Enantioselective uptake, translocation, and biotransformation of pydiflumetofen in wheat (Triticum aestivum L.): Insights from chiral profiling and molecular simulation

Pydiflumetofen (PYD), a highly effective and broad-spectrum fungicide, is commonly employed for the control of fungal diseases. In this study, the uptake, translocation, and biotransformation of PYD by wheat (Triticum aestivum L.) were firstly investigated at a chiral level. The findings revealed that the residue concentration of R-PYD in wheat was higher than that of S-PYD, because of its higher uptake rate (k1 = 0.0421 h-1) and lower elimination rate (k2 = 0.0459 h-1). Additionally, R-PYD exhibited higher root bioconcentration factors and translocation factors compared with S-enantiomer, indicating R-PYD was more easily accumulating in roots and translocating to shoots. Furthermore, a total of 9 metabolites, including hydroxylated, demethylated, demethoxylated, dechlorinated, hydrolyzed, and glycosylated-conjugated products, were detected qualitatively in wheat roots or shoots. Symplastic pathway-mediated uptake, which predominantly relied on aquaporins and anion channels, was confirmed by root adsorption and inhibition experiments, without displaying any enantioselective effect. Molecular simulations demonstrated that R-PYD exhibited stronger binding affinity with TaLTP 1.1 with a lower grid score (-6.79 kcal/mol), whereas weaker interaction with the metabolic enzyme (CYP71C6v1) compared to the S-enantiomer. These findings highlight the significance of plant biomacromolecules in the enantioselective bioaccumulation and biotransformation processes. Importantly, a combination of experimental and theoretical evidence provide a comprehensive understanding of the fate of chiral pesticides in plants from an enantioselective perspective.

Bibliographic Details

Main Authors:	Wang, Zhen, Li, Yanhong, Tan, Yuting, Li, Rui, Zhou, Liangliang, He, Zongzhe, Barceló, Damià, Shi, Haiyan, Wang, Minghua
Format:	artículo biblioteca
Language:	English
Published:	Elsevier 2023-08-10
Subjects:	Uptake mechanism, Enantioselectivity, Metabolic pathways, Plant biomacromolecules, Pydiflumetofen, http://metadata.un.org/sdg/6, Ensure availability and sustainable management of water and sanitation for all,
Online Access:	http://hdl.handle.net/10261/334366 https://api.elsevier.com/content/abstract/scopus_id/85167795258
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