Mode-of-action of the natural herbicide radulanin A as an inhibitor of photosystem II.

Autor: Thuillier S; Laboratoire de Biologie du Développement, Institut de Biologie Paris Seine, Sorbonne Université, CNRS, Paris, France.; Laboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, Institut Polytechnique de Paris, Palaiseau, France., Viola S; Department of Life Sciences, Imperial College-South Kensington Campus, London, UK., Lockett-Walters B; Laboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, Institut Polytechnique de Paris, Palaiseau, France., Nay B; Laboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, Institut Polytechnique de Paris, Palaiseau, France., Bailleul B; Chloroplast Biology and Light-sensing in Microalgae-UMR7141, IBPC, CNRS-Sorbonne Université, Paris, France., Baudouin E; Laboratoire de Biologie du Développement, Institut de Biologie Paris Seine, Sorbonne Université, CNRS, Paris, France.
Jazyk: angličtina
Zdroj: Pest management science [Pest Manag Sci] 2024 Jan; Vol. 80 (1), pp. 156-165. Date of Electronic Publication: 2023 Jun 23.
DOI: 10.1002/ps.7609
Abstrakt: Background: Radulanin A is a natural 2,5-dihydrobenzoxepin synthesized by several liverworts of the Radula genus. Breakthroughs in the total synthesis of radulanin A paved the way for the discovery of its phytotoxic activity. Nevertheless, its mode-of-action (MoA) has remained unknown so far and thus was investigated, in Arabidopsis thaliana.
Results: Radulanin A phytotoxicity was associated with cell death and partially depended on light exposure. Photosynthesis measurements based on chlorophyll-a fluorescence evidenced that radulanin A and a Radula chromene inhibited photosynthetic electron transport with IC 50 of 95 and 100 μm, respectively. We established a strong correlation between inhibition of photosynthesis and phytotoxicity for a range of radulanin A analogs. Based on these data, we also determined that radulanin A phytotoxicity was abolished when the hydroxyl group was modified, and was modulated by the presence of the heterocycle and its aliphatic chain. Thermoluminescence studies highlighted that radulanin A targeted the Q B site of the Photosystem II (PSII) with a similar MoA as 3-(3,4-dichloropheny)-1,1-dimethylurea (DCMU).
Conclusion: We establish that radulanin A targets PSII, expanding Q B sites inhibitors to bibenzyl compounds. The identification of an easy-to-synthesize analog of radulanin A with similar MoA and efficiency might be useful for future herbicide development. © 2023 Society of Chemical Industry.
(© 2023 Society of Chemical Industry.)
Databáze: MEDLINE
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