tannins and procyanidin

Type I IFN signaling is a central pathway that provides critical innate protection from viral and bacterial infection and can have regulatory outcomes in inflammatory settings. We determined previously that OPCs contained in the dietary supplement APP enhanced responses to type I IFN in vitro. Here, we confirm that OPCs from two different sources significantly increased pSTAT1, whereas a monomeric form of procyanidin did not. We hypothesized that similar responses could be induced in vivo following ingestion of APP. Ingestion of APP before injection of polyI:C enhanced in vivo responses to type I IFNs in mice. When human subjects ingested APP, enhanced responses to type I IFN and enhanced pSTAT1 ex vivo were detected, whereas ingestion of RES, a monomeric polyphenol, induced minimal such changes. Polyphenols are best known for induction of anti-inflammatory and antioxidant responses; however, our findings suggest a unique, nonantioxidant aspect of OPCs that is broadly applicable to many disease settings. The capacity of oral OPCs to enhance type I IFN signaling in vivo can augment innate protection and may, in part, contribute to the noted anti-inflammatory outcome of ingestion of OPCs from many sources.

Topics: Administration, Oral; Animals; Biflavonoids; Catechin; Chlorogenic Acid; Double-Blind Method; Female; Flavonoids; Humans; Immunity, Innate; Interferon Type I; Male; Mice; Mice, Inbred BALB C; Proanthocyanidins; Tannins

Plant polyphenols have beneficial antioxidant effects on human health; practices aimed at preserving their content in foods and/or reusing food by-products are encouraged. The impact of the traditional practice of the water curing procedure of chestnuts, which prevents insect/mould damage during storage, was studied to assess the release of polyphenols from the fruit. Metabolites extracted from pericarp and integument tissues or released in the medium from the water curing process were analyzed by matrix-assisted laser desorption ionization-time of flight-mass spectrometry (MALDI-TOF-MS) and electrospray-quadrupole-time of flight-mass spectrometry (ESI-qTOF-MS). This identified: (i) condensed and hydrolyzable tannins made of (epi)catechin (procyanidins) and acid ellagic units in pericarp tissues; (ii) polyphenols made of gallocatechin and catechin units condensed with gallate (prodelphinidins) in integument counterparts; (iii) metabolites resembling those reported above in the wastewater from the chestnut curing process. Comparative experiments were also performed on aqueous media recovered from fruits treated with processes involving: (i) tap water; (ii) tap water containing an antifungal

Topics: Aesculus; Antioxidants; Biflavonoids; Catechin; Fruit; Humans; Nuts; Plant Extracts; Polyphenols; Proanthocyanidins; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Tannins; Water

Topics: Antioxidants; Biflavonoids; Biological Availability; Catechin; Cicer; Correlation of Data; Flavonoids; Flavonols; Inhibitory Concentration 50; Iron Chelating Agents; Lens Plant; Mass Spectrometry; Metabolomics; Phenols; Polyphenols; Proanthocyanidins; Seeds; Tannins; Vicia faba

In this study, we optimized the HCl-butanol-acetone-iron (HBAI) assay for the analysis of B-linked procyanidin (PC) and prodelphinidin (PD) condensed tannins (CTs) by direct analysis of whole tissue and sequential analysis of acetone-water extracts and insoluble residues prepared from forage, woody plant, food, and food byproduct samples. Yields of anthocyanidins (cyanidin and delphinidin) were optimized by heating ≤0.25 mg mL

Topics: 1-Butanol; Acetone; Biflavonoids; Catechin; Chemistry Techniques, Analytical; Food Analysis; Hydrochloric Acid; Iron; Plant Extracts; Proanthocyanidins; Tannins

The major areas of the world where viticulture is practiced enjoy temperate or cool temperature climates. When wine grapes are grown in tropical regions, edaphoclimatic factors result in distinct grape quality attributes, and production techniques also require significant adjustment. The objective of this study was to characterize the chemical compositions, in particular of phenolic compounds, of Syrah grapes grown in two location in northeast Brazil - these are also at widely different altitudes. A range of methods of phenolic extraction were used, along with classical chemical analyses including for organic acids, sugars, monomeric anthocyanins, flavonols, stilbene, condensed tannins and some of the monomeric and small oligomeric procyanidins. The regions and their diverse environments had a larger influence than harvest year. The grapes at higher altitude (Bahia, 1.100 m asl (metres above sea level) were characterized by higher levels of malic acid, anthocyanins and condensed tannins in the skins. The low-altitude grapes (Pernambuco, 350 m asl (metres above sea level) had higher levels of glucose, fructose, 3-O-acetylglucoside anthocyanins and condensed tannins in the seeds. Fruit composition was highly influenced by the region. In the low-altitude region, the grapes were characterized by higher tartaric and citric acid in the must, also of flavonols in skins and of tannins in the seeds. Meanwhile, the fruit from the high altitude, contained higher levels of malic and succinic acid in the must, and of anthocyanins and condensed tannins in the skins.

Topics: Altitude; Anthocyanins; Antioxidants; Benzaldehydes; Biflavonoids; Brazil; Catechin; Chromatography, High Pressure Liquid; Color; Farms; Flavonols; Fructose; Fruit; Glucose; Molecular Weight; Phenols; Principal Component Analysis; Proanthocyanidins; Seeds; Stilbenes; Tannins; Tropical Climate; Vitis; Wine

In this study, the content, structure, antityrosinase activity, and mechanism of longan bark condensed tannins were evaluated. The findings obtained from mass spectrometry demonstrated that longan bark condensed tannins were mixtures of procyanidins, propelargonidins, prodelphinidins, and their acyl derivatives (galloyl and p-hydroxybenzoate). The enzyme analysis indicated that these mixtures were efficient, reversible, and mixed (competitive is dominant) inhibitor of tyrosinase. What's more, the mixtures showed good inhibitions on proliferation, intracellular enzyme activity and melanogenesis of mouse melanoma cells (B

Topics: Animals; Anthocyanins; Biflavonoids; Catechin; Cell Proliferation; Enzyme Inhibitors; Hydrogen Bonding; Hydrophobic and Hydrophilic Interactions; Mass Spectrometry; Melanins; Melanoma, Experimental; Mice; Models, Molecular; Molecular Docking Simulation; Monophenol Monooxygenase; Oxidoreductases; Parabens; Plant Bark; Proanthocyanidins; Sapindaceae; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Static Electricity; Structure-Activity Relationship; Tannins

Protein-tannin interactions on a molecular level were investigated by using a model system containing peptides of α-lactalbumin and berry tannins (procyanidins). Oxidation of isolated tryptic peptide LDQWLCEK (m/z 1034) with procyanidin B2 or procyanidin fraction (PF) isolated from aronia juice was monitored by LC-ESI-MS. Procyanidin B2 and PF showed radical scavenging activities toward oxidation of the peptide with the peptide also preventing procyanidin B2 from degradation. Oxidation enhanced the cleavage of peptide between tryptophan and glutamine. Interaction products arising from WLCEK or WLCE residue and degradation product of procyanidin B2 were also identified using both size exclusion chromatography and LC-MS. Tryptophan and lysine were the amino acids most prone to interact with procyanidin B2. The study shows that protein-tannin interaction takes place during oxidation leading to both degradation of the parent compounds and formation of interaction products. This may in turn affect the quality of protein and tannin containing food.

Topics: Animals; Biflavonoids; Catechin; Cattle; Chromatography, High Pressure Liquid; Dietary Proteins; Fruit and Vegetable Juices; Lactalbumin; Oxidation-Reduction; Photinia; Proanthocyanidins; Spectrometry, Mass, Electrospray Ionization; Tannins

A diverse panel of condensed tannins was used to resolve the confounding effects of size and subunit composition seen previously in tannin-protein interactions. Turbidimetry revealed that size in terms of mean degree of polymerisation (mDP) or average molecular weight (amw) was the most important tannin parameter. The smallest tannin with the relatively largest effect on protein aggregation had an mDP of ~7. The average size was significantly correlated with aggregation of bovine serum albumin, BSA (mDP: r = -0.916; amw: r = -0.925; p<0.01; df = 27), and gelatin (mDP: r = -0.961; amw: r = -0.981; p<0.01; df = 12). The procyanidin/prodelphinidin and cis-/trans-flavan-3-ol ratios gave no significant correlations. Tryptophan fluorescence quenching indicated that procyanidins and cis-flavan-3-ol units contributed most to the tannin interactions on the BSA surface and in the hydrophobic binding pocket (r = 0.677; p<0.05; df = 9 and r = 0.887; p<0.01; df = 9, respectively). Circular dichroism revealed that higher proportions of prodelphinidins decreased the apparent α-helix content (r = -0.941; p<0.01; df = 5) and increased the apparent β-sheet content (r = 0.916; p<0.05; df = 5) of BSA.

Topics: Anthocyanins; Biflavonoids; Catechin; Flavonoids; Gelatin; Hydrophobic and Hydrophilic Interactions; Kinetics; Molecular Structure; Plant Extracts; Plants, Medicinal; Proanthocyanidins; Protein Aggregates; Protein Binding; Serum Albumin, Bovine; Solutions; Tannins; Tryptophan

Medicinal plant materials are not usually analysed for condensed tannins (CT). Thirty commercially available European medicinal plants and herbal products were screened for CT and fourteen CT samples were analysed in detail. This is also the first comprehensive CT analysis of pine buds, walnut leaves, heather flowers and great water dock roots. Acetone/water extracts contained between 3.2 and 25.9 g CT/100g of extract, had CT with mean degrees of polymerisation of 2.9 to 13.3, procyanidin/prodelphinidin ratios of 1.6/98.4 to 100/0 and cis/trans flavan-3-ol ratios of 17.7/82.3 to 97.3/2.7. The majority of samples contained procyanidins, four contained A-type linkages (blackthorn flowers, heather flowers, bilberry leaves and cowberry leaves) and one sample also had galloylated procyanidins (great water dock roots).

Topics: Biflavonoids; Catechin; Europe; Flavonoids; Flowers; Plant Extracts; Plant Leaves; Plant Roots; Plants, Medicinal; Proanthocyanidins; Tannins

In this work, the effect of water availability on astringency of seed and skin extracts of Vitis vinifera cv. Syrah berries under the typical semiarid conditions of Greece was investigated. Moreover, astringency was assessed in relation to proanthocyanidin composition. For this purpose, three irrigation treatments were applied starting at berry set through harvest of 2011 and 2012: full irrigation (FI) at 100% of crop evapotranspiration, deficit irrigation (DI) at 50% and non-irrigated (NI). FI skin and seed extracts were perceived significantly more astringent than NI. Total phenol, total tannin, (+)-catechin, (-)-epicatechin and procyanidin C1 concentrations were positively correlated with astringency. Positive correlations were also obtained among astringency and average degree of polymerization and proportion of the extension units of shorter tannins while astringency of larger tannins was correlated with the proportion of terminal units. On the contrary, total anthocyanin and epigallocatechin contents were negatively correlated with astringency.

Topics: Agricultural Irrigation; Anthocyanins; Biflavonoids; Catechin; Desert Climate; Fruit; Greece; Humans; Phenols; Plant Extracts; Proanthocyanidins; Seeds; Tannins; Taste; Vitis; Water

Depolymerization of procyanidin polymers into oligomers enhances their bioavailability and bioactivity because oligomers are bioavailable. Hydrogenolysis was applied in this study to depolymerize hi-tannin sorghum bran procyanidin polymers into oligomers. The yield and composition of oligomers under different hydrogenolysis conditions was investigated. Results showed that raising temperature from 50 to 100 °C significantly increased total yield of oligomers. Higher temperatures (150 and 200 °C) produced monomers with lower yield. The highest yield of oligomers (38.8%) was obtained using 1 MPa hydrogen whereas 3 MPa hydrogen in reaction vessel decreased yield. Total yield of oligomers reached the highest at 1-3 h and then decreased with prolonged reaction time. Yield increased with palladium-on-carbon (Pd/C, a catalyst) amount from 0.5 to 3 mg and plateaued with Pd/C amount from 3 to 10 mg. The maximum yield of produced oligomers was achieved under 100 °C, 1 MPa hydrogen pressure, 1-3 h, and 3-10 mg Pd/C.

Topics: Biflavonoids; Biopolymers; Catechin; Chromatography, High Pressure Liquid; Dietary Fiber; Hot Temperature; Polymerization; Proanthocyanidins; Sorghum; Tannins

Condensed tannins extracted from European softwood bark are recognized as alternatives to synthetic phenolics. The extraction is generally performed in hot water, leading to simultaneous extraction of other bark constituents such as carbohydrates, phenolic monomers and salts. Characterization of the extract's composition and identification of the extracted tannins' molecular structure are needed to better identify potential applications. Bark from Silver fir (Abies alba [Mill.]), European larch (Larix decidua [Mill.]), Norway spruce (Picea abies [Karst.]), Douglas fir (Pseudotsuga menziesii [Mirb.]) and Scots pine (Pinus sylvestris [L.]) were extracted in water at 60°C. The amounts of phenolic monomers, condensed tannins, carbohydrates, and inorganic compounds in the extract were determined. The molecular structures of condensed tannins and carbohydrates were also investigated (HPLC-UV combined with thiolysis, MALDI-TOF mass spectrometry, anion exchange chromatography). Distinct extract compositions and tannin structures were found in each of the analysed species. Procyanidins were the most ubiquitous tannins. The presence of phenolic glucosides in the tannin oligomers was suggested. Polysaccharides such as arabinans, arabinogalactans and glucans represented an important fraction of all extracts. Compared to traditionally used species (Mimosa and Quebracho) higher viscosities as well as faster chemical reactivities are expected in the analysed species. The most promising species for a bark tannin extraction was found to be larch, while the least encouraging results were detected in pine. A better knowledge of the interaction between the various extracted compounds is deemed an important matter for investigation in the context of industrial applications of such extracts.

Topics: Biflavonoids; Catechin; Chromatography, High Pressure Liquid; Flavonoids; Glucosides; Hot Temperature; Molecular Structure; Norway; Picea; Pinus; Plant Bark; Plant Extracts; Proanthocyanidins; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Tannins; Water

Using α-amylase inhibition as a separation guide, polyphenolic compounds from almond ( Prunus dulcis ) seed skin were purified using ultrafiltration and Sephadex LH-20 and ODS columns. The purified fraction specifically and strongly inhibited α-amylase; the IC50 value was 2.2 μg/mL for pig pancreatic α-amylase. The fraction contained about 62% of the total polyphenols, 33.8% flavanol-type tannins and 30% procyanidins. Oral administration of the polyphenol fraction to rats fed corn starch significantly suppressed an increase in blood glucose levels and area under the curve (AUC), in a dose-dependent manner. High-resolution MALDI-TOF mass spectra showed that the structure of this sample is a series of polyflavan-3-ol polymers composed of catechin/epicatechin units and gallocatechin/epigallocatechin units up to 11-mer with several interflavanoid ether linkages. The results suggest almond seed skin contains highly polymerized polyphenols with strong α-amylase inhibitory activity, which retard absorption of carbohydrate.

Topics: Absorption; Amino Acids; Animals; Area Under Curve; Biflavonoids; Blood Glucose; Carbohydrates; Catechin; Chromium; Dextrans; Enzyme Inhibitors; Inhibitory Concentration 50; Male; Nicotinic Acids; Nuts; Pancreatic alpha-Amylases; Plant Extracts; Polyphenols; Proanthocyanidins; Prunus; Rats; Seeds; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Tannins

Antioxidant capacities and polyphenolic contents of two mango cultivars from northern Chile, one of them endemic of an oasis in the Atacama Desert, were compared for the first time. Twenty one phenolic compounds were detected in peel and pulp of mango fruits varieties Pica and Tommy Atkins by HPLC-PDA-MS and tentatively characterized. Eighteen compounds were present in Pica pulp (ppu), 13 in Pica peel (ppe) 11 in Tommy Atkins pulp (tpu) and 12 in Tommy Atkins peel (tpe). Three procyanidin dimers (peaks 6, 9 and 10), seven acid derivatives (peaks 1-4, 11, 20 and 21) and four xanthones were identified, mainly mangiferin (peak 12) and mangiferin gallate, (peak 7), which were present in both peel and pulp of the two studied species from northern Chile. Homomangiferin (peak 13) was also present in both fruit pulps and dimethylmangiferin (peak 14) was present only in Tommy pulp. Pica fruits showed better antioxidant capacities and higher polyphenolic content (73.76/32.23 µg/mL in the DPPH assay and 32.49/72.01 mg GAE/100 g fresh material in the TPC assay, for edible pulp and peel, respectively) than Tommy Atkins fruits (127.22/46.39 µg/mL in the DPPH assay and 25.03/72.01 mg GAE/100 g fresh material in the TPC assay for pulp and peel, respectively). The peel of Pica mangoes showed also the highest content of phenolics (66.02 mg/100 g FW) measured by HPLC-PDA. The HPLC generated fingerprint can be used to authenticate Pica mango fruits and Pica mango food products.

Topics: Antioxidants; Biflavonoids; Catechin; Chile; Chromatography, High Pressure Liquid; Flavonoids; Fruit; Mangifera; Mass Spectrometry; Phenols; Plant Extracts; Polyphenols; Proanthocyanidins; Tannins; Xanthones

While the definition of tannins has been historically associated with its propensity to bind proteins in a nonspecific way, it is now admitted that specific interaction also occurs. The case of the astringency perception is a good example to illustrate this phenomenon: astringency is commonly described as a tactile sensation induced by the precipitation of a complex composed of proline-rich proteins present in the human saliva and tannins present in beverages such as tea or red wines. In the present work, the interactions between a human saliva protein segment and three different procyanidins (B1, B3, and C2) were investigated at the atomic level by NMR and molecular dynamics. The data provided evidence for (i) an increase in affinity compared to shortest human saliva peptides, which is accounted for by protein "wraping around" the tannin, (ii) a specificity in the interaction below tannin critical micelle concentration (CMC) of ca. 10 mM, with an affinity scale such that C2 > B1 > B3, and (iii) a nonspecific binding above tannin CMC that conducts irremediably to the precipitation of the tannins/protein complex. Such physicochemical findings describe in accurate terms saliva protein-tannin interactions and provide support for a more subtle description by oenologists of wine astringency perception in the mouth.

Topics: Biflavonoids; Catechin; Humans; Micelles; Molecular Dynamics Simulation; Nuclear Magnetic Resonance, Biomolecular; Proanthocyanidins; Protein Binding; Protein Structure, Tertiary; Salivary Proline-Rich Proteins; Tannins

In organoleptic science, the association of tannins to saliva proteins leads to the poorly understood phenomenon of astringency. To decipher this interaction at molecular and colloidal levels, the binding of 4 procyanidin dimers (B1-4) and 1 trimer (C2) to a human saliva proline-rich peptide, IB7(14), was studied. Interactions have been characterized by measuring dissociation constants, sizes of complexes, number, and nature of binding sites using NMR (chemical shift variations, diffusion-ordered spectroscopy, and saturation transfer diffusion). The binding sites were identified using molecular mechanics, and the hydrophilic/hydrophobic nature of the interactions was resolved by calculating the molecular lipophilicity potential within the complexes. The following comprehensive scheme can be proposed: 1) below the tannin critical micelle concentration (CMC), interaction is specific, and the procyanidin anchorage always occurs on the same three IB7(14) sites. The tannin 3-dimensional structure plays a key role in the binding force and in the tannin's ability to act as a bidentate ligand: tannins adopting an extended conformation exhibit higher affinity toward protein and initiate the formation of a network. 2) Above the CMC, after the first specific hydrophilic interaction has taken place, a random hydrophobic stacking occurs between tannins and proteins. The whole process is discussed in the general frame of wine tannins eliciting astringency.

Topics: Antioxidants; Astringents; Biflavonoids; Catechin; Colloids; Dimerization; Humans; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Dynamics Simulation; Molecular Structure; Proanthocyanidins; Protein Binding; Salivary Proteins and Peptides; Tannins; Wine

Phenolic compounds are present at very high concentrations in the bark of Acacia mangium. These compounds are known to have strong antioxidant activity and thus different beneficial effects on human health. Phenolic compounds in bark of A. mangium were extracted and their antioxidant activities were investigated using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical-scavenging and ferric-reducing antioxidant power (FRAP) assays. A central composite design has been employed to optimize the experimental conditions for a high total phenolic content and antioxidant activity. The desirability function approach has been employed to simultaneously optimize the three responses: total phenols, antiradical activity and FRAP. An extraction time of 90 min, liquid-solid ratio of 5, and temperature of 50 degrees C was predicted for the optimum experimental conditions using the desirability function. A significant linear relationship between antioxidant potency, antiradical activity and the content of phenolic compounds of bark extracts was observed. The structures of condensed tannins isolated from A. mangium were characterized by MALDI-TOF MS analyses. Condensed tannin oligomers from A. mangium were shown to be heterogeneous mixtures consisting of procyanidin and prodelphinidin structural units with polymerization degrees up to 9.

Topics: Acacia; Anthocyanins; Antioxidants; Biflavonoids; Catechin; Humans; Phenols; Plant Bark; Plant Extracts; Proanthocyanidins; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Tannins

The three-dimensional structures of 5 procyanidin dimers have been determined in a hydro-alcoholic medium and in water using 2D NMR and molecular mechanics. They are made from monomers of catechin (CAT) and epicatechin (EPI)-B1: EPI-CAT, B2: EPI-EPI, B3: CAT-CAT, B4: CAT-EPI and B2g: EPI-EPI-3-O-gallate. These tannins exist in two conformations that are in slow exchange in the NMR timescale (s), one is compact and the other extended. The compact form is found to dominate (76-98%) when the dimer is made of at least one CAT monomer (B1, B3, B4). Both forms are found in even proportions only in the case of procyanidin B2. The latter tannin can be converted into a dominant compact form when the lower EPI unit is galloylated. The finding of a predominant compact form for procyanidin dimers is discussed in relation with tannin-saliva protein interactions that are of importance for the wine-tasting/making processes.

Topics: Alcohols; Biflavonoids; Catechin; Dimerization; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Conformation; Proanthocyanidins; Tannins; Water

For two successive years, cell walls were isolated from the internal part of skin cells of Vitis vinifera L. cv. Cabernet Sauvignon grape berries grown in a vineyard. Procyanidin localization and composition were determined over the course of development. Tannins were mainly localized in the inner cell fraction, due to their biosynthesis and storage. Cell wall tannins always exhibited a higher mean degree of polymerization as compared to the internal cell fraction, which had a constant mDP. The mDP of cell wall tannins also tended to increase at the end of maturation. Our results suggest tannin polymerization near the cell wall but an aggregation in the vacuole during growth. The tannin composition was typical of skins, and small differences were noted between the two cell parts. Surprisingly, epigallocatechin-3-gallate was also detected, although in a very small amount. Epicatechin was present in significant proportions in both fractions, especially as an extension subunit, while epigallocatechin was likewise abundant, also as a terminal subunit. Last, procyanidin composition and organization seemed to be characteristic of the Cabernet Sauvignon variety.

Topics: Biflavonoids; Catechin; Cell Wall; Chromatography, High Pressure Liquid; Flavonoids; Fruit; Phenols; Polymers; Polyphenols; Proanthocyanidins; Tannins; Vitis

Although it is already known that Tamarind (Tamarindus indica L.) seeds contain phenolic substances, the individual components of the seeds have not been fully identified and quantitated, and in the case of Tamarind pericarp not reported. Therefore, major polyphenolic compounds were extracted using organic solvents and the metabolites were isolated by semi-preparative high performance liquid chromatography. Their structures were elucidated by liquid chromatography-electrospray-ionisation-mass spectrometry (LC-ESI-MS), nano-electrospray-ionisation mass spectrometry (ESI-MS), and where possible by gas chromatography-mass spectrometry (GC-MS) and 1H and 13C NMR. Quantitative analysis of polyphenolic compounds in Tamarind seeds and pericarp was conducted by analytical high performance liquid chromatography (HPLC), calculated against standard curves of authentic compounds. The yields of total phenolic compounds after Soxhlet extraction with methanol were 6.54 and 2.82 g/kg (dry weight) in the seeds and pericarp respectively. The profile (%) of polyphenolics in Tamarind pericarp was dominated by proanthcyanidins (73.4) in various forms (+)-catechin (2.0), procyanidin B2 (8.2), (-)-epicatechin (9.4), procyanidin trimer (11.3), procyanidin tetramer (22.2), procyanidin pentamer (11.6), procyanidin hexamer (12.8) along with taxifolin (7.4), apigenin (2.0), eriodictyol (6.9), luteolin (5.0) and naringenin (1.4) of total phenols, respectively. The content of Tamarind seeds comprised only procyanidins, represented (%) mainly by oligomeric procyanidin tetramer (30.2), procyanidin hexamer (23.8), procyanidin trimer (18.1), procyanidin pentamer (17.6) with lower amounts of procyanidin B2 (5.5) and (-)-epicatechin (4.8). Extraction of Tamarind pericarp and seeds using acetone:methanol:acetic acid gave only procyanidin oligomers, but in much higher yield and variety. The antioxidant capacities of the Soxhlet methanolic extracts were determined, and indicates that Tamarind may be an important source of cancer chemopreventive natural products in tropical regions.

Topics: Antioxidants; Biflavonoids; Catechin; Chromatography, High Pressure Liquid; Deoxyguanosine; Fruit; Gas Chromatography-Mass Spectrometry; Magnetic Resonance Spectroscopy; Phenols; Plant Extracts; Proanthocyanidins; Seeds; Spectrometry, Mass, Electrospray Ionization; Tamarindus; Tannins; Xanthine Oxidase

A Chardonnay white wine enriched in polyphenols was obtained by modification of winemaking and characterized by its enrichment in total polyphenolic content (1346 mg/L as compared to 316 mg/L for traditional Chardonnay) and in various individual polyphenols (catechin, epicatechin, procyanidins dimers B1-B4, gallic acid, cafeic acid, and caftaric acid), as determined from HPLC coupled to a diode array detector. The polyphenols-enriched white wine (W) or its ethanol-free derivative (EFW) was then administered by gavage (10 mL/kg, twice a day) for 6 weeks to rats that have been rendered diabetic by a single iv injection of streptozotocin (55 mg/kg). Treatments had no effect on the symptoms associated with hyperglycemia. However, while a reduction in plasma antioxidant capacity was associated with the diabetic state, administration of W or EFW restored plasma antioxidant capacities to a level not significantly different from that of nondiabetic control animals. In addition, the effect of both treatments was manifested by the enlargement of mesenteric arteries, as determined by quantitative histomorphometry. In summary, our study indicates that white wine, when enriched in polyphenols, is able to induce ethanol-independent in vivo effects in a model of insulin-deficient diabetes characterized by a major oxidative stress.

Topics: Animals; Anthocyanins; Antioxidants; Biflavonoids; Caffeic Acids; Catechin; Chromatography, High Pressure Liquid; Diabetes Mellitus, Experimental; Flavonoids; Gallic Acid; Male; Mesenteric Arteries; Oxidative Stress; Phenols; Polymers; Proanthocyanidins; Rats; Rats, Wistar; Tannins; Wine

MALDI-TOF mass spectrometry and 13C NMR spectroscopy were applied to unveil typical characteristics of condensed tannins of leaves and needles from willow (Salix alba), spruce (Picea abies) and beech (Fagus sylvatica) of three tree species that are ubiquitous in German forests and landscapes. For further evaluation, lime (Tilia cordata) was included. The 13C NMR spectroscopy confirmed the purity of the condensed tannin fractions and the efficiency of the procedure used for their extraction. While signals representative for procyanidin units are observable in all liquid-state 13C NMR spectra, resonance lines of prodelphinidin were only detected in those obtained from the condensed tannins of spruce needles and beech leaves. Typical signals in the chemical shift region between 70 and 90 ppm demonstrated the presence of stereoisomers (catechin/epicatechin; gallocatechin/ epigallocatechin). The MALDI-TOF mass spectra of the condensed tannins show signals of polymers of up to undecamers. Supporting the observations from the NMR spectroscopy, the mass spectra of the willow and lime leaf condensed tannins were identified as polymers with mainly procyanidin units, while the polymers of the spruce needle and beech leaves exhibit varying procyanidin/prodelphinidin ratios. Post source decay (PSD) fragmentation lead to a sequential loss of monomers and allowed a detailed characterization and sequencing of individual chains. In the case of the condensed tannins of lime this technique clearly excludes a pelargonidin terminal unit followed by a prodelphinidin unit, which would result in the same molecular masses as a polymer solely built up of procyanidin units.

Topics: Biflavonoids; Catechin; Magnetic Resonance Spectroscopy; Plant Leaves; Proanthocyanidins; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Tannins; Trees

Cell walls were isolated from seeds of grape berries (Vitis vinifera L.), and proanthocyanidin composition was determined over the course of ripening for different levels of vine water status. During the ripening period the tannins from the cell walls were always more polymerized than those from the inner part of the cell. At maturity this difference becomes more significant compared to véraison, due to a significant increase in the mean degree of polymerization of the cell wall tannins. The tannin composition was typical of grape seed tannins and was quite similar in the two cell fractions studied, but the epicatechin gallate proportion was significantly higher in the cell wall fraction. There were no significant effects of water deficit on composition and polymerization of seed tannins.

Topics: Biflavonoids; Catechin; Fruit; Phenols; Polymers; Proanthocyanidins; Seeds; Tannins; Vitis; Water

A reverse phase C(18) HPLC method with potential for high automated throughput has been developed for the quantitative analysis of polymeric procyanidins (tannins) in grape seed extracts. Chromatography gave rise to 13 distinct UV-absorbing peaks with good baseline separation. The UV-absorbing peak eluting last is distinct and therefore easily quantified. Biochemical analyses including ultrafiltration, protein precipitation, and Sephadex LH20 chromatography combined with electrospray mass spectrometric analyses establish that this peak predominantly contains polymeric procyanidins. The polymers, which appear to be galloylated to various degrees and seem to fragment in a characteristic manner during electrospray mass spectrometry, are well separated from catechins and procyanidin oligomers of up to 4 units. The recovery of polymeric grape seed tannins with this HPLC method was 86%, which is similar to the 89% recovery achieved with commercial quebracho tannins. The concentration of tannins in seeds from ripe Vitis vinifera cv. Shiraz grapes ranged from 1360 to 2830 mg/kg of berries.

Topics: Antioxidants; Biflavonoids; Catechin; Chromatography, High Pressure Liquid; Fruit; Polymers; Proanthocyanidins; Seeds; Species Specificity; Tannins

The effect of procyanidin solutions on superoxide anion radicals was studied with an enzymatic method and their EC(50) values were determined. A comparative study of the results suggested that the free radical scavenger potential of these phenolic compounds closely depends on their chemical and stereochemical structures. Oligomeric procyanidins were isolated in different fractions from grapes and wines by low- and high-pressure liquid chromatography. These compounds were found to be efficient free radical scavengers even for the weak concentrations in wines. Their activity in grapes or wines was much stronger than that of other commercially available natural antioxidants (such as ascorbic acid and gallic acid). The effect of tannins isolated from grapes on different radicals was analyzed according to three distinct methods: an enzymatic method for superoxide anion radicals (O(2)(*)(-)), a chemical method for the stable 1,1-diphenyl-2-picrylhydrazyl radical (DPPH(*)), and an immunochemical method to study the scavenging activity of seed procyanidins on DNA lesions induced by the radical HO(*).

Topics: Bepridil; Biflavonoids; Biphenyl Compounds; Catechin; DNA; Flavonoids; Free Radical Scavengers; Indicators and Reagents; Phenols; Picrates; Polymers; Proanthocyanidins; Rosales; Superoxides; Tannins; Wine; Xanthine Oxidase

To study the tannins from Tripterygium hypoglaucum.. Compounds were isolated by column chromatography and elucidated on the basis of spectroscopic analysis and comparison of references.. The compounds obtained were determined as (+)catechin, (-)epigallocatechin, procyanidin B-3, procyanidin B-4 and gallocatechin-(4 alpha-->8) epicatechin.. All the compounds were obtained from this plant for the first time.

Topics: Biflavonoids; Catechin; Molecular Structure; Plants, Medicinal; Proanthocyanidins; Tannins; Tripterygium

Topics: Biflavonoids; Catechin; Medicine, Chinese Traditional; Plants, Medicinal; Proanthocyanidins; Tannins