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United States Department of Agriculture

Agricultural Research Service

Research Project: DISCOVERY AND DEVELOPMENT OF NATURAL PRODUCT-BASED WEED MANAGEMENT METHODS

Location: Natural Products Utilization Research

Title: p-Hydroxyphenylpyruvate Dioxygenase, a Herbicide Target Site for Natural B-Triketones

Authors
item Dayan, Franck
item Cantrell, Charles
item Duke, Stephen
item Van Klink, John - UNIV. OTAGO-NEW ZEALAND
item Perry, Nigel - UNIV. OTAGO-NEW ZEALAND

Submitted to: Meeting Proceedings
Publication Type: Proceedings
Publication Acceptance Date: April 21, 2009
Publication Date: May 9, 2009
Citation: Dayan, F.E., Cantrell, C.L., Duke, S.O., Van Klink, J.W., Perry, N.B. 2009. p-Hydroxyphenylpyruvate Dioxygenase, a Herbicide Target Site for Natural B-Triketones in ENDURE International Conference, pp 1-4, La Grande-Motte, France.

Interpretive Summary: Weed control relies primarily on the use of synthetic herbicides. However, concerns over their potential impact on the environment and health necessitate the development of alternative and safer weed management tools. Natural herbicides present themselves as a potential bridge between traditional and organic agriculture. Natural products belonging to the triketone class inhibit p-hydroxyphenylpyruvate dioxygenase (HPPD) that is important for the biosynthesis of some plant pigments. This study reports the biological activity of a series of natural triketone herbicides (e.g., flavesone, grandiflorone and leptospermone) and several analogues against HPPD. Computer modeling methods such as conformational molecular field analysis and hydropathic interaction were used to analyze the data. This work provided a structure-activity relationship between the inhibitors and their potency against HPPD.

Technical Abstract: Weed control relies primarily on the use of synthetic herbicides. However, concerns over their potential impact on the environment and health necessitate the development of alternative and safer weed management tools. Natural herbicides present themselves as a potential bridge between traditional and organic agriculture (Duke et al. 2000). p-Hydroxyphenylpyruvate dioxygenase (HPPD) is a key enzyme in the biosynthesis of prenyl quinones. Inhibition of HPPD reduces plastoquinone levels and has deleterious effects on carotenoid synthesis and the photosynthetic apparatus. This enzyme is the target site of ß-triketone herbicides (e.g., sulcotrione and mesotrione) (Lee et al., 1997). The inhibitory activity of natural ß-triketones (e.g., flavesone, grandiflorone and leptospermone) and several analogues against HPPD was tested. Modeling of the binding of the triketones to HPPD and conformational molecular field analysis (CoMFA) determined that bulky substituents on the ring structure hindered binding to HPPD. The length of the aliphatic tail also modulated the activity of the compounds. Preliminary greenhouse data indicates that while these natural ß-triketones may not have optimal structural features of their synthetic counterparts for in vivo herbicidal activity, the activity of the ß-triketone enriched essential oil can be improved with the use of surfactants to a level sufficiently high to be potentially developed as natural tools for weed management.

Last Modified: 7/28/2014
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