1Chemistry Education, Sultan Ageng Tirtayasa University, Serang, Banten 42117, Indonesia
2Research Center for Pharmaceutical Ingredients and Traditional Medicine, National Research and Innovation Agency (BRIN), Tangerang Selatan, Banten 15314, Indonesia
3Department of Chemistry, Faculty of Military Mathematics and Natural Sciences, Universitas Pertahanan Republik Indonesia, Bogor 16810, Indonesia
4 Department of Chemistry, Universitas Negeri Semarang, Kampus Sekaran, Gunungpati, Semarang 50229, Indonesia
5 Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University, Jl. Prof. Soedarto, SH., Tembalang, Semarang, Indonesia
BibTex Citation Data :
@article{JKSA88063, author = {Nela Fatmasari and Clara Shabrina Parameswary and Ken Hastu Mulamawarni and Faris Hermawan and Minarti Minarti and Yoga Mulya Ramadhan and Fadhil Ardiyan Syahputra and Minandre Wiratama and Reinhard Sharon Lase and Muhammad Badrul Huda}, title = {Synthesis of 1-Hydroxy-6-methoxyxanthone and Comparison of Its α-Glucosidase Inhibitory and Antibacterial Activities with Hydroxyxanthone Derivatives}, journal = {Jurnal Kimia Sains dan Aplikasi}, volume = {29}, number = {9}, year = {2026}, keywords = {Antibacterial activity; Molecular docking; Synthesis; 1-Hydroxy-6-methoxyxanthone; α- Glucosidase inhibition}, abstract = { Xanthone derivatives have attracted considerable interest owing to their broad spectrum of biological activities, making them promising scaffolds for the development of multifunctional therapeutic agents. In this study, 1-hydroxy-6-methoxyxanthone ( MX1 ) was synthesized via cyclodehydration using Eaton’s reagent, affording the target compound in 18.50% yield, and structurally characterized by FTIR, LC–MS, and NMR spectroscopy. MX1 was obtained as a yellow solid in 18.50% yield, with a melting point of 145–147°C. The α - glucosidase inhibitory and antibacterial activities of MX1 were evaluated in comparison with those of previously reported hydroxyxanthone derivatives ( HX1–HX3 ), while molecular docking was performed to investigate their binding interactions with α -glucosidase. Among the evaluated compounds, MX1 exhibited the most potent α -glucosidase inhibitory activity with an IC 50 value of 203.23 μg/mL, followed by HX2 (223.53 μg/mL), whereas HX1 and HX3 showed weaker inhibition, with IC 50 values of 463.74 and 482.86 μg/mL, respectively. Molecular docking demonstrated that all compounds occupied a common binding pocket and formed favorable interactions with key active-site residues through hydrogen bonding, π–π, and π–anion interactions, supporting the proposed structure–activity relationships. In contrast, MX1 exhibited limited antibacterial activity, with MIC values of 500 μg/mL against Pseudomonas aeruginosa and Bacillus subtilis and >1000 μg/mL against Escherichia coli and Staphylococcus aureus . Collectively, these findings indicate that replacement of the C-6 hydroxyl group with a methoxy group enhances α -glucosidase inhibitory activity while reducing antibacterial activity, underscoring the pivotal role of C-6 substitution in modulating the biological activities of xanthone derivatives. }, issn = {2597-9914}, pages = {631--640} doi = {10.14710/jksa.29.9.631-640}, url = {https://ejournal.undip.ac.id/index.php/ksa/article/view/88063} }
Refworks Citation Data :
Xanthone derivatives have attracted considerable interest owing to their broad spectrum of biological activities, making them promising scaffolds for the development of multifunctional therapeutic agents. In this study, 1-hydroxy-6-methoxyxanthone (MX1) was synthesized via cyclodehydration using Eaton’s reagent, affording the target compound in 18.50% yield, and structurally characterized by FTIR, LC–MS, and NMR spectroscopy. MX1 was obtained as a yellow solid in 18.50% yield, with a melting point of 145–147°C. The α- glucosidase inhibitory and antibacterial activities of MX1 were evaluated in comparison with those of previously reported hydroxyxanthone derivatives (HX1–HX3), while molecular docking was performed to investigate their binding interactions with α-glucosidase. Among the evaluated compounds, MX1 exhibited the most potent α-glucosidase inhibitory activity with an IC50 value of 203.23 μg/mL, followed by HX2 (223.53 μg/mL), whereas HX1 and HX3 showed weaker inhibition, with IC50 values of 463.74 and 482.86 μg/mL, respectively. Molecular docking demonstrated that all compounds occupied a common binding pocket and formed favorable interactions with key active-site residues through hydrogen bonding, π–π, and π–anion interactions, supporting the proposed structure–activity relationships. In contrast, MX1 exhibited limited antibacterial activity, with MIC values of 500 μg/mL against Pseudomonas aeruginosa and Bacillus subtilis and >1000 μg/mL against Escherichia coli and Staphylococcus aureus. Collectively, these findings indicate that replacement of the C-6 hydroxyl group with a methoxy group enhances α-glucosidase inhibitory activity while reducing antibacterial activity, underscoring the pivotal role of C-6 substitution in modulating the biological activities of xanthone derivatives.
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