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PubMed2002

Toxicity of tannins towards the free-living nematode Caenorhabditis elegans and the brine shrimp Artemia salina.

Toxicities of gallo- and condensed tannins towards the free-living nematode Caenorhabditis elegans is dependent on the tannins' molecular sizes. In the present paper we investigate the toxicity of ellagitannins to C elegans and the toxicity of ellagi-, gallo-, and condensed tannins to the brine shrimpArtemia salina. Ellagitannins 1 and 2 were isolated from Euphorbia supina and identified as tellimagrandin I and rugosin A methyl ester, respectively. An ellagitannin preparation from Cornus officinalis was chromatographically fractionated into ellagitannins A through H, having different molecular weights and specific rotations. Three of the ten ellagitannins, 2, G, and H produced significant toxicity towards C. elegans, showing the presence of an activity-structure relationship, as opposed to the results from tests of gallo- and condensed tannins. Ellagi-, gallo-, and condensed tannins also produced toxicity in A. salina.

Animals↗
PubMed2003

[Review in the studies on tannins activity of cancer prevention and anticancer].

This paper reviewed the biological activities of tannins in cancer prevention and anticancer, and mainly discussed related mechanisms. The results suggest that tannins, whether total tannins or pure tannin compound, have remarkable activity in cancer prevention and anticancer. It has wealthy foreground for developing new cancer prevention agents and/or new anticancer drugs screening among tannin compounds.

Animals↗
PubMed2003

The gastroprotective effect of tannins extracted from duhat (Syzygium cumini Skeels) bark on HCl/ethanol induced gastric mucosal injury in Sprague-Dawley rats.

The gastroprotective effect of quantified tannins (13.4%) from Syzygium cumini was determined. Gastric mucosal damage was induced in sixty eight rats by oral gavage administration of HCl/ethanol solution. For macroscopic and microscopic studies, 30 rats were divided into three groups consisting of a negative control, an Omeprazole group and a Tannins group. There was no significant difference in the number, size and surface area of macroscopic lesions between the three groups. Microscopic examination using Best's Ulcer Staging Index showed that Tannins had a very significant decrease in gastric mucosal damage with p<0.01. Average lymphocyte populations in the three groups showed no significant difference, although both the Tannins and Omeprazole group had fewer lymphocytes. Thirty-eight rats were studied for the amount of free radicals present after induction of gastric damage. A dose which consisted of 20.0 g tannins/kg rat weight showed significantly lower stomach free radical concentrations. These findings suggest that tannins extracted from S. cumini have gastroprotective and anti-ulcerogenic effects.

Animals↗
PubMed1986

Toxicity to endothelial cells mediated by cotton bract tannin. Potential contribution to the pathogenesis of byssinosis.

Byssinosis is an occupational disease of textile workers caused by exposure to the bract portion of the cotton plant in the form of mill dust. The authors established an in vitro cytotoxicity assay using 51Cr release to assess time- and dose-dependent toxicity of condensed tannin, a component of bracts, on porcine aortic and pulmonary arterial endothelial cells. Tannin produced dose-dependent toxicity to both types of endothelial cells; aortic endothelial cells were more sensitive than were endothelial cells from the pulmonary artery. Skin fibroblasts were relatively insensitive to tannin. Cytotoxicity was not immediate. Release of 51Cr was preceded by a several-hour period during which the endothelial cells underwent profound morphologic changes (as assessed by light and electron microscopy). Even brief exposure of endothelial cells to tannin produced later toxicity and morphologic changes. Condensed tannin causes time- and dose-dependent injury to endothelial cells in vitro at doses potentially achievable in vivo.

Animals↗
PubMed2000

Short-term changes in eating patterns explain the effects of condensed tannins on feed intake in heifers.

Ingestion of condensed tannins decreases feed intake in ruminants. Polyethylene glycol (PEG) forms high-affinity complexes with tannins. In two experiments carried out on Holstein heifers, quebracho (Q) from the Aspidosperma quebracho served as source of condensed tannins. The aims of the study were (i) to quantify the effect of Q on feed intake and eating behaviour in cattle fed complete mixed diets (CMDs); (ii) to clarify if changes induced in ingestive behaviour and feed intake by Q in cattle can be reversed by feeding PEG; and (iii) to clarify if the decrease in feed intake is associated with short-term (astringency, post-ingestive malaise) or longer-term effects. In experiment 1, 500 g/day of Q was found to be the minimal dose that decreased feed intake in heifers. A ratio of PEG:Q equal to 1:12.5 did not fully restore feed intake. In experiment 2, four heifers received a random sequence of four rations in a Latin-square design with feeding cycles of ca. 7 days: CMD containing no supplements (C), or supplemented with 625 g/day of Q without PEG (Q), with 625 g/day of Q and 250 g/day of PEG (Q-PEG), or with 250 g/day of PEG without Q (PEG). Individual rations were continuously weighed in the trough and the behaviour of heifers was observed for 180 min after distribution of CMD. Overall, feeding Q was associated with lowered feed intake and shorter duration of eating bouts, mainly of the first eating bout, immediately after distribution of the diet. A larger portion of the diet was consumed subsequent to 180 min after distribution in Q-fed heifers. Eating rate and the water to food ratio were not affected by Q. The effects of Q on feed intake were attenuated by feeding PEG. Heifers adapted effectively to condensed tannins by increasing the number of eating bouts and the portion of diet consumed subsequent to 180 min after distribution, so that no differences in feed intake were noted on the last day of each feeding cycle. Data are interpreted to show that: (i) negative effects of Q on feed intake derive from astringency of CT and short-term post-ingestive malaise; (ii) the increased number of eating bouts and their wider partition throughout the day are means to preserve the ruminal environment in Q-fed heifers; (iii) PEG has the potential to neutralize negative effects of condensed tannins in cattle.

Journal Article↗
PubMed2001

Immunocytochemical studies on the origin and deposition sites of hydrolyzable tannins.

Two specific antibodies, directed toward hydrolyzable tannins, i.e. polygalloylated or oxidized derivatives of 1,2,3,4,6-penta-O-galloylglucose, and toward an acyltransferase from oak leaves that catalyzes the biosynthesis of this principal precursor, were used in immunocytochemical studies to determine the intracellular sites of origin and deposition of these polyphenolic plant constituents. Immunostaining of semi-thin sections from leaves and roots of young pedunculate oak (Quercus robur, syn. Quercus pedunculata) plants with marker enzymes and immunogold labeling of ultra-thin sections revealed immunoreactive sites for both enzyme and hydrolyzable tannins in chloroplasts, cell walls and intercellular spaces. The latter non-cytoplasmic (apoplast) compartments displayed characteristic aggregations of these two epitopes, thus indicating an intimate association of the biocatalyst and its products. Identical distribution patterns for hydrolyzable tannins were observed in leaves of Rhus typhina (sumac) and Tellima grandiflora (fringe cups) which, however, displayed no affinity toward the galloyltransferase antibody that had been raised against enzyme from oak. Controls with spinach leaves, known to be devoid of tannins, were inactive in all cases. The conclusion that, besides chloroplasts, cell walls and intercellular space serve as sites for the biosynthesis and deposition of hydrolyzable tannins was confirmed by analyzing extracts from these non-cytoplasmic compartments.

Journal Article↗
PubMed2000

Phenolic glycosides and condensed tannins in Salix sericea, S. eriocephala and their F1 hybrids: not all hybrids are created equal.

The performance of hybrids depends upon the inheritance and expression of resistance traits. Secondary chemicals are one such resistance trait. In this study, we measured the concentrations of phenolic glycosides and condensed tannins in parental and F1 hybrid willows to examine the sources of chemical variation among hybrids. S. sericea produces phenolic glycosides, salicortin and 2'-cinnamoylsalicortin, and low concentrations of condensed tannin in its leaves. In contrast, S. eriocephala produces no phenolic glycosides but high concentrations of condensed tannins in its leaves. These traits are inherited quantitatively in hybrids. On average, F1 hybrids are intermediate for condensed tannins, suggesting predominantly additive inheritance or balanced ambidirectional dominance of this defensive chemical from the parental species. In contrast, the concentration of phenolic glycosides is lower than the parental midpoint, indicating directional dominance. However, there is extensive variation among F1 hybrids. The concentration of tannin and phenolic glycosides in F1 hybrid families is either (1) lower than the midpoint, (2) higher than the midpoint, or (3) indistinguishable from the midpoint of the two parental taxa. It appears that the production of the phenolic glycosides, especially 2'-cinnamoylsalicortin, is controlled by one or more recessive alleles. We also observed a two-fold or greater difference in concentration between some hybrid families. We discuss how chemical variation may effect the relative susceptibility of hybrid willows to herbivores.

Journal Article↗
PubMed1998

Genetic manipulation of condensed tannins in higher plants. Ii. Analysis Of birdsfoot trefoil plants harboring antisense dihydroflavonol reductase constructs

We have produced and analyzed transgenic birdsfoot trefoil (Lotus corniculatus L.) plants harboring antisense dihydroflavonol reductase (AS-DFR) sequences. In initial experiments the effect of introducing three different antisense Antirrhinum majus L. DFR constructs into a single recipient genotype (S50) was assessed. There were no obvious effects on plant biomass, but levels of condensed tannins showed a statistical reduction in leaf, stem, and root tissues of some of the antisense lines. Transformation events were also found, which resulted in increased levels of condensed tannins. In subsequent experiments a detailed study of AS-DFR phenotypes was carried out in genotype S33 using pMAJ2 (an antisense construct comprising the 5' half of the A. majus cDNA). In this case, reduced tannin levels were found in leaf and stem tissues and in juvenile shoot tissues. Analysis of soluble flavonoids and isoflavonoids in tannin down-regulated shoot tissues indicated few obvious default products. When two S33 AS-DFR lines were outcrossed, there was an underrepresentation of transgene sequences in progeny plants and no examples of inheritance of an antisense phenotype were observed. To our knowledge, this is the first report of the genetic manipulation of condensed tannin biosynthesis in higher plants.

Journal Article↗
PubMed1999

Genotypic variation for condensed tannin production in trembling aspen (POPULUS TREMULOIDES, salicaceae) under elevated CO2 and in high- and low-fertility soil.

The carbon/nutrient balance hypothesis suggests that leaf carbon to nitrogen ratios influence the synthesis of secondary compounds such as condensed tannins. We studied the effects of rising atmospheric carbon dioxide on carbon to nitrogen ratios and tannin production. Six genotypes of Populus tremuloides were grown under elevated and ambient CO(2) partial pressure and high- and low-fertility soil in field open-top chambers in northern lower Michigan, USA. During the second year of exposure, leaves were harvested three times (June, August, and September) and analyzed for condensed tannin concentration. The carbon/nutrient balance hypothesis was supported overall, with significantly greater leaf tannin concentration at high CO(2) and low soil fertility compared to ambient CO(2) and high soil fertility. However, some genotypes increased tannin concentration at elevated compared to ambient CO(2), while others showed no CO(2) response. Performance of lepidopteran leaf miner (Phyllonorycter tremuloidiella) larvae feeding on these plants varied across genotypes, CO(2), and fertility treatments. These results suggest that with rising atmospheric CO(2), plant secondary compound production may vary within species. This could have consequences for plant-herbivore and plant-microbe interactions and for the evolutionary response of this species to global climate change.

Journal Article↗
PubMed1992

Tannin content of tea and coffee.

The tannin content of over-the-counter Indian tea, of green coffee beans and of the roasted coffee beans prepared from the same green beans was determined with a radial diffusion-protein precipitation technique and with a spectrophotometric method. The green beans contained 6.6 +/- 0.6 mg g-1 weight tannic acid equivalents as found by protein precipitation (n = 5, +/- SD) or 6.8 +/- 2.3 mg g-1 by spectrophotometry. The same figures for roasted beans were 18 +/- 1.7 and 17 +/- 2.7 mg g-1, respectively. Tea contained 37 +/- 2.6 mg g-1 weight tannic acid equivalents as analysed by spectrophotometry and 24 +/- 2.8 mg g-1 by the protein precipitation technique. The latter finding may show that the biological reactivity of tannins is variable, although no major changes in the tannin-precipitated albumin occurred as shown by electrophoretic analysis. Both methods provide an easy analysis of the reportedly carcinogenic plant tannins.

Coffee↗
PubMedDate not supplied

Tannins, xenobiotic metabolism and cancer chemoprevention in experimental animals.

Tannins are plant polyphenolic compounds that are contained in large quantities in food and beverages (tea, red wine, nuts, etc.) consumed by humans daily. It has been shown that various tannins exert broad cancer chemoprotective activity in a number of animal models. This review summarizes the recent literature regarding both the mechanisms involved, and the specific organ cancer models used in laboratory animals. An increasing body of evidence demonstrates that tannins act as both anti-initiating and antipromoting agents. In view of the fact that tannins may be of valid medicinal efficacy in human clinical trials, the present review attempts to integrate results from animal studies, and considers their possible application in humans.

Animals↗
PubMed2003

Antioxidant and pro-oxidant effects of tannins in digestive cells of the freshwater mussel Unio tumidus.

Bivalve molluscs, particularly mussels, are sensitive biomarkers of aquatic ecosystem pollution. The tannins, water-soluble plant polyphenols, may play an important role in this environment and, mainly as a consequence of interaction with pollutants, their toxicity may change. We studied three naturally occurring compounds, tannic acid, ellagic acid and gallic acid, for their ability to modulate DNA damage produced by these tannins alone and in the presence of the oxidative stress inducer H(2)O(2), in cells of the digestive gland of mussels (Unio tumidus). After the treatment of the cells with polyphenols at different concentrations (1, 5, 15, 30, 60, 80, 100, 120, 180, 240 microM) and with hydrogen peroxide in the range of 0.04 and 0.1mM, single-strand breaks (ssb) in DNA were investigated, using the comet assay. The ability of phenolic acids to decrease DNA damage through their antioxidant properties was also assessed. The results show that the phenols, which are known as antioxidative agents, could also act as pro-oxidants. They induced ssb in DNA of the digestive gland at concentrations higher that 10 microM, but lower doses (1 and 5 microM) did not contribute to the DNA damage. This study was also designed to evaluate the protective effect of these tannins against H(2)O(2)-mediated DNA damage in the cells. In this treatment, the two concentrations (1 and 5 microM) significantly decreased the amount of lesions induced by H(2)O(2) (0.04 and 0.1mM). In conclusion, our results demonstrate that antioxidative properties of tannins may change to pro-oxidative activities at the higher concentrations. This suggests that the biologic actions of these compounds may be rather complicated.

Animals↗
PubMed2003

Effect of tannins from Quercus suber and Quercus coccifera leaves on ethanol-induced gastric lesions in mice.

The gastroprotective effects of 70% acetone extracts of Quercus suber and Quercus coccifera leaves and of tannins (pedunculagin, castalagin, phillyraeoidin A, and acutissimin B) purified from these extracts were examined in the mouse using the ethanol-induced gastric ulcer model. Both extracts (25, 50, and 100 mg/kg), given orally, prevented the formation of ethanol-induced lesions in the stomach. The percent protection varied between 68 and 91%. Purified tannins (50 mg/kg) were also effective in protecting the stomach against ethanol, and the percent protection varied from 66 to 83%. Castalagin was the most potent. Both extracts and all of the tannins tested (10, 25, and 50 microg/mL) strongly inhibited (55-65%) the lipid peroxidation of rabbit brain homogenate. These results suggest that the gastroprotective effects of extracts of Q. suber and Q. coccifera leaves and the purified tannins in this experimental model are related to their anti-lipoperoxidant properties.

Acetone↗
PubMed2000

Biotreatment of tannin-rich beer-factory wastewater with white-rot basidiomycete Coriolopsis gallica monitored by pyrolysis/gas chromatography/mass spectrometry.

Some fractions of beer-factory wastewaters represent an important environmental concern owing to their high content of polyphenols and dark-brown color. The capacity of Coriolopsis gallica to preferentially degrade lignin has been successfully applied in our laboratory to the biotreatment and decolorization of paper-industry effluents. In this work, the ability of this white-rot fungus to degrade high-tannin-containing wastewaters is evaluated. Under all the conditions studied, effluent decolorization and chemical oxygen demand reduction achieved by C. gallica at day 12 of incubation were close to 50 and 65%, respectively. No adhesion of dark color to the fungal mycelium was observed suggesting that decolorization could be ascribed to C. gallica degradation systems. Mycelium dry-weight values showed that C. gallica is tolerant to relatively high tannin content present in the effluent samples. In the sample containing the highest effluent concentration (60% v/v), dry-weight values suggested an inhibition of fungal growth at day 6 of incubation and a further adaptation of the fungus to the stressing tannin effect at day 12 of fungal treatment. Pyrolysis/gas chromatography/mass spectrometry results showed a decrease of polyphenols pyrolysis products, mainly phenol and guaiacol, with the incubation time. All these results indicate the potential use of C. gallica in bioremediation of tannin-containing industrial wastewaters and in other applications where a reduction in polyphenols content is required.

Beer↗
PubMedDate not supplied

Reactions of tannins with human serum proteoglycans.

Incubation of an isolated human serum proteoglycan fraction with a tannic acid or oak tannin fraction caused a dose-dependent decrease in the total glycan content and a special diminution of a major proteoglycan band with molecular weight 112 kDa in samples as analyzed by polyacrylamide electrophoresis and with carbohydrate staining. Tannic acid was more active than oak tannins while the spruce tannin fraction caused almost no effects. The concentration of plant tannin extracts is often expressed as tannic acid equivalents, which may overestimate their biological activity in this model. This cell-free model may act as a versatile tool for studies on macromolemular interactions of plant polyphenols.

Drug Interactions↗
PubMed1979

Immobilization of aminoacylase by adsorption to tannin immobilized on aminohexyl cellulose.

The immobilization of aminoacylase (N-acylamino acid amidohydrolase, EC 3.5.1.14) was investigated by using tannin immobilized on aminohexyl cellulose. The most active immobilized aminoacylase was obtained when aminoacylase was adsorbed to the immobilized tannin in a weak alkaline medium containing sodium chloride and n-butanol at 37 degrees C. The activity of the immobilized tannin-aminoacylase complex per unit volume was five times higher than that of the DEAE-Sephadex-aminoacylase complex used for industrial production of L-amino acids in our plants. The half-life of the immobilized tannin-aminoacylase complex was 20 days under continuous operation at a high concentration of substrate; on the contrary, that of the DEAE-Sephadex-aminoacylase complex was 0.5 days.

Adsorption↗
PubMedDate not supplied

Woodworkers' exposure to tannins.

The tannin concentration of hard- and soft-wood dust was determined in dust powder and in samples on filters. It varied from 1.6 +/- 0.3 mg g-1 (+/- SD) for fir, which is a soft wood, to 80 +/- 30 mg g-1 (+/- SD) for oak, which is a hard wood. The low detection limit of the spectrophotometric method (1.5 micrograms per sample) made the analysis possible with no interference from cellulose ester filters. In five woodworking shops the concentrations of the total dust varied from 0.2 to 20 mg m-3, while those of tannins varied from 2 to 341 micrograms m-3. As hard woods like oak or mahogany have a higher tannin concentration than soft woods, tannin concentration analysis in wood dust can be used as an indicator of exposure to hard-wood dust.

Air Pollutants, Occupational↗
PubMed1993

Tannins as potent inhibitors of DNA topoisomerase II in vitro.

Fifty-two out of 60 tannins, including gallo-, ellagi-, condensed, and complex tannins, are inhibitors of human DNA topoisomerase II in vitro. Thirty-six compounds that completely inhibited enzyme activity at a concentration of 500 nM or less, as assessed by ATP-dependent unknotting of P4 phage DNA, were at least 100-fold more potent than the clinically useful antitumor agent etoposide (VP-16). Relative inhibitory activity was primarily related to the number of phenolic hydroxyl groups (galloyl and hexahydroxydiphenoyl moieties) found in the active structures, with more groups generally conferring increased potencies. Unlike VP-16 and some DNA intercalative agents that stabilize the topoisomerase II-DNA cleavage intermediate, none of the active compounds induced protein-linked DNA breaks in cultured cells. Some of the tannins reduced VP-16-induced protein-linked DNA breaks by 20% or more, but one of these compounds, (-)-epicatechin, was not an inhibitor in vitro. Our data suggest that some tannins, such as sangiin H-6, that are potent inhibitors of catalytic double DNA-strand passage in vitro may target intracellular enzyme activity in a similar fashion to known poisons that interfere with formation of the enzyme-DNA covalent intermediate.

DNA↗