Citation: Yang Yimeng, Chen Xingyu, Wu Ya, Chen Congmei. Structure and Antioxidant Activities Relationship of Dandelion Flavonoids[J]. Chemistry, ;2020, 83(11): 1031-1037. shu

Structure and Antioxidant Activities Relationship of Dandelion Flavonoids

Yang Yimeng ^1,, ,
Chen Xingyu ¹ ,
Wu Ya ¹ ,
Chen Congmei ²

1.
College of Biological & Chemical Engineering, Chongqing University of Education, Chongqing, 400067
2.
National Supercomputing Center in Shenzhen, Shenzhen, 518055

Corresponding author: Yang Yimeng, yangmeng0306@163.com
Received Date: 16 April 2020
Accepted Date: 10 July 2020

Figures(4)

To study the intrinsic relationship between the structure and its antioxidant activity of dandelion flavonoids from the molecular level, five important flavonoids in dandelion (quercetin, rutin, luteolin, apigenin, diosmetin) were systematically analyzed by density functional theory (DFT) calculations. The optimized geometric configuration, the relative change in energy (ΔH) associated with the formation of various flavonoid radicals, the NBO charges and spin densities analysis of the five aforementioned flavonoids were compared. The results indicated that the order of antioxidant properties is rutin > quercetin > luteolin≫diosmetin > apigenin, the location of phenol hydroxyl group significantly affects the antioxidant properties of dandelion flavonoids. The radical scavenging activity of different reactive site (-OH group) is related to the charges on H atom and the stability of flavonoid radicals, the electron delocalization and intramolecular hydrogen bond finally lead to the high activity of 4'-OH in ring B of dandelion flavonoids.
- Dandelion flavonoids,
- antioxidant properties,
- DFT calculations,
- structure-activities relationship
1. [1]
  Grauso L, Emrick S, de Falco B, et al. Phytochem. Rev., 2019, 18(4): 1115~1132.
2. [2]
  Guo H J, Zhang W D, Jiang Y, et al. Molecules, 2019, 24(8): 1485.
3. [3]
  Panche A N, Diwan A D, Chandra S R, et al. J. Nutr. Sci., 2016, 5: 1~15.
4. [4]
  Pietta P G. J. Nat. Prod., 2000, 63(7): 1035~1042.
5. [5]
  Miller A L. Altern. Med. Rev., 1996, 1(2): 103~111.
6. [6]
  Knekt P, Kumpulainen J, Järvinen R, et al. Am. J. Clin. Nutr., 2002, 76(3): 560~568.
7. [7]
  Huang D, Gu Y. Animal Husband. Feed Sci., 2016, 8(6): 336~343.
8. [8]
  Biel W, Jaroszewska A, Łysoń E, et al. Can. J. Plant Sci., 2017, 97(6): 1165~1174.
9. [9]
  Jędrejek D, Kontek B, Lis B, et al. Chem-Biol. Interact., 2017, 262(25): 29~37.
10. [10]
  Seyoum A, Asres K, El-Fiky F K, et al. Phytochemistry, 2006, 67(18): 2058~2070.
11. [11]
  Sarkar A, Middya T R, Jana A D, et al. J. Mol. Model., 2012, 18(6): 2621~2631.
12. [12]
  Sroka Z, Zbikowska B, Hładyszowski J, et al. J. Mol. Model., 2015, 21(12): 307.
13. [13]
  Chen X, Deng Z Y, Zhang C Y, et al. Food Res. Int., 2018, doi: 10.1016/j.foodres.2018.11.018.
14. [14]
  Boots A W, Haenen G R M M, Bast A. Eur. J. Pharmacol., 2008, 585(2/3): 325~337.
15. [15]
  Yang J, Guo J, Yuan J. LWT-Food Sci. Technol., 2008, 41(6): 1060~1066.
16. [16]
  Romanova D, Vachalkova A, Cipak L, et al. Neoplasma, 2001, 48(2): 104~107.
17. [17]
  González-Castejón M, Visioli F, Rodriguez-Casado A, et al. Nutr. Rev., 2012, 70(9): 534~547.
18. [18]
  Amić D, Davidović-Amić D, Bešlo D et al. Croat. Chem. Acta, 2003, 76(1): 55~61.
19. [19]
  Cotelle N. Curr. Top. Med. Chem., 2001, 1(6): 569~590.
20. [20]
  van Acker S A B E, de Groot M J, van den Berg D J, et al. Chem. Res. Toxicol., 1996, 9(8): 1305~1312.
21. [21]
  Lu T, Chen F W. J. Comput. Chem., 2012, 33(5): 580~592.
22. [22]
  Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian, Inc., Wallingford CT, 2009, Gaussian 09, Revision A.1.
23. [23]
  Zhao Y, Truhlar D G. Theor. Chem. Acc., 2008, 120: 215~241.
24. [24]
  Zhao Y, Truhlar D G. Acc. Chem. Res., 2008, 41(2): 157~167.
25. [25]
  Marenich A V, Cramer C J, Truhlar D G, et al. J. Phys. Chem. B, 2009, 113(18): 6378~6369.
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沈阳化工大学材料科学与工程学院沈阳 110142