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Diversifying the benzenesulfonamide scaffold for potential V-ATPase inhibitors: synthesis and insecticidal activity evaluation

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Abstract

Celangulin V is a natural β-dihydroagarofuran derivative isolated from Celastrus angulatus which shows insecticidal activity in many agricultural pests. Using celangulin V as a molecular probe, we find out a new pesticide target: subunit H of V-ATPase. To explore the potential application of this novel target, lead sulfonamides have been found through virtual screening. Combined with the previous work, 46 sulfonamide derivatives are designed and synthesized. All target compounds are first screened for their insecticidal activities against Mythimna separata. The results of bioassay reveal that most of the designed compounds exhibit significant insecticidal activities against third-instar larvae of M. separata under the concentration of 10 mg/mL, and compound 8.4 shows the highest activity with LC50 value of 1.72 mg/mL, 15-fold smaller than that of celangulin V (25.89 mg/mL). Molecular docking results further indicated that compound 8.4 might serve as a potential inhibitor of the subunit H of V-ATPase. This study provides a potential sulfonamide candidate compound for the M. separata control.

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Funding

This work was supported by the National Natural Science Foundation of China [Grant No. 21977083].

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Authors and Affiliations

  1. College of Chemistry & Pharmacy, Shaanxi Key Laboratory of Natural Products & Chemical Biology, Northwest A&F University, Yangling, 712100, People’s Republic of China

    Hao Qian, Tao Guo, Yingkun Hu, Keyin Yu & Jiwen Zhang

  2. Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, 712100, People’s Republic of China

    Jinyu Zhang, Wenjun Wu & Jiwen Zhang

  3. Xi’an Customs Technology Center, Xi’an, 710068, People’s Republic of China

    Changzhao Wang

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  1. Hao Qian
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  2. Tao Guo
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  3. Jinyu Zhang
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  4. Yingkun Hu
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  5. Changzhao Wang
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  6. Keyin Yu
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  7. Wenjun Wu
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  8. Jiwen Zhang
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Contributions

HQ,·TG, JZ, and YH planned and performed the experiments with advice from ·WW, JZ, and KY. HQ wrote the manuscript with the help from CW.

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Correspondence to Jiwen Zhang.

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Qian, H., Guo, T., Zhang, J. et al. Diversifying the benzenesulfonamide scaffold for potential V-ATPase inhibitors: synthesis and insecticidal activity evaluation. Mol Divers (2024). https://doi.org/10.1007/s11030-023-10800-w

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