Abstract
In the present work, three hydroxyxanthones were synthesized in 11.15–33.42% yield from 2,6-dihydroxybenzoic acid as the starting material. The chemical structures of prepared hydroxyxanthones have been elucidated by using spectroscopic techniques. Afterward, the hydroxyxanthones were evaluated as antioxidant agents through radical scavenging assay; and anticancer agents through in vitro assays against WiDr, MCF-7, and HeLa cancer cell lines. Hydroxyxanthone 3b was categorized as a strong antioxidant agent (IC50 = 349 ± 68 µM), while the other compounds were categorized as moderate antioxidant agents (IC50 > 500 µM). On the other hand, hydroxyxanthone 3a exhibited the highest anticancer activity (IC50 = 184 ± 15 µM) and the highest selectivity (SI = 18.42) against MCF-7 cancer cells. From the molecular docking study, it was found that hydroxyxanthone 3a interacted with the active sites of Topoisomerase II protein through Hydrogen bonding with DG13 and π–π stacking interactions with DA12 and DC8. These findings revealed that hydroxyxanthones are potential candidates to be developed as antioxidant and anticancer agents in the future.
Highlights
In the present work, three hydroxyxanthones were synthesized in 11.15–33.42% yield from 2,6-dihydroxybenzoic acid as the starting material
The Fourier transform infrared (FTIR) spectra of hydroxyxanthones showed the appearance of O–H hydroxyl groups at 3425–3448 cm−1 while the C=O functional group appeared as a sharp signal at 1604–1612 cm−1
From the reported quantitative structure–activity relationship (QSAR) study, we found that the IC50 value of hydroxyxanthone as the anticancer agent against WiDr cancer cell line depends on the net atomic charge on carbon atoms, dipole moment, and octanol/water partition c oefficient[33]
Summary
Three hydroxyxanthones were synthesized in 11.15–33.42% yield from 2,6-dihydroxybenzoic acid as the starting material. From the molecular docking study, it was found that hydroxyxanthone 3a interacted with the active sites of Topoisomerase II protein through Hydrogen bonding with DG13 and π–π stacking interactions with DA12 and DC8 These findings revealed that hydroxyxanthones are potential candidates to be developed as antioxidant and anticancer agents in the future. The synthesis of xanthone was firstly established in 1892 by Michael and Kostanecki by reacting phenol, acetic acid-o-hydroxybenzoate, and acetic anhydride. This method generates an unfavorable side reaction; the obtained yield was very low. Synthesis and modification of other xanthone derivatives are important to find the active antioxidant agents to be used for commercial purposes
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