Chlorogenic acid in coffee can prevent the formation of dinitrogen trioxide by scavenging nitrogen dioxide generated in the human oral cavity

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 22, 2007, Pages 9251-9258

  Takahama, Umeo ^a   Ryu, Kanako ^b   Hirota, Sachiko ^b  

^a KYUSHU DENTAL COLLEGE   (Japan)

^b KYUSHU WOMEN'S UNIVERSITY   (Japan)

Author keywords

4,5 diaminofluorescein; Chlorogenic acid; Coffee; Human saliva; N2O3; NO2

Indexed keywords

CHLOROGENIC ACID; NITROGEN DIOXIDE; NITROGEN OXIDE; NITROGEN TRIOXIDE; SCAVENGER; UNCLASSIFIED DRUG;

ARTICLE; BACTERIUM; CHEMISTRY; COFFEE; DRUG ANTAGONISM; HUMAN; METABOLISM; MICROBIOLOGY; OXIDATION REDUCTION REACTION; SALIVA; SPECTROFLUOROMETRY;

BACTERIA; CHLOROGENIC ACID; COFFEE; FREE RADICAL SCAVENGERS; HUMANS; NITROGEN DIOXIDE; NITROGEN OXIDES; OXIDATION-REDUCTION; SALIVA; SPECTROMETRY, FLUORESCENCE;

BACTERIA (MICROORGANISMS);

EID: 36148947154     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf071700r     Document Type: Article

References (53)

1. Zetterquist, W.; Pedroletti, C.; Lundberg, J. O.; Alving, K. Salivary contribution to exhaled nitric oxide. Eur. Respir. J 1999, 13, 327-333.
2. 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.
3. Palmerini, C. A.; Palombari, R.; Perito, S.; Arienti, G. NO synthesis in human saliva. Free Radical Res. 2003, 37, 29-31.
4. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine; Oxford University Press: Oxford, 1999.
5. Tenovuo, J. Nonimmunoglobulin defense factors in human saliva. In Human Saliva. Clinical Chemistry and Microbiology; Tenovuo, J., Ed.; CRC Press: Boca Raton, FL, 1989; Vol. II, pp 55-91.
6. Yamamoto, M.; Saeki, K.; Utsumi, K. Isolation of human salivary polymorphonuclear leukocytes and their stimulation-couples responses. Arch. Biochem. Biophys 1991, 289, 76-82.
7. 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. 199455, PL333-PL338.
8. 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.
9. Brück, T. B.; Fielding, R. J.; Symons, M. C. R.; Harvey, P. J. Mechanism of nitrite-stimulated catalysis by lactoperoxidase. Eur. J. Biochem. 2001, 268, 3214-3222.
10. Bian, K.; Gao, Z.; Weisbrodt, N.; Murad, F. The nature of heme/ion-induced protein tyrosine nitration. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5712-5717.
11. 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.
12. Radi, R. Nitric oxide, oxidants, and protein tyrosine nitration. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 4003-4008.
13. Monzani, E.; Roncone, R.; Galliano, M.; Koppenol, W. K.; Casella, L. Mechanistic insight into the peroxidase catalyzed nitration of tyrosine derivatives by nitrite and hydrogen peroxide. Eur. J. Biochem. 2004, 271, 895-906.
14. Lakshmi, V. M.; Nauseef, W. M.; Zenser, T. V. Myeloperoxidase potentiates nitric oxide-nitrosation. J. Biol. Chem. 2005, 280, 1746-1753.
15. Goldstein, S.; Lind, J.; Merenyi, G. Chemistry of peroxynitrites as compared to peroxynittrates. Chem. Rev. 2005, 105, 2457-2470.
16. Kirsch, M.; Lehnig, M.; Korth, H. G.; Sustmann, R.; de Groot, H. Inhibition of peroxynitrite-induced nitration of tyrosine by glutathione in the presence of carbon dioxide through both radical repair and peroxynitrate formation. Chemistry 2001, 7, 3313-3320.
17. Chapple, I. L. C. Reactive oxygen species and antioxidants in inflammatory diseases. J. Clin. Periodontal 1997, 24, 287-296.
18. Ohashi, M.; Iwase, M.; Nagumo, M. Elevated production of salivary nitric oxide in oral mucosal diseases. J. Oral Pathol. Med. 1999, 28, 355-359.
19. Diab-Ladki, R.; Pellat, B.; Chahine, R. Decrease in the total antioxidant activity of saliva in patients wit periodontal diseases. Clin. Oral Invest. 2003, 7, 103-107.
20. Sculley, D. Y.; Langley-Evans, S. C. Periodontal disease is associated with lower antioxidant capacity in whole saliva and evidence on increased protein oxidation. Clin. Sci. 2003, 105, 167-172.
21. Beevi, S. S.; Rasheed, A. M.; Geetha, A. Evaluation of oxidative stress and nitric oxide levels in patients with oral cavity cancer. Jpn. J. Clin. Oncol. 2004, 34, 379-385.
22. Brock, G. R.; Butterworth, C. J.; Mathwes, J. B.; Chappie, I. L. C. Local and systemic total antioxidant capacity in periodontitis and health. J. Clin. Periodontal 2004, 31, 515-521.
23. Kono, Y.; Kobayashi, K.; Tagawa, S.; Adachi, K.; Ueda, A.; Sawa, Y.; Shibata, H. Antioxidant activity of polyohenolics in diets. Rate constants of reactions of chlorogenic acid and caffeic acid with reactive oxygen and nitrogen. Biochim. Biophys. Acta 1997, 1335, 335-342.
24. Higdon, J. V.; Frei, B. Coffee and health: a review of recent human research. Crit. Rev. Food Sci. Nutr. 2006, 46, 101-123.
25. Delgado-Andrade, C.; Rufian-Henares, J. A.; Morales, F. J. Assessing the antioxidant activity of melamoidins from coffee brews by different antioxidant methods. J. Agric. Food Chem. 2005, 53, 7832-7836.
26. Takenaka, M.; Sato, N.; Asakawa, H.; Wen, X.; Murata, M.; Homma, S. Characterization of a metal-chelating substance in coffee. Biosci. Biotechnol. Biochem. 2005, 69, 26-30.
27. Clifford, M. N. Chlorogenic acid. In Coffee; Clarke, R. J., Macrae, R., Eds.; Elsevier Applied Science: London, UK, 1985; Vol. 1; pp 186-187.
28. Takahama, U.; Hirata, 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, 39, 737-745.
29. Takahama, U.; Hirota, S.; Oniki, T. Quercetin-dependent scavenging of reactive nitrogen species derived from nitric oxide and nitrite in the human oral cavity: Interaction of quercetin with salivary redox components. Arch. Oral Biol. 2006, 51, 629-639.
30. Takahama, U.; Hirota, S.; Oniki, T. Thiocyanate cannot inhibit the formation of reactive nitrogen species in human oral cavity in the presence of high concentrations of nitrite: detection of reactive nitrogen species with 4,5-diaminofluorescein. Chem. Res. Toxicol. 2006, 19, 1066-1073.
31. Takahama, U.; Hirota, S.; Yamamoto, A.; Oniki, T. Oxygen uptake during the mixing of saliva with ascorbic acid under acidic conditions: Possibility of its occurrence in the stomach. FEBS Lett. 2003, 550, 64-68.
32. Nakatsubo, N.; Kojima, H.; Kikuchi, K.; Nagoshi, H.; Hirata, Y.; Maeda, D.; Imai, Y.; Irimura, T.; Nagano, T. 1998. Direct evidence of nitric oxide production from bovine aortic endothelial cells using new fluorescent indicators: Diaminofluorescein. FEBS Lett. 1998, 427, 263-266.
33. Setsukinai, K.; Urano, Y.; Kakinuma, K.; Majima, H. J.; Nagano, T. Development of novel fluorescence probes that can reliably detect reactive oxygen species and distinguish specific species. J. Biol. Chem. 2003, 278, 3170-3175.
34. Johnston, K. L.; Clifford, M. N.; Morgan, L. M. Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine. Am. J. Clin. Nutr. 2003, 78, 728-733.
35. Nakatani, N.; Kayano, S.; Kikuzaki, H.; Sumino, K.; Katagiri, K.; Mitani, T. Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica L.). J. Agric. Food Chem. 2000, 48, 5512-5516.
36. Iwai, K.; Kishimoto, N.; Kakino, Y.; Mochida, K.; Fujita, T. In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans. J. Agric. Food Chem. 2004, 52, 4893-4898.
37. Murata, M.; Sugiura, M.; Sonokawa, Y.; Shimamura, T.; Homma, S. Properties of chlorogenic acid quinone: relationship between browning and formation of hydrogen peroxide from quinone solution. Biosci. Biotechnol Biochem. 2002, 66, 2525-2530.
38. Takahama, U.; Tanaka, M.; Oniki, T.; Hirota, S.; Yamauchi, R. Formation of the thiocyanate conjugate of chlorogenic acid in coffee under acidic conditions in the presence of thiocyanate and nitrite: possible occurrence in the stomach. J. Agric. Food Chem. 2007, 55, 4169-4176.
39. Kono, Y.; Shibata, H.; Kodama, Y.; Sawa, H. The suppression of the N-nitrosating reaction by chlorogenic acid. Biochem. J. 1995, 312, 947-963.
40. Espey, M. G.; Thomas, D. D.; Miranda, K. M.; Wink, D. A. Focusing of nitric oxide mediated nitrosation and oxidative nitrosylation as a consequence of reaction with superoxide. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11127-11132.
41. Jourd'heuil, D. Increased nitric oxide-dependent nitrosylation of 4,5-diaminofluorescein by oxidants: implications for the measurement of intercellular nitric oxide. Free Radical Biol. Med. 2002, 33, 676-684.
42. Hirota, S.; Nishioka, T.; Shimoda, T.; Miura, K.; Ansai, T.; Takahama, U. Quercetin glucosides are hydrolyzed to quercetin in the human oral cavity to participate in peroxidase-dependent scavenging of hydrogen peroxide. Food Sci. Technol. Res. 2001, 7, 239-245.
43. 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.
44. Hirota, S.; Takahama, U. Quercetin and the glucosides inhibit nitration of a salivary component 4-hydroxyphenylacetic acid catalyzed by salivary polymorphonuclear leukocytes. Food Sci. Techol. Res. 2003, 9, 378-382.
45. Pannala, A.; Rice-Evans, C. A.; Halliwell, B.; Singh, S. Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols. Biochem. Biophys. Res. Commun. 1997, 232, 164-168.
46. 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.
47. Carroll, R. T.; Galatsis, P.; Borosky, S.; Kopec, K. K.; Kumar, V.; Althaus, J. S.; Hall, E. D. 4-Hydroxy-2,2,6,6-tetramethylpiperidine-1- oxyl(Tempol) inhibits peroxynitrite-mediated phenol nitration. Chem. Res. Toxicol. 2000, 13, 294-300.
48. Terao, J.; Yamaguchi, S.; Shirai, M.; Miyoshi, M.; Moon, J.-H.; Oshima, S.; Inakuma, T.; Tsushida, T.; Kato, Y. Protection by quercetin and quercetin 3-O-β-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein. Free Radical Res. 2001, 35, 925-931.
49. Haenen, G. R. M.; Paquay, J. B. G.; Korthouwer, R. E. M.; Bast, A. Peroxynitrite scavenging by flavonoids. Biochem. Biophys. Res. Commun. 1997, 236, 591-593.
50. Moridani, M. Y.; Scobie, H.; Jamshidzadeh, A.; Salehi, P.; O'Brien, P. J. Caffeic acid, chlorogenic acid, and dihydrocaffeic acid metabolism: glutathione conjugate formation. Drug. Metabol. Dispos. 2001, 29, 1432-1439.
51. Takahama, U. Spectrophotometric study on the oxidation of rutin by horseradish peroxidase and characteristics of the oxidation products. Biochim. Biophys. Acta 1986, 882, 445-451.
52. Nagler, R. M.; Klein, I.; Zarzhevsky, N.; Drigues, N.; Reznick, A. Z. Characterization of the differentiated antioxidant profile of human saliva. Free Radical Biol. Med. 2002, 32, 268-277.
53. Tanaka, T.; Kojima, T.; Kawamori, T.; Wang, A.; Suzui, M.; Okamoto, K.; Mori, H. Inhibition of 4-nitroquinoline-1-oxide-induced rat tongue carcinogenesis by the naturally occurring plant phenolics caffeic, ellagic, chlorogenic and ferulic acids. Carcinogenesis 1993, 14, 1321-1325.