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The peel represents a significant portion of the araticum fruit (about 40%), which becomes waste after its consumption or processing. Previous studies have shown that the araticum peel is rich in phenolic compounds; however, little is known about the ideal conditions for recovering these compounds. Therefore, response surface methodology, using a central composite rotatable design, was employed to optimize the extraction process to maximize the total phenolic compounds (TPCs) and enhance the Trolox equivalent antioxidant capacity (TEAC) from araticum peel. The variables optimized were ethanol concentration (EC; 20-80%, v/v ), extraction time (ET; 5-45 min), and solid-solvent ratio (SSR; 10-100 mg/mL). Additionally, condensed tannins, antioxidant capacity against synthetic free radicals (TEAC and FRAP) and reactive oxygen species (ROS), and the phenolic compounds profile, were evaluated. Optimum extraction conditions were 50% ( v/v ) ethanol concentration, 5 min of extraction time, and 10 mg/mL solid-solvent ratio. Under these conditions, experimental TPCs and TEAC values were 70.16 mg GAE/g dw and 667.22 µmol TE/g dw, respectively, comparable with predicted models (68.47 mg GAE/g dw for TPCs and 677.04 µmol TE/g dw for TEAC). A high condensed tannins content (76.49 mg CE/g dw) was also observed and 12 phenolic compounds were identified, predominantly flavonoids (97.77%), including procyanidin B2, epicatechin, and catechin as the major compounds. Moreover, a potent antioxidant activity was observed against synthetic free radicals and ROS, especially in scavenging peroxyl and hydroxyl radicals. From this study, we obtained the ideal conditions for recovering phenolic compounds from araticum peel using a simple, fast, sustainable, and effective method, offering a promising opportunity for the management of this plant byproduct.

The influence of oxygen on the thermal treatment (TT) of secondary metabolite-enriched extracts (SMEEs) from Tórtola beans and procyanidin C1 (PC1) on the inhibition of advanced glycation end products (AGEs) generation in proteins was investigated. SMEE was incubated at 4 °C (control) or thermally treated at 60 °C for 2 h, at either 0 % O 2 (I) or 20 % O 2 (II). Treatments I and II increased the content of procyanidin dimers B2. Treatment II was more effective than the control or treatment I in preventing homocysteine oxidation and AGEs generation. TT of PC1 at 0 % or 20 % O 2 generated procyanidin dimers and tetramers. PC1 TT at 20 % O 2 exhibited higher oxidation potentials and lower IC 50 values of fluorescent AGEs than those of controls or TT at 0 % O 2 . These findings indicate that SMEE from Tórtola beans after treatment II changes the degree of polymerization and oxidation procyanidins, thereby increasing their antiglycation activity., Competing Interests: Declaration of competing interest The authors declare that they have no competing financial interests or personal relationships that could have appeared to influence the work related to this manuscript., (Copyright © 2024. Published by Elsevier Ltd.)

Scope: The absorption, disposition, metabolism, and excretion (ADME) of phenolic compounds are key factors in determining their bioactivity. The group demonstrates that the ADME of a Grape Seed Proanthocyanidin Extract (GSPE) depends on sex in adult rats and specifically, methylated metabolites are only quantified in brain male adult rats. The aim of this study is to determine whether these differences exist before puberty., Methods and Results: Prepubescent 4-week-old male and female Wistar rats are administered GSPE at a dose of 1000 mg kg -1 . Plasma, liver, mesenteric white adipose tissue (MWAT), brain, and kidneys are extracted excised 2 h after GSPE administration, and the PAs metabolite profile is studied by HPLC-ESI-MS/MS. Moreover, plasma estradiol and brain and liver catechol-O-methyltransferase (COMT) protein levels are also studied. Results showed that there are no differences in plasma and brain among sexes and only differences are observed in liver, MWAT, and kidney with individual metabolites. This agrees with the lack of differences in estradiol and COMT levels among sexes. However, the ADME of PAs metabolites is higher in male rats., Conclusions: The results demonstrate lack of sex-dependence in metabolite profile in prepubescent rats, suggesting that sex differences in the metabolism of GSPE occur due to puberty., (© 2024 The Author(s). Molecular Nutrition & Food Research published by Wiley‐VCH GmbH.)

Diet is of major importance in modulating intestinal inflammation, as the gastrointestinal tract is directly exposed to high concentrations of dietary components. Procyanidins are flavan-3-ol oligomers abundant in fruits and vegetables. Although with limited or no intestinal absorption, they can have GI health benefits which can promote overall health. We previously observed that epicatechin gallate (ECG) and epigallocatechin gallate (EGCG) dimers inhibit in vitro colorectal cancer cell proliferation and invasiveness. Inflammation-mediated intestinal barrier permeabilization can result in a chronic inflammatory condition and promote colorectal cancer onset/progression. Thus, this study investigated the structure-dependent capacity of ECG, EGCG and (-)-epicatechin (EC) dimers to inhibit tumor necrosis factor alpha (TNFα)-induced inflammation, oxidative stress, and loss of barrier integrity in Caco-2 cells differentiated into an intestinal epithelial cell monolayer. Cells were incubated with TNFα (10 ng/ml), in the absence/presence of ECG, EGCG and EC dimers. The three dimers inhibited TNFα-mediated Caco-2 cell monolayer permeabilization, modulating events involved in the loss of barrier function and inflammation, i.e. decreased tight junction protein levels; increased matrix metalloproteinases expression and activity; increased NADPH oxidase expression and oxidant production; activation of the NF-κB and ERK1/2 pathways and downstream events leading to tight junction opening. For some of these mechanisms, the galloylated ECG and EGCG dimers had stronger protective potency than the non-galloylated EC dimer. These differences could be due to differential membrane interactions as pointed out by molecular dynamics simulation of procyanidin dimers-cell membrane interactions and/or by differential interactions with NOX1. Results show that dimeric procyanidins, although poorly absorbed, can promote health by alleviating intestinal inflammation, oxidative stress and barrier permeabilization., Competing Interests: Declaration of competing interest Authors have no conflict of interest to declare., (Copyright © 2024 The Authors. Published by Elsevier B.V. All rights reserved.)

The calla lily (Zantedeschia hybrida) is a valued ornamental plant due to its unique shape and color variations. To determine the mechanisms responsible for color development in the calla lily spathe, we conducted a comparative transcriptomic analysis of the spathes of the black [Black Girl (B)], pink [Romantic (P)], and white [Ventura (W)] cultivars. The gene expression patterns in six spathe colors, including the preceding three colors as well as the amaranth [Promise (N)], red [Figo (F)], and yellow [Sun Club (Y)] cultivars were analyzed by real-time quantitative polymerase chain reaction (PCR). Transcriptomic analysis identified 25,165 differentially expressed genes. The transcription abundance and expression level of genes annotated as anthocyanidin reductase (ANR1, ANR2), basic-helix-loop-helix (bHLH1), and glutathione S-transferases (GST1) were significantly upregulated in B, and the expression of anthocyanidin synthase (ANS) was highest in B except for N. However, chalcone isomerase (CHI2) and dihydroflavonol 4-reductase (DFR1, DFR2) were expressed at significantly lower levels in P, W, and Y. Correlation analysis revealed that bHLH1 might act as a positive regulator of ANS expression, promoting anthocyanin synthesis. Moreover, GST1-encoded proteins may be related to the accumulation and transport of both anthocyanin and procyanidin in the calla lily spathe. It is speculated that the formation of the black spathe is related to the accumulation of anthocyanins and procyanidins. However, the low expression of CHI2, DFR1, and DFR2 may result in the inhibition of anthocyanin synthesis, which may lead to lightening of the spathe color. This preliminary study revealed the mechanism responsible for calla lily spathe color, identifying the key genes involved, thus providing effective gene resources and a theoretical basis for flower color molecular breeding.

Avocado peel and seed are the main by-products of avocado processing and are considered as promising sources of phenolic compounds with biological activities. Thus, this research focuses on the establishment, for the first time, of ultrasound-assisted extraction of flavan-3-ols with high antioxidant activity from avocado peel and seed using a sonotrode. Indeed, 2 Box–Behnken designs were performed for 15 experiments, with each design having three independent factors (ratio ethanol/water (v/v), time (min) and amplitude (%)). In both models, the responses included total procyanidins (flavan-3-ols) measured via HPLC-FLD and antioxidant activity measured via DPPH, ABTS and FRAP. The results showed that applying the sonotrode extraction method could increase flavan-3-ols recovery by 54% and antioxidant activity by 62–76% compared to ultrasound bath technology. Therefore, this technology was demonstrated to be a non-thermal, low time-consuming and scalable method that allowed the recovery of flavan-3-ols from avocado by-products that could be used as functional ingredients.

High-quality dark chocolates (70% cocoa content) can have shades from light to dark brown color. This work aimed at revealing compounds that discriminate black and brown chocolates. From 37 fine chocolate samples from years 2019 and 2020 provided by Valrhona,8 dark black samples and 8 light brown samples were selected. A non-targeted metabolomics study was performed based on ultra-high performance liquid chromatography—high resolution mass spectrometry/mass spectrometry experiments, univariate, multivariate, and feature-based molecular networking analyses. Twenty-seven overaccumulated discriminating compounds were found for black chocolates. Among them, glycosylated flavanols including monomers and glycosylated A-type procyanidin dimers and trimers were highly representative. Fifty overaccumulated discriminating compounds were found for brown chocolates. Most of them were B-type procyanidins (from trimers to nonamers). These phenolic compounds may be partially related to the chocolate colors as precursors of colored compounds. This study increases the knowledge on the chemical diversity of dark chocolates by providing new information about the phenolic profiles of black and brown chocolates.

Background: Procyanidins is a polyphenolic compound with multiple properties. However, the application of exogenous procyanidins in crops has not been reported. Aromatic rice is a high-quality rice with a special aroma and popular with consumers. The 2-acetyl-1-pyrroline (2-AP) is a key compound of aromatic rice aroma. In the current study, aromatic rice plants were sprayed with procyanidins solutions at 0.25 (Pr0.25), 0.50 (Pr0.50), 1.00 (Pr1.00), 2.00 (Pr2.00) g L−1, respectively and treatment sprayed with distilled water was taken as control (CK). The effects of exogenous procyanidins on growth and 2-AP biosynthesis of aromatic rice plants were explored. Results: Compared with CK, Pr1.00 and Pr2.00 treatments significantly increased 2-AP content by 16.67% and 37.68%, respectively. Higher proline, 1-pyrroline-5-carboxylic acid (P5C), 1-pyrroline, methylglyoxal contents, and lower γ- aminobutyric acid (GABA) content were recorded in Pr1.00 and Pr2.00 treatments than CK. Compared with CK, Pr1.00 and Pr2.00 treatments significantly improved the activities of P5CS and OAT and diminished the activity of BADH. Furthermore, compared with CK, Pr1.00 and Pr2.00 treatments significantly up-regulated the transcript levels of P5CS2, P5CR, OAT, DAO4 and down-regulated the transcript levels of BADH2. Exogenous procyanidins had no substantial effects on plant height, stem diameter, fresh weight, and dry weight of aromatic rice plants. Conclusions: In conclusion, our findings reported the increment of 2-AP content in aromatic rice under exogenous procyanidins. Our results indicated that the application of exogenous procyanidins enhanced 2-AP biosynthesis by improving proline biosynthesis and inhibiting GABA formation. [ABSTRACT FROM AUTHOR]

The objective of this study was to investigate the protective effects and potential molecular mechanisms of procyanidin B2 (PB2) in MAC-T (mammary alveolar cells-large T antigen) cells during heat stress (HS). The MAC-T cells were divided into three treatment groups: control (37 °C), HS (42 °C), and PB2 + HS (42 °C). Compared with MAC-T cells that were consistently cultured at 37 °C, acute HS treatment remarkably decreased cell viability, reduced activities of catalase (CAT), superoxide dismutase (SOD), and total antioxidant capacity (T-AOC), and elevated intracellular levels of malondialdehyde (MDA) and reactive oxygen species (ROS). Additionally, nuclear factor erythroid 2-related factor 2 (Nrf2) was activated and translocated to the nucleus, in accompaniment with upregulation of Nrf2, heme oxygenase 1 (HO-1), thioredoxin reductase 1 (Txnrd1), and heat shock protein 70 (HSP70). In parallel, both mRNA transcript and actual protein secretion of pro-inflammatory cytokines, including tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β), were increased by heat stress. Pretreatment of MAC-T cells with 0~25 μM PB2 alleviated the decline of cell viability by HS in a dose-dependent fashion and protected cells against HS-induced oxidative stress, as evidenced by significantly improved CAT, SOD, and T-AOC activity, as well as with decreased MDA and ROS generation. Furthermore, PB2 further activated the Nrf2 signaling pathway and reversed the inflammatory response induced by HS. Silencing of Nrf2 by si-Nrf2 transfection not only exacerbated HS-induced cell death and provoked oxidative stress and the inflammatory response, but also greatly abolished the cytoprotective effects under HS of PB2. In summary, PB2 protected MAC-T cells against HS-induced cell death, oxidative stress, and inflammatory response, partially by operating at the Nrf2 signal pathway. [ABSTRACT FROM AUTHOR]

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Annona crassiflora Mart., the marolo fruit of the Cerrado biome, is one of the most frequently consumed species from the Brazilian Midwest. This study aimed to evaluate the chemical composition and the antioxidant and cytotoxic properties of the fruit pulp of A. crassiflora collected at Chapada das Mesas, Maranhão, Brazil. The volatile concentrate was identified as mainly ethyl octanoate, ethyl hexanoate, and methyl octanoate. From the ethanol (LFP-E) and ethyl acetate (LFP-A) extracts were identified phenolic acids (p-coumaric, gallic, quinic, and ferulic), flavones and derivatives (apigenin, epicatechin, 2′-5-dimethoxyflavone, 3′,7-dimethoxy-3-hydroxyflavone, kaempferol-3-O-glucoside and 3-O-rutinoside, quercetin-3-O-glucoside, procyanidin B2, and rutin), aporphine alkaloids (xylopine, stephagine, and romucosine), and acetogenin (annonacin). For the LFP-E and LFP-A extracts, the total phenolic compound values were 15.89 and 33.16 mg GAE/g, the flavonoid compound content values were 2.53 and 70.55 mg QE/g, the DPPH radical scavenging activity showed EC50 values of 182.54 and 57.80 µg/mL, and the ABTS radical activity showed TEAC values of 94.66 and 192.61 µM TE/g. The LFP-E extract showed significant cytotoxicity and cell selectivity for the U251-glioma strain, presenting a GI50 value of 21.34 µg/mL, which is close to doxorubicin (11.68 µg/mL), the standard chemotherapeutic drug. The marolo fruit seems to be a promising source for developing innovative and healthy products for the food industry. [ABSTRACT FROM AUTHOR]

Lewis acid mediated self-condensation of epicatechin gallate derivative was examined. We found that Yb(OTf)3 afforded good yield of the dimeric epicatechin gallate derivative. The condensed product was applied to the synthesis of procyanidin B2 3,3′′-digallate. [ABSTRACT FROM AUTHOR]

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 (TNF‐α, IL‐β, 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 applications: We 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. [ABSTRACT FROM AUTHOR]

Background: Cocoa flavanols and procyanidins (CF) are flavonoids whose consumption is associated with health benefits, resulting in increasing attention from consumers, industry, researchers, and regulators. Methods that can provide appropriate characterization and quantification of the distinct mixture found in cocoa-based products thus offer important scientific and commercial value. Objective: This study validated the precision of AOAC Official Method of AnalysisSM 2020.05, which measures CF with a degree of polymerization DP1-7. Method: Method precision (repeatability and reproducibility) was evaluated for seven cocoa matrixes in blind duplicates with total CF content from 1.0 to 500 mg/g. Ten of the 12 laboratories from multiple sectors invited to implement the method returned data for statistical analysis. Precision was evaluated per AOAC INTERNATIONAL guidelines for collaborative studies using RSDr and RSDR as indicators of method repeatability and reproducibility. Results: RSDr ranged from 1.6 to 4.8%, and RSDR ranged from 5.8 to 22.4%, demonstrating excellent within-laboratory repeatability and good method precision across different laboratories. RSDR values were below 10% with the exception of chocolate, potentially due to very low CF content and sampling inhomogeneity. Conclusions: These data demonstrate that acceptable method repeatability and reproducibility is achieved when measuring cocoa flavanols and procyanidins using AOAC Method 2020.05 and support the advancement of the AOAC Official Method of Analysis status to Final Action for evaluated matrixes. Highlights: This collaborative study evaluated the repeatability and reproducibility of AOAC Official Method of Analysis 2020.05. [ABSTRACT FROM AUTHOR]

Background: β-catenin is an important unit of the Wnt/β-catenin signaling pathway, a conserved process involving several physiological activities, encompassing differentiation and cell proliferation, etc. The dysfunction or mutation in β-catenin causing the initiation and advancement of various neoplasm types, including colorectal cancer, breast cancer, etc., has been reported. Therefore, β-catenin is a therapeutic target. Hence, designing new inhibitors targeted against β-catenin will prevent cancerous cells' involvement and eliminate the diseases. Studies showed that Vitis vinifera, a well-known grape species, contains different phytochemical substances, including aromatic acids, flavonoids, phenolic compounds, proanthocyanins, etc. V.vinifera exerts different anticancer properties such as apoptosis, cell proliferation, cell cycle arrest, and inhibition in cancerous cells. Structural bioinformatics methods, including molecular docking, molecular mechanics generalized Born surface area (MM/GBSA), absorption, distribution, metabolism, excretion studies (ADMET), and pharmacophore modeling approach, were used to determine the potential β-catenin inhibitors from V.vinifera bioactive compounds. Result: Cis-astringin, rutin, caftaric acid, trans-caftaric acid, procyanidin B3, cis-Miyabenol C, and ampelopsin H are shown to be suitable inhibitors against β-catenin due to their binding affinity and interaction with the amino acids residues at the binding sites of β-catenin compared to Food and Drug Administration (FDA) approved drugs leucovorin Calcium and Xeloda prescribed to cure colorectal cancer. Conclusions: This study suggests that V. vinifera could be a good plant source for compounds that might treat cancer by inhibiting the Wnt/β-catenin signaling pathway. [ABSTRACT FROM AUTHOR]

The distinct dark-red skin of Huaniu apples renders them attractive to customers. However, the mechanism that leads to the development of the color of the fruit is unclear. In this study, we found that compared with red Fuji (a bright-red apple cultivar), Huaniu apples had higher contents of (−)-epicatechin (EC), (−)-epigallocatechin (EGC), (−)-gallocatechin gallate (GCG), and procyanidins (PCs) B2 and C1 in the peel, which implies that the polymerization of the flavanols and PCs may be correlated with the dark-red skin of the fruit. Using EC as a substrate, we purified an enzyme from Huaniu peel. We performed protein sequencing and discovered that the enzyme was a polyphenol oxidase (PPO). The molecular weight of the enzyme was approximately 140 kDa, which we estimated by native-PAGE and SDS-PAGE, while it was 61 kDa by urea-SDS-PAGE, from which we discovered that the PPO was a dimer. We observed the lowest Km value for catechol (0.60 mM), and the best substrate was 4-methylcatechol, with a Vmax of 526.32 U mg−1 protein. EC is a suitable natural substrate, with a Km value of 1.17 mM, and 55.27% of the Vmax/Km of 4-methylcatechol. When we used EC as a substrate, the optimum temperature and pH of the PPO were 25 °C and 5.0, respectively. In summary, we purified a dimeric PPO from Huaniu apples that showed high activity to EC, which might catalyze the polymerization of flavanols and PCs and lead to the dark-red color development of the fruit. [ABSTRACT FROM AUTHOR]

Green soybean (Glycine max L.) seeds (GSS) are rich in various antioxidants and phytonutrients that are linked to various health benefits. Ultrasound-assisted extraction (UAE) technology was used for extracting the effective components from GSS. A response surface method (RSM) was used to examine the influence of liquid-to-solid ratio and extraction temperature on the bioactive compounds and antioxidant characteristics. The optimal conditions were a liquid-to-solid ratio of 25:1 and a UAE temperature of 40 °C. The observed values coincided well with the predicted values under optimal conditions. Additionally, the effects of drying methods on the procyanidins and antioxidant activities of GSS extract were evaluated. The spray-dried GSS extract contained the highest levels of procyanidins (21.4 ± 0.37 mg PC/g), DPPH (199 ± 0.85 µM Trolox eq/g), and FRAP (243 ± 0.26 µM Trolox eq/g). Spray drying could be the most time- and energy-efficient technique for drying the GSS extract. The present study also assessed the effects of storage temperature and time on procyanidins and antioxidant activities in GSS extract powder. Procyanidins were found to degrade more rapidly at 45 °C than at 25 °C and 35 °C. Storage under 25 °C was appropriate for maintaining the procyanidin contents, DPPH, and FRAP activities in the GSS extract powder. This study contributed to the body of knowledge by explaining the preparation of procyanidin extract powder from GSS, which might be employed as a low-cost supply of nutraceutical compounds for the functional food industry and pharmaceutical sector. [ABSTRACT FROM AUTHOR]

Engineering the surface of materials with desired multifunctionalities is an effective way to fight against multiple adverse factors during tissue repair process. Recently, metal-polyphenol networks (MPNs) have gained increasing attention because of their rapid and simple deposition process onto various substrates (silicon, quartz, gold and polypropylene sheets, etc.). However, the coating mechanism has not been clarified, and multifunctionalized MPNs remain unexplored. Herein, the flavonoid polyphenol procyanidin (PC) was selected to form PC-MPN coatings with Fe3+, and the effects of different assembly parameters, including pH, molar ratio between PC and Fe3+, and material priority during coating formation, were thoroughly evaluated. We found that the material priority (addition sequence of PC and Fe3+) had a great influence on the thickness of the formed PC-MPNs. Various surface techniques (e.g., ultraviolet–visible spectrophotometry, quartz crystal microbalance, X-ray photoelectron spectroscopy, atomic force microscopy, and scanning electron microscopy) were used to investigate the formation mechanism of PC-MPNs. Then PC-MPNs were further engineered with multifunctionalities (fastening cellular attachment in the early stage, promoting long-term cellular proliferation, antioxidation and antibacterial activity). We believe that these findings could further reveal the coating formation mechanism of MPNs and guide the future design of MPN coatings with multifunctionalities, thereby greatly broadening their application prospects, such as in sensors, environments, drug delivery, and tissue engineering. [ABSTRACT FROM AUTHOR]

Seasonality is gaining attention in the modulation of some physiological and metabolic functions in mammals. Furthermore, the consumption of natural compounds, such as GSPE, is steadily increasing. Consequently, in order to study the interaction of seasonal variations in day length over natural compounds' molecular effects, we carried out an animal study using photo-sensitive rats which were chronically exposed for 9 weeks to three photoperiods (L6, L18, and L12) in order to mimic the day length of different seasons (winter/summer/and autumn-spring). In parallel, animals were also treated either with GSPE 25 (mg/kg) or vehicle (VH) for 4 weeks. Interestingly, a seasonal-dependent GSPE modulation on the hepatic glucose and lipid metabolism was observed. For example, some metabolic genes from the liver (SREBP-1c, Gk, Acacα) changed their expression due to seasonality. Furthermore, the metabolomic results also indicated a seasonal influence on the GSPE effects associated with glucose-6-phosphate, D-glucose, and D-ribose, among others. These differential effects, which were also reflected in some plasmatic parameters (i.e., glucose and triglycerides) and hormones (corticosterone and melatonin), were also associated with significant changes in the expression of several hepatic circadian clock genes (Bmal1, Cry1, and Nr1d1) and ER stress genes (Atf6, Grp78, and Chop). Our results point out the importance of circannual rhythms in regulating metabolic homeostasis and suggest that seasonal variations (long or short photoperiods) affect hepatic metabolism in rats. Furthermore, they suggest that procyanidin consumption could be useful for the modulation of the photoperiod-dependent changes on glucose and lipid metabolism, whose alterations could be related to metabolic diseases (e.g., diabetes, obesity, and cardiovascular disease). Furthermore, even though the GSPE effect is not restricted to a specific photoperiod, our results suggest a more significant effect in the L18 condition. [ABSTRACT FROM AUTHOR]

Cynomorium songaricum is a traditional medicine and also a food material that is eaten raw or processed as tea or beverages. As a featured plant in semi-desert grasslands, C. songaricum is also eaten by the cattle and sheep in the area. This research study fed dairy sheep C. songaricum to determine the flavan-3-ols in sheep milk. Catechin (Cat), epicatechin (Epi), procyanidin A1 (A1), procyanidin A2 (A2), and procyanidin B1 (B1) were detected in sheep milk with the concentration being Epi > A2 > Cat > B1 > A1 at 24 h after the administration of C. songaricum. Neither A1 nor A2 were detected in the methanol extract of C. songaricum. Cysteine degradation of the plant revealed that in addition to Epi, A2 was the extending unit of the polymeric flavan-3-ols in C. songaricum , indicating that A2 is released digestively from the polymers and enters the milk. Procyanidin B-1 was converted to A1 on incubation in raw but not heated milk, indicating that the A1 in milk is the enzymatically transformed product of B1. Accelerated oxidation showed that the flavan-3-ols, B1, Cat, and Epi significantly protects the unsaturated triacyglycerols in the milk from oxidation. The flavan-3-ol could slow down the oxidation of glutathione and the latter may play an important role in preventing the milk triglycerides from oxidation. Flavan-3-ols are polyphenols with many health benefits. The present research revealed the antioxidant activities of flavan-3-ols that could be absorbed to sheep milk, adding new evidences for the values of these flavan-3-ols and for the milk. [Display omitted] [ABSTRACT FROM AUTHOR]

Proanthocyanidins are the most abundant phenols with high biological activities in chokeberry. The effects of ultrasonic-microwave assisted extraction (UMAE), ultrasound-assisted extraction (UAE), microwave-assisted extraction (MAE), and traditional solvent extraction (TSE) on the yield, purity, antioxidant and antibacterial activities of crude chokeberry proanthocyanidins (CCP) were evaluated in this study. Results showed that UMAE exhibited the maximum yield (31.52 ± 0.8 mg/g fresh weight) and purity (16.34 ± 0.59%). The method of UMAE not only significantly aggravated the destruction of cells but also accelerated the release rate of proanthocyanidins from cells. Moreover, the CCP extracted by UMAE had the greatest antioxidant and antibacterial activities in the four methods. The IC50 of ABTS·+, DPPH, superoxide anion scavenging abilities were 102.52 ± 0.84, 22.03 ± 0.55, 214.93 ± 1.33 μg/mL, respectively, and the MBC and MIC of Staphylococcus aureus, Streptococcus mutans, Pseudomonas aeruginosa, and Escherichia coli were 5, 5, 10, 5 mg/mL, and 1.25, 1.25, 2.5, 1.25 mg/mL, respectively. According to the analysis of high performance liquid chromatography-mass spectrometry (HPLC-MS), the main proanthocyanidins in purified chokeberry proanthocyanidins (PCP) were B-type procyanidins, including procyanidin B2, B5 dimer, and procyanidin C1 trimer, with the degree of polymerization (DP) of 14. Therefore, UMAE is an effective extraction to obtain chokeberry proanthocyanidins, which is a potential antioxidant or antibacterial agent. [ABSTRACT FROM AUTHOR]

Wineries produce considerable amounts of grape pomace, which is a readily available natural source of bioactive phenolic compounds. In this study, grape pomace was used as a substrate for the cultivation of eleven filamentous fungi (Trametes versicolor TV6, Trametes versicolor TV8, Trametes versicolor AG613, Trametes gibbosa, Phanerochaete chrysosporium, Ceriporiopsis subvermispora, Pleurotus eryngii, Ganoderma lucidum, Ganoderma resinaceum, Humicola grisea, and Rhizopus oryzae) under solid-state conditions (SSF) for 15 days with the aim of improving the recovery of the individual phenolic compounds. Twenty-one phenolic compounds were quantified and the recovery of seventeen of them (gallic acid, ellagic acid, p-hydroxybenzoic acid, syringic acid, vanillic acid, 3,4-dihydroxybenzoic acid, ferulic acid, o-coumaric acid, p-coumaric acid, epicatechin gallate, galocatechin gallate, quercetin, kaempferol, procyanidin B1, procyanidin B2, resveratrol, and ε-viniferin) were positively affected by SSF. Ellagic acid is the most recovered compound, whose content increased 8.8-fold after 15 days of biological treatment with Ceriporiopsis subvermispora compared to the untreated initial sample. Among the microorganisms tested, the fungi Pleurotus eryngii and Rhizopus oryzae proved to be the most effective in increasing the recovery of most phenolic compounds (1.1–4.5-fold). In addition, the nutrient composition (proteins, ash, fats) of grape pomace was positively affected by the biological treatments. [ABSTRACT FROM AUTHOR]

Dried Prunus spinosa fruits (sloes) are folk phytotherapeutics applied to treat chronic inflammatory disorders. However, their pharmacological potential, activity vectors, and drying-related changes in bioactive components remain unexplored. Therefore, the present research aimed to evaluate the anti-inflammatory and antioxidant effects of dried sloes in ex vivo models of human neutrophils and peripheral blood mononuclear cells (PMBCs) and establish their main active components. It was revealed that the fruit extracts significantly and dose-dependently inhibited the respiratory burst, downregulated the production of elastase (ELA-2) and TNF-α, and upregulated the IL-10 secretion by immune cells under pro-inflammatory and pro-oxidant stimulation. The slightly reduced IL-6 and IL-8 secretion was also observed. The structural identification of active compounds, including 45 phenolics and three Maillard reaction products (MRPs) which were formed during drying, was performed by an integrated approach combining LC-MS/MS, preparative HPLC isolation, and NMR studies. The cellular tests of four isolated model compounds (chlorogenic acid, quercetin, procyanidin B2, and 5-hydroxymethylfurfural), supported by statistical correlation studies, revealed a significant polyphenolic contribution and a slight impact of MRPs on the extracts' effects. Moreover, a substantial synergy was observed for phenolic acids, flavonoids, condensed proanthocyanidins, and MPRs. These results might support the phytotherapeutic use of dried P. spinosa fruits to relieve inflammation and establish the quality control procedure for the extracts prepared thereof. [ABSTRACT FROM AUTHOR]

Sorghum is ranked the fifth most commonly used cereal and is rich in many kinds of bioactive compounds. Food processing can affect the accumulation and decomposition of bioactive compounds in sorghum grains, and then change the biological activities of sorghum grains. The present review aims to analyze the effects of processing technologies on bioactive compounds and the biological activities of sorghum grains. Decortication reduces the total phenols, tannins, and antioxidant activity of sorghum grains. The effects of thermal processes on bioactive compounds and potential biological activities of sorghum grains are complicated due to thermal treatment method and thermal treatment conditions, such as extrusion cooking, which has different effects on the bioactive compounds and antioxidant capacity of sorghum due to extrusion conditions, such as temperature and moisture, and food matrices, such as whole grain and bran. Emerging thermal processes, such as microwave heating and high-pressure processing, could promote the release of bound phenolic substances and procyanidins, and are recommended. Biological processes can increase the nutritive and nutraceutical quality and reduce antinutritional compounds, except for soaking which reduces water-soluble compounds in sorghum. [ABSTRACT FROM AUTHOR]

Insoluble bound polyphenols (ISBP) are polyphenolic compounds linked to the food matrix with different interactions limiting both their water extractability and consequent bioaccessibility. The health-promoting potential of polyphenols is historically known and well-demonstrated; specifically, Annurca apple polyphenols were studied both in vitro and in vivo for their effect in controlling cholesterol plasma levels. The aim of the study was the preparation of nutraceutical products based on Annurca apple polyphenolic fraction through the application of a technological process (acid treatment) able to release the ISBP from Annurca apple food matrix and increase polyphenol bioaccessibility. Lyophilized annurca apple (LAA) underwent acid treatment (ATLAA), and differences in released polyphenol levels were analysed by DAD-HPLC. Free-polyphenol levels in samples treated under acid conditions were higher than in untreated ones; in particular, for oligomeric flavan-3-ols (+168% procyanidin B2, +42.97% procyanidin B1 and B2, +156.99% procyanidin C1), catechin (+512.20%), and gallic acid (+707.77%). Furthermore, ATLAA underwent an in vitro gastrointestinal digestion to evaluate the bioaccessibility of contained polyphenols, in comparison to the untreated Annurca apple. The bioaccessibility study indicates a valuable preservation of polyphenolic fraction compared to the control. [ABSTRACT FROM AUTHOR]

Pear is a kind of common temperate fruit, whose metabolite composition that contributes to the difference in fruit quality is unclear. This study identified and quantified the metabolites using a widely targeted LC-MS/MS approach in three pear species, including Pyrus bretschneideri (PB), Pyrus usssuriensis (PU) and Pyrus pyrifolia (PP). A total of 493 metabolites were identified, consisting of 68 carbohydrates, 47 organic acids, 50 polyphenols, 21 amino acids, 20 vitamins, etc. The results of PCA and OPLS-DA demonstrated that the metabolite compositions differed distinctly with cultivar variability. Our results also involved some metabolic pathways that may link to the fruit quality based on KEGG pathway analysis, the pathway of phenylalanine metabolism revealed significant differences between PB and PP (p < 0.05). Furthermore, the study selected D-xylose, formononetin, procyanidin A1 and β-nicotinamide mononucleotide as the major differentially expressed metabolites in the three species. The present study can open new avenues for explaining the differences in fruit quality of the major commercial pear cultivars in China. [ABSTRACT FROM AUTHOR]

(1) Background: Chemotherapy-induced cognitive impairment (CICI) is often observed in cancer patients and impairs their life quality. Grape-seed-orientated procyanidin has been shown to have anti-inflammatory and neuroprotective effects, yet its effects in preventing CICI have not been investigated. (2) Method: Adult male mice received 2.3 mg/kg cisplatin or saline injections for three cycles consisting of five daily injections followed by 5 days of rest. Procyanidin or saline was administered 1 h prior to cisplatin treatment. Cognitive testing, gelatin zymography, and blood–brain-barrier (BBB) penetration tests were performed after treatment cessation. RAW264.7 cells were treated by stimulated supernatant of SHSY5Y cells. In addition, high-mobility group protein B1 (HMGB1) expression and MMP-9 activity were tested. (3) Results: Repeated cisplatin treatment increased BBB penetration, MMP-9 activity, impaired performance in contextual fear conditioning, and novel object recognition tasks. The knockout of MMP-9 rescues cognitive impairment and cisplatin-induced upregulation of HMGB1 in SHSY5Y cells. HMGB1/TLR4/IP3K/AKT signaling contributes to the increased MMP-9 activity in RAW264.7 cells. Procyanidin treatment attenuates MMP-9 activity, BBB damage, and CICI. (4) Conclusions: The results indicated that MMP-9 activation and BBB disruption is involved in CICI. Procyanidin may effectively alleviate the harmful effects of cisplatin. [ABSTRACT FROM AUTHOR]

Procyanidins, as a kind of dietary flavonoid, have excellent pharmacological properties, such as antioxidant, antibacterial, anti-inflammatory and anti-tumor properties, and so they can be used to treat various diseases, including Alzheimer's disease, diabetes, rheumatoid arthritis, tumors, and obesity. Given the low bioavailability of procyanidins, great efforts have been made in drug delivery systems to address their limited use. Nowadays, the heavy burden of oral diseases such as dental caries, periodontitis, endodontic infections, etc., and their consequences on the patients' quality of life indicate a strong need for developing effective therapies. Recent years, plenty of efforts are being made to develop more effective treatments. Therefore, this review summarized the latest researches on versatile effects and enhanced bioavailability of procyanidins resulting from innovative drug delivery systems, particularly focused on its potential against oral diseases. [ABSTRACT FROM AUTHOR]

Black soybean has been used in traditional medicine to treat inflammatory diseases, cancer, and diabetes and as a nutritional source since ancient times. We found that Korean black soybean cultivar A63 has more cyanidin-3-O-glucoside, (C3G), procyanidin B2 (PB2), and epicatechin (EPC) contents than other cultivars and has beneficial effects on cell viability and anti-oxidation. Given the higher concentration of anthocyanidins and their strong anti-oxidant activity, we predicted that A63 extract could relieve inflammatory disease symptoms, including those of atopic dermatitis (AD). Here, we evaluated the anti-AD activity of A63 extract in an oxazolone (OXA)-induced mouse model. A63 extract treatment significantly reduced epidermal thickness and inflammatory cell infiltration, downregulated the expression of AD gene markers, including Interleukin (IL)-4 and IL-5, and restored damaged skin barrier tissues. Furthermore, A63 extract influenced the activation of the signal transducer and activator of transcription (STAT) 3 and STAT6, extracellular regulatory kinase (ERK), and c-Jun N-terminal kinase (JNK) signaling pathways, which play a crucial role in the development of AD. Altogether, our results suggest that A63 can ameliorate AD-like skin inflammation by inhibiting inflammatory cytokine production and STAT3/6 and Mitogen-activated protein kinase (MAPK) signaling and restoring skin barrier function. [ABSTRACT FROM AUTHOR]

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Throughout history, people of different cultures have acknowledged the relationship between food properties and health. The pseudo-fruits of different Rosa species contain high levels of vitamin C and other beneficial biological active agents such as phenolics, and others. The purpose of the research was to determine the variability of the phenolic compound profiles in the fruit of different species of Rosa L. and to evaluate the antioxidant activity of fruit extracts in vitro. The total contents of phenolics, flavonoids, procyanidins, and hydroxycinnamic acid derivatives were performed using the spectrophotometric method. Qualitative and quantitative analysis of individual phenolics in rosehip samples was carried out by applying the HPLC method. The largest amounts of phenolic compounds 26.49 ± 1.32 mg GRE/g were found in rosehip samples of the Rosa pisocarpa species. (+)-Catechin was the predominant phenolic compound in rosehip fruit samples, and the highest content 522.48 ± 26.12 µg/g was found in rosehip samples of the Rosa subcanina species. A strong correlation was found between the total amount of phenolic compounds determined in rosehip extracts and the radical scavenging and reducing the activity of their extracts in vitro (r = 0.759 and 0.761, accordingly, p < 0.001). [ABSTRACT FROM AUTHOR]

Carob syrup is one of the most important carob products, which can have applications in pastry and confectionery, as a fruit preservative, but also in the pharmaceutical field because of the antimicrobial activity due to its polyphenol content. Carob syrup is traditionally made through a very time-consuming process, involving solid–liquid extraction in boiling water and concentration at a high temperature (>100 °C), which potentially causes the degradation of the active compounds (i.e., procyanidins or flavonol glycosides). Therefore, in this work, an alternative and less drastic method based on ultrasound technology was proposed to produce carob syrup. Processing conditions (i.e., time, temperature, and liquid–solid ratio) influencing the extraction of total soluble solids (TSS) and total phenolic compounds (TPC) were optimized using a central composite design coupled to response surface methodology. Reliable mathematical models allowed us to predict the highest TSS (24 ± 2 °Brix) and TPC (1.7 ± 0.5 mg/mL) values that could be obtained at 15 min, 35 °C, and 2 mL/g. Finally, a different HPLC-DAD phenolic pattern was determined between syrups produced by traditional and ultrasound methods; epicatechin, 4-hydroxycoumaric acid, and ferulic acid were more concentrated in the former, while procyanidin B2, myricitrin, and quercitrin were prevalent in the latter one. [ABSTRACT FROM AUTHOR]

Tea is an important woody crop whose cultivation is severely limited by cold stress. Although 5-aminolevulinic acid (ALA) is known to be effective in alleviating abiotic stresses in plants, knowledge of the detailed metabolic response of tea plants to exogenous ALA-induced cold resistance is still limited—a lack which restricts our ability to protect tea plants from cold stress. In the present study, we performed an in-depth metabolomics analysis to elucidate the metabolic responses of tea plants to cold stress and explore the role of ALA in improving tea plants' cold-resistance capability. Metabolic profiles showed that cold stress altered various metabolisms in tea plants, especially galactose composition and flavonoid contents. Furthermore, exogenous ALA application altered a series of metabolisms associated with cold stress. Importantly, increases in metabolites, including catechin, 3,4-dihydroxyphenylacetic acid and procyanidin B2, involved in the mechanisms of ALA improved tea plants' cold resistance. Overall, our study deciphered detailed metabolic responses of tea plants to cold stress and elucidated the mechanisms of ALA in enhancing cold resistance through rebuilding compositions of soluble carbohydrates and flavonoids. Therefore, we have provided a basis for exogenous usage of ALA to protect tea plants from cold stress. [ABSTRACT FROM AUTHOR]

Currently the standard surgical treatment for bladder defects is augmentation cystoplasty with autologous tissues, which has many side effects. Biomaterials such as small intestine submucosa (SIS) can provide an alternative scaffold for the repair as bladder patches. Previous studies have shown that SIS could enhance the capacity and compliance of the bladder, but its application is hindered by issues like limited smooth muscle regeneration and stone formation since the fast degradation and poor mechanical properties of the SIS. Procyanidins (PC), a natural bio-crosslinking agent, has shown anti-calcification, anti-inflammatory and anti-oxidation properties. More importantly, PC and SIS can crosslink through hydrogen bonds, which may endow the material with enhanced mechanical property and stabilized functionalities. In this study, various concentrations of PC-crosslinked SIS (PC-SIS) were prepared to repair the full-thickness bladder defects, with an aim to reduce complications and enhance bladder functions. In vitro assays showed that the crosslinking has conferred the biomaterial with superior mechanical property and anti-calcification property, ability to promote smooth muscle cell adhesion and upregulate functional genes expression. Using a rabbit model with bladder defects, we demonstrated that the PC-SIS scaffold can rapidly promote in situ tissue regrowth and regeneration, in particular smooth muscle remodeling and improvement of urinary functions. The PC-SIS scaffold has therefore provided a promising material for the reconstruction of a functional bladder.

The longan pericarp turns brown dramatically after harvesting, but the mechanism is not well understood. In this work, two peroxidases were purified from longan pericarp and found to be identical to the class III peroxidases PRX53-2 and PRX53-3. In vitro , PRX53-2/3 catalyzed the browning of several pericarp abundant proanthocyanidin and lignin monomers, such as (−)-epicatechin (EC), (+)-catechin (CT) and coniferyl alcohol (ConA). PRX53–2 was upregulated and highly-expressed, while PRX53-3 was expressed at low levels after harvesting; thus, PRX53-2 was considered a browning-related gene. The reaction with both proanthocyanidin and lignin presented a greater degree of brown coloration compared to the single substrate reactions. Several procyanidins isomers, EC-ConA and CT-ConA were detected in the double-substrate reaction. These results not only demonstrate that the effects of PRX53-2 on proanthocyanidin and lignin polymerization may be crucial for longan pericarp browning, but also help in developing new strategies or preservatives to delay pericarp browning. • PRX53-2/3 was purified from longan pericarp and showed high activity to guaiacol. • PRX53-2 is highly expressed during longan pericarp browning in postharvest storage. • PRX53-2 catalyzes proanthocyanidin and lignin monomers polymerization in vitro. • The polymerization of (epi)catechin is enhanced when ConA is present. • A new proposed mechanism helps in developing strategies to delay pericarp browning. [ABSTRACT FROM AUTHOR]

Elevated blood sugar levels caused by starch digestion was a target for controlling diabetes mellitus. The in vitro and in vivo digestibility of wheat starch was evaluated to find that adding 15 % persimmon leaf extract (PLE) to starch reduced its digestibility by 69.50 % and the peak postprandial blood glucose by 23.63 %. Subsequently, we observed under scanning electron microscopy and atomic force microscopy that the presence of PLE led to the destruction of starch structure and the aggregation of α-glucosidase so as to decrease starch digestion and hinder the binding of starch to α-glucosidase. Through multi-spectral analysis, PLE hindered the clathrate of iodine and starch, and also increased the crystallinity of starch by 48.58 %. For α-glucosidase inhibitory activity (IC 50 = 72.49 μg/mL), PLE preferentially occupied the active center of α-glucosidase, changed its fluorescence characteristics and secondary structure through hydrogen bonding and hydrophobic interaction. Moreover, among the 23 potential α-glucosidase inhibitors screened from PLE, combined with molecular simulation, Procyanidin B2 had the strongest inhibitory effect (IC 50 = 33.22 μg/mL) and binding energy (−7.09 kcal/mol), which was most effectively inhibitory on digestion. These results indicated the potential of PLE in hypoglycemia targeting both starch and α-glucosidase. • Persimmon leaf extract (PLE) effectively delayed starch digestion in vitro and in vivo. • Clarify how PLE upraised the ordered crystal structure of starch. • PLE inhibited α-glucosidase through hydrogen bonding and hydrophobic interactions. • Procyanidin B2 showed the strongest inhibition among the 23 PLE-derived inhibitors. • Hypoglycemic effect of PLE was due to its dual action on starch and α-glucosidase. [ABSTRACT FROM AUTHOR]