Norcoclaurine synthase is a member of the pathogenesis-related 10/Bet v1 protein family

Plant Cell

Volumn 22, Issue 10, 2010, Pages 3489-3503

  Lee, Eun Jeong ^a   Facchini, Peter ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COPTIS; COPTIS JAPONICA; PAPAVER SOMNIFERUM; THALICTRUM; THALICTRUM FLAVUM;

EID: 78649499936     PISSN: 10404651     EISSN: 1532298X     Source Type: Journal    
DOI: 10.1105/tpc.110.077958     Document Type: Article

References (53)

1. Alcantara, J., Bird, D.A., Franceschi, V.R., and Facchini, P.J. (2005). Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment. Plant Physiol. 138: 173-183.
2. Amann, M., Wanner, G., and Zenk, M.H. (1986). Intracellular compartmentation of two enzymes of berberine biosynthesis in plant cell cultures. Planta 167: 310-320.
3. Ames, B.D., Korman, T.P., Zhang, W., Smith, P., Vu, T., Tang, Y., and Tsai, S.-C. (2008). Crystal structure and functional analysis of tetracenomycin ARO/CYC: Implications for cyclization specificity of aromatic polyketides. Proc. Natl. Acad. Sci. USA 105: 5349-5354.
4. Bais, H.P., Vepachedu, R., Lawrence, C.B., Stermitz, F.R., and Vivanco, J.M. (2003). Molecular and biochemical characterization of an enzyme responsible for the formation of hypericin in St. John's wort (Hypericum perforatum L.). J. Biol. Chem. 278: 32413-32422.
5. Berkner, H., Schweimer, K., Matecko, I., and Rösch, P. (2008). Conformation, catalytic site, and enzymatic mechanism of the PR10 allergen-related enzyme norcoclaurine synthase. Biochem. J. 413: 281-290.
6. Bonamore, A., Barba, M., Botta, B., Boffi, A., and Macone, A. (2010). Norcoclaurine synthase: Mechanism of an enantioselective pictetspengler catalyzing enzyme. Molecules 15: 2070-2078.
7. Bradford, M.M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of proteindye binding. Anal. Biochem. 72: 248-254.
8. Bird, D.A., and Facchini, P.J. (2001). Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar sorting determinant. Planta 213: 888-897.
9. Bird, D.A., Franceschi, V.R., and Facchini, P.J. (2003). A tale of three cell types: alkaloid biosynthesis is localized to sieve elements in opium poppy. Plant Cell 15: 2626-2635.
10. Bufe, A., Spangfort, M.D., Kahlert, H., Schlaak, M., and Becker, W.M. (1996). The major birch pollen allergen, Bet v 1, shows ribonuclease activity. Planta 199: 413-415.
11. Britsch, L., Dedio, J., Saedler, H., and Forkmann, G. (1993). Molecular characterization of flavanone 3 b-hydroxylases. Consensus sequence, comparison with related enzymes and the role of conserved histidine residues. Eur. J. Biochem. 217: 745-754.
12. Chadha, P., and Das, R.H. (2006). A pathogenesis related protein, AhPR10 from peanut: An insight of its mode of antifungal activity. Planta 225: 213-222.
13. Davies, K.M. (1993). A Malus cDNA with homology to Anthirrhinum candida and Zea A2 genes. Plant Physiol. 103: 1015.
14. De-Eknamkul, W., Ounaroon, A., Tanahashi, T., Kutchan, T.M., and Zenk, M.H. (1997). Enzymatic condensation of dopamine and secologanin by cell-free extracts of Alangium lamarckii. Phytochemistry 45: 477-484.
15. Dinesh-Kumar, S.P., Anandalakshmi, R., Marathe, R., Schiff, M., and Liu, Y. (2003). Virus-induced gene silencing. Methods Mol. Biol. 236: 287-294.
16. Facchini, P.J., Johnson, A.G., Poupart, J., and de Luca, V. (1996). Uncoupled defense gene expression and antimicrobial alkaloid accumulation in elicited opium poppy cell cultures. Plant Physiol. 111: 687-697.
17. Fujimoto, Y., Nagata, R., Fukasawa, H., Yano, K., Azuma, M., Iida, A., Sugimoto, S., Shudo, K., and Hashimoto, Y. (1998). Purification and cDNA cloning of cytokinin-specific binding protein from mung bean (Vigna radiata). Eur. J. Biochem. 258: 794-802.
18. Gamborg, O.L., Miller, R.A., and Ojima, K. (1968). Nutrient requirements of suspension cultures of soybean root cells. Exp. Cell Res. 50: 151-158.
19. Hagel, J.M., and Facchini, P.J. (2010a). Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy. Nat. Chem. Biol. 6: 273-275.
20. Hagel, J.M., and Facchini, P.J. (July 15, 2010b.) Biochemistry and occurrence of O-demethylation in plant metabolism. Front. Physio. 1 (online), doi/10.3389/fphys.2010.00014.
21. Hausinger, R.P. (2004). Fe(II)/a-ketoglutarate-dependent hydroxylases and related enzymes. Crit. Rev. Biochem. Mol. Biol. 39: 21-68.
22. Hileman, L.C., Drea, S., Martino, G., Litt, A., and Irish, V.F. (2005). Virus-induced gene silencing is an effective tool for assaying gene function in the basal eudicot species Papaver somniferum (opium poppy). Plant J. 44: 334-341.
23. Hirose, T., Sunazuka, T., Zhi-Ming, T., Handa, M., Uchida, R., Shiomi, K., Harigaya, Y., and Omura, S. (2000). Total syntheses of kurasoins a and b, novel protein farnesyltransferase inhibitors, and absolute structures of kurasoins a and b. Heterocycles 53: 777-784.
24. Holdsworth, M.J., Bird, C.R., Ray, J., Schuch, W., and Grierson, D. (1987). Structure and expression of an ethylene-related mRNA from tomato. Nucleic Acids Res. 15: 731-739.
25. Holton, T.A., Brugliera, F., and Tanaka, Y. (1993). Cloning and expression of flavonol synthase from Petunia hybrida. Plant J. 4: 1003-1010.
26. Ilari, A., Franceschini, S., Bonamore, A., Arenghi, F., Botta, B., Macone, A., Pasquo, A., Bellucci, L., and Boffi, A. (2009). Structural basis of enzymatic (S)-norcoclaurine biosynthesis. J. Biol. Chem. 284: 897-904.
27. Kovaleva, E.G., and Lipscomb, J.D. (2008). Versatility of biological non-heme Fe(II) centers in oxygen activation reactions. Nat. Chem. Biol. 4: 186-193.
28. Liscombe, D.K., MacLeod, B.P., Loukanina, N., Nandi, O.I., and Facchini, P.J. (2005). Evidence for the monophyletic evolution of benzylisoquinoline alkaloid biosynthesis in angiosperms. Phytochemistry 66: 2501-2520.
29. Logemann, J., Schell, J., and Willmitzer, L. (1987). Improved method for the isolation of RNA from plant tissues. Anal. Biochem. 163: 16-20.
30. Loenarz, C., and Schofield, C.J. (2008). Expanding chemical biology of 2-oxoglutarate oxygenases. Nat. Chem. Biol. 4: 152-156.
31. Luk, L.Y., Bunn, S., Liscombe, D.K., Facchini, P.J., and Tanner, M.E. (2007). Mechanistic studies on norcoclaurine synthase of benzylisoquinoline alkaloid biosynthesis: An enzymatic Pictet-Spengler reaction. Biochemistry 46: 10153-10161.
32. Ma, X., Panjikar, S., Koepke, J., Loris, E., and Stöckigt, J. (2006). The structure of Rauvolfia serpentina strictosidine synthase is a novel sixbladed b-propeller fold in plant proteins. Plant Cell 18: 907-920.
33. Matsuda, J., Okabe, S., Hashimoto, T., and Yamada, Y. (1991). Molecular cloning of hyoscyamine 6 b-hydroxylase, a 2-oxoglutaratedependent dioxygenase, from cultured roots of Hyoscyamus niger. J. Biol. Chem. 266: 9460-9464.
34. Michalska, K., Fernandes, H., Sikorski, M., and Jaskolski, M. (2010). Crystal structure of Hyp-1, a St. John's wort protein implicated in the biosynthesis of hypericin. J. Struct. Biol. 169: 161-171.
35. Minami, H., Dubouzet, E., Iwasa, K., and Sato, F. (2007). Functional analysis of norcoclaurine synthase in Coptis japonica. J. Biol. Chem. 282: 6274-6282.
36. Minami, H., Kim, J.-S., Ikezawa, N., Takemura, T., Katayama, T., Kumagai, H., and Sato, F. (2008). Microbial production of plant benzylisoquinoline alkaloids. Proc. Natl. Acad. Sci. USA 105: 7393-7398.
37. Nessler, C.L., Allen, R.D., and Galewsky, S. (1985). Identification and characterization of latex-specific proteins in opium poppy. Plant Physiol. 79: 499-504.
38. Osmark, P., Boyle, B., and Brisson, N. (1998). Sequential and structural homology between intracellular pathogenesis-related proteins and a group of latex proteins. Plant Mol. Biol. 38: 1243-1246.
39. Page, R.D. (1996). Tree View: An application to display phylogenetic trees on personal computers. Comput. Appl. Biosci. 12: 357-358.
40. Ramón, D., Carramolino, L., Patiño, C., Sánchez, F., and Peñalva, M.A. (1987). Cloning and characterization of the isopenicillin N synthetase gene mediating the formation of the b-lactam ring in Aspergillus nidulans. Gene 57: 171-181.
41. Rotenberg, D., Thompson, T.S., German, T.L., and Willis, D.K. (2006). Methods for effective real-time RT-PCR analysis of virus-induced gene silencing. J. Virol. Methods 138: 49-59.
42. Samanani, N., Alcantara, J., Bourgault, R., Zulak, K.G., and Facchini, P.J. (2006). The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy. Plant J. 47: 547-563.
43. Samanani, N., and Facchini, P.J. (2001). Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy. Planta 213: 898-906.
44. Samanani, N., and Facchini, P.J. (2002). Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants. J. Biol. Chem. 277: 33878-33883.
45. Samanani, N., Liscombe, D.K., and Facchini, P.J. (2004). Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis. Plant J. 40: 302-313.
46. Samanani, N., Park, S.U., and Facchini, P.J. (2005). Cell typespecific localization of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis. Plant Cell 17: 915-926.
47. Schmidt, J., Raith, K., Boettcher, C., and Zenk, M.H. (2005). Analysis of benzylisoquinoline-type alkaloids by electrospray tandem mass spectrometry and atmospheric pressure photoionization. Eur. J. Mass Spectrom. (Chichester, Eng.) 11: 325-333.
48. Shockey, J.M., Gidda, S.K., Chapital, D.C., Kuan, J.-C., Dhanoa, P.K., Bland, J.M., Rothstein, S.J., Mullen, R.T., and Dyer, J.M. (2006). Tung tree DGAT1 and DGAT2 have nonredundant functions in triacylglycerol biosynthesis and are localized to different subdomains of the endoplasmic reticulum. Plant Cell 18: 2294-2313.
49. Stadler, R., Kutchan, T.M., and Zenk, M.H. (1989). (S)-Norcoclaurine is the central intermediate in benzylisoquinoline alkaloid biosynthesis. Phytochemistry 28: 1083-1086.
50. Swoboda, I., Hoffmann-Sommergruber, K., O'Ríordáin, G., Scheiner, O., Heberle-Bors, E., and Vicente, O. (1996). Bet v1 proteins, the major birch pollen allergens and members of a family of conserved pathogenesis-related proteins, show ribonuclease activity in vitro. Physiol. Plant. 96: 433-438.
51. Vazquez-Flota, F., De Carolis, E., Alarco, A.M., and De Luca, V. (1997). 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 Mol. Biol. 34: 935-948.
52. Ziegler, J., and Facchini, P.J. (2008). Alkaloid biosynthesis: Metabolism and trafficking. Annu. Rev. Plant Biol. 59: 735-769.
53. Zulak, K.G., Cornish, A., Daskalchuk, T.E., Deyholos, M.K., Goodenowe, D.B., Gordon, P.M., Klassen, D., Pelcher, L.E., Sensen, C.W., and Facchini, P.J. (2007). Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism. Planta 225: 1085-1106.