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Research Articles

In vitro and computational studies on the antiglycation activity of compounds isolated from antidiabetic Tetracera alnifolia stem bark

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Pages 9742-9751 | Received 07 Oct 2020, Accepted 20 May 2021, Published online: 07 Jun 2021

Reference

  • Ahmed, Q. U., Dogarai, B. B., Amiroudine, M. Z. A. M., Taher, M., Latip, J., Umar, A., & Muhammad, B. Y. (2012). Antidiabetic activity of the leaves of Tetracera indica Merr.(Dilleniaceae) in vivo and in vitro. Journal of Medicinal Plants Research, 6(49), 5912–5922.
  • Arodola, O. A., & Soliman, M. E. (2016). Molecular dynamics simulations of ligand-induced flap conformational changes in cathepsin-D-A comparative study. Journal of Cellular Biochemistry, 117(11), 2643–2657. https://doi.org/10.1002/jcb.25564
  • Arowosegbe, S., Olanipekun, M. K., & Kayode, J. (2015). Ethnobotanical survey of medicinal plants used for the treatment of diabetes mellitus in Ekiti South Senatorial District, Nigeria. European Journal of Botany, Plant Sciences and Phytology, 2(4), 1–8.
  • Brealey, D., & Singer, M. (2009). Hyperglycemia in critical illness: a review. SAGE Publications.
  • Caravella, J. A., Carbeck, J. D., Duffy, D. C., Whitesides, G. M., & Tidor, B. (1999). Long-range electrostatic contributions to protein − Ligand binding estimated using protein charge ladders, affinity capillary electrophoresis, and continuum electrostatic theory. Journal of the American Chemical Society, 121(18), 4340–4347. https://doi.org/10.1021/ja984195a
  • Case, D., Darden, T., Cheatham, T., Simmerling, C., Wang, J., Duke, R., Luo, R. , Walker, R. C., Zhang, W., Merz, K. M., Roberts, B., Hayik, S., Roitberg, A., Seabra, G., Swails, J., Götz, A. W., Kolossváry, I., Wong, K. F., Paesani, F., ... Zhang, W. (2005). Amber 10 software package J. Journal of Computational Chemistry, 26, 1668–1688.
  • Case, D., Darden, T., Cheatham, T., III, Simmerling, C., Wang, J., Duke, R., Luo, R., Crowley, M., Walker, R., Zhang, W., Merz, K. M., Wang, B., Hayik, S., Roitberg, A., Seabra, G., Kolossváry, I., Wong, K. F., Paesani, F., Vanicek, J., … Zhang, W. (2008). AMBER, version 10. University of California.
  • Cottrell, D., & Tupper, P. (2007). Energy drift in molecular dynamics simulations. BIT Numerical Mathematics, 47(3), 507–523. https://doi.org/10.1007/s10543-007-0134-z
  • Fakhar, Z., Govender, T., Maguire, G. E., Lamichhane, G., Walker, R. C., Kruger, H. G., & Honarparvar, B. (2017). Differential flap dynamics in l, d-transpeptidase2 from mycobacterium tuberculosis revealed by molecular dynamics. Molecular BioSystems, 13(6), 1223–1234. https://doi.org/10.1039/C7MB00110J
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Petersson, G. A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A., Bloino, J., Janesko, B. G., Gomperts, R., Mennucci, B., Hratchian, H. P., Ortiz, J. V., … Fox, D. J. (2009). Gaussian 09, revision D. 01. : Gaussian, Inc.
  • Fukumoto, H., Kayano, T., Buse, J., Edwards, Y., Pilch, P., Bell, G., & Seino, S. (1989). Cloning and characterization of the major insulin-responsive glucose transporter expressed in human skeletal muscle and other insulin-responsive tissues. Journal of Biological Chemistry, 264(14), 7776–7779. https://doi.org/10.1016/S0021-9258(18)83106-4
  • Genheden, S., & Ryde, U. (2015). The MM/PBSA and MM/GBSA methods to estimate ligand-binding affinities. Expert Opinion on Drug Discovery, 10(5), 449–461. https://doi.org/10.1517/17460441.2015.1032936
  • Gohlke, H., Kiel, C., & Case, D. A. (2003). Insights into protein-protein binding by binding free energy calculation and free energy decomposition for the Ras-Raf and Ras-RalGDS complexes. Journal of Molecular Biology, 330(4), 891–913. https://doi.org/10.1016/S0022-2836(03)00610-7
  • Gurni, A. A., & Kubitzki, K. (1981). Flavonoid chemistry and systematics of the Dilleniaceae. Biochemical Systematics and Ecology, 9(2–3), 109–114. https://doi.org/10.1016/0305-1978(81)90028-4
  • Harvey, M., & De Fabritiis, G. (2009). An implementation of the smooth particle mesh Ewald method on GPU hardware. Journal of Chemical Theory and Computation, 5(9), 2371–2377. https://doi.org/10.1021/ct900275y
  • Honarparvar, B., Govender, T., Maguire, G. E., Soliman, M. E., & Kruger, H. G. (2014). Integrated approach to structure-based enzymatic drug design: Molecular modeling, spectroscopy, and experimental bioactivity. Chemical Reviews, 114(1), 493–537. https://doi.org/10.1021/cr300314q
  • Horn, J. W. (2009). Phylogenetics of Dilleniaceae using sequence data from four plastid loci (rbcL, infA, rps4, rpl16 intron). International Journal of Plant Sciences, 170(6), 794–813. https://doi.org/10.1086/599239
  • Hornak, V., Abel, R., Okur, A., Strockbine, B., Roitberg, A., & Simmerling, C. (2006). Comparison of multiple Amber force fields and development of improved protein backbone parameters. Proteins: Structure, Function, and Bioinformatics, 65(3), 712–725. https://doi.org/10.1002/prot.21123
  • Ibeji, C. U. (2020). Molecular dynamics and DFT study on the structure and dynamics of N-terminal domain HIV-1 capsid inhibitors. Molecular Simulation, 46(1), 62–70. https://doi.org/10.1080/08927022.2019.1674850
  • Jain, A., Soni, M., Deb, L., Jain, A., Rout, S., Gupta, V., & Krishna, K. (2008). Antioxidant and hepatoprotective activity of ethanolic and aqueous extracts of Momordica dioica Roxb. leaves. Journal of Ethnopharmacology, 115(1), 61–66. https://doi.org/10.1016/j.jep.2007.09.009
  • Jewell, J. L., Oh, E., & Thurmond, D. C. (2010). Exocytosis mechanisms underlying insulin release and glucose uptake: Conserved roles for Munc18c and syntaxin 4. American Journal of Physiology-Regulatory, Integrative and Comparative Physiology, 298(3), R517–R531. https://doi.org/10.1152/ajpregu.00597.2009
  • Kim, J. M., Lee, E. K., Kim, D. H., Yu, B. P., & Chung, H. Y. (2010). Kaempferol modulates pro-inflammatory NF-κB activation by suppressing advanced glycation endproducts-induced NADPH oxidase. AGE, 32(2), 197–208. https://doi.org/10.1007/s11357-009-9124-1
  • Kumalo, H., & Soliman, M. E. (2016). A comparative molecular dynamics study on BACE1 and BACE2 flap flexibility. Journal of Receptors and Signal Transduction, 36(5), 505–514. https://doi.org/10.3109/10799893.2015.1130058
  • Lawal, T., Adeniyi, B., Wan, B., Franzblau, S., & Mahady, G. (2011). In-vitro susceptibility of Mycobacterium tuberculosis to extracts of Uvaria afzelli Scott Elliot and Tetracera alnifolia Willd. African Journal of Biomedical Research, 14(1), 17–21.
  • Li, X., Zheng, T., Sang, S., & Lv, L. (2014). Quercetin inhibits advanced glycation end product formation by trapping methylglyoxal and glyoxal. Journal of Agricultural and Food Chemistry, 62(50), 12152–12158. https://doi.org/10.1021/jf504132x
  • Lima, C. C., Lemos, R. P., & Conserva, L. M. (2014). Dilleniaceae family: An overview of its ethnomedicinal uses, biological and phytochemical profile. Journal of Pharmacognosy and Phytochemistry, 3(2), 181–204.
  • Lobanov, M. Y., Bogatyreva, N., & Galzitskaya, O. (2008). Radius of gyration as an indicator of protein structure compactness. Molecular Biology, 42(4), 623–628. https://doi.org/10.1134/S0026893308040195
  • Martinez, L. (2015). Automatic identification of mobile and rigid substructures in molecular dynamics simulations and fractional structural fluctuation analysis. PloS One, 10, e0119264.
  • Minkara, M. S., Ucisik, M. N., Weaver, M. N., & Merz, K. M. (2014). Molecular dynamics study of Helicobacter pylori urease. Journal of Chemical Theory and Computation, 10(5), 1852–1862. https://doi.org/10.1021/ct5000023
  • Mohan, S. S., Perry, J. J. P., Poulose, N., Nair, B. G., & Anilkumar, G. (2009). Homology modeling of GLUT4, an insulin regulated facilitated glucose transporter and docking studies with ATP and its inhibitors. Journal of Biomolecular Structure and Dynamics, 26(4), 455–464. https://doi.org/10.1080/07391102.2009.10507260
  • Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. https://doi.org/10.1002/jcc.21256
  • Markham, K. R., Temai, B., Stanley, M., Geiger, H., & Mabry, T. J. (1978). 13CNMR of Flavonoids. III. Naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahedron, 34, 1389–1397.
  • Negre-Salvayre, A., Salvayre, R., Auge, N., Pamplona, R., & Portero-Otin, M. (2009). Hyperglycemia and glycation in diabetic complications. Antioxidants & Redox Signaling, 11(12), 3071–3109. https://doi.org/10.1089/ars.2009.2484
  • Nsonde Ntandou, G., BoumbaL, S., Gouollaly, T., Makambila, M., Ouamba, J., & Abena, A. (2017). Acute toxicity, anti-inflammatory and analgesic effects of aqueous extract of Tetracera alnifolia Willd.(Dilleniaceae). Research Journal of Pharmacology and Pharmacy, 1(2), 1–13.
  • Ohtsubo, K., & Marth, J. D. (2006). Glycosylation in cellular mechanisms of health and disease. Cell, 126(5), 855–867. https://doi.org/10.1016/j.cell.2006.08.019
  • Onufriev, A., Bashford, D., & Case, D. A. (2000). Modification of the generalized Born model suitable for macromolecules. The Journal of Physical Chemistry B, 104(15), 3712–3720. https://doi.org/10.1021/jp994072s
  • Oyebode, O. A., Erukainure, O. L., Chukwuma, C. I., Ibeji, C. U., Koorbanally, N. A., & Islam, S. (2018). Boerhaavia diffusa inhibits key enzymes linked to type 2 diabetes in vitro and in silico; and modulates abdominal glucose absorption and muscle glucose uptake ex vivo. Biomedicine & Pharmacotherapy, 106, 1116–1125. https://doi.org/10.1016/j.biopha.2018.07.053
  • Perez, A., MacCallum, J. L., Brini, E., Simmerling, C., & Dill, K. A. (2015). Grid-based backbone correction to the ff12SB protein force field for implicit-solvent simulations. Journal of Chemical Theory and Computation, 11(10), 4770–4779. https://doi.org/10.1021/acs.jctc.5b00662
  • Rahbar, S., & Figarola, J. L. (2003). Novel inhibitors of advanced glycation endproducts. Archives of Biochemistry and Biophysics, 419(1), 63–79. https://doi.org/10.1016/j.abb.2003.08.009
  • Richter, E. A., & Hargreaves, M. (2013). Exercise, GLUT4, and skeletal muscle glucose uptake. Physiological Reviews, 93(3), 993–1017.
  • Ryckaert, J.-P., Ciccotti, G., & Berendsen, H. J. (1977). Numerical integration of the Cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes. Journal of Computational Physics, 23(3), 327–341. https://doi.org/10.1016/0021-9991(77)90098-5
  • Sadowska-Bartosz, I., Galiniak, S., & Bartosz, G. (2014). Kinetics of glycoxidation of bovine serum albumin by glucose, fructose and ribose and its prevention by food components. Molecules, 19(11), 18828–18849. https://doi.org/10.3390/molecules191118828
  • Samak, G., Shenoy, R. P., Manjunatha, S., & Vinayak, K. (2009). Superoxide and hydroxyl radical scavenging actions of botanical extracts of Wagatea spicata. Food Chemistry, 115(2), 631–634. https://doi.org/10.1016/j.foodchem.2008.12.078
  • Sanner, M. F. (1999). Python: A programming language for software integration and development. Journal of Molecular Graphic and Modeling, 17(1), 57–61.
  • Srinivasan, J., Cheatham, T. E., Cieplak, P., Kollman, P. A., & Case, D. A. (1998). Continuum solvent studies of the stability of DNA, RNA, and phosphoramidate − DNA helices. Journal of the American Chemical Society, 120(37), 9401–9409. https://doi.org/10.1021/ja981844+
  • Tolufashe, G. F., Halder, A. K., Ibeji, C. U., Lawal, M. M., Ntombela, T., Govender, T., Maguire, G. E. M., Lamichhane, G., Kruger, H. G., & Honarparvar, B. (2018). Inhibition of Mycobacterium tuberculosis L, D‐transpeptidase 5 by carbapenems: MD and QM/MM mechanistic studies. ChemistrySelect, 3(48), 13603–13612. https://doi.org/10.1002/slct.201803184
  • Wan, L. L., Xia, J., Ye, D., Liu, J., Chen, J., and Wang, G. (2009). Effects of quercetin on gene and protein expression of NOX and NOS after myocardial ischemia and reperfusion in rabbits. Cardiovascular Therapeutics, 27, 28–33.https://doi.org/10.1111/j.1755-5922.2009.00071.x
  • Wang, J., Wang, W., Kollman, P. A., & Case, D. A. (2001). Antechamber: An accessory software package for molecular mechanical calculations. Journal of the American Chemical Society, 222, U403.
  • Wang, J., Wolf, R. M., Caldwell, J. W., Kollman, P. A., & Case, D. A. (2004). Development and testing of a general amber force field. Journal of Computational Chemistry, 25(9), 1157–1174. https://doi.org/10.1002/jcc.20035
  • Yang, B., Hao, F., Li, J., Chen, D., & Liu, R. (2013). Binding of chrysoidine to catalase: Spectroscopy, isothermal titration calorimetry and molecular docking studies. Journal of Photochemistry and Photobiology B: Biology, 128, 35–42. https://doi.org/10.1016/j.jphotobiol.2013.08.006
  • Yonekura, H., Yamamoto, Y., Sakurai, S., Watanabe, T., & Yamamoto, H. (2005). Roles of the receptor for advanced glycation endproducts in diabetes-induced vascular injury. Journal of Pharmacological Sciences, 97(3), 305–311.
  • Zhang, Y., Zhang, H., Yao, X-g., Shen, H., Chen, J., Li, C., Chen, L., Zheng, M., Ye, J., Hu, L., Shen, X., & Jiang, H. (2012). Rutamarin as a dual inducer of both GLUT4 translocation and expression efficiently ameliorates glucose homeostasis in insulin-resistant mice. PLoS One, 7(2), e31811. https://doi.org/10.1371/journal.pone.0031811
  • Zhou, Z., & Madura, J. D. (2004). Relative free energy of binding and binding mode calculations of HIV‐1 RT inhibitors based on dock‐MM‐PB/GS. Proteins: Structure, Function, and Bioinformatics, 57(3), 493–503. https://doi.org/10.1002/prot.20223
  • Zhou, Z., Wang, Y., & Bryant, S. H. (2009). Computational analysis of the cathepsin B inhibitors activities through LR‐MMPBSA binding affinity calculation based on docked complex. Journal of Computational Chemistry, 30(14), 2165–2175.

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