Published September 30, 2021
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A detailed DFT-based study of the free radical scavenging activity and mechanism of daphnetin in physiological environments
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Boulebd, Houssem, Khodja, Imene Amine (2021): A detailed DFT-based study of the free radical scavenging activity and mechanism of daphnetin in physiological environments. Phytochemistry (112831) 189: 1-7, DOI: 10.1016/j.phytochem.2021.112831, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112831
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References
- Alberto, M.E., Russo, N., Grand, A., Galano, A., 2013. A physicochemical examination of the free radical scavenging activity of Trolox: mechanism, kinetics and influence of the environment. Phys. Chem. Chem. Phys. 15, 4642-4650. https://doi.org/ 10.1039/C3CP43319F.
- Amine Khodja, I., Boulebd, H., 2020. Synthesis, biological evaluation, theoretical investigations, docking study and ADME parameters of some 1,4- bisphenylhydrazone derivatives as potent antioxidant agents and acetylcholinesterase inhibitors. Mol. Divers. 25, 279-290. https://doi.org/10.1007/ s11030-020-10064-8.
- Amine Khodja, I., Boulebd, H., Bensouici, C., Belfaitah, A., 2020. Design, synthesis, biological evaluation, molecular docking, DFT calculations and in silico ADME analysis of (benz)imidazole-hydrazone derivatives as promising antioxidant, antifungal, and anti-acetylcholinesterase agents. J. Mol. Struct. 1218, 128527 https://doi.org/10.1016/j.molstruc.2020.128527.
- Atala, E., Fuentes, J., Wehrhahn, M.J., Speisky, H., 2017. Quercetin and related flavonoids conserve their antioxidant properties despite undergoing chemical or enzymatic oxidation. Food Chem. 234, 479-485. https://doi.org/10.1016/j. foodchem.2017.05.023.
- Barnham, K.J., Masters, C.L., Bush, A.I., 2004. Neurodegenerative diseases and oxidative stress. Nat. Rev. Drug Discov. 3, 205-214. https://doi.org/10.1038/nrd1330.
- Boulebd, H., 2020. Theoretical insights into the antioxidant activity of moracin T. Free Radic. Res. 54, 221-230. https://doi.org/10.1080/10715762.2020.1747616.
- Boulebd, H., 2021. Are thymol, rosefuran, terpinolene and umbelliferone good scavengers of peroxyl radicals? Phytochemistry 184, 112670. https://doi.org/ 10.1016/j.phytochem.2021.112670.
- Boulebd, H., Amine Khodja, I., Bay, M.V., Hoa, N.T., Mechler, A., Vo, Q.V., 2020a. Thermodynamic and kinetic studies of the radical scavenging behavior of hydralazine and dihydralazine: theoretical insights. J. Phys. Chem. B 124, 4123-4131. https://doi.org/10.1021/acs.jpcb.0c02439.
- Boulebd, H., Mechler, A., Hoa, N.T., Vo, Q.V., 2020b. Thermodynamic and kinetic studies of the antiradical activity of 5-hydroxymethylfurfural: computational insights. New J. Chem. 44, 9863-9869. https://doi.org/10.1039/D0NJ01567A.
- Boulebd, H., Tam, N.M., Mechler, A., Vo, Q.V., 2020c. Substitution effects on the antiradical activity of hydralazine: a DFT analysis. New J. Chem. 44, 16577-16583. https://doi.org/10.1039/D0NJ03753B.
- Burton, G.J., Jauniaux, E., 2011. Oxidative stress. Best Pract. Res. Clin. Obstet. Gynaecol. 25, 287-299. https://doi.org/10.1016/j.bpobgyn.2010.10.016.
- Chen, J., Liu, X., Shi, Y.-P., 2004. Determination of daphnetin in Daphne tangutica and its medicinal preparation by liquid chromatography. Anal. Chim. Acta 523, 29-33.
- Collins, F.C., Kimball, G.E., 1949. Diffusion-controlled reaction rates. J. Colloid Sci. 4, 425-437. https://doi.org/10.1016/0095-8522(49)90023-9.
- Corchado, J.C., Coitino, E.L., Chuang, Y.-Y., Fast, P.L., Truhlar, D.G., 1998. Interpolated variational transition-state theory by mapping. J. Phys. Chem. 102, 2424-2438. https://doi.org/10.1021/jp9801267.
- Cottigli, F., Loy, G., Garau, D., Floris, C., Caus, M., Pompei, R., Bonsignore, L., 2001. Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L. Phytomedicine 8, 302-305. https://doi.org/10.1078/0944-7113-00036.
- Dhiman, P., Malik, N., Khatkar, A., Kulharia, M., 2017. Antioxidant, xanthine oxidase and monoamine oxidase inhibitory potential of coumarins: a review. Curr. Org. Chem. 21, 294-304.
- Dzib, E., Cabellos, J.L., Ortiz-Chi, F., Pan, S., Galano, A., Merino, G., 2019. Eyringpy: a program for computing rate constants in the gas phase and in solution. Int. J. Quant. Chem. 119, e25686 https://doi.org/10.1002/qua.25686.
- Eckart, C., 1930. The penetration of a potential barrier by electrons. Phys. Rev. 35, 1303. https://doi.org/10.1103/PhysRev.35.1303.
- Evans, M.G., Polanyi, M., 1935. Some applications of the transition state method to the calculation of reaction velocities, especially in solution. Trans. Faraday Soc. 31, 875-894. https://doi.org/10.1039/TF9353100875.
- Eyring, H., 1935. The activated complex in chemical reactions. J. Chem. Phys. 3, 107-115. https://doi.org/10.1063/1.1749604.
- Fang, Y.-Z., Yang, S., Wu, G., 2002. Free radicals, antioxidants, and nutrition. Nutrition 18, 872-879. https://doi.org/10.1016/S0899-9007(02)00916-4.
- Fern´andez-Ramos, A., Ellingson, B.A., Meana-Paneda t, R., Marques, J.M., Truhlar, D.G., 2007. Symmetry numbers and chemical reaction rates. Theor. Chem. Accounts 118, 813-826. https://doi.org/10.1007/s00214-007-0328-0.
- Filipsky, T., Riha, M., Macakova, K., Anzenbacherov´a, E., Karlickova, J., Mladenka, P., 2015. Antioxidant effects of coumarins include direct radical scavenging, metal chelation and inhibition of ROS-producing enzymes. Curr. Top. Med. Chem. 15, 415-431. https://doi.org/10.2174/1568026615666150206152233.
- Finn, G.J., Kenealy, E., Creaven, B.S., Egan, D.A., 2002. In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines. Canc. Lett. 183, 61-68.
- Finn, G.J., Creaven, B.S., Egan, D.A., 2004. Daphnetin induced differentiation of human renal carcinoma cells and its mediation by p38 mitogen-activated protein kinase. Biochem. Pharmacol. 67, 1779-1788. https://doi.org/10.1016/j.bcp.2004.01.014.
- Kobayashi, R., Normand, J., Rendell, K.R.A.P., Burant, J.C., Iyengar, S.S., Cossi, J.T. M., Rega, N., Millam, N.J., Klene, M., Cross, J.E.K.J.B., Bakken, V., Adamo, C., Jaramillo, J., Stratmann, R.G.R.E., Yazyev, O., Austin, A.J., Pomelli, R.C.C., Ochterski, J.W., Martin, R.L., Zakrzewski, K.M.V.G., Voth, G.A., Salvador, P., Dapprich, J.J.D.S., Daniels, A.D., Farkas, O., Ortiz, J.B.F.J.V., Cioslowski, J., Fox, D. J., 2009. Gaussian 09. Gaussian, Inc., Wallingford CT.
- Fukui, K., 1981. The path of chemical reactions - the IRC approach. Accounts Chem. Res. 14, 363-368. https://doi.org/10.1021/ar00072a001.
- Furuncuoglu, T., Ugur, I., Degirmenci, I., Aviyente, V., 2010. Role of chain transfer agents in free radical polymerization kinetics. Macromolecules 43, 1823-1835. https://doi.org/10.1021/ma902803p.
- Fylaktakidou, K.C., Hadjipavlou-Litina, D.J., Litinas, K.E., Nicolaides, D.N., 2004. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities. Curr. Pharmaceut. Des. 10, 3813-3833.
- Galano, A., Alvarez-Idaboy, J.R., 2014. Kinetics of radical-molecule reactions in aqueous solution: a benchmark study of the performance of density functional methods. J. Comput. Chem. 35, 2019-2026. https://doi.org/10.1002/jcc.23715.
- Galano, A., Alvarez-Idaboy, J.R., 2013. A computational methodology for accurate predictions of rate constants in solution: application to the assessment of primary antioxidant activity. J. Comput. Chem. 34, 2430-2445. https://doi.org/10.1002/ jcc.23409.
- Galano, A., Alvarez-Idaboy, J.R., 2019. Computational strategies for predicting free radical scavengers' protection against oxidative stress: where are we and what might follow? Int. J. Quant. Chem. 119, e25665 https://doi.org/10.1002/qua.25665.
- Galano, A., Alvarez-Idaboy, J.R., Francisco-M´arquez, M., 2011. Physicochemical insights on the free radical scavenging activity of sesamol: importance of the acid/base equilibrium. J. Phys. Chem. B 115, 13101-13109. https://doi.org/10.1021/ jp208315k.
- Galano, A., Alvarez-Idaboy, J.R., Francisco-M´arquez, M., Medina, M.E., 2012. A quantum chemical study on the free radical scavenging activity of tyrosol and hydroxytyrosol. Theor. Chem. Accounts 131, 1173. https://doi.org/10.1007/s00214-012-1173-3.
- Galano, A., Mazzone, G., Alvarez-Diduk, R., Marino, T., Alvarez-Idaboy, J.R., Russo, N., 2016a. Food antioxidants: chemical insights at the molecular level. Annu. Rev. Food Sci. Technol. 7, 335-352. https://doi.org/10.1146/annurev-food-041715-033206.
- Galano, A., Mazzone, G., Alvarez-Diduk, R., Marino, T., Alvarez-Idaboy, J.R., Russo, N., 2016b. Food antioxidants: chemical insights at the molecular level. Annu. Rev. Food Sci. Technol. 7, 335-352. https://doi.org/10.1146/annurev-food-041715-033206.
- Halliwell, B., 1996. Antioxidants in human health and disease. Annu. Rev. Nutr. 16, 33-50. https://doi.org/10.1146/annurev.nu.16.070196.000341.
- Hoult, J.R.S., Forder, R.A., de las Heras, B., Lobo, I.B., Pay´a, M., 1994. Inhibitory activity of a series of coumarins on leukocyte eicosanoid generation. Agents Actions 42, 44-49.
- Iuga, C., Alvarez-Idaboy, J.R.l., Russo, N., 2012. Antioxidant activity of trans-resveratrol toward hydroxyl and hydroperoxyl radicals: a quantum chemical and computational kinetics study. J. Org. Chem. 77, 3868-3877. https://doi.org/10.1021/jo3002134.
- Kostova, I., Bhatia, S., Grigorov, P., Balkansky, S., Parmar, V.S., Prasad, A.K., Saso, L., 2011. Coumarins as antioxidants. Curr. Med. Chem. 18, 3929-3951.
- Krishnan, R., Binkley, J.S., Seeger, R., Pople, J.A., 1980. Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J. Chem. Phys. 72, 650-654. https://doi.org/10.1063/1.438955.
- Le´on-Carmona, J.R., Galano, A., 2011. Is caffeine a good scavenger of oxygenated free radicals? J. Phys. Chem. B 115, 4538-4546. https://doi.org/10.1021/jp201383y.
- Leopoldini, M., Russo, N., Toscano, M., 2011. The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem. 125, 288-306. https://doi.org/ 10.1016/j.foodchem.2010.08.012.
- Lu, Y., Wang, A., Shi, P., Zhang, H., Li, Z., 2016. Kinetic reaction mechanism of sinapic acid scavenging NO2 and OH radicals: a theoretical study. PloS One 11, e0162729. https://doi.org/10.1371/journal.pone.0162729.
- Marenich, A.V., Cramer, C.J., Truhlar, D.G., 2009. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J. Phys. Chem. B 113, 6378-6396. https://doi.org/10.1021/jp810292n.
- Maritim, A.C., Sanders, a., Watkins Iii, J.B., 2003. Diabetes, oxidative stress, and antioxidants: a review. J. Biochem. Mol. Toxicol. 17, 24-38. https://doi.org/ 10.1002/jbt.10058.
- Mittler, R., 2017. ROS are good. Trends Plant Sci. 22, 11-19. https://doi.org/10.1016/j. tplants.2016.08.002.
- Moldogazieva, N.T., Mokhosoev, I.M., Feldman, N.B., Lutsenko, S.V., 2018. ROS and RNS signalling: adaptive redox switches through oxidative/nitrosative protein modifications. Free Radic. Res. 52, 507-543. https://doi.org/10.1080/ 10715762.2018.1457217.
- Nanzhen, K., Jieying, W., Wenwei, Z., Xiaoping, Z., Yingyuan, F., 2018. Toxicological Studies of Daphnetin. Pharmacognosy Magazine, vol. 14, p. 561.
- Nasipuri, R., Ramstad, E., 1973. Isolation of Daphnetin-8-β- Glucoside from Daphne Papyracea. Journal of Pharmaceutical Sciences, vol. 62, pp. 1359-1360.
- Niwa, M., Sugino, H., Takashima, S., Sakai, T., Wu, Y.-C., Wu, T.-S., Kuoh, C.-S., 1991. A new coumarin glucoside from Daphne arisanensis. Chem. Pharm. Bull. 39, 2422-2424. https://doi.org/10.1248/cpb.39.2422.
- Pinto, D.C.G.A., Silva, A., 2017. Anticancer natural coumarins as lead compounds for the discovery of new drugs. Curr. Top. Med. Chem. 17, 3190-3198.
- Pisoschi, A.M., Pop, A., 2015. The role of antioxidants in the chemistry of oxidative stress: a review. Eur. J. Med. Chem. 97, 55-74.
- Pollak, E., Pechukas, P., 1978. Symmetry numbers, not statistical factors, should be used in absolute rate theory and in Broensted relations. J. Am. Chem. Soc. 100, 2984-2991. https://doi.org/10.1021/ja00478a009.
- Raghavan, N.V., Steenken, S., 1980. Electrophilic reaction of the hydroxyl radical with phenol. Determination of the distribution of isomeric dihydroxycyclohexadienyl radicals. J. Am. Chem. Soc. 102, 3495-3499. https://doi.org/10.1021/ja00530a031.
- Rasouli, H., Farzaei, M.H., Khodarahmi, R., 2017. Polyphenols and their benefits: a review. Int. J. Food Prop. 20, 1700-1741. https://doi.org/10.1080/ 10942912.2017.1354017.
- Reuter, S., Gupta, S.C., Chaturvedi, M.M., Aggarwal, B.B., 2010. Oxidative stress, inflammation, and cancer: how are they linked? Free Radic. Biol. Med. 49, 1603-1616. https://doi.org/10.1016/j.freeradbiomed.2010.09.006.
- Roder, M., Wojn´arovits, L., F¨oldi´ak, G., Emmi, S.S., Beggiato, G., D' Angelantonio, M., 1999. Addition and elimination kinetics in OH radical induced oxidation of phenol and cresols in acidic and alkaline solutions. Radiat. Phys. Chem. 54, 475-479. https://doi.org/10.1016/S0969-806X(98)00294-1.
- Sauerwald, N., Schwenk, M., Polster, J., Bengsch, E., 1998. Spectrometric pK determination of daphnetin, chlorogenic acid and quercetin. Z. Naturforsch. B Chem. Sci. 53, 315-321. https://doi.org/10.1515/znb-1998-0310.
- Shan, J.-j., Di, L.-q., Zhao, X.-l., Xu, J.-y., 2011. Determination of equilibrium solubility and apparent oil/water partition coefficient of daphnetin [J]. J. Nanjing. Univ. Tradit. Chin. Med. 27, 449-450.
- Shang, Y., Zhou, H., Li, X., Zhou, J., Chen, K., 2019. Theoretical studies on the antioxidant activity of viniferifuran. New J. Chem. 43, 15736-15742. https://doi. org/10.1039/C9NJ02735A.
- Shen, L., Zhou, T., Wang, J., Sang, X., Lan, L., Luo, L., Yin, Z., 2017. Daphnetin reduces endotoxin lethality in mice and decreases LPS-induced inflammation. In: Raw 264. 7 Cells via Suppressing JAK/STATs Activation and ROS Production. Inflammation Research 66, pp. 579-589.
- Thuong, P.T., Hung, T.M., Ngoc, T.M., Ha, D.T., Min, B.S., Kwack, S.J., Kang, T.S., Choi, J.S., Bae, K., 2010. Antioxidant activities of coumarins from Korean medicinal plants and their structure-activity relationships. Phytother Res. 24, 101-106. https://doi.org/10.1002/ptr.2890.
- Truhlar, D.G., Hase, W.L., Hynes, J.T., 1983. Current status of transition-state theory. J. Phys. Chem. 87, 2664-2682. https://doi.org/10.1021/jp953748q.
- Uc, V.H., Alvarez-Idaboy, J.R., Galano, A., Vivier-Bunge, A., 2008. Theoretical explanation of nonexponential OH decay in reactions with benzene and toluene under pseudo-first-order conditions. J. Phys. Chem. 112, 7608-7615. https://doi. org/10.1021/jp8026258.
- V´asquez-Espinal, A., Yatnez, O., Osorio, E., Areche, C., Garcia-Beltr´an, O., Ruiz, L.M., Cassels, B.K., Tiznado, W., 2019. Theoretical study of the antioxidant activity of quercetin oxidation products. Front. Chem. 7, 818. https://doi.org/10.3389/ fchem.2019.00818.
- V´elez, E., Quijano, J., Notario, R., Pab´on, E., Murillo, J., Leal, J., Zapata, E., Alarc´on, G., 2009. A computational study of stereospecifity in the thermal elimination reaction of menthyl benzoate in the gas phase. J. Phys. Org. Chem. 22, 971-977. https://doi. org/10.1002/poc.1547.
- Vo, Q.V., Bay, M.V., Nam, P.C., Quang, D.T., Flavel, M., Hoa, N.T., Mechler, A., 2020. Theoretical and experimental studies of the antioxidant and antinitrosant activity of syringic acid. J. Org. Chem. 85, 15514-15520. https://doi.org/10.1021/acs. joc.0c02258.
- Witaicenis, A., Seito, L.N., da Silveira Chagas, A., de Almeida Junior, L.D., Luchini, A.C., Rodrigues-Orsi, P., Cestari, S.H., Di Stasi, L.C., 2014. Antioxidant and intestinal anti-inflammatory effects of plant-derived coumarin derivatives. Phytomedicine 21, 240-246.
- Xia, Y., Chen, C., Liu, Y., Ge, G., Dou, T., Wang, P., 2018. Synthesis and structure-activity relationship of daphnetin derivatives as potent antioxidant agents. Molecules 23, 2476. https://doi.org/10.3390/molecules23102476.
- Xue, Y., Liu, Y., Luo, Q., Wang, H., Chen, R., Liu, Y., Li, Y., 2018. Antiradical activity and mechanism of coumarin-chalcone hybrids: theoretical insights. J. Phys. Chem. 122, 8520-8529. https://doi.org/10.1021/acs.jpca.8b06787.
- Xue, Y., Liu, Y., Xie, Y., Cong, C., Wang, G., An, L., Teng, Y., Chen, M., Zhang, L., 2020. Antioxidant activity and mechanism of dihydrochalcone C-glycosides: effects of Cglycosylation and hydroxyl groups. Phytochemistry 179, 112393. https://doi.org/ 10.1016/j.phytochem.2020.112393.
- Yadav, A., Kumari, R., Yadav, A., Mishra, J.P., Srivatva, S., Prabha, S., 2016. Antioxidants and its functions in human body-A Review. Res. Environ. Life Sci. 9, 1328-1331.
- Yang, Y.-Z., Ranz, A., Pan, H.-Z., Zhang, Z.-N., Lin, X.-B., Meshnick, S.R., 1992. Daphnetin: a novel antimalarial agent with in vitro and in vivo activity. Am. J. Trop. Med. Hyg. 46, 15-20. https://doi.org/10.4269/ajtmh.1992.46.15.
- Yu, W.-w., Lu, Z., Zhang, H., Kang, Y.-h., Mao, Y., Wang, H.-h., Ge, W.-h., Shi, L.-y., 2014. Anti-inflammatory and protective properties of daphnetin in endotoxin-induced lung injury. J. Agric. Food Chem. 62, 12315-12325.
- Zhao, Y., Truhlar, D.G., 2008. How well can new-generation density functionals describe the energetics of bond-dissociation reactions producing radicals? J. Phys. Chem. 112, 1095-1099. https://doi.org/10.1021/jp7109127.
- Zhao, Y., Schultz, N.E., Truhlar, D.G., 2006a. Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J. Chem. Theor. Comput. 2, 364-382. https://doi.org/10.1021/ct0502763.
- Zhao, Y., Schultz, N.E., Truhlar, D.G., 2006b. Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J. Chem. Theor. Comput. 2, 364-382. https://doi.org/10.1021/ct0502763.
- Zobel, A.M., Brown, S.A., 1989. Localization of daphnetin and umbelliferone in different tissues of Daphne mezereum shoots. Can. J. Bot. 67, 1456-1459.