Design, Synthesis and Biological Evaluation of Novel Phenyl-Substituted Naphthoic Acid Ethyl Ester Derivatives as Strigolactone Receptor Inhibitor

Int J Mol Sci. 2024 Mar 31;25(7):3902. doi: 10.3390/ijms25073902.

Abstract

Strigolactones (SLs) are plant hormones that regulate several key agronomic traits, including shoot branching, leaf senescence, and stress tolerance. The artificial regulation of SL biosynthesis and signaling has been considered as a potent strategy in regulating plant architecture and combatting the infection of parasitic weeds to help improve crop yield. DL1b is a previously reported SL receptor inhibitor molecule that significantly promotes shoot branching. Here, we synthesized 18 novel compounds based on the structure of DL1b. We performed rice tillering activity assay and selected a novel small molecule, C6, as a candidate SL receptor inhibitor. In vitro bioassays demonstrated that C6 possesses various regulatory functions as an SL inhibitor, including inhibiting germination of the root parasitic seeds Phelipanche aegyptiaca, delaying leaf senescence and promoting hypocotyl elongation of Arabidopsis. ITC analysis and molecular docking experiments further confirmed that C6 can interact with SL receptor proteins, thereby interfering with the binding of SL to its receptor. Therefore, C6 is considered a novel SL receptor inhibitor with potential applications in plant architecture control and prevention of root parasitic weed infestation.

Keywords: molecular design; seed germination; senescence; strigolactone inhibitor; tillering.

MeSH terms

  • Arabidopsis*
  • Carboxylic Acids
  • Esters*
  • Heterocyclic Compounds, 3-Ring*
  • Lactones*
  • Molecular Docking Simulation
  • Naphthalenes*

Substances

  • 1-naphthoic acid
  • Esters
  • GR24 strigolactone
  • Carboxylic Acids
  • Heterocyclic Compounds, 3-Ring
  • Lactones
  • Naphthalenes