Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2017 Aug 8;7(1):7543.
doi: 10.1038/s41598-017-08024-8.

Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study

Yan-Zhen Zheng  1 , Geng Deng  2 , Qin Liang  1 , Da-Fu Chen  3 , Rui Guo  1 , Rong-Cai Lai  1
Affiliations

Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study

Yan-Zhen Zheng et al. Sci Rep. .

Abstract

Among the multiple components of propolis, flavonoids contribute greatly to the antioxidant activities of propolis. Flavonoids mainly exist in the form of sugar-conjugated derivatives. Quercetin glycosides represent the predominant flavonoid fraction in propolis. In this work, density functional theory (DFT) calculations were applied to analyze the antioxidative properties of quercetin and its glucosides in the gas and in the liquid phase (ethanol, water). Three main antioxidant mechanisms, hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) were used to analyze the antioxidative capacity of the investigated compounds. Solvent effects dominantly affect SET-PT and SPLET. Thus, the thermodynamically preferred mechanism can be altered. HAT and SPLET are the thermodynamically dominant mechanisms in gas and solvent phases, respectively. Therefore, in the gas phase, the sequence of the antioxidative capacity is similar with the bond dissociation enthalpy values: quercetin > quercetin-5-O-glucoside > quercetin-7-O-glucoside > quercetin-3-O-glucoside > quercetin-3'-O-glucoside > quercetin-4'-O-glucoside. While, in the solvent phases, the sequence is similar with the proton affinity values: quercetin-4'-O-glucoside > quercetin-5-O-glucoside > quercetin > quercetin-3-O-glucoside > quercetin-7-O-glucoside > quercetin-3'-O-glucoside. OH groups in B-ring and C-ring contribute mainly to the antioxidative activities of quercetin and glucosides compared with A-ring.

PubMed Disclaimer

Conflict of interest statement

The authors declare that they have no competing interests.

Figures

Figure 1
Figure 1
The chemical structure and atom numbering for quercetin and its glucosides.
Figure 2
Figure 2
Spin density distribution of quercetin radical computed at the M062X/6–311 + G** level of theory in the gas phase.
Figure 3
Figure 3
The energy and distribution of HOMO and LUMO for quercetin and its glucosides in the gas phase.
See this image and copyright information in PMC

References

    1. Nagai T, Sakai M, Inoue R, Inoue H, Suzuki N. Antioxidative activities of some commercially honeys, royal jelly, and propolis. Food Chem. 2001;75:237–240. doi: 10.1016/S0308-8146(01)00193-5. - DOI
    1. Diplock AT, Rice-Evans CA, Burdon RH. Is there a significant role for lipid peroxidation in the causation of malignancy and for antioxidants in cancer prevention. Cancer Res. 1994;54:1952–1956. - PubMed
    1. Ames BN, Shigenaga MK, Hagen TM. Oxidants, antioxidants, and the degenerative disease of aging. Proc Natl Acad Sci USA. 1993;90:7915–7922. doi: 10.1073/pnas.90.17.7915. - DOI - PMC - PubMed
    1. Bankova VS, de Castro SL, Marcucci MC. Propolis: Recent advances in chemistry and plant origin. Apidologie. 2000;31:3–15. doi: 10.1051/apido:2000102. - DOI
    1. Burdock GA. Review of the biological properties and toxicity of bee propolis (propolis) Food Chem Toxicol. 1998;36:347–363. doi: 10.1016/S0278-6915(97)00145-2. - DOI - PubMed

Publication types