1. Academic Validation
  2. Bioassay-Guided and DeepSAT-Driven Precise Mining of Monoterpenoid Coumarin Derivatives with Antifeedant Effects from the Leaves of Ailanthus altissima

Bioassay-Guided and DeepSAT-Driven Precise Mining of Monoterpenoid Coumarin Derivatives with Antifeedant Effects from the Leaves of Ailanthus altissima

  • J Agric Food Chem. 2024 May 15;72(19):10958-10969. doi: 10.1021/acs.jafc.4c01049.
Zhi-Kang Duan 1 Xu Wang 2 Mei-Ya Lian 1 Shan-Shan Guo 1 Zhi-Heng Gao 1 Ming Bai 1 Xiao-Xiao Huang 1 3 Shao-Jiang Song 1
Affiliations

Affiliations

  • 1 Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.
  • 2 School of Pharmacy, Shenyang Pharmaceutical University, No. 103, Wenhua Road, Shenyang, Liaoning 110016, P. R. China.
  • 3 Basic Science Research Center Base (Pharmaceutical Science), Shandong province, Yantai University, Yantai 264005, China.
Abstract

Demand for the exploration of botanical pesticides continues to increase due to the detrimental effects of synthetic chemicals on human health and the environment and the development of resistance by pests. Under the guidance of a bioactivity-guided approach and HSQC-based DeepSAT, 16 coumarin derivatives were discovered from the leaves of Ailanthus altissima (Mill.) Swingle, including seven undescribed monoterpenoid Coumarins, three undescribed monoterpenoid Phenylpropanoids, and two new coumarin derivatives. The structure and configurations of these compounds were established and validated via extensive spectroscopic analysis, acetonide analysis, and quantum chemical calculations. Biologically, 5 exhibited significant antifeedant activity toward the Plutella xylostella. Moreover, Tyrosinase being closely related to the growth and development of larva, the inhibitory potentials of 5 against Tyrosinase was evaluated in vitro and in silico. The bioactivity evaluation results highlight the prospect of 5 as a novel category of botanical insecticide.

Keywords

Ailanthus altissima (Mill.) Swingle; antifeedant; monoterpenoid coumarin derivatives; tyrosinase.

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