Xanthones as potential α-glucosidase non-competition inhibitors: Synthesis, inhibitory activities, and in silico studies.
molecular docking
synthesis
xanthone compound
α-glucosidase non-competition inhibition
Journal
Chemical biology & drug design
ISSN: 1747-0285
Titre abrégé: Chem Biol Drug Des
Pays: England
ID NLM: 101262549
Informations de publication
Date de publication:
09 2023
09 2023
Historique:
revised:
12
04
2023
received:
23
02
2023
accepted:
08
05
2023
medline:
14
8
2023
pubmed:
30
5
2023
entrez:
30
5
2023
Statut:
ppublish
Résumé
α-glucosidase inhibitors (AGIs) were commonly used in clinical for the treatment of type 2 diabetes. Xanthones were naturally occurring antioxidants, and they may also be potential AGIs. In this study, eleven 1,6- and 1,3-substituted xanthone compounds were designed and synthesized, of which four were new compounds. Their α-glucosidase inhibitory activities in vitro and in silico were evaluated. Five xanthone compounds with higher activity than acarbose were screened out, and the xanthones substituted at the 1,6-positions were more likely to be potential α-glucosidase non-competitive inhibitors. The binding mode of xanthones with α-glucosidase was further studied by molecular docking method, and the results showed that the inhibitory effect of non-competitive inhibitors on site 1 of α-glucosidase may be related to the hydrogen bonds formed by the compounds with amino acid residues ASN165, HIS209, TRY207, ASP243, and SER104. This study provided a theoretical basis of the rapid discovery and structural modification of non-competitive xanthone inhibitors of α-glucosidase.
Substances chimiques
Glycoside Hydrolase Inhibitors
0
alpha-Glucosidases
EC 3.2.1.20
Xanthones
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
547-556Informations de copyright
© 2023 John Wiley & Sons A/S.
Références
Ahmad, I. (2016). Recent insight into the biological activities of synthetic xanthone derivatives. European Journal of Medicinal Chemistry, 30, 267-280. https://doi.org/10.1016/j.ejmech.2016.03.058
Barraclough, D., Locksley, H. D., Scheinmann, F., Magalhaes, M. T., & Gottlieb, O. R. (1970). Applications of proton magnetic resonance spectroscopy in the structural investigation of xanthones. Journal of the Chemical Society B: Physical Organic, 603-612. https://doi.org/10.1039/j29700000603
De Almeida, R. B. M., de Almeida Luz, R. L. S., Leite, F. H. A., & Botura, M. B. (2021). A review on the in vitro evaluation of the anticholinesterase activity based on Ellman's method. Mini Reviews in Medicinal Chemistry, 22, 1803-1813. https://doi.org/10.2174/1389557521666211027104638
Jiang, D. J., Dai, Z., & Li, Y. J. (2004). Pharmacological effects of xanthones as cardiovascular protective agents. Cardiovascular Drug Reviews, 22, 91-102. https://doi.org/10.1111/j.1527-3466.2004.tb00133.x
Jin, C. Q., Liu, S. H., Wang, L. L., & He, X. (2022). Sceen of xanthone glucosidase inhibitors based on combined computer approaches. West China Journal of Pharmaceutical Sciences, 37, 115-120. https://doi.org/10.13375/j.cnki.wcjps.2022.02.002
Joshi, S. R., Standl, E., Tong, N., Shah, P., Kalra, S., & Rathod, R. (2015). Therapeutic potential of α-glucosidase inhibitors in type 2 diabetes mellitus: An evidence-based review. Expert Opinion on Pharmacotherapy, 16, 1959-1981. https://doi.org/10.1517/14656566.2015.1070827
Kim, J. H., Ahn, J. H., Kim, S. K., Lee, D. H., Kim, H. S., Shon, H. S., Jeon, H. J., Kim, T. H., Cho, Y. W., Kim, J. T., & Han, S. M. (2015). Combined use of basal insulin analog and acarbose reduces postprandial glucose in patients with uncontrolled type 2 diabetes. Diabetes Investigation, 6, 219-226. https://doi.org/10.1111/jdi.12261
Kojima, K., Tsujimoto, T., & Fujii, H. (2010). Pneumatosis cystoides intestinalis induced by the alpha-glucosidase inhibitor miglitol. Internal Medicine, 49, 1545-1548. https://doi.org/10.2169/internalmedicine.49.3634
Lien Do, T. M., Duong, T. H., Nguyen, V. K., Phuwapraisirisan, P., Doungwichitrkul, T., Niamnont, N., Jarupinthusophon, S., & Sichaem, J. (2021). Schomburgkixanthone, a novel bixanthone from the twigs of Garcinia schomburgkiana. Natural Product Research, 35, 3613-3618. https://doi.org/10.1080/14786419.2020.1716351
Lin, C. N., Liou, S. S., Ko, F. N., & Teng, C. M. (1993). γ-Pyrone compounds. IV: Synthesis and antiplatelet effects of mono-and dioxygenated xanthones and xanthonoxypropanolamine. Journal of Pharmaceutical Sciences, 82, 11-16. https://doi.org/10.1002/jps.2600820103
Liu, J., Zhang, C., Wang, H., Zhang, L., Jiang, Z., Zhang, J., Liu, Z., & Chen, H. (2018). Incorporation of nitric oxide donor into 1,3-dioxyxanthones leads to synergistic anticancer activity. European Journal of Medicinal Chemistry, 151, 158-172. https://doi.org/10.1016/j.ejmech.2018.03.072
Liu, Y., Ma, L., Chen, W. H., Park, H., Ke, Z., & Wang, B. (2013). Binding mechanism and synergetic effects of xanthone derivatives as noncompetitive α-glucosidase inhibitors: A theoretical and experimental study. The Journal of Physical Chemistry B, 117, 13464-13471. https://doi.org/10.1021/jp4067235
Pinto, M. M., Sousa, M. E., & Nascimento, M. S. (2005). Xanthone derivatives: New insights in biological activities. Current Medicinal Chemistry, 12, 2517-2538. https://doi.org/10.2174/092986705774370691
Pinto, M. M. M., Palmeira, A., Fernandes, C., Resende, D. I. S. P., Sousa, E., Cidade, H., Tiritan, M. E., Correia-da-Silva, M., & Cravo, S. (2021). From natural products to new synthetic small molecules: A journey through the world of Xanthones. Molecules, 26, 431. https://doi.org/10.3390/molecules26020431
Proença, C., Freitas, M., Ribeiro, D., Oliveira, E. F. T., Sousa, J. L. C., Tomé, S. M., Ramos, M. J., Silva, A. M. S., Fernandes, P. A., & Fernandes, E. (2017). α-Glucosidase inhibition by flavonoids: An in vitro and in silico structure-activity relationship study. Journal of Enzyme Inhibition and Medicinal Chemistry, 32, 1216-1228. https://doi.org/10.1080/14756366.2017.1368503
Santos, C. M., Freitas, M., & Fernandes, E. (2018). A comprehensive review on xanthone derivatives as α-glucosidase inhibitors. European Journal of Medicinal Chemistry, 157, 1460-1479. https://doi.org/10.1016/j.ejmech.2018.07.073
Shen, R., Wang, W., & Yang, G. (2014). DNA binding property and antitumor evaluation of Xanthone with dimethylamine side chain. Journal of Fluorescence, 24, 959-966. https://doi.org/10.1007/s10895-014-1380-5
Şöhretoğlu, D., Sari, S., Özel, A., & Barut, B. (2017). α-Glucosidase inhibitory effect of Potentilla astracanica and some isoflavones: Inhibition kinetics and mechanistic insights through in vitro and in silico studies. International Journal of Biological Macromolecules, 105, 1062-1070. https://doi.org/10.1016/j.ijbiomac.2017.07.132
Sousa, M. E., & Pinto, M. M. (2005). Synthesis of xanthones: An overview. Current Medicinal Chemistry, 12, 2447-2479. https://doi.org/10.2174/092986705774370736
Wang, M., Zhang, G., Bao, N., Chen, A., Bai, S., & Wang, Q. (2021). Structural elucidation and α-glucosidase inhibitory activity of a new xanthone glycoside from Lomatogonium rotatum (L.). Natural Product Research, 3, 1-5. https://doi.org/10.1080/14786419.2021.1995864
Zhou, B. D., Zeng, L. L., Tong, Y. G., Fang, J. Y., Ruan, Z. P., Zeng, X. Y., Fang, Y. Y., Xu, G. F., & Hu, D. B. (2018). Synthesis and antitumor, antityrosinase, and antioxidant activities of xanthone. Journal of Asian Natural Products Research, 20, 467-476. https://doi.org/10.1080/10286020.2018.1454437
Zou, Y., Zhao, Q., Hu, H., Hu, L., Yu, S., Xu, M., & Wu, Q. (2012). Synthesis and in vitro antitumor activities of xanthone derivatives containing 1,4-disubstituted-1,2,3-triazole moiety. Archives of Pharmacal Research, 35, 2093-2104. https://doi.org/10.1007/s12272-012-1206-4