Abstract
The relation between the total alkaloid content and the activity of strictosidine synthase (EC 4.3.3.2), a key enzyme in alkaloid biosynthesis, was studied in distinct parts of six-month-old plants of Cinchona ledgeriana Moens. Strictosidine-synthase activity was present in the tops of the stems, including the young developing leaflets, and in the roots. The highest alkaloid contents of the plant were also found in these parts; however, the types of alkaloids differed, cinchophyllines being present in the aerial parts and quinoline alkaloids in the roots. In the stem and in old leaves, both strictosidine-synthase activity and alkaloid content were low. These results indicate that in young Cinchona plants the alkaloids are mainly synthesized in the axial extremities of the plant and that they are stored at the site of their synthesis.
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Abbreviations
- HPLC:
-
high-performance liquid chromatography
- SSS:
-
strictosidine synthase
References
Aerts, R.J., Van der Leer, T., Van der Heijden, R., Verpoorte, R. (1990) Developmental regulation of alkaloid production in Cinchona seedlings. J. Plant Physiol. 136, 86–91
Bernays, E.A., Chapman, R.F. (1976) Antifeedant properties of seedling grasses. In: The host-plant in relation to insect behaviour and reproduction, pp. 41–46, Jermy, T., ed. Symp. Biol. Hung. 16, Plenum Press, New York
Cordell, G.A. (1981) Introduction to alkaloids. A biogenetic approach. Wiley, New York
Davies, P.J. (1987) The plant hormones: their nature, occurrence, and functions. In: Plant hormones and their role in plant growth and development, pp. 1–11, Davies, P.J., ed. Martinus Nijhoff, Dordrecht
De Luca, V., Fernandez, J.A., Campbell, D., Kurz, W.G.W. (1988) Developmental regulation of enzymes of indole alkaloid biosynthesis in Catharanthus roseus. Plant Physiol. 86, 447–450
De Moerloose, P. (1954) Studie met behulp van het koolstofisotoop C14 over de biosynthese van de kina-alkaloïden. Pharm. Weekbl. 89, 541–572
De Vrij, J.E. (1896) Kinologische Studien, no 10. Ned. Tijdschr. Pharm. Chem. Tox., 101–105
Eilert, U., De Luca, V., Constabel, F., Kurz, W.G.W. (1987) Elicitor-mediated induction of tryptophan decarboxylase and strictosidine synthase activities in cell suspension cultures of Catharanthus roseus. Arch. Biochem. Biophys. 254, 491–497
Evans, W.H. (1987) In: Biological membranes, pp. 1–35, Findlay, J.B.C., Evans, W.H., eds. IRL Press, Oxford
Frischknecht, P.M., Ulmer-Dufek, J., Baumann, T.W. (1986) Purine alkaloid formation in buds and developing leaflets of Coffea arabica: expression of an optimal defence strategy? Phytochemistry 25, 613–616
Frischknecht, P.M., Bättig, M., Baumann, T.W. (1987) Effect of drought and wounding stress on indole alkaloid formation in Catharanthus roseus. Phytochemistry 26, 707–710
Giroud, C., Van der Leer, T., Van der Heijden, R., Verpoorte, R., Heeremans, C.E.M., Niessen, W.M.A., Van der Greef, J. (1990) Thermospray liquid chromatography/mass spectrometry (TSP LC/MS) analysis of the alkaloids from Cinchona in vitro cultures: identification and fate of 10-methoxytryptamine. Planta Med., in press
Hampp, N., Zenk, M.H. (1988) Homogeneous strictosidine synthase from cell suspension cultures of Rauvolfia serpentina. Phytochemistry 27, 3811–3815
Howell, K.E., Devaney, E., Gruenberg, J. (1989) Subcellular fractionation of tissue culture cells. TIBS 14, 44–47
Hughes, D.W., Genest, K. (1973) Alkaloids. In: Phytochemistry, vol II, pp. 151–154, Miller, L.P., ed. Van Nostrand Reinhold, New York
Keene, A.T., Anderson, L.A., Phillipson, J.D. (1983) Investigation of Cinchona leaf alkaloids by high-performance liquid chromatography. J. Chromatogr. 260, 123–128
Klein Horsman-Relijk, J. (1960) Onderzoek naar de biosynthese van enkele alkaloïden in Cinchona succirubra P. Thesis, University of Amsterdam, The Netherlands
Knobloch, K.-H., Hansen, B., Berlin, J. (1981) Medium-induced formation of indole alkaloids and concomitant changes of inter-related enzyme activities in cell suspension cultures of Catharanthus roseus. Z. Naturforsch. 36c, 40–43
Loomis, W.D., Battaile, J. (1966) Plant phenolic compounds and the isolation of plant enzymes. Phytochemistry 5, 423–438
McHale, D. (1986) The Cinchona tree. Biologist 33, 45–53
Moens, J.C.B. (1882) De kinacultuur in Azië. Ernst en Co., Batavia
Mulder-Krieger, Th., Verpoorte, R., De Water, A., Van Gessel, M., Van Oeveren, B.C.J.A., Baerheim Svendsen, A. (1982) Identification of the alkaloids and anthraquinones in Cinchona ledgeriana callus cultures. Planta Med. 46, 19–24
Nagakura, N., Rüffer, M., Zenk, M.H. (1979) The biosynthesis of monoterpenoid indole alkaloids from strictosidine. J. Chem. Soc. (Perkin I), 2308–2312
Noé, W., Berlin, J. (1985) Induction of de-novo synthesis of tryptophan decarboxylase in cell suspensions of Catharanthus roseus. Planta 166, 500–504
Pennings, E.J.M., Van der Bosch, R., Van der Heijden, R., Van der Leer, T., Verpoorte, R. (1988) Rapid assay of tryptophan decarboxylase from plant cell cultures. In: Manipulating secondary metabolism in culture, pp. 79–82, Robins, R.J., Rhodes, M.J.C., eds. Cambridge University Press, Cambridge
Pennings, E.J.M., Van der Bosch, R.A., Van der Heijden, R., Stevens, L.H., Duine, J.A., Verpoorte, R. (1989) Assay of strictosidine synthase from plant cell cultures by high-performance liquid chromatography. Anal. Biochem. 176, 412–415
Pfitzner, U., Zenk, M.H. (1989) Homogeneous strictosidine synthase isoenzymes from cell suspension cultures of Catharanthus roseus. Planta Med. 55, 525–530
Robinson, T. (1974) Metabolism and function of alkaloids in plants. Science 184, 430–435
Scott, A.I., Lee, S.L., De Capite, P., Culver, M.G. (1977) The role of isovincoside (strictosidine) in the biosynthesis of the indole alkaloids. Heterocycles 7, 979–984
Skinner, S.E., Walton, N.J., Robins, R.J., Rhodes, M.J.C. (1987) Tryptophan decarboxylase, strictosidine synthase and alkaloid production by Cinchona ledgeriana suspension cultures. Phytochemistry 26, 721–725
Stahl, E. (1967) Dünnschicht-Chromatographie. Ein Laboratoriumshandbuch, p. 837. Springer, Berlin Heidelberg New York
Stöckigt, J. (1980) The biosynthesis of heteroyohimbine-type alkaloids. In: Indole and biogenetically related alkaloids, p. 113, Phillipson, J.D., Zenk, M.H., eds. Academic Press, London
Stöckigt, J., Zenk, M.H. (1977) Strictosidine (Isovincoside): the key intermediate in the biosynthesis of monoterpenoid indole alkaloids. J. Chem. Soc. Chem. Commun., 646–648
Treimer, J.F., Zenk, M.H. (1979) Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation. Eur. J. Biochem. 101, 225–233
Waller, G.R., Nowacki, E.K. (1978) Alkaloid biology and metabolism in plants, pp. 143–181. Plenum Press, New York
Williams, R.D., Ellis, B.E. (1989) Age and tissue distribution of alkaloids in Papaver somniferum. Phytochemistry 28, 2085–2088
Wink, M. (1987) Chemical ecology of quinolizidine alkaloids. In: Allelochemicals, pp. 524–533, Waller, G.R., ed. American Chemical Society, Washington
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We wish to thank Wim Snoeijer for excellent technical assistance, and Dr. H.J.v.d. Meulen, Multiplant Holding B.V. (Maarssen), for kindly providing us with Cinchona ledgeriana Moens seeds. Financial support by Multiplant Holding B.V. (Maarssen) is gratefully acknowledged.
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Aerts, R.J., de Waal, A., Pennings, E.J.M. et al. The distribution of strictosidine-synthase activity and alkaloids in Cinchona plants. Planta 183, 536–541 (1991). https://doi.org/10.1007/BF00194275
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DOI: https://doi.org/10.1007/BF00194275