Research Article
BibTex RIS Cite

Comparison of the activities of Hyoscyamus niger L. extracts against SARS-CoV-2 virus

Year 2025, Volume: 9 Issue: 5, 96 - 109

Gülşen Güçlü , Burak Tüzün , Esra Uçar , Nuraniye Eruygur

Abstract

In this study, the antiviral potential of ethanol (80%) extracts of Hyoscyamus niger L. leaves and seeds was theoretically investigated against SARS-CoV-2 proteins (PDB IDs: 7MRV, 7QO7, and 7U0N) using molecular docking and ADME/T analysis. The chemical composition of the extracts was determined by GC-MS, revealing significant variations in phytochemical profiles between plant organs. Docking simulations were performed on 31 major compounds identified from the extracts. Among them, 6-Amino-2,4-dimethyl-5-methoxyquinoline, Isosteviol methyl ester, and 6-Hydroxy-1,4-dimethylisoquinoline exhibited the most favorable binding affinities and interaction profiles across all target proteins. The ADME/T properties of 6-Amino-2,4-dimethyl-5-methoxyquinoline were further analyzed, demonstrating ideal pharmacokinetic characteristics such as high membrane permeability, good solubility, and excellent oral absorption potential. The results suggest that specific bioactive components in H. niger may serve as promising lead compounds for antiviral drug development against SARS-CoV-2 and warrant further in vitro and in vivo validation.

Keywords

Hyoscyamus niger L Molecular docking ADME/T Drug GC-MS

Supporting Institution

Scientific Research Project Fund of Sivas Cumhuriyet University (CUBAP)

Project Number

RGD-020

References

  • [1] WHO. COVID-19 epidemiological update – 12 March 2025. Ed.177. (2025). Available: https://www.who.int/publications/m/item/covid-19-epidemiological-update-edition-177
  • [2] M. Rodriguez-Guerra, P. Jadhav, T. J. Vittorio, Current treatment in COVID-19 disease: a rapid review. Drugs in Context (2021) 10, 2020–10.
  • [3] Y. Xie, T. Choi, Z. Al-Aly, Mortality in patients hospitalized for COVID-19 vs influenza in fall-winter 2023–2024. JAMA (2024) 331(22), 1963–1965.
  • [4] J. Pang, M. X. Wang, I. Y. H. Ang, S. H. X. Tan, R. F. Lewis, J. I. P. Chen, … L. Y. Hsu, Potential rapid diagnostics, vaccine and therapeutics for 2019 novel coronavirus (2019-nCoV): a systematic review. J. Clin. Med. (2020) 9(3), 623.
  • [5] M. Kavurmacı, E. Çetindağ, COVID-19 Pandemisi, Kronik Hastalıklar ve Geleneksel, Tamamlayıcı ve Fonksiyonel Tıp Uygulamaları. Curr. Res. Health Sci. (2025) 2(1), 33–37.
  • [6] S. S. Gadge, Antiviral and Immunity-modulating Natural Herbs in the Prevention of COVID-19. Res. J. Pharmacogn. Phytochem. (2021) 13(2), 81–94.
  • [7] C. Huang, Y. Wang, X. Li, L. Ren, J. Zhao, Y. Hu, … B. Cao, Clinical features of patients infected with 2019 novel coronavirus in Wuhan, China. Lancet (2020) 395(10223), 497–506.
  • [8] M. M. Parvizi, S. Forouhari, R. Shahriarirad, S. Shahriarirad, R. D. Bradley, L. Roosta, Prevalence and associated factors of complementary and integrative medicine use in patients afflicted with COVID-19. BMC Complement. Med. Ther. (2022) 22(1), 251.
  • [9] I. D. Passos, M. Maria Mironidou-Tzouveleki, Hallucinogenic Plants in the Mediterranean Countries. Neuropathol. Drug Addict. Subst. Misuse, Vol. 2: Stimulants, Club and Dissociative Drugs, Hallucinogens, Steroids, Inhalants and International Aspects, Chapter 71 (2016) 761–772.
  • [10] A. Bahmanzadegan, F. Sefidkon, A. Sonboli, Determination of hyoscyamine and scopolamine in four Hyoscyamus species from Iran. Iran. J. Pharm. Res. (2010) 65–70.
  • [11] O. Michalak, P. Krzeczyński, M. Cieślak, P. Cmoch, M. Cybulski, K. Królewska-Golińska, … K. Ostrowska, Synthesis and anti-tumour, immunomodulating activity of diosgenin and tigogenin conjugates. J. Steroid Biochem. Mol. Biol. (2020) 198, 105573.
  • [12] W. Zhang, W. Zhang, J. Luo, L. Kong, A new steroidal glycoside from the seeds of Hyoscyamus niger. Nat. Prod. Res. (2013) 27(21), 1971–1974.
  • [13] M. Dahmani, A. Titi, S. Kadri, A. ET-Touhami, A. Yahyi, B. Tüzün, … I. Warad, Synthesis of two new Sn(IV) carboxylate complexes: Crystal structures, density functional theory and Hirshfeld surface analysis computation, antibacterial, antifungal, and bioinformatics potential determination. Inorg. Chem. Commun. (2025) 114683.
  • [14] A. E. M. A. Allah, S. Mortada, B. Tüzün, W. Guerrab, M. Qostal, J. T. Mague, … Y. Ramli, Novel thiohydantoin derivatives: design, synthesis, spectroscopic characterization, crystal structure, SAR, DFT, molecular docking, pharmacological and toxicological activities. J. Mol. Struct. (2025) 1335, 141995.
  • [15] H. Yalazan, D. Koç, F. A. Kose, M. İ. Akgül, S. Fandaklı, B. Tüzün, … H. Kantekin, Chalcone-based schiff bases: Design, synthesis, structural characterization and biological effects. J. Mol. Struct. (2025) 1337, 142211..
  • [16] H. Yalazan, D. Koç, F. A. Kose, M. İ. Akgül, S. Fandaklı, B. Tüzün, … H. Kantekin, Chalcone-based schiff bases: Design, synthesis, structural characterization and biological effects. J. Mol. Struct. (2025) 1337, 142211.
  • [17] E. Chen, K. Reiss, D. Shah, R. Manjula, B. Allen, E. L. Murphy, … G. P. Lisi, A structurally preserved allosteric site in the MIF superfamily affects enzymatic activity and CD74 activation in D-dopachrome tautomerase. J. Biol. Chem. (2021) 297(3).
  • [18] D. Ni, K. Lau, P. Turelli, C. Raclot, B. Beckert, S. Nazarov, … D. Trono, Structural analysis of the Spike of the Omicron SARS-COV-2 variant by cryo-EM and implications for immune evasion. bioRxiv (2021) 2021-12.
  • [19] Q. Geng, K. Shi, G. Ye, W. Zhang, H. Aihara, F. Li, Structural basis for human receptor recognition by SARS-CoV-2 Omicron variant BA. 1. J. Virol. (2022) 96(8), e00249-22.
  • [20] G. Sacchetti, S. Maietti, M. Muzzoli, M. Scaglianti, S. Manfredini, M. Radice, R. Bruni, Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods. Food Chem. (2005) 91, 621–632.
  • [21] N. Eruygur, E. Dural, Determination of 1-Deoxynojirimycin by a developed and validated HPLC-FLD method and assessment of in-vitro antioxidant, α-Amylase and α-Glucosidase inhibitory activity in mulberry varieties from Turkey. Phytomedicine (2019) 53, 234–242.
  • [22] Schrödinger Release 2022-4: Maestro, Schrödinger, LLC, New York, NY, (2022).
  • [23] Schrödinger Release 2022-4: Protein Preparation Wizard; Epik, Schrödinger, LLC, New York, NY, 2022; Impact, Schrödinger, LLC, New York, NY; Prime, Schrödinger, LLC, New York, NY, (2022).
  • [24] Schrödinger Release 2022-4: LigPrep, Schrödinger, LLC, New York, NY, (2022).
  • [25] I. Shahzadi, A.F. Zahoor, B. Tüzün, A. Mansha, M.N. Anjum, A. Rasul, ... M. Mojzych, Repositioning of acefylline as anti-cancer drug: Synthesis, anticancer and computational studies of azomethines derived from acefylline tethered 4-amino-3-mercapto-1,2,4-triazole. PLOS ONE, 17(12) (2022) e0278027.
  • [26] M. El Faydy, L. Lakhrissi, N. Dahaieh, K. Ounine, B. Tüzün, N. Chahboun, ... A. Zarrouk, Synthesis, biological properties, and molecular docking study of novel 1,2,3-triazole-8-quinolinol hybrids. ACS Omega, 9(23) (2024) 25395–25409.
  • [27] Schrödinger Release 2022-4: QikProp, Schrödinger, LLC, New York, NY, 2022.
  • [28] G. Güçlü, B. Tüzün, E. Uçar, N. Eruygur, M. Ataş, M. İnanır, ... B. Coşge Şenkal, Phytochemical and biological activity evaluation of Globularia orientalis L. Korean Journal of Chemical Engineering (2025) 1–17.
  • [29] B. Tüzün, T. Agbektas, F.N. Naghiyev, A. Tas, C. Zontul, U. Ozum, ... I.G. Mamedov, In vitro cytotoxicity, gene expression, bioinformatics, biochemical analysis, and in silico analysis of synthesized carbonitrile derivatives. Monatshefte für Chemie - Chemical Monthly (2025) 1–22.
  • [30] A. Bouabbadi, M. Rbaa, B. Tüzün, A. Hmada, K. Dahmani, O. Kharbouch, ... M. Harcharras, Novel 8-hydroxyquinoline compounds used to inhibit mild steel corrosion in the presence of hydrochloric acid 1.0 M: an experimental and theoretical electrochemical study. Canadian Metallurgical Quarterly (2025) 1–18.
  • [31] N. Maliyakkal, P. Taslimi, B. Tüzün, S. Menadi, E. Cacan, A.A. Beeran, ... B. Mathew, Cholinesterase inhibition and anticancer properties of [4-(benzyloxy)phenyl]{methylidene}hydrazinylidene]-1,3-dihydro-2H-indol-2-ones using Swiss Target-guided prediction. Current Computer-Aided Drug Design (2025).
  • [32] U.A. Cevik, H. Ünver, H.E. Bostancı, B. Tüzün, N.İ. Gedik, Ü.M. Kocyigit, New hydrazone derivatives: synthesis, characterization, carbonic anhydrase I-II enzyme inhibition, anticancer activity and in silico studies. Zeitschrift für Naturforschung C (2025).
  • [33] H. Karatas, İ.B. Kul, M. Aydin, B. Tüzün, P. Taslimi, Z. Kokbudak, Alzheimer’s disease drug design by synthesis, characterization, enzyme inhibition, in silico, SAR analysis and MM-GBSA analysis of Schiff bases derivatives. Korean Journal of Chemical Engineering (2025) 1–19.
  • [34] B. Tüzün, Evaluation of cytotoxicity, chemical composition, antioxidant potential, apoptosis relationship, molecular docking, and MM-GBSA analysis of Rumex crispus leaf extracts. Journal of Molecular Structure, 1323 (2025) 140791.
  • [35] M. Akkus, M. Kirici, A. Poustforoosh, M.K. Erdogan, R. Gundogdu, B. Tüzün, P. Taslimi, Phenolic compounds: Investigating their anti-carbonic anhydrase, anti-cholinesterase, anticancer, anticholinergic, and antiepileptic properties through molecular docking, MM-GBSA, and dynamics analyses. Korean Journal of Chemical Engineering (2025) 1–20.
  • [36] N. Ullah, A. Alam, B. Tüzün, N.U. Rehman, M. Ayaz, A.A. Elhenawy, ... M. Ahmad, Synthesis of novel thiazole derivatives containing 3-methylthiophene carbaldehyde as potent anti α-glucosidase agents: In vitro evaluation, molecular docking, dynamics, MM-GBSA, and DFT studies. Journal of Molecular Structure, 1321 (2025) 140070.
  • [37] S. Çiçek, Y.B. Korkmaz, B. Tüzün, S. Işik, M.T. Yilmaz, F. Özoğul, A study on insecticidal activity of the fennel (Foeniculum vulgare) essential oil and its nanoemulsion against stored product pests and molecular docking evaluation. Industrial Crops and Products, 222 (2024) 119859.
  • [38] S. Kapancık, M.S. Çelik, M. Demiralp, K. Ünal, S. Çetinkaya, B. Tüzün, Chemical composition, cytotoxicity, and molecular docking analyses of Thuja orientalis extracts. Journal of Molecular Structure, 1318 (2024) 139279.
  • [39] S. Manap, H. Medetalibeyoğlu, A. Kılıç, O.F. Karataş, B. Tüzün, M. Alkan, ... H. Yüksek, Synthesis, molecular modeling investigation, molecular dynamic and ADME prediction of some novel Mannich bases derived from 1,2,4-triazole, and assessment of their anticancer activity. Journal of Biomolecular Structure and Dynamics, 42(21) (2024) 11916–11930.
  • [40] O. Myroslava, A. Poustforoosh, B. Inna, V. Parchenko, B. Tüzün, B. Gutyj, Molecular descriptors and in silico studies of 4-((5-(decylthio)-4-methyl-4n-1,2,4-triazol-3-yl)methyl)morpholine as a potential drug for the treatment of fungal pathologies. Computational Biology and Chemistry, 113 (2024) 108206.
  • [41] K. Ganbarov, A. Huseynzada, G. Binate, K. Sayin, N. Sadikhova, V. Ismailov, ... A. Algherbawi, Biological and in silico studies of methyl 2-(2-methoxy-2-oxoethyl)-4-methylfuran-3-carboxylate as a promising antimicrobial agent. Acta Scientiarum-Technology, 47(1) (2025).
  • [42] K. Prabha, S. Rajendran, B.M. Gnanamangai, K. Sayin, K.R. Prasad, G. Tüzün, Synthesis of novel isostere analogues of naphthyridines using CuI catalyst: DFT computations (FMO, MEP), molecular docking and ADME analysis. Tetrahedron, 168 (2024) 134323.
  • [43] A. Huseynzada, M. Mori, F. Meneghetti, A. Israyilova, G. Tuzun, K. Sayin, ... V. Abbasov, Synthesis, crystal structure, Hirshfeld surface, computational and antibacterial studies of a 9-phenanthrenecarboxaldehyde-based thiodihydropyrimidine derivative. Journal of Molecular Structure, 1267 (2022) 133571.
  • [44] C.A. Lipinski, Lead-and drug-like compounds: the rule-of-five revolution. Drug Discovery Today: Technologies, 1(4) (2004) 337–341.
  • [45] C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 23 (1997) 3–25.
  • [46] W.J. Jorgensen, E.M. Duffy, Prediction of drug solubility from structure. Advanced Drug Delivery Reviews, 54(3) (2002) 355–366.
There are 46 citations in total.

Details

Primary Language English
Subjects Molecular Imaging
Journal Section Research Article
Authors

Gülşen Güçlü 0000-0002-3599-213X

Burak Tüzün 0000-0002-0420-2043

Esra Uçar 0000-0001-6327-4779

Nuraniye Eruygur 0000-0002-4674-7009

Project Number RGD-020
Early Pub Date July 2, 2025
Publication Date
Submission Date May 29, 2025
Acceptance Date June 2, 2025
Published in Issue Year 2025 Volume: 9 Issue: 5

Cite

APA Güçlü, G., Tüzün, B., Uçar, E., Eruygur, N. (2025). Comparison of the activities of Hyoscyamus niger L. extracts against SARS-CoV-2 virus. Turkish Computational and Theoretical Chemistry, 9(5), 96-109.
AMA Güçlü G, Tüzün B, Uçar E, Eruygur N. Comparison of the activities of Hyoscyamus niger L. extracts against SARS-CoV-2 virus. Turkish Comp Theo Chem (TC&TC). July 2025;9(5):96-109.
Chicago Güçlü, Gülşen, Burak Tüzün, Esra Uçar, and Nuraniye Eruygur. “Comparison of the Activities of Hyoscyamus Niger L. Extracts Against SARS-CoV-2 Virus”. Turkish Computational and Theoretical Chemistry 9, no. 5 (July 2025): 96-109.
EndNote Güçlü G, Tüzün B, Uçar E, Eruygur N (July 1, 2025) Comparison of the activities of Hyoscyamus niger L. extracts against SARS-CoV-2 virus. Turkish Computational and Theoretical Chemistry 9 5 96–109.
IEEE G. Güçlü, B. Tüzün, E. Uçar, and N. Eruygur, “Comparison of the activities of Hyoscyamus niger L. extracts against SARS-CoV-2 virus”, Turkish Comp Theo Chem (TC&TC), vol. 9, no. 5, pp. 96–109, 2025.
ISNAD Güçlü, Gülşen et al. “Comparison of the Activities of Hyoscyamus Niger L. Extracts Against SARS-CoV-2 Virus”. Turkish Computational and Theoretical Chemistry 9/5 (July 2025), 96-109.
JAMA Güçlü G, Tüzün B, Uçar E, Eruygur N. Comparison of the activities of Hyoscyamus niger L. extracts against SARS-CoV-2 virus. Turkish Comp Theo Chem (TC&TC). 2025;9:96–109.
MLA Güçlü, Gülşen et al. “Comparison of the Activities of Hyoscyamus Niger L. Extracts Against SARS-CoV-2 Virus”. Turkish Computational and Theoretical Chemistry, vol. 9, no. 5, 2025, pp. 96-109.
Vancouver Güçlü G, Tüzün B, Uçar E, Eruygur N. Comparison of the activities of Hyoscyamus niger L. extracts against SARS-CoV-2 virus. Turkish Comp Theo Chem (TC&TC). 2025;9(5):96-109.

Journal Full Title: Turkish Computational and Theoretical Chemistry


Journal Abbreviated Title: Turkish Comp Theo Chem (TC&TC)