Skip to main content

Comparison of radical scavenging behavior of chromones dihydrogenistein and demethyltexasin—a DFT approach

Abstract

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.

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

References

  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):1046–1085

    Google Scholar 

  2. Ahmad A, Ramasamy K, Majeed ABA, Mani V (2015) Enhancement of b-secretase inhibition and antioxidant activities of tempeh, a fermented soybean cake through enrichment of bioactive aglycones. Pharm Biol 53:758–766

    CAS  Article  Google Scholar 

  3. Klus K, Borger-Papendorf G, Barz W (1993) Formationof 6,7,4′-trihydroxyisoflavone (factor 2) from soybean seedisoflavones by bacteria isolated from tempe. Phytochemistry 34:979–981

    CAS  Article  Google Scholar 

  4. Toscano M, Russo N (2016) Soybean aglycones antioxidant activity. A theoretical investigation. Computational and Theoretical Chemistry 1077:119–124

    CAS  Article  Google Scholar 

  5. Lechner D, Gibbons S, Bucar F (2008) Plant phenoliccompounds as ethidium bromide efflux inhibitors in Mycobacterium smegmatis. J Antimicrob Chemother 62:345–348

    CAS  Article  Google Scholar 

  6. Novy P, Urban J, Vadlejch J, Kokoska L (2011) Invitrosynergistic effects of baicalin with oxytetracycline and tetracycline against Staphylococcus aureus. J Antimicrob Chemother 66:1298–1300

    CAS  Article  Google Scholar 

  7. Lengyel J, Rimarcík J, Vagánek A, Klein E (2013) On the radical scavenging activity of isoflavones: thermodynamics of O–H bond cleavage. Phys Chem Chem Phys 15:10895–10903

    CAS  Article  Google Scholar 

  8. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789

    CAS  Article  Google 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., Wallingford

    Google 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

    CAS  Article  PubMed  Google Scholar 

  11. Leopoldini M, Prieto Pitarch I, Russo N, Toscano M (2004) Structure, conformation, and electronic properties of apigenin, luteolin, and taxifolin antioxidants. A first principle theoretical study. J Phys Chem B 108:92–94

    CAS  Article  Google Scholar 

  12. Deepha V, Praveena R (2015) Sadasivam. K J Mol Struct 1082:131e142

    Google Scholar 

  13. Senthilkumar K (2011) Kumaresan. R Int J Quantum Chem 111:4483e4496

    Google Scholar 

  14. Luque FJ, Lopez JM (2000) Orozco. M Theor Chem Acc 103:343

    CAS  Article  Google Scholar 

  15. Deepha V, Praveena R, Sivakumar R, Sadasivam K (2014). Spectrochim Acta A 121:737e745

    Article  Google Scholar 

  16. Scrocco E (1979) Tomasi. J Adv Quantum Chem 11:115e193

    Google Scholar 

  17. Jeevitha D, Sadasivam K, Praveena R, Jayaprakasam R (2016) DFT study of glycosyl group reactivity in quercetin derivatives. J Mol Struct 1120:15e24

    Article  Google Scholar 

  18. Ferrali M, Signorini C, Caciotti B, Sugherini L, Ciccoli L, Giachetti D, Comporti M (1997) Protection against oxidative damage oferythrocyte membranes by the flavonoid quercetin and its relation toiron chelating activity. FEBS Lett 416:123–129

    CAS  Article  Google Scholar 

  19. Elliott AJ, Scheiber SA, Thomas C, Pardini RS (1992) Inhibition of glutathione reductase by flavonoids. Biochem Pharmacol 44:1603–1608

    CAS  Article  Google Scholar 

  20. Lu T, Chen F (2012) Multiwfn: a multifunctional wavefunction analyzer. J Comp Chem 33:580–592

    Article  Google Scholar 

  21. Lu T, Chen F (2012) Quantitative analysis of molecular surface based on improved marching Tetrahedra algorithm. J Mol Graph Model 38:314–323

    Article  Google Scholar 

  22. Parr RG, Szentpaly LV, Liu S (1999) Electrophilicity index. J Am Chem Soc 121:1922–1924

    CAS  Article  Google 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 Nutr

  24. Gfeller D, Michielin O, Zoete V (2013) Shaping the interaction landscape of bioactive molecules. Bioinformatics 29:3073–3079

    CAS  Article  Google 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

  26. Häfner A-K, Beilstein K, Graab P, Ball A-K, Saul MJ, Hofmann B et al (2016) Identification and characterization of a new protein isoform of human 5-lipoxygenase. PLoS One 11(11):e0166591

    Article  Google Scholar 

Download references

Funding

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).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to R. Praveena.

Ethics declarations

Conflict of interest

The authors declare that there is no conflict of interest.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Anbazhakan, K., Sadasivam, K. & Praveena, R. Comparison of radical scavenging behavior of chromones dihydrogenistein and demethyltexasin—a DFT approach. Struct Chem 30, 167–173 (2019). https://doi.org/10.1007/s11224-018-1185-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-018-1185-2

Keywords

  • DFT
  • Chromones
  • Frontier molecular orbital analysis and molecular docking