Protective activity of (-)- Epicatechin 3-O-gallate against peroxynitrite-mediated renal damage

Free Radical Research

Volumn 37, Issue 5, 2003, Pages 561-571

  Yokozawa, Takako ^a   Rhyu, Dong Young ^a   Cho, Eun Ju ^a   Aoyagi, Kazumasa ^b  

^a UNIVERSITY OF TOYAMA   (Japan)

^b TSUKUBA UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

( ) Epicatechin 3 O gallate; Ischemia reperfusion; Lipopolysaccharide; LLC PK1 cell; Peroxynitrite; Renal damage

Indexed keywords

3 NITROTYROSINE; ANTIOXIDANT; CATALASE; CREATININE; DNA FRAGMENT; EPICATECHIN GALLATE; GLUTATHIONE; GLUTATHIONE PEROXIDASE; LINSIDOMINE; LIPOPOLYSACCHARIDE; METHYLGUANIDINE; NITRATE; PEROXYNITRITE; SUPEROXIDE DISMUTASE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UREA;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; APOPTOSIS; CELL CULTURE; CELL CYCLE G2 PHASE; CELL NUCLEUS; CELL PROTECTION; CELL STRUCTURE; CELL VIABILITY; CONTROLLED STUDY; CREATININE URINE LEVEL; DOSE RESPONSE; DRUG ACTIVITY; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVITY; IN VIVO STUDY; KIDNEY CELL; KIDNEY EPITHELIUM; KIDNEY INJURY; KIDNEY ISCHEMIA; MALE; MITOCHONDRION; MITOSIS INHIBITION; NONHUMAN; PROTEIN BLOOD LEVEL; RAT; REGULATORY MECHANISM; REPERFUSION INJURY; REVIEW; UREA NITROGEN BLOOD LEVEL;

ANIMALS; ANTIOXIDANTS; CASPASES; CATECHIN; CELL CYCLE; CELL LINE; CELL SURVIVAL; DNA FRAGMENTATION; DOSE-RESPONSE RELATIONSHIP, DRUG; FLOW CYTOMETRY; GLUTATHIONE; GLUTATHIONE PEROXIDASE; KIDNEY; LIPID PEROXIDES; LIPOPOLYSACCHARIDES; LLC-PK1 CELLS; MALE; MOLSIDOMINE; PEROXYNITROUS ACID; RATS; RATS, WISTAR; REACTIVE OXYGEN SPECIES; REPERFUSION INJURY; RHODAMINES; SUPEROXIDE DISMUTASE; THIOBARBITURIC ACID REACTIVE SUBSTANCES; TIME FACTORS; TYROSINE;

ANIMALIA;

EID: 0037402497     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/1071576031000083134     Document Type: Review

References (80)

1. Meylan, P.R., Markert, M., Bille, J. and Glauser, M.P. (1989) "Relationship between neutrophil-mediated oxidative injury during acute experimental pyelonephritis and chronic renal scarring", Infect. Immun. 57, 2196-2202.
2. Salas, A., Panes, J., Rosenbloom, C.L., Elizalde, J.I., Anderson, D.C., Granger, D.N. and Pique, J.M. (1999) "Differential effects of a nitric oxide donor on reperfusion-induced microvascular dysfunction in diabetic and non-diabetic rats", Diabetologia 42, 1350-1358.
3. Noiri, E., Nakao, A., Uchida, K., Tsukahara, H., Ohno, M., Fujita, T., Brodsky, S. and Goligorsky, M.S. (2001) "Oxidative and nitrosative stress in acute renal ischemia", Am. J. Physiol. 281, F948-F957.
4. Wojcicka, G. and Beltowski, J. (2001) "Oxidative stress in glomerulonephritis", Postepy Hig. Med. Dosw. 55, 855-869.
5. Kaplowitz, N. (2002) "Biochemical and cellular mechanisms of toxic liver injury", Semin. Liver Dis. 22, 137-144.
6. Radi, R., Beckman, J.S., Bush, K.M. and Freeman, B.A. (1991) "Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide", Arch. Biochem. Biophys. 288, 481-487.
7. Douki, T., Cadet, J. and Ames, B.N. (1996) "An adduct between peroxynitrite and 2′-deoxyguanosine: 4,5-dihydro-5-hydroxy-4-(nitrosooxy)-2′-deoxyguanosine", Chem. Res. Toxicol. 9, 3-7.
8. Koppenol, W.H., Moreno, J.J., Pryor, W.A., Ischiropoulos, H. and Beckman, J.S. (1992) "Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide", Chem. Res. Toxicol. 5, 834-842.
9. Mallozzi, C., Di Stasi, M.A. and Minetti, M. (2001) "Peroxynitrite-dependent activation of src tyrosine kinase lyn and hck in erythrocytes is under mechanistically different pathways of redox control", Free Radic. Biol. Med. 30, 1108-1117.
10. Radi, R., Cassina, A. and Hodara, R. (2002) "Nitric oxide and peroxynitrite interactions with mitochondria", Biol. Chem. 383, 401-409.
11. Oura, H., Zheng, P.D. and Yokozawa, T. (1984) "Effect of Ompi-to in rats with chronic renal failure", J. Med. Pharm. Soc. WAKAN-YAKU 1, 209-217.
12. Yokozawa, T., Dong, E., Liu, Z.W. and Oura, H. (1996) "Antiperoxiation activity of Wen-Pi-Tang in vitro", Nat. Med. 50, 243-246.
13. Yokozawa, T., Sekiya, M., Rhyu, D.Y., Hattori, M. and Chung, H.Y. (2000) "Radical-scavenging activity of Wen-Pi-Tang and its component crude drugs: with special reference to the effects on nitric oxide, superoxide and peroxynitrite", J. Trad. Med. 17, 41-47.
14. Yokozawa, T., Rhyu, D.Y. and Owada, S. (2001) "Increase of radical in rats with adenine-induced renal failure is suppressed by Wen-Pi-Tang", J. Trad. Med. 18, 147-153.
15. Yokozawa, T., Suzuki, N., Zheng, P.D., Oura, H. and Nishioka, I. (1994) "Effect of orally administered rhubarb extract in rats with chronic renal failure", Chem. Pharm. Bull. 32, 4506-4513.
16. Yokozawa, T., Fujioka, K., Oura, H., Nonaka, G. and Nishioka, I. (1991) "Effects of rhubarb tannins on uremic toxins", Nephron 58, 155-160.
17. Yokozawa, T., Chen, C.P., Tanaka, T. and Kouno, I. (1998) "Isolation from Wen-Pi-Tang of the active principles possessing antioxidation and radical-scavenging activities", Phytomedicine 5, 367-373.
18. Nanjo, F., Goto, K., Seto, R., Suzuki, M., Sakai, M. and Hara, Y. (1996) "Scavenging effects of tea catechins and their derivatives on 1,1-diphenyl-2-picrylhydrazyl radical", Free Radic. Biol. Med. 21, 895-902.
19. Chung, H.Y., Yokozawa, T., Soung, D.Y., Kye, I.S., No, J.K. and Baek, B.S. (1998) "Peroxynitrite-scavenging activity of green tea tannin", J. Agric. Food Chem. 46, 4484-4486.
20. Nonaka, G., Nishioka, I., Nagasawa, T. and Oura, H. (1981) "Tannins and related compounds. I. Rhubarb (1)", Chem. Pharm. Bull. 29, 2862-2870.
21. Yokozawa, T., Chen, C.P., Rhyu, D.Y., Tanaka, T., Park, J.C. and Kitani, K. (2002) "Potential of sanguiin H-6 against oxidative damage in renal mitochondria and apoptosis mediated by peroxynitrite in vivo", Nephron 92, 133-141.
22. van der Vliet, A., O'Neill, C.A., Halliwell, B., Cross, C.E. and Kaur, H. (1994) "Aromatic hydroxylation and nitration of phenylalanine and tyrosine by peroxynitrite: evidence for hydroxyl radical production from peroxynitrite", FEBS Lett. 339, 89-92.
23. Kaur, H., Lyras, L., Jenner, P. and Halliwell, B. (1998) "Artefacts in HPLC detection of 3-nitrotyrosine in human brain tissue", J. Neurochem. 70, 2220-2223.
24. Elstner, E.F. and Heupel, A. (1976) "Inhibition of nitrite formation from hydroxylammonium chloride: a simple assay for superoxide dismutase", Anal. Biochem. 70, 616-620.
25. Oyanagui, Y. (1984) "Reevaluation of assay methods and establishment of kit for superoxide dismutase activity", Anal. Biochem. 142, 290-296.
26. Aebi, H. (1974) Γatalase", In: Bergmeyer, H.U., ed, Methods of Enzymatic Analysis (Verlag Chemie, New York), pp 673-684.
27. Hafeman, D.G., Sunde, R.A. and Hoekstra, W.G. (1974) "Effect of dietary selenium on erythrocyte and liver glutathione peroxidase in the rat", J. Nutr. 104, 580-587.
28. Itzhaki, R.F. and Gill, D.M. (1964) "A micro-biuret method for estimating proteins", Anal. Biochem. 9, 401-410.
29. Jung, K. and Pergande, M. (1985) "Influence of cyclosporin A on the respiration of isolated rat kidney mitochondria", FEBS Lett. 183, 167-169.
30. Mihara, M. and Uchiyama, M. (1978) "Determination of malonaldehyde precursor in tissues by thiobarbituric acid test", Anal. Biochem. 86, 271-278.
31. Floreani, M., Petrone, M., Debetto, P. and Palatini, P. (1997) "A comparison between different methods for the determination of reduced and oxidized glutathione in mammalian tissues", Free Radic. Res. 26, 449-455.
32. Higashidate, S., Maekubo, T., Saito, M., Senda, M. and Hoshino, T. (1984) "Rapid and highly sensitive method for the determination of guanidino compounds in body fluids", Bunseki Kagaku 33, 366-370.
33. Haddad, I.Y., Crow, J.P., Hu, P., Ye, Y., Beckman, J. and Matalon, S. (1994) "Concurrent generation of nitric oxide and superoxide damages surfactant protein A", Am. J. Physiol. 267, L242-L249.
34. Mosmann, T. (1983) "Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays", J. Immunol. Methods 65, 55-63.
35. Sellins, K.S. and Cohen, J.J. (1987) "Gene induction by γ-irradiation leads to DNA fragmentation in lymphocytes", J. Immunol. 139, 3199-3206.
36. Burton, K. (1956) "A study of the conditions and mechanism of the diphenylamine reaction for the colorimetric estimation of deoxyribonucleic acid", Biochem. J. 62, 315-323.
37. Fabisiak, J.P., Kagan, V.E., Ritov, V.B., Johnson, D.E. and Lazo, J.S. (1997) "Bcl-2 inhibits selective oxidation and externalization of phosphatidylserine during paraquat-induced apoptosis", Am. J. Physiol. 272, C675-C684.
38. Block, A.L., Bauer, K.D., Williams, T.J. and Seidenfeld, J. (1987) "Experimental parameters and a biological standard for acridine orange detection of drug-induced alterations in chromatin condensation", Cytometry 8, 163-169.
39. Ho, H.Y., Cheng, M.L., Lu, F.J., Chou, Y.H., Stern, A., Liang, C.M. and Chiu, D.T. (2000) "Enhanced oxidative stress and accelerated cellular senescence in glucose-6-phosphate dehydrogenase (G6PD)-deficient human fibroblasts", Free Radic. Biol. Med. 29, 156-169.
40. Lin, Y.L., Juan, I.M., Chen, Y.L., Liang, Y.C. and Lin, J.K. (1996) "Composition of polyphenols in fresh tea leaves and associations of their oxygen-radical-absorbing capacity with antiproliferative actions in fibroblast cells", J. Agric. Food Chem. 44, 1387-1394.
41. Jain, A.K., Shimoi, K., Nakamura, Y., Kada, T., Hara, Y. and Tomita, I. (1989) "Crude tea extracts decrease the mutagenic activity of N-methyl-N′-nitro-N-nitrosoguanidine in vitro and in intragastric tract of rats", Mutat. Res. 210, 1-8.
42. Wang, Z.Y., Wang, L.D., Lee, M.J., Ho, C.T., Huang, M.T., Conney, A.H. and Yang, C.S. (1995) "Inhibition of N-nitrosomethylbenzylamine-induced esophageal tumorigenesis in rats by green and black tea", Carcinogenesis 16, 2143-2148.
43. Yang, G., Wang, Z.Y., Kim, S., Liao, J., Seril, D.N., Chen, X., Smith, T.J. and Yang, C.S. (1997) "Characterization of early pulmonary hyperproliferation and tumor progression and their inhibition by black tea in a 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis model with A/J mice", Cancer Res. 57, 1889-1894.
44. Sano, M., Suzuki, M., Miyase, T., Yoshino, K. and Maeda-Yamamoto, M. (1999) "Novel antiallergic catechin derivatives isolated from oolong tea", J. Agric. Food Chem. 47, 1906-1910.
45. Yoshino, K., Nakamura, Y., Ikeya, H., Sei, T., Inoue, A., Sano, M. and Tomita, I. (1996) "Antimicrobial activity of tea extracts on carcinogenic bacterium (Streptococcus mutants)", J. Food Hyg. Soc. Jpn. 37, 104-108.
46. Miura, Y., Chiba, T., Tomita, I., Koizumi, H., Miura, S., Umegaki, K., Hara, Y., Ikeda, M. and Tomita, T. (2001) "Tea catechins prevent the development of atherosclerosis in apoprotein E-deficient mice", J. Nutr. 131, 27-32.
47. Ischiropoulos, H., al-Mehdi, A.B. and Fisher, A.B. (1995) "Reactive species in ischemic rat lung injury: contribution of peroxynitrite", Am. J. Physiol. 269, L158-L164.
48. Chiao, H., Kohda, Y., McLeroy, P., Craig, L., Housini, I. and Star, R.A. (1997) "α-Melanocyte-stimulating hormone protects against renal injury after ischemia in mice and rat", J. Clin. Investig. 99, 1165-1172.
49. Bian, K., Davis, K., Kuret, J., Binder, L. and Murad, F. (1999) "Nitrotyrosine formation with endotoxin-induced kidney injury detected by immunohistochemistry", Am. J. Physiol. 277, F33-F40.
50. Venditti, P., Agnisola, C. and Meo, S.D. (2002) "Effect of ischemia-reperfusion on heart mitochondria from hyperthyroid rats", Cardiovasc. Res. 56, 76-85.
51. Chatterjee, P.K., Brown, P.A.J., Cuzzocrea, S., Zacharowski, K., Stewart, K.N., Mota-Filipe, H., McDonald, M.C. and Thiemermann, C. (2001) "Calpain inhibitor-1 reduces renal ischemia/reperfusion injury in the rat", Kidney Int. 59, 2073-2083.
52. Depre, C., Havaux, X., Renkin, J., Vanoverschelde, J.L. and Wijns, W. (1999) "Expression of inducible nitric oxide synthase in human coronary atherosclerotic plaque", Cardiovasc. Res. 41, 465-472.
53. Whiteman, M. and Halliwell, B. (1996) "Protection against peroxynitrite-dependent tyrosine nitration and alpha 1-antiproteinase inactivation by ascorbic acid. A comparison with other biological antioxidants", Free Radic. Res. 25, 275-283.
54. Gobe, G., Willgoss, D., Hogg, N., Schoch, E. and Endre, Z. (1999) "Cell survival or death in renal tubular epithelium after ischemia-reperfusion injury", Kidney Int. 56, 1299-1304.
55. Schena, F.P, Grandaliano, G. and Gesualdo, L. (2001) "The role of tubular cells in the progression of renal damage: guilty or innocent?", Renal Fail. 23, 589-596.
56. Pautz, A., Franzen, R., Dorsch, S., Boddinghaus, B., Briner, V.A., Pfeilschifter, J. and Huwiler, A. (2002) "Cross-talk between nitric oxide and superoxide determines ceramide formation and apoptosis in glomerular cells", Kidney Int. 61, 790-796.
57. Castro, L.A., Robalinho, R.L., Cayota, A., Meneghini, R. and Radi, R. (1998) "Nitric oxide and peroxynitrite-dependent aconitase inactivation and iron-regulatory protein-1 activation in mammalian fibroblasts", Arch. Biochem. Biophys. 359, 215-224.
58. B site", J. Biol. Chem. 274, 35763-35767.
59. Poderoso, J.J., Carreras, M.C., Schopfer, F., Lisdero, C.L., Riobo, N.A., Giulivi, C., Boveris, A.D., Boveris, A. and Cadenas, E. (1999) "The reaction of nitric oxide with ubiquinol: kinetic properties and biological significance", Free Radic. Biol. Med. 26, 925-935.
60. Lizasoain, I., Moro, M.A., Knowles, R.G., Darley-Usmar, V. and Moncada, S. (1996) "Nitric oxide and peroxynitrite exert distinct effects on mitochondrial respiration which are differentially blocked by glutathione or glucose", Biochem. J. 314, 877-880.
61. Quijano, C., Alvarez, B., Gatti, R.M., Augusto, O. and Radi, R. (1997) "Pathways of peroxynitrite oxidation of thiol groups", Biochem. J. 322, 167-173.
62. Yen, G.C. and Lai, H.H. (2002) "Inhibitory effects of isoflavones on nitric oxide- or peroxynitrite-mediated DNA damage in RAW 264.7 cells and phiX 174 DNA", Food Chem. Toxicol. 40, 1433-1440.
63. Paller, M.S. (1988) "Renal work, glutathione and susceptibility to free radical-mediated postischemic injury", Kidney Int. 33, 843-849.
64. Brezis, M., Rosen, S., Silva, P. and Epstein, F.H. (1983) "Selective glutathione depletion on function and structure of the isolated perfused rat kidney", Kidney Int. 24, 178-184.
65. Scott, B.C., Butler, J., Halliwell, B. and Aruoma, O.I. (1993) "Evaluation of the antioxidant actions of ferulic acid and catechins", Free Radic. Res. Commun. 19, 241-253.
66. Hanasaki, Y., Ogawa, S. and Fukui, S. (1994) "The correlation between active oxygens scavenging and antioxidative effects of flavonoids", Free Radic. Biol. Med. 16, 845-850.
67. Kashima, M. (1999) "Effects of catechins on superoxide and hydroxyl radical", Chem. Pharm. Bull. 47, 279-283.
68. Depner, T.A. and Gulyassy, P.F. (1979) "Chronic renal failure", In: Earley, L.E. and Gottschalk, C.W., eds, Strauss and Welt's Diseases of the Kidney (Little, Brown and Company, Boston), pp 211-262.
69. Fujitsuka, N., Yokozawa, T., Oura, H., Nakamura, K. and Ienaga, K. (1994) "Major role of hydroxyl radical in the conversion of creatinine to creatol", Nephron 68, 280-281.
70. Yokozawa, T., Suzuki, N., Okuda, I., Oura, H. and Nishioka, I. (1985) "Uremia-preventive effect of rhubarb extract in rats", J. Med. Pharm. Soc. WAKAN-YAKU 2, 344-350.
71. Yokozawa, T., Fujioka, K., Oura, H., Nonaka, G. and Nishioka, I. (1993) "Effects of rhubarb tannins on renal function in rats with renal failure", Jpn. J. Nephrol. 35, 13-18.
72. Lin, K.T., Xue, J.Y., Nomen, M., Spur, B. and Wong, P.Y. (1995) "Peroxynitrite-induced apoptosis in HL-60 cells", J. Biol. Chem. 270, 16487-16490.
73. Beckman, J.S. and Koppenol, W.H. (1996) "Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and the ugly", Am. J. Physiol. 271, C1424-C1437.
74. Lieberthal, W. and Levine, J.S. (1996) "Mechanisms of apoptosis and its potential role in renal tubular epithelial cell injury", Am. J. Physiol. 271, F477-F488.
75. Sandoval, M., Zhang, X.J., Liu, X., Mannick, E.E., Clark, D.A. and Miller, M.J. (1997) "Peroxynitrite-induced apoptosis in T84 and RAW 264.7 cells: attenuation by L-ascorbic acid", Free Radic. Biol. Med. 22, 489-495.
76. Patel, R.P., McAndrew, J., Sellak, H., White, C.R., Jo, H., Freeman, B.A. and Darley-Usmar, V.M. (1999) "Biological aspects of reactive nitrogen species", Biochim. Biophys. Acta 1411, 385-400.
77. Doulias, P.T., Barbouti, A., Galaris, D. and Ischiropoulos, H. (2001) "SIN-1-induced DNA damage in isolated human peripheral blood lymphocytes as assessed by single cell gel electrophoresis (comet assay)", Free Radic. Biol. Med. 30, 679-685.
78. Chen, C.P., Yokozawa, T. and Tanaka, T. (1999) "Protective effect of Sanguisorbae Radix against apoptosis and function of renal tissues subjected to ischemia-reperfusion", J. Trad. Med. 16, 97-101.
79. Poot, M., Schindler, D., Kubbies, M., Hoehn, H. and Rabinovitch, P.S. (1988) "Bromodeoxyuridine amplifies the inhibitory effect of oxygen on cell proliferation", Cytometry 9, 332-338.
80. Poot, M. (1991) "Oxidants and antioxidants in proliferative senescence", Mutat. Res. 256, 177-189.