RNAi suppression of the morphine biosynthetic gene salAT and evidence of association of pathway enzymes

Phytochemistry

Volumn 70, Issue 5, 2009, Pages 579-589

  Kempe, Katja ^a,b   Higashi, Yasuhiro ^a   Frick, Susanne ^a,b   Sabarna, Khaled ^b   Kutchan, Toni M ^a,b  

^a DONALD DANFORTH PLANT SCIENCE CENTER   (United States)

^b LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

Co immunoprecipitation; Morphine biosynthesis; Opium poppy; Papaver somniferum; Papaveraceae; RNAi; Salutaridine reductase; Salutaridinol 7 O acetyltransferase; Yeast two hybrid

Indexed keywords

ACYLTRANSFERASE; MORPHINE; PRIMER DNA;

ARTICLE; BIOSYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYMOLOGY; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEOTIDE SEQUENCE; PAPAVER; POLYMERASE CHAIN REACTION; RNA INTERFERENCE; TWO HYBRID SYSTEM;

ACETYLTRANSFERASES; BASE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA PRIMERS; MORPHINE; PAPAVER; POLYMERASE CHAIN REACTION; RNA INTERFERENCE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TWO-HYBRID SYSTEM TECHNIQUES;

PAPAVER SOMNIFERUM; PAPAVERACEAE;

EID: 64949176017     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.03.002     Document Type: Article

References (38)

1. Allen R.S., Millgate A.G., Chitty J.A., Thisleton J., Miller J.A.C., Fist A.J., Gerlach W.L., and Larkin P.J. RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy. Nat. Biotechnol. 22 (2004) 1526-1527
2. Allen R.S., Miller J.A., Chitty J.A., Fist A.J., Gerlach W.L., and Larkin P.J. Metabolic engineering of morphinan alkaloids by over-expression and RNAi suppression of salutaridinol 7-O-acetyltransferase in opium poppy. Plant Biotech. J. 6 (2008) 22-30
3. Burbulis I.E., and Winkel-Shirley B. Interactions among enzymes of the Arabidopsis flavonoid biosynthetic pathway. Proc. Natl. Acad. Sci. USA 96 (1999) 12929-12934
4. Chitty J.A., Allen R.S., Fist A.J., and Larkin P.J. Genetic transformation in commercial Tasmanian cultivars of opium poppy, Papaver somniferum, and movement of transgenic pollen in the field. Funct. Plant Biol. 30 (2003) 1045-1058
5. Chomczynski P., and Sacchi N. Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. Anal. Biochem. 162 (1987) 156-159
6. Czichi U., and Kindl H. Phenylalanine ammonia lyase and cinnamic acid hydroxylases as assembled consecutive enzymes on microsomal membranes of cucumber cotyledons: cooperation and subcellular distribution. Planta 134 (1977) 133-143
7. Dixon R.A., and Steele C.L. Flavonoids and isoflavonoids - a gold mine for metabolic engineering. Trends Plant Sci. 4 (1999) 394-400
8. Frick S., Chitty J.A., Kramell R., Schmidt J., Allen R.S., Larkin P.J., and Kutchan T.M. Transformation of opium poppy (Papaver somniferum L.) with antisense berberine bridge enzyme gene (anti-bbe) via somatic embryogenesis results in an altered ratio of alkaloids in latex but not in roots. Transgenic Res. 13 (2004) 607-613
9. Frick S., Kramell R., Schmidt J., Fist A.J., and Kutchan T.M. Comparative qualitative and quantitative determination of alkaloids in narcotic and condiment Papaver somniferum cultivars. J. Nat. Prod. 68 (2005) 666-673
10. Frick S., Kramell R., and Kutchan T.M. Metabolic engineering of a morphine biosynthetic P450 in opium poppy surpasses breeding. Metab. Eng. 9 (2007) 169-176
11. Gerardy R., and Zenk M.H. Purification and characterization of salutaridine: NADPH 7-oxidoreductase from Papaver somniferum. Phytochemistry 34 (1993) 125-132
12. Gleave A.P. A versatile binary vector system with a T-DNA organisational structure conducive to efficient integration of cloned DNA into the plant genome. Plant Mol. Biol. 20 (1992) 1203-1207
13. Grothe T., Lenz R., and Kutchan T.M. Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. J. Biol. Chem. 276 (2001) 30717-30723
14. Huang F.C., and Kutchan T.M. Distribution of morphinan and benzo[c]phenanthridine alkaloid gene transcript accumulation in Papaver somniferum. Phytochemistry 53 (2000) 555-564
15. Hughes E.H., and Shanks J.V. Metabolic engineering of plants for alkaloid production. Metab. Eng. 4 (2002) 41-48
16. Kristensen C., Morant M., Olsen C.E., Ekstrøm C.T., Galbraith D.W., Møller B.L., and Bak S. Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome. Proc. Natl. Acad. Sci. USA 102 (2005) 1779-1784
17. Kutchan T.M. Molecular genetics of plant alkaloid biosynthesis. In: Cordell G.A. (Ed). The Alkaloids: Chemistry and Pharmacology vol. 50 (1998), Academic Press, San Diego 257-316
18. Kutchan T.M., Ayabe S., Krueger R.J., Coscia E.M., and Coscia C.J. Cytodifferentiation and alkaloid accumulation in cultured cells of Papaver bracteatum. Plant Cell Rep. 2 (1983) 281-284
19. Kutchan, T.M., Frick, S., Weid, M. 2007. Engineering plant alkaloid biosynthetic pathways - progress and prospects. In: Bohnert, H.J., Nguyen, H.T. (Eds.), Advances in Plant Biochemistry and Molecular Biology. In: Nes, W.D., Lewis, N.G. (Eds.), Bioengineering and Molecular Biology of Plant Pathways, vol. 1. Elsevier Science Ltd., Oxford, pp. 281-308.
20. Larkin, P.J., Chitty, J.A., Brettell, R.I.S. 1999. Methods for Plant Transformation and Regeneration. International Patent Publication Number WO 99/34663.
21. Lazo G.R., Stein P.A., and Ludwig R.A. A DNA transformation-competent Arabidopsis genomic library in Agrobacterium. Bio-Technol. 9 (1991) 963-967
22. Lednicer D., and Mitscher L.A. The Organic Chemistry of Drug Synthesis vol. 4 (1990), John Wiley and Sons Canada Ltd., New York
23. Lindberg-Møller B., and Conn E.E. The biosynthesis of cyanogenic glucosides in higher plants. J. Biol. Chem. 255 (1980) 3049-3056
24. Maniatis, T., Fritsch, E.F., Sambrook, J. (Eds.), 1982. Molecular Cloning: A Laboratory Manual, second ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York.
25. Morais J.M., Barbosa-Filho J.M., and Almeida R.N. Central depressant effects of reticuline extracted from Oceta duckei in rats and mice. J. Ethno. Pharmacol. 62 (1998) 57-61
26. Nakaoji K., Nayeshiro H., and Tanahashi T. Norreticuline and reticuline as possible new agents for hair growth acceleration. Biol. Pharm. Bull. 20 (1997) 586-588
27. Ounaroon A., Decker G., Schmidt J., Lottspeich F., and Kutchan T.M. (R, S)-Reticuline 7-O-methltransferase and (R, S)-norcoclaurine 6-O-methltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy. Plant J. 36 (2003) 808-819
28. Panicot M., Minguet E.G., Ferrando A., Alcazar R., Blazquez M.A., Carbonell J., Altabella T., Koncz C., and Tiburcio A.F. A polyamine metabolon involving aminopropyl transferase complexes in Arabidopsis. Plant Cell 14 (2002) 2539-2551
29. Pauli H.H., and Kutchan T.M. 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 monooxygenase of benzylisoquinoline alkaloid biosynthesis. Plant J. 13 (1998) 793-801
30. Pfaffl M.W. Quantification strategies in real-time PCR. In: Bustin S.A. (Ed). A-Z of Quantitative PCR. No. 5 (2004), International University Line, La Jolla 87-120
31. Rice K.C. Synthetic opium alkaloids and derivatives. A short total synthesis of (+)-dihydrothebainone, (+)-dihydrocodeinone, and (+)-nordihydrocodeinone as an approach to a practical synthesis of morphine, codeine, and congeners. J. Org. Chem 45 (1980) 3135-3137
32. Tattersall D.B., Bak S., Jones P.R., Olsen C.E., Nielsen J.K., Hansen M.L., Høj P.B., and Møller B.L. Resistance to an herbivore through engineered cyanogenic glucoside synthesis. Science 293 (2001) 1826-1828
33. Unterlinner B., Lenz R., and Kutchan T.M. Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum. Plant J. 18 (1999) 465-475
34. Verpoorte E., van der Heijden R., and Memelink J. Engineering the plant cell factory for secondary metabolite production. Trans. Res. 9 (2000) 323-343
35. Weid M., Ziegler J., and Kutchan T.M. The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy Papaver somniferum. Proc. Natl. Acad. Sci. USA 101 (2004) 13957-13962
36. Wesley S.V., Helliwell C.A., Smith N.A., Wang M., Rouse D.T., Liu Q., Gooding P.S., Singh S.P., Abbott D., Stoutjesdijk P.A., Robinson S.P., Gleave A.P., Green A.G., and Waterhouse P.M. Construct design for efficient, effective and high-throughput gene silencing in plants. Plant J. 27 (2001) 581-590
37. Winkel B.S.J. Metabolic channeling in plants. Annu. Rev. Plant Biol. 55 (2004) 85-107
38. Ziegler J., Voigtländer S., Schmidt J., Kramell R., Miersch O., Ammer C., Gesell A., and Kutchan T.M. Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis. Plant J. 48 (2006) 177-192