Abstract
Some xanthone derivatives isolated from plants possess antifungal, antimicrobial, antioxidative and cytotoxic activities. Therefore, products manufactured from plants that contain xanthones are used as botanical dietary supplements. The operative mechanism of antioxidative action of 1,2,4-trihydroxyxanthone is investigated in this contribution. For this purpose, M06-2X/6-311++G(d,p) method is used. Antioxidative capacity of investigated xanthone is determined in benzene and water as mediums. It is found that, among three possible radicals that this xanthone can generate, the most stable is the one obtained by homolytic cleavage of O-H group in position 4. It was found that HAT (Hydrogen Atom Transfer) is the only operative mechanism for xanthone in benzene. On the other hand, the most favorable mechanism in water is SPLET (Sequential Proton Loss Electron Transfer). It should be emphasized that SET-PT (Single-Electron Transfer followed by Proton Transfer) is not plausible mechanistic pathway in both solvents. Antioxidants express their scavenger capacity in the presence of free radicals. Therefore here is examined scavenger capacity of 1,2,4-trihydroxyxanthone toward HO\( ^{\bullet}\), HOO\( ^{\bullet}\) and CH3OO\( ^{\bullet}\) radicals. It is found that the investigated xanthone is able to deactivate free radicals via competitive HAT and SPLET mechanisms. The observed reactivity of the xanthone toward free radicals decreases following the order: HO\( ^{\bullet}\) ≫ HOO\( ^{\bullet}\) > CH3OO\( ^{\bullet}\). It should be pointed out that reactivity of the xanthone to selected free radicals slightly increases with an increase in solvent polarity.
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Percival, M.: Antioxidants-a review. Clin. Nutr. Insights 31, 201–205 (1998)
Jung, H.A., Su, B.N., Keller, W.J., Mehta, R.G., Kinghorn, A.D.: Antioxidant xanthones from the pericarp of Garcinia mangostana (Mangosteen). J. Agric. Food Chem. 54(6), 2077–2082 (2006)
Chase, M., et al.: An update of the Angiosperm Phylogeny Group classification for the orders and families offlowering plants: APG II. Bot. J. Linn. Soc. 141(4), 399–436 (2003)
Donnenberg, V., Donnenberg, A.: Multiple drug resistance in cancer revisited: the cancer stem cell hypothesis. J. Clin. Pharmacol. 45(8), 872–877 (2005)
Marković, Z.: Study of the mechanisms of antioxidative action of different antioxidants. J. Serb. Soc. Comput. Mech. 10(1), 135–150 (2016)
Galano, A., Mazzone, G., Alvarez-Diduk, R., Marino, T., Alvarez-Idaboy, R., Russo, N.: Food antioxidants: chemical insights at the molecular level. Annu. Rev. Food Sci. Technol. 7, 335–352 (2016)
Knight, J.A.: Review: free radicals, antioxidants, and the immune system. Ann. Clin. Lab. Sci. 30(2), 145–158 (2000)
Yoshida, Y., Umeno, A., Shichiri, M.: Lipid peroxidation biomarkers for evaluating oxidative stress and assessing antioxidant capacity in vivo. J. Clin. Biochem. Nutr. 52(1), 9–16 (2013)
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.J., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, A.D., Rabuck, K.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Baboul, A.G., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Replogle, E.S., Pople, J.A.: Gaussian 09, Revision B.01. Gaussian Inc., Wallingford (2009)
Zhao, Y., Truhlar, D.G.: The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theoret. Chem. Acc. 120(1), 215–241 (2008)
Takano, Y., Houk, K.N.: Benchmarking the Conductor-like Polarizable Continuum Model (CPCM) for aqueous solvation free energies of neutral and ionic organic molecules. J. Chem. Theory Comput. 1(1), 70–77 (2005)
Tošović, J., Marković, S., Milenković, D., Marković, Z.: Solvation enthalpies and Gibbs energies of the proton and electron – influence of solvation models. J. Serb. Soc. Comput. Mech. 10(2), 66–76 (2016)
Aller, S., Yu, J., Ward, A., Weng, Y., Chittaboina, S., Zhuo, R., Harrell, P., Trinh, Y., Zhang, Q., Urbatsch, I., Chang, G.: Structure of P-glycoprotein reveals a molecular basis for poly-specific drug binding. Science 323(5922), 1718–1722 (2009)
Humphrey, W., Dalke, A., Schulten, K.: VMD: visual molecular dynamics. J. Mol. Graph. 14(1), 33–38 (1996)
Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., Olson, A.J.: AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J. Comput. Chem. 30(16), 2785–2791 (2009)
Fuhrmann, J., Rurainski, A., Lenhof, H.P., Neumann, D.: A new Lamarckian genetic algorithm for flexible ligand-receptor docking. J. Comput. Chem. 31(9), 1911–1918 (2010)
BIOVIA Discovery Studio (2016). http://accelrys.com/products/collaborative-science/biovia-discovery-studio/. Accessed 07 May 2016
Marković, Z., Marković, S., Dimitrić Marković, J., Milenković, D.: Structure and reactivity of baicalein radical cation. Int. J. Quant. Chem. 112(8), 2009–2017 (2012)
Marković, Z., Jeremić, S., Dimitrić Marković, J., Stanojević Pirković, M., Amić, D.: Influence of structural characteristics of substituents on the antioxidant activity of some anthraquinone derivatives. Comput. Theor. Chem. 1077, 25–31 (2016)
Jeremić, S., Šehović, S., Manojlović, N., Marković, Z.: Antioxidant and free radical scavenging activity of purpurin. Monatshefte für Chemie - Chemical Monthly 143(3), 427–435 (2012)
Jeremić, S., Filipović, N., Peulić, A., Marković, Z.: Thermodynamical aspect of radical scavenging activity of alizarin and alizarin red S. Theoretical comparative study. Comput. Theor. Chem. 1047, 15–21 (2014)
Reed, A.E., Curtiss, L.A., Weinhold, F.: Intermolecular interactions from a natural bond orbital donor-acceptor viewpoint. Chem. Rev. 88(6), 899–926 (1988)
Sharom, F.J.: ABC multidrug transporters: structure, function and role in chemoresistance. Pharmacogenomics 9(1), 105–127 (2008)
Loe, D.W., Deeley, R.G., Cole, S.P.C.: Biology of the multidrug resistance-associated protein, MRP. Eur. J. Cancer 32(6), 945–957 (1996)
Jeremić, S., Amić, A., Stanojević-Pirković, M., Marković, Z.: Selected anthraquinones as potential free radical scavengers and P-glycoprotein inhibitors. Org. Biomol. Chem. 16(11), 1890–1902 (2018)
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This work was supported by the Ministry of Education, Science and Technological Development of the Republic of Serbia (Projects No. 172015 and 174028).
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Jeremić, S., Marković, Z. (2020). Free Radical Scavenger Activity and P-glycoprotein Inhibition Capacity of 1,2,4-Trihydroxyxanthone. In: Filipovic, N. (eds) Computational Bioengineering and Bioinformatics. ICCB 2019. Learning and Analytics in Intelligent Systems, vol 11. Springer, Cham. https://doi.org/10.1007/978-3-030-43658-2_9
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DOI: https://doi.org/10.1007/978-3-030-43658-2_9
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