Bridging in silico and in vitro perspectives to unravel molecular mechanisms underlying the inhibition of β-glucuronidase by coumarins from Hibiscus trionum

Biophys Chem. 2024 Oct:313:107304. doi: 10.1016/j.bpc.2024.107304. Epub 2024 Jul 26.

Abstract

Unraveling the intricacies of β-glucuronidase inhibition is pivotal for developing effective strategies in applications specific to gastrointestinal health and drug metabolism. Our study investigated the efficacy of some Hibiscus trionum phytochemicals as β-glucuronidase inhibitors. The results showed that cleomiscosin A and mansonone H emerged as the most potent inhibitors, with IC50 values of 3.97 ± 0.35 μM and 10.32 ± 1.85 μM, respectively. Mechanistic analysis of β-glucuronidase inhibition indicated that cleomiscosin A and the reference drug EGCG displayed a mixed inhibition mode against β-glucuronidase, while mansonone H exhibited noncompetitive inhibition against β-glucuronidase. Docking studies revealed that cleomiscosin A and mansonone H exhibited the lowest binding affinities, occupying the same site as EGCG, and engaged significant key residues in their binding mechanisms. Using a 30 ns molecular dynamics (MD) simulation, we explored the interaction dynamics of isolated compounds with β-glucuronidase. Analysis of various MD parameters showed that cleomiscosin A and mansonone H exhibited consistent trajectories and significant energy stabilization with β-glucuronidase. These computational insights complemented experimental findings, underscoring the potential of cleomiscosin A and mansonone H as β-glucuronidase inhibitors.

Keywords: Enzyme inhibition; Enzyme kinetics; In Vitro study; Molecular dynamic simulations; β-Glucuronidase.

MeSH terms

  • Coumarins* / chemistry
  • Coumarins* / metabolism
  • Coumarins* / pharmacology
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology
  • Glucuronidase* / antagonists & inhibitors
  • Glucuronidase* / chemistry
  • Glucuronidase* / metabolism
  • Glycoproteins
  • Hibiscus* / chemistry
  • Humans
  • Molecular Docking Simulation*
  • Molecular Dynamics Simulation*

Substances

  • Glucuronidase
  • Coumarins
  • beta-glucuronidase inhibitor
  • Enzyme Inhibitors
  • Glycoproteins