Quercetin metabolites and protection against peroxynitrite-induced oxidative hepatic injury in rats

Free Radical Research

Volumn 43, Issue 10, 2009, Pages 913-921

  Yokoyama, Akiyuki ^a   Sakakibara, Hiroyuki ^a   Crozier, Alan ^b   Kawai, Yoshichika ^c   Matsui, Asako ^a   Terao, Junji ^c   Kumazawa, Shigenori ^a   Shimoi, Kayoko ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

^c UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Nitrotyrosine; Peroxynitrite induced oxidative hepatotoxicity; Quercetin glycosides; Quercetin metabolites; Quercetin 3 sulphate; Quercetin 3 glucuronide

Indexed keywords

3 HYDROXYPHENYLACETIC ACID; 3 NITROTYROSINE; 3,4 DIHYDROXYPHENYLACETIC ACID; 4 G ALPHA DEXTRO GLUCOPYRANOSYLRUTIN; ALANINE AMINOTRANSFERASE; ANTIOXIDANT; ASPARTATE AMINOTRANSFERASE; DIHYDRO META COUMARIC ACID; GALACTOSAMINE; HOMOVANILLIC ACID; LIPOPOLYSACCHARIDE; PEROXYNITRITE; PROTOCATECHUIC ACID; QUERCETIN 3 O GLUCURONIDE; QUERCETIN 3' O SULPHATE; QUERCETIN DERIVATIVE; SERUM ALBUMIN; UNCLASSIFIED DRUG;

ALANINE AMINOTRANSFERASE BLOOD LEVEL; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIOXIDANT ACTIVITY; ARTICLE; ASPARTATE AMINOTRANSFERASE BLOOD LEVEL; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; IN VITRO STUDY; IN VIVO STUDY; LIVER INJURY; LIVER PROTECTION; LIVER TOXICITY; MALE; METABOLITE; NONHUMAN; OXIDATIVE STRESS; RAT;

ANIMALS; GALACTOSAMINE; HUMANS; LIPOPOLYSACCHARIDES; LIVER; LIVER FAILURE, ACUTE; MALE; OXIDATIVE STRESS; PEROXYNITROUS ACID; QUERCETIN; RATS; RATS, SPRAGUE-DAWLEY; TYROSINE;

RATTUS;

EID: 70450273254     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760903137010     Document Type: Article

References (40)

1. Sakakibara H, Honda Y, Nakagawa S, Ashida H, Kanazawa K. Simultaneous determination of all polyphenols in vegetables, fruits, and teas. J Agric Food Chem 2003;51:571-581.
2. Sakakibara H, Ashida H, Kanazawa K. A novel method using 8-hydroperoxy-2?-deoxyguanosine formation for evaluating antioxidative potency. Free Radic Res 2002;36:307-316.
3. Hertog MG, Kromhout D, Aravanis C, Blackburn H, Buzina R, Fidanza F, Giampaoli S, Jansen A, Menotti A, Nedeljkovic S, Pekkarinen M, Simic BS, Toshima H, Feskens EJ, Hollman PC, Katan MB. Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study. Arch Intern Med 1995;155:381-386.
4. Skibola CF, Smith MT. Potential health impacts of excessive flavonoid intake. Free Radic Biol Med 2000;29:375-383.
5. de Boer VC, Dihal AA, van der Woude H, Arts IC, Wolffram S, Alink GM, Rietjens IM, Keijer J, Hollman PC. Tissue distribution of quercetin in rats and pigs. J Nutr 2005;135: 1718-1725.
6. Bokkenheuser VD, Shackleton CH, Winter J. Hydrolysis of dietary flavonoid glycosides by strains of intestinal Bacteroides from humans. Biochem J 1987;248:953-956.
7. Day AJ, Mellon F, Barron D, Sarrazin G, Morgan MR, Williamson G. Human metabolism of dietary flavonoids: identification of plasma metabolites of quercetin. Free Radic Res 2001;35:941-952.
8. Moon JH, Tsushida T, Nakahara K, Terao J. Identification of quercetin 3-O-beta-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Free Radic Biol Med 2001;30:1274-1285.
9. Mullen W, Boitier A, Stewart AJ, Crozier A. Flavonoid metabolites in human plasma and urine after the consumption of red onions: analysis by liquid chromatography with photodiode array and full scan tandem mass spectrometric detection. J Chromatogr A 2004;1058:163-168.
10. Cao G, Sofic E, Prior RL. Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radic Biol Med 1997;22:749-760.
11. Sadeghipour M, Terreux R, Phipps J. Flavonoids and tyrosine nitration: structure-activity relationship correlation with enthalpy of formation. Toxicol In Vitro 2005;19:155-165.
12. Gross M, Pfeiffer M, Martini M, Campbell D, Slavin J, Potter J. The quantitation of metabolites of quercetin flavonols in human urine. Cancer Epidemiol Biomarkers Prev 1996;5:711-720.
13. Mullen W, Rouanet JM, Auger C, Teissedre PL, Caldwell ST, Hartley RC, Lean ME, Edwards CA, Crozier A. Bioavailability of [2-(14)C]quercetin-4?- glucoside in rats. J Agric Food Chem 2008;56:12127-12137.
14. Williamson G, Barron D, Shimoi K, Terao J. In vitro biological properties of flavonoid conjugates found in vivo. Free Radic Res 2005;39:457-469
15. Crow JP, Ischiropoulos H. Detection and quantitation of nitrotyrosine residues in proteins: in vivo marker of peroxyni-trite. Methods Enzymol 1996;269:185-194.
16. Pannala AS, Razaq R, Halliwell B, Singh S, Rice-Evans CA. Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates: nitration or electron donation? Free Radic Biol Med 1998;24:594-606.
17. Mesenge C, Charriaut-Marlangue C, Verrecchia C, Allix M, Boulu RR, Plotkine M. Reduction of tyrosine nitration after N(omega)-nitro-L-arginine- methylester treatment of mice with traumatic brain injury. Eur J Pharmacol 1998;353: 53-57.
18. Neumann P, Gertzberg N, Vaughan E, Weisbrot J, Woodburn R, Lambert W, Johnson A. Peroxynitrite mediates TNF-alpha-induced endothelial barrier dysfunction and nitration of actin. Am J Physiol Lung Cell Mol Physiol 2006;290: L674-L684.
19. Ippoushi K, Azuma K, Ito H, Horie H, Higashio H. [6]-Gingerol inhibits nitric oxide synthesis in activated J774.1 mouse macrophages and prevents peroxynitrite-induced oxidation and nitration reactions. Life Sci 2003;73:3427-3437.
20. Hayashi T, Suda K, Imai H, Era S. Simple and sensitive high-performance liquid chromatographic method for the investigation of dynamic changes in the redox state of rat serum albumin. J Chromatogr B Analyt Technol Biomed Life Sci 2002;772:139-146.
21. Morikawa A, Sugiyama T, Kato Y, Koide N, Jiang GZ, Takahashi K, Tamada Y, Yokochi T Apoptotic cell death in the response of D-galactosamine-sensitized mice to lipopoly-saccharide as an experimental endotoxic shock model. Infect Immun 1996;64:734-738.
22. Fang FC. Perspectives series: host/pathogen interactions. Mechanisms of nitric oxide-related antimicrobial activity. J Clin Invest 1997;99:2818-2825.
23. Ischiropoulos H, Zhu L, Chen J, Tsai M, Martin JC, Smith CD, Beckman JS. Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch Biochem Biophys 1992;298:431-437
24. Nakama T, Hirono S, Moriuchi A, Hasuike S, Nagata K, Hori T, Ido A, Hayashi K, Tsubouchi H. Etoposide prevents apoptosis in mouse liver with D-galactosamine/lipopolysac-charide-induced fulminant hepatic failure resulting in reduction of lethality. Hepatology 2001;33:1441-1450.
25. Wang F, Wen T, Chen XY, Wu H. Protective effects of pirfenidone on D-galactosamine and lipopolysaccharide-induced acute hepatotoxicity in rats. Inflamm Res 2008;57: 183-188.
26. Aniya Y, Koyama T, Miyagi C, Miyahira M, Inomata C, Kinoshita S, Ichiba T Free radical scavenging and hepato-protective actions of the medicinal herb, Crassocephalum crepidioides from the Okinawa Islands. Biol Pharm Bull 2005;28:19-23.
27. Wen T, Wu ZM, Liu Y, Tan YF, Ren F, Wu H. Upregulation of heme oxygenase-1 with hemin prevents D-galactosamine and lipopolysaccharide-induced acute hepatic injury in rats. Toxicology 2007;237:184-193. (Pubitemid 47031416)
28. Neihorster M, Inoue M, Wendel A. A link between extracellular reactive oxygen and endotoxin-induced release of tumour necrosis factor alpha in vivo. Biochem Pharmacol 1992;43:1151-1154.
29. Shiratori Y, Kawase T, Shiina S, Okano K, Sugimoto T, Teraoka H, Matano S, Matsumoto K, Kamii K. Modulation of hepatotoxicity by macrophages in the liver. Hepatology 1988;8:815-821.
30. Shimoi K, Shen B, Toyokuni S, Mochizuki R, Furugori M, Kinae N. Protection by alpha G-rutin, a water-soluble antioxidant flavonoid, against renal damage in mice treated with ferric nitrilotriacetate. Jpn J Cancer Res 1997;88: 453-460
31. Shimoi K, Yoshizumi K, Kido T, Usui Y, Yumoto T Absorption and urinary excretion of quercetin, rutin, and alphaG-rutin, a water soluble flavonoid, in rats. J Agric Food Chem 2003;51:2785-2789.
32. Jiao K, Mandapati S, Skipper PL, Tannenbaum SR, Wishnok JS. Site-selective nitration of tyrosine in human serum albumin by peroxynitrite. Anal Biochem 2001;293:43-52.
33. Shirai M, Moon JH, Tsushida T, Terao J. Inhibitory effect of a quercetin metabolite, quercetin 3-O-beta-D-glucuronide, on lipid peroxidation in liposomal membranes. J Agric Food Chem 2001;49:5602-5608.
34. Janisch KM, Williamson G, Needs P, Plumb GW. Properties of quercetin conjugates: modulation of LDL oxidation and binding to human serum albumin. Free Radic Res 2004;38: 877-884.
35. Brunmark P, Harriman S, Skipper PL, Wishnok JS, Amin S, Tannenbaum SR. Identification of subdomain IB in human serum albumin as a major binding site for polycyclic aromatic hydrocarbon epoxides. Chem Res Toxicol 1997;10:880-886.
36. Shimoi K, Saka N, Nozawa R, Sato M, Amano I, Nakayama T, Kinae N. Deglucuronidation of a flavonoid, luteolin monoglucuronide, during inflammation. Drug Metab Dispos 2001;29:1521-1524.
37. Croft KD. The chemistry and biological effects of flavonoids and phenolic acids. Ann NY Acad Sci 1998;854:435-442.
38. Hataishi R, Kobayashi H, Takahashi Y, Hirano S, Zapol WM, Jones RC. Myeloperoxidase-associated tyrosine nitration after intratracheal administration of lipopolysaccharide in rats. Anesthesiology 2002;97:887-895.
39. Sampson JB, Ye Y, Rosen H, Beckman JS. Myeloperoxidase and horseradish peroxidase catalyze tyrosine nitration in proteins from nitrite and hydrogen peroxide. Arch Biochem Biophys 1998;356:207-213.
40. Shiba Y, Kinoshita T, Chuman H, Taketani Y, Takeda E, Kato Y, Naito M, Kawabata K, Ishisaka A, Terao J, Kawai Y. Flavonoids as substrates and inhibitors of myeloperoxidase: molecular actions of aglycone and metabolites. Chem Res Toxicol 2008;21:1600-1609.