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PubMed2004

Identification and quantification of polyphenols in carob fruits (Ceratonia siliqua L.) and derived products by HPLC-UV-ESI/MSn.

The polyphenolic patterns of carob pods (Ceratonia siliqua L.) and derived products were identified and quantified using high-performance liquid chromatography-UV absorption-electrospray ion trap mass spectrometry after pressurized liquid extraction and solid-phase extraction. In carob fiber, 41 individual phenolic compounds could be identified. In addition, spectrophotometric quantification using the Folin-Ciocalteu and vanillin assays was performed, and the antioxidative activity was determined as the 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity. Carob pods contain 448 mg/kg extractable polyphenols comprising gallic acid, hydrolyzable and condensed tannins, flavonol-glycosides, and traces of isoflavonoids. Among the products investigated, carob fiber, a carob pod preparation rich in insoluble dietary fiber (total polyphenol content = 4142 mg/kg), shows the highest concentrations in flavonol-glycosides and hydrolyzable tannins, whereas roasted carob products contain the highest levels of gallic acid. The production process seems to have an important influence on the polyphenolic patterns and quantities in carob products.

Antioxidants↗
PubMed2004

Chemical and sensory characterization of DOC red wines from Marche (Italy) related to vintage and grape cultivars.

Monomeric phenols, color and copigmentation parameters, pigments with different chemical structure, tannin, glucose, fructose, glycerol, ethanol, and organic acids were determined in DOC red wines from Marche (Italy), obtained during three different vintages ranging from 1996 to 2000. The intensity of the bitter and astringent tastes of the wines was determined with panel tastings. Lacrima di Morro and Vernaccia di Serrapetrona (obtained from local cultivars) were different from Rosso Piceno, Rosso Piceno Superiore, and Rosso Conero (produced from different percentages of Sangiovese and Montepulciano). Vernaccia, a red, sweet, "spumante" wine, was an outlier. Lacrima showed a low tannin content, a high content of small pigments and phenols, and a high ratio of copigmented color, which persisted after 3 years of aging. The chemical determinations accounted for a high percentage of variability of measured panel astringency, copigmented color, and measured wine absorbance at 520 nm. It was not possible to create a predictive model for bitterness.

Fruit↗
PubMed2004

Antioxidant phenolic constituents in roots of Rheum officinale and Rubia cordifolia: structure-radical scavenging activity relationships.

The phenolic constituents in the roots of Rheum officinale and Rubia cordifolia were identified with the aid of high-performance liquid chromatography and liquid chromatography-mass spectrometry and by comparison with authentic standards. A total of 17 hydroxyanthraquinones, gallic acid, and tannins were separated, and 14 of them were identified, being the main phenolic constituents present. Their antioxidant activity (Trolox equivalent antioxidant capacity) was evaluated using the improved 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)diammonium salt method. Hydroxyanthraquinones were the predominant antioxidant phenolic constituents in the roots of R. cordifolia, and tannins and gallic acid were the predominant antioxidant phenolic constituents in the roots of R. officinale. The structure-radical scavenging activity relationships of the tested hydroxyanthraquinones were systematically demonstrated as follows: Hydroxy groups on one benzene ring of the anthraquinone structure were essential for hydroxyanthraquinones to show activity, the ortho-dihydroxy structure in the hydroxyanthraquinone molecules could greatly enhance their radical scavenging effect, and glycosylation of the hydroxyanthraquinones reduced activity.

Anthraquinones↗
PubMed2005

Decorticating sorghum to concentrate healthy phytochemicals.

The growing prominence of nutrition-related health problems demands strategies that explore nontraditional natural ingredients to expand healthy food alternatives. Specialty sorghums were decorticated using a tangential abrasive dehulling device (TADD) to remove successive bran layers, which were collected at 1 min intervals and analyzed for phenols, tannins, 3-deoxyanthocyanins, dietary fiber, and antioxidant activity. The first two bran fractions had the highest levels of phenols and antioxidant activity (3-6 times as compared to whole grain). Brown (tannin-containing) and black sorghums had at least 10 times higher antioxidant activity than white sorghum or red wheat brans. Black sorghums had the highest 3-deoxyanthocyanin content (up to 19 mg/g bran). Dietary fiber in sorghum brans ranged between 36 and 45%, as compared to 48% for wheat bran. Specialty sorghum brans are rich in valuable dietary components and present promising opportunities for improving health attributes of food.

Anthocyanins↗
PubMed2006

A simple method to separate red wine nonpolymeric and polymeric phenols by solid-phase extraction.

Simple polyphenols and tannins differ in the way that they contribute to the organoleptic profile of wine and their effects on human health. Very few straightforward techniques to separate red wine nonpolymeric phenols from the polymeric fraction are available in the literature. In general, they are complex, time-consuming, and generate large amounts of waste. In this procedure, the separation of these compounds was achieved using C18 cartridges, three solvents with different elution strengths, and pH adjustments of the experimental matrices. Two full factorial 2(3) experimental designs were performed to find the optimal critical variables and their values, allowing for the maximization of tannin recovery and separation efficiency (SE). Nonpolymeric phenols such as phenolic acids, monomers, and oligomers of flavonol and flavan-3-ols and anthocyanins were removed from the column by means of an aqueous solvent followed by ethyl acetate. The polymeric fraction was then eluted with a combination of methanol/acetone/water. The best results were attained with 1 mL of wine sample, a 10% methanol/water solution (first eluant), ethyl acetate (second eluant), and 66% acetone/water as the polymeric phenols-eluting solution (third eluant), obtaining a SE of ca. 90%. Trials with this method on fruit juices also showed high separation efficiency. Hence, this solid-phase extraction method has been shown to be a simple and efficient alternative for the separation of nonpolymeric phenolic fractions and the polymeric ones, and this method could have important applications to sample purification prior to biological testing due to the nonspecific binding of polymeric phenolics to nearly all enzymes and receptor sites.

Acetone↗
PubMed2007

Polyphenols and antioxidant capacity of seed coat and cotyledon from Brazilian and Peruvian bean cultivars (Phaseolus vulgaris L.).

Seed coats and cotyledons from 25 Brazilian and 3 Peruvian bean cultivars were investigated in relation to their phenolic profiles and antioxidant capacity. Condensed tannins, anthocyanins, and flavonols such as kaempferol and quercetin glycosides were mostly found in seed coats. Cotyledons were rich in phenolic acids, such as ferulic, sinapic, chlorogenic, and other hydroxycinnamic acids. In general, the seed coat color pattern and the type of cultivar showed an important influence on the variability of phenolic profiles and levels, respectively. Total phenolics and antioxidant capacity assessed by the DPPH method were higher in seed coats than in cotyledons. The antioxidant capacity had a significant correlation with condensed tannins for all samples and with total anthocyanins in black and red seed coats, whereas in cotyledons, it was more related to the total phenolic content.

Anthocyanins↗
PubMedDate not supplied

Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.

Inhibition of human immunodeficiency virus reverse transcriptase is currently considered a useful approach in the prophylaxis and intervention of acquired immunodeficiency syndrome (AIDS), and natural products have not been extensively explored as inhibitors of this enzyme. We currently report that the reverse transcriptase assay developed for the detection of the enzyme in virions involving polyadenylic acid.oligodeoxythymidylic acid (poly rA.oligo dT) and radiolabeled thymidine 5'-triphosphate (TTP), can be applied as a simple method for screening the human immunodeficiency virus type 1 reverse transcriptase (HIV-1 RT) inhibitory potential of natural products. As reported herein, 156 pure natural products have been examined in this system. Benzophenanthridine alkaloids such as faragaronine chloride [1] and nitidine chloride, which are known inhibitors of avian myeloblastosis virus reverse transcriptase, demonstrated potent activity in the HIV-1 RT system, and 1 (IC50 10 micrograms/ml) was adopted as a positive-control substance. Additional inhibitors found were columbamine iodide [2] and other protoberberine alkaloids, the isoquinoline alkaloid O-methylpsychotrine sulfate [3], and the iridoid fulvoplumierin [4]. A number of indolizidine, pyrrolizidine, quinolizidine, indole, and other alkaloids, as well as compounds of many other structural classes, were tested and found to be inactive. A total of 100 plant extracts have also been evaluated, and 15 of these extracts showed significant inhibitory activity. Because tannins and other polyphenolic compounds are potent reverse transcriptase inhibitors, methods were evaluated for the removal of these from plant extracts prior to testing. Polyphenolic compounds were found to be responsible for the activity demonstrated by the majority of plant extracts. After appropriate tannin removal procedures were established, the bioassay system was shown to be generally applicable to both pure natural products and plant extracts. The method also proved useful in directing an isolation procedure with Plumeria rubra to yield fulvoplumierin [4] as an active compound (IC50 45 micrograms/ml).

Antiviral Agents↗
PubMed1997

Composition and functional properties of protein isolates obtained from commercial legumes grown in northern Spain.

Pea (Pisum sativum), faba bean (Vicia faba) and soybean (Glycine max) seeds were characterized, and protein isolates were prepared following an isoelectric point precipitation procedure. Soybean seeds showed the highest protein content (36.7%) and carbohydrate was the major constituent in the pea (59.4%) and the faba bean seeds (52.1%). Protein contents were higher than 80% in all the protein isolates. The amino acid contents in the protein isolates were, in general, higher than those in their own starting seeds. The antinutritional factor contents were reduced after the protein isolate preparation. The highest reductions achieved for tannins were 95% in the faba bean protein isolate, and for phytates (45%) and trypsin inhibitor activity (46%) in the pea protein isolate. Haemagglutinating activity was not detected in any of the protein isolates. Minimum solubility values were observed at a pH range between 4.0 and 6.0, and maximal solubilities were obtained at basic pH values. The faba bean protein isolate showed the highest water and oil absorption capacities, and the best gelling properties. The soybean protein isolate had the best foam expansion capacity. Thus, the protein isolates had an improvement in some of the characteristics compared to their original seeds with lower contents in tannins, phytates and haemagglutinating activity, but had weak functional properties.

Amino Acids↗
PubMed1999

Chemical evaluation of waste from Thaumatococcus danielli (Benth) processing.

Three different batches of Thaumatococcus danielli (Benth) fruits were collected at different fruiting seasons. The proximate compositions of the pericarp and seeds were determined on a dry weight basis. Partial characterization of the lipid extract was carried out and tannin content determined. The average moisture, ash and lipid contents of the pericarp were higher (89.2+/-4.17%, 20.7+/-1.10% and 11.6+/-1.23%, respectively) than those of the seed (31.2+/-4.66%, 9.1+/-0.71% and 8.2+/-1.64%, respectively). Crude protein and total carbohydrate were, however, higher in the seed (9.5+/-4.38% and 69.4+/-11.52%, respectively) than in the pericarp (4.5+/-2.21% and 6.3+/-3.94%, respectively). The dietary fiber contents of both pericarp and seed were high. Starch content was very low in the pericarp (0.4+/-0.0%) compared to the seed (66.28+/-9.21%). Tannin content in the pericarp and seeds was 12.1+/-1.52 mg/g and 21.9+/-2.28 mg/g, respectively. The oil extracted from both pericarp and seeds was light-yellow in color and slightly solid at room temperature. Unsaturation level of T. danielli oil was low, while free fatty acids were high. The results obtained suggested that T. danielli waste could potentially be a raw material in livestock feed formulation.

Analysis of Variance↗
PubMed2000

Influence of the flocculating agent in sedimentation and performance of a non flocculent strain of Zymomonas mobilis in the ethanol production process.

The influence of the flocculating agent was studied in the performance (measured by microbial growth and ethanol production) of a non flocculent strain of Zymomonas mobilis, as well as the potentiality of the sedimentation process in the separation of the biomass from the fermentation broth. Among the flocculating agents studied, it was verified that both tannin and the polyelectrolyte yielded good results with regard to cellular performance. However, with regard to sedimentation tannin is more adequate to be used in processes involving Zymomonas mobilis.

Acrylic Resins↗
PubMed2001

Effects of genotype, nutrient availability, and defoliation on aspen phytochemistry and insect performance.

Genetic and environmental variability, and their interactions, influence phytochemical composition and, in turn, herbivore performance. We evaluated the independent and interactive effects of plant genotype, nutrient availability, and defoliation on the foliar chemistry of quaking aspen (Populus tremuloides) and consequences for performance of gypsy moths (Lymantria dispar). Saplings of four genotypes were grown under two conditions of nutrient availability and subjected to three levels of artificial defoliation. Concentrations of all secondary and primary metabolites evaluated responded to at least one or more of the experimental treatments. Of the secondary metabolites, phenolic glycosides were affected strongly by genotype, less so by nutrient availability, and not induced by defoliation. Condensed tannins were strongly dependent upon genotype, soil nutrient availability, and their interaction, and, in contrast to phenolic glycosides, were induced by artificial defoliation. Of the primary metabolites, foliar nitrogen was affected by genotype and soil nutrient availability. Starch concentrations were affected by genotype, nutrient availability, defoliation and interactions among these factors. Foliar water content responded to genotype, nutrient availability, and defoliation, and the effect of nutrient availability depended on genotype. Herbivore performance on these plants was strongly influenced by plant genotype and soil nutrient availability, but much less so by defoliation. Although several of the compound types (condensed tannins, starch, and water) responded to defoliation, quantitative variation in these compounds did not contribute to substantive changes in herbivore performance. Rather, the primary source of variation in insect performance was due to plant genotype (phenolic glycoside levels), while nutrient availability (foliar nitrogen levels) was of secondary importance. These results suggest that genetic variation in aspen plays a major role in determining patterns of insect performance, whereas environmental variation, such as was tested, here is of negligible importance.

Animals↗
PubMed2002

Biochemical responses of Pinus pinaster trees to fire-induced trunk girdling and crown scorch: secondary metabolites and pigments as needle chemical indicators.

The biochemical responses to varying levels of localized heat damage to stems and crowns were studied in Pinus pinaster trees in Galicia, Spain. The objective was to ascertain the utility of secondary metabolites (total polyphenols. condensed tannins, astringency, free and esterified phenolic acids) and pigments (chlorophylls and carotenoids) as chemical indicators of localized fire damage. The study involved three levels of girdling by trunk heating (0%, 60%, and 75%), three levels of crown scorching (0%, 50%, and 75%), and all combinations of those trunk and crown treatment levels. Secondary metabolites and pigments were analyzed in needles before, during, and up to 8 months after fire treatments. High levels of polyphenols, condensed tannin, and pigments occurred in situations where the sole treatment was 75% crown scorching. Low levels of hydroxycinnamic acids were the result when the treatment was 75% trunk girdling. These responses occurred in the first two months after fire. Thereafter, normal values were observed. Low values of chlorophyll a/b ratio and high levels of free protocatechuic and esterified syringic acids were found to be long-term indicators of trunk girdling damage combined with crown scorching.

Analysis of Variance↗
PubMed2003

Leaf ontogeny influences leaf phenolics and the efficacy of genetically expressed Bacillus thuringiensis cry1A(a) d-endotoxin in hybrid poplar against gypsy moth.

We tested the hypothesis that ontogenetic variation in leaf chemistry could affect the efficacy of genetically expressed Bacillus thuringiensis cry1A(a) d-endotoxin, and thus provide spatial variation in (1) foliage protection and (2) selective pressures that could delay the resistance of folivores. Our model consisted of clonal hybrid Populus plants (NC5339). Consumption of foliage and relative growth rates of gypsy moth, Lymantria dispar (L.) increased, and phenolic glycoside concentrations decreased, as leaves from transformed plants containing the cry1A(a) d-endotoxin and nontransformed plants matured from leaf plastochron index (LPI) 1-6. Feeding and growth rates were negatively correlated with phenolic glycosides in both transformed and nontransformed foliage. The presence of the B. thuringiensis d-endotoxin was at most, additive to the effect of the phenolic glycosides. Feeding and growth rates were positively correlated with condensed tannins in transformed foliage, but there was no relationship with condensed tannins in nontransformed foliage. The results indicate that the presence of foliar allelochemicals of poplar can enhance the effectiveness of genetically expressed B. thuringiensis d-endotoxin against gypsy moth larvae. However, the spatial variation in gypsy moth performance in response to the combination of foliar allelochemicals and d-endotoxin was not greater than the effect of ontogenetic variation in foliar allelochemicals alone. These results suggest that for this important pest, foliage protection may be obtained without genetically engineered defenses, and instead, by relying on ontogenetic and clonal variation in allelochemicals. The benefits of combining novel resistance mechanisms with natural ones will depend upon the specific folivore's adaptation to natural resistance mechanisms, such as allelochemicals. Moreover, some of the greatest benefits from transgenic resistance may arise from the need to protect trees from multiple pests, some of which may not be deterred by, or may even prefer, allelochemicals that confer protection from a few species.

Animals↗
PubMed2006

Influence of germination and fermentation on bioaccessibility of zinc and iron from food grains.

OBJECTIVE AND DESIGN: Food grains such as green gram, chickpea and finger millet are often subjected to traditional processing involving germination and fermentation. This study was designed to assess the effect of germination of these grains on the bioaccessibility of zinc and iron. The effect of fermentation of a cereal-pulse combination as encountered in the preparation of breakfast dishes - idli, dosa and dhokla - on the same was also evaluated. Bioaccessibility measurement was made employing an in vitro simulated digestion method. RESULT: Zinc bioaccessibility was significantly decreased by germination (48 h) of finger millet (38%) and green gram (44%), while iron bioaccessibility was increased by 62% (green gram), 39% (chickpea) and 20% (finger millet), concomitant with a reduction in tannin content. A fermented batter of rice+black gram - 2:1 (idli) and 3:1 (dosa) - had higher bioaccessibility values for zinc (71 and 50%, respectively), while iron bioaccessibility values were increased in these cases of fermentation to an even greater extent, namely 277 and 127%, respectively. Zinc and iron bioaccessibility was not improved by fermentation of the combination of chickpea, green gram, black gram and rice (1:1:0.5:0.5; dhokla). A fermentation of cereal-legume combinations of idli and dosa batter significantly reduced both phytate and tannin, while in the case of dhokla batter there was a continued significant presence of phytate associated with additional legumes - chickpea and green gram. CONCLUSION: Germination of food grains improved the bioaccessibility of iron but not that of zinc. Fermentation of a batter of cereal-pulse combination in the preparation of idli and dosa enhanced the bioaccessibility of both zinc and iron, but not that of the combination used for the preparation of dhokla.

Biological Availability↗
PubMed2002

Identification in traditional herbal medications and confirmation by synthesis of factors that inhibit cholera toxin-induced fluid accumulation.

Kampo formulations are traditional herbal medications used in China and Japan for many centuries to treat diarrheal diseases such as cholera. Our studies were undertaken to identify and verify by chemical synthesis the active components that inhibited cholera toxin (CT), the virulence factor secreted by Vibrio cholerae, the causative agent of cholera. The Kampo formulation, Daio-kanzo-to, inhibited CT activities (i.e., ADP-ribosylation, Chinese hamster ovary cell elongation); in Daio-kanzo-to, Daio (Rhei rhizoma) was responsible for this effect. Among several components purified from Daio extract, rhubarb galloyl-tannin, a compound characterized by a polygallate structure, was the most effective. To define the active component, gallate analogues similar to rhubarb galloyl-tannin were synthesized. These gallate compounds inhibited all CT activities including ADP-ribosylation, elongation of Chinese hamster ovary cells, and importantly, fluid accumulation in ileal loops. Thus, Kampo formulations or their gallate components might be effective adjunctive therapy with oral rehydration solution for the severe diarrhea of cholera.

Adenosine Diphosphate Ribose↗
PubMed2003

Antimicrobial activity of some Hypericum species.

The crude methanolic extracts of six species of Hypericum [H. caprifoliatum Cham. & Schlecht., H. carinatum Griseb., H. connatum Lam., H. ternum A. St. Hil., H. myrianthum Cham. & Schlecht. and H. polyanthemum Klotzsch ex Reichardt] growing in southern Brazil were analyzed for antimicrobial activity against several microorganisms (bacteria and fungi). The most active plant was H. caprifoliatum, which showed activity against Staphylococcus aureus. Only H. polyanthemum and H. ternum extracts were active against Bacillus subtilis. None of the crude methanolic extracts showed activity against S. epidermidis, Escherichia coli or Saccharomyces cerevisiae. Extracts from these species were evaluated chemically and tannin, flavonoid and phenolic acids were the prominent compounds. The plants contained quercitrin, hyperoside (except H. connatum) and, less frequently, isoquercitrin and chlorogenic acid. In contrast to H. perforatum, which has high concentrations of rutin, these species do not produce this flavonoid or it appears as traces. The tannin concentration varied between 5.1 and 16.7% in H. myrianthum and H. ternum, respectively.

Anti-Infective Agents↗
PubMed1983

The influence of dietary tea, coffee and cocoa on protein and energy utilization of soya-bean meal and barley in rats.

Two series of balance experiments were performed with growing rats to test the effect of black tea, green tea, coffee and cocoa on protein and energy utilization. In Expt 1 soya-bean meal was fed as a basal diet and supplemented with freeze-dried materials from 11 black tea, green tea or coffee/500 g dry matter. Cocoa powder, corresponding to 11 of the beverage, was also added to the basal diet. In Expt 2 the procedure was repeated with a barley-based diet. In both experiments both tea varieties and coffee had significantly negative effects on true protein digestibility and biological value, while digestible energy was only slightly affected in the barley-based diet. Cocoa had no effect on protein or energy utilization in either soya-bean meal or barley diets, although the protein in cocoa powder was completely indigestible. As the tannin concentration in both tea varieties and coffee was very high it is assumed that the observed deleterious effects might, in part, be explained by anti-nutritional effects of tannin. The strongest deleterious effect was recorded for black tea.

Amino Acids↗
PubMed1984

The voluntary food intake by growing pigs of diets containing 'treated' rapeseed meals or extracts of rapeseed meal.

The intake by growing pigs of a diet containing British rapeseed meal (Brsm) extracted once with water was greater than that of a similar diet containing untreated Brsm, and a diet containing Brsm extracted twice with water was eaten more readily than one containing Brsm extracted once with water. Treatment of Brsm with slaked lime increased slightly its acceptability by growing pigs. The addition of a water extract of Brsm to a soya-bean meal (Sbm) diet reduced voluntary intake compared with the voluntary intake of the same Sbm diet with water added. Addition to the diet of a water extract passed through an anion exchange column increased food intake but if a cation exchange column was used there was no effect on intake. Treated rapeseed meals and extracts were analysed for glucosinolates, sinapine and tannins; the results indicated that glucosinolates rather than sinapine or tannin were associated with low feed intake.

Animal Feed↗