel, F. M., Brent, R., Kingston, R. E., Moore, D. D., Seidman, J. G., Smith, J. A. and Struhl, K. (eds.), pp. 22-24, John Wiley and Sons, New York, USA.
49. Small, I., Peeters, N., Legeai, F. and Lurin, C. (2004) Predotar: a tool for rapidly screening proteomes for N-terminal targeting sequences. Proteomics 4, 1581-1590.
50. Takai, D. and Jones, P. A. (2002) Comprehensive analysis of CpG islands in human chromosomes 21 and 22. Proc. Natl. Acad. Sci. USA 99, 3740-3745.
51. Teutsch, H. G., Hasenfratz, M.-P., Lesot, A., Stoltz, C., Garnier, J.-M., Jeltsch, J.-M., Durst, F. and Werck-Reichhart, D. (1993) Isolation and sequence of a cDNA encoding the Jerusalem artichoke cinnamate-4-hydroxylase, a major plant cytochrome P450 involved in the general phenylpropanoid pathway. Proc. Natl. Acad. Sci. USA 90, 4102-4107.
52. Weisshaar, B. and Jenkins, G. I. (1998) Phenylpropanoid biosynthesis and its regulation. Curr. Opin. Plant Biol. 1, 251-257.
53. Werck-Reichhart, D., Bak, S. and Paquette, S. (2002) Cytochromes P450; in The Arabidopsis Book, Somerville, C. R. and Meyerowitz, E. M. (eds.), pp. 1-28, American Society of Plant Biologists, Rockville, USA.
54. Winkel-Shirley, B. (1999) Evidence for enzyme complexes in the phenylpropanoid and flavonoid pathways. Physiol. Plant. 107, 142-149.