Molecular cloning and characterization of desacetoxyvindoline-4-hydroxylase, a 2-oxoglutarate dependent-dioxygenase involved in the biosynthesis of vindoline in Catharanthus roseus (L.) G. Don

Plant Molecular Biology

Volumn 34, Issue 6, 1997, Pages 935-948

  Vazquez Flota, Felipe ^a   De Carolis, Emidio ^a,b   Alarco, Anne Marie ^a,c   De Luca, Vincenzo ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b PFIZER INC   (United States)

^c CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

Author keywords

Catharanthus roseus; Dioxygenases; Indole alkaloids; Molecular regulation; Secondary metabolism

Indexed keywords

2 OXOGLUTARIC ACID; ALPHA-KETOGLUTARIC ACID; COMPLEMENTARY DNA; CRSD4H PROTEIN, CATHARANTHUS ROSEUS; DRUG DERIVATIVE; MIXED FUNCTION OXIDASE; OXYGENASE; RECOMBINANT PROTEIN; VEGETABLE PROTEIN; VINBLASTINE; VINDOLINE;

AMINO ACID SEQUENCE; ARTICLE; BIOSYNTHESIS; COMPARATIVE STUDY; DNA SEQUENCE; ENZYMOLOGY; ESCHERICHIA COLI; GENE DOSAGE; GENE EXPRESSION REGULATION; GENE LIBRARY; GENETICS; LIGHT; MEDICINAL PLANT; METABOLISM; MOLECULAR CLONING; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; RADIATION EXPOSURE; SEQUENCE HOMOLOGY; TISSUE DISTRIBUTION;

AMINO ACID SEQUENCE; BASE SEQUENCE; CLONING, MOLECULAR; DNA, COMPLEMENTARY; ESCHERICHIA COLI; GENE DOSAGE; GENE EXPRESSION REGULATION, PLANT; GENOMIC LIBRARY; KETOGLUTARIC ACIDS; LIGHT; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; OXYGENASES; PLANT PROTEINS; PLANTS, MEDICINAL; RECOMBINANT PROTEINS; SEQUENCE ANALYSIS, DNA; SEQUENCE HOMOLOGY, AMINO ACID; TISSUE DISTRIBUTION; VINBLASTINE;

CATHARANTHUS ROSEUS; ESCHERICHIA COLI; HYOSCYAMUS NIGER;

EID: 0031214493     PISSN: 01674412     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1005894001516     Document Type: Article

References (67)

1. Aebersol RH, Leavitt S, Saavedra RA, Hood LE, Kent SBH: Internal amino acid sequence analysis of protein separated by one- or two-dimensional electrophoresis after in situ protease digestion on nitrocellulose. Proc Natl Acad Sci USA 84: 6970-69-74 (1987).
2. Aerts R, Alarco AM, De Luca V: Auxins induce tryptophan decarboxylase activity in radicles of Catharanthus seedlings. Plant Physiol 100: 1014-1019 (1992).
3. Aerts R, De Luca V: Phytochrome is involved in the light-regulation of vindoline biosynthesis in Catharanthus. Plant Physiol 100: 1029-1032 (1992).
4. Aerts R, Gisi D, De Carolis E, De Luca V, Baumann TW: Methyl jasmonate vapor increases the developmentally controlled synthesis of alkaloids in Catharanthus and Cinchona seedlings. Plant J 5: 635-643 (1994).
5. Alvarez-Fernandez J, De Luca V: Ubiquitin-mediated degradation of tryptophan decarboxylase from Catharanthus roseus. Phytochemistry 36: 1123-1128 (1994).
6. Alvarez-Fernandez J, Owens TG, Kurz WGW, De Luca V: Immunological detection and quantitation of tryptophan decarboxylase in developing Catharanthus roseus seedlings. Plant Physiol 91: 79-84 (1989).
7. Balsevich J, De Luca V, Kurz WGW: Altered alkaloid pattern in dark grown seedlings of Catharanthus roseus. The isolation and characterization of 4-desacetoxyvindoline: a novel indole alkaloid an proposed precursor of vindoline. Heterocycles 24: 2415-2421 (1986).
8. Bristsch L, Dedio J, Saedler H, Forkmann G: Molecular characterization of flavanone 3β-hydroxylases. Consensus sequence, comparison with related enzyme and the role of conserved histidine residues. Eur J Biochem 217: 745-754 (1993).
9. 2+ oxidase with metal coordination sites for small molecules and substrate. J Biol Chem 264: 21677-21681 (1989).
10. Constabel F, Gaudet LaPraire P, Kurz WGW, Kutney JP: Alkaloid production in Catharanthus roseus cell cultures XII. Biosynthetic capacity of callus from original explants and regenerated shoots. Plant Cell Rep 1: 139-142 (1982).
11. Corpet F: Multiple sequence alignment with hierarchical clustering. Nucl Acid Res 16: 10881-10890 (1988).
12. Davis KM: A Malus cDNA with homology to Anthirrhinum candida and Zea A2 genes. Plant Physiol 103: 1015 (1993).
13. De Carolis E: Enzymology of vindoline biosynthesis. Purification, characterization and molecular cloning of a 2-oxoglutarate dependent-dioxygenase involved in the biosynthesis of vindoline in Catharanthus roseus. Ph. D. thesis, Université de Montréal, Montréal, Canada (1994).
14. De Carolis E, Chan F, Balsevich J, De Luca V: Isolation and characterization of a 2-oxoglutarate dependent dioxygenase involved in the second-to-last step in vindoline biosynthesis. Plant Physiol 94: 1323-1329 (1990).
15. De Carolis E, De Luca V: Purification, characterization, and kinetic analysis of a 2-oxoglutarate-dependent dioxygenase involved in vindoline biosynthesis from Catharanthus roseus. J Biol Chem 268: 5504-5511 (1993).
16. De Carolis E, Luca V: 2-oxoglutarate-dependent dioxygenase and related enzymes: Biochemical characterization. Phytochemistry 36: 1093-1107 (1994).
17. Deikman J, Fischer RL: Interaction of a DNA binding factor with the 5′-flanking region of an ethylene-responsive fruit ripening gene from tomato. EMBO J 7: 3315-3320 (1988).
18. De Luca V, Alvarez-Fernández JA, Campbell D, Kurz WGW: Developmental regulation of enzymes of indole alkaloid biosynthesis in Catharanthus roseus. Plant Physiol 86: 447-450 (1988).
19. De Luca V, Balsevich J, Kurz WGW: Acetyl coenzyme A: deacetoxyvindoline O-acetyltransferase, a novel enzyme from Catharanthus. J Plant Physiol 121: 417-428 (1985).
20. De Luca V, Balsevich J, Tyler RT, Eilert U, Panchuk BD, Kurz WGW: Biosynthesis of indole alkaloids: Developmental regulation of the biosynthetic pathway from taberonine to vindoline in Catharanthus roseus. J Plant Physiol 125: 147-156 (1986).
21. De Luca V, Balsevich J, Tyler RT, Kurz WGW: Characterization of a novel N-methyltransferase (NMT) from Catharanthus roseus. Plant Cell Rep 6: 458-461 (1987).
22. De Luca V, Cutler AJ: Subcellular localization of enzymes involved in indole alkaloid biosynthesis in Catharanthus roseus. Plant Physiol 85: 1099-1102 (1987).
23. De Luca V, Marineau C, and Brisson N: Molecular cloning and analysis of cDNA encoding a plant tryptophan decarboxylase: Comparison with animal dopa decarboxylases. Proc Natl Acad Sci USA 88: 9969-9973 (1989).
24. Dethier M, De Luca V: Partial purification of an N-methyltransferase involved in vindoline biosynthesis in Catharanthus roseus. Phytochemistry 32: 673-678 (1993).
25. Eilert U, Constabel F, Kurz WGW: Elicitor stimulation of monoterpene indole alkaloid formation in suspension cultures of Catharanthus roseus. J Plant Physiol 126: 11-22 (1986).
26. Feinberg AP, Vogelstein B: A technique for radiolabeling DNA restriction endonuclease fragments to high specific activity. Anal Biochem 137: 266-267 (1984).
27. French DL, Laskov R, Scharff MD: The role of somatic hypermutation in the generation of antibody diversity. Science 244: 152-1157 (1989).
28. Gamborg OL, Miller RA, Ojima K: Nutrient requirements of suspension cultures of soybean root cell. Exp Cell Res 50: 151-158 (1968).
29. Goddijn O, Lohman FP, de Kam RJ, Schilperoort RA, Hoge JHC: Nucleotide sequence of the tryptophan decarboxylase gene of Catharanthus roseus and expression of a tdc-gusA gene fusion in Nicotiana tabacum. Mol Gen Genet 242: 217-225 (1994).
30. Gubler U, Hoffman BJ: A simple and very efficient method for generating cDNA libraries. Gene 25: 263-269 (1983).
31. Han S, Eltis LD, Timmis KN, Muchmore SW, Bolin JT: Crystal structure of the biphenyl-cleaving extradiol dioxygenase from a PCB-degrading pseudomonad. Science 270: 976-980 (1995).
32. Holdsworth MJ, Bird CR, Ray J, Schuch W, Grierson D: Structure and expression of an ethylene-related mRNA from tomato. Nucl Acid Res 15: 731-739 (1987).
33. Holdsworth MJ, Schuch W, Grieson D: Nucleotide sequence of an ethylene-related gene from tomato. Nucl Acid Res 15: 10600 (1987).
34. Holton TA, Brugleira F, Tanaka Y: Cloning and expression of flavonol synthase from Petunia hybrida. Plant J 4: 1003-1010 (1993).
35. Jia S, Van Dusen WJ, Diehl RE, Dixon RA, Elliston KO, Stern AM, Friedman PA: cDNA cloning and expression of bovine aspartyl (asparinyl)β-hydroxylase. J Biol Chem 267: 14322-14327 (1992).
36. Johnson IS, Wright HF, Svoboda GH, Vlantis J: Antitumor principles derived from Vinca rosea Linn I. Vincaleukoblastine and leurosine. Cancer Res 20: 1016-1022 (1960).
37. Jones JDG, Dunsmuir P, Bedbrook J: High level expression of introduce chimeric gene. EMBO J 4: 2411-2418 (1985).
38. Joshi CP: An inspection of the domain between putative TATA box and translation start site in 79 plant genes. Nucl Acid Res 15: 6643-6653 (1987).
39. Joshi CP: Putative polyadenilation signal in nuclear genes of higher plants: a compilation and analysis. Nucl Acid Res 15: 9627-9640 (1987).
40. Kanegae T, Kajiya H, Amano Y, Hashimoto T, Yamada Y: Species-dependent expression of the hyoscyamine 6β-hydroxylase gene in the pericycle. Plant Physiol 105: 483-490 (1994).
41. Kurz WGW, Chatson KB, Constabel F, Kutney JP, Choi LSL, Kolodziejczyk P, Sleigh SK, Stuart KL, Worth BR: Alkaloid production in Catharanthus roseus cell cultures: Initial studies on cell lines and their alkaloid content. Phytochemistry 19: 2583-2587 (1980).
42. Kutchan TM, Hampp N, Lottspeich F, Beyreuther K, Zenk MH: The cDNA clone for strictosidine synthase from Rauvolfia serpentina. DNA sequence determination and expression in Escherichia coli. FEBS Lett 237: 40-44 (1988).
43. Kutney JB, Choi LSL, Kolodziejczyk P, Sleigh SK, Worth BR, Kurz WGW, Chatson KB, Constabel F: Alkaloid production in Catharanthus roseus cell cultures: Isolation and characterization of alkloids from one cell line. Phytochemistry 19: 2589-2595 (1980).
44. Lipman DJ, Pearson WR: Rapid and sensitive protein similarity searches. Science 227: 1435-1441 (1985).
45. Madyastha KM, Meehan TD, Coscia CJ: Characterization of a cytochrome P-450 dependent monoterpene hydroxylase from the higher plant Vinca rosea. Biochemistry 15: 1097-102 (1976).
46. Matsuda J, Okabe S, Hashimoto T, Yamada Y: Molecular cloning of hyoscyamine 6β-hydroxylase, a 2-oxoglutarate-dependent dioxygenase from cultured roots of Hyoscyamus niger. J Biol Chem 226: 9460-9464 (1991).
47. McKnight TD, Bergey DR, Burnett RJ, Nessler CL: Expression of an enzymatically active and correctly targeted strictosidine synthase in transgenic tobacco plants. Planta 185: 148-152 (1991).
48. McKnight TD, Roessner CA, Devagupta R, Scott AI, Nessler CL: Nucleotide sequence of a cDNA enconding the vacuolar protein strictosidine synthase from Catharanthus roseus. Nucl Acids Res 18: 4939 (1990).
49. Ming L-J, Que L Jr, Kriauciunas A, Frolick CA, Chen VJ: NMR studies of the active site of isopenicillin-N-synthase, a non-heme iron (II) enzyme. Biochemistry 30: 11653-11659 (1991).
50. Moreno PRH, van der Heijden R, Verpoorte R: Cell and tissue culture of Catharanthus roseus: a literature survey II. Updating from 1988-1993. Plant Cell Tissue Organ Cult 42: 1-25 (1995).
51. Murray M, Thompson WF: Rapid isolation of high molecular weight plant DNA. Nucl Acids Res 8: 4321-4325 (1980).
52. Nakai C, Uyeyama H, Kagayama H, Nakasawa T, Inouye S, Kishi F, Kakazawa A, Nuzaki M: Cloning, DNA sequencing and aminoacid sequencing of catechol 1,2-dioxygenases (pyrocatechase) from Pseudomonas putida mt-2 and Pseudomonas arvilla C-1. Arch Biochem Biophys 321: 353-362 (1995).
53. Pasquali G, Goddjin OJM, de Waal A, Verpoorte R, Schilperoot RA, Hoge JHC, Memelink J: Coordinate regulation of two indole alkaloid biosynthetic genes from Catharanthus roseus by auxin and elicitors. Plant Mol Biol 18: 1121-1131 (1992).
54. Phillips A, Ward DA, Ukness S, Appleford NFJ, Lange T, Huttly AK, Gaskin P, Graebe JE, Hedden P: Isolation and expression of three gibberellin 20-oxidase cDNA clones from Arabidopsis. Plant Physiol 108: 1049-1057 (1995).
55. Power R, Kurz WGW, De Luca V: Purification and characterization of acetylcoenzyme A: deacetylvindoline 4-O-acetyltransferase from Catharanthus roseus. Arch Biochem Biophys 279: 370-376 (1990).
56. Prescott AG, John P: Dioxygenases: molecular structure and role in plant metabolism. Annu Rev Plant Physiol Plant Mol Biol 47: 245-271 (1996).
57. Ramon D, Carramolino L, Patiño C, Sánchez F, Peñalva MA: Cloning and characterization of the isopenicillin N synthase gene mediating for formation of the β-lactam ring in Aspergillus nidulans. Gene 57: 171-181 (1987).
58. Roach PL, Clifton IJ, Fülöp V, Harlos K, Barton GJ, Hajdu J, Andersson I, Schofield CJ, Baldwin JE: Crystal structure of isopenicillin N synthase is the first from a new structural family of enzymes. Nature 375: 700-704 (1994).
59. Roewer IA, Clouthier N, Nessler C, De Luca V: Transient induction of tryptophan decarboxylase (TDC) and strictosidine synthase (SS) genes in cell suspension cultures of Catharanthus roseus. Plant Cell Rep 11: 86-89 (1992).
60. Sambrook J, Fritsch EF, Maniatis T: Molecular Cloning: A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY (1989).
61. Sanger F, Nicklen S, Coulson AR: DNA sequencing with chainterminating inhibitors. Proc Natl Acad Sci USA 83: 8073-8076 (1977).
62. Stearn WT: A synopsis of the genus Catharanthus (Apocyn-aceae). In: Taylor WI, Farnsworth NR (eds) The Catharanthus Alkaloids: Botany, Chemistry, Pharmacology and Clinical Uses, pp. 9-44. Marcel Dekker, New York (1975).
63. St-Pierre B, De Luca V: A cytochrome P-450 monooxygenase catalyzes the first step in the conversion of tabersonine to vindoline in Catharanthus roseus. Plant Physiol 109: 131-139 (1995).
64. Svoboda GH, Blake DA: The phytochemistry and pharmacology of Catharanthus roseus. In: Taylor WI, Farnsworth NR (eds) The Catharanthus Alkaloids: Botany, Chemistry, Pharmacology and Clinical Uses, pp. 45-83. Marcel Dekker, New York (1975).
65. Tan DSH, Sim T-S: Functional analysis of conserved histidine residues in Cephalosporium acremonium isopenicillin N synthase by site-directed mutagenesis. J Biol Chem 271: 889-894 (1996).
66. Van der Heijden R, Verpoorte R, ten Hoopen HJG: Cell and tissue cultures of Catharanthus roseus (L.) G. Don: a literature survey. Plant Cell Tissue Organ Cult 18: 231-280 (1989).
67. Westerkemper P, Wieczorek U, Gueritte F, Langlois N, Langlois Y, Potier P, Zenk MH: Radioimmunoassay for the determination of the indole alkaloid vindoline in Catharanthus. Planta Med 39: 24-37 (1980).