Terpenoid indole alkaloid biosynthesis

Cathenamine (100) has been identified as an early intermediate in terpenoid indole alkaloid biosynthesis (cf. Vol. 8, p. 27). It has also been isolated from Guettarda eximia. Another alkaloid, 4,21-dehydrogeissoschizine (99), has now been isolated from this plant it is readily converted into (100) in alkaline solution.29 On incubation with an enzyme preparation from Catharanthus roseus cell cultures in the presence of NADPH at pH 7, (99) was converted into ajmalicine (102), 19-ep/-ajmalicine (103), and tetrahydroalstonine (104), which are the normal products with this enzyme preparation. In the absence of NADPH, cathenamine (100) accumulated.30 The reaction to give (100) proceeded linearly with time, and was dependent on the concentration of protein and substrate. No conversion occurred in the absence of enzyme. 

Figure 7.9 Intercellular and subcellular trafficking in alkaloid biosynthesis. A. Tropane alkaloid biosynthesis in Hyoscyamus muticus. B. Terpenoid indole alkaloid biosynthesis in Catharanthus roseus. C. Trafficking of the berberine bridge enzyme in Papaver somniferum cell cultures.

COLLU, G., UNVER, N., PELTENBURG-LOOMAN, A.M.G., VAN DER HEIJDEN, R., VERPOORTE, R MEMELINK, J., Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis. FEBSLett., 2001, 508,215-220. 

GEERLINGS, A., MARTINEZ-LOZANO IBANEZ, M., MEMELINK, J., VAN DER HEIJDEN, R., VERPOORT, R., Molecular cloning and analysis of strictosidine P-D-glucosidase, an enzyme in terpenoid indole alkaloid biosynthesis in Catharanthus roseus. J. Biol. Chem., 2000,275,3051-3056. 

MEIJER, A.H., VERPOORTE, R., HOGE, J.H.C., Regulation of enzymes and genes involved in terpenoid indole alkaloid biosynthesis in Catharanthus roseus. J. Plant Res., 1993, Special Issue 3, 145-164. 

Goddijn, O.J.M. (1992) Regulation of terpenoid indole alkaloid biosynthesis in Catha-ranthus roseus the tryptophan decarboxylase gene. Ph.D. Thesis, Leiden University. 

Rischer, H., Oresic, M., Seppanen-Laakso, T., Katajamaa, M., Lammertyn, R, Ardiles-Diaz, W., von Montagu, M.C.E., Inze, D., Oksman-Caldentey, K.-M. and Goosens, A. (2006) Gene-to-metabolite networks for terpenoid indole alkaloid biosynthesis in Catharanthus roseus cells. Proc. Natl. Acad. Sci. USA, 103,5614—9. 

Early steps of terpenoid indole alkaloid biosynthesis... 

Here we discuss the intermediates and enzymes involved in the terpenoid indole alkaloid biosynthesis, following the subdivision into the five parts mentioned earlier (Fig. 2). In Table II the characteristics of the various... 

Terpenoid indole alkaloid biosynthesis actually starts with the coupling of tryptamine and secologanin (Fig. 12). In the next step, a glucosidase splits off the sugar moiety and the reactive dialdehyde formed is further converted through different pathways to a cascade of products, including ajmalicine, catharanthine, tabersonine, and vindoline. 

Riseher H, Oresie M, Seppanen-Laakso T, Kata-jamaa M, Lammertyn F, Ardiles-Diaz W, Van Montagu MC, Inze D, Oksman-Caldentey KM, Goossens A (2006) Gene-to-metabolite networks for terpenoid indole alkaloid biosynthesis in Cath-aranthus roseus cells. Proc Natl Acad Sci USA 103 5614-5619... 

Overexpression of Enzymes Involved in Terpenoid Indole Alkaloid Biosynthesis... 

Incorporation of Genes from the Terpenoid Indole Alkaloid Biosynthesis in Other Plants and Microorganisms... 

Shukla AK, Shasany AK, Verma RK, Gupta MM, Mathur AK, Khanuja PSP (2010) Influence of cellular differentiation and elicitation on intermediate and late steps of terpenoid indole alkaloid biosynthesis in Catharanthus roseus. Protoplasma 24 35-47. doi 10.1007/s00709-010-0120-1... 

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