The radical scavenger capacity and mechanism of prenylated coumestan-type compounds: a DFT analysis

References

• Sies H. On the history of oxidative stress: concept and some aspects of current development. Curr Opin Toxicol. 2018;7:122–126.
   Google Scholar
• Umeno A, Biju V, Yoshida Y. In vivo ROS production and use of oxidative stress-derived biomarkers to detect the onset of diseases such as Alzheimer's disease, Parkinson's disease, and diabetes. Free Radic Res. 2017;51(4):413–427.
   PubMed Web of Science ®Google Scholar
• Harrison DG, Gongora MC. Oxidative stress and hypertension. Med Clin North Am. 2009;93(3):621–635.
   PubMed Web of Science ®Google Scholar
• Sosa V, Moliné T, Somoza R, et al. Oxidative stress and cancer: an overview. Ageing Res Rev. 2013;12(1):376–390.
   PubMed Web of Science ®Google Scholar
• Niedowicz DM, Daleke DL. The role of oxidative stress in diabetic complications. Cell Biochem Biophys. 2005;43(2):289–330.
   PubMed Web of Science ®Google Scholar
• Singh A, Kukreti R, Saso L, et al. Oxidative stress: a key modulator in neurodegenerative diseases. Molecules. 2019;24(8):1583.
   PubMed Web of Science ®Google Scholar
• Pisoschi AM, Pop A. The role of antioxidants in the chemistry of oxidative stress: a review. Eur J Med Chem. 2015;97:55–74.
   PubMed Web of Science ®Google Scholar
• Rasouli H, Farzaei MH, Khodarahmi R. Polyphenols and their benefits: a review. Int J Food Prop. 2017;20(sup2):1–1741.
   Google Scholar
• Wang G, Xue Y, An L, et al. Theoretical study on the structural and antioxidant properties of some recently synthesised 2,4,5-trimethoxy chalcones. Food Chem. 2015;171:89–97.
   PubMed Web of Science ®Google Scholar
• Amine Khodja I, Boulebd H. 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. 2021;25(1):279–290.
   PubMedGoogle Scholar
• Tu Y, Yang Y, Li Y, et al. Naturally occurring coumestans from plants, their biological activities and therapeutic effects on human diseases. Pharmacol Res. 2021;169:105615.
   PubMedGoogle Scholar
• Williams CA, Harborne JB. 12 – Isoflavonoids. In: Harborne JB, editor. Methods in plant biochemistry. Vol. 1: Academic Press; 1989. p. 421–449.doi:https://doi.org/10.1016/B978-0-12-461011-8.50018-4.
   Google Scholar
• Yang X, Jiang Y, Yang J, et al. Prenylated flavonoids, promising nutraceuticals with impressive biological activities. Trends in Food Science & Technology. 2015;44(1):93–104.
   Web of Science ®Google Scholar
• Chen X, Mukwaya E, Wong M-S, et al. A systematic review on biological activities of prenylated flavonoids. Pharm Biol. 2014;52(5):655–660.
   PubMed Web of Science ®Google Scholar
• Simons R, Gruppen H, Bovee TFH, et al. Prenylated isoflavonoids from plants as selective estrogen receptor modulators (phytoSERMs). Food Funct. 2012;3(8):810–827.
   PubMed Web of Science ®Google Scholar
• Araya-Cloutier C, Vincken J-P, van de Schans MGM, et al. QSAR-based molecular signatures of prenylated (iso)flavonoids underlying antimicrobial potency against and membrane-disruption in gram positive and gram negative bacteria. Sci Rep. 2018;8(1):9267.
   PubMedGoogle Scholar
• Venturelli S, Burkard M, Biendl M, et al. Prenylated chalcones and flavonoids for the prevention and treatment of cancer. Nutrition. 2016;32(11–12):1171–1178.
   PubMed Web of Science ®Google Scholar
• Jiang M-Y, Luo M, Tian K, et al. α-Glucosidase inhibitory and anti-inflammatory coumestans from the roots of dolichos trilobus. Planta Med. 2019;85(2):112–117.
   PubMed Web of Science ®Google Scholar
• Galano A, Alvarez-Idaboy JR. Kinetics of radical-molecule reactions in aqueous solution: a benchmark study of the performance of density functional methods. J Comput Chem. 2014;35(28):2019–2026.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Truhlar DG. How well can new-generation density functionals describe the energetics of bond-dissociation reactions producing radicals? J Phys Chem A. 2008;112(6):1095–1099.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Schultz NE, Truhlar DG. Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J Chem Theory Comput. 2006;2(2):364–382.
   PubMed Web of Science ®Google Scholar
• Marenich AV, Cramer CJ, Truhlar DG. 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. 2009;113(18):6378–6396.
   PubMed Web of Science ®Google Scholar
• Martins SA, Sousa SF. Comparative assessment of computational methods for the determination of solvation free energies in alcohol-based molecules. J Comput Chem. 2013;34(15):1354–1362.
   PubMedGoogle Scholar
• Galano A, Alvarez‐Idaboy JR. A computational methodology for accurate predictions of rate constants in solution: application to the assessment of primary antioxidant activity. J Comput Chem. 2013;34(28):2430–2445.
   PubMedGoogle Scholar
• Galano A, Alvarez-Idaboy JR. Computational strategies for predicting free radical scavengers' protection against oxidative stress: where are we and what might follow? Int J Quantum Chem. 2019;119(2):e25665.
   Web of Science ®Google Scholar
• Boulebd H. Are thymol, rosefuran, terpinolene and umbelliferone good scavengers of peroxyl radicals?. Phytochemistry. 2021;184:112670.
   PubMed Web of Science ®Google Scholar
• Boulebd H, Tam NM, Mechler A, et al. Substitution effects on the antiradical activity of hydralazine: a DFT analysis. New J Chem. 2020;44(38):16577–16583.
   Web of Science ®Google Scholar
• Chiodo SG, Leopoldini M, Russo N, et al. The inactivation of lipid peroxide radical by quercetin. A theoretical insight. Phys Chem Chem Phys. 2010;12(27):7662–7670.
   PubMedGoogle Scholar
• Evans MG, Polanyi M. Some applications of the transition state method to the calculation of reaction velocities, especially in solution. Trans Faraday Soc. 1935;31:875–894.
   Google Scholar
• Eyring H. The activated complex in chemical reactions. J Chem Phys. 1935;3(2):107–115.
   Google Scholar
• Truhlar DG, Hase WL, Hynes JT. Current status of transition-state theory. J Phys Chem. 1983;87(15):2664–2682.
   Google Scholar
• Furuncuoglu T, Ugur I, Degirmenci I, et al. Role of chain transfer agents in free radical polymerization kinetics. Macromolecules. 2010;43(4):1823–1835.
   Web of Science ®Google Scholar
• Vélez E, Quijano J, Notario R, et al. A computational study of stereospecifity in the thermal elimination reaction of menthyl benzoate in the gas phase. J Phys Org Chem. 2009;22(10):971–977.
   Google Scholar
• Pollak E, Pechukas P. Symmetry numbers, not statistical factors, should be used in absolute rate theory and in broensted relations. J Am Chem Soc. 1978;100(10):2984–2991.
   Google Scholar
• Fernández-Ramos A, Ellingson BA, Meana-Pañeda R, et al. Symmetry numbers and chemical reaction rates. Theor Chem Account. 2007;118(4):813–826.
   Google Scholar
• Eckart C. The penetration of a potential barrier by electrons. Phys Rev. 1930;35(11):1303–1309.
   Google Scholar
• Collins FC, Kimball GE. Diffusion-controlled reaction rates. J Colloid Sci. 1949;4(4):425–437.
   Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09 [computer program]. Wallingford, CT: 2009.
   Google Scholar
• Dzib E, Cabellos JL, Ortíz‐Chi F, et al. Eyringpy: a program for computing rate constants in the gas phase and in solution. Int J Quantum Chem. 2019;119(2):e25686.
   Google Scholar
• Boulebd H, Lahneche YD, Khodja IA, et al. New schiff bases derived from benzimidazole as efficient mercury-complexing agents in aqueous medium. J Mol Struct. 2019;1196:58–65.
   Web of Science ®Google Scholar
• Leopoldini M, Russo N, Toscano M. The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem. 2011;125(2):288–306.
   Web of Science ®Google Scholar
• Galano A, Mazzone G, Alvarez-Diduk R, et al. Food antioxidants: chemical insights at the molecular level. Annu Rev Food Sci Technol. 2016;7(1):335–352.
   PubMedGoogle Scholar
• Mayer JM, Hrovat DA, Thomas JL, et al. Proton-coupled electron transfer versus hydrogen atom transfer in benzyl/toluene, methoxyl/methanol, and phenoxyl/phenol self-exchange reactions. J Am Chem Soc. 2002;124(37):11142–11147.
   PubMed Web of Science ®Google Scholar
• Hammes-Schiffer S. Proton-coupled electron transfer: classification scheme and guide to theoretical methods. Energy Environ Sci. 2012;5(7):7696–7703.
   Google Scholar
• Hammes-Schiffer S. Theoretical perspectives on proton-coupled electron transfer reactions. Acc Chem Res. 2001;34(4):273–281.
   PubMedGoogle Scholar
• Boulebd H. Radical scavenging behavior of butylated hydroxytoluene against oxygenated free radicals in physiological environments: insights from DFT calculations. Int J Chem Kinet. 2022;54(1):50–57.
   Google Scholar
• Leopoldini M, Chiodo SG, Russo N, et al. Detailed investigation of the OH radical quenching by natural antioxidant caffeic acid studied by quantum mechanical models. J Chem Theory Comput. 2011;7(12):4218–4233.
   PubMed Web of Science ®Google Scholar
• Xue Y, Liu Y, Xie Y, et al. Antioxidant activity and mechanism of dihydrochalcone C-glycosides: effects of C-glycosylation and hydroxyl groups. Phytochemistry. 2020;179:112393.
   PubMed Web of Science ®Google Scholar
• Boulebd H. Modeling the peroxyl radical scavenging behavior of carnosic acid: mechanism, kinetics, and effects of physiological environments. Phytochemistry. 2021;192:112950.
   PubMed Web of Science ®Google Scholar
• Boulebd H, Amine Khodja I. Amine khodja I. A detailed DFT-based study of the free radical scavenging activity and mechanism of daphnetin in physiological environments. Phytochemistry. 2021;189:112831.
   PubMed Web of Science ®Google Scholar
• Boulebd H. Is cannabidiolic acid an overlooked natural antioxidant? Insights from quantum chemistry calculations. New J Chem. 2022;46(1):162–168.
   Google Scholar
• Vo QV, Tam NM, Hieu LT, et al. The antioxidant activity of natural diterpenes: theoretical insights. RSC Adv. 2020;10(25):14937–14943.
   PubMed Web of Science ®Google Scholar
• Boulebd H, Mechler A, Hoa NT, et al. Insights into the mechanisms and kinetics of the hydroperoxyl radical scavenging activity of artepillin C. New J Chem. 2021;45(17):7774–7780.
   Google Scholar
• Galano A. Free radicals induced oxidative stress at a molecular level: the current status, challenges and perspectives of computational chemistry based protocols. J Mex Chem Soc. 2015;59:231–262.
   Web of Science ®Google Scholar
• Anouar EH, Shah SAA, Hassan NB, et al. Antioxidant activity of hispidin oligomers from medicinal fungi: a DFT study. Molecules. 2014;19(3):3489–3507.
   PubMedGoogle Scholar