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Synthesis and Evaluation of New Phytotoxic Fluorinated Chalcones as Photosystem II and Seedling Growth Inhibitors
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2024-02-19 , DOI: 10.1002/cbdv.202301564 Geilly Mara Silva de Pádua 1 , Taciane Santos Pitteri 1 , Marcelo Augusto Ferreira Basso 1 , Leonardo Gomes de Vasconcelos 1 , Akbar Ali 2 , Evandro Luiz Dall'Oglio 1 , Olívia Moreira Sampaio 1 , Lucas Campos Curcino Vieira 1
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2024-02-19 , DOI: 10.1002/cbdv.202301564 Geilly Mara Silva de Pádua 1 , Taciane Santos Pitteri 1 , Marcelo Augusto Ferreira Basso 1 , Leonardo Gomes de Vasconcelos 1 , Akbar Ali 2 , Evandro Luiz Dall'Oglio 1 , Olívia Moreira Sampaio 1 , Lucas Campos Curcino Vieira 1
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The development of novel phytotoxic compounds has been an important aim of weed control research. In this study, we synthesized fluorinated chalcone derivatives featuring both electron-donating and electron-withdrawing groups. These compounds were evaluated both as inhibitors of the photosystem II (PSII) electron chain as well as inhibitors of the germination and seedling growth of Amaranthus plants. Chlorophyll a (Chl a) fluorescence assay was employed to evaluate their effects on PSII, while germination experiments were conducted to assess their impact on germination and seedling development. The results revealed promising herbicidal activity for (E)-3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (7 a) and (E)-1-(4-fluorophenyl)-3-phenylprop-2-en-1-one (7 e). Compounds 7 a and 7 e exhibited a reduction in Chl a parameters associated with performance indexes and electron transport per reaction center. This reduction suggests a decrease in PSII activity, attributed to the blockage of electron flow at the quinone pool. Molecular docking analyses of chalcone derivatives with the D1 protein of PSII revealed a stable binding conformation, wherein the carbonyl and fluorine groups interacted with Phe265 and His215 residues, respectively. Additionally, at a concentration of 100 μM, compound 7 e demonstrated pre- and post-emergent herbicidal activity, resulting in a reduction of the seed germination index, radicle and hypocotyl lengths of Amaranthus weeds.
中文翻译：
新型植物毒性氟化查耳酮光系统 II 和幼苗生长抑制剂的合成与评价
新型植物毒性化合物的开发一直是杂草控制研究的重要目标。在这项研究中，我们合成了具有给电子基团和吸电子基团的氟化查耳酮衍生物。这些化合物既可以作为光系统 II (PSII) 电子链的抑制剂，也可以作为苋属植物发芽和幼苗生长的抑制剂进行评估。采用叶绿素a （Chl a ）荧光测定法评估它们对PSII的影响，同时进行发芽实验评估它们对发芽和幼苗发育的影响。结果表明 ( E )-3-(4-溴苯基)-1-(4-氟苯基)prop-2-en-1-one ( 7a ) 和 ( E )-1-(4-氟苯基) 具有良好的除草活性)-3-苯基丙-2-en-1-酮( 7e )。化合物7a和7e表现出与每个反应中心的性能指数和电子传输相关的叶绿素a参数的降低。这种减少表明 PSII 活性降低，这是由于醌池电子流受阻所致。查耳酮衍生物与 PSII D1 蛋白的分子对接分析揭示了稳定的结合构象，其中羰基和氟基团分别与 Phe265 和 His215 残基相互作用。此外，浓度为 100 μM 时，化合物7e表现出芽前和芽后除草活性，导致苋属杂草的种子发芽指数、胚根和下胚轴长度降低。
更新日期：2024-02-19
中文翻译：
新型植物毒性氟化查耳酮光系统 II 和幼苗生长抑制剂的合成与评价
新型植物毒性化合物的开发一直是杂草控制研究的重要目标。在这项研究中，我们合成了具有给电子基团和吸电子基团的氟化查耳酮衍生物。这些化合物既可以作为光系统 II (PSII) 电子链的抑制剂，也可以作为苋属植物发芽和幼苗生长的抑制剂进行评估。采用叶绿素a （Chl a ）荧光测定法评估它们对PSII的影响，同时进行发芽实验评估它们对发芽和幼苗发育的影响。结果表明 ( E )-3-(4-溴苯基)-1-(4-氟苯基)prop-2-en-1-one ( 7a ) 和 ( E )-1-(4-氟苯基) 具有良好的除草活性)-3-苯基丙-2-en-1-酮( 7e )。化合物7a和7e表现出与每个反应中心的性能指数和电子传输相关的叶绿素a参数的降低。这种减少表明 PSII 活性降低，这是由于醌池电子流受阻所致。查耳酮衍生物与 PSII D1 蛋白的分子对接分析揭示了稳定的结合构象，其中羰基和氟基团分别与 Phe265 和 His215 残基相互作用。此外，浓度为 100 μM 时，化合物7e表现出芽前和芽后除草活性，导致苋属杂草的种子发芽指数、胚根和下胚轴长度降低。
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