Abstract
Two chromenes, eupatoriochromene (1) and encecalin (2), have been isolated from yellow starthistle (Centaurea solstitialis L.). Both chromenes retard seed germination and reduce radicle and hypocotyl growth of weed and crop plant seedlings. In addition,1 increases adventitious root formation of mung bean cuttings.
Similar content being viewed by others
References
Anthonsen, T. 1969. New chromenes fromEupatorium species.Acta Chem. Scand. 23:3605–3607.
Bjeldanes, L.F., andGeissman, T.A. 1969. Euparinoid constituents ofEncelia california.Phytochemistry 8:1293–1296.
Bohlmann, F., andGrenz, M. 1970. Neue Isopentenyl-acetonphenon-Derivate ausHelianthella uniflora.Chem. Ber. 103:90–96.
Bohlmann, F., andGrenz, M. 1977. Uber Inhaltstoffe der GattungFlourensia.Chem. Ber. 110:295–300.
Bowers, W.S., Ohta, T., Cleere, J.S., andMarsell, P.A. 1976. Discovery of insect hormones in plants.Science 193:542–546.
Buttery, R.G., Maddox, D.M., Light, D.M., andLing, L.C. 1986. Volatile components of yellow starthistle.J. Agric. Food Chem. 34:786–788.
Cassady, J.M., andHokanson, G.C. 1978. 3α-6α-Dihydrotaraxene-3-acetate: A new triterpene fromCentaurea solstitialis.Phytochemistry 17:324–325.
Cassady, J.M., Abramson, D., Cowall, P., Chang, C.J., McLaughlin, J.L., andAynechi, Y. 1979. Centaurepensin: A cytotoxic constituent ofCentaurea solstitialis andC. repens (Asteracea).J. Nat. Prod. 42:427–429.
Elakovich, S.D., andStevens, K.L. 1985. Phytotoxic properties of nordihydroguaiaretic acid, a lignan fromLarrea tridentata (creosote bush).J. Chem. Ecol. 11:27–33.
Goodwin, P.B. 1978. Phytohormones and growth and development of organs of the vegetative plant, pp. 31–173,in D.S. Letham, P.B. Goodwin, and T.J.V. Higgins, (eds.).Phytohormones and Related Compounds: A Comprehensive Treatise, Vol. II. Elsevier-North Holland Biomedical Press, Amsterdam.
Hegnauer, R. 1977. The Chemistry of theCompositae, pp. 283–336,in V.H. Heywood, J.B. Harborne, B.L. Turner, (eds.).The Biology and Chemistry of the Compositae. Academic Press, London.
Kalsi, P.S., Gupta, D., Dhillon, R.S., Arora, G.S., Talwar, K.K., andWadia, M.S. 1981. Plant growth activity of guaianolides with a C-4 oxygen-containing groups.Phytochemistry 20:1539–1542.
Kamanzi, K., andRaynaud J. 1976. Contribution a l'étude des glycosides flavonques deCentaurea solstitialis L. (Composées).Plant Med. Phytother. 10:78–84.
Klocke, J.A., Balandrin, M.F., Adams, R.P., andKingsford E. 1985. Insecticidal chromenes from the volatile oil ofHemizonia fitchii.J. Chem. Ecol. 11:701–712.
Koehler, J.W. 1965.1965 Noxious Weed Acreage Report. California Department of Agriculture, Sacramento.
Maddox, D.M. 1981.Introduction, Phenology and Density of Yellow Starthistle in Coastal, Inter-coastal, and Central Valley Situations in California. Agricultural Research Reports ARR-W-20, U.S. Department of Agriculture, Washington, D.C.
Maddox, D.M., andMayfield, A. 1985. Yellow Starthistle infestations are on the increase.Calif. Agric. 39(11, 12):10–12.
Maddox, D.M., Mayfield, A., andPortz, N.H. 1985. Distribution of yellow starthistle (Centaurea solstitialis) and Russian knapweed (Centaurea repens).Weed Sci. 33:315–327.
Mamedov, G.M. 1956.Centaurea solstitialis from Azerbaidzhan.Aptechn. Delo 5:57.
Masso, J.L., Bertran, M.N., andAdzet, T. 1979. Chemical and pharmocological study of someCentaurea species (Compositae).Plant Med. Phytother. 13:41–45.
Merrill, G.B., andStevens, K.L. 1985. Sesquiterpene lactones fromCentaurea solstitialis.Phytochemistry 24:2013–2018.
Mukhametshanov, M.N., Shreter, A.I., andPakaln, D.A. 1972. Stizolicin fromCentaurea solstitialis.Chem. Nat. Comp. 5:503.
Proksch, P., andRodriguez, E. 1983. Chromenes and benzofurans of theAsteraceae, their chemistry and biological significance.Phytochemistry 22:2335–2348.
Proksch, P., Proksch, M., Towers, G.H.N., andRodriouez, E. 1983. Phototoxic and insecticidal activities of chromenes and benzofurans fromEncelia.J. Nat. Prod. 46:331–334.
Steelink, C., andMarshall, G.P. 1979. Structures, syntheses, and chemotaxonomic significance of some new acetophenone derivatives fromEncelia farinosa Gray.J. Org. Chem. 44:1429–1433.
Stevens, K.L., andMerrill, G.B. 1985. Sesquiterpene lactone and allelochemicals fromCentaurea species, pp. 82–98,in A.C. Thompson (ed.).The Chemistry of Allelopathy Biochemical Interactions Among Plants. ACS Symposium Series 268, American Chemical Society, Washington, D.C.
Sunderland, A. 1976. Yellow starthistle: A major range weed problem.Down Earth 32(1):28–32.
Theissen, W.E., Hope, H., Zarghami, N., Heinz, D.E., Deuel, P., andHanh, E.A. 1969. A new Sesquiterpene lactone fromCentaurea solstitialis (yellow star thistle).Chem. Ind. (London). 1969:460–461.
Wisdom, C., andRodriguez, E. 1982. Quantitative variation of sesquiterpene lactones and chromenes ofEncelia farinosa. Biochem.Syst. Ecol. 10:43–48.
Wisdom, C.S., Smiley, J.T., andRodriguez, E. 1983. Toxicity and deterrency of sesquiterpene lactones and chromenes to the corn earworm (Lepidoptera: Noctuidae).J. Econ. Entomol. 76:993–998.
Zarghami, N., andHeinz, D.E. 1969. Solstitialin acetate: A sesquiterpene lactone fromCentaurea solstitialis L. (yellow star thistle).Chem. Ind. (London). 1969:1556–1557.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Merrill, G.B. Eupatoriochromene and encecalin, plant growth regulators from yellow starthistle (Centaurea solstitialis L.). J Chem Ecol 15, 2073–2087 (1989). https://doi.org/10.1007/BF01207439
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01207439