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The yields of proanthocyanidins isolated from the initial and deresinated (extracted with hexane) bark of the Siberian cedar (Pínus sibírica) by water, 15% water-ethanol solution and ethyl acetate in a Soxhlet apparatus were compared. It was shown, that the preliminary removal of resinous substances from the cedar bark does not affect the yields of proanthocyanidins extracted with water and 15% water-ethanol solution (for the initial bark is 0.44% (wt.) and 0.57% (wt.) and for the deresinated bark is 0.43% (wt.) and 0.57% (wt.), respectively). It was established that the extraction of deresinated bark with ethyl acetate makes it possible to increase the yield of proanthocyanidins about 2 times to 1.04% (wt.). The composition of the proanthocyanidins isolated from the cedar bark was characterized by UV, FTIR, and 13C NMR spectroscopy methods. The flavonoids cyanidin and delphinidin were identified using the conversion proanthocyanidins to anthocyanidins. The proanthocyanidins isolated from cedar bark mainly consist of procyanidin and prodelphinidin, regardless of the method of their isolation – extraction by water, 15% aqueous ethanol solution or ethyl acetate. It was established that the proanthocyanidins isolated from the bark of cedar, in contrast to those isolated from the bark of pine (Pinus maritima) and (Pinus radiata), contain gallic acid residues., Сопоставлены выходы проантоцианидинов, выделенных из исходной и обессмоленной (проэкстрагированной гексаном) коры кедра сибирского (Pínus sibírica) водой, 15% водно-этанольным раствором и этилацетатом в аппарате Сокслета. Показано, что предварительное удаление смолистых веществ из коры кедра не влияет на выход проантоцианидинов при ее экстракции водой и 15% водно-этанольным раствором (составляет для исходной коры 0.44% (вес.) и 0.57% (вес.) и обессмоленной коры 0.43% (вес.) и 0.57% (вес.) соответственно). Установлено, что экстракция обессмоленной коры этилацетатом позволяет увеличить выход проантоцианидинов примерно в 2 раза до 1.04% (вес.). Методами УФ-, ИК- и 13C ЯМР-спектроскопии охарактеризован состав выделенных из коры кедра проантоцианидинов. Путем превращения проантоцианидинов в антоцианидины в их составе идентифицированы флавоноиды цианидин и дельфинидин. Проантоцианидины коры кедра, в основном состоят из процианидина и продельфинидина, вне зависимости от способа их выделения – экстракцией водой, 15% водно-этанольным раствором или этилацетатом. Установлено, что проантоцианидины из коры кедра, в отличие от выделенных из коры сосны (Pinus maritima) и (Pinus radiata), содержат остатки галловой кислоты.

Tyrosinases are essential metal-containing enzymes in the biosynthesis of melanin, therefore responsible for pigmentation of the skin. The upregulation of tyrosinase enzyme activities leads to hyperpigmentation that will become a health problems and interfere psychosocially. Inhibition of tyrosinase enzyme activity, both competitive and non-competitive become widely developed for most anti hyperpigmentation agent. Natural antioxidants are one of the potential compounds for this purpose. Red grape seeds contain high levels of antioxidant compounds, such as procyanidin, prodelphinidin, and propelargonidin. In this research in silico studies, including molecular docking, molecular dynamics simulations, and toxicity predictions, were used to assess the activity of the three molecules of polyphenolic compounds on macromolecules of the tyrosinase enzyme. Molecular docking studies show that the compound propelargonidin has the highest affinity against the macromolecule of the tyrosinase enzyme, with a binding free energy value of −32.87 kJ/mol. These results were confirmed in molecular dynamics simulations that show strong interactions at the macromolecular active site of the tyrosinase enzyme. Toxicity prediction results show that the three polyphenolic compound molecules were classified in the High-Class Category, which shows that safety is not guaranteed, but is likely, not carcinogenic and nongenotoxic. Therefore, the compound propelargonidin is predicted to be able to interact strongly with the tyrosinase enzyme. The results in this research are useful for further study in the development of tyrosinase enzyme inhibitors.

The purpose of this research was to identify metabolite change during barley (Hordeum vulgare) germination and reveal active principles for the anti-wrinkle activity. Barley was germinated with deionized water (DW) and mineral-rich water (MRW) for the comparison of the effect of mineral contents on the metabolites changes during germination. The effects of germinated barley extracts (GBEs) on collagen production and collagenase inhibition were evaluated in vitro using human dermal fibroblasts (HDFs). A pronounced anti-wrinkle activity was observed in the test group treated with the MRW-GBEs. In order to find out the active components related to the anti-wrinkle activity, an orthogonal projection to latent structure-discriminant analysis (OPLS-DA) was performed, using the data from secondary metabolites profiling conducted by UPLC–PDA–ESI–MS. The anti-wrinkle activity of MRW-GBEs was revealed to be associated with the increase of oligomeric compounds of procyanidin and prodelphinidin, indicating that it can be used as an active ingredient for anti-wrinkle agents.

In this study, the combined effect of partial postharvest dehydration and long-term ozone treatment was evaluated at 10 and 20% weight loss as a strategy to induce compositional changes in grape skin flavanols. Two separate trials were carried out in thermohygrometric-controlled chambers at 20 °C and 70% relative humidity. The first trial was conducted under an ozone-enriched atmosphere at 30 μL/L, whereas the second trial was performed under an air atmosphere as a control. Two red wine grape varieties were studied, Barbera and Nebbiolo (Vitis vinifera L.), for their different phenolic composition. Berry skin flavanol composition was determined by high-performance liquid chromatography after phloroglucinolysis and size-exclusion chromatography. The results showed that dehydration and ozone effects were variety-dependent. In Barbera skins, being characterized by lower proanthocyanidin contents, the two effects were significant and their combination showed interesting advantages related to lower proanthocyanidin loss as well as higher prodelphinidin and lower galloylation percentages. In Nebbiolo, skin flavanol composition was barely affected.

Condensed tannins (CT) have been the focus of increasing interest in the last years as a result of their potent biological properties, which have prompted their use in the food and feed sector as functional ingredients. The possible exploitation of these compounds as multifunctional additives for the implementation of active food packaging has also been recently appreciated. In this perspective, an overview of the structural features, accessible sources, methods of analysis, and functional properties of CT is provided, with the aim of critically emphasizing the opportunities offered by this widespread class of natural phenolic compounds for the rational design of multifunctional and sustainable food packaging materials.

Substantial efforts have been made in incorporating tannin-rich forages into grassland-based livestock production systems. However, the structural and functional diversity of tannins in different species limits their potential use at the field scale. We conducted a greenhouse experiment with 17 cultivars from 8 forage species and their cultivars. Ultraperformance liquid chromatography tandem mass spectrometry was used to analyze their polyphenolic profile and proanthocyanidin (PA) structural features in leaves. Our results highlight large inter- and intraspecies variability of plants in terms of polyphenol and tannin concentrations in the leaves. A concomitant and significant variation was also registered in the structural features of PA-rich forages such as the mean degree of polymerization and prodelphinidin percentage. The concentration of PA also varied within plant organs; the highest concentration was in flowers, but leaves had the highest contribution to harvestable PA biomass. Our research highlights that identifying these variations helps in identifying the representativeness of bioactivity and provides the basis for targeted breeding programs.

The process of proanthocyanidins isolation from abies bark by water and water-alcohol solutions containing 5, 10, 15 and 20 % ethanol was studied for the first time. The optimal conditions providing the maximum yield of proanthocyanidins were determined experimentally. It was shown that the use of 15-20 % water-alcohol solutions allows to increase the yield of proanthocyanidins from 0.33 to 0.38 %. The composition of the obtained proanthocyanidins was studied by UV, IR, and 13C NMR spectroscopy. The obtained proanthocyanidins were transformed into colored anthocyanidins in ethanol medium in the presence of hydrochloric acid. The flavonoids cyanidin and delphinidin were isolated and identified. It was established that the obtained proanthocyanidins mainly consist of procyanidin and prodelphinidin. It was shown that proanthocyanidins obtained from abies bark, in contrast to the proanthocyanidins isolated from pine bark described in the literature, contain gallic acid residues, which is typical for proanthocyanidins isolated from various types of tea

Summary Although tannins have been an important focus of studies of plant–animal interactions, traditional tannin analyses cannot differentiate between the diversity of structures present in plants. This has limited our understanding of how different mixtures of these widespread secondary metabolites contribute to variation in biological activity.We used UPLC‐MS/MS to determine the concentration and broad composition of tannins and polyphenols in 628 eucalypt (Eucalyptus, Corymbia and Angophora) samples, and related these to three in vitro functional measures believed to influence herbivore defence: protein precipitation capacity, oxidative activity at high pH and capacity to reduce in vitro nitrogen (N) digestibility.Protein precipitation capacity was most strongly correlated with concentrations of procyanidin subunits in proanthocyanidins (PAs), and late‐eluting ellagitannins. Capacity to reduce in vitro N digestibility was affected most by the subunit composition and mean degree of polymerisation (mDP) of PAs. Finally, concentrations of ellagitannins and prodelphinidin subunits of PAs were the strongest determinants of oxidative activity.The results illustrate why measures of total tannins rarely correlate with animal feeding responses. However, they also confirm that the analytical techniques utilised here could allow researchers to understand how variation in tannins influence the ecology of individuals and populations of herbivores, and, ultimately, other ecosystem processes.

Limonium brasiliense (Boiss.) Kuntze (Plumbaginaceae) is a medicinal plant that is popularly used in the folk medicine. In this study, we examined xanthine oxidase (XO) inhibitory activity of the aqueous fraction of Limonium brasiliense extract and its polar bioactive constituents using the enzymatic hypoxanthine (HX)–XO system in vitro. Seven active compounds isolated from the aqueous extract proved to be strong XO inhibitors. Prodelphinidin B1-3,3′-digallate (1) showed the most potent inhibitory activity with an IC50 value of 6.61 µM, comparable to allopurinol. This study provides basis for the potential use of the aqueous fraction of L. brasiliense against hyperuricemia, displaying potent XO inhibitory activity with an IC50 value of 48.3 µg/mL. This inhibitory effect is compatible with the presence of (1) in this extract.

Proanthocyanidins are plant specialized metabolites which are beneficial to animal nutrition and health. This study determined how proanthocyanidin profiles of sainfoin (Onobrychis viciifolia) and birdsfoot trefoil (Lotus corniculatus) change during the forage conservation process and along the digestive tract of lamb. We determined soluble, protein- and fiber-bound proanthocyanidins by spectrophotometric methods and soluble proanthocyanidin profiles by UPLC-MS/MS. During the conservation process, the total proanthocyanidin contents reduced in both forages and the relative proportion of insoluble proanthocyanidins increased, especially in sainfoin. The soluble proanthocyanidins, their mean degree of polymerization and the relative prodelphinidin share declined in both feed species. In the abomasum of lambs fed sainfoin silage, most of the proanthocyanidins were in insoluble form bound to proteins and fibers, but in the small and large intestines, the proportion of soluble proanthocyanidins increased again. For lambs fed birdsfoot trefoil, the trend was not so clear as proanthocyanidins were already mainly soluble in the abomasum. Nevertheless, a large part of soluble proanthocyanidins was recovered in the digestive tract but could not be detected by the UPLC-MS/MS method used. This study suggests that proanthocyanidins have probably been metabolized in the digestive tract by the resident microbiota.

Proanthocyanidins (PAs) are highly bioactive plant specialized metabolites. One of their most characteristic features is their ability to precipitate proteins. In this study, eleven plant species were used to study the structure&ndash, activity patterns between PAs and their protein precipitation capacity (PPC) with bovine serum albumin. To obtain a comprehensive selection of PAs with highly variable procyanidin to prodelphinidin ratios and mean degree of polymerizations, nearly 350 subfractions were produced from the eleven plant species by semi-preparative liquid chromatography. Their PA composition was defined by tandem mass spectrometry and high-resolution mass spectrometry, and their PPC was measured with a turbidimetry-based well-plate reader assay. The distribution of the PPC within plant species varied significantly. The mean degree of polymerization of the PAs had a strong correlation with the PPC (r = 0.79). The other structural features were significant from the PPC point of view as well, but they contributed to the PPC in different ways in different plant species. Retention time, prodelphinidin proportion, and mean degree of polymerization explained 64% of the measured variance of the PPC.

Berries of genus Vaccinium are rich in flavonoids and proanthocyanidins (PAs). We studied the PA composition and biosynthesis in bilberry (Vaccinium myrtillus L.) tissues and during fruit development. Soluble PAs, analyzed by UHPLC–MS/MS, were most abundant in stem and rhizome with the mean PA polymerization level varying between 4 and 6 in all tissues. Both A- and B-type PAs were present in all tissues. Procyanidin subunits were more common than prodelphinidin subunits in PAs. During fruit ripening, the amount of procyanidin subunits decreased while prodelphinidin subunits and F3′5′H expression increased, indicating a shift in biosynthesis toward the delphinidin branch of the flavonoid pathway. Epicatechin was the most abundant flavan-3-ol in all tissues. Expression of ANR and three isolated LAR genes, analyzed by qRT-PCR, showed connection to accumulation of PAs and flavan-3-ols biosynthesized from different flavonoid branches. Insoluble PAs accumulated during berry development, suggesting that PAs are not recycled after biosynthesis.

Chinese bayberry leaves proanthocyanidins (BLPs) belongs to the prodelphinidin category with potent EGCG unit, whose inhibition effect on α-amylase and their interaction were investigated by in vitro digestion and enzyme kinetic analysis, multi fluorescence spectroscopies (fluorescence quenching, synchronous fluorescence, and three-dimensional fluorescence), circular dichroism spectra, Fourier transform infrared spectroscopy and in silico modelling. The results revealed that BLPs was a mixed inhibitor to α-amylase with the IC50 value of 3.075 ± 0.073 μg/mL. BLPs could lead to a static fluorescence quenching of α-amylase, mainly by means of interacting with amino acids (mainly Try and Tyr residues) in one site on α-amylase molecule under the action of hydrogen bonding and/or Van der Waals force. This interaction further induced the change of secondary conformational structure, functional group structure and hydrophobicity of α-amylase, thus resulting in lowering activity. Molecular docking simulated that this binding occurred in a cavity on the surface of the α-amylase molecule, and BLPs trimer showed a relatively high binding energy. The present study provided a new insight of BLPs as an α-amylase inhibitor, which could be considered in anti-diabetic therapy.

International audience; A solid-phase extraction method was applied for the identification of a series of unconventional crown (macrocyclic) B-type proanthocyanidin tetramers (m/z 1169.2557, 1185.2507, 1201.2456, and 1217.2405) and pentamers (m/z 1457.3191, 1473.3140, 1489.3090, 1505.3039, and 1521.2988) containing (epi)catechins only (procyanidins) or (epi)catechins and (epi)gallocatechins (prodelphinidins). These compounds were identified in red wine by high-performance liquid chromatography–high-resolution mass spectrometry coupled with online hydrogen/deuterium exchange (HDX) after purification with a C18 solid-phase extraction phase from the original wine sample. The number and type of monomer units present in each procyanidin and prodelphinidin are discussed on the basis of the experimental measured masses, their retention time distribution among observed isomers, tandem mass spectrometry fragmentations, and the HDX-induced shift of the theoretical monoisotopic mass. The elution in reverse-phase high-performance liquid chromatography shifted to lower retention times when the ratio of (epi)gallocatechin units in these molecules increased with respect to the content of (epi)catechin units, as a consequence of the increase of polarity.

Isoetes sinensis Palmer is a critically endangered, first-class protected plant in China. Until now, researchers have primarily focused on the ultrastructure, phylogeny, and transcriptomes of the plant. However, flavonoid profiles and bioactivity of I. sinensis have not been extensively investigated. To develop the endangered I. sinensis for edible and medicinal purposes, flavonoid content, chemical constitution, and antioxidant activities were investigated in this study. Results revealed the following. 1) The total flavonoid content was determined as 10.74 ± 0.25 mg/g., 2) Antioxidant activities were stronger than most ferns, especially ABTS free radical scavenging activities. 3) Four flavones, containing apigenin, apigenin-7-glucuronide, acacetin-7-O-glcopyranoside, and homoplantageninisoetin; four flavonols, namely, isoetin, kaempferol-3-O-glucoside, quercetin-3-O-[6”-O-(3-hydroxy-3-methylglutaryl)-β-D-glucopyranoside], and limocitrin-Neo; one prodelphinidin (procyanidins;) and one nothofagin (dihydrochalcone) were tentatively identified in the mass spectrometry-DAD (254nm) chromatograms. This study was the first to report on flavonoid content and antioxidant activities of I. sinensis. Stronger antioxidant activity and flavonoid content suggests that the endangered I. sinensis is an important and potentially edible and medicinal plant.

In this study, a semipreparative liquid chromatography method was developed for the isolation of chemically well-defined proanthocyanidin (PA) oligomer and polymer fractions. The aim was to achieve better separation than traditionally achieved for the PAs with other chromatographic methods. The method was tested with eleven PA rich Sephadex LH-20 fractions, which originated from eleven different plant species. The resulting semipreparative fractions were analyzed by both triple quadrupole and high-resolution mass spectrometry assisted by ultrahigh-performance liquid chromatography (UPLC) separation. The results showed remarkable differences in the procyanidin to prodelphinidin ratio, mean degree of polymerization, and specific oligomeric and polymeric content. However, some of these features indicated consistent patterns between species as the function of UPLC retention time. The developed method enables the production of tens of well-defined fractions of PA oligomers and polymers from the unresolved chromatographic PA hump. Accordingly, this allows researchers to explore the most bioactive parts of the complex PA humps of any plant species, which have not been possible earlier.

A procedure based on 13C CPMAS NMR was developed to study procyanidins (PCs) and prodelphinidins (PDs) directly in milled sainfoin plant tissues. Blackcurrant and Tilia samples enabled reference spectra of purified proanthocyanidin (PA) fractions, crude extracts, and milled plant tissues, with characteristic resonances at 155, 144, and 132 ppm. PC/PD ratios were estimated from the I132/I155 intensity ratio and differed by 2.5 to 5.9% compared to thiolysis data. Normalization to the 155 ppm signal intensity from reference spectra enabled analysis of PA contents with an error of ca. 8 g PAs/100 g plant tissue. The procedure estimates the lignin contribution and allows for a correction of the PA content. In six sainfoin accessions, estimated PA contents were 1.6- to 20.8-fold higher than the thiolysis and 1.4- to 2.6-fold higher than the HCl–butanol–acetone results. Method differences may reflect the presence of unextractable, possibly high molecular weight PAs in sainfoin.

Stryphnodendron rotundifolium Mart., popularly known as “barbatimão”, is a plant species traditionally used by topical and oral routes for the treatment of infectious and inflammatory diseases. Considering the well-described antioxidant properties of this species, this study investigated the protective effects of its keto-aqueous extract using an in vitro model of iron overload. Phenolic compounds were quantified and identified by Ultra-Performance Liquid Chromatography coupled with quadrupole Time-Of-Flight Electrospray Ionization Mass Spectrometry (UPLC–ESI-qTOF-MS/MS) in positive and negative ions mode analysis. Antioxidant activity was analyzed following the iron-chelating–reducing capacity and deoxyribose degradation (2-DR) protection methods. The analysis identified condensed tannins (54.8 mg catechin/g dry fraction (DF), polyphenols (25 mg gallic acid/g DF), and hydrolyzable tannins (28.8 mg tannic acid/g DF). Among the constituents, prodelphinidin, procyanidin, and prorobinetinidine were isolated and identified. The extract significantly protected 2-DR degradation induced by Fe2+ (72% protection) or •OH (43% protection). The ortho-phenanthroline test revealed Fe2+-chelating and Fe3+-reducing activities of 93% and 84%, respectively. A preliminary toxicological analysis using Artemia salina revealed mortality below 10%, at a concentration of 0.25 mg/mL, indicating low toxicity under the present experimental conditions. In conclusion, the findings of the present study indicate that Stryphnodendron rotundifolium is a source of antioxidant compounds with the potential to be used in drug development in the context of iron overload disorders, which remains to be further investigated in vivo.

To improve the sensory quality of Moroccan red press wines, press wines were separately submitted to micro-oxygenation and three fining agents (gelatin, Polyvinylpolypyrrolidone (PVPP) based formulation and pea protein) treatments at the winery Chateau Roslane, Morocco. The results showed that each treatment has a distinct behavior in relation with interactions and precipitation monomeric fiavan-3-ol and fractions apparent and total condensed tannins. The fining agent corresponding to the vegetable protein has a greater affinity with the fraction of oligomeric condensed tannins with apparent aDP: 3.2. However, gelatin and PVPP based fining agent have an affinity with the catechin and epicatechin as well as with the fraction of polymeric tannins (apparent aDP: 6.6). For the structural parameters of proanthocyanidins, no significant differences were found out in global aDP and percentage of prodelphinidin between the different treatments. The global percentage of galloylation appeared slightly affected, while the global percentage of oxidized proanthocyanidins increased (9%) significantly (P < 0,05) for micro oxygenation treatment, unlike the fining agent has basic vegetable protein has decreased 36% the percentage of oxidation. For the Saliva Precipitation Index (SPI) and sensory analysis, the greatest reduction of SPI, bitterness and astringency was observed for both basic PVPP and vegetable protein fining agents.

This work investigates the physico-chemical and mechanical properties of tannins extracted from wood for composite materials manufacturing. Sustainable knowledge (in terms of physico-chemical properties and behaviours) of the material is needed to further enhance its applications. The condensed tannins extracted from the Bark of Ficus platyphylla (BFP) and the Bark of Vitellaria paradoxa (BVP) were analyzed using Matrix Assisted Laser Desorption/Ionization Time-Of-Flight (MALDI-TOF), Mass Spectroscopy and Attenuated Total Reflectance Fourier Transform Mid-InfraRed (ATR-FT MIR) spectra in the ranges 1800 cm-1 and 600 cm-1, as well as using CP MAS 13C-NMR. It was found that, these two tannins are procyanidin/prodelphinidin and made up of catechin/epicatechin, gallocatechin/epigallocatechin units, fisetinidin, galloyl and carbohydrates residues. Furthermore, BFP and BVP tannin bonded particleboard densities lie in the range recommended by NF EN 326-1994 standard. The resins also yielded good internal bond strength results of the panels, above relevant international standard specifications minimum requirements for interior-grade panels. The Transmission Electron Microscopy with Energy Dispersive X-ray Spectroscopy Analysis (TEM/ EDXA) are showing the ultrastructure and reveal that most of the resin material appears to be in an amorphous phase mainly composed of carbon/oxygen with small amounts of K, Ca and Mg. These particles have a very irregular morphology.

Proanthocyanidins (PAC) were isolated from pecan kernel and shell; one fraction was obtained from kernel (KR I ) and 3 fractions from shell (SH I , SH II and SH III ). The average degree of polymerization (ADP) of these fractions was estimated by phloroglucinolysis and the coupling of butanolysis and vanillin reactions. ADP decreased in the order SH I > SH II > SH III > KR I . Prodelphinidin in monomer distribution decreased in the same order. Fractions were tested as inhibitors of carbohydrate, lipid and protein hydrolysis in a simulated human digestive system. Fraction KR I was the best inhibitor. Fraction SH III , inhibited carbohydrate and lipid hydrolysis but was a poor inhibitor of proteolysis. This suggests that PAC oligomers from pecan kernel and shell could help to slow dietary carbohydrate and fat absorption, and that structural features like monomer composition and ADP are responsible from their different inhibitory potency.

Lotus seed epicarp, the main by-product of lotus seed processing, is abundant in polyphenols. In this study, polyphenols in lotus seed epicarp were separated by Sephadex LH-20 gel filtration chromatography to yield Fraction-I (F-I), Fraction-II (F-II), and Fraction-III (F-III). The polyphenol compounds in the three fractions were identified by UPLC-MI-TOF-MS. Six kinds of polyphenol compounds including cyanidin-3-O-glucoside, procyanidin trimer, and phlorizin were identified in F-I, and prodelphinidin dimer B, procyanidin dimer, and quercetin hexoside isomer were found in F-II. However, there was only procyanidin dimer identified in F-III. The in vitro antioxidant activities of the three fractions were also investigated. We found F-I, F-II, and F-III had strong potential antioxidant activities in the order of F-III > F-II > F-I. Our results suggested that polyphenols from lotus seed epicarp might be suitable for use as a potential food additive.

Astringency is a parameter of great importance for wine quality. During wine maturation in wooden barrels it can be enhanced by tannins extracted by the wood. However, their concentration is not directly correlated with astringency. Mean Degree of Polymerization (mDP) is often employed to characterize the structural characteristics of tannins in wines, providing also information on their proanthocyanidin content. The prodelphinidin content (%P), as well as the percentage of epigallocatechin (EGC) in extension and terminal units, have been negatively linked with astringency. Since the intensity of astringency is a decisive factor for the quality of a barrel-aged wine in this experiment, the structural characteristics of wine proanthocyanidins were determined in four different Greek wines, two white (Vilana and Dafni) and two red (Kotsifali and Mandilari). All wines matured for nine months in different types of containers (stainless steel tanks and barrels made of different woods). The prodelphinidin (terminal or extension) content was determined by means of phloroglucinolysis, followed by HPLC-UV-MS analysis, while astringency was assessed by a panel of trained tasters. Multivariate analysis showed that only white wines that matured in Acacia barrels contained high %P values independently of the variety used and were characterized as less astringent by the panel. Moreover, the determination of %extension and terminal EGC units revealed that the tannins of the wines maturing in Acacia barrels, contain higher amounts of EGC as terminal units. These findings could be used by winemakers in order to select the appropriate type of barrel according to the type of wine. Keywords: Astringency, proanthocyanidin, tannin, barrel

This data article contains raw and processed data related to research published in Teixeira et al. (2016) [1]. Here we introduce data acquired from the synthesis of a prodelphinidin dimer gallate. All synthesis steps are described and a dataset for the removal of the protecting on prodelphinidin synthesis is presented. With hydrogenolysis in situ with triethylsilane the hydrogen required is produced and used at the same time, making the reaction possible without resorting to bottled hydrogen. Full NMR and HPLC-ESI-MS analysis data is also provided. Keywords: Prodelphinidins, Synthesis, Hydrogenation

Our study investigated the effects of condensed tannins (CT) on rumen in vitro methane (CH4) production and fermentation characteristics by incubating lucerne in buffered rumen fluid in combination with different CT extracts at 0 (control), 40, 80 and 120 g CT/kg of substrate DM. Condensed tannins were extracted from four sainfoin accessions: Rees ‘A’, CPI63763, Cotswold Common and CPI63767. Gas production (GP) was measured using a fully automated GP apparatus with CH4 measured at distinct time points. Condensed tannins differed substantially in terms of polymer size and varied from 13 (Rees ‘A’) to 73 (CPI63767) mean degree of polymerization, but had relatively similar characteristics in terms of CT content, procyanidin: prodelphinidin (PC: PD) and cis:trans ratios. Compared to control, addition of CT from CPI63767 and CPI63763 at 80 and 120 g CT/kg of substrate DM reduced CH4 by 43% and 65%, and by 23% and 57%, respectively, after 24-h incubation. Similarly, CT from Rees ‘A’ and Cotswold Common reduced CH4 by 26% and 46%, and by 28% and 46% respectively. Addition of increasing level of CT linearly reduced the maximum rates of GP and CH4 production, and the estimated in vitro organic matter digestibility. There was a negative linear and quadratic (p < 0.01) relation between CT concentration and total volatile fatty acid (VFA) production. Inclusion of 80 and 120 g CT/kg of substrate DM reduced (p < 0.001) branched-chain VFA production and acetate: propionate ratio and was lowest for CPI63767. A decrease in proteolytic activity as indirectly shown by a change in VFA composition favouring a shift towards propionate and reduction in branched-chain VFA production varied with type of CT and was highest for CPI63767. In conclusion, these results suggest that tannin polymer size is an important factor affecting in vitro CH4 production which may be linked to the CT interaction with dietary substrate or microbial cells.

Made available in DSpace on 2020-12-12T01:09:38Z (GMT). No. of bitstreams: 0 Previous issue date: 2020-04-06 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Ethnopharmacological relevance: Eugenia dysenterica (ED) leaves are used in Brazil to treat cardiac diseases; however, there are no scientific data describing the effects of this species on cardiac activity. Aim of the study: To investigate the effect of ED aqueous leaf extract (EDLE) on hear rate (HR) and mean arterial pressure (MAP) of anaesthetised rats and its underlying mechanism of action. Material and methods: EDLE was analysed, and its proanthocyanidin composition was determined. After performing dose-effect curves for EDLE on HR and MAP, EDLE-induced hypotension was evaluated before and after atropine (AT), L-N(ω)-nitro-L-arginine methyl ester (L-NAME), hexamethonium (HXT), indomethacin (IND), carbenoxolone (CBX), or nifedipine (NFD) administration. The effect of proanthocyanidin-depleted extract (EDLE/P-) was also determined and compared to that of the EDLE with proanthocyanidins. Results: EDLE decreased the MAP in a dose-dependent manner; HR was decreased only with the highest and most toxic dose. Only CBX and NFD decreased EDLE-induced hypotension. Five polymeric series of proanthocyanidins were identified, which were mainly constituted by procyanidin and prodelphinidin units with B-type linkage and up to 12 flavan-3-ol units. EDLE/P- induced hypotension did not differ from that induced by EDLE. Conclusions: The cardiovascular effects of EDLE were primarily related to its vascular action. EDLE-induced hypotensive effect appeared to involve L-type calcium channel blockage as well as myoendothelial gap junction signalling. The higher molecular weight proanthocyanidins from EDLE are unlikely to contribute to its cardiovascular effect. São Paulo State University/UNESP Department of Physiology Institute of Biosciences Federal University of Mato Grosso do Sul/UFMS Laboratório de Produtos Naturais e Espectrometria de Massas (LAPNEM) Federal University of Uberlândia/UFU Department of Pharmacology Institute of Biomedical Sciences Campus Umuarama São Paulo State University/UNESP Department of Physiology Institute of Biosciences FAPESP: 2013/18382-7

The objective of this work was to characterize condensed tannins (CT) from six tropical forage legumes and to determine their biological activity. The monomers propelargonidin, prodelphinidin and procyanidin were analyzed, as well as extractable condensed tannin (ECT), protein-bound CT (PBCT) and fiber-bound CT (FBCT), molecular weight, degree of polymerization, polydispersity index, and biological activity by protein precipitate by phenols (PPP) of leaves of the legumes Cajanus cajan, Gliricidia sepium, Stylosanthes capitata x Stylosanthes macrocephala (stylo), Flemingia macrophylla, Cratylia argentea, and Mimosa caesalpiniifolia, and of the bark of this latter species. Differences were observed in the concentrations of ECT, PBCT, PPP, and total condensed tannin among species, but not in that of FBCT. The highest value of PBCT occurred in F. macrophylla. Total CT varied from nondetected concentration in C. argentea to the highest concentration in M. caesalpiniifolia leaves that contain the greatest levels of PPP. No differences were observed for polymerization degree in stylo, F. macrophylla, and M. caesalpiniifolia. Leaves of stylo, C. cajan, and G. sepium, all containing between 20 and 50 g kg-1 total CT, should be beneficial CT sources, if offered as sole feeds in ruminant diets. The ratio of prodelphinidin:procyanidin varies from 10:80 (stylo) to 65:35 (F. machrophylla), and propelargonidin is only determined in C. argentea. Resumo: O objetivo deste trabalho foi caracterizar taninos condensados de seis leguminosas forrageiras e determinar sua atividade biológica. Os monômeros propelargonidina, prodelfinidina e procianidina foram analisados, assim como taninos condensados extraíveis (TCE), taninos condensados ligados a proteínas (TCLP) e ligados a fibras (TCLF), massa molecular, grau de polimerização, índice de polidispersão e atividade biológica, por meio de proteínas precipitadas por fenóis (PPF), em folhas das leguminosas Cajanus cajan, Gliricidia sepium, Stylosanthes capitata x Stylosanthes macrocephala (estilosantes), Flemingia macrophylla, Cratylia argentea e Mimosa caesalpiniifolia, e na casca desta última espécie. Foram observadas diferenças nas concentrações de TCE, TCLP, PPF e total de taninos condensados entre as espécies, mas não na de TCLF. O maior valor de TCLP ocorreu em F. macrophylla. O total de TC variou de não detectável em C. argentea à maior concentração em folhas de M. caesalpiniifolia, que contêm os maiores níveis de PPF. Não se observaram diferenças quanto ao grau de polimerização em estilosantes, F. macrophylla e M. caesalpiniifolia. Folhas de estilosantes, C. cajan e G. sepium, todas com total de TC entre 20 e 50 g kg-1, poderiam ser fontes benéficas de TC, se oferecidas como única fonte de alimentos em dietas de ruminantes. A proporção prodelfinidina:procianidina variou de 10:80 (stylo) a 65:35 (F. machrophylla), e a propelargonidina é determinada somente em C. argentea.

Salal ( Gaultheria shallon Pursh.) is a wild perennial shrub of the Ericaceae and common in coastal forests of western North America, and its berries were an important traditional food for First Nations in British Columbia. Salal berries were investigated for phytochemical content and antioxidant capacity over the course of fruit development. The proanthocyanidin content was extremely high in young berries (280.7 mg/g dry wt) but dropped during development to 52.8 mg/g dry wt. By contrast, anthocyanins accumulated only at the late berry stages. Total antioxidant capacity, as measured by the 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method, reflected both proanthocyanidin and anthocyanin content, and in mature berries reached 36 mmol Trolox equivalents/100 g dry wt. More detailed phytochemical analysis determined that delphinidin 3- O -galactoside is the dominant anthocyanin, and that the berries are also rich in procyanidins, including procyanidin A2 which has been implicated in anti-adhesion activity for uropathogenic E. coli . Proanthocyanidins were 60% prodelphinidin, and overall concentrations were higher than reported for many Vaccinium species including blueberry, lingonberry, and cranberry. Overall, the phenolic profile of salal berries indicates that these fruit contain a diversity of health-promoting phenolics.

The objective of this study is to investigate the bioactive compounds and antioxidant activity of coffee and tea mangrove (locally known in Indonesia) produced from the fruit of Rhizophora stylosa. Furthermore, three raw materials of coffee mangrove were also investigated to clarify their potencies. The crude extracts of five samples were subjected to antioxidant assay using DPPH. The results show that the extract of tea mangrove has the strongest activity; then, it was successfully fractionated using different polarity of solvents and yielded acetone and methanol fractions that had high antioxidant activity. The acetone fraction was purified and gave fractions A1, A2, A3, A4, A5, and A6, but only A2 and A3 indicated antioxidant activity and, therefore, they were subjected to further purification. Fractions A3 (caffeine) and A2 gave AS1 (N,N-dimethyl-L-alanine), AS2 (quercetin-3-O-galactopyranoside), AS3 (dodecanoic acid), and AS4 that had the similar 1H-NMR spectrometric results with AS2, while the methanol fraction did not exhibit clear peaks on the chromatogram by HPLC. Therefore, the precipitation method was conducted to purify this fraction, and the precipitate was analyzed by NMR spectra. The results from 1H and 13C NMR indicate that this fraction is a typical polymer of condensed tannins, containing procyanidin and prodelphinidin units.

International audience; The variable anthelmintic efficacy of condensed tannins (CT) against gastrointestinal nematodes may depend on CT concentration, composition, or fate along the digestive tract. We analyzed CT concentration and composition by acetone-HCl-butanol and thiolysis coupled to HPLC-MS in digesta and feces of lambs. Lambs had been infected with Haemonchus contortus and Trichostrongylus colubriformis and received sainfoin pellets and hazelnut skins of contrasting prodelphinidin/procyanidin ratios. The digesta and feces had lower CT concentrations than the original feeds but similar concentration patterns across the digestive compartments. The changes in assayable CT concentrations between rumen, abomasum, and small intestine may be due to complex formation between CT and other dietary components. However, the large CT disappearance (61-85%) from feed to feces could also indicate that CT may have been structurally modified, degraded, or absorbed during digestion. Interestingly, there were no changes in the structural features of assayable CT in the digesta.

Free, esterified, and insoluble-bound phenolics were extracted from selected lentil cultivars. Total phenolics, flavonoids and proanthocyanidin contents were determined. Catechin, epicatechin and procyanidins B were predominant in all fractions of all tested samples as evaluated using HPLC-DAD-ESI-MSn. Methyl vanillate, procyanidin dimer A, and prodelphinidin dimer A were identified and quantified in lentils for the first time. Procyanidin dimer A was detected only in the insoluble-bound form, methyl vanillate was present in the esterified and insoluble-bound one and prodelphinidin dimer A was found in all forms. The presence of unrevealed compounds present only in the insoluble-bound form shows that ignoring the presence of phenolics linked to the cell wall of lentils may underestimate their potential health benefits. The antioxidant activities and the inhibition of cupric ion-induced human low-density lipoprotein peroxidation and peroxyl radical induced supercoiled plasmid DNA strand scission demonstrated that lentil seeds may be considered as a functional food.

Two new proanthocyanidin trimers have been isolated from Cistus incanus herb; gallocatechin-(4α→6)-gallocatechin-(4α→8)-gallocatechin (compound 1) and epigallocatechin-3-O-gallate-(4ß→8)-epigallocatechin-3-O-gallate-(4ß→8)-gallocatechin (compound 2). The structures were determined on the basis of 1D- and 2D-NMR (HSQC, HMBC) of their peracetylated derivatives, MALDI-TOF-MS and by acid-catalysed degradation with phloroglucinol. A more abundant proanthocyanidin oligomer was also isolated, purified and its chemical constitution studied by (13)C-NMR and phloroglucinol degradation. The mean molecular weight of the polymer was estimated to be about 7 to 8 flavan-3-ol-units with a ratio of procyanidin : prodelphinidin units at 1:5, some of which are derivatised by gallic acid. Water extract and higher oligomeric proanthocyanidin fractions of C. incanus significantly inhibited TPA-induced oedema when applied topically at doses of 0.5 and 1 mg/ear in mice. Furthermore, the extracts and the pure compounds inhibited COX-1 and COX-2 activities. In addition, compound 2 exhibited an IC50 of 4.5 μM against COX-2 indicating its high selectivity towards COX-2.

Studies with a diverse array of 22 purified condensed tannin (CT) samples from nine plant species demonstrated that procyanidin/prodelphinidin (PC/PD) and cis/trans-flavan-3-ol ratios can be appraised by 1H–13C HSQC NMR spectroscopy. The method was developed from samples containing 44–∼100% CT, PC/PD ratios ranging from 0/100 to 99/1, and cis/trans ratios ranging from 58/42 to 95/5 as determined by thiolysis with benzyl mercaptan. Integration of cross-peak contours of H/C-6′ signals from PC and of H/C-2′,6′ signals from PD yielded nuclei-adjusted estimates that were highly correlated with PC/PD ratios obtained by thiolysis (R2 = 0.99). cis/trans-Flavan-3-ol ratios, obtained by integration of the respective H/C-4 cross-peak contours, were also related to determinations made by thiolysis (R2 = 0.89). Overall, 1H–13C HSQC NMR spectroscopy appears to be a viable alternative to thiolysis for estimating PC/PD and cis/trans ratios of CT if precautions are taken to avoid integration of cross-peak contours of contaminants.

The phenolic composition of leaves from Phyllanthus acuminatus L., a plant commonly used in Costa Rica as traditional medicine, was studied using UPLC-ESI-MS on an enriched phenolic extract. A total of 20 phenolic compounds were identified, comprising eight flavonoids (two flavanones—pinocembrin isomers and six derivatives from apigenin, chrysin, quercetin, and kaempferol); seven ellagitannins, two flavan-3-ols (prodelphinidin B dimer and (epi)gallocatechin); and three phenolic acids (ellagic acid, trimethylellagic acid, and ferulic acid). All of these compounds are reported for the first time in P. acuminatus, while previously reported in the genus Phyllanthus. Antioxidant evaluation was performed for P. acuminatus phenolic extract obtaining DPPH results with a remarkably low IC50 value of 0.15 µg/mL. Also, cytotoxicity on gastric AGS and colon SW20 adenocarcinoma cell lines was evaluated, and highly promising results were obtained, with IC50 values of 11.3 µg/mL and 10.5 µg/mL, respectively. Furthermore, selectivity index values obtained when comparing cytotoxicity on normal Vero cells was SI > 20 for both cancer cell lines, indicating a particularly high selectivity. Additionally, Justicidin B, a metabolite extensively studied for its antitumoral activity, was isolated from a non-polar extract of P. acuminatus, and comparatively evaluated for both bioactivities. The DPPH value obtained for Justicidin B was moderate (IC50 = 14.28 µg/mL), while cytotoxicity values for both AGS (IC50 = 19.5 µg/mL) and SW620 (IC50 = 24.8 µg/mL) cell lines, as well as selectivity when compared with normal Vero cells (SI = 5.4 and 4.2 respectively), was good, but lower than P. acuminatus extract. These preliminary results suggest that P. acuminatus enriched phenolic extract containing flavonoids, ellagitannins, flavan-3-ols, and phenolic acids, reported for the first time in this plant, could be of interest for further cancer cytotoxicity studies to elucidate structure–bioactivity relationships, and the molecular mechanisms and pathways. Consejo Nacional de Rectores/[Ref 115B0653]/CONARE/Costa Rica Universidad de Costa Rica/[]/UCR/Costa Rica Instituto Tecnológico de Costa Rica/[]/TEC/Costa Rica UCR::Vicerrectoría de Docencia::Ciencias Básicas::Facultad de Ciencias::Escuela de Química UCR::Vicerrectoría de Docencia::Salud::Facultad de Medicina::Escuela de Medicina UCR::Vicerrectoría de Docencia::Ciencias Básicas::Facultad de Ciencias::Escuela de Biología

The structural chemistry of proanthocyanidin molecules has been investigated in temperate zone plants, but few studies have been done with plants of the Amazonian lowland tropical wet forests where herbivore pressure is more extensive and diverse. Using MALDI-TOF mass spectrometry, we report unique properties of the proanthocyanidin structural chemistry in two neotropical Cecropia species, C. polystachya, a myrmecophyte with mutualistic ants, and C. sciadophylla, a non-myrmecophyte lacking mutualistic ants. Our preliminary data suggests the presence of reportedly uncommon propelargonidin subunits in a majority of proanthocyanidin oligomers. The presence of 3-O-gallate proanthocyanidin monomers was also detected in the mass spectra of both species. Unlike other studies that have examined species growing at higher latitudes, oligomers composed of procyanidin, propelargonidin, and their 3-O-gallates were present in both Cecropia species while the presence of oligomers containing prodelphinidin units were absent or at lower levels. These distinctive features may suggest that proanthocyanidins in some tropical plant species may be an untapped source of proanthocyanidin structural complexity that warrants further investigation. Several differences between spectra of the two Cecropia species could also point to the presence of anti-herbivore defense tradeoffs between chemical defense quality and biotic defense between the two species.

We applied a taxonomic approach to select the Eugenia dysenterica (Myrtaceae) leaf extract, known in Brazil as "cagaita," and evaluated its gastroprotective effect. The ability of the extract or carbenoxolone to protect the gastric mucosa from ethanol/HCl-induced lesions was evaluated in mice. The contributions of nitric oxide (NO), endogenous sulfhydryl (SH) groups and alterations in HCl production to the extract's gastroprotective effect were investigated. We also determined the antioxidant activity of the extract and the possible contribution of tannins to the cytoprotective effect. The extract and carbenoxolone protected the gastric mucosa from ethanol/HCl-induced ulcers, and the former also decreased HCl production. The blockage of SH groups but not the inhibition of NO synthesis abolished the gastroprotective action of the extract. Tannins are present in the extract, which was analyzed by matrix assisted laser desorption/ionization (MALDI); the tannins identified by fragmentation pattern (MS/MS) were condensed type-B, coupled up to eleven flavan-3-ol units and were predominantly procyanidin and prodelphinidin units. Partial removal of tannins from the extract abolished the cytoprotective actions of the extract. The extract exhibits free-radical-scavenging activity in vitro, and the extract/FeCl3 sequence stained gastric surface epithelial cells dark-gray. Therefore, E. dysenterica leaf extract has gastroprotective effects that appear to be linked to the inhibition of HCl production, the antioxidant activity and the endogenous SH-containing compounds. These pleiotropic actions appear to be dependent on the condensed tannins contained in the extract, which bind to mucins in the gastric mucosa forming a protective coating against damaging agents. Our study highlights the biopharmaceutical potential of E. dysenterica.

Total synthesis of prodelphinidin B1, B2, and B4 has been accomplished. The key step is Lewis acid-mediated equimolar condensations between an epigallocatechin and/or a gallocatechin nucleophile and an epigallocatechin and/or a gallocatechin electrophile. The antitumor effects of synthetic prodelphinidin B1-B4 against human PC-3 prostate cancer cell lines have been investigated. These compounds showed significant antitumor effects. Their activity seemed to be little bit stronger than EGCG and prodelphinidin B3, known antitumor agent., Article, TETRAHEDRON LETTERS. 54(52):7188-7192 (2013)

Stryphnodendron adstringenshas a high tannin content and is used as an antiseptic and antimicrobial and in the treatment of leucorrhea, gonorrhea, wound healing, and gastritis. The present study evaluated the toxic effects of the heptamer prodelphinidin (F2) from the stem bark ofS. adstringensin rodents. In the acute toxicity test, the mice that received oral doses exhibited reversible effects, with an LD50of 3.015 mg·kg−1. In the chronic toxicity test at 90 days, Wistar rats were treated with different doses of F2 (10, 100, and 200 mg·kg−1). In the biochemical, hematological, and histopathological examinations and open-field test, the different dose groups did not exhibit significant differences compared with controls. The present results indicate that F2 from the stem bark ofS. adstringenscaused no toxicity with acute and chronic oral treatment in rodents at the doses administered.

Plants containing condensed tannins (CT) may have potential to control gastrointestinal nematodes (GIN) of cattle. The aim was to investigate the anthelmintic activities of four flavan-3-ols, two galloyl derivatives and 14 purified CT fractions, and to define which structural features of CT determine the anti-parasitic effects against the main cattle nematodes. We used in vitro tests targeting L1 larvae (feeding inhibition assay) and adults (motility assay) of Ostertagia ostertagi and Cooperia oncophora. In the larval feeding inhibition assay, O. ostertagi L1 were significantly more susceptible to all CT fractions than C. oncophora L1. The mean degree of polymerization of CT (i.e. average size) was the most important structural parameter: large CT reduced larval feeding more than small CT. The flavan-3-ols of prodelphinidin (PD)-type tannins had a stronger negative influence on parasite activity than the stereochemistry, i.e. cis- vs trans-configurations, or the presence of a gallate group. In contrast, for C. oncophora high reductions in the motility of larvae and adult worms were strongly related with a higher percentage of PDs within the CT fractions while there was no effect of size. Overall, the size and the percentage of PDs within CT seemed to be the most important parameters that influence anti-parasitic activity Plants containing condensed tannins (CT) may have potential to control gastrointestinal nematodes (GIN) of cattle. The aim was to investigate the anthelmintic activities of four flavan-3-ols, two galloyl derivatives and 14 purified CT fractions, and to define which structural features of CT determine the anti-parasitic effects against the main cattle nematodes. We used in vitro tests targeting L1 larvae (feeding inhibition assay) and adults (motility assay) of Ostertagia ostertagi and Cooperia oncophora. In the larval feeding inhibition assay, O. ostertagi L1 were significantly more susceptible to all CT fractions than C. oncophora L1. The mean degree of polymerization of CT (i.e. average size) was the most important structural parameter: large CT reduced larval feeding more than small CT. The flavan-3-ols of prodelphinidin (PD)-type tannins had a stronger negative influence on parasite activity than the stereochemistry, i.e. cis- vs trans-configurations, or the presence of a gallate group. In contrast, for C. oncophora high reductions in the motility of larvae and adult worms were strongly related with a higher percentage of PDs within the CT fractions while there was no effect of size. Overall, the size and the percentage of PDs within CT seemed to be the most important parameters that influence anti-parasitic activity.

In the present study, the relative contribution of individual/classes of polyphenols in barley, to its antioxidant properties, was evaluated. Flash chromatography was used to fractionate the total polyphenol extract of Irish barley cultivar 'Irina', and fractions with highest antioxidant properties were identified using total phenolic content and three in vitro antioxidant assays: DPPH, FRAP, and ORAC. Flavanols (catechin, procyanidin B, prodelphinidin B, procyanidin C) and a novel substituted flavanol (catechin dihexoside, C27H33O16(-), m/z 613.17), were identified as constituents of the fraction with highest antioxidant capacity. Upon identification of phenolics in the other active fractions, the order of most potent contributors to observed antioxidant capacity of barley extract were, flavanols>flavonols (quercetin)>hydroxycinnamic acids (ferulic, caffeic, coumaric acids). The most abundant polyphenol in the overall extract was ferulic acid (277.7μg/gdw barley), followed by procyanidin B (73.7μg/gdw barley).

Phenolics in food and agricultural processing by-products exist in the soluble and insoluble-bound forms. The ability of selected enzymes in improving the extraction of insoluble-bound phenolics from the starting material (experiment I) or the residues containing insoluble-bound phenolics (experiment II) were evaluated. Pronase and Viscozyme improved the extraction of insoluble-bound phenolics as evaluated by total phenolic content, antioxidant potential as determined by ABTS and DPPH assays, and hydroxyl radical scavenging capacity, reducing power as well as evaluation of inhibition of alpha-glucosidase and lipase activities. Viscozyme released higher amounts of gallic acid, catechin, and prodelphinidin dimer A compared to Pronase treatment. Furthermore, p-coumaric and caffeic acids, as well as procyanidin dimer B, were extracted with Viscozyme but not with Pronase treatment. Solubility plays an important role in the bioavailability of phenolic compounds, hence this study may assist in better exploitation of phenolics from winemaking by-products as functional food ingredients and/or supplements.

Parasitic gastrointestinal nematodes (GIN) of livestock are increasingly developing resistance to synthetic nematocidal drugs. Moreover, the use of nematocides can induce ecotoxicity by affecting free-living nematodes. Condensed tannins (CT) are a structurally diverse group of bioactive plant compounds possessing anthelmintic activity against GIN. We investigated the relationship between the chemical structure of contrasting, purified CT and nematocidal effects using Caenorhabditis elegans. We also explored whether the nematocidal activity of CT could synergize with trans-cinnamaldehyde (CIN). A non-significant correlation was evident between the ability of CT fractions to inhibit C. elegans motility and the molar proportion of prodelphinidin subunits in purified CT samples. Synergistic inhibition of motility was achieved by combinations of CT and CIN. Galloylation of procyanidins was also a key factor for synergy. To increase the nematocidal effect of CT, plant sources containing CT with specific structural features could be selected and combined with compounds acting in synergy.