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Two extracts derived from plant material rich in hydrolysable (Tara, T; Caesalpinia spinosa) or condensed (Mimosa, M; Acacia mearnsii) tannins were added to lamb’s diet and their effects on meat quality and on microbial population were evaluated; a diet without tannins represented the Control (C). Meat pH, vitamin E, intramuscular fat content and muscle fatty acid composition were determined. Oxidative stability and microbiological analyses were performed on meat samples after 0, 4 and 7 days of refrigerated storage. Psychrotrophic bacteria were identified through MALDI-TOF MS analysis. Regarding meat fatty acids, Tara treatment decreased the percentage of monounsaturated fatty acids. The counts of all microbial groups were similar among dietary treatments at day 0, while a significant reduction of microbial loads was observed in T-group at day 7. Pseudomonas fluorescens group count was significantly affected by T extract supplementation. The MALDI-TOF MS identification revealed the dominance of Pseudomonas fragi species in all samples while Pseudomonas lundensis, Brochothrix thermosphacta and Candida famata were revealed only in control ones. In conclusions, the tannin extract supplementation is a promising dietary strategy to preserve lamb meat quality.

A bio-guided study of leaf extracts allowed the isolation of two new macrobicyclic hydrolysable tannins, namely merianin A (1) and merianin B (2), and oct-1-en-3-yl β-xylopyranosyl-(1„-6’)-β-glucopyranoside (3) from Meriania hernandoi, in addition to 11 known compounds reported for the first time in the Meriania genus. The structures were elucidated by spectroscopic analyses including one- and two-dimensional NMR techniques and mass spectrometry. The bioactivities of the compounds were determined by measuring the DPPH radical scavenging activity and by carrying out antioxidant power assays (FRAP), etiolated wheat coleoptile assays and phytotoxicity assays on the standard target species Lycopersicum esculentum W. (tomato). Compounds 1 and 2 exhibited the best free radical scavenging activities, with FRS50 values of 2.0 and 1.9 µM, respectively.

Java plum ( Syzygium cumini Lam.) is a rich source of polyphenolics with many purported health benefits, but the effect of maturation on polyphenolic content is unknown. Freeze-dried samples of Java plum from seven different maturity stages were analyzed for anthocyanin, flavonol, flavanonol and hydrolysable tannin composition by HPLC. Anthocyanins were first detected at the green-pink stage of maturity and increased throughout maturation with the largest increase occurring from the dark purple to black stages of maturation. Levels of gallotannins, ellagitannins, flavonols, gallic acid and ellagic acid were highest at early stages of maturation and decreased as the fruit ripened. For production of antioxidant-rich nutraceutical ingredients, fruit should be harvested immature to obtain extracts rich in hydrolysable tannins and flavonols. The exceptional anthocyanin content of black fruit may prove useful as a source of a natural colorant. [ABSTRACT FROM AUTHOR]

1,2,3,4,6-Penta-O-Galloyl-β- d -Glucose (PGG) is a hydrolysable tannin that belongs to the group of gallotannins but also participates in the formation of ellagitannins. PGG is composed of five galloyl groups with a glucose at its core and has structural characteristics that confer a high biological power. In this paper, we describe the chemistry of PGG, which is analyzed from a critical point regarding the types of synthesis, new sources of production from plants and by-products, highlighting the PGG obtaining, and its main functional properties recently reported in scientific literature. PGG has attracted attention because of its therapeutic potential and has shown functional properties as antimicrobial, anti-inflammatory, anti-carcinogenic, antidiabetic and antioxidant. Bioconversion from tannic acid can be potentialized with the use of biotechnological techniques. PGG can be obtained from natural sources as by-products. Research should continue to obtain pure molecules, in adequate quantity and with great biological activity. [ABSTRACT FROM AUTHOR]

Main conclusion : The polyphenol profiles of 18 cell cultures from 12 plant species were screened. The detected polyphenol fingerprints were diverse and differed from polyphenol profiles typically found in corresponding plant species. Cell cultures originating from 12 different plant species growing or grown in the Nordic countries were screened for their ability to synthesize polyphenols to assess their suitability for future studies and applications. The focus was on plant families Rosaceae and Ericaceae. On average, the Rosaceae cultures were the most efficient to produce hydrolysable tannins and the Ericaceae cultures were the most efficient to produce proanthocyanidins. This is in line with the general trend of polyphenols found in Rosaceae and Ericaceae leaves and fruits, even though several individual cell cultures differed from natural plants in their polyphenolic composition. Overall, several of the studied cell cultures exhibited capability in producing a large variety of polyphenols, including tannins with a high molecular weight, thus also showing promise for further studies concerning, for example, the accumulation of specific polyphenols or biosynthesis of polyphenols in the cell cultures. [ABSTRACT FROM AUTHOR]

Wine aging in wooden barrels improves the final products' sensory profile and increases the price. Among the different types of woods, the International Enological Codex of the International Organisation of Vine and Wine (OIV) approves only the use of Oak and Chestnut, thus producing a need for fast and cost-effective authentication methods. In this study Fourier Transform (FT)-mid-infrared (IR) spectroscopy combined with chemometrics was employed to analyze and discriminate wines aged in barrels made from different type of wood species and in stainless steel tanks, over a period of 12 months. The wines used were made from four indigenous Greek grape varieties, two white and two red. A complete differentiation of the samples was achieved according to grape variety, the container type and the aging time based on two spectral regions (from 1800 to 1500 cm−1 and from 1300 to 900 cm−1) of their FT-IR spectra. [ABSTRACT FROM AUTHOR]

Environmental stresses not only influence production of plant metabolites but could also modify their resorption during leaf senescence. The production-resorption dynamics of polyphenolic tannins, a class of defense compound whose ecological role extends beyond tissue senescence, could amplify the influence of climate on ecosystem processes. We studied the quantity, chemical composition, and tissue-association of tannins in green and freshly-senesced leaves of Quercus rubra exposed to different temperature (Warming and No Warming) and precipitation treatments (Dry, Ambient, Wet) at the Boston-Area Climate Experiment (BACE) in Massachusetts, USA. Climate influenced not only the quantity of tannins, but also their molecular composition and cell-wall associations. Irrespective of climatic treatments, tannin composition in Q. rubra was dominated by condensed tannins (CTs, proanthocyanidins). When exposed to Dry and Ambient*Warm conditions, Q. rubra produced higher quantities of tannins that were less polymerized. In contrast, under favorable conditions (Wet), tannins were produced in lower quantities, but the CTs were more polymerized. Further, even as the overall tissue tannin content declined, the content of hydrolysable tannins (HTs) increased under Wet treatments. The molecular composition of tannins influenced their content in senesced litter. Compared to the green leaves, the content of HTs decreased in senesced leaves across treatments, whereas the CT content was similar between green and senesced leaves in Wet treatments that produced more polymerized tannins. The content of total tannins in senesced leaves was higher in Warming treatments under both dry and ambient precipitation treatments. Our results suggest that, though climate directly influenced the production of tannins in green tissues (and similar patterns were observed in the senesced tissue), the influence of climate on tannin content of senesced tissue was partly mediated by the effect on the chemical composition of tannins. These different climatic impacts on leaves over the course of a growing season may alter forest dynamics, not only in decomposition and nutrient cycling dynamics, but also in herbivory dynamics. [ABSTRACT FROM AUTHOR]

Purpose: We investigated the effects of dietary supplementation with strawberry extracts rich in ETs and fructo-oligosaccharides (FOS) on the intestinal microbiota and the formation of bacterial metabolites in the distal intestine, as well as the absorption of ET metabolites and antioxidant status in rats. Methods: Rats were allocated into six groups of eight animals each and fed for 4 weeks with a control diet (group C), a control diet supplemented with FOS (group C + FOS) or modifications of these diets, in which a monomeric or dimeric ET-rich extract was added (groups ME and ME + FOS or DE and DE + FOS, respectively). Results: The extract addition, the FOS addition and their interaction significantly affected the total and selected bacterial counts in the caecal digesta (all P < 0.005). The total bacterial count was the highest in group C + FOS, lower in group DE and the lowest in group ME + FOS (10.6, 10.3 and 8.52 log cells/g, respectively; P ≤ 0.05). The total caecal content of ET metabolites was higher in the ME and ME + FOS group than in the DE and DE + FOS group, respectively (67.8 and 89.5 vs. 13.0 and 18.0 µg/g, respectively; P < 0.001). The total plasma concentration of ET metabolites was higher in the ME + FOS and DE + FOS group than in the ME group (248 and 281 vs. 8.13 ng/mL, respectively; P < 0.001). Conclusions: ETs of the monomeric ET-rich extract are more prone to intestinal breakdown than those of the dimeric ET-rich extract, and absorption of their metabolites can be increased by dietary FOS; however, together, they evoke strong antibacterial activity. [ABSTRACT FROM AUTHOR]

Castanea sativa Mill(ENC®), containing tannins against 33Chlamydiastrains, was compared to SMAP-29 with inhibitory effect againstC. trachomatisandC. pneumoniae. The ENC® activity againstChlamydiaspp. was evaluated determining the lowest concentration to achieve more than half reduction of intact chlamydial inclusions versus controls. ENC® reduced allChlamydiastrains tested at 1 µg/mL, while SMAP-29 induced reductions ofC. trachomatisandC. pneumoniaeinfectivity at 10 µg/mL. A great reduction ofC. trachomatis, C. pneumoniae, andC. abortusinfectivity was achieved with a 10 µg/mL ENC® concentration, whereas their infectivity was almost inhibited at 100 µg/mL ENC® concentration. [ABSTRACT FROM AUTHOR]

Background: Many plants of boreal forest of Quebec have been used by Native Americans to treat a variety of microbial infections. However, the antiviral activities of these plants have been seldom evaluated on cellular models to validate their in vitro efficiencies. In this study, Cornus canadensis L. (Cornaceae), a plant used in Native American traditional medicine to treat possible antiviral infections, has been selected for further examination. Methods: The plant was extracted by decoction and infusion with water, water/ethanol 1:1 and ethanol to obtain extracts similar to those used by Native Americans. The effects of the extracts were tested on herpes simplex virus type-1 (HSV-1) using a plaque reduction assay. Moreover, bioassay-guided fractionation was achieved to isolate bioactive compounds. Results: Water/ethanol 1:1 infusion of C. canadensis leaves were the most active extracts to inhibit virus absorption with EC50 of about 9 µgm L-1, whereas for direct mode, both extraction methods using water or water/ethanol 1:1 as solvent were relatively similar with EC50 ranging from 11 to 17 µgm L-1. The fractionation led to the identification of active fractions containing hydrolysable tannins. Tellimagrandin I was found the most active compound with an EC50 of 2.6 µM for the direct mode and 5.0 µM for the absorption mode. Conclusion: Altogether, the results presented in this work support the antiviral activity of Cornus canadensis used in Native American traditional medicine. [ABSTRACT FROM AUTHOR]

Terminalia catappa L. belonging to Combretaceae family is a folk medicine, known for its multiple pharmacological properties, but the neuro-modulatory effect of TC against chronic mild stress was seldom explored. The present study was designed to elucidate potential antidepressant-like effect of Terminalia cattapa (leaf) hydro-alcoholic extract (TC) by using CMS model for a period of 7 weeks. Identification of hydrolysable tannins was done by using LC–MS. After the CMS exposure, mice groups were administered with imipramine (IMP, 10 mg/kg, i.p.) and TC (25, 50 and 100 mg/kg of TC, p.o.). Behavioural paradigms used for the study included forced swimming test (FST), tail suspension test (TST) and sucrose preference test (SPT). After behavioural tests, monoamine neurotransmitter, cortisol, AchE, oxidative stress levels and mRNA expression studies relevant to depression were assessed. TC supplementation significantly reversed CMS induced immobility time in FST and other behavioural paradigms. Moreover, TC administration significantly restored CMS induced changes in concentrations of hippocampal neurotransmitters (5-HT, DA and NE) as well as levels of acetyl cholinesterase, cortisol, monoamine oxidases (MAO-A, MAO-B), BDNF, CREB, and p-CREB. It suggests that TC supplementation could supress stress induced depression by regulating monoamine neurotransmitters, CREB, BDNF, cortisol, AchE level as well as by amelioration of oxidative stress. Hence TC can be used as a complementary medicine against depression-like disorder. [ABSTRACT FROM AUTHOR]

The discovery of the ellagitannin geraniin was made exactly 40 years ago. It is a secondary metabolite found in plants and is categorised as a hydrolysable tannin under the huge family of polyphenolic compounds. At present, the occurrence of geraniin has been verified in at least 71 plant species, many of which are used in traditional medicine. Hence, like other polyphenols, geraniin has also received widespread interest as a research focus to unearth its beneficial biological effects and therapeutic values apart from understanding its chemical properties, biosynthesis and interaction with the body system. Indeed, it has been demonstrated that geraniin possesses antioxidant, antimicrobial, anticancer, cytoprotective, immune-modulatory, analgesic properties besides exerting promising therapeutic effects on hypertension, cardiovascular disease and metabolic dysregulation. The objective of this review is to summarise the current knowledge about the basic chemistry, natural sources, isolation techniques, biosynthesis, pharmacokinetics and pharmacodynamics of geraniin. With reference to this information, the clinical significance, obstacles and future perspectives in geraniin research will also be scrutinised. [ABSTRACT FROM AUTHOR]

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Solvent extracted commercial Tara tanninextract have been examined by Matrix Assisted LaserDesorption/Ionisation Time-of-Flight (MALDI-TOF)mass spectrometry and by High Pressure LiquidChromatography (HPLC). The Tara extract has beenfound to be composed of a series of oligomers ofpolygallic acid attached by an ester link to one quinicacid. They constitute the oligomers in higherproportion in the extract. Other polygallic chains linkedto one only or two repeating units such as caffeic acidand methylated quinic, methylated gallic andmethylated caffeic acids are also present. Negativeion mode MALDI-TOF showed that somecarbohydrate residues appear to still be present,linked to the polyphenolic material of the extract buttheir proportion is very low as would be expected of asolvent extracted tannin.

Hydrolysable tannins, total phenols and flavonoids in Eugenia uniflora leaves were monthly analysed for one year. The results were correlated with climate conditions (rainfall, humidity, cloudiness and mean temperature) through chemometric methods. Principal component analysis revealed high levels of hydrolysable tannins in the rainy season, whereas flavonoids were mainly produced in the dry season. These facts suggest that climatic changes may be one of the factors affecting phenol levels in Eugenia uniflora.Taninos hidrolisáveis, fenóis totais e flavonóides presentes em folhas de Eugenia uniflora foram quantificados mensalmente durante um ano. Os resultados foram correlacionados com as condições climáticas (pluviosidade, umidade, nebulosidade e temperatura média) através de métodos quimiométricos. Análise de componentes principais revelou a ocorrência de altos teores de taninos hidrolisáveis durante a estação de chuvas, enquanto os flavonóides foram produzidos principalmente na estação seca. Estes fatos sugerem que mudanças climáticas podem ser um dos fatores que afetam os níveis de fenóis em Eugenia uniflora.

Both condensed and hydrolysable tannins (CTs and HTs, respectively) have the ability to reduce enteric CH 4 production in ruminants. However, the precise mechanism of action is not fully understood. Among the proposed hypotheses are the reduction of ruminal digestibility, direct control action on protozoa, reduction of archaea, and a hydrogen sink mechanism. In this in vitro study, which simulated rumen fermentation, two additives, one containing CTs (70% based on DM) from quebracho and one with HTs (75% based on DM) from chestnut, at four levels of inclusion (2, 4, 6, 8% on an as-fed basis) were added to the fermentation substrate and tested against a negative control. Both types of tannins significantly reduced total gas (GP) and CH 4 (ml/g DM) production during the 48 h of incubation. The lower GP and CH 4 production levels were linked to the reduction in dry matter digestibility caused by CTs and HTs. Conversely, no significant differences were observed for the protozoan and archaeal populations, suggesting a low direct effect of tannins on these rumen microorganisms in vitro . However, both types of tannins had negative correlations for the families Bacteroidales&#95;BS11 and F082 and positive correlations for the genera Prevotella and Succinivibrio . Regarding the fermentation parameters, no differences were observed for pH and total volatile fatty acid production, while both CTs and HTs linearly reduced the NH 3 content. CTs from quebracho were more effective in reducing CH 4 production than HTs from chestnut. However, for both types of tannins, the reduction in CH 4 production was always associated with a lower digestibility without any changes in archaea or protozoa. Due to the high variability of tannins, further studies investigating the chemical structure of the compounds and their mechanisms of action are needed to understand the different results reported in the literature., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2023 Battelli, Colombini, Parma, Galassi, Crovetto, Spanghero, Pravettoni, Zanzani, Manfredi and Rapetti.)

Polyphenols are known to interact with protein fractions of feed ingredients in the digestive tract thereby affecting the digestibility. These effects may differ depending on the chemical composition of the protein fractions. Thus, the objective of the study was to study the impact of a tannin-rich chestnut extract (CHE) on the in-vitro digestibility (IVD) of soy protein isolate (SPI), screw-pressed soybean (SPS) and solvent-extracted soybean (SES). In addition, CHE-derived metabolites were tested for their effects on intestinal epithelial integrity. The SPI, SPS, and SES were digested in vitro without (SPI-, SPS-, SES-) or with CHE (SPI+, SPS+, SES+) or as a control (C) solely CHE. The metabolites and the polyphenols content after digestion of the soy-based products with or without CHE were quantified. The trans-epithelial resistance (TEER) was monitored in porcine jejuna in the presence of CHE-derived metabolites at three dilutions (1:4, 1:8, and 1:16 v/v) or in their absence. The claudin-1 (CLDN1), occludin (OCLN) and zonula occludens-1 (ZO1) tight junctions-protein expressions were determined. Finally, the effects of CHE-metabolites against indomethacin (INDO)-induced decrease of TEER were tested ex vivo. The CHE decreased the IVD (P < 0.05) and decreased the detectable polyphenol content (P < 0.05) after digestion of CHE with SPI, SPS, or SES. The SPI and SPI+CHE were the samples with the highest content of metabolites generated after the digestion, while CHE presented the lowest content of metabolites. No detrimental effects on TEER were observed. The 1:8 dilution increased (P < 0.05) both ZO1 and OCLN protein expression by up to + 60% compared to the control, while the dilution 1:16 increased ZO1 expression by + 100% without affecting OCLN expression. The 1:16 dilution also protected the jejunum from the effects induced by INDO. These results suggest that the anti-nutritional effects exerted by CHE on soy-based meals IVD may depend on the meal's chemical composition. Moreover, we showed that CHE polyphenols exert protective effects on the intestinal epithelium integrity ex vivo at low concentrations. • Chestnut extracts inhibit in vitro digestibility and the total polyphenol content in soy-based products depends on their chemical composition. • Chestnut extracts are an important source of polyphenols and digestive processes affect their bioavailability. • Low concentrations of metabolites obtained by the chestnut extracts' digestion exert protective effects at intestinal level. [ABSTRACT FROM AUTHOR]

To evaluate behavior of E. coli in feces of dairy cows added with hydrolysable tannins, an experiment was conducted, in which aliquots of 100 g were randomly assigned to two hydrolysable tannins levels (0 or 10%), three values of pH 5.2, 6.5 and 8.3, and cultured at 0, 2, 6, 9, 15, 22, and 30 days after tannins addition. Feces added with HT 10% shown the highest E. coli growth (P < 0.01) compared to those that did not received HT (Log10 5.071 vs. Log10 4.401). Feces with 6.5-pH value had lower values (P < 0.01) of E. coli (Log10 4.525) vs. pH 5.2 (Log10 4.866), and pH 8.3 (Log10 4.816). In all cases the E. coli growth diminished (P < 0.01) as increased days number (Log10 = 5.51 day 0; Log10 = 3.36 at day 30). The results suggest that HT did not inhibit E. coligrowth in feces of cows; however, at pH values close to neutrality the E. coli growth decreases. [ABSTRACT FROM AUTHOR]

Microscopic studies on isolated ozone (O 3 ) effects or on those in synergy with light stress commonly report the induction of polyphenols that exhibit different aspects within the vacuole of photosynthesizing cells. It has been assumed that these different aspects are randomly spread in the symptomatic (injured) regions of the leaf blade. Interestingly, secretory ducts that constitutively produce polyphenols also exhibit these same variations in their vacuolar aspect, in a spatial sequence related to the destiny of these cells (e.g., programmed cell death (PCD) in lytic secretion processes). Here, we demonstrate that the deposition pattern of polyphenols prior to the establishment of the hypersensitive-like response, a type of PCD caused by O 3 , follows the same one observed in the epithelial cells of the constitutive lysigenous secretory ducts. Astronium graveolens , an early secondary Brazilian woody species, was selected based on its susceptibility to high light and presence of secretory ducts. The synergism effects were assessed by exposing plants to the high O 3 concentrations at an urban site in São Paulo City. Confocal, widefield and light microscopies were used to examine polyphenols' occurrence and aspects. The spatial pattern of polyphenols distribution along the leaflets of plants submitted to the synergism condition, in which a dense vacuolar aspect is the target of a cell destined to death, was also observed in the constitutive secretory cells prior to lysis. This similar structural pattern may be a case of homology of process involving both the constitutive (secretory ducts) and the induced (photosynthesizing cells) defenses. [ABSTRACT FROM AUTHOR]

Hydrolysable tannins (HTs) are secondary metabolites from plants, which are roughly classified into gallotannins and ellagitannins having gallic acid and ellagic acid residues respectively attached to the hydroxyl group of glucose by ester linkage. The presence of hexahydroxydiphenoyl and nonahydroxyterphenoyl moieties is considered to render antimicrobial property to HTs. HTs also show considerable synergy with antibiotics. Nevertheless, they have low pharmacokinetic property. The present review presents the scope of HTs as future antimicrobial agent. Copyright © 2016 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

Ethnopharmacological relevance The dried fruit of Terminalia chebula (fructus chebulae) is an important Traditional Medicine used for intestinal and hepatic detoxification. Gurigumu-7 which is made of fructus chebulae and 6 other traditional medicines is one of the most frequently used compound Mongolian and Tibet medicines for liver diseases. Terminalia phenolics are considered as the bioactive constituents of fructus chebulae and consequently of Gurigumu-7. Aim of the study To compare the pharmacokinetic profiles of Terminalia phenolics after intragastric administration of the aqueous extracts of fructus chebulae and Gurigumu-7 and to evaluate the possible influence of intestinal bacterial metabolism on these pharmacokinetic profiles. Materials and methods An ultra performance liquid chromatography with triple quadrupole mass spectrometry method was established and validated for simultaneously determining the pharmacokinetic profiles of seven Terminalia phenolics after intragastric administration of pure compounds, fructus chebulae extract, and Gurigumu-7 extract. In vitro rat fecal lysates experiments were carried out to explore the metabolic discrepancy between fructus chebulae and Gurigumu-7. Results Seven Terminalia phenolics were detected in rat plasma after intragastric administration of the aqueous extracts of fructus chebulae and Gurigumu-7. Administration of Gurigumu-7 could promote the absorption and increase the C max and AUC values of these phenolic constituents compared to fructus chebulae administration. The fecal lysates studies showed that the Terminalia phenolics in Gurigumu-7 were less rapidly bio-transformed than those in fructus chebulae. This may be a contributing factor to the pharmacokinetic discrepancy between the phenolics in fructus chebulae and Gurigumu-7. Conclusion Administration of Gurigumu-7 could increase the absorption of Terminalia phenolics through slowing down the intestinal bacteria metabolism. These results provide, in part, an in vivo rationale for the formulation of the traditional Mongolia / Tibet medicine, Gurigumu-7. [ABSTRACT FROM AUTHOR]

Ellagitannins are a subclass of hydrolysable tannins that have been suggested to function as defensive compounds of plants against herbivores. However, it is known that the conditions in the digestive tracts of different herbivores are variable, so it seems reasonable to anticipate that the reactivities and modes of actions of these ingested defensive compounds would also be different. A previous study on a few ellagitannins has shown that these polyphenolic compounds are highly oxidizable at high pH and that their bioactivity can be attributed to certain structural features. Herein, the activities of 13 ellagitannins using the deoxyribose assay were measured. The results provided information about the anti-oxidant, pro-oxidant and metal chelating properties of ellagitannins. Surprisingly, many of the tested ellagitannins exhibited pro-oxidant activities even at neutral pH and only moderate to low radical scavenging activities, although the metal chelating capacities of all tested ellagitannins were relatively high. [ABSTRACT FROM AUTHOR]

Activity-guided isolation of 80% acetone extract of Cornus alba, which is traditionally used as an anti-inflammatory, hemostatic and diuretic in Korea, yielded one novel compound, tentatively designated cornusiin H (13), together with 12 known compounds. The known compounds included four flavonoids (catechin (1), quercetin-3-O-β-D-glucuronide (2), quercetin-3-O-β-D-glucopyranoside (3), kaempferol-3-O-β-D-glucopyranoside (4)) and eight hydrolysable tannins (gallic acid (5), 2,6-di-O-galloyl-hamamelofuranoside (6), 2-galloyl-4-caffeoyl-L-threonic acid (7) 2,3-di-O-galloyl-4-caffeoyl-Lthreonic acid (8), 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranoside (9), cornusiin B (10), cornusiin A (11) and camptothin B (12)). All compounds exhibited potent 1,1-diphenyl-2-picrylhydrazyl (DPPH)-free radical scavenging activity. Especially, the radical scavenging activities of 6 and 9-13 were higher than that of vitamin C. Compounds 9, 11, 12 and 13 inhibited the production of nitric oxide (NO) in lipopolysaccharide-stimulated RAW264.7 cells to the same degree as NG-Monomethyl-L-arginine (L-NMMA). When the antiproliferative effects of the isolated compounds were assessed in prostate cancer cells, the dimeric ellagitannins (11-13) selectively inhibited LNCaP hormone-dependent prostate cancer cells. Flow cytometry analysis indicated that the dimeric ellagitannins induced apoptosis and S-phase arrest. These results suggest that dimeric ellagitannins from Cornus alba can be developed as functional materials or herbal medicines for prostate tumors such as benign prostate hyperplasia and early-stage prostate cancer. [ABSTRACT FROM AUTHOR]

The coupling of matrix-assisted laser desorption/ionisation time-of-flight (MALDI-TOF) mass spectrometry with 13C nuclear magnetic resonance (NMR) is a suitable method for examining the composition of hydrolysable tannins and has been applied to the investigation of valonia oak (Quercus aegylops) acorn tannin extract. Such methods can determine the extract's structural aspects and other characteristics. It was determined that valonia oak acorn tannin extract is composed of mainly pentagalloylglucose structures; their rearrangement structures, vescalagin/castalagin (with linkages to flavogallonic acid) and vescalin/castalin; ellagic acid and vescavaloneic/castavaloneic acid; and free gallic acid and glucose. Traces of catechin gallate were also observed in this tannin extract. The tannin from acorns of valonia oak was used to substitute up to 50% of the phenol used in the preparation of phenolic resins as adhesives for wood particleboard. These phenol-tannin-formaldehyde resins showed comparable performance to phenol-formaldehyde resins. [ABSTRACT FROM AUTHOR]

This paper describes for the first time a complete characterization and quantification of the phenolic compounds in raw and heat-treated northern red oak (Quercus rubra L.) seeds using UHPLC-DAD-ESI-HRMS/MS. A total 42 phenolic compounds belonging to five different groups of compounds, including ellagitannins, gallotannins, phenolic glycosides, hydroxybenzoic acid derivatives (HBA derivatives) and ellagic acid derivatives (EA derivatives), were identified, and most of them were reported in Q. rubra seeds for the first time. Significant variability of phenolic composition existed among raw and roasted samples under different temperature and time conditions. The total content of the phenolics, ellagitannins, gallotannins and phenolic glycosides was drastically reduced by roasting, regardless of the thermal processing conditions. In turn, an increase the roasting temperature from 135° to 200°C led to an increment in the total content of HBA and EA derivatives. Among the roasted seeds, the highest total phenolics content was found in the samples thermally treated at 185 °C for 25 min, while the lowest amounts were observed in those roasted at 135 °C for 80 min. Ellagitannins were the dominant class of phenolic compounds in the raw samples, while EA derivatives were more abundant in heat-treated seeds. Interestingly, the second most abundant phenolic group in both unroasted and roasted samples were phenolic glycosides. The predominant individual phenolic compounds, in raw seeds, were cretanin, oenothein B and rugosin E isomers. Since, among the phenolics found in the raw seeds, cretanin had the highest thermal stability, while dimeric ellagitannins and high molecular weight gallotannins exhibited the least thermal stability. The roasted samples contained mainly compounds formed by further decomposition of abovementioned compounds. [Display omitted] • A total of 42 phenolics were found in Quercus rubra L. seeds for the first time. • In raw oak seeds, the dominant phenolics were cretanin and dimeric ellagitannins. • Ellagitannins and gallotannins showed higher heat sensitivity than other phenolics. • Roasting effectively increased the content of low-molecular-weight phenolics. • The raw and roasted Q. rubra seeds are a valuable source of bioactive phenolics. [ABSTRACT FROM AUTHOR]

This paper reviews how tannins, through their effects on rumen lipid metabolism, can affect the composition of ruminants' meat and milk fat. Tannins are a heterogeneous group of plant secondary compounds known for both beneficial and detrimental effects on animals' digestive physiology. Tannins supplementation of ruminants' diets alters both in vivo and in vitro unsaturated fatty acids biohydrogenation and hence the profile of fatty acids outflowing the rumen, which can influence milk and meat content of beneficial fatty acids such as linolenic acid (c9,c12,c15-18:3), vaccenic acid (t11-18:1) and rumenic acid (c9,t11-18:2), among others. Published information indicates that tannins could inhibit biohydrogenation though affecting ruminal microorganisms. Some studies found increments in linolenic, rumenic and/or vaccenic acids in meat and milk fat using different sources of tannins; however, the effects of tannins supplementation on milk and meat fatty acid profile are not consistent, and there are contradictory results published in the literature. Effects of tannin supplementation on fatty acids biohydrogenation are affected by the chemical type of tannins, the complexity of their interactions with dietary components, and the potential microbial adaptation to tannins. In addition, the duration of the tannins-feeding period may also affect milk and meat fatty acid profile. Characterizing the effects of each specific tannic compound on different biohydrogenation steps and on the microbial species conducting them, as well as the interaction between specific tannin compounds and other dietary components can help to take greater advantage of tannins potential to contribute to improve human health through promoting beneficial fatty acids in ruminants products. [ABSTRACT FROM AUTHOR]

A phytochemical investigation of Eugenia uniflora's leaf extract resulted in the isolation of eleven phenolic compounds: 2,3-di-O-galloyl-β-D-glucose (1), 1,2,3,4,6-penta-O-galloyl-β-D-glucose (2), gemin D (3), hippomanin A (4), oenothein B (5), eugeniflorin D2 (6), camptothin A (7), afzelin (8), quercitrin (9), myricitrin, (10) and desmanthin-1 (11). These compounds were identified by spectroscopic methods including 1D- and 2DNMR, UV, IR, and TOF/MS. Compounds 1, 2, 3, 4, 7, 8, 9, and 11 were isolated from this species for the first time. Ten isolates were evaluated for antioxidant activity by DPPH free radical and Oxygen Radical Absorbance Capacity (ORAC-Fluorecein) assay. Dimeric tannins, oenothein B (5), eugeniflorin D2 (6), and camptothin A (7) showed a remarkable radical scavenging capacity. [ABSTRACT FROM AUTHOR]

Rhus coriaria L. (sumac) is an important crop widely used in the Mediterranean basin as a food spice, and also in folk medicine, due to its health-promoting properties. Phytochemicals present in plant foods are in part responsible for these consequent health benefits. Nevertheless, detailed information on these bioactive compounds is still scarce. Therefore, the present work was aimed at investigating the phytochemical components of sumac fruit epicarp using HPLC-DAD-ESI-MS/MS in two different ionisation modes. The proposed method provided tentative identification of 211 phenolic and other phyto-constituents, most of which have not been described so far in R. coriaria fruits. More than 180 phytochemicals (tannins, (iso)flavonoids, terpenoids, etc.) are reported herein in sumac fruits for the first time. The obtained results highlight the importance of R. coriaria as a promising source of functional ingredients, and boost its potential use in the food and nutraceutical industries. [ABSTRACT FROM AUTHOR]

Individual phenolic compounds, total phenolic content and antioxidant potential were assessed in kernels, oils and bagasse pellets (residues of oil pressing) of different walnut cultivars. Twenty-seven phenolic compounds were detected in kernels and pellets conducting high-performance liquid chromatography–tandem mass spectrometry. The main polyphenolic subclass comprised hydrolysable tannins, which accounted approximately 60.80% (kernels) and 61.66% (pellets) of the total phenolics identified (TPI). Walnut oil was poor in phenolics and contained only six different compounds but due to their low content (from 0.15 to 1.44 μg g − 1 ) just two compounds have been identified. Glansreginin A and glansreginin B were detected in all analyzed walnut products. A comparison of average amount of total phenolic content revealed that walnut oil contains as much as 154 fold less phenolics (0.05 mg GAE g − 1 FW) compared to kernels (7.7 mg GAE g − 1 FW) or pellets (7.9 mg GAE g − 1 FW). [ABSTRACT FROM AUTHOR]

Two new hydrolysable tannins, chebumeinin A ( 1 ) and chebumeinin B ( 2 ), together with eight known related compounds ( 3-10 ), were isolated from the fruits of Terminalia chebula . The new compounds were structurally determined by analysis of their spectroscopic data and the known compounds characterized by comparing their spectroscopic data with literature values. All isolates were evaluated by an HCV protease inhibition assay, and some compounds were found to be potently active. [ABSTRACT FROM AUTHOR]

• Tropical forages containing tannins can have beneficial or negative effects on ruminants. • Hydrolysable and condensed tannin fractions may influence forage degradation. • Tannins affected colonisation by rumen fibrolytic bacteria and methanogens. • Rumen degradation and fermentation were not associated to specific tannin fractions. • Methanogenesis and degradation of tannin-rich forages linked to colonising microbes. Condensed tannins in plants are found free and attached to protein and fibre but it is not known whether these fractions influence rumen degradation and microbial colonisation. This study explored the rumen degradation of tropical tannin-rich plants and the relationship between the disappearance of free and bound condensed tannin fractions and microbial communities colonising plant particles using in situ and in vitro experiments. Leaves from Calliandra calothyrsus , Gliricidia sepium , and Leucaena leucocephala , pods from Acacia nilotica and the leaves of two agricultural by-products: Manihot esculenta and Musa spp. were incubated in situ in the rumen of three dairy cows to determine their degradability for up to 96 h. Tannin disappearance was determined at 24 h of incubation, and adherent microbial communities were examined at 3 and 12 h of incubation using a metataxonomic approach. An in vitro approach was also used to assess the effects of these plants on rumen fermentation parameters. All plants contained more than 100 g/kg of condensed tannins with a large proportion (32–61%) bound to proteins. Calliandra calothyrsus had the highest concentration of condensed tannins at 361 g/kg, whereas Acacia nilotica was particularly rich in hydrolysable tannins (350 g/kg). Free condensed tannins from all plants completely disappeared after 24-h incubation in the rumen. Disappearance of protein-bound condensed tannins was variable with values ranging from 93% for Gliricidia sepium to 21% for Acacia nilotica. In contrast, fibre-bound condensed tannin disappearance averaged ∼ 82% and did not vary between plants. Disappearance of bound fractions of condensed tannins was not associated with the degradability of plant fractions. The presence of tannins interfered with the microbial colonisation of plants. Each plant had distinct bacterial and archaeal communities after 3 and 12 h of incubation in the rumen and distinct protozoal communities at 3 h. Adherent communities in tannin-rich plants had a lower relative abundance of fibrolytic microbes, notably Fibrobacter spp. whereas, archaea diversity was reduced in high-tannin-containing Calliandra calothyrsus and Acacia nilotica at 12 h of incubation. Concurrently, in vitro methane production was lower for Calliandra calothyrsus , Acacia nilotica and Leucaena leucocephala although for the latter total volatile fatty acids production was not affected and was similar to control. Here, we show that the total amount of hydrolysable and condensed tannins contained in a plant govern the interaction with rumen microbes affecting degradability and fermentation. The effect of protein- and fibre-bound condensed tannins on degradability is less important. [ABSTRACT FROM AUTHOR]

[Display omitted] • Novel information on the influence of oxygen and chestnut wood on hydrolysable tannins. • LC-ESI-HRMS/MS analysis of WS produced under distinct ageing technologies. • Hydrolysable tannins formation/degradation pathways in WS ageing. • Alternative technologies using micro-oxygenation for sustainable wine spirits' ageing. This research was focused on identifying gallotannins and ellagitannins degradation pathways to better understand their behavior in complex media such as wine spirits (WS). A WS was aged with chestnut wood staves with three levels of micro-oxygenation, nitrogen, and using wooden barrels. Gallotannins and ellagitannins were identified by LC-ESI-HRMS/MS using a Q-TOF in samples collected at 8, 21, 60, 180, 270, and 365 days of ageing, allowed comparing their relative abundances according to the ageing technology. It was established for the first time, the importance of oxygen in gallotannins and ellagitannins formation/degradation pathways in WS and shading light into the explanation for the steady increase of gallic and ellagic acid contents on WS during ageing. The results also highlighted the presence of penta- O -galloyl-β- d -glucose, tetra- O -galloyl-β- d -glucose, tri- O -galloyl-β- d -glucose, di- O -galloyl-β- d -glucose, and mono- O -galloyl-β- d -glucose, 2,3-(S)-hexahydroxydiphenoyl-β- d -glucose, pedunculagin, isomers vescalagin/castalagin and two products stemming from ethanol-promoted oxidation of castalagin/vescalagin and vescalin/castalin, in the composition WS aged with chestnut wood. [ABSTRACT FROM AUTHOR]

Bergenia crassifolia L., Saxifragaceae, is an evergreen perennial plant known in traditional medicine of Russia, Mongolia and China. Polyphenols are responsible for the number of pharmacological effects of Bergenia. UPLC-DAD-QqQ-MS and LC-DAD-ESI-QTOF-MS were used for the rapid profiling of phenolic compounds, mainly hydrolysable tannins. Green leaves consisted of 55% ellagitannins, 29% gallic acid derivatives and 11% flavonoids, with the remaining gallic acid, arbutin, bergenin and caffeoyl quinic acid. In fermented leaves, 31% of gallic acid was found, followed with 28% ellagitannins, 18% gallic acid derivatives and 18% flavonoids, with the remaining caffeoyl quinic acid, bergenin and arbutin. Tellimagrandin I, pedunculagin, caffeoyl quinic acid, monogalloyl quinic acid, 1-O-galloylglucose and 1,2,6-tri-O-galloylglucose were identified for the very first time. [ABSTRACT FROM AUTHOR]

Previous work revealed that the defatted methanol (MeOH) extract of fruits of Conocarpus erectus L. (Combretaceae family) exhibited antioxidant, antibacterial and anti-cancer activities. In further studies of this valuable plant, the defatted MeOH extract of C. erectus fruits was subjected to chromatographic fractionation in a silica gel glass column followed by reversed-phase high-performance liquid chromatography-ultraviolet-electrospray ionisation spectrometry analysis (RP-HPLC-UV-ESI-MS). The major and sharp peaks in each sample were identified or tentatively identified based on matching with some standard compounds and a review of the literature. Ellagic acid, vescalagin/castalagin isomer and di-(hexahydroxy diphenoyl) galloyl hexose isomer were tentatively identified as major components with many hydrolysable types of tannins on the basis of a comparison of its mass patterns with relevant items in the literature. Gallic acid, kaempferol 3-O- β- d-glucopyranoside and quercetin 3-O- β- d-glucopyranoside were identified on the basis of matching retention time ( t) and mass spectra with the standards. Polymethoxylated flavonoid isomers were also tentatively identified. The antioxidant properties of all samples were found to be associated with the total content of phenolic compounds. This may be considered as the first detailed phytochemical report in identifying the phytochemicals in C. erectus fruits. Due to the high antioxidant activity exhibited by both the crude MeOH extract and its fractions, it could be used as an effective natural antioxidant after further in vitro and in vivo studies. [ABSTRACT FROM AUTHOR]

Hydrolysable chestnut tannins, which contain several hydroxyl groups, were reacted with dimethyl carbonate, and then with hexamethylenediamine. The dried product was analyzed in MALDI-TOF, 13C NMR and FTIR spectrometry. The spectra revealed the presence of urethane functions and their yield was relatively high. This synthesis of polyurethanes is interesting because it does not depend on using isocyanates as reactants while instead utilizing a natural material, hydrolysable chestnut tannin, as their major constituent. [ABSTRACT FROM AUTHOR]

Pomegranate (Punica granatum (Linn.)) husk is an agri-food residual material, particularly rich in polyphenolic phytochemicals. An experimental setup based on a 2³-full factorial central composite design was implemented with the aim to optimising recovery of polyphenol extraction from pomegranate husks, using ethanol/water/citric acid as the extracting medium. The factors considered were (i) the pH of the medium, (ii) the ethanol concentration and (iii) the extraction time. Optimal extraction afforded extracts exceptionally enriched in total polyphenols, with the yield being 324.9mg gallic acid equivalents per g of dry weight. Liquid chromatography-electrospray ionisation mass spectrometry of the optimally obtained extract revealed that the principal phytochemicals recovered were punicalins A and B and ellagic acid. [ABSTRACT FROM AUTHOR]