Original Article

Molecular docking of 5-o-benzoylpinostrobin derivatives from Boesenbergia pandurata roxb. as anti-inflammatory

Anang S. Wiyono, Siswandono Siswandono, Nuzul W. Diyah
Journal of Public Health in Africa | Vol 14, S 1 : 4th Joint Conference of UNAIR-USM, International Conference of Pharmacy and Health Sciences ICPHS| a137 | DOI: https://doi.org/10.4081/jphia.2023.2532 | © 2024 Anang S. Wiyono, Siswandono Siswandono, Nuzul W. Diyah | This work is licensed under CC Attribution 4.0
Submitted: 03 April 2024 | Published: 30 March 2023

About the author(s)

Anang S. Wiyono, Doctoral Program of Pharmaceutical Sciences, Faculty of Pharmacy, Universitas Airlangga, Surabaya, Indonesia; and, Diploma III Study Program of Pharmaceutical and Food Analysis, Faculty of Pharmacy, Institut Ilmu Kesehatan Bhakti Wiyata, Kediri, Indonesia
Siswandono Siswandono, epartment of Pharmaceutical Sciences, Faculty of Pharmacy, Universitas Airlangga, Surabaya, Indonesia
Nuzul W. Diyah, epartment of Pharmaceutical Sciences, Faculty of Pharmacy, Universitas Airlangga, Surabaya, Indonesia

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Abstract

Background: The use of NSAIDs, also known as non-steroidal anti-inflammatory drugs, has numerous adverse effects and consequences. For this reason, it is necessary to develop rational drugs as safer anti-inflammatory drugs with fewer side effects. Temu Kunci rhizome contains Pinostrobin (5-hydroxy-7- methoxyflavanone), which is believed to have anti-inflammatory properties. Objective: This study aims to determine the strongest anti-inflammatory activity at the cyclooxygenase-2 (COX-2) receptor through the 5-O-Benzoylpinostrobin derivative design. Methods: AutoDockTools on the COX-2 receptor (PDB code: 5IKR) were used in molecular docking in this study. The metrics employed were binding afinity (ΔG), inhibition constant (Ki), which serve as indicators of affinities, and amino acid residue similarity, which serves as a measure of the similarity of interactions. Predictive scores were confirmed by Molecular Docking Simulation. Results: The top five 5-O-Benzoylpinostrobin derivatives show a high affinity for the COX-2 receptor compared to Pinostrobin as a marker compound of Boesenbergia pandurata Roxb and furthermore give the lowest inhibition constant (Ki) and the highest negative binding free energy (ΔG), 35.40, 45.21, 54.75, 64.43, 76.97 nM and -10.16, -10.02, -9.91, -9.81, -9.7 kcal/mol. Interestingly, the five 5-O-Benzoylpinostrobin derivatives also have higher affinity than the native ligand Mefenamic acid, which is known to be a non-selective COX-2 inhibitor. The highest predicted affinity was shown by 4-Nitro-5-O-benzoylpinostrobin for the COX-2 receptor (PDP ID: 5IKR), with a higher predicted affinity for Mefenamic acid. Conclusion: The five selected 5-O-Benzoylpinostrobin derivatives were potent modifications of pinostrobin as an anti-inflammatory because they showed a higher affinity than Pinostrobin and Mefenamic acid. This study demonstrated that it is highly feasible to produce and test the novel 5-O-Benzoylpinostrobin derivative in vivo, specifically 4-Nitro-5-O-benzoylpinostrobin.

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