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?

Peri, Laura; Pietraforte, Donatella; Scorza, Giuseppe; Napolitano, Aurora; Fogliano, Vincenzo; Minetti, Maurizio

doi:10.1016/j.freeradbiomed.2005.04.021

Cited by 134 publications

(122 citation statements)

References 53 publications

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“…The resulting spectrum is shown in line 3. The formation of the o-semiquinone radical, corresponding to the one-electron oxidation of the parent phenol is in accordance with results by others, showing the formation of chlorogenic and quercetin radicals upon reaction with acidic nitrite [18,19].…”

Section: μM (Line 4)supporting

confidence: 91%

“…Therefore, these compounds are likely candidates to undergo a redox reaction with nitrite during digestion, yielding U NO. Accordingly, chlorogenic acid and quercetin (phenolics exhibiting a catechol moiety) were shown to enhance the production of U NO from nitrite at acidic pH [18,19]. On the other hand, ascorbic acid, a compound that exhibits a low redox potential, and actively secreted in the stomach, has also been shown to be an efficient one-electron reductant of nitrite [42,43].…”

Section: Discussionmentioning

confidence: 99%

“…Yet, dietary polyphenols that, depending on its structure, have been shown to redox interact with oxidant radicals, thus preventing oxidative reactions, may be present in large amounts in the stomach in a diet-dependent way and likely promote U NO formation at high fluxes. Accordingly, it has been demonstrated that chlorogenic acid and quercetin enhance the production of U NO from nitrite at acidic pH [18,19].…”

Section: Introductionmentioning

confidence: 99%

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Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Gago

Lundberg

Barbosa

et al. 2007

Free Radical Biology and Medicine

155

111

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Nitrite may be a source for nitric oxide ( U NO), particularly in highly acidic environments, such as the stomach. Diet products contribute also with reductants that dramatically increase the production of U NO from nitrite. Red wine has been attributed health promoting properties largely on basis of the reductive antioxidant properties of its polyphenolic fraction. We show in vitro that wine, wine anthocyanin fraction and wine catechol (caffeic acid) dose-and pH-dependently promote the formation of U NO when mixed with nitrite, as measured electrochemically. The production of U NO promoted by wine from nitrite was substantiated in vivo in healthy volunteers by measuring U NO in the air expelled from the stomach, following consumption of wine, as measured by chemiluminescence. Mechanistically, the reaction involves the univalent reduction of nitrite, as suggested by the formation of U NO and by the appearance of EPR spectra assigned to wine phenolic radicals. Ascorbic and caffeic acids cooperate in the reduction of nitrite to U NO. Moreover, reduction of nitrite is critically dependent on the phenolic structure and nitro-derivatives of phenols are also formed, as suggested by caffeic acid UV spectral modifications. The reduction of nitrite may reveal previously unrecognized physiologic effects of red wine in connection with U NO bioactivity.

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Section: μM (Line 4)supporting

confidence: 91%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Gago

Lundberg

Barbosa

et al. 2007

Free Radical Biology and Medicine

155

111

View full text Add to dashboard Cite

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“…Recent studies suggest that the combination of flavonoids and nitrates can enhance NO production in the stomach (Bondonno et al 2012, Peri et al 2005). Furthermore, it was shown that diets high in nitrates rich apples flavonoids and spinach (Spinacia oleracea) may increase independently NO levels, improve the endothelial function and reduce BP acutely, all of which can benefit cardiovascular health (Bondonno et al 2012).…”

Section: Nitratesmentioning

confidence: 99%

Mechanisms of Endothelial Protection by Natural Bioactive Compounds from Fruit and Vegetables

Monsalve

Concha-Meyer

Palomo

et al. 2017

An. Acad. Bras. Ciênc.

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The endothelium is fundamental for the regulation of vascular tone and structure. Under disease conditions, including the presence of cardiovascular disease risk factors, the endothelium loses its protective role and becomes a proatherosclerotic structure. In this article we searched for strategies from PUBMED and Science Direct databases using the following key words: endothelium, natural bioactive compounds, polyphenols and cardiovascular diseases. The search was restricted to english language papers. Studies have identified the contribution of diet to the risk of developing cardiovascular diseases. In this context, high intakes of fruit and vegetables are associated with the decrease of cardiovascular diseases. Thus the most important fruit/vegetables and bioactive compounds to prevent endothelial diseases are berries, apples, virgin olive oil, tomatoes, soybeans, and polyphenols, carotenoids and unsaturated fatty acids, respectively. The bioactive compounds from fruit and vegetables provide endothelial protection through the following mechanisms: improved eNOS/NO bioavailability, attenuates oxidative stress, inhibited NF-κB pathway and decreased cell adhesion molecules expression. In this article natural bioactive compound mechanisms of endothelium protection are thoroughly reviewed.

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“…In the stomach, nitrite is protonated producing nitrous acid (pKa = 3.3), an oxidizing and nitrosating agent, to react with food components. It is well known that nitrous acid can transform amines into carcinogenic compounds nitrosoamines [10], and it has been reported that phenolic compounds can reduce nitrous acid to a functional compound nitric oxide ( • NO) [11,12]. The functions of • NO produced in the gastric lumen include the increase in gastric mucosal blood flow, the increase in gastric mucus thickness, and the relaxation of gastric smooth muscle [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

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

Takahama

Hirota

2017

Preprint

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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.

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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?

Cited by 134 publications

References 53 publications

Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Red wine-dependent reduction of nitrite to nitric oxide in the stomach

Mechanisms of Endothelial Protection by Natural Bioactive Compounds from Fruit and Vegetables

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

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