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手性药物酮康唑对蛋白核小球藻抗氧化防御系统和光合作用系统的立体选择性毒性。

Stereoselective toxicity of metconazole to the antioxidant defenses and the photosynthesis system of Chlorella pyrenoidosa.

机构信息

Department of Applied Chemistry, China Agricultural University, Yuanmingyuan West Road 2, Beijing, 100193, China; Beijing Advanced Innovation Center for Food Nutrition and Human Health, Yuanmingyuan West Road 2, Beijing, 100193, China.

Department of Applied Chemistry, China Agricultural University, Yuanmingyuan West Road 2, Beijing, 100193, China; Beijing Advanced Innovation Center for Food Nutrition and Human Health, Yuanmingyuan West Road 2, Beijing, 100193, China.

出版信息

Aquat Toxicol. 2019 May;210:129-138. doi: 10.1016/j.aquatox.2019.02.017. Epub 2019 Feb 25.

Abstract

Metconazole (MEZ) is a broad-spectrum fungicide with four optical stereoisomers. Compared to traditional fungicides, it achieves better control effect at lower dosages. However, its toxicity to non-target organisms has rarely been investigated. This study investigated the stereoselective toxicity of metconazole to Chlorella pyrenoidosa (C. pyrenoidosa). The results indicate that the presence of the racemate and four stereoisomers of MEZ caused a sudden increase of reactive oxygen species (ROS). This in turn stimulated antioxidant defense, impaired photosynthesis and responses of subcellular structure, and eventually inhibited cell growth. The 96 h-EC of the racemate, cis-1R,5S-MEZ, cis-1S,5R-MEZ, trans-1S,5S-MEZ, and trans-1R,5R-MEZ were 0.058, 0.182, 0.129, 0.032, and 0.038 mg/L, respectively. Furtheromre, the generation of ROS, antioxidant response, and the loss of photosynthetic function in C. pyrenoidosa were all preferentially trans-1S,5S-MEZ induced. These results aid the understanding of the stereoselective effects of chiral pesticides on C. pyrenoidosa. Such stereoselective differences must be considered when assessing the risk of metconazole to environment.

摘要

咪鲜胺(MEZ)是一种具有四个光学对映异构体的广谱杀菌剂。与传统杀菌剂相比,它在较低剂量下就能达到更好的控制效果。然而,其对非靶标生物的毒性很少被研究。本研究调查了咪鲜胺对栅藻(Chlorella pyrenoidosa,C. pyrenoidosa)的立体选择性毒性。结果表明,外消旋体和 MEZ 的四个对映异构体的存在会导致活性氧(ROS)的突然增加。这反过来又刺激了抗氧化防御,损害了光合作用和亚细胞结构的反应,最终抑制了细胞生长。外消旋体、顺-1R,5S-MEZ、顺-1S,5R-MEZ、反-1S,5S-MEZ 和反-1R,5R-MEZ 的 96 h-EC50 分别为 0.058、0.182、0.129、0.032 和 0.038 mg/L。此外,ROS 的产生、抗氧化反应以及栅藻光合作用功能的丧失均优先由反-1S,5S-MEZ 诱导。这些结果有助于理解手性农药对栅藻的立体选择性影响。在评估咪鲜胺对环境的风险时,必须考虑到这种立体选择性差异。

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