Preprint Review Version 1 This version is not peer-reviewed

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

Version 1 : Received: 27 June 2017 / Approved: 28 June 2017 / Online: 28 June 2017 (07:41:14 CEST)

A peer-reviewed article of this Preprint also exists.

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

Journal reference: Antioxidants 2017, 6, 53
DOI: 10.3390/antiox6030053

Abstract

Foods are mixed with saliva in the oral cavity and swallowed. During staying in the stomach, saliva is contentiously provided to mix with the ingested foods. Because a salivary component 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.

Subject Areas

flavonoids; nitric oxide (•NO); nitrosation; nitrous acid; quinones; redox reactions; stomach; thiocyanic acid.

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