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Original Article

Protection by quercetin and quercetin 3-O-β-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein

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Pages 925-931 | Received 15 Aug 2000, Published online: 07 Jul 2009

References

  • Steinberg D., Parthasarathy S., Carew T.E., Khoo J.C., Witztum J.L. Beyond cholesterol; modification of low-density lipoprotein that increases its atherogenecity. New England Journal of Medicine 1989; 320: 915–924
  • Parthasarathy S., Santanam N., Ramachandran S., Meilhac O. Oxidants and antioxidants in atherogenesis: an appraisal. Journal of Lipid Research 1999; 40: 2143–2157
  • Stocker R. Dietary and pharmacological antioxidants in atherosclerosis. Current Opinion in Lipidology 1999; 10: 589–597
  • Kaplan M., Aviram M. Oxidized low-density lipoprotein: atherogenic and proinflammatory characteristics during macrophase foam cell formation. An inhibitory role for nutritional antioxidants and serum paraoxonase. Clinical Chemistry and Laboratory Medicine 1999; 37: 777–787
  • Beckman J.S., Beckman T.W., Chen J., Marshall P.A., Freeman B.A. Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proceedings of the National Academy of Sciences USA 1990; 87: 1620–1624
  • Radi R., Beckman J.S., Bush K.M., Freeman B.A. Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Archives of Biochemistry and Biophysics 1991; 288: 481–487
  • Shi H., Noguchi N., Xu Y., Niki E. Formation of phospholipid hydroperoxides and its inhibition by α-tocopherol in rat brain synaptosomes induced by peroxynitrite. Biochemical and Biophysical Research Communication 1999; 257: 651–656
  • Darley-Usmar V.M., Hogg N., O'leary V.J., Wilson M.T., Moncada S. The simultaneous generation of superoxide and nitric oxide can initiate lipid peroxidation in human low-density lipoprotein. Free Radical Research Communication 1992; 17: 9–20
  • Graham A., Hogg N., Kalyanaraman B., O'leary V., Darley-Usmar V., Moncada S. Peroxynitrite modification of lower-density lipoprotein leads to recognition by the macrophage scavenger receptor. FEBS Letters 1993; 330: 181–185
  • Hogg N., Darley-Usmar V.M., Wilson M.T., Moncada S. The oxidation of α-tocopherol in human low-density lipoprotein by the simultaneous generation of superoxide and nitric oxide. FEBS Letters 1993; 326: 199–203
  • Patel R.P., Darley-Usmar V.M. Using peroxynitrite as oxidant with low-density lipoprotein. Methods in Enzymology 1996; 269: 375–384
  • Leeuwenburgh C., Hardy M.M., Hazen S.L., Wagner P., Oh-ishi S., Steinbrecher U.P., Heinecke J.W. Reactive nitrogen intermediates promote low-density lipoprotein oxidation in human athrosclerotic intima. Journal of Biological Chemistry 1997; 272: 1433–1436
  • Thomas S.R., Davies M.J., Stocker R. Oxidation and antioxidation of human low-density lipoprotein and plasma exposed to 3-morpholinosyldnonimine and reagent peroxynitrite. Chemical Research in Toxicology 1998; 11: 484–494
  • Hertog M.G.L., Hollman P.C.H., Katan M.B. Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in The Netherlands. Journal of Agricultural and Food Chemistry 1992; 40: 2379–2383
  • Rice-Evans C., Miller N.J., Paganga G. Structure-activity relationship of flavonoids and phenolic acids. Free Radical Biology and Medicine 1996; 20: 933–956
  • Haenen G.R.M.M., Paquay J.B.G., Korthouwer E.M., Bast A. Peroxynitrite scavenging by flavonoids. Biochemical and Biophysical Research Communication 1997; 236: 591–593
  • Manach C., Morand C., Crespy V., Demigne C.M., Texier O., Regerat F., Remesy C. Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Letters 1998; 426: 331–336
  • Moon J.-H., Nakata R., Oshima S., Inakuma T., Terao J. Accumulation of quercetin conjugates in blood plasma after the short-term ingestion of onion by women. American Journal of Physiology 2000; 279: R461–R467
  • 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 Radical Biology and Medicine 2001; 30: 1274–1285
  • Huges M.W., Nicklin H.G. The chemistry of peroxynitrite part II. Copper (II)-catalyzed reaction between hydroxylamine and peroxynitrite in alkali. Journal of Chemical Society A 1970; 925–928
  • Beckman J.S., Chen J., Ischiropoulos H., Crow J.P. Oxidative chemistry of peroxynitrite. Methods in Enzymology 1994; 233: 229–240
  • da Silva E.L., Tsushida T., Terao J. Inhibition of mammalian 15-lipoxygenase-dependent lipid peroxidation in low-density lipoprotein by quercetin and quercetin monoglucosides. Archives of Biochemistry and Biophysics 1999; 349: 313–320
  • Lowry O.H., Rosebrough J.N., Farr A.L., Randall R.J. Protein measurement with Folin phenol reagent. Journal of Biological Chemistry 1951; 193: 165–175
  • Koppenol W.H. The basic chemistry of nitrogen monoxide and peroxynitrite. Free Radical Biology and Medicine 1998; 25: 385–391
  • Pannala A.S., Rice-Evans C., Sampson J., Singh S. Interaction of peroxynitrite with carotenoids and tocopherols within low-density lipoprotein. FEBS Letters 1998; 423: 297–301
  • Panasenko O.M., Sharow V.S., Briviba K., Sies H. Interaction of peroxynitrite with carotenoids in human low-density lipoproteins. Archives of Biochemistry and Biophysics 2000; 373: 302–305
  • Pannala A.S., Rice-Evans C.A., Halliwell B., Singh S. Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols. Biochemical and Biophysical Research Communication 1997; 232: 164–168
  • Chung H.Y., Yokozawa T., Soung D.Y., Kye I.S., No J.K., Bark B.S. Peroxynitrite-scavenging activity of green tea tannin. Journal of Agricultural and Food Chemistry 1998; 46: 4484–4486
  • Arteel G.E., Sies H. Protection against peroxynitrite by cocoa polyphenol oligomers. FEBS Letters 1999; 462: 167–170
  • Kato Y., Ogino Y., Aoki T., Uchida K., Kawakishi S., Osawa T. Phenolic antioxidants prevent peroxynitrite-derived collagen modification in vitro. Journal of Agricultural and Food Chemistry 1997; 45: 3004–3009
  • Tsuda T., Kato Y., Osawa T. Mechanism for the peroxynitrite scavenging activity by antioxidants. FEBS Letters 2000; 484: 207–210
  • Kerry N., Rice-Evans C.A. Inhibition of peroxynitrite-mediated oxidation of dopamine by flavonoid and phenolic antioxidants and their structural relationship. Journal of Neurochemistry 1999; 73: 247–253
  • Minetti M., Mallozzi C., di Stasi M., Pietraforte D. Bilirubin is an effective antioxidant of peroxynitrite-mediate protein oxidation in human blood plasma. Archives of Biochemistry and Biophysics 1998; 352: 165–174
  • Skinner K.A., White C.R., Patel R., Tan S., Barnes S., Kirk M., Darley-Usmar V., Parks D.A. Nitrosation of uric acid by peroxynitrite. Journal of Biological Chemistry 1998; 273: 24491–24497

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