A combination of experimental research and computational chemistry in investigating antioxidant potential of gallic acid
Vol. 132 No. 1A (2023), Original Article
Vol. 132 No. 1A (2023)

A combination of experimental research and computational chemistry in investigating antioxidant potential of gallic acid

Original Article
https://doi.org/10.26459/hueunijns.v132i1A.6892
Published 2023-03-31
Dinh Quy Huong*
Department of Chemistry, University of Education, Hue University, 34 Le Loi St., Hue, Vietnam
http://orcid.org/0000-0002-2610-7151
PDF (Vietnamese)

Keywords

quantum chemical calculation
reaction mechanism
antioxidant gallic acid
tính toán hoá lượng tử
cơ chế phản ứng
chống oxi hoá

How to Cite

1.
Đinh QH. A combination of experimental research and computational chemistry in investigating antioxidant potential of gallic acid. hueuni-jns [Internet]. 2023Mar.31 [cited 2024Jun.26];132(1A):41-8. Available from: https://jos.hueuni.edu.vn/index.php/hujos-ns/article/view/6892
ACM ACS APA ABNT Chicago Harvard IEEE MLA Turabian Vancouver

Download Citation

Endnote/Zotero/Mendeley (RIS) BibTeX
Crossref
Scopus
Google Scholar
Europe PMC

Abstract

The antioxidant capacity of 3,4,5-trihydroxybenzoic acid (gallic acid) was investigated with spectroscopic methods, including 2,2-diphenyl-1-picrylhydrazyl (DPPH•), 2,2'-azinobis(3)-ethylbenzothiazoline-6-sulfonate) (ABTS•+), and phosphomolybdenum and quantum chemical calculations at the theoretical level of w-B97XD/6-311++G(d,p). The results show that gallic acid had stronger DPPH• and ABTS•+ free radical scavenging ability than trolox with IC50DPPH and IC50ABTS values ​​of 2.23 ± 0.02 and 12.20 ± 0.03 μM. In the phosphomolybdenum method, Mo(VI) to Mo(V) reducing ability of gallic acid was equivalent to that of trolox. According to quantum research results, the reaction mechanism between gallic acid and HOO• is primarily the hydrogen atom transfer.

https://doi.org/10.26459/hueunijns.v132i1A.6892
PDF (Vietnamese)

References

  1. Badhani B, Sharma N, Kakkar R. Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications. RSC Advances. 2015; 5(35):27540-57.
  2. Kim DO, Lee KW, Lee HJ, Lee CY. Vitamin C equivalent antioxidant capacity (VCEAC) of phenolic phytochemicals. Journal of agricultural and food chemistry. 2002;50(13):3713-7.
  3. Schlesier K, Harwat M, Bohm V, Bitsch R. (2002) Assessment of antioxidant activity by using different in vitro methods. Free radical research. 2002;36(2):177-87.
  4. Chai JD, Head-Gordon M. Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Physical chemistry chemical physics: PCCP. 2008;10(44):6615-20.
  5. Masek A, Chrzescijanska E, Latos M, Zaborski M, Podsędek A. Antioxidant and Antiradical Properties of Green Tea Extract Compounds. International Journal of Electrochemical Science. 2017;12:6600-10.
  6. Prieto P, Pineda M, Aguilar M. Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: specific application to the determination of vitamin E. Analytical biochemistry. 1999;269(2):337-41.
  7. Capaldo L, Ravelli D. Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis. European journal of organic chemistry. 2017;(15):2056-71.
  8. Mayer JM. Understanding hydrogen atom transfer: from bond strengths to Marcus theory. Accounts of chemical research. 2011;44(1):36-46.
  9. Milenković DA, Dimić DS, Avdović EH, Amić AD, Dimitrić Marković JM, Marković ZS. Advanced oxidation process of coumarins by hydroxyl radical: Towards the new mechanism leading to less toxic products. Chemical Engineering Journal. 2020; 395:124971.
  10. Ahmadi S, Marino T, Prejano M, Russo N, Toscano M. Antioxidant Properties of the Vam3 Derivative of Resveratrol. Molecules. 2018;23(10).
  11. Nithya P, Madhavi C. Antioxidant activity of 3-arylidene-4-piperidones in the 1,1-diphenyl-2-picrylhydrazyl scavenging assay. J Taibah Univ Sci. 2018;11(1):40-5.
  12. Martinez-Morales F, Alonso-Castro AJ, Zapata-Morales JR, Carranza-Álvarez C, Aragon-Martinez OH. Use of standardized units for a correct interpretation of IC50 values obtained from the inhibition of the DPPH radical by natural antioxidants. Chemical Papers. 2020;74(10):3325-34.
  13. Echegaray N, Pateiro M, Munekata PES, Lorenzo JM, Chabani Z, Farag MA, et al. Measurement of Antioxidant Capacity of Meat and Meat Products: Methods and Applications. Molecules. 2020;26(13).
  14. Uddin MN, Mitra K, Haque MZ. Comparative Bio-Active Compounds Determination andIn VitroAntioxidant Properties of Newly Developed Soy Mixed Wheat Flour and Traditional Wheat Flour. Int J Food Prop. 2016;19(9):2113-26.
  15. Bibi Sadeer N, Montesano D, Albrizio S, Zengin G, Mahomoodally MF. The Versatility of Antioxidant Assays in Food Science and Safety-Chemistry, Applications, Strengths, and Limitations. Antioxidants. 2020;9(8).
  16. Galano A, Alvarez-Idaboy JR. A computational methodology for accurate predictions of rate constants in solution: application to the assessment of primary antioxidant activity. J Comput Chem. 2013;34(28):2430-45.
  17. Wright JS, Johnson ER, DiLabio GA. Predicting the Activity of Phenolic Antioxidants: Theoretical Method, Analysis of Substituent Effects, and Application to Major Families of Antioxidants. Journal of the American Chemical Society. 2001;123(6):1173-83.
  18. Galano A, Alvarez-Idaboy JR. A computational methodology for accurate predictions of rate constants in solution: application to the assessment of primary antioxidant activity. Journal of computational chemistry. 2013;34(28):2430-45.
Creative Commons License

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

Copyright (c) 2023 Array