Interaction between ascorbic acid and chlorogenic acid During the formation of nitric oxide in acidified saliva

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 21, 2008, Pages 10406-10413

  Takahama, Umeo ^a   Tanaka, Mariko ^a   Hirota, Sachiko ^b  

^a KYUSHU DENTAL COLLEGE   (Japan)

^b KYUSHU WOMEN'S UNIVERSITY   (Japan)

Author keywords

Ascorbic acid; Chlorogenic acid; Free radicals; Nitric oxide; Nitrous acid; SCN

Indexed keywords

ASCORBIC ACID; CHLOROGENIC ACID; NITRIC OXIDE; NITRITE;

ARTICLE; CHEMISTRY; HUMAN; OXIDATION REDUCTION REACTION; SALIVA; STOMACH JUICE;

ASCORBIC ACID; CHLOROGENIC ACID; GASTRIC JUICE; HUMANS; NITRIC OXIDE; NITRITES; OXIDATION-REDUCTION; SALIVA;

EID: 58149333542     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8018535     Document Type: Article

References (42)

1. Carlsson. S.; Wiklund, N. P.; Engstrand, L.; Weitzberg, E.; Lundberg, J. N. O. Effects of pH, nitrite and ascorbic acid on nonenzymatic nitric oxide generation and bacterial growth in urine. Nitric Oxide 2001, 5, 580-586.
2. Duncan, C.; Dougall, H.; Johnston, P.; Green, S.; Brogan, R.; Leifert. C.; Smith. L.; Golden, M.; Benjamin, N. Chemical generation of nitric oxide in the mouth from then entersalivary circulation of dietary nitrite. Nat. Med. 1995, 1. 546-551.
3. 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.
4. Peri. L.; Pietraforte. D.; Scorza, G.; Napolitano, A.; Fogliano, V.; Mietti, M. Apples increase nitric oxide production by human saliva at the acidic pH of the stomach: A new biological function for polyphenols with a catechol group. Free Radical Biol. Med. 2005, 39, 668-681.
5. Pietraforte, D.; Castelli, M.; Metere, A.; Scorza, G.; Samoggia, P.; Menditto, A.; Mietti, M. Salivary uric acid at the acidic pH of the stomach is the principal defense against nitrite-derived reactive species: Sparing effects of chlorogenic acid and serum albumin. Free Radical Biol. Med. 2006, 41, 1753-1763.
6. 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.
7. Takahama, U.; Ryu, K: Hirota, S. Chlorogenic acid in coffee can prevent the formation of dinitrogen trioxide by scavenging nitrogen dioxide generated in the human oral cavity. J. Agric. Food Chem. 2007, 55, 9251-9258.
8. Brown, J. F.; Hanson, P. J.; Whittle, B. J. Nitric oxide donors increase mucus gel thickness in rat stomach. Eur. J. Pharmacol. 1992, 223, 103-104.
9. Desai, K. M.; Sessa, W. C.; Vane, J. R. Involvement of nitric oxide in the reflux relaxation of the stomach to accommodation of food or fluid. Nature 1991, 351, 477-479.
10. Pique, J. M.; Whittle, B. J.; Esplugues, J. V. The vasodilator role of endogenous nitric oxide in the rat gastric microcirculation. Eur. J. Pharmacol. 1989, 174, 293-296.
11. Whittle, B. J. Neuronal and endothelium-derived mediators in the modulation of gastric microcirculation: Integrity in the balance. Br. J. Pharmacol. 1993, 110, 3-17.
12. Benjamin, N.; O'Driscoll, F.; Dougall, H.; Duncan, C.; Smith, L.; Golden, M.: McKenzie, H. Stomach NO synthesis. Nature 1994, 368, 502.
13. Xu, J.; Xu, X.; Verstraete, W. The bactericidal effects and chemical reactions of acidified nitrite under conditions simulating the stomach. J. Appl. Microbiol. 2001, 90, 523-529.
14. McColl, K. E. L. When saliva meets acid: Chemical warfare at the oesophagogastric junction. Gut 2005, 54, 1-3.
15. 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.
16. 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. Metab. Dispos. 2001, 29, 1432-1439.
17. Panzella. L.; Napolitano, A.; d'Ischia, M. Oxidative conjugation of chlorogenic aicd with glutathione: Structural characterization of addition products and a new nitrite-protonated pathway. Bioorg. Med. Chem. 2003, 11, 4797-4805.
18. Dobrowska-Ufniarz. E.; Dzieniszwski, J.; Jarosz, M.; Wartanowicz, M. Vitamin C concentration in gastric juice in patients with precancerous lesion of the stomach and gastric cancer. Med. Sci. Monit. 2002, 8, CR96-CR103.
19. O'Conner, H. J.; Achorah, C. J.; Habibzedah, N.; Axon, A. T. R.; Cockel, R. Vitamin C in the human stomach: Relation to gastric pH, gastrodoudenal disease and possible sources. Gut 1989, 30, 436-442.
20. Takahama, U. Oxidation of vacuolar and apoplastic phenolic substrates by peroxidases: Physiological significance of the oxidation reactions. Phytochem. Rev. 2004, 3, 207-219.
21. Licht, W. R.; Tannenbaum, S. R.; Deen, W. M. Use of ascorbic acid to inhibit nitrosation: Kinetic and mass transfer considerations for an in vitro system. Carcinogenesis 1988, 9, 365-372.
22. 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.
23. Pannala, A. S.; Mani, A. R.; Spencer, J. P. E.; 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.
24. Tsuge, K.; Kataoka, M.; Seto, Y. Cyanide and thiocyanate levels in blood and saliva of healthy adult volunteers. J. Health Sci. 2000, 46, 343-350.
25. Fujii, S.; Yoshimura, T.: Kamada, H. Nitric oxide trapping efficientcies of water-soluble iron (III) complexes with dithiocarbamate derivatives. Chem. Lett. 1996, 785-786.
26. Jensen, B. O.; Skeidsvoll. J.; Holmsen, H. A polarogarphic method for measuring of dissolved nitric oxide. J. Biochem. Biophys. Method. 1997, 35, 185-195.
27. Lewis, R. S.; Deen, W. M. Kinetics of the reaction of nitric oxide with oxygen in aqueous solutions. Chem. Res. Toxicol. 1994, 7, 568-574.
28. Venkataraman, S.; Martin, S. M.; Schafer, F. Q.; Buettner, G. R. Detailed methods for the quantification of nitric oxide in aqueous solutions using either an oxygen monitor or EPR. Free Radical Biol. Med. 2000, 29, 580-585.
29. Doherty, A. M. M.; Garley, M. S.; Haine, N.; Stedman, G. Formation of an adduct between thiocyanate ion and nitrosyl thiocyanate. J. Chem, Soc., Dalton Trans. 1997, 2163-2166.
30. Bielski, B. H.: Allen, A. O.; Schwarz, H. A. Mechanism of disproportionaltion of ascorbate radicals. J. Am. Chem. Soc. 1981, 103, 3516-3518.
31. Laroff, G. P.; Fessenden, R. W.; Schuler, R. H. The electron spin resonance spectra of radical intermediates in the oxidation of ascorbic acid and related substances. J. Am. Chem. Soc. 1972, 94, 9062-9073.
32. Tsuchiya, K.; Yoshizumi, M.; Houchi, H.; Mason, R. P. Nitric oxide-formation between the iron-N-melhyl-D-glucamine dithiocarbamate complex and nitrite. J. Biol. Chem. 2000, 275, 1551-1556.
33. Holmes, A. J.; Williams, D. L. H. Reaction of ascorbic acid with S-nitrosothiols: Clear evidence for two distinct reaction pathways. J. Chem. Soc., Perkin Trans. 2 2000, 1639-1644.
34. Amado. S.: Blakelock, L.; Holmes. A. J.; Williams. D. L. H. Kinetics and mechanism of the formation of and reactions of S-nitroso derivatives of some heterocyclic thiones. J. Chem. Soc., Perkin Trans. 2 2001, 441-447.
35. Takahama, U.; Tanaka, M.: Hirota, S. Transformation of ethyl alcohol to ethyl nitrite in acidified saliva: Possibility of its occurrence in the stomach. Arch. Biochem. Biophys. 2008, 475, 135-139.
36. 2. Toxicology 1994, 89, 193-216.
37. Larauche, M.; Anton, P. M.; Gratia Villar, R.; Frexinos, J.; Bueno, L.; Firoramonti, J. Protective effect of dietary nitrate on experimental gastrisis in rats. Br J. Nutr. 2003, 89, 777-786.
38. Miyoshi, M.; Kasahara, E.; Park, A. M.; Hiramoto, K.; Mi-namiyama. Y.; Takemura, S.; Sato, E. F.; Inoue, M. Dietary nitrate inhibits stress-induced gastric mucosal injury in the rat. Free Radical Res. 2003, 37, 85-90.
39. Jannson, E. A.; Petersson, J.; Reinders, C.; Sobko, T.: Bjöne, H.; Philipson, M.; Weitzberg, E.; Holm, L.; Lundberg, J. O. Protection from nonsteroidal anti-inflammatory drug (NSAlD) -induced gastric ulcers by dietary nitrate. Free Radical Biol. Med. 2007, 42, 510-518.
40. Björne, H.; Petersson, J.; Phillipson, M.; Weitzberg, E.; Holm, L.; Lundberg, J. O. Nitrite in saliva increases gastric mucosal blood flow and mucus thickness. J. Clin. Invest. 2004, 113, 106-114.
41. Larauche, M.; Anton, P. M.; Gracia. Villar, R.; Theodorou. V.; Frexinos, J.; Bueno, L.; Fioramonti, J. Protective effect of dietary nitrate on experimental gastris in rats. Br. J. Nutr. 2003, 89, 777-786.
42. Suschek. C. V.; Schewe, T.; Sies, H.; Kroncke, K.-D. Nitrite, a naturally occurring precursor of nitric oxide that acts like a 'prodrug'. Biol. Chem. 2006, 387, 499-506.