Reactions of (+)-catechin with salivary nitrite and thiocyanate under conditions simulating the gastric lumen: Production of dinitrosocatechin and its thiocyanate conjugate

References

• Ölschläger C, Regos I, Zeller FJ, Treutter D. Identification of galloylated propelargonidins and procyanidins in buckwheat grain and quantification of rutin and flavanols from homostylous hybrids originating from F. esculentum×F. homotropicum. Phytochemistry 2008;69:1389–1397.
   Google Scholar
• Danila A-M, Kotani A, Hakamata H, Kusu F. Determination of rutin, catechin, epicatechin, and epicatechingallate in buckwheat Fagopyrum esculentum Moench by micro-high-performance liquid chromatography with electrochemical detection. J Agric Food Chem 2007;55:1139–1143.
   PubMed Web of Science ®Google Scholar
• Haslam E. Proanthocyanidins. In: Harborne JB, Mabry TJ (eds.). The Flavonoids: Advances in Research. London: Chapman and Hall; 1982. pp. 417–447.
   Google Scholar
• Pierpoint WS. Flavonoids in the human diet. In: Cody V, Middleton E Jr, Harborne JB (eds.). Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological, and Structure-Activity Relationships. New York: Alan R. Liss, Inc.; 1985. pp. 125–140.
   Google Scholar
• Bhagwat S, Haytowitz DB, Holden JM. USDA database for the flavonoid content of selected foods. Release 3.1. 2013 Available from: http://www.ars.usda.gov/SP2UserFiles/Place/12354500/Data/Flav/Flav3–1.pdf. Accessed on 7-March-2014.
   Google Scholar
• Yoshida K, Kondo T, Ito M, Kondo T. Analysis of polyphenols in water extract of red adzuki bean, Vigna angularis. ITE Lett New Tech Med 2005;6:226–231.
   Google Scholar
• Hoshiyama Y, Kawaguchi T, Miura Y, Mizoue T, Tokui N, Yatsuya H, et al.; JACC Study Group. Green tea and stomach cancer− a short review of prospective studies. J Epidemiol 2005;2:S109–S112.
   Google Scholar
• Sasazuki S, Inoue M, Miura T, Iwasaki M, Tsugane S. Plasma tea polyphenols and gastric cancer risk: a case-control study nested in a large population-based prospective study in Japan. Cancer Epidemiol Biomarkers Prev 2008;17:343–351.
   PubMed Web of Science ®Google Scholar
• Venables MC, Hulston CJ, Cox HR, Jeukendrup AE. Green tea extract ingestion, fat oxidation, and glucose tolerance in healthy humans. Am J Clin Nutr 2008;87:778–784.
   PubMed Web of Science ®Google Scholar
• Brown AL, Lane J, Coverly J, Stocks J, Jackson S, Stephen A, et al. Effects of dietary supplementation with the green tea polyphenol epigallocatechin-3-gallate on insulin resistance and associated metabolic risk factors: randomized controlled trial. Br J Nutr 2009;101:886–894.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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;39:668–681.
   Google Scholar
• Hirota S, Takahama U. Reactions of apple fruit polyphenols with nitrite under conditions of the gastric lumen: Generation of nitric oxide and formation of nitroso catechins. Food Sci Technol Res 2014;20:439–447.
   Web of Science ®Google Scholar
• Panzella L, Manini P, Napolitano A, D’Ischia M. The acid-promoted reaction of the green tea polyphenol epigallocatechin gallate with nitrite ions. Chem Res Toxicol 2005;18:722–729.
   PubMed Web of Science ®Google Scholar
• Lee SYH, Muerol B, Pollard S, Youdim KA, Pannala AS, Kuhnle GGC, et al. The reaction of flavonols with nitrous acid protects against N-nitrosamine formation and leads to the formation of nitroso derivatives which inhibit cancer cell growth. Free Radic Biol Med 2006;40:323–334.
   PubMed Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• Maoela MS, Arotiba OA, Baker PGL, Mabusela, WT, Jahed N, Songa EA, Iwuoha EI. Electroanalytical determination of catechin flavonoid in ethyl acetate extracts of medicinal plants. Int J Electrochem Sci 2009;4:1497–1510.
   Web of Science ®Google Scholar
• Konieczny MT, Konieczny W, Sabisz M, Skladanowski A, Wakiec R, Augustynowicz-Kopec E, Zwolska Z. Synthesis of isomeric, oxathiolone fused chalcones, and comparison of their activity toward various microorganisms and human cancer cells line. Chem Pharm Bull 2007;55: 817–820.
   Google Scholar
• 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.
   Google Scholar
• 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.
   Google Scholar
• Shen CC, Chang YS, Ho LK. Nuclear magnetic resonance studies of 5,7-dihydroxyflavonoids. Phytochemistry 1993;34:843–845.
   Web of Science ®Google Scholar
• Fossen T, Rayyan S, Andersen Ø M. Dimeric anthocyanidins from strawberry (Fragaria ananasa) consisting of pelargonidin 3-glucoside covalently linked to four flavan 3-ols. Phytochemistry 2004;65:1421–1428.
   PubMed Web of Science ®Google Scholar
• Takahama U, Yamauchi R, Hirota S. Isolation and characterization of a cyanidin-catechin pigment from adzuki bean (Vigna angularis). Food Chem 2013;141:282–288.
   Google Scholar
• Veljovic-Jovanovic S, Morina F, Yamauchi R, Hitota S, Takahama U. Interaction between (+)-catechin and quercetin during their oxidation by nitrite under the conditions simulating the stomach. J Agric Food Chem 2014;62:4951–4959.
   Google Scholar
• Takahama U, Tanaka M, Hirota S. Formation of nitric oxide, ethyl nitrite and an oxathiolone derivative of caffeic acid in the mixture of saliva and white wine. Free Radic Res 2010;44:293–303.
   Web of Science ®Google Scholar
• Kharitonov VG, Sundquist AR, Sharma VS. Kinetics of nitric oxide autoxidation in aqueous solution. J Biol Chem 1994;269:5581–5583.
   Google Scholar
• Venkataraman S, Martin SM, Schafer FQ, Buettner GR. Detailed methods for the quantification of nitric oxide in aqueous solutions using either an oxygen monitor or EPR. Free Radic Biol Med 2000;29:580–585.
   PubMed Web of Science ®Google Scholar
• Gorelik S, Lapidot T, Shaham I, Granit R, Ligumsky M, Kohen R, Kanner J. Lipid peroxidation and coupled vitamin oxidation in simulated and human gastric fluid inhibited by dietary polyphenols: health implications. J Agric Food Chem 2005;53:3397–3402.
   PubMed Web of Science ®Google Scholar
• Jacobi CA, Zieren HU, Muller JM, Adili F, Pichlmaier H. Patients with esophageal carcinoma. Eur Surg Res 1996;28: 26–31.
   Google Scholar
• Simonian HP, Vo L, Doma S, Fisher RS, Parkman HP. Regional postprandial differences in pH within the stomach and gastroesophageal junction. Dig Dis Sci 2005;50:2276–2285.
   PubMed Web of Science ®Google Scholar
• Issacs NS, van Eldik R. A mechanismtic study of the reaction of quinones by ascorbic acid. J Chem Soc Perkin Trans 1997;2:1465–1468.
   Google Scholar
• Rocha BS, Gago B, Barbosa RM, Laranjinha J. Dietary polyphenols generate nitric oxide from nitrite in the stomach and induce smooth muscle relaxation. Toxicology 2009;265: 41–48.
   PubMed Web of Science ®Google Scholar
• Takahama U, Tanaka M, Hirota S. Proanthocyanidins in buckwheat flour can reduce salivary nitrite to nitric oxide in the stomach. Plant Food Hum Nutr 2010;65:1–7.
   PubMed Web of Science ®Google Scholar
• Tanaka K, Hayatsu T, Negishi T, Hayatsu H. Inhibition of N-nitrosation of secondary amines in vitro by tea extracts and catechins. Mutat Res 1998;412:91–98.
   PubMed Web of Science ®Google Scholar
• Masuda S, Uchida S, Terashima Y, Kuramoto H, Serozawa M, Deguchi Y, et al. Effect of green tea on the formation of nitrosoamines, and cancer mortality. J Health Sci 2006;52: 211–220.
   Google Scholar
• Jovanovic SV, Steenken S, Simic MG, Hara Y. Antioxidant properties of flavonoids: reduction potentials and electron transfer reactions of flavonoid radicals. In: Rice-Evans CA, Packer L, (eds.). Flavonoids in Health and Disease. New York: Marcel Dekker Inc. 1998. pp. 137–161.
   Google Scholar
• Gunther MP, His LC, Curtis JF, Gierse JK, Marnett LJ, Eling, TE, Mason RP. Nitric oxide trapping of the tyrosyl radical of prostaglandin H synthase-2 leads to tyrosine iminoxyl radical and nitrotyrosine formation. J Biol Chem 1997;272: 17086–17090.
   PubMed Web of Science ®Google Scholar
• Uppu RM, Lemercier J-N, Squadrito GL, Zhang H, Bolzan RM, Pryor1 WA. Nitrosation by peroxynitrite: Use of phenol as a probe. Arch Biochem Biophys 1998;358:1–16.
   Google Scholar
• Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ. Role of quinones in toxicology. Chem Res Toxicol 2000;13:135–160.
   PubMed Web of Science ®Google Scholar
• Hord NG, Tang Y, Bryan NS. Food sources of nitrates and nitrites: the physiologic context for potential health benefits. Am J Clin Nutr 2009;90:1–10.
   PubMed Web of Science ®Google Scholar
• Schönthal AH. Adverse effects of concentrated green tea extracts. Mol Nutr Food Res 2011;55:874–85.
   PubMed Web of Science ®Google Scholar
• Lambert JD, Sang S, Yang CS. Biotransformation of green tea polyphenols and the biological activities of those metabolites. Mol Pharmaceutics 2007;4:819–25.
   PubMed Web of Science ®Google Scholar