Study on Absorption, Distribution, Metabolism, and Excretion Properties of Novel Insecticidal GABA Receptor Antagonist, Pyraquinil, in Diamondback Moth Combining MALDI Mass Spectrometry Imaging and High-Resolution Mass Spectrometry,Journal of Agricultural and Food Chemistry

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Study on Absorption, Distribution, Metabolism, and Excretion Properties of Novel Insecticidal GABA Receptor Antagonist, Pyraquinil, in Diamondback Moth Combining MALDI Mass Spectrometry Imaging and High-Resolution Mass Spectrometry
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2022-05-16 , DOI: 10.1021/acs.jafc.2c00468
Kai Wan _{1,

2} , Xunyuan Jiang ₂ , Xuemei Tang ₂ , Lu Xiao ₂ , Yan Chen ₂ , Congling Huang ₂ , Fuwei Zhu ₂ , Fuhua Wang ₂ , Hanhong Xu ₁

Affiliation

A thorough understanding of absorption, distribution, metabolism, and excretion (ADME) of insecticide candidates is essential in insecticide development and structural optimization. Here, ADME of pyraquinil, a novel insecticidal GABA receptor antagonist, in Plutella xylostella larvae during the accumulation phase and depuration phase was investigated separately using a combination of UHPLC-Q-Orbitrap, HPLC-MS/MS, and MALDI-MSI. Five new metabolites of pyraquinil were identified, and a metabolic pathway was proposed. The oxidative metabolite (pyraquinil-sulfone) was identified as the main metabolite and confirmed by its standard. Quantitative results showed that pyraquinil was taken up by the larvae rapidly and then undergone a cytochrome P450s-mediated oxidative transformation into pyraquinil-sulfone. Both fecal excretion and oxidative metabolism were demonstrated to be predominant ways to eliminate pyraquinil in P. xylostella larvae during accumulation, while oxidative metabolism followed by fecal excretion was probably the major pathway during depuration. MALDI-MSI revealed that pyraquinil was homogeneously distributed in the larvae, while pyraquinil-sulfone presented a continuous enrichment in the midgut during accumulation. Conversely, pyraquinil-sulfone located in hemolymph can be preferentially eliminated during depuration, suggesting its tissue tropism. It improves the understanding of the fate of pyraquinil in P. xylostella and provides useful information for insecticidal mechanism elucidation and structural optimization of pyraquinil.

中文翻译：

结合MALDI质谱成像和高分辨率质谱研究小菜蛾新型杀虫GABA受体拮抗剂吡喹啉的吸收、分布、代谢和排泄特性

全面了解杀虫剂候选物的吸收、分布、代谢和排泄 (ADME) 对杀虫剂开发和结构优化至关重要。在这里，使用 UHPLC-Q-Orbitrap、HPLC-MS/MS 和 MALDI-MSI 的组合，分别研究了小菜蛾幼虫在小菜蛾幼虫积累阶段和净化阶段中吡喹尼的 ADME，这是一种新型杀虫 GABA 受体拮抗剂。鉴定出5种吡喹啉新代谢物，并提出了代谢途径。氧化代谢物（吡喹啉砜）被确定为主要代谢物，并通过其标准确认。定量结果表明，吡虫啉被幼虫迅速摄取，然后经过细胞色素P450s介导的氧化转化为吡喹啉砜。. 粪便排泄和氧化代谢都被证明是在小菜蛾幼虫积累过程中消除吡喹啉的主要途径，而氧化代谢和粪便排泄可能是净化过程中的主要途径。MALDI-MSI显示吡喹啉在幼虫中均匀分布，而吡喹啉砜在积累过程中在中肠中呈连续富集。相反，位于血淋巴中的吡喹酮砜可以在净化过程中优先消除，表明其组织趋向性。它提高了对小菜蛾中吡喹的归宿的认识，为吡喹的杀虫机理阐明和结构优化提供了有用的信息。

更新日期：2022-05-16

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