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Calmodulin-Targeting Molecules from Ageratina grandifolia.

José A Gutiérrez-González1, Araceli Pérez-Vásquez1, Martín González-Andrade2

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Four new natural compounds were isolated from Ageratina grandifolia. Four compounds (8, 10, 11, 12) showed high affinity for calmodulin, indicating therapeutic potential.

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Area of Science:

  • Natural Product Chemistry
  • Medicinal Chemistry
  • Pharmacology

Background:

  • Ageratina grandifolia is a plant species known for its diverse chemical constituents.
  • Natural products serve as a valuable source for novel therapeutic agents.
  • Calmodulin (CaM) is a crucial calcium-binding protein involved in numerous cellular processes.

Purpose of the Study:

  • To isolate and characterize new and known compounds from the aerial parts of Ageratina grandifolia.
  • To investigate the potential of isolated compounds as calmodulin inhibitors.
  • To explore the therapeutic and research tool potential of these natural products.

Main Methods:

  • Isolation and purification of compounds using chromatographic techniques.
  • Structure elucidation employing spectroscopic methods (HR-MS, NMR) and computational analysis (DFT, DP4+).
  • In vitro binding assays to assess calmodulin affinity and molecular dynamics simulations to evaluate complex stability.

Main Results:

  • Four new natural chemical entities (2-hydroxy-α-truxillic acid, compound 3, N-tricosanoyltyramine, and grandifolamide) were identified.
  • Eleven known compounds were also isolated and characterized.
  • Compounds 3,5-Diprenyl-4-hydroxyacetophenone (8), O-methylencecalinol (10), encecalin (11), and encecalinol (12) exhibited higher binding affinity to calmodulin compared to chlorpromazine.
  • Molecular dynamics simulations confirmed the stability of the complexes formed between compounds 8, 10, 11, 12 and calmodulin.

Conclusions:

  • The study successfully identified novel compounds from Ageratina grandifolia.
  • Compounds 8, 10, 11, and 12 demonstrate significant potential as calmodulin modulators.
  • These findings highlight the therapeutic utility and value of these compounds as research tools in pharmacology.