Citation: LIU Hui-Qing, YU Mei-Xuan, SONG Jing-Lei, YAN Xi, XU Ning, HAO Hai-Jun. Anti-hemolysis of Human Erythrocytes by Two Daidzein Derivatives Containing Nitrogen[J]. Chinese Journal of Inorganic Chemistry, ;2019, 35(11): 2168-2176. doi: 10.11862/CJIC.2019.240 shu

Anti-hemolysis of Human Erythrocytes by Two Daidzein Derivatives Containing Nitrogen

LIU Hui-Qing ¹ ,
YU Mei-Xuan ¹ ,
SONG Jing-Lei ¹ ,
YAN Xi ^1,, ,
XU Ning ^2,, ,
HAO Hai-Jun ^3,,

1.
College of Chemistry, Beijing Normal University, Beijing 100875, China
2.
Department of Rheumatology and Immunology, Third Hospital of Peking University, Beijing 100083, China
3.
Department of Organic Chemistry, College of Science, Beijing University of Chemical Technology, Beijing 100029, China

Corresponding author: YAN Xi, yanxi@bnu.edu.cn XU Ning, xvning@163.com HAO Hai-Jun, haohaijun@163.com
Received Date: 14 September 2019
Revised Date: 5 October 2019

Figures(6)

Two new daidzein derivatives containing nitrogen, 4', 7-bis(((sodium glycinate)carbonyl)methoxy) isoflavone (L1) and 4', 7-bis((hydrazinocarbonyl) methoxy) isoflavone (L2), have been synthesized and characterized by elemental analysis, IR and ¹H NMR. The antioxidant properties of the daidzein derivatives were studied by evaluating its ability to capture the hydroxyl free radical, the superoxide anion free radical, and to protect erythrocytes of human blood against oxidative damage induced from AAPH (2, 2'-azobis(2-amidinopropane) hydrochloride). Results of the experiments suggest that the daidzein derivatives show excellent antioxidant activity in physiological pH condition compared with vitamin C. Especially in the hydroxyl radical scavenging activity and suppressing the hemolysis of erythrocytes of human blood, the antioxidant capacity of the daidzein derivatives is more outstanding. The IC₅₀ values of the daidzein derivatives were in the range of 0.1~1 μmol·L^-1 on hydroxyl free radical scavenging activity, which was 104 times higher than that of vitamin C.
- daidzein derivatives,
- antioxidant,
- human erythrocytes
1. [1]
  Suzuki Y J, Forman H J, Sevanian A. Free Radical Biol. Med., 1997, 22:269-285 doi: 10.1016/S0891-5849(96)00275-4
2. [2]
  Babior M B. Am. J. Med., 2000, 109:33-44 doi: 10.1016/S0002-9343(00)00481-2
3. [3]
  Gülin I. Toxicology, 2006, 217:213-220 doi: 10.1016/j.tox.2005.09.011
4. [4]
  Halliwell B. Nutr. Rev., 1997, 55:S44-S52
5. [5]
  Comporti M. Lab. Invest., 1985, 53:599-623
6. [6]
  Bulkley G B. Surgery, 1983, 94:407-411
7. [7]
  Dormandy T L. Lancet, 1983, 11:1010-1014
8. [8]
  Slater T F. Biochem. J., 1984, 222:1-15 doi: 10.1042/bj2220001
9. [9]
  Beckman K B, Ames B N. Physiol. Rev., 1998, 78:547-581 doi: 10.1152/physrev.1998.78.2.547
10. [10]
  Wiseman H, Kaur H, Halliwell B. Cancer Lett., 1995, 93:113-120 doi: 10.1016/0304-3835(95)03792-U
11. [11]
  Dirnagl U, Iadecola C, Moskowitz M A. Trends Neurosci., 1999, 22:391-397 doi: 10.1016/S0166-2236(99)01401-0
12. [12]
  Lewen A, Matz P, Chan P H. J. Neurotrauma, 2000, 17:871-890 doi: 10.1089/neu.2000.17.871
13. [13]
  Love S. Brain Pathol., 1999, 9:119-131
14. [14]
  Doble A. Pharmacol. Ther., 1999, 81:163-221 doi: 10.1016/S0163-7258(98)00042-4
15. [15]
  Dyatlov V A, Makovetskaia V V, Leonhardt R, et al. Biol. Med., 1998, 25:793-802
16. [16]
  Yeo J E, Kang S K. Biochim. Biophys. Acta:Mol. Basis Dis., 2007, 1772:1199-1210 doi: 10.1016/j.bbadis.2007.09.004
17. [17]
  Wang T, Gu J, Wu P F, et al. Free Radical Biol. Med., 2009, 47:229-240 doi: 10.1016/j.freeradbiomed.2009.02.027
18. [18]
  Regnström J, Nilsson J, Tornvall P, et al. Lancet, 1992, 339:1183-1186 doi: 10.1016/0140-6736(92)91129-V
19. [19]
  Ross R. Nature, 1993, 362:801-809 doi: 10.1038/362801a0
20. [20]
  Feldmann M, Brennan F M, and Maini R N. Cell, 1996, 85:307-310 doi: 10.1016/S0092-8674(00)81109-5
21. [21]
  Valko M, Rhodes C J, Moncol J, et al. Chem. Biol. Interact., 2006, 160:1-40 doi: 10.1016/j.cbi.2005.12.009
22. [22]
  Valko M, Leibfritz D, Moncol J, et al. Int J Biochem Cell Biol., 2007, 39:44-84 doi: 10.1016/j.biocel.2006.07.001
23. [23]
  De Bandt M, Grossin M, Driss F, et al. Arthritis Rheumatol., 2002, 46:522-532 doi: 10.1002/art.10085
24. [24]
  Gelderman K A, Hultqvist M, Olsson L M, et al. Antioxid. Redox Signaling, 2007, 9:1541-1568 doi: 10.1089/ars.2007.1569
25. [25]
  Sies H. Eur. J. Biochem., 1993, 215:213-219 doi: 10.1111/j.1432-1033.1993.tb18025.x
26. [26]
  Fridovich I. J. Biol. Chem., 1997, 272:18515-18517 doi: 10.1074/jbc.272.30.18515
27. [27]
  Hodis H N, Mack W J, Labree L, et al. JAMA:J. Am. Med. Assoc., 1995, 273:1849-1854 doi: 10.1001/jama.1995.03520470057032
28. [28]
  Cherubini A, Vigna G B, Ruggiero C, et al. Curr. Pharm. Des., 2005, 11:2017-2032 doi: 10.2174/1381612054065783
29. [29]
  Salonen J, Nyyssonen K, Kaikkonen J, et al. Circulation, 2003, 107:947-953 doi: 10.1161/01.CIR.0000050626.25057.51
30. [30]
  Kritharides L, Stocker R. Atherosclerosis, 2002, 164:211-219 doi: 10.1016/S0021-9150(02)00011-4
31. [31]
  Carr A C, Zhu B Z, Frei B. Circ. Res., 2000, 87:349-354 doi: 10.1161/01.RES.87.5.349
32. [32]
  Giugliano D. Cardiovasc. Dis., 2000, 10:38-44
33. [33]
  Wiseman H, O'Reilly J D, Adlercreutz H, et al. Clin. Nutr., 2000, 72:395-400
34. [34]
  Shohami E, Yannai E B, Horowitz M, et al. Metabolism, 1997, 17:1007-1019
35. [35]
  Dieber-Rotheneder M D, Puhl H, Waeg G, et al. Lipid Res., 1991, 32:1325-1332
36. [36]
  Burris R L, Xie C H, Thampi P, et al. Atherosclerosis, 2010, 212:107-115 doi: 10.1016/j.atherosclerosis.2010.05.018
37. [37]
  Tijburg L B M, Wiseman S A, Meijer G W, et al. Atheros-clerosis, 1997, 135:37-47 doi: 10.1016/S0021-9150(97)00139-1
38. [38]
  Anthony M S, Clarkson T B, Bullock B C. Vasc. Biol., 1997, 17:2524-2531 doi: 10.1161/01.ATV.17.11.2524
39. [39]
  Borriello A, Cucciolla V, Della Ragione F, et al. Nutr. Metab. Carbiovasc. Dis., 2010, 20:618-625 doi: 10.1016/j.numecd.2010.07.004
40. [40]
  Kalka-Moll W M, Tzianabos A O. J. Immunol., 2002, 169:6149-6153 doi: 10.4049/jimmunol.169.11.6149
41. [41]
  Mackay C R. Nature, 1999, 401:659-660 doi: 10.1038/44309
42. [42]
  Rich S, McLaughlin V V. J. Circulation, 2003, 108:2184-2190 doi: 10.1161/01.CIR.0000094397.19932.78
43. [43]
  Ball L J, Berge S L. Clin. Geriatr. Med., 2002, 18:485-503 doi: 10.1016/S0749-0690(02)00027-7
44. [44]
  Van den Ende W, Peshev D, De Gara L. Trends Food Sci. Technol., 2011, 22:689-697 doi: 10.1016/j.tifs.2011.07.005
45. [45]
  Yang X F, Guo X Q. Analyst, 2001, 126:928-932 doi: 10.1039/b100085n
46. [46]
  Baxendale J H, Wilson J A. Trans. Faraday Soc., 1957, 53:344-356 doi: 10.1039/tf9575300344
47. [47]
  Hunt J P, Taube H. J. Am. Chem. Soc., 1952, 74:5999-6002 doi: 10.1021/ja01143a052
48. [48]
  Volman D H, Chen J C. J. Am. Chem. Soc., 1959, 81:4141-4144 doi: 10.1021/ja01525a004
49. [49]
  Walter R I. J. Am. Chem. Soc., 1966, 88:1923-1930 doi: 10.1021/ja00961a014
50. [50]
  Wickens A P. Respir. Physiol. Neurobiol., 2001, 128:379-391 doi: 10.1016/S0034-5687(01)00313-9
51. [51]
  Filip R, Sebastian T, Ferraro G, et al. Food Chem. Toxicol., 2007, 45:649-655 doi: 10.1016/j.fct.2006.10.014
52. [52]
  Gao R M, Yuan Z B, Zhao Z Q, et al. Bioelectrochem. Bioenerg., 1998, 45:41-45 doi: 10.1016/S0302-4598(98)00072-5
53. [53]
  Han T, Cheng G, Liu Y, et al. Food Chem. Toxicol., 2012, 50:409-414 doi: 10.1016/j.fct.2011.10.066
54. [54]
  Kunwar A, Mishra B, Barik A, et al. Chem. Res. Toxicol., 2007, 20:1482-1487 doi: 10.1021/tx700137a
55. [55]
  Niki E. Methods Enzymol., 1990, 186:100-108 doi: 10.1016/0076-6879(90)86095-D
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