Published November 30, 2020
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Antioxidant activity and mechanism of dihydrochalcone C-glycosides: Effects of C-glycosylation and hydroxyl groups
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Xue, Yunsheng, Liu, Yunping, Xie, Yuxin, Cong, Chunxue, Wang, Guirong, An, Lin, Teng, Yangxin, Chen, Mohan, Zhang, Ling (2020): Antioxidant activity and mechanism of dihydrochalcone C-glycosides: Effects of C-glycosylation and hydroxyl groups. Phytochemistry (112393) 179: 1-10, DOI: 10.1016/j.phytochem.2020.112393, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112393
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References
- Ami c, A., Lu c i c, B., Stepani c, V., Markovi c, Z., Markovi c, S., Dimitri c Markovi c, J.M., Ami c, D., 2017. Free radical scavenging potency of quercetin catecholic colonic metabolites: thermodynamics of 2H+/2e- processes. Food Chem. 218, 144-151.
- Amic, A., Markovic, Z., Dimitric Markovic, J.M., Milenkovic, D., Stepanic, V., 2020. Antioxidative potential of ferulic acid phenoxyl radical. Phytochemistry 170, 112218.
- Andreescu, S., Hepel, M. (Eds.), 2011. Oxidative Stress: Diagnostics, Prevention, and Therapy. American Chemical Society.
- Anouar, E.H., Raweh, S., Bayach, I., Taha, M., Baharudin, M.S., Di Meo, F., Hasan, M.H., Adam, A., Ismail, N.H., Weber, J.-F.F., Trouillas, P., 2013. Antioxidant properties of phenolic Schiff bases: structure-activity relationship and mechanism of action. J. Comput. Aided Mol. Des. 27, 951-964.
- Arokia, V.A.M., Ramachandran, V., Vinothkumar, R., Vijayalakshmi, S., Sathish, V., Ernest, D., 2019. Pharmacological aspects and potential use of phloretin: a systemic review. Mini Rev. Med. Chem. 19, 1060-1067.
- Bader, R.F.W., 1991. A quantum theory of molecular structure and its applications. Chem. Rev. 91, 893-928.
- Bartmess, J.E., 1994. Thermodynamics of the electron and the proton. J. Phys. Chem. 98, 6420-6424.
- Behzad, S., Sureda, A., Barreca, D., Nabavi, S.F., Rastrelli, L., Nabavi, S.M., 2017. Health effects of phloretin: from chemistry to medicine. Phytochemistry Rev. 16, 527-533.
- Bentes, A.L., Borges, R.S., Monteiro, W.R., de Macedo, L.G., Alves, C.N., 2011. Structure of dihydrochalcones and related derivatives and their scavenging and antioxidant activity against oxygen and nitrogen radical species. Molecules 16, 1749-1760.
- Bizarro, M.M., Costa Cabral, B.J., dos Santos, R.M.B., Martinho Simoes, J.A., 1999. Substituent effects on the O-H bond dissociation enthalpies in phenolic compounds: agreements and controversies. Pure Appl. Chem. 71, 1249-1256.
- Boulebd, H., 2019. DFT study of the antiradical properties of some aromatic compounds derived from antioxidant essential oils: C-H bond vs. O-H bond. Free Radic. Res. 53, 1125-1134.
- Cai, W., Chen, Y., Xie, L., Zhang, H., Hou, C., 2013. Characterization and density functional theory study of the antioxidant activity of quercetin and its sugar-containing analogues. Eur. Food Res. Technol. 238, 121-128.
- Chan, B., Easton, C.J., Radom, L., 2018. Effect of hydrogen bonding and partial deprotonation on the oxidation of peptides. J. Phys. Chem. A. 122, 1741-1746.
- Choi, J.S., Islam, M.N., Ali, M.Y., Kim, E.J., Kim, Y.M., Jung, H.A., 2014a. Effects of Cglycosylation on anti-diabetic, anti-Alzheimer's disease and anti-inflammatory potential of apigenin. Food Chem. Toxicol. 64, 27-33.
- Choi, J.S., Islam, M.N., Ali, M.Y., Kim, Y.M., Park, H.J., Sohn, H.S., Jung, H.A., 2014b. The effects of C-glycosylation of luteolin on its antioxidant, anti-Alzheimer's disease, anti-diabetic, and anti-inflammatory activities. Arch Pharm. Res. (Seoul) 37, 1354-1363.
- Courts, F.L., Williamson, G., 2015. The occurrence, fate and biological activities of Cglycosyl flavonoids in the human diet. Crit. Rev. Food Sci. Nutr. 55, 1352-1367.
- Cuendet, M., Potterat, O., Salvi, A., Testa, B., Hostettmann, K., 2000. A stilbene and dihydrochalcones with radical scavenging activities from Loiseleuria procumbens. Phytochemistry 54, 871-874.
- da Veiga, A.A.S., de Jesus Chaves Neto, A.M., da Silva, A.B.F., Herculano, A.M., Oliveira, K.R.M., dos Santos Borges, R., 2018. Sugar moiety has a synergistic effect on hydroxylated xanthone for better antioxidant activity of mangiferin. Med. Chem. Res. 27, 1276-1282.
- Duge de Bernonville, T., Guyot, S., Paulin, J.P., Gaucher, M., Loufrani, L., Henrion, D., Derbre, S., Guilet, D., Richomme, P., Dat, J.F., Brisset, M.N., 2010. Dihydrochalcones: implication in resistance to oxidative stress and bioactivities against advanced glycation end-products and vasoconstriction. Phytochemistry 71, 443-452.
- Dziedzic, S.Z., Hudson, B.J.F., Barnes, G., 1985. Polyhydroxydihydrochalcones as antioxidants for lard. J. Agric. Food Chem. 33, 244-246.
- Elder, T., Carlos Del Rio, J., Ralph, J., Rencoret, J., Kim, H., Beckham, G.T., 2019. Radical coupling reactions of piceatannol and monolignols: a density functional theory study. Phytochemistry 164, 12-23.
- Estevez, L., Otero, N., Mosquera, R.A., 2010. A computational study on the acidity dependence of radical-scavenging mechanisms of anthocyanidins. J. Phys. Chem. B 114, 9706-9712.
- Frisch, M.J., Trucks, G.W., Schlegel, H.B., et al., 2013. Gaussian 09, Revision D. 01. Gaussian, Inc., Wallingford, CT.
- Galano, A., 2015. Free radicals induced oxidative stress at a molecular level: the current status, challenges and perspectives of computational chemistry based protocols. J. Mex. Chem. Soc. 59, 231-262.
- Galano, A., Raul Alvarez-Idaboy, J., 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.
- Huang, H.Y., Ko, H.H., Jin, Y.J., Yang, S.Z., Shih, Y.A., Chen, I.S., 2012. Dihydrochalcone glucosides and antioxidant activity from the roots of Anneslea fragrans var. lanceolata. Phytochemistry 78, 120-125.
- Ingold, K.U., Pratt, D.A., 2014. Advances in radical-trapping antioxidant chemistry in the 21st century: a kinetics and mechanisms perspective. Chem. Rev. 114, 9022-9046.
- Jayasinghe, U.L., Ratnayake, R.M., Medawala, M.M., Fujimoto, Y., 2007. Dihydrochalcones with radical scavenging properties from the leaves of Syzygium jambos. Nat. Prod. Res. 21, 551-554.
- Jesus, A.R., Vila-Vicosa, D., Machuqueiro, M., Marques, A.P., Dore, T.M., Rauter, A.P., 2017. Targeting type 2 diabetes with C-glucosyl dihydrochalcones as selective sodium glucose Co-transporter 2 (SGLT2) inhibitors: synthesis and biological evaluation. J. Med. Chem. 60, 568-579.
- Johnson, R., Beer, D., Dludla, P.V., Ferreira, D., Muller, C.J.F., Joubert, E., 2018. Aspalathin from rooibos (aspalathus linearis): a bioactive C-glucosyl dihydrochalcone with potential to target the metabolic syndrome. Planta Med. 84, 568-583.
- Klein, E., Rimar c ik, J., Senajova, E., Vaganek, A., Lengyel, J., 2016. Deprotonation of flavonoids severely alters the thermodynamics of the hydrogen atom transfer. Comput. Theor. Chem. 1085, 7-17.
- Kozlowski, D., Trouillas, P., Calliste, C., Marsal, P., Lazzaroni, R., Duroux, J.-L., 2007. Density functional theory study of the conformational, electronic, and antioxidant properties of natural chalcones. J. Phys. Chem. A. 111, 1138-1145.
- Ku, S.K., Kwak, S., Kim, Y., Bae, J.S., 2015. Aspalathin and Nothofagin from Rooibos (Aspalathus linearis) inhibits high glucose-induced inflammation in vitro and in vivo. Inflammation 38, 445-455.
- Leopoldini, M., Russo, N., Toscano, M., 2011. The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem. 125, 288-306.
- Lespade, L., Bercion, S., 2012. Theoretical investigation of the effect of sugar substitution on the antioxidant properties of flavonoids. Free Radic. Res. 46, 346-358.
- Li, D.D., Han, R.M., Liang, R., Chen, C.H., Lai, W., Zhang, J.P., Skibsted, L.H., 2012. Hydroxyl radical reaction with trans-resveratrol: initial carbon radical adduct formation followed by rearrangement to phenoxyl radical. J. Phys. Chem. B 116, 7154-7161.
- Li, X., Chen, B., Xie, H., He, Y., Zhong, D., Chen, D., 2018. Antioxidant Structure (-)Activity relationship analysis of five dihydrochalcones. Molecules 23, 1162.
- Lu, T., Chen, F., 2012. Multiwfn: a multifunctional wavefunction analyzer. J. Comput. Chem. 33, 580-592.
- Maciel, E.N., Soares, I.N., da Silva, S.C., de Souza, G.L.C., 2019. A computational study on the reaction between fisetin and 2,2-diphenyl-1-picrylhydrazyl (DPPH). J. Mol. Model. 25, 103.
- Martinez, A., Vargas, R., Galano, A., 2018. Citric acid: a promising copper scavenger. Comput. Theor. Chem. 1133, 47-50.
- Mathiesen, L., Malterud, K.E., Sund, R.B., 1997. Hydrogen bond formation as basis for radical scavenging activity: a structure-activity study of C-methylated dihydrochalcones from myrica gale and structurally related acetophenones. Free Radic.Bio. Med. 22, 307-311.
- Mazzone, G., Russo, N., Toscano, M., 2016. Antioxidant properties comparative study of natural hydroxycinnamic acids and structurally modified derivatives: computational insights. Comput. Theor. Chem. 1077, 39-47.
- Mendes, R.A., Bls, E.S., Takeara, R., Freitas, R.G., Brown, A., de Souza, G.L.C., 2018. Probing the antioxidant potential of phloretin and phlorizin through a computational investigation. J. Mol. Model. 24, 101.
- Michalik, M., Poliak, P., Lukes, V., Klein, E., 2019. From phenols to quinones: thermodynamics of radical scavenging activity of para-substituted phenols. Phytochemistry 166, 112077.
- Mikulski, D., Molski, M., 2012. Quantum-mechanical computations on the electronic structure of trans-resveratrol and trans-piceatannol: a theoretical study of the stacking interactions in trans-resveratrol dimers. J. Mol. Model. 18, 3255-3266.
- Musialik, M., Kuzmicz, R., Paw l owski, T.S., Litwinienko, G., 2009. Acidity of hydroxyl groups: an overlooked influence on antiradical properties of flavonoids. J. Org. Chem. 74, 2699-2709.
- Nakamura, Y., Watanabe, S., Miyake, N., Kohno, H., Osawa, T., 2003. Dihydrochalcones: evaluation as novel radical scavenging antioxidants. J. Agric. Food Chem. 51, 3309-3312.
- Nenadis, N., Stavra, K., 2017. Effect of cα-cβ bond type on the radical scavenging activity of hydroxy stilbenes: theoretical insights in the gas and liquid phase. J. Phys. Chem. A. 121, 2014-2021.
- Nenadis, N., Tsimidou, M.Z., 2012. Contribution of DFT computed molecular descriptors in the study of radical scavenging activity trend of natural hydroxybenzaldehydes and corresponding acids. Food Res. Int. 48, 538-543.
- Parker, V.D., 1992. Homolytic bond (H-A) dissociation free energies in solution. Applications of the standard potential of the (H+/H.bul.) couple. J. Am. Chem. Soc. 114, 7458-7462.
- 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.
- Ponomarenko, J., Trouillas, P., Martin, N., Dizhbite, T., Krasilnikova, J., Telysheva, G., 2014. Elucidation of antioxidant properties of wood bark derived saturated diarylheptanoids: a comprehensive (DFT-supported) understanding. Phytochemistry 103, 178-187.
- Quideau, S., Deffieux, D., Douat-Casassus, C., Pouysegu, L., 2011. Plant polyphenols: chemical properties, biological activities, and synthesis. Angew. Chem. Int. Ed. 50, 586-621.
- Rezk, B.M., Haenen, G.R.M.M., van der Vijgh, W.J.F., Bast, A., 2002. The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem. Bioph. Res. Co. 295, 9-13.
- Rimar c ik, J., Luke s, V., Klein, E., Il c in, M., 2010. Study of the solvent effect on the enthalpies of homolytic and heterolytic N-H bond cleavage in p-phenylenediamine and tetracyano-p-phenylenediamine. J. Mol. Struc.THEOCHEM 952, 25-30.
- Rozas, I., Alkorta, I., Elguero, J., 2000. Behavior of ylides containing N, O, and C atoms as hydrogen bond acceptors. J. Am. Chem. Soc. 122, 11154-11161.
- Rozmer, Z., Perjesi, P., 2016. Naturally occurring chalcones and their biological activities. Phytochemistry Rev. 15, 87-120.
- Smith, C., Swart, A., 2018. Aspalathus linearis (Rooibos) - a functional food targeting cardiovascular disease. Food Funct. 9, 5041-5058.
- Snijman, P.W., Joubert, E., Ferreira, D., Li, X.C., Ding, Y., Green, I.R., Gelderblom, W.C., 2009. Antioxidant activity of the dihydrochalcones aspalathin and nothofagin and their corresponding flavones in relation to other rooibos ( aspalathus linearis ) flavonoids, epigallocatechin gallate, and trolox. J. Agric. Food Chem. 57, 6678-6684.
- Su, C., Xia, X., Shi, Q., Song, X., Fu, J., Xiao, C., Chen, H., Lu, B., Sun, Z., Wu, S., Yang, S., Li, X., Ye, X., Song, E., Song, Y., 2015. Neohesperidin dihydrochalcone versus CCl(4)- induced hepatic injury through different mechanisms: the implication of free radical scavenging and Nrf2 activation. J. Agric. Food Chem. 63, 5468-5475.
- Suarez, J., Herrera, M.D., Marhuenda, E., 1998. In vitro scavenger and antioxidant properties of hesperidin and neohesperidin dihydrochalcone. Phytomedicine 5, 469-473.
- Thong, N.M., Vo, Q.V., Huyen, T.L., Bay, M.V., Tuan, D., Nam, P.C., 2019. Theoretical study for exploring the diglycoside substituent effect on the antioxidative capability of isorhamnetin extracted from anoectochilus roxburghii. ACS Omega 4, 14996-15003.
- Tomasi, J., Mennucci, B., Cammi, R., 2005. Quantum mechanical continuum solvation models. Chem. Rev. 105, 2999-3093.
- To s ovi c, J., Markovi c, S., 2019. Antioxidative activity of chlorogenic acid relative to trolox in aqueous solution - DFT study. Food Chem. 278, 469-475.
- van der Merwe, J.D., Joubert, E., Manley, M., de Beer, D., Malherbe, C.J., Gelderblom, W.C., 2010. In vitro hepatic biotransformation of aspalathin and nothofagin, dihydrochalcones of rooibos (Aspalathus linearis), and assessment of metabolite antioxidant activity. J. Agric. Food Chem. 58, 2214-2220.
- Viet, M.H., Chen, C.Y., Hu, C.K., Chen, Y.R., Li, M.S., 2013. Discovery of dihydrochalcone as potential lead for Alzheimer's disease: in silico and in vitro study. PloS One 8, e79151.
- von Gadow, A., Joubert, E., Hansmann, C.F., 1997. Comparison of the antioxidant activity of aspalathin with that of other plant phenols of rooibos tea (aspalathus linearis), α- tocopherol, BHT, and BHA. J. Agric. Food Chem. 45, 632-638.
- Wang, G.R., Xue, Y.S., An, L., Zheng, Y.G., Dou, Y.Y., Zhang, L., Liu, Y., 2015. Theoretical study on the structural and antioxidant properties of some recently synthesised 2,4,5- trimethoxy chalcones. Food Chem. 171, 89-97.
- Wang, G., Liu, Y., Zhang, L., An, L., Chen, R., Liu, Y., Luo, Q., Li, Y., Wang, H., Xue, Y., 2020. Computational study on the antioxidant property of coumarin-fused coumarins. Food Chem. 304, 125446.
- Wen, L., Zhao, Y., Jiang, Y., Yu, L., Zeng, X., Yang, J., Tian, M., Liu, H., Yang, B., 2017. Identification of a flavonoid C-glycoside as potent antioxidant. Free Radic.Bio. Med. 110, 92-101.
- Xiao, J., Capanoglu, E., Jassbi, A.R., Miron, A., 2016. Advance on the flavonoid C-glycosides and health benefits. Crit. Rev. Food Sci. Nutr. 56, S29-S45.
- Xiao, Z., Wang, Y., Wang, J., Li, P., Ma, F., 2019. Structure-antioxidant capacity relationship of dihydrochalcone compounds in Malus. Food Chem. 275, 354-360.
- Xue, Y.S., Liu, Y.P., Luo, Q.Q., Wang, H., Chen, R., Liu, Y., Li, Y., 2018. Antiradical activity and mechanism of coumarin-chalcone hybrids: theoretical insights. J. Phys. Chem. A. 122, 8520-8529.
- Yan, M.X., Gong, J.D., Shen, P., Yang, C.Y., 2014. The theory investigation for the antioxidant activity of phloretin: a comparation with naringenin. Appl. Mech. Mater. 513-517, 359-362.
- Yang, D., Xie, H., Jia, X., Wei, X., 2015. Flavonoid C-glycosides from star fruit and their antioxidant activity. J. Funct. Foods 16, 204-210.
- Zheng, Y.-Z., Deng, G., Liang, Q., Chen, D.-F., Guo, R., Lai, R.-C., 2017. Antioxidant activity of quercetin and its glucosides from propolis: a theoretical study. Sci. Rep. 7, 7543.
- Zheng, Y.Z., Deng, G., Guo, R., Fu, Z.M., Chen, D.F., 2019. Theoretical insight into the antioxidative activity of isoflavonoid: the effect of the C2=C3 double bond. Phytochemistry 166, 112075.
- Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C., Miao, Z., 2017. Chalcone: a privileged structure in medicinal chemistry. Chem. Rev. 117, 7762-7810.