Insights into the metabolism and microbial biotransformation of dietary flavan-3-ols and the bioactivity of their metabolites

Monagas, Marı́a; Urpí-Sardà, Mireia; Sánchez-Patán, Fernando; Llorach, Rafaël; Garrido, Ignacio; Gómez‐Cordovés, Carmen; Andrés‐Lacueva, Cristina; Bartolomé, Begoña

doi:10.1039/c0fo00132e

Cited by 529 publications

(592 citation statements)

References 109 publications

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“…From this study, the authors reported characterization of metabolism products arising from catechin acting as a hydrogen atom acceptor (hydrogen sink). These findings parallel compounds isolated from biotransformations of flavan-3-ols by human microflora (Feng, 2006;Monagas et al, 2010). Briefly, catechin is converted to transient intermediate 2, which accepts two hydrogen atoms to provide reduced compound 3 (Figure 7).…”

Section: Ct-enteric Fermentation Interactionsmentioning

confidence: 72%

The role of condensed tannins in ruminant animal production: advances, limitations and future directions

et al. 2017

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-Tannins represent one of the most abundant polyphenolic compounds in plants. Tannins exist as a multitude of chemically unique entities in nature. The most commonly occurring tannins are typically divided into two major classes based on chemical structure: hydrolysable (HT) or condensed tannins (CT). Hydrolysable tannins are esters of gallic or ellagic acid linked to a polyol core, typically glucose. Condensed tannins or proanthocyanidins consist of flavan-3-ol subunits linked together to form oligomers and polymers. Both HT and CT are defined as astringent, medium-to-high-molecular weight polyphenolic compounds that characteristically bind and precipitate soluble proteins. The objective of this paper was to present recent advances in CT-ruminant interactions, the limitations associated with understanding and using CT in ruminant animal production, and future needs for research to further advance our knowledge of the role of CT in optimization of ruminant animal production. Condensed tannins pose some anti-nutritional problems to ruminants due to their astringent property that reduces feed intake and, consequently, animal performance. Ruminants can, however, tolerate CT by slowly adapting the ruminal microbes to the toxic effects of CT and by releasing CT-binding salivary proteins. The protein-binding ability of CT has some benefits to the ruminant due to complexes formed with essential amino acids, preventing their degradation in the rumen, but releasing them in the lower gut for absorption by the animal. Recent data have suggested increased N retention when CT is given to growing animals. There are potential benefits of using CT and HT for anthelmintic purposes due to their ability to inhibit egg hatching and larval motility of gastrointestinal nematode parasites, especially in small ruminants. Condensed tannins also bind to minerals (Al, Ca, Co, Cu, Fe, Mg, Mn, P, and Zn). Although studies with ruminants have been contradictory, it has been reported that because the CT-metal ion complex is stable over a wide pH range, CT may reduce the bioavailability of minerals. Methane mitigation by feeding CT might be the most impactful benefit for ruminant production. Many empirical equations have been developed to predict ruminal methane emissions, but very few have included CT. Future research should focus on the improvement of methodology to assess CT biological activity, interaction with other plant-specialized metabolites, and associated physiological and nutritional impacts on ruminants.

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Section: Ct-enteric Fermentation Interactionsmentioning

confidence: 72%

The role of condensed tannins in ruminant animal production: advances, limitations and future directions

et al. 2017

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“…Cocoa has a relatively high content of flavanols such as catechin and epicatechin and unique long procyanidins which, while most of them cannot be directly absorbed, are metabolized by microbiota to phenolic metabolites that are eventually absorbed [23]. Cocoa also contains lower amounts of flavonols such as quercetin, flavones such as luteolin, and flavanones such as naringenin [15,24].…”

Section: Discussionmentioning

confidence: 99%

A diet enriched with cocoa prevents IgE synthesis in a rat allergy model

Abril-Gil¹,

Massot-Cladera²,

Pérez-Cano³

et al. 2012

Pharmacological Research

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Previous studies in young rats reported the impact of cocoa intake on healthy immune status and allow suggesting it may have a role in the prevention of some immune-mediated diseases. The aim of this study was to ascertain the effect of a cocoa diet in a model of allergy in young rats. Three-week-old Brown Norway rats were immunized by i.p. injection of ovalbumin (OVA) with alum as adjuvant and Bordetella pertussis toxin. During the next 4 weeks rats received either a cocoa diet (containing 0.2% polyphenols, w/w) or a standard diet. Animals fed a standard diet showed high concentrations of anti-OVA IgG1, IgG2a, IgG2b and high anti-OVA IgE titres, which is the antibody involved in allergic response. In contrast, animals fed a cocoa diet showed significantly lower concentrations of anti-OVA IgG1 and IgG2a antibodies. Interestingly, the cocoa diet prevented anti-OVA IgE synthesis and decreased total serum IgE concentration. Analysis of cytokine production in lymph node cells at the end of the study revealed that, in this compartment, the cocoa diet decreased the tumor necrosis factor (TNF) -α and the interleukin (IL) -10 secretion but not IL-4 production. In conclusion, a cocoa-enriched diet in young rats produces an immunomodulatory effect that prevents anti-allergen IgE synthesis, suggesting a potential role for cocoa flavonoids in the prevention or treatment of allergic diseases. 3

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“…hydrolysis, oxidation), originating different metabolites that include propionic, phenylacetic and benzoic acids derivatives. When these forms reach the liver through blood circulation, they are partially conjugated into glucuronides, sulfates and O-methyl derivatives [7]. Furthermore, these compounds had been detected in human urine and faeces after moderate and regular wine consumption [8,9], meanwhile several evidences have suggested the capacity of these compounds to go through the blood-brain barrier (BBB) [10,11].…”

Section: Introductionmentioning

confidence: 99%

Understanding the protective effects of wine components and their metabolites in the brain function

et al. 2016

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Abstract. Moderate wine consumption has been suggested to exert a positive effect in prevention of neurodegenerative process and cognitive impairment. With the ultimate aim of achieving a better understanding of the molecular mechanisms behind this benefit, we have investigated the role of certain winederived phenolic metabolites and aroma compounds in the MAPK cascade (including ERK1/2, p38), one of the routes directly related to inflammation in neuronal cells. Some of the tested phenolic compounds, especially in the case of 3,4-dihydroxyphenylacetic acid, showed a significant neuroprotective effect against SIN-1-induced neuronal death. Regarding their effect over MAPK phosphorylation, inmunoblotting technique revealed a beneficial and significant decrease on the phosphorylation of p38 and ERK1/2 kinases after incubation with wine constituents. In addition, activity of caspase3-like protease, an executor of neuronal apoptosis and a downstream signal of MAPK, was significantly diminished by 3-(3-hydroxyphenyl) propionic acid and linalool, counterbalancing the increase produced by SIN-1. Altogether, these results suggest that wine aroma, phenolic compounds and their gut metabolites could exert neuroprotective actions by modulating MAPK signalling and caspase-3 proteases activation, which are known to play a key role in oxidative/ nitrosative stress-induced response.

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Insights into the metabolism and microbial biotransformation of dietary flavan-3-ols and the bioactivity of their metabolites

Cited by 529 publications

References 109 publications

The role of condensed tannins in ruminant animal production: advances, limitations and future directions

The role of condensed tannins in ruminant animal production: advances, limitations and future directions

A diet enriched with cocoa prevents IgE synthesis in a rat allergy model

Understanding the protective effects of wine components and their metabolites in the brain function

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