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Articles

In vitro evaluation of the antioxidant and anti-inflammatory activities of sulphated metabolites of catechins
Evaluación in vitro de las actividades antioxidante y antiinflamatoria de metabolitos sulfatados de catequinas

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Pages 257-264 | Received 12 Apr 2011, Accepted 27 May 2011, Published online: 04 Nov 2011

References

  • Baba , S. , Osakabe , N. and Natsume , M. 2001 . In vivo comparison of the bioavailability of (+)-catechin, (−)-epicatechin and their mixture in orally administered rats . Journal of Nutrition , 131 : 2885 – 2892 .
  • Baba , S. , Osakabe , N. , Yasuda , A. , Natsume , M. , Takizawa , T. , Nakamura , T. and Terao , J. 2000 . Bioavailability of (−)-epicatechin upon intake of chocolate and cocoa in human volunteers . Free Radical Research , 33 : 635 – 641 .
  • Beckman , J. S. and Koppenol , W. H. 1996 . Nitric oxide, superoxide, and peroxynitrite: The good, the bad, and the ugly . American Journal of Physiology-Cell Physiology , 271 : C1424 – C1437 .
  • Benzie , I. F.F. and Strain , J. J. 1996 . The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: The FRAP assay . Analytical Biochemistry , 239 : 70 – 76 .
  • Bomser , J. A. , Singletary , K. W. , Wallig , M. A. and Smith , M. A.L. 1999 . Inhibition of TPA-induced tumor promotion in CD-1 mouse epidermis by a polyphenolic fraction from grape seeds . Cancer Letters , 135 : 151 – 157 .
  • Cao , G. , Sofic , E. and Prior , R. L. 1997 . Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships . Free Radical Biology and Medicine , 22 : 749 – 760 .
  • Cook , N. C. and Samman , S. J. 1996 . Flavonoids – Chemistry, metabolism, cardioprotective effects, and dietary sources . Journal of Nutritional Biochemistry , 7 : 66 – 76 .
  • Cooke , J. P. and Dzau , V. J. 1997 . Nitric oxide synthase: Role in the genesis of vascular disease . Annual Review of Medicine , 48 : 489 – 509 .
  • Cooper , K. A. , Donovan , J. L. , Waterhouse , A. L. and Williamson , G. 2008 . Cocoa and health: A decade of research . British Journal of Nutrition , 99 : 1 – 11 .
  • Cren-Olivé , C. and Rolando , C. 2003 . “ Polyphenols: Measurement and calculation of their physical chemistry properties ” . In Methods in polyphenols analysis , Edited by: Santos-Buelga , C. and Williamson , G. 157 – 176 . Cambridge , UK : Royal Society of Chemistry .
  • Day , A. J. , Bao , Y. P. , Morgan , M. R.A. and Williamson , G. 2000 . Conjugation position of quercetin glucuronides and effect on biological activity . Free Radical Biology and Medicine , 29 : 1234 – 1243 .
  • Donovan , J. L. , Bell , J. R. , Kasim-Karakas , S. , German , J. B. , Walzem , R. L. , Hansen , R. J. and Waterhouse , A. L. 1999 . Catechin is present as metabolites in human plasma after consumption of red wine . Journal of Nutrition , 129 : 1662 – 1668 .
  • Donovan , J. L. , Crespy , V. , Manach , C. , Morand , C. , Besson , C. , Scalbert , A. and Remesy , C. 2001 . Catechin is metabolized by both the small intestine and liver of rats . Journal of Nutrition , 131 : 1753 – 1764 .
  • Dueñas , M. , Gonzalez-Manzano , S. , Gonzalez-Paramas , A. and Santos-Buelga , C. 2010 . Antioxidant evaluation of O-methylated metabolites of catechin, epicatechin and quercetin . Journal of Pharmaceutical and Biomedical Analysis , 51 : 443 – 449 .
  • Dueñas , M. , Gonzalez-Manzano , S. , Gonzalez-Paramas , A. M. and Santos-Buelga , C. Characterization of sulfated quercetin and catechin metabolites Submitted for publication
  • Dueñas , M. , Surco-Laos , F. , Gonzalez-Manzano , S. , Gonzalez-Paramas , A. M. and Santos-Buelga , C. 2011 . Antioxidant properties of major metabolites of quercetin . European Food Research and Technology , 232 : 103 – 111 .
  • Gonzalez-Manzano , S. , Gonzalez-Paramas , A. , Santos-Buelga , C. and Duenas , M. 2009 . Preparation and characterization of catechin sulfates, glucuronides and methylethers with metabolic interest . Journal of Agricultural and Food Chemistry , 57 : 1231 – 1238 .
  • Ho , S. C. , Hwang , L. S. , Shen , Y. J. and Lin , C. C. 2007 . Suppressive effect of a proanthocyanidin-rich extract from longan (Dimocarpus longan Lour.) flowers on nitric oxide production in LPS-stimulated macrophage cells . Journal of Agricultural and Food Chemistry , 55 : 10664 – 10670 .
  • Jones , D. J.L. , Jukes-Jones , R. , Verschoyle , R. D. , Farmer , P. B. and Gescher , A. A. 2005 . A synthetic approach to the generation of quercetin sulfates and the detection of quercetin 3′-O-sulfate as a urinary metabolite in the rat . Bioorganic & Medicinal Chemistry , 13 : 6727 – 6731 .
  • Kashiwada , Y. , Nonaka , G. , Nishioka , I. and Chang Lee , J. J. 1992 . Antitumor agents, 129. Tannins and related-compounds as selective cytotoxic agents . Journal of Natural Products , 55 : 1033 – 1043 .
  • Kroon , P. A. , Clifford , M. N. , Crozier , A. , Day , A. J. , Donovan , J. L. , Manach , C. and Williamson , G. 2004 . How should we assess the effects of exposure to dietary polyphenols in vitro? . American Journal of Clinical Nutrition , 80 : 15 – 21 .
  • Laranjinha , J. 2010 . “ Translation of chemical properties of polyphenols into biological activity with impact in human health ” . In Research Advances in Polyphenol Research , Edited by: Santos-Buelga , C. , Escribano-Bailon , M. T. and Lattanzio , V. 269 – 282 . Oxford , UK : Wiley-Blackwell .
  • Lemanska , K. , Szymusiak , H. , Tyrakowska , B. , Zielinski , R. , Soffers , A. E.M.F. and Rietjens , I. M.C.M. 2001 . The influence of pH on antioxidant properties and the mechanism of antioxidant action of hydroxyflavones . Free Radical Biology and Medicine , 31 : 869 – 881 .
  • Loke , W. M. , Jenner , A. M. , Proudfoot , J. M. , McKinley , A. J. , Hodgson , J. M. , Halliwell , B. and Croft , K. D. 2009 . A metabolite profiling approach to identify biomarkers of flavonoid intake in humans . Journal of Nutrition , 139 : 2309 – 2314 .
  • Miller , N. J. , Diplock , A. T. , Rice-Evans , C. , Davies , M. J. , Gopinathan , V. and Milner , A. 1993 . A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates . Clinical Science , 84 : 407 – 412 .
  • Mira , L. , Fernandez , M. T. , Santos , M. , Rocha , R. , Florencio , M. H. and Jennings , K. R. 2002 . Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity . Free Radical Research , 36 : 1199 – 1208 .
  • Mira , L. , Silva , M. , Rocha , R. and Manso , C. F. 1999 . Measurement of relative antioxidant activity of compounds: A methodological note . Redox Report , 4 : 69 – 74 .
  • Morand , C. , Manach , C. , Donovan , J. and Remesy , C. 2001 . Preparation and characterization of flavonoid metabolites present in biological samples . Methods in Enzymology , 335 : 115 – 121 .
  • Muzolf , M. , Szymusiak , H. , Gliszczynska-Swiglo , A. , Rietjens , I. M.C.M. and Tyrakowska , B. 2008 . pH-dependent radical scavenging capacity of green tea catechins . Journal of Agricultural and Food Chemistry , 56 : 816 – 823 .
  • Nakachi , K. , Suemasu , K. and Suga , K. 1998 . Influence of drinking green tea on breast cancer malignancy among Japanese patients . Japanese Journal of Cancer Research , 89 : 254 – 263 .
  • Natsume, M., Osakabe, N., Oyama, M., Sasaki, M., Baba, S., Nakamura, Y., Osawa, T., Terao, J. (2003). Structures of (−)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (−)-epicatechin: Differences between human and rat. Free Radical Biology and Medicine, 34, 840–849
  • Park , Y. C. , Rimbach , G. , Saliou , C. , Valacchi , G. and Packer , L. 2000 . Activity of monomeric, dimeric, and trimeric flavonoids on NO production, TNF-alpha secretion, and NF-kappa B-dependent gene expression in RAW 264.7 macrophages . FEBS Letters , 465 : 93 – 97 .
  • Radi , R. , Beckman , J. S. , Bush , K. M. and Freeman , B. A. 1991a . Peroxynitrite oxidation of sulfhydryls the cytotoxic potential of superoxide and nitric-oxide . Journal of Biological Chemistry , 266 : 4244 – 4250 .
  • Radi , R. , Beckman , J. S. , Bush , K. M. and Freeman , B. A. 1991b . Peroxynitrite-induced membrane lipid-peroxidation – The cytotoxic potential of superoxide and nitric-oxide . Archives of Biochemistry and Biophysics , 288 : 481 – 487 .
  • Rice-Evans , C. A. , Miller , N. J. and Paganga , G. 1996 . Structure-antioxidant activity relationships of flavonoids and phenolic acids . Free Radical Biology and Medicine , 20 : 933 – 956 .
  • Saint-Cricq de Gaulejac , N. , Vivas , N. , De-Freitas , V. and Bourgeois , G. 1999 . The influence of various phenolic compounds on scavenging activity assessed by an enzymatic method . Journal of the Science of Food and Agriculture , 79 : 1081 – 1090 .
  • Saito , M. , Hosoyama , H. , Ariga , T. , Kataoka , S. and Yamaji , N. 1998 . Antiulcer activity of grape seed extract and procyanidins . Journal of Agricultural and Food Chemistry , 46 : 1460 – 1464 .
  • Silva , M. M. , Santos , M. R. , Caroco , G. , Rocha , R. , Justino , G. and Mira , L. 2002 . Structure-antioxidant activity relationships of flavonoids: A re-examination . Free Radical Research , 36 : 1219 – 1227 .
  • Simonetti , P. , Ciappellano , S. , Gardana , C. , Bramati , L. and Pietta , P. J. 2002 . Procyanidins from Vitis vinifera seeds: In vivo effects on oxidative stress . Journal of Agricultural and Food Chemistry , 50 : 6217 – 6221 .
  • Spencer , J. P.E. , El Mohsen , M. M.A. , Minihane , A. M. and Mathers , J. C. 2008 . Biomarkers of the intake of dietary polyphenols: Strengths, limitations and application in nutrition research . British Journal of Nutrition , 99 : 12 – 22 .
  • Steinberg , F. M. , Bearden , M. M. and Keen , C. L.J. 2003 . Cocoa and chocolate flavonoids: Implications for cardiovascular health . American Dietetic Association , 103 : 215 – 223 .
  • Stevens , J. F. , Miranda , C. L. , Wolthers , K. R. , Schimerlik , M. , Deinzer , M. L. and Buhler , D. R. 2002 . Identification and in vitro biological activities of hop proanthocyanidins: Inhibition of nNOS activity and scavenging of reactive nitrogen species . Journal of Agricultural and Food Chemistry , 50 : 3435 – 3443 .
  • Terra , X. , Valls , J. , Vitrac , X. , Merrillon , J. M. , Arola , L. , Ardevol , A. , … and Blay , M. 2007 . Grape-seed procyanidins act as antiinflammatory agents in endotoxin-stimulated RAW 264.7 macrophages by inhibiting NFkB signaling pathway . Journal of Agricultural and Food Chemistry , 55 : 4357 – 4365 .
  • Tsai , P. J. , Tsai , T. H. , Yu , C. H. and Ho , S. C. 2007 . Comparison of NO-scavenging and NO-suppressing activities of different herbal teas with those of green tea . Food Chemistry , 103 : 181 – 187 .
  • Villaño , D. , Fernández-Pachón , M. S. , Troncoso , A. M. and García-Parrilla , M. C. 2004 . The antioxidant activity of wines determined by the ABTS*+ method: Influence of sample dilution and time . Talanta , 64 : 501 – 509 .
  • Williamson , G. , Barron , D. , Shimoi , K. and Terao , J. 2005 . In vitro biological properties of flavonoid conjugates found in vivo . Free Radical Research , 39 : 457 – 469 .
  • Williamson , G. and Manach , C. 2005 . Bioavailability and bioefficacy of polyphenols in humans. II. Review of 93 intervention studies . American Journal of Clinical Nutrition , 81 : 243 – 255 .
  • Yermilov , V. , Rubio , J. and Ohshima , H. 1995 . Formation of 8-nitroguanine in DNA treated with peroxynitrite in-vitro and its rapid removal from DNA by depurination . FEBS Letters , 376 : 207 – 210 .

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