Microbiota facilitates the formation of the aminated metabolite of green tea polyphenol (-)-epigallocatechin-3-gallate which trap deleterious reactive endogenous metabolites

Zhang, Shuwei; Zhao, Yantao; Ohland, Christina; Jobin, Christian; Sang, Shengmin

doi:10.1016/j.freeradbiomed.2018.12.023

Cited by 71 publications

(78 citation statements)

References 53 publications

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“…Cell growth inhibition of myricetin and 4′‐NH 2 ‐myricetin was determined by MTT colorimetric assay as described previously in HCT‐116 and HT‐29 cells for 24 h. The HCT‐116 and HT‐29 cells were plated in 96‐well microplates with 5000 cells per well and allowed to attach for 24 h at 37 °C. The test compounds were added to cell culture medium to the desired final concentrations.…”

Section: Methodsmentioning

confidence: 99%

“…Briefly, cells in 48‐well plates were pre‐incubated with different doses of myricetin and 4′‐NH 2 ‐myricetin for 1 h, and then treated with LPS (100 ng mL –1 ) plus designated doses of myricetin and 4′‐NH 2 ‐myricetin for 24 h. The nitrite concentration in the culture medium was measured as an indicator of NO production using Griess reagent as described previously …”

Section: Methodsmentioning

confidence: 99%

“…Previous studies have been demonstrated that several polyphenols with a vic ‐trihydroxyl group such as epigallocatechin (EGC) and pyrogallol have the capacity to chemically react with ammonia and generate aminated products in in vitro systems . Recently, we demonstrated for the first time that tea polyphenol epigallocatechin‐3‐gallate (EGCG) could react with ammonia in vivo to generate the aminated metabolites . However, it is still unknown whether amination is a common metabolic pathway to flavonoids with a vic ‐trihydroxy B‐ring.…”

Section: Introductionmentioning

confidence: 99%

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Biotransformation of Myricetin: A Novel Metabolic Pathway to Produce Aminated Products in Mice

Zhang

Wang

Zhao

et al. 2019

Molecular Nutrition Food Res

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Scope: In this study, whether amination is a novel metabolic pathway of myricetin, one of the major dietary flavonoids found in fruits, vegetables, and tea, and whether the aminated metabolite of myricetin remains bioactive, are investigated. Methods and results: It is found that myricetin with a vic-trihydroxyl group on the B ring can chemically react with ammonia via the formation of myricetin quinone to generate the aminated product in vitro. As expected, the amination occurs on position 4´of the B-ring of myricetin. The structure of this new product is confirmed by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography-mass spectrometry and is named 4´-NH 2 -myricetin. Using the synthetic 4´-NH 2 -myricetin as a standard, the presence of this compound is searched for in fecal samples collected from myricetin-treated mice using LC-MS, and 4´-NH 2 -myricetin is confirmed as the metabolite of myricetin in mice for the first time. Furthermore, two metabolites of myricetin, the mono-methylated myricetin and the microbial-derived metabolite 3,4,5-trihydroxyphenylacetic acid, are confirmed to be aminated in vivo based on LC-MS data analysis. After administration of different doses of myricetin through oral gavage, the amination of myricetin shows a dose-dependent response in feces. A similar trend is observed for the amination of the mono-methylated myricetin, but not for the microbial-derived metabolite 3,4,5-trihydroxyphenylacetic acid. In plasma, the trend of a dose-dependent response for the amination of myricetin and its mono methylated metabolite is observed, and the plasma concentration of the aminated 3,4,5-trihydroxyphenylacetic acid at 200 mg kg -1 dose is significantly higher than those at the 100 and 400 mg kg -1 doses. Interestingly, it is observed that the aminated myricetin retains the anti-inflammatory activity of myricetin. Conclusion: This result demonstrates that amination is a novel biotransformation mechanism of myricetin to produce aminated metabolites.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Biotransformation of Myricetin: A Novel Metabolic Pathway to Produce Aminated Products in Mice

Zhang

Wang

Zhao

et al. 2019

Molecular Nutrition Food Res

Self Cite

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“…By using a Zeta CAD (CAD, Les Essarts le Roi, France), the zeta potential analysis of the Mg 0.99 Zn 0.01 O nanoparticles were measured. The preparation of the nanoparticles was held at a pH of 7, and the samples were examined at least three times [18].…”

Section: Zeta Potentialmentioning

confidence: 99%

Green Synthesis of Mg0.99 Zn0.01O Nanoparticles for the Fabrication of κ-Carrageenan/NaCMC Hydrogel in order to Deliver Catechin

et al. 2020

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Currently, the role of the nanoparticles in the structure of the composites and their benefits for the health of the body is valuable. In this study, the effects of the doping on the structural and morphological properties of the hydrogels using a Mg co-doped ZnO hydrogel, which has been fabricated by the sol-gel process, have been investigated. Then, a hydrogel containing nanoparticle and a hydrogel without any nanoparticles was produced as a control. The hydrogels were loaded with catechin and the related characterization was evolved based on the new structure of the matrices. The Mg 0.99 Zn 0.01 O nanoparticles were synthesized using a green synthesis method. To investigate the properties of the nanoparticles, zeta potential and XRD were studied. The field emission scanning electron microscopy (FESEM), FTIR, TGA, swelling Ratio, and compression tests were investigated for the hydrogels. Based on the results, FESEM showed a more compressed structure for hydrogels including nanoparticles rather than the hydrogels without a nanoparticle. The TGA showed a higher decomposition temperature in the hydrogels including nanoparticles. The swelling ratio of hydrogels containing a nanoparticle was higher than the control hydrogel. κ-Carrageenan/ Mg 0.99 Zn 0.01 O/NaCMC/Catechin had the highest swelling ratio (44.15%) rather than the κ-Carrageenan/NaCMC (33.22%). Mg 0.99 Zn 0.01 O nanoparticles presented a stronger structure of hydrogels in the compression test. It is concluded that the role of the synthesized nanoparticle is critical in the structure of the hydrogel.Polymers 2020, 12, 861 2 of 15 property of inhibiting free radicals and acts as a biological antioxidant [4]. Biological properties of tea like the antioxidant, antimicrobial, anti-cancer, and anti-mutagenic properties are related to catechins. They naturally have demonstrated potential in both treatment and prevention and a wide range of diseases including cardiovascular diseases, Parkinson's disease, cancer, diabetes, osteoporosis, and Alzheimer's disease [5]. In addition to the direct effects of antioxidants of catechins, they can indirectly increase the body's androgenic antioxidants [6]. In a research study, mice who received the extracted green tea have shown the increased levels of intrinsic antioxidants such as glutathione peroxidase, reductase, superoxide dismutase, and catalase [7].Nanoparticles are particles smaller than 100 nm in diameter [8]. Nanomaterials can easily cross cellular barriers compared to larger particles and move to a cell or organ due to their special properties [9]. Pure hydrogels have a low mechanical strength. To optimize the thermal, mechanical, optical, and chemical properties of hydrogels, it is necessary to use-nanoparticle-loaded hydrogels. Nanoparticle-loaded hydrogels present many benefits in drug delivery such as improvement of bioavailability and efficacy and safety of the drugs (catechin) by providing targeted delivery of drugs, and or extending drug in the target tissue. Based on the methodology of nanoparticles prepa...

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“…Tea is known to exert a prebiotic-like effect and modulate the gut microbiota [11]. Conversely, the gut microbiota also contributes to the metabolism of tea polyphenols to facilitate the clearance of toxic reactive metabolites in cells [12], suggesting the cross-talk between gut microbiota and host oxidative and in ammatory response is pivotal to maintain intestinal health and barrier function [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Oral, but not rectal delivery of epigallocatechin-3-gallate alleviates colitis by regulating the gut microbiota, oxidative stress, inflammation, and barrier integrity

Huang

et al. 2020

Preprint

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Background: Alteration of the gut microbiota may contribute to the development of inflammatory bowel diseases (IBDs). Epigallocatechin-3-gallate (EGCG), a major bioactive constituent of green tea, is known to be beneficial in IBDs alleviation. However, it is unclear whether EGCG attenuates IBDs through direct improvement of gastrointestinal function or indirect alteration of the structure and function of the gut microbiota.Results: We first investigated the therapeutic effects of EGCG on disease severity, oxidative stress, inflammation, barrier function, and gut microbiota in murine colitis model, and further demonstrate it via EGCG pre-supplementation. We revealed that, oral, but not rectal, delivery of EGCG alleviated the severity of colitis through attenuation of anti-oxidative and anti-inflammatory response. Mucin-secreting goblet cell number, barrier function gene expression levels, and the integrity of tight junctions in the colon were also enhanced by oral EGCG. Additionally, we observed distinct EGCG-mediated alternation in the gut microbiome, as highlighted by increased Akkermansia abundance and butyrate production. Furthermore, we revealed that prophylactic oral application of EGCG for 21 days prior to the onset of dextran sodium sulfate (DSS)-induced colitis also ameliorated colonic damage, oxidative stress, and inflammatory response. Prophylactic EGCG significantly enriched Akkermansia, Faecalibaculum, and Bifidobacterium and enhanced acetate, propionate and butyrate production in DSS-treated mice. Moreover, scores of differential microbes, in particular Akkermansia, showed a strong positive correlation with short-chain fatty acids (SCFAs) and antioxidant enzyme levels in both the plasma and colon, but a negative association with inflammatory cytokines and malondialdehyde.Conclusions: EGCG is capable of treating DSS-induced colitis both therapeutically and prophylactically by inducing a pronounced anti-oxidative and anti-inflammatory response. Attenuation of colitis by oral, but not rectal administration of, EGCG suggests an intimate involvement of the gut microbiota. Increased Akkermansia and subsequent protective SCFAs production may be largely responsible for the anti-inflammatory and anti-oxidative function of EGCG, leading to restoration of intestinal epithelial homeostasis of the host. These findings provide novel insights into EGCG-mediated remission of IBDs and the rationale for devising more effective therapeutic strategies for IBDs.

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Microbiota facilitates the formation of the aminated metabolite of green tea polyphenol (-)-epigallocatechin-3-gallate which trap deleterious reactive endogenous metabolites

Cited by 71 publications

References 53 publications

Biotransformation of Myricetin: A Novel Metabolic Pathway to Produce Aminated Products in Mice

Biotransformation of Myricetin: A Novel Metabolic Pathway to Produce Aminated Products in Mice

Green Synthesis of Mg0.99 Zn0.01O Nanoparticles for the Fabrication of κ-Carrageenan/NaCMC Hydrogel in order to Deliver Catechin

Oral, but not rectal delivery of epigallocatechin-3-gallate alleviates colitis by regulating the gut microbiota, oxidative stress, inflammation, and barrier integrity

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