Formation of nitric oxide, ethyl nitrite and an oxathiolone derivative of caffeic acid in a mixture of saliva and white wine

Free Radical Research

Volumn 44, Issue 3, 2010, Pages 293-303

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

^a KYUSHU DENTAL COLLEGE   (Japan)

^b KYUSHU WOMEN'S UNIVERSITY   (Japan)

Author keywords

Ethyl nitrite; Nitric oxide (NO); Nitrite; Oxathiolone derivative; Saliva; Stomach; Wine

Indexed keywords

CAFFEIC ACID; NITRIC OXIDE; NITRITE; THIOL DERIVATIVE;

ADULT; ARTICLE; CONTROLLED STUDY; HUMAN; HUMAN EXPERIMENT; INGESTION; MOUTH CAVITY; NORMAL HUMAN; PH; SALIVA; STOMACH; WINE;

ANTIOXIDANTS; CAFFEIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; MIDDLE AGED; NITRIC OXIDE; NITRITES; SALIVA; WINE;

EID: 77249107851     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.3109/10715760903486057     Document Type: Article

References (42)

1. Teissedre PL, Landrault T. Wine phenolics: contribution to dietary intake and bioavailability. Food Res Int 2000;33: 461-467.
2. Gago B, Lundberg JO, Barbosa RM, Laranjinha J. Red wine-dependent reduction of nitrite to nitric oxide in the stomach. Free Radic Biol Med 2007;43:1233-1242.
3. 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.
4. Takahama U, Yamamoto A, Hirota S, Oniki T. Quercetin-dependent reduction of 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, Tanaka M, Hirota S. Interaction between ascorbic acid and chlorogenic acid during the formation of nitric oxide in acidifi ed saliva. J Agric Food Chem 2008;56: 10406-10413.
6. Peri L, Pietraforte D, Scorza G, Napolitano A, Fogliano V, Minetti 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 Radic Biol Med 2005;3:668-681.
7. Pannala AS, Mani AR, Spencer JPE, Skinner Y, Bruckdorfer KR, Moore KP, Rice-Evans CA. The effect of dietary nitrate on salivary, plasma and urinary nitrate metabolism in humans. Free Radic Biol Med 2003;34:576-584.
8. Palmerini CA, Palombari R, Perito S, Arienti G. NO synthesis in human saliva. Free Radic Res 2003;37:29-31.
9. Zetterquist W, Pedroletti C, Lundberg JO, Alving K. Salivary contribution to exhaled nitric oxide. Eur Respir J 1999;13: 327-333.
10. Doel JJ, Hector MP, Amirtham CV, Al-Anzan LA, Benjamin N, Allaker R P. Protective effect of salivary nitrite and microbial nitrate reductase activity against caries. Eur J Oral Sci 2004;112:424-428.
11. Benjamin N, Hector MP, Rogers M, Allaker RP. Evaluation of bacterial nitrate reduction in the human oral cavity. Eur J Oral Sci 2005;113:14-19.
12. Björne H, Petersson J, Phillipson M, Weitzberg E, Holm L, Lundberg JO. Nitrite in saliva increases gastric mucosal blood fl ow and mucus thickness. J Clinic Invest 2004;113: 106-114.
13. Whittle BJ, Lopez-Belmonte J, Moncada S. Regulation of gastric mucosal integrity by endogenous nitric oxide: interactions with prostanoids and sensory neuropeptides in the rat. Br J Pharmacol 1990;99:607-611.
14. Gago B, Nyström T, Cavaleiro C, Rocha BS, Barbosa RM, Laranjinha J, Lundberg JO. The potent vasodilator ethyl nitrite is formed upon reaction of nitrite and ethanol under gastric conditions. Free Radic Biol Med 2008;45:404-412.
15. Takahama U, Tanaka M, Hirota S. Transformation of ethyl alcohol to ethyl nitrite in acidifi ed saliva: possibility of its occurrence in the stomach. Arch Biochem Biophys 2008; 475:135-139.
16. Tenovuo J. Nonimmunoglobulin defense factors in human saliva. In: Tenovuo JO, editor. Human saliva: Clinical chemistry and microbilology. Vol II. Boca Raton, FL: CRC Press; 1989. p. 55-91.
17. Licht WR, Tannenbaum SR, Deen WM. Use of ascorbic aicd to inhibit nitrosation: kinetic and mass transfer consideration for an in vitro system. Carcinogenesis 1988;9:365-372.
18. Takahama U, Tanaka M, Oniki T, Hirota S, Yamauchi R. Formation of 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.
19. Takahama U, Tanaka M, Hirota S, Yamauchi R. Formation of an oxathiolone compound from rutin in acidic mixture of saliva and buckwheat dough: possibility of its occurrence in the stomach. Food Chem 2009;116:214-219.
20. Caccetta RA-A, Croft KD, Beilin LJ, Puddey IB. Ingestion of red wine signifi cantly increases plasma phenolic acid concentrations but does not acutely affect ex vivo lipoprotein oxidizability. Am J Clin Nutr 2000;71:67-74.
21. Soleas GJ, Dam J, Carey M, Goldberg DM. Toward the fi ngerprinting of wines: cultivar-related patterns of poly-phenolic constituents in Ontario wines. J Agric Food Chem 1997;45:3871-3880.
22. Kallithraka S, Salacha MI, Tzourou I. Changes in phenolic composition and antioxidant activity of white wine during bottle storage: accelerated browning test versus bottle storage. Food Chem 2008;113:500-505.
23. Lundberg JO, Weitzberg E, Lundberg JM, Alving K. Intragastric nitric oxide production in humans: measurement in expelled air. Gut 1994;35:1543-1546.
24. Hisatsne IC, Zafonte L. Kinetic study of some third-order reactions of nitric oxide. J Phys Chem 1969;73:2980-2989.
25. Deng XB, Bludeau P, Deitrich RA. Formation of ethyl nitrite in vivo after ethanol administration. Alcohol 2004;34: 217-223.
26. Napolitano A, d'Ischia M. New insights into the acid-promoted reaction of caffeic acid and its esters with nitrite: decarboxylation drives chain nitrosation pathways toward novel oxime derivatives and oxidation/fragmentation products thereof. J Org Chem 2002;67:803-810.
27. Lutter M, Clark AC, Prenzler PD, Scollary GR. Oxidation of caffeic acid in a wine-like medium: production of dihydroben-zaldehyde and its subsequent reactions with (+)-catechin. Food Chem 2007;105:968-975.
28. Rousseau B, Rosazza JPN. Reaction of ferulic acid with nitrite: formation of 7-hydroxy-6-methoxy-1,2-(4 H)-benzoxazin-4-one. J Agric Food Chem 1998;46:3314-3317.
29. Kikugawa K, Hakamada T, Hasunuma M, Kurechi T. Reaction of p-hydroxycinnamic acid derivatives with nitrite and its relevance to nitrosoamin formation. J Agric Food Chem 1983;31:780-785.
30. Galanti LM. Specifi city of salivary thiocyanate as marker of cigarette smoking is not affected by alimentary sources. Clin Chem 1997;43:184-185.
31. Tsuge K, Kataoka M, Seto Y. Cyanide and thiocyanaide levels in blood and saliva of healthy adult volunteers. J Health Environ 2000;46:343-350.
32. Lius V, Sennerfeldt P. Local treatment of acne with thiox-olone. Lakartidningen 1979;76:39-41.
33. Konieczny MT, Konieczny W, Sabisz M, Skladanowski A, Wakiec R, Augustynowicz-Kopec E, Zwolska Z. Synthesis of isomeric, oxathiolone fused to chalcones, and comparison of their activity toward various microorganisms and human cancer cells line. Chem Pharm Bull 2007;55:817-820. (Pubitemid 46708617)
34. Kim BH, Roh E, Lee HY, Lee IJ, Ahn B, Jung SH, Lee H, Han SB, Kim Y. Benzoxathiole derivative blocks lipopolysac-charide-induced nuclear factor-kappaB activation and nuclear factor-kappaB-regulated gene transcription through inactivating inhibitory kappaB kinase beta. Mol Pharmacol 2008;73: 1309-1318.
35. Innocenti A, Maresca A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors; thioxolone versus sulfonamides for obtaining isozyme-selective inhibitors? Bioorg Med Chem Lett 2008;18:3938-3941.
36. Povalishev VN, Polozov GI, Shadyro OI. Effects of α-tocopherol and related compounds on reactions involving various organic radicals. Bioorg Med Chem Lett 2006;16:1236-1239.
37. Desai KM, Sessa WC, Vane JR. Involvement of nitric oxide in the reflex relaxation of the stomach to accommodate food and fluid. Nature 1991;351:477-479.
38. Benjamin N, O'Driscoll F, Dougall H, Duncan C, McKenzie H. Stomach NO sysnthesis. Nature 1994;368:502.
39. Yu H, Sato EF, Nagata K, Nishikawa M, Kashiba M, Arakawa T, Kobayashi K, Tamura T, Inoue M. Oxygen-dependent regulation of the respiration and growth of Escherichia coli by nitric oxide. FEBS Lett 1997;409:161-165.
40. Xu J, Xu X, Verstraete W. The bactericidal effect and chemical reactions of acidifi ed nitrite under conditions simulating the stomach. J Appl Microbiol 2001;90:523-529.
41. Larauche M, Anton PM, Gracia-Villar R, Theodorou V, Frex-inos J, Bueno L, Fioramonti J. Protective effect of dietary nitrate on experimental gastritis in rates. Br J Nutr 2003; 89:777-786.
42. Jansson EA, Petersson J, Reinders C, Sobko T, Bjorne H, Phillipson M, Weitberg E, Holm L, Lundberg JO. Protection from nonsteroidal anti-infl ammatory drug (NSAID)-induced gastric ulcers by dietary nitrate. Free Radic Biol Med 2007;42:510-518.