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Antioxidants 2017, 6(3), 53; doi:10.3390/antiox6030053

Possible Reactions of Dietary Phenolic Compounds with Salivary Nitrite and Thiocyanate in the Stomach

Department of Health and Nutrition Care, Faculty of Allied Health Sciences, University of East Asia, Shimonoseki 751-8503, Japan
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Received: 7 June 2017 / Revised: 27 June 2017 / Accepted: 1 July 2017 / Published: 5 July 2017
(This article belongs to the Special Issue Bioactive Phenolic Compounds)
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Abstract

Foods are mixed with saliva in the oral cavity and swallowed. While staying in the stomach, saliva is contentiously provided to mix with the ingested foods. Because a salivary component of nitrite is protonated to produce active nitrous acid at acidic pH, the redox reactions of nitrous acid with phenolic compounds in foods become possible in the stomach. In the reactions, nitrous acid is reduced to nitric oxide (•NO), producing various products from phenolic compounds. In the products, stable hydroxybezoyl benzofuranone derivatives, which are produced from quercetin and its 7-O-glucoside, are included. Caffeic acid, chlorogenic acid, and rutin are oxidized to quinones and the quinones can react with thiocyanic acid derived from saliva, producing stable oxathiolone derivatives. 6,8-Dinitrosocatechis are produced from catechins by the redox reaction, and the dinitrocatechins are oxidized further by nitrous acid producing the quinones, which can make charge transfer complexes with the dinitrosocatechin and can react with thiocyanic acid producing the stable thiocyanate conjugates. In this way, various products can be produced by the reactions of salivary nitrite with dietary phenolic compounds, and reactive and toxic quinones formed by the reactions are postulated to be removed in the stomach by thiocyanic acid derived from saliva. View Full-Text
Keywords: flavonoids; nitric oxide (•NO); nitrosation; nitrous acid; quinones; redox reactions; stomach; thiocyanic acid flavonoids; nitric oxide (•NO); nitrosation; nitrous acid; quinones; redox reactions; stomach; thiocyanic acid
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Takahama, U.; Hirota, S. Possible Reactions of Dietary Phenolic Compounds with Salivary Nitrite and Thiocyanate in the Stomach. Antioxidants 2017, 6, 53.

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