Citation: XIE Hu-Jun, MOU Wang-Shu, LIN Fu-Rong, XU Jie-Hui, LEI Qun-Fang. Radical Scavenging Activity of Myricetin[J]. Acta Physico-Chimica Sinica, ;2013, 29(07): 1421-1432. doi: 10.3866/PKU.WHXB201304222 shu

Radical Scavenging Activity of Myricetin

1.
1 Department of Applied Chemistry, Zhejiang ngshang University, Hangzhou 310035, P. R. China;
2 Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China

Received Date: 21 February 2013
Available Online: 22 April 2013
Fund Project: 国家自然科学基金(21203166, 21073164) (21203166, 21073164) 浙江省自然科学基金(Y4100620, LY12B04003) (Y4100620, LY12B04003)浙江省大学生创新基金(2012R408007)资助项目 (2012R408007)

Density functional theory (DFT) calculations have been performed to explore the molecular structure, electronic structure, and O－H bond dissociation enthalpy of myricetin. Possible antioxidation mechanisms between lipid peroxide radical CH₃OO· and myricetin have been discussed. DFT calculations at the M06-2X/6-31++G(d,p) level indicated that the 4'-OH group of myricetin is the most active site on the basis of the stability of dehydrogenated myricetin radicals, O－H bond dissociation enthalpy, and hydrogen abstraction activation barrier, as well as kinetic data for myricetin determined at different temperatures. The relatively high activity of the 4'-OH site can be ascribed to weak hydrogen-bonding interactions between the oxygen radical of the reactive OH group and the adjacent OH group in the B-ring, which is retained upon ing from free myricetin to reactant complex to product according to atoms in molecule (AIM) analysis. The hydrogen-bond helps to stabilize the electronic deficiency generated on the oxygen radical during the hydrogen abstraction reaction. All calculations are in agreement with the structure-activity relationship previously established for myricetin by considering its antioxidant activity. Present calculations provide theoretical basis for the designing new antioxidants.
- DFT calculation,
- Reaction mechanism,
- Myricetin,
- Antioxidant activity,
- Bond dissociation enthalpy
1. [1]
  
  (1) Kuhnau, J. World Rev. Nutr. Diet. 1976, 24, 117.
2. [2]
  (2) Miean, K. H.; Mohamed, S. J. Agric. Food Chem. 2001, 49,3106. doi: 10.1021/jf000892m
3. [3]
  (3) Li, M. J.; Zhang, L. M.; Liu,W. X.; Lu,W. C. Chin. J. Chem. Phys. 2011, 24, 173.
4. [4]
  (4) Rüfer, C. E.; Kulling, S. E. J. Agric. Food Chem. 2006, 54,2926. doi: 10.1021/jf053112o
5. [5]
  (5) Amat, A.; Clementi, C.; De Angelis, F.; Sgamellotti, A.;Fantaccia, S. J. Phys. Chem. A 2009, 113, 15118. doi: 10.1021/jp9052538
6. [6]
  (6) Horvath, C. R.; Martos, P. A.; Saxena, P. K. J. Chromatogr. A2005, 1062, 199. doi: 10.1016/j.chroma.2004.11.030
7. [7]
  (7) Nenadis, N.; Sigalas, M. P. J. Phys. Chem. A 2008, 112, 12196.doi: 10.1021/jp8058905
8. [8]
  (8) Rashid, U.; Anwar, F.; Moser, B. R.; Knothe, G. Bioresour. Technol. 2008, 99, 8175. doi: 10.1016/j.biortech.2008.03.066
9. [9]
  (9) Gunesekaran, R.; Ubeda, A.; Alcaraz, M. J.; Jayaprakasam, R.;Nair, A. G. R. Pharmazie 1993, 48, 230.
10. [10]
  (10) Mehrdad, M.; Zebardast, M.; Abedi, G.; Koupaei, M. N.;Rasouli, H.; Talebi, M. J. Aoac. Int. 2009, 92, 1035.
11. [11]
  (11) Burda, S.; Oleszek,W. J. Agric. Food. Chem. 2001, 49, 2774.doi: 10.1021/jf001413m
12. [12]
  (12) Mira, L.; Fernandez, M. T.; Santos, M.; Rocha, R.; Florencio,M. H.; Jennings, K. R. Free Radic. Res. 2002, 36, 1199.doi: 10.1080/1071576021000016463
13. [13]
  (13) Ko, C. H.; Shen, S. C.; Lee, T. J.; Chen, Y. C. Mol. Cancer Ther.2005, 4, 281.
14. [14]
  (14) Morales, P.; Haza, A. I. J. Appl. Toxicol. 2012, 32, 986.doi: 10.1002/jat.v32.12
15. [15]
  (15) Rasulev, B. F.; Abdullaev, N. D.; Syrov, V. N. Leszczynski, J.QSAR Comb. Sci. 2005, 24, 1056.
16. [16]
  (16) DeToma, A. S.; Choi, J. S.; Braymer, J. J.; Lim, M. H.ChemBioChem 2011, 12, 1198. doi: 10.1002/cbic.v12.8
17. [17]
  (17) Delgado, M. E.; Haza, A. I.; Garcia, A.; Morales, P. Toxicolin. In Vitro 2009, 23, 1292. doi: 10.1016/j.tiv.2009.07.022
18. [18]
  (18) Oyama, Y.; Fuchs, P. A.; Katayama, N.; Noda, K. Brain Res.1994, 635, 125. doi: 10.1016/0006-8993(94)91431-1
19. [19]
  (19) rdon, M. H.; Roedig-Penmanm, A. Chem. Phys. Lipids 1998,97, 79. doi: 10.1016/S0009-3084(98)00098-X
20. [20]
  (20) Lalas, S.; Tsaknis, J. J. Am. Oil. Chem. Soc. 2002, 79, 677.doi: 10.1007/s11746-002-0542-2
21. [21]
  (21) Shahidi, F.;Wanasundara, U. Dev. Food Sci. 1995, 37A, 469.
22. [22]
  (22) Robak, J.; Gryglewski, R. J. Biochem. Pharmacol. 1988, 37,837. doi: 10.1016/0006-2952(88)90169-4
23. [23]
  (23) Angelone, T.; Pasqua, T.; Di Majo, D.; Quintieri, A. M.; Filice,E.; Amodio, N.; Tota, B.; Giammanco, M.; Cerra, M. C. Nutr. Metab. Cardiovas. 2011, 21, 362. doi: 10.1016/j.numecd.2009.10.011
24. [24]
  (24) Wang, Z. H.; Kang, K. A.; Zhang, R.; Piao, M. J.; Jo, S. H.;Kim, J. S.; Kang, S. S.; Lee, J. S.; Park, D. H.; Hyun, J.W.Environ. Toxicol. Phar. 2010, 29, 12. doi: 10.1016/j.etap.2009.08.007
25. [25]
  (25) Moser, B. R. Eur. J. Lipid Sci. Technol. 2008, 110, 1167.doi: 10.1002/ejlt.v110:12
26. [26]
  (26) Justino, G. C.; Vieira, A. J. S. C. J. Mol. Model. 2010, 16, 863.doi: 10.1007/s00894-009-0583-1
27. [27]
  (27) Mendoza-Wilson, A. M.; Sotelo-Mundo, R. R.; Balandran-Quintana, R. R.; Glossman-Mitnik, D.; Santiz- mez, M. A.;Garcia-Orozco, K. D. J. Mol. Struct. 2010, 981, 187.doi: 10.1016/j.molstruc.2010.08.005
28. [28]
  (28) Leon-Carmona, J. R.; Galano, A. J. Phys. Chem. B 2011, 115,4538. doi: 10.1021/jp201383y
29. [29]
  (29) Anouar, E.; Calliste, C. A.; Kosinova, P.; Di Meo, F.; Duroux, J.L.; Champavier, Y.; Marakchi, K.; Trouillas, P. J. Phys. Chem. A2009, 113, 13881. doi: 10.1021/jp906285b
30. [30]
  (30) Sadasivam, K.; Kumaresan, R. Spectrochim. Acta A 2011, 79,282. doi: 10.1016/j.saa.2011.02.042
31. [31]
  (31) Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215.doi: 10.1007/s00214-007-0310-x
32. [32]
  (32) Zhao, Y.; Truhlar, D. G. Accounts Chem. Res. 2008, 41, 157.doi: 10.1021/ar700111a
33. [33]
  (33) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.doi: 10.1021/jp9716997
34. [34]
  (34) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem.2003, 24, 669. doi: 10.1002/jcc.10189
35. [35]
  (35) Frisch, M. J.; Trucks, G..W.; Schlegel, H. B.; et al. Gaussian 09, Revision A.01; Gaussian Inc.:Wallingford, CT, 2009.
36. [36]
  (36) Bader, R. F.W. Chem. Res. 1991, 91, 893.
37. [37]
  (37) Bader, R. F.W. J. Phys. Chem. A 1998, 102, 7314. doi: 10.1021/jp981794v
38. [38]
  (38) Biegler-Konig, F. AIM2000; University of Applied Sciences:Bielefeld, Germany.
39. [39]
  (39) Eyring, H. J. Chem. Phys. 1935, 3, 107. doi: 10.1063/1.1749604
40. [40]
  (40) Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1935, 31, 875.doi: 10.1039/tf9353100875
41. [41]
  (41) Wigner, E. J. Chem. Phys. 1937, 5, 720.
42. [42]
  (42) Russo, N.; Toscano, M.; Uccella, N. J. Agric. Food Chem.2000, 48, 3232. doi: 10.1021/jf990469h
43. [43]
  (43) Bors,W.; Heller,W.; Saran, M. Methods in Enzymology;Academic Press: San Die , 1990; Vol. 186, p 343.
44. [44]
  (44) Leopoldini, M.; Rondinelli, F.; Russo, N.; Toscano, M. J. Agric. Food Chem. 2010, 58, 8862. doi: 10.1021/jf101693k
45. [45]
  (45) Estvez, L.; Mosquera, R. A. J. Phys. Chem. A 2007, 111, 11100.doi: 10.1021/jp074941a
46. [46]
  (46) Xie, H. J.; Lei, Q. F.; Fang,W. J. Acta Chim. Sin. 2010, 68,1467.
47. [47]
  (47) Markovic, Z. S.; Dimitric, J. M.; Markovic, D.; Dolicanin, C.B. Theor. Chem. Acc. 2010, 127, 69. doi: 10.1007/s00214-009-0706-x
48. [48]
  (48) Sadasivam, K.; Kumaresan, R. Comput. Theor. Chem. 2011,963, 227. doi: 10.1016/j.comptc.2010.10.025
49. [49]
  (49) Van Acker, S. A. B. E.; DeGroot, M. J.; Van den Berg, D. J.;Tromp, M. N. J. L.; Den Kelder, G. D. O.; Van der Vijgh,W. J.F.; Bast, A. Chem. Res. Toxicol. 1996, 9, 1305. doi: 10.1021/tx9600964
50. [50]
  (50) Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Free Radic. Biol. Med. 1996, 20, 933. doi: 10.1016/0891-5849(95)02227-9
51. [51]
  (51) Van Acker, S. A. B. E.; Van Den Berg, D. J.; Tromp, M. N. J. L.;Griffioen, D. H.; Van Bennekom,W. P.; Van Der Vijgh,W. J. F.;Bast, A. Free Radic. Biol. Med. 1996, 20, 331. doi: 10.1016/0891-5849(95)02047-0
52. [52]
  (52) Guzman, R.; Santia , C.; Sanchez, M. J. Mol. Struct. 2009,935, 110. doi: 10.1016/j.molstruc.2009.06.048
53. [53]
  (53) Chiodo, S. G.; Leopoldini, M.; Russo, N.; Toscano, M. Phys. Chem. Chem. Phys. 2010, 12, 7662. doi: 10.1039/b924521a
54. [54]
  (54) Li, M. J.; Li, Y. J.; Peng, C. R.; Lu,W. C. Acta Phys. -Chim. Sin. 2010, 26, 466. [李敏杰, 李亚军, 彭淳容, 陆文聪. 物理化学学报, 2010, 26, 466.] doi: 10.3866/PKU.WHXB20100230
55. [55]
  (55) Wright, J. S.; Johnson, E. R.; Di Labio, G. A. J. Am. Chem. Soc.2001, 123, 1173. doi: 10.1021/ja002455u
56. [56]
  (56) Trouillas, P.; Fagnere, C.; Lazzaroni, R.; Calliste, C.; Marfak,A.; Duroux, J. L. Food Chem. 2004, 88, 571. doi: 10.1016/j.foodchem.2004.02.009
57. [57]
  (57) Aparicio, S. Int. J. Mol. Sci. 2010, 11, 2017. doi: 10.3390/ijms11052017
58. [58]
  (58) Zhang, J. H.; Du, F. P.; Peng, B.; Lu, R. H.; Gao, H. X.; Zhou,Z. Q. J. Mol. Struct. -Theochem 2010, 955, 1. doi: 10.1016/j.theochem.2010.04.036
59. [59]
  (59) Kosinova, P.; Di Meo, F.; Anouar, E. H.; Duroux, J. L.;Trouillas, P. Int. J. Quantum Chem. 2011, 11, 1131.
60. [60]
  (60) Zhang, H. Y.;Wang, L. F.; Sun, Y. M. Bioorg. Med. Chem. Lett.2003, 13, 909. doi: 10.1016/S0960-894X(03)00013-1
61. [61]
  (61) Zhang, I. Y.;Wu, J. M.; Luo, Y.; Xu, X. J. Comput. Chem. 2011,32, 1824. doi: 10.1002/jcc.v32.9
62. [62]
  (62) Wu, J. M.; Zhang, I. Y.; Xu, X. ChemPhysChem 2010, 11, 2561.doi: 10.1002/cphc.201000273
63. [63]
  (63) Alecu, I. M.; Truhlar, D. G. J. Phys. Chem. A 2011, 115, 2811.doi: 10.1021/jp110024e
64. [64]
  (64) Dhaouadi, Z.; Nsan u, M.; Garrab, N.; Anouar, E. H.;Marakchi, K.; Lahmar, S. J. Mol. Struct. -Theochem 2009, 904,35. doi: 10.1016/j.theochem.2009.02.034
65. [65]
  (65) Mikulski, D.; rniak, R.; Molski, M. Eur. J. Med. Chem. 2010,45, 1015. doi: 10.1016/j.ejmech.2009.11.044
66. [66]
  (66) Trouillas, P.; Marsal, P.; Siri, D.; Lazzaroni, R.; Duroux, J. L.Food Chem. 2006, 97, 679. doi: 10.1016/j.foodchem.2005.05.042
67. [67]
  (67) Leopoldini, M.; Pitarch, I. P.; Russo, N.; Toscano, M. J. Phys. Chem. A 2004, 108, 92. doi: 10.1021/jp035901j
68. [68]
  (68) Bowater, L.; Fairhurst, S. A.; Just, V. J.; Bornemann, S. FEBS Lett. 2004, 557, 45. doi: 10.1016/S0014-5793(03)01439-X
69. [69]
  (69) Lien, E. J.; Ren, S.; Bui, H. H.;Wang, R. Free Radic. Biol. Med. 1999, 26, 285. doi: 10.1016/S0891-5849(98)00190-7
70. [70]
  (70) Tejero, I.; nzalez-Garcia, N.; nzalez-Lafont, A.; Lluch, J.M. J. Am. Chem. Soc. 2007, 129, 5846. doi: 10.1021/ja063766t
1. [1]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
2. [2]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
3. [3]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
4. [4]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
5. [5]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
6. [6]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
7. [7]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
8. [8]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
9. [9]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
10. [10]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
11. [11]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
12. [12]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
13. [13]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
14. [14]
  Ji-Quan Liu , Huilin Guo , Ying Yang , Xiaohui Guo . Calculation and Discussion of Electrode Potentials in Redox Reactions of Water. University Chemistry, 2024, 39(8): 351-358. doi: 10.3866/PKU.DXHX202401031
15. [15]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
16. [16]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
17. [17]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
18. [18]
  Yi Li , Zhaoxiang Cao , Peng Liu , Xia Wu , Dongju Zhang . Revealing the Coloration and Color Change Mechanisms of the Eriochrome Black T Indicator through Computational Chemistry and UV-Visible Absorption Spectroscopy. University Chemistry, 2025, 40(3): 132-139. doi: 10.12461/PKU.DXHX202405154
19. [19]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
20. [20]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

Get Citation

PDF

XML

Metrics

PDF Downloads(698)
Abstract views(1486)
HTML views(66)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142