Skip to main content
Log in

The distribution of strictosidine-synthase activity and alkaloids in Cinchona plants

  • Published:
Planta Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

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

    Google Scholar 

  • 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

    Google Scholar 

  • Cordell, G.A. (1981) Introduction to alkaloids. A biogenetic approach. Wiley, New York

    Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • De Moerloose, P. (1954) Studie met behulp van het koolstofisotoop C14 over de biosynthese van de kina-alkaloïden. Pharm. Weekbl. 89, 541–572

    Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • Howell, K.E., Devaney, E., Gruenberg, J. (1989) Subcellular fractionation of tissue culture cells. TIBS 14, 44–47

    Google Scholar 

  • Hughes, D.W., Genest, K. (1973) Alkaloids. In: Phytochemistry, vol II, pp. 151–154, Miller, L.P., ed. Van Nostrand Reinhold, New York

    Google Scholar 

  • 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

    Google Scholar 

  • Klein Horsman-Relijk, J. (1960) Onderzoek naar de biosynthese van enkele alkaloïden in Cinchona succirubra P. Thesis, University of Amsterdam, The Netherlands

    Google Scholar 

  • 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

    Google Scholar 

  • Loomis, W.D., Battaile, J. (1966) Plant phenolic compounds and the isolation of plant enzymes. Phytochemistry 5, 423–438

    Google Scholar 

  • McHale, D. (1986) The Cinchona tree. Biologist 33, 45–53

    Google Scholar 

  • Moens, J.C.B. (1882) De kinacultuur in Azië. Ernst en Co., Batavia

    Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • Pfitzner, U., Zenk, M.H. (1989) Homogeneous strictosidine synthase isoenzymes from cell suspension cultures of Catharanthus roseus. Planta Med. 55, 525–530

    Google Scholar 

  • Robinson, T. (1974) Metabolism and function of alkaloids in plants. Science 184, 430–435

    Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • Stahl, E. (1967) Dünnschicht-Chromatographie. Ein Laboratoriumshandbuch, p. 837. Springer, Berlin Heidelberg New York

    Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • Waller, G.R., Nowacki, E.K. (1978) Alkaloid biology and metabolism in plants, pp. 143–181. Plenum Press, New York

    Google Scholar 

  • Williams, R.D., Ellis, B.E. (1989) Age and tissue distribution of alkaloids in Papaver somniferum. Phytochemistry 28, 2085–2088

    Google Scholar 

  • Wink, M. (1987) Chemical ecology of quinolizidine alkaloids. In: Allelochemicals, pp. 524–533, Waller, G.R., ed. American Chemical Society, Washington

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

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.

To whom correspondence should be addressed.

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00194275

Key words

Navigation