Formation, physicochemical properties, and biological activities of theabrownins.

Theabrownins (TBs) are heterogeneous mixtures of water-soluble brown tea pigments, and important constituents to evaluate the quality of dark tea. TBs have numerous hydroxyl and carboxyl groups and are formed by the oxidative polymerization of tea polyphenols. Many biological activities attributed to TBs, including antioxidant, anti-obesity, and lipid-regulating, have been demonstrated. This review summarizes the research progress made on the formation mechanism and physicochemical properties of TBs. It also discusses their protective effects against various diseases and associated potential molecular mechanisms. Additionally, it examines the signaling pathways mediating the bioactivities of TBs and highlights the difficulties and challenges of TBs research as well as their research prospects and applications.

Senolytic and senomorphic agent procyanidin C1 alleviates structural and functional decline in the aged retina.

Increased cellular senescence burden contributes in part to age-related organ dysfunction and pathologies. In our study, using mouse models of natural aging, we observed structural and functional decline in the aged retina, which was accompanied by the accumulation of senescent cells and senescence-associated secretory phenotype factors. We further validated the senolytic and senomorphic properties of procyanidin C1 (PCC1) both in vitro and in vivo, the long-term treatment of which ameliorated age-related retinal impairment. Through high-throughput single-cell RNA sequencing (scRNA-seq), we comprehensively characterized the retinal landscape after PCC1 administration and deciphered the molecular basis underlying the senescence burden increment and elimination. By exploring the scRNA-seq database of age-related retinal disorders, we revealed the role of cellular senescence and the therapeutic potential of PCC1 in these pathologies. Overall, these results indicate the therapeutic effects of PCC1 on the aged retina and its potential use for treating age-related retinal disorders.

Study on the interaction mechanism between (-)-epigallocatechin-3-gallate and myoglobin: Multi-spectroscopies and molecular simulation.

(-)-Epigallocatechin-3-gallate (EGCG) is remarkably efficacious in inhibiting the browning of red meat. We therefore propose a hypothesis that EGCG forms complexes with myoglobin, thereby stabilizing its structure and thus preventing browning. This study investigated the interaction mechanism between EGCG and myoglobin. EGCG induced static quenching of myoglobin. Noncovalent forces, including hydrogen bonds and van der Waals, primarily governing the interactions between myoglobin and EGCG. The interactions primarily disrupted myoglobin's secondary structure, thus significantly reducing surface hydrophobicity by 53% (P < 0.05). The modification augmented the solubility and thermal stability of myoglobin. The radius of gyration (Rg) value fluctuated between 1.47 and 1.54 nm, and the hydroxyl groups in EGCG formed an average of 2.93 hydrogen bonds with myoglobin. Our findings elucidated the formation of stable myoglobin-EGCG complexes and the myoglobin-EGCG interaction, thus confirming our initial hypothesis.

Identifying the temporal contributors and their interactions during dynamic formation of black tea cream.

Tea cream formed in hot and strong tea infusion while cooling deteriorates quality and health benefits of tea. However, the interactions among temporal contributors during dynamic formation of tea cream are still elusive. Here, by deletional recombination experiments and molecular dynamics simulation, it was found that proteins, caffeine (CAF), and phenolics played a dominant role throughout the cream formation, and the contribution of amino acids was highlighted in the early stage. Furthermore, CAF was prominent due to its extensive binding capacity and the filling complex voids property, and caffeine-theaflavins (TFs) complexation may be the core skeleton of the growing particles in black tea infusion. In addition to TFs, the unidentified phenolic oxidation-derived products (PODP) were confirmed to contribute greatly to the cream formation.

Modification mechanism of soybean protein isolate-soluble soy polysaccharide complex by EGCG through covalent and non-covalent interaction: Structural, interfacial, and functional properties.

Soybean protein isolate was modified with polysaccharides and polyphenols to prepare a natural emulsifier with antioxidant capacity. Physicochemical, structural, interfacial, and functional properties of SPI-SSPS complex were investigated after covalent and non-covalent interacted with EGCG. SPI-SSPS-EGCG ternary complex with low EGCG concentrations (0.0625 and 0.125 mg/mL) showed a significant increase in absolute potential value and a decrease in turbidity. EGCG destroyed the original rigid structure of SPI-SSPS complex, and the covalent complexes had an ordered structure, while the non-covalent interaction resulted in disordered. The ternary complex with high EGCG concentrations (0.25 and 0.5 mg/mL) exhibited stronger EGCG binding capacity and lower surface hydrophobicity, which in turn affected its interfacial properties. The EAI and ESI of SPI-SSPS-EGCG covalent complex increased significantly, while the non-covalent complex had a significant change in EAI but no significant change in ESI with increasing EGCG concentration. The ternary complex showed significantly enhanced antioxidant capacity. The SPI-SSPS-EGCG ternary complex, with excellent antioxidant capacity and emulsifying property, making it suitable for emulsion delivery systems.

Discrimination and prediction of Qingzhuan tea storage year using quantitative chemical profile combined with multivariate analysis: Advantages of MRMHR based targeted quantification metabolomics.

The duration of storage significantly influences the quality and market value of Qingzhuan tea (QZT). Herein, a high-resolution multiple reaction monitoring (MRMHR) quantitative method for markers of QZT storage year was developed. Quantitative data alongside multivariate analysis were employed to discriminate and predict the storage year of QZT. Furthermore, the content of the main biochemical ingredients, catechins and alkaloids, and free amino acids (FAA) were assessed for this purpose. The results show that targeted marker-based models exhibited superior discrimination and prediction performance among four datasets. The R2Xcum, R2Ycum and Q2cum of orthogonal projection to latent structure-discriminant analysis discrimination model were close to 1. The correlation coefficient (R2) and the root mean square error of prediction of the QZT storage year prediction model were 0.9906 and 0.63, respectively. This study provides valuable insights into tea storage quality and highlights the potential application of targeted markers in food quality evaluation.

A novel EGCG-Histidine complex improves gelling and physicochemical properties of porcine myofibrillar proteins: Insight into underlying mechanisms.

Herein, an EGCG-Histidine complex is prepared, characterized, and further used to improve gel properties of myofibrillar proteins (MP). Results of FTIR, XRD, UV-Vis spectroscopy showed that histidine is covalently bound to EGCG by Michael addition or Schiff base reaction to form EGCG-Histidine complex, and antioxidant activity of EGCG-Histidine complex is significantly increased compared to EGCG or histidine alone (P < 0.05). The addition of EGCG-Histidine complex results in cooking loss of gel decreasing from 66.7 ± 0.23 % to 40.3 ± 2.02 %, and improves rheological properties of MP, and enhances gel strength from 0.10 ± 0.01 N to 0.22 ± 0.03 N, indicating positive effect of EGCG-Histidine complex on MP gel formation, above results is supported by results of SEM, CD spectroscopy, SDS-PAGE, and tryptophan fluorescence. These results indicated that EGCG-Histidine complex can be used as a functional ingredient to improve gel quality of meat products.

Novel l-Cysteine Incomplete Degradation Method for Preparation of Procyanidin B2-3'-O-Gallate and Exploration of its in Vitro Anti-inflammatory Activity and in Vivo Tissue Distribution.

In this study, an effective method for preparation of bioactive galloylated procyanidin B2-3'-O-gallate (B2-3'-G) was first developed by incomplete depolymerization of grape seed polymeric procyanidins (PPCs) using l-cysteine (Cys) in the presence of citric acid. The structure-activity relationship of B2-3'-G was further evaluated in vitro through establishing lipopolysaccharide (LPS)-induced inflammation in RAW264.7 cells. The results suggested that the better protective effects of B2-3'-G against inflammation were attributed to its polymerization degree and the introduction of the galloyl group, compared to its four corresponding structural units. In vivo experiments demonstrated that the B2-3'-G prototype was distributed in plasma, small intestine, liver, lung, and brain. Remarkably, B2-3'-G was able to penetrate the blood-brain barrier and appeared to play an important role in improving brain health. Furthermore, a total of 18 metabolites were identified in tissues. Potential metabolic pathways, including reduction, methylation, hydration, desaturation, glucuronide conjugation, and sulfation, were suggested.

Effect of epigallocatechin-3-gallate modification on the structure and emulsion stability of rice bran protein in the presence of soybean protein isolate.

For improving the emulsion stability of rice bran protein (RBP), RBP was modified by different concentrations of epigallocatechin-3-gallate (EGCG) in the presence of soybean protein isolate (SPI), and RBP-EGCG-SPI conjugate was prepared by alkaline pH-shifting. The results showed that the addition of EGCG led to an increase in the bound phenol content and the flexibility of the secondary structure, a decrease in the free sulfhydryl and disulfide bond content of the RBP-EGCG-SPI conjugate. EGCG covalently bound to RBP and SPI through non-disulfide bonds. When the concentration of EGCG was 10 % (w/v), the emulsifying activity index and emulsion stability index of conjugate reached the maximum value (36.61 m2/g and 255.61 min, respectively), and the conjugate had the best emulsion stability. However, an EGCG concentration above 10 % (w/v) negatively affected the emulsion stability, with increasing particle size due to protein aggregation. Summarily, the modification of EGCG improved the emulsion stability of conjugate by regulating the spatial structure of RBP-EGCG-SPI conjugate. The work provided an important guide to further improve the emulsion stability of RBP.

Epigallocatechin-3-gallate stabilizes aqueous curcumin by generating nanoparticles and its application in beverages.

In this study, we addressed the limited water solubility of curcumin by utilizing epigallocatechin-3-gallate to form nanoparticles through self-assembly. The resulting particles, ranging from 100 to 150 nm, exhibited a redshift in the UV-visible spectrum, from 425 nm to 435 nm, indicative of potential π-π stacking. Molecular docking experiments supported this finding. Curcumin loaded with epigallocatechin-3-gallate showed exceptional dispersibility in aqueous solutions, with 90.92 % remaining after 60 days. The electrostatic screening effect arises from the charge carried by epigallocatechin-3-gallate on the nanoparticles, leading to enhanced retention of curcumin under different pH, temperature, and ionic strength conditions. Furthermore, epigallocatechin-3-gallate can interact with other hydrophobic polyphenols, improving their dispersibility and stability in aqueous systems. Applying this principle, a palatable beverage was formulated by combining turmeric extract and green tea. The nanoparticles encapsulated with epigallocatechin-3-gallate show potential for improving the applicability of curcumin in aqueous food systems.

Covalent conjugation of Inca peanut albumin and polyphenols with different phenolic hydroxyl numbers through laccase catalysis to improve functional properties.

BACKGROUND: Enzymatic crosslinking is a method that can be used to modify Inca peanut albumin (IPA) using polyphenols, and provides desirable functionalities; however, the effect of polyphenol structures on conjugate properties is unclear. In this study, we selected four polyphenols with different numbers of phenolic hydroxyl groups [para-hydroxybenzoic acid (HBA), protocatechuic acid (PCA), gallic acid (GA), and epigallocatechin gallate (EGCG)] for covalent modification of IPA by enzymatic crosslinking, and explored the structure-function changes of the IPA-polyphenol conjugates. RESULTS: Sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) analysis showed that laccase successfully promoted covalent crosslinking of IPA with polyphenols, with the order of degree of conjugation as EGCG > GA > PCA > HBA, the IPA-EGCG conjugate showed the highest polyphenol binding equivalents (98.35 g kg-1 protein), and a significant reduction in the content of free amino, sulfhydryl, and tyrosine group. The oxidation of polyphenols by laccase forms quinone or semiquinone radicals that are covalently crosslinked to the reactive groups of IPA, leading to significant changes in the secondary and tertiary structures of IPA, with spherical structures transforming into dense lamellar structures. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging ability and emulsification stability of IPA-EGCG conjugates improved by almost 6-fold and 2.7-fold, respectively, compared with those of unmodified IPA. CONCLUSION: These data suggest that the higher the number of polyphenol hydroxyl groups, the higher the degree of IPA-polyphenol conjugation; additionally, enzymatic crosslinking can significantly improve the functional properties of IPA. © 2024 Society of Chemical Industry.

Effects of processing technology on tea quality analyzed using high-resolution mass spectrometry-based metabolomics.

Fixation is a crucial step in green tea processing that can impact quality. In this study, we explored the differences in the chemical components of steamed and fried green teas made from the same batch of fresh tea leaves using different fixing methods. Results showed that concentrations of sucrose and free amino acids were significantly higher in steamed green tea. Abundances of 12 compounds including purine nucleoside, pyrimidine nucleoside derivatives, and catechins were higher in fried green tea, while 34 compounds such as amino acids and their derivatives, benzofurans and flavonoids were higher in steamed green tea. Thus, steaming retained more compounds associated with sweet and fresh tastes, such as free amino acids, while frying produced more compounds with bitter tastes, such as catechin. This might explain why steamed green tea is mellower than fried tea.

Effects of catechin on the stability of myofibrillar protein-soybean oil emulsion and the adsorbed properties of myosin at the oil-water interface.

The effects of different concentrations of catechin on the stability of myofibrillar protein-soybean oil emulsions and the related mechanisms were investigated. Adding 10 µmol/g catechin had no obvious effects on the emulsion stability and myosin structure, but 50, 100 and 200 µmol/g catechin decreased the emulsion stability. The microstructure observations showed that 10 µmol/g catechin caused a dense and uniform emulsion to form, whereas 50, 100 and 200 µmol/g catechin induced the merging of oil droplets. The addition of 50, 100 and 200 µmol/g catechin caused a decline in both the total sulfhydryl content and surface hydrophobicity, suggesting protein aggregation, which decreased the adsorption capacity of myosin and the elasticity of interfacial film. These results suggested that higher concentrations of catechin were detrimental to the emulsifying properties of myosin and that the dose should be considered when it is used as an antioxidant.

[Dynamic Chemistry of Tannins].

Tannins are a group of polyphenols that possess the ability to precipitate proteins, causing an undesirable astringent taste by interacting with salivary peptides. This interaction deactivates the digestive enzymes; therefore, tannins are considered as plant defense substances. The health benefits of tannins and related polyphenols in foods and beverages have been demonstrated by biological and epidemiological studies; however, their metabolism in living plants and the chemical changes observed during processing of foods and medicinal herbs raises some questions. This review summarizes our studies concerning dynamic changes observed in tannins. Ellagitannins present in the young leaves of Camellia japonica and Quercus glauca undergo oxidative degradation as the leaves mature. Similar oxidative degradation is also observed in whiskey when it is kept for aging in oak barrels, and in decaying wood caused by fungi in natural forests. In contrast, ellagitannins have been observed to undergo reduction in the leaves of Carpinus, Castanopsis, and Triadica species as the leaves mature. This phenomenon of reductive metabolism in leaves enabled us to propose a new biosynthetic pathway for the most fundamental ellagitannin acyl groups, which was also supported by biomimetic synthetic studies. Polyphenols undergo dynamic changes during the process of food processing. Catechin in tea leaves undergo oxidation upon mechanical crushing to generate black tea polyphenols. Though detailed production mechanisms of catechin dimers have been elucidated, structures of thearubigins (TRs), which are complex mixtures of oligomers, remain ambiguous. Our recent studies suggested that catechin B-ring quinones couple with catechin A-rings during the process of oligomerization.

Insight into the chemical compositions of Anhua dark teas derived from identical tea materials: A multi-omics, electronic sensory, and microbial sequencing analysis.

Anhua dark teas (DTs), including Tianjian tea, Qianliang tea, Hei brick tea, and Fu brick tea, are unique fermented teas from China's Anhua County; yet their chemical composition differences remain unclear. Herein, metabolomics, volatolomics, and electronic sensory assessments were employed to analyze and compare chemical compositions and sensory characteristics of five types of Anhua DTs. All of these teas were derived from identical tea materials. Chemical compositions differed significantly among Anhua DTs, with Tianjian tea remarkable. Long-lasting fermentation and complex processing methods led to transformation of multiple compounds, particularly catechins. Eighteen volatile compounds with OVA > 1 were key aroma contributors in Anhua DTs. Internal transcribed spacer and 16S ribosomal DNA sequencing showed that Eurotium, Pseudomonas, and Bacillus are dominant microorganisms in Anhua DTs. Furthermore, this study unveiled notable differences in chemical compositions between Anhua DTs and five other traditional types of tea. This research enhances our understanding of Anhua DTs processing.

Identification and structural characterization of a novel (+)-catechin-caffeic acid adduct present in wines.

A new compound with a molecular ion mass of m/z 467 in the negative ion mode was found to occur in a white wine aged 30 months in bottle. In this latter, fragment ions compatible with the loss of a carboxylic acid (-44 a.m.u.), a caffeic acid unit (-178 a.m.u.), and a Retro-Diels Alder (-152 a.m.u.) were observed. The present work reports the synthesis of a (+)-catechin-caffeic acid adduct resulting from the condensation reaction between caffeic acid and (+)-catechin. The structural characterization by NMR showed that this adduct is formed by the linkage between carbon 8 at ring A from (+)-catechin and carbon 9 from caffeic acid. In addition, the similarity in the HPLC retention time and UV-Visible spectra of the synthesized compound with the one detected in white wine and the bottling experiments, confirms the presence of this novel (+)-catechin-derived compound in those matrices.

The substitution sites of hydroxyl and galloyl groups determine the inhibitory activity of human pancreatic α-amylase in twelve tea polyphenol monomers.

Tea polyphenols have been reported as potential α-amylase inhibitors. However, the quantitative structure-activity relationship (QSAR) between tea polyphenols and human pancreas α-amylase (HPA) is not well understood. Herein, the inhibitory effect of twelve tea polyphenol monomers on HPA was investigated in terms of inhibitory activity, as well as QSAR analysis and interaction mechanism. The results revealed that the HPA inhibitory activity of theaflavins (TFs), especially theaflavin-3'-gallate (TF-3'-G, IC50: 0.313 mg/mL), was much stronger than that of catechins (IC50: 18.387-458.932 mg/mL). The QSAR analysis demonstrated that the determinant for the inhibitory activity of HPA was not the number of hydroxyl and galloyl groups in tea polyphenol monomers, while the substitution sites of these groups potentially might play a more important role in modulating the inhibitory activity. The inhibition kinetics and molecular docking revealed that TF-3'-G as a mixed-type inhibitor had the lowest inhibition constant and bound to the active sites of HPA with the lowest binding energy (-7.74 kcal/mol). These findings could provide valuable insights into the structures-activity relationships between tea polyphenols and the HPA inhibitors.

Recent insights into catechins-rich Assam tea extract for photoaging and senescent ageing.

Tea (Camellia spp.) is an important medicinal herb. C. sinensis var. sinensis is the most studied tea variety due to its more preferred flavor than C. sinensis var. assamica (Assam tea), the less economic importance with more bitter variety. A bitter taste highlights its potential as a candidate source for tea catechins, the health beneficial actives applicable for ageing treatment. Nonetheless, indicative data for tea on UV-induced and senescent ageing remain unclarified. Assam tea extract (ATE) was prepared and standardized in terms of TPC, TFC and TTC. EGCG was HPLC quantified as the prime ATE catechin. In vitro antioxidant activity of ATE was exhibited with ABTS, DPPH and FRAP assays. ATE's cellular antioxidant activity was indicated in HDFs at a stronger degree than ascorbic acid. The photoaging protection of ATE was evidenced in a coculture of HaCaT cells and HDFs. ATE markedly suppressed UV-induced IL-6, IL-8, MMP-1 and MMP-9 expressions. The proficiency of ATE targeting on senescent ageing was demonstrated in an ex vivo human skin model, where IL-6 and MMP-1 expressions were suppressed, whilst hyaluronic acid and collagen syntheses were promoted. ATE was chemically stabled as indicated by the catechin contents and color parameters following 6 months storage under conditions recommended for topical product. ATE enriched in catechins warrants its applicability as a new generation of photoaging protectant agent promising for the prevention and treatment for senescent ageing. The findings indicate the proficiency of ATE for innovative anti-ageing agent.

Network pharmacology based pharmacokinetic assessment and evaluation of the therapeutic potential of catechin derivatives as a potential myostatin inhibitor: A special view on Sarcopenic Obesity.

Sarcopenic obesity has become a significant age-related metabolic problem. Catechins are flavanol, derivatives which poses a strong antioxidant activity. The major components of catechin derivatives. were identified through our physicochemical and pharmacokinetic parameters estimation. Therefore, in this study, network pharmacology was used to explore the multiple targets related to Sarcopenia, Metabolic syndrome, and obesity. The targets were identified from network analysis. The catechin derivatives were screened using Lipinski's rule of five, Veber scale, Egan scale, and Muegge scale. From this drugglikness property catechin and Epicatechin was selected which were docked towards the myostatin inhibition PDB ID: 3HH2. Furthermore, the computational docking method on Catechin and Epicatechin with the stronger interaction towards myostatin inhibition receptor with the binding energy of -6.90 kcal/mol. and -7.0 kcal/mol from autodock software, respectively, for catechin and Epicatechin. Higher binding energy confirms the pharmacotherapeutic activity of Catechin and Epicatechin toward the myostatin inhibitor target.

The structural and functional properties of hemp protein isolate-epigallocatechin-3-gallate biopolymer covalent complex during heating.

BACKGROUND: It is well known that hemp proteins have the disadvantages of poor solubility and poor emulsification. To improve these shortcomings, an alkali covalent cross-linking method was used to prepare hemp protein isolate-epigallocatechin-3-gallate biopolymer (HPI-EGCG) and the effects of different heat treatment conditions on the structure and emulsifying properties of the HPI-EGCG covalent complex were studied. RESULTS: The secondary and tertiary structures, solubility, and emulsification ability of the HPI-EGCG complexes were evaluated using particle size, zeta potential, circular dichroism (CD), and fluorescence spectroscopy indices. The results showed that the absolute value of zeta potential of HPI-EGCG covalent complex was the largest, 18.6 mV, and the maximum binding amount of HPI to EGCG was 29.18 µmol g-1 . Under heat treatment at 25-35 °C, the α-helix content was reduced from 1.87% to 0%, and the ß-helix content was reduced from 82.79% to 0% after the covalent binding of HPI and EGCG. The solubility and emulsification properties of the HPI-EGCG covalent complexes were improved significantly, and the emulsification activity index (EAI) and emulsion stability index (ESI) were increased by 2.77-fold and 1.21-fold, respectively. CONCLUSION: A new HPI-EGCG covalent complex was developed in this study to provide a theoretical basis for the application of HPI-EGCG in food industry. © 2023 Society of Chemical Industry.