Abstract
The involvement of the glucoalkaloid strictosidine in antimicrobial and antifeedant activity inCatharanthus roseus leaves was investigated. Strictosidine and its deglucosylation product, specifically formed by the enzyme strictosidine glucosidase, were shown to be active against several microorganisms. In contrast, neither the intact glucoside, nor the aglycone product(s) was found to exhibit antifeedant activity againstSpodoptera exigua larvae, as was found for intactC. roseus leaves and leaf extracts. Besides alkaloids further downstream in the biosynthesis pathway, a more apolar, yet unidentified compound may be involved in this activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Aerts, R. J., de Waal, A., Pennings, E. J. M., andVerpoorte, R. 1991. The distribution of strictosidine synthase activity and alkaloids inCinchona plants.Planta 183:536–541.
Al-Shamma, A., Guagliardi, L. E., Mitscher, L. A., andSwayze, J. K. 1982. Antimicrobial alkaloids fromBoehmeria cylindrica.Phytochemistry 21:485–487.
Beijersbergen, J. C. M., andLemmers, C. B. G. 1972. Enzymic and non-enzymic liberation of tulipalin A (α-methylene butyrolactone) in extracts of tulip.Physiol. Plant Pathol. 2:265–270.
Chockalingam, S., Nalina Sundari, M. S., andThenmozhi, S. 1989. Impact of the extract ofCatharanthus roseus on feeding and enzymatic digestive activities ofSpodoptera litura.J. Environ. Biol. 10:303–307.
DeConti, R. C., andCreasey, W. A. 1975. Clinical aspects of the dimericCatharanthus alkaloids. pp. 237–279,in W. I. Taylor and N. R. Farnsworth (eds.). The Catharanthus Alkaloids. Marcel Dekker, New York.
Frischknecht, P. M., Bättig, M., andBaumann, T. W. 1987. Effect of drought and wounding stress on indole alkaloid formation inCatharanthus roseus.Phytochemistry 26:707–710.
Grünweller, S., andKesselmeier, J. 1985. Characterization of a membrane bound β-glucosidase responsible for the activation of oat leaf saponins.Phytochemistry 24:1941–1943.
Hernandez, N. M. R. 1979. Evaluación de la actividad antimicrobiana de alcaloides indólicos.Rev. Cubana Med. Trop. 31:199–204.
Hesse, M. 1964. Indolalkaloide in tabellen. Springer-Verlag, Berlin.
Hesse, M. 1968. Indolalkaloids in tabellen, Ergänzungswerk. Springer-Verlag, Berlin.
Kesselmeier, J., andUrban, B. 1983. Subcellular localization of saponins in green and etiolated leaves and green protoplasts of oat (Avena sativa L.).Protoplasma 114:133–140.
Kogan, M., Fischer, D. C. 1991. Inducible defenses in soybean against herbivorous insects, pp. 347–378,in D. W. Tallamy and M. J. Raupp (eds.). Phytochemical induction by herbivores. Wiley & Sons, New York.
Kubo, I. 1991. Screening techniques for plant-insect interactions.Methods Plant Biochem. 6:179–193.
McKnight, T. D., Bergey, D. R., Burnett, R. J., andNessler, C. L. 1991. Expression of enzymatically active and correctly targeted strictosidine synthase in transgenic tobacco plants.Planta 185:148–152.
Meisner, J., Weissenberg, M., Palevitch, D., andAharonson, N. 1981. Phagodeterrency induced by leaves and leaf extracts ofCatharanthus roseus in the larva ofSpodoptera littoralis.J. Econ. Entomol. 74:131–135.
Mersey, B. G., andCutler, A. J. 1986. Differential distribution of specific indole alkaloids in leaves ofCatharanthus roseus.Can. J. Bot. 64:1039–1045.
Naaranlahti, T., Auriola, S., andLapinjoki, S. P. 1991. Growth-related dimerization of vindoline and catharanthine inCatharanthus roseus and effect of wounding on stress.Phytochemistry 30:1451–1453.
Neuss, N., andNeuss, M. N. 1990. Therapeutic use of bisindole alkaloids fromCatharanthus, pp. 229–240,in A. Brossi and M. Suffness (eds.). The Alkaloids, Vol. 37. Academic Press, San Diego.
Pfitzner, U., andZenk, M. H. 1982. Immobilisation of strictosidine synthase fromCatharanthus cell cultures and preparative synthesis of strictosidine.Planta Med. 46:10–14.
Stevens, L. H. 1994. Formation and conversion of strictosidine in the biosynthesis of monoterpenoid indole and quinoline alkaloids. PhD dissertation. Leiden University, The Netherlands.
Stevens, L. H., Blom, T. J. M., andVerpoorte, R. 1993. Subcellular localization of tryptophan decarboxylase, strictosidine synthase and strictosidine glucosidase in suspension cultured cells ofCatharantus roseus andTabernaemontana divaricata.Plant Cell Rep. 12:573–576.
Stöckigt, J., andZenk, M. H. 1977. Strictosidine (isovincoside)—the key intermediate in the biosynthesis of monoterpenoid indole alkaloids.J. Chem. Soc., Chem. Commun. 1977:646–648.
Stöckigt, J., Ruffer, M., Zenk, M. H., andHoyer, G.-A. 1978. Indirect identification of 4,21-dehydrocorynantheine aldehyde as an intermediate in the biosynthesis of ajmalicine and related alkaloids.Planta Med. 33:188–192.
van der Heijden, R., Lamping, P. J., Out, P. P., Wijnsma, R., andVerpoorte, R. 1987. High-performance liquid chromatographic determination of indole alkaloids in a suspension culture ofTabernaemontana divaricata.J. Chromatogr. 396:287–295.
Woloshuk, C. P., Meulenhoff, J. S., Sela-Buurlage, M., van den Elzen, P. J. M., andCornelissen, B. J. C. 1991. Pathogen-induced proteins with inhibitory activity towardPhytophthora infestans.Plant Cell 3:619–628.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Luijendijk, T.J.C., van der Meijden, E. & Verpoorte, R. Involvement of strictosidine as a defensive chemical inCatharanthus roseus . J Chem Ecol 22, 1355–1366 (1996). https://doi.org/10.1007/BF02027718
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02027718