Recent advances in the antioxidant activity and mechanisms of chalcone derivatives: a computational review

References

• Mittal A, Devi SP, Kakkar R. A DFT study of the conformational and electronic properties of echinatin, a retrochalcone, and its anion in the gas phase and aqueous solution. Struct Chem. 2020;31(6):2513–2524.
   Web of Science ®Google Scholar
• Mittal A, Kakkar R. A theoretical assessment of the structural and electronic features of some retrochalcones. Int J Quantum Chem. 2021;121(24):e26797.
   Web of Science ®Google Scholar
• Panche AN, Diwan AD, Chandra SR. Flavonoids: an overview. J Nutr Sci. 2016;5:e47.
   PubMed Web of Science ®Google Scholar
• Zhou K, Yang S, Li SM. Naturally occurring prenylated chalcones from plants: structural diversity, distribution, activities and biosynthesis. Nat Prod Rep. 2021;38(12):2236–2260.
   PubMed Web of Science ®Google Scholar
• Michalkova R, Mirossay L, Gazdova M, et al. Molecular mechanisms of antiproliferative effects of natural chalcones. Cancers. 2021;13(11):2730.
   PubMed Web of Science ®Google Scholar
• Rudrapal M, Khan J, Dukhyil AAB, et al. Chalcone scaffolds, bioprecursors of flavonoids: chemistry, bioactivities, and pharmacokinetics. Molecules. 2021;26(23):7177.
   PubMed Web of Science ®Google Scholar
• Murti Y, Goswam A, Mishra P. Synthesis and antioxidant activity of some chalcones and flavanoids. Inter J Pharm Tech Res. 2013;5:811–818.
   Google Scholar
• Murti Y, Pathak D, Pathak K. Green chemistry approaches to the synthesis of flavonoids. COC. 2021;25(17):2005–2027.
   Google Scholar
• Gupta J, Gupta R, Varshney B. Green approaches of flavonoids in cancer: chemistry, applications, management, healthcare and future perspectives. JPRI. 2021;33(59A):130–143.
   Google Scholar
• Rammohan A, Reddy JS, Sravya G, et al. Chalcone synthesis, properties and medicinal applications: a review. Environ Chem Lett. 2020;18(2):433–458.
   Web of Science ®Google Scholar
• Mittal A, Kakkar R. Synthetic methods and biological applications of retrochalcones isolated from the root of glycyrrhiza species: a review. Results Chem. 2021;3:100216.
   Google Scholar
• Cao Y, Xu W, Huang Y, et al. Licochalcone B, a chalcone derivative from glycyrrhiza inflata, as a multifunctional agent for the treatment of Alzheimer’s disease. Nat Prod Res. 2020;34(5):736–739.
   PubMed Web of Science ®Google Scholar
• Shrivastava A, Gupta JK, Goyal MK. Flavonoids and antiepileptic drugs: a comprehensive review on their neuroprotective potentials. JMPAS. 2022;11(1):4179–4186.
   Google Scholar
• Jasim HA, Nahar L, Jasim MA, et al. Chalcones: synthetic chemistry follows where nature leads. Biomolecules. 2021;11(8):1203.
   PubMed Web of Science ®Google Scholar
• Farhadi F, Khameneh B, Iranshahi M, et al. Antibacterial activity of flavonoids and their structure–activity relationship: an update review. Phytother Res. 2019;33(1):13–40.
   PubMed Web of Science ®Google Scholar
• Maria Pia GD, Sara F, Mario F, et al. Biological effects of licochalcones. Mini Rev Med Chem. 2019;19(8):647–656.
   PubMed Web of Science ®Google Scholar
• Zhang Z, Yang L, Hou J, et al. Molecular mechanisms underlying the anticancer activities of licorice flavonoids. J Ethnopharmacol. 2021;267:113635.
   PubMed Web of Science ®Google Scholar
• Elkhalifa D, Al-Hashimi I, Al-Moustafa AE, et al. A comprehensive review on the antiviral activities of chalcones. J Drug Target. 2021;29(4):403–419.
   PubMed Web of Science ®Google Scholar
• Nordberg J, Arner ES. Reactive oxygen species, antioxidants, and the mammalian thioredoxin system. Free Radic Biol Med. 2001;31(11):1287–1312.
   PubMed Web of Science ®Google Scholar
• Valko M, Leibfritz D, Moncol J, et al. Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol. 2007;39(1):44–84.
   PubMed Web of Science ®Google Scholar
• Ahmed OM, Mohammed MT. Oxidative stress: the role of reactive oxygen species (ROS) and antioxidants in human diseases. Plant Arch. 2020;20:4089–4095.
   Google Scholar
• Hameister R, Kaur C, Dheen ST, et al. Reactive oxygen/nitrogen species (ROS/RNS) and oxidative stress in arthroplasty. J Biomed Mater Res B Appl Biomater. 2020;108(5):2073–2087.
   PubMed Web of Science ®Google Scholar
• Sies H, Berndt C, Jones DP. Oxidative stress. Annu Rev Biochem. 2017;86:715–748.
   PubMed Web of Science ®Google Scholar
• Shlapakova TI, Kostin RK, Tyagunova EE. Reactive oxygen species: participation in cellular processes and progression of pathology. Russ J Bioorg Chem. 2020;46(5):657–674.
   Web of Science ®Google Scholar
• Kapoor D, Singh S, Kumar V, et al. Antioxidant enzymes regulation in plants in reference to reactive oxygen species (ROS) and reactive nitrogen species (RNS). Plant Gene. 2019;19:100182.
   Google Scholar
• Ifeanyi OE. A review on free radicals and antioxidants. Int J Curr Res Med Sci. 2018;4(2):123–133.
   Google Scholar
• Turkan I. ROS and RNS: key signalling molecules in plants. J Exp Bot. 2018;69(14):3313–3315.
   PubMed Web of Science ®Google Scholar
• Giles GI, Jacob C. Reactive sulfur species: an emerging concept in oxidative stress. De Gruyter. 2002;383:375–388.
   Google Scholar
• Galano A, Raúl Alvarez‐Idaboy J. 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
• Ferreira CA, Ni D, Rosenkrans ZT, et al. Scavenging of reactive oxygen and nitrogen species with nanomaterials. Nano Res. 2018;11(10):4955–4984.
   PubMed Web of Science ®Google Scholar
• Manahan SE. Toxicological chemistry and biochemistry. Boca Raton, Florida: CRC Press; 2002.
   Google Scholar
• Gruhlke MC, Slusarenko AJ. The biology of reactive sulfur species (RSS). Plant Physiol Biochem. 2012;59:98–107.
   PubMed Web of Science ®Google Scholar
• Lau N, Pluth MD. Reactive sulfur species (RSS): persulfides, polysulfides, potential, and problems. Curr Opin Chem Biol. 2019;49:1–8.
   PubMed Web of Science ®Google Scholar
• Zheng YZ, Deng G, Zhang YC. Multiple free radical scavenging reactions of flavonoids. Dyes Pigm. 2022;198:109877.
   Web of Science ®Google Scholar
• Zheng YZ, Zhou Y, Guo R, et al. Structure-antioxidant activity relationship of ferulic acid derivatives: effect of ester groups at the end of the carbon side chain. Lwt. 2020;120:108932.
   Web of Science ®Google Scholar
• Kabanda MM, Gbashi S, Madala NE. Proportional coexistence of okanin chalcone glycoside and okanin flavanone glycoside in Bidens pilosa leaves and theoretical investigation on the antioxidant properties of their aglycones. Free Radic Res. 2021;55(1):53–70.
   PubMed Web of Science ®Google Scholar
• Mahapatra DK, Bharti SK, Asati V, et al. Perspectives of medicinally privileged chalcone based metal coordination compounds for biomedical applications. Eur J Med Chem. 2019;174:142–158.
   PubMed Web of Science ®Google Scholar
• Mittal A, Kakkar R. The antioxidant potential of retrochalcones isolated from liquorice root: a comparative DFT study. Phytochemistry. 2021;192:112964.
   PubMed Web of Science ®Google Scholar
• Biela M, Rimarčík J, Senajová E, et al. Antioxidant action of deprotonated flavonoids: thermodynamics of sequential proton-loss electron-transfer. Phytochemistry. 2020;180:112528.
   PubMed Web of Science ®Google Scholar
• Xue Y, Teng Y, Chen M, et al. Antioxidant activity and mechanism of avenanthramides: double H+/e– processes and role of the catechol, guaiacyl, and carboxyl groups. J Agric Food Chem. 2021;69(25):7178–7189.
   PubMed Web of Science ®Google Scholar
• Amić A, Marković Z, Dimitrić Marković JM, et al. The role of guaiacyl moiety in free radical scavenging by 3, 5-dihydroxy-4-methoxybenzyl alcohol: thermodynamics of 3H+/3e− mechanisms. Mol Phys. 2019;117(2):207–217.
   Web of Science ®Google Scholar
• Amić A, Marković Z, Marković JMD, et al. The 2H+/2e− free radical scavenging mechanisms of uric acid: thermodynamics of N-H bond cleavage. Comput Theor Chem. 2016;1077:2–10.
   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;7:335–352.
   PubMed Web of Science ®Google Scholar
• Hammes-Schiffer S, Soudackov AV. Proton-coupled electron transfer in solution, proteins, and electrochemistry. J Phys Chem B. 2008;112(45):14108–14123.
   PubMed Web of Science ®Google Scholar
• Milenković DA, Dimić DS, Avdović EH, et al. Advanced oxidation process of coumarins by hydroxyl radical: towards the new mechanism leading to less toxic products. Chem Eng J. 2020;395:124971.
   Web of Science ®Google Scholar
• Marković Z. Study of the mechanisms of antioxidative action of different antioxidants. J Serb Soc Comput Mech. 2016;10(1):135–150.
   Google Scholar
• Spiegel M. Current trends in computational quantum chemistry studies on antioxidant radical scavenging activity. J Chem Inf Model. 2022;62(11):2639–2658.
   PubMed Web of Science ®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
• Tsiepe TJ, Kabanda MM, Serobatse K. Antioxidant properties of kanakugiol revealed through the hydrogen atom transfer, electron transfer and M2+ (M2+= Cu (II) or Co (II) ion) coordination ability mechanisms. A DFT study in vacuo and in solution. Food Biophys. 2015;10(3):342–359.
   Web of Science ®Google Scholar
• Serobatse KR, Kabanda MM. A theoretical study on the antioxidant properties of methoxy-substituted chalcone derivatives: a case study of kanakugiol and pedicellin through their Fe (II and III) coordination ability. J Theor Comput Chem. 2016;15(06):1650048.
   Google Scholar
• Serobatse K, Kabanda MM. Antioxidant and antimalarial properties of butein and homobutein based on their ability to chelate iron (II and III) cations: a DFT study in vacuo and in solution. Eur Food Res Technol. 2016;242(1):71–90.
   Web of Science ®Google Scholar
• Tajammal A, Batool M, Ramzan A, et al. Synthesis, antihyperglycemic activity and computational studies of antioxidant chalcones and flavanones derived from 2,5 dihydroxyacetophenone. J Mol Struct. 2017;1148:512–520.
   Web of Science ®Google Scholar
• Tavadyan LA, Minasyan SH. Synergistic and antagonistic co-antioxidant effects of flavonoids with trolox or ascorbic acid in a binary mixture. J Chem Sci. 2019;131(5):1–11.
   Web of Science ®Google Scholar
• Hamlaoui I, Bencheraiet R, Bensegueni R, et al. Experimental and theoretical study on DPPH radical scavenging mechanism of some chalcone quinoline derivatives. J Mol Struct. 2018;1156:385–389.
   Web of Science ®Google Scholar
• Xue Y, Liu Y, Zhang L, et al. Antioxidant and spectral properties of chalcones and analogous aurones: theoretical insights. Int J Quantum Chem. 2019;119(3):e25808.
   Web of Science ®Google Scholar
• Stepanić V, Matijašić M, Horvat T, et al. Antioxidant activities of alkyl substituted pyrazine derivatives of chalcones—in vitro and in silico study. Antioxidants. 2019;8(4):90.
   Web of Science ®Google Scholar
• Ferreira MKA, da Silva AW, Silva FCO, et al. Anxiolytic-like effect of chalcone N-{(4′-[(E)-3-(4-fluorophenyl)-1-(phenyl) prop-2-en-1-one]} acetamide on adult zebrafish (Danio rerio): involvement of the GABAergic system. Behav Brain Res. 2019;374:111871.
   PubMed Web of Science ®Google Scholar
• Almeida-Neto FWQ, da Silva LP, Ferreira MKA, et al. Characterization of the structural, spectroscopic, nonlinear optical, electronic properties and antioxidant activity of the N-{4’-[(E)-3-(fluorophenyl)-1-(phenyl)-prop-2-en-1-one]}-acetamide. J Mol Struct. 2020;1220:128765.
   Web of Science ®Google Scholar
• Diaz-Uribe C, Vallejo W, Flórez J, et al. Furanyl chalcone derivatives as efficient singlet oxygen quenchers. An experimental and DFT/MRCI study. Tetrahedron. 2020;76(24):131248.
   Web of Science ®Google Scholar
• Boulebd H. The role of benzylic-allylic hydrogen atoms on the antiradical activity of prenylated natural chalcones: a thermodynamic and kinetic study. J Biomol Struct Dyn. 2021;39(6):1955–1964.
   PubMed Web of Science ®Google Scholar
• Lin Y, Kuang Y, Li K, et al. Nrf2 activators from glycyrrhiza inflata and their hepatoprotective activities against CCl4-induced liver injury in mice. Bioorg Med Chem. 2017;25(20):5522–5530.
   PubMed Web of Science ®Google Scholar
• Yun SR, Jun JG. An efficient first synthesis of licochalcone G. Bull Korean Chem Soc. 2015;36(11):2784–2787.
   Web of Science ®Google Scholar
• Mittal A, Kakkar R. The effect of solvent polarity on the antioxidant potential of echinatin, a retrochalcone, towards various ROS: a DFT thermodynamic study. Free Radic Res. 2020;54(10):777–786.
   PubMed Web of Science ®Google Scholar
• Ali Z, Hawwal M, Ahmed MM, et al. Licochalcone L, an undescribed retrochalcone from glycyrrhiza inflata roots. Nat Prod Res. 2022;36(1):200–206.
   PubMed Web of Science ®Google Scholar
• Liang M, Li X, Ouyang X, et al. Antioxidant mechanisms of echinatin and licochalcone A. Molecules. 2018;24(1):3.
   PubMed Web of Science ®Google Scholar
• Prabakaran G, Manivarman S, Bharanidharan M. Catalytic synthesis, ADMET, QSAR and molecular modeling studies of novel chalcone derivatives as highly potent antioxidant agents. Mater Today: Proceedings. 2022;48:400–408.
   Google Scholar
• Moreira CA, Faria EC, Queiroz JE, et al. Structural insights and antioxidant analysis of a tri-methoxy chalcone with potential as a diesel-biodiesel blend additive. Fuel Process Technol. 2022;227:107122.
   Web of Science ®Google Scholar
• Amić A, Marković Z, Klein E, et al. Theoretical study of the thermodynamics of the mechanisms underlying antiradical activity of cinnamic acid derivatives. Food Chem. 2018;246:481–489.
   PubMed Web of Science ®Google Scholar
• Pelucchi M, Cavallotti C, Cuoci A, et al. Detailed kinetics of substituted phenolic species in pyrolysis bio-oils. React Chem Eng. 2019;4(3):490–506.
   Web of Science ®Google Scholar
• Biela M, Kleinová A, Klein E. Phenolic acids and their carboxylate anions: thermodynamics of primary antioxidant action. Phytochem. 2022;200:113254.
   PubMed Web of Science ®Google Scholar
• Shang C, Zhang Y, Sun C, et al. Tactfully improve the antioxidant activity of 2'-hydroxychalcone with the strategy of substituent, solvent and intramolecular hydrogen bond effects. J Mol Liq. 2022;362:119748.
   Web of Science ®Google Scholar
• Aly MRES, Fodah H, Saleh SY. Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes. Eur J Med Chem. 2014;76:517–530.
   PubMed Web of Science ®Google Scholar
• Venkatesh T, Bodke YD, Kenchappa R, et al. Synthesis, antimicrobial and antioxidant activity of chalcone derivatives containing thiobarbitone nucleus. Med Chem. 2016;6(7):440–448.
   Google Scholar
• Zainuri DA, Arshad S, Khalib NC, et al. Synthesis, XRD crystal structure, spectroscopic characterization (FT-IR, 1H and 13C NMR), DFT studies, chemical reactivity and bond dissociation energy studies using molecular dynamics simulations and evaluation of antimicrobial and antioxidant activities of a novel chalcone derivative, (E)-1-(4-bromophenyl)-3-(4-iodophenyl) prop-2-en-1-one. J Mol Struct. 2017;1128:520–533.
   Web of Science ®Google Scholar
• El-Sayed YS, Gaber M. Studies on chalcone derivatives: complex formation, thermal behavior, stability constant and antioxidant activity. Spectrochim Acta A Mol Biomol Spectrosc. 2015;137:423–431.
   PubMed Web of Science ®Google Scholar
• Sulpizio C, Müller ST, Zhang Q, et al. Synthesis, characterization, and antioxidant activity of Zn2+ and Cu2+ coordinated polyhydroxychalcone complexes. Monatsh Chem. 2016;147(11):1871–1881.
   PubMed Web of Science ®Google Scholar