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In planta Mechanism of Action of Leptospermone: Impact of Its Physico-Chemical Properties on Uptake, Translocation, and Metabolism.
MedLine Citation:
PMID:  23314892     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Daniel K Owens; N P Dhammika Nanayakkara; Franck E Dayan
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-1-13
Journal Detail:
Title:  Journal of chemical ecology     Volume:  -     ISSN:  1573-1561     ISO Abbreviation:  J. Chem. Ecol.     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-1-14     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7505563     Medline TA:  J Chem Ecol     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, P.O. Box 8048, University, MS, 38677, USA.
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