Synthesis of Analogs of Strigolactones and Evaluation of Their Stability in Solution

Methods Mol Biol. 2021:2309:37-55. doi: 10.1007/978-1-0716-1429-7_5.

Abstract

Strigolactones (SLs) are new plant hormones that play an important role in the control development of plants. They are germination stimulants for seed of parasitic weeds, are the branching factor of arbuscular mycorrhizal fungi and inhibitors for bud outgrowth and shoot branching. Natural SLs contain an annulated system of three rings (ABC scaffold) connected to a furanone (the D-ring) by an enol ether unit. The natural distribution of strigolactones is low, and their synthesis is long and difficult. Therefore, SL analogs are designed to have the same bioactiphore as natural SLs and an appreciable bioactivity. For the design a model is used based on the natural bioactiphore. Typical SL analogs are GR24, Nijmegen-1, and EM1 (derived from ethyl 2-phenylacetate). The synthesis of these SL analogs is reported together with their stability in aqueous solution.

Keywords: Bioactiphore; GR24; Simple strigolactone analogs; Stability in solution; Strigolactone.

MeSH terms

  • Drug Stability
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / pharmacology
  • Hydrogen-Ion Concentration
  • Lactones / chemical synthesis*
  • Lactones / pharmacology
  • Molecular Structure
  • Plant Growth Regulators / chemical synthesis*
  • Plant Growth Regulators / pharmacology
  • Solubility
  • Solutions
  • Structure-Activity Relationship

Substances

  • GR24 strigolactone
  • Heterocyclic Compounds, 3-Ring
  • Lactones
  • Plant Growth Regulators
  • Solutions