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

Published online by Cambridge University Press:  20 January 2017

Antonio L. Cerdeira ,
Charles L. Cantrell ,
Franck E. Dayan ,
John D. Byrd  and
Stephen O. Duke
Antonio L. Cerdeira
Affiliation:
Brazilian Department of Agriculture, Agricultural Research Service, EMBRAPA/Environment, Jaguariúna, São Paulo, 13820-000 Brazil
Charles L. Cantrell
Affiliation:
United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, University, MS 38677
Franck E. Dayan
Affiliation:
United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, University, MS 38677
John D. Byrd
Affiliation:
Plant and Soil Sciences, Mississippi State University, Mississippi State, MS 39762
Stephen O. Duke*
Affiliation:
United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, University, MS 38677
*
Corresponding author's E-mail: Stephen.Duke@ars.usda.gov
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Abstract

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.

Keywords

Tabanone, 4-(2-butenylidene)-3,5,5-trimethyl-2-cyclohexen-1-onecogongrass, Imperata cylindrica (L.) Beauv. IMCYcreeping bentgrass, Agrostis stolonifera Llesser duckweed, Lemna aequinoctialis Welwgarden lettuce, Lactuca sativa Lgarden onion, Allium cepa LAllelochemicalallelopathyphytotoxinessential oil
Type
Weed Biology and Ecology
Information
Weed Science , Volume 60 , Issue 2 , June 2012 , pp. 212 - 218
Copyright
Copyright © Weed Science Society of America 

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