Metabolomic profiles of A-type procyanidin dimer and trimer with gut microbiota in vitro

Chen, Wanbing; Zhang, Li; Zhao, Li; Yan, Fangfang; Zhu, Xiaoling; Lu, Qun; Li, Rui

doi:10.1016/j.jff.2021.104637

Cited by 20 publications

(23 citation statements)

References 37 publications

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“…[56] Regarding 5C-RFM and A-type PACs, this is the first study, to the best of our knowledge, to have demonstrated the production of 5-(3′,4′-dihydroxyphenyl)-𝛾-valerolactone following human faecal incubation of dimer A2. Recently, Chen et al [28] identified 5-(3′,4′-dihydroxyphenyl)-𝛾-valerolactone after in vitro fermentation of dimer A2 using rat faecal microbiota. However, there is an absence of information with human microbiota.…”

Section: Discussionmentioning

confidence: 99%

“…[ 5 , 22 , 23 ] The structural properties of parent flavan‐3‐ol monomers and PACs may affect the native compound‐colonic microflora interaction and could represent a key aspect of the beneficial properties associated with the intake of these phytochemicals. The catabolism of PCs has been investigated with in vivo [ 24 , 25 , 26 ] and in vitro studies, [ 27 , 28 , 29 ] and the production of PVLs from B‐type dimers as well as from PCs contained in complex matrices such as nuts and fruits, has been well‐established. [ 30 , 31 , 32 , 33 , 34 , 35 , 36 ] However, less is known about the interaction of the human gut microbiota with A‐type dimers, [ 27 ] the ability of the microbiota to catabolize A‐ and/or B‐type oligomers, and the possible production of PVLs and PVAs from these flavan‐3‐ol structures.…”

Section: Introductionmentioning

confidence: 99%

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In Vitro Faecal Fermentation of Monomeric and Oligomeric Flavan‐3‐ols: Catabolic Pathways and Stoichiometry

Pede

Bresciani

Brighenti

et al. 2022

Molecular Nutrition Food Res

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Scope The study evaluates the influence of flavan‐3‐ol structure on the production of phenolic catabolites, principally phenyl‐γ‐valerolactones (PVLs), and phenylvaleric acids (PVAs). Methods and Results A set of 12 monomeric flavan‐3‐ols and proanthocyanidins (degree of polymerization (DP) of 2–5), are fermented in vitro for 24 h using human faecal microbiota, and catabolism is analyzed by UHPLC‐ESI‐MS/MS. Up to 32 catabolites strictly related to microbial catabolism of parent compounds are detected. (+)‐Catechin and (−)‐epicatechin have the highest molar mass recoveries, expressed as a percentage with respect to the incubated concentration (75 µmol L–1) of the parent compound, for total PVLs and PVAs, both at 5 h (about 20%) and 24 h (about 40%) of faecal incubation. Only A‐type dimer and B‐type procyanidins underwent the ring fission step, and no differences are found in total PVL and PVA production (≃1.5% and 6.0% at 5 and 24 h faecal incubation, respectively) despite the different DPs. Conclusion The flavan‐3‐ol structure strongly affects the colonic catabolism of the native compounds, influencing the profile of PVLs and PVAs produced in vitro. This study opens new perspectives to further elucidate the colonic fate of oligomeric flavan‐3‐ols and their availability in producing bioactive catabolites.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In Vitro Faecal Fermentation of Monomeric and Oligomeric Flavan‐3‐ols: Catabolic Pathways and Stoichiometry

Pede

Bresciani

Brighenti

et al. 2022

Molecular Nutrition Food Res

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“…Another new conclusion is that the DP has little or no influence on biomechanical properties among B-type trimers and pentamers as both showed similar E * values, most likely because they are already in the range of DP with optimum biomechanical performance . Some biological studies have reported that A-type PAC fractions were more effective and stable than B-type PAC fractions. , Trimeric PACs from red wine (Vitis vinifera) with 4 → 8 linkages showed stronger skin-whitening effects than 4 → 6 linkages by the PAC in vitro assay . Although the underlying mechanisms are still unclear, the present results further consolidate our proposal that DP, interflavan linkage types, and linkage sites are structural features that collectively determine which PACs are most suitable with regard to size and hydrophilic–hydrophobic properties, unfolding the most robust interaction with biomacromolecules such as dentin collagen.…”

Section: Resultsmentioning

confidence: 99%

B-type Proanthocyanidins with Dentin Biomodification Activity from Cocoa (Theobroma cacao)

Jing

Reis

Alania

et al. 2022

J. Agric. Food Chem.

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To enable translational studies, a scalable preparative isolation scheme was developed for underivatized cocoa (Theobroma cacao) proanthocyanidins (PACs), affording six all-B-type oligomeric PACs, including a new tetramer 4. Their structures, including absolute configuration, were unambiguously established by comprehensive spectroscopic and chemical methods. Evaluation of the PACs’ dentin biomodification properties employed dynamic mechanical and infrared spectroscopic analyses in dentin bioassay models. PAC treatment enhanced the biomechanical strength of dentin by 5- to 15-fold compared to untreated dentin. Among the PAC agents, the pentamer, cinnamtannin A3 (6), led to the highest complex modulus value of 131 MPa, whereas the “branched” tetramer, 4, showed the lowest, yet still significant bioactivity. This study of specifically singly linked medium-length oligomeric PACs indicates that the linkage site is paramount in determining the potency of these PACs as dentin biomodifiers.

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“…The bioactivities of procyanidins are closely related to their source, structure, and polymerization degree (Gu et al, 2004). For example, A-type procyanidins showed a better activity against urinary tract infection than B-type procyanidins (Chen et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

“…The bioactivities of procyanidins are closely related to their source, structure, and polymerization degree (Gu et al, 2004). For example, A‐type procyanidins showed a better activity against urinary tract infection than B‐type procyanidins (Chen et al, 2021). And peanut skin procyanidins (PSP) has a low polymerization degree (about 3.4 on average), which is conducive to human absorption and utilization of the procyanidins (Sarnoski et al, 2012; Yu et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

The underlying mechanism of A‐type procyanidins from peanut skin on DSS ‐induced ulcerative colitis mice by regulating gut microbiota and metabolism

Huang

Wang

Liu

et al. 2022

Journal of Food Biochemistry

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Ulcerative colitis (UC) is a kind of inflammatory bowel disease. Procyanidins have been found to prevent UC. However, most research has been focused on the alleviation effect of B-type procyanidins on UC and ignored those of A-type procyanidins.Hence, this study aims to investigate the anti-UC effect and the potential mechanism of A-type procyanidins by combining gut microbiome and metabolic profile. UC was induced by dextran sulfate sodium (DSS) in Balb/c mice, and then the mice were administrated with peanut skin procyanidins (PSP; rich in A-type procyanidins) for 9 days. Administration of PSP can ameliorate DSS-induced UC by mediating the intestinal barrier, the expression of inflammatory cytokines (TNFα, ILβ, IL-6, and IL-10) and oxidative stress (MDA, T-SOD, NO, and iNOS) in mice. We observed that PSP affects the gut microbiota and colon metabolomic patterns of mice. The 16S rDNA sequencing showed increase in abundance of Lachnospiraceae_NK4A136_group, Oscillibacter and Roseburia and decrease of Bacteroides, Helicobacter, Parabacteroides, Escherichia-Shigella, and Enterobacter after PSP treatment. The colon tissue metabolome was significantly altered, as reflected by regulating taste transduction, mTOR signaling pathway, PI3K-Akt signaling pathway, and FoxO signaling pathway to improve the protection against UC. Practical applicationsWe investigated the anti-ulcerative colitis (UC) effect and its potential mechanism of peanut skin procyanidins (PSP). This suggests that PSP with abundant A-type procyanidins may be an effective candidate for dietary supplementation to alleviate the symptoms of UC by regulating gut microbiota and metabolism.

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Metabolomic profiles of A-type procyanidin dimer and trimer with gut microbiota in vitro

Cited by 20 publications

References 37 publications

In Vitro Faecal Fermentation of Monomeric and Oligomeric Flavan‐3‐ols: Catabolic Pathways and Stoichiometry

In Vitro Faecal Fermentation of Monomeric and Oligomeric Flavan‐3‐ols: Catabolic Pathways and Stoichiometry

B-type Proanthocyanidins with Dentin Biomodification Activity from Cocoa (Theobroma cacao)

The underlying mechanism of A‐type procyanidins from peanut skin on DSS ‐induced ulcerative colitis mice by regulating gut microbiota and metabolism

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