Computational study of conformational, electronic and antioxidant properties of prenylated dihydrochalcone

Afnan Azzahra" Ahmad Kamal, Norazah Basar, Shajarahtunnur Jamil, Hasmerya Maarof

Abstract


The main aim of this study was to compare the antioxidant properties from theoretical results and experimental results.  Theoretical calculations obtained by DMoL3 based on density functional theory (DFT) were used to rationalize the antioxidant activities. The theoretical investigation emphasized on a hydrogen atom transfer (HAT) mechanism and single electron transfer (SET) mechanism. Inhibition of free radical using 2’,4’-dihydroxy-4-methoxy-3’-prenyldihydrochalcone (1), 2’,4’,4-trihydroxy-3’-prenylchalcone (2), and 2’,4dihydroxy-3’,4’-(2,2-dimethylchromene)chalcone (3) were examined to determine their antioxidant effects and the structure–activity relationships of chalcone.  Density functional theory calculations under the level of generalized gradient approximation (GGA) hybrid with Perdew-Burke-Ernzerhof (PBE) functional and double numerical polarization (DNP) basis set had been utilized to explore the structure, molecular properties and antioxidant abilities of the three chalcone.  Bond dissociation enthalpy (BDE), ionization potential (IP), frontier molecular orbital energy gap, molecular electrostatic potential surface (MEPS), and spin density were investigated. They were compared with the previous experimental results.  Scavenging activity determined by half maximal inhibitory concentration (IC50) values of the three chalcone increase from compound 2, followed by 3 and 1. The calculations showed that compound 2 owns the lowest ionization potential and lowest band energy, which agree well with the experimental results of antioxidant activity determined by IC50 values.


Keywords


Calcone; antioxidant activity; density functional theory; bond dissociation energy; ionization potential

Full Text:

PDF

References


Rozmer, Z., and Perjési, P. (2016). Naturally occurring chalcones and their biological activities. Phytochemistry Reviews, 15(1), 87–120.

Jamil, S., Sirat, H. M., Jantan, I., Aimi, N., and Kitajima, M. (2008). A new prenylated dihydrochalcone from the leaves of Artocarpus lowii. Journal of Natural Medicines, 62(3), 321–324.

Kozlowski, D., Trouillas, P., Calliste, C., Marsal, P., Lazzaroni, R., and Duroux, J.-L. (2007). Density functional theory study of the conformational, electronic, and antioxidant properties of natural chalcones. The Journal of Physical Chemistry. A, 111(6), 1138–1145.

Jamil, S., Taher, M., Sirat, H. M., and Othman, N. A. (2012). Flavonoids and triterpenes from the leaves of artocarpus fulvicortex. Natural Product Communications, 7(12), 29–31.

Hijova, E. (2006). Bioavailability of chalcones. Bratislavsk Lekrske Listy., 107(3), 80–84.

Kareem, H. S., Ariffin, A., Nordin, N., Heidelberg, T., Abdul-Aziz, A., Kong, K. W., and Yehye, W. A. (2015). Correlation of antioxidant activities with theoretical studies for new hydrazone compounds bearing a 3,4,5-trimethoxy benzyl moiety. European Journal of Medicinal Chemistry, 103, 497–505.

Cai, W., Chen, Y., Xie, L., Zhang, H., and Hou, C. (2014). Characterization and density functional theory study of the antioxidant activity of quercetin and its sugar-containing analogues. European Food Research and Technology, 238(1), 121–128.

Kumar, K. S. and Kumaresan, R. (2010). A quantum chemical study on the antioxidant properties of aureusidin and bracteatin. International Journal of Quantum Chemistry, 111, 4483-4496.

Urbaniak, A., Molski, M., and Szeląg, M. (2012). Quantum-chemical Calculations of the Antioxidant Properties of trans-p-coumaric Acid and trans-sinapinic Acid. Computational Methods in Science and Technology, 18(2), 117–128.

Mohamed, M. E., and Elssamani, A. O. (2015). Density Functional Theory ( DFT ) B3LYP Study of Antioxidant Activity of Bichalcophenes Derivatives. Journal of Applied and Industrial Sciences, 3(4), 126–132.

Al-Amiery, A. A., Kadhum, A. A. H., Obayes, H. R., and Mohamad, A. B. (2013). Synthesis and antioxidant activities of novel 5-chlorocurcumin, complemented by semiempirical calculations. Bioinorganic Chemistry and Applications, 2013.

Chen, Y., Xiao, H., Zheng, J., and Liang, G. (2015). Structure-Thermodynamics-Antioxidant Activity Relationships of Selected Natural Phenolic Acids and Derivatives: An Experimental and Theoretical Evaluation. PLOS One, 10(3), 1–20.

Bhawani, P. and Paras, N. C. (2013). Molecular structure, mesp, homo-lumo and vibrational analysis of β-asarone using density functional theory. Kathmandu University Journal of Science, Engineering and Technology, 9(11), 1-14.

Jursic, B. S. (1999). Complete basis set and gaussian computational study of bond dissociation energies, enthalpy of formation and rearrangement barriers for the XNO nitric oxide derivatives. Journal of Molecular Structure: THEOCHEM, 492, 35–43.


Refbacks

  • There are currently no refbacks.


Copyright (c) 2018 eProceedings Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

Copyright © 2016 Department of Chemistry, Universiti Teknologi Malaysia.

Disclaimer : This website has been updated to the best of our knowledge to be accurate. However, Universiti Teknologi Malaysia shall not be liable for any loss or damage caused by the usage of any information obtained from this web site.
Best viewed: Mozilla Firefox 4.0 & Google Chrome at 1024 × 768 resolution.