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Investigation of the Skin Anti-photoaging Potential of Swertia chirayita Secoiridoids Through the AP-1/Matrix Metalloproteinase Pathway by Molecular Modeling

  • Pathomwat Wongrattanakamon
  • Piyarat Nimmanpipug
  • Busaban Sirithunyalug
  • Wantida Chaiyana
  • Supat Jiranusornkul
Article
  • 116 Downloads

Abstract

Secoiridoids are bioactive compounds, which are present in plants and exhibit anti-inflammatory activity. In this work, to understand the structural basis of five secoiridoids; amarogentin, amaroswerin, gentiopicrin, sweroside, and swertiamarin for potent inhibitors of the target proteins associated with the collagen degradation pathway, namely MMP-1, MMP-3, MMP-9 and transcription factor AP-1, molecular docking, binding mode modeling, and MD simulations were carried out. The binding inhibitory effects of the secoiridoids were screened on these proteins. The obtained results in terms of binding conformation, binding free energy, protein–ligand interaction profile, structural flexibility, and binding energy decomposition of the secoiridoid inhibitors were elucidated. The molecular modeling clarified inhibitory effect on account of the five secoiridoids towards all three Matrix metalloproteinases (MMPs). Moreover, amarogentin and gentiopicrin may interfere with gene expression via binding to AP-1. Among all screened secoiridoids, amarogentin and gentiopicrin exhibited an interesting binding affinity to the MMPs and AP-1. The results suggest that amarogentin has the highest potential for application as an anti-aging agent with the MMP inhibitory and anti-transcriptional activities, even though further studies are needed to determine the anti-aging effect in vitro, in vivo and by clinical evaluation.

Keywords

Anti-aging Matrix metalloproteinases Molecular docking Molecular dynamics simulation Photoaging Secoiridoids Swertia chirayita 

Notes

Acknowledgements

The authors would like to thank Inte:Ligand Software-Entwicklungs und Consulting GmbH for providing an academic free license for LigandScout 4.1.

Compliance with Ethical Standards

Conflict of interest

Every author declares no conflict of interest.

Research Involving Human and Animal Rights

This article does not contain any study with human or animal subjects performed by any of the authors.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Laboratory for Molecular Design and Simulation (LMDS), Department of Pharmaceutical Sciences, Faculty of PharmacyChiang Mai UniversityChiang MaiThailand
  2. 2.Computational Simulation and Modelling Laboratory (CSML), Department of Chemistry, Faculty of ScienceChiang Mai UniversityChiang MaiThailand
  3. 3.Department of Pharmaceutical Sciences, Faculty of PharmacyChiang Mai UniversityChiang MaiThailand

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