Enantiomers of chiral pesticides usually display different toxic effects on non-target organisms in surrounding environment, but there are few studies on its enantioselective toxicity of paclobutrazol to aquatic organisms such as Chlorella vulgaris (C. vulgaris). In this study, the enantioselective bioaccumulation and toxicities, such as acute toxicity and oxidative stress, of the racemate, (2S, 3S)-enantiomer (S-enantiomer) and (2R, 3R)-enantiomer (R-enantiomer) of paclobutrazol to the C. vulgaris cells were investigated. The results showed that the algae cells were able to accumulate the paclobutrazol in a short time, while this bioaccumulation had no enantioselective distinction between the two enantiomers during biological metabolism. However, the racemate and two enantiomers of paclobutrazol significantly inhibited the growth of C. vulgaris, displayed different median lethal concentrations. The photosynthetic pigments, photosynthesis-related genes as well as antioxidation-related biomarkers in treated C. vulgaris were also investigated. In general, R-enantiomer was found to be more toxic to C. vulgaris cells than its racemate and S-enantiomer. Additionally, transmission electron microscopy (TEM) analysis showed the R-enantiomer caused more serious changes than S-enantiomer. Moreover, contents of two plant hormones (gibberellin, GA and indoleacetic acid, IAA) were determined in treated C. vulgaris. Higher paclobutrazol concentrations caused lower IAA contents significantly. Nevertheless, the two enantiomers showed no enantioselective effects on the biosynthesis of GA in C. vulgaris. Our results are helpful to understand the enantioselective effects of paclobutrazol enantiomers on non-target organisms, and useful for evaluating their environmental risks.
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http://dx.doi.org/10.1016/j.envpol.2019.04.027 | DOI Listing |
Chirality
February 2024
Qinghai Tongren City Agriculture and Animal Husbandry Comprehensive Service Center, Xianyang, Shaanxi Province, People's Republic of China.
Chiral pesticides have the special chiral structures, so enantioselective biological effects are usually observed in living organisms. Current study used paclobutrazol as a case study and explored the enantioselective degradation and oxidative stress effect on wheat. The results demonstrated that the degradation of R-paclobutrazol was faster than S-paclobutrazol significantly and improved the content of MDA and O in wheat plants, which proved that the R-paclobutrazol induced oxidative damage in wheat, showing selective biological effects, and S-paclobutrazol was friendly to wheat.
View Article and Find Full Text PDFMikrochim Acta
December 2023
Department of Sanitary Inspection, School of Public Health, Shenyang Medical College, No. 146, North Huanghe Street, Liaoning Province, Shenyang, 110034, China.
An efficient method is presented for simultaneous enantioselective determination of three chiral triazole fungicides (namely paclobutrazol, hexaconazole, and diniconazole) in water samples by DSPE-HPLC-UV. The perfect chiral separation of the enantiomers was achieved on a Chiralpak IH column within 15 min. In order to adsorb and enrich the analytes from water matrices, a cross-linked hydroxypropyl β-cyclodextrin polymer was synthesized.
View Article and Find Full Text PDFPestic Biochem Physiol
August 2023
School of Chemistry, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, and GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, South China Normal University, Guangzhou 510006, China; MOE Key laboratory of Laser Life Science & Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou 510631, China; Guangdong Provincial Key Laboratory of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou 510631, China. Electronic address:
Paclobutrazol is a plant growth inhibitor widely used in agricultural production. However, toxicology studies of paclobutrazol enantiomers towards aquatic organisms are limited. Herein, effects of paclobutrazol and its two enantiomers (2R, 3R; 2S, 3S) on glycolipid metabolism of zebrafish have been systemically explored at the concentration of 10 mg/L through biochemical analyses, LC-MS/MS, molecular dynamics simulation, and gene expression.
View Article and Find Full Text PDFChemistry
June 2023
Department of Molecular Chemistry, Materials and Catalysis, Institute of Condensed Matter and Nanosciences, Université Catholique de Louvain, Place Louis Pasteur, 1 bte L4.01.06, 1348, Louvain-La-Neuve, Belgium.
We report the first case of mechanochemical deracemization by using liquid-assisted abrasive grinding. The target molecule is a precursor of Paclobutrazol, an important fungicide and plant growth inhibitor. Using mechanochemical deracemization, we are even able to transform a 10 % ee scalemic mixture of this latter in an enantioenriched product of 97 % ee in a couple of hours.
View Article and Find Full Text PDFChirality
June 2023
State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products/Key Laboratory of Detection for Pesticide Residues and Control of Zhejiang, Institute of Agro-product Safety and Nutrition, Zhejiang Academy of Agricultural Sciences, Hangzhou, P. R. China.
Studies on the differences between chiral pesticide enantiomers have caused widespread concern in the last decade. In the current work, the selective behaviors and different biological activities of paclobutrazol enantiomers during Chinese cabbage pickling process were evaluated. Results of degradation kinetics indicated that when paclobutrazol reside in raw material (Chinese cabbage) and was introduced into the pickling process, the degradation rates of the two paclobutrazol enantiomers were significantly different, the half-lives of (2R, 3R)-paclobutrazol (R-paclobutrazol) and (2S, 3S)-paclobutrazol (S-paclobutrazol) were 18.
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