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

References

• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Skibola CF, Smith MT. Potential health impacts of excessive flavonoid intake. Free Radic Biol Med 2000; 29: 375–383
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Bokkenheuser VD, Shackleton CH, Winter J. Hydrolysis of dietary flavonoid glycosides by strains of intestinal Bacteroides from humans. Biochem J 1987; 248: 953–956
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Cao G, Sofic E, Prior RL. Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radic Biol Med 1997; 22: 749–760
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Crow JP, Ischiropoulos H. Detection and quantitation of nitrotyrosine residues in proteins: in vivo marker of peroxynitrite. Methods Enzymol 1996; 269: 185–194
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMedGoogle Scholar
• 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
   Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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 lipopolysaccharide as an experimental endotoxic shock model. Infect Immun 1996; 64: 734–738
   PubMed Web of Science ®Google Scholar
• Fang FC. Perspectives series: host/pathogen interactions. Mechanisms of nitric oxide-related antimicrobial activity. J Clin Invest 1997; 99: 2818–2825
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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/lipopolysaccharide-induced fulminant hepatic failure resulting in reduction of lethality. Hepatology 2001; 33: 1441–1450
   PubMedGoogle Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Aniya Y, Koyama T, Miyagi C, Miyahira M, Inomata C, Kinoshita S, Ichiba T. Free radical scavenging and hepatoprotective actions of the medicinal herb, Crassocephalum crepidioides from the Okinawa Islands. Biol Pharm Bull 2005; 28: 19–23
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMedGoogle Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Croft KD. The chemistry and biological effects of flavonoids and phenolic acids. Ann NY Acad Sci 1998; 854: 435–442
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar