Comparison of radical scavenging behavior of chromones dihydrogenistein and demethyltexasin—a DFT approach
- 77 Downloads
The present work deals with the validation of radical scavenging behavior of two identical chromones: 4′,5,7 trihydroxy isoflavone dihydrogenistein (DGT) and 4′,6,7 trihydroxy isoflavone demethyltexasin (DMT) through structural activity analysis to study the influence of H atom on the radical scavenging behavior. Structural optimization and thermochemical calculations for the studied chromones is supported by DFT under the correlation functional B3LYP and M062X under 6-311G(d,p) basis set using Gaussian 09 package. Computations are carried out in gas phase and polar environment. Comparative analyses of radical scavenging ability of the two isoflavones are validated with the aid of two different levels of theory in three different environments which facilitates the antioxidant mechanism. Higher binding probability of DMT than DGT towards the selected enzyme target ALOX5 is observed in molecular docking analysis. This work paves a way to the elucidation of the beneficial effects on health of these compounds.
KeywordsDFT Chromones Frontier molecular orbital analysis and molecular docking
Funding was provided by Science and Engineering Research Board, Department of Science and Technology (DST-SERB), Government of India, through the research grant (EMR/2016/002892).
Compliance with ethical standards
Conflict of interest
The authors declare that there is no conflict of interest.
- 1.Tawfik HA, Ewies EF, El-Hamouly WS (2014) Synthesis of chromones and their applications during the last ten years during the last ten years. IJRPC 4(4):1046–1085Google Scholar
- 9.Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, revision D.01. Gaussian Inc., WallingfordGoogle Scholar
- 10.Galano A, Mazzone G, Alvarez-Diduk R, Marino T, Alvarez-Idaboy JR, Russo N (2016) 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 CrossRefPubMedGoogle Scholar
- 12.Deepha V, Praveena R (2015) Sadasivam. K J Mol Struct 1082:131e142Google Scholar
- 13.Senthilkumar K (2011) Kumaresan. R Int J Quantum Chem 111:4483e4496Google Scholar
- 16.Scrocco E (1979) Tomasi. J Adv Quantum Chem 11:115e193Google Scholar
- 23.Gammelmark A et al (2017) Interactions between 5-lipoxygenase polymorphisms and adipose tissue contents of arachidonic and eicosapentaenoic acids do not affect risk of myocardial infarction in middle-aged men and women in a Danish case-cohort study. J NutrGoogle Scholar
- 25.Mendoza-Wilson AM, Carmelo-Luna FJ, Astiazarán-García H, Pacheco-Moreno BI, Anduro-Corona I, Rascón-Durán ML DFT study of the physicochemical properties of A- and B-type procyanidin oligomers. J Theor Comput Chem. https://doi.org/10.1142/S0219633616500693