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Cypyrafluone, a 4-Hydroxyphenylpyruvate Dioxygenase Inhibitor to Control Weed in Wheat Fields
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-06-01 , DOI: 10.1021/acs.jafc.3c01239 Lei Lian 1, 2 , Hengzhi Wang 3 , Fengwen Zhang 3 , Weitang Liu 3 , Xingtao Lu 2 , Tao Jin 2 , Jinxin Wang 3 , Xiuhai Gan 1 , Baoan Song 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-06-01 , DOI: 10.1021/acs.jafc.3c01239 Lei Lian 1, 2 , Hengzhi Wang 3 , Fengwen Zhang 3 , Weitang Liu 3 , Xingtao Lu 2 , Tao Jin 2 , Jinxin Wang 3 , Xiuhai Gan 1 , Baoan Song 1
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As a bleaching herbicide, cypyrafluone was applied postemergence in wheat fields for annual weed control; especially, this herbicide possesses high efficacy against cool-season grass weed species such as Alopecurus aequalis and Alopecurus japonicus. In this study, the target of action of cypyrafluone on 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibition was confirmed. This herbicide caused severe foliar whitening symptoms at 5–7 days after treatment (DAT) and death of the whole plant within 10 DAT. Significant increases in phytoene content and significant decreases in kinds of carotenoid and chlorophyll pigments were observed. The content of chlorophyll pigments in cypyrafluone-treated Spirodela polyrhiza decreased upon the addition of homogentisic acid (HGA), which indicated that cypyrafluone prevents the HGA production, possibly by inhibiting the catalytic activity of 4-HPPD. Indeed, cypyrafluone strongly inhibited the catalytic activity of Arabidopsis thaliana HPPD produced by Escherichia coli, which was approximately 2 times less effective than mesotrione. In addition, overexpression of Oryza sativa HPPD in rice and A. thaliana both conferred a high tolerance level to cypyrafluone on them. Molecular docking found that cypyrafluone bonded well to the active site of the HPPD and formed a bidentate coordination interaction with the Fe2+ atom, with distances of 2.6 and 2.7 Å between oxygen atoms and the Fe2+ atom and a binding energy of −8.0 kcal mol–1.
中文翻译：
Cypyrafluone，一种用于控制麦田杂草的 4-羟基苯丙酮酸双加氧酶抑制剂
cypyrafluone作为漂白除草剂在麦田进行苗后防除一年生杂草；特别是，该除草剂对冷季型禾本科杂草如木槿、木槿等具有较高的药效。在这项研究中，cypyrafluone 对 4-羟基苯丙酮酸双加氧酶 (HPPD) 抑制作用的作用靶点得到证实。这种除草剂在处理后 5-7 天 (DAT) 引起严重的叶面变白症状，并在 10 DAT 内导致整株植物死亡。观察到八氢番茄红素含量显着增加，类胡萝卜素和叶绿素色素种类显着减少。环吡氟酮处理多根紫菜中叶绿素色素的含量在加入尿黑酸 (HGA) 后降低，这表明 cypyrafluone 可能通过抑制 4-HPPD 的催化活性来阻止 HGA 的产生。实际上，cypyrafluone 强烈抑制了大肠杆菌产生的拟南芥HPPD的催化活性，其效果比甲基磺草酮低约 2 倍。此外，Oryza sativa HPPD在水稻和拟南芥中的过表达均赋予它们对环吡氟酮的高耐受性。分子对接发现cypyrafluone与HPPD的活性位点结合良好，与Fe 2+形成双齿配位相互作用 原子，氧原子和 Fe 2+原子之间的距离为 2.6 和 2.7 Å，结合能为 −8.0 kcal mol –1。
更新日期：2023-06-01
中文翻译：
Cypyrafluone，一种用于控制麦田杂草的 4-羟基苯丙酮酸双加氧酶抑制剂
cypyrafluone作为漂白除草剂在麦田进行苗后防除一年生杂草；特别是，该除草剂对冷季型禾本科杂草如木槿、木槿等具有较高的药效。在这项研究中，cypyrafluone 对 4-羟基苯丙酮酸双加氧酶 (HPPD) 抑制作用的作用靶点得到证实。这种除草剂在处理后 5-7 天 (DAT) 引起严重的叶面变白症状，并在 10 DAT 内导致整株植物死亡。观察到八氢番茄红素含量显着增加，类胡萝卜素和叶绿素色素种类显着减少。环吡氟酮处理多根紫菜中叶绿素色素的含量在加入尿黑酸 (HGA) 后降低，这表明 cypyrafluone 可能通过抑制 4-HPPD 的催化活性来阻止 HGA 的产生。实际上，cypyrafluone 强烈抑制了大肠杆菌产生的拟南芥HPPD的催化活性，其效果比甲基磺草酮低约 2 倍。此外，Oryza sativa HPPD在水稻和拟南芥中的过表达均赋予它们对环吡氟酮的高耐受性。分子对接发现cypyrafluone与HPPD的活性位点结合良好，与Fe 2+形成双齿配位相互作用 原子，氧原子和 Fe 2+原子之间的距离为 2.6 和 2.7 Å，结合能为 −8.0 kcal mol –1。
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