410
Views
26
CrossRef citations to date
0
Altmetric
Research Articles

Exploration of interaction mechanism of tyrosol as a potent anti-inflammatory agent

ORCID Icon, ORCID Icon, , , , & show all
Pages 382-397 | Received 14 Nov 2018, Accepted 22 Jan 2019, Published online: 19 Mar 2019

References

  • Adhami, H. R., Zehl, M., Dangl, C., Dorfmeister, D., Stadler, M., Urban, E., … Krenn, L. (2015). Preparative isolation of oleocanthal, tyrosol, and hydroxytyrosol from olive oil by HPCCC. Food Chemistry, 170, 154–159.
  • Ahn, E. Y., Jiang, Y., Zhang, Y., Son, E. M., You, S., Kang, S. W., … Kim, D. K. (2008). Cytotoxicity of p-tyrosol and its derivatives may correlate with the inhibition of DNA replication initiation. Oncology Reports, 19(2), 527–534.
  • Arfeen, M., Patel, R., Khan, T., & Bharatam, P. V. (2015). Molecular dynamics simulation studies of GSK-3β ATP competitive inhibitors: Understanding the factors contributing to selectivity. Journal of Biomolecular Structure & Dynamics, 33(12), 2578–2593.
  • Balasco, N., Barone, D., & Vitagliano, L. (2015). Structural conversion of the transformer protein RfaH: New insights derived from protein structure prediction and molecular dynamics simulations. Journal of Biomolecular Structure & Dynamics, 33(10), 2173–2179.
  • Becke, A. D. (1993). Density functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics., 98(7), 5648–5652. doi:10.1063/1.464913
  • Bertelli, A. A., Migliori, M., Panichi, V., Longoni, B., Origlia, N., Ferretti, A., … Giovannini, L. (2002). Oxidative stress and inflammatory reaction modulation by white wine. Annals of the New York Academy of Sciences, 957, 295–301.
  • Beutler, J. A. (2009). Natural products as a foundation for drug discovery. Current Protocols in Pharmacology, 46, 9.11.1–9.11.21.
  • Bowers, K. J., Chow, E., Xu, H., Dror, R. O., Eastwood, M. P., Gregersen, B., & Shaw, D. E. (2006). Scalable algorithms for molecular dynamics simulations on commodity clusters. In SC 2006 Conference, Proceedings of the ACM/IEEE (p. 43). Tampa, FL: IEEE.
  • Brandenburg, K. (1999). DIAMOND: Visual Crystal Structure Information System. Version 2.1c. Bonn, Germany: Crystal Impact GbR.
  • Brenes, M., García, A., García, P., & Garrido, A. (2000). Rapid and complete extraction of phenols from olive oil and determination by means of a coulometric electrode array system. Journal of Agricultural and Food Chemistry, 48(11), 5178–5183.
  • Bu, Y., Rho, S., Kim, J., Kim, M. Y., Lee, D. H., Kim, S. Y., … Kim, H. (2007). Neuroprotective effect of tyrosol on transient focal cerebral ischemia in rats. Neuroscience Letters, 414(3), 218–221.
  • Carluccio, M. A., Siculella, L., Ancora, M. A., Massaro, M., Scoditti, E., Storelli, C., … De Caterina, R. (2003). Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: Antiatherogenic properties of Mediterranean diet phytochemicals. Arteriosclerosis, Thrombosis, and Vascular Biology, 23(4), 622–629.
  • Chandramohan, R., Pari, L., Rathinam, A., & Sheikh, B. A. (2015). Tyrosol, a phenolic compound, ameliorates hyperglycemia by regulating key enzymes of carbohydrate metabolism in streptozotocin induced diabetic rats. Chemico-Biological Interactions, 229, 44–54.
  • Cheki, M., Yahyapour, R., Farhood, B., Rezaeyan, A., Shabeeb, D., Amini, P., … Najafi, M. (2018). COX-2 in radiotherapy: A potential target for radioprotection and radiosensitization. Current Molecular Pharmacology, 11(3), 173–183.
  • Chinery, R., Beauchamp, R. D., Shyr, Y., Kirkland, S. C., Coffey, R. J., & Morrow, J. D. (1998). Antioxidants reduce cyclooxygenase-2 expression, prostaglandin production, and proliferation in colorectal cancer cells. Cancer Research, 58(11), 2323–2327.
  • Darvas, F., Keseru, G., Papp, A., Dormán, G., Urge, L., & Krajcsi, P. (2002). In silico and ex silico ADME approaches for drug discovery. Current Topics in Medicinal Chemistry, 2(12), 1287–1304.
  • Dhanjal, J. K., Sreenidhi, A. K., Bafna, K., Katiyar, S. P., Goyal, S., Grover, A., & Sundar, D. (2015). Computational structure-based de novo design of hypothetical inhibitors against the anti-inflammatory target COX-2. PLoS One, 10(8), e0134691.
  • Dinnella, C., Minichino, P., D’Andrea, A. M., & Monteleone, E. (2007). Bioaccessibility and antioxidant activity stability of phenolic compounds from extra-virgin olive oils during in vitro digestion. Journal of Agricultural and Food Chemistry, 55(21), 8423–8429. doi:10.1021/jf072244+
  • Dubois, R. N., Abramson, S. B., Crofford, L., Gupta, R. A., Simon, L. S., Van De Putte, L. B., & Lipsky, P. E. (1998). Cyclooxygenase in biology and disease. FASEB Journal: Official Publication of the Federation of American Societies for Experimental Biology, 12(12), 1063–1073.
  • Ferguson, L. R., Zhu, S-T., & Harris, P. J. (2005). Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 cells. Molecular Nutrition & Food Research, 49(6), 585–593.
  • Frisch, M. J. (2009). Gaussian 09, Revision A.1. Wallingford, CT.
  • Fuggetta, M. P., Cottarelli, A., Lanzilli, G., Tricarico, M., & Bernini, R. (2012). In vitro antitumor activity of olive oil tyrosol and hydroxytyrosol and their methyl carbonate derivatives. Medicinal and Aromatic Plant Science and Biotechnology, 6, 25–30.
  • Funk, C. D., Funk, L. B., Kennedy, M. E., Pong, A. S., & Fitzgerald, G. A. (1991). Human platelet/erythroleukemia cell prostaglandin G/H synthase: cDNA cloning, expression, and gene chromosomal assignment. FASEB Journal: Official Publication of the Federation of American Societies for Experimental Biology, 5(9), 2304–2312.
  • Giovannini, C., Straface, E., Modesti, D., Coni, E., Cantafora, A., De Vincenzi, M., … Masella, R. (1999). Tyrosol, the major olive oil biophenol, protects against oxidized-LDL-induced injury in Caco-2 cells. The Journal of Nutrition, 129(7), 1269–1277.
  • Gleeson, M. P., Hersey, A., & Hannongbua, S. (2011). In-silico ADME models: A general assessment of their utility in drug discovery applications. Current Topics in Medicinal Chemistry, 11(4), 358–381.
  • Goel, N., & Kumar, N. (2017). A stable nonanuclear Tb(III) cluster for selective sensing of picric acid. Inorganica Chimica Acta, 463, 14–19. doi:10.1016/j.ica.2017.04.010
  • Goel, N., & Kumar, N. (2018). A dual-functional luminescent Tb(iii) metal–organic framework for the selective sensing of acetone and TNP in water. RSC Advances, 8(20), 10746–10755. doi:10.1039/C7RA13494K
  • Guo, Z., Mohanty, U., Noehre, J., Sawyer, T. K., Sherman, W., & Krilov, G. (2010). Probing the alpha-helical structural stability of stapled p53 peptides: Molecular dynamics simulations and analysis. Chemical Biology & Drug Design, 75(4), 348–359.
  • Halgren, T. A. (2009). Identifying and characterizing binding sites and assessing druggability. Journal of Chemical Information and Modeling, 49(2), 377–389.
  • Halgren, T. A., Murphy, R. B., Friesner, R. A., Beard, H. S., Frye, L. L., Pollard, W. T., & Banks, J. L. (2004). Glide: A new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. Journal of Medicinal Chemistry, 47(7), 1750–1759.
  • Harvey, A. L. (2008). Natural products in drug discovery. Drug Discovery Today, 13(19–20), 894–901.
  • Hempel, S. L., Monick, M. M., & Hunninghake, G. W. (1994). Lipopolysaccharide induces prostaglandin H synthase-2 protein and mRNA in human alveolar macrophages and blood monocytes. The Journal of Clinical Investigation, 93(1), 391–396.
  • Hockridge, M. R., Knight, S. M., Robertson, E. G., Simons, J. P., McCombie, J., & Walker, M. (1999). Conformational landscapes in flexible organic molecules: 4-Hydroxy phenyl ethanol (p-tyrosol) and its singly hydrated complex. Physical Chemistry Chemical Physics, 1(3), 407–413. doi:10.1039/a808701f
  • Hodgson, J. (2001). ADMET-turning chemicals into drugs. Nature Biotechnology, 19(8), 722–726.
  • Jorgensen, W. L., Chandrasekhar, J., Madura, J. D., Impey, R. W., & Klein, M. L. (1983). Comparison of simple potential functions for simulating liquid water. Journal of Chemical Physics, 79(2), 926–935. doi:10.1063/1.445869
  • Kelley, D. J., Mestre, J. R., Subbaramaiah, K., Sacks, P. G., Schantz, S. P., Tanabe, T., … Dannenberg, A. J. (1997). Benzo[a]pyrene up-regulates cyclooxygenase-2 gene expression in oral epithelial cells. Carcinogenesis, 18(4), 795–799. doi:10.1093/carcin/18.4.795
  • Klaus, B. (1999). DIAMOND version 1.2c. Bonn, Germany: University of Bonn.
  • Koehn, F. E., & Carter, G. T. (2005). The evolving role of natural products in drug discovery. Nature Reviews. Drug Discovery, 4(3), 206–220.
  • Kontou, N., Psaltopoulou, T., Panagiotakos, D., Dimopoulos, M. A., & Linos, A. (2011). The mediterranean diet in cancer prevention: A review. Journal of Medicinal Food, 14(10), 1065–1078.
  • Koopmans, T. (1934). About the allocation of wave functions and eigenvalues of the individual electrons one atom. Physica, 1(1–6), 104–113.
  • Kumar, N., & Garg, A. (2014). Structural optimization and docking studies of anatoxin-a: A potent neurotoxin. African Journal of Biotechnology, 13(30), 3092–3100. doi:10.5897/AJB2014.13671
  • Kumar, N., Goel, N., Yadav, T. C., & Pruthi, V. (2017). Quantum chemical, ADMET and molecular docking studies of ferulic acid amide derivatives with a novel anti-cancer drug target. Medicinal Chemistry Research, 26(8), 1822–1834. doi:10.1007/s00044-017-1893-y
  • Kumar, N., Gupta, S., Yadav, T. C., Pruthi, V., Varadwaj, P. K., & Goel, N. (2018). Extrapolation of phenolic compounds as multi-target agents against cancer and inflammation. Journal of Biomolecular Structure and Dynamics, 1. doi:10.1080/07391102.2018.1481457
  • Kumar, N., Kumar, S., Abbat, S., Nikhil, K., Sondhi, S. M., Bharatam, P. V., … Pruthi, V. (2016). Ferulic acid amide derivatives as anticancer and antioxidant agents: Synthesis, thermal, biological and computational studies. Medicinal Chemistry Research, 25(6), 1175–1192. doi:10.1007/s00044-016-1562-6
  • Kumar, N., & Pruthi, V. (2014). Potential applications of ferulic acid from natural sources. Biotechnology Reports (Amsterdam)), 4, 86–93.
  • Kumar, N., & Pruthi, V. (2015). Structural elucidation and molecular docking of ferulic acid from Parthenium hysterophorus possessing COX-2 inhibition activity. 3 Biotech, 5(4), 541–551.
  • Kumar, N., Pruthi, V., & Goel, N. (2015). Structural, thermal and quantum chemical studies of p-coumaric and caffeic acids. Journal of Molecular Structure, 1085, 242–248. doi:10.1016/j.molstruc.2014.12.064
  • 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(1–3), 3–25. doi:10.1016/S0169-409X(96)00423-1
  • Lombardo, F., Gifford, E., & Shalaeva, M. Y. (2003). In silico ADME prediction: Data, models, facts and myths. Mini Reviews in Medicinal Chemistry, 3(8), 861–875.
  • Loru, D., Incani, A., Deiana, M., Corona, G., Atzeri, A., Melis, M. P., … Dessi, M. A. (2009). Protective effect of hydroxytyrosol and tyrosol against oxidative stress in kidney cells. Toxicology and Industrial Health, 25(4–5), 301–310.
  • Lucido, M. J., Orlando, B. J., Vecchio, A. J., & Malkowski, M. G. (2016). Crystal structure of aspirin-acetylated human cyclooxygenase-2: Insight into the formation of products with reversed stereochemistry. Biochem, 55(8), 1226–1238. doi:10.1021/acs.biochem.5b01378
  • Manach, C., Williamson, G., Morand, C., Scalbert, A., & Rémésy, C. (2005). Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. The American Journal of Clinical Nutrition, 81(1 Suppl), 230S–242S.
  • Mestre, J. R., Chan, G., Zhang, F., Yang, E. K., Sacks, P. G., Boyle, J. O., … Dannenberg, A. J. (1999). Inhibition of cyclooxygenase-2 expression. An approach to preventing head and neck cancer. Annals of the New York Academy of Sciences, 889, 62–71.
  • Montedoro, G., Servili, M., Baldioli, M., & Miniati, E. (1992). Simple and hydrolyzable phenolic compounds in virgin olive oil. 1. Their extraction, separation, and quantitative and semiquantitative evaluation by HPLC. Journal of Agricultural and Food Chemistry, 40(9), 1571–1576. doi:10.1021/jf00021a019
  • Navia, M. A., & Chaturvedi, P. R. (1996). Design principles for orally bioavailable drugs. Drug Discovery Today, 1(5), 179–189. doi:10.1016/1359-6446(96)10020-9
  • Nile, S. H., Ko, E. Y., Kim, D. H., & Keum, Y. S. (2016). Screening of ferulic acid related compounds as inhibitors of xanthine oxidase and cyclooxygenase-2 with anti-inflammatory activity. Brazilian J Pharmacognosy, 26(1), 50–55. doi:10.1016/j.bjp.2015.08.013
  • Ou, S., Li, Y., & Gao, K. (1999). A study on scavenging activity of wheat bran dietary fiber for free radical. Acta Nutrimenta Sinica, 21, 191–194.
  • Pang, L. Y., Hurst, E. A., & Argyle, D. J. (2016). Cyclooxygenase-2: A role in cancer stem cell survival and repopulation of cancer cells during therapy. Stem Cells International, 2016, 1–11. doi:10.1155/2016/2048731
  • Panossian, A., Nikoyan, N., Ohanyan, N., Hovhannisyan, A., Abrahamyan, H., Gabrielyan, E., & Wikman, G. (2008). Comparative study of Rhodiola preparations on behavioral despair of rats. Phytomedicine: International Journal of Phytotherapy and Phytopharmacology, 15(1–2), 84–91.
  • Panossian, A., Wikman, G., Kaur, P., & Asea, A. (2009). Adaptogens exert a stress-protective effect by modulation of expression of molecular chaperones. Phytomedicine, 16(6–7), 617–622. doi:10.1016/j.phymed.2008.12.003
  • Pearson, R. G. (1988). Absolute electronegativity and hardness: Application to inorganic chemistry. Inorganic Chemistry, 27(4), 734–740. doi:10.1021/ic00277a030
  • Petroni, A., Blasevich, M., Salami, M., Papini, N., Montedoro, G. F., & Galli, C. (1995). Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil. Thrombosis Research, 78(2), 151–160.
  • Puerta, R., Martínez Domínguez, M. E., Ruíz-Gutíerrez, V., Flavill, J. A., & Hoult, J. R. (2001). Effects of virgin olive oil phenolics on scavenging of reactive nitrogen species and upon nitrergic neurotransmission. Life Sciences, 69(10), 1213–1222.
  • Raj, U., Kumar, H., Gupta, S., & Varadwaj, P. K. (2015). Novel DOT1L receptor natural inhibitors involved in mixed lineage leukemia: a virtual screening, molecular docking and dynamics simulation study. Asian Pacific Journal of Cancer Prevention: APJCP, 16(9), 3817–3825.
  • Romero, C., & Brenes, M. (2012). Analysis of total contents of hydroxytyrosol and tyrosol in olive oils. Journal of Agricultural and Food Chemistry, 60(36), 9017–9022.
  • SAINT version 7.34 (2004). Software for the integration of CCD detector system. Madison, WI: Bruker Analytical X-ray Systems.
  • Salucci, S., Burattini, S., Battistelli, M., Buontempo, F., Canonico, B., Martelli, A. M., … Falcieri, E. (2015). Tyrosol prevents apoptosis in irradiated keratinocytes. Journal of Dermatological Science, 80(1), 61–68.
  • 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.
  • Shaw, D. E., Yibing, S., John, L. K., Michael, P. E., & Ron, O. D. (2005). Gaussian split Ewald: A fast Ewald mesh method for molecular simulation. Journal of Chemical Physics, 122, 1–13.
  • Sheldrick, G. M. (1990). Phase annealing in SHELX-90: Direct methods for larger structures. Acta Crystallographica Section A Foundations of Crystallography, A46, 467–473. doi:10.1107/S0108767390000277
  • Sheldrick, G. M. (1996). SADABS: Program for empirical absorption correction of area detector data. Gottingen, Germany: University of Gottingen.
  • Sheldrick, G. M. (2000). SHELXTL-NT, Version 6.12, Reference manual. Germany: University of Gottingen.
  • Shen, B. (2015). A new golden age of natural products drug discovery. Cell, 163(6), 1297–1300.
  • Shivakumar, D., Williams, J., Wu, Y., Damm, W., Shelley, J., & Sherman, W. (2010). Prediction of absolute solvation free energies using molecular dynamics free energy perturbation and the OPLS force field. Journal of Chemical Theory and Computation, 6(5), 1509–1519. doi:10.1021/ct900587b
  • Thibault, S. L. C., Arseneault, M., Longpre, F., & Ramassamy, C. (2011). Tyrosol and hydroxytyrosol, two main components of olive oil, protect N2a cells against amyloid-b-induced toxicity. Involvement of the NF-kB signaling. Current Alzheimer Research, 8, 543–551. doi:10.2174/156720511796391845
  • Toshihiro, A., Ken, Y., Miho, Y., Motohiko, U., Yumiko, K., Naoto, S., & Koichi, A. (2000). Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects. Journal of Agricultural and Food Chemistry, 48, 2313–2319.
  • Tsuneda, T., & Hirao, K. (2014). Long-range correction for density functional theory. Wiley Interdisciplinary Reviews: Computational Molecular Science, 4(4), 375–390. doi:10.1002/wcms.1178
  • Vasilescu, D., & Adrian-Scotto, M. (2010). From Democritus to Schrödinger: A reflection on quantum molecular modeling. Structural Chemistry, 21(6), 1289–1314. doi:10.1007/s11224-010-9665-z
  • Verma, A. (2012). Lead finding from Phyllanthus debelis with hepatoprotective potentials. Asian Pacific Journal of Tropical Biomedicine, 2, 1735–1737.
  • Yadav, T. C., Srivastava, A. K., Dey, A., Kumar, N., Raghuwanshi, N., & Pruthi, V. (2018). Application of computational techniques to unravel structure–function relationship and their role in therapeutic development. Current Topics in Medicinal Chemistry, 18(20), 1769–1791.
  • Zhang, G., & Musgrave, C. B. (2007). Comparison of DFT methods for molecular orbital eigenvalue calculations. The Journal of Physical Chemistry A, 111(8), 1554–1561.

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.