Biochemical and molecular characterizations of nicotine demethylase in tobacco

Physiologia Plantarum

Volumn 129, Issue 2, 2007, Pages 307-319

  Xu, Dongmei ^a   Shen, Yanxin ^a   Chappell, Joe ^b   Cui, Mingwu ^a   Nielsen, Mark ^a  

^a GenApps Inc   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; ENZYME KINETICS; ETHYLENE; GENES; METABOLITES;

NICOTINE DEMETHYLASE; PHENYLPROPANOIDS; PLANT GENOMES; PRECURSOR;

TOBACCO;

ENZYMES; GENES; NICOTINE; TOBACCO;

NICOTIANA TABACUM;

EID: 33846093407     PISSN: 00319317     EISSN: 13993054     Source Type: Journal    
DOI: 10.1111/j.1399-3054.2006.00811.x     Document Type: Article

References (57)

1. Affymetrix technical Notes (2002) Statistical Algorithms Description Document. Affymetrix Inc., Santa Clara, CA
2. Amacher DE, Schomaker SJ (1998) Ethylmorphine N-demethylase activity as a marker for cytochrome P450 CYP3A activity in rat hepatic microsomes. Toxicol Lett 94: 115-125
3. Bartholomeusz TA, Bhogal RK, Molinie R, Felpin FX, Mathe-Allainmat M, Meier AC, Drager B, Lebreton J, Roscher A, Robins RJ, Mesnard F (2005) Nicotine demethylation in Nicotiana cell suspension cultures: N#-formylnornicotine is not involved. Phytochemistry 66: 2432-2440
4. Botte M, Mabon F, LeMouillour M, Robins RJ (1997) Biosynthesis of nornicotine in root cultures of Nicotiana alata does not involve oxidation at C-5# of nicotine. Phytochemistry 46: 117-122
5. Bush LP (1999) Alkaloids biosynthesis. In: Davis DL, Nielsen MT (eds) Tobacco - Production, Chemistry and Technology. Blackwell Science, Oxford, UK, pp 285-291
6. Bush LP, Hempfling WP, Burton HR (1999) Biosynthesis of nicotine and related alkaloids. In: Gorrod, JW, Jacob P (eds) Analytical Determination of Nicotine and Related Compounds and their Metabolites. Elsevier, Amsterdam, pp 13-44
7. Bush LP, Cui M, Shi H, Burton HR (2001) Formation of tobacco-specific nitrosamines in air-cured tobacco. Rec Adv Tob Sci 27: 23-46
8. Carlson T, Jones J, Peterson LA, Castagnoli NJ, Iyer K, Trager W (1995) Stereoselectivity and isotopic effects associated with cytochrome P450-catalyzed oxidation of (S)-nicotine. Drug Metab Dispos 2: 749-756
9. Cassels BK, Breitmaier E, Zenk MH (1987) Bisbenzylisoquinoline alkaloids in Berberis cell cultures. Phytochemistry 26: 1005-1008
10. Chaple C (1998) Molecular-genetic analysis of plant cytochrome P450-dependent monooxygenase. Annu Rev Plant Physiol Plant Mol Biol 49: 311-343
11. Chelvarajan RL, Fannin FF, Bush LP (1993), Study of nicotine demethylation in Nicotiana otophora. J Agric Food Chem 41: 858-862
12. Chou WM, Kutchan TM (1998) Enzymatic oxidations in the biosynthesis of complex alkaloids. Plant J 15: 289-300
13. Collu G, Unver N, Peltenburg-Looman AM, van der Heijden R, Verpoorte R, Memelink J (2001) Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis. FEBS Lett 508: 215-220
14. Dixon RA, Paiva NL (1995) Stress-induced phenylpropanoid metabolism. Plant Cell 7: 1085-1097
15. Fannin FF, Bush LP (1992) Nicotine demethylation in Nicotiana. Med Sci Res 20: 867-868
16. Feyereisen R (2005) Insect cytochrome P450. In: Gilbert LI, Iatrou K, Gill SS (eds) Comprehensive Molecular Insect Science. Elsevier, Amsterdam, The Netherlands pp 1-77
17. Flanagan JU, Marechal JD, Ward R, Kemp CA, McLaughlin LA, Sutcliffe MJ, Roberts GC, Paine MJ, Wolf CR (2004) Phe120 contributes to the regiospecificity of cytochrome P450 2D6: mutation leads to the formation of a novel dextromethorphan metabolite. Biochem J 380: 353-360
18. Frank MR, Deyneka JM, Schuler MA (1996) Cloning of wound-induced cytochrome P450 monooxygenases expressed in pea. Plant Physiol 110: 1035-1046
19. Franke R, Hemm MR, Denault JW, Ruegger MO, Humphreys JM, Chapple C (2002) Changes in secondary metabolism and deposition of an unusual lignin in the ref8 mutant of Arabidopsis. Plant J 30: 47-59
20. Gotoh O (1992) Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J Biol Chem 267: 83-90
21. Grausem B, Chaubet N, Gigot C, Loper JC, Benveniste P (1995) Functional expression of Saccharomyces cerevisiae CYP51A1 encoding lanosterol-14-demethylase in tobacco results in bypass of endogenous sterol biosynthetic pathway and resistance to an obtusifoliol-14-demethylase herbicide inhibitor. Plant J 7: 761-770
22. Hao D, Yeoman MM (1996a) Mechanism of nicotine N-demethylation in tobacco cell suspension cultures. Phytochemistry 41: 477-482
23. Hao D, Yeoman MM (1996b) Nicotine N-demethylase in cell-free preparations from tobacco cell cultures. Phytochemistry 42: 325-329
24. Heyn H, White RB, Stevens JC (1996) Catalytic role of cytochrome P4502B6 in the N-demethylation of S-mephenytoin. Drug Metab Dispos 24: 948-954
25. Huala E, Dickerman AW, Garcia-Hernandez M, Weems D, Reiser L, LaFond F, Hanley D, Kiphart D, Zhuang M, Huang W, Mueller LA, Bhattacharyya D, Bhaya D, Sobral BW, Beavis W, Meinke DW, Town CD, Somerville C, Rhee SY (2001) The Arabidopsis Information Resource TAIR: a comprehensive database and web-based information retrieval, analysis, and visualization system for a model plant. Nucleic Acids Res 29: 102-105. Available at http://wwwarabidopsisorg/agihtml
26. Irmler S, Schroder G, St-Pierre B, Crouch NP, Hotze M, Schmidt J, Strack D, Matern U, Schroder J (2000) Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Plant J 24: 797-804
27. 14alpha- demethylase CYP51 antisense Arabidopsis shows slow growth and long life. Biochem Biophys Res Commun 285: 98-104
28. Leete E (1983) Biosynthesis and metabolism of the tobacco alkaloids. In: Pelletier S (ed) Alkaloids: Chemical and Biological Perspectives. Wiley, Chichester, pp 85-152
29. Meijer AH, Souer E, Verpoorte R, Hoge JH (1993) Isolation of cytochrome P-450 cDNA clones from the higher plant Catharanthus roseus by a PCR strategy. Plant Mol Biol 22: 379-383
30. Mesnard F, Girard S, Fliniaux O, Bhogal RK, Gillet F, Lebreton J, Fliniaux M-A, Robins RJ (2001) Chiral specificity of the degradation of nicotine by Nicotiana plumbaginifolia cell suspension cultures. Plant Sci 161: 1011-1018
31. Mesnard F, Roscher A, Garlick AP, Girard S, Baguet E, Arroo RR, Lebreton J, Robins RJ, Ratcliffe G (2002) Evidence for the involvement of tetrahydrofolate in the demethylation of nicotine by Nicotiana plumbaginifolia cell-suspension cultures. Planta 214: 911-919
32. Mihaliak CA, Karp F, Croteau R (1993) Cytochrome P450 terpene hydroxylases, In: PJ Lea (ed) Methods in Plant Biochemistry. Academic Press, New York 9: 261-279
33. Morant M, Bak S, Moller BL, Werck-Reichhart D (2003) Plant cytochromes P450: tools for pharmacology, plant protection and phytoremediation. Curr Opin Biotechnol 14: 151-162
34. Nelson DR, Schuler MA, Paquette SM, Werck-Reichhart D, Bak S (2004a) 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
35. Nelson DR, Zeldin DC, Hoffman SM, Maltais LJ, Wain HM, Nebert DW (2004b) Comparison of cytochrome P450 CYP genes from the mouse and human genomes, including nomenclature recommendations for genes, pseudogenes and alternative-splice variants. Pharmacogenetics 14: 1-18
36. O'Brien M, Chantha SC, Rahier A, Matton DP (2005) Lipid signaling in plants. Cloning and expression analysis of the obtusifoliol 14α- demethylase from Solanum chacoense Bitt, a pollination- and fertilization-induced gene with both obtusifoliol and lanosterol demethylase activity. Plant Physiol 139: 734-749
37. Ochman H, Gerber AS, Hartl DL (1988) Genetic applications of an inverse polymerase chain reaction. Genetics 1203: 621-623
38. Ohmori S, Takeda S, Rikihisa T, Kiuchi M, Kanakubo Y, Kitada M (1993) Studies on cytochrome P450 responsible for oxidative metabolism of imipramine in human liver microsomes. Biol Pharm Bull 16: 571-575
39. Omura T, Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. J Biol Chem 239: 2370-2378
40. Pauli HH, Kutchan TM (1998) Molecular cloning and functional heterologous expression of two alleles encoding S-N-methylcoclaurine 3′-hydroxylase CYP80B1, a new methyl jasmonate-inducible cytochrome P-450-dependent mono-oxygenase of benzylisoquinoline alkaloid biosynthesis. Plant J 13: 793-801
41. 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
42. Ralston L, Kwon ST, Schoenbeck M, Ralston J, Schenk DJ, Coates RM, Chappell J (2001) Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum). Arch Biochem Biophys 393: 222-235
43. Sambrook J, Russel DW (2001) Molecular Cloning: a Laboratory Manual: 3rd Edn. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY
44. Schopfer CR, Ebel J (1998) Identification of elicitor-induced cytochrome P450s of soybean (Glycine max L.) using differential display of mRNA Mol Gen Genet 258: 315-322
45. Schroder G, Unterbusch E, Kaltenbach M, Schmidt J, Strack D, De Luca V, Schroder J (1999) Light-induced cytochrome P450-dependent enzyme in indole alkaloid biosynthesis: tabersonine 16-hydroxylase. FEBS Lett 458: 97-102
46. Siminszky B, Gavilano L, Bowen SW, Dewey RE (2005) Conversion of nicotine to nornicotine in Nicotiana tabacum is mediated by CYP82E4, a cytochrome P450 monooxygenase. Proc Natl Acad Sci USA 102: 14919-14924
47. Specker S, Matern U (2004) Ammi majus cytochrome P450 CYP82H1 mRNA, complete cds. Direct Submission to GenBank (AY532373)
48. Takahashi S, Zhao Y, O'Maille PE, Greenhagen BT, Noel JP, Coates RM, Chappell J (2005) Kinetic and molecular analysis of 5-epiaristolochene 1,3-dihydroxylase, a cytochrome P450 enzyme catalyzing successive hydroxylations of sesquiterpenes. J Biol Chem 280: 3686-3696
49. Takemoto D, Hayashi M, Doke N, Nishimura M, Kawakita K (1999) Molecular cloning of a defense-response-related cytochrome P450 gene from tobacco. Plant Cell Physiol 40: 1232-1242
50. Taton M, Rahier A (1991) Properties and structural requirements for substrate specificity of cytochrome P-450-dependent obtusifoliol 14 alpha-demethylase from maize (Zea mays) seedlings. Biochem J 277: 483-492
51. Tijet N, Helvig C, Feyereisen R (2001) The cytochrome P450 gene superfamily in Drosophila melanogaster: annotation, intron-exon organization and phylogeny. Gene 262: 189-198
52. Truan G, Cullin C, Reisdorf P, Urban P, Pompon D (1993) Enhanced in vivo monooxygenase activities in mammalian P450s in engineered yeast cells producing high levels of NADPH-P450 reductase and human cytochrome b5. Gene 125: 49-55
53. Werck-Reichhart D, Bak S, Paquette S (2002) Cytochromes P450. In: Somerville CR, Meyerowitz EM (eds) The Arabidopsis Book. American Society of Plant Biologists, Rockville MD, pp 1-28. Available at http://www.aspb.org/ publications/arabidopsis/
54. Whitbred JM, Schuler MA (2000) Molecular characterization of CYP73A9 and CYP82A1 P450 genes involved in plant defense in pea. Plant Physiol 124: 47-58
55. Yamanaka H, Nakajima M, Fukami T, Sakai H, Nakamura A, Katoh M, Takamiya M, Aoki Y, Yokoi T (2005) CYP2A6 and CYP2B6 are involved in nornicotine formation from nicotine in humans: interindividual differences in these contributions. Drug Metab Dispos 33: 1811-1818
56. Yano JK, Wester MR, Schoch GA, Griffin KJ, Stout CD, Johnson EF (2004) The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 205-A resolution. J Biol Chem 279: 38091-38094
57. Yu A, Dong H, Lang D, Haining RL (2001) Characterization of dextromethorphan O- and N-demethylation catalyzed by highly purified recombinant human CYP2D6. Drug Metab Dispos 29: 1362-1365