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In planta Mechanism of Action of Leptospermone: Impact of Its Physico-Chemical Properties on Uptake, Translocation, and Metabolism

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Abstract

Leptospermone is a natural β-triketone that specifically inhibits the enzyme p-hydrophyphenylpyruvate dioxygenase, the same molecular target site as that of the commercial herbicide mesotrione. The β-triketone-rich essential oil of Leptospermum scoparium has both preemergence and postemergence herbicidal activity, resulting in bleaching of treated plants and dramatic growth reduction. Radiolabeled leptospermone was synthesized to investigate the in planta mechanism of action of this natural herbicide. Approximately 50 % of the absorbed leptospermone was translocated to the foliage suggesting rapid acropetal movement of the molecule. On the other hand, very little leptospermone was translocated away from the point of application on the foliage, indicating poor phloem mobility. These observations are consistent with the physico-chemical properties of leptospermone, such as its experimentally measured logP and pK a values, and molecular mass, number of hydrogen donors and acceptors, and number of rotatable bonds. Consequently, leptospermone is taken up readily by roots and translocated to reach its molecular target site. This provides additional evidence that the anecdotal observation of allelopathic suppression of plant growth under β-triketone-producing species may be due to the release of these phytotoxins in soils.

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Acknowledgments

We are thankful for the excellent technical assistance provided by J’Lynn Howell (USDA-ARS NPURU, University MS) and Krishna N. Reddy and Efren Ford (USDA-ARS CPSRU, Stoneville, MS) for giving us access to their laboratory biological oxidizer.

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Authors and Affiliations

  1. United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, P.O. Box 8048, University, MS, 38677, USA

    Daniel K. Owens & Franck E. Dayan

  2. National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, University, MS, 38677, USA

    N. P. Dhammika Nanayakkara

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  1. Daniel K. Owens
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  2. N. P. Dhammika Nanayakkara
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  3. Franck E. Dayan
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Correspondence to Franck E. Dayan.

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Owens, D.K., Nanayakkara, N.P.D. & Dayan, F.E. In planta Mechanism of Action of Leptospermone: Impact of Its Physico-Chemical Properties on Uptake, Translocation, and Metabolism. J Chem Ecol 39, 262–270 (2013). https://doi.org/10.1007/s10886-013-0237-8

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