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Vol. 36 No. 1 (2024): Vol 36 Issue 1, 2024

Copyright (c) 2023 Mongkol Nontakitticharoen, Thidathep Mahaamnart, Siripit Pitchuanchom, Thanaset Senawong, Surapon Saensouk

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This work is licensed under a Creative Commons Attribution 4.0 International License.

Cytotoxicity and Molecular Docking to Histone Deacetylase of Phytochemicals from Ventilago denticulata Leaves

https://doi.org/10.14233/ajchem.2024.30551
Thidathep Mahaamnart
Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand
https://orcid.org/0009-0009-5928-2907
Siripit Pitchuanchom
Multidisciplinary Research Unit of Pure and Applied Chemistry, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahasarakham University, Maha Sarakham 44150, Thailand
https://orcid.org/0000-0001-7712-152X
Thanaset Senawong
Natural Products Research Unit, Department of Biochemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand
https://orcid.org/0000-0001-8788-5291
Surapon Saensouk
Diversity of Family Zingiberaceae and Vascular Plant for Its Applications Research Unit, Walai Rukhavej Botanical Research Institute, Mahasarakham University, Maha Sarakham 44150, Thailand
https://orcid.org/0000-0002-9178-188X
Mongkol Nontakitticharoen
Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand
https://orcid.org/0000-0002-2931-5917

Corresponding Author(s) : Mongkol Nontakitticharoen

mongbu@kku.ac.th

Asian Journal of Chemistry, Vol. 36 No. 1 (2024): Vol 36 Issue 1, 2024

Abstract

Phytochemical investigation of the ethyl acetate and methanol extracts of Ventilago denticulata leaves resulted in the isolation of five flavonoids (1-5) and three anthraquinones (6-8). Their structures were characterized using spectroscopic techniques including UV, IR, 1H NMR, 13C NMR, and 2D NMR, as well as mass spectrometry (MS). Among these, compounds 4 (rhamnetin) and 6 (frangulin B) emerged as potential HDAC inhibitors, displaying significant inhibitory activities against HeLa nuclear extract. Molecular docking with HDAC isoforms revealed their affinity, particularly for class II HDAC4 enzyme. Both compounds exhibited promising physicochemical properties compliant with Lipinski’s rule of five, indicative of their drug-like potential. In vitro antiproliferative assays demonstrated that compound 6 exhibited superior activity against HeLa, A549 and MCF-7 cancer cell lines with the IC50 values ranging from 8.35 to 20.93 mM, whereas compound 4 showed reduced cytotoxicity in non-cancerous Vero cells. Furthermore, compound 6 was isolated from V. denticulata for the first time.

Keywords

Ventilago denticulata Cytotoxicity Molecular docking Flavonoid Anthraquinone
Mahaamnart, T., Pitchuanchom, S., Senawong, T., Saensouk, S., & Nontakitticharoen, M. (2023). Cytotoxicity and Molecular Docking to Histone Deacetylase of Phytochemicals from Ventilago denticulata Leaves. Asian Journal of Chemistry, 36(1), 25–31. https://doi.org/10.14233/ajchem.2024.30551
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