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

Owens, Daniel K., Nanayakkara, N. P. Dhammika, Dayan, Franck E.
Journal of chemical ecology 2013 v.39 no.2 pp. 262-270
Leptospermum scoparium, bleaching, essential oils, growth retardation, herbicidal properties, hydrogen, leaves, mechanism of action, mesotrione, metabolism, molecular weight, phloem, phytotoxins, plant growth, roots, soil
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.