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

机译:饮食中酚类化合物与唾液中亚硝酸盐和硫氰酸盐的可能反应

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摘要

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.
机译:食物会与口腔中的唾液混合并被吞咽。在停留在胃中时,有争议地提供唾液以与摄入的食物混合。由于亚硝酸盐的唾液成分被质子化,从而在酸性pH下产生活性亚硝酸,因此在胃中亚硝酸与酚类化合物的氧化还原反应成为可能。在反应中,亚硝酸还原为一氧化氮(•NO),由酚类化合物生产出多种产物。在产物中,包括由槲皮素及其7-O-葡糖苷生产的稳定的羟基苯甲酰基苯并呋喃酮衍生物。咖啡酸,绿原酸和芦丁被氧化成醌,并且醌可以与唾液衍生的硫氰酸反应,生成稳定的氧杂硫酮衍生物。儿茶素通过氧化还原反应生成6,8-二亚硝基儿茶酚,亚硝基酸进一步氧化二硝基儿茶素,生成醌,后者可与二亚硝基儿茶素形成电荷转移络合物,并可与硫氰酸反应生成稳定的硫氰酸盐共轭物。以此方式,唾液亚硝酸盐与饮食酚类化合物的反应可制得各种产品,并且推测由该反应形成的反应性和有毒醌在胃中被唾液衍生的硫氰酸除去。

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