98
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Phytochemical profiling, in vitro analysis for anti-inflammatory, immunomodulatory activities, structural elucidation and in silico evaluation of potential selective COX-2 and TNF-α inhibitor from Hydrilla verticillata (L.f.) Royle

, , , &
Received 16 Mar 2023, Accepted 09 Nov 2023, Published online: 29 Nov 2023

References

  • Abdelkhalek, A. A., Sharaf, A.-M. M., Rabie, M., & El-Subbagh, H. I. (2017). Derivatives of Cucurbitacin-E-glucoside produced by Curvularia lunata NRRL 2178: Anti-inflammatory, antipyretic, antitumor activities, and effect on biochemical parameters. Future Journal of Pharmaceutical Sciences, 3(2), 124–130. https://doi.org/10.1016/j.fjps.2017.04.006
  • Alam, M. J., Alam, O., Khan, S. A., Naim, M. J., Islamuddin, M., & Deora, G. S. (2016). Synthesis, anti-inflammatory, analgesic, COX1/2-inhibitory activity, and molecular docking studies of hybrid pyrazole analogues. Drug Design, Development and Therapy, 10, 3529–3543. https://doi.org/10.2147/DDDT.S118297
  • Aravindaram, K., & Yang, N. S. (2010). Anti-inflammatory plant natural products for cancer therapy. Planta Medica, 76(11), 1103–1117. https://doi.org/10.1055/s-0030-1249859
  • Balkwill, F., & Mantovani, A. (2001). Inflammation and cancer: Back to Virchow? Lancet, 357(9255), 539–545. https://doi.org/10.1016/S0140-6736(00)04046-0
  • Bilal, M. S., Ejaz, S. A., Zargar, S., Akhtar, N., Wani, T. A., Riaz, N., Aborode, A. T., Siddique, F., Altwaijry, N., Alkahtani, H. M., & Umar, H. I. (2022). Computational investigation of 1, 3, 4 oxadiazole derivatives as lead inhibitors of VEGFR 2 in comparison with EGFR: Density functional theory, molecular docking and molecular dynamics simulation studies. Biomolecules, 12(11), 1612. https://doi.org/10.3390/biom12111612
  • Borkotoky, S., & Murali, A. A. (2018). Computational assessment of pH-dependent differential interaction of T7 lysozyme with T7 RNA polymerase. BMC Structural Biology, 17, 1–11. https://doi.org/10.1186/s12900-017-0077-9
  • Bradley, J. (2008). TNF‐mediated inflammatory disease. The Journal of Pathology, 214(2), 149–160. https://doi.org/10.1002/path.2287
  • Brooks, B. R., Brooks, C. L., Mackerell, A. D., Nilsson, L., Petrella, R. J., Roux, B., Won, Y., Archontis, G., Bartels, C., Boresch, S., Caflisch, A., Caves, L., Cui, Q., Dinner, A. R., Feig, M., Fischer, S., Gao, J., Hodoscek, M., Im, W., … Karplus, M. (2009). CHARMM: The biomolecular simulation program. Journal of Computational Chemistry, 30(10), 1545–1614. https://doi.org/10.1002/jcc.21287
  • Gemala, A., Fitriyono, A., & Rafika, E. (2022). Critical review on the immunomodulatory activities of carrot’s β-carotene and other bioactive compounds. Journal of Functional Foods, 99, 105303. https://doi.org/10.1016/j.jff.2022.105303
  • Guo, Z. (2017). The modification of natural products for medical use. Acta Pharmaceutica Sinica. B, 7(2), 119–136. https://doi.org/10.1016/j.apsb.2016.06.003
  • Haines, H. H. (1921–1925). The botany of Bihar and Odisha, Vol. 1-6 parts. Adlard and Sons and West Newman, Ltd.
  • Haque, R. A., Iqbal, M. A., Asekunowo, P., Majid, A. M. S. A., Khadeer Ahamed, M. B., Umar, M. I., Al-Rawi, S. S., & Al-Suede, F. S. R. (2013). Synthesis, structure, anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag(I) N-heterocyclic carbene complexes (part-II). Medicinal Chemistry Research, 22(10), 4663–4676. https://doi.org/10.1007/s00044-012-0461-8
  • He, M. M., Smith, A. S., Oslob, J. D., Flanagan, W. M., Braisted, A. C., Whitty, A., Cancilla, M. T., Wang, J., Lugovskoy, A. A., Yoburn, J. C., Fung, A. D., Farrington, G., Eldredge, J. K., Day, E. S., Cruz, L. A., Cachero, T. G., Miller, S. K., Friedman, J. E., Choong, I. C., & Cunningham, B. C. (2005). Small-molecule inhibition of TNF-α. Science, 310(5750), 1022–1025. https://doi.org/10.1126/science.1116304
  • Hess, B., Bekker, H., Berendsen, H. J., & Fraaije, J. G. (1997). LINCS: A linear constraint solver for molecular simulations. Journal of Computational Chemistry, 18(12), 1463–1472. https://doi.org/10.1021/ct5007983
  • Horiuchi, T., Mitoma, H., Harashima, S. I., Tsukamoto, H., & Shimoda, T. (2010). Transmembrane TNF-α: Structure, function and interaction with anti-TNF agents. Rheumatology, 49(7), 1215–1228. https://doi.org/10.1093/rheumatology/keq031
  • Ibrahim, H., Uttu, A. J., Sallau, M. S., & Iyun, O. R. A. (2021). Gas chromatography–mass spectrometry (GC–MS) analysis of ethyl acetate root bark extract of Strychnos innocua (Delile). Beni-Suef University Journal of Basic and Applied Sciences, 10(1), 1-8. https://doi.org/10.1186/s43088-021-00156-1
  • Jiang, F., Jiang, Y., Zhi, H., Dong, Y., Li, H., Ma, S., Wang, Y., Dong, Q., Shen, H., & Wang, Y. (2017). Artificial intelligence in healthcare: Past, present and future. Stroke and Vascular Neurology, 2(4), 230–243. https://doi.org/10.1136/svn-2017-000101
  • Jo, S., Kim, T., Iyer, V. G., & Im, W. (2008). CHARMM-GUI: A web-based graphical user interface for CHARMM. Journal of Computational Chemistry, 29(11), 1859–1865. https://doi.org/10.1002/jcc.20945
  • Kashefolgheta, S., & Verde, A. V. (2017). Developing force fields when experimental data is sparse: AMBER/GAFF-compatible parameters for inorganic and alkyl oxoanions. Physical Chemistry Chemical Physics: PCCP, 19(31), 20593–20607. https://doi.org/10.1039/c7cp02557b
  • Khalifa, I., Nawaz, A., Sobhy, R., Althwab, S. A., & Barakat, H. (2020). Polyacylated anthocyanins constructively network with catalytic dyad residues of 3CLpro of 2019-nCoV than monomeric anthocyanins: A structural-relationship activity study with 10 anthocyanins using in-silico approaches. Journal of Molecular Graphics & Modelling, 100, 107690. https://doi.org/10.1016/j.jmgm.2020.107690
  • Kong, M., Xie, K., Lv, M., Li, J., Yao, J., Yan, K., Wu, X., Xu, Y., & Ye, D. (2021). Anti-inflammatory phytochemicals for the treatment of diabetes and its complications: Lessons learned and future promise. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 133, 110975. https://doi.org/10.1016/j.biopha.2020.110975
  • Lindorff‐Larsen, K., Piana, S., Palmo, K., Maragakis, P., Klepeis, J. L., Dror, R. O., & Shaw, D. E. (2010). Improved side‐chain torsion potentials for the Amber ff99SB protein force field. Proteins, 78(8), 1950–1958. https://doi.org/10.1002/prot.22711
  • McInnes, I. B., & Gravallese, E. M. (2021). Immune-mediated inflammatory disease therapeutics: Past, present and future. Nature Reviews. Immunology, 21(10), 680–686. https://doi.org/10.1038/s41577-021-00603-1
  • Medzhitov, R. (2008). Origin and physiological roles of inflammation. Nature, 454(7203), 428–435. https://doi.org/10.1038/nature07201
  • Meher, R. K., Mir, S. A., & Anisetti, S. S. (2023). In silico and in vitro investigation of dual targeting Prima-1MET as precision therapeutic against lungs cancer. Journal of Biomolecular Structure & Dynamics, 41(10), 1–16. https://doi.org/10.1080/07391102.2023.2219323
  • Meher, R. K., Nagireddy, P. K. R., Pragyandipta, P., Kantevari, S., Singh, S. K., Kumar, V., & Naik, P. K. (2022). In silico design of novel tubulin binding 9-arylimino derivatives of noscapine, their chemical synthesis and cellular activity as potent anticancer agents against breast cancer. Journal of Biomolecular Structure & Dynamics, 40(15), 6725–6736. https://doi.org/10.1080/07391102.2021.1889668
  • Meher, R. K., Naik, M. R., Bastia, B., & Naik, P. K. (2018). Comparative evaluation of anti-angiogenic effects of noscapine derivatives. Bioinformation, 14(5), 236–240. https://doi.org/10.6026/97320630014236
  • Meher, R. K., Pragyandipta, P., Pedapati, R. K., Nagireddy, P. K., Kantevari, S., Nayek, A. K., & Naik, P. K. (2021). Rational design of novel N‐alkyl amine analogues of noscapine, their chemical synthesis and cellular activity as potent anticancer agents. Chemical Biology & Drug Design, 98(3), 445–465. https://doi.org/10.1111/cbdd.13901
  • Meier, F. M. P., Frerix, M., Hermann, W., & Müller-Ladner, U. (2013). Current immunotherapy in rheumatoid arthritis. Immunotherapy, 5(9), 955–974. https://doi.org/10.2217/imt.13.94
  • Mir, S. A., Dash, G. C., Meher, R. K., Mohanta, P. P., Chopdar, K. S., Mohapatra, P. K., Baitharu, I., Behera, A. K., Raval, M. K., & Nayak, B. (2022). In silico and in vitro evaluations of fluorophoric thiazolo-[2,3-b] quinazolinones as anti-cancer agents targeting EGFR-TKD. Applied Biochemistry and Biotechnology, 194(10), 4292–4318. https://doi.org/10.1007/s12010-022-03893-w
  • Mir, S. A., Meher, R. K., & Nayak, B. (2023). Molecular modeling and simulations of some antiviral drugs, benzylisoquinoline alkaloid, and coumarin molecules to investigate the effects on Mpro main viral protease inhibition. Biochemistry and Biophysics Reports, 34, 101459. https://doi.org/10.1016/j.bbrep.2023.101459
  • Mir, S. A., Muhammad, A., Padhiary, A., Ekka, N. J., Baitharu, I., Naik, P. K., & Nayak, B. (2023). Identification of potent EGFR-TKD inhibitors from NPACT database through combined computational approaches. Journal of Biomolecular Structure & Dynamics, 39, 1–14. https://doi.org/10.1080/07391102.2023.2171133
  • Mir, S. A., Paramita Mohanta, P., Kumar Meher, R., Baitharu, I., Kumar Raval, M., Kumar Behera, A., & Nayak, B. (2022). Structural insights into conformational stability and binding of thiazolo-[2,3-b] quinazolinone derivatives with EGFR-TKD and in-vitro study. Saudi Journal of Biological Sciences, 29(12), 103478. https://doi.org/10.1016/j.sjbs.2022.103478
  • Patel, A. K., Meher, R. K., Reddy, P. K., Pedapati, R. K., Pragyandipta, P., Kantevari, S., Naik, M. R., & Naik, P. K. (2021). Rational design, chemical synthesis and cellular evaluation of novel 1, 3-diynyl derivatives of noscapine as potent tubulin binding anticancer agents. Journal of Molecular Graphics & Modelling, 106, 107933. https://doi.org/10.1016/j.jmgm.2021.107933
  • Philip, M., Rowley, D. A., & Schreiber, H. (2004). Inflammation as a tumor promoter in cancer induction. Seminars in Cancer Biology, 14(6), 433–439. https://doi.org/10.1016/j.semcancer.2004.06.006
  • Ramakrishna Pillai, J., Wali, A. F., Menezes, G. A., Rehman, M. U., Wani, T. A., Arafah, A., Zargar, S., & Mir, T. M. (2022). Chemical composition analysis, cytotoxic, antimicrobial and antioxidant activities of Physalis angulata L.: A comparative study of leaves and fruit. Molecules, 27(5), 1480. https://doi.org/10.3390/molecules27051480
  • Reis-Sobreiro, M., Teixeira da Mota, A., Jardim, C., & Serre, K. (2021). Bringing macrophages to the frontline against cancer: Current immunotherapies targeting macrophages. Cells, 10(9), 2364. https://doi.org/10.3390/cells10092364
  • Roda, G., Jharap, B., Neeraj, N., & Colombel, J. F. (2016). Loss of response to anti-TNFs: Definition, epidemiology, and management. Clinical and Translational Gastroenterology, 7(1), e135. https://doi.org/10.1038/ctg.2015.63
  • Saleem, A., Farooq, U., Bukhari, S. M., Khan, S., Zaidi, A., Wani, T. A., Shaikh, A. J., Sarwar, R., Mahmud, S., Israr, M., Khan, F. A., & Shahzad, S. A. (2022). Isoxazole derivatives against carbonic anhydrase: Synthesis, molecular docking, MD simulations, and free energy calculations coupled with in vitro studies. ACS Omega, 7(34), 30359–30368. https://doi.org/10.1021/acsomega.2c03600
  • Saluja, T. S., Kumar, V., Agrawal, M., Tripathi, A., Meher, R. K., Srivastava, K., Gupta, A., Singh, A., Chaturvedi, A., & Singh, S. K. (2020). Mitochondrial stress–mediated targeting of quiescent cancer stem cells in oral squamous cell carcinoma. Cancer Management and Research, 12, 4519–4530. https://doi.org/10.2147/CMAR.S252292
  • Saxena, H. O., & Brahmam, M. (1994–96). The flora of Orissa (Vol. 1–4). Bhubaneswar: RRL and Orissa Forest Development Corporation Ltd.
  • Sobolewski, C., Cerella, C., Dicato, M., Ghibelli, L., & Diederich, M. (2010). The role of cyclooxygenase-2 in cell proliferation and cell death in human malignancies. International Journal of Cell Biology, 2010, 215158. https://doi.org/10.1155/2010/215158
  • Sousa da Silva, A. W., & Vranken, W. F. (2012). ACPYPE-Antechamber python parser interface. BMC Research Notes, 5(1), 367. https://doi.org/10.1186/1756-0500-5-367
  • Subedi, L., Lee, S. E., Madiha, S., Gaire, B. P., Jin, M., Yumnam, S., & Kim, S. Y. (2020). Phytochemicals against TNF α-mediated neuroinflammatory diseases. International Journal of Molecular Sciences, 21(3), 764.
  • Vaou, N., Stavropoulou, E., Voidarou, C., Tsigalou, C., & Bezirtzoglou, E. (2021). Towards advances in medicinal plant antimicrobial activity: A review study on challenges and future perspectives. Microorganisms, 9(10), 2041. https://doi.org/10.3390/microorganisms9102041
  • Wang, J., Wang, W., Kollman, P. A., & Case, A. A. (2006). Automatic atom type and bond type perception in molecular mechanical calculations. Journal of Molecular Graphics & Modelling, 25(2), 247–260. https://doi.org/10.1016/j.jmgm.2005.12.005
  • Wang, J. L., Limburg, D., Graneto, M. J., Springer, J., Hamper, J. R. B., Liao, S., Pawlitz, J. L., Kurumbail, R. G., Maziasz, T., Talley, J. J., Kiefer, J. R., & Carter, J. (2010). The novel benzopyran class of selective cyclooxygenase-2 inhibitors. Part 2: The second clinical candidate having a shorter and favorable human half-life. Bioorganic & Medicinal Chemistry Letters, 20(23), 7159–7163. https://doi.org/10.1016/j.bmcl.2010.07.054
  • Wani, T. A., & Zargar, S. (2023). Molecular spectroscopy evidence of 1, 3, 5-Tris (4-carboxyphenyl) benzene binding to DNA: Anticancer potential along with the comparative binding profile of intercalation via modeling studies. Cells, 12(8), 1120. https://doi.org/10.3390/cells12081120
  • Watanabe, S., Alexander, M., Misharin, A. V., & Budinger, G. R. S. (2019). Budinger GRS. The role of macrophages in the resolution of inflammation. The Journal of Clinical Investigation, 129(7), 2619–2628. PMID: 31107246; PMCID: PMC6597225. https://doi.org/10.1172/JCI124615
  • Windsor, J. S., Rodway, G. W., Middleton, P. M., & McCarthy, S. (2006). Digital photography. Postgraduate Medical Journal, 82(972), 688–692. https://doi.org/10.1136/pgmj.2006.044990
  • Yao, H., Liu, J., Xu, S., Zhu, Z., & Xu, J. (2017). The structural modification of natural products for novel drug discovery. Expert Opinion on Drug Discovery, 12(2), 121–140. https://doi.org/10.1080/17460441.2016.1272757
  • Yoon, E.-J., Kim, J. O., Kim, D., Lee, H., Yang, J. W., Lee, K. J., & Jeong, S. H. (2018). Klebsiella pneumoniae carbapenemase producers in South Korea between 2013 and 2015. Frontiers in Microbiology, 9, 56. https://doi.org/10.3389/fmicb.2018.00056
  • Zahedipour, F., Hosseini, S. A., Henney, N. C., Barreto, G. E., & Sahebkar, A. (2022). Phytochemicals as inhibitors of tumor necrosis factor alpha and neuroinflammatory responses in neurodegenerative diseases. Neural Regeneration Research, 17(8), 1675–1684. https://doi.org/10.4103/1673-5374.332128
  • Zidar, N., Odar, K., Glavac, D., Jerse, M., Zupanc, T., & Stajer, D. (2009). Cyclooxygenase in normal human tissues–is COX‐1 really a constitutive isoform, and COX‐2 an inducible isoform? Journal of Cellular and Molecular Medicine, 13(9b), 3753–3763. https://doi.org/10.1111/j.1582-4934.2008.00430.x
  • Zimmermann-Klemd, A. M., Konradi, V., Steinborn, C., Ücker, A., Falanga, C. M., Woelfle, U., Huber, R., Jürgenliemk, G., Rajbhandari, M., & Gründemann, C. (2019). Influence of traditionally used Nepalese plants on wound healing and immunological properties using primary human cells in vitro. Journal of Ethnopharmacology, 235, 415–423. https://doi.org/10.1016/j.jep.2019.02.034

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.