In vitro bioactivities and in silico enzyme interactions of abietatrien-3β-ol by bio-guided isolation from Nepeta italica subsp. italica

References

• Abbaz, T., Bendjeddou, A., & Villemin, D. (2019). Density functional theory studies on molecular structure and electronic properties of sulfanilamide, sulfathiazole, E7070 and furosemide molecules. Journal of Applied Chemistry, 12(1), 60–69. https://doi.org/10.9790/5736-1201016069
   Google Scholar
• Abdel El‐wahab, H. A., Hamdy, A. K., Schulzke, C., Aboul‐Fadl, T., & Qayed, W. S. (2021). Crystal structure and quantum chemical calculations of (E) 1‐benzyl‐3‐((4‐methoxyphenyl) imino)‐5‐methylindolin‐2‐one. Journal of Heterocyclic Chemistry, 58(8), 1601–1609. https://doi.org/10.1002/jhet.4284
   Web of Science ®Google Scholar
• Abdel-Rhman, M. H., El-Asmy, A. A., Ibrahim, R., & Hosny, N. M. (2023). New Schiff base ligand and some of its coordination compounds: Synthesis, spectral, molecular modeling and biological studies. Journal of Molecular Structure, 1279, 135023. https://doi.org/10.1016/j.molstruc.2023.135023
   Web of Science ®Google Scholar
• Abraham, C. S., Muthu, S., Prasana, J. C., Armaković, S., Armaković, S. J., Rizwana B, F., Geoffrey, B., & David R, H. A. (2019). Computational evaluation of the reactivity and pharmaceutical potential of an organic amine: A DFT, molecular dynamics simulations and molecular docking approach. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 222, 117188. https://doi.org/10.1016/j.saa.2019.117188
   PubMed Web of Science ®Google Scholar
• Abraham, M. J., Murtola, T., Schulz, R., Páll, S., Smith, J. C., Hess, B., & Lindahl, E. (2015). GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX, 1–2, 19–25. https://doi.org/10.1016/j.softx.2015.06.001
   Google Scholar
• Acquaviva, A., Di Simone, S. C., Nilofar Bouyahya, A., Zengin, G., Recinella, L., Leone, S., Brunetti, L., Uba, A. I., Guler, O., Balos, M., Cakilcioğlu, U., Menghini, L., Ferrante, C., Orlando, G., Libero, M. L., & Chiavaroli, A. (2023). Screening for chemical characterization and pharmacological properties of different extracts from Nepeta italica. Plants, 12(15), 2785. https://doi.org/10.3390/plants12152785
   Google Scholar
• Addar, L., Bensouici, C., Zennia, S. S. A., Haroun, S. B., & Mati, A. (2019). Antioxidant, tyrosinase and urease inhibitory activities of camel αS-casein and its hydrolysate fractions. Small Ruminant Research, 173, 30–35. https://doi.org/10.1016/j.smallrumres.2019.01.015
   Web of Science ®Google Scholar
• Ahmed, B., Ali Ashfaq, U., & Usman Mirza, M. (2018). Medicinal plant phytochemicals and their inhibitory activities against pancreatic lipase: Molecular docking combined with molecular dynamics simulation approach. Natural Product Research, 32(10), 1123–1129. https://doi.org/10.1080/14786419.2017.1320786
   PubMed Web of Science ®Google Scholar
• Ahmed, S. A., Salau, S., Khan, A., Saeed, M., & Ul-Haq, Z. (2022). Inhibitive property of catechin and chlorogenic acid against human pancreatic lipase: Molecular docking and molecular dynamics simulation investigations. Advanced Journal of Chemistry, Section A, 5, 226–240. https://doi.org/10.22034/AJCA.2022.338380.1311
   Google Scholar
• Aispuro-Pérez, A., López-Ávalos, J., García-Páez, F., Montes-Avila, J., Picos-Corrales, L. A., Ochoa-Terán, A., Bastidas, P., Montaño, S., Calderón-Zamora, L., Osuna-Martínez, U., & Sarmiento-Sánchez, J. I. (2020). Synthesis and molecular docking studies of imines as α-glucosidase and α-amylase inhibitors. Bioorganic Chemistry, 94, 103491. https://doi.org/10.1016/j.bioorg.2019.103491
   Web of Science ®Google Scholar
• Akkoc, S., Karatas, H., Muhammed, M. T., Kökbudak, Z., Ceylan, A., Almalki, F., Laaroussi, H., & Ben Hadda, T. (2023). Drug design of new therapeutic agents: Molecular docking, molecular dynamics simulation, DFT and POM analyses of new Schiff base ligands and impact of substituents on bioactivity of their potential antifungal pharmacophore site. Journal of Biomolecular Structure & Dynamics, 41(14), 6695–6708. https://doi.org/10.1080/07391102.2022.2111360
   PubMed Web of Science ®Google Scholar
• Akman, S., Akkoc, S., Zeyrek, C. T., Muhammed, M. T., & Ilhan, I. O. (2023). Density functional modeling, and molecular docking with SARS-CoV-2 spike protein (Wuhan) and omicron S protein (variant) studies of new heterocyclic compounds including a pyrazoline nucleus. Journal of Biomolecular Structure & Dynamics, 41(22), 12951–12965. https://doi.org/10.1080/07391102.2023.2169765
   PubMedGoogle Scholar
• Akpinar, N., Akpinar, M., Gorgun, S., Dirmenci, T., & Aktumsek, A. (2008). Fatty acid composition of the seeds of five Nepeta species from Turkey. Chemistry of Natural Compounds, 44(1), 90–92. https://doi.org/10.1007/s10600-008-0025-9
   Web of Science ®Google Scholar
• Almaz, Z., Oztekin, A., Tan, A., & Ozdemir, H. (2021). Biological evaluation and molecular docking studies of 4-aminobenzohydrazide derivatives as cholinesterase inhibitors. Journal of Molecular Structure, 1244, 130918. https://doi.org/10.1016/j.molstruc.2021.130918
   Web of Science ®Google Scholar
• Alyar, S., & Adem, Ş. (2014). Synthesis, characterization, antimicrobial activity and carbonic anhydrase enzyme inhibitor effects of salicilaldehyde-N-methyl p-toluenesulfonylhydrazone and its Palladium (II), Cobalt (II) complexes. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 131, 294–302. https://doi.org/10.1016/j.saa.2014.04.121
   PubMed Web of Science ®Google Scholar
• Alyar, S., Özmen, Ü. Ö., Adem, Ş., Alyar, H., Bilen, E., & Kaya, K. (2021). Synthesis, spectroscopic characterizations, carbonic anhydrase II inhibitory activity, anticancer activity and docking studies of new Schiff bases of sulfa drugs. Journal of Molecular Structure, 1223, 128911. https://doi.org/10.1016/j.molstruc.2020.128911
   Web of Science ®Google Scholar
• Alyar, S., Şen, C., Alyar, H., Adem, Ş., Kalkanci, A., & Ozdemir, U. O. (2018). Synthesis, characterization, antimicrobial activity, carbonic anhydrase enzyme inhibitor effects, and computational studies on new Schiff bases of Sulfa drugs and their Pd (II), Cu (II) complexes. Journal of Molecular Structure, 1171, 214–222. https://doi.org/10.1016/j.molstruc.2018.06.004
   Web of Science ®Google Scholar
• Anigboro, A. A., Avwioroko, O. J., Ohwokevwo, O. A., Pessu, B., & Tonukari, N. J. (2021). Phytochemical profile, antioxidant, α-amylase inhibition, binding interaction and docking studies of Justicia carnea bioactive compounds with α-amylase. Biophysical Chemistry, 269, 106529. https://doi.org/10.1016/j.bpc.2020.106529
   Web of Science ®Google Scholar
• Aras, A., Dogru, M., & Bursal, E. (2016). Determination of antioxidant potential of Nepeta nuda subsp. lydiae. Analytical Chemistry Letters, 6(6), 758–765. https://doi.org/10.1080/22297928.2016.1265467
   Google Scholar
• Attia, A., Aboelnaga, A., & Fahim, A. M. (2023). Isonicotinohydrazide chalcone and its Ni complex as corrosion ınhibitors during acid cleaning: Theoretical and experimental approaches. Egyptian Journal of Chemistry, 0(0), 0–0. https://doi.org/10.21608/ejchem.2022.166142.7046
   Google Scholar
• Azimi, S. G., Bagherzade, G., Saberi, M. R., & Amiri Tehranizadeh, Z. (2023). Discovery of new ligand with quinoline scaffold as potent allosteric ınhibitor of HIV-1 and its copper complexes as a powerful catalyst for the synthesis of chiral benzimidazole derivatives, and in silico anti-HIV-1 studies. Bioinorganic Chemistry and Applications, 2023, 2881582. https://doi.org/10.1155/2023/2881582
   Web of Science ®Google Scholar
• Bahadori, M. B., Dinparast, L., Valizadeh, H., Farimani, M. M., & Ebrahimi, S. N. (2016). Bioactive constituents from roots of Salvia syriaca L.: Acetylcholinesterase inhibitory activity and molecular docking studies. South African Journal of Botany, 106, 1–4. https://doi.org/10.1016/j.sajb.2015.12.003
   Web of Science ®Google Scholar
• Baiseitova, A., Jenis, J., Kim, J. Y., Li, Z. P., & Park, K. H. (2019). Phytochemical analysis of aerial part of Ikonnikovia kaufmanniana and their protection of DNA damage. Natural Product Research, 35(5), 880–883. https://doi.org/10.1080/14786419.2019.1607858
   PubMed Web of Science ®Google Scholar
• Başar, Y., Demirtaş, İ., Yenigün, S., İpek, Y., Özen, T., & Behçet, L. (2024). Molecular docking, molecular dynamics, MM/PBSA approaches and bioactivity studies of nepetanudoside B isolated from endemic Nepeta aristata. Journal of Biomolecular Structure & Dynamics, 42, 1–14. https://doi.org/10.1080/07391102.2024.2309641
   Google Scholar
• Başar, Y., Yenigün, S., İpek, Y., Behçet, L., Gül, F., Özen, T., & Demirtaş, İ. (2024). DNA protection, molecular docking, enzyme inhibition and enzyme kinetic studies of 1,5,9-epideoxyloganic acid isolated from Nepeta aristata with bio-guided fractionation. Journal of Biomolecular Structure & Dynamics, 42, 1–14. https://doi.org/10.1080/07391102.2023.2250461
   Web of Science ®Google Scholar
• Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review. A, General Physics, 38(6), 3098–3100. https://doi.org/10.1103/PhysRevA.38.3098
   PubMedGoogle Scholar
• BIOVIA, D. S. (2019). BIOVIA Discovery Studio Visualize 2019, version 2019. Dassault Systèmes BIOVIA.
   Google Scholar
• Bjelkmar, P., Larsson, P., Cuendet, M. A., Hess, B., & Lindahl, E. (2010). Implementation of the CHARMM force field in GROMACS: Analysis of protein stability effects from correction maps, virtual interaction sites, and water models. Journal of Chemical Theory and Computation, 6(2), 459–466. https://doi.org/10.1021/ct900549r
   PubMed Web of Science ®Google Scholar
• Blois, M. S. (1958). Antioxidant determinations by the use of a stable free radical. Nature, 181(4617), 1199–1200. https://doi.org/10.1038/1811199a0
   Web of Science ®Google Scholar
• Boualia, I., Derabli, C., Boulcina, R., Bensouici, C., Yildirim, M., Birinci Yildirim, A., Mokrani, E. H., & Debache, A. (2019). Synthesis, molecular docking studies, and biological evaluation of novel alkyl bis (4‐amino‐5‐cyanopyrimidine) derivatives. Archiv der Pharmazie, 352(11), e1900027. https://doi.org/10.1002/ardp.201900027
   Web of Science ®Google Scholar
• Calixto, J. B. (2019). The role of natural products in modern drug discovery. Anais da Academia Brasileira de Ciências, 91, 1–7. https://doi.org/10.1590/0001-3765201920190105
   Web of Science ®Google Scholar
• Celik, I., Erol, M., Temiz Arpaci, O., Sezer Senol, F., & Erdogan Orhan, I. (2022). Evaluation of activity of some 2,5-disubstituted benzoxazole derivatives against acetylcholinesterase, butyrylcholinesterase and tyrosinase: ADME prediction, DFT and comparative molecular docking studies. Polycyclic Aromatic Compounds, 42(2), 412–423. https://doi.org/10.1080/10406638.2020.1737827
   Web of Science ®Google Scholar
• Chanda, J., Mukherjee, P. K., Biswas, R., Biswas, S., Tiwari, A. K., & Pargaonkar, A. (2019). UPLC‐QTOF‐MS analysis of a carbonic anhydrase‐inhibiting extract and fractions of Luffa acutangula (L.) Roxb (ridge gourd). Phytochemical Analysis, 30(2), 148–155. https://doi.org/10.1002/pca.2800
   Web of Science ®Google Scholar
• Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7(1), 42717. https://doi.org/10.1038/srep42717
   PubMed Web of Science ®Google Scholar
• Dinis, T. C., Maderia, V. M., & Almeida, L. M. (1994). Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Archives of Biochemistry and Biophysics, 315(1), 161–169. https://doi.org/10.1006/abbi.1994.1485
   PubMed Web of Science ®Google Scholar
• Ditchfield, R., Hehre, W. J., & Pople, J. A. (1971). Self‐consistent molecular‐orbital methods. IX. An extended Gaussian‐type basis for molecular‐orbital studies of organic molecules. The Journal of Chemical Physics, 54(2), 724–728. https://doi.org/10.1063/1.1674902
   Web of Science ®Google Scholar
• Djeujo, F. M., Stablum, V., Pangrazzi, E., Ragazzi, E., & Froldi, G. (2023). Luteolin and vernodalol as bioactive compounds of leaf and root vernonia amygdalina extracts: Effects on α-glucosidase, glycation, ROS, cell viability, and in silico ADMET parameters. Pharmaceutics, 15(5), 1541. https://doi.org/10.3390/pharmaceutics15051541
   Web of Science ®Google Scholar
• Doharey, P. K., Verma, P., Dubey, A., Singh, S. K., Kumar, M., Tripathi, T., Alonazi, M., Siddiqi, N. J., & Sharma, B. (2024). Biophysical and in-silico studies on the structure-function relationship of Brugia malayi protein disulfide isomerase. Journal of Biomolecular Structure & Dynamics, 42(3), 1533–1543. https://doi.org/10.1080/07391102.2023.2201849
   PubMed Web of Science ®Google Scholar
• Dong, Y-W., Liao, M-L., Meng, X-L., & Somero, G. N. (2018). Structural flexibility and protein adaptation to temperature: Molecular dynamics analysis of malate dehydrogenases of marine molluscs. Proceedings of the National Academy of Sciences of the United States of America, 115(6), 1274–1279. https://doi.org/10.1073/pnas.1718910115
   PubMed Web of Science ®Google Scholar
• 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(2), 88–95. https://doi.org/10.1016/0006-2952(61)90145-9
   PubMed Web of Science ®Google Scholar
• Eser, F., Altun, M., Demirtas, I., Behcet, L., & Aktas, E. (2022). Three new iridoids from the aerial parts of Nepeta teucriifolia Willd. and antiproliferative activities of extracts. Natural Product Research, 37(13), 2205–2214. https://doi.org/10.1080/14786419.2022.2036148
   Web of Science ®Google Scholar
• Etsassala, N. G., Badmus, J. A., Marnewick, J. L., Iwuoha, E. I., Nchu, F., & Hussein, A. A. (2020). Alpha-glucosidase and alpha-amylase inhibitory activities, molecular docking, and antioxidant capacities of Salvia aurita constituents. Antioxidants, 9(11), 1149. https://doi.org/10.3390/antiox9111149
   Web of Science ®Google Scholar
• Fahim, A. M., Magar, H. S., & Mahmoud, N. H. (2023). Synthesis, antimicrobial, antitumor activity, docking simulation, theoretical studies, and electrochemical analysis of novel Cd (II), Co (II), Cu (II), and Fe (III) complexes containing barbituric moiety. Applied Organometallic Chemistry, 37(4), e7023. https://doi.org/10.1002/aoc.7023
   Web of Science ®Google Scholar
• Fatima, A., Singh, M., Abualnaja, K. M., Althubeiti, K., Muthu, S., Siddiqui, N., & Javed, S. (2023). Experimental spectroscopic, structural (monomer and dimer), molecular docking, molecular dynamics simulation and hirshfeld surface analysis of 2-amino-6-methylpyridine. Polycyclic Aromatic Compounds, 43(5), 3910–3940. https://doi.org/10.1080/10406638.2022.2080726
   Web of Science ®Google Scholar
• Formisano, C., Rigano, D., & Senatore, F. (2011). Chemical constituents and biological activities of Nepeta species. Chemistry & Biodiversity, 8(10), 1783–1818. https://doi.org/10.1002/cbdv.201000191
   PubMed Web of Science ®Google Scholar
• Frisch, M., Trucks, G., Schlegel, H., Scuseria, G., Robb, M., Cheeseman, J., Scalmani, G., Barone, V., Mennucci, B., & Petersson, G. (2013). Gaussian 09, revision C. 01. Gaussian Inc. https://doi.org/10.1039/C4DT02443E
   Google Scholar
• Gerni, S., Ozturk, C., Almaz, Z., Bayrak, C., & Tan, A. (2023). Celecoxib derivatives containing pyrazole linked‐sulfonamide moiety: Carbonic anhydrase I–II and acetylcholinesterase ınhibition profiles, molecular docking studies. ChemistrySelect, 8(29), e202302088. https://doi.org/10.1002/slct.202302088
   Web of Science ®Google Scholar
• Goel, N., Garg, A., Nagendra, C., Reddy, A. M., Biswas, R., Natarajan, R., & Jaisankar, P. (2024). In-vitro and in-silico cholinesterase inhibitory activity of bioactive molecules isolated from the leaves of Andrographis nallamalayana JL Ellis and roots of Andrographis beddomei CB Clarke. Journal of Molecular Structure, 1301, 137406. https://doi.org/10.1016/j.molstruc.2023.137406
   Web of Science ®Google Scholar
• Guerrab, W., Lgaz, H., Kansiz, S., Mague, J. T., Dege, N., Ansar, M., Marzouki, R., Taoufik, J., Ali, I. H., Chung, I.-M., & Ramli, Y. (2020). Synthesis of a novel phenytoin derivative: Crystal structure, Hirshfeld surface analysis and DFT calculations. Journal of Molecular Structure, 1205, 127630. https://doi.org/10.1016/j.molstruc.2019.127630
   Web of Science ®Google Scholar
• Gulcin, İ. (2020). Antioxidants and antioxidant methods: An updated overview. Archives of Toxicology, 94(3), 651–715. https://doi.org/10.1007/s00204-020-02689-3
   PubMed Web of Science ®Google Scholar
• Gülcin, I. (2012). Antioxidant activity of food constituents: An overview. Archives of Toxicology, 86(3), 345–391. https://doi.org/10.1007/s00204-011-0774-2
   PubMed Web of Science ®Google Scholar
• Hassan, M., Ashraf, Z., Abbas, Q., Raza, H., & Seo, S.-Y. (2018). Exploration of novel human tyrosinase inhibitors by molecular modeling, docking and simulation studies. Interdisciplinary Sciences, Computational Life Sciences, 10(1), 68–80. https://doi.org/10.1007/s12539-016-0171-x
   PubMed Web of Science ®Google Scholar
• Hehre, W. J., Ditchfield, R., & Pople, J. A. (1972). Self—consistent molecular orbital methods. XII. Further extensions of Gaussian—type basis sets for use in molecular orbital studies of organic molecules. The Journal of Chemical Physics, 56(5), 2257–2261. https://doi.org/10.1063/1.1677527
   Web of Science ®Google Scholar
• Jachak, S. M., & Saklani, A. (2007). Challenges and opportunities in drug discovery from plants. Current Science, 92(9), 1251–1257. Retrieved from https://www.jstor.org/stable/24097892
   Web of Science ®Google Scholar
• Joshi, R. K., Satyal, P., & Setzer, W. N. (2016). Himalayan aromatic medicinal plants: A review of their ethnopharmacology, volatile phytochemistry, and biological activities. Medicines, 3(1), 6. https://doi.org/10.3390/medicines3010006
   Google Scholar
• Kamel, E. M., Bin-Ammar, A., El-Bassuony, A. A., Alanazi, M. M., Altharawi, A., Ahmeda, A. F., Alanazi, A. S., Lamsabhi, A. M., & Mahmoud, A. M. (2023). Molecular modeling and DFT studies on the antioxidant activity of Centaurea scoparia flavonoids and molecular dynamics simulation of their interaction with β-lactoglobulin. RSC Advances, 13(18), 12361–12374. https://doi.org/10.1039/D3RA01661G
   Web of Science ®Google Scholar
• Karakaya, G., Türe, A., Ercan, A., Öncül, S., & Aytemir, M. D. (2019). Synthesis, computational molecular docking analysis and effectiveness on tyrosinase inhibition of kojic acid derivatives. Bioorganic Chemistry, 88, 102950. https://doi.org/10.1016/j.bioorg.2019.102950
   PubMed Web of Science ®Google Scholar
• Kaska, A., Çiçek, M., & Mammadov, R. (2019). Biological activities, phenolic constituents and mineral element analysis of two endemic medicinal plants from Turkey: Nepeta italica subsp. cadmea and Teucrium sandrasicum. South African Journal of Botany, 124, 63–70. https://doi.org/10.1016/j.sajb.2019.04.037
   Web of Science ®Google Scholar
• Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review. B, Condensed Matter, 37(2), 785–789. https://doi.org/10.1103/PhysRevB.37.785
   PubMed Web of Science ®Google Scholar
• Li, F-J., Liu, Y., Yuan, Y., Yang, B., Liu, Z-M., & Huang, L-Q (2017). Molecular interaction studies of acetylcholinesterase with potential acetylcholinesterase inhibitors from the root of Rhodiola crenulata using molecular docking and isothermal titration calorimetry methods. International Journal of Biological Macromolecules, 104(Pt A), 527–532. https://doi.org/10.1016/j.ijbiomac.2017.06.066
   Google Scholar
• Lima, C. R., Silva, J. R. A., De Tássia Carvalho Cardoso, É., Silva, E. O., Lameira, J., Do Nascimento, J. L. M., Do Socorro Barros Brasil, D., & Alves, C. N. (2014). Combined kinetic studies and computational analysis on kojic acid analogs as tyrosinase inhibitors. Molecules, 19(7), 9591–9605. https://doi.org/10.3390/molecules19079591
   Web of Science ®Google Scholar
• Liu, Y., Zhan, L., Xu, C., Jiang, H., Zhu, C., Sun, L., Sun, C., & Li, X. (2020). α-Glucosidase inhibitors from Chinese bayberry (Morella rubra Sieb. et Zucc.) fruit: Molecular docking and interaction mechanism of flavonols with different B-ring hydroxylations. RSC Advances, 10(49), 29347–29361. https://doi.org/10.1039/D0RA05015F
   Web of Science ®Google Scholar
• Mahomoodally, M. F., Zengin, G., Aladag, M. O., Ozparlak, H., Diuzheva, A., Jekő, J., Cziáky, Z., & Aumeeruddy, M. Z. (2019). HPLC-MS/MS chemical characterization and biological properties of Origanum onites extracts: A recent insight. International Journal of Environmental Health Research, 29(6), 607–621. https://doi.org/10.1080/09603123.2018.1558184
   PubMed Web of Science ®Google Scholar
• Maity, D., Singh, D., & Bandhu, A. (2023). Mce1R of Mycobacterium tuberculosis prefers long-chain fatty acids as specific ligands: A computational study. Molecular Diversity, 27(6), 2523–2543. https://doi.org/10.1007/s11030-022-10566-7
   Web of Science ®Google Scholar
• Mathada, B. S., Basha, N. J., Karunakar, P., Periyasamy, G., Somappa, S. B., Javeed, M., & Vanishree, S. (2023). Investigation of embelin synthetic hybrids as potential COVID-19 and COX inhibitors: Synthesis, spectral analysis, DFT calculations and molecular docking studies. Journal of Molecular Structure, 1273, 134356. https://doi.org/10.1016/j.molstruc.2022.134356
   PubMed Web of Science ®Google Scholar
• Mayur, B., Sandesh, S., Shruti, S., & Sung-Yum, S. (2010). Antioxidant and α-glucosidase inhibitory properties of Carpesium abrotanoides L. Journal of Medicinal Plants Research, 4(15), 1547–1553. https://doi.org/10.5897/JMPR.9000218
   Google Scholar
• Menteşe, E., Akyüz, G., Emirik, M., & Baltaş, N. (2019). Synthesis, in vitro urease inhibition and molecular docking studies of some novel quinazolin-4(3H)-one derivatives containing triazole, thiadiazole and thiosemicarbazide functionalities. Bioorganic Chemistry, 83, 289–296. https://doi.org/10.1016/j.bioorg.2018.10.031
   PubMed Web of Science ®Google Scholar
• Mousavi, Z., Hosaini, A. S., Asgarpanah, J., & Najafizadeh, P. (2016). Antinociceptive effect of the endemic species Nepeta depauperata Benth. Jundishapur Journal of Natural Pharmaceutical Products, 11(2), e25623, 1-7. https://doi.org/10.17795/jjnpp-25623
   Google Scholar
• Naguib, A. M. M., Ebrahim, M. E., Aly, H. F., Metawaa, H. M., Mahmoud, A. H., Mahmoud, E. A., & Ebrahim, F. M. (2012). Phytochemical screening of Nepeta cataria extracts and their in vitro inhibitory effects on free radicals and carbohydrate-metabolising enzymes. Natural Product Research, 26(23), 2196–2198. https://doi.org/10.1080/14786419.2011.635342
   PubMed Web of Science ®Google Scholar
• Nazari Montazer, M., Asadi, M., Bahadorikhalili, S., Hosseini, F. S., Amanlou, A., Biglar, M., & Amanlou, M. (2021). Design, synthesis, docking study and urease inhibitory activity evaluation of novel 2-((5-amino-1,3,4-thiadiazol-2-yl) thio)-N-arylacetamide derivatives. Medicinal Chemistry Research, 30(3), 729–742. https://doi.org/10.1007/s00044-020-02683-5
   Web of Science ®Google Scholar
• Nguyen, P. T. V., Huynh, H. A., Truong, D. V., Tran, T.-D., & Vo, C.-V. T. (2020). Exploring aurone derivatives as potential human pancreatic lipase inhibitors through molecular docking and molecular dynamics simulations. Molecules, 25(20), 4657. https://doi.org/10.3390/molecules25204657
   PubMed Web of Science ®Google Scholar
• Ni, L., Zhong, X.-H., Chen, X.-J., Zhang, B.-J., Bao, M.-F., & Cai, X.-H. (2018). Bioactive norditerpenoids from Cephalotaxus fortunei var. alpina and C. lanceolata. Phytochemistry, 151, 50–60. https://doi.org/10.1016/j.phytochem.2018.04.007
   PubMed Web of Science ®Google Scholar
• Nishikimi, M., Appaji, N., & Yagi, K. (1972). The occurrence of superoxide anion in the reaction of reduced phenazine methosulfate and molecular oxygen. Biochemical and Biophysical Research Communications, 46(2), 849–854. https://doi.org/10.1016/s0006-291x(72)80218-3
   PubMed Web of Science ®Google Scholar
• Nna, V. U., McGrowder, D., & Nwokocha, C. (2023). Nutraceutical management of metabolic syndrome as a palliative and a therapeutic to coronavirus disease (COVID) crisis. Archives of Physiology and Biochemistry, 129(5), 1123–1142. https://doi.org/10.1080/13813455.2021.1903041
   PubMed Web of Science ®Google Scholar
• Noureddine, O., Issaoui, N., & Al-Dossary, O. (2021). DFT and molecular docking study of chloroquine derivatives as antiviral to coronavirus COVID-19. Journal of King Saud University. Science, 33(1), 101248. https://doi.org/10.1016/j.jksus.2020.101248
   PubMed Web of Science ®Google Scholar
• Oyaizu, M. (1986). Studies on products of browning reaction. The Japanese Journal of Nutrition and Dietetics, 44(6), 307–315. https://doi.org/10.5264/eiyogakuzashi.44.307
   Google Scholar
• Ozen, T., Bora, N., Yenigun, S., & Korkmaz, H. (2020). An investigation of chemical content, enzyme inhibitory propert, antioxidant and antibacterial activity of Aristolochia bodamae Dingler (develiotu)(Aristolochiaceae) root extracts from Samsun, Turkey. Flavour and Fragrance Journal, 35(3), 270–283. https://doi.org/10.1002/ffj.3559
   Web of Science ®Google Scholar
• Ozen, T., Kizil, D., Yenigun, S., Cesur, H., & Turkekul, I. (2019). Evaluation of bioactivities, phenolic and metal content of ten wild edible mushrooms from Western Black Sea Region of Turkey. International Journal of Medicinal Mushrooms, 21(10), 979–994. https://doi.org/10.1615/intjmedmushrooms.2019031927
   Web of Science ®Google Scholar
• Ozen, T., Yenigun, S., & Toka, M. (2022). Phenolic profile, antioxidant, DNA protection, acetylcholinesterase, butyrylcholinesterase and urease inhibition activities of Coriandrum sativum L. leaf, seed and flower extracts. International Journal of Chemistry and Technology, 6(1), 21–32. https://doi.org/10.32571/ijct.1024979
   Google Scholar
• Ozen, T., Yenigun, S., Altun, M., & Demirtas, I. (2017). Phytochemical constituents, ChEs and urease ınhibitions, antiproliferative and antioxidant properties of Elaeagnus umbellata Thunb. Combinatorial Chemistry & High Throughput Screening, 20(6), 559–578. https://doi.org/10.2174/1386207320666170127161837
   PubMed Web of Science ®Google Scholar
• Parthasarathi, R., Subramanian, V., Roy, D. R., & Chattaraj, P. (2004). Electrophilicity index as a possible descriptor of biological activity. Bioorganic & Medicinal Chemistry, 12(21), 5533–5543. https://doi.org/10.1016/j.bmc.2004.08.013
   PubMed Web of Science ®Google Scholar
• Pires, D. E., Blundell, T. L., & Ascher, D. B. (2015). pkCSM: Predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures. Journal of Medicinal Chemistry, 58(9), 4066–4072. https://doi.org/10.1021/acs.jmedchem.5b00104
   PubMed Web of Science ®Google Scholar
• Prieto, P., Pineda, M., & Aguilar, M. (1999). Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: Specific application to the determination of vitamin E. Analytical Biochemistry, 269(2), 337–341. https://doi.org/10.1006/abio.1999.4019
   PubMed Web of Science ®Google Scholar
• Puopolo, T., Liu, C., Ma, H., & Seeram, N. P. (2022). Inhibitory effects of cannabinoids on acetylcholinesterase and butyrylcholinesterase enzyme activities. Medical Cannabis and Cannabinoids, 5(1), 85–94. https://doi.org/10.1159/000524086
   Google Scholar
• 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. https://doi.org/10.1016/s0891-5849(98)00315-3
   PubMed Web of Science ®Google Scholar
• Russo, A., Izzo, A. A., Borrelli, F., Renis, M., & Vanella, A. (2003). Free radical scavenging capacity and protective effect of Bacopa monniera L. on DNA damage. Phytotherapy Research, 17(8), 870–875. https://doi.org/10.1002/ptr.1061
   PubMed Web of Science ®Google Scholar
• Sameeh, M. Y., Khowdiary, M. M., Nassar, H. S., Abdelall, M. M., Alderhami, S. A., & Elhenawy, A. A. (2021). Discovery potent of thiazolidinedione derivatives as antioxidant, α-amylase inhibitor, and antidiabetic agent. Biomedicines, 10(1), 24. https://doi.org/10.3390/biomedicines10010024
   Web of Science ®Google Scholar
• Sayed, H. M., Ahmed, A. S., Khallaf, I. S., Qayed, W. S., Mohammed, A. F., Farghaly, H. S., & Asem, A. (2023). Phytochemical investigation, molecular docking studies and DFT calculations on the antidiabetic and cytotoxic activities of Gmelina philippensis CHAM. Journal of Ethnopharmacology, 303, 115938. https://doi.org/10.1016/j.jep.2022.115938
   Web of Science ®Google Scholar
• Sghyar, R., Basavarajaiah, S. M., Chda, A., Moussaoui, O., El Hadrami, E. M., Ben-Tama, A., Aarab, L., Mague, J. T., Prashantha, K., Javeed, M., Sebbar, N. K., & Essassi, E. M. (2023). Design, synthesis, biological evaluation on immune cell proliferation, crystal structures, spectroscopic characterizations, DFT calculations, ADME analysis, and molecular docking studies with COX of novel tetrazole-galactopyranosyl analogues. Journal of Molecular Structure, 1287, 135695. https://doi.org/10.1016/j.molstruc.2023.135695
   Web of Science ®Google Scholar
• Shalaby, M. A., Fahim, A. M., & Rizk, S. A. (2023). Antioxidant activity of novel nitrogen scaffold with docking investigation and correlation of DFT stimulation. RSC Advances, 13(21), 14580–14593. https://doi.org/10.1039/D3RA02393A
   Web of Science ®Google Scholar
• Sharma, A., Cooper, R., Bhardwaj, G., & Cannoo, D. S. (2021). The genus Nepeta: Traditional uses, phytochemicals and pharmacological properties. Journal of Ethnopharmacology, 268, 113679. https://doi.org/10.1016/j.jep.2020.113679
   PubMed Web of Science ®Google Scholar
• Sharma, A., Nayik, G., & Cannoo, D. S. (2019). Pharmacology and toxicology of Nepeta cataria (Catmint) species of genus Nepeta: A review. In Plant and human health, volume 3: Pharmacology and therapeutic uses (pp. 285–299). Springer. https://doi.org/10.1007/978-3-030-04408-4_13
   Google Scholar
• Sonboli, A., Salehi, P., & Yousefzadi, M. (2004). Antimicrobial activity and chemical composition of the essential oil of Nepeta crispa Willd. from Iran. Zeitschrift Für Naturforschung C, 59(9–10), 653–656. https://doi.org/10.1515/znc-2004-9-1008
   Web of Science ®Google Scholar
• Şahin, Ö., Özmen Özdemir, Ü., Seferoğlu, N., Adem, Ş., & Seferoğlu, Z. (2022). Synthesis, characterization, molecular docking and in vitro screening of new metal complexes with coumarin Schiff base as anticholine esterase and antipancreatic cholesterol esterase agents. Journal of Biomolecular Structure & Dynamics, 40(10), 4460–4474. https://doi.org/10.1080/07391102.2020.1858163
   PubMed Web of Science ®Google Scholar
• Talebi, M., Hamidian, E., Niasari-Naslaji, F., Rahmani, S., Hosseini, F. S., Boumi, S., Montazer, M. N., Asadi, M., & Amanlou, M. (2021). Synthesis, molecular docking, and biological evaluation of nitroimidazole derivatives as potent urease inhibitors. Medicinal Chemistry Research, 30(6), 1220–1229. https://doi.org/10.1007/s00044-021-02727-4
   Web of Science ®Google Scholar
• Thomsen, R., & Christensen, M. H. (2006). MolDock: A new technique for high-accuracy molecular docking. Journal of Medicinal Chemistry, 49(11), 3315–3321. https://doi.org/10.1021/jm051197e
   PubMed Web of Science ®Google Scholar
• Trentin, R., Custódio, L., Rodrigues, M. J., Moschin, E., Sciuto, K., da Silva, J. P., & Moro, I. (2020). Exploring Ulva australis Areschoug for possible biotechnological applications: In vitro antioxidant and enzymatic inhibitory properties, and fatty acids contents. Algal Research, 50, 101980. https://doi.org/10.1016/j.algal.2020.101980
   Google Scholar
• Turkan, F., Cetin, A., Taslimi, P., Karaman, M., & Gulçin, İ. (2019). Synthesis, biological evaluation and molecular docking of novel pyrazole derivatives as potent carbonic anhydrase and acetylcholinesterase inhibitors. Bioorganic Chemistry, 86, 420–427. https://doi.org/10.1016/j.bioorg.2019.02.013
   PubMed Web of Science ®Google Scholar
• Urones, J. G., Marcos, I. S., Ferreras, J. F., & Barcala, P. B. (1988). Terpenoids from Nepeta tuberosa subsp. reticulata (II). Phytochemistry, 27(2), 523–526. https://doi.org/10.1016/0031-9422(88)83133-9
   Web of Science ®Google Scholar
• Velázquez-Jiménez, R., González-Montiel, S., Sánchez-Ortega, I., Villagómez-Ibarra, J. R., & Acevedo-Sandoval, O. A. (2023). ADMET prediction, docking, DM analysis and antibacterial screening of epoxy furan-clerodanes from Croton hypoleucus. Journal of Molecular Structure, 1277, 134840. https://doi.org/10.1016/j.molstruc.2022.134840
   Web of Science ®Google Scholar
• Xavier, S., & Periandy, S. (2015). Spectroscopic (FT-IR, FT-Raman, UV and NMR) investigation on 1-phenyl-2-nitropropene by quantum computational calculations. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 149, 216–230. https://doi.org/10.1016/j.saa.2015.04.055
   PubMed Web of Science ®Google Scholar
• Yang, X.-W., Huang, M.-Z., Jin, Y.-S., Sun, L.-N., Song, Y., & Chen, H.-S. (2012). Phenolics from Bidens bipinnata and their amylase inhibitory properties. Fitoterapia, 83(7), 1169–1175. https://doi.org/10.1016/j.fitote.2012.07.005
   PubMed Web of Science ®Google Scholar
• Yenigun, S., Ipek, Y., Marah, S., Demirtas, I., & Ozen, T. (2024). DNA protection, molecular docking, antioxidant, antibacterial, enzyme inhibition, and enzyme kinetic studies for parietin, isolated from Xanthoria parietina (L.) Th. Fr. Journal of Biomolecular Structure & Dynamics, 42(2), 848–862. https://doi.org/10.1080/07391102.2023.2196693
   PubMed Web of Science ®Google Scholar
• Yenigün, S., Başar, Y., İpek, Y., Behçet, L., Özen, T., & Demirtaş, İ. (2024). Determination of antioxidant, DNA protection, enzyme inhibition potential and molecular docking studies of a biomarker ursolic acid in Nepeta species. Journal of Biomolecular Structure & Dynamics, 42, 1–18. https://doi.org/10.1080/07391102.2023.2229440
   Web of Science ®Google Scholar
• Zhang, A., Wei, N., Liu, X., Wu, M., & Xuan, G. (2021). Inhibitory evaluation and molecular docking analysis of benzenesulfonamides on carbonic anhydrase II. Russian Journal of Bioorganic Chemistry, 47(1), 261–269. https://doi.org/10.1134/S1068162021010283
   Web of Science ®Google Scholar
• Zhang, L., Mulrooney, S. B., Leung, A. F., Zeng, Y., Ko, B. B., Hausinger, R. P., & Sun, H. (2006). Inhibition of urease by bismuth (III): İmplications for the mechanism of action of bismuth drugs. Biometals, 19(5), 503–511. https://doi.org/10.1007/s10534-005-5449-0
   PubMed Web of Science ®Google Scholar