Reduction of nitrous acid to nitric oxide by coffee melanoidins and enhancement of the reduction by thiocyanate: Possibility of its occurrence in the stomach

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 12, 2008, Pages 4736-4744

  Takahama, Umeo ^a   Hirota, Sachiko ^b  

^a KYUSHU DENTAL COLLEGE   (Japan)

^b KYUSHU WOMEN'S UNIVERSITY   (Japan)

Author keywords

Coffee; Melanoidins; Nitric oxide (NO); Nitrous acid; Oxygen uptake

Indexed keywords

CHLOROGENIC ACID; MELANOIDIN POLYMERS; NITRIC OXIDE; NITROUS ACID; POLYMER; THIOCYANATE; THIOCYANIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; COFFEE; ELECTRON SPIN RESONANCE; OXIDATION REDUCTION REACTION; SALIVA; STOMACH JUICE;

CHLOROGENIC ACID; COFFEE; ELECTRON SPIN RESONANCE SPECTROSCOPY; GASTRIC JUICE; NITRIC OXIDE; NITROUS ACID; OXIDATION-REDUCTION; POLYMERS; SALIVA; THIOCYANATES;

EID: 47349109640     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf703660k     Document Type: Article

References (36)

1. Takahama, U.; Hirota, S.; Oniki, T. Thiocyanate cannot inhibit the formation of reactive nitrogen species in the 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.
2. 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.
3. Peri, L.; Pietraforte, D.; Scoza, G.; Napolitano, A.; Fogliano, V.; Minetti, M. Apples increase nitric oxide production by human saliva at acidic pH of the stomach: A new biological function for polyphenols with a catechol group. Free Radical Biol. Med. 2005, 39, 668-681.
4. 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.
5. 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.
6. Gonis, J.; Hewitt, D. G.; Troup, G.; Hutton, D. R.; Hunter, C. R. The chemical origin of free radicals in coffee and other beverages. Free Radical Res. 1995, 23, 393-399.
7. Pascual, E. C.; Goodman, B. A.; Yeretzian, C. Characterization of free radicals in soluble coffee by electron paramagnetic resonance spectroscopy. J. Agric. Food Chem. 2002, 50, 6114-6122.
8. Delgado-Andrade, C.; Rufián-Henares, J. A.; Morales, F. J. Assesing the antioxidant activity of melanoidins from coffee brews by different antioxidant methods. J. Agric. Food Chem. 2005, 53, 7832-7836.
9. Borrelli, R. C.; Visconti, A.; Mennella, C.; Anese, M.; Fogliano, V. Chemical characterization and antioxidant properties of coffee melanoidins. J. Agric. Food Chem. 2002, 50, 6527-6533.
10. Glösl, S.; Wagner, K. H.; Draxler, A.; Kaniak, M.; Lichtenecker, S.; Sonnleitner, A.; Somoza, V.; Erbersdobler, H.; Elmadfa, I. Genotoxicity and mutagenicity of melanoidins isolated from a roasted glucose-glycine model in human lymphocyte cultures, intestinal Caco-2 cells and in the Salmonella typhimurium strains TA98 and TA102 applying the AMES test. Food Chem. Toxicol. 2004, 42, 1487-1495.
11. Fujii, S.; Yoshimura, T.; Kamada, H. Nitric oxide trapping efficiencies of water-soluble iron(III) complexes with dithiocarbamate derivatives. Chem. Lett. 1996, 785-786.
12. Kalyanaraman, B. Detection of nitric oxide by electron spin resonance in chemical, photochemical, cellular, physiological, and pathophysiological systems. Methods Enzymol. 1996, 268, 168-187.
13. 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.
14. Takahama, U.; Oniki, T.; Hirota, S. Phenolic components of brown scales of onion bulbs produce hydrogen peroxide by autooxidation. J. Plant Res. 2001, 114, 395-402.
15. Chio, S.-S.; Hyde, J. S.; Sealy, R. C. Paramagnetism in melanins: pH dependence. Arch. Biochem. Biophys. 1982, 215, 100-106.
16. Arnaud, R.; Perbet, G.; Defladre, A.; Lang, G. Electron spin resonance of melanin from hair. Effects of temperature, pH and light irradiation. Photochem. Photobiol. 1983, 38, 161-168.
17. Bekedam, K. E.; Schlos, H. A.; van Boekel, M. A. J. S.; Smit, G. High molecular weight melanoidins from coffee brew. J. Agric. Food Chem. 2006, 54, 7658-7666.
18. Bekedam, E. K.; Schols, H. A.; Van Boekel, M. A. J. S.; Smit, G. Incorporation of chlorogenic acids in coffee brew melanoidins. J. Agric. Food Chem. 2008, 56, 2055-2063.
19. Maegawa, Y.; Sugino, K.; Sakurai, H. Identification of free radical species derived from caffeic acid and related polyphenols. Free Radical Res. 2007, 41, 110-119.
20. Namiki, M.; Yabuta, G.; Koizumi, Y.; Yano, M. Development of free radical products during the greening reaction of caffeic acid esters (or chlorogenic acid) and a primary amino compound. Biosci., Biotechnol., Biochem. 2001, 65, 2131-2136.
21. 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.
22. Verkatraraman, S.; Martin, S. M.; Schafer, F. Q.; Buettner, G. R. Detailed methods for the quantification of nitric oxide in aqueous solutions using either oxygen monitor or EPR. Free Radical Biol. Med. 2000, 29, 580-585.
23. Lewis, R. S.; Deen, W. M. Kinetics of the reaction nitric oxide with oxygen in aqueous solutions. Chem. Res. Toxicol. 1994, 7, 568-574.
24. 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.
25. 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.
26. Benjamin, N.; O'Driscoll, F.; Dougall, H.; Duncan, C.; Smith, L.; Golden, M.; McKenzie, H. Stomach NO synthesis. Nature 1994, 368, 502.
27. 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.
28. Yu, H.; Sato, E. F.; Nagata, K.; Nishikawa, M.; Kashiba, M.; Arakawa, T.; Kobayashi, K.; Tamura, T.; Inoue, M. Oxygen-dependent regulation of respiration and growth of Escherichia coli by nitric oxide. FEBS Lett. 1997, 409, 161-165.
29. Rufián-Henares, J. A.; Morales, F. J. Functional properties of melanoidins: In vitro antioxidant, antimicrobial and antihypertensive activities. Food Res. Int. 2007, 40, 995-1002.
30. Daglia, M.; Cuzzoni, M. T.; Dacarro, C. Antibacterial activity of coffee. J. Agric. Food Chem. 1994, 42, 2270-2272.
31. Daglia, M.; Cuzzoni, M. T.; Dacarro, C. Antibacterial activity of coffee: Relationship between biological activity and chemical markers. J. Agric. Food Chem. 1994, 42, 2273-2277.
32. 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.
33. 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.
34. 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.
35. 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.
36. Tottrup, A.; Ny, L.; Aim, P.; Larsson, B.; Forman, A.; Andersson, K.-E. The role of the arginine/nitric oxide pathway for relaxation of the human lower oesophagal sphincter. Acta Physiol. Scand. 1993, 149, 451-459.