Characterization of the plastidial geraniol synthase from Madagascar periwinkle which initiates the monoterpenoid branch of the alkaloid pathway in internal phloem associated parenchyma

Phytochemistry

Volumn 85, Issue , 2013, Pages 36-43

  Simkin, Andrew J ^a,f   Miettinen, Karel ^b   Claudel, Patricia ^c   Burlat, Vincent ^d,e   Guirimand, Grégory ^a   Courdavault, Vincent ^a   Papon, Nicolas ^a   Meyer, Sophie ^c   Godet, Stéphanie ^a,g   St Pierre, Benoit ^a   Giglioli Guivarc'H, Nathalie ^a   Fischer, Marc J C ^c   Memelink, Johan ^b   Clastre, Marc ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b LEIDEN UNIVERSITY   (Netherlands)

^c UNIVERSITÉ DE STRASBOURG   (France)

^d UNIVERSITÉ DE TOULOUSE   (France)

^e Centre National de la Recherche Scientifique   (France)

^f UNIVERSITY OF ESSEX   (United Kingdom)

^g AGROCAMPUS OUEST   (France)

Author keywords

Alkaloid; Catharanthus roseus; Geraniol synthase; Internal phloem associated parenchyma

Indexed keywords

PHOSPHATASE; TERPENE; VEGETABLE PROTEIN;

ARTICLE; CATHARANTHUS; ENZYMOLOGY; GENE EXPRESSION REGULATION; METABOLISM; PHLOEM;

CATHARANTHUS; GENE EXPRESSION REGULATION, PLANT; MONOTERPENES; PHLOEM; PHOSPHORIC MONOESTER HYDROLASES; PLANT PROTEINS;

APOCYNACEAE; CATHARANTHUS; CATHARANTHUS ROSEUS; ESCHERICHIA COLI; SACCHAROMYCES CEREVISIAE;

EID: 84871290284     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.09.014     Document Type: Article

References (37)

1. V. Burlat, A. Oudin, M. Courtois, M. Rideau, and B. St-Pierre Co-expression of three MEP pathway genes and geraniol-10-hydroxylase in internal phloem parenchyma of Catharanthus roseus implicates multicellular translocation of intermediates during the biosynthesis of monoterpene indole alkaloids and isoprenoid-derived primary metabolites Plant J. 38 2004 131 141 (Pubitemid 38448450)
2. F. Chen, D. Tholl, J. Bohlmann, and E. Pichersky The family of terpene synthases in plants: a mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom Plant J. 66 2011 212 229
3. D.W. Christianson Structural biology and chemistry of the terpenoid cyclases Chem. Rev. 106 2006 3412 3442 (Pubitemid 44376943)
4. E. Coelho, R. Perestrelo, N.R. Neng, J.S. Câmara, M.A. Coimbra, J.M.F. Nogueira, and S.M. Rocha Optimisation of stir bar sorptive extraction and liquid desorption combined with large volume injection-gas chromatography- quadrupole mass spectrometry for the determination of volatile compounds in wines Anal. Chim. Acta 624 2008 79 89
5. G. Collu, N. Unver, A.M.G. Peltenburg-Looman, R. van der Heijden, R. Verpoorte, and J. Memelink Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis FEBS Lett. 508 2001 215 220 (Pubitemid 33079248)
6. M.J.C. Fischer, S. Meyer, P. Claudel, M. Bergdoll, and F. Karst Metabolic engineering of monoterpene synthesis in yeast Biotechnol. Bioeng. 108 2011 1883 1892
7. O.L. Gamborg, R.A. Miller, and K. Ojima Nutrient requirements of suspension cultures of soybean root cells Exp. Cell Res. 50 1968 151 158
8. P. Gantet, N. Imbault, M. Thiersault, and P. Doireau Necessity of a functional octadecanoic pathway for indole alkaloid synthesis by Catharanthus roseus cell suspension cultured in an auxin-starved medium Plant Cell Physiol. 39 1998 220 225 (Pubitemid 28129776)
9. G. Guirimand, V. Burlat, A. Oudin, A. Lanoue, B. St-Pierre, and V. Courdavault Optimization of the transient transformation of Catharanthus roseus cells by particle bombardment and its application to the subcellular localization of hydroxymethylbutenyl 4-diphosphate synthase and geraniol 10-hydroxylase Plant Cell Rep. 28 2009 1215 1234
10. G. Guirimand, V. Courdavault, A. Lanoue, S. Mahroug, A. Guihur, N. Blanc, N. Giglioli-Guivarc'h, B. St-Pierre, and V. Burlat Strictosidine activation in Apocynaceae: towards a "nuclear time bomb"? BMC Plant Biol. 10 2010 182
11. G. Guirimand, A. Guihur, O. Ginis, P. Poutrain, F. Héricourt, A. Oudin, A. Lanoue, B. St-Pierre, V. Burlat, and V. Courdavault The subcellular organization of strictosidine biosynthesis in Catharanthus roseus epidermis highlights several trans-tonoplast translocations of intermediate metabolites FEBS J. 278 2011 749 763
12. G. Guirimand, A. Guihur, P. Poutrain, F. Héricourt, S. Mahroug, B. St-Pierre, V. Burlat, and V. Courdavault Spatial organization of the vindoline biosynthetic pathway in Catharanthus roseus J. Plant Physiol. 168 2011 549 557
13. G. Guirimand, A. Guihur, M.A. Phillips, A. Oudin, G. Glévarec, C. Melin, N. Papon, M. Clastre, B. St-Pierre, M. Rodríguez- Concepción, V. Burlat, and V. Courdavault A single gene encodes isopentenyl diphosphate isomerase isoforms targeted to plastids, mitochondria and peroxisomes in Catharanthus roseus Plant Mol. Biol. 79 2012 443 459
14. Y. Iijima, D.R. Gang, E. Fridman, E. Lewinsohn, and E. Pichersky Characterization of geraniol synthase from the peltate glands of sweet basil Plant Physiol. 134 2004 370 379 (Pubitemid 38178709)
15. S. Irmler, G. Schroder, B. St-Pierre, N.P. Crouch, M. Hotze, J. Schmidt, D. Strack, U. Matern, and J. Schroder Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase Plant J. 24 2000 797 804 (Pubitemid 32100477)
16. M. Ito, and G. Honda Geraniol synthases from perilla and their taxonomical significance Phytochemistry 68 2007 446 453 (Pubitemid 46186439)
17. C.W. Lee-Parsons, and A.J. Royce Precursor limitation in methyl jasmonate-induced Catharanthus roseus cell cultures Plant Cell Rep. 25 2006 607 612 (Pubitemid 43787390)
18. C. Lin, B. Shen, Z. Xu, T.G. Kollner, J. Degenhardt, and H.K. Dooner Characterisation of the monoterpene synthase gene tps26, the ortholog of a gene induced by insect herbivory in maize Plant Physiol. 146 2008 940 951 (Pubitemid 352844109)
19. S. Mahroug, V. Courdavault, M. Thiersault, B. St-Pierre, and V. Burlat Epidermis is a pivotal site of at least four secondary metabolic pathways in Catharanthus roseus aerial organs Planta 223 2006 1191 1200
20. J.A. Morgan, and J.V. Shanks Determination of metabolic rate-limitations by precursor feeding in Catharanthus roseus hairy root cultures J. Biotechnol. 79 2000 137 145 (Pubitemid 30254205)
21. J. Murata, and V. De Luca Localization of tabersonine 16-hydroxylase and 16-OH tabersonine-16-O-methyltransferase to leaf epidermal cells defines them as a major site of precursor biosynthesis in the vindoline pathway in Catharanthus roseus Plant J. 44 2005 581 594
22. J. Murata, J. Roepke, H. Gordon, and V. De Luca The leaf epidermome of Catharanthus roseus reveals its biochemical specialization Plant Cell 20 2008 524 542 (Pubitemid 352843990)
23. D.A. Nagegowda, M. Gutensohn, C.G. Wilkerson, and N. Dudareva Two nearly identical terpene synthases catalyze the formation of nerolidol and linalool in snapdragon flowers Plant J. 55 2008 224 239
24. S.K. Natesan, J.A. Sullivan, and J.C. Gray Stromules: a characteristic cell-specific feature of plastid morphology J. Exp. Bot. 56 2005 787 797 (Pubitemid 40428381)
25. B.K. Nelson, X. Cai, and A. Nebenführ A multicolored set of in vivo organelle markers for co-localization studies in Arabidopsis and other plants Plant J. 51 2007 1126 1136 (Pubitemid 47373577)
26. M. Oswald, M. Fischer, N. Dirninger, and F. Karst Monoterpenoid biosynthesis in Saccharomyces cerevisiae FEMS Yeast Res. 7 2007 413 421 (Pubitemid 46555504)
27. A. Oudin, M. Courtois, M. Rideau, and M. Clastre The iridoid pathway in Catharanthus roseus alkaloid biosynthesis Phytochem. Rev. 6 2007 259 276 (Pubitemid 46870976)
28. A. Oudin, S. Mahroug, V. Courdavault, N. Hervouet, C. Zelwer, M. Rodriguez-Concepcion, B. St-Pierre, and V. Burlat Spatial distribution and hormonal regulation of gene products from methyl erythritol phosphate and monoterpene-secoiridoid pathways in Catharanthus roseus Plant Mol. Biol. 65 2007 13 30 (Pubitemid 47247222)
29. M. Schattat, K. Barton, B. Baudisch, R.B. Klösgen, and J. Mathur Plastid stromule branching coincides with contiguous endoplasmic reticulum dynamics Plant Physiol. 155 2011 1667 1677
30. B. St-Pierre, F.A. Vazquez-Flota, and V. de Luca Multicellular compartmentation of Catharanthus roseus alkaloid biosynthesis predicts intercellular translocation of a pathway intermediate Plant Cell 11 1999 887 900
31. G. Turner, J. Gershenzon, E.E. Nielson, J.E. Froehlich, and R. Croteau Limonene synthase, the enzyme responsible for monoterpene biosynthesis in peppermint, is localized to leucoplasts of oil gland secretory cells Plant Physiol. 120 1999 879 886 (Pubitemid 29384518)
32. L. van der Fits, and J. Memelink ORCA3, a jasmonate-responsive transcriptional regulator of plant primary and secondary metabolism Science 289 2000 295 297 (Pubitemid 30469906)
33. L. van der Fits, and J. Memelink The jasmonate-inducible AP2/ERF-domain transcription factor ORCA3 activates gene expression via interaction with a jasmonate-responsive promoter element Plant J. 25 2001 43 53 (Pubitemid 32143325)
34. R. van der Heijden, D.I. Jacobs, W. Snoeijer, D. Hallard, and R. Verpoorte The Catharanthus alkaloids: pharmacognosy et biotechnology Curr. Med. Chem. 11 2004 1241 1253
35. T. Yang, J. Li, H.X. Wang, and Y. Zeng A geraniol-synthase gene from Cinnamomum tenuipilum Phytochemistry 66 2005 285 293 (Pubitemid 40169988)
36. T. Yang, G. Stoopen, N. Yalpani, J. Vervoort, R. de Vos, A. Voster, F.W. Verstappen, H.J. Bouwmeester, and M.A. Jongsma Metabolic engineering of geranic acid in maize to achieve fungal resistance is compromised by novel glycosylation patterns Metab. Eng. 13 2011 414 425
37. M.L. Zhou, H.L. Hou, X.M. Zhu, J.R. Shao, Y.M. Wu, and Y.X. Tang Molecular regulation of terpenoid indole alkaloids pathway in the medicinal plant, Catharanthus roseus J. Med. Plants Res. 5 2011 663 676