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At least 19 recordsLinked to original sources

PubMed1992

The effect of proanthocyanidin-rich hulls and proanthocyanidin extracts from bean (Vicia faba L.) hulls on nutrient digestibility and digestive enzyme activities in young chicks.

Proanthocyanidins were prepared from three bean (Vicia faba L.) varieties by extracting hulls in aqueous acetone. The amounts of freeze-dried extracts recovered were 74, 89 and 97 g/kg hull for the varieties Brunette, Statissa and Minica respectively. Chicks (3 weeks old) were fed on a maize-soya-bean control diet or the same control diet substituted with either 30 g proanthocyanidin extracts/kg or 300 g proanthocyanidin-rich hulls/kg. Chicks were tube-fed diets twice daily for 4 d. Nutrient digestibilities were calculated from amounts present in diets and freeze-dried excreta with the aid of titanium dioxide as a marker. Enzyme activities were measured in digesta removed from the jejunum. Extracts of proanthocyanidins depressed the digestibility of protein by 34%, starch by 3% and had no effect on the digestibility of lipid. Proanthocyanidin-rich hulls depressed the digestibility of protein by 62%, starch by 6% and lipid by 4%. Digestive enzyme activities were depressed to the same extent by extracts and hulls, trypsin (EC 3.4.21.4) by 55 and 62%, alpha-amylase (EC 3.2.1.1) by 75 and 78% and lipase (EC 3.1.1.3) by 31 and 32% for proanthocyanidin-extract and proanthocyanidin-rich-hull diets respectively. The susceptibility of substrates as well as enzymes to the effects of proanthocyanidins is discussed.

Animals↗

PubMed1999

Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits.

The aim of this study was to evaluate the antiatherosclerotic effect of proanthocyanidin-rich extracts from grape seeds in cholesterol-fed rabbits. Proanthocyanidin-rich extracts (0.1% and 1% in diets [w/w]) did not appreciably affect the changes in serum lipid profile of cholesterol-fed rabbits. The level of cholesteryl ester hydroperoxides (ChE-OOH) induced by 2,2'-azobis(2-amidinopropane-dihydrochloride (AAPH) were lower in the plasma of rabbits fed proanthocyanidin-rich extract plus cholesterol than in the plasma of rabbits fed cholesterol alone, but not in the low-density lipoprotein (LDL). Aortic malondialdehyde (MDA) content decreased in rabbits fed proanthocyanidin-rich extract. Feeding proanthocyanidin-rich extracts (0.1 and 1% in the diet) to rabbits significantly reduced severe atherosclerosis in the aorta. Immunohistochemical analysis revealed a decrease in the number of oxidized LDL-positive macrophage-derived foam cells in atherosclerotic lesions in the aorta of rabbits fed proanthocyanidin-rich extract. When proanthocyanidin-rich extract was administered orally to rats, proanthocyanidin was detected in the plasma by Porters method but not in the lipoproteins (LDL plus VLDL). In an in vitro experiment using human plasma, proanthocyanidin-rich extract added to the plasma inhibited the oxidation of cholesteryl linoleate in LDL, but not in the LDL isolated after the plasma and the extract were incubated in advance. These results suggested that proanthocyanidins, the major polyphenols in red wine, might trap reactive oxygen species in aqueous series such as plasma and interstitial fluid of the arterial wall, thereby inhibiting oxidation of LDL and showing an antiatherosclerotic activity.

Amidines↗

PubMed1993

The influence of proanthocyanidin-rich bean hulls and level of dietary protein on energy metabolizability and nutrient digestibility by adult cockerels.

Cotyledons and hulls were prepared from twelve varieties of field beans (Vicia faba L.). Adult cockerels were tube-fed either beans, cotyledons or hull diets containing high or low levels of protein. Metabolizable energy coefficients and starch digestibility coefficients were determined for beans, cotyledons and hull diets. Lipid digestibility coefficients from hull diets were also determined. When cotyledons were fed there were no significant differences in the way in which adult cockerels metabolized energy or digested starch from the proanthocyanidin-free and proanthocyanidin-rich varieties (0.780, 0.908, 0.775 and 0.918 respectively). When beans were fed, however, both energy metabolizability and starch digestibility decreased due to the presence of hulls, with proanthocyanidin-rich hulls decreasing values the most to 0.660 and 0.819 respectively, and proanthocyanidin-free hulls decreasing values to a lesser extent to 0.709 and 0.886 respectively. Diets composed of proanthocyanidin-rich hulls depressed metabolizable energy and maize starch digestibility. Their effect on maize starch digestibility, however, was considerably less than that on bean starch. Lipid digestibility was enhanced by proanthocyanidins but only when the protein content of the diet was high. There was a significant correlation (P < 0.05) between the vanillin and anthocyanidin formation methods for the estimation of proanthocyanidins (r 0.779). There was also a highly significant regression of bean starch digestibility v. proanthocyanidin content of coloured-flowered bean hulls (P < 0.001). The regression of maize starch digestibility v. hull proanthocyanidins was also significant at P < 0.005.

Animal Nutritional Physiological Phenomena↗

PubMed2002

Changes in proanthocyanidin chain length in winelike model solutions.

Reactions of seed and skin proanthocyanidins in the presence or absence of (-)-epicatechin were followed in winelike solutions over 53 days at 30 degrees C. Proanthocyanidins were separated from flavanol monomers by sequential elution from a Sep Pak cartridge, and changes in proanthocyanidin composition were monitored by thiolysis analysis of the proanthocyanidin fraction. In solutions containing no free (-)-epicatechin, trace amounts of monomers were released and important losses of proanthocyanidins were measured, but their average composition and mean degree of polymerization (mDP) were hardly modified. In the presence of (-)-epicatechin, the mDP value decreased and oligomeric proanthocyanidins accumulated throughout the incubation while losses of total units were dramatically reduced. Our data indicate that interflavanic bond cleavage of proanthocyanidins occurred under mild acidic conditions such as encountered in wine and that the resulting carbocation proceeded to unknown species. The latter reaction did not take place in the presence of (-)-epicatechin. Epicatechin added to the intermediate carbocation, thus being incorporated as the end unit of a shorter proanthocyanidin chain. The results of this study are discussed in relation to the loss of astringency reported during wine aging.

Anthocyanins↗

PubMed1999

Increase of antioxidative potential of rat plasma by oral administration of proanthocyanidin-rich extract from grape seeds.

The effect of a single oral administration of proanthocyanidins, oligomeric and polymeric polyhydroxyflavan-3-ol units, on the antioxidative potential of blood plasma was studied in rats. Proanthocyanidin-rich extract from grape seeds was administered by intragastric intubation to fasted rats at 250 mg/kg of body weight. The plasma obtained from water- or proanthocyanidin-administered rats was oxidized by incubation with copper sulfate or 2, 2'-azobis(2-amidinopropane) dihydrochloride (AAPH) at 37 degrees C, and the formation of cholesteryl ester hydroperoxides (CE-OOH) was followed. The plasma obtained from proanthocyanidin-administered rats was significantly more resistant against both copper ion-induced and AAPH-induced formation of CE-OOH than that from control rats. The lag phase in the copper ion-induced oxidation of rat plasma was remarkably increased at 15 min after administration of proanthocyanidins and reached a maximum level at 30 min. When the plasma from proanthocyanidin-administered rat was hydrolyzed by sulfatase and beta-glucuronidase following analysis by high-performance liquid chromatography with electrochemical detection, metabolites of proanthocyanidins occurred in rat plasma at 15 min after administration, three peaks of which were identified as gallic acid, (+)-catechin, and (-)-epicatechin. These results suggest that the intake of proanthocyanidins, the major polyphenols in red wine, increases the resistance of blood plasma against oxidative stress and may contribute to physiological functions of plant food including wine through their in vivo antioxidative ability.

Administration, Oral↗

PubMed1999

Cardioprotective effects of grape seed proanthocyanidin against ischemic reperfusion injury.

There is increasing evidence to indicate cardioprotective effects of red wine consumption. Such cardioprotective properties of wine have been attributed to certain polyphenolic constituents of grapes. The purpose of this investigation was to examine whether proanthocyanidins derived from grape seeds possess cardioprotective properties. Rats were randomly divided into two groups: grape-seed proanthocyanidin was administered orally to one group of rats (100 mg/kg/day) for 3 weeks while the other group served as control. After 3 weeks, rats were killed, hearts excised, mounted on the perfusion apparatus and perfused with Krebs-Henseleit bicarbonate (KHB) buffer. After stabilization hearts were perfused in the working mode for baseline measurements of contractile functions. Hearts were then subjected to 30 min of global ischemia followed by 2 h of reperfusion. Coronary perfusates were collected to monitor malonaldehyde formation, a presumptive marker for oxidative stress development. At the end of each experiment, the heart was processed for infarct size determination. Peroxyl radical scavenging activity of proanthocyanidin was determined by examining its ability to remove peroxyl radical generated by 2,2'-azobis (2-amidinopropane) dihydrochloride while hydroxyl radical scavenging activity was tested with its ability to reduce 7-OH.-coumarin-3-carboxylic acid. The results of our study demonstrated that proanthocyanidin-fed animals were resistant to myocardial ischemia reperfusion injury as evidenced by improved recovery of post-ischemic contractile functions. The proanthocyanidin-fed group revealed reduced extent of myocardial infarction compared to the control group. Fluorimetric study demonstrated the antioxidant property of proanthocyanidin as judged by its ability to directly scavenge peroxyl radicals. Taken together, the results of this study showed that grape seed-proanthocyanidins possess a cardioprotective effect against ischemia reperfusion injury. Such cardioprotective property, at least in part, may be attributed to its ability to directly scavenge peroxyl and hydroxyl radicals and to reduce oxidative stress developed during ischemia and reperfusion.

Animals↗

PubMed2001

Rapid quantification of proanthocyanidins (condensed tannins) with a continuous flow analyzer.

Proanthocyanidins (condensed tannins) frequently need to be quantified in large numbers of samples in food, plant, and environmental studies. An automated colorimetric method to quantify proanthocyanidins with sulfuric acid (H(2)SO(4)) was therefore developed for use in a continuous flow analyzer. Assay conditions were optimized using 50% methanol extracts of paper birch, sugar maple, and quaking aspen leaves. Short extraction times and centrifugation of samples prevented proanthocyanidin degradation that otherwise occurred in 50% methanol extracts of aspen leaves. Extraction of birch and maple proanthocyanidins with 50% methanol was comparable to or better than that with 70% acetone. Proanthocyanidin levels in aspen were lower when extracted with aqueous methanol, but relative differences among samples were consistent with those found in aqueous acetone extracts. Results from the automated sulfuric acid assay were highly correlated with those of the conventional BuOH-HCl method for proanthocyanidins and, except for birch, with the Folin--Denis assay for total phenolics. This new technique significantly improves assay processing rate and repeatability compared to conventional colorimetric proanthocyanidin assays.

Anthocyanins↗

PubMed1993

Pigmented Soybean (Glycine max) Seed Coats Accumulate Proanthocyanidins during Development.

The dominant I gene inhibits accumulation of anthocyanin pigments in the epidermal layer of soybean (Glycine max) seed coats. Seed-coat color is also influenced by the R locus and by the pubescence color alleles (T, tawny; t, gray). Protein and RNA from cultivars with black (i,R,T) and brown (i,r,T) seed coats are difficult to extract. To determine the nature of the interfering plant products, we examined seed-coat extracts from Clark isogenic lines for flavonoids, anthocyanins, and possible proanthocyanidins by thin-layer chromatography. We show that yellow seed-coat varieties (I) do not accumulate anthocyanins (anthocyanidin glycosides) or proanthocyanidins (polymeric anthocyanidins). Mature, black (i,R,T) and imperfect-black (i,R,t) seed coats contained anthocyanins, whereas mature, brown (i,r,T) and buff (i,r,t) seed coats did not contain anthocyanins. In contrast, all colored (i) genotypes tested positive for the presence of proanthocyanidins by butanol/ HCl and 0.5% vanillin assays. Immature, black (i,R,T) and brown (i,r,T) seed coats contained significant amounts of procyanidin, a 3[prime],4[prime]-hydroxylated proanthocyanidin. Immature, black (i,R,T) or brown (i,r,T) seed-coat extracts also tested positive for the ability to precipitate proteins in a radial diffusion assay and to bind RNA in vitro. Imperfect-black (i,R,t) or buff (i,r,t) seed coats contained lesser amounts of propelargonidin, a 4[prime]-hydroxylated proanthocyanidin. Seed-coat extracts from these genotypes did not have the ability to precipitate protein or bind to RNA. In summary, the dominant I gene controls inhibition of not only anthocyanins but also proanthocyanidins in soybean seed coats. In homozygous recessive i genotypes, the T-t gene pair determines the types of proanthocyanidins present, which is consistent with the hypothesis that the T locus encodes a microsomal 3[prime]-flavonoid hydroxylase.

Journal Article↗

PubMed2003

Analysis of proanthocyanidins by high-performance gel permeation chromatography.

A high-performance gel permeation chromatography method was developed for the analysis of proanthocyanidins. The isocratic method consisted of two porous polystyrene-divinylbenzene columns (300 x 7.5 mm each, 5 microm, 100 and 500 A individual pore size) and a mobile phase consisting of N,N-dimethylformamide containing 1% (v/v) acetic acid, 5% (v/v) water and 0.15 M lithium chloride. The flow-rate was maintained at 1 ml/min, with a column temperature of 60 degrees C and with detection at 280 nm. The method was used to analyze proanthocyanidin fractions of increasing molecular mass and from different plant tissues. The average molecular mass of proanthocyanidin fractions as determined by acid catalysis in the presence of phloroglucinol, related well with their gel permeation chromatography column retention, yet significant differences in the retention properties between individual plant tissue isolates existed. Proanthocyanidin compositional differences between isolates may explain these differences. A second-order calibration curve was generated from fractionated grape seed proanthocyanidins and this curve was used to analyze grape seed proanthocyanidins isolated from grapes harvested at extremes of maturity.

Chromatography, Gel↗

PubMed2003

Direct method for determining seed and skin proanthocyanidin extraction into red wine.

A method was developed for determining the amount of seed and skin proanthocyanidin extraction into wines by direct measurement. This method was based upon the analysis of proanthocyanidin cleavage products after acid catalysis in the presence of excess phloroglucinol. On the basis of the analysis of proanthocyanidin extracts from grape tissues, two observations were made as follows: (i) the seed and skin proanthocyanidin extension subunit compositions were considerably different from each other, and (ii) their composition did not vary with extraction time. Thus, by comparing the proportional extension subunit composition of proanthocyanidins in wine relative to their proportional composition in corresponding grape seed and skin, it was possible to determine the contribution of each to wine. To provide additional information, the procedure was used to investigate seed and skin proanthocyanidin extraction during commercial-scale fermentations that had undergone 4 or 10 day low temperature prefermentation skin contact prior to the onset of fermentation. The results for both fermentations indicated that the proportion of skin tannin declined during fermentation and also showed that at the end of fermentation the amount and proportion of skin tannin were the same.

Anthocyanins↗

PubMed2001

Effect of grape seed proanthocyanidins on colon aberrant crypts and breast tumors in a rat dual-organ tumor model.

Cancers of the colon and breast are two of the most prevalent cancers in developed countries. The present experiments were conducted to determine the influence of several dietary doses of grape seed proanthocyanidins on 7,12-dimethylbenz[a]anthracene-induced mammary tumorigenesis and azoxymethane (AOM)-induced colonic aberrant crypt foci (ACF) formation in a dual-organ tumor model. In addition, the effects of the grape seed proanthocyanidins on liver cytochrome P-450 1A and 2E1 and glutathione S-transferase activities and on colonic ornithine decarboxylase activity were examined to determine possible mechanisms of action. Feeding female rats diets containing 0.1-1.0% grape seed proanthocyanidins was associated with a significant 72-88% inhibition of AOM-induced aberrant crypt foci formation and a 20-56% inhibition of ornithine decarboxylase activity in the distal third of the colon. Feeding the grape proanthocyanidins resulted in no significant effect on the activity of liver cytochrome P-450 2E1. There was no effect of feeding these doses of proanthocyanidins on 7,12-dimethylbenz[a]anthracene-induced rat mammary tumorigenesis. This lack of action on mammary tumorigenesis in part may be due to lack of effect of dietary proanthocyanidins on the liver carcinogen-metabolizing enzymes cytochrome P-450 1A and glutathione S-transferase. These results indicate that grape polyphenolics warrant further evaluation as potential colon cancer chemopreventive agents.

9,10-Dimethyl-1,2-benzanthracene↗

PubMed2003

New perspectives on proanthocyanidin biochemistry and molecular regulation.

Our understanding of proanthocyanidin (syn. condensed tannin) synthesis has been recently extended by substantial developments concerning both structural and regulatory genes. A gene encoding leucoanthocyanidin reductase has been obtained from the tropical forage, Desmodium uncinatum, with the latter enzyme catalyzing formation of (+)-catechin. The BANYULS gene in Arabidopsis thaliana, previously proposed to encode leucoanthocyanidin reductase or to regulate proanthocyanidin biosynthesis, has been shown instead to encode anthocyanidin reductase, which in turn converts anthocyanidins (pelargonidin, cyanidin, or delphinidin) into 2,3-cis-2R,3R-flavan-3-ols (respectively, (-)-epiafzelechin, (-)-epicatechin and (-)-epigallocatechin). However, the enzyme which catalyzes the polymerization reaction remains unknown. Nevertheless, a vacuolar transmembrane protein TT12, defined by the Arabidopsis tt12 mutant, is involved in transport of proanthocyanidin polymer into the vacuole for accumulation. Six different types of regulatory elements, e.g. TFIIIA-like, WD-40-like, WRKY-like, MADS-box-like, myb-like, and bHLH (myc-like), have been cloned and identified using mutants from Arabidopsis (tt1, ttg1, ttg2, tt2, tt16, tt2, tt8) and two other species (Hordeum vulgare [ant13] and Lotus spp [tan1]). Accordingly, increases in proanthocyanidin levels have been induced in the the world's major forage, alfalfa. These advances may now lead to a detailed understanding of how PA synthesis is controlled and to useful alterations in proanthocyanidin concentration for the improvement of forage species, pulses, and other crop plants.

Arabidopsis↗

PubMed2001

Composition of grape skin proanthocyanidins at different stages of berry development.

The composition of grape (Vitis vinifera L. cv. Shiraz) skin proanthocyanidins has been determined at different stages of berry development. Beginning approximately 3 weeks after fruit set and concluding at commercial ripeness, the composition of isolated skin proanthocyanidins was determined using the following analytical techniques: elemental analysis, UV-Vis absorption spectroscopy, reversed-phase HPLC after acid-catalysis in the presence of excess phloroglucinol, gel permeation chromatography, electrospray ionization mass spectrometry (ESI-MS), and (13)C NMR. On the basis of these analyses, berry development was correlated with an increase in proanthocyanidin mean degree of polymerization, an increase in the proportion of (-)-epigallocatechin extension subunits, and increases in the level of anthocyanins associated with the proanthocyanidin fraction. Additionally, data acquired from ESI-MS of the isolates following acid-catalysis in the presence of excess phloroglucinol is consistent with pectin-bound proanthocyanidins.

Anthocyanins↗

PubMed1999

Quantitative fractionation of grape proanthocyanidins according to their degree of polymerization.

A method was developed for the fractionation of grape (seed or skin) proanthocyanidins according to their degree of polymerization. After precipitation in chloroform/methanol (75:25, v/v), the grape proanthocyanidins were deposited onto an inert glass powder column and sequentially dissolved in several fractions by increasing proportions of methanol in the solvent. Each fraction from each proanthocyanidin source was quantified and characterized after acidic degradation with phenylmethanethiol (i.e., thiolysis). The comparison of data from total extract and successive fractions showed that a quantitative separation was achieved so that estimation of polymer size distribution in relation to other compositional characteristics (proportions of prodelphinidin units, galloylation rate) was thus possible. Mean degree of polymerization of separated proanthocyanidins ranged increasingly from 4.7 to 17.4 in seed (8.1 for total extract) and from 9.3 to 73.8 in skin (34.9 for total extract). The method proposed is very interesting for the study of grape proanthocyanidins according to their degree of polymerization because it gives both qualitative and quantitative information especially on the highly polymerized forms, which were not fractionated by previous techniques.

Anthocyanins↗

PubMed2000

Gibberellic acid (GA3) induced changes in proanthocyanidins and malt quality of two- and six-row husked barleys.

Analysis of husked barleys for proanthocyanidins and malt quality attributes has shown that not a single variety is free of proanthocyanidins. The proanthocyanidins in barley grains varied from 3.85 to 4.94 mg/g as catechin equivalent. The concentration of proanthocyanidins decreased, while total soluble sugars, reducing sugars, diastatic power and beta-amylase activity increased during maltings as well as with exogenous gibberellic acid (GA3) application. Alfa 93 (two-row) and RD2560 (six-row) varieties appeared to be superior for malting and brewing purposes on the basis of proanthocyanidins, total phenols, diastatic power and beta-amylase activity. It is suggested that exogenous application of GA3 at 15 ppm may be useful for producing good quality malt from barley grains.

Anthocyanins↗

PubMed2002

Oligomeric proanthocyanidins: naturally occurring O-heterocycles.

This review covers the flavan-3-ols (catechins), flavan-4-ols/flavan-3,4-diols (leucoanthocyanidins), A-type proanthocyanidins, B-type proanthocyanidins including the procyanidins, prodelphinidins, propelargonidins, proteracacinidins, promelacacinidins, procassinidins, probutinidins, and non-proanthocyanidins with flavan-3-ol constituent units. Newly isolated proanthocyanidins, structure elucidation, syntheses, HPLC/MS analysis, NMR/ conformational analysis, and the effects of proanthocyanidins on human nutrition and health are reported. The literature from January 1999 to December 2001 is reviewed, and 130 references are cited.

Animals↗

PubMed2002

Safety evaluation of proanthocyanidin-rich extract from grape seeds.

Proanthocyanidins, extracted from grape seeds, are widely used mainly as nutritional supplements. However, there has not been a systematic report to investigate toxicological studies on proanthocyanidins, especially in oral administration. In our studies, proanthocyanidin-rich extract from grape seeds was subjected to a series of toxicological tests to document its safety for use in various foods. The grape seed extract (GSE) was examined for acute and subchronic oral toxicity using Fischer 344 rats and for mutagenic potential by the reverse mutation test using Salmonella typhimurium, the chromosomal aberration test using CHL cells, and the micronucleus test using ddY mice. No evidence of acute oral toxicity at dosages of 2 and 4 g/kg, and no evidence of mutagenicity in the above tests was found. Administration of GSE as a dietary admixture at levels of 0.02, 0.2 and 2% (w/w) to the rats for 90 days did not induce noticeable signs of toxicity. The no-observed-adverse-effect level (NOAEL) of GSE in the subchronic toxicity study was 2% in the diet (equal to 1410 mg/kg body weight/day in males and 1501 mg/kg body weight/day in females). The results of our studies indicate a lack of toxicity and support the use of proanthocyanidin-rich extract from grape seeds for various foods.

Animals↗

PubMed2000

Chemopreventive effects of grape seed proanthocyanidin extract on Chang liver cells.

In an attempt to ameliorate the chemotherapy associated normal cell toxicity, in this study a known antioxidant, grape seed proanthocyanidin extract (GSPE) using Chang liver cells has been used. Chang liver cells were treated in vitro with idarubicin (Ida) (30 nM) and 4-hydroxyperoxycyclophosphamide (4-HC) (1 microg/ml) with or without proanthocyanidin (25 microg/ml). The cells were grown in vitro and the growth rate of the cells were determined using MTT assay. The results showed that the GSPE decreased growth inhibitory effects of Ida and 4-HC on Chang liver cells in vitro. Since these chemotherapeutic agents are known to induce apoptosis in the target cells, these cells were also analyzed for presence of apoptotic cells using flow cytometry. The GSPE decreased the number of apoptotic cell population induced by either chemotherapy. In an attempt to determine the mechanisms of ameliorating effects of proanthocyanidin, the expression of apoptosis/cell cycle/growth related genes, Bcl-2, p53 and c-myc was determined in the treated and control cells using Western blotting or reverse transcriptase-polymerase chain reaction (RT-PCR) techniques. There was an increased expression of Bcl-2 in the cells treated with GSPE. However, there was a significant decrease in the expression of other cell cycle related genes such as p53 and c-myc in these cells following treatment with GSPE. Thus, these results indicate that proanthocyanidin can be a potential candidate to ameliorate the toxic effects associated with chemotherapeutic agents used in treatment of cancer.

Anthocyanins↗