Skip to main content
Log in

Phytotoxic properties of cnicin, a sesquiterpene lactone fromcentaurea maculosa (spotted knapweed)

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

Water and solvent extracts from the aerial tissues ofCentaurea maculosa, spotted knapweed, inhibited the root growth of lettuce. Column chromatography and lettuce bioassay of a chloroform extract led to the isolation of cnicin, a sesquiterpene lactone. Pure cnicin was bioassayed at 0, 1, 2, 4, 6, 8, and 10 mg/5 ml water with lettuce, created wheatgrass, bluebunch wheatgrass, rough fescue, western larch, lodgepole pine, and spotted knapweed. Germination was inhibited at one or more concentrations for all species except lodgepole pine and spotted knapweed. Growth, particularly of the roots, was retarded between 1 and 4 mg of cnicin. Lettuce, bluebunch wheatgrass, and spotted knapweed were inhibited significantly at all concentrations tested.

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.

Institutional subscriptions

Similar content being viewed by others

References

  • Abeysekera, B.F., Abramowsi, Z., andTowers, G.H.N. 1985. Chromosomal aberrations caused by sesquiterpene lactones in Chinese hamster ovary cells.Biochem. Syst. Ecol. 13:365–369.

    Google Scholar 

  • Amo, S.D., andAnaya, A.L. 1978. Effect of some sesquiterpenic lactones on the growth of certain secondary tropical species.J. Chem. Ecol. 4:305–313.

    Google Scholar 

  • Asakawa, Y., andTakemoto, T. 1979. Sesquiterpene lactones ofConocephalum conicum.Phytochemistry. 18:285–288.

    Google Scholar 

  • Belles, W.S.,Wattenbarger, D.W., andLee, G.A. 1980. Effects of various herbicide treatments and subsequent fertilization on spotted knapweed control and forage production in Bonner County. Western Society Weed Science Research Progress Report, pp. 57–60.

  • Blakeman, J.P., andAtkinson, P. 1979. Antimicrobial properties and possible role in host-pathogen interactions of parthenolide, a sequiterpene lactone isolated from glands ofChrysanthemum parthenium.Physiol. Plant Pathol. 15:183–192.

    Google Scholar 

  • Bucher R.F. 1984. The potential cost of spotted knapweed to Montana range users. Cooperative Extension Service Bull. 1316, Montana State University, Bozeman.

    Google Scholar 

  • Burnett, W.C., Jr., Jones, S.B., Jr., Mabry, T.J., andPadolina, W.G., 1974. Sesquiterpene lactones—insect feeding deterrents inVernonia.Biochem. Syst. Ecol. 2:25–29.

    Google Scholar 

  • Burnett, W.C., Jones, S.B., andMabry, T.J. 1977. Evolutionary implications of sesquiterpene lactones inVernonia (Compositae) and mammalian herbivores.Taxon 26:203–207.

    Google Scholar 

  • Burnett, W.C., Jr., Jones, S.B., Jr., andMabry, T.J. 1978. The role of sesquiterpene lactones in plant-animal coevolution, pp. 233–257,in J.B. Harborne (ed.). Biochemical Aspects of Plant and Animal Coevolution. Academic Press, London.

    Google Scholar 

  • Cavallito, C.J., andBailey, J.H. 1949. An antibacterial principle fromCentaurea maculosa.J. Bacterial. 57:207–212.

    Google Scholar 

  • Chicoine, T.K. 1984. Spotted knapweed (Centaurea maculosa L.) control, seed longevity and migration in Montana. MS thesis, Montana State University, Bozeman.

    Google Scholar 

  • Dalvi, R.R., Singh, B., andSalunkhe, D.K. 1971. A study on phytotoxicity of alantolactone.Chem.-Biol. Interact. 3:13–18.

    Google Scholar 

  • Dupuis, G., Benezra, C., Schlewer, G., andStampf, J.L. 1980. Allergic contact dermatitis to α-methylene-7-butyrolactones.Mol. Immunol. 17:1045–1051.

    Google Scholar 

  • Elissalde, M.H., Ivie, G.W., Rowe, L.D., andElissalde, G.S. 1983. Considerations of the structure of sesquiterpene lactones on biological activity: Influence of the α-methylene-γ-lactone moiety on mast cell degranulation.Am. J. Vet. Res. 44:1894–1897.

    Google Scholar 

  • Fischer, N.H., andQuijano, L. 1985. Allelopathic agents from common weeds, pp. 133–147,in A.C. Thompson (ed.). The Chemistry of Allelopathy, ACS Symposium Series 268. American Chemical Society, Washington, D.C.

    Google Scholar 

  • Fletcher, R.A., andRenney, A.J. 1963. A growth inhibitor found inCentaurea spp.Can. J. Plant Sci. 43:475–481.

    Google Scholar 

  • French, R.A., andLacey, J.R. 1983. Knapweed: Its cause, effect and spread in Montana. Cooperative Extension Service Circular 307, Montana State University, Bozeman.

    Google Scholar 

  • Garciduenas, M.R., Domingeuz, X.A., Fernandez, J., andAlanis, G. 1972. New growth inhibitors fromParthenium hysterophorus.Rev. Latinoam. Quim. 2:52–53.

    Google Scholar 

  • Geppert, B., Drozdz, B.,Kielczewski, M., andHolub, M. 1983. Sesquiterpene lactones. XXIII. Isolation of sesquiterpene lactones fromCentaurea L. species.Acta Soc. Bot. Pol. 52:23–34.

    Google Scholar 

  • Gonzalez, A.G., Darias, V., Alonso, G., Boada, J.N., andFeria, M. 1978. Cytostatic activity of sesquiterpene lactones from Compositae of the Canary Islands.Planta Med. 33:356–359.

    Google Scholar 

  • Hall, I.H., Lee, K.H., Starnes, C.O., Muraoka, O., Sumida, Y., andWaddell, T.G. 1980a. Antihyperlipidemic activity of sesquiterpene lactones and related compounds.J. Pharm. Sci. 69:694–697.

    Google Scholar 

  • Hall, I.H., Starnes, C.O., Jr., Lee, K.H., andWaddell, T.G. 1980b. Mode of action of sesquiterpene lactones as antiinflammatory agents.J. Pharm. Sci. 69:537–543.

    Google Scholar 

  • Harmatha, J., andNawrot, J. 1984. Comparison of the feeding deterrent activity of some sesquiterpene lactones and a lignan lactone towards selected insect storage pests.Biochem. Syst. Ecol. 12:95–98.

    Google Scholar 

  • Harris, P., andCranston, R. 1979. An economic evaluation of control methods for diffuse and spotted knapweed in western Canada.Can. J. Plant. Sci. 59:375–382.

    Google Scholar 

  • Jones, S.B., Jr., Burnett. W.C. Jr., Coile, N.C., Mabry, T.J., andBetkouski, M.F. 1979. Sesquiterpene lactones ofVernonia—Influence of glaucolide-A on the growth rate and survival of lepidopterous larvae.Oecologia 39:71–77.

    Google Scholar 

  • Kanchan, S.D., andJayachandra. 1979a. Allelopathic effects ofParthenium hysterophorus L. I. Exudation of inhibitors through roots.Plant Soil 53:27–35.

    Google Scholar 

  • Kanchan, S.D., andJayachandra. 1979a. Allelopathic effects ofParthenium hysterophorous L. I. Exudation of inhibitors through roots.Plant Soil 53:27–35.

    Google Scholar 

  • Kanchan, S.D., andJayachandra. 1979b. Allelopathic effects ofParthenium hysterophorus L. III. Inhibitory effects of the weed residue.Plant Soil 53:37–47.

    Google Scholar 

  • Kanchan, S.D., andJayachandra 1980. Allelopathic effects ofParthenium hysterophorus L. Part IV. Identification of inhibitors.Plant Soil 55:67–75.

    Google Scholar 

  • Lacey, J.R. 1983. A complete takeover by knapweed in 2001?Mont. Farmer-Stockman 70:32–34.

    Google Scholar 

  • Lee, K.H., Huang, E.S., Piantadosi, C., Pagano, J.S., andGeissman, T.A. 1971. Cytotoxicity of sesquiterpene lactones.Cancer Res. 31:1649–1654.

    Google Scholar 

  • Lee, K.H., Hall, I.H., Mar, E.C., Starnes, C.O., Elgebaly, S.A., Waddell, T.G., Had-graft, R.I., Ruffner, C.G., andWeidner, I. 1977a. Sesquiterpene antitumor agents: Inhibitors of cellular metabolism.Science 196:533–536.

    Google Scholar 

  • Lee, K.H., Ibuka, T., Wu, R.Y., andGeissman, T.A. 1977b. Structure-antimicrobial activity relationships among the sesquiterpene lactones and related compounds.Phytochemistry 16:1177–1181.

    Google Scholar 

  • Lee, K.H., Ibuka, T., Sims, D., Muraoka, O., Kiyokawa, H., Hall, I.H., andKim, H.L. 1981. Antitumor agents. 44. Bis(helenalinyl) esters and related derivatives as novel potential anti leukemic agents.J. Med. Chem. 24:924–927.

    Google Scholar 

  • Liou, Y.F., Hall, I.H., Lee, K.H., Williams, W.L., Jr., andChaney, S.G. 1983. Investigation of sesquiterpene lactones as protein synthesis inhibitors of p-388 lymphocytic leukemia cells.Biochim. Biophys. Acta 739:190–196.

    Google Scholar 

  • Mabry, T.J., andGill, J.E., 1979. Sesquiterpene lactones and other terpenoids, pp. 501–537, in G.A. Rosenthal and D.H. Janzen (eds.). Herbivores: Their Interaction with Secondary Plant Metabolites. Academic Press, New York.

    Google Scholar 

  • Maddox, D.M. 1979. The knapweeds: Their economics and biological control in the western states,U.S.A. Rangelands 1:139–141.

    Google Scholar 

  • Mandava, N.B. 1985. Chemistry and biology of allelopathic agents, pp. 33–54,in A.C. Thompson (ed.). The Chemistry of Allelopathy, ACS Symposium Series 268. American Chemical Society, Washington, D.C.

    Google Scholar 

  • Marchant, Y.Y., Balza, F., Abeysekera, B.F., andTowers, G.H.N. 1984. Molluscicidal activity of sesquiterpene lactones.Biochem. Syst. Ecol. 12:285–286.

    Google Scholar 

  • McCahon, C.B., Kelsey, R.G., Sheridan, R.P., andSharizadeh, F. 1973. Physiological effects of compounds extracted from sagebrush.Bull. Torrey Bot. Club. 100:23–28.

    Google Scholar 

  • Muir, A.D., andMajak, W. 1983. Allelopathic potential of diffuse knapweed (Centaurea diffusa) extracts.Can. J. Plant Sci. 63:989–996.

    Google Scholar 

  • Picman, A.K. 1984. Antifungal activity of sesquiterpene lactones.Biochem. Syst. Ecol. 12:13–18.

    Google Scholar 

  • Picman, J., andPicman, A.K. 1984a. Autotoxicity inParthenium hysterophorus and its possible role in control of germination.Biochem. Syst. Ecol. 12:287–292.

    Google Scholar 

  • Picman, A.K., andPicman, J. 1984b. Effect of selected pseudoguaianolides on survival of the flour beetle,Tribolium confusum.Biochem. Syst. Ecol. 12:89–93.

    Google Scholar 

  • Picman, A.K., andTowers, G.H.N. 1983. Antibacterial activities of sesquiterpene lactones.Biochem. Syst. Ecol. 11:321–327.

    Google Scholar 

  • Politis, M.J. 1946a. Sur la formation des glucosides amers dans les poils glanduleux de certaines plantes.C.R. Acad. Sci. (Paris) 222:910–911.

    Google Scholar 

  • Politis, J. 1946b. Sur le mode de formation des essences dans certains poils glanduleux.C.R. Acad. Sci. (Paris) 222:1244–1245.

    Google Scholar 

  • Rodriguez, E., Towers, G.H.N., andMitchell, J.C. 1976. Biological activities of sesquiterpene lactones.Phytochemistry. 15:1573–1580.

    Google Scholar 

  • Rustaiyan, A., Niknejad, A., andAynehchi, Y. 1982. Chemical constituents ofCentaurea brugueriana.Planta Med. 44:185–186.

    Google Scholar 

  • Samek, Z., Holub, M., Herout, V., andSorm, F. 1969. Revision of the structure of cnicin.Tetrahedron Lett. 34:2931–2934.

    Google Scholar 

  • Schirman, R. 1981. Seed production and spring seedling establishment of diffuse and spotted knapweed.J. Range Manage. 34:45–47.

    Google Scholar 

  • Schirman, R. 1984. Seedling establishment and seed production of diffuse and spotted knapweed, pp. 7–10, Proceedings of the Knapweed Symposium, Cooperative Extension Service Bull. 1315, Montana State University, Bozeman.

    Google Scholar 

  • Seaman, F.C. 1982. Sesquiterpene lactones as taxonomic characteristics in the Asteraceae.Bot. Rev. 48:121–595.

    Google Scholar 

  • Spencer, G.F., Wolf, R.B., andWeisleder, D. 1984. Germination and growth inhibitory sesquiterpenes fromIva axillaris seeds.J. Nat. Prod. 47:730–732.

    Google Scholar 

  • Spring, O., andHager, A. 1982. Inhibition of elongation growth by two sesquiterpene lactones isolated fromHelianthus annuus L.Planta 156:433–440.

    Google Scholar 

  • Spring, O., Kupka, J., Maier, B., andHager, A. 1982. Biological activities of sesquiterpene lactones fromHelianthus annuus: Antimicrobial and cytotoxic properties; influence on DNA, RNA, and protein synthesis.Z. Naturforsch. 37:1087–1091.

    Google Scholar 

  • Stevens, K.L. 1982. Sesquiterpene lactones fromCentaures repens.Phytochemistry 21:1093–1098.

    Google Scholar 

  • Stevens, K.L., andMerrill, G.B. 1985. Sesquiterpene lactones and allelochemicals fromCentraurea species, pp. 83–98,in A.C. Thompson (ed.). The Chemistry of Allelopathy, ACS Symposium Series 268. American Chemical Society, Washington, D.C.

    Google Scholar 

  • Strang, R.M., Lindsay, K.M., andPrice, R.S. 1979. Knapweeds: British Columbia's undesirable aliens.Rangelands 1:141–143.

    Google Scholar 

  • Suchy, M., andHerout, V. 1962. On terpenes. CXXXVI. Identity of the bitter principle fromCentaurea stoebe (L.) Sch. et Thell. with cnicin.Collect. Czech. Chem. Commun. 27:1510–1512.

    Google Scholar 

  • Suchy, M., Benesova, V., Herout, V., andSorm, F. 1959. Contribution on the structure of cnicin, the bitter principle fromCnicus benedictus L.Tetrahedron Lett. 10:5–9.

    Google Scholar 

  • Suchy, M., Herout, V., andSorm, F. 1962. On terpenes. CXLI. Absolute configuration of cnicin and scabiolide.Collect. Czech. Chem. Commun. 27:2398–2403.

    Google Scholar 

  • Suchy, M., Samek, Z., Herout, V., andSorm, F. 1965. On terpenes. CLXXV. Revision of structure of artiopicrin, cnicin and scabiolide.Collect. Czech. Chem. Commun. 30:3473–3477.

    Google Scholar 

  • Van Aswegen, C.H., Potgieter, D.J.J., andVermeulen, N.M.J. 1982. Site of respiratory inhibition by sesquiterpene lactones fromGeigeria.S. Afr. J. Sci. 78:125–127.

    Google Scholar 

  • Vanhaelen-Fastré, R. 1972. Activities antibiotique et cytotoxique de la cnicine, isolee deCnicus benedictus L.J. Pharm. Belg. 27:683–688.

    Google Scholar 

  • Vanhaelen-Fastré, R., andVanhaelen, M. 1976. Activite antibiotique et cytotoxique de la cnicine et de ses produits d'hydrolyse.Planta Med. 29:179–189.

    Google Scholar 

  • Wagner, H. 1977. Pharmaceutical and economic uses of the Compositae, pp. 411–433,in V.H. Heywood, J.B. Harborne, and B.L. Turner (eds.). The Biology and Chemistry of the Compositae, Vol. I. Academic Press, London.

    Google Scholar 

  • Watson, A.K., andRenney, A.J. 1974. The biology of Canadian weeds. 6.Centaurea diffusa andC. maculosa.Can. J. Plant Sci. 54:687–701.

    Google Scholar 

  • Woynarowski, J.M., andKonopa, J. 1981. Inhibition of DNA biosynthesis in HeLa cells by cytotoxic and antitumor sesquiterpene lactones.Mol. Pharmacol. 19:97–102.

    Google Scholar 

  • Woynarowski, J.W., Beerman, T.A., andKonopa, J. 1981. Induction of deoxyribonucleic acid damage in HeLa S3 cells by cytotoxic and antitumor sesquiterpene lactones.Biochem. Pharmacol. 30:3005–3007.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kelsey, R.G., Locken, L.J. Phytotoxic properties of cnicin, a sesquiterpene lactone fromcentaurea maculosa (spotted knapweed). J Chem Ecol 13, 19–33 (1987). https://doi.org/10.1007/BF01020348

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01020348

Key words

Navigation