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Research Articles

Biological effects and molecular docking studies of Catechin 5-O-gallate: antioxidant, anticholinergics, antiepileptic and antidiabetic potentials

ORCID Icon, ORCID Icon, &
Pages 2489-2497 | Received 10 Jun 2020, Accepted 18 Oct 2020, Published online: 04 Nov 2020

References

  • Acar, M. F., Sari, S., & Dalkara, S. (2019). Synthesis, in vivo anticonvulsant testing, and molecular modeling studies of new nafimidone derivatives. Drug Development Research, 80(5), 606–616. https://doi.org/https://doi.org/10.1002/ddr.21538
  • Alaşehirli, B. (2005). Kolinesteraz İnhibitörleri (Antikolinesterazlar). Turkiye Klinikleri Journal of Internal Medical Sciences, 1, 47–57.
  • Alterio, V., Monti, S. M., Truppo, E., Pedone, C., Supuran, C. T., & De Simone, G. (2010). The first example of a significant active site conformational rearrangement in a carbonic anhydrase-inhibitor adduct: The carbonic anhydrase I–topiramate complex. Organic & Biomolecular Chemistry, 8, 3528–3533.
  • Apak, R. A. (2019). Current issues in antioxidant measurement. Journal of Agricultural and Food Chemistry, 67(33), 9187–9202. https://doi.org/https://doi.org/10.1021/acs.jafc.9b03657
  • Atmaca, U., Kaya, R., Karaman, H. S., Celik, M., & Gülçin, İ. (2019). Synthesis of oxazolidinone from enantiomerically enriched allylic alcohols and determination of their molecular docking and biologic activities. Bioorganic Chemistry, 88, 102980. https://doi.org/https://doi.org/10.1016/j.bioorg.2019.102980
  • Bayindir, S., Caglayan, C., Karaman, M., & Gülcin, İ. (2019). The green synthesis and molecular docking of novel N-substituted rhodanines as effective inhibitors for carbonic anhydrase and acetylcholinesterase enzymes. Bioorganic Chemistry, 90, 103096. https://doi.org/https://doi.org/10.1016/j.bioorg.2019.103096
  • Blois, M. S. (1958). Antioxidant deteminations by the use of a stable free radical. Nature, 26, 1199–1200.
  • Burmaoglu, S., Yilmaz, A. O., Polat, M. F., Kaya, R., Gulcin, İ., & Algul, O. (2019). Synthesis and biological evaluation of novel tris-chalcones as potent carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase and α-glycosidase inhibitors. Bioorganic Chemistry, 85, 191–197. https://doi.org/https://doi.org/10.1016/j.bioorg.2018.12.035
  • Bursal, E., Köksal, E., Gülçin, İ., Bilsel, G., & Gören, A. C. (2013). Antioxidant activity and polyphenol content of cherry stem (Cerasus avium L.) determined by LC–MS/MS. Food Research International, 51, 66–74.
  • Bytyqi-Damoni, A., Kestane, A., Taslimi, P., Tuzun, B., Zengin, M., Bilgicli, H. G., & Gulcin, İ. (2020). Novel carvacrol based new oxypropanolamine derivatives: Design, synthesis, characterization, biological evaluation, and molecular docking studies. Journal of Molecular Structure, 1202, 127297.
  • Chen, G.-H., Yang, C.-Y., Lee, S.-J., Wu, C.-C., & Tzen, J. T. (2014). Catechin content and the degree of its galloylation in oolong tea are inversely correlated with cultivation altitude. Journal of Food and Drug Analysis, 22(3), 303–309. https://doi.org/https://doi.org/10.1016/j.jfda.2013.12.001
  • Durmaz, L. (2019). Antioxidant, antiepileptic, and anticholinergic properties of 4′, 5, 7-Trihydroxy-3, 6-dimethoxyflavone as natural phenolic compound: A toxicology approach. Toxin Reviews, 1–8.
  • Ellman, G. L., Courtney, K. D., Andres, V., & Feather-Stone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7, 88–95.
  • Eruygur, N., Koçyiğit, U., Taslimi, P., Ataş, M., Tekin, M., & Gülçin, İ. (2019). Screening the in vitro antioxidant, antimicrobial, anticholinesterase, antidiabetic activities of endemic Achillea cucullata (Asteraceae) ethanol extract. South African Journal of Botany, 120, 141–145.
  • Friesner, R. A., Murphy, R. B., Repasky, M. P., Frye, L. L., Greenwood, J. R., Halgren, T. A., Sanschagrin, P. C., & Mainz, D. T. (2006). Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. Journal of Medicinal Chemistry, 49(21), 6177–6196. https://doi.org/https://doi.org/10.1021/jm051256o
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., … Fox, D. J. (2009). Gaussian 09, revision D.01. Gaussian Inc.
  • Garman, S. C., & Garboczi, D. N. (2004). The molecular defect leading to Fabry disease: structure of human alpha-galactosidase. Journal of Molecular Biology, 337(2), 319–335. https://doi.org/10.1016/j.jmb.2004.01.03515003450
  • Genç Bilgiçli, H., Bilgiçli, A. T., Günsel, A., Tüzün, B., Ergön, D., Yarasir, M. N., & Zengin, M. (2020). Turn‐on fluorescent probe for Zn2+ ions based on thiazolidine derivative. Applied Organometallic Chemistry, 34, e5624.
  • Göcer, H., Akıncıoğlu, A., Göksu, S., & Gülçin, İ. (2017). Carbonic anhydrase inhibitory properties of phenolic sulfonamides derived from dopamine related compounds. Arabian Journal of Chemistry, 10, 398–402.
  • Göçer, H., Akıncıoğlu, A., Öztaşkın, N., Göksu, S., & Gülçin, İ. (2013). Synthesis, Antioxidant, and Antiacetylcholinesterase Activities of Sulfonamide Derivatives of dopamine-related compounds . Archiv Der Pharmazie, 346(11), 783–792. https://doi.org/https://doi.org/10.1002/ardp.201300228
  • Göçer, H., & Gülçin, İ. (2011). Caffeic acid phenethyl ester (CAPE): Correlation of structure and antioxidant properties. International Journal of Food Sciences and Nutrition, 62(8), 821–825. https://doi.org/https://doi.org/10.3109/09637486.2011.585963
  • Gülçin, İ. (2006). Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid)). Toxicology, 217(2–3), 213–220. https://doi.org/https://doi.org/10.1016/j.tox.2005.09.011
  • Gülçin, İ. (2010). Antioxidant properties of resveratrol: A structure–activity insight. Innovative Food Science & Emerging Technologies, 11, 210–218.
  • Gulcin, İ. (2020). Antioxidants and antioxidant methods: An updated overview. Archives of Toxicology, 1–65.
  • Huang, S.-T., Hung, Y.-A., Yang, M.-J., Chen, I.-Z., Yuann, J.-M P., & Liang, J.-Y. (2019). Effects of epigallocatechin gallate on the stability of epicatechin in a photolytic process. Molecules, 24, 787.
  • Ivanova, J., Leitans, J., Tanc, M., Kazaks, A., Zalubovskis, R., Supuran, C. T., & Tars, K. (2015). X-ray crystallography-promoted drug design of carbonic anhydrase inhibitors. Chemical Communications (Cambridge, England), 51(33), 7108–7111. https://doi.org/https://doi.org/10.1039/c5cc01854d
  • Jayarajan, R., Satheeshkumar, R., Kottha, T., Subbaramanian, S., Sayin, K., & Vasuki, G. (2020). Water mediated synthesis of 6-amino-5-cyano-2-oxo-N-(pyridin-2-yl)-4-(p-tolyl)-2H-[1,2'-bipyridine]-3-carboxamide and 6-amino-5-cyano-4-(4-fluorophenyl)-2-oxo-N-(pyridin-2-yl)-2H-[1,2'-bipyridine]-3-carboxamide - An experimental and computational studies with non-linear optical (NLO) and molecular docking analyses. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 229, 117861. https://doi.org/https://doi.org/10.1016/j.saa.2019.117861
  • Jorgensen, W. L., & Duffy, E. M. (2002). Prediction of drug solubility from structure. Advanced Drug Delivery Reviews, 54(3), 355–366. https://doi.org/https://doi.org/10.1016/s0169-409x(02)00008-x
  • Koçyiğit, Ü. M. (2018). Investigation of inhibition effect of oxytocin on carbonic anhydrase and acetylcholinesterase enzymes in the heart tissues of rats. Igdir University Journal of the Institute of Science and Technology, 8(1), 199–207.
  • Kocyigit, U. M., Taslimi, P., Gezegen, H., Gulçin, İ., & Ceylan, M. (2017). Evaluation of acetylcholinesterase and carbonic anhydrase inhibition profiles of 1, 2, 3, 4, 6‐pentasubstituted‐4‐hydroxy‐cyclohexanes. Journal of Biochemical and Molecular Toxicology, 31, e21938.
  • Köse, L. P., Gülcin, I., Gören, A. C., Namiesnik, J., Martinez-Ayala, A. L., & Gorinstein, S. (2015). LC–MS/MS analysis, antioxidant and anticholinergic properties of galanga (Alpinia officinarum Hance) rhizomes. Industrial Crops and Products, 74, 712–721.
  • Lineweaver, H., & Burk, D. (1934). The determination of enzyme dissociation constants. Journal of the American Chemical Society, 56, 658–666.
  • Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (1997). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 23, 3–25.
  • Mai, T. T., Thu, N. N., Tien, P. G., & Van Chuyen, N. (2007). Alpha-glucosidase inhibitory and antioxidant activities of Vietnamese edible plants and their relationships with polyphenol contents. Journal of Nutritional Science and Vitaminology, 53(3), 267–276. https://doi.org/https://doi.org/10.3177/jnsv.53.267
  • Menteşe, E., Emirik, M., & Sökmen, B. B. (2019). Design, molecular docking and synthesis of novel 5,6-dichloro-2-methyl-1H-benzimidazole derivatives as potential urease enzyme inhibitors. Bioorganic Chemistry, 86, 151–158. https://doi.org/https://doi.org/10.1016/j.bioorg.2019.01.061
  • Mermer, A., Bayrak, H., Şirin, Y., Emirik, M., & Demirbaş, N. (2019). Synthesis of novel Azol-β-lactam derivatives starting from phenyl piperazine and investigation of their antiurease activity and antioxidant capacity comparing with their molecular docking studies. Journal of Molecular Structure, 1189, 279–287.
  • Ojha, L. K., Tüzün, B., & Bhawsar, J. (2020). Experimental and theoretical study of effect of Allium sativum extracts as corrosion inhibitor on mild steel in 1 M HCl medium. Journal of Bio-and Tribo-Corrosion, 6(2), 1–10.
  • Rahim, F., Zaman, K., Taha, M., Ullah, H., Ghufran, M., Wadood, A., Rehman, W., Uddin, N., Shah, S. A. A., Sajid, M., Nawaz, F., & Khan, K. M. (2020). Synthesis, in vitro alpha-glucosidase inhibitory potential of benzimidazole bearing bis-Schiff bases and their molecular docking study. Bioorganic Chemistry, 94, 103394. https://doi.org/https://doi.org/10.1016/j.bioorg.2019.103394
  • Rajurkar, N. S., & Hande, S. (2011). Estimation of phytochemical content and antioxidant activity of some selected traditional Indian medicinal plants. Indian Journal of Pharmaceutical Sciences, 73(2), 146–151. https://doi.org/https://doi.org/10.4103/0250-474x.91574
  • Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology & Medicine, 26(9–10), 1231–1237.
  • Release, S. (2020). 1: Maestro 019-3 SR. Glide, ligprep, protein preparation wizard, prime, desmond molecular dynamics system. Maestro-Desmond Interoperability Tools.
  • Sağlık, B. N., Çevik, U. A., Osmaniye, D., Levent, S., Çavuşoğlu, B. K., Demir, Y., Ilgın, S., Özkay, Y., Koparal, A. S., Beydemir, Ş., & Kaplancıklı, Z. A. (2019). Synthesis, molecular docking analysis and carbonic anhydrase I-II inhibitory evaluation of new sulfonamide derivatives. Bioorganic Chemistry, 91, 103153. https://doi.org/https://doi.org/10.1016/j.bioorg.2019.103153
  • Sastry, G. M., Adzhigirey, M., Day, T., Annabhimoju, R., & Sherman, W. (2013). Protein and ligand preparation: Parameters, protocols, and influence on virtual screening enrichments. Journal of Computer-Aided Molecular Design, 27(3), 221–234. https://doi.org/https://doi.org/10.1007/s10822-013-9644-8
  • Sayin, K., & Karakaş, D. (2017). Determination of structural, spectral, electronic and biological properties of tosufloxacin boron complexes and investigation of substituent effect. Journal of Molecular Structure, 1146, 191–197.
  • Sayin, K., & Karakaş, D. (2018a). Investigation of structural, electronic properties and docking calculations of some boron complexes with norfloxacin: A computational research. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 202, 276–283. https://doi.org/https://doi.org/10.1016/j.saa.2018.05.055
  • Sayin, K., & Karakaş, D. (2018b). Quantum chemical investigation of levofloxacin-boron complexes: A computational approach. Journal of Molecular Structure, 1158, 57–65.
  • Sayin, K., & Üngördü, A. (2019a). Investigations of structural, spectral and electronic properties of enrofloxacin and boron complexes via quantum chemical calculation and molecular docking. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 220, 117102. https://doi.org/https://doi.org/10.1016/j.saa.2019.05.007
  • Sayin, K., & Üngördü, A. (2019b). Investigation of anticancer properties of caffeinated complexes via computational chemistry methods. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 193, 147–155. https://doi.org/https://doi.org/10.1016/j.saa.2017.12.013
  • Sayin, K., & Üngördü, A. (2019c). Quantum chemical calculations on sparfloxacin and boron complexes. Chemical Physics Letters, 733, 136677.
  • Schrodinger, L. (2019). Small-Molecule Drug Discovery Suite 2019-4 Schrödinger Release 2019-4. Schrödinger, LLC.
  • Schrödinger Release 2019-4. (2019a) LigPrep. Schrödinger, LLC.
  • Schrödinger Release 2019-4. (2019b). Protein Preparation Wizard. Epik, Schrödinger, LLC.
  • Schrödinger Release 2020-1. (2020). QikProp. Schrödinger, LLC.
  • Sever, B., Altıntop, M. D., Özdemir, A., Tabanca, N., Estep, A. S., Becnel, J. J., & Bloomquist, J. R. (2019). Biological evaluation of a series of benzothiazole derivatives as mosquitocidal agents. Open Chemistry, 17, 288–294.
  • Subhani, S., Jayaraman, A., & Jamil, K. (2015). Homology modelling and molecular docking of MDR1 with chemotherapeutic agents in non-small cell lung cancer. Biomedicine & Pharmacotherapy, 71, 37–45. https://doi.org/https://doi.org/10.1016/j.biopha.2015.02.009
  • Tao, Y., Zhang, Y., Cheng, Y., & Wang, Y. (2013). Rapid screening and identification of α-glucosidase inhibitors from mulberry leaves using enzyme-immobilized magnetic beads coupled with HPLC/MS and NMR. Biomedical Chromatography, 27(2), 148–155. https://doi.org/https://doi.org/10.1002/bmc.2761
  • Taslimi, P., Caglayan, C., & Gulcin, İ. (2017). The impact of some natural phenolic compounds on carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase, and α‐glycosidase enzymes: An antidiabetic, anticholinergic, and antiepileptic study. Journal of Biochemical and Molecular Toxicology, 31, e21995.
  • Taslimi, P., Erden, Y., Mamedov, S., Zeynalova, L., Ladokhina, N., Tas, R., Tuzun, B., Sujayev, A., Sadeghian, N., & Alwasel, S. H. (2020). The biological activities, molecular docking studies, and anticancer effects of 1-arylsuphonylpyrazole derivatives. Journal of Biomolecular Structure and Dynamics, 1–20.
  • Topal, M., & Gülcin, İ. (2014). Rosmarinic acid: A potent carbonic anhydrase isoenzymes inhibitor. Turkish Journal of Chemistry, 38, 894–902.
  • Türe, A., Kahraman, D. C., Cetin-Atalay, R., Helvacıoğlu, S., Charehsaz, M., & Küçükgüzel, İ. (2019). Synthesis, anticancer activity, toxicity evaluation and molecular docking studies of novel phenylaminopyrimidine-(thio)urea hybrids as potential kinase inhibitors. Computational Biology and Chemistry, 78, 227–241. https://doi.org/https://doi.org/10.1016/j.compbiolchem.2018.12.003
  • Turkan, F., Cetin, A., Taslimi, P., Karaman, H. S., & Gulçin, İ. (2019). Synthesis, characterization, molecular docking and biological activities of novel pyrazoline derivatives. Archiv Der Pharmazie, 352, 1800359.
  • Türkan, F., Taslimi, P., Abdalrazaq, S. M., Aras, A., Erden, Y., Celebioglu, H. U., Tuzun, B., Ağırtaş, M. S., & Gülçin, İ. (2020). Determination of anticancer properties and inhibitory effects of some metabolic enzymes including acetylcholinesterase, butyrylcholinesterase, alpha glycosidase of some compounds with molecular docking study. Journal of Biomolecular Structure and Dynamics, 1–17.
  • Tutar, U., Koçyiğit, Ü. M., & Gezegen, H. (2019). Evaluation of antimicrobial, antibiofilm and carbonic anhydrase inhibition profiles of 1,3-bis-chalcone derivatives . Journal of Biochemical and Molecular Toxicology, 33(4), e22281. https://doi.org/https://doi.org/10.1002/jbt.22281
  • Tüzün, B., Çağlar Yavuz, S., & Sarıpınar, E. (2018). 4D-QSAR analysis and pharmacophore modeling: Propoxy methylphenyl oxasiazole derivatives by electron conformatitional-genetic algorithm method. Journal of Physical & Theoretical Chemistry, 14, 149–164.
  • Tüzün, B., & Saripinar, E. (2020). Molecular docking and 4D-QSAR model of methanone derivatives by electron conformational-genetic algorithm method. Journal of the Iranian Chemical Society, 17, 985–1000.
  • Verpoorte, J. A., Mehta, S., & Edsall, J. T. (1967). Esterase activities of human carbonic anhydrases B and C. Journal of Biological Chemistry, 242, 4221–4229.

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