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PubMed2001

Isoterchebulin and 4,6-O-isoterchebuloyl-D-glucose, novel hydrolyzable tannins from Terminalia macroptera.

Two new hydrolyzable tannins, isoterchebulin (1) and 4,6-O-isoterchebuloyl-D-glucose (2), together with six known tannins, 3-8, were isolated from the bark of Terminalia macroptera. Their structures were elucidated by extensive 1D and 2D NMR studies, MS, and chemical transformations. Biological activities of all compounds were evaluated against the snail Biomphalaria glabrata, the bacteria Bacillus subtilis and Pseudomonas fluorescens, the nematode Caenorhabditis elegans, and four cancer cell lines (Hep G2, MCF-7/S, MDA-MB-231, and 5637 cells). All compounds except 3 showed antimicrobial activities against B. subtilis (MIC 8-64 microg/mL), whereas only 1 was active against C. elegans (100 microg/mL) and B. glabrata(LC(100) = 60 microg/mL). 3 and 8 were toxic against 5637 cells with LC(50) = 84.66 and 41.40 microM, respectively.

Africa↗

PubMed2002

Dimeric and trimeric hydrolyzable tannins from Quercus coccifera and Quercus suber.

Three new hydrolyzable tannins, cocciferins D(1) (1), D(2) (2), and T(1) (4), were isolated from the leaves of Quercus coccifera. Cocciferin D(2) (2) and two additional new tannins, cocciferins D(3) (3) and T(2) (5), were also obtained from the leaves of Quercus suber. Their oligomeric structures were elucidated on the basis of spectroscopic methods and chemical evidence. Compounds 2, 3, and 5 were rare oligomers possessing glucose cores with both open-chain and pyranose forms.

Algeria↗

PubMed1998

Effects of tannins from Geum japonicum on the catalytic activity of thrombin and factor Xa of blood coagulation cascade.

Bioassay-guided fractionation of the MeOH extract of the whole plant of Geum japonicum led to the isolation of seven known tannins. They were identified by spectroscopic methods as penta-O-galloyl-beta-glucoside (1), pedunculagin (2), 2, 3-(S)-hexahydroxydiphenoyl-D-glucose (3), tellimagrandin II (4), 2, 6-di-O-galloyl-D-glucose (5), casuariin (6), and 5-desgalloylstachyurin (7). Compounds 1, 2, 4, 6, and 7 showed potent anticoagulant activity by significantly prolonging the clotting of rabbit plasma. The inhibitory effect of 2 was competitively directed against thrombin. Its IC50 values for inhibition of the enzymatic activity of thrombin on synthetic substrate and fibrinogen were 0.18 and 0.15 microM, respectively. On the other hand, compounds 1, 4, 6, and 7 are mixed noncompetitive inhibitors of thrombin. Their IC50 values for inhibition of fibrinogen hydrolysis were twofold to sevenfold lower than those for the inhibition of synthetic substrate hydrolysis. Factor Xa was competitively inhibited by compounds 1, 2, 4, 6, and 7. The phenolic hydroxyl groups of the active tannins appear to play an important role in their inhibitory effect on the enzymes.

Animals↗

PubMed2001

Antibacterial action of several tannins against Staphylococcus aureus.

We examined the antibacterial action of several tannins on plasma coagulation by Staphylococcus aureus and the effect of conventional chemotherapy combined with tannic acid below the MIC. Coagulation was inhibited in plasma containing tannic acid (100 mg/L), gallic acid (5000 mg/L), ellagic acid (5000 mg/L), (-)-epicatechin (1500 mg/L), (-)-epicatechin gallate (500 mg/L) or (-)-epigallocatechin gallate (200 mg/L) after incubation for 24 h. All tannins inhibited coagulation at a concentration below the MIC. The MICs of oxacillin and cefdinir for S. aureus were reduced to < or = 0.06 mg/L in Mueller-Hinton agar plates with tannic acid (100 mg/L) at a concentration below the MIC. The antistaphylococcal activity of tannic acid was reduced in plates with 10% rabbit blood, but not in those with 10% rabbit plasma. Membranous structures formed in a culture medium containing equal proportions of plasma and tryptic soy broth after incubation for 24 h. The colony counts of S. aureus in membranous structures in the medium containing oxacillin (40 mg/L) and tannic acid (100 mg/L) were c. 10-fold lower than those in medium containing oxacillin (40 mg/L) alone (P < 0.01). Tannic acid merits further investigation as a possible adjuvant agent against S. aureus skin infections treated with beta-lactam antibiotics.

Anti-Bacterial Agents↗

PubMed1996

New hydrolyzable tannins, shephagenins A and B, from Shepherdia argentea as HIV-1 reverse transcriptase inhibitors.

Two new hydrolyzable tannins, shephagenins A and B, were isolated along with hippophaenin A and strictinin from the leaf extract of Shepherdia argentea, which showed a remarkable inhibitory activity against human immunodeficiency virus (HIV)-1 reverse transcriptase. Their structures, having a gluconic acid core, have been elucidated on the basis of spectroscopic and chemical methods. The inhibitory effect of the leaf extract on HIV-1 reverse transcriptase was found to be due to tannins, and their activities were stronger than that of (-)-epigallocatechin gallate as a positive control.

Antiviral Agents↗

PubMedDate not supplied

Antioxidant and free radical scavenging effects of the tannins of Terminalia catappa L.

Reactive oxygen species (ROS) react with biological molecules and destroy the structure of cells and eventually cause free radical-induced disease such as inflammation and cancer. Previous studies showed that an aqueus extract of Terminalia catappa L. exhibited superoxide radical scavenger activity and modification of mitomycin C-induced clasto-genicity. In order to investigate the multiple antioxidant effect of the tannin components of T. catappa L., their ability to prevent lipid peroxidation, superoxide formation and their free radical scavenging activity were evaluated. The results indicated that all of these components showed potent antioxidant activity. Punicalagin and punicalin were the most abundant components and had the strongest anti-oxidative effects of this group of tannins.

Antioxidants↗

PubMedDate not supplied

Agrimoniin, an antitumor tannin of Agrimonia pilosa Ledeb., induces interleukin-1.

The induction of interleukin-1 (IL-1) by agrimoniin, a tannin of Agrimonia pilosa Ledeb., in human peripheral blood mononuclear cells (PBMC) in vitro and in mouse adherent peritoneal exudate cells (PEC) in vivo was studied. A significant amount of IL-1 beta in the culture supernatant of the human PBMC stimulated with agrimoniin was detected with an enzyme-linked immunoadherent assay. Agrimoniin induced IL-1 beta secretion dose- and time-dependently. The adherent PEC from mice intraperitoneally injected with agrimoniin (10 mg/kg) also secreted IL-1 4 days later. These results suggest that agrimoniin, a plant tannin, is a novel cytokine inducer.

Adult↗

PubMed1993

Clinical studies on marginal gingiva around abutment tooth (Part 3). Effect of tannin-fluoride preparation on gingival health.

It was examined whether the tannin-fluoride preparation (HY preparation), which might have a caries-reductive, plaque inhibiting and astringent action, could reduce the incidence of gingival inflammation around abutment teeth. Zinc oxide eugenol cement mixed with the HY preparation was packed in the cavity prepared in the resin base facing the abutment tooth. Gingival crevicular fluid (Periotron units:GCF), gingival index (GI), plaque index (PlI) and probing depth around the abutment teeth were measured over a 3 month period. The following results were obtained: 1. GCF decreased at month 1 and showed low values at months 2 and 3. 2. GI showed a decreasing tendency. 3. PlI and probing depth did not show obvious changes. These results indicate that the tannin-fluoride preparation reduces gingival inflammation around abutment teeth.

Adolescent↗

PubMed1993

Uptake and recovery of gold by immobilized persimmon tannin.

Some attempts were made to recover gold from aqueous systems using immobilized persimmon tannin. This adsorbent adsorbed gold from solutions containing hydrogen tetrachloroaurate (III) with high efficiency, whereas there was minimal adsorption from solutions containing gold(I) sodium thiomalate and sodium dicyanoaurate(I). The adsorption of gold was rapid, and was affected by the pH of the solution, temperature, external gold concentration and amount of adsorbent. Adsorbed gold was easily desorbed with 1 mol dm-3 thiourea solution, indicating that immobilized persimmon tannin can be repeatedly re-used for the recovery of gold using adsorption-desorption cycles.

Adsorption↗

PubMed2004

Determination of hydrolyzable tannins in the fruit of Terminalia chebula Retz. by high-performance liquid chromatography and capillary electrophoresis.

A RP-HPLC method for determining fourteen components (gallic acid, chebulic acid, 1,6-di-O-galloyl-D-glucose, punicalagin, 3,4,6-tri-O-galloyl-D-glucose, casuarinin, chebulanin, corilagin, neochebulinic acid, terchebulin, ellagic acid, chebulagic acid, chebulinic acid, and 1,2,3,4,6-penta-O-galloyl-D-glucose) in the fruit of Terminalia chebula Retz. is described. The separation was achieved within 80 min using a binary gradient with mobile phases consisting of a pH 2.7 phosphoric acid solution and an 80% CH3CN solution. Capillary electrophoretic analyses were also attempted, and it was found that CZE (25 mM Na2B4O7, 5 mM NaH2PO4, pH 7.0) was an efficient method for the separation of gallotannins, while an MEKC method (25 mM Na2B4O7, 5 mM NaH2PO4, 20 mM SDS, pH 7.0, and 10% acetonitrile) provided a better separation for most of the tannins examined. The HPLC and CE methods developed were both successfully applied to the assay of tannins in commercial samples of Chebulae Fructus.

Calibration↗

PubMedDate not supplied

Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatography--electrospray ionisation mass spectrometry.

The first detailed analysis of the phenolic constituents of the reaction zones (tissue of antimicrobial defence) from the sapwood of a Eucalyptus spp. is presented. Plantation-grown Eucalyptus nitens trees with stem decay resulting from pruning wounds were sampled and extracts were prepared from healthy sapwood and from reaction zone tissue. Analysis by HPLC with ESI-MS revealed that a diverse range of hydrolysable tannins are present in both healthy sapwood and in reaction zone extracts, including over 30 gallotannins, ellagitannins and phenols. Eight tannins were unequivocally identified, including the gallotannins tri-O-galloyl-beta-D-glucose, tetra-O-galloyl-beta-D-glucose and penta-O-galloyl-beta-D-glucose, and the ellagitannins pedunculagin, tellimagrandin I, casuarinin, casuarictin and tellimagrandin II. The phenols gallic acid, ellagic acid and catechin were also identified. The ellagitannins (particularly pedunculagin) are considerably more abundant in the reaction zone than in the healthy sapwood and may contribute to the effectiveness of the reaction zone as an antimicrobial barrier.

Chromatography, High Pressure Liquid↗

PubMedDate not supplied

Fractionation of grape tannins and analysis by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry.

Polymeric tannins, extracted from grape berries (Gamay variety), were fractionated according to their mean degree of polymerisation (mDP) on a styrene-divinylbenzene phase eluted with a gradient of methanol:chloroform. Increasing the percentage of methanol led to the solubilisation of higher molecular weight tannins. The mean mDP of each collected fraction was determined by acid-catalysed degradation in the presence of a nucleophilic reagent. The fractionation method produced a linear gradient of mDP varying between 1.84 and 19.34. The fractions were partially characterised by matrix assisted laser desorption/ionisation time-of-flight mass spectrometry (MALDI-TOF/MS). The spectra showed a complex mixture of proanthocyanidins and galloylated proanthocyanidins up to 4000 amu.

Anthocyanins↗

PubMed2007

Antiinflammatory and antiulcer properties of tannins from Myracrodruon urundeuva Allemão (Anacardiaceae) in rodents.

Myracrodruon urundeuva Allemão is a plant utilized in Northeast Brazil as an antiinflammatory, wound healing and in gynecological illnesses. The objectives of the present study were to evaluate the antiinflammatory and antiulcer properties of the tannin-enriched fraction (TEF) isolated from the stem bark of M. urundeuva, in the formalin test, in mice, and in carrageenan-induced paw edema and gastric ulcer models, in rats. The results showed that TEF dose-dependently inhibited both phases of the formalin test. However, the effect was predominant in the 2nd phase of the response where inhibitions of 47%, 76% and 85% were observed, with doses of 5, 10 and 50 mg/kg, i.p. In the carrageenan-induced paw edema, significant inhibitions were observed at 3 h (44%) and 4 h (28%), with a dose of 10 mg/kg, i.p. TEF also significantly decreased by 37%, 43% and 57% gastric ulceration induced by indomethacin, at doses of 10, 20 and 50 mg/kg p.o. In the ethanol-induced gastric ulcer model, TEF was less effective, and significant inhibitions (42% to 46%) were observed only with doses of 100 and 200 mg/kg, p.o., respectively. In conclusion, it was shown that TEF presents antiinflammatory and antiulcer effects, partly due to its antioxidant action, known to be present in polyphenols, including tannins.

Administration, Oral↗

PubMed1987

Digestion and metabolism of high-tannin Eucalyptus foliage by the brushtail possum (Trichosurus vulpecula) (Marsupialia: Phalangeridae).

The digestion and metabolism of Eucalyptus melliodora foliage was studied in captive brushtail possums (Trichosurus vulpecula). The foliage was low in nitrogen and silica but high in lignified fibre and phenolics compared with diets consumed by most other herbivores. The high lignin content was suggested as the main cause of the low digestibility of E. melliodora cell walls (24%); microscopic observations of plant fragments in the caecum and faeces revealed few bacteria attached to lignified tissues. The conversion of digestible energy (0.34 MJ X kg-0.75 X d-1) to metabolizable energy (0.26 MJ X kg-0.75 X d-1) was low compared to most other herbivores, probably because of excretion of metabolites of leaf essential oils and phenolics in the urine. When the inhibitory effect of leaf tannins on fibre digestion was blocked by supplementing the animals with polyethylene glycol (PEG), intake of dry matter, metabolizable energy and digestible fibre increased. These effects were attributed to the reversal by PEG of tannin-microbial enzyme complexes. It was concluded that the gut-filling effect of a bulk of indigestible fibre is a major reason why the brushtail possum does not feed exclusively on Eucalyptus foliage in the wild.

Animals↗

PubMed2002

Isolation from a shea cake digester of a tannin-tolerant Escherichia coli strain decarboxylating p-hydroxybenzoic and vanillic acids.

A facultatively anaerobic, mesophilic, Gram-negative, non-motile, non-sporulated bacterium, designated strain C2, was isolated from an anaerobic digester fed with shea cake rich in tannins and aromatic compounds and previously inoculated with anaerobic sludge from the pit of a slaughterhouse, after enrichment on tannic acid. The straight rods occurred singly or in pairs. Strain C2 fermented numerous carbohydrates (fructose, galactose, glucose, lactose, mannose, maltose, melibiose, raffinose, rhamnose, ribose, saccharose, sorbitol, trehalose, and xylose) and peptides (Biotrypcase, Casamino acids, and yeast extract), producing acid and gas, and had a G + C content of 51.6 +/- 0.1 mol %. Strain C2 was very closely related to Escherichia coli (= DSM 30083(T)) phylogenetically (similarity of 99%), genotypically (DNA homology of 79%), and phenotypically. The isolate tolerated tannic acid (hydrolyzable tannin) and decarboxylated by non-oxidative decarboxylation only p-hydroxybenzoic and vanillic acids to their corresponding phenol and guaicol, under anaerobic and aerobic conditions without further degradation. Adding glucose increased growth and the rate of conversion. High concentrations of p-hydroxybenzoic acid or vanillic acid inhibited growth, and decarboxylation could not occur completely, suggesting phenol toxicity. In contrast, the type strain of E. coli cannot metabolize p-hydroxybenzoic and vanillic acids, anaerobically or aerobically, with or without glucose added.

Aerobiosis↗

PubMed1999

Effect of complex polyphenols and tannins from red wine (WCPT) on chemically induced oxidative DNA damage in the rat.

BACKGROUND: Flavonoids are polyphenolic antioxidants occurring in vegetables and fruits as well as beverages such as tea and wine which have been thought to influence oxidative damage. AIM OF THE STUDY: We wanted to verify whether a complex mixture of wine tannins (wine complex polyphenols and tannins, WCPT) prevent chemically-induced oxidative DNA damage in vivo. METHODS: Oxidative DNA damage was evaluated by measuring the ratio of 8-hydroxy-2'-deoxyguanosine (80HdG)/ 2-deoxyguanosine (2dG) x 10(-6) in hydrolyzed DNA using HPLC coupled with electrochemical and UV detectors. RESULTS: We treated rats with WCPT (57 mg/kg p.o.) for 14 d, a dose 10-fold higher than what a moderate wine drinker would be exposed to. WCPT administration significantly reduced the ratio of 80HdG/2dG x 10(-6) in liver DNA obtained from rats treated with 2-nitropropane (2NP) relative to controls administered 2NP only (33. 3 +/- 2.5 vs. 44.9 +/- 3.2 x 10(-6) 2dG; micro +/- SE; p<0.05). On the contrary, pretreatment with WCPT for 10 d did not protect the colon mucosa from oxidative DNA damage induced by 1, 2-dimethylhydrazine (DMH). 2NP and DMH are hepatic and colon carcinogens, respectively, capable of inducing oxidative DNA damage. CONCLUSIONS: WCPT have protective action against some types of chemically-induced oxidative DNA damage in vivo.

1,2-Dimethylhydrazine↗

PubMed2000

Effect of complex polyphenols and tannins from red wine on DNA oxidative damage of rat colon mucosa in vivo.

BACKGROUND: Dietary polyphenols have been reported to have a variety of biological actions, including anti-carcinogenic, antioxidant and anti-inflammatory activities. AIM OF THE STUDY: In the present study we have evaluated the effect of an oral treatment with complex polyphenols and tannins from red wine and tea on DNA oxidative damage in the rat colon mucosa. METHODS: Isolated colonocytes were prepared from the colon mucosa of rats treated for ten days with either wine complex polyphenols (57.2 mg/kg/d) or thearubigin (40 mg/kg/d) by oral gavage. Colonocyte oxidative DNA damage was analysed at the single cell level using a modification of the comet assay technique. RESULTS: The results show that wine complex polyphenols and tannins induce a significant decrease (-62% for pyrimidine and -57% for purine oxidation) in basal DNA oxidative damage in colon mucosal cells without affecting the basal level of single-strand breaks. On the other hand, tea polyphenols, namely a crude extract of thearubigin, did not affect either strand breaks or pyrimidine oxidation in colon mucosal cells. CONCLUSIONS: Our experiments are the first demonstration that dietary polyphenols can modulate in vivo oxidative damage in the gastrointestinal tract of rodents. These data support the hypothesis that dietary polyphenols might have both a protective and a therapeutic potential in oxidative damage-related pathologies.

Animals↗

PubMed2005

Extraction of condensed tannins from cervid feed and feces and quantification using a radial diffusion assay.

A radial diffusion assay was employed to quantify condensed tannins (CT) in feed and feces of mule deer (Odocoileus hemionus) and white-tailed deer (O. virginianus). This biological assay measures the precipitation of bovine serum albumin (BSA), with the area of the precipitation ring being proportional to the amount of extracted CT applied to the well. CT extracted from the bark of white spruce (Picea glauca) was used as the standard. CT were extracted with 70% (v/v) aqueous acetone and precipitated with 50% (v/v) aqueous methanol or 70% (v/v) aqueous acetone. Functional range of CT weights for suitable ring measurement was 0.5-4.0 mg, and equilibrium was achieved within an incubation period of 24 hr. Methanol (50%) was a more effective precipitation solvent than acetone (70%) having 13 +/- 4% greater specific activity (P < 0.05) and superior capabilities for predicting CT content. Precipitation rings were evaluated on images magnified on a photocopier. Ring diameters measured on a 200% enlarged photocopy provided the most precise estimate of ring area (R2 = 0.98). This convenient method reduced analysis times and enhanced accuracy and precision of tannin quantification. Analytical consequences and future research requirements are considered.

Animal Feed↗