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

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 10, 2007, Pages 4169-4176

  Takahama, Umeo ^a   Tanaka, Mariko ^a   Oniki, Takayuki ^a   Hirota, Sachiko ^b   Yamauchi, Ryo ^c  

^a KYUSHU DENTAL COLLEGE   (Japan)

^b KYUSHU WOMEN'S UNIVERSITY   (Japan)

^c GIFU UNIVERSITY   (Japan)

Author keywords

Chlorogenic acid; Coffee; Nitrous acid; Saliva; Thiocyanate

Indexed keywords

CHLOROGENIC ACID; NITRITE; THIOCYANIC ACID DERIVATIVE;

CHEMISTRY; COFFEE; CONFERENCE PAPER; CYTOLOGY; EPITHELIUM CELL; HUMAN; METABOLISM; PH; SALIVA; STOMACH JUICE;

CHLOROGENIC ACID; COFFEE; EPITHELIAL CELLS; GASTRIC JUICE; HUMANS; HYDROGEN-ION CONCENTRATION; NITRITES; SALIVA; THIOCYANATES;

EID: 34249885888     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0634606     Document Type: Conference Paper

References (32)

1. Higdon, J. V.; Frei, B. Coffee and health: a review of recent human research. Crit. Rev. Food Sci. Nutr. 2006, 46, 101-123.
2. 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.
3. Walle, T.; Browning, A. M.; Steed, L. L.; Reed, S. G.; Walle, U. K. Flavonoid glucosides are hydrolyzed and thus activated in the oral cavity in humans. J. Nutr. 2005, 135, 48-52.
4. 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.
5. Ferguson, D. B. Salivary electrolytes. In Human Saliva. Clinical Chemistry and Microbiology; Tenovuo, J., Ed.; Vol. I; CRC Press: Boca Raton, FL, 1989; pp 75-99.
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. 2003, 50, 4317-4322.
7. 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.
8. 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.
9. Kono, Y.; Shibata, H.; Kodama, Y.; Sawa, Y. The suppression of the N-nitrosating reaction by chlorogenic acid. Biochem. J. 1995, 312, 947-953.
10. 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.
11. Fan, T.-Y.; Tannenbaum, S. R. Factors influencing the rate of formation of nitrosomorpholine for morpholine and nitrite: acceleration by thiocyanate and other anions. J. Agric. Food Chem. 1973, 21, 237-240.
12. Takahama, U.; Oniki, T. Salivary thiocyanate/nitrite inhibits hydroxylation of 2-hydroxybenzoic acid induced by hydrogen peroxide/Fe(II) systems under acidic conditions; possibility of thiocyanate/nitrite-dependent scavenging of hydroxyl radical in the stomach. Biochim. Biophys. Acta 2004, 1675, 130-138.
13. 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.
14. Takahama, U.; Oniki, T.; Murata, H. The presence of 4-hydroxyphenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach. FEBS Lett. 2002, 518, 116-118.
15. Kou, F.; Takahama, U. Hydrogen peroxide-induced luminescence and evolution of molecular oxygen in human saliva. Arch. Oral Biol. 1995, 40, 15-21.
16. Fujii, S.; Yoshimura, T.; Kamada, H. Nitric oxide trapping efficiencies of water-soluble iron (III) complex with dithiocarbamate derivatives. Chem. Lett. 1996, 785-786.
17. Kalyanaraman, B. Detection of nitric oxide by electron spin resonance in chemical, photochemical, cellular, physiological, and pathophysiological systems. Methods Enzymol. 1996, 268, 168-187.
18. Venkataraman, S.; Martin, S. M.; Schafer, F. Q.; Buettner, G. R. Detailed method for the quantification of nitric oxide in aqueous solutions using either an oxygen electrode or EPR. Free Radical Biol. Med. 2000, 29, 580-585.
19. Iwai, K.; Kishimoto, N.; Kakino, Y.; Mochida, K.; Fujita, T. In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxinnamoyl derivatives in green coffee beans. J. Agric. Food Chem. 2004, 52, 4893-4898.
20. 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.
21. Murata, M.; Sugiura, M.; Sonokawa, Y.; Shimamura, T.; Homma, S. Properties of chlorogenic acid quinone: relationship between browning and the formation of hydrogen peroxide from a quinone solution. Biosci. Biotechnol. Biochem. 2002, 66, 2525-253.
22. Oury, T. D.; Tatro, L.; Ghio, A. J.; Piantadosi, C. A. Nitration of tyrosine by hydrogen peroxide and nitrite. Free Radical Res. 1995, 23, 537-547.
23. 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.
24. Degado-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.
25. 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.
26. 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.
27. Cilliers, J. J. L.; Singleton, V. L. Characterization of the products of nonenzymic autoxidative phenolic reactions in a caffeic acid model system. J. Agric. Food Chem. 1991, 39, 1298-1303.
28. Saito, S.; Kawabata, J. Synergistic effects of thiols and amines on antiradical efficiency of protocatechuic acid. J. Agric. Food Chem. 2004, 52, 8163-8168.
29. Richard, F. C.; Goupy, P. M.; Nicolas, J. J.; Lacombe, J.-M.; Pavia, A. A. Cysteine as an inhibitor of enzymatic browning. 1. Isolation and characterization of addition compounds formed during oxidation of phenolics by apple polyphenol oxidase. J. Agric. Food Chem. 1991, 39, 841-847.
30. Katayama, Y.; Narahara, Y.; Inoue, Y.; Amano, F.; Kanagawa, T.; Kuraishi, H. A thiocyanate hydrolase of Thiobacillus thioparru. A novel enxyme catalyzing the formation of carbonyl sulfide from thiocyanate. J. Biol. Chem. 1992, 267, 9170-9175.
31. Tenovuo, J. Nonimmunoglobulin defense factors in human saliva. In Human Saliva. Clinical Chemistry and Microbiology: Tenovuo, J., Ed.; Vol. II; CRC Press: Boca Raton, FL, 1989; pp 55-91.
32. Takahama, U.; Hirota, S.; Nishioka, T.; Oniki, T. Human salivary peroxidase-catalyzed oxidation of nitrite and nitration of salivary component 4-hydroxyphenylacetic acid and proteins. Arch. Oral. Biol. 2003, 48, 679-690.