Neohesperidin Dihydrochalcone versus CCl4-Induced Hepatic Injury through Different Mechanisms: The Implication of Free Radical Scavenging and Nrf2 Activation

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 22, 2015, Pages 5468-5475

  Su, Chuanyang ^a   Xia, Xiaomin ^a   Shi, Qiong ^a   Song, Xiufang ^a   Fu, Juanli ^a   Xiao, Congxue ^a   Chen, Hongjun ^a   Lu, Bin ^a   Sun, Zhiyin ^a   Wu, Shanmei ^a   Yang, Siyu ^a   Li, Xuegang ^a   Ye, Xiaoli ^a   Song, Erqun ^a   Song, Yang ^a  

^a SOUTHWEST UNIVERSITY   (China)

Author keywords

HO 1; Keap1; liver; MAPK; NHDC; NQO1; ubiquitination

Indexed keywords

ANTIOXIDANTS; CHEMICAL ACTIVATION; ENZYME ACTIVITY; LIVER; PIGMENTS;

KEAP1; MAPK; NHDC; NQO1; UBIQUITINATION;

FREE RADICALS;

CITRUS;

CARBON TETRACHLORIDE; CHALCONE DERIVATIVE; HEME OXYGENASE 1; HESPERIDIN; NEOHESPERIDIN DIHYDROCHALCONE; REACTIVE OXYGEN METABOLITE; SCAVENGER; STRESS ACTIVATED PROTEIN KINASE; TRANSCRIPTION FACTOR NRF2;

ANALOGS AND DERIVATIVES; ANIMAL; DRUG EFFECTS; DRUG-INDUCED LIVER INJURY; GENETICS; HUMAN; LIVER; METABOLISM; MOUSE; OXIDATIVE STRESS; SIGNAL TRANSDUCTION;

ANIMALS; CARBON TETRACHLORIDE; CHALCONES; DRUG-INDUCED LIVER INJURY; FREE RADICAL SCAVENGERS; HEME OXYGENASE-1; HESPERIDIN; HUMANS; JNK MITOGEN-ACTIVATED PROTEIN KINASES; LIVER; MICE; NF-E2-RELATED FACTOR 2; OXIDATIVE STRESS; REACTIVE OXYGEN SPECIES; SIGNAL TRANSDUCTION;

EID: 84935862032     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b01750     Document Type: Article

References (34)

1. Weber, L. W.; Boll, M.; Stampfl, A. Hepatotoxicity and mechanism of action of haloalkanes: carbon tetrachloride as a toxicological model Crit. Rev. Toxicol. 2003, 33, 105 - 36 10.1080/713611034
2. Hu, L.; Li, L.; Xu, D.; Xia, X.; Pi, R.; Xu, D.; Wang, W.; Du, H.; Song, E.; Song, Y. Protective effects of neohesperidin dihydrochalcone against carbon tetrachloride-induced oxidative damage in vivo and in vitro Chem.-Biol. Interact. 2014, 213, 51 - 9 10.1016/j.cbi.2014.02.003
3. Kumar, H.; Kim, I. S.; More, S. V.; Kim, B. W.; Choi, D. K. Natural product-derived pharmacological modulators of Nrf2/ARE pathway for chronic diseases Nat. Prod. Rep. 2014, 31, 109 - 39 10.1039/C3NP70065H
4. Jeong, W. S.; Jun, M.; Kong, A. N. Nrf2: a potential molecular target for cancer chemoprevention by natural compounds Antioxid. Redox Signaling 2006, 8, 99 - 106 10.1089/ars.2006.8.99
5. Kim, H. J.; Suh, H. J.; Kim, J. H.; Park, S.; Joo, Y. C.; Kim, J. S. Antioxidant activity of glyceollins derived from soybean elicited with Aspergillus sojae J. Agric. Food Chem. 2010, 58, 11633 - 8 10.1021/jf102829z
6. Sun, J.; He, H.; Xie, B. J. Novel antioxidant peptides from fermented mushroom Ganoderma lucidum J. Agric. Food Chem. 2004, 52, 6646 - 52 10.1021/jf0495136
7. Wang, L.; Tu, Y. C.; Lian, T. W.; Hung, J. T.; Yen, J. H.; Wu, M. J. Distinctive antioxidant and antiinflammatory effects of flavonols J. Agric. Food Chem. 2006, 54, 9798 - 804 10.1021/jf0620719
8. Tanigawa, S.; Fujii, M.; Hou, D. X. Action of Nrf2 and Keap1 in ARE-mediated NQO1 expression by quercetin Free Radical Biol. Med. 2007, 42, 1690 - 703 10.1016/j.freeradbiomed.2007.02.017
9. Su, C.; Zhang, P.; Song, X.; Shi, Q.; Fu, J.; Xia, X.; Bai, H.; Hu, L.; Xu, D.; Song, E.; Song, Y. Tetrachlorobenzoquinone activates nrf2 signaling by keap1 cross-linking and ubiquitin translocation but not keap1-cullin3 complex dissociation Chem. Res. Toxicol. 2015, 28, 765 - 74 10.1021/tx500513v
10. Gulcin, I.; Bursal, E.; Sehitoglu, M. H.; Bilsel, M.; Goren, A. C. Polyphenol contents and antioxidant activity of lyophilized aqueous extract of propolis from Erzurum, Turkey Food Chem. Toxicol. 2010, 48, 2227 - 38 10.1016/j.fct.2010.05.053
11. Kowaltowski, A. J.; Vercesi, A. E. Mitochondrial damage induced by conditions of oxidative stress Free Radical Biol. Med. 1999, 26, 463 - 71 10.1016/S0891-5849(98)00216-0
12. Shackelford, R. E.; Kaufmann, W. K.; Paules, R. S. Oxidative stress and cell cycle checkpoint function Free Radical Biol. Med. 2000, 28, 1387 - 404 10.1016/S0891-5849(00)00224-0
13. Sanders, L. H.; Greenamyre, J. T. Oxidative damage to macromolecules in human Parkinson disease and the rotenone model Free Radical Biol. Med. 2013, 62, 111 - 20 10.1016/j.freeradbiomed.2013.01.003
14. Choi, J. M.; Yoon, B. S.; Lee, S. K.; Hwang, J. K.; Ryang, R. Antioxidant properties of neohesperidin dihydrochalcone: inhibition of hypochlorous acid-induced DNA strand breakage, protein degradation, and cell death Biol. Pharm. Bull. 2007, 30, 324 - 30 10.1248/bpb.30.324
15. Nakamura, Y.; Watanabe, S.; Miyake, N.; Kohno, H.; Osawa, T. Dihydrochalcones: evaluation as novel radical scavenging antioxidants J. Agric. Food Chem. 2003, 51, 3309 - 12 10.1021/jf0341060
16. Klaassen, C. D.; Reisman, S. A. Nrf2 the rescue: effects of the antioxidative/electrophilic response on the liver Toxicol. Appl. Pharmacol. 2010, 244, 57 - 65 10.1016/j.taap.2010.01.013
17. Vasiliou, V.; Ross, D.; Nebert, D. W. Update of the NAD(P)H:quinone oxidoreductase (NQO) gene family Hum. Genomics 2006, 2, 329 - 35 10.1186/1479-7364-2-5-329
18. Donovan, E. L.; McCord, J. M.; Reuland, D. J.; Miller, B. F.; Hamilton, K. L. Phytochemical activation of Nrf2 protects human coronary artery endothelial cells against an oxidative challenge Oxid. Med. Cell. Longevity 2012, 2012, 132931 10.1155/2012/132931
19. Choi, J. H.; Kim, D. W.; Yun, N.; Choi, J. S.; Islam, M. N.; Kim, Y. S.; Lee, S. M. Protective effects of hyperoside against carbon tetrachloride-induced liver damage in mice J. Nat. Prod. 2011, 74, 1055 - 60 10.1021/np200001x
20. Lee, I. C.; Kim, S. H.; Baek, H. S.; Moon, C.; Kim, S. H.; Kim, Y. B.; Yun, W. K.; Kim, H. C.; Kim, J. C. Protective effects of diallyl disulfide on carbon tetrachloride-induced hepatotoxicity through activation of Nrf2 Environ. Toxicol. 2015, 30, 538 - 48 10.1002/tox.21930
21. de Vries, H. E.; Witte, M.; Hondius, D.; Rozemuller, A. J.; Drukarch, B.; Hoozemans, J.; van Horssen, J. Nrf2-induced antioxidant protection: a promising target to counteract ROS-mediated damage in neurodegenerative disease? Free Radical Biol. Med. 2008, 45, 1375 - 83 10.1016/j.freeradbiomed.2008.09.001
22. Kobayashi, A.; Kang, M. I.; Okawa, H.; Ohtsuji, M.; Zenke, Y.; Chiba, T.; Igarashi, K.; Yamamoto, M. Oxidative stress sensor Keap1 functions as an adaptor for Cul3-based E3 ligase to regulate proteasomal degradation of Nrf2 Mol. Cell. Biol. 2004, 24, 7130 - 9 10.1128/MCB.24.16.7130-7139.2004
23. Baird, L.; Dinkova-Kostova, A. T. The cytoprotective role of the Keap1-Nrf2 pathway Arch. Toxicol. 2011, 85, 241 - 72 10.1007/s00204-011-0674-5
24. He, X.; Chen, M. G.; Lin, G. X.; Ma, Q. Arsenic induces NAD(P)H-quinone oxidoreductase I by disrupting the Nrf2 x Keap1 x Cul3 complex and recruiting Nrf2 x Maf to the antioxidant response element enhancer J. Biol. Chem. 2006, 281, 23620 - 31 10.1074/jbc.M604120200
25. Zhang, D. D.; Lo, S. C.; Sun, Z.; Habib, G. M.; Lieberman, M. W.; Hannink, M. Ubiquitination of Keap1, a BTB-Kelch substrate adaptor protein for Cul3, targets Keap1 for degradation by a proteasome-independent pathway J. Biol. Chem. 2005, 280, 30091 - 9 10.1074/jbc.M501279200
26. Zhang, D. D.; Hannink, M. Distinct cysteine residues in Keap1 are required for Keap1-dependent ubiquitination of Nrf2 and for stabilization of Nrf2 by chemopreventive agents and oxidative stress Mol. Cell. Biol. 2003, 23, 8137 - 51 10.1128/MCB.23.22.8137-8151.2003
27. Zhang, D. D.; Lo, S. C.; Cross, J. V.; Templeton, D. J.; Hannink, M. Keap1 is a redox-regulated substrate adaptor protein for a Cul3-dependent ubiquitin ligase complex Mol. Cell. Biol. 2004, 24, 10941 - 53 10.1128/MCB.24.24.10941-10953.2004
28. Gao, L.; Wang, J.; Sekhar, K. R.; Yin, H.; Yared, N. F.; Schneider, S. N.; Sasi, S.; Dalton, T. P.; Anderson, M. E.; Chan, J. Y.; Morrow, J. D.; Freeman, M. L. Novel n-3 fatty acid oxidation products activate Nrf2 by destabilizing the association between Keap1 and Cullin3 J. Biol. Chem. 2007, 282, 2529 - 37 10.1074/jbc.M607622200
29. Satoh, T.; Kosaka, K.; Itoh, K.; Kobayashi, A.; Yamamoto, M.; Shimojo, Y.; Kitajima, C.; Cui, J.; Kamins, J.; Okamoto, S.; Izumi, M.; Shirasawa, T.; Lipton, S. A. Carnosic acid, a catechol-type electrophilic compound, protects neurons both in vitro and in vivo through activation of the Keap1/Nrf2 pathway via S-alkylation of targeted cysteines on Keap1 J. Neurochem. 2008, 104, 1116 - 31 10.1111/j.1471-4159.2007.05039.x
30. Fourquet, S.; Guerois, R.; Biard, D.; Toledano, M. B. Activation of NRF2 by nitrosative agents and H2O2 involves KEAP1 disulfide formation J. Biol. Chem. 2010, 285, 8463 - 71 10.1074/jbc.M109.051714
31. Hong, F.; Sekhar, K. R.; Freeman, M. L.; Liebler, D. C. Specific patterns of electrophile adduction trigger Keap1 ubiquitination and Nrf2 activation J. Biol. Chem. 2005, 280, 31768 - 75 10.1074/jbc.M503346200
32. Hong, F.; Freeman, M. L.; Liebler, D. C. Identification of sensor cysteines in human Keap1 modified by the cancer chemopreventive agent sulforaphane Chem. Res. Toxicol. 2005, 18, 1917 - 26 10.1021/tx0502138
33. Yu, R.; Lei, W.; Mandlekar, S.; Weber, M. J.; Der, C. J.; Wu, J.; Kong, A. N. Role of a mitogen-activated protein kinase pathway in the induction of phase II detoxifying enzymes by chemicals J. Biol. Chem. 1999, 274, 27545 - 52 10.1074/jbc.274.39.27545
34. Yu, R.; Mandlekar, S.; Lei, W.; Fahl, W. E.; Tan, T. H.; Kong, A. N. p38 mitogen-activated protein kinase negatively regulates the induction of phase II drug-metabolizing enzymes that detoxify carcinogens J. Biol. Chem. 2000, 275, 2322 - 7 10.1074/jbc.275.4.2322