Oxidative metabolism mechanism of terpenoid compound ZQ-8 by cytochrome P450 enzyme in Helicoverpa armigera

Int J Biol Macromol. 2024 Dec 20:138989. doi: 10.1016/j.ijbiomac.2024.138989. Online ahead of print.

Abstract

In our previous research, we identified that treatment of Helicoverpa armigera with ZQ-8 led to upregulation of CYP450 genes. To clarify the metabolic pathway of ZQ-8, this study analyzed the expression of CYP450 genes and proteins in H. armigera after ZQ-8 treatment through transcriptomics and proteomics. Molecular docking, recombinant protein expression, and surface plasmon resonance techniques were employed to investigate the interactions between ZQ-8 and P450 proteins. The oxidative reduction related pathways were significantly enriched in H. armigera larvae treated with ZQ-8, with an increase in the expression of CYP6B2 and CYP6B6 genes. The CYP6B2 and CYP6B6 proteins exhibited significant expression following ZQ-8 treatment. ZQ-8 demonstrated rapid binding and stable dissociation characteristics with CYP6B6, characterized by a dissociation constant (KD) of 88.15 μM. In contrast, ZQ-8 also showed rapid binding and dissociation with CYP6B2, but with a lower KD of 74.77 μM indicating that CYP6B2 has a stronger binding affinity for ZQ-8 compared to CYP6B6, and is capable of oxidizing ZQ-8 to the corresponding carboxylic acid. This study provides a reference for the metabolism and mechanism of action of ZQ-8 as a potential drug molecule, laying the foundation for future drug design and optimization, paving the way for environmentally sustainable pest control strategies and reducing reliance on traditional chemical pesticides.

Keywords: Binding affinity; CYP450 proteins; Helicoverpa armigera; Oxidative metabolism; ZQ-8.