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PubMed1998

Natural dietary polyphenolic compounds cause endothelium-dependent vasorelaxation in rat thoracic aorta.

This study investigated the possible active principles which support the endothelial nitric oxide-dependent relaxation produced by red wine and other plant polyphenolic compounds in thoracic aorta from male Wistar rats (12-14 wk old). Relaxation experiments were recorded isometrically on vessels precontracted with norepinephrine. Ten different chromatographic fractions (3-18 mg) isolated from red wine polyphenolic compounds (RWPC) and some available defined polyphenols (10-15 mg) were tested. Fractions enriched into either anthocyanins or oligomeric condensed tannins exhibited endothelium-dependent vasorelaxant activity (maximal relaxation in the range of 59-77%) comparable to the original RWPC. However, polymeric condensed tannins elicited a weaker vasorelaxant activity than the original RWPC (maximal relaxation ranged between 20-47%, P < 0.01). Moreover, the representative of either phenolic acid derivatives (benzoic acid, vanillic acid, gallic acid), hydroxycinnamic acid (p-coumaric acid, caffeic acid) or the flavanol [(+)-epicatechin] classes failed to induce this type of response. Among the anthocyanins, delphinidin (maximal relaxation being 89%), but not malvidin or cyanidin, showed endothelium-dependent vasorelaxation. These results show that anthocyanins and oligomeric-condensed tannins exhibited a pharmacological profile comparable to the original RWPC. These compounds may be involved in the reduction of cardiovascular mortality related to the presence of wine, fruits and vegetables in the diet.

Animals↗
PubMed2000

Clonal variation in morphology, growth, physiology, anatomy and ultrastructure of container-grown white spruce somatic plants.

We assessed clonal variation in morphological variables, mineral nutrition, root growth capacity, net photosynthesis, tannin distribution, and cuticle and epicuticular wax features within four families of white spruce (Picea glauca (Moench) Voss). Seeds were collected from four families obtained through controlled crosses among selected genotypes. For each family, plants were produced either from seeds (zygotic) or by somatic embryogenesis (clones). Each family was therefore represented by its zygotic seedlings and three clones. Within a family and under similar growth conditions, several clones differed significantly from the zygotic seedlings in height, root-collar diameter, needle dry mass, branch density, shoot dry mass, root dry mass, and length of needles. Branch density (number of first-order branches per cm height) of zygotic seedlings and clones varied from 0.8 to 1.4 branches cm(-1) and from 0.6 to 1.3 branches cm(-1), respectively. Mean needle length of zygotic seedlings and clones ranged from 11 to 14 mm and from 11 to 17 mm, respectively. For many variables (height, dry mass of new roots, needle dry mass and branch density), differences among clones were significantly greater than differences among zygotic seedlings within a family. Tannins were more abundant in needles of clones than in needles of zygotic seedlings. In some clones, tannins occurred as a ribbon along the central vacuole, whereas in others they appeared as aggregates dispersed in the vacuole. Within a family, N, P and K showed considerable variations in their use efficiency. Interclonal variations were observed in root growth potential and net photosynthesis. Variations in growth and physiology reflect genetically determined differences among clones within a family.

Genetic Variation↗
PubMed1997

Increased Expression of Vacuolar Aquaporin and H+-ATPase Related to Motor Cell Function in Mimosa pudica L.

Mature motor cells of Mimosa pudica that exhibit large and rapid turgor variations in response to external stimuli are characterized by two distinct types of vacuoles, one containing large amounts of tannins (tannin vacuole) and one without tannins (colloidal or aqueous vacuole). In these highly specialized cells we measured the abundance of two tonoplast proteins, a putative water-channel protein (aquaporin belonging to the [gamma]-TIPs [tonoplast intrinsic proteins]) and the catalytic A-subunit of H+-ATPase, using either high-pressure freezing or chemical fixation and immunolocalization. [gamma]-TIP aquaporin was detected almost exclusively in the tonoplast of the colloidal vacuole, and the H+-ATPase was also mainly localized in the membrane of the same vacuole. Cortex cells of young pulvini cannot change shape rapidly. Development of the pulvinus into a motor organ was accompanied by a more than 3-fold increase per length unit of membrane in the abundance of both aquaporin and H+-ATPase cross-reacting protein. These results indicate that facilitated water fluxes across the vacuolar membrane and energization of the vacuole play a central role in these motor cells.

Journal Article↗
PubMed2002

TRANSPARENT TESTA GLABRA2, a trichome and seed coat development gene of Arabidopsis, encodes a WRKY transcription factor.

Mutants of a new gene, TRANSPARENT TESTA GLABRA2 (TTG2), show disruptions to trichome development and to tannin and mucilage production in the seed coat. The gene was tagged by the endogenous transposon Tag1 and shown to encode a WRKY transcription factor. It is the first member of this large, plant-specific family known to control morphogenesis. The functions of all other WRKY genes revealed to date involve responses to pathogen attack, mechanical stress, and senescence. TTG2 is strongly expressed in trichomes throughout their development, in the endothelium of developing seeds (in which tannin is later generated) and subsequently in other layers of the seed coat, and in the atrichoblasts of developing roots. TTG2 acts downstream of the trichome initiation genes TTG1 and GLABROUS1, although trichome expression of TTG2 continues to occur if they are inactivated. Later, TTG2 shares functions with GLABRA2 in controlling trichome outgrowth. In the seed coat, TTG2 expression requires TTG1 function in the production of tannin. Finally, TTG2 also may be involved in specifying atrichoblasts in roots redundantly with other gene(s) but independently of TTG1 and GLABRA2.

Amino Acid Sequence↗
PubMed1998

Mechanism of the protective effects of sumac gall extract and gallic acid on the progression of CCl4-induced acute liver injury in rats.

To examine the mechanism of the preventive effect of tannins on the progression of carbon tetrachloride (CCl4)-induced acute liver injury in rats, sumac gall (SG) extract and gallic acid (GA) were used as substitutes for crude tannins, because SG is a kind of Chinese traditional medicinal herb containing large amounts of various tannins, and GA is one of the major constituents of SG. The protective effect of oral (p.o.) and intraperitoneal (i.p.) administration of each substance on progression of CCl4-induced hepatitis was investigated in rats. Speculating that the superoxide dismutase (SOD)-like activities (O2 radical-scavenging activities) and/or protective effects of these substances on cell membranes might play a key role in the mechanism opposing the progression of CCl4-induced hepatitis, the O2 radical-scavenging activities in liver cells and serum in rats were monitored. Both substances significantly prevented the progression of acute liver injury with both p.o. and i.p. administration. These findings suggest that the mechanism for this prevention might be due mainly to the protective effect of these substances on cell membranes rather than O2 radical-scavenging activities.

Acute Disease↗
PubMed1995

Effects of a component of green tea on the proliferation of vascular smooth muscle cells.

The effects of a component of green tea on the proliferation of smooth muscle cells were measured in terms of [3H]thymidine uptake. When green tea tannin mixture was added to the medium of cultured smooth muscle cells, it suppressed the proliferation of the cells dose-dependently. Similarly to the effects of the green tea tannin mixture, (-)-epigallocatechin 3-O-gallate, its main ingredient, had an inhibitory effect on smooth muscle cell proliferation at a low concentration. (-)-Epicatechin 3-O-gallate was also an effective component. Among four types of gallate-free tannin, (-)-epigallocatechin, (-)-epicatechin, and (+)-catechin showed significant dose-dependent inhibition of smooth muscle cell proliferation. However, caffeine and theanine were found to have no such action.

Animals↗
PubMedDate not supplied

Antioxidative and antiradical properties of plant phenolics.

The plant phenolic compounds such as flavonoids, tannins and phenolic acids appeared to be strong antiradical and antioxidant compounds. The number of hydroxy groups and the presence of a 2,3-double bond and orthodiphenolic structure enhance antiradical and antioxidative activity of flavonoids. The glycosylation, blocking the 3-OH group in C-ring, lack of a hydroxy group or the presence of only a methoxy group in B-ring have a decreasing effect on antiradical or antioxidative activity of these compounds. Tannins show strong antioxidative properties. Some tannins in red wine or gallate esters were proved to have antioxidative effect in vivo. The number of hydroxy groups connected with the aromatic ring, in ortho or para position relative to each other, enhance antioxidative and antiradical activity of phenolic acids. The substitution of a methoxy group in ortho position to the OH in monophenols seems to favour the antioxidative activity of the former.

Antioxidants↗
PubMed2004

Ruminal fermentation and degradation patterns, protozoa population and urinary purine derivatives excretion in goats and wethers fed diets based on olive leaves.

Olives leaves, accrued during the processing of olive harvests for oil extraction, are poor in N, rich in crude fat and ADF (1.19, 8.03 and 28.2 g/100 g of DM, respectively), and relatively low in condensed tannins (11.1 mg/g of DM). Three experiments were conducted in a 2 x 3 (two animal species: goats vs. wethers; and three experimental diets: olive leaves without or with polyethylene glycol supply and olive leaves supplemented with barley and faba beans) factorial design to evaluate ruminal degradation and passage kinetics (Exp. 1), fermentation pattern and protozoa population (Exp. 2), and urinary purine derivatives excretion (Exp. 3). Polyethylene glycol was supplied to evaluate the effects of condensed tannins contained in olive leaves. Ruminal degradability of CP was low in both goats and wethers, although goats showed higher (P < 0.05) values than wethers. Supplementation of olive leaves with barley and faba beans increased (P < 0.001) ruminal degradability of DM and CP. Both goats and wethers fed olive leaves showed similarly low particulate fractional passage rates (0.021 and 0.023/h, respectively). Ingestion of olive leaves promoted low NH3-N and VFA concentrations, which reflect poor microbial activity. These concentrations, especially that of VFA, increased when barley and faba beans were added. Ingestion of olive leaves affected ruminal protozoa: Entodiniomorphida showed low concentrations and Holotricha completely disappeared. When animals received a diet based on olive leaves, barley, and faba beans, Holotricha appeared in the ruminal liquor and Entodiniomorphida increased (P < 0.001). In goats and wethers fed olive leaves alone, urinary allantoin excretion was very low (163 and 164 micromol/kg BW0.75 in goats and wethers, respectively), and moderate values (352 and 389 micromol/kg BW0.75 in goats and wethers, respectively) were observed when a diet of olive leaves, barley, and faba beans was fed. The polyethylene glycol supply did not have an effect in goats or in wethers, indicating the lack of an effect of condensed tannins in olive leaves. Ingestion of olive leaves promotes a low microbial activity, although its supplementation with readily degraded carbohydrates and protein improves microbial activity and, as a consequence, increases its ruminal degradation. In general, for most of the measured variables, there were no animal species x diet interactions. Thus, goats and wethers had similar ruminal activities when fed diets based on olive leaves.

Animal Feed↗
PubMed1998

[Effect of cooking on the chemical and nutritional value of the Pithecellobium flexicaule (Bent) seed].

The leguminous P. flexicaule grows at the Northeast of Mexico. People living at this region traditionally consume the seeds (unripe cooked or toasted mature). Three localities samples of mature seeds were analyzed. The main results were: Protein (Nx6.25) 35.3%, lipids 25% and total dietary fiber (TDF) 13.2%. After a toasted treatment during 10 minutes (80-90 degrees C), the true protein digestibility increased from 79.3-91.8%, the phytate content and protein inhibitors decreased up to 35 an 96% respectively. Tannin concentration increased from 12.4 to 236 mg eq. cathequine/100 g, probably because during the treatment they passed from the shell to the cotyledons. Unripe seeds gave; protein 12.7%, lipids 6.6%, TDF 3.5%. When the unripe seeds in their sheath were boiling, the true protein digestibility was 85.8% (same value of the raw seeds), phytate content was reduced 68.4% and tannin concentration rose from 4.9 to 226 mg. Due to these results, the seeds free of the shell and sheaths were boiling, this time the tannin and phytate concentration were reduced 73.5 and 88.6% respectively, the true protein digestibility was 94.5%. The sulphur containing amino acids were the limit, as in other leguminous, the protein digestibility corrected amino acid score was 50.6% (unripe seeds), similar to that of pinto beans.

Cooking↗
PubMed2005

Anti-HIV activity against immunodeficiency virus type 1 (HIV-I) and type II (HIV-II) of compounds isolated from the stem bark of Combretum molle.

In vitro anti-HIV activity of various extracts prepared from the stem bark of Combretum molle (R. Br. Ex. G. Don.) Engl & Diels (Combretaceae), a plant widely used in Ethiopian traditional medicine for the treatment of liver diseases, malaria and tuberculosis has been assessed against human imnmuunodeficiencvy virus type 1 (HIV-1) and type 2 (HIV-2). The total extract was prepared by percolation with 80% methanol whilst the petroleum ether, chloroform, acetone and 100% methanol fractions were obtained by successive hot extraction using Soxhlet apparatus. Selective inhibition of viral growth was assessed by the simultaneous determination of the in vitro cytotoxicity of each of the extracts against MT-4 cells. Results obtained in this study indicate that the acetone fraction possessed the highest selective inhibition of HIV-1 replicatuon. Phytochemical investigation of the acetone fraction resulted in the isolation of two tannins and two oleanane-type pentacyclic triterpene glycosides. One of the tannins was identified as puncalagin (an ellagitannin), whilst the structure of the other (CM-A) has not yet been fully elucidated. The saponins that were characterized as arjunglucoside (also called 4-epi-sericoside) and sericoside did not inhibit replication of either HIV-1 or HIV-2. On the other hand, both punicalgin and CM-A displayed selective inhibition of HIV-1 replication with selectrvitv indices (ratio of 50% cytotoxic concentration to 50% effective antiviral concentration) of 16 and 25, respectivelvy and afforded cell protection of viral induced cytopathic effect of 100% when compared with control samples. Neither of the tannins exhibited a selective inhibition to HIV-2 replication at nontoxic doses.

Antiviral Agents↗
PubMed1989

Iron absorption and phenolic compounds: importance of different phenolic structures.

The phenolic compounds (phenolic monomers, polyphenols, tannins) are considered to interfere with iron absorption by complex formation with iron in the gastro-intestinal lumen, making the iron less available for absorption. Very little is known about the extent to which different types of phenolic compounds of different size and chemical structure inhibit iron absorption. The relationship between iron absorption and the amount and type of phenolic compounds was studied by the extrinsic tag method. The aims of the studies were as follows: (i) To study the effect of small phenolic compounds with different hydroxylation patterns (gallic acid, catechin, chlorogenic acid) on iron absorption, (ii) To study the effect of different amounts of a hydrolysable tannin containing ten gallic acid residues (tannic acid) on iron absorption. (iii) To study the degree of inhibition of iron absorption by some foods and beverages (oregano, spinach, coffee and tea) in relation to their respective content of iron-binding phenolic groups, measured by a newly developed method. The inhibition of iron absorption by tannic acid was strongly dose-related. The smallest amount (5 mg) inhibited absorption by 20 per cent, 25 mg by 67 per cent and 100 mg by 88 per cent. Gallic acid inhibited iron absorption to the same extent as tannic acid, per mol galloyl groups, whereas no inhibition was observed when catechin was added to the test meal. Chlorogenic acid inhibited iron absorption to a lesser extent. Oregano and tea inhibited iron absorption in proportion to their respective content of galloyl groups, whereas the inhibitory effect of spinach was less marked. The inhibiting effect of coffee was explained mainly by its content of galloyl groups, but also by some other factor, probably chlorogenic acid. It is concluded that the content of iron-binding galloyl groups might be a major determinant of the inhibitory effect of phenolic compounds on iron absorption from the diet, whereas the phenolic catechol groups seem to be of minor importance. The results further suggest that the group of condensed tannins do not interfere with iron absorption.

Absorption↗
PubMed1979

Inhibition of DNA synthesis in cultured lymphocytes and tumor cells by extracts of betel nut, tobacco, and miang leaf, plant substances associated with cancer of the ororespiratory epithelium.

The high incidence of oropharyngeal, esophageal, and laryngeal cancers in certain parts of the world has been ascribed to conjugated tannins found in certain folk medicinal herbs. We extracted miang leaf and betel nut with phosphate-buffered saline (0.14 M NaCl, 0.15 M potassium phosphate buffer, pH 7.4) and found that the extracts inhibited [3H]thymidine incorporation by phytohemagglutinin-stimulated human lymphocytes and by rat mammary tumor and mouse L-cells in logarithmic growth. Pretreating the lymphocytes for 1 or 4 hr with the extracts inhibited phytohemagglutinin-induced thymidine incorporation 72 hr later. At concentrations of 2.5 volumes % or lower, miang and betel nut extracts inhibited thymidine incorporation by 40 to 98% without any apparent signs of toxicity as demonstrated by the 66Rb equilibrium assay. In addition, neither extract inhibited cytotoxicity of rat mammary tumor cells by immune syngeneic spleen cells. The molecular weights of the inhibitory factors were between 1,000 and 10,000 daltons as determined by ultrafiltration and were unaffected by boiling for 3 min or by treatment with alcohol and, therefore, are probably not proteins. This in vitro demonstration of inhibition of DNA synthesis by these plant extracts presumably enriched for conjugated tannins may relate to inhibition of growth of rats and chicks fed conjugated tanin-contaminated sorghum feed. The carcinogenic potential of either these extracts or conjugated tannins is not yet established.

Animals↗
PubMedDate not supplied

[Differentiation of natural red wines from white wines blended with oenocyanine (author's transl)].

A method is proposed for the differentiation of natural red wines from those obtained by addition of oenocyanine to white wines. The procedure is based on the determination of tannin phenolics and nontannin phenolics by selective precipitation with methyl cellulose and subsequent estimation of the intensity of absorption at 450 nm and 520 nm. The sum of ratio: mg/1 non tannin phenolics/absorption at 450 nm X 1000 and mg/1 tannin phenolics/absorption at 520 nm X 1000, furnishes values which are in correlation with the origin of two wines and such as to consent their differentiation.

Cyanates↗
PubMed2007

Induction of salivary polypeptides associated with parotid hypertrophy by gallotannins administered topically into the mouse mouth.

Isoproterenol-induced salivary polypeptides (IISP), a group of proline-rich proteins synthesized by mouse parotids, have been considered as markers for isoproterenol-induced parotid hypertrophy. Rodents fed diets containing high-tannin cereals (sorghum), also develop parotid hypertrophy. To test whether tannins are directly involved in provoking sialotrophic growth, we studied the effect of intraperitoneal and topical oral administrations of tannic acid (TA) on the induction of IISP polypeptides in endogamic mice (A/Snell). TA was characterized by HPLC chromatography and spectral analysis and shown to be composed solely of gallotannins, a complex family of glucose and gallic acid esters. IISP polypeptides were monitored in saliva by SDS-polyacrylamide gel electrophoresis during 36 h after ending TA stimulation. Single daily intraperitoneal administrations of TA for 3 consecutive days (0.033 mg/g bw/day), at variance of parallel administrations of isoproterenol (0.042 mg/g bw/day) failed to induce IISP polypeptides. However, repeated topical applications of TA into the mouse mouths (1.21 mg/g bw divided into three equal doses given at 4-h intervals within a single day) resulted in unequivocal induction of IISP polypeptides. That response was clearly intensified by increasing the stimulation frequency to eight equivalent doses given at 1.5-h intervals within a single day (corresponding to 3.23 mg/g bw) and even further by repeating this protocol for 3 days. Under these productive schemes of stimulations by TA, electrophoretic fractionation of parotid homogenates showed new polypeptide bands migrating in parallel to salivary IISP. These results suggest that topically administered gallotannins are effective inducers of trophic growth in mouse parotids.

Administration, Oral↗
PubMed1997

Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation.

Polyphenols (tannins) in the diet not only precipitate oral proteins, producing an astringent sensation, but also interact with dietary proteins and digestive enzymes in the gut, resulting in a variety of antinutritive and toxic effects. Salivary proline-rich proteins (PRPs), which are secreted into the oral cavity, form complexes with and precipitate dietary polyphenols, and thus, they constitute the primary mammalian defense directed against ingested tannins. In order to characterize the interaction, NMR studies were performed which involved titrating a series of polyphenols into a synthetic 19-residue PRP fragment. The results show that the predominant mode of association is a hydrophobic stacking of the polyphenol ring against the pro-S face of proline and that the first proline residue of a Pro-Pro sequence is a particularly favored binding site. Measurement of dissociation constants indicates that the larger and more complex polyphenols interact more strongly with the PRP fragment; the order of binding affinity was determined as procyanidin dimer B-2 > pentagalloylglucose > trigalloylglucose >> proanthocyanidin monomer (-)-epicatechin approximately propyl gallate. Smaller polyphenols can bind with one phenolic ring stacked against each proline residue, whereas larger polyphenols occupy two or three consecutive prolines. The more complex polyphenols interact with the PRP fragment in a multidentate fashion; moreover, they self-associate or stack when bound. Thus, a model is proposed in which multiple polyphenol/polyphenol and polyphenol/PRP interactions act cooperatively to achieve precipitation.

Amino Acid Sequence↗
PubMed1965

CONFIGURATION OF GUIBOURTACACIDIN, AND SYNTHESIS OF ISOMERIC RACEMATES.

1. Diacetates of the four possible racemates of 4',7-dimethoxyflavan-3,4-diol have been synthesized. 2. Comparison of their nuclear-magnetic-resonance spectra and the ionophoretic mobilities of the diols in borate buffer with those of the corresponding derivatives of guibourtacacidin shows that the natural 4',7-dihydroxyflavan-3,4-diol has a 2,3-cis-3,4-trans configuration, but is accompanied by 2,3-trans-3,4-trans and 2,3-trans-3,4-cis isomers. These occur in the approximate proportions 5:1:1. 3. The occurrence of guibourtacacidins in Guibourtia coleosperma appears to be of taxonomic significance. Their association with a large excess of related tannins in the heartwood suggests that flavan-3,4-diols with these configurations are suitable precursors in tannin biosynthesis.

Benzopyrans↗
PubMed1977

Tannic acid and oxidized tannic acid on the functional state of rat intestinal epithelium.

Diets containing tannic acid at the level of 3% of dry matter were fed to rats in order to ascertain the origin of fecal nitrogen and the effect of tannic acid on the intestinal mucosa. At the same time in order to explain the effect of oxidation of tannins, we administered diets containing oxidized tannic acid or tannic acid associated with an antioxidizer (sodium sulfite) at the level of 1% of dry matter. The increased excretion of sialic acid and glucosamine during ingestion of tannic acid indicated that the excess of fecal nitrogen mainly corresponds to the mucus hypersecretion observed by histology. Fecal analysis revealed perturbations in movements of water and ions. The study of the metabolic activity of isolated enterocytes and the activity of some enzymes in a homogenate of these cells showed an inhibition of oxygen consumption and succinic dehydrogenase activity. Addition of reducing agent (sodium sulfite) to the diet had little effect on the action of tannic acid; but previous oxidation of the tannin reduced the effects observed, particularly in the case of fecal nitrogen loss.

Animals↗
PubMed1979

Effects of tannic acid and its related compounds upon Chikungunya virus.

The present report describes not only the effects of tannic acid (TA; belonging to hydrolyzable tannins) and its related compounds upon the infectivity of Chikungunya virus (CHIKV) but also the mechanism involved in this phenomenon. Our data show that TA inactivates CHIKV in vitro. Since the inactivating effect turned out to be pH-dependent and was suppressed by bovine serum albumin, it is most probable that the virus-inactivating capacity of TA is attributable to its preferential binding to proteins of virus particles. Examination on the virus-inactivating capacities of some TA-related compounds and comparison of their structures indicated that the active site of TA and its analogues might be the phenolic hydroxyl groups in their molecules. It seems that the active groups interact with the proteins of virus particles, resulting in a reduction or loss of viral infectivity. Discussion is made on the specificity of the actions of tannins and the possibility of application thereof to chemicals which are useful to investigate the nature and properties of viral proteins.

Animals↗