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Tabanone, a New Phytotoxic Constituent of Cogongrass (Imperata cylindrica)

  • Antonio L. Cerdeira (a1), Charles L. Cantrell (a2), Franck E. Dayan (a2), John D. Byrd (a3) and Stephen O. Duke (a2)...


Cogongrass is a troublesome, invasive weedy species with reported allelopathic properties. The phytotoxicity of different constituents isolated from roots and aerial parts of this species was evaluated on garden lettuce and creeping bentgrass. No significant phytotoxic activity was detected in the methylene chloride, methanol, or water extracts when tested at 1.0 mg ml−1. However, the total essential oil extract of cogongrass aerial parts was active. Bioactivity-guided fractionation of this extract using silica gel column chromatography led to the identification of megastigmatrienone, 4-(2-butenylidene)-3,5,5-trimethyl-2-cyclohexen-1-one (also called tabanone), as a mixture of four stereoisomers responsible for most of the activity. Tabanone inhibited growth of frond area of lesser duckweed, root growth of garden onion, and fresh weight gain of garden lettuce with 50% inhibition values of 0.094, 3.6, and 6.5 mM, respectively. The target site of tabanone is not known, but its mode of action results in rapid loss of membrane integrity and subsequent reduction in the rate of photosynthetic electron flow.


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Aasen, A. J., Kimland, B., Almqvist, S., and Enzell, C. R. 1972. Tobacco chemistry, 15: new tobacco constituents—the structures of five isomeric megastigmatrienones. Acta Chem. Scand. 26:25732576.
Blum, U. 1996. Allelopathic interactions involving phenolic acids. J. Nematol. 28:259267.
Bryson, C. T., Krutz, L. J., Ervin, G. N., Reddy, K. N., and Byrd, J. D. 2010. Ecotype variability and edaphic characteristics for cogongrass (Imperata cylindrica) populations in Mississippi. Invasive Plant Sci. 3:199207.
Cantrell, C. L., Duke, S. O., Fronczek, F. R., Osbrink, W. L. A., Mamonov, L. K., Vassilyev, J. I., Wedge, D. E., and Dayan, F. E. 2007. Phytotoxic eremophilanes from Ligularia macrophylla . J. Agric. Food Chem. 55:1065610663.
Castro, A., Cantrell, C. L., Hale, A. L., and Duke, S. O. 2010. Phytotoxic activity of flavonoids from Dicranostyles ampla . Nat. Prod. Commun. 5:12331237.
Chang, I-F. 2008. Ecotypic variation of a medicinal plant Imperata cylindrica populations in Taiwan: mass spectrometry-based proteomic evidence. J. Med. Plants Res. 2:7176.
Dayan, F. E. and Duke, S. O. 2009. Biological activity of allelochemicals. Pages 361384 in Osbourn, A. E., and Lanzotti, V., eds. Plant-Derived Natural Products: Synthesis, Function, and Application. New York, NY Springer.
Dayan, F. E., Howell, J. L., and Weidenhamer, J. D. 2009. Dynamic root exudation of sorgoleone and its in planta mechanism of action, J. Exp. Bot. 60:21072117.
Dayan, F. E., Howell, J. L., Marais, J. M., Ferreira, D., and Koivunen, M. E. 2011. Manuka oil, a natural herbicide with preemergence activity. Weed Sci. 59:464469.
Dayan, F. E., Romagni, J. G., and Duke, S. O. 2000. Investigating the mode of action of natural phytotoxins. J. Chem. Ecol. 26:20792094.
Dayan, F. E. and Watson, S. B. 2011. Plant cell membrane integrity as a marker for light-dependent and light-independent mechanisms of action. Pestic. Biochem. Physiol. 101:182190.
Duke, S. O. and Kenyon, W. H. 1993. Peroxidizing activity determined by cellular leakage, in target assays for modern herbicides and related compounds. Pages 6166 in Böger, P. and Sandmann, G., eds. Target Assays for Modern Herbicides and Related Compounds. Boca Raton, FL Lewis.
Eussen, J. H. H. and Niemann, G. J. 1981. Growth inhibiting substances from leaves of Imperata cylindrica (L) Beauv. Z. Pflanzenphysiol. 102:263266.
Hussain, F. and Abidi, N. 1991. Allelopathy exhibited by Imperata cylindrica (L) Beauv. Pak. J. Bot. 23:1525.
Inderjit, and Dakshini, K. M. M. 1991. Investigations on some aspects of chemical ecology of cogongrass, Imperata cylindrica (L.) Beauv. J. Chem. Ecol. 17:343352.
Koger, C. H. and Bryson, C. T. 2004. Effect of cogongrass (Imperata cylindrica) extracts on germination and seedling growth of selected grass and broadleaf species. Weed Technol. 18:236242.
Koger, C. H., Bryson, C. T., and Byrd, J. D. 2004. Response of selected grass and broadleaf species to cogongrass (Imperata cylindrica) residues. Weed Technol. 18:353357.
MacDonald, G. E. 2004. Cogongrass (Imperata cylindrica)—biology, ecology, and management. Crit. Rev. Plant Sci. 23:367380.
Matsunaga, K., Ikeda, M., Shibuya, M., and Ohizumi, Y. 1994a. Cylindol-a, a novel biphenyl ether with 5-lipoxygenase inhibitory activity, and a related compound from Imperata cylindrica . J. Nat. Prod. 57:12901293.
Matsunaga, K., Shibuya, M., and Ohizumi, Y. 1994b. Cylindrene, a novel sesquiterpenoid from Imperata cylindrica with inhibitory activity on contractions of vascular smooth-muscle. J. Nat. Prod. 57:11831184.
Matsunaga, K., Shibuya, M., and Ohizumi, Y. 1994c. Graminone-B, a novel lignan with vasodilative activity from Imperata cylindrica . J. Nat. Prod. 57:17341736.
Matsunaga, K., Shibuya, M., and Ohizumi, Y. 1995. Imperanene, a novel phenolic compound with platelet aggregation inhibitory activity from Imperata cylindrica . J. Nat. Prod. 58:138139.
Michel, A., Johnson, R. D., Duke, S. O., and Scheffler, B. E. 2004. Dose-response relationships between herbicides with different modes of action and growth of Lemna paucicostata: an improved ecotoxicological method. Environ. Toxicol. Chem. 23:10741079.
Morimoto, M., Cantrell, C. L., Libous-Bailey, L., and Duke, S. O. 2009. Phytotoxicity of constituents of glandular trichomes and the leaf surface of camphorweed, Heterotheca subaxillaris . Phytochemistry. 70:6974.
R-Development-Core-Team. 2009. R: A language and environment for statistical computing. 2.9.0 ed. Vienna, Austria R Foundation for Statistical Computing.
Ritz, C. and Streibig, J. C. 2005. Bioassay analysis using R. J. Stat. Softw. 12: issue 5.
Tharayil, N., Bhowmik, P. C., and Xing, B. 2008. Bioavailability of allelochemicals as affected by companion compounds in soil matrices. J. Agric. Food Chem. 56:37063713.
Xuan, T. D., Toyama, T., Fukuta, M., Khanh, T. D., and Tawata, S. 2009. Chemical interaction in the invasiveness of cogongrass (Imperata cylindrica (L.) Beauv.). J Agric. Food Chem. 57:94489453.
Yoon, J. S., Lee, M. K., Sung, S. H., and Kim, Y. C. 2006. Neuroprotective 2-(2-phenylethyl) chromones of Imperata cylindrica . J. Nat. Prod. 69:290291.


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Tabanone, a New Phytotoxic Constituent of Cogongrass (Imperata cylindrica)

  • Antonio L. Cerdeira (a1), Charles L. Cantrell (a2), Franck E. Dayan (a2), John D. Byrd (a3) and Stephen O. Duke (a2)...


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