Startseite Design of gossypetin derivatives based on naturally occurring flavonoid in Hibiscus sabdariffa and the molecular docking as antibacterial agents
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Design of gossypetin derivatives based on naturally occurring flavonoid in Hibiscus sabdariffa and the molecular docking as antibacterial agents

  • Nuzul W. Diyah EMAIL logo , Isnaeni , Shabrina W. Hidayati , Bambang T. Purwanto und Siswandono
Veröffentlicht/Copyright: 25. Juni 2021

Abstract

Objectives

This study was purposed to design gossypetin derivatives which have higher activity than the parent compound found in Hibiscus sabdariffa and to find the most potent compound as the antibacterial agent.

Methods

Twenty-five gossypetin derivatives were designed by conjugation the molecular structure of gossypetin with acyl group from some natural phenolic acids. The antibacterial activity was predicted by docking simulation on Escherischia coli DNA gyrase (PDB. 1KZN) which was performed by Molegro Virtual Docker. Potency as an antibacterial agent was evaluated based on binding affinity, hydrogen bond, and similarity of binding pattern with reference ligand Clorobiocin.

Results

Almost all derivatives showed higher binding affinity than gossypetin (docking score −113.43 kcal/mol). The most active compound was 3G19 with docking score −167.42 kcal/mol which was comparable to clorobiocin (docking score −167.75 kcal/mol). The compounds displaying higher activity than gossypetin were belonged to 7,4′-dimethyl and 3,7,4′-trimethylgossypetin of coumaric acid, caffeic acid, and also ferulic acid. The compounds showed similar binding mode with clorobiocin especially in interaction with Asn46.

Conclusions

Gossypetin derivatives designed by conjugating the gossypetin with phenolic acyl increased in silico antibacterial activity of the parent compound. The 3,7,4′-trimethylgossypetin of coumaric acid was selected as the most potent compound for antibacterial agents.


Corresponding author: Nuzul W. Diyah, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Airlangga, Kampus C, UNAIR. Jl. Mulyerejo, Surabaya, 60115, Indonesia, E-mail:

Funding source: Airlangga University

Award Identifier / Grant number: PUF 2019

Acknowledgments

The authors thank the Prof. Dr. Siswandono, M.S., Apt. who has the MVD program license for his permission to use the software in performing docking simulation.

  1. Research funding: This research was financially supported by the Primary Research Grant (PUF 2019) from Faculty of Pharmacy Airlangga University.

  2. Author contributions: All authors have accepted responsibility for the entire content of this manuscript and approved its submission.

  3. Competing interests: Authors state that this article content has no conflicts of interest.

  4. Informed consent: Not applicable.

  5. Ethical approval: Not applicable.

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Received: 2020-11-29
Accepted: 2021-02-03
Published Online: 2021-06-25

© 2021 Walter de Gruyter GmbH, Berlin/Boston

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