Quercetin-dependent inhibition of nitration induced by peroxidase/H 2O2/nitrite systems in human saliva and characterization of an oxidation product of quercetin formed during the inhibition

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 9, 2005, Pages 3265-3272

  Hirota, Sachiko ^a   Takahama, Umeo ^b   Ly, Tram Ngoc ^c   Yamauchi, Ryo ^c  

^a KYUSHU WOMEN'S UNIVERSITY   (Japan)

^b KYUSHU DENTAL COLLEGE   (Japan)

^c GIFU UNIVERSITY   (Japan)

Author keywords

Inhibition of nitration; Nitration; nitrite; Oxidation product of quercetin; Quercetin; Salivary peroxidase

Indexed keywords

4 HYDROXYPHENYLACETIC ACID; 4-HYDROXYPHENYLACETIC ACID; HYDROGEN PEROXIDE; NITRATE; NITRITE; PEROXIDASE; PHENYLACETIC ACID DERIVATIVE; QUERCETIN;

ARTICLE; CHEMISTRY; HUMAN; METABOLISM; OXIDATION REDUCTION REACTION; PH; SALIVA;

HUMANS; HYDROGEN PEROXIDE; HYDROGEN-ION CONCENTRATION; NITRATES; NITRITES; OXIDATION-REDUCTION; PEROXIDASE; PHENYLACETATES; QUERCETIN; SALIVA;

BACTERIA (MICROORGANISMS);

EID: 19944374808     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0404389     Document Type: Article

References (41)

1. Ferguson, D. B. Salivary electrolytes. In Human Saliva. Clinical Chemistry and Microbiology Vol. I; Tenovuo, J., Ed.; CRC Press: Boca Raton, FL, 1989; pp 75-99.
2. Li, H.; Duncan, C.; Townend, J.; Killham, K.; Smith, L. M.; Johnston, P.; Dykhuizen, R.; Kelly, D.; Golden, M.; Benjamin, N.; Leifert, C. Nitrate-reducing bacteria on rat tongues. Appl. Environ. Microbiol. 1997, 63, 924-930.
3. Takahama, U.; Oniki, T.; Murata, H. The presence of 4-hydroxy- phenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach. FEBS Lett. 2002, 518, 116-118.
4. McKnight, G. M.; Smith, L. M.; Drummond, R. S.; Duncan, C. W.; Golden, M.; Benjamin, N. Chemical synthesis of nitric oxide in the stomach from dietary nitrate in humans. Gut 1997, 40, 211-214.
5. Pannala, A. S.; Mani, A. R.; Spencer, J. P.; Skinner, V.; Bruckdorfer, K. R.; Moore, K. P.; Rice-Evans, C. A. The effect of dietary nitrate on salivary, plasma, and urinary nitrate metabolism in humans. Free Radical Biol. Med. 2003, 34, 576-584.
6. Hirota, S.; Nishioka, T.; Shimoda, T.; Miura, K.; Ansai, T.; Takahama, U. Quercetin glucosides are hydrolyzed to quercetin in human oral cavity to participate in peroxidase-dependent scavenging of hydrogen peroxide. Food Sci. Technol. Res. 2001, 7, 239-245.
7. Tenovuo, J. Nonimmunoglobulin defense factors in human saliva. In Human Saliva. Clinical Chemistry and Microbiology Vol. II; Tenovuo, J., Ed.; CRC Press: Boca Raton, FL, 1989; pp 55-91.
8. Thomas, E. L.; Jefferson, M. M.; Joyer, R. E.; Cook, G. S.; King, C. C. Leukocyte myeloperoxidase and salivary lactoperoxidase: Identification and quantification in human mixed saliva. J. Dent. Res. 1994, 73, 544-55.
9. Al-Essa, L.; Niwa, K.; Kohno, K.; Tsurumi, K. A proposal for purification of salivary polymorphonuclear leukocytes by combination of nylon mesh filtration and density-gradient method: A validation by Superoxide- and cyclic AMP-generating responses. Life Sci. 1994, 55, PL333-338.
10. Nakahara, H.; Sato, E. F.; Ishisaka, R.; Kanno, T.; Yoshioka, T.; Yasuda, T.; Inoue, M.; Utsumi, K. Biochemical properties of human oral polymorphonuclear leukocytes. Free Radical Res. 1998, 28, 485-495.
11. Yamamoto, M.; Saeki, K.; Utsumi, K. Isolation of human salivary polymorphonuclear leukocytes and their stimulation-coupled responses. Arch. Biochem. Biophys. 1991, 289, 76-82.
12. Halliwell, B.; Zhao, K.; Whiteman, M. Nitric oxide and peroxynitrite. The ugly, the uglier and the not so good. Free Radical Res. 1999, 31, 651-669.
13. Ricoux, R.; Boucher, J. L.; Mansuy, D.; Mahy, J. P. Microperoxidase 8 catalyzes nitration of phenol by nitrogen dioxide radicals. Eur. J. Biochem. 2001, 268, 3783-3788.
14. van Dalen, C. J.; Winterbourn, C. C.; Senthilmohan, R.; Kettle, A. J. Nitrite as a substrate and inhibitor of myeloperoxidase. J. Biol. Chem. 2000, 275, 11638-11644.
15. Shibata, H.; Kono, Y.; Yamashita, S.; Sawa, Y.; Ochiai, H.; Tanaka, K. Degradation of chlorophyll by nitrogen dioxide generated from nitrite by peroxidase reaction. Biochim. Biophys. Acta 1995, 1230, 45-50.
16. van der Vliet, A.; Eiserich, J. P.; Halliwell, B.; Cross, C. E. Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. A potential additional mechanism of nitric oxide-dependent toxicity. J. Biol. Chem. 1997, 272, 7617-7625.
17. Wu, W.; Chen, Y.; Hazen, S. L. Eosinophil peroxidase nitrates protein tyrosyl residues. Implications for oxidative damage by nitrating intermediates in eosinophilic inflammatory disorders. J. Biol. Chem. 1999, 274, 25933-25944.
18. Hirota, S.; Takahama, U. Quercetin and the glucosides inhibit nitration of a salivary component 4-hydroxyphenylacetic acid catalyzed by salivary polymorphonuclear leukocytes. Food Sci. Technol. Res. 2003, 9, 378-382.
19. Takahama, U.; Hirota, S.; Nishioka, T.; Oniki, T. Human salivary peroxidase-catalyzed oxidation of nitrite and nitration of salivary components 4- hydroxyphenylacetic acid and proteins. Arch. Oral Biol. 2003, 48, 679-690.
20. Oldreive, C.; Rice-Evans, C. The mechanism for nitration and nitrotyrosine formation in vitro and in vivo: Impact of diet. Free Radical Res. 2001, 25, 215-231.
21. Oldreive, C.; Zhao, K.; Paganga, G.; Halliwell, B.; Rice-Evans, C. Inhibition of nitrous acid-dependent tyrosine nitration and DNA base deamination by flavonoids and other phenolic compounds. Chem. Res. Toxicol. 1998, 11, 1574-1579.
22. Takahama, U.; Hirota, S. Deglucosidation of quercetin glucosides to the aglycone and formation of antifungal agents by peroxidase-dependent oxidation of quercetin on browning of onion scales. Plant Cell Physiol. 2000, 41, 1021-1029.
23. Jungbluth, G.; Ternes, W. Development of a sample preparation method for the analysis of oxidized flavonols in onion and leek. Nahrung 2002, 46, 349-352.
24. Jørgensen, L. V.; Cornett, C.; Justesen, U.; Skibsted, L. H.; Dragsted, L. O. Two-electron electrochemical oxidation of quercetin and kaempferol changes only the flavonoid C-ring. Free Radical Res. 1998, 29, 339-350.
25. Jungbluth, C.; Rühling, I.; Ternes, W. Oxidation of flavonols with Cu(II), Fe(II) and Fe(III) in aqueous media. J. Chem. Soc., Perkin Trans. 2 2000, 1946-1952.
26. Hargreaves, K. R.; McGookin, A.; Robertson, A. Polyhydroxy- phenylglyoxylic acids. J. Appl. Chem. 1958, 8, 273-285.
27. Burner, U.; Furtmüller, P. G.; Kettle, A. J.; Koppenol, W.; Obinger, C. Mechanism of reaction of myeloperoxidase with nitrite. J. Biol. Chem. 2000, 275, 20597-20601.
28. Nishioka, T.; Maki, K.; Kimura, M.; Takahama, U. Determination of salivary peroxidase activity in human mixed whole saliva. Arch. Oral Biol. 2003, 48, 397-400.
29. Jungbluth, G.; Ternes, W. HPLC separation of flavonols, flavones and oxidized flavonols with UV-, DAD-, electrochemical and ESI-ion trap MS detection. Fresenius' J. Anal. Chem. 2000, 367, 661-666.
30. Barz, W.; Köster, J.; Weltring, K.-M.; Strack, D. Recent advances in the metabolism and degradation of phenolic compounds in plants and animals. Annu. Proc. Phytochem. Soc. Eur. 1985, 25, 307-347.
31. Schreier, P.; Miller, E. Studies on flavonoid degradation by peroxidase: Quercetin. Food Chem. 1985, 17, 301-317.
32. Takahama, U. Oxidation of vacuolar and apoplastic phenolic substrates by peroxidase: Physiological significance of the oxidation reaction. Phytochem. Rev. 2004, 3, 207-219.
33. Hirota, S.; Takahama, U.; Ansai, T.; Yoshitama, K. Oxidation of quercetin by salivary components II. Effects of quercetin on reactive oxygen metabolism by salivary polymorphonuclear leukocytes. Food Sci. Technol. Res. 2002, 8, 276-280.
34. Takahama, U.; Oniki, T.; Hirota, S. Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide. J. Agric. Food Chem. 2002, 50, 4317-4322.
35. Takahama, U.; Yamamoto, A.; Hirota, S.; Oniki, T. Quercetin-dependent reduction of salivary nitrite to nitric oxide under acidic conditions and interaction between quercetin and ascorbic acid during the reduction. J. Agric. Food Chem. 2003, 51, 6014-6020.
36. Jiménez, M.; Garcia-Carmona, F. Oxidation of the flavonol quercetin by polyphenol oxidase. J. Agric. Food Chem. 1999, 47, 56-60.
37. Takahama, U.; Oniki, T.; Hirota, S. Phenolic components of brown scales of onion bulbs produce hydrogen peroxide by autoxidation. J. Plant Res. 2001, 114, 395-402.
38. Carossa, S.; Pera, P.; Doglio, P.; Lombardo, S.; Colagrande, P.; Brussino, L.; Rolla, G.; Bucca, C. Oral nitric oxide during plaque deposition. Eur. J. Clin. Invest. 2001, 31, 876-879.
39. Palmerini, C. A.; Palombari, R.; Perito, S.; Arienti, G. NO synthesis in human saliva. Free Radical Res. 2003, 37, 29-31.
40. Zatterquist, W.; Pedroletti, C.; Lundberg, J. O.; Alving, K. Salivary contribution to exhaled nitric oxide. Eur. Respir. J. 1999, 13, 327-333.
41. Takahama, U.; Hirota, S.; Oniki, T. Production of nitric oxide-derived reactive nitrogen species in human oral cavity and their scavenging by salivary redox components. Free Radical Res. 2005, in press.