Effect of a conjugated quercetin metabolite, quercetin 3-glucuronide, on lipid hydroperoxide-dependent formation of reactive oxygen species in differentiated PC-12 cells

References

• Herrmasnn K. Flavonoids and flavones in food plants: A review. J Food Technol 1976; 11: 433–448
   Google Scholar
• Hertog MG, Kromhout D, Aravanis C, Blackburn H, Buzina D, Fidanza F, Giampauli S, Jansen A, Menott A, Nedeljkovic S, et al. Flavonoids 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
• Arts ICW, Hollman PCH. Polyphenols and disease risk in epidemiologic studies. Am J Clin Nutr 2005; 81: 317s–325s
   PubMed Web of Science ®Google Scholar
• Perrig WJ, Perrig P, Stahelin HB. The relation between antioxidants and memory performance in old and very old. J Am Geriatr Soc 1997; 45: 718–724
   PubMed Web of Science ®Google Scholar
• Perkins AJ, Hendrie HC, Callahan CM, Gao S, Unverzagt FW, Xu Y, Hall KS, Hui SL. Association of antioxidant with the memory in a multiethnic elderly sample using the Third National Health and Nutrition Examination survey. Am J Epidemiol 1999; 50: 37–44
   Google Scholar
• Smith MA, Rottkamp CA, Nunomura A, Raina AK, Perry G. Oxidative stress in Alzheimer's disease. Biochim Biophys Acta 2000; 1502: 139–144
   PubMed Web of Science ®Google Scholar
• Youdim KA, Joseph JA. A possible emerging role of phytochemicals in improvingage-related neurological dysfunctions: A multiplicity of effects. Free Radic Biol Med 2001; 30: 583–594
   PubMed Web of Science ®Google Scholar
• Wang H, Joseph JA. Structure–activity relationships of quercetin in antagonizing hydrogen peroxide-induced calcium dysregulation in PC12 cells. Free Radic Biol Med 1999; 27: 683–694
   PubMed Web of Science ®Google Scholar
• Murota K, Terao J. Antioxidative flavonoid quercetin: Implication of its intestinal absorption and metabolism. Arch Biochem Biophys 2003; 417: 12–17
   PubMed Web of Science ®Google Scholar
• Walle T. Absorption and metabolism of flavonoids. Free Radic Biol Med 2004; 36: 829–837
   PubMed Web of Science ®Google Scholar
• Day AJ, Mellon F, Barron D, Sarrazin G, Morgan MRA, 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
• Mullen W, Boitier A, Stewart AJ, Crozier A. Flavonoid metabolites in human plasma photodiode array and full scan tandem mass spectrometric detection. J Chromatogr A 2004; 1058: 163–168
   PubMed Web of Science ®Google Scholar
• Youdim KA, Dobbie MS, Kuhnmle G, Proteggente AR, Abbott NJ, Rice-Evans C. Interaction between flavonoids and the blood–brain barrier: In vitro studies. J Neurochem 2003; 85: 180–192
   PubMed Web of Science ®Google Scholar
• Youdim KA, Qaiser MZ, Begley DJ, Rice-Evans CA, Abbott NJ. Flavonoid permeability across an in situ model of the blood–brain barrier. Free Radic Biol Med 2004; 36: 592–604
   PubMed Web of Science ®Google Scholar
• de Boer VCJ, Dihal AA, van der Woude H, Arts ICW, Wolffram S, Alink GM, Rietjens IMCM, Keijer J. Tissue distribution of quercetin in rats and pigs. J Nutr 2005; 135: 1617–1618
   PubMed Web of Science ®Google Scholar
• Paulke A, Schubert-Zsilavecz M, Wurglics M. Determination of St. John's wort flavonoid-metabolites in rat brain through high performance liquid chromatography coupled with fluorescence detection. J Chromatogr B 2006, in press
   PubMedGoogle Scholar
• Moon J-H, Tsushida T, Nakahara K, Terao J. Identification of quercetin 3-O-β-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
• Terao J, Shibata SS, Matsushita M. Selective quantification of arachidonic acid hydroperoxides and their hydroxyl derivatives in reversed phase high-performance liquid chromatography. Anal Biochem 1988; 169: 191–193
   Web of Science ®Google Scholar
• Wang H, Joseph JA. Quantifying cellular oxidative stress by dichlorofluorescein assay using microplate reader. Free Radic Biol Med 1999; 27: 612–616
   PubMed Web of Science ®Google Scholar
• Blois MS. Antioxidant determinations by the use of a stable free radical. Nature 1958; 181: 1199–1200
   Web of Science ®Google Scholar
• BioByte Corp., CA, USA. http://www.biobyte.com/
   Google Scholar
• Rekker R. The hydrophobic fragmental constant. Elsevier, Amsterdam 1977
   Google Scholar
• Hansch C, Leo A. Calculation of octanol–water partition coefficients by fragment. Exploring QSAR: Fundamentals and applications in chemistry and biology. American Chemical Society, Washington DC 1995; 125–168
   Google Scholar
• van Kujik FJGM, Sevanian A, Handleman GJ, Dratz EA. A new role of phospholipase A2: Protection of membranes from lipid peroxidation damage. Trend Biochem Sci 1987; 12: 31–34
   Web of Science ®Google Scholar
• Terao J. Reactions of lipid hydroperoxides in membrane lipid oxidation, C Viogo-Pelfrey. CRC Press, Boca Raton, FL 1990; 1: 219–238
   Google Scholar
• Wardman P, Burkitt MJ, Patel KB, Lawrence A, Jones CM, Everett SA, Vojnovic B. Pitfalls in the use of common luminescent probes for oxidative and nitrosative stress. J Fluorescence 2002; 12: 65–68
   Web of Science ®Google Scholar
• LeBel CP, Ischiropoulos H, Bondy SC. Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress. Chem Res Toxicol 1992; 5: 227–231
   PubMed Web of Science ®Google Scholar
• Yoshida Y, Shimakawa S, Itoh N, Niki E. Action of DCFH and BODIPY as a probe for radical oxidation in hydrophilic and lipophilic domain. Free Radic Res 2003; 37: 861–872
   PubMed Web of Science ®Google Scholar
• Sasaki N, Tada T, Kaneko T, Baba N, Matsuo M. Protective effects of flavonoids on the cytotoxicity of linoleic acid hydroperoxide toward rat pheochromocytoma PC12 cells. Chem Biol Interact 2003; 145: 101–116
   PubMed Web of Science ®Google Scholar
• Rice-Evans CA, Miller NJ, Paganga G. Structure–antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 1996; 20: 933–956
   PubMed Web of Science ®Google Scholar
• Shirai M, Yamanishi R, Moon J-H, Murota K, Terao J. Effect of quercetin and its conjugated metabolite on the hydrogen peroxide-induced intracellular production of reactive oxygen species in mouse fibroblasts. Biosci Biotechnol Biochem 2002; 66: 1015–1021
   PubMed Web of Science ®Google Scholar
• Shirai M, Moon J-H, 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
• Spencer JPE, Schroeter H, Cressthwaithe AJ, Kuhnle G, Williams RJ, Rice-Evans C. Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts. Free Radic Biol Med 2001; 31: 1139–1146
   PubMed Web of Science ®Google Scholar
• Youdim KA, Shukitt-Hale B, Joseph JA. Flavonoids and the brain: Interactions at the blood–brain barrier and their physiological effects on the central nervous system. Free Radic Biol Med 2004; 37: 1683–1693
   PubMed Web of Science ®Google Scholar