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Structural Chemistry

, Volume 30, Issue 5, pp 1795–1803 | Cite as

A quantum chemical study on the reactivity of four licorice flavonoids scavenging ·OOCl3C

  • Aihua Wang
  • Yang Lu
  • Xia Du
  • Peng Shi
  • Hui ZhangEmail author
Original Research
  • 27 Downloads

Abstract

Isoliquiritigenin, liquiritigen, uralenol, and neouralenol are four natural licorice flavonoid compounds extracted from licorice, which have the ability of scavenging free radicals. In this paper, the density functional theory (DFT) was used to study the microscopic reaction mechanism of the four kinds of licorice flavonoids respectively scavenging ·OOCl3C in vivo. At the level of M06-2X/6-311+G(d,p), the geometries of all stationary points for hydrogen atom transfer (HAT) and radical adduct formation (RAF) pathways were optimized. The thermodynamic parameters and kinetic parameters of each reaction pathway were obtained, and the potential energy surface information of each reaction pathway was obtained too. Using the continuum solvation model based on solute electron density (SMD), the influence of the solvation effect on the reaction was calculated. The main mechanisms and reactive sites for the capture of ·OOCl3C by four licorice flavonoids, liquiritigen, isoliquiritigenin, uralenol, and neouralenol, were determined. Research indicates liquiritigen captures ·OOCl3C by HAT mechanism. The HAT pathway on the B′ ring of liquiritigen is the main reactive site. Isoliquiritigenin captures ·OOCl3C in the body through HAT and RAF mechanism. The RAF pathway is the dominant reaction pathway. The C1 site on the carbon–carbon double bond linking the two benzene rings is the main reactive site. Uralenol and neouralenol capture ·OOCl3C by HAT mechanism. The main reactive site of uralenol is B6 site, and the main reactive site of neouralenol is B′ 2 site. By this study, the potential energy surface information difficult to capture by experimental research is obtained, which provides a reliable theoretical basis for the further screening of highly active natural free radical scavengers of flavonoids in licorice and provides the support for the improvement of the development and application technology of licorice.

Keywords

Licorice flavonoids Radical Potential energy surface Quantum chemical 

Notes

Acknowledgments

We thank the grid computing server provided by the Chinese Academy of Sciences.

Funding information

This work is supported by the National Basic Research Program of China (2012CB723308), the National Natural Science Foundation of China (51337002 and 50977019), the Doctoral Foundation by the Ministry of Education of China (20112303110005), and the Science Foundation for Distinguished Young Scholar of Heilongjiang Province (JC201206).

Compliance with ethical standards

Competing interests

The authors declare that they have no competing interests.

Supplementary material

11224_2019_1312_MOESM1_ESM.doc (1.2 mb)
ESM 1 (DOC 1257 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Aihua Wang
    • 1
    • 2
  • Yang Lu
    • 3
  • Xia Du
    • 1
  • Peng Shi
    • 1
  • Hui Zhang
    • 1
    Email author
  1. 1.College of Chemical and Environmental Engineering & College of Chemical and Environmental EngineeringHarbin University of Science and TechnologyHarbinPeople’s Republic of China
  2. 2.Heilongjiang Institute for Food and Drug ControlHarbinPeople’s Republic of China
  3. 3.College of Materials and Chemical EngineeringHeilongjiang Institute of TechnologyHarbinPeople’s Republic of China

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