Abstract
Plants possess the inherent ability to produce unique natural product chemistries as a result of differences that have been selected for throughout evolution. Selection through gene mutation and subsequent adaptation of metabolic pathways create new secondary products. The biosynthesis and accumulation of many secondary products, however, remain under remarkable control of the biotic and abiotic environments. The readiness of secondary metabolic pathways to sense the environment appears to be intimitely related to their ability to evolve and is represented by the existence of several hundred thousand plant-based secondary metabolites. Catharanthus roseus which produces nearly 200 different monoterpenoid indole alkaloids, displays a cell- tissue- development- and environment-specific control over their biosynthesis and accumulation. This chapter describes the experimental approaches which have helped to understand various aspects of indole alkaloid biosynthesis in Catharanthus and which make it a good model system to study its regulation.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Balsevich J, De Luca V, Kurz WGW (1986) Altered alkaloid pattern in dark grown seedlings of Catharanthus roseus. The isolation and characterization of 4-desacetoxyvindoline: A novel indole alkaloid and proposed precursor of vindoline. Heterocycles 24: 2415–2421.
Bristsch L, Dedio J, Saedler H, Forkmann G (1993) Molecular characterization of flavanone 3ß-hydroxylases. Consensus sequence, comparison with related enzyme and the role of conserved histidine residues. Eur J Biochem 217: 745–754.
Constabel F, Gaudet LaPraire P, Kurz WGW, Kutney JP (1982) Alkaloid production in Catharanthus roseus cell cultures XII. Biosynthetic capacity of callus from original explants and regenerated shoots Plant Cell Rep 1: 139–142.
Cutler, A., Mersey, B (1986) Differential distribution of specific indole alkaloids in leaves of Catharanthus roseus. Can J Bot 64: 1039–1045.
Davis KM (1993) A Malus cDNA with homology to Anthirrhinun Candida and Zlea A2 genes. Plant Physiol 103: 1015.
De Carolis E, Chan F, Balsevich J, De Luca V (1990) Isolation and characterization of a 2-oxoglutarate dependent dioxygenase involved in the second-to-last step in vindoline biosynthesis. Plant Physiol 94: 1323–1329.
De Carolis and V. De Luca (1993) Purification to homogeneity and characterization of a 2-oxoglutarate dependent dioxygenase involved in vindoline biosynthesis in Catharanthus roseus. J. Biol. Chem. 268: 5504–5511.
De Luca V, Cutler AJ (1987) Subcellular localization of enzyme involved in indole alkaloid biosynthesis in Catharanthus roseus. Plant Physiol 85: 1099–1102.
De Luca V, Balsevich J, Tyler RT, Kurz WGW (1987) Characterization of a novel A/-methyltransferase (NMT) from Catharanthus roseus. Plant Cell Rep 6: 458–461.
De Luca V, Marineau C, Brisson N (1989) Molecular cloning and analysis of cDNA encoding a plant tryptophan decarboxylase: comparison with animal dopa decarboxylase. Proc Nat Acad Sci USA 86: 2582–2586.
De Luca V (1993) Indole Alkaloid Biosynthesis. In Methods in Plant Biochemistry. “Enzymes of Secondary Metabolism” (P. Lea ed.) 9: 345–368 Academic Press.
De Luca V, R. Aerts, S. Chavadej, E. De Carolis and A.M. Alarco (1993) The biosynthesis of monoterpenoid indole alkaloids in Catharanthus roseus. In Current Topics in Plant Physiology, Proceedings of the Seventh Annual Penn. State Symposium, “Biosynthesis of Amino Acids”, (H.E. Flores and B.K. Singh, eds). 6: 275–284.
De Luca V, W.G.W. Kurz (1988) Monoterpenoid Indole Alkaloids. In Cell Culture and Somatic Cell Genetics of Plants (F. Constabel and I Vasil, eds.) De Luca V, W.G.W. Kurz: 385–401, Academic Press.
Dethier M. and V. De Luca (1993) Partial purification of an N-methyltransferase which catalyses the third to last step in vindoline biosynthesis in Catharanthus roseus. Phytochemistiy 32: 673–678.
Farnsworth NR (1975) The Catharanthus alkaloids ( WI Taylor and NR Farnsworth eds) M.Dekker, New York.
Fahn W, Lausermair E, Deus-Neumann B, Stöckigt J (1985) The late enzymes in vindoline biosynthesis. S-adenosyl-L-Methionine: 11-O-demethy1-17-O- deacetylvindoline ll-O-methyltransferase, and unspecific acetylesterase. Plant Cell Rep 4: 337–340.
Fahn W, Stockigt J (1990) Purification of acetyl-CoA: 17-0-deacetyl 17-0- acetyltransferase from Catharanthus roseus leaves. Plant Cell Rep 8: 613–616.
Frohman MA, Dush MK, Martin GR (1988) Rapid production of fall length cDNAs from rare transcripts: Amplification using a single gene-specific oligonucleotide primer. Proc Nat. Acad Sci USA 85: 8998–9002.
Holdsworth MJ, Bird CR, Ray J, Schuch W, Grierson D (1987) Structure and expression of an ethylene-related mRNA from tomato. Nuc Acid Res 15: 731–739.
Holton TA, Brugleira F, Tanaka Y (1993) Cloning and expression of flavonol synthase from Petunia hybrida. Plant J. 4: 1003–1010.
Hotz M, Schroder G, Schröder J (1995) Cinnamate 4-hydroxylase from Catharanthus roseus, and a strategy for the functional expression of plant cytochrome P450 proteins as translational fusions with P450 reductase in Escherichia coli FEBS Letters 374: 345–350.
Kutney JP, Hibino T, Jahngen E, Okutani T, Ratcliffe AH, Treasurywala AM, Wunderly S (1976) Total synthesis of indole and dihydroindole alkaloids. IX. Studies on the synthesis of bisindole alkaloids in the vinblastine-vincristine series. The biogenetic approach. (1976) Helv Chim Acta 59: 2858–2882.
Langlois N., Gueritte F., Langlois Y., Potier P (1976) Application of a modification of the Polonovski reaction to the synthesis of vinblastine-type alkaloids. J Am Chem Soc 98: 7017–7024.
Lingner J, Kellermann J, Keller W: (1991) Cloning and expression of the essential gene for poly(A) polymerase from S. cerevisiae. Nature 354: 496–498.
Matsuda J, Okabe S, Hashimoto T, Yamada Y (1991)Molecular cloning of hyoscyamine 6B-hydroxylase, a 2–oxoglutarate-dependent dioxygenase from cultured roots of Hyoscyamus niger. J Biol Chem 226: 9460–9464.
Matsuda, A., Sugiura, A., Matsuyama, K., Matsumoto, H., Ichikawa, S., Komatsu, K (1992) Molecular cloning of acetyl Co A: deacetylcephalosporin C O- acetyltransferase cDNA from Acremonium chrysogenium: sequence and expression of catalytic activity in yeast. Biochem. Biophys. Res. Comm. 182: 995–1001.
McKnight TD, Roessner CA, Devagupta R, Scott AI, Nessler CI (1990) Nucleotide sequence of a cDNA encoding the vacuolar protein strictosidine synthase from Catharanthus roseus. Nucl Acids Res 18: 4939.
McKnight TD, Bergey DR, Burnett RJ, Nessler CL (1991) Expression of enzymatically active and correctly targeted strictosidine synthase in transgenic tobacco plants. Planta 185: 148–152.
Meijer AM, Verpoorte R, Hoge JH (1993a) Regulation of enzymes and genes involved in terpenoid indole alkaloid biosyntheis in Catharanthus roseus. J. Plant Res. Special Issue 3: 145–164.
Meijer AM, Sour E, Verpoorte R, Hoge JH (1993b) Isolation of cytochrome P450 cDNA clones from the higher plant Catharanthus roseus by a PCR strategy. Plant Mol Biol 22: 379–383.
O’Keefe BR, Mahady GB, Gills JJ, Beecher CWW (1997) Stable vindoline production in transformed cell cultures of Catharanthus roseus. J Nat Prod 60:261–264.
Phillips A, Ward DA, Ukness S, Appleford NEJ, Lange T, Huttly AK, Gaskin, P, Graebe JE, Hedden P (1995) Isolation and expression of three gibberellin 20-oxidase cDNA clones from Arabidopsis. Plant Physiol 108: 1049–1057.
Power R, Kurz WGW, De Luca V (1990) Purification and characterization of acetylcoenzyme A:deacetylvindoline 4-O-acetyltransferase from Catharanthus roseus. Arch Biochem Biophys 279: 370–376.
Ramon D, Carramolino L, Patiño C, Sánchez F, Peñtalva MA (1987) Cloning and characterization of the isopenicillin N synthase gene mediating the formation of the ß-lactam ring in Aspergillus nidulans. Gene 57: 171–181.
Shaw WV, Leslie AGW (1991) Chloramphenicol acetyltransferase. Ann Rev Biophys Chem 20: 363–386.
St-Pierre B, De Luca V (1995) A cytochrome P450 monooxygenase catalyzes the first step in the conversion of tabersonine to vindoline in Catharanthus roseus. Plant Physiol 109: 131–139.
St-Pierre B, Laflamme P, Alarco AM, De Luca V (1997) Molecular cloning and characterization of DAT from Catharanthus roseus. Submitted for publication.
Van der Heijden R, Verpoorte R, Ten Hoopen HJG (1989) Cell and tissue cultures of Catharanthus roseus (L.) G. Don: a literature survey. Plant Cell Tissue Org Culture 18: 231–280.
Vazquez-Flota F, De Carolis E, Alarco AM, 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.
Wu D, Ahmed SN, Lian W, Hersh LB (1995) Activation of rat choline acetyltransferase by limited proteolysis. J. Biol. Chem 270: 19395–19401.
Yoder LR, Mahlberg PG: (1976) Reactions of alkaloid and histochemical indicators in laticifers and specialized parenchyma of Catharanthus roseus. Am J Bot 63: 1167– 1173.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1998 Springer-Verlag Berlin Heidelberg
About this paper
Cite this paper
De Luca, V., St-Pierre, B., Vazquez Flota, F., Laflamme, P. (1998). Indole Alkaloid Biosynthesis in Catharanthus roseus: The Establishment of a Model System. In: Lo Schiavo, F., Last, R.L., Morelli, G., Raikhel, N.V. (eds) Cellular Integration of Signalling Pathways in Plant Development. NATO ASI Series, vol 104. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-72117-5_16
Download citation
DOI: https://doi.org/10.1007/978-3-642-72117-5_16
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-72119-9
Online ISBN: 978-3-642-72117-5
eBook Packages: Springer Book Archive