Catharanthus roseus, terpenoid indole biosynthesis

Catharanthus roseus, biosynthesis of terpenoid indole alkaloids in, 49, 222 (1997) Celastraceae alkaloids, 16, 215 (1977)... 

Verpoorte R, van der Heijden R and Moreno PRH (1997) Biosynthesis of terpenoid indole alkaloids in Catharanthus roseus cells. The Alkaloids, Chemistry and Pharmacology (ed Cordell GA) Vol 49. Academic, San Diego, pp 221-299. 

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. 

Terpenoid Indole Alkaloids.—Current knowledge on the biosynthesis of terpenoid indole alkaloids, with particular emphasis on the very important results obtained with enzyme preparations from tissue cultures of Catharanthus roseus, has been authoritatively reviewed.53 Further work on cell lines of C. roseus that are able to produce Aspidosperma-type alkaloids has been published54 (cf. Vol. 11, p. 19). 

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.

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. 

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. 

Terpenoid Indole Alkaloids.—Crude preparations from Catharanthus roseus seedlings and from tissue cultures have been shown to be capable of synthesizing in good yield from tryptamine (110) and secologanin (111) with added co-factors, geisso-schizine (112) and ajmalicine (113), representatives of the first major class of terpenoid indole alkaloids (Corynanthe). Geissoschizine was metabolized to ajmalicine and several other unidentified alkaloids (for reviews of biosynthesis in intact plants see ref. 106). The catabolic turnover of vindoline and catharanthine in C. roseus has been studied. ... 

Fig. (4). Early steps of the biosynthesis of terpenoid indole alkaloids in Catharanthus roseus. Triple arrowheads indicate multiple steps. G10H geraniol 16-hydroxylase TDC tryptophan decarboxylase STR strictosidine synthase.

BIOSYNTHESIS OF TERPENOID INDOLE ALKALOIDS IN Catharanthus roseus CELLS... 

In the present review we divide the pathway leading to the Catharanthus alkaloids into five parts (Fig. 2). The first two concern the biosynthesis of tryptophan and geraniol diphosphate they are similar to (or even part of) primary metabolism and occur in all plant species. Whether these pathways in C. roseus are differently regulated, or whether even an additional pathway exists parallel to the normal primary metabolism, is a question not yet answered. The third and the fourth part coneern the steps from tryptophan to tryptamine and from geraniol to secologanin, respectively. Both pathways occur also in other plants, including plants that do not produce terpenoid indole alkaloids. The fifth part is the condensation of secologanin and tryptamine to strictosidine and the subsequent conversion into a plethora... 

Indicative Range of Activities of Some Enzymes Involved in the Biosynthesis of Terpenoid Indole Alkaloids in Catharanthus roseus Suspension-Cultured Cells"... 

O. J. M. Goddijn, Regulation of terpenoid indole alkaloid biosynthesis in Catharanthus roseus." Ph.D. Thesis, Leiden University, 1992. 

Terpenoid Indole Alkaloids.—It has been confirmed recently for ajmalicine (84), vindoline (89), and catharanthine (90), in Catharanthus roseus Vinca rosea) that strictosidine (79), and not vincoside (86), is the key intermediate in terpenoid alkaloid biosynthesis cf. ref. 9). 

Sottomayor M, Lopes Cardoso I, Pereira LG, Ros Barcelo A (2004) Peroxidase and the biosynthesis of terpenoid indole alkaloids in the medicinal plant Catharanthus roseus (L.) G. Don. Phytochem Rev 3 159-171. doi 10.1023/B PHYT.0000047807.66887.09... 

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... 

Jasmonate Signalling in Terpenoid Indole Alkaloid Biosynthesis in Catharanthus roseus... 

Liu, D.H. et al. (2007) Terpenoid Indole Alkaloids biosynthesis and metabolic engineering in Catharanthus roseus. JIntegrat. Plant Biol. 49, 961-974... 

Kulshrestha, M., Patra, B. et al. (2011) The transcription factor CrWRKYl positively regulates the terpenoid indole alkaloid biosynthesis in Catharanthus roseus. Plant Physiol, 157, 2081-2093. 

---