Insecticidal Endostemonines A-J Produced by Endophytic Streptomyces from Stemona sessilifolia

J Agric Food Chem. 2020 Feb 12;68(6):1588-1595. doi: 10.1021/acs.jafc.9b06755. Epub 2020 Jan 29.

Abstract

The discovery of new, safe, and effective pesticides is one of the main means for modern crop protection and parasitic disease control. During the search for new insecticidal secondary metabolites from endophytes in Stemona sessilifolia (a traditional Chinese medicine with a long history as an insecticide), 10 new insecticidal endostemonines A-J (1-10) were identified from an endophytic Streptomyces sp. BS-1. Their structures were determined by comprehensive spectroscopic analysis. Endostemonines A-J represent the first reported naturally occurring pyrrole-2-carboxylic ester derivatives, which consisted of different fatty acid chains at the C-2 of pyrrole ring were produced by traditional Chinese medicine endophytic microbes. All new tested compounds exhibited strong lethal activity against Aphis gossypii (LC50 value range of 3.55-32.00 mg/L after 72 h). This research highlighted the discovery of pesticide natural products from insecticidal medicinal plant endophytes for the first time, paving a new pathway for the development of pest control.

Keywords: Stemona sessilifolia; endophyte; endostemonine; insecticidal activity; secondary metabolite.

MeSH terms

  • Animals
  • Aphids / drug effects
  • Endophytes / chemistry*
  • Endophytes / metabolism
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Heterocyclic Compounds, 3-Ring / metabolism*
  • Heterocyclic Compounds, 3-Ring / toxicity
  • Insecticides / chemistry
  • Insecticides / metabolism*
  • Insecticides / toxicity
  • Secondary Metabolism
  • Stemonaceae / microbiology*
  • Streptomyces / chemistry*
  • Streptomyces / metabolism*

Substances

  • Heterocyclic Compounds, 3-Ring
  • Insecticides
  • stemoninine