Cardiac Glycoside Glucoevatromonoside Induces Cancer Type-Specific Cell Death

PubMed Central

Schneider, Naira F. Z.; Cerella, Claudia; Lee, Jin-Young; Mazumder, Aloran; Kim, Kyung Rok; de Carvalho, Annelise; Munkert, Jennifer; Pádua, Rodrigo M.; Kreis, Wolfgang; Kim, Kyu-Won; Christov, Christo; Dicato, Mario; Kim, Hyun-Jung; Han, Byung Woo; Braga, Fernão C.; Simões, Cláudia M. O.; Diederich, Marc

2018-01-01

Cardiac glycosides (CGs) are natural compounds used traditionally to treat congestive heart diseases. Recent investigations repositioned CGs as potential anticancer agents. To discover novel cytotoxic CG scaffolds, we selected the cardenolide glucoevatromonoside (GEV) out of 46 CGs for its low nanomolar anti-lung cancer activity. GEV presented reduced toxicity toward non-cancerous cell types (lung MRC-5 and PBMC) and high-affinity binding to the Na+/K+-ATPase α subunit, assessed by computational docking. GEV-induced cell death was caspase-independent, as investigated by a multiparametric approach, and culminates in severe morphological alterations in A549 cells, monitored by transmission electron microscopy, live cell imaging and flow cytometry. This non-canonical cell death was not preceded or accompanied by exacerbation of autophagy. In the presence of GEV, markers of autophagic flux (e.g. LC3I-II conversion) were impacted, even in presence of bafilomycin A1. Cell death induction remained unaffected by calpain, cathepsin, parthanatos, or necroptosis inhibitors. Interestingly, GEV triggered caspase-dependent apoptosis in U937 acute myeloid leukemia cells, witnessing cancer-type specific cell death induction. Differential cell cycle modulation by this CG led to a G2/M arrest, cyclin B1 and p53 downregulation in A549, but not in U937 cells. We further extended the anti-cancer potential of GEV to 3D cell culture using clonogenic and spheroid formation assays and validated our findings in vivo by zebrafish xenografts. Altogether, GEV shows an interesting anticancer profile with the ability to exert cytotoxic effects via induction of different cell death modalities. PMID:29545747

Quantification of tannins and related polyphenols in commercial products of tormentil (Potentilla tormentilla).

PubMed

Fecka, Izabela; Kucharska, Alicja Zofia; Kowalczyk, Adam

2015-01-01

Potentilla tormentilla has many biological and pharmacological properties and can be used as an ingredient of some herbal medicines or beverages. The aim of this study was to evaluate the content of individual polyphenols, especially condensed and hydrolysable tannins in commercially available tormentil rhizomes and tinctures using chromatographic methods. A quantitative analysis (HPLC-PDA) was preceded by qualitative studies (UPLC-qTOF-MS/MS) and the isolation (CC) of the major tannin compounds. The tested plant material is characterised by a high content of tannins and related polyphenols, i.e. in rhizomes even at the level above 20% and in tinctures above 2%. The main components of tormentil rhizomes are procyanidin B3 (mean ~ 3.6%), procyanidin C2 (mean ~ 2.8%), agrimoniin (mean ~ 2.5%), 3-O-galloylquinic acid (mean ~ 1.7%), catechin (mean ~ 1.6%), other flavan-3-ol oligomers (mean ~ 0.5-1.1) and laevigatins (mean ~ 0.2-0.6%). Free ellagic acid and glycosides of ellagic and methylellagic acids are secondary components. Underground parts of tormentil are a source of oligomeric proanthocyanidins and ellagitannins, but in smaller quantity of gallotannins. Monogalloylquinic acids are new identified compounds, which had not been described in Potentilla tormentilla before we started our research. In the analysed tormentil tinctures agrimoniin concentration is lower in relation to other tannins. Copyright © 2015 John Wiley & Sons, Ltd.

Tannins in plant-herbivore interactions.

PubMed

Barbehenn, Raymond V; Peter Constabel, C

2011-09-01

Tannins are the most abundant secondary metabolites made by plants, commonly ranging from 5% to 10% dry weight of tree leaves. Tannins can defend leaves against insect herbivores by deterrence and/or toxicity. Contrary to early theories, tannins have no effect on protein digestion in insect herbivores. By contrast, in vertebrate herbivores tannins can decrease protein digestion. Tannins are especially prone to oxidize in insects with high pH guts, forming semiquinone radicals and quinones, as well as other reactive oxygen species. Tannin toxicity in insects is thought to result from the production of high levels of reactive oxygen species. Tannin structure has an important effect on biochemical activity. Ellagitannins oxidize much more readily than do gallotannins, which are more oxidatively active than most condensed tannins. The ability of insects to tolerate ingested tannins comes from a variety of biochemical and physical defenses in their guts, including surfactants, high pH, antioxidants, and a protective peritrophic envelope that lines the midgut. Most work on the ecological roles of tannins has been correlative, e.g., searching for negative associations between tannins and insect performance. A greater emphasis on manipulative experiments that control tannin levels is required to make further progress on the defensive functions of tannins. Recent advances in the use of molecular methods has permitted the production of tannin-overproducing transgenic plants and a better understanding of tannin biosynthetic pathways. Many research areas remain in need of further work, including the effects of different tannin types on different types of insects (e.g., caterpillars, grasshoppers, sap-sucking insects). Copyright © 2011 Elsevier Ltd. All rights reserved.

[Concentrations of alkaloids, cyanogenic glycosides, polyphenols and saponins in selected medicinal plants from Ecuador and their relationship with acute toxicity against Artemia salina].

PubMed

Jaramillo Jaramillo, Carmita; Jaramillo Espinoza, Anyi; D'Armas, Haydelba; Troccoli, Luis; Rojas de Astudillo, Luisa

2016-09-01

Alkaloids, polyphenols, cyanogenic glycosides and saponins are among the main chemical compounds synthesized by plants but not considered essential for their basic metabolism. These compounds have different functions in plants, and have been recognized with medicinal and pharmacological properties. In this research, concentrations of the mentioned secondary metabolites were determined in the medicinal plants Artemisia absinthium, Cnidoscolus aconitifolius, Parthenium hysterophorus, Piper carpunya and Taraxacum officinale, from Ecuador, and related with cytotoxic effects against Artemia salina. Alcoholic and aqueous extracts from leaves of these selected plants were prepared at different concentrations. To assess cytotoxicity of these extracts, different bioassays with A. salina were undertaken, and the mortality rates and LC50 were obtained. Besides, concentrations of alkaloids, cyanogenic glycosides, phenols, tannins and saponins were determined by spectrophotometric methods; this constituted the first report of quantification of secondary metabolites in the selected plants from Ecuador. T. officinale had the highest concentration of total phenols (22.30 ± 0.23 mg/g) and tannins (11.70 ± 0.10 mg/g), C. aconitifolius of cyanogenic glycosides (5.02 ± 0.37 µg/g) and P. hysterophorus of saponins (6.12 ± 0.02 mg/g). Tannins values obtained were not adverse to their consumption. Alcoholic and aqueous extracts of selected plants had hemolytic activity depending on the concentration of saponins. Although the values of cyanogenic glycosides were permissible, it was necessary to monitor the presence of this metabolite in plants to minimize health problems. LC50 values ranged from extremely toxic (3.37 µg/mL) to highly toxic (274.34 μg/mL), in P. carpunya and T. officinale, respectively. From correlation analysis, it was observed that increase values of alkaloids concentrations had highly significant (p<0.001) acute toxicity against A. salina, while at a higher

Cardiotonic action of two tannins

PubMed Central

Broadbent, J. L.

1962-01-01

A tannin isolated from Paullinia pinnata Linn., and tannic acid, have cardiotonic actions on the isolated perfused frog heart. Paullinia tannin is more firmly “fixed” than tannic acid. Tannin solutions contain peroxide, but the cardiotonic action is not dependent on this, since drugs believed to prevent peroxide formation, and sodium pyruvate which destroys peroxides, do not prevent the cardiotonic action. Maximal stimulation by tannin greatly reduces subsequent stimulation by ouabain. If calcium is omitted from the Ringer solution tannins cannot stimulate the heart. In this respect they differ from ouabain. However, the ouabain stimulation can be prevented by prior perfusion with tannin. It is suggested that the antagonism between tannin and ouabain is due to the former preventing ouabain from reaching its receptor sites, and that tannin stimulation is dependent on the formation of a calcium-tannin complex at the heart surface. In the isolated perfused mammalian heart preparation tannins increase diastolic tonus and coronary flow. PMID:13873207

Salivary amylase induction by tannin-enriched diets as a possible countermeasure against tannins.

PubMed

da Costa, G; Lamy, E; Capela e Silva, F; Andersen, J; Sales Baptista, E; Coelho, A V

2008-03-01

Tannins are characterized by protein-binding affinity. They have astringent/bitter properties that act as deterrents, affecting diet selection. Two groups of salivary proteins, proline-rich proteins and histatins, are effective precipitators of tannin, decreasing levels of available tannins. The possibility of other salivary proteins having a co-adjuvant role on host defense mechanisms against tannins is unknown. In this work, we characterized and compared the protein profile of mice whole saliva from animals fed on three experimental diets: tannin-free diet, diet with the incorporation of 5% hydrolyzable tannins (tannic acid), or diet with 5% condensed tannins (quebracho). Protein analysis was performed by one-dimensional gel electrophoresis combined with Matrix-Assisted Laser Desorption Ionization-Time of Flight mass spectrometry to allow the dynamic study of interactions between diet and saliva. Since abundant salivary proteins obscure the purification and identification of medium and low expressed salivary proteins, we used centrifugation to obtain saliva samples free from proteins that precipitate after tannin binding. Data from Peptide Mass Fingerprinting allowed us to identify ten different proteins, some of them showing more than one isoform. Tannin-enriched diets were observed to change the salivary protein profile. One isoform of alpha-amylase was overexpressed with both types of tannins. Aldehyde reductase was only identified in saliva of the quebracho group. Additionally, a hypertrophy of parotid salivary gland acini was observed by histology, along with a decrease in body mass in the first 4 days of the experimental period.

Saliva tannin interactions.

PubMed

Prinz, J F; Lucas, P W

2000-11-01

Many plant foods contain tannins, compounds that bind proteins, such as mammalian enzymes. Although described as tasteless, tannins can be detected orally by their astringency. However, the actual mechanism of oral detection and the effect of tannins on mastication and swallowing have been little investigated. Here, we show from in vitro tests that tannic acid, a common standard in tests used to detect tannins, significantly reduces the lubricating qualities of human saliva both by decreasing its viscosity and increasing friction, both factors lending support to the notion that astringency is a tactile phenomenon. From the literature, it is clear that this effect depends on the presence of salivary proline-rich proteins (PRP). In a mammalian context, ingestion of tannin-rich foods in a species with salivary PRP will be signalled by interference with bolus formation during mastication while the increase in friction may also be detectable and lead to increased tooth wear if the signal is ignored. In a human context, cross-cultural preferences for tannin-rich beverages such as tea, coffee and red wine at the end of meals may be explained by reduction in adhesion of food particles to the oral mucosa allowing their rapid oral clearance.

Defensive strategies in Geranium sylvaticum. Part 1: organ-specific distribution of water-soluble tannins, flavonoids and phenolic acids.

PubMed

Tuominen, Anu; Toivonen, Eija; Mutikainen, Pia; Salminen, Juha-Pekka

2013-11-01

A combination of high-resolution mass spectrometry and modern HPLC column technology, assisted by diode array detection, was used for accurate characterization of water-soluble polyphenolic compounds in the pistils, stamens, petals, sepals, stems, leaves, roots and seeds of Geranium sylvaticum. The organs contained a large variety of polyphenols, five types of tannins (ellagitannins, proanthocyanidins, gallotannins, galloyl glucoses and galloyl quinic acids) as well as flavonoids and simple phenolic acids. In all, 59 compounds were identified. Geraniin and other ellagitannins dominated in all the green photosynthetic organs. The other organs seem to produce distinctive polyphenol groups: pistils accumulated gallotannins; petals acetylglucose derivatives of galloylglucoses; stamens kaempferol glycosides, and seeds and roots accumulated proanthocyanidins. The intra-plant distribution of the different polyphenol groups may reflect the different functions and importance of various types of tannins as the defensive chemicals against herbivory. Copyright © 2013 Elsevier Ltd. All rights reserved.

Co-occurrence of tannin and tannin-less vacuoles in sensitive plants.

PubMed

Fleurat-Lessard, Pierrette; Béré, Emile; Lallemand, Magali; Dédaldéchamp, Fabienne; Roblin, Gabriel

2016-05-01

Vacuoles of different types frequently coexist in the same plant cell, but the duality of the tannin/tannin-less vacuoles observed in Mimosa pudica L. is rare. In this plant, which is characterized by highly motile leaves, the development and original features of the double vacuolar compartment were detailed in primary pulvini from the young to the mature leaf stage. In young pulvini, the differentiation of tannin vacuoles first occurred in the epidermis and progressively spread toward the inner cortex. In motor cells of nonmotile pulvini, tannin deposits first lined the membranes of small vacuole profiles and then formed opaque clusters that joined together to form a large tannin vacuole (TV), the proportion of which in the cell was approximately 45%. At this stage, transparent vacuole profiles were rare and small, but as the parenchyma cells enlarged, these profiles coalesced to form a transparent vacuole with a convexity toward the larger-sized tannin vacuole. When leaf motility began to occur, the two vacuole types reached the same relative proportion (approximately 30%). Finally, in mature cells displaying maximum motility, the large transparent colloidal vacuole (CV) showed a relative proportion increasing to approximately 50%. At this stage, the proportion of the tannin vacuole, occurring in the vicinity of the nucleus, decreased to approximately 10%. The presence of the condensed type of tannins (proanthocyanidins) was proven by detecting their fluorescence under UV light and by specific chemical staining. This dual vacuolar profile was also observed in nonmotile parts of M. pudica (e.g., the petiole and the stem). Additional observations of leaflet pulvini showing more or less rapid movements showed that this double vacuolar structure was present in certain plants (Mimosa spegazzinii and Desmodium gyrans), but absent in others (Albizzia julibrissin, Biophytum sensitivum, and Cassia fasciculata). Taken together, these observations strongly suggest that a

Lipoxygenase-inhibiting phenolic glycosides and monoterpene glycosides from Paeonia lactiflora.

PubMed

Zou, Liang; Hu, Lin-Feng; Guo, Yi-Dong; Song, Yu; Fu, Qiang

2015-01-01

The EtOH extract of the roots of Paeonia lactiflora afforded a new phenolic glycoside paenoside A (1) and a new monoterpene glycoside paeonin D (2), and five known monoterpene glycosides. Their structures were elucidated on the basis of spectroscopic means and hydrolysis products. All compounds displayed inhibitory potential against enzyme lipoxygenase.

Anthocyanins influence tannin-cell wall interactions.

PubMed

Bautista-Ortín, Ana Belén; Martínez-Hernández, Alejandro; Ruiz-García, Yolanda; Gil-Muñoz, Rocío; Gómez-Plaza, Encarna

2016-09-01

The rate of tannin extraction was studied in a vinification of red grapes and the results compared with another vinification made with white grapes fermented as for typical red wine, in the presence of skins and seeds. Even though the grapes presented a quite similar skin and seed tannin content, the differences in tannin concentration between both vinifications was very large, despite the fact that the only apparent difference between the phenolic composition of both wines was the anthocyanin content. This suggests that anthocyanins play an important role in tannin extractability, perhaps because they affect the extent of the tannin-cell wall interaction, a factor that largely controls the resulting quantity of tannins in wines. To confirm this observation, the effect of anthocyanins on the tannin extractability from grape seeds and skin and on the interaction between tannins and grape cell walls suspended in model solutions were studied. The results indicated that anthocyanins favored skin and seed tannin extraction and that there is a competition for the adsorption sites between anthocyanins and tannins that increases the tannin content when anthocyanins are present. Copyright © 2016 Elsevier Ltd. All rights reserved.

Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.

PubMed

Gau, Jana; Prévost, Martine; Van Antwerpen, Pierre; Sarosi, Menyhárt-Botond; Rodewald, Steffen; Arnhold, Jürgen; Flemmig, Jörg

2017-05-26

Several hydrolyzable tannins, proanthocyanidins, tannin derivatives, and a tannin-rich plant extract of tormentil rhizome were tested for their potential to regenerate the (pseudo-)halogenating activity, i.e., the oxidation of SCN - to hypothiocyanite - OSCN, of lactoperoxidase (LPO) after hydrogen peroxide-mediated enzyme inactivation. Measurements were performed using 5-thio-2-nitrobenzoic acid in the presence of tannins and related substances in order to determine kinetic parameters and to trace the LPO-mediated - OSCN formation. The results were combined with docking studies and molecular orbital analysis. The - OSCN-regenerating effect of tannin derivatives relates well with their binding properties toward LPO as well as their occupied molecular orbitals. Especially simple compounds like ellagic acid or methyl gallate and the complex plant extract were found as potent enzyme-regenerating compounds. As the (pseudo-)halogenating activity of LPO contributes to the maintenance of oral bacterial homeostasis, the results provide new insights into the antibacterial mode of action of tannins and related compounds. Furthermore, chemical properties of the tested compounds that are important for efficient enzyme-substrate interaction and regeneration of the - OSCN formation by LPO were identified.

Variability in tannin content, chemistry and activity in a diverse group of tannin containing sorghum cultivars.

PubMed

Kaufman, Rhett C; Herald, Thomas J; Bean, Scott R; Wilson, Jeff D; Tuinstra, Mitch R

2013-03-30

Tannins are large polyphenolic polymers and are known to bind proteins, limiting their digestibility, but are also excellent antioxidants. Numerous studies investigating the functional properties of sorghum tannin have been conducted by comparing grain samples from different sorghum lines without considering the other intrinsic characteristics of the grain. The purpose of this study was to remove the confounding intrinsic factors present in the endosperm so the effect of the tannins could be evaluated utilizing a unique decortication/reconstitution procedure. The tannin content of the 14 cultivars tested ranged from 2.3 to 67.2 catechin equivalents. The bran fractions were studied for their impact on protein binding and antioxidant capacity. Protein digestibility by pepsin ranged from 8% to 58% at the highest tannin level addition. Protein binding ranged from 3.11 to 16.33 g blue bovine serum albumin kg⁻¹ bran. Antioxidant capacity ranged from 81.33 to 1122.54 µmol Trolox equivalents g⁻¹ bran. High-performance size-exclusion chromatography detailed molecular size distributions of the tannin polymers and relationship to tannin functionality. The tannin content and composition play a significant role in determining tannin functionality. These differences will allow for selections of high-tannin sorghums with consideration of the biological activities of the tannins. Published 2012. This article is a U.S. Government work and is in the public domain in the USA.

Tannins from Acacia mearnsii De Wild. Bark: Tannin Determination and Biological Activities.

PubMed

Ogawa, Sosuke; Yazaki, Yoshikazu

2018-04-05

The bark of Acacia mearnsii De Wild. (black wattle) contains significant amounts of water-soluble components acalled "wattle tannin". Following the discovery of its strong antioxidant activity, a wattle tannin dietary supplement has been developed and as part of developing new dietary supplements, a literature search was conducted using the SciFinder data base for " Acacia species and their biological activities". An analysis of the references found indicated that the name of Acacia nilotica had been changed to Vachellia nilotica , even though the name of the genus Acacia originated from its original name. This review briefly describes why and how the name of A. nilotica changed. Tannin has been analyzed using the Stiasny method when the tannin is used to make adhesives and the hide-powder method is used when the tannin is to be used for leather tanning. A simple UV method is also able to be used to estimate the values for both adhesives and leather tanning applications. The tannin content in bark can also be estimated using NIR and NMR. Tannin content estimations using pyrolysis/GC, electrospray mass spectrometry and quantitative 31 P-NMR analyses have also been described. Tannins consists mostly of polyflavanoids and all the compounds isolated have been updated. Antioxidant activities of the tannin relating to anti-tumor properties, the viability of human neuroblastoma SH-SY5Y cells and also anti-hypertensive effects have been studied. The antioxidant activity of proanthocyanidins was found to be higher than that of flavan-3-ol monomers. A total of fourteen papers and two patents reported the antimicrobial activities of wattle tannin. Bacteria were more susceptible to the tannins than the fungal strains tested. Several bacteria were inhibited by the extract from A. mearnsii bark. The growth inhibition mechanisms of E. coli were investigated. An interaction between extracts from A. mearnsii bark and antibiotics has also been studied. The extracts from A. mearnsii

Factors affecting skin tannin extractability in ripening grapes.

PubMed

Bindon, Keren A; Madani, S Hadi; Pendleton, Phillip; Smith, Paul A; Kennedy, James A

2014-02-05

The acetone-extractable (70% v/v) skin tannin content of Vitis vinifera L. cv. Cabernet Sauvignon grapes was found to increase during late-stage ripening. Conversely, skin tannin content determined following ethanol extraction (10, 20, and 50% v/v) did not consistently reflect this trend. The results indicated that a fraction of tannin became less extractable in aqueous ethanol during ripening. Skin cell walls were observed to become more porous during ripening, which may facilitate the sequestering of tannin as an adsorbed fraction within cell walls. For ethanol extracts, tannin molecular mass increased with advancing ripeness, even when extractable tannin content was constant, but this effect was negligible in acetone extracts. Reconstitution experiments with isolated skin tannin and cell wall material indicated that the selectivity of tannin adsorption by cell walls changed as tannin concentration increased. Tannin concentration, tannin molecular mass, and cell wall porosity are discussed as factors that may influence skin tannin extractability.

Tannins, Peptic Ulcers and Related Mechanisms

PubMed Central

de Jesus, Neyres Zinia Taveira; de Souza Falcão, Heloina; Gomes, Isis Fernandes; de Almeida Leite, Thiago Jose; de Morais Lima, Gedson Rodrigues; Barbosa-Filho, Jose Maria; Tavares, Josean Fechine; da Silva, Marcelo Sobral; de Athayde-Filho, Petrônio Filgueiras; Batista, Leonia Maria

2012-01-01

This review of the current literature aims to study correlations between the chemical structure and gastric anti-ulcer activity of tannins. Tannins are used in medicine primarily because of their astringent properties. These properties are due to the fact that tannins react with the tissue proteins with which they come into contact. In gastric ulcers, this tannin-protein complex layer protects the stomach by promoting greater resistance to chemical and mechanical injury or irritation. Moreover, in several experimental models of gastric ulcer, tannins have been shown to present antioxidant activity, promote tissue repair, exhibit anti Helicobacter pylori effects, and they are involved in gastrointestinal tract anti-inflammatory processes. The presence of tannins explains the anti-ulcer effects of many natural products. PMID:22489149

Tannins, peptic ulcers and related mechanisms.

PubMed

de Jesus, Neyres Zinia Taveira; de Souza Falcão, Heloina; Gomes, Isis Fernandes; de Almeida Leite, Thiago Jose; de Morais Lima, Gedson Rodrigues; Barbosa-Filho, Jose Maria; Tavares, Josean Fechine; da Silva, Marcelo Sobral; de Athayde-Filho, Petrônio Filgueiras; Batista, Leonia Maria

2012-01-01

This review of the current literature aims to study correlations between the chemical structure and gastric anti-ulcer activity of tannins. Tannins are used in medicine primarily because of their astringent properties. These properties are due to the fact that tannins react with the tissue proteins with which they come into contact. In gastric ulcers, this tannin-protein complex layer protects the stomach by promoting greater resistance to chemical and mechanical injury or irritation. Moreover, in several experimental models of gastric ulcer, tannins have been shown to present antioxidant activity, promote tissue repair, exhibit anti Helicobacter pylori effects, and they are involved in gastrointestinal tract anti-inflammatory processes. The presence of tannins explains the anti-ulcer effects of many natural products.

Protein Binding Capacity of Different Forages Tannin

NASA Astrophysics Data System (ADS)

Yusiati, L. M.; Kurniawati, A.; Hanim, C.; Anas, M. A.

2018-02-01

Eight forages of tannin sources(Leucaena leucocephala, Arachis hypogaea, Mimosa pudica, Morus alba L, Swietenia mahagoni, Manihot esculenta, Gliricidia sepium, and Bauhinia purpurea)were evaluated their tannin content and protein binding capacity. The protein binding capacity of tannin were determined using precipitation of bovine serum albumin (BSA). Swietenia mahagonihas higest total tannin level and condensed tannin (CT) compared with other forages (P<0.01). The Leucaena leucocephala has highest hydrolysable tannin (HT) level (P<0.01). The total and condensed tannin content of Swietenia mahagoni were 11.928±0.04 mg/100 mg and 9.241±0.02mg/100mg dry matter (DM) of leaves. The hydrolysable tannin content of Leucaena leucocephala was 5.338±0.03 mg/100 mg DM of leaves. Binding capacity was highest in Swietenia mahagoni and Leucaena leucocephala compared to the other forages (P<0.01). The optimum binding of BSA to tannin in Leucaena leucocephala and Swietenia mahagoniwere1.181±0.44 and 1.217±0.60mg/mg dry matter of leaves. The present study reports that Swietenia mahagoni has highest of tannin content and Leucaena leucocephala and Swietenia mahagoni capacity of protein binding.

Tannin-assisted aggregation of natively unfolded proteins

NASA Astrophysics Data System (ADS)

Zanchi, D.; Narayanan, T.; Hagenmuller, D.; Baron, A.; Guyot, S.; Cabane, B.; Bouhallab, S.

2008-06-01

Tannin-protein interactions are essentially physical: hydrophobic and hydrogen-bond-mediated. We explored the tannin-assisted protein aggregation on the case of β-casein, which is a natively unfolded protein known for its ability to form micellar aggregates. We used several tannins with specified length. Our SAXS results show that small tannins increase the number of proteins per micelle, but keeping their size constant. It leads to a tannin-assisted compactization of micelles. Larger tannins, with linear dimensions greater than the crown width of micelles, lead to the aggregation of micelles by a bridging effect. Experimental results can be understood within a model where tannins are treated as effective enhancers of hydrophobic attraction between specific sites in proteins.

Inoculation of tannin-degrading bacteria into novel hosts increases performance on tannin-rich diets.

PubMed

Kohl, Kevin D; Stengel, Ashley; Dearing, M Denise

2016-06-01

It has been hypothesized that herbivores host tannin-degrading bacteria (TDB) to overcome the toxic challenges posed by plant tannins. While TDB have been isolated from the guts of numerous mammals, their functional significance to their hosts has never been explicitly tested. We introduced TDB into lab rats, which do not host TDB, and measured host performance on tannin-rich diets. We first isolated three species of TDB, Escherichia coli, Bacillus subtilis and Enterococcus faecalis, from the guts of the desert woodrat (Neotoma lepida), which regularly feeds on tannin-rich plants. Then, we inoculated isolated TDB, as well as full woodrat microbial communities into laboratory rats. A control group was inoculated with sterilized woodrat faeces. Recipient lab rats were fed increasing concentrations of tannic acid, and we monitored tannic acid intake, body mass and liver damage as measured by serum alanine aminotransferase activity. Lab rats given TDB as isolates or full communities exhibited increased tannic acid intake, higher maintenance of body mass and lower indicators of liver damage compared with control animals. These differences were maintained when the trial was repeated after 6 weeks of feeding on tannin-free diets. Our results are the first to demonstrate that TDB significantly increase host performance on tannin-rich diets. © 2015 Society for Applied Microbiology and John Wiley & Sons Ltd.

Colloidal stability of tannins: astringency, wine tasting and beyond

NASA Astrophysics Data System (ADS)

Zanchi, D.; Poulain, C.; Konarev, P.; Tribet, C.; Svergun, D. I.

2008-12-01

Tannin-tannin and tannin-protein interactions in water-ethanol solvent mixtures are studied in the context of red wine tasting. While tannin self-aggregation is relevant for the visual aspect of wine tasting (limpidity and related colloidal phenomena), tannin affinities for salivary proline-rich proteins is fundamental for a wide spectrum of organoleptic properties related to astringency. Tannin-tannin interactions are analyzed in water-ethanol wine-like solvents and the precipitation map is constructed for a typical grape tannin. The interaction between tannins and human salivary proline-rich proteins (PRP) are investigated in the framework of the shell model for micellization, known for describing tannin-induced aggregation of β-casein. Tannin-assisted micellization and compaction of proteins observed by SAXS are described quantitatively and discussed in the case of astringency.

Interaction of gut microflora with tannins in feeds

NASA Astrophysics Data System (ADS)

Goel, Gunjan; Puniya, A. K.; Aguilar, C. N.; Singh, Kishan

2005-11-01

Tannins (hydrolyzable and condensed) are water-soluble polyphenolic compounds that exert antinutritional effects on ruminants by forming complexes with dietary proteins. They limit nitrogen supply to animals, besides inhibiting the growth and activity of ruminal microflora. However, some gastrointestinal microbes are able to break tannin-protein complexes while preferentially degrading hydrolyzable tannins (HTs). Streptococcus gallolyticus, Lonepinella koalarum and Selenomonas ruminantium are the dominant bacterial species that have the ability to degrade HTs. These tanninolytic microorganisms possess tannin-degrading ability and have developed certain mechanisms to tolerate tannins in feeds. Hence, selection of efficient tanninolytic microbes and transinoculation among animals for long-term benefits become areas of intensive interest. Here, we review the effects of tannins on ruminants, the existence and significance of tannin-degrading microorganisms in diverse groups of animals and the mechanisms that tannin-degrading microorganisms have developed to counter the toxic effects of tannin.

Interaction of gut microflora with tannins in feeds.

PubMed

Goel, Gunjan; Puniya, A K; Aguilar, C N; Singh, Kishan

2005-11-01

Tannins (hydrolyzable and condensed) are water-soluble polyphenolic compounds that exert antinutritional effects on ruminants by forming complexes with dietary proteins. They limit nitrogen supply to animals, besides inhibiting the growth and activity of ruminal microflora. However, some gastrointestinal microbes are able to break tannin-protein complexes while preferentially degrading hydrolyzable tannins (HTs). Streptococcus gallolyticus, Lonepinella koalarum and Selenomonas ruminantium are the dominant bacterial species that have the ability to degrade HTs. These tanninolytic microorganisms possess tannin-degrading ability and have developed certain mechanisms to tolerate tannins in feeds. Hence, selection of efficient tanninolytic microbes and transinoculation among animals for long-term benefits become areas of intensive interest. Here, we review the effects of tannins on ruminants, the existence and significance of tannin-degrading microorganisms in diverse groups of animals and the mechanisms that tannin-degrading microorganisms have developed to counter the toxic effects of tannin.

Use of whole grain and refined flour from tannin and non-tannin sorghum (Sorghum bicolor (L.) Moench) varieties in frybread.

PubMed

Rose, Devin J; Williams, Emily; Mkandawire, Nyambe L; Weller, Curtis L; Jackson, David S

2014-07-01

Frybreads were prepared using wheat flour and wheat-sorghum composite flours (refined and whole grain; white, tannin-free and red, tannin-containing) at 0, 25, 50, and 75% sorghum flour. Hardness, volume, specific volume, color, and oil uptake were determined. Frybreads made with refined white, tannin-free sorghum were also evaluated in a sensory panel. Substitution of sorghum flour for wheat flour reduced the volume and increased the darkness of the fried dough pieces compared with wheat flour controls. Oil absorption was unaffected when using white, tannin-free sorghum. When using red, tannin-containing sorghum, oil absorption increased for refined flour and decreased for whole grain flour, suggesting that a component only present in the whole grain tannin-containing Sorghum--perhaps tannins themselves--may decrease oil uptake. Panelists rated frybreads containing up to 50% white, tannin-free sorghum flour as not significantly different from control frybreads made with refined wheat flour.

Interactions of Condensed Tannins with Saccharomyces cerevisiae Yeast Cells and Cell Walls: Tannin Location by Microscopy.

PubMed

Mekoue Nguela, Julie; Vernhet, Aude; Sieczkowski, Nathalie; Brillouet, Jean-Marc

2015-09-02

Interactions between grape tannins/red wine polyphenols and yeast cells/cell walls was previously studied within the framework of red wine aging and the use of yeast-derived products as an alternative to aging on lees. Results evidenced a quite different behavior between whole cells (biomass grown to elaborate yeast-derived products, inactivated yeast, and yeast inactivated after autolysis) and yeast cell walls (obtained from mechanical disruption of the biomass). Briefly, whole cells exhibited a high capacity to irreversibly adsorb grape and wine tannins, whereas only weak interactions were observed for cell walls. This last point was quite unexpected considering the literature and called into question the real role of cell walls in yeasts' ability to fix tannins. In the present work, tannin location after interactions between grape and wine tannins and yeast cells and cell walls was studied by means of transmission electron microscopy, light epifluorescence, and confocal microscopy. Microscopy observations evidenced that if tannins interact with cell walls, and especially cell wall mannoproteins, they also diffuse freely through the walls of dead cells to interact with their plasma membrane and cytoplasmic components.

Cardiac glycosides use and the risk of lung cancer: a nested case-control study.

PubMed

Couraud, Sébastien; Azoulay, Laurent; Dell'Aniello, Sophie; Suissa, Samy

2014-08-08

Two studies have reported statistically significant associations between the use of cardiac glycosides (CGs) and an increased risk of lung cancer. However, these studies had a number of methodological limitations. Thus, the objective of this study was to assess this association in a large population-based cohort of patients. We used the United Kingdom Clinical Practice Research Datalink (CPRD) to identify a cohort of patients, at least 40 years of age, newly-diagnosed with heart failure, or supra-ventricular arrhythmia. A nested case-control analysis was conducted where each incident case of lung cancer identified during follow-up was randomly matched with up to 10 controls. Exposure to CGs was assessed in terms of ever use, cumulative duration of use and cumulative dose. Rate ratios (RRs) with 95% confidence intervals (CIs) were estimated using conditional logistic regression after adjusting for potential confounders. A total of 129,002 patients were included, and followed for a mean (SD) of 4.7 (3.8) years. During follow-up, 1237 patients were newly-diagnosed with lung cancer. Overall, ever use of CGs was not associated with an increased risk of lung cancer when compared to never use (RR = 1.09, 95% CI: 0.94-1.26). In addition, no dose-response relationship was observed in terms of cumulative duration of use and cumulative dose with all RRs around the null value across quartile categories. The results of this large population-based study indicate that the use of CGs is not associated with an increased risk of lung cancer.

Effects of different tannin-rich extracts and rapeseed tannin monomers on methane formation and microbial protein synthesis in vitro.

PubMed

Wischer, G; Boguhn, J; Steingaß, H; Schollenberger, M; Rodehutscord, M

2013-11-01

Tannins, polyphenolic compounds found in plants, are known to complex with proteins of feed and rumen bacteria. This group of substances has the potential to reduce methane production either with or without negative effects on digestibility and microbial yield. In the first step of this study, 10 tannin-rich extracts from chestnut, mimosa, myrabolan, quebracho, sumach, tara, valonea, oak, cocoa and grape seed, and four rapeseed tannin monomers (pelargonidin, catechin, cyanidin and sinapinic acid) were used in a series of in vitro trials using the Hohenheim gas test, with grass silage as substrate. The objective was to screen the potential of various tannin-rich extracts to reduce methane production without a significant effect on total gas production (GP). Supplementation with pelargonidin and cyanidin did not reduce methane production; however, catechin and sinapinic acid reduced methane production without altering GP. All tannin-rich extracts, except for tara extract, significantly reduced methane production by 8% to 28% without altering GP. On the basis of these results, five tannin-rich extracts were selected and further investigated in a second step using a Rusitec system. Each tannin-rich extract (1.5 g) was supplemented to grass silage (15 g). In this experiment, nutrient degradation, microbial protein synthesis and volatile fatty acid production were used as additional response criteria. Chestnut extract caused the greatest reduction in methane production followed by valonea, grape seed and sumach, whereas myrabolan extract did not reduce methane production. Whereas chestnut extract reduced acetate production by 19%, supplementation with grape seed or myrabolan extract increased acetate production. However, degradation of fibre fractions was reduced in all tannin treatments. Degradation of dry matter and organic matter was also reduced by tannin supplementation, and no differences were found between the tannin-rich extracts. CP degradation and ammonia

Biodegradability of tannin-containing wastewater from leather industry.

PubMed

He, Qiang; Yao, Kai; Sun, Danhong; Shi, Bi

2007-08-01

Tannins occur commonly in the wastewaters from forestry, plant medicine, paper and leather industries. The treatment of this kind of wastewaters, including settling and biodegradation, is usually difficult because tannins are highly soluble in water and would inhibit the growth of microorganisms in activated sludge. The objective of this study is to investigate biodegradability of tannin-containing wastewaters, so as to characterize the pollution properties of such wastewaters and provide a reference for their biological treatment in wastewater treatment plants. The research was typified by using the wastewater collected from vegetable tanning process in leather industry. A model was developed to describe the activated sludge process, and the biodegradation kinetics of vegetable tanning wastewater (VET wastewater) was studied. It was found that the biodegradability of tannin-containing wastewater varies heavily with the content of tannins in wastewater. The biodegradation of VET wastewater with tannin content around 4,900 mg/l occurred inefficiently due to the inhibition of tannins to the activated sludge process, and only 34.7% of biodegradation extent was reached in 14 days of incubation. The optimal biodegradability of VET wastewater was observed when its tannin content was diluted to 490 mg/l, where the COD and tannin removals reached 51.3% and 45.1% respectively in 6 days. Hence, it is suggested that a proper control of tannin content is necessary to achieve an effective biodegradation of tannin-containing wastewaters in wastewater treatment plants.

Oligomeric hydrolyzable tannins from Monochaetum multiflorum.

PubMed

Isaza, José H; Ito, Hideyuki; Yoshida, Takashi

2004-02-01

Four hydrolyzable tannins, nobotanins Q, R, S, and T, were isolated from the aqueous acetone extract of the dried leaves of Monochaetum multiflorum (Melastomataceae), a plant indigenous to Colombia. Their dimeric and tetrameric structures were elucidated by spectral and chemical methods. Eight known hydrolyzable tannin monomers and eight ellagitannin oligomers characteristic of melastomataceous plants were also characterized as tannin constituents of the plant.

Red Wine Tannin Structure-Activity Relationships during Fermentation and Maceration.

PubMed

Yacco, Ralph S; Watrelot, Aude A; Kennedy, James A

2016-02-03

The correlation between tannin structure and corresponding activity was investigated by measuring the thermodynamics of interaction between tannins isolated from commercial red wine fermentations and a polystyrene divinylbenzene HPLC column. Must and/or wine samples were collected throughout fermentation/maceration from five Napa Valley wineries. By varying winery, fruit source, maceration time, and cap management practice, it was considered that a reasonably large variation in commercially relevant tannin structure would result. Tannins were isolated from samples collected using low pressure chromatography and were then characterized by gel permeation chromatography and acid-catalyzed cleavage in the presence of excess phloroglucinol (phloroglucinolysis). Corresponding tannin activity was determined using HPLC by measuring the thermodynamics of interaction between isolated tannin and a polystyrene divinylbenzene HPLC column. This measurement approach was designed to determine the ability of tannins to hydrophobically interact with a hydrophobic surface. The results of this study indicate that tannin activity is primarily driven by molecular size. Compositionally, tannin activity was positively associated with seed tannins and negatively associated with skin and pigmented tannins. Although measured indirectly, the extent of tannin oxidation as determined by phloroglucinolysis conversion yield suggests that tannin oxidation at this stage of production reduces tannin activity. Based upon maceration time, this study indicates that observed increases in perceived astringency quality, if related to tannin chemistry, are driven by tannin molecular mass as opposed to pigmented tannin formation or oxidation. Overall, the results of this study give new insight into tannin structure-activity relationships which dominate during extraction.

Modulation of in vitro rumen biohydrogenation by Cistus ladanifer tannins compared with other tannin sources.

PubMed

Costa, Mónica; Alves, Susana P; Cabo, Ângelo; Guerreiro, Olinda; Stilwell, George; Dentinho, Maria T; Bessa, Rui Jb

2017-01-01

Tannins are polyphenolic compounds able to modify the ruminal biohydrogenation (BH) of unsaturated fatty acids, but their activity may vary among different tannin sources. The effect of rockrose (Cistus ladanifer) on BH has never been compared with other more common tannin sources. Tannin extracts (100 g kg -1 substrate dry matter) from chestnut (CH), quebracho (QB), grape seed (GS) and rockrose (CL) were incubated in vitro for 6 h with ruminal fluid using as substrate a feed containing 60 g kg -1 of sunflower oil. A control treatment with no added tannins was also included. Compared with the control, GS and CL, but not CH and QB, increased (P < 0.05) the disappearance of c9,c12-18:2 with a consequent larger production of c9,t11-18:2 and t11-18:1. However, no differences among treatments (P > 0.05) were observed for the disappearance of c9-18:1 and c9,c12,c15-18:3. The production of 18:0 was not different (P > 0.05) among treatments, although its proportion in the total BH products was lower (P < 0.05) for GS than for the other treatments. Condensed tannins from GS and, to a lesser extent, from CL stimulate the first steps of BH, without a clear inhibition of 18:0 production. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

Tannin quantification in red grapes and wine: comparison of polysaccharide- and protein-based tannin precipitation techniques and their ability to model wine astringency.

PubMed

Mercurio, Meagan D; Smith, Paul A

2008-07-23

Quantification of red grape tannin and red wine tannin using the methyl cellulose precipitable (MCP) tannin assay and the Adams-Harbertson (A-H) tannin assay were investigated. The study allowed for direct comparison between the repeatability of the assays and for the assessment of other practical considerations such as time efficiency, ease of practice, and throughput, and assessed the relationships between tannin quantification by both analytical techniques. A strong correlation between the two analytical techniques was observed when quantifying grape tannin (r(2) = 0.96), and a good correlation was observed for wine tannins (r(2) = 0.80). However, significant differences in the reported tannin values for the analytical techniques were observed (approximately 3-fold). To explore potential reasons for the difference, investigations were undertaken to determine how several variables influenced the final tannin quantification for both assays. These variables included differences in the amount of tannin precipitated (monitored by HPLC), assay matrix variables, and the monomers used to report the final values. The relationship between tannin quantification and wine astringency was assessed for the MCP and A-H tannin assays, and both showed strong correlations with perceived wine astringency (r(2) = 0.83 and r(2) = 0.90, respectively). The work described here gives guidance to those wanting to understand how the values between the two assays relate; however, a conclusive explanation for the differences in values between the MCP and A-H tannin assays remains unclear, and further work in this area is required.

Effects of tannins on population dynamics of sympatric seed-eating rodents: the potential role of gut tannin-degrading bacteria.

PubMed

Zhang, Yihao; Bartlow, Andrew W; Wang, Zhenyu; Yi, Xianfeng

2018-05-07

Chemical compounds in seeds exert negative and even lethal effects on seed-consuming animals. Tannin-degrading bacteria in the guts of small mammals have been associated with the ability to digest seeds high in tannins. At the population level, it is not known if tannins influence rodent species differently according to the composition of their gut microbiota. Here, we test the hypothesis that sympatric tree species with different tannins exert contrasting effects on population fluctuations of seed-eating rodents. We collected a 10-year dataset of seed crops and rodent population sizes and sequenced 16S rRNA of gut microbes. The abundance of Apodemus peninsulae was not correlated with seed crop of either high-tannin Quercus mongolica or low-tannin Corylus mandshurica, but positively correlated with their total seed crops. Abundance of Tamias sibiricus was negatively correlated with seed crop of Q. mongolica but positively correlated with C. mandshurica. Body masses of A. peninsulae and T. sibiricus decreased when given high-tannin food; however, only the survival of T. sibiricus was reduced. The abundance of microbial genus Lactobacillus exhibiting potential tannin-degrading activity was significantly higher in A. peninsulae than in T. sibiricus. Our results suggest that masting tree species with different tannin concentrations may differentially influence population fluctuations of seed predators hosting different gut microbial communities. Although the conclusion is based on just correlational analysis of a short time-series, seeds with different chemical composition may influence rodent populations differently. Future work should examine these questions further to understand the complex interactions among seeds, gut microbes, and animal populations.

Ruminal biohydrogenation as affected by tannins in vitro.

PubMed

Vasta, Valentina; Makkar, Harinder P S; Mele, Marcello; Priolo, Alessandro

2009-07-01

The aim of the present work was to study the effects of tannins from carob (CT; Ceratonia siliqua), acacia leaves (AT; Acacia cyanophylla) and quebracho (QT; Schinopsis lorentzii) on ruminal biohydrogenation in vitro. The tannins extracted from CT, AT and QT were incubated for 12 h in glass syringes in cow buffered ruminal fluid (BRF) with hay or hay plus concentrate as a substrate. Within each feed, three concentrations of tannins were used (0.0, 0.6 and 1.0 mg/ml BRF). The branched-chain volatile fatty acids, the branched-chain fatty acids and the microbial protein concentration were reduced (P < 0.05) by tannins. In the tannin-containing fermenters, vaccenic acid was accumulated (+23 %, P < 0.01) while stearic acid was reduced ( - 16 %, P < 0.0005). The concentration of total conjugated linoleic acid (CLA) isomers in the BRF was not affected by tannins. The assay on linoleic acid isomerase (LA-I) showed that the enzyme activity (nmol CLA produced/min per mg protein) was unaffected by the inclusion of tannins in the fermenters. However, the CLA produced by LA-I (nmol/ml per min) was lower in the presence of tannins. These results suggest that tannins reduce ruminal biohydrogenation through the inhibition of the activity of ruminal micro-organisms.

Condensed tannins. Structure of the "phenolic scids"

Treesearch

Peter E. Laks; Richard W. Hemingway

1987-01-01

Conifer bark-derived condensed tannins can be used in formulating adhesives. Under some extraction conditions and during normal adhesive formulation, the tannin is exposed to strongly alkaline conditions. Alkaline rearrangement results in partial or total rearrangement of tannins of the procyanidin class to "phenolic acids" which have less phloroglucinol...

HPLC retention thermodynamics of grape and wine tannins.

PubMed

Barak, Jennifer A; Kennedy, James A

2013-05-08

The effect of grape and wine tannin structure on retention thermodynamics under reversed-phase high-performance liquid chromatography conditions on a polystyrene divinylbenzene column was investigated. On the basis of retention response to temperature, an alternative retention factor was developed to approximate the combined temperature response of the complex, unresolvable tannin mixture. This alternative retention factor was based upon relative tannin peak areas separated by an abrupt change in solvent gradient. Using this alternative retention factor, retention thermodynamics were calculated. Van't Hoff relationships of the natural log of the alternative retention factor against temperature followed Kirchoff's relationship. An inverse quadratic equation was fit to the data, and from this the thermodynamic parameters for tannin retention were calculated. All tannin fractions exhibited exothermic, spontaneous interaction, with enthalpy-entropy compensation observed. Normalizing for tannin size, distinct tannin compositional effects on thermodynamic parameters were observed. The results of this study indicate that HPLC can be valuable for measuring the thermodynamics of tannin interaction with a hydrophobic surface and provides a potentially valuable alternative to calorimetry. Furthermore, the information gathered may provide insight into understanding red wine astringency quality.

Aroma Glycosides in Grapes and Wine.

PubMed

Liu, Jibin; Zhu, Xiao-Lin; Ullah, Niamat; Tao, Yong-Sheng

2017-02-01

The major aroma components in grapes and wine include free volatile compounds and glycosidic nonvolatile compounds. The latter group of compounds is more than 10 times abundant of the former, and constitutes a big aroma reserve in grapes and wine. This review summarizes the research results obtained recently for the identification of aroma glycosides in grapes and wine, including grape glycoside structures, differences in aroma glycosides among grape varieties, hydrolysis mechanisms, and the factors that influence them. It also presents the analytical techniques used to identify the glycosidic aroma precursors. The operational strategies, challenges, and improvements of each step encountered in the analysis of glycosidic aroma precursors are described. This review intends to provide a convenient reference for researchers interested in the methods used for the determination of the aroma glucosides composition and the recognition of their chemical structures. © 2017 Institute of Food Technologists®.

Coriariin M, a trimeric hydrolysable tannin with dehydrodigalloyl and valoneoyl groups as linking units, and accompanying dimeric hydrolysable tannins from Coriaria japonica.

PubMed

Shimozu, Yuuki; Hirai, Takayasu; Hatano, Tsutomu

2018-07-01

Three oligomeric hydrolysable tannins, coriariins K, L, and M, which were previously undescribed, together with five known hydrolysable tannins were isolated from dried leaves of Coriaria japonica. Their structures were determined based on 1D and 2D NMR spectroscopy, HR-ESI-MS, and ECD spectroscopy experiments. Among the isolated compounds, coriariin M has a unique trimer structure where both dehydrodigalloyl and valoneoyl group linkages were found between the hydrolysable tannin monomers. Dimeric hydrolysable tannins coriariins K and L, having a dehydrodigalloyl group as the linking unit, were structurally related to coriariin A, the main hydrolysable tannin of this plant species. Additionally, the complexation of the eight hydrolysable tannins isolated in this study with bovine serum albumin (BSA) to form water-soluble macromolecules was analyzed using native polyacrylamide gel electrophoresis (PAGE). A comparison of the behaviors of the oligomeric hydrolysable tannins suggested the participation of the hexahydroxydiphenoyl group and the importance of the molecular sizes of the hydrolysable tannins in the formation of macromolecules. Copyright © 2018 Elsevier Ltd. All rights reserved.

Effect of tannins on the in vitro growth of Clostridium perfringens.

PubMed

Elizondo, Ana M; Mercado, Elsa C; Rabinovitz, Bettina C; Fernandez-Miyakawa, Mariano E

2010-10-26

Vegetable tannins are water-soluble polyphenolic compounds of varying molecular weights that occur abundantly in nature. The diet of many free-ranging wild animals contains significant amounts of tannins. Also, commercial tannins are used in animal industry as food additives to improve animal performance. In order to further determine the capacity of tannins to inhibit the development of intestinal diseases produced by Clostridium pefringens, we evaluated here the effect of tannins from quebracho, chestnut or combinations of both on C. perfringens and their toxins. The C. perfringens (types A, B, C, D and E) growth obtained from the intestine of healthy and diseased animals was reduced in a dose-dependent manner in the presence of quebracho tannins, chestnut tannins, combinations of both or a commercial formula based in these tannins. Although the minimal inhibitory concentration of both tannins varied between isolates, no statistically significant differences were observed between isolates from healthy or sick animals. Comparative analysis showed that the concentrations of quebracho tannin inhibiting the growth of C. perfringens were higher than chestnut tannin. In fact, antibacterial effect of quebracho tannin was increased up to 20 times with the addition of 25% of chestnut tannin and 85 times with 75% of chestnut tannin. Antibacterial activity of the commercial product was up to ~50 times higher than quebracho tannin alone. Quebracho tannin showed partial bactericidal activity, whereas chestnut tannin activity was stronger. Both tannins were able to reduce the alpha toxin lecithinase activity and epsilon toxin cytotoxicity in MDCK cells. These results suggest that tannin-supplemented diet could be useful to prevent some clostridial diseases. Copyright © 2010 Elsevier B.V. All rights reserved.

Recovery of uranium from seawater by immobilized tannin

DOE Office of Scientific and Technical Information (OSTI.GOV)

Sakaguchi, T.; Nakajima, A.

1987-06-01

Tannin compounds having multiple adjacent hydroxy groups have an extremely high affinity for uranium. To prevent the leaching of tannins into water and to improve the adsorbing characteristics of these compounds, the authors tried to immobilize tannins. The immobilized tannin has the most favorable features for uranium recovery; high selective adsorption ability to uranium, rapid adsorption rate, and applicability in both column and batch systems. The immobilized tannin can recover uranium from natural seawater with high efficiency. About 2530 ..mu..g uranium is adsorbed per gram of this adsorbent within 22 h. Depending on the concentration in seawater, an enrichment ofmore » up to 766,000-fold within the adsorbent is possible. Almost all uranium adsorbed is easily desorbed with a very dilute acid. Thus, the immobilized tannin can be used repeatedly in the adsorption-desorption process.« less

Pregnane glycosides from Sansevieria trifasciata.

PubMed

Mimaki, Y; Inoue, T; Kuroda, M; Sashida, Y

1997-01-01

Phytochemical analysis of the whole plant of Sansevieria trifasciata, one of the most common Agavaceae plants, has resulted in the isolation of four new pregnane glycosides. Their structures have been determined by spectroscopic analysis and acid- and alkaline-catalysed hydrolysis to be 1 beta,3 beta-dihydroxypregna-5,16-dien-20-one glycosides. This is believed to be the first report of the isolation of the pregnane glycosides from a plant of the family Agavaceae.

Hydrolyzable Tannins, Flavonol Glycosides, and Phenolic Acids Show Seasonal and Ontogenic Variation in Geranium sylvaticum.

PubMed

Tuominen, Anu; Salminen, Juha-Pekka

2017-08-09

The seasonal variation of polyphenols in the aboveground organs and roots of Geranium sylvaticum in four populations was studied using UPLC-DAD-ESI-QqQ-MS/MS. The content of the main compound, geraniin, was highest (16% of dry weight) in the basal leaves after the flowering period but stayed rather constant throughout the growing season. Compound-specific mass spectrometric methods revealed the different seasonal patterns in minor polyphenols. Maximum contents of galloylglucoses and flavonol glycosides were detected in the small leaves in May, whereas the contents of further modified ellagitannins, such as ascorgeraniin and chebulagic acid, increased during the growing season. In flower organs, the polyphenol contents differed significantly between ontogenic phases so that maximum amounts were typically found in the bud phase, except in pistils the amount of gallotannins increased significantly in the fruit phase. These results can be used in evaluating the role of polyphenols in plant-herbivore interactions or in planning the best collection times of G. sylvaticum for compound isolation purposes.

The susceptibility of soil enzymes to inhibition by leaf litter tannins is dependent on the tannin chemistry, enzyme class and vegetation history.

PubMed

Triebwasser, Daniella J; Tharayil, Nishanth; Preston, Caroline M; Gerard, Patrick D

2012-12-01

By inhibiting soil enzymes, tannins play an important role in soil carbon (C) and nitrogen (N) mineralization. The role of tannin chemistry in this inhibitory process, in conjunction with enzyme classes and isoforms, is less well understood. Here, we compared the inhibition efficiencies of mixed tannins (MTs, mostly limited to angiosperms) and condensed tannins (CTs, produced mostly by gymnosperms) against the potential activity of β-glucosidase (BG), N-acetyl-glucosaminidase (NAG), and peroxidase in two soils that differed in their vegetation histories. Compared with CTs, MTs exhibited 50% more inhibition of almond (Prunus dulcis) BG activity and greater inhibition of the potential NAG activity in the gymnosperm-acclimatized soils. CTs exhibited lower BG inhibition in the angiosperm-acclimated soils, whereas both types of tannins exhibited higher peroxidase inhibition in the angiosperm soils than in gymnosperm soils. At all of the tested tannin concentrations, irrespective of the tannin type and site history, the potential peroxidase activity was inhibited two-fold more than the hydrolase activity and was positively associated with the redox-buffering efficiency of tannins. Our finding that the inhibitory activities and mechanisms of MTs and CTs are dependent on the vegetative history and enzyme class is novel and furthers our understanding of the role of tannins and soil isoenzymes in decomposition. © 2012 The Authors. New Phytologist © 2012 New Phytologist Trust.

Phenolic glycosides and ionone glycoside from the stem of Sargentodoxa cuneata.

PubMed

Chang, Jun; Case, Ryan

2005-12-01

Four phenolic glycosides, cuneatasides A-D (1-4), and one ionone glycoside cuneataside E (5), together with seven known phenolic compounds (6-12) were isolated from the water-soluble constituents of the stem of Sargentodoxa cuneata (Sargentodoxaceae). Their structures were elucidated by spectroscopic analysis. In vitro tests for antimicrobial activity showed compounds 1 and 2 to possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Micrococcus epidermidis.

High-performance liquid chromatography determination of red wine tannin stickiness.

PubMed

Revelette, Matthew R; Barak, Jennifer A; Kennedy, James A

2014-07-16

Red wine astringency is generally considered to be the sensory result of salivary protein precipitation following tannin-salivary protein interaction and/or tannin adhering to the oral mucosa. Astringency in red wine is often described using qualitative terms, such as hard and soft. Differences in qualitative description are thought to be due in part to the tannin structure. Tannin chemistry contributions to qualitative description have been shown to correlate with the enthalpy of interaction between tannin and a hydrophobic surface. On the basis of these findings, a method was developed that enabled the routine determination of the thermodynamics of the tannin interaction with a hydrophobic surface (polystyrene divinylbenzene) for tannins in red wine following direct injection. The optimized analytical method monitored elution at four different column temperatures (25-40 °C, in 5 °C increments), had a 20 min run time, and was monitored at 280 nm. The results of this study confirm that the calculated thermodynamics of the interaction are intensive and, therefore, provide specific thermodynamic information. Variation in the enthalpy of interaction between tannin and a hydrophobic surface (tannin stickiness) is a unique, concentration-independent analytical parameter. The method, in addition to providing information on tannin stickiness, provides the tannin concentration.

Accumulation of uranium by immobilized persimmon tannin

DOE Office of Scientific and Technical Information (OSTI.GOV)

Sakaguchi, Takashi; Nakajima, Akira

1994-01-01

We have discovered that the extracted juice of unripe astringent persimmon fruit, designated as kakishibu or shibuol, has an extremely high affinity for uranium. To develop efficient adsorbents for uranium, we tried to immobilize kakishibu (persimmon tannin) with various aldehydes and mineral acids. Persimmon tannin immobilized with glutaraldehyde can accumulate 1.71 g (14 mEq U) of uranium per gram of the adsorbent. The uranium accumulating capacity of this adsorbent is several times greater than that of commercially available chelating resins (2-3 mEq/g). Immobilized persimmon tannin has the most favorable features for uranium recovery; high selective adsorption ability, rapid adsorption rate,more » and applicability in both column and batch systems. The uranium retained on immobilized persimmon tannin can be quantitatively and easily eluted with a very dilute acid, and the adsorbent can thus be easily recycled in the adsorption-desorption process. Immobilized persimmon tannin also has a high affinity for thorium. 23 refs., 13 figs., 7 tabs.« less

Hydrolyzable tannins of tamaricaceous plants. V. Structures of monomeric-trimeric tannins and cytotoxicity of macrocyclic-type tannins isolated from Tamarix nilotica (1).

PubMed

Orabi, Mohamed A A; Taniguchi, Shoko; Sakagami, Hiroshi; Yoshimura, Morio; Yoshida, Takashi; Hatano, Tsutomu

2013-05-24

Three new ellagitannin monomers, nilotinins M5-M7 (1-3), a dimer, nilotinin D10 (4), and a trimer, nilotinin T1 (5), together with three known dimers, hirtellin D (7) and tamarixinins B (8) and C (9), and a trimer, hirtellin T2 (6), were isolated from Tamarix nilotica dried leaves. The structures of the tannins were elucidated by intensive spectroscopic methods and chemical conversions into known tannins. The new trimer (5) is a unique macrocyclic type whose monomeric units are linked together by an isodehydrodigalloyl and two dehydrodigalloyl moieties. Additionally, dimeric and trimeric macrocyclic-type tannins isolated from T. nilotica in this study were assessed for possible cytotoxic activity against four human tumor cell lines. Tumor-selective cytotoxicities of the tested compounds were higher than those of synthetic and natural potent cytotoxic compounds, including polyphenols, and comparable with those of 5-fluorouracil and melphalan.

New lignan glycosides from Justicia procumbens.

PubMed

Jin, Hong; Yang, Shu; Dong, Jun-Xing

2017-01-01

Four new lignan glycosides (1-4), named procumbenosides I, K, L, and M, together with cleistanthin B (5) reported for the first time in the genus Justicia, and 5 other known arylnaphthalene lignan glycosides (6-10) were isolated from the whole plant of Justicia procumbens. The structures of the new compounds were elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. Procumbenoside M (4) was a rare sesquilignan glycoside never previously reported in the species of Justicia. The paper also provided insight into the conformational equilibria existing in the lignan glycosides of the plant.

Tannins: current knowledge of food sources, intake, bioavailability and biological effects.

PubMed

Serrano, José; Puupponen-Pimiä, Riitta; Dauer, Andreas; Aura, Anna-Marja; Saura-Calixto, Fulgencio

2009-09-01

Tannins are a unique group of phenolic metabolites with molecular weights between 500 and 30 000 Da, which are widely distributed in almost all plant foods and beverages. Proanthocyanidins and hydrolysable tannins are the two major groups of these bioactive compounds, but complex tannins containing structural elements of both groups and specific tannins in marine brown algae have also been described. Most literature data on food tannins refer only to oligomeric compounds that are extracted with aqueous-organic solvents, but a significant number of non-extractable tannins are usually not mentioned in the literature. The biological effects of tannins usually depend on their grade of polymerisation and solubility. Highly polymerised tannins exhibit low bioaccessibility in the small intestine and low fermentability by colonic microflora. This review summarises a new approach to analysis of extractable and non-extractable tannins, major food sources, and effects of storage and processing on tannin content and bioavailability. Biological properties such as antioxidant, antimicrobial and antiviral effects are also described. In addition, the role of tannins in diabetes mellitus has been discussed.

Grape seed and apple tannins: emulsifying and antioxidant properties.

PubMed

Figueroa-Espinoza, Maria Cruz; Zafimahova, Andrea; Alvarado, Pedro G Maldonado; Dubreucq, Eric; Poncet-Legrand, Céline

2015-07-01

Tannins are natural antioxidants found in plant-based foods and beverages, whose amphiphilic nature could be useful to both stabilize emulsions and protect unsaturated lipids from oxidation. In this paper, the use of tannins as antioxidant emulsifiers was studied. The main parameters influencing the stability of emulsions (i.e. tannins structure and concentration, aqueous phase pH, and ionic strength) were identified and optimized. Oil in water emulsions stabilized with tannins were compared with those stabilized with two commercial emulsifying agents, poly(vinyl alcohol) (PVA) and polyoxyethylene hydrogenated castor oil. In optimized conditions, the condensed tannins allowed to obtain a stability equivalent to that of PVA. Tannins presented good antioxidant activity in oil in water emulsion, as measured by the conjugated autoxidizable triene (CAT) assay. Copyright © 2015 Elsevier Ltd. All rights reserved.

A role for anthocyanin in determining wine tannin concentration in Shiraz.

PubMed

Kilmister, Rachel L; Mazza, Marica; Baker, Nardia K; Faulkner, Peta; Downey, Mark O

2014-01-01

Four wines were made to investigate the effect of different anthocyanin and tannin fruit concentrations on wine phenolics and colour. Wines that were made from fruit with high anthocyanin concentration had high tannin concentrations regardless of the concentration of tannin in fruit, while wines made from fruit with low anthocyanin also had low tannin concentration. It was found that fruit anthocyanin concentration correlated with wine tannin concentration, wine colour and polymeric pigment formation. Anthocyanin concentration might be a key component for increasing tannin solubility and extraction into wine and the formation of polymeric pigments. Industry implications include managing tannin and anthocyanin fruit concentration for targeting tannin extraction and polymeric pigment formation in wine. Crown Copyright © 2013. Published by Elsevier Ltd. All rights reserved.

Powdered hide model for vegetable tanning II. hydrolyzable tannin

USDA-ARS?s Scientific Manuscript database

Vegetable tannages employ both condensed and hydrolyzable tannins. As part of our exploration of tanning mechanisms, we reported last year on interactions of the condensed tannin, quebracho, with powdered hide. In this study, the interactions of chestnut extract, a hydrolyzable tannin, with powdere...

Hydrolyzable and condensed tannins resistance in Clostridium perfringens.

PubMed

Redondo, L M; Dominguez, J E; Rabinovitz, B C; Redondo, E A; Fernández Miyakawa, M E

2015-08-01

Tannins added in the diet are being used to improve nutrition and health in farm animals as an alternative to antibiotic growth promoters and to control enteric clostridial diseases. However, the capacity of Clostridium perfringens to develop resistance under the selective pressure of tannins is unknown. The purpose of this study was to determine if C. perfringens possess the ability to develop resistance against tannins in comparison with antimicrobial agents. Susceptibility for 7 AGPs (antimicrobial growth promoters), 9 therapeutic antimicrobials and 2 tannin based extracts was determined for 30 C. perfringens strains isolated from poultry and cattle. Two susceptible strains were selected and cultured in presence of sub-inhibitory concentrations of tannins and AGPs for resistant sub-populations selection. Tannin resistance of C. perfringens isolates from both animal species revealed no statistically significant differences in MICs (minimum inhibitory concentration). Poultry isolates showed higher MICs to several AGPs compared with cattle isolates. All isolates were susceptible to the therapeutic antimicrobials tested, but avian isolates showed a significantly lower susceptibility to these antimicrobials which was highly correlated with an increased resistance to bacitracin and others AGPs. In-vitro selection of resistant clones suggests that C. perfringens was unable to develop resistance against tannins at least compared to AGPs like bacitracin and avilamycin. Avian origin strains, which were previously exposed to antibiotics showed higher resistance, compared to cattle origin strains. These results suggest that the evolution of resistance against tannins in C. perfringens would be more difficult and slower than to the determined AGPs. Copyright © 2015 Elsevier Ltd. All rights reserved.

Cardiac arrhythmias from a malpositioned Greenfield filter in a traumatic quadriplegic.

PubMed

Bach, J R; Zaneuski, R; Lee, H

1990-10-01

A case study is presented of premature Greenfield filter discharge with intracardiac migration and resulting life-threatening arrhythmias. These arrhythmias also interfered with the patient's transition from ventilatory support via orotracheal intubation to noninvasive positive airway pressure ventilatory support methods. The patient's arrhythmias were controlled by a demand cardiac pacemaker and cardiac glycoside therapy. No anticoagulants were used. She had no further filter migration nor significant complications for 16 months after hospital discharge.

Interactions of tea tannins and condensed tannins with proteins.

PubMed

Frazier, Richard A; Deaville, Eddie R; Green, Rebecca J; Stringano, Elisabetta; Willoughby, Ian; Plant, John; Mueller-Harvey, Irene

2010-01-20

Binding parameters for the interactions of four types of tannins: tea catechins, grape seed proanthocyanidins, mimosa 5-deoxy proanthocyanidins, and sorghum procyanidins (mDP=17), with gelatin and bovine serum albumin (BSA) have been determined from isothermal titration calorimetry data. Equilibrium binding constants determined for the interaction with gelatin were in the range 10(4) to 10(6) M(-1) and in the order: sorghum procyanidins > grape seed proanthocyanidins > mimosa 5-deoxy proanthocyanidins > tea catechins. Interaction with BSA was generally weaker, with equilibrium binding constants of < or =10(3)M(-1) for grape seed proanthocyanidins, mimosa 5-deoxy proanthocyanidins and tea catechins, and 10(4)M(-1) for the sorghum procyanidins. In all cases the interactions with proteins were exothermic and involved multiple binding sites on the protein. The data are discussed in relation to the structures and the known nutritional effects of the condensed tannins.

Monoterpene glycosides from Paeonia veitchii.

PubMed

Fu, Qiang; Tan, Mao-Ling; Yuan, Hai-Mei; Chen, Jiang; Fu, Jia

2017-01-01

The EtOH extract of the roots of Paeonia veitchii afforded two new monoterpene glycosides paeonidanin I (1) and paeonidanin J (2), and a new dimeric monoterpene glycoside paeonidanin K (3). Their structures were elucidated on the basis of spectroscopic means and hydrolysis products.

Perspectives for the industrial enzymatic production of glycosides.

PubMed

de Roode, B Mattheus; Franssen, Maurice C R; van der Padt, Albert; Boom, Remko M

2003-01-01

Glycosides are of commercial interest for industry in general and specifically for the pharmaceutical and food industry. Currently chemical preparation of glycosides will not meet EC food regulations, and therefore chemical preparation of glycosides is not applicable in the food industry. Thus, enzyme-catalyzed reactions are a good alternative. However, until now the low yields obtained by enzymatic methods prevent the production of glycosides on a commercial scale. Therefore, high yields should be established by a combination of optimum reaction conditions and continuous removal of the product. Unfortunately, a bioreactor for the commercial scale production of glycosides is not available. The aim of this article is to discuss the literature with respect to enzymatic production of glycosides and the design of an industrially viable bioreactor system.

Identification and quantification of cardiac glycosides in blood and urine samples by HPLC/MS/MS.

PubMed

Guan, F; Ishii, A; Seno, H; Watanabe-Suzuki, K; Kumazawa, T; Suzuki, O

1999-09-15

Cardiac glycosides (CG) are of forensic importance because of their toxicity and the fact that very limited methods are available for identification of CG in biological samples. In this study, we have developed an identification and quantification method for digoxin, digitoxin, deslanoside, digoxigenin, and digitoxigenin by high-performance liquid chromatography tandem mass spectrometry (HPLC/MS/MS). CG formed abundant [M + NH4]+ ions and much less abundant [M + H]+ ions as observed with electrospray ionization (ESI) source and ammonium formate buffer. Under mild conditions for collision-induced dissociation (CID), each [M + NH4]+ ion fragmented to produce a dominant daughter ion, which was essential to the sensitive method of selected reaction monitoring (SRM) quantification of CG achieved in this study. SRM was compared with selected ion monitoring (SIM) regarding the effects of sample matrixes on the methodology. SRM produced lower detection limits with biological samples than SIM, while both methods produced equal detection limits with CG standards. On the basis of the HPLC/MS/MS results for CG, we have proposed some generalized points for conducting sensitive SRM measurements, in view of the property of analytes as well as instrumental conditions such as the type of HPLC/MS interface and CID parameters. Analytes of which the molecular ion can produce one abundant daughter ion with high yield under CID conditions may be sensitively measured by SRM. ESI is the most soft ionization source developed so far and can afford formation of the fragile molecular ions that are necessary for sensitive SRM detection. Mild CID conditions such as low collision energy and low pressure of collision gas favor production of an abundant daughter ion that is essential to sensitive SRM detection. This knowledge may provide some guidelines for conducting sensitive SRM measurements of very low concentrations of drugs or toxicants in biological samples.

Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales

PubMed Central

Yoshida, Takashi; Amakura, Yoshiaki; Yoshimura, Morio

2010-01-01

Plant tannins, including hydrolysable and condensed varieties, are well known antioxidants in medicinal plants, foods, and edible fruits. Their diverse biological properties and potential for disease prevention have been demonstrated by various in vitro and in vivo assays. A number of ellagitannins, the largest group of hydrolysable tannins, have been isolated from dicotyledoneous angiosperms and characterized. This diverse class of tannins is sub-grouped into simple ellagitannins, C-glycosidic ellagitannins, complex tannins (condensates of C-glycosidic tannins with flavan-3-ol), and oligomers up to pentamers. This review outlines and describes the chemotaxonomic significance of structural features in various types of ellagitannins found in plants belonging to the Myrtaceae, Onagraceae, and Melastomataceae families, which are all included in the order Myrtales. Any biological activities that have been reported, including antitumor and antibacterial effects as well as enzyme inhibition, are also reviewed. PMID:20162003

Salivary proline-rich protein may reduce tannin-iron chelation: a systematic narrative review.

PubMed

Delimont, Nicole M; Rosenkranz, Sara K; Haub, Mark D; Lindshield, Brian L

2017-01-01

Tannins are often cited for antinutritional effects, including chelation of non-heme iron. Despite this, studies exploring non-heme iron bioavailability inhibition with long-term consumption have reported mixed results. Salivary proline-rich proteins (PRPs) may mediate tannin-antinutritional effects on non-heme iron bioavailability. To review evidence regarding biochemical binding mechanisms and affinity states between PRPs and tannins, as well as effects of PRPs on non-heme iron bioavailability with tannin consumption in vivo. Narrative systematic review and meta-analysis. Common themes in biochemical modeling and affinity studies were collated for summary and synthesis; data were extracted from in vivo experiments for meta-analysis. Thirty-two studies were included in analysis. Common themes that positively influenced tannin-PRP binding included specificity of tannin-PRP binding, PRP and tannin stereochemistry. Hydrolyzable tannins have different affinities than condensed tannins when binding to PRPs. In vivo, hepatic iron stores and non-heme iron absorption are not significantly affected by tannin consumption ( d  = -0.64-1.84; -2.7-0.13 respectively), and PRP expression may increase non-heme iron bioavailability with tannin consumption. In vitro modeling suggests that tannins favor PRP binding over iron chelation throughout digestion. Hydrolyzable tannins are not representative of tannin impact on non-heme iron bioavailability in food tannins because of their unique structural properties and PRP affinities. With tannin consumption, PRP production is increased, and may be an initial line of defense against tannin-non-heme iron chelation in vivo . More research is needed to compare competitive binding of tannin-PRP to tannin-non-heme iron complexes, and elucidate PRPs' role in adaption to non-heme iron bioavailability in vivo.

Sorption of polyphenolics (tannins) to natural soils

USDA-ARS?s Scientific Manuscript database

Tannins enter soil systems via rainfall through the leaf canopy, leaf litter decomposition, and root exudation and decomposition. For tannins released into soils, the relative importance of sorption to soil; chemical reactions with soil minerals; and biological decomposition is unknown. Determinin...

Advance on the Flavonoid C-glycosides and Health Benefits.

PubMed

Xiao, Jianbo; Capanoglu, Esra; Jassbi, Amir Reza; Miron, Anca

2016-07-29

The dietary flavonoids, especially their glycosides, are the most vital phytochemicals in diets and are of great general interest due to their diverse bioactivity. Almost all natural flavonoids exist as their O-glycoside or C-glycoside forms in plants. The dietary flavonoid C-glycosides have received less attention than their corresponding O-glycosides. This review summarizes current knowledge regarding flavonoid C-glycosides and their influence on human health. Among the flavonoid C-glycosides, flavone C-glycosides, especially vitexin, isoorientin, orientin, isovitexin and their multiglycosides are more frequently mentioned than others. Flavonoid C-monoglycosides are poorly absorbed in human beings with very few metabolites in urine and blood and are deglycosylated and degraded by human intestinal bacteria in colon. However, flavonoid C-multiglycosides are absorbed unchanged in the intestine and distributed to other tissues. Flavonoid C-glycosides showed significant antioxidant activity, anticancer and antitumor activity, hepatoprotective activity, anti-inflammatory activity, anti-diabetes activity, antiviral activity, antibacterial and antifungal activity, and other biological effects. It looks like that the C-glycosylflavonoids in most cases showed higher antioxidant and anti-diabetes potential than their corresponding O-glycosylflavonoids and aglycones. However, there is a lack of in vivo data on the biological benefits of flavonoid C-glycosides. It is necessary to investigate more on how flavonoid C-glycosides prevent and handle the diseases.

Nutrient retention and fate of iron-binding phenolic compounds during the injera processing of tannin-free and high-tannin sorghum.

PubMed

Seyoum, Yohannes; Retta, Negussie; Baye, Kaleab

2016-03-30

Traits such as bird-, insect- and mould-resistance are the focus in selecting improved sorghum varieties, but this often increases the tannin content, which can negatively affect iron bioavailability. The grain characteristics, nutrient retention, and the fate of iron-binding polyphenols (IBPs) during injera processing, an Ethiopian traditional fermented pancake, were investigated using agriculturally improved tannin-free (TFC) and high-tannin (HTC) sorghum cultivars. The HTC had significantly higher IBP contents than the TFC (P < 0.05). Decortication led to iron (24-27%), calcium (18-43%), IBP (catechol 35-41%, galloyl 35-42%), and tannin (12-35%) losses. Sourdough fermentation reduced the IBP and tannin concentrations in HTC, but had no effect on the IBP concentrations in TFC. The modified injera processing that included pre-soaking resulted in the highest IBP reductions (galloyl 73% and catechol 71%). Nutrient retention in HTC and TFC processing was different. Including a pre-soaking step during injera processing of HTC could counter the negative effects of IBP on iron absorption, while benefiting from the agronomic features of HTC. © 2015 Society of Chemical Industry.

Anticancer and antioxidant tannins from Pimenta dioica leaves.

PubMed

Marzouk, Mohamed S A; Moharram, Fatma A; Mohamed, Mona A; Gamal-Eldeen, Amira M; Aboutabl, Elsayed A

2007-01-01

Two galloylglucosides, 6-hydroxy-eugenol 4-O-(6'-O-galloyl)-beta-D-4C1-glucopyranoside (4) and 3-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol-2-O-(2',6'-di-O-galloyl)-beta-D -4C1-glucopyranoside (7), and two C-glycosidic tannins, vascalaginone (10) and grandininol (14), together with fourteen known metabolites, gallic acid (1), methyl gallate (2), nilocitin (3), 1-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-(alpha/beta)-D-glucopyranose (5), 4,6-(S)-hexahydroxydiphenoyl-(alpha/beta)-D-glucopyranose (6), 3,4,6-valoneoyl-(alpha/beta)-D-glucopyranose (8), pedunculagin (9), casuariin (11), castalagin (12), vascalagin (13), casuarinin (15), grandinin (16), methyl-flavogallonate (17) and ellagic acid (18), were identified from the leaves of Pimenta dioica (Merr.) L. (Myrtaceae) on the basis of their chemical and physicochemical analysis (UV, HRESI-MS, 1D and 2D NMR). It was found that 9 is the most cytotoxic compound against solid tumour cancer cells, the most potent scavenger against the artificial radical DPPH and physiological radicals including ROO*, OH*, and O2-*, and strongly inhibited the NO generation and induced the proliferation of T-lymphocytes and macrophages. On the other hand, 3 was the strongest NO inhibitor and 16 the highest stimulator for the proliferation of T-lymphocytes, while 10 was the most active inducer of macrophage proliferation.

[Study on the kinetic fluorimetric determination of tannins in tea].

PubMed

Feng, Su-ling; Tang, Jun-ming; Fan, Jing

2003-04-01

A simple and highly sensitive kinetic fluorimetric method is proposed for the determination of trace tannins, based on the activation of tannins on the oxidation of pyronine Y by hydrogen peroxide catalyzed by Cu(II) ion. The effects of some experimental conditions were investigated and discussed in detail. The fixed reaction time procedure was used to determine the fluorescence intensity of the system. The calibration curve of tannin was linear in the range of 0.06-0.96 mg.L-1, and the detection limit for tannin was 0.032 mg.L-1. The relative standard deviation for the measurement of 0.32 mg.L-1 tannin (n = 11) was 2.3%. The proposed method has been successfully applied to the determination of tannins in tea. The results obtained were compared with those provided by the Folin-Ciocalteu method.

Tree resistance to Lymantria dispar caterpillars: importance and limitations of foliar tannin composition.

PubMed

Barbehenn, Raymond V; Jaros, Adam; Lee, Grace; Mozola, Cara; Weir, Quentin; Salminen, Juha-Pekka

2009-04-01

The ability of foliar tannins to increase plant resistance to herbivores is potentially determined by the composition of the tannins; hydrolyzable tannins are much more active as prooxidants in the guts of caterpillars than are condensed tannins. By manipulating the tannin compositions of two contrasting tree species, this work examined: (1) whether increased levels of hydrolyzable tannins increase the resistance of red oak (Quercus rubra L.), a tree with low resistance that produces mainly condensed tannins, and (2) whether increased levels of condensed tannins decrease the resistance of sugar maple (Acer saccharum Marsh.), a tree with relatively high resistance that produces high levels of hydrolyzable tannins. As expected, when Lymantria dispar L. caterpillars ingested oak leaves coated with hydrolyzable tannins, levels of hydrolyzable tannin oxidation increased in their midgut contents. However, increased tannin oxidation had no significant impact on oxidative stress in the surrounding midgut tissues. Although growth efficiencies were decreased by hydrolyzable tannins, growth rates remained unchanged, suggesting that additional hydrolyzable tannins are not sufficient to increase the resistance of oak. In larvae on condensed tannin-coated maple, no antioxidant effects were observed in the midgut, and levels of tannin oxidation remained high. Consequently, neither oxidative stress in midgut tissues nor larval performance were significantly affected by high levels of condensed tannins. Post hoc comparisons of physiological mechanisms related to tree resistance revealed that maple produced not only higher levels of oxidative stress in the midgut lumen and midgut tissues of L. dispar, but also decreased protein utilization efficiency compared with oak. Our results suggest that high levels of hydrolyzable tannins are important for producing oxidative stress, but increased tree resistance to caterpillars may require additional factors, such as those that produce

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

PubMed

Li, Haixia; Wang, Zhao; Liu, Yanze

2003-06-01

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.

Tannins from Canarium album with potent antioxidant activity*

PubMed Central

Zhang, Liang-liang; Lin, Yi-ming

2008-01-01

The contents of total phenolics and extractable condensed tannins in the leaves, twigs and stem bark of Canarium album were determined. The structural heterogeneity of condensed tannins from stem bark was characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and nuclear magnetic resonance (NMR) analyses. The results show the predominance of signals representative of procyanidins and prodelphinidins. In addition, epicatechin and epigallocatechin polymers with galloylated procyanidin or prodelphinidin were also observed. The tannins were screened for their potential antioxidant activities using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric reducing/antioxidant power (FRAP) model systems. Tannins extracted from leaves, twigs and stem bark all showed a very good DPPH radical scavenging activity and ferric reducing power. PMID:18500781

Tannins from Canarium album with potent antioxidant activity.

PubMed

Zhang, Liang-liang; Lin, Yi-ming

2008-05-01

The contents of total phenolics and extractable condensed tannins in the leaves, twigs and stem bark of Canarium album were determined. The structural heterogeneity of condensed tannins from stem bark was characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and nuclear magnetic resonance (NMR) analyses. The results show the predominance of signals representative of procyanidins and prodelphinidins. In addition, epicatechin and epigallocatechin polymers with galloylated procyanidin or prodelphinidin were also observed. The tannins were screened for their potential antioxidant activities using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric reducing/antioxidant power (FRAP) model systems. Tannins extracted from leaves, twigs and stem bark all showed a very good DPPH radical scavenging activity and ferric reducing power.

Tannins occurring in the toxic Brazilian plant Thiloa glaucocarpa.

PubMed

Itakura, Y; Habermehl, G; Mebs, D

1987-01-01

Four tannins were isolated from dried leaves of Thiloa glaucocarpa, which is one of the plants causing poisoning of cattle in Brazil. These four tannins were determined from spectrometric and chemical evidence to be the ellagic C-glucosyl tannins vescalagin, castalagin, stachyurin and casuarinin. The main components, vescalagin and castalagin, are also known as constituents of oak (Quercus spp.), the toxicity of which for cattle is supposed to be due to tannins. Suggestions concerning the resemblance of the symptoms of poisoning by Thiloa glaucocarpa and by oak are supported by the presence of the constituents in both plants.

Research observation: Hydrolyzable and condensed tannins in plants of the northwest

USGS Publications Warehouse

Gonzalez-Hernandez, M. P.; Karchesy, J.; Starkey, Edward E.

2003-01-01

Tannins are secondary metabolites that may influence feeding by mammals on plants. We analyzed hydrolyzable and condensed tannins in 30 plant species consumed by livestock and deer, as a preliminary attempt to study their possible implications on browsing and grazing in forest ecosystems. Heathers (Ericaceae) and plants of the Rose (Rosaceae) family had tannins, while forbs, grasses and shrubs other than the heathers did not show astringency properties. We found the highest tannin content of all the species in Rubus sp., with the highest value around 180 mg TAE/g dry weight in spring. Potentilla erecta, Alnus glutinosa and Quercus robur were next with 57 to 44 mg TAE/g dw. Total tannins in heathers ranged from 22 to 36 mg TAE/g dw. Levels of condensed tannins were higher than hydrolyzable for most of the species. Only Betula alba, Calluna vulgaris, Pteridium aquilinum and Vaccinium myrtillus had 100% hydrolyzable tannins. Tannin content of the species changed seasonally with highest values during the growing season, corresponding to late winter or early spring, depending on the species.

Recent Advances in Anticancer Activities and Drug Delivery Systems of Tannins.

PubMed

Cai, Yuee; Zhang, Jinming; Chen, Nelson G; Shi, Zhi; Qiu, Jiange; He, Chengwei; Chen, Meiwan

2017-07-01

Tannins, polyphenols in medicinal plants, have been divided into two groups of hydrolysable and condensed tannins, including gallotannins, ellagitannins, and (-)-epigallocatechin-3-gallate (EGCG). Potent anticancer activities have been observed in tannins (especially EGCG) with multiple mechanisms, such as apoptosis, cell cycle arrest, and inhibition of invasion and metastases. Furthermore, the combinational effects of tannins and anticancer drugs have been demonstrated in this review, including chemoprotective, chemosensitive, and antagonizing effects accompanying with anticancer effect. However, the applications of tannins have been hindered due to their poor liposolubility, low bioavailability, off-taste, and shorter half-life time in human body, such as EGCG, gallic acid, and ellagic acid. To tackle these obstacles, novel drug delivery systems have been employed to deliver tannins with the aim of improving their applications, such as gelatin nanoparticles, micelles, nanogold, liposomes, and so on. In this review, the chemical characteristics, anticancer properties, and drug delivery systems of tannins were discussed with an attempt to provide a systemic reference to promote the development of tannins as anticancer agents. © 2016 Wiley Periodicals, Inc.

Molecular Interaction Between Salivary Proteins and Food Tannins.

PubMed

Silva, Mafalda Santos; García-Estévez, Ignacio; Brandão, Elsa; Mateus, Nuno; de Freitas, Victor; Soares, Susana

2017-08-09

Polyphenols interaction with salivary proteins (SP) has been related with organoleptic features such as astringency. The aim of this work was to study the interaction between some human SP and tannins through two spectroscopic techniques, fluorescence quenching, and saturation transfer difference-nuclear magnetic resonance (STD-NMR). Generally, the results showed a significant interaction between SP and both condensed tannins and ellagitannins. Herein, STD-NMR proved to be a useful tool to map tannins' epitopes of binding, while fluorescence quenching allowed one to discriminate binding affinities. Ellagitannins showed the greatest binding constants values (K SV from 20.1 to 94.1 mM -1 ; K A from 0.7 to 8.3 mM -1 ) in comparison with procyanidins (K SV from 5.4 to 40.0 mM -1 ; K A from 1.1 to 2.7 mM -1 ). In fact, punicalagin was the tannin that demonstrated the highest affinity for all three SP. Regarding SP, P-B peptide was the one with higher affinity for ellagitannins. On the other hand, cystatins showed in general the lower K SV and K A values. In the case of condensed tannins, statherin was the SP with the highest affinity, contrasting with the other two SP. Altogether, these results are evidence that the distinct SP present in the oral cavity have different abilities to interact with food tannins class.

Oxygen consumption rates by different oenological tannins in a model wine solution.

PubMed

Pascual, Olga; Vignault, Adeline; Gombau, Jordi; Navarro, Maria; Gómez-Alonso, Sergio; García-Romero, Esteban; Canals, Joan Miquel; Hermosín-Gutíerrez, Isidro; Teissedre, Pierre-Louis; Zamora, Fernando

2017-11-01

The kinetics of oxygen consumption by different oenological tannins were measured in a model wine solution using the non-invasive method based on luminiscence. The results indicate that the oxygen consumption rate follows second-order kinetics depending on tannin and oxygen concentrations. They also confirm that the oxygen consumption rate is influenced by temperature in accordance with Arrhenius law. The indications are that ellagitannins are the fastest oxygen consumers of the different oenological tannins, followed in decreasing order by quebracho tannins, skin tannins, seed tannins and finally gallotannins. This methodology can therefore be proposed as an index for determining the effectiveness of different commercial tannins in protecting wines against oxidation. Copyright © 2017 Elsevier Ltd. All rights reserved.

Exploitation of dietary tannins to improve rumen metabolism and ruminant nutrition.

PubMed

Patra, Amlan K; Saxena, Jyotisna

2011-01-15

Tannins (hydrolysable and condensed tannin) are polyphenolic polymers of relatively high molecular weight with the capacity to form complexes mainly with proteins due to the presence of a large number of phenolic hydroxyl groups. They are widely distributed in nutritionally important forage trees, shrubs and legumes, cereals and grains, which are considered as anti-nutritional compounds due to their adverse effects on intake and animal performance. However, tannins have been recognised to modulate rumen fermentation favourably such as reducing protein degradation in the rumen, prevention of bloat, inhibition of methanogenesis and increasing conjugated linoleic acid concentrations in ruminant-derived foods. The inclusion of tannins in diets has been shown to improve body weight and wool growth, milk yields and reproductive performance. However, the beneficial effects on rumen modulation and animal performance have not been consistently observed. This review discusses the effects of tannins on nitrogen metabolism in the rumen and intestine, and microbial populations (bacteria, protozoa, fungi and archaea), metabolism of tannins, microbial tolerance mechanisms to tannins, inhibition of methanogenesis, ruminal biohydrogenation processes and performance of animals. The discrepancies of responses of tannins among different studies are attributed to the different chemical structures (degree of polymerisation, procyanidins to propdelphinidins, stereochemistry and C-C bonding) and concentrations of tannins, and type of diets. An establishment of structure-activity relationship would be required to explain differences among studies and obtain consistent beneficial tannin effects. Copyright © 2010 Society of Chemical Industry.

Tannin structural elucidation and quantitative ³¹P NMR analysis. 2. Hydrolyzable tannins and proanthocyanidins.

PubMed

Melone, Federica; Saladino, Raffaele; Lange, Heiko; Crestini, Claudia

2013-10-02

An unprecedented analytical method that allows simultaneous structural and quantitative characterization of all functional groups present in tannins is reported. In situ labeling of all labile H groups (aliphatic and phenolic hydroxyls and carboxylic acids) with a phosphorus-containing reagent (Cl-TMDP) followed by quantitative ³¹P NMR acquisition constitutes a novel fast and reliable analytical tool for the analysis of tannins and proanthocyanidins with significant implications for the fields of food and feed analyses, tannery, and the development of natural polyphenolics containing products.

Variants of glycoside hydrolases

DOEpatents

Teter, Sarah; Ward, Connie; Cherry, Joel; Jones, Aubrey; Harris, Paul; Yi, Jung

2013-02-26

The present invention relates to variants of a parent glycoside hydrolase, comprising a substitution at one or more positions corresponding to positions 21, 94, 157, 205, 206, 247, 337, 350, 373, 383, 438, 455, 467, and 486 of amino acids 1 to 513 of SEQ ID NO: 2, and optionally further comprising a substitution at one or more positions corresponding to positions 8, 22, 41, 49, 57, 113, 193, 196, 226, 227, 246, 251, 255, 259, 301, 356, 371, 411, and 462 of amino acids 1 to 513 of SEQ ID NO: 2 a substitution at one or more positions corresponding to positions 8, 22, 41, 49, 57, 113, 193, 196, 226, 227, 246, 251, 255, 259, 301, 356, 371, 411, and 462 of amino acids 1 to 513 of SEQ ID NO: 2, wherein the variants have glycoside hydrolase activity. The present invention also relates to nucleotide sequences encoding the variant glycoside hydrolases and to nucleic acid constructs, vectors, and host cells comprising the nucleotide sequences.

Variants of glycoside hydrolases

DOEpatents

Teter, Sarah [Davis, CA; Ward, Connie [Hamilton, MT; Cherry, Joel [Davis, CA; Jones, Aubrey [Davis, CA; Harris, Paul [Carnation, WA; Yi, Jung [Sacramento, CA

2011-04-26

The present invention relates to variants of a parent glycoside hydrolase, comprising a substitution at one or more positions corresponding to positions 21, 94, 157, 205, 206, 247, 337, 350, 373, 383, 438, 455, 467, and 486 of amino acids 1 to 513 of SEQ ID NO: 2, and optionally further comprising a substitution at one or more positions corresponding to positions 8, 22, 41, 49, 57, 113, 193, 196, 226, 227, 246, 251, 255, 259, 301, 356, 371, 411, and 462 of amino acids 1 to 513 of SEQ ID NO: 2 a substitution at one or more positions corresponding to positions 8, 22, 41, 49, 57, 113, 193, 196, 226, 227, 246, 251, 255, 259, 301, 356, 371, 411, and 462 of amino acids 1 to 513 of SEQ ID NO: 2, wherein the variants have glycoside hydrolase activity. The present invention also relates to nucleotide sequences encoding the variant glycoside hydrolases and to nucleic acid constructs, vectors, and host cells comprising the nucleotide sequences.

Variants of glycoside hydrolases

DOEpatents

Teter, Sarah; Ward, Connie; Cherry, Joel; Jones, Aubrey; Harris, Paul; Yi, Jung

2017-07-11

The present invention relates to variants of a parent glycoside hydrolase, comprising a substitution at one or more positions corresponding to positions 21, 94, 157, 205, 206, 247, 337, 350, 373, 383, 438, 455, 467, and 486 of amino acids 1 to 513 of SEQ ID NO: 2, and optionally further comprising a substitution at one or more positions corresponding to positions 8, 22, 41, 49, 57, 113, 193, 196, 226, 227, 246, 251, 255, 259, 301, 356, 371, 411, and 462 of amino acids 1 to 513 of SEQ ID NO: 2 a substitution at one or more positions corresponding to positions 8, 22, 41, 49, 57, 113, 193, 196, 226, 227, 246, 251, 255, 259, 301, 356, 371, 411, and 462 of amino acids 1 to 513 of SEQ ID NO: 2, wherein the variants have glycoside hydrolase activity. The present invention also relates to nucleotide sequences encoding the variant glycoside hydrolases and to nucleic acid constructs, vectors, and host cells comprising the nucleotide sequences.

Sensory properties of wine tannin fractions: implications for in-mouth sensory properties.

PubMed

McRae, Jacqui M; Schulkin, Alex; Kassara, Stella; Holt, Helen E; Smith, Paul A

2013-01-23

Different molecular structures of grape tannins have been shown to influence astringency, however, the in-mouth sensory effects of different molecular structures in red wine tannins remains to be established. The objective of this research was to assess the impact of wine tannin structure on in-mouth sensory properties. Wine tannin was isolated from Cabernet Sauvignon wines of two vintages (3 and 7 years old) and separated into two structurally distinct subfractions with liquid-liquid fractionation using butanol and water. The aqueous subfractions had greater mean degree of polymerization (mDp) and contained a higher proportion of epigallocatechin subunits than the butanol-soluble subfractions, while the older wine tannin fractions showed fewer epicatechin gallate subunits than the younger tannin fractions. The red wine had approximately 3:1 mass ratio of the aqueous and butanol tannin subfractions which approximated an equimolar ratio of tannin in each subfraction. Descriptive sensory analysis of the tannin subfractions in model wine at equimolar concentrations revealed that the larger, more water-soluble wine tannin subfractions from both wines were perceived as more astringent than the smaller, more hydrophobic and more highly pigmented butanol-soluble subfractions, which were perceived as hotter and more bitter. Partial least squares analysis indicated that the greater hydrophobicity and color incorporation in the butanol fractions was negatively associated with astringency, and these characteristics are also associated with aged wine tannins. As the larger, water-soluble tannins had a greater impact on the overall wine astringency, winemaking processes that modulate concentrations of these are likely to most significantly influence astringency.

Changes in the structural composition and reactivity of Acer rubrum leaf litter tannins exposed to warming and altered precipitation: climatic stress-induced tannins are more reactive.

PubMed

Tharayil, Nishanth; Suseela, Vidya; Triebwasser, Daniella J; Preston, Caroline M; Gerard, Patrick D; Dukes, Jeffrey S

2011-07-01

• Climate change could increase the frequency with which plants experience abiotic stresses, leading to changes in their metabolic pathways. These stresses may induce the production of compounds that are structurally and biologically different from constitutive compounds. • We studied how warming and altered precipitation affected the composition, structure, and biological reactivity of leaf litter tannins in Acer rubrum at the Boston-Area Climate Experiment, in Massachusetts, USA. • Warmer and drier climatic conditions led to higher concentrations of protective compounds, including flavonoids and cutin. The abundance and structure of leaf tannins also responded consistently to climatic treatments. Drought and warming in combination doubled the concentration of total tannins, which reached 30% of leaf-litter DW. This treatment also produced condensed tannins with lower polymerization and a greater proportion of procyanidin units, which in turn reduced sequestration of tannins by litter fiber. Furthermore, because of the structural flexibility of these tannins, litter from this treatment exhibited five times more enzyme (β-glucosidase) complexation capacity on a per-weight basis. Warmer and wetter conditions decreased the amount of foliar condensed tannins. • Our finding that warming and drought result in the production of highly reactive tannins is novel, and highly relevant to climate change research as these tannins, by immobilizing microbial enzymes, could slow litter decomposition and thus carbon and nutrient cycling in a warmer, drier world. © 2011 The Authors. New Phytologist © 2011 New Phytologist Trust.

A tannin-blocking agent does not modify the preference of sheep towards tannin-containing plants.

PubMed

Hernández-Orduño, G; Torres-Acosta, J F J; Sandoval-Castro, C A; Capetillo-Leal, C M; Aguilar-Caballero, A J; Alonso-Díaz, M A

2015-06-01

Sheep have been suggested to use their senses to perceive plant properties and associate their intake with consequences after ingestion. However, sheep with browsing experience do not seem to select against tannin-rich browsing materials in cafeteria trials. Thus, the objective of the present study was to evaluate the relationship between the chemical composition, selectivity index (SI), preference and intake rate (IR) of tannin-containing forage trees offered to sheep in cafeteria experiments. Four trees were selected for their condensed tannin content and their varying biological activities. Havardia albicans (high biological activity), Leucaena leucocephala (medium biological activity), Acacia gaumeri (low biological activity) and Brosimum alicastrum (very low biological activity) were used in this study. Ten hair sheep (23.7kg±1.43LW) with eight months of browsing experience in native vegetation were used in this study. Polyethylene glycol (PEG 3600MW) was administered to five sheep during all experiments. In experiment 1, fresh foliage from all trees was offered ad libitum for 4h. In experiment 2, B. alicastrum was withdrawn and the preference was determined again. The forage preference in experiment 1 was A. gaumeri (14.77gDM/kgLW)>B. alicastrum (11.77gDM/kgLW)>H. albicans (3.71gDM/kgLW)=L. leucocephala (1.87gDM/kgLW) (P<0.05). The preference in experiment 2 was A. gaumeri>H. albicans=L. leucocephala. PEG administration had no effect on the preference or IR. The intake rate seemed to have been affected by the plant density. Moreover, fiber compounds were found to be better predictors of DM intake than polyphenolic compounds at levels typically found in the evaluated forages. It was concluded that tannins and PEG did not modify the preferences of sheep in cafeteria trials. Thus, tannins are not involved in the preference regulation of animals with browsing experience. Copyright © 2015 Elsevier Inc. All rights reserved.

[Selective removal of tannins from Polygonum cuspidatum extracts using collagen fiber adsorbent].

PubMed

Li, Juan; Liao, Xuepin; Shu, Xingxu; Shi, Bi

2010-03-01

To investigate the selective removal of tannins from Polygonum cuspidatum extracts by using collagen fiber adsorbent, and to evaluate the adsorption and desorption performances of collagen fiber adsorbent to tannins. The adsorbent was prepared from bovine skin collagen fiber through crosslinking reaction of glutaraldehyde, and then used for the selective removal of tannins from P. cuspidatum extracts. Gelatin-turbidity method, gelatin-ultraviolet spectrometry method and HPLC were used for detection of tannins in the solutions. Ethanol-water solutions with varying concentration were used to test their desorption ability of tannins in order to choose proper desorption solution. On the basis of batch experimental results, the column adsorption and desorption tests were carried out, by using gelatin-turbidity method for detection of tannins. The collagen fiber adsorbent exhibited excellent adsorption selectivity to tannins. It was found that tannins of P. cuspidatum were completely removed, while nearly no adsorption of active components (resveratrol as representative) was found. Moreover, the collagen fiber adsorbent could be regenerated by using 30% ethanol-water solution and then reused. The collagen fiber adsorbent can be considered as a promising material for selective removal of tannins from P. cuspidatum extracts.

Phytotoxicity evaluation and phytochemical analysis of three medicinally important plants from Pakistan.

PubMed

Ullah, Nazif; Haq, Ihsan-Ul; Mirza, Bushra

2015-05-01

This work examines the crude methanolic extracts of three medicinally important plants native to Pakistan for potent phytotoxic activities and important phytochemicals. These plants include Euphorbia wallichii, Bergenia ciliata and Phytolacca latbenia. The phytotoxic effects were checked at 10,000, 1000, and 100 µg/ml against two economically important standard target species, Triticum aestivum (monocot representative) and Brassica napus (dicot representative). The phytotoxicity effects on seed germination, seedling growth and seedling weight were checked. A simple, cost-effective in vitro phytotoxicity assay (that uses petri plates) was used to evaluate the allelopathic properties of crude extracts. At highest concentration, extracts from all the three plants showed phytotoxic activities such that P. latbenia > E. wallichii > B. ciliata. In seedling growth, root length was affected more than shoot length, whereas among the target species B. napus was found to be more sensitive towards extracts when compared with T. aestivum. Phytochemical analysis showed that P. latbenia is rich in saponins and terpenoids, while E. wallichii and B. ciliata are rich in tannins, terpenoids and cardiac glycoside. P. latbenia also carries a moderate amount of cardiac glycosides. © The Author(s) 2012.

A new furostanol glycoside from Tribulus terrestris.

PubMed

Xu, Yajuan; Liu, Yonghong; Xu, Tunhai; Xie, Shengxu; Si, Yunshan; Liu, Yue; Zhou, Haiou; Liu, Tonghua; Xu, Dongming

2010-01-27

Besides two known glycosides, a new furostanol glycoside was isolated from the Fruits of Tribulus terrestris L. The structure of the new furostanol glycoside was established as 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furostane-20(22)-en-12-one-3beta, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside (1) on the basis of 1D and 2D-NMR techniques, including COSY, HMBC, and HMQC correlations.

Impact of Chestnut and Quebracho Tannins on Rumen Microbiota of Bovines

PubMed Central

Cabral, Claudio; Pin Viso, Natalia Daniela; Colombatto, Darío; Farber, Marisa Diana

2017-01-01

The use of phytogenic dietary additives is being evaluated as a means to improve animal productivity. The effect of tannins seems to be the influence not only directly on the digestive process through binding of dietary proteins but also indirectly over their effects on gastrointestinal microbiota. High-throughput sequencing of 16S rRNA gene was used to analyze the impact of dietary supplementation with a blend of chestnut and quebracho tannins on the rumen microbiota of Holstein steers. Bacterial richness was lower in tannins treated animals, while the overall population structure of rumen microbiota was not significantly disturbed by tannins. The ratio of the phyla Firmicutes and Bacteroidetes, a parameter associated with energy harvesting function, was increased in tannins supplemented animals, essentially due to the selective growth of Ruminococcaceae over members of genus Prevotella. Fibrolytic, amylolytic, and ureolytic bacterial communities in the rumen were altered by tannins, while methanogenic archaea were reduced. Furthermore, ruminal pH was significantly higher in animals supplemented with tannins than in the control group, while urease activity exhibited the opposite pattern. Further work is necessary to assess the relation between tannins impact on rumen microbiota and alteration of rumen fermentation parameters associated with bovine performance. PMID:29445749

Tannin bark Melalauca cajuputi powell (gelam) as green corrosion inhibitor of mild steel

NASA Astrophysics Data System (ADS)

Talib, Nur Atiqah Abu; Zakaria, Sarani; Hua, Chia Chin; Othman, Norinsan Kamil

2014-09-01

Tannin was extracted from gelam bark and used to produce corrosion inhibitor for mild steel. Tannin was extracted from gelam bark using 70% aqueous acetone for 6 hour. Tannin powder was characterization using fourier transform infrared spectroscopy to analyse chemical component in tannin and Scanning electron microscope (SEM) for tannin physical structure. The tannin effect on the corrosion inhibition of mild steel has been investigated in 1Mol HCl solution for 6 hour followed ASTM. The weight loss method were applied to study the mild steel corrosion behavior in the present and absend of different concentration of tannin (250, 300, 350)ppm. Tannin act good inhibitor as corrosion inhibitor for mild steel in acid medium. Surface morphology of carbon steel with and without inhibitor was investigated by scanning electron microscopy.

Research observation: Hydrolyzable and condensed tannins in plants of northwest Spain forests

USGS Publications Warehouse

Gonzalez-Hernandez, M. P.; Karchesy, J.; Starkey, E.E.

2003-01-01

Tannins are secondary metabolites that may influence feeding by mammals on plants. We analyzed hydrolyzable and condensed tannins in 30 plant species consumed by livestock and deer, as a preliminary attempt to study their possible implications on browsing and grazing in forest ecosystems. Heathers (Ericaceae) and plants of the Rose (Rosaceae) family had tannins, while forbs, grasses and shrubs other than the heathers did not show astringency properties. We found the highest tannin content of all the species in Rubus sp., with the highest value around 180 mg TAE/g dry weight in spring. Potentilla erecta, Alnus glutinosa and Quercus robur were next with 57 to 44 mg TAE/g dw. Total tannins in heathers ranged from 22 to 36 mg TAE/g dw. Levels of condensed tannins were higher than hydrolyzable for most of the species. Only Betula alba, Calluna vulgaris, Pteridium aquilinum and Vaccinium myrtillus had 100% hydrolyzable tannins. Tannin content of the species changed seasonally with highest values during the growing season, corresponding to late winter or early spring, depending on the species.

Multifunctional porous solids derived from tannins

NASA Astrophysics Data System (ADS)

Celzard, Alain; Fierro, Vanessa; Pizzi, Antonio; Zhao, Weigang

2013-03-01

Tannins are extremely valuable, non toxic, wood extractives combining reactivity towards aldehydes, low cost, natural origin and easy handling. When polymerized in the presence of suitable chemicals including blowing agent, ultra lightweight rigid tannin-based foams are obtained. If pyrolyzed under inert gas, reticulated carbon foams having the same pore structure and the same density are obtained. The most remarkable features of tannin-based foams are the following: mechanical resistance similar to, or higher than, that of commercial phenolic foams, tuneable pore size and permeability, infusibility, very low thermal conductivity, cheapness, ecological character, high resistance to flame and to chemicals. Carbon foams have even better properties and are also electrically conducting. Consequently, various applications are suggested for organic foams: cores of sandwich composite panels, sound and shock absorbers and thermal insulators, whereas carbon foams can be used as porous electrodes, filters for molten metals and corrosive chemicals, catalyst supports and adsorbents.

The effect of flavonol glycosides on opiate withdrawal.

PubMed

Capasso, Anna

2007-07-01

Our interest has been centered on flavonol glycosides from Croton Menthodorus (Euphorbiaceae) and Aristeguietia discolor (Asteraceae). In this respect, the effect of flavonol glycosides from Croton Menthodorus (Euphorbiaceae) and Aristeguietia discolor (Asteraceae) was investigated on the naloxone-precipitated withdrawal contracture of the acute morphine-dependent guinea-pig ileum in vitro. Furthermore, the effect of these flavonol glycosides was also considered on DAGO (highly selective micro-agonist) and U50-488H (highly selective k-agonist) withdrawal to test whether the possible interaction of flavonol glycosides on opioid withdrawal involves micro- and/or k-opioid receptors. Flavonol glycosides from Croton Menthodorus (1 x 10(-5), 5 x 10(-5) and 1 x 10(-4) M) and from Aristeguietia discolor (1 x 10(-7)-1 x 10(-6)-1 x 10(-5) M) before or after the opioid agonists were able to both prevent and reverse the naloxone-induced contracture after exposure to micro (morphine and DAGO) or k (U50-488H) opiate agonists in a concentration-dependent fashion. Both acetylcholine response and electrical stimulation were reduced by flavonol glycosides treatment as well as the final opiate withdrawal was still reduced. The results of the present study indicate that flavonol glycosides were able to produce significant influence on the opiate withdrawal in vitro and these compounds were able to exert their effects both at micro and k opioid agonists.

Tannin bark Melalauca cajuputi powell (gelam) as green corrosion inhibitor of mild steel

DOE Office of Scientific and Technical Information (OSTI.GOV)

Talib, Nur Atiqah Abu; Zakaria, Sarani; Hua, Chia Chin

Tannin was extracted from gelam bark and used to produce corrosion inhibitor for mild steel. Tannin was extracted from gelam bark using 70% aqueous acetone for 6 hour. Tannin powder was characterization using fourier transform infrared spectroscopy to analyse chemical component in tannin and Scanning electron microscope (SEM) for tannin physical structure. The tannin effect on the corrosion inhibition of mild steel has been investigated in 1Mol HCl solution for 6 hour followed ASTM. The weight loss method were applied to study the mild steel corrosion behavior in the present and absend of different concentration of tannin (250, 300, 350)ppm.more » Tannin act good inhibitor as corrosion inhibitor for mild steel in acid medium. Surface morphology of carbon steel with and without inhibitor was investigated by scanning electron microscopy.« less

Effect of tannins on growth performance and intestinal ecosystem in weaned piglets.

PubMed

Biagia, Giacomo; Cipollini, Irene; Paulicks, Brigitte R; Roth, Franz X

2010-04-01

Tannins are natural polyphenolic compounds that can reduce digestibility of dietary protein but also display antibacterial effects. The present study investigated, in vitro and in vivo, the effect of different levels of tannins (using a chestnut wood extract containing 75% tannins) on growth performance, intestinal microbiota and wall morphology in piglets. During a 24 h in vitro caecal fermentation, the utilisation of tannins at 0.75, 1.5, 3, and 6 g/l significantly reduced total gas production and concentrations of ammonia and volatile fatty acids and increased viable counts of enterococci and coliforms. When fed to piglets at 1.13, 2.25, and 4.5 g/kg, tannins significantly improved feed efficiency and reduced caecal concentrations of ammonia, iso-butyric, and iso-valeric acid. Viable counts of lactobacilli tended to be increased by tannins in the jejunum, while bacterial caecal counts were not affected. Depth of ileal crypts tended to decrease in piglets fed tannins at 2.25 and 4.5 g/kg. The present study showed that feeding weaned piglets with a tannin-rich wood extract can result in improved feed efficiency and reduction of intestinal bacterial proteolytic reactions. The growth-enhancing effect that tannins had on enterococci and coliforms under in vitro conditions deserves further investigation.

Transformation of Litchi Pericarp-Derived Condensed Tannin with Aspergillus awamori

PubMed Central

Lin, Sen; Li, Qing; Yang, Bao; Duan, Xuewu; Zhang, Mingwei; Shi, John; Jiang, Yueming

2016-01-01

Condensed tannin is a ubiquitous polyphenol in plants that possesses substantial antioxidant capacity. In this study, we have investigated the polyphenol extraction recovery and 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity of the extracted polyphenol after litchi pericarp is treated with Aspergillus awamori, Aspergillus sojae or Aspergillus oryzae. We have further explored the activity of A. awamori in the formation of condensed tannin. The treatment of A. awamori appeared to produce the highest antioxidant activity of polyphenol from litchi pericarp. Further studies suggested that the treatment of A. awamori releases the non-extractable condensed tannin from cell walls of litchi pericarp. The total extractable tannin in the litchi pericarp residue after a six-time extraction with 60% ethanol increased from 199.92 ± 14.47–318.38 ± 7.59 μg/g dry weight (DW) after the treatment of A. awamori. The ESI-TOF-MS and HPLC-MS2 analyses further revealed that treatment of A. awamori degraded B-type condensed tannin (condensed flavan-3-ol via C4–C8 linkage), but exhibited a limited capacity to degrade the condensed tannin containing A-type linkage subunits (C4–C8 coupled C2–O–C7 linkage). These results suggest that the treatment of A. awamori can significantly improve the production of condensed tannin from litchi pericarp. PMID:27420043

Transformation of Litchi Pericarp-Derived Condensed Tannin with Aspergillus awamori.

PubMed

Lin, Sen; Li, Qing; Yang, Bao; Duan, Xuewu; Zhang, Mingwei; Shi, John; Jiang, Yueming

2016-07-12

Condensed tannin is a ubiquitous polyphenol in plants that possesses substantial antioxidant capacity. In this study, we have investigated the polyphenol extraction recovery and 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity of the extracted polyphenol after litchi pericarp is treated with Aspergillus awamori, Aspergillus sojae or Aspergillus oryzae. We have further explored the activity of A. awamori in the formation of condensed tannin. The treatment of A. awamori appeared to produce the highest antioxidant activity of polyphenol from litchi pericarp. Further studies suggested that the treatment of A. awamori releases the non-extractable condensed tannin from cell walls of litchi pericarp. The total extractable tannin in the litchi pericarp residue after a six-time extraction with 60% ethanol increased from 199.92 ± 14.47-318.38 ± 7.59 μg/g dry weight (DW) after the treatment of A. awamori. The ESI-TOF-MS and HPLC-MS² analyses further revealed that treatment of A. awamori degraded B-type condensed tannin (condensed flavan-3-ol via C4-C8 linkage), but exhibited a limited capacity to degrade the condensed tannin containing A-type linkage subunits (C4-C8 coupled C2-O-C7 linkage). These results suggest that the treatment of A. awamori can significantly improve the production of condensed tannin from litchi pericarp.

Genetics and Biochemistry of Zero-Tannin Lentils.

PubMed

Mirali, Mahla; Purves, Randy W; Stonehouse, Rob; Song, Rui; Bett, Kirstin; Vandenberg, Albert

2016-01-01

The zero-tannin trait in lentil is controlled by a single recessive gene (tan) that results in a phenotype characterized by green stems, white flowers, and thin, transparent, or translucent seed coats. Genes that result in zero-tannin characteristics are useful for studies of seed coat pigmentation and biochemical characters because they have altered pigmentation. In this study, one of the major groups of plant pigments, phenolic compounds, was compared among zero-tannin and normal phenotypes and genotypes of lentil. Biochemical data were obtained by liquid chromatography-mass spectrometry (LC-MS). Genomic sequencing was used to identify a candidate gene for the tan locus. Phenolic compound profiling revealed that myricetin, dihydromyricetin, flavan-3-ols, and proanthocyanidins are only detected in normal lentil phenotypes and not in zero-tannin types. The molecular analysis showed that the tan gene encodes a bHLH transcription factor, homologous to the A gene in pea. The results of this study suggest that tan as a bHLH transcription factor interacts with the regulatory genes in the biochemical pathway of phenolic compounds starting from flavonoid-3',5'-hydroxylase (F3'5'H) and dihydroflavonol reductase (DFR).

Tannin diagenesis in mangrove leaves from a tropical estuary: A novel molecular approach

USGS Publications Warehouse

Hernes, P.J.; Benner, R.; Cowie, G.L.; Goi, M.A.; Bergamaschi, B.A.; Hedges, J.I.

2001-01-01

Molecular-level condensed tannin analyses were conducted on a series of mangrove (Rhizophora mangle) leaves at various stages of decomposition in a tropical estuary. Total molecular tannin yields ranged from 0.5% ash-free dry weight (AFDW) in the most highly degraded black leaves (6-7 weeks in the water) up to >7% AFDW in fresh leaves (80% procyanidin (PC) with the remainder being prodelphinidin (PD). PD tannin, with its higher degree of hydroxylation, proved to be more labile than PC tannin. Average chain length of condensed tannin (degree of polymerization) exhibited an initial increase in response to leaching, but later decreased in the subsequent shift toward abiotic or microbially mediated chemical reactions. Several trends point toward a possible condensation reaction in which tannin plays a role in nitrogen immobilization. These include an apparent inverse correlation between molecular tannin and nitrogen, a positive correlation between molecular tannin and percent basic amino acids, 13C-NMR data indicating transformation of tannin as opposed to remineralization, and 13C-NMR data showing loss of condensed tannin B-ring phenolic carbons coupled with preservation of A-ring phenolic carbon. In addition to condensed tannin, the molecular method used also yielded several triterpenoids. Triterpenoids accounted for up to 3.5% AFDW of the leaf material and exhibited a threefold increase between yellow senescent leaves entering the estuary and black leaves. This trend is likely due to the weakening of protective cuticular membranes during leaf decomposition, which leads to increased yields in the acidic conditions used for tannin analyses. Copyright ?? 2001 Elsevier Science Ltd.

Evidence for functional heterogeneity both between and within four sources of condensed tannin

DOE Office of Scientific and Technical Information (OSTI.GOV)

Asquith, T.N.

1985-01-01

Condensed tannins are polymers of flavan-3-ols that are produced by many plants in a wide variety of tissues. The ability of these compounds to actively precipitate proteins has been linked to nutritional deficiencies in many animals. Four purified tannins (quebracho, wattle, pinto bean and sorghum) were compared to chemical assays and astringency towards (/sup 14/C)-BSA. Quebracho and wattle tannins were much less astringent and had longer chain lengths that sorghum or pinto bean tannins. Quebracho tannin had a very high affinity for salivary proline-rich glycoproteins (PRPs) and pinto bean tannin alone had a measurable affinity for soybean trypsin inhibitor. Thismore » suggests that tannin/protein interactions in vivo may be very specific. Protein bound carbohydrate enhanced the binding of PRPs to tanning and conferred specificity on the interactions. Carbohydrate also increases the solubility of protein/tanning complexes, which may aid the animal in eliminating the complexes. (/sup 125/I)-labeled condensed tannin was shown to retain the ability to discriminate between high and low affinity proteins. (/sup 125/I)-labeled phenols were isolated from livers and kidneys of rats fed (/sup 125/I)-labeled tannin. The techniques described in this thesis should be widely applicable to studying in vivo functions of condensed tannins.« less

Synergistic inhibition of Haemonchus contortus exsheathment by flavonoid monomers and condensed tannins

PubMed Central

Klongsiriwet, Chaweewan; Quijada, Jessica; Williams, Andrew R.; Mueller-Harvey, Irene; Williamson, Elizabeth M.; Hoste, Hervé

2015-01-01

This study investigated the separate and combined anthelmintic (AH) effects of different phenolic compounds, including condensed tannins and flavonoids, all of which are known to occur in willow leaves, a potentially valuable dry season feed. A range of contrasting model tannins, which span the whole range of willow tannins, were isolated from tilia flowers, goat willow leaves, black currant leaves and red currant leaves. All together, the tested compounds represented the major tannin types (procyanidins and prodelphinidins) and flavonoid types (flavonols, flavones and flavanones). The larval exsheathment inhibition assay (LEIA) was used to assess their in vitro effects on Haemonchus contortus third stage larvae. Arbutin, vanillic acid, and taxifolin proved to be ineffective whereas naringenin, quercetin and luteolin were highly effective at 250 μM concentrations. Procyanidin (PC) tannins tended to be less active than prodelphinidin tannins (PD). Experiments with combinations of tannins and quercetin or luteolin revealed for the first time the existence of synergistic AH effects between tannins and flavonoid monomers. They also provided evidence that synergistic effects appear to occur at slightly lower concentrations of PC than PD. This suggests that the AH activity of condensed tannins can be significantly enhanced by the addition of quercetin or luteolin. This information may prove useful for plant breeding or selection and for designing optimal feed mixtures. PMID:26199861

Enhancement of both salivary protein-enological tannin interactions and astringency perception by ethanol.

PubMed

Obreque-Slíer, Elías; Peña-Neira, Alvaro; López-Solís, Remigio

2010-03-24

Red wine astringency has been associated with interactions of tannins with salivary proteins. Tannins are active protein precipitants. Not much evidence exists demonstrating contribution of other wine components to astringency. We aimed to investigate an eventual role of ethanol both in astringency and salivary protein-enological tannin interactions. A trained sensory panel scored perceived astringency. Salivary protein-tannin interactions were assessed by observing both tannin-dependent changes in salivary protein diffusion on cellulose membranes and tannin-induced salivary protein precipitation. Proanthocyanidins and gallotannins in aqueous and hydroalcoholic solutions were assayed. A biphasic mode of diffusion on cellulose membranes displayed by salivary proteins was unaffected after dilution with water or enological concentrations of ethanol. At those concentrations ethanol was not astringent. In aqueous solution, tannins provoked both restriction of salivary protein diffusion, protein precipitation, and astringency. Those effects were exacerbated by 13% ethanol. In summary, enological concentrations of ethanol exacerbate astringency and salivary protein-tannin interactions.

Assessment of tannin variation in Tamarisk foliage across a latitudinal gradient

USGS Publications Warehouse

Hussey, A.M.; Kimball, B.A.; Friedman, J.M.

2011-01-01

Certain phenotypic traits of plants vary with latitude of origin. To understand if tannin concentration varies among populations of tamarisk (Tamarix spp.) according to a latitudinal gradient, an analytical method was adapted from an enological tannin assay. The tannin content (wet basis) of tamarisk foliage collected from 160 plants grown in a common garden ranged from 8.26 to 62.36 mg/g and was not correlated with the latitude of the original North American plant collection site. Tannins do not contribute to observed differences in herbivory observed among these tamarisk populations.

UPLC-ESI-MS study of the oxidation markers released from tannin depolymerization: toward a better characterization of the tannin evolution over food and beverage processing.

PubMed

Mouls, Laetitia; Fulcrand, Hélène

2012-11-01

Condensed tannins take an important part in the sensory quality of food and beverage. Sensory analyses are usually carried out with various tannin fractions isolated from food or beverage, and their interpretation are limited by the lack of knowledge in the fine and accurate molecular composition of the tannin fractions. Besides, the studies of the chemical reactivity conducted in model solutions with 'simple' flavanols allow a better understanding of their evolution pathways, but they cannot take into account their reactivity as polymers, specifically regarding oxidation. In particular, competition between intramolecular and intermolecular reactions may strongly impact on the tannin structures (size, branching and conformation) and consequently on their properties. An ultra-performance liquid chromatography-mass spectrometry electrospray ionization mass spectrometer analytical method was thus developed in order to identify oxidized tannins generated by autoxidation. Given the difficulties to separate and detect tannins with high DP, samples were depolymerized by chemical depolymerization prior to analysis. Since the linkages created by oxidation are not cleavable in the usual depolymerization conditions (contrarily to the original interflavanic linkages), specific oxidation residues are released from tannins structures after their autoxidation. Oxidation markers of both intermolecular and intramolecular mechanisms have been identified; these are mainly dimers and trimers, more or less oxidized, and some contain additional hydroxyl groups. Furthermore, the nature of the subunits (extension vs terminal) making up these dimers and trimers was clearly established. Copyright © 2012 John Wiley & Sons, Ltd.

Selective determination of aluminum bound with tannin in tea infusion.

PubMed

Erdemoğlu, Sema B; Güçer, Seref

2005-08-01

In this study, an analytical method for indirect measurement of Al bound with tannin in tea infusion was studied. This method utilizes the ability of the tannins to precipitate with protein. Separation conditions were investigated using model solutions. This method is uncomplicated, inexpensive and suitable for real samples. About 34% of the total Al in brew extracted from commercially available teas was bound to condensed and hydrolyzable tannins.

Flavanoid biocides: Wood preservatives based on condensed tannins

Treesearch

Peter Laks; Peggy A. McKaig; Richard W. Hemingway

1988-01-01

The condensed tannins are natural wood preservatives found in high concentrations in the bark and wood of some tree species. Condensed tannin-containing bark extracts from loblolly pine (Pinus taeda) were evaluated as wood preservatives using standard methods. Bark extracts by themselves did not cause any reduction in weight loss of pressure-treated...

Persimmon-Tannin, an α-Amylase Inhibitor, Retards Carbohydrate Absorption in Rats.

PubMed

Tsujita, Takahiro

2016-01-01

Inhibitors of carbohydrate-hydrolyzing enzymes play an important role in controlling postprandial blood glucose levels. Thus the effect of persimmon tannin on pancreatic α-amylase and intestinal α-glucosidase has been investigated. Persimmon tannin inhibits pancreatic α-amylase and intestinal α-glucosidase in a concentration-dependent manner with the 50% inhibition concentration (IC50) for amylase, maltase and sucrase being 1.7 μg/mL, 632 μg/mL and 308 μg/mL, respectively. The effect of persimmon-tannin extract on carbohydrate absorption in rats has also been investigated. Oral administration of persimmon tannin to normal rats fed cornstarch (2 g/kg body weight) significantly suppressed the increase in blood glucose levels and the area under the curve (AUC) after starch loading in a dose-dependent manner. The effective dose of persimmon tannin required to achieve 50% suppression of the rise in blood glucose level was estimated to be 300 mg/kg body weight. Administration of persimmon tannin to rats fed maltose or sucrose delayed the increase of blood glucose level and slightly suppressed AUC, but not significantly. These results suggest that persimmon tannin retards absorption of carbohydrate and reduces post-prandial hyperglycemia mainly through inhibition of α-amylase.

Changes in mouse whole saliva soluble proteome induced by tannin-enriched diet

PubMed Central

2010-01-01

Background Previous studies suggested that dietary tannin ingestion may induce changes in mouse salivary proteins in addition to the primarily studied proline-rich proteins (PRPs). The aim of the present study was to determine the protein expression changes induced by condensed tannin intake on the fraction of mouse whole salivary proteins that are unable to form insoluble tannin-protein complexes. Two-dimensional polyacrylamide gel electrophoresis protein separation was used, followed by protein identification by mass spectrometry. Results Fifty-seven protein spots were excised from control group gels, and 21 different proteins were identified. With tannin consumption, the expression levels of one α-amylase isoform and one unidentified protein increased, whereas acidic mammalian chitinase and Muc10 decreased. Additionally, two basic spots that stained pink with Coomassie Brilliant Blue R-250 were newly observed, suggesting that some induced PRPs may remain uncomplexed or form soluble complexes with tannins. Conclusion This proteomic analysis provides evidence that other salivary proteins, in addition to tannin-precipitating proteins, are affected by tannin ingestion. Changes in the expression levels of the acidic mammalian chitinase precursor and in one of the 14 salivary α-amylase isoforms underscores the need to further investigate their role in tannin ingestion. PMID:21159160

Octanol-water partition coefficients for predicting the effects of tannins in ruminant nutrition.

PubMed

Mueller-Harvey, Irene; Mlambo, Victor; Sikosana, Joe L N; Smith, Tim; Owen, Emyr; Brown, Ron H

2007-07-11

Tannins can cause beneficial or harmful nutritional effects, but their great diversity has until now prevented a rational distinction between tannin structures and their nutritional responses. An attempt has been made to study this problem by examining the octanol-water solubilities of tannins. A relatively simple HPLC method has been developed for screening mixtures of plant tannins for their octanol-water partition coefficients (Kow coefficients). Tannins were isolated from the fruits and leaves of different Acacia, Calliandra, Dichrostachys, and Piliostigma species, which are known to produce beneficial or harmful effects. The Kow coefficients of these tannins ranged from 0.061 to 13.9, average coefficients of variation were 9.2% and recoveries were 107%. Acacia nilotica fruits and leaves had the highest Kow coefficients, that is, 2.0 and 13.9, respectively. These A. nilotica products also have high concentrations of tannins. The combined effects of high octanol solubilities and high tannin concentrations may explain their negative effects on animal nutrition and health. It is known that compounds with high octanol solubilities are more easily absorbed into tissues, and it is, therefore, proposed that such compounds are more likely to cause toxicity problems especially if consumed in large quantities. According to the literature, tannins in human foods tend to have low Kow coefficients, and this was confirmed for the tannins in Piliostigma thonningii fruits. Therefore, unconventional feeds or browse products should be screened not only for their tannin concentrations but also for low octanol-water partition coefficients in order to identify nutritionally safe feeds and to avoid potentially toxic feeds.

Rapid determination of tannins in tanning baths by adaptation of BSA method.

PubMed

Molinari, R; Buonomenna, M G; Cassano, A; Drioli, E

2001-01-01

A rapid and reproducible method for the determination of tannins in vegetable tanning baths is proposed as a modification of the BSA method for grain tannins existing in literature. The protein BSA was used instead of leather powder employed in the Filter Method, which is adopted in Italy and various others countries of Central Europe. In this rapid method the tannin contents is determined by means a spectrophotometric reading and not by means a gravimetric analysis of the Filter Method. The BSA method, which belongs to mixed methods (which use both precipitation and complexation of tannins), consists of selective precipitation of tannin from a solution containing also non tannins by BSA, the dissolution of precipitate and the quantification of free tannin amount by its complexation with Fe(III) in hydrochloric solutions. The absorbance values, read at 522 nm, have been expressed in terms of tannic acid concentration by using a calibration curve made with standard solutions of tannic acid; these have been correlated with the results obtained by using the Filter Method.

Effects of cardiac glycosides on sodium pump expression and function in LLC-PK1 and MDCK cells.

PubMed

Liu, Jiang; Periyasamy, Sankaridrug M; Gunning, William; Fedorova, Olga V; Bagrov, Alexei Y; Malhotra, Deepak; Xie, Zijian; Shapiro, Joseph I

2002-12-01

The decreases in proximal tubule sodium reabsorption seen with chronic renal failure and volume expansion have been ascribed to circulating digitalis-like substances (DLS). However, the circulating concentrations of DLS do not acutely inhibit the sodium pump to a degree consistent with the observed changes in proximal tubule sodium reabsorption. We examined how cell lines that simulated proximal (LLC-PK1) and distal tubule (MDCK) cells responded to acute (30 min) and long-term (up to 12 hours) Na+,K+-ATPase inhibition with DLS. In LLC-PK1, but not MDCK cells, low concentrations of ouabain decreased 86Rb uptake profoundly in a time and dose dependent manner. In LLC-PK1 cells grown to confluence, transcellular 22Na flux was markedly reduced in concert with the decreases in 86Rb uptake. Similar findings were observed with marinobufagenin (MBG) and deproteinated extract of serum derived from patients with chronic renal failure. However, inhibition of the Na+,K+-ATPase with low extracellular potassium concentrations did not produce any of these effects. Western and Northern blots detected no change in alpha1 Na+,K+-ATPase protein and message RNA, respectively, in LLC-PK1 cells treated with ouabain for 12 hours. However, the decrease in enzymatic activity of Na+,K+-ATPase of these cells was comparable to observed decreases in 86Rb uptake. Differential centrifugation as well as biotinylation experiments demonstrated a shift of the Na+,K+-ATPase from the plasmalemma with prolonged ouabain treatment. The results show that binding of cardiac glycosides by proximal (but not distal) tubular cells results in internalization of Na+,K+-ATPase with the net effect to amplify inhibition of the Na+,K+-ATPase. As the circulating concentrations of DLS increase with chronic renal failure and volume expansion, we suggest that this phenomenon explains some of the decreased sodium reabsorption by the proximal tubule seen in these conditions.

Phytosterol glycosides reduce cholesterol absorption in humans

PubMed Central

Lin, Xiaobo; Ma, Lina; Racette, Susan B.; Anderson Spearie, Catherine L.; Ostlund, Richard E.

2009-01-01

Dietary phytosterols inhibit intestinal cholesterol absorption and regulate whole body cholesterol excretion and balance. However, they are biochemically heterogeneous and a portion is glycosylated in some foods with unknown effects on biological activity. We tested the hypothesis that phytosterol glycosides reduce cholesterol absorption in humans. Phytosterol glycosides were extracted and purified from soy lecithin in a novel two-step process. Cholesterol absorption was measured in a series of three single-meal tests given at intervals of 2 wk to each of 11 healthy subjects. In a randomized crossover design, participants received ∼300 mg of added phytosterols in the form of phytosterol glycosides or phytosterol esters, or placebo in a test breakfast also containing 30 mg cholesterol-d7. Cholesterol absorption was estimated by mass spectrometry of plasma cholesterol-d7 enrichment 4–5 days after each test. Compared with the placebo test, phytosterol glycosides reduced cholesterol absorption by 37.6 ± 4.8% (P < 0.0001) and phytosterol esters 30.6 ± 3.9% (P = 0.0001). These results suggest that natural phytosterol glycosides purified from lecithin are bioactive in humans and should be included in methods of phytosterol analysis and tables of food phytosterol content. PMID:19246636

Effect of Condensed Tannins on Bacterial Diversity and Metabolic Activity in the Rat Gastrointestinal Tract

PubMed Central

Smith, Alexandra H.; Mackie, Roderick I.

2004-01-01

The effect of dietary condensed tannins (proanthocyanidins) on rat fecal bacterial populations was ascertained in order to determine whether the proportion on tannin-resistant bacteria increased and if there was a change in the predominant bacterial populations. After 3 weeks of tannin diets the proportion of tannin-resistant bacteria increased significantly (P < 0.05) from 0.3% ± 5.5% to 25.3% ± 8.3% with a 0.7% tannin diet and to 47.2% ± 5.1% with a 2% tannin diet. The proportion of tannin-resistant bacteria returned to preexposure levels in the absence of dietary tannins. A shift in bacterial populations was confirmed by molecular fingerprinting of fecal bacterial populations by denaturing gradient gel electrophoresis (DGGE). Posttreatment samples were generally still distinguishable from controls after 3.5 weeks. Sequence analysis of DGGE bands and characterization of tannin-resistant isolates indicated that tannins selected for Enterobacteriaceae and Bacteroides species. Dot blot quantification confirmed that these gram-negative bacterial groups predominated in the presence of dietary tannins and that there was a corresponding decrease in the gram-positive Clostridium leptum group and other groups. Metabolic fingerprint patterns revealed that functional activities of culturable fecal bacteria were affected by the presence of tannins. Condensed tannins of Acacia angustissima altered fecal bacterial populations in the rat gastrointestinal tract, resulting in a shift in the predominant bacteria towards tannin-resistant gram-negative Enterobacteriaceae and Bacteroides species. PMID:14766594

Activities of Tannins--From In Vitro Studies to Clinical Trials.

PubMed

Sieniawska, Elwira

2015-11-01

Tannins are considered as valuable plant secondary metabolites providing many benefits for human health. In this review information was gathered about bioactivity in vitro and in vivo, as well as about conducted clinical trials. The literature research was based on ScienceDirect, Scopus, and Cochrane databases and presents a wide range of tested activities of tannins. The described clinical trials verify laboratory tests and show the effective health benefits taken from supplementation with tannins.

Disruption of methicillin-resistant Staphylococcus aureus protein synthesis by tannins

PubMed Central

Adnan, Siti-Noor-Adnalizawati; Ibrahim, Nazlina; Yaacob, Wan Ahmad

2017-01-01

Introduction Methicillin-resistant Staphylococcus aureus (MRSA) is a worldwide public health threat, displaying multiple antibiotic resistance that causes morbidity and mortality. Management of multidrug-resistant (MDR) MRSA infections is extremely difficult due to their inherent resistance to currently used antibiotics. New antibiotics are needed to combat the emergence of antimicrobial resistance. Methods The in vitro effect of tannins was studied against MRSA reference strain (ATCC 43300) and MRSA clinical strains utilizing antimicrobial assays in conjunction with both scanning and transmission electron microscopy. To reveal the influence of tannins in MRSA protein synthesis disruption, we utilized next-generation sequencing (NGS) to provide further insight into the novel protein synthesis transcriptional response of MRSA exposed to these compounds. Results Tannins possessed both bacteriostatic and bactericidal activity with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of 0.78 and 1.56 mg/mL, respectively, against all tested MRSA. Scanning and transmission electron microscopy of MRSA treated with tannins showed decrease in cellular volume, indicating disruption of protein synthesis. Conclusion Analysis of a genome-wide transcriptional profile of the reference strain ATCC 43300 MRSA in response to tannins has led to the finding that tannins induced significant modulation in essential ribosome pathways, which caused a reduction in the translation processes that lead to inhibition of protein synthesis and obviation of bacterial growth. These findings highlight the potential of tannins as new promising anti-MRSA agents in clinical application such as body wash and topical cream or ointments. PMID:29264356

Steviol glycosides in purified stevia leaf extract sharing the same metabolic fate.

PubMed

Purkayastha, Sidd; Markosyan, Avetik; Prakash, Indra; Bhusari, Sachin; Pugh, George; Lynch, Barry; Roberts, Ashley

2016-06-01

The safety of steviol glycosides is based on data available on several individual steviol glycosides and on the terminal absorbed metabolite, steviol. Many more steviol glycosides have been identified, but are not yet included in regulatory assessments. Demonstration that these glycosides share the same metabolic fate would indicate applicability of the same regulatory paradigm. In vitro incubation assays with pooled human fecal homogenates, using rebaudiosides A, B, C, D, E, F and M, as well as steviolbioside and dulcoside A, at two concentrations over 24-48 h, were conducted to assess the metabolic fate of various steviol glycoside classes and to demonstrate that likely all steviol glycosides are metabolized to steviol. The data show that glycosidic side chains containing glucose, rhamnose, xylose, fructose and deoxy-glucose, including combinations of α(1-2), β-1, β(1-2), β(1-3), and β(1-6) linkages, were degraded to steviol mostly within 24 h. Given a common metabolite structure and a shared metabolic fate, safety data available for individual steviol glycosides can be used to support safety of purified steviol glycosides in general. Therefore, steviol glycosides specifications adopted by the regulatory authorities should include all steviol glycosides belonging to the five groups of steviol glycosides and a group acceptable daily intake established. Copyright © 2016 Elsevier Inc. All rights reserved.

Stability of steviol glycosides in several food matrices.

PubMed

Jooken, Etienne; Amery, Ruis; Struyf, Tom; Duquenne, Barbara; Geuns, Jan; Meesschaert, Boudewijn

2012-10-24

As steviol glycosides are now allowed as a food additive in the European market, it is important to assess the stability of these steviol glycosides after they have been added to different food matrices. We analyzed and tested the stability of steviol glycosides in semiskimmed milk, soy drink, fermented milk drink, ice cream, full-fat and skimmed set yogurt, dry biscuits, and jam. The fat was removed by centrifugation from the dairy and soy drink samples. Proteins were precipitated by the addition of acetonitrile and also removed by centrifugation. Samples of jam were extracted with water. Dry biscuits were extracted with ethanol. The resulting samples were concentrated with solid-phase extraction and analyzed by high-performance liquid chromatography on a C18 stationary phase and a gradient of acetonitrile/aqueous 25 mM phosphoric acid. The accuracy was checked using a standard addition on some samples. For assessing the stability of the steviol glycosides, samples were stored in conditions relevant to each food matrix and analyzed periodically. The results indicate that steviol glycosides can be analyzed with good precision and accuracy in these food categories. The recovery was between 96 and 103%. The method was also validated by standard addition, which showed excellent agreement with the external calibration curve. No sign of decomposition of steviol glycosides was found in any of the samples.

Contributions to the phytochemical study of Bidens tripartitae herba from Romania. I. Tannins.

PubMed

Zagnat, M; Cheptea, Corina; Spac, A F

2013-01-01

To analyze qualitatively and quantitatively tannins in the native plant, collected during the whole vegetation period from different areas of the country, and in its different organs (flower, stem, leaf). For quantitative analysis, the plant product was extracted by repeated maceration (3 days) with 80% methanol. Proanthocyanidins in the extract were quantified by spectrophotometric methods. condensed tannins were present while hydrolyzed tannins were absent. Chromatographic analysis showed that tannins spectrum is similar in all plant organs and in plants collected at different times throughout the vegetation period. The differences are only quantitative. The maximum amount of tannins was found during the flowering stage (10.32%). In terms of tannin content, flowering is the best time to collect. However, collection throughout the whole vegetation period is acceptable.

Enhanced antioxidant activity of polyolefin films integrated with grape tannins.

PubMed

Olejar, Kenneth J; Ray, Sudip; Kilmartin, Paul A

2016-06-01

A natural antioxidant derived from an agro-waste of the wine industry, grape tannin, was incorporated by melt blending into three different polyolefins (high-density polyethylene, linear low-density polyethylene and polypropylene) to introduce antioxidant functionality. Significant antioxidant activity was observed at 1% tannin inclusion in all polymer blends. The antioxidant activity was observed to increase steadily with a greater concentration of grape tannins, the highest increases being seen with polypropylene. The mechanical and thermal properties of the polymer films following antioxidant incorporation were minimally altered with up to 3% grape tannins. All of the polyolefin-grape tannin films successfully passed the leachability test following USP661 standard protocol. Superior antioxidant activity was established in polyolefin thin films by utilization of a bulk grape extract obtained from winery waste. Significant increases in antioxidant activity were seen with 1% extract inclusion. This not only demonstrates the potential for food packaging applications of the polyolefin blends, but also valorizes the agro-waste. © 2015 Society of Chemical Industry. © 2015 Society of Chemical Industry.

Tannin structural elucidation and quantitative ³¹P NMR analysis. 1. Model compounds.

PubMed

Melone, Federica; Saladino, Raffaele; Lange, Heiko; Crestini, Claudia

2013-10-02

Tannins and flavonoids are secondary metabolites of plants that display a wide array of biological activities. This peculiarity is related to the inhibition of extracellular enzymes that occurs through the complexation of peptides by tannins. Not only the nature of these interactions, but more fundamentally also the structure of these heterogeneous polyphenolic molecules are not completely clear. This first paper describes the development of a new analytical method for the structural characterization of tannins on the basis of tannin model compounds employing an in situ labeling of all labile H groups (aliphatic OH, phenolic OH, and carboxylic acids) with a phosphorus reagent. The ³¹P NMR analysis of ³¹P-labeled samples allowed the unprecedented quantitative and qualitative structural characterization of hydrolyzable tannins, proanthocyanidins, and catechin tannin model compounds, forming the foundations for the quantitative structural elucidation of a variety of actual tannin samples described in part 2 of this series.

Antioxidant activity of commercial food grade tannins exemplified in a wine model.

PubMed

Ricci, Arianna; Olejar, Kenneth J; Parpinello, Giuseppina P; Mattioli, Alessia U; Teslić, Nemanja; Kilmartin, Paul A; Versari, Andrea

2016-12-01

Although commercial tannins are widely used in foods and beverages, an improved understanding of the structure and composition of vegetable tannins is needed to promote the exploitation of agri-food by-products and waste and their valorisation in more sustainable industrial applications. This study aims to characterise the phytochemical composition and antioxidant activity of 13 food grade tannins using multiple analytical approaches, including spectrophotometry and HPLC-ECD to determine the amount of targeted polyphenolic compounds. Moreover, the antioxidant activity of tannins was assessed in terms of radical scavenging activity (DPPH• assay), reducing power (FRAP assay), and redox properties (cyclic voltammetry, CV). A statistical univariate and multivariate correlation analysis was performed on 17 parameters including tannin content (range: 0.71-1.62 mM), gallic acid, (+)-catechin, syringic acid and (‒)-epicatechin. The compositional profile of tannins was related to their chemical moiety, antioxidant activity and the botanical origin of the extracts. In particular, the CV signal at 500 mV was highly correlated with DPPH• value due to the catechol ring of flavonoids and trigalloyl moieties of gallic acid-based compounds. Practical examples of tannins application in winemaking are discussed.

Neolignan and flavonoid glycosides in Juniperus communis var. depressa.

PubMed

Nakanishi, Tsutomu; Iida, Naoki; Inatomi, Yuka; Murata, Hiroko; Inada, Akira; Murata, Jin; Lang, Frank A; Iinuma, Munekazu; Tanaka, Toshiyuki

2004-01-01

Two neolignan glycosides (junipercomnosides A and B) were isolated from aerial parts of Juniperus communis var. depressa along with two known neolignan glycosides and seven flavonoid glycosides. The structures of the isolated compounds were determined by spectral analysis, in particular by 2D-NMR analysis. The significance of distribution of flavonoids in the chemotaxonomy of genus Juniperus was also discussed.

Understanding the Relationship between Red Wine Matrix, Tannin Activity, and Sensory Properties.

PubMed

Watrelot, Aude A; Byrnes, Nadia K; Heymann, Hildegarde; Kennedy, James A

2016-11-30

One major red wine mouthfeel characteristic, astringency, is derived from grape-extracted tannins and is considered to be a result of interaction with salivary proteins and the oral mucosa. To improve our understanding of the role that the enthalpy of interaction of tannin with a hydrophobic surface (tannin activity) has in astringency perception, a chromatographic method was used to determine the tannin concentration and activity of 34 Cabernet Sauvignon wines, as well as sensory analysis done on 13 of those wines. In addition, astringency-relevant matrix parameters (pH, titratable acidity, ethanol, glucose, and fructose) were measured across all wines. Tannin activity was not significantly correlated with any matrix variables, and the perception of drying and grippy was not correlated with tannin concentration and activity. However, ethanol content was well related to mouthfeel attributes and appeared to drive perceived drying. Although fructose and glucose content were well correlated, they did not drive the perception of sweetness, which is explained by the well-known mixture suppression effect.

Fate of tannins in Corsican pine litter.

PubMed

Nierop, Klaas G J; Verstraten, Jacobus M

2006-12-01

Tannins are ubiquitous in higher plants and also in litter and soils where they affect many biogeochemical processes. Despite this well-recognized role, their fate in litter and mineral soils is hardly known, as often only trace amounts, if any, are measured. In this study, we conducted an incubation experiment with Corsican pine litter to which known amounts of tannic acid (TA) or condensed tannins (CTs) from Corsican pine were added. Using Folin-Ciocalteu as a measure for total phenolics and HCl-butanol as an assay specific for CTs, acetone/water extractable phenolics and tannins decreased with time towards very low levels. Application of thermally assisted hydrolysis and methylation to litter before and after acetone/water extraction revealed that TA concentration decreased. By contrast, CTs remained to a great extent in the litter and could not be extracted suggesting that they were tightly bound.

Radical Scavenging Activities of Tannin Extracted from Amaranth (Amaranthus caudatus L.).

PubMed

Jo, Hyeon-Ju; Chung, Kang-Hyun; Yoon, Jin A; Lee, Kwon-Jai; Song, Byeong Chun; An, Jeung Hee

2015-06-01

This study investigates the bioactivity of tannin from amaranth (Amaranthus caudatus L.) extracts. The antioxidant activities of the extracts from amaranth leaves, flowers, and seeds were evaluated. Tannin from leaves of amaranth has been evaluated for superoxide scavenging activity by using DPPH and ABTS(+) analysis, reducing power, protective effect against H2O2-induced oxidative damage in L-132 and BNL-CL2 cells, and inhibition of superoxide radical effects on HL-60 cells. At a concentration of 100 μg/ml, tannin showed protective effects and restored cell survival to 69.2% and 41.8% for L-132 and BNL-CL2 cells, respectively. Furthermore, at the same concentration, tannin inhibited 41% of the activity of the superoxide radical on HL-60 cells and 43.4% of the increase in nitric oxide levels in RAW 264.7 cells. The expression levels of the antioxidant-associated protein SOD-1 were significantly increased in a concentration-dependent manner in RAW 264.7 cells treated with tannin from amaranth leaves. These results suggest that tannin from the leaves of Amaranthus caudatus L. is a promising source of antioxidant component that can be used as a food preservative or nutraceutical.

Characterization of tannin-metal complexes by UV-visible spectrophotometry

USDA-ARS?s Scientific Manuscript database

Tannins enter soils by plant decay and rain throughfall, but little is known of their effects on soils. Tannins may influence bioavailability and toxicity of metals by forming complexes and by mediating redox reactions. We evaluated the affinity and stoichiometry of Al(III) for a gallotannin, pent...

Condensed tannins from acacia mangium bark: Characterization by spot tests and FTIR

NASA Astrophysics Data System (ADS)

Bharudin, Muhammad Azizi; Zakaria, Sarani; Chia, Chin Hua

2013-11-01

This paper describes the adaptation and evaluation of one chemical tests for tannins characterization in acacia mangium bark. Acid butanol test developed to identify respectively condensed tannins is described. The two traditional tests used for tannin characterization namely ferric test and vanillin test were also performed and their functional also discussed. Condensed tannins were extracted from acacia mangium bark using water medium in presence of three different concentration basic reagent of NaOH(5%,10% and 15%) and were characterized by FT-IR spectrometry.

Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties.

PubMed

Mondol, Muhammad Abdul Mojid; Shin, Hee Jae; Rahman, M Aminur; Islam, Mohamad Tofazzal

2017-10-17

Sea cucumbers belonging to echinoderm are traditionally used as tonic food in China and other Asian countries. They produce abundant biologically active triterpene glycosides. More than 300 triterpene glycosides have been isolated and characterized from various species of sea cucumbers, which are classified as holostane and nonholostane depending on the presence or absence of a specific structural unit γ(18,20)-lactone in the aglycone. Triterpene glycosides contain a carbohydrate chain up to six monosaccharide units mainly consisting of d-xylose, 3-O-methy-d-xylose, d-glucose, 3-O-methyl-d-glucose, and d-quinovose. Cytotoxicity is the common biological property of triterpene glycosides isolated from sea cucumbers. Besides cytotoxicity, triterpene glycosides also exhibit antifungal, antiviral and hemolytic activities. This review updates and summarizes our understanding on diverse chemical structures of triterpene glycosides from various species of sea cucumbers and their important biological activities. Mechanisms of action and structural-activity relationships (SARs) of sea cucumber glycosides are also discussed briefly.

Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties

PubMed Central

Mondol, Muhammad Abdul Mojid; Shin, Hee Jae; Rahman, M. Aminur; Islam, Mohamad Tofazzal

2017-01-01

Sea cucumbers belonging to echinoderm are traditionally used as tonic food in China and other Asian countries. They produce abundant biologically active triterpene glycosides. More than 300 triterpene glycosides have been isolated and characterized from various species of sea cucumbers, which are classified as holostane and nonholostane depending on the presence or absence of a specific structural unit γ(18,20)-lactone in the aglycone. Triterpene glycosides contain a carbohydrate chain up to six monosaccharide units mainly consisting of d-xylose, 3-O-methy-d-xylose, d-glucose, 3-O-methyl-d-glucose, and d-quinovose. Cytotoxicity is the common biological property of triterpene glycosides isolated from sea cucumbers. Besides cytotoxicity, triterpene glycosides also exhibit antifungal, antiviral and hemolytic activities. This review updates and summarizes our understanding on diverse chemical structures of triterpene glycosides from various species of sea cucumbers and their important biological activities. Mechanisms of action and structural–activity relationships (SARs) of sea cucumber glycosides are also discussed briefly. PMID:29039760

Cattle and sheep develop preference for drinking water containing grape seed tannin.

PubMed

Kronberg, S L; Schauer, C S

2013-10-01

Ingestion of small amounts of some types of condensed tannins (CTs) by ruminant livestock can provide nutritional, environmental and economic benefits. However, practical methods are needed to make these tannins more available to ruminant livestock. Results from previous trials with crude quebracho and black wattle tannin indicated that cattle and/or sheep would not preferentially drink water containing these tannins. Therefore, we conducted preference trials to determine if cattle and sheep would learn to prefer water containing purified grape seed tannin (GST) that provided up to 2% of their daily dry matter (DM) intake. After gradual exposure to increasing amounts of this tannin in water during a pre-trial period, five adult ewes and five yearling heifers fed lucerne (Medicago sativa) pellets (19% CP) were offered water and several concentrations of GST solutions for either 15 (sheep trial) or 20 days (cattle trial). We measured intake of all liquids daily. Concentrations of blood urea were also measured for heifers when they drank only tannin solutions or water. Both sheep and cattle developed preferences for water with GST in it over water alone (P < 0.01) although this preference appeared earlier in the trial for sheep than for cattle. For the sheep, mean daily intake of water alone and all tannin solutions (in total) was 0.6 and 6.1 l, respectively. For the cattle, mean daily intake of water and all tannin solutions in total was 21.8 and 20.6 l, respectively, in the first half of the trial and 10.8 and 26.1 l, respectively, in the second half of the trial. Compared with the other tannin solutions, both sheep and cattle drank more of the solution with the highest tannin concentration (2% of daily DM intake as GST) than of water on more trial days (P < 0.05). Ingestion of water with the highest concentration of GST reduced blood plasma urea concentration in the cattle by 9% to 14% (P ≤ 0.10) compared with ingestion of water alone. Results from the trials

Yeast effects on Pinot noir wine phenolics, color, and tannin composition.

PubMed

Carew, Anna L; Smith, Paul; Close, Dugald C; Curtin, Chris; Dambergs, Robert G

2013-10-16

Extraction and stabilization of wine phenolics can be challenging for wine makers. This study examined how yeast choice affected phenolic outcomes in Pinot noir wine. Five yeast treatments were applied in replicated microvinification, and wines were analyzed by UV-visible spectrophotometry. At bottling, yeast treatment Saccharomyces cerevisiae RC212 wine had significantly higher concentrations of total pigment, free anthocyanin, nonbleachable pigment, and total tannin and showed high color density. Some phenolic effects were retained at 6 months' bottle age, and RC212 and S. cerevisae EC1118 wines showed increased mean nonbleachable pigment concentrations. Wine tannin composition analysis showed three treatments were associated with a higher percentage of trihydroxylated subunits (skin tannin indicator). A high degree of tannin polymerization was observed in wines made with RC212 and Torulaspora delbruekii , whereas tannin size by gel permeation chromatography was higher only in the RC212 wines. The results emphasize the importance of yeast strain choice for optimizing Pinot noir wine phenolics.

Interference of condensed tannin in lignin analyses of dry bean and forage crops.

PubMed

Marles, M A Susan; Coulman, Bruce E; Bett, Kirstin E

2008-11-12

Legumes with high concentrations of condensed tannin (pinto bean [Phaseolus vulgaris L.], sainfoin [Onobrychis viciifolia Scop.], and big trefoil [Lotus uliginosus Hoff.]), were compared to a selection of forages, with low or zero condensed tannin (smooth bromegrass [ Bromus inermis Leyss], Lotus japonicus [Regel] K. Larsen, and alfalfa [Medicago sativa L.]), using four methods to estimate fiber or lignin. Protocols were validated by using semipurified condensed tannin polymers in adulteration assays that tested low-lignin tissue with polyphenolic-enriched samples. The effect on lignin assay methods by condensed tannin concentration was interpreted using a multivariate analysis. There was an overestimation of fiber or lignin in the presence of condensed tannin in the acid detergent fiber (ADF) and Klason lignin (KL) assays compared to that in the thioglycolic acid (TGA) and acid detergent lignin (ADL) methods. Sulfite reagents (present in TGA lignin method) or sequential acidic digests at high temperatures (ADF followed by ADL) were required to eliminate condensed tannin. The ADF (alone) and KL protocols are not recommended to screen nonwoody plants, such as forages, where condensed tannin has accumulated in the tissue.

Hydrolyzable tannins as "quantitative defenses": limited impact against Lymantria dispar caterpillars on hybrid poplar.

PubMed

Barbehenn, Raymond V; Jaros, Adam; Lee, Grace; Mozola, Cara; Weir, Quentin; Salminen, Juha-Pekka

2009-04-01

The high levels of tannins in many tree leaves are believed to cause decreased insect performance, but few controlled studies have been done. This study tested the hypothesis that higher foliar tannin levels produce higher concentrations of semiquinone radicals (from tannin oxidation) in caterpillar midguts, and that elevated levels of radicals are associated with increased oxidative stress in midgut tissues and decreased larval performance. The tannin-free leaves of hybrid poplar (Populus tremulaxP. alba) were treated with hydrolyzable tannins, producing concentrations of 0%, 7.5% or 15% dry weight, and fed to Lymantria dispar caterpillars. As expected, larvae that ingested control leaves contained no measurable semiquinone radicals in the midgut, those that ingested 7.5% hydrolyzable tannin contained low levels of semiquinone radicals, and those that ingested 15% tannin contained greatly increased levels of semiquinone radicals. Ingested hydrolyzable tannins were also partially hydrolyzed in the midgut. However, increased levels of semiquinone radicals in the midgut were not associated with oxidative stress in midgut tissues. Instead, it appears that tannin consumption was associated with increased metabolic costs, as measured by the decreased efficiency of conversion of digested matter to body mass (ECD). Decreased ECD, in turn, decreased the overall efficiency of conversion of ingested matter to body mass (ECI). Contrary to our hypothesis, L. dispar larvae were able to maintain similar growth rates across all tannin treatment levels, in part, because of compensatory feeding. We conclude that hydrolyzable tannins act as "quantitative defenses" in the sense that high levels appear to be necessary to increase levels of semiquinone radicals in the midguts of caterpillars. However, these putative resistance factors are not sufficient to decrease the performance of tannin-tolerant caterpillars such as L. dispar.

Relation ofSpodoptera eridania choice to tannins and protein oflotus corniculatus.

PubMed

Briggs, M A

1990-05-01

Plant secondary compounds such as tannins may influence herbivore choice. To determine if herbivory was influenced by tannin concentration,Spodoptera eridania larvae were given a choice ofLotus corniculatus plants whose chemical profiles were altered by fertilization. Herbivores chose plants that had been grown with symbiotic nitrogen fixation as their only nitrogen source more often than fertilized plants. Choice was related to protein concentration, but not to tannin concentration.

Effectiveness of green tea tannin on rats with chronic renal failure.

PubMed

Yokozawa, T; Chung, H Y; He, L Q; Oura, H

1996-06-01

The effects of green tea tannin on nephrectomized rats were examined. There were increases in blood urea nitrogen, serum creatinine, and urinary protein, and a decrease in creatinine clearance in the nephrectomized control rats, whereas better results for these parameters were obtained in rats given green tea tannin after nephrectomy, demonstrating a suppressed progression of the renal failure. When the renal parenchyma was partially resected, the remnant kidney showed a decrease in the activity of radical scavenger enzymes. Green tea tannin, however, was found to lighten the kidney under such oxidative stress. Mesangial proliferation and glomerular sclerotic lesions, which were conspicuous in the rats that were not given green tea tannin after nephrectomy, were also relieved.

Tropical tannin-rich fodder intake modifies saliva-binding capacity in growing sheep.

PubMed

Vargas-Magaña, J J; Aguilar-Caballero, A J; Torres-Acosta, J F J; Sandoval-Castro, C A; Hoste, H; Capetillo-Leal, C M

2013-12-01

We evaluated the effect of feeding dietary tannins from Lysiloma latisiliquum fresh forage on the saliva tannin-binding capacity of hair sheep lambs without previous exposure to tannin-rich (TR) fodder. Twenty-four hair sheep lambs (13.6±3.04 kg LW) were fed a tannin-free diet at the beginning of the experimental period (from day 10 to 13). On day 14, lambs were distributed into three groups (n=8): control group (CG), fed with the tannin-free diet (from D10 to D112); tannin short-term group (TST), fed the basal diet and 650 g of L. latisiliquum forage (from D14 to D55); tannin long-term group (TLT), fed the basal diet and 650 g of L. latisiliquum forage (from D14 to D112). Saliva samples were collected from the mouth of each lamb in the morning before feeding time on D10 and D14 (baseline period), on D49 and D56 (period 1) and on D97 and D112 (period 2). The tannin binding response of salivary protein (∆% turbidity) was determined with the haze development test (HDT) using either tannic acid or L. latisiliquum forage acetone extract. A turbidity protein index (TPI) was calculated as (∆% turbidity/[salivary protein (mg)]). Differences in HDT and TPI in the different groups were compared by repeated measures ANOVA using Proc Mixed. All groups had similar ∆% turbidity throughout the experiment (P>0.05). At baseline and period 1, the TPI of the different groups was similar (P>0.05). On period 2 the TLT group showed higher TPI compared with CG (P<0.05). Meanwhile, CG and TST showed similar salivary TPI. The saliva of hair sheep lambs consuming TR L. latisiliquum fresh fodder (TLT group) increased their TPI compared with control lambs not exposed to tannins.

Extraction, purification and anti-radiation activity of persimmon tannin from Diospyros kaki L.f.

PubMed

Zhou, Zhide; Huang, Yong; Liang, Jintao; Ou, Minglin; Chen, Jiejing; Li, Guiyin

2016-10-01

In this study, persimmon tannin was extracted from Diospyros kaki L.f. using ultrasound-assisted extraction and purified by D101 macroporous resin column chromatography and polysulfone ultrafiltration membrane. The tannin content of the final persimmon tannin extracts was attained to 39.56% calculated as catechin equivalents. Also, the radioprotective effects of persimmon tannin for HEK 293T cells proliferation and apoptosis after Gamma irradiation were investigated by CCK-8, Hoechst 33258 staining, flow cytometry assay and intracellular reactive oxygen species assay (ROS). Persimmon tannin was pre-incubated with HEK 293T cells for 12 h prior to Gamma irradiation. It was found that pretreatment with persimmon tannin increased cell viability and inhibited generation of Gamma-radiation induced ROS in HEK 293T cells exposed to 8 Gy Gamma-radiation. The percentage of apoptotic cells were only 6.7% when the radiation dose was 8 Gy and pretreated with 200 μg/ml of persimmon tannin. All these results indicated that persimmon tannin offered a potent radioprotective effect on cell vitality and cell apoptosis of Gamma-radiation exposure in HEK 293T cells. This study would serve as a pre-clinical evaluation of persimmon tannin for use in people with radiation protection. Copyright © 2016 Elsevier Ltd. All rights reserved.

Thermodynamics of grape and wine tannin interaction with polyproline: implications for red wine astringency.

PubMed

McRae, Jacqui M; Falconer, Robert J; Kennedy, James A

2010-12-08

The astringency of red wine is largely due to the interaction between wine tannins and salivary proline-rich proteins and is known to change as wine ages. To further understand the mechanisms behind wine astringency change over time, thermodynamics of the interactions between poly(l-proline) (PLP) and grape seed and skin tannins (preveraison (PV) and commercially ripe) or Shiraz wine tannins (2 years old and 9-10 years old) was analyzed using isothermal titration calorimetry (ITC). The nature of these interactions varied with changes to the tannin structure that are associated with maturation. The change in enthalpy associated with hydrophobic interaction and hydrogen bonding decreased with tannin age and the stoichiometry of binding indicated that grape tannins associated with more proline residues than wine tannins, irrespective of molecular size. These results could provide an explanation for the observed change in wine astringency quality with age.

Effect of condensed tannins addition on the astringency of red wines.

PubMed

Soares, Susana; Sousa, André; Mateus, Nuno; de Freitas, Victor

2012-02-01

Astringency has been defined as a group of sensations involving dryness, tightening, and shrinking of the oral surface. It has been accepted that astringency is due to the tannin-induced interaction and/or precipitation of the salivary proline-rich proteins (PRPs) in the oral cavity, as a result of the ingestion of food products rich in tannins, for example, red wine. The sensory evaluation of astringency is difficult, and the existence of fast and reliable methods to its study in vitro is scarce. So, in this work, the astringency of red wine supplemented with oligomeric procyanidins (condensed tannins), and the salivary proteins (SP) involved in its development were evaluated by high-performance liquid chromatography analysis of human saliva after its interaction with red wine and by sensorial evaluation. The results show that for low concentration of tannins, the decrease of acidic PRPs and statherin is correlated with astringency intensity, with these families having a high relative complexation and precipitation toward condensed tannins comparatively to the other SP. However, for higher concentrations of tannins, the relative astringency between wines seems to correlate's to the glycosylated PRPs changes. This work shows for the first time that the several families of SP could be involved in different stages of the astringency development.

Polymeric tannins significantly alter properties and in vitro digestibility of partially gelatinized intact starch granule.

PubMed

Amoako, Derrick B; Awika, Joseph M

2016-10-01

Excess calorie intake is a growing global problem. This study investigated effect of complexing partially gelatinized starch with condensed tannins on in vitro starch digestibility. Extracts from tannin and non-tannin sorghum, and cellulose control, were reacted with normal and waxy maize starch in 30% (30E) and 50% ethanol (50E) solutions at 70°C/20min. More tannins complexed with the 30E than 50E starches (mean 6.2 vs 3.5mg/g, respectively). In the 30E treatments, tannins significantly increased crystallinity, pasting temperature, peak viscosity, and slow digesting starch (from 100 to 274mg/g) in normal, but not waxy starch, suggesting intragranular cross-linking with amylose. Tannins doubled resistant starch (RS) to approx. 300mg/g in both starches. In 50E treatments, tannins made both maize starches behave like raw potato starch (>90% RS), suggesting granule surface interactions dominated. Non-tannin treatments generally behaved similar to cellulose. Condensed tannins could be used to favorably alter starch digestion profile. Copyright © 2016 Elsevier Ltd. All rights reserved.

Formation of vacuolar tannin deposits in the chlorophyllous organs of Tracheophyta: from shuttles to accretions.

PubMed

Brillouet, Jean-Marc; Romieu, Charles; Lartaud, Marc; Jublanc, Elodie; Torregrosa, Laurent; Cazevieille, Chantal

2014-11-01

Most Tracheophyta synthesize-condensed tannins (also called proanthocyanidins), polymers of catechins, which appear in the vacuole as uniformly stained deposits-termed tannin accretions-lining the inner face of the tonoplast. A large body of evidence argues that tannins are formed in recently described thylakoid-derived organelles, the tannosomes, which are packed in membrane-bound shuttles (Brillouet et al. 2013); it has been suggested that shuttles agglomerate into tannin accretions. The aim of the study was to describe the ontogenesis of tannin accretions in members of the Tracheophyta. For this purpose, fresh specimens of young tissues from diverse Tracheophyta were cut, gently lacerated in paraformaldehyde, and examined using light, epifluorescence, confocal, and transmission electron microscopy. Fresh samples were also incubated with gelatin-Oregon Green, a fluorescent marker of condensed tannins. Our observations showed that vacuolar accretions (1 → 40 μm), that constitute the typical form of tannin storage in tannin-producing Tracheophyta, are formed by agglomeration (not fusion) of shuttles containing various proportions of chlorophylls and tannins.

No major role for binding by salivary proteins as a defense against dietary tannins in Mediterranean goats.

PubMed

Hanovice-Ziony, Michal; Gollop, Nathan; Landau, Serge Yan; Ungar, Eugene David; Muklada, Hussein; Glasser, Tzach Aharon; Perevolotsky, Avi; Walker, John Withers

2010-07-01

We investigated whether Mediterranean goats use salivary tannin-binding proteins to cope with tannin-rich forages by determining the affinity of salivary or parotid gland proteins for tannic acid or quebracho tannin. Mixed saliva, sampled from the oral cavity, or parotid gland contents were compared to the intermediate affinity protein bovine serum albumin with a competitive binding assay. Goats that consume tannin-rich browse (Damascus) and goats that tend to avoid tannins (Mamber) were sequentially fed high (Pistacia lentiscus L.), low (vetch hay), or zero (wheat hay) tannin forages. Affinity of salivary proteins for tannins did not differ between goat breeds and did not respond to presence or absence of tannins in the diet. Proteins in mixed saliva had slightly higher affinity for tannins than those in parotid saliva, but neither source contained proteins with higher affinity for tannins than bovine serum albumin. Similarly, 3 months of browsing in a tannin-rich environment had little effect on the affinity of salivary proteins for tannin in adult goats of either breed. We sampled mixed saliva from young kids before they consumed forage and after 3 months of foraging in a tannin-rich environment. Before foraging, the saliva of Mamber kids had higher affinity for tannic acid (but not quebracho tannin) than the saliva of Damascus kids, but there was no difference after 3 months of exposure to tannin-rich browse, and the affinity of the proteins was always similar to the affinity of bovine serum albumin. Our results suggest there is not a major role for salivary tannin-binding proteins in goats. Different tendencies of goat breeds to consume tannin-rich browse does not appear be related to differences in salivary tannin-binding proteins.

Endothelial cell cytotoxicity of cotton bracts tannin and aqueous cotton bracts extract

DOE Office of Scientific and Technical Information (OSTI.GOV)

Johnson, C.M.; Hanson, M.N.; Rohrbach, M.S.

1986-04-01

Using an in vitro cytotoxicity assay based on the release of /sup 51/Cr from cultured porcine thoracic aortic and pulmonary arterial endothelial cells, we have demonstrated that cotton bracts tannin is a potent endothelial cell cytotoxin. It produces dose-dependent lethal injury to both types of endothelial cells with the aortic cells, being somewhat more sensitive to tannin-mediated injury than the pulmonary arterial cells. Cytotoxic injury to the cells was biphasic. During the first 3 hr of exposure to tannin, no lethal injury was detected. However, during this period, profound changes in morphology were observed suggesting sublethal injury to the cellsmore » preceded the ultimate toxic damage. Comparison of the cytotoxicity dose curves for aqueous bracts extracts with those for tannin demonstrated that tannin was major cytotoxin present in bracts.« less

The role of condensed tannins in animal production: advances, limitations and future directions

USDA-ARS?s Scientific Manuscript database

Tannins represent one of the most abundant polyphenolic compounds in plants, second only to lignin. Tannins exist as a multitude of chemically unique entities in nature. The most commonly occurring tannins are typically divided into two major classes based on chemical structure: hydrolysable or cond...

Fungi from industrial tannins: potential application in biotransformation and bioremediation of tannery wastewaters.

PubMed

Prigione, Valeria; Trocini, Bruno; Spina, Federica; Poli, Anna; Romanisio, Davide; Giovando, Samuele; Varese, Giovanna Cristina

2018-05-01

Tannins are a complex family of polyphenolic compounds, widely distributed in the plant kingdom where they act as growth inhibitors towards many microorganisms including bacteria, yeasts, and fungi. Tannins are one of the major components of tannery wastewaters and may cause serious environmental pollution. In the present study, four different tannins (the hydrolysable chestnut ellagitannin and tara gallotannin and the condensed quebracho and wattle tannins) were characterized from a mycological point of view with the aim of selecting fungal strains capable of growing in the presence of high tannin concentration and thus potentially useful in industrial biotransformations of these compounds or in the bioremediation of tannery wastewaters. A total of 125 isolates of filamentous fungi belonging to 10 species and four genera (Aspergillus, Paecilomyces, Penicillium, and Talaromyces) were isolated from the tannin industrial preparations. Miniaturized biotransformation tests were set up with 10 fungal strains and the high-performance liquid chromatography (HPLC) analysis pointed out a strong activity of all the tested fungi on both chestnut and tara tannins. Two strains (Aspergillus tubingensis MUT 990 and Paecilomyces variotii MUT 1125), tested against a real tannery wastewater, were particularly efficient in chemical oxygen demand (COD) and tannin removal (> 60%), with a detoxification above 74%. These results indicate that these fungi are potentially exploitable in the treatment of tannery wastewaters.

Membrane lipids protected from oxidation by red wine tannins: a proton NMR study.

PubMed

Furlan, Aurélien L; Jobin, Marie-Lise; Buchoux, Sébastien; Grélard, Axelle; Dufourc, Erick J; Géan, Julie

2014-12-01

Dietary polyphenols widespread in vegetables and beverages like red wine and tea have been reported to possess antioxidant properties that could have positive effects on human health. In this study, we propose a new in situ and non-invasive method based on proton liquid-state nuclear magnetic resonance (NMR) to determine the antioxidant efficiency of red wine tannins on a twice-unsaturated phospholipid, 1,2-dilinoleoyl-sn-glycero-3-phosphocholine (DLiPC), embedded in a membrane model. Four tannins were studied: (+)-catechin (C), (-)-epicatechin (EC), (-)-epicatechin gallate (ECG), and (-)-epigallocatechin gallate (EGCG). The lipid degradation kinetics was determined by measuring the loss of the bis-allylic protons during oxidation induced by a radical initiator, 2,2'-Azobis(2-methylpropionamidine) dihydrochloride (AAPH). The antioxidant efficiency, i.e. the ability of tannins to slow down the lipid oxidation rate, was shown to be higher for galloylated tannins, ECG and EGCG. Furthermore, the mixture of four tannins was more efficient than the most effective tannin, EGCG, demonstrating a synergistic effect. To better understand the antioxidant action mechanism of polyphenols on lipid membranes, the tannin location was investigated by NMR and molecular dynamics. A correlation between antioxidant action of tannins and their location at the membrane interface (inserted at the glycerol backbone level) could thus be established. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

Chelation of Cu(II), Zn(II), and Fe(II) by tannin constituents of selected edible nuts.

PubMed

Karamać, Magdalena

2009-12-22

The tannin fractions isolated from hazelnuts, walnuts and almonds were characterised by colorimetric assays and by an SE-HPLC technique. The complexation of Cu(II) and Zn(II) was determined by the reaction with tetramethylmurexide, whereas for Fe(II), ferrozine was employed. The walnut tannins exhibited a significantly weaker reaction with the vanillin/HCl reagent than hazelnut and almond tannins, but the protein precipitation capacity of the walnut fraction was high. The SE-HPLC chromatogram of the tannin fraction from hazelnuts revealed the presence of oligomers with higher molecular weights compared to that of almonds. Copper ions were most effectively chelated by the constituents of the tannin fractions of hazelnuts, walnuts and almonds. At a 0.2 mg/assay addition level, the walnut tannins complexed almost 100% Cu(II). The Fe(II) complexation capacities of the tannin fractions of walnuts and hazelnuts were weaker in comparison to that of the almond tannin fraction, which at a 2.5 mg/assay addition level, bound Fe(II) by approximately 90%. The capacity to chelate Zn(II) was quite varied for the different nut tannin fractions: almond tannins bound as much as 84% Zn(II), whereas the value for walnut tannins was only 8.7%; and for hazelnut tannins, no Zn(II) chelation took place at the levels tested.

Chelation of Cu(II), Zn(II), and Fe(II) by Tannin Constituents of Selected Edible Nuts

PubMed Central

Karamać, Magdalena

2009-01-01

The tannin fractions isolated from hazelnuts, walnuts and almonds were characterised by colorimetric assays and by an SE-HPLC technique. The complexation of Cu(II) and Zn(II) was determined by the reaction with tetramethylmurexide, whereas for Fe(II), ferrozine was employed. The walnut tannins exhibited a significantly weaker reaction with the vanillin/HCl reagent than hazelnut and almond tannins, but the protein precipitation capacity of the walnut fraction was high. The SE-HPLC chromatogram of the tannin fraction from hazelnuts revealed the presence of oligomers with higher molecular weights compared to that of almonds. Copper ions were most effectively chelated by the constituents of the tannin fractions of hazelnuts, walnuts and almonds. At a 0.2 mg/assay addition level, the walnut tannins complexed almost 100% Cu(II). The Fe(II) complexation capacities of the tannin fractions of walnuts and hazelnuts were weaker in comparison to that of the almond tannin fraction, which at a 2.5 mg/assay addition level, bound Fe(II) by ~90%. The capacity to chelate Zn(II) was quite varied for the different nut tannin fractions: almond tannins bound as much as 84% Zn(II), whereas the value for walnut tannins was only 8.7%; and for hazelnut tannins, no Zn(II) chelation took place at the levels tested. PMID:20054482

Annotation and comparative analysis of the glycoside hydrolase genes in Brachypodium distachyon

DOE Office of Scientific and Technical Information (OSTI.GOV)

Tyler, Ludmila; Bragg, Jennifer; Wu, Jiajie

2010-01-01

Background Glycoside hydrolases cleave the bond between a carbohydrate and another carbohydrate, a protein, lipid or other moiety. Genes encoding glycoside hydrolases are found in a wide range of organisms, from archea to animals, and are relatively abundant in plant genomes. In plants, these enzymes are involved in diverse processes, including starch metabolism, defense, and cell-wall remodeling. Glycoside hydrolase genes have been previously cataloged for Oryza sativa (rice), the model dicotyledonous plant Arabidopsis thaliana, and the fast-growing tree Populus trichocarpa (poplar). To improve our understanding of glycoside hydrolases in plants generally and in grasses specifically, we annotated the glycoside hydrolasemore » genes in the grasses Brachypodium distachyon (an emerging monocotyledonous model) and Sorghum bicolor (sorghum). We then compared the glycoside hydrolases across species, both at the whole-genome level and at the level of individual glycoside hydrolase families. Results We identified 356 glycoside hydrolase genes in Brachypodium and 404 in sorghum. The corresponding proteins fell into the same 34 families that are represented in rice, Arabidopsis, and poplar, helping to define a glycoside hydrolase family profile which may be common to flowering plants. Examination of individual glycoside hydrolase familes (GH5, GH13, GH18, GH19, GH28, and GH51) revealed both similarities and distinctions between monocots and dicots, as well as between species. Shared evolutionary histories appear to be modified by lineage-specific expansions or deletions. Within families, the Brachypodium and sorghum proteins generally cluster with those from other monocots. Conclusions This work provides the foundation for further comparative and functional analyses of plant glycoside hydrolases. Defining the Brachypodium glycoside hydrolases sets the stage for Brachypodium to be a monocot model for investigations of these enzymes and their diverse roles in planta

Effects of tannin source and concentration from tree leaves on two species of tadpoles.

PubMed

Earl, Julia E; Semlitsch, Raymond D

2015-01-01

Vegetation in and around freshwater ecosystems can affect aquatic organisms through the production of secondary compounds, which are retained in leaves after senescence and are biologically active. Tannins can be toxic to tadpoles, but the plant source of tannins and tannin concentration have been confounded in experimental designs in previous studies. To examine the effects of the concentration and source of tannins (tree species), we examined the effects of 4 factors on tadpole survival, growth, and development: tannin source (red oak [Quercus rubra], white oak [Quercus alba], or sugar maple [Acer saccharum]); tannin concentration (including a control); diet protein level; and tadpole species (American toad [Anaxyrus americanus] and spring peepers [Pseudacris crucifer]). Tannin source and concentration affected spring peeper survival, but American toads had uniformly high survival. Spring peepers had a lower survival rate in high tannin concentrations of oak leachate but a high survival rate in both concentrations of sugar maple leachate. These differences in survival did not correspond with changes in dissolved oxygen, and no effect of dietary protein level on tadpole performance was observed. The presence of plant leachate resulted in increased tadpole growth in both species, but the mechanism for this finding is unclear. The results of the present study show that tannin concentration and source are important factors for tadpole performance, adding further evidence that plant chemistry can affect aquatic organisms. © 2014 SETAC.

Interactions between grape skin cell wall material and commercial enological tannins. Practical implications.

PubMed

Bautista-Ortín, Ana Belén; Cano-Lechuga, Mario; Ruiz-García, Yolanda; Gómez-Plaza, Encarna

2014-01-01

Commercial enological tannins were used to investigate the role that cell wall material plays in proanthocyanidin adsorption. Insoluble cell wall material, prepared from the skin of Vitis vinifera L. cv. Monastrell berries, was combined with solutions containing six different commercial enological tannins (proanthocyanidin-type tannins). Analysis of the proanthocyanidins in the solution, after fining with cell wall material, using phloroglucinolysis and size exclusion chromatography, provided quantitative and qualitative information on the non-adsorbed compounds. Cell wall material showed strong affinity for the proanthocyanidins, one of the commercial tannins being bound up to 61% in the experiment. Comparison of the molecular mass distribution of the commercial enological tannins in solution, before and after fining, suggested that cell walls affinity for proanthocyanidins was more related with the proanthocyanidin molecular mass than with their percentage of galloylation. These interactions may have some enological implications, especially as regards the time of commercial tannins addition to the must/wine. Copyright © 2013 Elsevier Ltd. All rights reserved.

Tannin profile of different Monastrell wines and its relation to projected market prices.

PubMed

Gómez-Plaza, Encarna; Olmos, Oscar; Bautista-Ortín, Ana Belén

2016-08-01

This study focuses on the differences or similarities in tannin composition and concentration in Monastrell wines from different wineries from the same geographic area and, within each winery, from wines elaborated based on different projected market prices, to determine whether there is any relationship between the wine tannin composition and the projected price. The tannin composition of the different wines, all of them analyzed at the same point during winemaking, indicated that those elaborated as premium wines presented higher phenol and tannin contents. The mean degree of polymerization of these wines was also positively related with the projected price, which agreed with the results obtained by size exclusion chromatography, that showed that wines with high projected prices had a higher proportion of polymeric tannins, suggesting that techniques favoring the extraction of skin tannins were mostly used in those wines projected as premium wines, probably looking for greater mouthfeel complexity. Copyright © 2016 Elsevier Ltd. All rights reserved.

Flavonol glycosides in the petal of Rosa species as chemotaxonomic markers.

PubMed

Sarangowa, Ochir; Kanazawa, Tsutomu; Nishizawa, Makoto; Myoda, Takao; Bai, Changxi; Yamagishi, Takashi

2014-11-01

Thirteen flavonol glycosides were isolated from the petals of Rosa species belonging to the section Gallicanae, and their structures were identified from their spectroscopic data. These flavonol glycosides, along with two flavonol glycosides isolated from Rosa rugosa, in the petals of 31 Rosa species belonging to sections Gallicanae, Cinnamomeae, Caninae, and Synstylae were quantitatively analyzed by UPLC. The results indicated that the species belonging to these sections could be classified into four types (Type A, B, C and D) based on the pattern of flavonol glycoside contents, whereas the R. rugosa flavonol glycosides were detected only in section Cinnamomeae. A principal components analysis (PCA) calculated from the 15 flavonol glycosides contained in these samples supported the presence of four types. The distribution of the species in Type D (a group of Cinnamomeae) was shown to reflect close interrelationships, but species in Type B (one group of Gallicanae) could be subdivided into two groups, one of which contained species in section Synstylae. Moreover, the flavonol glycosides were grouped by sugar moieties: a disaccharide composed of two hexoses (S1), a hexose (S2), including a hexose with galloyl group, a pentose (S3), and a disaccharide composed of a hexose and a pentose (S4). The ratios of the amounts of S1-S4 to total flavonol glycoside content indicated that differences among the four sections were more distinctive than the amounts of the 15 flavonol glycosides. The 31 samples were divided into Type B, composed of one type of Gallicanae and Synstylae, Type A+C, composed of another type of Gallicanae and Caninae, and Type D, composed of Cinnamomeae. The R. rugosa flavonol glycosides were shown to be important chemotaxonomic markers for the classification of species in Cinnamomeae, and this method of using flavonol glycosides as chemotaxonomic markers could be useful for the identification of Rosa species belonging to sections Gallicanae, Cinnamomeae

The tannosome is an organelle forming condensed tannins in the chlorophyllous organs of Tracheophyta.

PubMed

Brillouet, Jean-Marc; Romieu, Charles; Schoefs, Benoît; Solymosi, Katalin; Cheynier, Véronique; Fulcrand, Hélène; Verdeil, Jean-Luc; Conéjéro, Geneviève

2013-10-01

Condensed tannins (also called proanthocyanidins) are widespread polymers of catechins and are essential for the defence mechanisms of vascular plants (Tracheophyta). A large body of evidence argues for the synthesis of monomeric epicatechin on the cytosolic face of the endoplasmic reticulum and its transport to the vacuole, although the site of its polymerization into tannins remains to be elucidated. The aim of the study was to re-examine the cellular frame of tannin polymerization in various representatives of the Tracheophyta. Light microscopy epifluorescence, confocal microscopy, transmission electron microscopy (TEM), chemical analysis of tannins following cell fractionation, and immunocytochemistry were used as independent methods on tannin-rich samples from various organs from Cycadophyta, Ginkgophyta, Equisetophyta, Pteridophyta, Coniferophyta and Magnoliophyta. Tissues were fixed in a caffeine-glutaraldehyde mixture and examined by TEM. Other fresh samples were incubated with primary antibodies against proteins from both chloroplastic envelopes and a thylakoidal chlorophyll-carrying protein; they were also incubated with gelatin-Oregon Green, a fluorescent marker of condensed tannins. Coupled spectral analyses of chlorophyll and tannins were carried out by confocal microscopy on fresh tissues and tannin-rich accretions obtained through cell fractionation; chemical analyses of tannins and chlorophylls were also performed on the accretions. The presence of the three different chloroplast membranes inside vacuolar accretions that constitute the typical form of tannin storage in vascular plants was established in fresh tissues as well as in purified organelles, using several independent methods. Tannins are polymerized in a new chloroplast-derived organelle, the tannosome. These are formed by pearling of the thylakoids into 30 nm spheres, which are then encapsulated in a tannosome shuttle formed by budding from the chloroplast and bound by a membrane

The tannosome is an organelle forming condensed tannins in the chlorophyllous organs of Tracheophyta

PubMed Central

Brillouet, Jean-Marc; Romieu, Charles; Schoefs, Benoît; Solymosi, Katalin; Cheynier, Véronique; Fulcrand, Hélène; Verdeil, Jean-Luc; Conéjéro, Geneviève

2013-01-01

Background and Aims Condensed tannins (also called proanthocyanidins) are widespread polymers of catechins and are essential for the defence mechanisms of vascular plants (Tracheophyta). A large body of evidence argues for the synthesis of monomeric epicatechin on the cytosolic face of the endoplasmic reticulum and its transport to the vacuole, although the site of its polymerization into tannins remains to be elucidated. The aim of the study was to re-examine the cellular frame of tannin polymerization in various representatives of the Tracheophyta. Methods Light microscopy epifluorescence, confocal microscopy, transmission electron microscopy (TEM), chemical analysis of tannins following cell fractionation, and immunocytochemistry were used as independent methods on tannin-rich samples from various organs from Cycadophyta, Ginkgophyta, Equisetophyta, Pteridophyta, Coniferophyta and Magnoliophyta. Tissues were fixed in a caffeine–glutaraldehyde mixture and examined by TEM. Other fresh samples were incubated with primary antibodies against proteins from both chloroplastic envelopes and a thylakoidal chlorophyll-carrying protein; they were also incubated with gelatin–Oregon Green, a fluorescent marker of condensed tannins. Coupled spectral analyses of chlorophyll and tannins were carried out by confocal microscopy on fresh tissues and tannin-rich accretions obtained through cell fractionation; chemical analyses of tannins and chlorophylls were also performed on the accretions. Key Results and Conclusions The presence of the three different chloroplast membranes inside vacuolar accretions that constitute the typical form of tannin storage in vascular plants was established in fresh tissues as well as in purified organelles, using several independent methods. Tannins are polymerized in a new chloroplast-derived organelle, the tannosome. These are formed by pearling of the thylakoids into 30 nm spheres, which are then encapsulated in a tannosome shuttle formed by

Phytosteryl glycosides reduce cholesterol absorption: mechanisms in mice

USDA-ARS?s Scientific Manuscript database

Phytosteryl glycosides occur in natural foods but little is known about their metabolism and bioactivity. Purified acylated steryl glycosides (ASG) were compared with phytosteryl esters (PSE) in mice. Animals on a phytosterol-free diet received ASG or PSE by gavage in purified soybean oil along with...

Adaptations of quaking aspen for defense against damage by herbivores and related environmental agents

Treesearch

Richard L. Lindroth

2001-01-01

Quaking aspen (Populus tremuloides) employs two major systems of defense against damage by environmental agents: chemical defense and tolerance. Aspen accumulates appreciable quantities of phenolic glycosides (salicylates) and condensed tannins in most tissues and accumulates coniferyl benzoate in flower buds. Phenolic glycosides are toxic and/or deterrent to pathogens...

In Vitro Ruminal Degradability of Soybean Meal Protein Protected with Natural Tannin

NASA Astrophysics Data System (ADS)

Prasetiyono, B. W. H. E.; Subrata, A.; Tampoebolon, B. I. M.; Surono; Widiyanto

2018-02-01

The influence of tannin from tea waste and gambier as natural tannin sources on ruminal protein degradability was studied in this investigation. The soybean meal was used as protein source in this investigation. There were three treatments in this investigation mainly without protection (NT); protection with tea waste (Tt); and protection with gambier (Tg). The measured parameters consisted of in vitro dry matter digestibility (IVDMD), in vitro organic matter digestibility (IVOMD), and the ruminal fermentation characteristics. Results of this experiment showed that protection with tannin from tea waste as well as gambier increased (p<0.05) the IVDMD (77.0 vs 85.10 and 86.20%) and IVOMD (75.70 vs 83.40 and 84.40%). The highest IVDMD and IVOMD (p<0.05) was found in Tg treatment group. The Ruminal Undegradable Protein (RUP) in Tt and Tg group was higher than that in NT group (66.29 and 69.20 vs 51.10%). The ruminal protozoa population decreased (p<0.05) as a result of tannin protection (6690 vs 3790 and 5480 microorganism/ml rumen fluid). The Tt treatment group showed the lowest (p<0.05) ruminal protozoa population. The ammonia concentration in Tt and Tg tend to be lower compared to NT (4.67 and 4.69 vs 5.00 mM). The soybean meal protein protection with tea waste and gambier tannin increased IVDMD, IVOMD, RUP. The ruminal protozoa population and ammonia concentration, on the other hand, were decreased by tannin protection from those tannin natural sources. The natural tannin from gambier was the most effective protection agent for soybean meal protein.

Flavonoid glycosides and limonoids from Citrus molasses.

PubMed

Kuroyanagi, Masanori; Ishii, Hiromi; Kawahara, Nobuo; Sugimoto, Hiroyuki; Yamada, Hideo; Okihara, Kiyoshi; Shirota, Osamu

2008-01-01

Molasses of tangerine orange (Citrus unshiu Markovich) is obtained as a waste product in the course of tangerine orange juice production. This molasses is expected to be a useful source of organic compounds such as flavonoids and limonoids. To elucidate a use for this molasses waste, we isolated and identified its organic constituents. Two new flavanonol glycosides were isolated from tangerine orange molasses, along with several flavonoids such as hesperidine, narirutin, eriodictyol, 3',4',5,6,7,8-hexamethoxy-3-O-beta-D-glucopyranosyloxyflavone, and 3',4',5,6,7,8-hexamethoxy- 3-beta-D-[4-O-(3-hydroxy-3-methylglutaloyl)]-glucopyranosyloxyflavone, and limonoids such as limonin, nomilin, and cyclic peptide, citrusin III. The structures of the new flavanonol glycosides were determined as (2R,3R)-7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-aromadendrin and 7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-3,3',5,7-tetrahydroxy-4'-methoxyflavanone by means of spectral analyses using (1)H-NMR, (13)C-NMR, and 2D-NMR. Of these compounds, flavanone glycoside, hesperidin and narirutin were isolated as the main constituents. Thus, molasses is a promising source of flavonoid glycosides.

Antioxidant potential of polyphenols and tannins from burs of Castanea mollissima Blume.

PubMed

Zhao, Shan; Liu, Jie Yuan; Chen, Si Yu; Shi, Ling Ling; Liu, Yu Jun; Ma, Chao

2011-10-12

Spiny burs of Castanea mollissima Blume (Chinese chestnut) are usually discarded as industrial waste during post-harvesting processing. The objective of this study was to establish an extraction and isolation procedure for tannins from chestnut burs, and to assess their potential antioxidant activity. Aqueous ethanol solution was used as extraction solvent, and HPD 100 macroporous resin column was applied for isolation. The influence of solvent concentration in the extraction and elution process on extraction yield, tannins and polyphenols content, as well as antioxidant potential, including DPPH and ABTS radical scavenging ability, reducing power ability and cellular antioxidant ability were assessed. In both the extraction and isolation process, 50% aqueous ethanol led to superior total tannins and polyphenols content as well as significantly higher antioxidant activity. In addition, the antioxidant activity and the total tannins content in extracts and fractions had a positive linear correlation, and the predominant components responsible for antioxidant activities were characterized as hydrolysable tannins. To the best of our knowledge, this is the first report on the enrichment of tannins from burs of C. mollissim using macroporous resin chromatography, and to assess the cellular antioxidant activity of them.

Apoptotic activities of cardenolide glycosides from Asclepias subulata.

PubMed

Rascón-Valenzuela, L A; Velázquez, C; Garibay-Escobar, A; Vilegas, W; Medina-Juárez, L A; Gámez-Meza, N; Robles-Zepeda, R E

2016-12-04

Asclepias subulata Decne. (Apocynaceae) is a shrub occurring in Sonora-Arizona desert. The ethnic groups of Sonora, Mexico, Seris and Pimas, use this plant for the treatment of sore eyes, gastrointestinal disorders and cancer. To determine the cell death pathways that the cardenolide glycosides with antiproliferative activity found in the methanol extract of A. subulata are able to activate. The effect of cardenolide glycosides isolated of A. subulata on induction of apoptosis in cancer cells was evaluated through the measuring of several key events of apoptosis. A549 cells were treated for 12h with doses of 3.0, 0.2, 3.0 and 1.0µM of 12, 16-dihydroxicalotropin, calotropin, corotoxigenin 3-O-glucopyranoside and desglucouzarin, respectively. Apoptotic and necrotic cell levels were measured by double staining with annexin V-FITC/PI. Mitochondrial membrane depolarization was examined through JC-1 staining. Apoptosis cell death and the apoptosis pathways activated by cardenolide glycosides isolated of A. subulata were further characterized by the measurement of caspase-3, caspase-8 and caspase-9 activity. Apoptotic assays showed that the four cardenolide glycosides isolated of A. subulata induced apoptosis in A549 cells, which was evidencing by phosphatidylserine externalization in 18.2%, 17.0%, 23.9% and 22.0% for 12, 16-dihydroxicalotropin, calotropin, corotoxigenin 3-O-glucopyranoside and desglucouzarin, respectively, compared with 4.6% of control cells. Cell death was also associated with a decrease in mitochondrial membrane potential, which was more than 75% in the treated cultures respect to control. The activation of caspase-3 was observed in all cardenolide glycosides-treated cancer cells indicating the caspase-dependent apoptosis of A549 cells. Extrinsic and intrinsic apoptosis pathways were activated by cardenolide glycosides treatment at the doses tested. In this study was found that cardenolide glycosides, 12, 16-dihydroxicalotropin, calotropin

Relationship between red wine grade and phenolics. 2. Tannin composition and size.

PubMed

Kassara, Stella; Kennedy, James A

2011-08-10

Commercial red wines ( Vitis vinifera L. cv. Shiraz) produced during the 2009 vintage underwent winemaker assessment for allocation grade soon after production. The wines were then subjected to phenolic analysis to measure wine color (total anthocyanin, SO(2) nonbleachable pigment, and wine color density) and tannins (concentration, composition, and average degree of polymerization). A positive relationship was found between wine phenolic concentration and projected bottle price. Tannin compositional analysis suggested that there was specifically a relationship between wine grade and skin-derived tannins. These results suggest that maximization of skin tannin concentration and/or proportion is related to an increase in projected wine bottle price.

Salivary tannin-binding proteins are a pervasive strategy used by the folivorous/frugivorous black howler monkey.

PubMed

Espinosa-Gómez, Fabiola Carolina; Serio-Silva, Juan Carlos; Santiago-García, Juan Diego; Sandoval-Castro, Carlos Alfredo; Hernández-Salazar, Laura Teresa; Mejía-Varas, Fernando; Ojeda-Chávez, Javier; Chapman, Colin Austin

2018-02-01

Dietary tannins can affect protein digestion and absorption, be toxic, and influence food selection by being astringent and bitter tasting. Animals that usually ingest tannins may regularly secrete tannin-binding salivary proteins (TBSPs) to counteract the negative effects of tannins or TBSPs production can be induced by a tannin-rich diet. In the wild, many primates regularly eat a diet that contains tannin-rich leaves and unripe fruit and it has been speculated that they have the physiological ability to cope with dietary tannins; however, details of their strategy remains unclear. Our research details the salivary protein composition of wild and zoo-living black howler monkeys (Alouatta pigra) feeding on natural versus manufactured low-tannin diets, and examines differences in TBSPs, mainly proline-rich proteins (PRPs), to determine whether production of these proteins is dependent on the tannin content of their food. We measured the pH, flow rate, and concentration of total protein and trichloroacetic acid soluble proteins (an index of PRPs) in saliva. Howler monkeys produced slightly alkaline saliva that may aid in the binding interaction between tannin and salivary proteins. We used gel electrophoresis to describe the salivary protein profile and this analysis along with a tannin-binding assay allowed us to detect several TBSPs in all individuals. We found no differences in the characteristics of saliva between wild and zoo-living monkeys. Our results suggest that black howler monkeys always secrete TBSPs even when fed on foods low in tannins. This strategy of constantly using this salivary anti-tannin defense enables them to obtain nutrients from plants that sometimes contain high levels of tannins and may help immediately to overcome the astringent sensation of their food allowing howler monkeys to eat tanniferous plants. © 2018 Wiley Periodicals, Inc.

Anti-inflammatory Hydrolyzable Tannins from Myricaria bracteata.

PubMed

Liu, Jia-Bao; Ding, Ya-Si; Zhang, Ying; Chen, Jia-Bao; Cui, Bao-Song; Bai, Jin-Ye; Lin, Ming-Bao; Hou, Qi; Zhang, Pei-Cheng; Li, Shuai

2015-05-22

Twelve hydrolyzable tannins were obtained from the twigs of Myricaria bracteata, including two new hellinoyl-type dimers, bracteatinins D1 (1) and D2 (2); a new hellinoyl-type trimer, bracteatinin T1 (3); two known monomers, nilotinin M4 (4) and 1,3-di-O-galloyl-4,6-O-(aS)-hexahydroxydiphenoyl-β-d-glucose (5); six known dimers, tamarixinin A (6), nilotinin D8 (7), hirtellins A (10), B (9), and E (8), and isohirtellin C (11); and a known trimer, hirtellin T3 (12). The structures of the tannins were elucidated by spectroscopic data analysis and comparisons to known tannins. All compounds were evaluated as free radical scavengers using 1,1-diphenyl-2-picrylhydrazyl and hydroxy radicals and compared to the activity of BHT and Trolox. Compound 6 showed a significant anti-inflammatory effect on croton oil-induced ear edema in mice (200 mg/kg, inhibition rate 69.8%) and on collagen-induced arthritis in DBA/1 mice (20 mg/kg, inhibition rate 46.0% at day 57).

Antioxidant tannins from stem bark and fine root of Casuarina equisetifolia.

PubMed

Zhang, Shang-Ju; Lin, Yi-Ming; Zhou, Hai-Chao; Wei, Shu-Dong; Lin, Guang-Hui; Ye, Gong-Fu

2010-08-16

Structures of condensed tannins from the stem bark and fine root of Casuarina equisetifolia were identified using MALDI-TOF MS and HPLC analyses. The condensed tannins from stem bark and fine root consist predominantly of procyanidin combined with prodelphinidin and propelargonidin, and epicatechin is the main extension unit. The condensed tannins had different polymer chain lengths, varying from trimers to tridecamer for stem bark and to pentadecamer for fine root. The antioxidant activities were measured by two models: 1,1-diphenyl-2- picrylhydrazyl (DPPH) radical scavenging activity and ferric reducing/ antioxidant power (FRAP). The condensed tannins extracted from C. equisetifolia showed very good DPPH radical scavenging activity and ferric reducing/ antioxidant power, suggesting that these extracts may be considered as new sources of natural antioxidants for food and nutraceutical products.

Condensed Tannins from Ficus virens as Tyrosinase Inhibitors: Structure, Inhibitory Activity and Molecular Mechanism

PubMed Central

Chai, Wei-Ming; Feng, Hui-Ling; Zhuang, Jiang-Xing; Chen, Qing-Xi

2014-01-01

Condensed tannins from Ficus virens leaves, fruit, and stem bark were isolated and their structures characterized by 13C nuclear magnetic resonance spectrometry, high performance liquid chromatography electrospray ionization mass spectrometry, and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. The results showed that the leaves, fruit, and stem bark condensed tannins were complex mixtures of homo- and heteropolymers of B-type procyanidins and prodelphinidins with degrees of polymerization up to hexamer, dodecamer, and pentadecamer, respectively. Antityrosinase activities of the condensed tannins were studied. The results indicated that the condensed tannins were potent tyrosinase inhibitors. The concentrations for the leaves, fruit, and stem bark condensed tannins leading to 50% enzyme activity were determined to be 131.67, 99.89, and 106.22 μg/ml on monophenolase activity, and 128.42, 43.07, and 74.27 μg/ml on diphenolase activity. The inhibition mechanism, type, and constants of the condensed tannins on the diphenolase activity were further investigated. The results indicated that the condensed tannins were reversible and mixed type inhibitors. Fluorescence quenching, copper interacting, and molecular docking techniques were utilized to unravel the molecular mechanisms of the inhibition. The results showed that the hydroxyl group on the B ring of the condensed tannins could chelate the dicopper irons of the enzyme. Moreover, the condensed tannins could reduce the enzyme product o-quinones into colourless compounds. These results would contribute to the development and design of antityrosinase agents. PMID:24637701

The role of tannins in conventional and membrane treatment of tannery wastewater.

PubMed

Munz, G; De Angelis, D; Gori, R; Mori, G; Casarci, M; Lubello, C

2009-05-30

The role that tannins play in tannery wastewater treatment has been evaluated employing a pilot Membrane Bioreactor (MBR) plant and a full scale Conventional Activated Sludge Process (CASP) plant conducted in parallel. The proposed methodology has established the preliminary use of respirometry to examine the biodegradability of a selection of commercial products (synthetic and natural tannins); the subsequent analysis, by means of spectrophotometric reading and RP-IPC (Reverse-Phase Ion-Pair) liquid chromatography, estimates the concentrations of natural tannins and naphthalenesulfonic tanning agents in the influent and effluent samples. The results show that a consistent percentage of the Total Organic Carbon (TOC) in the effluent of the biological phase of the plants is attributable to the presence of natural and synthetic (Sulfonated Naphthalene-Formaldehyde Condensates, SNFC) tannins (17% and 14% respectively). The titrimetric tests that were aimed at evaluating the levels of inhibition on the nitrifying biomass samples did not allow a direct inhibiting effect to be associated with the concentration levels of the tannin in the effluent. Nonetheless, the reduced specific growth rates of ammonium and nitrite oxidising bacteria imply that a strong environmental pressure is present, if not necessarily due to the concentration of tannins, due to the wastewater as a whole. The differences that have emerged by comparing the two technologies (CASP and MBR), in regards to the role that tannins play in terms of biodegradability, did not appear to be significant.

Inhibition of α-amylase and glucoamylase by tannins extracted from cocoa, pomegranates, cranberries, and grapes.

PubMed

Barrett, Ann; Ndou, Tshinanne; Hughey, Christine A; Straut, Christine; Howell, Amy; Dai, Zifei; Kaletunc, Gonul

2013-02-20

Proanthocyanidins and ellagitannins, referred to as "tannins", exist in many plant sources. These compounds interact with proteins due to their numerous hydroxyl groups, which are suitable for hydrophobic associations. It was hypothesized that tannins could bind to the digestive enzymes α-amylase and glucoamylase, thereby inhibiting starch hydrolysis. Slowed starch digestion can theoretically increase satiety by modulating glucose "spiking" and depletion that occurs after carbohydrate-rich meals. Tannins were isolated from extracts of pomegranate, cranberry, grape, and cocoa and these isolates tested for effectiveness to inhibit the activity of α-amylase and glucoamylase in vitro. The compositions of the isolates were confirmed by NMR and LC/MS analysis, and tannin-protein interactions were investigated using relevant enzyme assays and differential scanning calorimetry (DSC). The results demonstrated inhibition of each enzyme by each tannin, but with variation in magnitude. In general, larger and more complex tannins, such as those in pomegranate and cranberry, more effectively inhibited the enzymes than did less polymerized cocoa tannins. Interaction of the tannins with the enzymes was confirmed through calorimetric measurements of changes in enzyme thermal stability.

Use of condensed tannin extract from quebracho trees to reduce methane emissions from cattle.

PubMed

Beauchemin, K A; McGinn, S M; Martinez, T F; McAllister, T A

2007-08-01

Our objective was to determine if condensed tannin extract from quebracho trees (Schinopsis quebracho-colorado; red quebracho) could be used to reduce enteric methane emissions from cattle. The experiment was designed as a repeated 3 x 3 Latin square (4 squares) with 3 treatments (0, 1, and 2% of dietary DM as quebracho tannin extract) and 3 28-d periods. Six spayed Angus heifers (238 +/- 13.3 kg of initial BW) and 6 Angus steers (207 +/- 8.2 kg of initial BW) were each assigned to 2 squares. The measured condensed tannin content of the extract was 91%, and the basal diet contained 70% forage (DM basis). Feeding quebracho tannin extract had no effect on BW, ADG, or nutrient intakes. Furthermore, it had no effect on DM, energy, or fiber (ADF and NDF) digestibility, but apparent digestibility of CP decreased linearly (P < 0.001) by 5 and 15% with 1 and 2% quebracho tannin extract, respectively. There were no effects of quebracho tannin extract on methane emissions (g/d, g/kg of DM, % of GE intake, or % of DE intake). Feeding up to 2% of the dietary DM as quebracho tannin extract failed to reduce enteric methane emissions from growing cattle, although the protein-binding effect of the quebracho tannin extract was evident.

In vitro anti-HIV and antioxidant activity of Hoodia gordonii (Apocynaceae), a commercial plant product.

PubMed

Kapewangolo, Petrina; Knott, Michael; Shithigona, Regina E K; Uusiku, Sylvia L; Kandawa-Schulz, Martha

2016-10-24

Hoodia gordonii products are widely commercialized for anti-obesity purposes; however, minimal research is available on the other health properties demonstrated by this popular herbal plant. H. gordonii crude extracts (ethanol and ethyl acetate) were assayed for in vitro anti-HIV-1 protease (PR), reverse transcriptase (RT) and integrase activity. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) and reducing power assays were used for the antioxidant analysis. In addition, qualitative and quantitative phytochemical analyses of the extracts were determined using standard methods. H. gordonii extract demonstrated good inhibition against HIV RT with IC 50 values of 73.55 ± 0.04 and 69.81 ± 9.45 μg/mL for ethanol and ethyl acetate extracts, respectively. Both extracts also demonstrated inhibitory activity against HIV PR with IC 50 values of 97.29 ± 0.01 and 63.76 ± 9.01 μg/mL for ethanol and ethyl acetate extracts. In addition, H. gordonii also showed good antioxidant activity with IC 50 values of 124.6 ± 11.3 and 126.2 ± 3.15 μg/mL obtained for ethanol and ethyl acetate extracts, respectively. The reducing power of H. gordonii extracts increased as the concentration increased which confirmed the presence of antioxidants (reductants) in the extracts. Phytochemical screening of H. gordonii revealed the presence of phenolics, alkaloids, terpenes, steroids, cardiac glycosides and tannins in the ethanolic extract, while the ethyl acetate extract only showed the presence of phenolics, cardiac glycosides and steroids. The total phenolic content was 420 ± 0.17 and 319.9 ± 0.2 mg GAE/g for the ethanol and ethyl acetate extracts, respectively. The ethanol extract, which revealed the presence of tannins, had a tannin content of 330 ± 0.2 mg TAE/g extract. This data suggests that H. gordonii has good in vitro inhibition against selected HIV-1 enzymes as well as antioxidant properties, suggesting new potential uses for this commercial

The influence of condensed tannin structure on rate of microbial mineralization and reactivity to chemical assays.

PubMed

Norris, Charlotte E; Preston, Caroline M; Hogg, Karen E; Titus, Brian D

2011-03-01

We examined how tannin structure influences reactivity in tannin assays and carbon and nitrogen mineralization. Condensed tannins from the foliage of ten tree and shrub species and from pecan shells (Carya illinoensis) had different proportions of: (a) epicatechin (cis) and catechin (trans) isomers, (b) procyanidin (PC) and prodelphinidin (PD) monomers, and (c) different chain lengths. The response of each tannin to several widely used tannin assays was determined. Although there was some variation in response to proanthocyanidin (butanol/HCl) and Folin Ciocalteu assays, we did not deduce any predictable relationship between tannin structure and response to either assay. There was little variation in protein precipitation among the different tannins. To assess biological activity, six of the tannins were incubated with forest humus for 22 days. We determined that, while PC-based tannins remained at least partly extractable for the duration of the incubation, tannins with a high proportion of PD subunits rapidly became unextractable from soil. There was a positive correlation between net nitrogen mineralization and cis chemical structure. Carbon mineralization was enhanced initially by the addition of tannins to humus, but after 22 days, a negative correlation between the proportion of cis subunits and respiration was determined. Overall, we were not able to demonstrate consistent effects of structure on either microbial mineralization or reactivity to chemical assays; such relationships remain elusive.

Formaldehyde condensation products of model phenols for conifer bark tannins

Treesearch

Richard W. Hemingway; Gerald W. McGraw

1978-01-01

Gel permeation chromatography of the condensation products of phenols and formaldehyde proved effective in understanding the reactions of condensed tannins with formaldehyde. Rates of condensation of phloroglucinols, resorcinols, catechols, (+)catechins, and (-)epicatechin were examined to determine if methylol-tannins from southern pine bark could be prepared as resin...

Formaldehyde condensation products of model phenols for conifer bark tannins

Treesearch

R.W. Hemingway; G.W. McGraw

1978-01-01

Gel permeation chromatograpy of the condensation products of phenols and formaldehyde proved effective in understanding the reactions of condensed tannins with formaldehyde. Rates of condensation of phloroglucinols, resorcinols, catechols, (+)catechin, and (-)epicatechin were examined to determine if methylol-tannins from southern pine bark could be prepared as resin...

Univariate and multivariate analysis of tannin-impregnated wood species using vibrational spectroscopy.

PubMed

Schnabel, Thomas; Musso, Maurizio; Tondi, Gianluca

2014-01-01

Vibrational spectroscopy is one of the most powerful tools in polymer science. Three main techniques--Fourier transform infrared spectroscopy (FT-IR), FT-Raman spectroscopy, and FT near-infrared (NIR) spectroscopy--can also be applied to wood science. Here, these three techniques were used to investigate the chemical modification occurring in wood after impregnation with tannin-hexamine preservatives. These spectroscopic techniques have the capacity to detect the externally added tannin. FT-IR has very strong sensitivity to the aromatic peak at around 1610 cm(-1) in the tannin-treated samples, whereas FT-Raman reflects the peak at around 1600 cm(-1) for the externally added tannin. This high efficacy in distinguishing chemical features was demonstrated in univariate analysis and confirmed via cluster analysis. Conversely, the results of the NIR measurements show noticeable sensitivity for small differences. For this technique, multivariate analysis is required and with this chemometric tool, it is also possible to predict the concentration of tannin on the surface.

Inhibition of α-Amylases by Condensed and Hydrolysable Tannins: Focus on Kinetics and Hypoglycemic Actions

PubMed Central

Kato, Camila Gabriel; Gonçalves, Geferson de Almeida; Peralta, Rosely Aparecida; Seixas, Flavio Augusto Vicente; de Sá-Nakanishi, Anacharis Babeto; Bracht, Lívia; Comar, Jurandir Fernando

2017-01-01

The aim of the present study was to compare the in vitro inhibitory effects on the salivary and pancreatic α-amylases and the in vivo hypoglycemic actions of the hydrolysable tannin from Chinese natural gall and the condensed tannin from Acacia mearnsii. The human salivary α-amylase was more strongly inhibited by the hydrolysable than by the condensed tannin, with the concentrations for 50% inhibition (IC50) being 47.0 and 285.4 μM, respectively. The inhibitory capacities of both tannins on the pancreatic α-amylase were also different, with IC50 values being 141.1 μM for the hydrolysable tannin and 248.1 μM for the condensed tannin. The kinetics of the inhibition presented complex patterns in that for both inhibitors more than one molecule can bind simultaneously to either the free enzyme of the substrate-complexed enzyme (parabolic mixed inhibition). Both tannins were able to inhibit the intestinal starch absorption. Inhibition by the hydrolysable tannin was concentration-dependent, with 53% inhibition at the dose of 58.8 μmol/kg and 88% inhibition at the dose of 294 μmol/kg. For the condensed tannin, inhibition was not substantially different for doses between 124.4 μmol/kg (49%) and 620 μmol/kg (57%). It can be concluded that both tannins, but especially the hydrolysable one, could be useful in controlling the postprandial glycemic levels in diabetes. PMID:28589038

The basic mechanism of inotropic action of digitalis glycosides.

PubMed

Smith, T W

1984-01-01

A broad survey of the experimental literature suggests that the only unifying concept of digitalis action is that these drugs, at pharmacologically relevant doses, bind with high affinity and specificity to sites on the NaK-ATPase complex that face the outer surface of nearly all eukaryotic cells. Alternative receptors, if they exist, have not been defined. As might be expected, a broad range of biologic effects results from this basic interaction. The clinical therapeutic effects of digitalis include enhancement of myocardial contractility and changes in the properties of the cardiac conduction system; the latter, in turn, result from both direct and autonomically mediated effects [44]. Autonomic effects involve alterations in both parasympathetic and sympathetic activity, and these are attributable to both central and peripheral neural mechanisms [44]. As we have reviewed, there is compelling evidence that one mechanism leading to sustained positive inotropic effects of digitalis glycosides in heart muscle is partial inhibition of sodium transport. Earlier evidence [16, 17] is now supported by electrophysiologic studies [29, 30, 45, 46], intracellular ion-sensitive microelectrode methods [47, 48], and ion flux measurements using radioisotope tracers [14, 15, 49]. Inhibition of myocardial monovalent cation transport has been documented in intact glycoside-sensitive animal models at doses and plasma and myocardial levels causing a positive inotropic effect without overt toxicity [12]. However, these findings do not preclude other mechanisms that may be operative in addition to, or in some circumstances instead of, myocardial Na-K pump inhibition. In the context of much seemingly conflicting evidence [35, 36, 37, 50, 51], the hypothesis advanced by Akera and Brody is of interest [17]. These authors suggest that interaction of subtoxic digitalis concentrations with myocardial NaK-ATPase reduces maximum sodium transport capacity, resulting in an enhanced transient

Amelioration of High Fructose-Induced Cardiac Hypertrophy by Naringin.

PubMed

Park, Jung Hyun; Ku, Hyeong Jun; Kim, Jae Kyeom; Park, Jeen-Woo; Lee, Jin Hyup

2018-06-21

Heart failure is a frequent unfavorable outcome of pathological cardiac hypertrophy. Recent increase in dietary fructose consumption mirrors the rise in prevalence of cardiovascular diseases such as cardiac hypertrophy leading to concerns raised by public health experts. Mitochondria, comprising 30% of cardiomyocyte volume, play a central role in modulating redox-dependent cellular processes such as metabolism and apoptosis. Furthermore, mitochondrial dysfunction is a key cause of pathogenesis of fructose-induced cardiac hypertrophy. Naringin, a major flavanone glycoside in citrus species, has displayed strong antioxidant potential in models of oxidative stress. In this study, we evaluated protective effects of naringin against fructose-induced cardiac hypertrophy and associated mechanisms of action, using in vitro and in vivo models. We found that naringin suppressed mitochondrial ROS production and mitochondrial dysfunction in cardiomyocytes exposed to fructose and consequently reduced cardiomyocyte hypertrophy by regulating AMPK-mTOR signaling axis. Furthermore, naringin counteracted fructose-induced cardiomyocyte apoptosis, and this function of naringin was linked to its ability to inhibit ROS-dependent ATM-mediated p53 signaling. This result was supported by observations in in vivo mouse model of cardiac hypertrophy. These findings indicate a novel role for naringin in protecting against fructose-induced cardiac hypertrophy and suggest unique therapeutic strategies for prevention of cardiovascular diseases.

Strawberry tannins inhibit IL-8 secretion in a cell model of gastric inflammation.

PubMed

Fumagalli, Marco; Sangiovanni, Enrico; Vrhovsek, Urska; Piazza, Stefano; Colombo, Elisa; Gasperotti, Mattia; Mattivi, Fulvio; De Fabiani, Emma; Dell'Agli, Mario

2016-09-01

In the present study we chemically profiled tannin-enriched extracts from strawberries and tested their biological properties in a cell model of gastric inflammation. The chemical and biological features of strawberry tannins after in vitro simulated gastric digestion were investigated as well. The anti-inflammatory activities of pure strawberry tannins were assayed to get mechanistic insights. Tannin-enriched extracts from strawberries inhibit IL-8 secretion in TNFα-treated human gastric epithelial cells by dampening the NF-κB signaling. In vitro simulated gastric digestion slightly affected the chemical composition and the biological properties of strawberry tannins. By using pure compounds, we found that casuarictin may act as a pure NF-κB inhibitor while agrimoniin inhibits IL-8 secretion also acting on other biological targets; in our system procyanidin B1 prevents the TNFα-induced effects without interfering with the NF-κB pathway. We conclude that strawberry tannins, even after in vitro simulated gastric digestion, exert anti-inflammatory activities at nutritionally relevant concentrations. Copyright © 2016 Elsevier Ltd. All rights reserved.

Novel Strategies for Upstream and Downstream Processing of Tannin Acyl Hydrolase

PubMed Central

Rodríguez-Durán, Luis V.; Valdivia-Urdiales, Blanca; Contreras-Esquivel, Juan C.; Rodríguez-Herrera, Raúl; Aguilar, Cristóbal N.

2011-01-01

Tannin acyl hydrolase also referred as tannase is an enzyme with important applications in several science and technology fields. Due to its hydrolytic and synthetic properties, tannase could be used to reduce the negative effects of tannins in beverages, food, feed, and tannery effluents, for the production of gallic acid from tannin-rich materials, the elucidation of tannin structure, and the synthesis of gallic acid esters in nonaqueous media. However, industrial applications of tannase are still very limited due to its high production cost. Thus, there is a growing interest in the production, recovery, and purification of this enzyme. Recently, there have been published a number of papers on the improvement of upstream and downstream processing of the enzyme. These papers dealt with the search for new tannase producing microorganisms, the application of novel fermentation systems, optimization of culture conditions, the production of the enzyme by recombinant microorganism, and the design of efficient protocols for tannase recovery and purification. The present work reviews the state of the art of basic and biotechnological aspects of tannin acyl hydrolase, focusing on the recent advances in the upstream and downstream processing of the enzyme. PMID:21941633

New benzophenone and quercetin galloyl glycosides from Psidium guajava L.

PubMed

Matsuzaki, Keiichi; Ishii, Rie; Kobiyama, Kaori; Kitanaka, Susumu

2010-07-01

New benzophenone and flavonol galloyl glycosides were isolated from an 80% MeOH extract of Psidium guajava L. (Myrtaceae) together with five known quercetin glycosides. The structures of the novel glycosides were elucidated to be 2,4,6-trihydroxybenzophenone 4-O-(6''-O-galloyl)-beta-D: -glucopyranoside (1, guavinoside A), 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6''-O-galloyl)-beta-D: -glucopyranoside (2, guavinoside B), and quercetin 3-O-(5''-O-galloyl)-alpha-L: -arabinofuranoside (3, guavinoside C) by NMR, MS, UV, and IR spectroscopies. Isolated phenolic glycosides showed significant inhibitory activities against histamine release from rat peritoneal mast cells, and nitric oxide production from a murine macrophage-like cell line, RAW 264.7.

40 CFR 721.10666 - Quaternary ammonium compounds, bis(fattyalkyl) dimethyl, salts with tannins (generic).

Code of Federal Regulations, 2014 CFR

2014-07-01

...(fattyalkyl) dimethyl, salts with tannins (generic). 721.10666 Section 721.10666 Protection of Environment..., bis(fattyalkyl) dimethyl, salts with tannins (generic). (a) Chemical substance and significant new... compounds, bis(fattyalkyl) dimethyl, salts with tannins (PMN P-12-437) is subject to reporting under this...

40 CFR 721.10666 - Quaternary ammonium compounds, bis(fattyalkyl) dimethyl, salts with tannins (generic).

Code of Federal Regulations, 2013 CFR

2013-07-01

...(fattyalkyl) dimethyl, salts with tannins (generic). 721.10666 Section 721.10666 Protection of Environment..., bis(fattyalkyl) dimethyl, salts with tannins (generic). (a) Chemical substance and significant new... compounds, bis(fattyalkyl) dimethyl, salts with tannins (PMN P-12-437) is subject to reporting under this...

Acylated-oxypregnane glycosides from the roots of Asclepias syriaca.

PubMed

Warashina, Tsutomu; Noro, Tadataka

2009-02-01

Twenty new pregnane glycosides were obtained from the roots of Asclepias syriaca L. (Asclepiadaceae). These glycosides were confirmed to contain ikemagenin, 12-O-nicotinoyllineolon, 5alpha,6-dihydroikemagenin, and 12-O-tigloylisolineolon, as their aglycones, using both spectroscopic and chemical methods.

Photochemistry and pharmacology of 9, 19-cyclolanostane glycosides isolated from genus Cimicifuga.

PubMed

Su, Yang; Chi, Wen-Cheng; Wu, Lun; Wang, Qiu-Hong; Kuang, Hai-Xue

2016-10-01

The constituents of Cimicifuga plants have been extensively investigated, and the principal metabolites are 9, 19-cyclolanostane triterpenoid glycosides, which often exhibit extensive pharmacological activities. 9, 19-Cyclolanostane triterpenoid glycosides are distributed widely in genus Cimicifuga rather than in other members of the Ranunculaceae family. So far, more than 140 cycloartane triterpene glycosides have been isolated from Cimicifuga spp.. The aim of this review was to summarize all 9, 19-cyclolanostane triterpenoid glycosides based on the available relevant scientific literatures from 2000 to 2014. Biological studies of cycloartane triterpene glycosides from Cimicifuga spp. are also discussed. Copyright © 2016 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

Steroidal glycosides from the roots of Asclepias curassavica.

PubMed

Warashina, Tsutomu; Noro, Tadataka

2008-03-01

Twenty-six new acylated-oxypregnane glycosides were obtained along with three known cardenolide glycosides from the roots of Asclepias curassavica (Asclepiadaceae). The new compounds were confirmed to contain 12-O-benzoylsarcostin, 12-O-benzoyldeacylmetaplexigenin, kidjolanin, and 12-O-benzoyltayloron, and one new acylated-oxypregnane, 12-O-(E)-cinnamoyltayloron, as their aglycones, using both spectroscopic and chemical methods.

Tannin extraction pretreatment and very high gravity fermentation of acorn starch for bioethanol production.

PubMed

Chao, Bin; Liu, Ruiliang; Zhang, Xueling; Zhang, Xu; Tan, Tianwei

2017-10-01

The bioethanol production from a novel non-grain feedstock, acorn starch, was studied in this work. The inhibition of tannin in strain growth was investigated, and the effect of tannin was negligible when the tannin concentration was lower than 1g/L in medium. Therefore, the extraction of tannin was performed using 40% (v/v) ethanol-water solution as the solvent for three times under the conditions of solid/liquid ratio 1:20, 60°C, 3h, by which more than 80% of tannin in acorn was extracted and the content of tannin in acorn decreased from 7.4% (w/w) to 1.5% (w/w). Very high gravity (VHG) fermentation technology was subsequently carried out to achieve a high ethanol concentration at 86.4g/L. A comprehensive process for bioethanol production from acorn starch was designed and a preliminary economic assessment was then performed revealing that this process appeared technically and economically justified. Copyright © 2017 Elsevier Ltd. All rights reserved.

SEPARATION OF THORIUM FROM RARE EARTHS WITH TANNIN (in Russian)

DOE Office of Scientific and Technical Information (OSTI.GOV)

Vlodavets, N.I.

1959-03-01

Thorium is quantitatively precipitated with tannin in a 0.005 N solution of nitric or hydrochloric acid. This permits its separation from trivalent rare earths, which are not precipitated with tannin in such relatively weak acid solutions. The accuracy of the determinations is as usual at the gravimetric determinations of macroquantities of elements. (auth)

Effect of wine pH and bottle closure on tannins.

PubMed

McRae, Jacqui M; Kassara, Stella; Kennedy, James A; Waters, Elizabeth J; Smith, Paul A

2013-11-27

The impact of wine pH and closure type on color, tannin concentration, and composition was investigated. A single vintage of Cabernet Sauvignon wine was divided into three batches, the pH was adjusted to 3.2, 3.5 or 3.8, and the wines were bottled under screw caps with either SaranTin (ST) or Saranex (Sx) liners. After 24 months, the tannin concentration, tannin percent yield (relating to the proportion of acid-labile interflavan bonds), and the mean degree of polymerization (mDp) had decreased significantly, all of which can contribute to the softening of wine astringency with aging. The higher pH wines contained less percent (-)-epicatechin 3-O-gallate subunits, whereas the Sx pH 3.2 wines were significantly lower in percent yield and mDp than the other wines. Overall, the tannin structure and wine color of the lower pH wines (pH 3.2) bottled under Sx screw caps changed more rapidly with aging than those of the higher pH wines (pH 3.8) bottled under ST screw caps.

Seed removal by scatter-hoarding rodents: the effects of tannin and nutrient concentration.

PubMed

Wang, Bo; Yang, Xiaolan

2015-04-01

The mutualistic interaction between scatter-hoarding rodents and seed plants have a long co-evolutionary history. Plants are believed to have evolved traits that influence the foraging behavior of rodents, thus increasing the probability of seed removal and caching, which benefits the establishment of seedlings. Tannin and nutrient content in seeds are considered among the most essential factors in this plant-animal interaction. However, most previous studies used different species of plant seeds, rendering it difficult to tease apart the relative effect of each single nutrient on rodent foraging behavior due to confounding combinations of nutrient contents across seed species. Hence, to further explore how tannin and different nutritional traits of seed affect scatter-hoarding rodent foraging preferences, we manipulated tannin, fat, protein and starch content levels, and also seed size levels by using an artificial seed system. Our results showed that both tannin and various nutrients significantly affected rodent foraging preferences, but were also strongly affected by seed size. In general, rodents preferred to remove seeds with less tannin. Fat addition could counteract the negative effect of tannin on seed removal by rodents, while the effect of protein addition was weaker. Starch by itself had no effect, but it interacted with tannin in a complex way. Our findings shed light on the effects of tannin and nutrient content on seed removal by scatter-hoarding rodents. We therefore, believe that these and perhaps other seed traits should interactively influence this important plant-rodent interaction. However, how selection operates on seed traits to counterbalance these competing interests/factors merits further study. Copyright © 2015 Elsevier B.V. All rights reserved.

Novel Soluble Dietary Fiber-Tannin Self-Assembled Film: A Promising Protein Protective Material.

PubMed

Song, Guo-Bin; Xu, Juan; Zheng, Hua; Feng, Ying; Zhang, Wen-Wen; Li, Kun; Ge, Shuang-shuang; Li, Kai; Zhang, Hong

2015-06-24

In this experiment, a natural promising protein protective film was fabricated through soluble dietary fiber (SDF)-tannin nanocluster self-assembly. FT-IR, XRD, and DSC tests were employed to investigate the interaction between the SDF and tannins before and after cross-linking induced by calcium ion. On the other hand, referring to the SEM and TEM results, the self-assembly process of the protein protective film could be indicated as follows: first, calcium ion, with its cross-ability, served as the "nucleus"; SDF and tannins were combined to prepare the nanoscale SDF-tannin clusters; then, the clusters were homogeneously deposited on the surface of protein to form a protective film by self-assembling hydrogen bond between tannin component of clusters as "adhesive" and protein in aqueous solutions under very mild conditions. Film thickness could also be controlled by tannin of different concentrations ranging from 114 to 1384 μm. Antibacterial test and in vitro cytotoxicity test proved that the film had a broad spectrum of antimicrobial properties and excellent cell biocompatibility, respectively, which might open up new applications in the food preservation and biomedical fields.

Presence of tannins in sorghum grains is conditioned by different natural alleles of Tannin1

PubMed Central

Wu, Yuye; Li, Xianran; Xiang, Wenwen; Zhu, Chengsong; Lin, Zhongwei; Wu, Yun; Li, Jiarui; Pandravada, Satchidanand; Ridder, Dustan D.; Bai, Guihua; Wang, Ming L.; Trick, Harold N.; Bean, Scott R.; Tuinstra, Mitchell R.; Tesso, Tesfaye T.; Yu, Jianming

2012-01-01

Sorghum, an ancient old-world cereal grass, is the dietary staple of over 500 million people in more than 30 countries in the tropics and semitropics. Its C4 photosynthesis, drought resistance, wide adaptation, and high nutritional value hold the promise to alleviate hunger in Africa. Not present in other major cereals, such as rice, wheat, and maize, condensed tannins (proanthocyanidins) in the pigmented testa of some sorghum cultivars have been implicated in reducing protein digestibility but recently have been shown to promote human health because of their high antioxidant capacity and ability to fight obesity through reduced digestion. Combining quantitative trait locus mapping, meta-quantitative trait locus fine-mapping, and association mapping, we showed that the nucleotide polymorphisms in the Tan1 gene, coding a WD40 protein, control the tannin biosynthesis in sorghum. A 1-bp G deletion in the coding region, causing a frame shift and a premature stop codon, led to a nonfunctional allele, tan1-a. Likewise, a different 10-bp insertion resulted in a second nonfunctional allele, tan1-b. Transforming the sorghum Tan1 ORF into a nontannin Arabidopsis mutant restored the tannin phenotype. In addition, reduction in nucleotide diversity from wild sorghum accessions to landraces and cultivars was found at the region that codes the highly conserved WD40 repeat domains and the C-terminal region of the protein. Genetic research in crops, coupled with nutritional and medical research, could open the possibility of producing different levels and combinations of phenolic compounds to promote human health. PMID:22699509

Manure total nitrogen flux from condensed tannin fed beef cattle

USDA-ARS?s Scientific Manuscript database

A study was conducted to determine the effects of three levels of condensed tannins fed to 27 beef feedyard steers on total nitrogen (N) flux from manure. Condensed tannins were fed at rates of 0, 0.5, and 1 percent of the daily ration on a dry matter basis. Manure and urine were collected over two ...

Phenotypic and phylogenetic characterization of ruminal tannin-tolerant bacteria.

PubMed

Nelson, K E; Thonney, M L; Woolston, T K; Zinder, S H; Pell, A N

1998-10-01

The 16S rRNA sequences and selected phenotypic characteristics were determined for six recently isolated bacteria that can tolerate high levels of hydrolyzable and condensed tannins. Bacteria were isolated from the ruminal contents of animals in different geographic locations, including Sardinian sheep (Ovis aries), Honduran and Colombian goats (Capra hircus), white-tail deer (Odocoileus virginianus) from upstate New York, and Rocky Mountain elk (Cervus elaphus nelsoni) from Oregon. Nearly complete sequences of the small-subunit rRNA genes, which were obtained by PCR amplification, cloning, and sequencing, were used for phylogenetic characterization. Comparisons of the 16S rRNA of the six isolates showed that four of the isolates were members of the genus Streptococcus and were most closely related to ruminal strains of Streptococcus bovis and the recently described organism Streptococcus gallolyticus. One of the other isolates, a gram-positive rod, clustered with the clostridia in the low-G+C-content group of gram-positive bacteria. The sixth isolate, a gram-negative rod, was a member of the family Enterobacteriaceae in the gamma subdivision of the class Proteobacteria. None of the 16S rRNA sequences of the tannin-tolerant bacteria examined was identical to the sequence of any previously described microorganism or to the sequence of any of the other organisms examined in this study. Three phylogenetically distinct groups of ruminal bacteria were isolated from four species of ruminants in Europe, North America, and South America. The presence of tannin-tolerant bacteria is not restricted by climate, geography, or host animal, although attempts to isolate tannin-tolerant bacteria from cows on low-tannin diets failed.

Phenotypic and Phylogenetic Characterization of Ruminal Tannin-Tolerant Bacteria

PubMed Central

Nelson, Karen E.; Thonney, Michael L.; Woolston, Tina K.; Zinder, Stephen H.; Pell, Alice N.

1998-01-01

The 16S rRNA sequences and selected phenotypic characteristics were determined for six recently isolated bacteria that can tolerate high levels of hydrolyzable and condensed tannins. Bacteria were isolated from the ruminal contents of animals in different geographic locations, including Sardinian sheep (Ovis aries), Honduran and Colombian goats (Capra hircus), white-tail deer (Odocoileus virginianus) from upstate New York, and Rocky Mountain elk (Cervus elaphus nelsoni) from Oregon. Nearly complete sequences of the small-subunit rRNA genes, which were obtained by PCR amplification, cloning, and sequencing, were used for phylogenetic characterization. Comparisons of the 16S rRNA of the six isolates showed that four of the isolates were members of the genus Streptococcus and were most closely related to ruminal strains of Streptococcus bovis and the recently described organism Streptococcus gallolyticus. One of the other isolates, a gram-positive rod, clustered with the clostridia in the low-G+C-content group of gram-positive bacteria. The sixth isolate, a gram-negative rod, was a member of the family Enterobacteriaceae in the gamma subdivision of the class Proteobacteria. None of the 16S rRNA sequences of the tannin-tolerant bacteria examined was identical to the sequence of any previously described microorganism or to the sequence of any of the other organisms examined in this study. Three phylogenetically distinct groups of ruminal bacteria were isolated from four species of ruminants in Europe, North America, and South America. The presence of tannin-tolerant bacteria is not restricted by climate, geography, or host animal, although attempts to isolate tannin-tolerant bacteria from cows on low-tannin diets failed. PMID:9758806

Mass spectrometric imaging of flavonoid glycosides and biflavonoids in Ginkgo biloba L.

PubMed

Beck, Sebastian; Stengel, Julia

2016-10-01

Ginkgo biloba L. is known to be rich in flavonoids and flavonoid glycosides. However, the distribution within specific plant organs (e.g. within leaves) is not known. By using HPLC-MS and MS/MS we have identified a number of previously known G. biloba flavonoid glycosides and biflavonoids from leaves. Namely, kaempferol, quercetin, isorhamnetin, myricetin, laricitrin/mearnsetin and apigenin glycosides were identified. Furthermore, biflavonoids like ginkgetin/isoginkgetin were also detected. The application of MALDI mass spectrometric imaging, enabled the compilation of concentration profiles of flavonoid glycosides and biflavonoids in G. biloba L. leaves. Both, flavonoid glycosides and biflavonoids show a distinct distribution in leaf thin sections of G. biloba L. Copyright © 2016 Elsevier Ltd. All rights reserved.

Interaction of α-synuclein with Rhus typhina tannin - Implication for Parkinson's disease.

PubMed

Sekowski, Szymon; Ionov, Maksim; Abdulladjanova, Nodira; Makhmudov, Rustam; Mavlyanov, Saidmukhtar; Milowska, Katarzyna; Bryszewska, Maria; Zamaraeva, Maria

2017-07-01

The etiology of Parkinson's disease (PD) relates to α-synuclein, a small protein with the ability to aggregate and form Lewy bodies. One of its prevention strategies is inhibition of α-synuclein oligomerization. We have investigated the interaction of α-synuclein and human serum albumin with 3,6-bis-О-di-О-galloyl-1,2,4-tri-О-galloyl-β-d-glucose (a tannin isolated from the plant Rhus typhina). Using fluorescence spectroscopy method we found that this tannin interacts strongly with α-synuclein forming complexes. Circular dichroism analysis showed a time-dependent inhibition of α-synuclein aggregation in the presence of the tannin. On the other hand, 3,6-bis-О-di-О-galloyl-1,2,4-tri-О-galloyl-β-d-glucose had a much stronger interaction with human serum albumin than α-synuclein. The calculated binding constant for tannin-protein interaction was considerably higher for albumin than α-synuclein. This tannin interacted with albumin through a "sphere of action" mechanism. The results lead to the conclusion that 3,6-bis-О-di-О-galloyl-1,2,4-tri-О-galloyl-β-d-glucose is a potent preventive compound against Parkinson's disease. However, this tannin interacts very strongly with human serum albumin, significantly reducing the bioavailability of this compound. Copyright © 2017 Elsevier B.V. All rights reserved.

Isolation and purification of condensed tannins from flamboyant tree and their antioxidant and antityrosinase activities.

PubMed

Feng, Hui-Ling; Tian, Ling; Chai, Wei-Ming; Chen, Xiao-Xin; Shi, Yan; Gao, Yu-Sen; Yan, Chong-Ling; Chen, Qing-Xi

2014-05-01

Flamboyant tree, a kind of medicinal plant, was studied as a source of condensed tannins. The antioxidant activities of the condensed tannins from the leaf, fruit, and stem bark of flamboyant tree were screened by ABTS radical and hydroxyl radical scavenging activity methods. The results indicated that these compounds possessed potent antioxidant activity. Their structures were then characterized by high-performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS) after thiolytic degradation. The results showed that the leaf condensed tannins were composed of afzelechin/epiafzelechin, catechin/epicatechin, and gallocatechin/epigallocatechin, while the fruit and stem bark condensed tannins had afzelechin/epiafzelechin and catechin/epicatechin. In addition, the condensed tannins were evaluated for their antityrosinase ability. They were found to have significant antityrosinase activity. The IC50 values were 35 ± 2.0 and 40 ± 0.5 μg/ml for the condensed tannins of fruit and stem bark, respectively. Further, fluorescence quenching and copper interacting techniques were utilized to unravel the molecular mechanisms of the inhibition. The results showed that the hydroxyl group of the condensed tannins could chelate the dicopper center of the enzyme and interact with tryptophan residues. Our studies revealed that condensed tannins might be suitable for use in food, agriculture, cosmetic, nutraceutical, and pharmaceutical applications.

How to gain insight into the polydispersity of tannins: a combined MS and LC study.

PubMed

Mouls, Laetitia; Hugouvieux, Virginie; Mazauric, Jean-Paul; Sommerer, Nicolas; Mazerolles, Gérard; Fulcrand, Hélène

2014-12-15

In the context of the potential health benefits of food polyphenols, the bioavailability of tannins (i.e. proanthocyanidins) is a major issue, which is strongly influenced by the polydispersity and the degree of polymerisation of tannins. The average degree of polymerisation (DP) of tannins is usually determined using depolymerisation methods, which do not provide any information about their polymer distribution. Moreover, it is still a challenge to characterise tannin fractions of high polydispersity and/or containing polymers of high molecular weights, due to the limit of detection of direct mass spectrometry (MS) analysis methods. In the present work, the polydispersity of several tannin fractions is investigated by two complementary methods: a MALDI-MS method and a semi-preparative sub-fractionation. Using a combination of these methods we are able to gain insight into the DP distributions of the fractions consisting of tannins of medium and high DP. Moreover combining analyses can be useful to assess and compare the DP distributions of most tannin fractions. Copyright © 2014 Elsevier Ltd. All rights reserved.

Botanical traceability of commercial tannins using the mineral profile and stable isotopes.

PubMed

Bertoldi, Daniela; Santato, Alessandro; Paolini, Mauro; Barbero, Alice; Camin, Federica; Nicolini, Giorgio; Larcher, Roberto

2014-09-01

Commercial tannins are natural polyphenolic compounds extracted from different plant tissues such as gall, the wood of different species and fruit. In the food industry they are mainly used as flavourings and food ingredients, whereas in winemaking they are classified as clarification agents for wine protein stabilisation, although colour stabilisation, metal removal, unpleasant thiol removal and rheological correction are also well-known and desired effects. Due to their particular technical properties and very different costs, the possibility of correct identification of the real botanical origin of tannins can be considered a primary target in oenology research and in fulfilling the technical and economic requirements of the wine industry. For some categories of tannins encouraging results have already been achieved by considering sugar or polyphenolic composition. For the first time this work verifies the possibility of determining the botanical origin of tannins on the basis of the mineral element profile and analysis of the (13) C/(12) C isotopic ratio. One hundred two commercial tannins originating from 10 different botanical sources (grapes, oak, gall, chestnut, fruit trees, quebracho, tea, acacia, officinal plants and tara) were analysed to determine 57 elements and the (13) C/(12) C isotopic ratio, using inductively coupled plasma mass spectrometry and isotope-ratio mass spectrometry, respectively. Forward stepwise discriminant analysis provided good discrimination between the 8 most abundant groups, with 100% correct re-classification. The model was then validated five times on subsets of 10% of the overall samples, randomly extracted, achieving satisfactory results. With a similar approach it was also possible to distinguish toasted and untoasted oak tannins as well as tannins from grape skin and grape seeds. Copyright © 2014 John Wiley & Sons, Ltd.

[Optimization of extraction process for tannins from Geranium orientali-tibeticum by supercritical CO2 method].

PubMed

Xie, Song; Tong, Zhi-Ping; Tan, Rui; Liu, Xiao-Zhen

2014-08-01

In order to optimize extraction process conditions of tannins from Geranium orientali-tibeticum by supercritical CO2, the content of tannins was determined by phosphomolybdium tungsten acid-casein reaction, with extraction pressure, extraction temper- ature and extraction time as factors, the content of tannins from extract of G. orientali-tibeticum as index, technology conditions were optimized by orthogonal test. Optimum technology conditions were as follows: extraction pressure was 25 MPa, extraction temperature was 50 °C, extracted 1.5 h. The content of tannins in extract was 12.91 mg x g(-1), extract rate was 3.67%. The method established could be used for assay the contents of tannin in G. orientali-tibeticum. The circulated extraction was an effective extraction process that was stable and feasible, and that provides a way of the extraction process conditions of tannin from G. orientali-tibeticum.

Identification of Structural Features of Condensed Tannins That Affect Protein Aggregation

PubMed Central

Ropiak, Honorata M.; Lachmann, Peter; Ramsay, Aina; Green, Rebecca J.; Mueller-Harvey, Irene

2017-01-01

A diverse panel of condensed tannins was used to resolve the confounding effects of size and subunit composition seen previously in tannin-protein interactions. Turbidimetry revealed that size in terms of mean degree of polymerisation (mDP) or average molecular weight (amw) was the most important tannin parameter. The smallest tannin with the relatively largest effect on protein aggregation had an mDP of ~7. The average size was significantly correlated with aggregation of bovine serum albumin, BSA (mDP: r = -0.916; amw: r = -0.925; p<0.01; df = 27), and gelatin (mDP: r = -0.961; amw: r = -0.981; p<0.01; df = 12). The procyanidin/prodelphinidin and cis-/trans-flavan-3-ol ratios gave no significant correlations. Tryptophan fluorescence quenching indicated that procyanidins and cis-flavan-3-ol units contributed most to the tannin interactions on the BSA surface and in the hydrophobic binding pocket (r = 0.677; p<0.05; df = 9 and r = 0.887; p<0.01; df = 9, respectively). Circular dichroism revealed that higher proportions of prodelphinidins decreased the apparent α-helix content (r = -0.941; p<0.01; df = 5) and increased the apparent β-sheet content (r = 0.916; p<0.05; df = 5) of BSA. PMID:28125657

Identification of Structural Features of Condensed Tannins That Affect Protein Aggregation.

PubMed

Ropiak, Honorata M; Lachmann, Peter; Ramsay, Aina; Green, Rebecca J; Mueller-Harvey, Irene

2017-01-01

A diverse panel of condensed tannins was used to resolve the confounding effects of size and subunit composition seen previously in tannin-protein interactions. Turbidimetry revealed that size in terms of mean degree of polymerisation (mDP) or average molecular weight (amw) was the most important tannin parameter. The smallest tannin with the relatively largest effect on protein aggregation had an mDP of ~7. The average size was significantly correlated with aggregation of bovine serum albumin, BSA (mDP: r = -0.916; amw: r = -0.925; p<0.01; df = 27), and gelatin (mDP: r = -0.961; amw: r = -0.981; p<0.01; df = 12). The procyanidin/prodelphinidin and cis-/trans-flavan-3-ol ratios gave no significant correlations. Tryptophan fluorescence quenching indicated that procyanidins and cis-flavan-3-ol units contributed most to the tannin interactions on the BSA surface and in the hydrophobic binding pocket (r = 0.677; p<0.05; df = 9 and r = 0.887; p<0.01; df = 9, respectively). Circular dichroism revealed that higher proportions of prodelphinidins decreased the apparent α-helix content (r = -0.941; p<0.01; df = 5) and increased the apparent β-sheet content (r = 0.916; p<0.05; df = 5) of BSA.

In situ analysis and structural elucidation of sainfoin (Onobrychis viciifolia) tannins for high-throughput germplasm screening.

PubMed

Gea, An; Stringano, Elisabetta; Brown, Ron H; Mueller-Harvey, Irene

2011-01-26

A rapid thiolytic degradation and cleanup procedure was developed for analyzing tannins directly in chlorophyll-containing sainfoin ( Onobrychis viciifolia ) plants. The technique proved suitable for complex tannin mixtures containing catechin, epicatechin, gallocatechin, and epigallocatechin flavan-3-ol units. The reaction time was standardized at 60 min to minimize the loss of structural information as a result of epimerization and degradation of terminal flavan-3-ol units. The results were evaluated by separate analysis of extractable and unextractable tannins, which accounted for 63.6-113.7% of the in situ plant tannins. It is of note that 70% aqueous acetone extracted tannins with a lower mean degree of polymerization (mDP) than was found for tannins analyzed in situ. Extractable tannins had between 4 and 29 lower mDP values. The method was validated by comparing results from individual and mixed sample sets. The tannin composition of different sainfoin accessions covered a range of mDP values from 16 to 83, procyanidin/prodelphinidin (PC/PD) ratios from 19.2/80.8 to 45.6/54.4, and cis/trans ratios from 74.1/25.9 to 88.0/12.0. This is the first high-throughput screening method that is suitable for analyzing condensed tannin contents and structural composition directly in green plant tissue.

Phenolic glycosides from sugar maple (Acer saccharum) bark.

PubMed

Yuan, Tao; Wan, Chunpeng; González-Sarrías, Antonio; Kandhi, Vamsikrishna; Cech, Nadja B; Seeram, Navindra P

2011-11-28

Four new phenolic glycosides, saccharumosides A-D (1-4), along with eight known phenolic glycosides, were isolated from the bark of sugar maple (Acer saccharum). The structures of 1-4 were elucidated on the basis of spectroscopic data analysis. All compounds isolated were evaluated for cytotoxicity effects against human colon tumorigenic (HCT-116 and Caco-2) and nontumorigenic (CCD-18Co) cell lines.

Phenylpropanoid-substituted procyanidins and tentatively identified procyanidin glycosides from hawthorn (Crataegus spp.).

PubMed

Sendker, Jandirk; Petereit, Frank; Lautenschläger, Marcus; Hellenbrand, Nils; Hensel, Andreas

2013-01-01

The rational use of hawthorn leafs and flowers from Crataegus spp. for declining cardiac performance is mainly due to flavon-C-glycosides and oligomeric procyanidins (OPC). From OPC-enriched extracts from different batches, a dimeric phenylpropanoid-substituted procyanidin (cinchonain II b, 1) was isolated and characterized by MS, CD, and NMR. Also the presence of higher oligomeric cinchonains (degree of polymerization 3 to 8) in hawthorn extracts was shown by a specific ultrahigh-pressure liquid chromatography-ESI-qTOF-MS method. Interestingly, strong evidence for the occurrence of oligomeric procyanidin hexosides was found by ultrahigh-pressure liquid chromatography-ESI-qTOF-MS analysis which additionally revealed the presence of peaks indicative of dimeric procyanidin hexosides by their exact mass, which were clearly distinguishable from the cinchonain II type peaks. Georg Thieme Verlag KG Stuttgart · New York.

The contribution of wine-derived monoterpene glycosides to retronasal odour during tasting.

PubMed

Parker, Mango; Black, Cory A; Barker, Alice; Pearson, Wes; Hayasaka, Yoji; Francis, I Leigh

2017-10-01

This study investigated the sensory significance of monoterpene glycosides during tasting, by retronasal perception of odorant aglycones released in-mouth. Monoterpene glycosides were isolated from Gewürztraminer and Riesling juices and wines, chemically characterised and studied using sensory time-intensity methodology, together with a synthesised monoterpene glucoside. When assessed in model wine at five times wine-like concentration, Gewürztraminer glycosides and geranyl glucoside gave significant fruity flavour, although at wine-like concentrations, or in the presence of wine volatiles, the effect was not significant. Gewürztraminer glycosides, geranyl glucoside and guaiacyl glucoside were investigated using a sensory panel (n=39), revealing large inter-individual variability, with 77% of panellists responding to at least one glycoside. The study showed for the first time that grape-derived glycosides can contribute perceptible fruity flavour, providing a means of enhancing flavour in wines, and confirms the results of previous studies that the effect is highly variable across individuals. Copyright © 2017 Elsevier Ltd. All rights reserved.

Tannin content and rate of ruminal protein degradation of legume hays

USDA-ARS?s Scientific Manuscript database

This work evaluated ruminal protein degradation rates of legume hays that varied in tannin content. Two cuttings of 5 varieties of birdsfoot trefoil, (Lotus corniculatus), selected for different tannin contents but similar NDF and CP contents, and Spredor 4 alfalfa (control) were conserved as hay. S...

Protein-Tannin Interactions of Tryptic Digests of α-Lactalbumin and Procyanidins.

PubMed

Wang, Bei; Heinonen, Marina

2017-01-11

Protein-tannin interactions on a molecular level were investigated by using a model system containing peptides of α-lactalbumin and berry tannins (procyanidins). Oxidation of isolated tryptic peptide LDQWLCEK (m/z 1034) with procyanidin B2 or procyanidin fraction (PF) isolated from aronia juice was monitored by LC-ESI-MS. Procyanidin B2 and PF showed radical scavenging activities toward oxidation of the peptide with the peptide also preventing procyanidin B2 from degradation. Oxidation enhanced the cleavage of peptide between tryptophan and glutamine. Interaction products arising from WLCEK or WLCE residue and degradation product of procyanidin B2 were also identified using both size exclusion chromatography and LC-MS. Tryptophan and lysine were the amino acids most prone to interact with procyanidin B2. The study shows that protein-tannin interaction takes place during oxidation leading to both degradation of the parent compounds and formation of interaction products. This may in turn affect the quality of protein and tannin containing food.

Analysis of supercooling activity of tannin-related polyphenols.

PubMed

Kuwabara, Chikako; Wang, Donghui; Endoh, Keita; Fukushi, Yukiharu; Arakawa, Keita; Fujikawa, Seizo

2013-08-01

Based on the discovery of novel supercooling-promoting hydrolyzable gallotannins from deep supercooling xylem parenchyma cells (XPCs) in Katsura tree (see Wang et al. (2012) [38]), supercooling capability of a wide variety of tannin-related polyphenols (TRPs) was examined in order to find more effective supercooling-promoting substances for their applications. The TRPs examined were single compounds including six kinds of hydrolyzable tannins, 11 kinds of catechin derivatives, two kinds of structural analogs of catechin and six kinds of phenolcarboxylic acid derivatives, 11 kinds of polyphenol mixtures and five kinds of crude plant tannin extracts. The effects of these TRPs on freezing were examined by droplet freezing assays using various solutions containing different kinds of identified ice nucleators such as the ice nucleation bacterium (INB) Erwinia ananas, the INB Xanthomonas campestris, silver iodide and phloroglucinol as well as a solution containing only unintentionally included unidentified airborne ice nucleators. Among the 41 kinds of TRPs examined, all of the hydrolyzable tannins, catechin derivatives, polyphenol mixtures and crude plant tannin extracts as well as a few structural analogs of catechin and phenolcarboxylic acid derivatives exhibited supercooling-promoting activity (SCA) with significant differences (p>0.05) from at least one of the solutions containing different kinds of ice nucleators. It should be noted that there were no TRPs exhibiting ice nucleation-enhancing activity (INA) in all solutions containing identified ice nucleators, whereas there were many TRPs exhibiting INA with significant differences in solutions containing unidentified ice nucleators alone. An emulsion freezing assay confirmed that these TRPs did not essentially affect homogeneous ice nucleation temperatures. It is thought that not only SCA but also INA in the TRPs are produced by interactions with heterogeneous ice nucleators, not by direct interaction with water

Pre-fermentation addition of grape tannin increases the varietal thiols content in wine.

PubMed

Larcher, Roberto; Tonidandel, Loris; Román Villegas, Tomás; Nardin, Tiziana; Fedrizzi, Bruno; Nicolini, Giorgio

2015-01-01

The recent finding that grape tannin may contain significant amount of S-glutathionylated (GSH-3MH) and S-cysteinylated (Cys-3MH) precursors of the varietal thiols 3-mercapto-1-hexanol and 3-mercaptohexyl acetate, characteristic of Sauvignon blanc wines, offers new opportunities for enhancing the tropical aroma in fermented beverages. In this study this new hypothesis was investigated: Müller Thurgau (17 samples) and Sauvignon blanc (15 samples) grapes were fermented with and without addition of a selected grape tannin. As expected, the tannin-added juices were higher in precursors, and they produced wines with increased free thiols. Preliminary informal sensory tests confirmed that in particular the Sauvignon wines produced with the tannin addition were often richer with increased "fruity/green" notes than the corresponding reference wines. This outcome confirms that grape tannin addition prior to fermentation can fortify the level of these compounds. Copyright © 2014 Elsevier Ltd. All rights reserved.

Relationship between red wine grades and phenolics. 1. Tannin and total phenolics concentrations.

PubMed

Mercurio, Meagan D; Dambergs, Robert G; Cozzolino, Daniel; Herderich, Markus J; Smith, Paul A

2010-12-08

Measuring chemical composition is a common approach to support decisions about allocating foods and beverages to grades related to market value. Red wine is a particularly complex beverage, and multiple compositional attributes are needed to account for its sensory properties, including measurement of key phenolic components such as anthocyanins, total phenolics, and tannin, which are related to color and astringency. Color has been shown to relate positively to red wine grade; however, little research has been presented that explores the relationship between astringency-related components such as total phenolic or tannin concentration and wine grade. The aim of this research has been to investigate the relationship between the wine grade allocations of commercial wineries and total phenolic and tannin concentrations, respectively, in Australian Shiraz and Cabernet Sauvignon wines. Total phenolic and tannin concentrations were determined using the methyl cellulose precipitable (MCP) tannin assay and then compared to wine grade allocations made by winemaker panels during the companies' postvintage allocation process. Data were collected from wines produced by one Australian wine company over the 2005, 2006, and 2007 vintages and by a further two companies in 2007 (total wines = 1643). Statistical analysis revealed a positive trend toward higher wine grade allocation and wines that had higher concentrations of both total phenolics and tannin, respectively. This research demonstrates that for these companies, in general, Cabernet Sauvignon and Shiraz wines allocated to higher market value grades have higher total phenolics and higher tannin concentrations and suggests that these compositional parameters should be considered in the development of future multiparameter decision support systems for relevant commercial red wine grading processes. In addition, both tannin and total phenolics would ideally be included because although, in general, a positive relationship

Constituent and induced tannin accumulations in roots of loblolly pines

Treesearch

Charles H. Walkinshaw

1999-01-01

Loblolly pine (Pinus taeda L [L.]) has become the most important source of wood fiber in the Southern United States. This tree is an excellent competitor and recovers well from a variety of adverse conditions. The author presents a histological study of tannin in pine roots to measure tannin abundance as a primary trait to evaluate root health at the...

Ethanol Concentration Influences the Mechanisms of Wine Tannin Interactions with Poly(L-proline) in Model Wine.

PubMed

McRae, Jacqui M; Ziora, Zyta M; Kassara, Stella; Cooper, Matthew A; Smith, Paul A

2015-05-06

Changes in ethanol concentration influence red wine astringency, and yet the effect of ethanol on wine tannin-salivary protein interactions is not well understood. Isothermal titration calorimetry (ITC) was used to measure the binding strength between the model salivary protein, poly(L-proline) (PLP) and a range of wine tannins (tannin fractions from a 3- and a 7-year old Cabernet Sauvignon wine) across different ethanol concentrations (5, 10, 15, and 40% v/v). Tannin-PLP interactions were stronger at 5% ethanol than at 40% ethanol. The mechanism of interaction changed for most tannin samples across the wine-like ethanol range (10-15%) from a combination of hydrophobic and hydrogen binding at 10% ethanol to only hydrogen binding at 15% ethanol. These results indicate that ethanol concentration can influence the mechanisms of wine tannin-protein interactions and that the previously reported decrease in wine astringency with increasing alcohol may, in part, relate to a decrease tannin-protein interaction strength.

Green synthesis of silver nanoparticles using tannins

NASA Astrophysics Data System (ADS)

Raja, Pandian Bothi; Rahim, Afidah Abdul; Qureshi, Ahmad Kaleem; Awang, Khalijah

2014-09-01

Colloidal silver nanoparticles were prepared by rapid green synthesis using different tannin sources as reducing agent viz. chestnut (CN), mangrove (MG) and quebracho (QB). The aqueous silver ions when exposed to CN, MG and QB tannins were reduced which resulted in formation of silver nanoparticles. The resultant silver nanoparticles were characterized using UV-Visible, X-ray diffraction (XRD), scanning electron microscopy (SEM/EDX), and transmission electron microscopy (TEM) techniques. Furthermore, the possible mechanism of nanoparticles synthesis was also derived using FT-IR analysis. Spectroscopy analysis revealed that the synthesized nanoparticles were within 30 to 75 nm in size, while XRD results showed that nanoparticles formed were crystalline with face centered cubic geometry.

Prenylated flavonol glycosides Epimedium grandiflorum: Cytotoxicity and evaluation against inflammation and metabolic disorders

USDA-ARS?s Scientific Manuscript database

Two new prenylated flavonol glycosides, epimedigrandiosides A and B (1 and 2), and 28 previously known compounds including prenylated flavonol derivatives, flavonol glycoside, megastigmanes, phenyl alkanoids, sesquiterpenoid glycoside, lignan, and hexene glucoside were isolated from the methanol ext...

Impact of condensed tannin size as individual and mixed polymers on bovine serum albumin precipitation.

PubMed

Harbertson, James F; Kilmister, Rachel L; Kelm, Mark A; Downey, Mark O

2014-10-01

Condensed tannins composed of epicatechin from monomer to octamer were isolated from cacao (Theobroma cacao, L.) seeds and added to bovine serum albumin (BSA) individually and combined as mixtures. When added to excess BSA the amount of tannin precipitated increased with tannin size. The amount of tannin required to precipitate BSA varied among the polymers with the trimer requiring the most to precipitate BSA (1000 μg) and octamer the least (50 μg). The efficacy of condensed tannins for protein precipitation increased with increased degree of polymerisation (or size) from trimers to octamers (monomers and dimers did not precipitate BSA), while mixtures of two sizes primarily had an additive effect. This study demonstrates that astringent perception is likely to increase with increasing polymer size. Further research to expand our understanding of astringent perception and its correlation with protein precipitation would benefit from sensory analysis of condensed tannins across a range of polymer sizes. Copyright © 2014 Elsevier Ltd. All rights reserved.

Rapid screening of tannase producing microbes by using natural tannin.

PubMed

Jana, Arijit; Maity, Chiranjit; Halder, Suman Kumar; Pati, Bikas Ranjan; Mondal, Keshab Chandra; Mohapatra, Pradeep Kumar Das

2012-07-01

Use of natural tannin in the screening of tannase producing microbes is really promising. The present work describes about the possibility and integrity of the newly formulated method over the previously reported methods. Tannin isolated from Terminalia belerica Roxb. (Bahera) was used to differentiate between tanninolytic and nontanninolytic microbes. The method is simple, sensitive and superior for the rapid screening and isolation of tannase-producing microbes.

Climate Influences the Content and Chemical Composition of Foliar Tannins in Green and Senesced Tissues of Quercus rubra

PubMed Central

Top, Sara M.; Preston, Caroline M.; Dukes, Jeffrey S.; Tharayil, Nishanth

2017-01-01

Environmental stresses not only influence production of plant metabolites but could also modify their resorption during leaf senescence. The production-resorption dynamics of polyphenolic tannins, a class of defense compound whose ecological role extends beyond tissue senescence, could amplify the influence of climate on ecosystem processes. We studied the quantity, chemical composition, and tissue-association of tannins in green and freshly-senesced leaves of Quercus rubra exposed to different temperature (Warming and No Warming) and precipitation treatments (Dry, Ambient, Wet) at the Boston-Area Climate Experiment (BACE) in Massachusetts, USA. Climate influenced not only the quantity of tannins, but also their molecular composition and cell-wall associations. Irrespective of climatic treatments, tannin composition in Q. rubra was dominated by condensed tannins (CTs, proanthocyanidins). When exposed to Dry and Ambient*Warm conditions, Q. rubra produced higher quantities of tannins that were less polymerized. In contrast, under favorable conditions (Wet), tannins were produced in lower quantities, but the CTs were more polymerized. Further, even as the overall tissue tannin content declined, the content of hydrolysable tannins (HTs) increased under Wet treatments. The molecular composition of tannins influenced their content in senesced litter. Compared to the green leaves, the content of HTs decreased in senesced leaves across treatments, whereas the CT content was similar between green and senesced leaves in Wet treatments that produced more polymerized tannins. The content of total tannins in senesced leaves was higher in Warming treatments under both dry and ambient precipitation treatments. Our results suggest that, though climate directly influenced the production of tannins in green tissues (and similar patterns were observed in the senesced tissue), the influence of climate on tannin content of senesced tissue was partly mediated by the effect on the

The Effects of Pre-Fermentative Addition of Oenological Tannins on Wine Components and Sensorial Qualities of Red Wine.

PubMed

Chen, Kai; Escott, Carlos; Loira, Iris; Del Fresno, Juan Manuel; Morata, Antonio; Tesfaye, Wendu; Calderon, Fernando; Benito, Santiago; Suárez-Lepe, Jose Antonio

2016-10-31

Today in the wine industry, oenological tannins are widely used to improve wine quality and prevent oxidation in wine aging. With the development of tannin products, new oenological tannins are developed with many specific functions, such as modifying antioxidant effect, colour stabilization and aroma modifications. The aim of this work is to investigate effects of pre-fermentative addition of oenological tannins on wine colour, anthocyanins, volatile compounds and sensorial properties. In this case, Syrah juice was extracted with classic flash thermovinification from fresh must in order to release more colour and tannins. Three types of oenological tannins, which are, respectively, derived from grape skin, seed ( Vitis vinifera ) and French oak ( Quercus robur and Querrus petraea ), were selected to carry out the experiments with seven treatments. Results indicated that tannin treatments significantly improved wine aroma complexity and sensorial properties. However, the concentration of some stable pigments such as Vitisin A, Vitisin A-Ac and Vitisin B was negatively affected by tannin additions. Nevertheless, by means of cluster analysis and principal component analysis, it was observed that higher alcohols were significantly promoted by grape seed tannin while most anthocyanins can be improved by addition of grape tannins. In conclusion, low amount of oenological tannin derived from grape seed is a promising method to be applied especially for young red wine making.

Sealing and anti-corrosive action of tannin rust converters

DOE Office of Scientific and Technical Information (OSTI.GOV)

Gust, J.; Bobrowicz, J.

1993-01-01

A possibility of the application of mercury porosimetry in the investigation on porosity in corrosion products of the carbon steel along with the degree of sealing by the use of tannin rust converters is presented. The effect of the atmospheric humidity on the rust conversion including the time of that conversion on the degree of rust sealing is discussed. The results of the corrosion investigation of carbon steel covered with a layer of the rust converted with tannin-containing agents are presented.

Effect of the prefermentative addition of five enological tannins on anthocyanins and color in red wines.

PubMed

Liu, Yan-Xia; Liang, Na-Na; Wang, Jun; Pan, Qiu-Hong; Duan, Chang-Qing

2013-01-01

The effects of prefermentation addition of 5 exogenous tannins with different-origin anthocyanins and color characteristics were investigated in "Cabernet Sauvignon wines" at the end of alcoholic fermentation and the end of malolactic fermentation, and after 6 mo and 9 mo of bottle aging, respectively. The results showed that the application of GSKT2 could significantly retard the degradation of most anthocyanins in the process of alcoholic fermentation and the decrease of some pyranoanthocyanins during the subsequent 3 stages, thus causing more yellowness of wine in comparison with the control. Three other condensed tannins, GSKT1, QUET, and GSET, had a positive impact only on several anthocyanin components. Four condensed tannins all contributed to more redness, suggesting that the action mechanism might be to protect wine against oxidation or contribute to form copigmented anthocyanidins, or polymeric pigments. The application of FOLT (hydrolysable tannin) did not produce any influence on wine redness even after 9 mo of bottle aging. This work provides some reasons for the reasonable application of tannin additives. The prefermentative application of condensed tannins overall could protect some pigment components from degradation and enhance wine redness. Tannin additives with different origins have different effectiveness. The tannin additive obtained from grape skins, like GSKT2, could produce significant promotion on both redness and yellowness in wine. The prefermentation addition of hydroxylase tannin like FOLT seems not to have a significant effect on wine color. © 2012 Institute of Food Technologists®

Hydrolyzable tannins of tamaricaceous plants. III. Hellinoyl- and macrocyclic-type ellagitannins from Tamarix nilotica.

PubMed

Orabi, Mohamed A A; Taniguchi, Shoko; Yoshimura, Morio; Yoshida, Takashi; Kishino, Kaori; Sakagami, Hiroshi; Hatano, Tsutomu

2010-05-28

Three new hellinoyl-type ellagitannins, nilotinins M4 (7), D7 (8), and D8 (9), and a new macrocyclic-type, nilotinin D9 (10), together with eight known tannins, hirtellins B (2), C (11), and F (12), isohirtellin C (13), tamarixinin A (3), tellimagrandins I and II, and 1,2,6-tri-O-galloyl-beta-d-glucose (14), were isolated from an aqueous acetone extract of Tamarix nilotica dried leaves. Nilotinin M4 (7) is a monomeric tannin possessing a hellinoyl moiety. The structure of 8 demonstrated replacement of one of the HHDP groups at the glucose core O-4/O-6 in ordinary dimeric tannins with a galloyl moiety at O-6. This is a new structural feature among the tamaricaceous ellagitannins. On the basis of the results, reported spectroscopic assignments for 2, 3, and the macrocyclic tannins 11-13 were revised. Unusual shifts in the NMR spectra of these macrocyclic tannins are also discussed in relation to their conformations. Several tannins isolated from T. nilotica were assessed for possible cytotoxic activity against four human tumor cell lines, and nilotinin D8 (9) and hirtellin A (1) showed high cytotoxic effects.

Degradation of tannins in spent coffee grounds by Pleurotus sajor-caju.

PubMed

Wong, Y S; Wang, X

1991-09-01

Pleurotus sajor-caju PL27, a white rot fungus, degraded up to 87% of the tannins in spent coffee grounds as a solid substrate over 32 days. Degradation of tannins was enhanced if potato and dextrose were included. The potential nutritive value of the substrate as animal feed may be improved by this process.

Incorporation of sup 14 C from ( sup 14 C)phenylalanine into condensed tannin of sorghum grain

DOE Office of Scientific and Technical Information (OSTI.GOV)

Reddy, V.; Butler, L.G.

A procedure is described for obtaining condensed tannin from sorghum (Sorghum bicolor (L.) Moench) seeds metabolically labeled from ({sup 14}C)phenylalanine. The ({sup 14}C)tannin should be useful in determining the metabolic fate of dietary condensed tannin.

Wine and grape tannin interactions with salivary proteins and their impact on astringency: a review of current research.

PubMed

McRae, Jacqui M; Kennedy, James A

2011-03-11

Astringency is an important characteristic of red wine quality. The sensation is generally thought to be produced by the interaction of wine tannins with salivary proteins and the subsequent aggregation and precipitation of protein-tannin complexes. The importance of wine astringency for marketability has led to a wealth of research on the causes of astringency and how tannins impact the quality of the sensation, particularly with respect to tannin structure. Ultimately, the understanding of how tannin structure impacts astringency will allow the controlled manipulation of tannins via such methods as micro-oxygenation or fining to improve the quality of wines.

Proof that green tea tannin suppresses the increase in the blood methylguanidine level associated with renal failure.

PubMed

Yokozawa, T; Dong, E; Oura, H

1997-02-01

The effects of a green tea tannin mixture and its individual tannin components on methylguanidine were examined in rats with renal failure. The green tea tannin mixture caused a dose-dependent decrease in methylguanidine, a substance which accumulates in the blood with the progression of renal failure. Among individual tannin components, the effect was most conspicuous with (-)-epigallocatechin 3-O-gallate and (-)-epicatechin 3-O-gallate, while other components not linked to gallic acid showed only weak effects. Thus, the effect on methylguanidine was found to vary among different types of tannin.

Rapid screening of tannase producing microbes by using natural tannin

PubMed Central

Jana, Arijit; Maity, Chiranjit; Halder, Suman Kumar; Pati, Bikas Ranjan; Mondal, Keshab Chandra; Mohapatra, Pradeep Kumar Das

2012-01-01

Use of natural tannin in the screening of tannase producing microbes is really promising. The present work describes about the possibility and integrity of the newly formulated method over the previously reported methods. Tannin isolated from Terminalia belerica Roxb. (Bahera) was used to differentiate between tanninolytic and nontanninolytic microbes. The method is simple, sensitive and superior for the rapid screening and isolation of tannase-producing microbes. PMID:24031931

Diterpenoid glycosides from the bitter fern Gleichenia quadripartita.

PubMed

Socolsky, Cecilia; Asakawa, Yoshinori; Bardón, Alicia

2007-12-01

Fifteen new diterpenoid glycosides (1a-n, 2) were isolated from an Argentine collection of the bitter fern Gleichenia quadripartita along with the known flavonoid glycoside afzelin. Structure elucidation was accomplished by 1D and 2D NMR spectroscopy and by high-resolution MS analyses. In addition, X-ray crystallographic analysis of a monocrystal of 1a as well as chemical derivatization of 1h and 1m were performed to confirm their structures.

[Determination of total tannins in the roots, branches, leaves and pericarps of Juglans mandshurica].

PubMed

Wang, Tianmin; Sun, Xiaoli; Peng, Xue; Zhai, Yanjun; Chu, Zhengyun; Zhang, Hui; Kang, Tingguo; Chen, Hubiao

2011-01-01

The roots, barks, branches and pericarps of Juglans mandshurica were used as folk medicine in China and reputed for its treatment of several cancers, such as gastric cancer, liver cancer and leukemia. The extracts of the roots, branches, leaves and pericarps of J. mandshurica have been experimentally proved to show anti-tumor activities. Tannins, which exhibited antioxidant and anti-tumor activities, were the main constituents in J. mandshurica. In this paper, a simple spectrophotometric method was developed for the determination of total tannins in the roots, branches, leaves and pericarps of J. mandshurica collected in Dalian and Anshan of Liaoning Province. Gallic acid was used as standard compound and the content of total tannins was calculated as gallic acid equivalent. As a result of the method validation, a good linearity (r = 0.9997, n = 5) and a high recovery of gallic acid (99.02%, RSD 3.7%, n = 9) was achieved. Eight samples including four parts of J. mandshurica collected in two places were analyzed for their total tannins with the established method. In the corresponding parts of J. mandshurica, except the pericarps, the contents of total tannins showed no significant difference between samples collected in Dalian and Anshan, while the content of total tannins in different parts of J. mandshurica were significantly different. The average content of total tannins in the roots, branches, leaves and pericarps of samples collected in Dalian and Anshan was 45.66, 23.40, 58.24, 3.58 mg g(-1), respectively.

Composition and biological activities of hydrolyzable tannins of fruits of Phyllanthus emblica.

PubMed

Yang, Baoru; Liu, Pengzhan

2014-01-22

Fruits of emblic leafflower have been used as food and traditional medicine in Asia. A wide range of biological activities have been shown in modern research suggesting potential of the fruits as healthy food and raw material for bioactive ingredients of food. Hydrolyzable tannins are among the major bioactive components of the fruits. Mucic acid gallate, mucic acid lactone gallate, monogalloylglucose, gallic acid, digalloylglucose, putranjivain A, galloyl-HHDP-glucose, elaeocarpusin, and chebulagic acid are the most abundant hydrolyzable tannins. The compositional profiles of tannins in the fruits vary depending on the cultivars as well as ripening stages. Fruits and tannin-rich extracts of fruits have shown antidiabetic, antimicrobial, anti-inflammatory, and immune-regulating activities in vitro and in animal studies. The fruits and fruit extracts have manifested protective effects on organs/tissues from damages induced by chemicals, stresses, and aging in animal models. The fruits and fruit extracts have potential in inhibiting the growth of cancer cells and reducing DNA damage induced by chemicals and radiation. Antioxidative activities are likely among the mechanisms of the biological activities and physiological effects. Human intervention/clinical studies are needed to investigate the bioavailability and metabolism of the tannins and to substantiate the health benefits in humans. Emblic leafflower may be a potential raw material for natural food preservatives.

Persimmon-derived tannin has bacteriostatic and anti-inflammatory activity in a murine model of Mycobacterium avium complex (MAC) disease.

PubMed

Matsumura, Yoko; Kitabatake, Masahiro; Ouji-Sageshima, Noriko; Yasui, Satsuki; Mochida, Naoko; Nakano, Ryuichi; Kasahara, Kei; Tomoda, Koichi; Yano, Hisakazu; Kayano, Shin-Ichi; Ito, Toshihiro

2017-01-01

Nontuberculous mycobacteria (NTM), including Mycobacterium avium complex (MAC), cause opportunistic chronic pulmonary infections. Notably, MAC susceptibility is regulated by various factors, including the host immune system. Persimmon (Ebenaceae Diospyros kaki Thunb.) tannin is a condensed tannin composed of a polymer of catechin groups. It is well known that condensed tannins have high antioxidant activity and bacteriostatic properties. However, it is hypothesized that condensed tannins might need to be digested and/or fermented into smaller molecules in vivo prior to being absorbed into the body to perform beneficial functions. In this study, we evaluated the effects of soluble persimmon-derived tannins on opportunistic MAC disease. Soluble tannins were hydrolyzed and evaluated by the oxygen radical absorbance capacity (ORAC) method. The ORAC value of soluble tannin hydrolysate was approximately five times greater than that of soluble tannin powder. In addition, soluble tannin hydrolysate exhibited high bacteriostatic activity against MAC in vitro. Furthermore, in an in vivo study, MAC infected mice fed a soluble tannin-containing diet showed significantly higher anti-bacterial activity against MAC and less pulmonary granuloma formation compared with those fed a control diet. Tumor necrosis factor α and inducible nitric oxide synthase levels were significantly lower in lungs of the soluble tannin diet group compared with the control diet group. Moreover, proinflammatory cytokines induced by MAC stimulation of bone marrow-derived macrophages were significantly decreased by addition of soluble tannin hydrolysate. These data suggest that soluble tannin from persimmons might attenuate the pathogenesis of pulmonary NTM infection.

Persimmon-derived tannin has bacteriostatic and anti-inflammatory activity in a murine model of Mycobacterium avium complex (MAC) disease

PubMed Central

Matsumura, Yoko; Kitabatake, Masahiro; Ouji-Sageshima, Noriko; Yasui, Satsuki; Mochida, Naoko; Nakano, Ryuichi; Kasahara, Kei; Tomoda, Koichi; Yano, Hisakazu; Kayano, Shin-ichi

2017-01-01

Nontuberculous mycobacteria (NTM), including Mycobacterium avium complex (MAC), cause opportunistic chronic pulmonary infections. Notably, MAC susceptibility is regulated by various factors, including the host immune system. Persimmon (Ebenaceae Diospyros kaki Thunb.) tannin is a condensed tannin composed of a polymer of catechin groups. It is well known that condensed tannins have high antioxidant activity and bacteriostatic properties. However, it is hypothesized that condensed tannins might need to be digested and/or fermented into smaller molecules in vivo prior to being absorbed into the body to perform beneficial functions. In this study, we evaluated the effects of soluble persimmon-derived tannins on opportunistic MAC disease. Soluble tannins were hydrolyzed and evaluated by the oxygen radical absorbance capacity (ORAC) method. The ORAC value of soluble tannin hydrolysate was approximately five times greater than that of soluble tannin powder. In addition, soluble tannin hydrolysate exhibited high bacteriostatic activity against MAC in vitro. Furthermore, in an in vivo study, MAC infected mice fed a soluble tannin-containing diet showed significantly higher anti-bacterial activity against MAC and less pulmonary granuloma formation compared with those fed a control diet. Tumor necrosis factor α and inducible nitric oxide synthase levels were significantly lower in lungs of the soluble tannin diet group compared with the control diet group. Moreover, proinflammatory cytokines induced by MAC stimulation of bone marrow-derived macrophages were significantly decreased by addition of soluble tannin hydrolysate. These data suggest that soluble tannin from persimmons might attenuate the pathogenesis of pulmonary NTM infection. PMID:28827842

[Comparative study of different extraction methods and assays of tannins in some pteridophytes].

PubMed

Laurent, S

1975-10-01

Various processes of extraction and quantitative analysis of a condensed tannin in a plant extract, which also includes some chlorogenic acids, have been examined. 60% methanol, at 50 degrees C, proved the most efficient extraction solvent. Several methods of analysis have been tried. The measure of the colour intensity obtained by the action of sulphuric vanilline on flavanols cannot be used because it depends on the tannin condensation stage. It is impossible to separate tannin from chlorogenic acids using the methods of adsorption by skin or nylon powders, or precipitation by polyvinylpyrrolidone. Only paper chromatography, followed by the distinct elution of the various phenolic compounds, allows the tannin evaluation by subtraction; but owing to the variability of the results, many more experiments are necessary. Some other processes are being studied.

Influence of wine pectic polysaccharides on the interactions between condensed tannins and salivary proteins.

PubMed

Carvalho, Elisabete; Mateus, Nuno; Plet, Benoit; Pianet, Isabelle; Dufourc, Erick; De Freitas, Victor

2006-11-15

Alpha-amylase, a major human salivary protein, and IB8c, a representative of the proline-rich proteins, were obtained by isolation from saliva and by solid-phase synthesis, respectively. The interactions between these proteins and condensed tannins isolated from grape seeds were studied at different protein and tannin concentrations by measuring their aggregation. Pectic polysaccharides were isolated from wine, and their effect on protein tannin aggregation was assessed. The results presented in this study showed that the most acidic fractions of arabinogalactan proteins have the ability to inhibit the formation of aggregates between the grape seed tannins and the two different salivary proteins. Rhamnogalacturonan II has the same ability toward alpha-amylase but not IB8c under the conditions of the present study. Polysaccharides show effects at concentrations at which they are present in wine, which could mean an influence in wine astringency. The interaction between condensed tannins and alpha-amylase is differently affected by ionic strength when compared with IB8c.

Heavy Metal-Free Tannin from Bark for Sustainable Energy Storage.

PubMed

Mukhopadhyay, Alolika; Jiao, Yucong; Katahira, Rui; Ciesielski, Peter N; Himmel, Michael; Zhu, Hongli

2017-12-13

A novel renewable cathode made from earth abundant, low-cost materials can contribute to the intermittent storage needs of renewable energy-based society. In this work, we report for the first-time tannin from Nature as a cathode material. Our approach exploits the charge storage mechanism of the redox active quinone moiety. Tannins extracted from tree bark using environmental friendly aqueous solvents have the highest phenol content (5.56 mol g -1 ) among all the natural phenolic biopolymers, 5000 times higher than lignin. Tannins coupled with a conductive polymer polypyrrole acquire high specific capacitance values of 370 F g -1 at 0.5 A g -1 as well as excellent rate performance of 196 F g -1 at 25 A g -1 . Additionally, we employed carbonized wood as an electrode substrate to produce a sustainable electrochemical device with dramatically improved performance compared to conventional devices. The high surface area provided by the well-aligned, cellular porosity of wood-derived substrate combined with the high mobility of ions and electrons in the carbonized cell walls and deposited tannin can achieve an areal capacitance of 4.6 F cm -2 at 1 mA cm -2 , which is 1.5 times higher than activated wood carbon.

Response of γδ T cells to plant-derived tannins

PubMed Central

Holderness, Jeff; Hedges, Jodi F.; Daughenbaugh, Katie; Kimmel, Emily; Graff, Jill; Freedman, Brett; Jutila, Mark A.

2008-01-01

Many pharmaceutical drugs are isolated from plants used in traditional medicines. Through screening plant extracts, both traditional medicines and compound libraries, new pharmaceutical drugs continue to be identified. Currently, two plant-derived agonists for γδ T cells are described. These plant-derived agonists impart innate effector functions upon distinct γδ T cell subsets. Plant tannins represent one class of γδ T cell agonist and preferentially activate the mucosal population. Mucosal γδ T cells function to modulate tissue immune responses and induce epithelium repair. Select tannins, isolated from apple peel, rapidly induce immune gene transcription in γδ T cells, leading to cytokine production and increased responsiveness to secondary signals. Activity of these tannin preparations tracks to the procyanidin fraction, with the procyanidin trimer (C1) having the most robust activity defined to date. The response to the procyanidins is evolutionarily conserved in that responses are seen with human, bovine, and murine γδ T cells. Procyanidin-induced responses described in this review likely account for the expansion of mucosal γδ T cells seen in mice and rats fed soluble extracts of tannins. Procyanidins may represent a novel approach for treatment of tissue damage, chronic infection, and autoimmune therpies. PMID:19166386

Heavy Metal-Free Tannin from Bark for Sustainable Energy Storage

DOE Office of Scientific and Technical Information (OSTI.GOV)

Mukhopadhyay, Alolika; Jiao, Yucong; Katahira, Rui

A novel renewable cathode made from earth abundant, low-cost materials can contribute to the intermittent storage needs of renewable energy-based society. In this work, we report for the first-time tannin from Nature as a cathode material. Our approach exploits the charge storage mechanism of the redox active quinone moiety. Tannins extracted from tree bark using environmental friendly aqueous solvents have the highest phenol content (5.56 mol g -1) among all the natural phenolic biopolymers, 5000 times higher than lignin. Tannins coupled with a conductive polymer polypyrrole acquire high specific capacitance values of 370 F g -1 at 0.5 A gmore » -1 as well as excellent rate performance of 196 F g -1 at 25 A g -1. Additionally, we employed carbonized wood as an electrode substrate to produce a sustainable electrochemical device with dramatically improved performance compared to conventional devices. The high surface area provided by the well-aligned, cellular porosity of wood-derived substrate combined with the high mobility of ions and electrons in the carbonized cell walls and deposited tannin can achieve an areal capacitance of 4.6 F cm -2 at 1 mA cm -2, which is 1.5 times higher than activated wood carbon.« less

Heavy Metal-Free Tannin from Bark for Sustainable Energy Storage

DOE PAGES

Mukhopadhyay, Alolika; Jiao, Yucong; Katahira, Rui; ...

2017-11-30

A novel renewable cathode made from earth abundant, low-cost materials can contribute to the intermittent storage needs of renewable energy-based society. In this work, we report for the first-time tannin from Nature as a cathode material. Our approach exploits the charge storage mechanism of the redox active quinone moiety. Tannins extracted from tree bark using environmental friendly aqueous solvents have the highest phenol content (5.56 mol g -1) among all the natural phenolic biopolymers, 5000 times higher than lignin. Tannins coupled with a conductive polymer polypyrrole acquire high specific capacitance values of 370 F g -1 at 0.5 A gmore » -1 as well as excellent rate performance of 196 F g -1 at 25 A g -1. Additionally, we employed carbonized wood as an electrode substrate to produce a sustainable electrochemical device with dramatically improved performance compared to conventional devices. The high surface area provided by the well-aligned, cellular porosity of wood-derived substrate combined with the high mobility of ions and electrons in the carbonized cell walls and deposited tannin can achieve an areal capacitance of 4.6 F cm -2 at 1 mA cm -2, which is 1.5 times higher than activated wood carbon.« less

Characterization of condensed tannins and carbohydrates in hot water bark extracts of European softwood species.

PubMed

Bianchi, Sauro; Kroslakova, Ivana; Janzon, Ron; Mayer, Ingo; Saake, Bodo; Pichelin, Frédéric

2015-12-01

Condensed tannins extracted from European softwood bark are recognized as alternatives to synthetic phenolics. The extraction is generally performed in hot water, leading to simultaneous extraction of other bark constituents such as carbohydrates, phenolic monomers and salts. Characterization of the extract's composition and identification of the extracted tannins' molecular structure are needed to better identify potential applications. Bark from Silver fir (Abies alba [Mill.]), European larch (Larix decidua [Mill.]), Norway spruce (Picea abies [Karst.]), Douglas fir (Pseudotsuga menziesii [Mirb.]) and Scots pine (Pinus sylvestris [L.]) were extracted in water at 60°C. The amounts of phenolic monomers, condensed tannins, carbohydrates, and inorganic compounds in the extract were determined. The molecular structures of condensed tannins and carbohydrates were also investigated (HPLC-UV combined with thiolysis, MALDI-TOF mass spectrometry, anion exchange chromatography). Distinct extract compositions and tannin structures were found in each of the analysed species. Procyanidins were the most ubiquitous tannins. The presence of phenolic glucosides in the tannin oligomers was suggested. Polysaccharides such as arabinans, arabinogalactans and glucans represented an important fraction of all extracts. Compared to traditionally used species (Mimosa and Quebracho) higher viscosities as well as faster chemical reactivities are expected in the analysed species. The most promising species for a bark tannin extraction was found to be larch, while the least encouraging results were detected in pine. A better knowledge of the interaction between the various extracted compounds is deemed an important matter for investigation in the context of industrial applications of such extracts. Copyright © 2015 Elsevier Ltd. All rights reserved.

Synthesis and anti-fungal activity of acetylated glycosides of 1,4-naphthoquinone

DOE Office of Scientific and Technical Information (OSTI.GOV)

Polonik, S.G.; Tolkach, A.M.; Uvarova, N.I.

1986-12-01

The authors synthesize a series of glycoside derivatives of 1,4-naphthoquinones (VIII-XXII) and study their anti-fungal activity in a search for more effective preparations for the medical and food industries. The structures of the newly prepared glycosides were verified by IR and /sup 1/H and /sup 13/C NMR spectroscopy. The properties of acetylated 1,4-naphthoquinone glycosides are presented.

Effects of green tea tannin on cisplatin-induced nephropathy in LLC-PK1 cells and rats.

PubMed

Yokozawa, T; Nakagawa, T; Lee, K I; Cho, E J; Terasawa, K; Takeuchi, S

1999-11-01

A study was conducted to clarify whether green tea tannin ameliorated cisplatin-induced renal injury in terms of lactate dehydrogenase and malondialdehyde leakage from a renal epithelial cell line, swine-derived LLC-PK1 cells in culture. Green tea tannin was shown to suppress the cytotoxicity of cisplatin, the suppressive effect increasing with the dose of green tea tannin. The effect of cisplatin was then investigated in rats given green tea tannin for 40 days before cisplatin administration and in control rats given no green tea tannin. In control rats, blood, urinary and renal parameters and the activities of antioxidative enzymes in renal tissue deviated from the normal range, indicating dysfunction of the kidneys. In contrast, rats given green tea tannin showed decreased blood levels of urea nitrogen and creatinine, and decreased urinary levels of protein and glucose, reflecting less damage to the kidney. In this group, the activity of catalase in the renal tissue was increased, while the level of malondialdehyde was decreased, suggesting the involvement of radicals in the normalizing of kidney function. Based on the evidence available it appeared that green tea tannin eliminated oxidative stress and was beneficial to renal function.

Effect of hydrolysable tannins on intestinal morphology, proliferation and apoptosis in entire male pigs.

PubMed

Bilić-Šobot, Diana; Kubale, Valentina; Škrlep, Martin; Čandek-Potokar, Marjeta; Prevolnik Povše, Maja; Fazarinc, Gregor; Škorjanc, Dejan

2016-10-01

This study aimed to evaluate the effect of hydrolysable tannin supplementation on morphology, cell proliferation and apoptosis in the intestine and liver of fattening boars. A total of 24 boars (Landrace × Large white) were assigned to four treatment groups: Control (fed commercial feed mixture) and three experimental groups fed the same diet supplemented with 1%, 2% and 3% of hydrolysable tannin-rich extract. Animals were housed individually with ad libitum access to feed and then slaughtered at 193 d of age and 122 ± 10 kg body weight. Diets supplemented with hydrolysable tannin affected the morphometric traits of the duodenum mucosa as reflected in increased villus height, villus perimeter and mucosal thickness. No effect was observed on other parts of the small intestine. In the large intestine, tannin supplementation reduced mitosis (in the caecum and descending colon) and apoptosis (in the caecum, ascending and descending colon). No detrimental effect of tannin supplementation on liver tissue was observed. The present findings suggest that supplementing boars with hydrolysable tannins at concentrations tested in this experiment has no unfavourable effects on intestinal morphology. On the contrary, it may alter cell debris production in the large intestine and thus reduce intestinal skatole production.

Effect of plant sterols and tannins on Phytophthora ramorum growth and sporulation

Treesearch

Rachel A. Stong; Eli Kolodny; Rick G. Kelsey; M.P. Gonzalez-Hernandez; Jorge M. Vivanco; Daniel K. Manter

2013-01-01

Elicitin-mediated acquisition of plant sterols is required for growth and sporulation of Phytophthora spp. This study examined the interactions between elicitins, sterols, and tannins. Ground leaf tissue, sterols, and tannin-enriched extracts were obtained from three different plant species (California bay laurel, California black oak, and Oregon...

Heating and reduction affect the reaction with tannins of wine protein fractions differing in hydrophobicity.

PubMed

Marangon, Matteo; Vincenzi, Simone; Lucchetta, Marco; Curioni, Andrea

2010-02-15

During the storage, bottled white wines can manifest haziness due to the insolubilisation of the grape proteins that may 'survive' in the fermentation process. Although the exact mechanism of this occurrence is not fully understood, proteins and tannins are considered two of the key factors involved in wine hazing, since their aggregation leads to the formation of insoluble particles. To better understand this complex interaction, proteins and tannins from the same unfined Pinot grigio wine were separated. Wine proteins were then fractionated by hydrophobic interaction chromatography (HIC). A significant correlation between hydrophobicity of the wine protein fractions and the haze formed after reacting with wine tannins was found, with the most reactive fractions revealing (by SDS-PAGE and RP-HPLC analyses) the predominant presence of thaumatin-like proteins. Moreover, the effects of both protein heating and disulfide bonds reduction (with dithiotreithol) on haze formation in the presence of tannins were assessed. These treatments generally resulted in an improved reactivity with tannins, and this phenomenon was related to both the surface hydrophobicity and composition of the protein fractions. Therefore, haze formation in wines seems to be related to hydrophobic interactions occurring among proteins and tannins. These interactions should occur on hydrophobic tannin-binding sites, whose exposition on the proteins can depend on both protein heating and reduction. Copyright 2009 Elsevier B.V. All rights reserved.

MATE2 Mediates Vacuolar Sequestration of Flavonoid Glycosides and Glycoside Malonates in Medicago truncatula[C][W][OA

PubMed Central

Zhao, Jian; Huhman, David; Shadle, Gail; He, Xian-Zhi; Sumner, Lloyd W.; Tang, Yuhong; Dixon, Richard A.

2011-01-01

The majority of flavonoids, such as anthocyanins, proanthocyanidins, and isoflavones, are stored in the central vacuole, but the molecular basis of flavonoid transport is still poorly understood. Here, we report the functional characterization of a multidrug and toxin extrusion transporter (MATE2), from Medicago truncatula. MATE 2 is expressed primarily in leaves and flowers. Despite its high similarity to the epicatechin 3′-O-glucoside transporter MATE1, MATE2 cannot efficiently transport proanthocyanidin precursors. In contrast, MATE2 shows higher transport capacity for anthocyanins and lower efficiency for other flavonoid glycosides. Three malonyltransferases that are coexpressed with MATE2 were identified. The malonylated flavonoid glucosides generated by these malonyltransferases are more efficiently taken up into MATE2-containing membrane vesicles than are the parent glycosides. Malonylation increases both the affinity and transport efficiency of flavonoid glucosides for uptake by MATE2. Genetic loss of MATE2 function leads to the disappearance of leaf anthocyanin pigmentation and pale flower color as a result of drastic decreases in the levels of various flavonoids. However, some flavonoid glycoside malonates accumulate to higher levels in MATE2 knockouts than in wild-type controls. Deletion of MATE2 increases seed proanthocyanidin biosynthesis, presumably via redirection of metabolic flux from anthocyanin storage. PMID:21467581

A novel glycoside from Acanthus hirsutus (Acanthaceae).

PubMed

Capanlar, Seval; Böke, Nazli; Yaşa, Ihsan; Kirmizigül, Süheyla

2010-04-01

A novel glycoside, hirsutusoide (1), characterized as 2-(o-hydroxyphenyl)-2-hydroxyethenyl-O-beta-glucopyranoside, was isolated from the endemic Acanthus hirsutus Boiss. In addition to compound 1, three known glycosides, luteolin-7-O-beta-D-glucuronide (2), beta-sitosterol-3-O-beta-D-glucopyranoside (3) and (2R)-2-O-beta-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (4), were also isolated. Compound 2 was the first report from this genus. Antimicrobial and antioxidant activity of the extracts and the novel compound were investigated by determining MIC (microg/mL) and IC50 (microg/mL) values, respectively.

A Novel Diterpene Glycoside with Nine Glucose Units from Stevia rebaudiana Bertoni.

PubMed

Prakash, Indra; Ma, Gil; Bunders, Cynthia; Charan, Romila D; Ramirez, Catherine; Devkota, Krishna P; Snyder, Tara M

2017-01-31

Following our interest in new diterpene glycosides with better taste profiles than that of Rebaudioside M, we have recently isolated and characterized Rebaudioside IX-a novel steviol glycoside-from a commercially-supplied extract of Stevia rebaudiana Bertoni. This molecule contains a hexasaccharide group attached at C-13 of the central diterpene core, and contains three additional glucose units when compared with Rebaudioside M. Here we report the complete structure elucidation-based on extensive Nuclear Magnetic Resonance (NMR) analysis (1H, 13C, Correlation Spectroscopy (COSY), Heteronuclear Single Quantum Coherence-Distortionless Enhancement Polarization Transfer (HSQC-DEPT), Heteronuclear Multiple Bond Correlation (HMBC), 1D Total Correlation Spectroscopy (TOCSY), Nuclear Overhauser Effect Spectroscopy (NOESY)) and mass spectral data-of this novel diterpene glycoside with nine sugar moieties and containing a relatively rare 16 α-linked glycoside. A steviol glycoside bearing nine glucose units is unprecedented in the literature, and could have an impact on the natural sweetener catalog.

The U.S. Dairy Forage Research Center (USDFRC) Condensed Tannin NMR Database.

PubMed

Zeller, Wayne E; Schatz, Paul F

2017-06-28

This Perspective describes a solution-state NMR database for flavan-3-ol monomers and condensed tannin dimers through tetramers obtained from the literature to 2015, containing data searchable by structure, molecular formula, degrees of polymerization, and 1 H and 13 C chemical shifts of the condensed tannins. Citations for all literature references are provided and should serve as valuable resource for scientists working in the field of condensed tannin research. The database will be periodically updated as additional information becomes available, typically on a yearly basis and is available for use, free of charge, from the U.S. Dairy Forage Research Center (USDFRC) Website.

The effects of high-tannin leaf litter from transgenic poplars on microbial communities in microcosm soils.

PubMed

Winder, Richard S; Lamarche, Josyanne; Constabel, C Peter; Hamelin, Richard C

2013-01-01

The impacts of leaf litter from genetically modified hybrid poplar accumulating high levels of condensed tannins (proanthocyanidins) were examined in soil microcosms consisting of moss growing on sieved soil. Moss preferentially proliferated in microcosms with lower tannin content; DGGE (denaturing gradient gel electrophoresis) detected increased fungal diversity in microcosms with low-tannin litter. The proportion of cloned rDNA sequences from Actinobacteria decreased with litter addition while Bacteroidetes, Chloroflexi, Cyanobacteria, and α-Proteobacteria significantly increased. β-Proteobacteria were proportionally more numerous at high-tannin levels. Tannins had no significant impact on overall diversity of bacterial communities analyzed with various estimators. There was an increased proportion of N-fixing bacteria corresponding to the addition of litter with low-tannin levels. The addition of litter increased the proportion of Ascomycota/Basidiomycota. Dothideomycetes, Pucciniomycetes, and Tremellomycetes also increased and Agaricomycetes decreased. Agaricomycetes and Sordariomycetes were significantly more abundant in controls, whereas Pucciniomycetes increased in soil with litter from transformed trees (P = 0.051). Richness estimators and diversity indices revealed no significant difference in the composition of fungal communities; PCoA (principal coordinate analyses) partitioned the fungal communities into three groups: (i) those with higher amounts of added tannin from both transformed and untransformed treatments, (ii) those corresponding to soils without litter, and (iii) those corresponding to microcosms with litter added from trees transformed only with a β-glucuronidase control vector. While the litter from transformed poplars had significant effects on soil microbe communities, the observed impacts reflected known impacts on soil processes associated with tannins, and were similar to changes that would be expected from natural variation in

A new cinnamic acid glycoside from roots of Heracleum dissectum.

PubMed

Wang, Zhi-Gang; Mi, Jie; Wang, Xin-Rui; Huo, Ya-Yu; Peng, Ya-Jie; Zhang, Hai-Min; Gao, Yang; Zhang, Hai-Long

2018-01-01

From the roots of Heracleum dissectum Lebb., one new cinnamic acid glycoside derivative named dissectumoside (1), together with eight known compounds including three phenolics, three phenolic glycosides and two phenylpropanoic glycoside were isolated using various chromatographic methods. Among them compound 2-9 was isolated from the plant for the first time. Their structures were elucidated and identified on the basis of their physicochemical properties and by extensive analyses of NMR spectroscopy and high-resolution mass spectrometry. The results of triglyceride accumulation screening in 3T3-L1 cells showed that compounds 1, 5 and 9 exhibited significantly accelerating activities of adipogenesis in adipocytes.

Free the tannins: the role of grape pathogenesis-related proteins in limiting condensed tannin extraction during winemaking

USDA-ARS?s Scientific Manuscript database

Grape-derived condensed tannins (CT) are important to the mouthfeel of red wines, but CT concentrations in red wines produced from wild Vitis species or their hybrids are often lower than corresponding wines produced from European wine grapes (V. vinifera), potentially decreasing their utility. Thes...

Fecalase: a model for activation of dietary glycosides to mutagens by intestinal flora

DOE Office of Scientific and Technical Information (OSTI.GOV)

Tamura, G.; Gold, C.; Ferro-Luzzi, A.

1980-08-01

Many substances in the plant kingdom and in man's diet occur as glycosides. Recent studies have indicated that many glycosides that are not mutagenic in tests such as the Salmonella test become mutagenic upon hydrolysis of the glycosidic linkages. The Salmonella test utilizes a liver homogenate to approximate mammalian metabolism but does not provide a source of the enzymes present in intestinal bacterial flora that hydrolyze the wide variety of glycosides present in nature. We describe a stable cell-free extract of human feces, fecalase, which is shown to contain various glycosidases that allow the in vitro activation of many naturalmore » glycosides to mutagens in the Salmonella/liver homogenate test. Many beverages, such as red wine (but apparently not white wine) and tea, contain glycosides of the mutagen quercetin. Red wine, red grape juice, and teas were mutagenic in the test when fecalase was added, and red wine contained considerable direct mutagenic activity in the absence of fecalase. The implications of quercetin mutagenicity and carcinogenicity are discussed.« less

Nutrient content, in vitro ruminal fermentation characteristics and methane reduction potential of tropical tannin-containing leaves.

PubMed

Bhatta, Raghavendra; Saravanan, Mani; Baruah, Luna; Sampath, Koratekere T

2012-12-01

Plant tannins as rumen modifiers are better than chemicals or antibiotic-based modifiers since these compounds are natural products which are environmentally friendly and therefore have a better acceptance with regard to feed safety issues. Tropical plants containing phenols such as tannins were found to suppress or eliminate protozoa from the rumen and reduce methane and ammonia production. The screening of these plants is an important step in the identification of new compounds and feed additives which might contribute to mitigate rumen methanogenesis. The present study was carried out to determine the efficacy of tannins from tropical tree leaves for their methane reduction properties. Activity of tannins, as represented by the increase in gas volume with the addition of polyethylene glycol (PEG)-6000 as a tannin binder (tannin bioassay) was highest in Ficus bengalensis (555%), followed by Azardirachta indica (78.5%). PEG addition did not alter (P > 0.05) methane percentage in Ficus racemosa, Glyricidia maculata, Leucena leucocephala, Morus alba and Semaroba glauca, confirming that tannins in these samples did not affect methanogenesis. The increase (P < 0.05) in protozoa population with PEG was maximal in Ficus religiosa (50), followed by Moringa oleifera (31.2), Azardirachta indica (29.9) and Semaroba glauca (27.5). There was no change (P > 0.05) in the protozoa population in Autocarpus integrifolia, Ficus bengalensis, Jatropha curcus, Morus alba and Sesbania grandiflora, demonstrating that methane reduction observed in these samples per se was not due to defaunation effect of the tannin. The increase in total volatile fatty acid concentration in samples with PEG ranged from 0.6% to > 70%. The highest increase (%) in NH(3)-N was recorded in Azardirachta indica (67.4), followed by Ficus mysoriensis (35.7) and Semaroba glauca (32.6) leaves, reflecting strong protein binding properties of tannin. The results of our study established that in vitro methanogenesis

Reconsidering the effects of tannin on seed dispersal by rodents: evidence from enclosure and field experiments with artificial seeds.

PubMed

Zhang, Mingming; Steele, Michael A; Yi, Xianfeng

2013-11-01

The question of how tannin affects feeding and hoarding preferences of rodents still remains poorly understood, in part, because it is difficult to control for other seed traits when considering the sole effect of tannin. Here, we constructed a series of artificial 'seeds' with different tannin levels, made from wheat flour, peanut powder and hydrolysable tannins, to determine the direct effects of tannin on both feeding and hoarding preferences. We first presented 'seeds' to individual rodents of two species (Tamias sibiricus and Apodemus peninsulae) confined in semi-natural enclosures and then monitored patterns of seed dispersal and consumption by free-ranging animals in a temperate forest in the Xiaoxing'an Mountains, Heilongjiang Province of China. Our results showed that small rodents displayed a significant preference for low-tannin 'seeds' for both consumption and caching in both captive and field experiments. Moreover, our two-year study consistently showed that tannin concentration was significantly and negatively correlated with the number of cached 'seeds' at both the individual and population levels. Seed size, compared with tannin concentrations, appeared to have little effect on dispersal distances and the number of 'seeds' cached. Low-tannin 'seeds' tended to be dispersed greater distances by rodents in the field than those with higher levels of tannin. These results failed to support those of previous reports indicating that acorns containing higher tannins are more likely to be cached by food hoarding animals. Copyright © 2013 Elsevier B.V. All rights reserved.

Selective hydrolysis of flavonoid glycosides by Curvularia lunata.

PubMed

Liu, Jing-Yuan; Yu, He-Shui; Feng, Bing; Kang, Li-Ping; Pang, Xu; Xiong, Cheng-Qi; Zhao, Yang; Li, Chun-Mei; Zhang, Yi; Ma, Bai-Ping

2013-11-01

Twelve flavonoid glycosides were involved in the biotransformation of the glycosyl moieties by Curvularia lunata 3.4381, and the products were analyzed by UPLC/PDA-Q-TOF-MS(E). Curvularia lunata displayed hydrolyzing activities on the terminal Rha or Glc units of some flavonoid glycosides. Terminal Rha with a 1 → 2 linkage of isorhamnetin-3-O-neohesperidoside and typhaneoside could be hydrolyzed by Curvularia lunata, but terminal Rha with a 1 → 6 linkage of rutin, typhaneoside, and quercetin-3-O-apiosyl-(1 → 2)-[rhamnosyl-(1 → 6)]-glucoside could not be hydrolyzed. Curvularia lunata could also hydrolyze the Glc of icariin, floramanoside B, and naringin. This is the first report of the hydrolysis of glycosyl units of flavonoid glycosides by Curvularia lunata. A new way to convert naringin to naringenin was found in this research. Copyright © 2013 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages

NASA Astrophysics Data System (ADS)

Hahm, Heung Sik; Hurevich, Mattan; Seeberger, Peter H.

2016-09-01

Automated glycan assembly (AGA) has advanced from a concept to a commercial technology that rapidly provides access to diverse oligosaccharide chains as long as 30-mers. To date, AGA was mainly employed to incorporate trans-glycosidic linkages, where C2 participating protecting groups ensure stereoselective couplings. Stereocontrol during the installation of cis-glycosidic linkages cannot rely on C2-participation and anomeric mixtures are typically formed. Here, we demonstrate that oligosaccharides containing multiple cis-glycosidic linkages can be prepared efficiently by AGA using monosaccharide building blocks equipped with remote participating protecting groups. The concept is illustrated by the automated syntheses of biologically relevant oligosaccharides bearing various cis-galactosidic and cis-glucosidic linkages. This work provides further proof that AGA facilitates the synthesis of complex oligosaccharides with multiple cis-linkages and other biologically important oligosaccharides.

Inactivation of tannins in milled sorghum grain through steeping in dilute NaOH solution.

PubMed

Adetunji, Adeoluwa I; Duodu, Kwaku G; Taylor, John R N

2015-05-15

Steeping milled sorghum in up to 0.4% NaOH was investigated as a method of tannin inactivation. NaOH steeping substantially reduced assayable total phenols and tannins in both Type III and Type II sorghums and with Type III sorghum caused a 60-80% reduction in α-amylase inhibition compared to a 20% reduction by water steeping. NaOH treatment also reduced starch liquefaction time and increased free amino nitrogen. Type II tannin sorghum did not inhibit α-amylase and consequently the NaOH treatment had no effect. HPLC and LC-MS of the tannin extracts indicated a general trend of increasing proanthocyanidin/procyanidin size with increasing NaOH concentration and steeping time, coupled with a reduction in total area of peaks resolved. These show that the NaOH treatment forms highly polymerised tannin compounds, too large to assay and to interact with the α-amylase. NaOH pre-treatment of Type III sorghums could enable their utilisation in bioethanol production. Copyright © 2014 Elsevier Ltd. All rights reserved.

Inhibition of hydrogen sulfide, methane, and total gas production and sulfate-reducing bacteria in in vitro swine manure by tannins, with focus on condensed quebracho tannins.

PubMed

Whitehead, Terence R; Spence, Cheryl; Cotta, Michael A

2013-09-01

Management practices from large-scale swine production facilities have resulted in the increased collection and storage of manure for off-season fertilization use. Odor and emissions produced during storage have increased the tension among rural neighbors and among urban and rural residents. Production of these compounds from stored manure is the result of microbial activity of the anaerobic bacteria populations during storage. In the current study, the inhibitory effects of condensed quebracho tannins on in vitro swine manure for reduction of microbial activity and reduced production of gaseous emissions, including the toxic odorant hydrogen sulfide produced by sulfate-reducing bacteria (SRB), was examined. Swine manure was collected from a local swine facility, diluted in anaerobic buffer, and mixed with 1 % w/v fresh feces. This slurry was combined with quebracho tannins, and total gas and hydrogen sulfide production was monitored over time. Aliquots were removed periodically for isolation of DNA to measure the SRB populations using quantitative PCR. Addition of tannins reduced overall gas, hydrogen sulfide, and methane production by greater than 90 % after 7 days of treatment and continued to at least 28 days. SRB population was also significantly decreased by tannin addition. qRT-PCR of 16S rDNA bacteria genes showed that the total bacterial population was also decreased in these incubations. These results indicate that the tannins elicited a collective effect on the bacterial population and also suggest a reduction in the population of methanogenic microorganisms as demonstrated by reduced methane production in these experiments. Such a generalized effect could be extrapolated to a reduction in other odor-associated emissions during manure storage.

Condensed Tannins from Longan Bark as Inhibitor of Tyrosinase: Structure, Activity, and Mechanism.

PubMed

Chai, Wei-Ming; Huang, Qian; Lin, Mei-Zhen; Ou-Yang, Chong; Huang, Wen-Yang; Wang, Ying-Xia; Xu, Kai-Li; Feng, Hui-Ling

2018-01-31

In this study, the content, structure, antityrosinase activity, and mechanism of longan bark condensed tannins were evaluated. The findings obtained from mass spectrometry demonstrated that longan bark condensed tannins were mixtures of procyanidins, propelargonidins, prodelphinidins, and their acyl derivatives (galloyl and p-hydroxybenzoate). The enzyme analysis indicated that these mixtures were efficient, reversible, and mixed (competitive is dominant) inhibitor of tyrosinase. What's more, the mixtures showed good inhibitions on proliferation, intracellular enzyme activity and melanogenesis of mouse melanoma cells (B 16 ). From molecular docking, the results showed the interactions between inhibitors and tyrosinase were driven by hydrogen bond, electrostatic, and hydrophobic interactions. In addition, high levels of total phenolic and extractable condensed tannins suggested that longan bark might be a good source of tyrosinase inhibitor. This study would offer theoretical basis for the development of longan bark condensed tannins as novel food preservatives and medicines of skin diseases.

Bioaccessibility, Intestinal Permeability and Plasma Stability of Isorhamnetin Glycosides from Opuntia ficus-indica (L.).

PubMed

Antunes-Ricardo, Marilena; Rodríguez-Rodríguez, César; Gutiérrez-Uribe, Janet A; Cepeda-Cañedo, Eduardo; Serna-Saldívar, Sergio O

2017-08-22

Isorhamnetin glycosides are representative compounds of Opuntia ficus-indica that possess different biological activities. There is slight information about the changes in bioaccessibility induced by the glycosylation pattern of flavonoids, particularly for isorhamnetin. In this study, the bioaccessibility and permeability of isorhamnetin glycosides extracted from O. ficus-indica were contrasted with an isorhamnetin standard. Also, the plasma stability of these isorhamnetin glycosides after intravenous administration in rats was evaluated. Recoveries of isorhamnetin after oral and gastric digestion were lower than that observed for its glycosides. After intestinal digestion, isorhamnetin glycosides recoveries were reduced to less than 81.0%. The apparent permeability coefficient from apical (AP) to basolateral (BL) direction (Papp (AP-BL) ) of isorhamnetin was 2.6 to 4.6-fold higher than those obtained for its glycosides. Isorhamnetin diglycosides showed higher Papp (AP-BL) values than triglycosides. Sugar substituents affected the Papp (AP-BL) of the triglycosides. Isorhamnetin glycosides were better retained in the circulatory system than the aglycone. After intravenous dose of the isorhamnetin standard, the elimination half-life was 0.64 h but increased to 1.08 h when the O. ficus-indica extract was administered. These results suggest that isorhamnetin glycosides naturally found in O. ficus-indica could be a controlled delivery system to maintain a constant plasmatic concentration of this important flavonoid to exert its biological effects in vivo.

Bioaccessibility, Intestinal Permeability and Plasma Stability of Isorhamnetin Glycosides from Opuntia ficus-indica (L.)

PubMed Central

Antunes-Ricardo, Marilena; Rodríguez-Rodríguez, César; Cepeda-Cañedo, Eduardo

2017-01-01

Isorhamnetin glycosides are representative compounds of Opuntia ficus-indica that possess different biological activities. There is slight information about the changes in bioaccessibility induced by the glycosylation pattern of flavonoids, particularly for isorhamnetin. In this study, the bioaccessibility and permeability of isorhamnetin glycosides extracted from O. ficus-indica were contrasted with an isorhamnetin standard. Also, the plasma stability of these isorhamnetin glycosides after intravenous administration in rats was evaluated. Recoveries of isorhamnetin after oral and gastric digestion were lower than that observed for its glycosides. After intestinal digestion, isorhamnetin glycosides recoveries were reduced to less than 81.0%. The apparent permeability coefficient from apical (AP) to basolateral (BL) direction (Papp(AP-BL)) of isorhamnetin was 2.6 to 4.6-fold higher than those obtained for its glycosides. Isorhamnetin diglycosides showed higher Papp(AP-BL) values than triglycosides. Sugar substituents affected the Papp(AP-BL) of the triglycosides. Isorhamnetin glycosides were better retained in the circulatory system than the aglycone. After intravenous dose of the isorhamnetin standard, the elimination half-life was 0.64 h but increased to 1.08 h when the O. ficus-indica extract was administered. These results suggest that isorhamnetin glycosides naturally found in O. ficus-indica could be a controlled delivery system to maintain a constant plasmatic concentration of this important flavonoid to exert its biological effects in vivo. PMID:28829356

Hormetic versus toxic effects of vegetable tannin in a multitest study.

PubMed

De Nicola, E; Gallo, M; Iaccarino, M; Meriç, S; Oral, R; Russo, T; Sorrentino, T; Tünay, O; Vuttariello, E; Warnau, M; Pagano, G

2004-04-01

Tannin from mimosa trees (Acacia sp.) utilized in traditional leather tanning was tested for toxicity in sea urchin (Sphaerechinus granularis and Paracentrotus lividus) embryos and sperm, marine, and freshwater algae (Selenastrum capricornutum and Dunaliella tertiolecta), and Daphnia magna. Based on a two-step tanning procedure used in traditional tanneries, two mimosa tannin preparations, i.e., fresh tannin (FT) and used tannin (UT), were tested as suspensions. The early results in S. granularis embryos showed that UT exerted lower acute toxicity than FT, namely, 1 vs 100 mg/L, to obtain 100% mortality, respectively. Subsequent bioassays were conducted on fresh tannin water extracts (TWE) corresponding to nominal tannin concentrations ranging from 0.1 to 30 mg/L. Developmental toxicity, up to embryonic mortality was exerted by TWE at levels > 1 mg/L, S. granularis being more sensitive than P. lividus embryos/larvae. At the concentration of 0.1 mg/L, the frequencies of larval malformations were significantly lower than in controls. This positive stimulatory effect (currently termed as hormesis) was observed in extended numbers of culture replicates (up to 14) and was significant in the embryo cultures characterized by a relatively poor control quality (with < 70% viable larvae in controls), whereas this effect was not observed in good-quality cultures (with > or = 70% viable larvae in controls). Cytogenetic analysis of S. granularis embryos reared in FT or UT suspensions (1 mg/L to 1 g/L) showed mitotoxic effects (decrease in active mitoses per embryo) in FT-exposed, but not in UT-exposed embryos. Mitotic aberrations were significantly increased by 10 mg/L UT. Sperm fertilization success in both sea urchin species showed an increasing fertilization rate (FR) up to 0.3 mg/L TWE and a dose-related decrease in FR up to 30 mg/L. Again, the offspring of P. lividus sperm exposed to TWE (0.1 and 0.3 mg/L) showed a decrease in larval malformations compared to controls

Physico-mechanical properties of plywood bonded with ecological adhesives from Acacia mollissima tannins and lignosulfonates

NASA Astrophysics Data System (ADS)

Rhazi, Naima; Oumam, Mina; Sesbou, Abdessadek; Hannache, Hassan; Charrier-El Bouhtoury, Fatima

2017-06-01

The objective of this research was to develop ecological adhesives for bonding plywood panels using lignosulfonates, a common waste product of the wood pulp industry, and natural tannin extracted from Moroccan bark of Acacia mollissima using different process. Natural tannin and lignin were used in wood adhesives formulation to substitute resins based on phenol and formaldehyde. To achieve this, the lignosulfonates were glyoxalated to enhance their reactivity and the used tannins obtained by three different extraction methods were compared with commercial mimosa tannin. The proportion of Acacia mollissima tannins and lignosulfonates, the pressing time, the pressing temperature, and the pressure used were studied to improve mechanical properties, and bonding quality of plywood panel. The properties of plywood panels produced with these adhesives were tested in accordance with normative tests. Thus, the tensile strength, and the shear strength were measured. The results showed that the performance of the plywood panels made using biobased tannin adhesives was influenced by physical conditions such as pressure, press temperature as well as by chemical conditions, such as the tannin-lignin ratio. It exhibited excellent mechanical properties comparable to commercially available phenol-formaldehyde plywood adhesives. This study showed that biobased adhesives formulations presented good and higher mechanical performance and no formaldehyde emission. Contribution to the topical issue "Materials for Energy harvesting, conversion and storage II (ICOME 2016)", edited by Jean-Michel Nunzi, Rachid Bennacer and Mohammed El Ganaoui

Quantitative analysis of red wine tannins using Fourier-transform mid-infrared spectrometry.

PubMed

Fernandez, Katherina; Agosin, Eduardo

2007-09-05

Tannin content and composition are critical quality components of red wines. No spectroscopic method assessing these phenols in wine has been described so far. We report here a new method using Fourier transform mid-infrared (FT-MIR) spectroscopy and chemometric techniques for the quantitative analysis of red wine tannins. Calibration models were developed using protein precipitation and phloroglucinolysis as analytical reference methods. After spectra preprocessing, six different predictive partial least-squares (PLS) models were evaluated, including the use of interval selection procedures such as iPLS and CSMWPLS. PLS regression with full-range (650-4000 cm(-1)), second derivative of the spectra and phloroglucinolysis as the reference method gave the most accurate determination for tannin concentration (RMSEC = 2.6%, RMSEP = 9.4%, r = 0.995). The prediction of the mean degree of polymerization (mDP) of the tannins also gave a reasonable prediction (RMSEC = 6.7%, RMSEP = 10.3%, r = 0.958). These results represent the first step in the development of a spectroscopic methodology for the quantification of several phenolic compounds that are critical for wine quality.

Dietary flavonoid aglycones and their glycosides: Which show better biological significance?

PubMed

Xiao, Jianbo

2017-06-13

The dietary flavonoids, especially their glycosides, are the most vital phytochemicals in diets and are of great general interest due to their diverse bioactivity. The natural flavonoids almost all exist as their O-glycoside or C-glycoside forms in plants. In this review, we summarized the existing knowledge on the different biological benefits and pharmacokinetic behaviors between flavonoid aglycones and their glycosides. Due to various conclusions from different flavonoid types and health/disease conditions, it is very difficult to draw general or universally applicable comments regarding the impact of glycosylation on the biological benefits of flavonoids. It seems as though O-glycosylation generally reduces the bioactivity of these compounds - this has been observed for diverse properties including antioxidant activity, antidiabetes activity, anti-inflammation activity, antibacterial, antifungal activity, antitumor activity, anticoagulant activity, antiplatelet activity, antidegranulating activity, antitrypanosomal activity, influenza virus neuraminidase inhibition, aldehyde oxidase inhibition, immunomodulatory, and antitubercular activity. However, O-glycosylation can enhance certain types of biological benefits including anti-HIV activity, tyrosinase inhibition, antirotavirus activity, antistress activity, antiobesity activity, anticholinesterase potential, antiadipogenic activity, and antiallergic activity. However, there is a lack of data for most flavonoids, and their structures vary widely. There is also a profound lack of data on the impact of C-glycosylation on flavonoid biological benefits, although it has been demonstrated that in at least some cases C-glycosylation has positive effects on properties that may be useful in human healthcare such as antioxidant and antidiabetes activity. Furthermore, there is a lack of in vivo data that would make it possible to make broad generalizations concerning the influence of glycosylation on the benefits of

Enological Tannin Effect on Red Wine Color and Pigment Composition and Relevance of the Yeast Fermentation Products.

PubMed

García-Estévez, Ignacio; Alcalde-Eon, Cristina; Puente, Víctor; Escribano-Bailón, M Teresa

2017-11-23

Enological tannins are widely used in the winemaking process either to improve different wine characteristics (color stability, among others) or to compensate for low tannin levels. In this work, the influence of the addition of two different enological tannins, mainly composed of hydrolysable (ellagitannins) and condensed tannins, on the evolution of color and pigment composition of two different types of model systems containing the five main grape anthocyanins was studied. In addition, the effect of the addition of an enological tannin on the color and pigment composition of red wines made from Vitis vinifera L. cv Tempranillo grapes was also studied by high-performance liquid chromatography with diode array detection coupled to mass spectrometry (HPLC-DAD-MS). Results showed that, in model systems, the addition of the enological tannin favored the formation of anthocyanin-derived pigments, such as A-type and B-type vitisins and flavanol-anthocyanin condensation products, provided that the yeast precursors were previously supplied. Moreover, model systems containing the enological tannins were darker and showed higher values of chroma at the end of the study than control ones. The higher formation of these anthocyanin-derived pigments was also observed in the red wines containing the enological tannin. Moreover, these wine also showed lower lightness (L*) values and higher chroma (C* ab ) values than control wines, indicating a higher stabilization of color.

The effect of tannins and pH on the corrosion of metals in wood extracts

Treesearch

Samuel Zelinka; D.S. Stone

2011-01-01

Tannins and pH are often cited as factors that affect the corrosiveness of wood yet there are few data to confirm these statements. The purpose of this paper is to systematically investigate the effect of tannins and pH on corrosion of metals in wood. Four wood species known to vary in both their pH and extractives were chosen and extracted with water. The pH, tannin...

Effects of Fat and Protein Levels on Foraging Preferences of Tannin in Scatter-Hoarding Rodents

PubMed Central

Wang, Bo; Chen, Jin

2012-01-01

Both as consumers and dispersers of seeds, scatter-hoarding rodents often play an important role in the reproductive ecology of many plant species. However, the seeds of many plant species contain tannins, which are a diverse group of water-soluble phenolic compounds that have a high affinity for proteins. The amount of tannins in seeds is expected to affect rodent foraging preferences because of their major impact on rodent physiology and survival. However, variable results have been obtained in studies that evaluated the effects of tannin on rodent foraging behavior. Hence, in this study, we aimed to explain these inconsistent results and proposed that a combination of seed traits might be important in rodent foraging behavior, because it is difficult to distinguish between the effects of individual traits on rodent foraging behavior and the interactions among them. By using a novel artificial seed system, we manipulated seed tannin and fat/protein levels to examine directly the univariate effects of each component on the seed preferences of free-ranging forest rats (Apodemus latronum and Apodemus chevrieri) during the behavioral process of scatter hoarding. Our results showed that both tannin and fat/protein had significant effects on rodent foraging behavior. Although only a few interactive effects of tannin and fat/protein were recorded, higher concentrations of both fat and protein could attenuate the exclusion of seeds with higher tannin concentrations by rodents, thus influencing seed fate. Furthermore, aside from the concentrations of tannin, fat, and protein, numerous other traits of plant seeds may also influence rodent foraging behavior. We suggest that by clarifying rodent foraging preferences, a better understanding of the evolution of plant seed traits may be obtained because of their strong potential for selective pressure. PMID:22808217

Evaluation of tannins interactions in grape (Vitis vinifera L.) skins.

PubMed

Rustioni, Laura; Fiori, Simone; Failla, Osvaldo

2014-09-15

Tannins have a central role in grapevine berries both for their physiological and enological implications. In the skin tissue they can be in vacuolar solution, or associated to the cell walls through weak or strong physicochemical interactions. The present work aims to separate vacuolar, non-covalently and covalently bonded tannins fractions. A specific extraction procedure was developed. A first extraction in ethanol at low temperature allowed the quantification of vacuolar tannins. An urea treatment followed by an ethanol extraction at room temperature was able to separate non-covalently bonded compounds. Finally an acid catalysis was used to break down proanthocyanidin covalent bonds. The method was validated on ripe grape samples of three cultivars, on berries developed in two sun exposure conditions. The Ethephon treatment effect was also evaluated. Beside the method development, a preliminary evaluation of the cultivar, exposition and Ethephon treatment effects are discussed. Copyright © 2014 Elsevier Ltd. All rights reserved.

Biomolecular Interactions of Tannin Isolated from Oenothera gigas with Liposomes.

PubMed

Sekowski, Szymon; Ionov, Maksim; Dubis, Alina; Mavlyanov, Saidmukhtar; Bryszewska, Maria; Zamaraeva, Maria

2016-04-01

We have examined the interaction between hydrolysable tannin 1-O-galloyl-4,6-hexahydroxydiphenoyl-β-D-glucose (OGβDG) with neutral liposomes as a model of cell membranes composed of three lipids: lecithin, 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) at different mass ratios. OGβDG in the concentration range 0.5-15 µg/ml (0.4-12 µM) strongly interacts with liposomal membranes by changing their structure, surface charge and fluidity. Used OGβDG molecules decrease and increase the rigidity of hydrophilic surface and hydrophobic parts of liposomes, respectively. At higher concentrations of tannin (>15 µM), liposomes are aggregated. Fourier Transform Infra-Red (FTIR) analysis showed that mainly -OH groups from OGβDG and also PO(2-) groups from phospholipids are responsible for the interaction. Obtained data indicate the importance of membrane lipid composition in interactions between tannins and cells.

[Contents of flavonoids, tannins and fiber in some species of vegetative tea].

PubMed

Berketova, L V; Kosheleva, O V

2010-01-01

The content of some biologically active substances such as flavonoids, tannins and soluble dietary fiber in various types of vegetative tea was analyzed. The results are shown that the content of flavonoids ranges from 0.28 to 9.87%, tannins--from 0.91 to 7.07% and soluble dietary fiber 0.37 up to 14.7%.

Manure ammonia and greenhouse gas emissions from beef cattle fed condensed tannins

USDA-ARS?s Scientific Manuscript database

A study was conducted to determine the effects of three levels of condensed tannins fed to 27 beef feed yard steers on ammonia and GHG emissions from manure. Condensed tannins were fed at rates of 0, 0.5 and 1.0 percent on a dry matter basis. Manure and urine were collected from two periods over 6 d...

Yellow colored blooms of Argemone mexicana and Turnera ulmifolia mediated synthesis of silver nanoparticles and study of their antibacterial and antioxidant activity

NASA Astrophysics Data System (ADS)

Chandrasekhar, N.; Vinay, S. P.

2017-11-01

In the present work, AgNPs were prepared using a simple bio-reduction method. This is ecologically welcoming and cost-effective method. Yellow colored blooms concentrate of Argemone mexicana and Turnera ulmifolia are used as bio reducing agents in the study. The formation of silver nanoparticles was confirmed by UV-Vis spectrophotometer and characterization of the nanoparticles was done by FTIR, SEM, XRD and EDX. The Antibacterial action of silver nanoparticles was tested against Staphylococus aureus, Pseudomonas aeruginosa, Escherichia coli and Klebsiella aerogenes. The phytochemical analysis of the blooms concentrate has shown the existence of saponins, alkaloids, amino acids, phenols, tannins, terpenoids, flavonoids and cardiac glycosides. In vitro anti-oxidant action of both A. mexicana and T. ulmifolia AgNPs were studied by DPPH assay and reducing power assay.

Screening of antibacterial potentials of some medicinal plants from Melghat forest in India.

PubMed

Tambekar, D H; Khante, B S; Chandak, B R; Titare, A S; Boralkar, S S; Aghadte, S N

2009-05-07

Cyperus rotundus, Caesalpinia bonducella, Tinospora cordifolia, Gardenia gummifera, Ailanthus excelsa, Acacia arabica, Embelia ribes and Ventilago maderspatana from Melghat forest were screened for their antibacterial potential against Escherichia coli, Staphylococcus aureus, Klebsiella pneumoniae, Proteus vulgaris, Salmonella typhi, Shigella flexneri, Salmonella paratyphi, Salmonella typhimurium, Pseudomonas aeruginosa, Enterobacter aerogenes by disc diffusion method. Out of these medicinal plants Caesalpinia bonducella, Gardenia gummifera and Acacia arabica showed remarkable antibacterial potential. The phytochemical analysis had showed the presence of Cardiac glycosides in all extracts (aqueous, acetone, ethanol and methanol) of Acacia arabica, Gardenia gummifera and ethanol, methanol extracts of Caesalpinia bonducella. Flavonoids were present in Gardenia gummifera, Ailanthus excelsa and acetone, methanol extracts of Acacia Arabica. Tannins and phenolic were present in Cyperus rotundus, Embelia ribes, and organic extracts of Ventilago maderspatana.

Red wine tannins fluidify and precipitate lipid liposomes and bicelles. A role for lipids in wine tasting?

PubMed

Furlan, Aurélien L; Castets, Aurore; Nallet, Frédéric; Pianet, Isabelle; Grélard, Axelle; Dufourc, Erick J; Géan, Julie

2014-05-20

Sensory properties of red wine tannins are bound to complex interactions between saliva proteins, membranes taste receptors of the oral cavity, and lipids or proteins from the human diet. Whereas astringency has been widely studied in terms of tannin-saliva protein colloidal complexes, little is known about interactions between tannins and lipids and their implications in the taste of wine. This study deals with tannin-lipid interactions, by mimicking both oral cavity membranes by micrometric size liposomes and lipid droplets in food by nanometric isotropic bicelles. Deuterium and phosphorus solid-state NMR demonstrated the membrane hydrophobic core disordering promoted by catechin (C), epicatechin (EC), and epigallocatechin gallate (EGCG), the latter appearing more efficient. C and EGCG destabilize isotropic bicelles and convert them into an inverted hexagonal phase. Tannins are shown to be located at the membrane interface and stabilize the lamellar phases. These newly found properties point out the importance of lipids in the complex interactions that happen in the mouth during organoleptic feeling when ingesting tannins.

Antioxidant status of faeces of captive black rhinoceros (Diceros bicornis) in relation to dietary tannin supplementation.

PubMed

Clauss, M; Pellegrini, N; Castell, J C; Kienzle, E; Dierenfeld, E S; Hummel, J; Flach, E J; Streich, W J; Hatt, J-M

2006-08-01

In context with the frequent observations of excessive iron (Fe) storage in captive black rhinoceroses (Diceros bicornis), it has been suggested that both an excessive dietary Fe content and a lack of dietary Fe-chelating substances, such as tannins, is the underlying cause. Therefore, studies on the effects of tannin supplementation to captive diet are warranted. Six captive rhinoceroses were fed their normal zoo diet (N), and a similar diet supplemented with either tannic acid (T, hydrolysable tannin) or quebracho (Q, condensed tannins), and the total antioxidant capacity (TAC) was measured as mmol Trolox equivalents per kg fresh faeces. The TAC values on diets N (1.24 +/- 0.39 mmol/kg fresh faeces) and T (1.34 +/- 0.33 mmol/kg fresh faeces) were similar, but significantly higher on diet Q (2.32 +/- 0.61 mmol/kg fresh faeces). In contrast to expectations, faecal TAC increased with increasing faecal Fe, possibly as a result of the fact that the faecal Fe content was positively correlated to the proportion of concentrate feeds in the diet, which also contain antioxidants, such as vitamin E, in addition to Fe. Increased antioxidant status caused by the use of tannin substances could have a beneficial effect on animal health, but if tannins should be incorporated in designed diets, other tannin sources, such as grape pomace should be tested.

Environment-friendly adhesives for surface bonding of wood-based flooring using natural tannin to reduce formaldehyde and TVOC emission.

PubMed

Kim, Sumin

2009-01-01

The objective of this research was to develop environment-friendly adhesives for face fancy veneer bonding of engineered flooring using the natural tannin form bark in the wood. The natural wattle tannin adhesive were used to replace UF resin in the formaldehyde-based resin system in order to reduce formaldehyde and volatile organic compound (VOC) emissions from the adhesives used between plywoods and fancy veneers. PVAc was added to the natural tannin adhesive to increase viscosity of tannin adhesive for surface bonding. For tannin/PVAc hybrid adhesives, 5%, 10%, 20% and 30% of PVAc to the natural tannin adhesives were added. tannin/PVAc hybrid adhesives showed better bonding than the commercial natural tannin adhesive with a higher level of wood penetration. The initial adhesion strength was sufficient to be maintained within the optimum initial tack range. The standard formaldehyde emission test (desiccator method), field and laboratory emission cell (FLEC) and VOC analyzer were used to determine the formaldehyde and VOC emissions from engineered flooring bonded with commercial the natural tannin adhesive and tannin/PVAc hybrid adhesives. By desiccator method and FLEC, the formaldehyde emission level of each adhesive showed the similar tendency. All adhesives satisfied the E(1) grade (below 1.5 mg/L) and E(0) grade (below 0.5 mg/L) with UV coating. VOC emission results by FLEC and VOC analyzer were different with the formaldehyde emission results. TVOC emission was slightly increased as adding PVAc.

Antiproliferative activity, antioxidant capacity and tannin content in plants of semi-arid northeastern Brazil.

PubMed

Gomes de Melo, Joabe; de Sousa Araújo, Thiago Antônio; Thijan Nobre de Almeida e Castro, Valérium; Lyra de Vasconcelos Cabral, Daniela; do Desterro Rodrigues, Maria; Carneiro do Nascimento, Silene; Cavalcanti de Amorim, Elba Lúcia; de Albuquerque, Ulysses Paulino

2010-11-24

The objective of this study was to evaluate antiproliferative activity, antioxidant capacity and tannin content in plants from semi-arid northeastern Brazil (Caatinga). For this study, we selected 14 species and we assayed the methanol extracts for antiproliferative activity against the HEp-2 (laryngeal cancer) and NCI-H292 (lung cancer) cell lines using the (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazole) (MTT) method. In addition, the antioxidant activity was evaluated with the DPPH (2,2-diphenyl-2-picrylhydrazyl) assay, and the tannin content was determined by the radial diffusion method. Plants with better antioxidant activity (expressed in a dose able to decrease the initial DPPH concentration by 50%, or IC50) and with higher levels of tannins were: Poincianella pyramidalis (42.95±1.77 µg/mL IC50 and 8.17±0.64 tannin content), Jatropha mollissima (54.09±4.36µg/mL IC50 and 2.35±0.08 tannin content) and Anadenanthera colubrina (73.24±1.47 µg/mL IC50 and 4.41±0.47 tannin content). Plants with enhanced antiproliferative activity (% living cells) were Annona muricata (24.94±0.74 in NCI-H292), Lantana camara (25.8±0.19 in NCI-H292), Handroanthus impetiginosus (41.8±0.47 in NCI-H292) and Mentzelia aspera (45.61±1.94 in HEp-2). For species with better antioxidant and antiproliferative activities, we suggest future in vitro and in vivo comparative studies with other pharmacological models, and to start a process of purification and identification of the possible molecule(s) responsible for the observed pharmacological activity. We believe that the flora of Brazilian semi-arid areas can be a valuable source of plants rich in tannins, cytotoxic compounds and antioxidant agents.

Condensed tannins from mangrove species Kandelia candel and Rhizophora mangle and their antioxidant activity.

PubMed

Zhang, Liang-Liang; Lin, Yi-Ming; Zhou, Hai-Chao; Wei, Shu-Dong; Chen, Jia-Hong

2010-01-20

The structures of condensed tannins isolated from two mangrove species, Kandelia candel and Rhizophora mangle, were characterized by 13C nuclear magnetic resonance (NMR) spectroscopy and matrix assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses. Results demonstrate that large heterogeneity occurs in degree of polymerization, pattern of hydroxylation, and substitution with monosaccharides in the structures of the condensed tannins. Condensed tannin oligomers from K. candel and R. mangle were shown to be heterogeneous mixtures consisting of procyanidin and prodelphinidin structural units with the former dominating. The MALDI-TOF mass spectra contained masses corresponding to a distinct oligomeric series of glycosylated heteropoly flavan units. In addition, condensed tannins from two mangrove plants were screened for their potential antioxidant activities using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) model systems.

Determination of hydrolyzable tannins (gallotannins and ellagitannins) after reaction with potassium iodate.

PubMed

Hartzfeld, Paul W; Forkner, Rebecca; Hunter, Mark D; Hagerman, Ann E

2002-03-27

A widely used method for analyzing hydrolyzable tannins afer reaction with KIO(3) has been modified to include a methanolysis step followed by oxidation with KIO(3). In the new method, hydrolyzable tannins (gallotannins and ellagitannins) are reacted at 85 degrees C for 20 h in methanol/sulfuric acid to quantitatively release methyl gallate. Dried plant samples can be methanolyzed under the same conditions to convert hydrolyzable tannins to methyl gallate. Oxidation of the methyl gallate by KIO(3) at pH 5.5, 30 degrees C, forms a chromophore with lambda(max) 525 nm, which is determined spectrophotometrically. The detection limit of the method is 1.5 microg of methyl gallate, and with plant samples, relative standard deviations of less than 3% were obtained.

Kinetics of non-catalyzed hydrolysis of tannin in high temperature liquid water*

PubMed Central

Lu, Li-li; Lu, Xiu-yang; Ma, Nan

2008-01-01

High temperature liquid water (HTLW) has drawn increasing attention as an environmentally benign medium for organic chemical reactions, especially acid-/base-catalyzed reactions. Non-catalyzed hydrolyses of gallotannin and tara tannin in HTLW for the simultaneous preparation of gallic acid (GA) and pyrogallol (PY) are under investigation in our laboratory. In this study, the hydrolysis kinetics of gallotannin and tara tannin were determined. The reaction is indicated to be a typical consecutive first-order one in which GA has formed as a main intermediate and PY as the final product. Selective decomposition of tannin in HTLW was proved to be possible by adjusting reaction temperature and time. The present results provide an important basic data and reference for the green preparation of GA and PY. PMID:18500780

Quantitation of sweet steviol glycosides by means of a HILIC-MS/MS-SIDA approach.

PubMed

Well, Caroline; Frank, Oliver; Hofmann, Thomas

2013-11-27

Meeting the rising consumer demand for natural food ingredients, steviol glycosides, the sweet principle of Stevia rebaudiana Bertoni (Bertoni), have recently been approved as food additives in the European Union. As regulatory constraints require sensitive methods to analyze the sweet-tasting steviol glycosides in foods and beverages, a HILIC-MS/MS method was developed enabling the accurate and reliable quantitation of the major steviol glycosides stevioside, rebaudiosides A-F, steviolbioside, rubusoside, and dulcoside A by using the corresponding deuterated 16,17-dihydrosteviol glycosides as suitable internal standards. This quantitation not only enables the analysis of the individual steviol glycosides in foods and beverages but also can support the optimization of breeding and postharvest downstream processing of Stevia plants to produce preferentially sweet and least bitter tasting Stevia extracts.

The swarming motility of Pseudomonas aeruginosa is blocked by cranberry proanthocyanidins and other tannin-containing materials.

PubMed

O'May, Che; Tufenkji, Nathalie

2011-05-01

Bacterial motility plays a key role in the colonization of surfaces by bacteria and the subsequent formation of resistant communities of bacteria called biofilms. Derivatives of cranberry fruit, predominantly condensed tannins called proanthocyanidins (PACs) have been reported to interfere with bacterial adhesion, but the effects of PACs and other tannins on bacterial motilities remain largely unknown. In this study, we investigated whether cranberry PAC (CPAC) and the hydrolyzable tannin in pomegranate (PG; punicalagin) affected the levels of motilities exhibited by the bacterium Pseudomonas aeruginosa. This bacterium utilizes flagellum-mediated swimming motility to approach a surface, attaches, and then further spreads via the surface-associated motilities designated swarming and twitching, mediated by multiple flagella and type IV pili, respectively. Under the conditions tested, both CPAC and PG completely blocked swarming motility but did not block swimming or twitching motilities. Other cranberry-containing materials and extracts of green tea (also rich in tannins) were also able to block or impair swarming motility. Moreover, swarming bacteria were repelled by filter paper discs impregnated with many tannin-containing materials. Growth experiments demonstrated that the majority of these compounds did not impair bacterial growth. When CPAC- or PG-containing medium was supplemented with surfactant (rhamnolipid), swarming motility was partially restored, suggesting that the effective tannins are in part acting by a rhamnolipid-related mechanism. Further support for this theory was provided by demonstrating that the agar surrounding tannin-induced nonswarming bacteria was considerably less hydrophilic than the agar area surrounding swarming bacteria. This is the first study to show that natural compounds containing tannins are able to block P. aeruginosa swarming motility and that swarming bacteria are repelled by such compounds.

The Swarming Motility of Pseudomonas aeruginosa Is Blocked by Cranberry Proanthocyanidins and Other Tannin-Containing Materials▿

PubMed Central

O'May, Che; Tufenkji, Nathalie

2011-01-01

Bacterial motility plays a key role in the colonization of surfaces by bacteria and the subsequent formation of resistant communities of bacteria called biofilms. Derivatives of cranberry fruit, predominantly condensed tannins called proanthocyanidins (PACs) have been reported to interfere with bacterial adhesion, but the effects of PACs and other tannins on bacterial motilities remain largely unknown. In this study, we investigated whether cranberry PAC (CPAC) and the hydrolyzable tannin in pomegranate (PG; punicalagin) affected the levels of motilities exhibited by the bacterium Pseudomonas aeruginosa. This bacterium utilizes flagellum-mediated swimming motility to approach a surface, attaches, and then further spreads via the surface-associated motilities designated swarming and twitching, mediated by multiple flagella and type IV pili, respectively. Under the conditions tested, both CPAC and PG completely blocked swarming motility but did not block swimming or twitching motilities. Other cranberry-containing materials and extracts of green tea (also rich in tannins) were also able to block or impair swarming motility. Moreover, swarming bacteria were repelled by filter paper discs impregnated with many tannin-containing materials. Growth experiments demonstrated that the majority of these compounds did not impair bacterial growth. When CPAC- or PG-containing medium was supplemented with surfactant (rhamnolipid), swarming motility was partially restored, suggesting that the effective tannins are in part acting by a rhamnolipid-related mechanism. Further support for this theory was provided by demonstrating that the agar surrounding tannin-induced nonswarming bacteria was considerably less hydrophilic than the agar area surrounding swarming bacteria. This is the first study to show that natural compounds containing tannins are able to block P. aeruginosa swarming motility and that swarming bacteria are repelled by such compounds. PMID:21378043

Dietary crude protein and tannin impact dairy manure chemistry and ammonia emissions from incubated soils.

PubMed

Powell, J M; Aguerre, M J; Wattiaux, M A

2011-01-01

Excess crude protein (CP) in dairy cow diets is excreted mostly as urea nitrogen (N), which increases ammonia (NH) emissions from dairy farms and heightens human health and environmental concerns. Feeding less CP and more tannin to dairy cows may enhance feed N use and milk production, abate NH emissions, and conserve the fertilizer N value of manure. Lab-scale ventilated chambers were used to evaluate the impacts of CP and tannin feeding on slurry chemistry, NH emissions, and soil inorganic N levels after slurry application to a sandy loam soil and a silt loam soil. Slurry from lactating Holstein dairy cows (Bos taurus) fed two levels of dietary CP (low CP [LCP], 155 g kg; high CP [HCP], 168 g kg) each fed at four levels of dietary tannin extract, a mixture from red quebracho (Schinopsis lorentzii) and chestnut (Castanea sativa) trees (0 tannin [0T]; low tannin [LT], 4.5 g kg; medium tannin [MT], 9.0 g kg; and high tannin [HT], 18.0 g kg) were applied to soil-containing lab-scale chambers, and NH emissions were measured 1, 3, 6, 12, 24, 36, and 48 h after slurry application. Emissions from the HCP slurry were 1.53 to 2.57 times greater ( < 0.05) than from the LCP slurry. At trial's end (48 h), concentrations of inorganic N in soils were greater ( < 0.05) in HCP slurry-amended soils than in LCP slurry-amended soils. Emissions from HT slurry were 28 to 49% lower ( < 0.05) than emissions from 0T slurry, yet these differences did not affect soil inorganic N levels. Emissions from the sandy loam soil were 1.07 to 1.15 times greater ( < 0.05) than from silt loam soil, a result that decreased soil inorganic N in the sandy loam compared with the silt loam soil. Larger-scale and longer-term field trails are needed to ascertain the effectiveness of feeding tannin extracts to dairy cows in abating NH loss from land-applied slurry and the impact of tannin-containing slurry on soil N cycles. Copyright © by the American Society of Agronomy, Crop Science Society of America, and

Flavonol Glycosides from Gaura Biennis

USDA-ARS?s Scientific Manuscript database

Phytochemical investigation of the native American plant Gaura biennis led to the isolation of three new flavonol glycosides (1-3), along with eight known ones. Their structures were established primarily by spectroscopic data as quercetin 3-O-(2"-O-a-L-rhamnopyranosyl-6"-O-E-p-coumaroyl)-ß-D- gluco...

Transition of phenolics and cyanogenic glycosides from apricot and cherry fruit kernels into liqueur.

PubMed

Senica, Mateja; Stampar, Franci; Veberic, Robert; Mikulic-Petkovsek, Maja

2016-07-15

Popular liqueurs made from apricot/cherry pits were evaluated in terms of their phenolic composition and occurrence of cyanogenic glycosides (CGG). Analyses consisted of detailed phenolic and cyanogenic profiles of cherry and apricot seeds as well as beverages prepared from crushed kernels. Phenolic groups and cyanogenic glycosides were analyzed with the aid of high-performance liquid chromatography (HPLC) and mass spectrophotometry (MS). Lower levels of cyanogenic glycosides and phenolics have been quantified in liqueurs compared to fruit kernels. During fruit pits steeping in the alcohol, the phenolics/cyanogenic glycosides ratio increased and at the end of beverage manufacturing process higher levels of total analyzed phenolics were detected compared to cyanogenic glycosides (apricot liqueur: 38.79 μg CGG per ml and 50.57 μg phenolics per ml; cherry liqueur 16.08 μg CGG per ml and 27.73 μg phenolics per ml). Although higher levels of phenolics are characteristic for liqueurs made from apricot and cherry pits these beverages nevertheless contain considerable amounts of cyanogenic glycosides. Copyright © 2016 Elsevier Ltd. All rights reserved.

Phenylethanoid glycosides from Phlomis integrifolia Hub.-Mor.

PubMed

Saracoglu, Iclal; Varel, Mehtap; Hada, Junko; Hada, Noriyasu; Takeda, Tadahiro; Donmez, Ali A; Calis, Ihsan

2003-01-01

Two new phenylethanoid glycosides integrifoliosides A (2) and B (3), along with a known phenylethanoid glycoside alyssonoside (1) and a flavone glucoside chrysoeriol-7-O-beta-D-glucopyranoside (4) were isolated from the aerial parts of Phlomis integrifolia. The structures of the new compounds were identified as 3,4-dihydroxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 3)-4-O-feruloyl-beta-D-glucopyranoside (2) and 3-hydroxy-4-methoxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 3)-4-O-feruloyl-beta-D-glucopyranoside (3), on the basis of spectroscopic (UV, IR, 1D- and 2D-NMR, and HR-FABMS) methods.

Characterisation of the ruminal fermentation and microbiome in lambs supplemented with hydrolysable and condensed tannins.

PubMed

Salami, Saheed A; Valenti, Bernardo; Bella, Marco; O'Grady, Michael N; Luciano, Giuseppe; Kerry, Joseph P; Jones, Eleanor; Priolo, Alessandro; Newbold, Charles J

2018-05-01

This study characterised the response of ruminal fermentation and the rumen microbiome in lambs fed commercial vegetal sources of hydrolysable tannins (HT) and condensed tannins (CT). Forty-four lambs (19.56 ± 2.06 kg) were randomly assigned to either a concentrate diet (CON, n = 8) or CON supplemented with 4% of two HT [chestnut (Castanea sativa, HT-c) and tara (Caesalpinia spinosa, HT-t)] and CT [mimosa (Acacia negra, CT-m) and gambier (Uncaria gambir, CT-g)] extracts (all, n = 9) for 75 days pre-slaughter. Tannin supplementation did not influence ruminal fermentation traits. Quantitative PCR demonstrated that tannins did not affect the absolute abundance of ruminal bacteria or fungi. However, CT-m (-12.8%) and CT-g (-11.5%) significantly reduced the abundance of methanogens, while HT-t (-20.7%) and CT-g (-20.8%) inhibited protozoal abundance. Ribosomal amplicon sequencing revealed that tannins caused changes in the phylogenetic structure of the bacterial and methanogen communities. Tannins inhibited the fibrolytic bacterium, Fibrobacter and tended to suppress the methanogen genus, Methanosphaera. Results demonstrated that both HT and CT sources could impact the ruminal microbiome when supplemented at 4% inclusion level. HT-t, CT-m and CT-g extracts displayed specific antimicrobial activity against methanogens and protozoa without compromising ruminal fermentation in a long-term feeding trial.

Levels of Tannins and Flavonoids in Medicinal Plants: Evaluating Bioprospecting Strategies

PubMed Central

Siqueira, Clarissa Fernanda de Queiroz; Cabral, Daniela Lyra Vasconcelos; Peixoto Sobrinho, Tadeu José da Silva; de Amorim, Elba Lúcia Cavalcanti; de Melo, Joabe Gomes; Araújo, Thiago Antônio de Sousa; de Albuquerque, Ulysses Paulino

2012-01-01

There are several species of plants used by traditional communities in the Brazilian semiarid. An approach used in the search for natural substances that possess therapeutic value is ethnobotany or ethnopharmacology. Active substances that have phenolic groups in their structure have great pharmacological potential. To establish a quantitative relationship between the species popularly considered to be antimicrobial, antidiabetic, and antidiarrheal, the contents of tannins and flavonoids were determined. The plant selection was based on an ethnobotanical survey conducted in a community located in the municipality of Altinho, northeastern Brazil. For determination of tannin content was utilized the technique of radial diffusion, and for flavonoids, an assay based on the complexation of aluminum chloride. The group of plants with antimicrobial indications showed a higher content of tannins compared to the control groups. The results evidence suggests a possible relationship between these compounds and the observed activity. PMID:21969842

Effects of tannins on fruit selection in three southern African frugivorous birds.

PubMed

Zungu, Manqoba M; Downs, Colleen T

2015-02-01

Tannins are common secondary compounds in plant material and are known for their ability to bind to protein which reduces nitrogen availability in the diet. In fruits, these compounds are responsible for their astringency which is thought to result in reduced food intake. In this study, the repellent effects of tannins were examined in three species of frugivorous birds: red-winged starlings Onychognathus morio, speckled mousebirds Colius striatus and Cape white-eyes Zosterops virens. Birds were fed artificial fruit diets containing varying levels of tannins in paired choice tests with the amount of food eaten by birds used to determine preference. Red-winged starlings were attracted to the control diet, indifferent to the medium tannin diet and deterred by the high tannin diet whereas speckled mousebirds and Cape white-eyes were not deterred at all concentrations. The discrepancy in the results was attributed to differences in taste sensitivity, tolerance levels and detoxification mechanisms of secondary compounds between species. Because fruit selection and ultimately fruit removal rates affect plant community composition, the disparity in the results suggests that frugivorous birds do not contribute equally to plant community dynamics. However, plant secondary compounds in fruits are diverse and their effects are similarly diverse and there is potential that different groups of secondary compounds generate disparate effects. Similar studies on other types of secondary compounds may thus contribute towards a broader understanding of the role of secondary compounds in mediating fruit-frugivore interactions. Copyright © 2014 Elsevier B.V. All rights reserved.

Habitat influence on antioxidant activity and tannin concentrations of Spondias tuberosa.

PubMed

de Sousa Araújo, Thiago Antônio; de Almeida e Castro, Valerium Thijan Nobre; de Amorim, Elba Lúcia Cavalcanti; de Albuquerque, Ulysses Paulino

2012-06-01

Different habitat conditions can be responsible for the production of secondary metabolites and for the antioxidant properties of plant products. Thus, the aim of this study was to evaluate whether the antioxidant activity and tannin concentrations in the stem bark of Spondias tuberosa Arruda (Anacardiaceae) varied with collection site. The bark was collected from 25 individual trees, distributed in five different landscape units, as follows: agroforestry gardens, areas of pastures, maize cultivation areas, mountain areas and mountain bases, with the former 3 being considered as anthropogenic habitats, and the latter 2 considered as habitats with native coverage. The study was conducted in the rural area of the city of Altinho, Pernambuco State (Northeast Brazil). The DPPH (1,1-diphenyl-2-picrylhydrazyl) method was used to measure the antioxidant activity and tannin concentrations were evaluated by using the radial diffusion method. The results demonstrated that there were no significant differences among the tannin concentrations of the individuals from the native (6.27% ± 1.75) or anthropogenic areas (4.63% ± 2.55), (H = 2.24; p > 0.05). In contrast, there were significant differences (H = 5.1723; p < 0.05) among the CE₅₀ means of the antioxidant activities of the individuals from the native (32.10 µg/ml ± 5.27) and anthropogenic areas (27.07 µg/ml ± 2.29). However, correlations between the tannin concentrations and antioxidant activity of the extracts were not observed in the native (r = 0.39; p > 0.05) or in the anthropogenic areas (r = 0.38; p > 0.05). Because the variation of the antioxidant capacity of S. tuberosa bark was not accompanied by a variation in the tannin concentration, this property may be related to the presence of other metabolite(s).

Tannin extracts from immature fruits of Terminalia chebula Fructus Retz. promote cutaneous wound healing in rats

PubMed Central

2011-01-01

Background Tannins extracted from immature fruits of Terminalia chebula Fructus Retz. are considered as effective components promoting the process of wound healing. The objective of this study is to explore the optimal extraction and purification technology (OEPT) of tannins, while studying the use of this drug in the treatment of a cutaneous wound of rat as well as its antibacterial effects. Methods The content of tannin extracts was measured by the casein method, and antibacterial ability was studied by the micro-dilution method in vitro. In wound healing experiment, animals in group Ⅰ, Ⅱ and Ⅲ were treated with vaseline ointment, tannin extracts (tannin content: 81%) and erythromycin ointment, respectively (5 mg of ointment were applied on each wound). To evaluate the process of wound healing, selected pharmacological and biochemical parameters were applied. Results After optimal extraction and purification, content of tannin extracts was increased to 81%. Tannin extracts showed the inhibition of Staphylococcus aureus and Klebsiella Pneumonia in vitro. After excision of wounds, on days 7 and 10, the percent of wound contraction of group Ⅱ was higher than that of group Ⅰ. After being hurt with wounds, on days 3, 7, and 10, the wound healing quality of group Ⅱ was found to be better than that of group Ⅰ in terms of granulation formation and collagen organization. After wound creation, on day 3, the vascular endothelial growth factor expression of group Ⅱ was higher than that of group Ⅰ. Conclusion The results suggest that tannin extracts from dried immature fruits of Terminalia chebula Fructus Retz. can promote cutaneous wound healing in rats, probably resulting from a powerful anti-bacterial and angiogenic activity of the extracts. PMID:21982053

Direct anthelmintic effects of condensed tannins from diverse plant sources against Ascaris suum.

PubMed

Williams, Andrew R; Fryganas, Christos; Ramsay, Aina; Mueller-Harvey, Irene; Thamsborg, Stig M

2014-01-01

Ascaris suum is one of the most prevalent nematode parasites in pigs and causes significant economic losses, and also serves as a good model for A. lumbricoides, the large roundworm of humans that is ubiquitous in developing countries and causes malnutrition, stunted growth and compromises immunity to other pathogens. New treatment options for Ascaris infections are urgently needed, to reduce reliance on the limited number of synthetic anthelmintic drugs. In areas where Ascaris infections are common, ethno-pharmacological practices such as treatment with natural plant extracts are still widely employed. However, scientific validation of these practices and identification of the active compounds are lacking, although observed effects are often ascribed to plant secondary metabolites such as tannins. Here, we extracted, purified and characterised a wide range of condensed tannins from diverse plant sources and investigated anthelmintic effects against A. suum in vitro. We show that condensed tannins can have potent, direct anthelmintic effects against A. suum, as evidenced by reduced migratory ability of newly hatched third-stage larvae and reduced motility and survival of fourth-stage larvae recovered from pigs. Transmission electron microscopy showed that CT caused significant damage to the cuticle and digestive tissues of the larvae. Furthermore, we provide evidence that the strength of the anthelmintic effect is related to the polymer size of the tannin molecule. Moreover, the identity of the monomeric structural units of tannin polymers may also have an influence as gallocatechin and epigallocatechin monomers exerted significant anthelmintic activity whereas catechin and epicatechin monomers did not. Therefore, our results clearly document direct anthelmintic effects of condensed tannins against Ascaris and encourage further in vivo investigation to determine optimal strategies for the use of these plant compounds for the prevention and/or treatment of

Direct Anthelmintic Effects of Condensed Tannins from Diverse Plant Sources against Ascaris suum

PubMed Central

Williams, Andrew R.; Fryganas, Christos; Ramsay, Aina; Mueller-Harvey, Irene; Thamsborg, Stig M.

2014-01-01

Ascaris suum is one of the most prevalent nematode parasites in pigs and causes significant economic losses, and also serves as a good model for A. lumbricoides, the large roundworm of humans that is ubiquitous in developing countries and causes malnutrition, stunted growth and compromises immunity to other pathogens. New treatment options for Ascaris infections are urgently needed, to reduce reliance on the limited number of synthetic anthelmintic drugs. In areas where Ascaris infections are common, ethno-pharmacological practices such as treatment with natural plant extracts are still widely employed. However, scientific validation of these practices and identification of the active compounds are lacking, although observed effects are often ascribed to plant secondary metabolites such as tannins. Here, we extracted, purified and characterised a wide range of condensed tannins from diverse plant sources and investigated anthelmintic effects against A. suum in vitro. We show that condensed tannins can have potent, direct anthelmintic effects against A. suum, as evidenced by reduced migratory ability of newly hatched third-stage larvae and reduced motility and survival of fourth-stage larvae recovered from pigs. Transmission electron microscopy showed that CT caused significant damage to the cuticle and digestive tissues of the larvae. Furthermore, we provide evidence that the strength of the anthelmintic effect is related to the polymer size of the tannin molecule. Moreover, the identity of the monomeric structural units of tannin polymers may also have an influence as gallocatechin and epigallocatechin monomers exerted significant anthelmintic activity whereas catechin and epicatechin monomers did not. Therefore, our results clearly document direct anthelmintic effects of condensed tannins against Ascaris and encourage further in vivo investigation to determine optimal strategies for the use of these plant compounds for the prevention and/or treatment of

Interspecific differences in tannin intakes of forest-dwelling rodents in the wild revealed by a new method using fecal proline content.

PubMed

Shimada, Takuya; Nishii, Eriko; Saitoh, Takashi

2011-12-01

Mammalian herbivores adopt various countermeasures against dietary tannins, which are among the most widespread plant secondary metabolites. The large Japanese wood mouse Apodemus speciosus produces proline-rich salivary tannin-binding proteins in response to tannins. Proline-rich proteins (PRPs) react with tannins to form stable complexes that are excreted in the feces. Here, we developed a new method for estimating the tannin intake of free-living small rodents, by measuring fecal proline content, and applied the method to a field investigation. A feeding experiment with artificial diets containing various levels of tannic acid revealed that fecal proline content was clearly related to dietary tannin content in three species (A. speciosus, Apodemus argenteus, and Myodes rufocanus). We then used fecal proline content to estimate the tannin intakes of these three forest-dwelling species in a forest in Hokkaido. In the autumn, estimated tannin intakes increased significantly in the Apodemus species, but not in M. rufocanus. We speculated that an increase in tannin intake during autumn may result from consumption of tannin-rich acorns. This hypothesis was consistent with population fluctuation patterns of the three species, which were well-synchronized with acorn abundance for the Apodemus species but not for M. rufocanus.

New procyanidin B3-human salivary protein complexes by mass spectrometry. Effect of salivary protein profile, tannin concentration, and time stability.

PubMed

Perez-Gregorio, Maria Rosa; Mateus, Nuno; De Freitas, Victor

2014-10-15

Several factors could influence the tannin-protein interaction such as the human salivary protein profile, the tannin tested, and the tannin/protein ratio. The goal of this study aims to study the effect of different salivas (A, B, and C) and different tannin concentrations (0.5 and 1 mg/mL) on the interaction process as well as the complex's stability over time. This study is focused on the identification of new procyanidin B3-human salivary protein complexes. Thus, 48 major B3-human salivary protein aggregates were identified regardless of the saliva and tannin concentration tested. A higher number of aggregates was found at lower tannin concentration. Moreover, the number of protein moieties involved in the aggregation process was higher when the tannin concentration was also higher. The selectivity of the different groups of proteins to bind tannin was also confirmed. It was also verified that the B3-human salivary protein complexes formed evolved over time.

Bacterial and protozoal communities and fatty acid profile in the rumen of sheep fed a diet containing added tannins.

PubMed

Vasta, Valentina; Yáñez-Ruiz, David R; Mele, Marcello; Serra, Andrea; Luciano, Giuseppe; Lanza, Massimiliano; Biondi, Luisa; Priolo, Alessandro

2010-04-01

This study evaluated the effects of tannins on ruminal biohydrogenation (BH) due to shifts in the ruminal microbial environment in sheep. Thirteen lambs (45 days of age) were assigned to two dietary treatments: seven lambs were fed a barley-based concentrate (control group) while the other six lambs received the same concentrate with supplemental quebracho tannins (9.57% of dry matter). At 122 days of age, the lambs were slaughtered, and the ruminal contents were subjected to fatty acid analysis and sampled to quantify populations of Butyrivibrio fibrisolvens, which converts C(18:2) c9-c12 (linoleic acid [LA]) to C(18:2) c9-t11 (rumenic acid [RA]) and then RA to C(18:1) t11 (vaccenic acid [VA]); we also sampled for Butyrivibrio proteoclasticus, which converts VA to C(18:0) (stearic acid [SA]). Tannins increased (P < 0.005) VA in the rumen compared to the tannin-free diet. The concentration of SA was not affected by tannins. The SA/VA ratio was lower (P < 0.005) for the tannin-fed lambs than for the controls, suggesting that the last step of the BH process was inhibited by tannins. The B. proteoclasticus population was lower (-30.6%; P < 0.1), and B. fibrisolvens and protozoan populations were higher (+107% and +56.1%, respectively; P < 0.05) in the rumen of lambs fed the tannin-supplemented diet than in controls. These results suggest that quebracho tannins altered BH by changing ruminal microbial populations.

Folding of a salivary intrinsically disordered protein upon binding to tannins.

PubMed

Canon, Francis; Ballivian, Renaud; Chirot, Fabien; Antoine, Rodolphe; Sarni-Manchado, Pascale; Lemoine, Jérôme; Dugourd, Philippe

2011-05-25

We used ion mobility spectrometry to explore conformational adaptability of intrinsically disordered proteins bound to their targets in complex mixtures. We investigated the interactions between a human salivary proline-rich protein IB5 and a model of wine and tea tannin: epigallocatechin gallate (EgCG). Collisional cross sections of naked IB5 and IB5 complexed with N = 1-15 tannins were recorded. The data demonstrate that IB5 undergoes an unfolded to folded structural transition upon binding with EgCG.

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

PubMed

Ito, Hideyuki; Yamaguchi, Koji; Kim, Tae-Hoon; Khennouf, Seddik; Gharzouli, Kamel; Yoshida, Takashi

2002-03-01

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

Cardiac glycoside overdose

MedlinePlus

... hot summer months). This problem usually occurs in older people. This is for information only and not for ... Symptoms may be vague, especially in the older people. They may occur in ... (*) next to them usually occur only in chronic overdoses. ...

Activity, purification, and analysis of condensed tannins

USDA-ARS?s Scientific Manuscript database

As a class of plant polyphenolic compounds contained in some forages (i.e., sanfoin, big trefoil, birdfoot trefoil), condensed tannins (CTs), also referred to as proanthocyanidins (PAs), exhibit a variety of biological effects on ruminants and on the dairy farm nitrogen cycle. Interest in CTs stems ...

The BaeSR Two-Component Regulatory System Mediates Resistance to Condensed Tannins in Escherichia coli▿ †

PubMed Central

Zoetendal, Erwin G.; Smith, Alexandra H.; Sundset, Monica A.; Mackie, Roderick I.

2008-01-01

The gene expression profiles of Escherichia coli strains grown anaerobically with or without Acacia mearnsii (black wattle) extract were compared to identify tannin resistance strategies. The cell envelope stress protein gene spy and the multidrug transporter-encoding operon mdtABCD, both under the control of the BaeSR two-component regulatory system, were significantly up-regulated in the presence of tannins. BaeSR mutants were more tannin sensitive than their wild-type counterparts. PMID:18039828

Bioactive amines in sorghum: method optimisation and influence of line, tannin and hydric stress.

PubMed

Paiva, Caroline Liboreiro; Evangelista, Warlley Pinheiro; Queiroz, Valéria Aparecida Vieira; Glória, Maria Beatriz Abreu

2015-04-15

The profile and levels of bioactive amines in different sorghum lines were reported for the first time. The amines were quantified by ion-pair HPLC, post-column derivatisation with o-phthalaldehyde and fluorimetric detection. The extraction procedure was optimised: 420 μm particle size, extraction with 5% trichloroacetic acid and three extractions. The screening of 22 sorghum lines showed that four of the ten amines investigated were detected. Spermine and spermidine were the prevalent amines (100%), followed by putrescine (77%) and cadaverine (14%). Total amines ranged from 5.8 to 41.4 mg/100 g, and the polyamines represented 60-100% of the total. Sorghum without tannin had higher amines levels compared to sorghum with tannin and cadaverine was specific to samples without tannin. Hydric stress caused accumulation of spermidine in the grains and affected the levels of other amines at rates depending on the presence or not of tannin. Sorghum is a significant source of polyamines. Copyright © 2014 Elsevier Ltd. All rights reserved.

How bonobo communities deal with tannin rich fruits: Re-ingestion and other feeding processes.

PubMed

Beaune, David; Hohmann, Gottfried; Serckx, Adeline; Sakamaki, Tetsuya; Narat, Victor; Fruth, Barbara

2017-09-01

This report describes bonobo (Pan paniscus, Hominidae) behavioral flexibility and inter-community differences with high tannin level fruit processing. In fruiting plants, tannin should discourage certain seed dispersers (direct deterrence hypothesis) such as primates. Based on data deriving from five study sites; LuiKotale, Lomako, Wamba, Malebo and Manzano, we compare consumption and dispersal of fruit species rich in tannins: Parinari and Musanga pulp was chewed across all communities probably for saliva tannin neutralisation. However, consumption of the fruits of Canarium schweinfurthii was observed in few communities only with differences in the food process: While bonobos of Wamba, Lomako and Manzano crunched and swallowed the pulp, bonobos of LuiKotale ingested entire fruits, extracted intact fruits from feces, and re-ingested their pulp, spitting the seed after a retention time of 24h in the digestive tract (i.e. endozoochory). We discuss potential functions of this peculiar feeding technique, likely to be a cultural behavior. Copyright © 2017 Elsevier B.V. All rights reserved.

Valorization of Tunisian alfa fibres and sumac tannins for the elaboration of biodegradable insulating panels

NASA Astrophysics Data System (ADS)

Saad, Houda; Charrier, Bertrand; Ayed, Naceur; Charrier-El-Bouhtoury, Fatima

2017-10-01

Alfa leaves are important renewable raw materials in Tunisia where they are used basically in handcrafts and paper industry. Sumac is also an abundant species in Tunisia known for its high tannin content and is basically used in traditional medicine. To valorize these natural resources, we studied, for the first time, the possibility of making insulating panels based on alfa fibres and sumac tannins based adhesive. Firstly, alfa leaves were treated with an alkali solution as it is one of the standard procedures commonly used in the paper industry to extract cellulosic fibres. Mercerization effects were studied by characterizing fibres thermal properties and fibres surface morphology. Secondly, the sumac tannin based resin was formulated and characterized. Finally, the insulating panel was elaborated and characterized by determining its thermal conductivity. The thermal gravimetric analysis results show improvement in the thermal stability of fibres after alkali treatment. Environmental Scanning Electron Microscopy showed changes on treated alfa surface which could promote the fibre-matrix adhesion. The reactivity of sumac tannins to formaldehyde test (Stiasny number) showed the possible use of sumac tannins in wood adhesive formulation. Thermomechanical analysis and strength analysis of sumac tannin/hexamin based resin highlighted acceptable bonding properties. The thermal conductivity measurement showed an average value equal to 0.110 W/m K. Contribution to the topical issue "Materials for Energy harvesting, conversion and storage II (ICOME 2016)", edited by Jean-Michel Nunzi, Rachid Bennacer and Mohammed El Ganaoui

Comparative study of wine tannin classification using Fourier transform mid-infrared spectrometry and sensory analysis.

PubMed

Fernández, Katherina; Labarca, Ximena; Bordeu, Edmundo; Guesalaga, Andrés; Agosin, Eduardo

2007-11-01

Wine tannins are fundamental to the determination of wine quality. However, the chemical and sensorial analysis of these compounds is not straightforward and a simple and rapid technique is necessary. We analyzed the mid-infrared spectra of white, red, and model wines spiked with known amounts of skin or seed tannins, collected using Fourier transform mid-infrared (FT-MIR) transmission spectroscopy (400-4000 cm(-1)). The spectral data were classified according to their tannin source, skin or seed, and tannin concentration by means of discriminant analysis (DA) and soft independent modeling of class analogy (SIMCA) to obtain a probabilistic classification. Wines were also classified sensorially by a trained panel and compared with FT-MIR. SIMCA models gave the most accurate classification (over 97%) and prediction (over 60%) among the wine samples. The prediction was increased (over 73%) using the leave-one-out cross-validation technique. Sensory classification of the wines was less accurate than that obtained with FT-MIR and SIMCA. Overall, these results show the potential of FT-MIR spectroscopy, in combination with adequate statistical tools, to discriminate wines with different tannin levels.

Effect of yeast strain and some nutritional factors on tannin composition and potential astringency of model wines.

PubMed

Rinaldi, Alessandra; Blaiotta, Giuseppe; Aponte, Maria; Moio, Luigi

2016-02-01

Nine Saccharomyces cerevisiae cultures, isolated from different sources, were tested for their ability to reduce tannins reactive towards salivary proteins, and potentially responsible for wine astringency. Strains were preliminary genetically characterized and evaluated for physiological features of technological interest. Laboratory-scale fermentations were performed in three synthetic media: CT) containing enological grape tannin; CTP) CT supplemented with organic nitrogen sources; CTPV) CTP supplemented with vitamins. Adsorption of total tannins, tannins reactive towards salivary proteins, yellow pigments, phenolics having antioxidant activity, and total phenols, characterizing the enological tannin, was determined by spectrophotometric methods after fermentation. The presence of vitamins and peptones in musts greatly influenced the adsorption of tannins reactive towards salivary proteins (4.24 g/L gallic acid equivalent), thus promoting the reduction of the potential astringency of model wines. With reference to the different phenolic classes, yeast strains showed different adsorption abilities. From a technological point of view, the yeast choice proved to be crucial in determining changes in gustative and mouthfeel profile of red wines and may assist winemakers to modulate colour and astringency of wine. Copyright © 2015 Elsevier Ltd. All rights reserved.

Selective detection and recovery of gold at tannin-immobilized non-conducting electrode.

PubMed

Banu, Khaleda; Shimura, Takayoshi; Sadeghi, Saman

2015-01-01

A tannin-immobilized glassy carbon electrode (TIGC) was prepared via electrochemical oxidation of the naturally occurring polyphenolic mimosa tannin, which generated a non-conducting polymeric film (NCPF) on the electrode surface. The fouling of the electrode surface by the electropolymerized film was evaluated by monitoring the electrode response of ferricyanide ions as a redox marker. The NCPF was permselective to HAuCl4, and the electrochemical reduction of HAuCl4 to metallic gold at the TIGC electrode was evaluated by recording the reduction current during cyclic voltammetry measurement. In the mixed electrolyte containing HAuCl4 along with FeCl3 and/or CuCl2, the NCPF remained selective toward the electrochemical reduction of HAuCl4 into the metallic state. The chemical reduction of HAuCl4 into metallic gold was also observed when the NCPF was inserted into an acidic gold solution overnight. The adsorption capacity of Au(III) on tannin-immobilized carbon fiber was 29±1.45 mg g(-1) at 60°C. In the presence of excess Cu(II) and Fe(III), tannin-immobilized NCPF proved to be an excellent candidate for the selective detection and recovery of gold through both electrochemical and chemical processes. Copyright © 2014 Elsevier B.V. All rights reserved.

Functional properties and in vitro antioxidant and antibacterial effectiveness of pigskin gelatin films incorporated with hydrolysable chestnut tannin.

PubMed

Peña-Rodriguez, Cristina; Martucci, Josefa F; Neira, Laura M; Arbelaiz, Aitor; Eceiza, Arantxa; Ruseckaite, Roxana A

2015-04-01

The impact of the incorporation of 10% w/w of hydrolyzable chestnut tannin into pigskin gelatin (G) films plasticized with glycerol (Gly) on the physicochemical properties as well as the in vitro antioxidant and antibacterial effectiveness against food-borne pathogens such as Escherichia coli and Streptococcus aureus was investigated. A higher tendency to both redness (a*) and yellowness (b*) coloration characterized gelatin films incorporated with chestnut tannin. The reduced lightness (L) and transparency of gelatin-chestnut tannin films plasticized with 30% w/w Gly might be associated with certain degree of phase separation which provoked the migration of the plasticizer to the film surface. The incorporation of chestnut tannin and glycerol affected the chemical structure of the resultant films due to the establishment of hydrogen interactions between components as revealed by Fourier transform infrared spectroscopy. These interactions reduced gelatin crystallinity and seemed to be involved in the substantial decrease of the water uptake of films with tannin, irrespective of the glycerol level. Such interactions had minor effect on tensile properties being similar to those of the control films (without chestnut tannin) at the same glycerol level. Films modified with 10% w/w chestnut tannin showed significant (P < 0.05) 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity, ca. from 0 ± 0.033 to 87.1 ± 0.002% for chestnut tannin-free and chestnut tannin-containing gelatin films. The limited inhibitory activity of films incorporated with 10% w/w chestnut tannin against the selected bacteria evidenced by disk diffusion method probably resulted from the interactions within the film restricting the diffusion of the active agent into the agar medium. The more modest protective effect observed against a Gram-positive bacterium (S. aureus) was also discussed. © The Author(s) 2014 Reprints and permissions: sagepub.co.uk/journalsPermissions.nav.

Agrobacterium Mediated Transient Gene Silencing (AMTS) in Stevia rebaudiana: Insights into Steviol Glycoside Biosynthesis Pathway

PubMed Central

Guleria, Praveen; Yadav, Sudesh Kumar

2013-01-01

Background Steviol glycoside biosynthesis pathway has emerged as bifurcation from ent-kaurenoic acid, substrate of methyl erythritol phosphate pathway that also leads to gibberellin biosynthesis. However, the genetic regulation of steviol glycoside biosynthesis has not been studied. So, in present study RNA interference (RNAi) based Agrobacterium mediated transient gene silencing (AMTS) approach was followed. SrKA13H and three SrUGTs (SrUGT85C2, SrUGT74G1 and SrUGT76G1) genes encoding ent-kaurenoic acid-13 hydroxylase and three UDP glycosyltransferases of steviol glycoside biosynthesis pathway were silenced in Stevia rebaudiana to understand its molecular mechanism and association with gibberellins. Methodology/Principal Findings RNAi mediated AMTS of SrKA13H and three SrUGTs has significantly reduced the expression of targeted endogenous genes as well as total steviol glycoside accumulation. While gibberellins (GA3) content was significantly enhanced on AMTS of SrUGT85C2 and SrKA13H. Silencing of SrKA13H and SrUGT85C2 was found to block the metabolite flux of steviol glycoside pathway and shifted it towards GA3 biosynthesis. Further, molecular docking of three SrUGT proteins has documented highest affinity of SrUGT76G1 for the substrates of alternate pathways synthesizing steviol glycosides. This could be a plausible reason for maximum reduction in steviol glycoside content on silencing of SrUGT76G1 than other genes. Conclusions SrKA13H and SrUGT85C2 were identified as regulatory genes influencing carbon flux between steviol glycoside and gibberellin biosynthesis. This study has also documented the existence of alternate steviol glycoside biosynthesis route. PMID:24023961

A Novel Diterpene Glycoside with Nine Glucose Units from Stevia rebaudiana Bertoni

PubMed Central

Prakash, Indra; Ma, Gil; Bunders, Cynthia; Charan, Romila D.; Ramirez, Catherine; Devkota, Krishna P.; Snyder, Tara M.

2017-01-01

Following our interest in new diterpene glycosides with better taste profiles than that of Rebaudioside M, we have recently isolated and characterized Rebaudioside IX—a novel steviol glycoside—from a commercially-supplied extract of Stevia rebaudiana Bertoni. This molecule contains a hexasaccharide group attached at C-13 of the central diterpene core, and contains three additional glucose units when compared with Rebaudioside M. Here we report the complete structure elucidation—based on extensive Nuclear Magnetic Resonance (NMR) analysis (1H, 13C, Correlation Spectroscopy (COSY), Heteronuclear Single Quantum Coherence-Distortionless Enhancement Polarization Transfer (HSQC-DEPT), Heteronuclear Multiple Bond Correlation (HMBC), 1D Total Correlation Spectroscopy (TOCSY), Nuclear Overhauser Effect Spectroscopy (NOESY)) and mass spectral data—of this novel diterpene glycoside with nine sugar moieties and containing a relatively rare 1→6 α-linked glycoside. A steviol glycoside bearing nine glucose units is unprecedented in the literature, and could have an impact on the natural sweetener catalog. PMID:28146121

The influence of stevia glycosides on the growth of Lactobacillus reuteri strains.

PubMed

Deniņa, I; Semjonovs, P; Fomina, A; Treimane, R; Linde, R

2014-03-01

Use of stevia-derived sweeteners was recently officially approved by the European Commission, and their application in the food industry has increased, especially in functional foods. However, there are scarce data about the influence of stevia on probiotic bacteria, which are important both as an inhabitant of the human gut and as a functional food additive. Taking into consideration the broad application of Lactobacillus reuteri in functional foods, the aim of the research was to evaluate the influence of stevia glycosides on its growth. Six Lact. reuteri strains were tested for their ability to grow in the presence of stevioside and rebaudioside A (0·2-2·6 g l(-1) ). The effect of stevia glycosides on biomass concentration, cell count, pH and lactic and acetic acid synthesis was analysed. Both glycosides impaired the growth of analysed strains. However, the inhibitory effect was strain specific, and the concentration-dependent effect was not observed for all parameters. The most pronounced concentration-dependent effect was on lactic and acetic acid production. Taking into account the observed strain-specific inhibitory effect of stevia glycosides, it could be suggested to evaluate the influence of them on each strain employed before their simultaneous application in functional foods. The study showed that the growth of Lactobacillus reuteri strains was inhibited in the presence of stevia sweeteners stevioside and rebaudioside A. Probiotics, for example Lact. reuteri strains, are often used as functional additives in health foods and are an important natural inhabitant of the human gastrointestinal tract. Stevia glycosides application in food is increasing; yet, there are no data about the influence of stevia glycosides on Lact. reuteri growth and very few data on growth of other lactobacilli, either in probiotic foods or in the gastrointestinal tract. This research shows that it is necessary to evaluate the influence of stevia glycosides on other groups

Effects of Condensed and Hydrolyzable Tannins on Rumen Metabolism with Emphasis on the Biohydrogenation of Unsaturated Fatty Acids.

PubMed

Costa, Mónica; Alves, Susana P; Cappucci, Alice; Cook, Shaun R; Duarte, Ana; Caldeira, Rui M; McAllister, Tim A; Bessa, Rui J B

2018-04-04

The hypothesis that condensed tannins have higher inhibitory effect on ruminal biohydrogenation than hydrolyzable tannins was tested. Condensed tannin extract from mimosa (CT) and hydrolyzable tannin extract from chestnut (HT) or their mixture (MIX) were incorporated (10%) into oil supplemented diets and fed to rumen fistulated sheep. Fatty acid and dimethyl acetal composition of rumen contents and bacterial biomass were determined. Selected rumen bacteria were analyzed by quantitative real time PCR. Lower ( P < 0.05) rumen volatile fatty acids concentrations were observed with CT compared to HT. Moreover, lower concentration ( P < 0.05) of Fibrobacter succinogenes, Ruminococcus flavefaciens, Ruminococcus albus, and Butyrivibrio proteoclasticus were observed with CT compared to HT. The extension of biohydrogenation of 18:2n-6 and 18:3n-3 did not differ among treatments but was much more variable with CT and MIX than with HT. The trans-/ cis-18:1 ratio in bacterial biomass was higher ( P < 0.05) with HT than CT. Thus, mimosa condensed tannins had a higher inhibitory effect on ruminal metabolism and biohydrogenation than chestnut hydrolyzable tannins.

The use of tannins in the local treatment of burn wounds - a pilot study.

PubMed

Chokotho, L; van Hasselt, E

2005-06-01

Twenty patients aged 3 years and above with fresh partial thickness burns of less than 20% total body surface area were randomly assigned to local treatment of the burn wound either with a solution containing tannins (tannin group), or one of the other commonly used topical agents, such as honey and ghee, silver sulfadiazine, etc (the other group). The effects on serum transaminase and alkaline phosphatase, the incidence and type of wound infection, the quality of the eschar, the formation of scar tissue, adverse effects, the alleviation of pain and possible adverse reactions were studied in both treatment groups. Surprisingly initial assessment of the burn wound depth proved more difficult than anticipated even in the hands of the more experienced health worker. Liver function tests were elevated in both the tannin (6 patients) and the other group (7 patients). Bacterial colonization of the wounds was equally distributed in both groups, although Staphylococcus aureus was found more often in the other group (9 versus 1). The quality of the eschar was better in the tannin group (6 patients had a supple eschar versus 3 in the other group). The most important observations were that no adverse reactions were encountered and that in the tannin group only one patient developed a hypertrophic scar compared to 5 patients in the other group. It proved difficult to quantify alleviation of pain especially in the children.

Characterization and Modeling of the Collision Induced Dissociation Patterns of Deprotonated Glycosphingolipids: Cleavage of the Glycosidic Bond

NASA Astrophysics Data System (ADS)

Rožman, Marko

2016-01-01

Glycosphingolipid fragmentation behavior was investigated by combining results from analysis of a series of negative ion tandem mass spectra and molecular modeling. Fragmentation patterns extracted from 75 tandem mass spectra of mainly acidic glycosphingolipid species (gangliosides) suggest prominent cleavage of the glycosidic bonds with retention of the glycosidic oxygen atom by the species formed from the reducing end (B and Y ion formation). Dominant product ions arise from dissociation of sialic acids glycosidic bonds whereas product ions resulting from cleavage of other glycosidic bonds are less abundant. Potential energy surfaces and unimolecular reaction rates of several low-energy fragmentation pathways leading to cleavage of glycosidic bonds were estimated in order to explain observed dissociation patterns. Glycosidic bond cleavage in both neutral (unsubstituted glycosyl group) and acidic glycosphingolipids was the outcome of the charge-directed intramolecular nucleophilic substitution (SN2) mechanism. According to the suggested mechanism, the nucleophile in a form of carboxylate or oxyanion attacks the carbon at position one of the sugar ring, simultaneously breaking the glycosidic bond and yielding an epoxide. For gangliosides, unimolecular reaction rates suggest that dominant product ions related to the cleavage of sialic acid glycosidic bonds are formed via direct dissociation channels. On the other hand, low abundant product ions related to the dissociation of other glycosidic bonds are more likely to be the result of sequential dissociation. Although results from this study mainly contribute to the understanding of glycosphingolipid fragmentation chemistry, some mechanistic findings regarding cleavage of the glycosidic bond may be applicable to other glycoconjugates.

Spectrophotometric determination of the tannin contents of various Turkish black tea, beer and wine samples.

PubMed

Tinkiliç, N; Uyanik, A

2001-05-01

This study reports tannin contents of various tea (19), beer (6) and wine (6) samples, produced or sold in Turkey under different brand names. Determinations were carried out by employing a previously reported UV-vis spectrophotometric method. The standard addition procedure was also compared to the direct determination procedure and found to be more reliable. The tannin contents of hot water extracts of tea, tea bag and herbal tea samples ranged between 6.20-8.33, 8.03-6.59 and 2.76-6.54 percent (w/w) respectively. Tannin contents of beer and wine samples determined without extraction were found ranging between 66.36-77.26 and 67.18-107.62 micrograms/mL respectively. Iron contents of analysed wine samples were also found ranging between 0.36 and 10.33 ppm by AAS and no relation is found between tannin and iron contents.

Neovascularization of Ischemic Myocardium by Newly Isolated Tannins Prevents Cardiomyocyte Apoptosis and Improves Cardiac Function

PubMed Central

Gu, Xuemei; Cheng, Lei; Chueng, Winghong L; Yao, Xinsheng; Liu, Hongwei; Qi, Guoqing; Li, Ming

2006-01-01

During remodeling progress post myocardial infarction, the contribution of neoangiogenesis to the infarct-bed capillary is insufficient to support the greater demands of the hypertrophied but viable myocardium resulting in further ischemic injury to the viable cardiomyocytes at risk. Here we reported the bio-assay-guided identification and isolation of angiogenic tannins (angio-T) from Geum japonicum that induced rapid revascularization of infarcted myocardium and promoted survival potential of the viable cardiomyocytes at risk after myocardial infarction. Our results demonstrated that angio-T displayed potent dual effects on up-regulating expression of angiogenic factors, which would contribute to the early revascularization and protection of the cardiomyocytes against further ischemic injury, and inducing antiapoptotic protein expression, which inhibited apoptotic death of cardiomyocytes in the infarcted hearts and limited infarct size. Echocardiographic studies demonstrated that angio-T-induced therapeutic effects on acute infarcted myocardium were accompanied by significant functional improvement by 2 days after infarction. This improvement was sustained for 14 days. These therapeutic properties of angio-T to induce early reconstitution of a blood supply network, prevent apoptotic death of cardiomyocytes at risk, and improve heart function post infarction appear entirely novel and may provide a new dimension for therapeutic angiogenesis medicine for the treatment of ischemic heart diseases. PMID:17380192

Toward the optical tongue: flow-through sensing of tannin-protein interactions based on FTIR spectroscopy.

PubMed

Edelmann, Andrea; Lendl, Bernhard

2002-12-11

The interaction of polyphenols (tannins) with proline-rich proteins (gelatin) has been studied using an automated flow injection system with Fourier transform infrared spectroscopic detection to gain insight into chemical aspects related to astringency. In the perception of astringency, a major taste property in red wines and other beverages such as beer, tea, or fruit juices, an interaction between proline-rich salivary proteins and tannins present in the sample takes place. To study this interaction, agarose beads carrying gelatin (a proline-rich protein) were placed in the IR flow cell in such a way that the beads were probed by the IR beam. Using an automated flow system, we injected samples in a carrier stream and flushed over the proteins in a highly reproducible manner. Simultaneously, any retardation due to tannin-protein interactions taking place inside the flow cell was monitored by infrared spectroscopy. Tannins of different sources (grapes, wooden barrels, formulations used in wine making) were investigated, and their flow-through behavior was characterized. Significant differences in their affinity toward gelatin could be observed. Furthermore, because of small but characteristic differences in the IR spectrum, it is possible to distinguish condensed from hydrolyzable tannins. Nonastringent substances such as alcohols, sugars, and acids did not show retention on gelatin. The selectivity of the flow-through sensor was also demonstrated on the example of red and white wine. In contrast to white wine, where no interaction could be observed, in red wine a major interaction of the red wine tannins was found.

A comparison of flavonoid glycosides by electrospray tandem mass spectrometry

NASA Astrophysics Data System (ADS)

March, Raymond E.; Lewars, Errol G.; Stadey, Christopher J.; Miao, Xiu-Sheng; Zhao, Xiaoming; Metcalfe, Chris D.

2006-01-01

A comparison is presented of product ion mass spectra of protonated and deprotonated molecules of kaempferol-3-O-glucoside, quercitin-3-O-glucoside (isoquercitrin), quercitin-3-O-galactoside (hyperoin), apigenin-7-O-glucoside, luteolin-7-O-glucoside, genistein-7-O-glucoside, naringenin-7-O-glucoside (prunin), luteolin-4'-O-glucoside, luteolin-6-C-glucoside (homoorientin, known also as isoorientin), apigenin-8-C-glucoside (vitexin), and luteolin-8-C-glucoside (orientin) together with the product ion mass spectrum of deprotonated kaempferol-7-O-glucoside. All isomeric ions were distinguishable on the basis of their product ion mass spectra. For protonated 3-O-, 7-O-, and 4'-O-glycosides at a collision energy of 46-47 eV, homolytic cleavage of the O-glycosidic bond yielded aglycon Y+ ions, whereas in deprotonated 3-O-, 7-O-, and 4'-O-glycosides, heterolytic and homolytic cleavage of the O-glycosidic bond yielded radical aglycon (Y-H)- and aglycon (Y-) ions. In each case, fragmentation of either the glycan or the aglycon or both was observed. For 6-C- and 8-C-glycosides at a collision energy of 46-47 eV, fragmentation was restricted almost exclusively to the glycan. For luteolin-6-C-glucoside, the integrity of the aglycon structure is preserved at the expense of the glycan for which some 30 fragmentations were observed. Breakdown curves were determined as a function of collision energy for protonated and deprotonated luteolin-6-C-glucoside. An attempt has been made to rationalize the product ion mass spectra derived from C-O- and C-C-luteolin glucosides in terms of computed structures that indicate significant intramolecular hydrogen bonding and rotation of the B-ring to form a coplanar luteolin structure. It is proposed that protonated and deprotonated luteolin-6-C-glucoside may afford examples of cooperative interactive bonding that plays a major role in directing fragmentation.

NMR and molecular modeling of wine tannins binding to saliva proteins: revisiting astringency from molecular and colloidal prospects.

PubMed

Cala, Olivier; Pinaud, Noël; Simon, Cécile; Fouquet, Eric; Laguerre, Michel; Dufourc, Erick J; Pianet, Isabelle

2010-11-01

In organoleptic science, the association of tannins to saliva proteins leads to the poorly understood phenomenon of astringency. To decipher this interaction at molecular and colloidal levels, the binding of 4 procyanidin dimers (B1-4) and 1 trimer (C2) to a human saliva proline-rich peptide, IB7(14), was studied. Interactions have been characterized by measuring dissociation constants, sizes of complexes, number, and nature of binding sites using NMR (chemical shift variations, diffusion-ordered spectroscopy, and saturation transfer diffusion). The binding sites were identified using molecular mechanics, and the hydrophilic/hydrophobic nature of the interactions was resolved by calculating the molecular lipophilicity potential within the complexes. The following comprehensive scheme can be proposed: 1) below the tannin critical micelle concentration (CMC), interaction is specific, and the procyanidin anchorage always occurs on the same three IB7(14) sites. The tannin 3-dimensional structure plays a key role in the binding force and in the tannin's ability to act as a bidentate ligand: tannins adopting an extended conformation exhibit higher affinity toward protein and initiate the formation of a network. 2) Above the CMC, after the first specific hydrophilic interaction has taken place, a random hydrophobic stacking occurs between tannins and proteins. The whole process is discussed in the general frame of wine tannins eliciting astringency.

Stryphnodendron adstringens and purified tannin on Pythium insidiosum: in vitro and in vivo studies.

PubMed

Trolezi, Rodrigo; Azanha, Juliana Maziero; Paschoal, Natália Rodrigues; Chechi, Jéssica Luana; Dias Silva, Marcelo José; Fabris, Viciany Eric; Vilegas, Wagner; Kaneno, Ramon; Fernandes Junior, Ary; Bosco, Sandra de Moraes Gimenes

2017-02-23

Pythium insidiosum is the etiological agent of pythiosis, an emerging life-threatening infectious disease in tropical and subtropical regions. The pathogen is a fungus-like organism resistant to antifungal therapy, for this reason, most cases need extensive surgical debridments as treatment, but depending on the size and anatomical region of the lesion, such approach is unfeasible. We investigate the fungicidal effect and toxicity of crude bark extract of Stryphnodendron adstringens and commercially available tannin on Pythium insidiosum both in vitro and in vivo. Standardized fragments of mycelia of fifteen isolates of P. insidiosum were tested with different concentrations of bark extract (10 to 30% v/v) and tannin (0.5, 1.0 and 1.5 mg/mL). For in vivo study, fifteen rabbits were experimentally infected with zoospores of P. insidiosum and treated by oral and intralesional applications of bark extract and tannin. Acute toxicity tests with both substances were also performed in rats. In vitro studies showed fungicidal effect for both substances at different concentrations and the SEM showed alteration on the cell wall surface of the pathogen. All infected rabbits developed a firm nodular mass that reached around 90 mm 2 ninety days after inoculation, but neither the intralesional inoculation of tannin, nor the oral administration of crude extract and tannin were able to promote remission of the lesions. Lesions developed by rabbits presented an encapsulated abscess being quite different of naturally acquired pythiosis, which is characterized by ulcerated lesions. Since no toxicity was observed in rats or rabbits inoculated with these products, while in vitro experiments showed direct antifungal effect, therapeutic activity of S. adstringens and tannin should be clinically tested as an alternative for healing wounds in naturally acquired pythiosis.

Identification of spectral regions for the quantification of red wine tannins with fourier transform mid-infrared spectroscopy.

PubMed

Jensen, Jacob S; Egebo, Max; Meyer, Anne S

2008-05-28

Accomplishment of fast tannin measurements is receiving increased interest as tannins are important for the mouthfeel and color properties of red wines. Fourier transform mid-infrared spectroscopy allows fast measurement of different wine components, but quantification of tannins is difficult due to interferences from spectral responses of other wine components. Four different variable selection tools were investigated for the identification of the most important spectral regions which would allow quantification of tannins from the spectra using partial least-squares regression. The study included the development of a new variable selection tool, iterative backward elimination of changeable size intervals PLS. The spectral regions identified by the different variable selection methods were not identical, but all included two regions (1485-1425 and 1060-995 cm(-1)), which therefore were concluded to be particularly important for tannin quantification. The spectral regions identified from the variable selection methods were used to develop calibration models. All four variable selection methods identified regions that allowed an improved quantitative prediction of tannins (RMSEP = 69-79 mg of CE/L; r = 0.93-0.94) as compared to a calibration model developed using all variables (RMSEP = 115 mg of CE/L; r = 0.87). Only minor differences in the performance of the variable selection methods were observed.

Condensed Tannin Reacts with SO2 during Wine Aging, Yielding Flavan-3-ol Sulfonates.

PubMed

Ma, Lingjun; Watrelot, Aude A; Addison, Bennett; Waterhouse, Andrew L

2018-06-08

Numerous monomeric and oligomeric flavanol sulfonation products were observed in 10 wines. Levels of 0.85-20.06 and 0-14.72 mg/L were quantified for two monomeric sulfonated flavan-3-ols and, surprisingly, were generally higher than the well-known native flavan-3-ol monomers. Increasing SO 2 levels during wine aging increased the sulfonate-modified flavan-3-ol monomers and dimers along with higher concentrations of native monomers. The results indicate that >10% of SO 2 is reacting with the C-4 carbocation, formed from acid cleavage of the interflavan bond, perhaps by a bimolecular S N 2-type reaction, and as a reducing agent. In addition, the high SO 2 wine had the lowest protein-binding tannin levels, tannin activity, and mean degree of polymerization (mDP), and acidic SO 2 treatment of condensed tannin abolishes protein binding. Thus, SO 2 changes tannin composition during wine aging, and the substantial formation of sulfonate-modified flavan-3-ols may provide an additional explanation for the reduction in astringency of aged red wines.

Isolation and characterization of an anaerobic ruminal bacterium capable of degrading hydrolyzable tannins.

PubMed Central

Nelson, K E; Pell, A N; Schofield, P; Zinder, S

1995-01-01

An anaerobic diplococcoid bacterium able to degrade hydrolyzable tannins was isolated from the ruminal fluid of a goat fed desmodium (Desmodium ovalifolium), a tropical legume which contains levels as high as 17% condensed tannins. This strain grew under anaerobic conditions in the presence of up to 30 g of tannic acid per liter and tolerated a range of phenolic monomers, including gallic, ferulic, and p-coumaric acids. The predominant fermentation product from tannic acid breakdown was pyrogallol, as detected by high-performance liquid chromatography and mass spectrometry. Tannic acid degradation was dependent on the presence of a sugar such as glucose, fructose, arabinose, sucrose, galactose, cellobiose, or soluble starch as an added carbon and energy source. The strain also demonstrated resistance to condensed tannins up to a level of 4 g/liter. PMID:7574640

[Effects of sanguisorba tannins and saponins compatibility on pharmacokinetic parameters of catechin, epicatechin and ziyuglycoside Ⅰ in rats].

PubMed

Xiong, Yong-Ai; Yang, Ming

2016-10-01

To study the effects of sanguisorba tannins and saponins compatibility at different proportions [tannins-saponins (1∶1) and tannins-saponins(8∶1)] after intragastric administration (50 mg•kg⁻¹) on pharmacokinetic parameters of catechin, epicatechin and ziyuglycoside Ⅰ in rats by using pharmacokinetic techniques and methods. Kinetica 5.0 software was used to calculate the pharmacokinetic parameters. The results showed that the specificity, linearity, recovery rate, precision and stability of the established detection method were in line with the test requirements. When the sanguisorba tannins and eaponins were combined at the rate of 1∶1, Vd and CL of catechin and epicatechin were increased significantly（P<0.05); MRT was significantly shortened(P<0.05); Cmax and AUC were significantly reduced(P<0.05). When the sanguisorba tannins and saponins were combined at the rate of 8∶1, Vd and CL of catechin and epicatechin were significantly reduced(P<0.05); MRT was significantly prolonged(P<0.05); Cmax and AUC were increased significantly(P<0.05). In addition, with the increase in proportion of sanguisorba tannins in the compatibility, Cmax and AUC of ziyuglycoside Ⅰ were increased significantly(P<0.05); Vd and CL were significantly reduced(P<0.05), Tmax was obviously lagging behind, and MRT was also significantly prolonged(P<0.05). In our present study, catechin, epicatechin and ziyuglycoside Ⅰ showed good pharmacokinetic behavior in rats when sanguisorba tannins and saponins were combined at the rate of 8∶1 in compatibility, which could be used as a reference for the proportion in sanguisorba tannins and saponins compatibility. Copyright© by the Chinese Pharmaceutical Association.

Tannins and terpenoids as major precursors of Suwannee River fulvic acid

USGS Publications Warehouse

Leenheer, Jerry A.; Rostad, Colleen E.

2004-01-01

Suwannee River fulvic acid (SRFA) was fractionated into 7 fractions by normal-phase chromatography on silica gel followed by reverse-phase fractionation on XAD-8 resin that produced 18 subfractions. Selected major subfractions were characterized by 13C-nuclear magnetic resonance (NMR), infrared spectrometry, and elemental analyses. 13C-NMR spectra of the subfractions were more indicative of precursor structures than unfractionated SRFA, and gave spectral profiles that indicated SRFA mass was about equally split between tannin precursors and terpenoid precursors. Lignin precursors were minor components. Synthesis of 13C-NMR data with elemental data for subfractions derived from both tannin and terpenoid precursors revealed high ring contents and low numbers of carbon per rings which is indicative of fused ring structures that are extensively substituted with carboxyl and methyl groups. These results ruled out extended chain structures for SRFA. This information is useful for determining sources and properties of fulvic acid in drinking water supplies as tannins are more reactive with chlorine to produce undesirable disinfection by-products than are terpenoids.

Tannins and related polyphenols of melastomataceous plants. VIII. Nobotanins L, M and N, trimeric hydrolyzable tannins from Tibouchina semidecandra.

PubMed

Yoshida, T; Nakata, F; Okuda, T

1999-06-01

Three hydrolyzable tannins, nobotannins L, M and N, were isolated from the water-soluble portion of the leaf extract of Tibouchina semidecandra, and their trimeric structures were elucidated from spectral and chemical evidence. Nobotanins L and N exist as equilibrium mixtures of four anomers due to the presence of two unacylated anomeric centers.

Tannins from Hamamelis virginiana bark extract: characterization and improvement of the antiviral efficacy against influenza A virus and human papillomavirus.

PubMed

Theisen, Linda L; Erdelmeier, Clemens A J; Spoden, Gilles A; Boukhallouk, Fatima; Sausy, Aurélie; Florin, Luise; Muller, Claude P

2014-01-01

Antiviral activity has been demonstrated for different tannin-rich plant extracts. Since tannins of different classes and molecular weights are often found together in plant extracts and may differ in their antiviral activity, we have compared the effect against influenza A virus (IAV) of Hamamelis virginiana L. bark extract, fractions enriched in tannins of different molecular weights and individual tannins of defined structures, including pseudotannins. We demonstrate antiviral activity of the bark extract against different IAV strains, including the recently emerged H7N9, and show for the first time that a tannin-rich extract inhibits human papillomavirus (HPV) type 16 infection. As the best performing antiviral candidate, we identified a highly potent fraction against both IAV and HPV, enriched in high molecular weight condensed tannins by ultrafiltration, a simple, reproducible and easily upscalable method. This ultrafiltration concentrate and the bark extract inhibited early and, to a minor extent, later steps in the IAV life cycle and tannin-dependently inhibited HPV attachment. We observed interesting mechanistic differences between tannin structures: High molecular weight tannin containing extracts and tannic acid (1702 g/mol) inhibited both IAV receptor binding and neuraminidase activity. In contrast, low molecular weight compounds (<500 g/mol) such as gallic acid, epigallocatechin gallate or hamamelitannin inhibited neuraminidase but not hemagglutination. Average molecular weight of the compounds seemed to positively correlate with receptor binding (but not neuraminidase) inhibition. In general, neuraminidase inhibition seemed to contribute little to the antiviral activity. Importantly, antiviral use of the ultrafiltration fraction enriched in high molecular weight condensed tannins and, to a lesser extent, the unfractionated bark extract was preferable over individual isolated compounds. These results are of interest for developing and improving plant

Tannins from Hamamelis virginiana Bark Extract: Characterization and Improvement of the Antiviral Efficacy against Influenza A Virus and Human Papillomavirus

PubMed Central

Theisen, Linda L.; Erdelmeier, Clemens A. J.; Spoden, Gilles A.; Boukhallouk, Fatima; Sausy, Aurélie; Florin, Luise; Muller, Claude P.

2014-01-01

Antiviral activity has been demonstrated for different tannin-rich plant extracts. Since tannins of different classes and molecular weights are often found together in plant extracts and may differ in their antiviral activity, we have compared the effect against influenza A virus (IAV) of Hamamelis virginiana L. bark extract, fractions enriched in tannins of different molecular weights and individual tannins of defined structures, including pseudotannins. We demonstrate antiviral activity of the bark extract against different IAV strains, including the recently emerged H7N9, and show for the first time that a tannin-rich extract inhibits human papillomavirus (HPV) type 16 infection. As the best performing antiviral candidate, we identified a highly potent fraction against both IAV and HPV, enriched in high molecular weight condensed tannins by ultrafiltration, a simple, reproducible and easily upscalable method. This ultrafiltration concentrate and the bark extract inhibited early and, to a minor extent, later steps in the IAV life cycle and tannin-dependently inhibited HPV attachment. We observed interesting mechanistic differences between tannin structures: High molecular weight tannin containing extracts and tannic acid (1702 g/mol) inhibited both IAV receptor binding and neuraminidase activity. In contrast, low molecular weight compounds (<500 g/mol) such as gallic acid, epigallocatechin gallate or hamamelitannin inhibited neuraminidase but not hemagglutination. Average molecular weight of the compounds seemed to positively correlate with receptor binding (but not neuraminidase) inhibition. In general, neuraminidase inhibition seemed to contribute little to the antiviral activity. Importantly, antiviral use of the ultrafiltration fraction enriched in high molecular weight condensed tannins and, to a lesser extent, the unfractionated bark extract was preferable over individual isolated compounds. These results are of interest for developing and improving plant

Characterization and attenuation study on tannin-added Rhizophora spp. particleboard at high energy photon and electron

NASA Astrophysics Data System (ADS)

Yusof, Mohd Fahmi Mohd; Hamid, Puteri Nor Khatijah Abd; Tajuddin, Abd Aziz; Abdullah, Reduan; Hashim, Rokiah; Bauk, Sabar; Isa, Norriza Mohd; Isa, Muhammad Jamal Md

2017-01-01

The effective atomic number of tannin-added Rhizophora spp. particleboards was determined based on elemental composition using Energy Dispersive X-ray Analysis (EDXA). The value of mass attenuation coefficients were measured using 137Cs and 60Co gamma energies. The attenuation properties of PDD curves and beam profile of tannin-added Rhizophora spp. particleboards were investigated using Gafchromic EBT2 film at 6 MV photon and 6 MeV electrons and compared to the value in water and solid water phantoms. The results showed that tannin-added Rhizophora spp. particleboards having effective atomic number close to the value of water. The mass attenuation coefficients were near to the value of water with χ2 values of 0.018 and 0.357 to 137Cs and 60Co gamma energies respectively. The PDD of tannin-added Rhizophora spp. particleboards at 6 MV photons showed good agreement within 3.21 and 5.91% to that in solid water phantoms and water respectively. The PDD at 6 MeV electrons showed a good agreement within 3.32 and 3.12% to that in solid water phantoms and water respectively. The depth of R50 and R90 in tannin-added Rhizophora spp. also showed a good agreement to that in water and solid water pahtoms. Lower surface dose was observed in tannin-added Rhizophora spp. particleboards at electron beams in comparison to solid water phantoms and water.

Synthesis and Photochromic Properties of Configurationally Varied Azobenzene Glycosides

PubMed Central

Chandrasekaran, Vijayanand; Johannes, Eugen; Kobarg, Hauke; Sönnichsen, Frank D; Lindhorst, Thisbe K

2014-01-01

Spatial orientation of carbohydrates is a meaningful parameter in carbohydrate recognition processes. To vary orientation of sugars with temporal and spatial resolution, photosensitive glycoconjugates with favorable photochromic properties appear to be opportune. Here, a series of azobenzene glycosides were synthesized, employing glycoside synthesis and Mills reaction, to allow “switching” of carbohydrate orientation by reversible E/Z isomerization of the azobenzene N=N double bond. Their photochromic properties were tested and effects of azobenzene substitution as well as the effect of anomeric configuration and the orientation of the sugars 2-hydroxy group were evaluated. PMID:25050228

Bacterial and Protozoal Communities and Fatty Acid Profile in the Rumen of Sheep Fed a Diet Containing Added Tannins ▿

PubMed Central

Vasta, Valentina; Yáñez-Ruiz, David R.; Mele, Marcello; Serra, Andrea; Luciano, Giuseppe; Lanza, Massimiliano; Biondi, Luisa; Priolo, Alessandro

2010-01-01

This study evaluated the effects of tannins on ruminal biohydrogenation (BH) due to shifts in the ruminal microbial environment in sheep. Thirteen lambs (45 days of age) were assigned to two dietary treatments: seven lambs were fed a barley-based concentrate (control group) while the other six lambs received the same concentrate with supplemental quebracho tannins (9.57% of dry matter). At 122 days of age, the lambs were slaughtered, and the ruminal contents were subjected to fatty acid analysis and sampled to quantify populations of Butyrivibrio fibrisolvens, which converts C18:2 c9-c12 (linoleic acid [LA]) to C18:2 c9-t11 (rumenic acid [RA]) and then RA to C18:1 t11 (vaccenic acid [VA]); we also sampled for Butyrivibrio proteoclasticus, which converts VA to C18:0 (stearic acid [SA]). Tannins increased (P < 0.005) VA in the rumen compared to the tannin-free diet. The concentration of SA was not affected by tannins. The SA/VA ratio was lower (P < 0.005) for the tannin-fed lambs than for the controls, suggesting that the last step of the BH process was inhibited by tannins. The B. proteoclasticus population was lower (−30.6%; P < 0.1), and B. fibrisolvens and protozoan populations were higher (+107% and +56.1%, respectively; P < 0.05) in the rumen of lambs fed the tannin-supplemented diet than in controls. These results suggest that quebracho tannins altered BH by changing ruminal microbial populations. PMID:20173064

Science Study Aids 5: Tannin - Nature's Filter.

ERIC Educational Resources Information Center

Boeschen, John; Randall, John M.

This publication is the fifth in a series of seven supplementary investigative materials for use in secondary science classes providing up-to-date research-related investigations. This unit is structured for grade levels 9 through 12. It is concerned with the removal of heavy divalent metals from water with the use of tannin-containing…

Phenolic Glycosides in Populus tremuloides and their Effects on Long-Term Ungulate Browsing.

PubMed

Lastra, R A; Kenkel, N C; Daayf, F

2017-10-01

In the aspen-grassland ecotone of Riding Mountain, Manitoba, lightly browsed vigorous clones of trembling aspen (Populus tremuloides Michx.) occur in close proximity to heavily browsed dieback clones. This study examines whether intraspecific variation in the production of phenolic glycosides is correlated with this strong dichotomy in clonal vigor. Individual clones were sampled over four years at three sites located along a gradient of increasing soil moisture stress. At each site, eight aspen clones of similar size and age were sampled: four vigorous and four dieback clones (total of 24 individual clones). The severity of wapiti (elk) browsing was assessed as the ratio of browse-damaged to total branches per aspen ramet. Statistically significant differences in foliar concentrations of the phenolic glycosides salicortin and tremulacin were observed between vigorous and dieback clones: a mean of 14.8% dry mass for lightly browsed (vigorous) clones, versus just 7.0% for heavily browsed (dieback) clones. Mean concentrations of foliar phenolics were also significantly greater in more moisture-stressed sites. These results demonstrate that the strong dichotomy in clonal vigor (vigorous versus dieback clones) is associated with large differences in phenolic glycoside production. Vigorous clone ramets produce high amounts of phenolic glycosides and have low levels of herbivore browsing and low mortality rates, whereas dieback clone ramets have low amounts of phenolic glycosides and much higher herbivore browsing and mortality rates. This suggests that intraspecific variation in phenolic glycosides in trembling aspen is an important predisposing factor leading to ramet mortality, and by extension to the decline of aspen clones.

Quantification of flavonol glycosides in Camellia sinensis by MRM mode of UPLC-QQQ-MS/MS.

PubMed

Wu, Yahui; Jiang, Xiaolan; Zhang, Shuxiang; Dai, Xinlong; Liu, Yajun; Tan, Huarong; Gao, Liping; Xia, Tao

2016-04-01

Phenolic compounds are major components of tea flavour, in which catechins and flavonol glycosides play important roles in the astringent taste of tea infusion. However, the flavonol glycosides are difficult to quantify because of the large variety, as well as the inefficient seperation on chromatography. In this paper, a total of 15 flavonol glycosides in the tea plant (Camellia sinensis) were identified by the high performance liquid chromatography (HPLC) coupled to a time-of-flight mass spectrometer (TOF-MS), and a quantitative method was established based on multiple reaction monitoring (MRM) mode of ultra-high performance liquid chromatography (UPLC) coupled to a triple quadrupole mass spectrometer (QQQ-MS/MS). It provided the limit of detection and quantification to the order of picogram, which was more sensitive than the HPLC detection of the order of nanogram. The relative standard deviations of the intra- and inter-day variations in retention time and signal intensity (peak area) of six analytes were less than 0.26% and 4%, respectively. The flavonol glycosides of four tea cultivars were relatively quantified using the signal intensity (peak area) of product ion, in which six flavonol glycosides were quantified by the authentic standards. The results showed that the flavonol mono-, di- and tri-glycoside mostly accumulated in young leaves of the four tea cultivars. Notably, the myricetin 3-O-galactoside was the major component among the six flavonol glycosides detected. Copyright © 2016 Elsevier B.V. All rights reserved.

Measuring the molecular dimensions of wine tannins: comparison of small-angle X-ray scattering, gel-permeation chromatography and mean degree of polymerization.

PubMed

McRae, Jacqui M; Kirby, Nigel; Mertens, Haydyn D T; Kassara, Stella; Smith, Paul A

2014-07-23

The molecular size of wine tannins can influence astringency, and yet it has been unclear as to whether the standard methods for determining average tannin molecular weight (MW), including gel-permeation chromatography (GPC) and depolymerization reactions, are actually related to the size of the tannin in wine-like conditions. Small-angle X-ray scattering (SAXS) was therefore used to determine the molecular sizes and corresponding MWs of wine tannin samples from 3 and 7 year old Cabernet Sauvignon wine in a variety of wine-like matrixes: 5-15% and 100% ethanol; 0-200 mM NaCl and pH 3.0-4.0, and compared to those measured using the standard methods. The SAXS results indicated that the tannin samples from the older wine were larger than those of the younger wine and that wine composition did not greatly impact on tannin molecular size. The average tannin MWs as determined by GPC correlated strongly with the SAXS results, suggesting that this method does give a good indication of tannin molecular size in wine-like conditions. The MW as determined from the depolymerization reactions did not correlate as strongly with the SAXS results. To our knowledge, SAXS measurements have not previously been attempted for wine tannins.

New cardenolide and acylated lignan glycosides from the aerial parts of Asclepias curassavica.

PubMed

Warashina, Tsutomu; Shikata, Kimiko; Miyase, Toshio; Fujii, Satoshi; Noro, Tadataka

2008-08-01

Three new cardenolide glycosides and six new acylated lignan glycosides were obtained along with nineteen known compounds from the aerial parts of Asclepias curassavica L. (Asclepiadaceae). The structure of each compound was determined based on interpretations of NMR and MS measurements and chemical evidence.

Comparison of extraction protocols to determine differences in wine-extractable tannin and anthocyanin in Vitis vinifera L. cv. Shiraz and Cabernet Sauvignon grapes.

PubMed

Bindon, Keren A; Kassara, Stella; Cynkar, Wieslawa U; Robinson, Ella M C; Scrimgeour, Neil; Smith, Paul A

2014-05-21

Cabernet Sauvignon and Shiraz grapes were sourced from different regions within Australia, and microvinified with a skin contact period of 6 days. Grape samples were extracted using two protocols: a 15% v/v ethanol, 10 g/L tartaric acid extract of gently crushed berries (wine-like, WL) and a 50% v/v ethanol, pH 2 extract of grape berry homogenate. It was found that in WL extracts, grape tannin and anthocyanin concentrations were strongly related to wine tannin, anthocyanin and color density achieved during the skin contact period. No relationship was observed for grape tannin concentration analyzed in homogenate extracts and wine tannin, but a strong, positive relationship was found for anthocyanin concentration. When the data obtained from homogenate extraction was treated separately by grape variety, a stronger relationship between grape and wine tannin concentration was observed. Tannin compositional analysis in wines indicated that higher tannin concentrations were due to the extraction of tannin of higher molecular mass during fermentation, most likely from grape skins.

8,14-Secopregnane glycosides from the aerial parts of Asclepias tuberosa.

PubMed

Warashina, Tsutomu; Noro, Tadataka

2009-07-01

Twenty pregnane glycosides, tuberoside A(1)-L(5), were isolated from the diethyl ether-soluble fraction of the MeOH extract from the aerial parts of Asclepias tuberosa (Asclepiadaceae). The pregnane glycosides were composed of 8,12;8,20-diepoxy-8,14-secopregnane as aglycon, and D-cymarose, D-oleandrose, D-digitoxose and/or D-glucose as the component sugars. Their structures were established using NMR spectroscopic analysis and chemical methodologies.

Use of qNMR for speciation of flaxseeds (Linum usitatissimum) and quantification of cyanogenic glycosides.

PubMed

Roulard, Romain; Fontaine, Jean-Xavier; Jamali, Arash; Cailleu, Dominique; Tavernier, Reynald; Guillot, Xavier; Rhazi, Larbi; Petit, Emmanuel; Molinie, Roland; Mesnard, François

2017-12-01

This report describes a routine method taking less than 20 min to quantify cyanogenic glycosides such as linustatin and neolinustatin from flaxseeds (Linum usitatissimum L.) using 1 H nuclear magnetic resonance. After manual dehulling, a higher linustatin content was shown in the almond fraction, while neolinustatin and total cyanogenic glycoside contents were significantly higher in hulls. Linustatin and neolinustatin were quantified in seven cultivars grown in two locations in three different years. Linustatin, neolinustatin, and total cyanogenic glycosides ranged between 91 and 267 mg/100 g, 78-272 mg/100 g, and 198-513 mg/100 g dry weight flaxseeds, respectively. NMR revealed differences of up to 70% between samples with standard deviation variations lower than 6%. This study shows that NMR is a very suitable tool to perform flaxseed varietal selection for the cyanogenic glycoside content. Graphical abstract qNMR can be used to perform flaxseed varietal selection for the cyanogenic glycoside content.

In vitro propagation and production of cardiotonic glycosides in shoot cultures of Digitalis purpurea L. by elicitation and precursor feeding.

PubMed

Patil, Jitendra Gopichand; Ahire, Mahendra Laxman; Nitnaware, Kirti Manik; Panda, Sayantan; Bhatt, Vijay P; Kishor, Polavarapu B Kavi; Nikam, Tukaram Dayaram

2013-03-01

Digitalis purpurea L. (Scrophulariaceae; Foxglove) is a source of cardiotonic glycosides such as digitoxin and digoxin which are commercially applied in the treatment to strengthen cardiac diffusion and to regulate heart rhythm. This investigation deals with in vitro propagation and elicited production of cardiotonic glycosides digitoxin and digoxin in shoot cultures of D. purpurea L. In vitro germinated seedlings were used as a primary source of explants. Multiple shoot formation was achieved for three explant types (nodal, internodal, and leaf) cultured on Murashige and Skoog (MS) medium with several treatments of cytokinins (6-benzyladenine-BA; kinetin-Kin; and thidiazuron-TDZ) and auxins (indole-3-acetic acid-IAA; α-naphthaleneacetic acid-NAA; and 2,4-dichlorophenoxy acetic acid-2,4-D). Maximum multiple shoots (12.7 ± 0.6) were produced from nodal explants on MS + 7.5 μM BA. Shoots were rooted in vitro on MS containing 15 μM IAA. Rooted plantlets were successfully acclimatized. To further maintain the multiple shoot induction, mother tissue was cut into four equal parts and repeatedly sub-cultured on fresh shoot induction liquid medium after each harvest. On adaptation of this strategy, an average of 18 shoots per explant could be produced. This strategy was applied for the production of biomass and glycosides digitoxin and digoxin in shoot cultures on MS medium supplemented with 7.5 μM BA and several treatments with plant growth regulators, incubation period, abiotic (salicylic acid, mannitol, sorbitol, PEG-6000, NaCl, and KCl), biotic (Aspergillus niger, Helminthosporium sp., Alternaria sp., chitin, and yeast extract) elicitors, and precursors (progesterone, cholesterol, and squalene). The treatment of KCl, mycelial mass of Helminthosporium sp., and progesterone were highly effective for the production of cardenolides. In the presence of progesterone (200 to 300 mg/l), digitoxin and digoxin accumulation was enhanced by 9.1- and 11.9-folds

Chitosan mediated enhancement of hydrolysable tannin in Phyllanthus debilis Klein ex Willd via plant cell suspension culture.

PubMed

V, Malayaman; N, Sisubalan; R P, Senthilkumar; S, Sheik Mohamed; R, Ranjithkumar; M, Ghouse Basha

2017-11-01

Phyllanthus debilis Klein ex Willd. is wild medicinal plant used in the traditional system of medicine. This plant has been actively used for hepatoprotection and to cure many diseases including jaundice and so on; which leads to complete extinction of this particular species. Therefore, the chitosan mediated cost effective cell suspension method has been developed for the production of hydrolysable tannin. The hydrolysable tannins are the main therapeutically active constituents with antioxidant, anticancer, and antimicrobial properties. An in vitro cell suspension culture was optimized by adding chitosan for production of hydrolysable tannin. According to the growth kinetics, a maximum biomass of 4.46±0.06g fresh cell weight and 1.33±0.04g dry cell weight were obtained from the optimal suspension medium consisted of MS medium+0.5mgL -1 BAP+1.5mgL -1 NAA. Chitosan was treated at the stationary phase which leads to the highest accumulation of hydrolysable tannin compared to the untreated control. Hydrolysable tannin was observed and compared using HPLC at the Rt of 4.91 in both chitosan treated and untreated cells. This is the first ever report where use of chitosan has been done to enhance the production of the hydrolysable tannin in P. debilis using cell suspension culture technique. Copyright © 2017 Elsevier B.V. All rights reserved.

Meta-analysis of the relationship between dietary tannin level and methane formation in ruminants from in vivo and in vitro experiments.

PubMed

Jayanegara, A; Leiber, F; Kreuzer, M

2012-06-01

A meta-analysis was conducted to evaluate the extent to which dietary tannin level is related to methane emissions from ruminants. Data from a total of 30 experiments comprising 171 treatments were entered in a database. In vitro batch culture and in vivo measurements were distinguished as experimental approaches. With any approach, methane declined when dietary tannins increased. The in vitro approach predicted the in vivo response quite accurately. However, in vitro, the response followed a quadratic response pattern (R(2) = 0.66; lower response with increasing tannin level), whereas in vivo, this decline was linear (R(2) = 0.29). This indicates that the in vitro batch culture is of limited accuracy for estimating effects at levels >100 g tannin/kg dry matter. The large variation in methane/digestible organic matter (OM) found at low tannin levels may explain contrasting literature reports. Methane reduction with tannins was associated with a reduced apparent digestion of OM, and especially fibre, but methane/apparently digestible OM declined also. The present findings are helpful as they identified an underlying general antimethanogenic effect of tannins across tannin sources and experimental conditions, thus allowing concentrating the search on sources with satisfactory palatability and low adverse effects on animal performance. © 2011 Blackwell Verlag GmbH.

Evaluation of the potential carcinogenic activity of Senna and Cascara glycosides for the rat colon.

PubMed

Mereto, E; Ghia, M; Brambilla, G

1996-03-19

Anthraquinone glycosides of Senna and Cascara were investigated for their ability to induce aberrant crypt foci (ACF) in the rat colon mucosa, which are considered putative preneoplastic lesions. Dietary exposure to high doses of these glycosides for 56 successive days did not cause the appearance of ACF or increase in incidence of ACF induced by 1,2-dimethyl-hydrazine (DMH). However, in rats treated with both DMH and the highest dose of glycosides, the average number of aberrant crypts per focus, considered a consistent predictor of tumor outcome, was higher than in rats given DMH alone. These findings suggest that Senna and Cascara glycoside might behave as weak promoters in rat colon carcinogenesis.

Hillasides A and B, two new cytotoxic triterpene glycosides from the sea cucumber Holothuria hilla Lesson.

PubMed

Wu, Jun; Yi, Yang-Hua; Tang, Hai-Feng; Wu, Hou-Ming; Zhou, Zhen-Rong

2007-01-01

Two new triterpene glycosides, hillasides A (1) and B (2), were isolated from the sea cucumber H. hilla Lesson, together with one known glycoside holothuria B (3). Their structures were deduced by extensive spectral analysis and chemical evidences. The presence of conjugated double bonds [22E,24-diene] in the aglycone of 1 is a rare structural feature among sea cucumber glycosides. The two glycosides showed significant cytotoxicity against eight human tumour cell lines (A-549, MCF-7, IA9, CAKI-1, PC-3, KB, KB-VIN and HCT-8) with IC(50) in the range of 0.1-3.8 microg/ml.

Proanthocyanidins and hydrolysable tannins: occurrence, dietary intake and pharmacological effects.

PubMed

Smeriglio, Antonella; Barreca, Davide; Bellocco, Ersilia; Trombetta, Domenico

2017-06-01

Tannins are a heterogeneous group of high MW, water-soluble, polyphenolic compounds, naturally present in cereals, leguminous seeds and, predominantly, in many fruits and vegetables, where they provide protection against a wide range of biotic and abiotic stressors. Tannins exert several pharmacological effects, including antioxidant and free radical scavenging activity as well as antimicrobial, anti-cancer, anti-nutritional and cardio-protective properties. They also seem to exert beneficial effects on metabolic disorders and prevent the onset of several oxidative stress-related diseases. Although the bioavailability and pharmacokinetic data for these phytochemicals are still sparse, gut absorption of these compounds seems to be inversely correlated with the degree of polymerization. Further studies are mandatory to better clarify how these molecules and their metabolites are able to cross the intestinal barrier in order to exert their biological properties. This review summarizes the current literature on tannins, focusing on the main, recently proposed mechanisms of action that underlie their pharmacological and disease-prevention properties, as well as their bioavailability, safety and toxicology. This article is part of a themed section on Principles of Pharmacological Research of Nutraceuticals. To view the other articles in this section visit http://onlinelibrary.wiley.com/doi/10.1111/bph.v174.11/issuetoc. © 2016 The British Pharmacological Society.

Proanthocyanidins and hydrolysable tannins: occurrence, dietary intake and pharmacological effects

PubMed Central

Smeriglio, Antonella; Bellocco, Ersilia; Trombetta, Domenico

2016-01-01

Tannins are a heterogeneous group of high MW, water‐soluble, polyphenolic compounds, naturally present in cereals, leguminous seeds and, predominantly, in many fruits and vegetables, where they provide protection against a wide range of biotic and abiotic stressors. Tannins exert several pharmacological effects, including antioxidant and free radical scavenging activity as well as antimicrobial, anti‐cancer, anti‐nutritional and cardio‐protective properties. They also seem to exert beneficial effects on metabolic disorders and prevent the onset of several oxidative stress‐related diseases. Although the bioavailability and pharmacokinetic data for these phytochemicals are still sparse, gut absorption of these compounds seems to be inversely correlated with the degree of polymerization. Further studies are mandatory to better clarify how these molecules and their metabolites are able to cross the intestinal barrier in order to exert their biological properties. This review summarizes the current literature on tannins, focusing on the main, recently proposed mechanisms of action that underlie their pharmacological and disease‐prevention properties, as well as their bioavailability, safety and toxicology. Linked Articles This article is part of a themed section on Principles of Pharmacological Research of Nutraceuticals. To view the other articles in this section visit http://onlinelibrary.wiley.com/doi/10.1111/bph.v174.11/issuetoc PMID:27646690

Tannins and Bacitracin Differentially Modulate Gut Microbiota of Broiler Chickens

PubMed Central

Pin Viso, Natalia Daniela; Farber, Marisa Diana

2018-01-01

Antibiotic growth promoters have been used for decades in poultry farming as a tool to maintain bird health and improve growth performance. Global concern about the recurrent emergence and spreading of antimicrobial resistance is challenging the livestock producers to search for alternatives to feed added antibiotics. The use of phytogenic compounds appears as a feasible option due to their ability to emulate the bioactive properties of antibiotics. However, detailed description about the effects of in-feed antibiotics and alternative natural products on chicken intestinal microbiota is lacking. High-throughput sequencing of 16S rRNA gene was used to study composition of cecal microbiota in broiler chickens supplemented with either bacitracin or a blend of chestnut and quebracho tannins over a 30-day grow-out period. Both tannins and bacitracin had a significant impact on diversity of cecal microbiota. Bacitracin consistently decreased Bifidobacterium while other bacterial groups were affected only at certain times. Tannins-fed chickens showed a drastic decrease in genus Bacteroides while certain members of order Clostridiales mainly belonging to the families Ruminococcaceae and Lachnospiraceae were increased. Different members of these groups have been associated with an improvement of intestinal health and feed efficiency in poultry, suggesting that these bacteria could be associated with productive performance of birds. PMID:29682522

Tissue and cellular localization of tannins in Tunisian dates (Phoenix dactylifera L.) by light and transmission electron microscopy.

PubMed

Hammouda, Hédi; Alvarado, Camille; Bouchet, Brigitte; Kalthoum-Chérif, Jamila; Trabelsi-Ayadi, Malika; Guyot, Sylvain

2014-07-16

A histological approach including light microscopy and transmission electron microscopy (TEM) was used to provide accurate information on the localization of condensed tannins in the edible tissues and in the stone of date fruits (Phoenix dactylifera L.). Light microscopy was carried out on fresh tissues after staining by 4-dimethylaminocinnamaldehyde (DMACA) for a specific detection of condensed tannins. Thus, whether under light microscopy or transmission electron microscopy (TEM), results showed that tannins are not located in the epidermis but more deeply in the mesocarp in the vacuole of very large cells. Regarding the stones, tannins are found in a specific cell layer located at 50 μm from the sclereid cells of the testa.

Triterpenoid glycosides from Bacopa monnieri.

PubMed

Sivaramakrishna, Chillara; Rao, Chirravuri V; Trimurtulu, Golakoti; Vanisree, Mulabagal; Subbaraju, Gottumukkala V

2005-12-01

Two triterpenoid glycosides have been isolated along with 10 known saponins from Bacopa monnieri. Structures of the compounds have been elucidated as 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] jujubogenin (1) and 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] pseudojujubogenin (2) by high resolution NMR spectral data and chemical correlations. Further, the chemical compositions of bacosides A and B have been delineated.

Influence of Tannin Extract and Yeast Extract on Color Preservation and Anthocyanin Content of Mulberry Wine.

PubMed

You, Yilin; Li, Na; Han, Xue; Guo, Jielong; Liu, Guojie; Huang, Weidong; Zhan, Jicheng

2018-04-01

The color of mulberry wine is extremely unstable in processing and aging. This paper investigates the effects of tannin extract and yeast extract on the color and color-preserving characteristics of mulberry wine made from the Dashi cultivar. The results showed that the maximum absorption wavelength in both tannin extract and yeast extract groups changed generating the red shift effect. The color of the tannin extract maintained a good gloss in the first 4 months, while the yeast extract group showed remarkable color preservation for the first 3 months. The total anthocyanin and cyanidin-3-rutinoside contents in both experiment groups were significantly higher than that of the control group, thus proving that tannin extract and yeast extract both exert a remarkably positive effect on preserving the color of mulberry wine during its aging. Moreover, sensory analysis indicated that the quality of mulberry wine treated with tannin extract was significantly higher than that of the control. The distinct color of mulberry wine is one of the foremost qualities that imprints on consumers' senses, but it is extremely unstable in processing and aging. However, the color protection of mulberry wine was not studied previously. In this study, we found that tannin extract and yeast extract both exert a remarkably positive effect on preserving the color of mulberry wine during aging. The study is of great significance as a guide to improving the color stability of mulberry wine, thereby also improving and promoting the development of the mulberry deep processing industry. © 2018 Institute of Food Technologists®.

Studies on Emblica officinalis Derived Tannins for Their Immunostimulatory and Protective Activities against Coccidiosis in Industrial Broiler Chickens

PubMed Central

Kaleem, Qari Muhammad; Akhtar, Masood; Awais, Mian Muhammad; Saleem, Muhammad; Zafar, Muddassar; Iqbal, Zafar; Muhammad, Faqir

2014-01-01

The present study reports the effect of Emblica officinalis (EO) derived tannins on humoral immune responses and their protective efficacy against Eimeria infection in chickens. Tannins were extracted from EO and characterized by HPLC. EO derived tannins (EOT) and commercial tannins (CT) were orally administered in broiler chicks in graded doses for three consecutive days, that is, 5th-7th days of age. On day 14 after administration of tannins, humoral immune response was detected against sheep red blood cells (SRBCs) by haemagglutination assay. Protective efficacy of tannins was measured against coccidial infection, induced by Eimeria species. Results revealed higher geomean titers against SRBCs in chickens administered with EOT as compared to those administered with CT and control group. Mean oocysts per gram of droppings were significantly lower (P < 0.05) in EOT administered chickens as compared to control group. Lesion scoring also showed the lowest caecal and intestinal lesion score of mild to moderate intensity in chickens administered with EOT. Further, significantly higher (P < 0.05) daily body weight gains and antibody titers were detected in EOT administered chickens as compared to those of CT administered and control groups. EOT showed the immunostimulatory properties in broilers and their administration in chickens boost the protective immunity against coccidiosis. PMID:24578631

Studies on Emblica officinalis derived tannins for their immunostimulatory and protective activities against coccidiosis in industrial broiler chickens.

PubMed

Kaleem, Qari Muhammad; Akhtar, Masood; Awais, Mian Muhammad; Saleem, Muhammad; Zafar, Muddassar; Iqbal, Zafar; Muhammad, Faqir; Anwar, Muhammad Irfan

2014-01-01

The present study reports the effect of Emblica officinalis (EO) derived tannins on humoral immune responses and their protective efficacy against Eimeria infection in chickens. Tannins were extracted from EO and characterized by HPLC. EO derived tannins (EOT) and commercial tannins (CT) were orally administered in broiler chicks in graded doses for three consecutive days, that is, 5th-7th days of age. On day 14 after administration of tannins, humoral immune response was detected against sheep red blood cells (SRBCs) by haemagglutination assay. Protective efficacy of tannins was measured against coccidial infection, induced by Eimeria species. Results revealed higher geomean titers against SRBCs in chickens administered with EOT as compared to those administered with CT and control group. Mean oocysts per gram of droppings were significantly lower (P < 0.05) in EOT administered chickens as compared to control group. Lesion scoring also showed the lowest caecal and intestinal lesion score of mild to moderate intensity in chickens administered with EOT. Further, significantly higher (P < 0.05) daily body weight gains and antibody titers were detected in EOT administered chickens as compared to those of CT administered and control groups. EOT showed the immunostimulatory properties in broilers and their administration in chickens boost the protective immunity against coccidiosis.

Identification of a flavonoid C-glycoside as potent antioxidant.

PubMed

Wen, Lingrong; Zhao, Yupeng; Jiang, Yueming; Yu, Limei; Zeng, Xiaofang; Yang, Jiali; Tian, Miaomiao; Liu, Huiling; Yang, Bao

2017-09-01

Flavonoids have been documented to have good antioxidant activities in vitro. However, reports on the cellular antioxidant activities of flavonoid C-glycosides are very limited. In this work, an apigenin C-glycoside was purified from Artocarpus heterophyllus by column chromatography and was identified to be 2″-O-β-D-xylosylvitexin by nuclear magnetic resonance spectroscopy. The cellular antioxidant activity and anticancer activity of 2″-O-β-D-xylosylvitexin were evaluated for the first time. The quantitative structure-activity relationship was analysed by molecular modeling. Apigenin presented an unexpected cellular antioxidation behaviour. It had an antioxidant activity at low concentration and a prooxidant activity at high concentration, whereas 2″-O-β-D-xylosylvitexin showed a dose-dependent cellular antioxidant activity. It indicated that C-glycosidation improved the cellular antioxidation performance of apigenin and eliminated the prooxidant effect. The ortho-dihydroxyl at C-3'/C-4' and C-3 hydroxyl in the flavonoid skeleton play important roles in the antioxidation behaviour. The cell proliferation assay revealed a low cytotoxicity of 2″-O-β-D-xylosylvitexin. Copyright © 2017 Elsevier Inc. All rights reserved.

Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives

PubMed Central

Pandey, Ramesh Prasad; Parajuli, Prakash; Shin, Ju Yong; Lee, Jisun; Lee, Seul; Hong, Young-Soo; Park, Yong Il; Kim, Joong Su

2014-01-01

A UDP glucosyltransferase from Bacillus licheniformis was overexpressed, purified, and incubated with nucleotide diphosphate (NDP) d- and l-sugars to produce glucose, galactose, 2-deoxyglucose, viosamine, rhamnose, and fucose sugar-conjugated resveratrol glycosides. Significantly higher (90%) bioconversion of resveratrol was achieved with α-d-glucose as the sugar donor to produce four different glucosides of resveratrol: resveratrol 3-O-β-d-glucoside, resveratrol 4′-O-β-d-glucoside, resveratrol 3,5-O-β-d-diglucoside, and resveratrol 3,5,4′-O-β-d-triglucoside. The conversion rates and numbers of products formed were found to vary with the other NDP sugar donors. Resveratrol 3-O-β-d-2-deoxyglucoside and resveratrol 3,5-O-β-d-di-2-deoxyglucoside were found to be produced using TDP-2-deoxyglucose as a donor; however, the monoglycosides resveratrol 4′-O-β-d-galactoside, resveratrol 4′-O-β-d-viosaminoside, resveratrol 3-O-β-l-rhamnoside, and resveratrol 3-O-β-l-fucoside were produced from the respective sugar donors. Altogether, 10 diverse glycoside derivatives of the medically important resveratrol were generated, demonstrating the capacity of YjiC to produce structurally diverse resveratrol glycosides. PMID:25239890

Nickel-catalyzed proton-deuterium exchange (HDX) procedures for glycosidic linkage analysis of complex carbohydrates

USDA-ARS?s Scientific Manuscript database

The structural analysis of complex carbohydrates typically requires the assignment of three parameters: monosaccharide composition, the position of glycosidic linkages between monosaccharides, and the position and nature of non-carbohydrate substituents. The glycosidic linkage positions are often de...

The role of condensed tannins in the nutritional value of Lotus pedunculatus for sheep. 2. Quantitative digestion of carbohydrates and proteins.

PubMed

Barry, T N; Manley, T R

1984-05-01

Primary growth vegetative Lotus pedunculatus containing 46 and 106 g/kg dry matter (DM) of total condensed tannin and 3 and 14 g/kg DM of free condensed tannin, was cut and fed fresh at hourly intervals (750 g DM/d) to sheep fitted with permanent cannulas into the rumen and duodenum. Low- and high-tannin lotus contained respectively 41.3 and 31.6 g total nitrogen/kg DM and 132 and 152 g lignin/kg DM. The two forms of lotus were similar in carbohydrate composition. Nutrient intake was recorded and faecal output measured by direct collection. Digesta flow to the duodenum was estimated by measuring dilution at the duodenum of inert ruthenium phenanthroline (Ru-P) and chromium-EDTA markers continuously infused into the rumen. Effects attributable to condensed tannins were assessed by comparing the digestion of the two diets, and by comparing the digestion of each with predicted values for non-tannin-containing fresh forages fed at similar intakes. Apparent digestibility of all nutrients measured was less for high- than for low-tannin lotus (P less than 0.01). The levels of cellulose digested ruminally and post- ruminally in both forms of lotus were similar to predicted values. However, less hemicellulose and readily fermentable carbohydrate (RFC; soluble carbohydrate + pectin) was digested in the rumen in sheep given both forms of lotus than would be predicted for non-tannin-containing fresh forage diets, but this was compensated for by greater post-ruminal absorption of both nutrients. Total N gains across the rumen (duodenal N flow--total N intake) were 1.8 and 10.5 g/d for low- and high-tannin lotus v. predicted losses of 3.7 and 2.1 g/d for non-tannin-containing fresh forages given at the same total N intakes. Post-ruminal digestion of non- amonia -N (NAN; proportion NAN flowing at duodenum) was 0.71 and 0.67 for low- and high-tannin lotus respectively v. 0.76 for comparable non-tannin-containing fresh forages. Energy absorbed as amino acids from the small

Solubility Enhancement of Steviol Glycosides and Characterization of Their Inclusion Complexes with Gamma-Cyclodextrin

PubMed Central

Upreti, Mani; Strassburger, Ken; Chen, You L.; Wu, Shaoxiong; Prakash, Indra

2011-01-01

Steviol glycosidesrebaudioside (reb) A, C and D have low aqueous solubilities. To improve their aqueous solubilities, inclusion complex of steviol glycosides, reb A, C and D and gamma cyclodextrin were prepared by freeze drying method and further characterized by means of differential scanning calorimetry, Fourier transform infrared spectroscopy and Raman spectroscopy. The effect of gamma cyclodextrin on chemical shifts of the steviol glycosides was also studied in proton NMR experiments as well as in solid state 13C CP/MAS NMR experiments. These results indicated that the steviol glycosides were clearly in inclusion complex formation with the gamma cyclodextrin which also results in solubility enhancement of these steviol glycosides. Phase solubility studies showed that amounts of soluble reb A, C and D increased with increasing amounts of gamma cyclodextrin indicating formation of 1:1 stoichiometric and higher order inclusion complexes. PMID:22174615

PHARMACOGNOSTIC STUDIES ON THE FRUITS OF JATROPHA CURCAS LINN

PubMed Central

Joseph, G.V.R.

2001-01-01

Present paper deals with the pharmacognostic studies of the fruits of J. curcas Linn. The 75-80 cells thick pericarp is differentiated into epicarp, mesocarp and endocarp. Mesocarpic zone embeds non-articulated laticifers, tannin containing idioblasts and randomly distributed vascular bundles. Endocarp shows the occurrence of fibrous sclereids. Preliminary phytochemical screening of the drug powder shows the presence of alkaloids, carbohydrates, glycosides and tannins. Clinical evaluation of the fresh fruit juice has shown it s anti gingivitic property. PMID:22557042

Preparative isolation and purification of five flavonoid glycosides and one benzophenone galloyl glycoside from Psidium guajava by high-speed counter-current chromatography (HSCCC).

PubMed

Zhu, Yindi; Liu, Yue; Zhan, Ying; Liu, Lin; Xu, Yajuan; Xu, Tunhai; Liu, Tonghua

2013-12-16

Psidium guajava leaves have a diverse phytochemical composition including flavonoids, phenolics, meroterpenoids and triterpenes, responsible for the biological activities of the medicinal parts. In particular, flavonol glycosides show beneficial effects on type II diabetes mellitus. A simple and efficient HSCCC method has been developed for the preparative separation of five flavonoid glycosides and one diphenylmethane glycoside from P. guajava. A solvent system composed of n-hexane-ethyl acetate-methanol-water (0.7:4:0.8:4, v/v/v/v) was optimized for the separation. The upper phase was used as the stationary phase, and the lower phase was used as the mobile phase. Under the optimized conditions, hyperoside (15.3 mg), isoquercitrin (21.1 mg), reynoutrin (65.2 mg), quercetin-3-O-β-D-arabinopyranoside (71.7 mg), quercetin-3-O-α-L-arabinofuranoside (105.6 mg) and 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6''-O-galloyl)-β-D-glucopyranoside (98.4 mg) were separated from crude sample (19.8 g). The structures of all the isolates were identified by ESI-MS, 1H- and 13C-NMR analyses and their purities (>95%) were determined using HPLC.

Condensed tannin-resorcinol adducts in laminating adhesives

Treesearch

Richard W. Hemingway; Roland E. Kreibich

1985-01-01

A condensed tannin-resorcinol adduct made by co-reaction of an extract from southern pine bark with resorcinol at a 2 to 1 weight ratio was used to prepare a laminating resin in which the entire amount of resorcinol normally used was replaced by this adduct. The resin was formulated into a room temperature setting adhesive that meets the basic criteria of product...

Glycoside hydrolases having multiple hydrolase activities

DOEpatents

Chen, Zhiwei; Friedland, Gregory D.; Chhabra, Swapnil R.; Chivian, Dylan C.; Simmons, Blake A

2017-08-08

Glycoside hydrolases having at least two different hydrolytic activities are provided. In one embodiment, an isolated recombinant hydrolase having at least two activities selected from a group including asparagine derivatives, glutamine derivatives, and histidine derivatives is provided. Further, a method of generating free sugars from a mixture comprising asparagine derivatives, glutamine derivatives, and histidine derivatives is provided.

Performance and characterization of a new tannin-based coagulant

NASA Astrophysics Data System (ADS)

Beltrán-Heredia, J.; Sánchez-Martín, J.; Gómez-Muñoz, C.

2012-09-01

Diethanolamine and formaldehyde were employed to cationize tannins from black wattle. This novel coagulant called CDF was functionally characterized in removing sodium dodecylbenzene sulfonate (anionic surfactant) and Palatine Fast Black WAN (azoic dye). Refined tannin-derived commercial coagulants exhibited similar efficiency, while CDF presented higher coagulant ability than alum, a usual coagulant agent. Low doses of CDF (ca. 100 mg L-1) were able to remove more than 70 % of surfactant and more than 85 % of dye (initial pollutant concentration of ca. 100 mg L-1) and it presented no temperature affection and worked at a relatively wide pH range. Surfactant and dye removal responded to the classical coagulant-and-adsorption models, such as Frumkin-Fowler-Guggenheim or Gu and Zhu in the case of surfactant, and Langmuir and Freundlich in the case of dye.

Towards high resolution ^1H NMR spectra of tannin colloidal aggregates

NASA Astrophysics Data System (ADS)

Mirabel, M.; Glories, Y.; Pianet, I.; Dufourc, E. J.

1999-10-01

The time dependent colloidal formation of tannins in hydro-alcoholic medium has been studied by 1H-NMR. Line broadening observed with time can be cancelled by making use of magic angle sample spinning (MASS) thus yielding sharp lines that allow structural studies. We used as an example catechin, a constitutive monomer of Bordeaux young red wine tannins. Chemical shift variations of polyphenol protons allow monitoring the time course of aggregation. La formation de tanins colloïdaux au cours du temps, en milieu hydroalcoolique, a été suivie par RMN-^1H. Un élargissement marqué des résonances est observé et peut être supprimé par la rotation de l'échantillon à l'angle magique ce qui ouvre tout un champ d'études structurales sur ces composés colloïdaux. L'exemple proposé est celui de la catéchine, monomère constitutif de tannins présents en grande quantité dans les vins rouges jeunes de Bordeaux. Des variations du déplacement chimique de certains protons polyphénoliques permettent de suivre l'évolution temporelle de l'agrégation.

Assessment of the effect of condensed (acacia and quebracho) and hydrolysable (chestnut and valonea) tannins on rumen fermentation and methane production in vitro.

PubMed

Hassanat, Fadi; Benchaar, Chaouki

2013-01-01

Tannins added to animal diets may have a positive effect on energy and protein utilisation in the rumen. The objective of this study was to examine the impact of different sources and concentrations (20, 50, 100, 150 and 200 g kg⁻¹ dry matter (DM)) of condensed (acacia and quebracho) and hydrolysable (chestnut and valonea) tannins on rumen microbial fermentation in vitro. The experiment also included a negative control with no tannins (control) and a positive control with monensin (10 mg L⁻¹). In vitro gas production and total volatile fatty acid (VFA) concentration decreased as tannin concentration increased. Addition of acacia, chestnut or valonea tannins at ≥ 50 g kg⁻¹ or quebracho tannins at ≥ 100 g kg⁻¹ resulted in a decrease (up to 40%) in methane (CH₄) production compared with the control. Valonea tannins were the only tannin source that reduced (-11%) CH₄ production at 50 g kg⁻¹ without affecting VFA concentration. Tannin treatments reduced ammonia (NH₃) and branched-chain VFA concentrations, indicating a reduction in ruminal protein degradation. Monensin reduced CH₄ production (-37%) and NH₃ concentration (-20%) without affecting total VFA concentration. Supplying acacia, chestnut or valonea tannins at 50 g kg⁻¹ has the potential to reduce CH₄ production and ruminal protein degradation with minimum detrimental effects on efficiency of ruminal fermentation. Copyright © 2012 Crown in the right of Canada. Published by John Wiley & Sons, Ltd.

N cycling and the composition of terpenes and tannins in boreal forest soils: Effects of logging residues

NASA Astrophysics Data System (ADS)

Smolander, Aino; Kitunen, Veikko; Kukkola, Mikko; Tamminen, Pekka

2014-05-01

There is increasing evidence available that certain terpenes and tannins may mediate substantial changes in nitrogen cycling processes in boreal forest soils. Terpenes and tannins are two important groups of plant secondary metabolites: Terpenes are hydrocarbons having different number of isoprene-derived units and tannins are complex polyphenolic compounds able to interact with proteins. Logging residues, consisting of fresh tree tops and branches with needles contain large amounts of terpenes and tannins. Currently there is increasing demand for forest biomass for bioenergy production. Therefore, harvesting of logging residues has become more common from both clear-cutting and thinning stands, instead of conventional stem-only harvest where logging residues are retained on the site. Our aim was to determine how logging residues affect soil N cycling processes in Scots pine and Norway spruce thinning stands in long-term, and how these processes are related to the composition of terpenes and tannins in the soil. Samples were taken from the humus layer of pine and spruce experiments which had been thinned 4-to-19 years before; in the thinning different amounts of logging residues had been distributed on the plots. Logging residues had only little effect on soil microbial biomass N or C. However, in several sites logging residues increased the rate of net N mineralization and the ratios net N mineralization/ C mineralization and net N mineralization/microbial biomass N, and these positive effects were very long-lasting. Logging residues also changed the composition of different terpenes and condensed tannins in soil. In general, with regard to the processes and ratios indicating N availability, stem-only harvest seems to be more favorable than whole-tree harvest. The results from long-term field experiments will be discussed in relation to the effects of different terpenes and tannins, observed in short-term laboratory experiments, on N cycling processes.

Changes in Tannin Composition of Syrah Grape Skins and Seeds during Fruit Ripening under Contrasting Water Conditions.

PubMed

Kyraleou, Maria; Kallithraka, Stamatina; Theodorou, Nikolaos; Teissedre, Pierre-Louis; Kotseridis, Yorgos; Koundouras, Stefanos

2017-09-01

Tannin accumulation and composition were determined in skins and seeds isolated from Vitis vinifera cv. Syrah grapes submitted to contrasting water regimes under semiarid climatic conditions. Three irrigation treatments were conducted, starting at berry set through harvest of two growing seasons, 2011 and 2012: irrigation at 100% of crop evapotranspiration ETc (FI), irrigation at 50% of ETc (DI) and non-irrigated (NI). Seed total tannins did not vary with maturity but those of skins underwent a progressive decline (especially in 2011), expressed both on a fresh weight and on a per berry basis. Skin total tannin concentration and content per berry were increased under NI and DI conditions, mainly in 2012. In contrast, seed total tannins (in 2012) and flavan-3-ol monomers and tannin oligomers (both years) were higher in the fully irrigated vines (FI). Skin polymer size increased during ripening, NI and DI skins showing higher mean degree of polymerization (mDP) compared to FI at harvest. NI was also associated with a lower percentage of galloylation (%G) in skin oligomeric fraction (in 2012) and a lower percentage of prodelphinidins in the skin polymeric fraction (both years) at harvest. The mDP and %G of seed extracts did not vary during ripening and were higher in NI but only in 2012. According to the results, management of vine water status was shown to influence tannin amount and composition of Syrah grapes grown under semiarid conditions.

Interactions of grape tannins and wine polyphenols with a yeast protein extract, mannoproteins and β-glucan.

PubMed

Mekoue Nguela, J; Poncet-Legrand, C; Sieczkowski, N; Vernhet, A

2016-11-01

At present, there is a great interest in enology for yeast derived products to replace aging on lees in winemaking or as an alternative for wine fining. These are yeast protein extracts (YPE), cell walls and mannoproteins. Our aim was to further understand the mechanisms that drive interactions between these components and red wine polyphenols. To this end, interactions between grape skin tannins or wine polyphenols or tannins and a YPE, a mannoprotein fraction and a β-glucan were monitored by binding experiments, ITC and DLS. Depending on the tannin structure, a different affinity between the polyphenols and the YPE was observed, as well as differences in the stability of the aggregates. This was attributed to the mean degree of polymerization of tannins in the polyphenol fractions and to chemical changes that occur during winemaking. Much lower affinities were found between polyphenols and polysaccharides, with different behaviors between mannoproteins and β-glucans. Copyright © 2016 Elsevier Ltd. All rights reserved.

Assessment of Anti-nutritive Activity of Tannins in Tea By-products Based on In vitro Rumen Fermentation.

PubMed

Kondo, Makoto; Hirano, Yoshiaki; Ikai, Noriyuki; Kita, Kazumi; Jayanegara, Anuraga; Yokota, Hiro-Omi

2014-11-01

Nutritive values of green and black tea by-products and anti-nutritive activity of their tannins were evaluated in an in vitro rumen fermentation using various molecular weights of polyethylene glycols (PEG), polyvinyl pyrrolidone (PVP) and polyvinyl polypyrrolidone as tannin-binding agents. Significant improvement in gas production by addition of PEG4000, 6000 and 20000 and PVP was observed only from black tea by-product, but not from green tea by-product. All tannin binding agents increased NH3-N concentration from both green and black tea by-products in the fermentation medium, and the PEG6000 and 20000 showed relatively higher improvement in the NH3-N concentration. The PEG6000 and 20000 also improved in vitro organic matter digestibility and metabolizable energy contents of both tea by-products. It was concluded that high molecular PEG would be suitable to assess the suppressive activity of tannins in tea by-products by in vitro fermentation. Higher responses to gas production and NH3-N concentration from black tea by-product than green tea by-product due to PEG indicate that tannins in black tea by-product could suppress rumen fermentation more strongly than that in green tea by-product.

The impact of tannins on protein, dry matter, and energy digestion in moose (Alces alces)

Treesearch

Donald E. Spalinger; W.B. Collins; Thomas A. Hanley; N.E. Cassara; A.M. Carnahan

2010-01-01

Recent work suggests that moose (Alces alces [L., 1758]) in the boreal ecoregion may be nutritionally limited by the availability of protein as a consequence of both low nitrogen (N) concentrations and high tannin levels in their principal foods. However, the ability of moose to digest protein in the presence of tannins is unknown. We undertook a...

Tannin is a key factor in the determination and prediction of energy content in sorghum grains fed to growing pigs.

PubMed

Pan, L; Li, P; Ma, X K; Xu, Y T; Tian, Q Y; Liu, L; Li, D F; Piao, X S

2016-07-01

This study was conducted to determine and compare the DE and ME content as well as the apparent total tract digestibility (ATTD) of GE in 28 samples of sorghum grain fed to growing pigs and to generate prediction equations for DE, ME, and the ATTD of GE based on chemical analysis. The 28 samples included 8 low-tannin sorghum cultivars (LTS; tannin ≤ 0.16%), 10 medium-tannin sorghum cultivars (MTS: 0.67% ≤ tannin ≤ 0.98%), and 10 high-tannin sorghum cultivars (HTS; 1.11% ≤ tannin ≤ 1.51%) obtained from 9 provinces in China and 3 samples of LTS cultivars were obtained internationally. The 28 diets were formulated to contain 96.9% of 1 of the 28 sorghum grains and 3.1% of vitamins and minerals. Eighty-four barrows (36.5 ± 3.4 kg initial BW) were used in a randomized complete block design conducted during 2 consecutive periods ( = 6 per treatment) with the pigs fed different diets during the 2 periods. For each period, pigs were placed in metabolic crates for a 5-d total collection of feces and urine following 7 d of adaptation to the diets. Among the 28 samples, GE, CP, and ADF content (DM basis) ranged from 4,363 to 4,496 kcal/kg, 8.26 to 13.41%, and 3.26 to 5.78%, respectively. The average tannin content was 0.08, 0.84, and 1.29% in the LTS, MTS, and HTS samples, respectively. The DE and ME content (DM basis) ranged from 3,861 to 3,989 and from 3,784 to 3,905 kcal/kg, respectively, in LTS; from 3,646 to 3,740 and from 3,588 to 3,669 kcal/kg, respectively, in MTS; and from 3,481 to 3,617 and from 3,418 to 3,538 kcal/kg, respectively, in HTS. The mean DE, ME, DE/GE, ME/GE, and ATTD of GE in MTS were less than those in LTS ( < 0.05) and greater than those in HTS ( < 0.05). The correlation coefficients between DE, ME, or the ATTD of GE and tannin content were all -0.96 ( < 0.01). The best-fit equations for DE and ME (kcal/kg DM) for the complete set of 28 sorghum grains were 6,974 - (236 × % tannin) - (43.27 × % ADF) + (24.96 × % CP) - (0.71 × % GE) for

Robust Ultraviolet-Visible (UV-Vis) Partial Least-Squares (PLS) Models for Tannin Quantification in Red Wine.

PubMed

Aleixandre-Tudo, José Luis; Nieuwoudt, Helené; Aleixandre, José Luis; Du Toit, Wessel J

2015-02-04

The validation of ultraviolet-visible (UV-vis) spectroscopy combined with partial least-squares (PLS) regression to quantify red wine tannins is reported. The methylcellulose precipitable (MCP) tannin assay and the bovine serum albumin (BSA) tannin assay were used as reference methods. To take the high variability of wine tannins into account when the calibration models were built, a diverse data set was collected from samples of South African red wines that consisted of 18 different cultivars, from regions spanning the wine grape-growing areas of South Africa with their various sites, climates, and soils, ranging in vintage from 2000 to 2012. A total of 240 wine samples were analyzed, and these were divided into a calibration set (n = 120) and a validation set (n = 120) to evaluate the predictive ability of the models. To test the robustness of the PLS calibration models, the predictive ability of the classifying variables cultivar, vintage year, and experimental versus commercial wines was also tested. In general, the statistics obtained when BSA was used as a reference method were slightly better than those obtained with MCP. Despite this, the MCP tannin assay should also be considered as a valid reference method for developing PLS calibrations. The best calibration statistics for the prediction of new samples were coefficient of correlation (R 2 val) = 0.89, root mean standard error of prediction (RMSEP) = 0.16, and residual predictive deviation (RPD) = 3.49 for MCP and R 2 val = 0.93, RMSEP = 0.08, and RPD = 4.07 for BSA, when only the UV region (260-310 nm) was selected, which also led to a faster analysis time. In addition, a difference in the results obtained when the predictive ability of the classifying variables vintage, cultivar, or commercial versus experimental wines was studied suggests that tannin composition is highly affected by many factors. This study also discusses the correlations in tannin values between the methylcellulose and protein

Anthelmintic effect of plant extracts containing condensed and hydrolyzable tannins on Caenorhabditis elegans and their antioxidant capacity

USDA-ARS?s Scientific Manuscript database

Although tannin-rich forages are known to increase protein uptake and to reduce gastrointestinal nematode infections in grazing ruminants, most published research involves forages with condensed tannins (CT), while published literature lacks information on the anthelmintic capacity, nutritional bene...

Protein-precipitable tannin in wines from Vitis vinifera and interspecific hybrid grapes (Vitis ssp.): differences in concentration, extractability, and cell wall binding.

PubMed

Springer, Lindsay F; Sacks, Gavin L

2014-07-30

Although they possess significant viticultural advantages, interspecific hybrid grapes (Vitis spp.) are reported to produce wine with lower tannin concentrations than European wine varieties (Vitis vinifera). However, extensive quantitative data on this phenomenon as well as mechanistic explanations for these differences are lacking. A survey of primarily commercial wines from the Finger Lakes American Viticultural Area (New York) using a protein precipitation method determined that hybrid-based wines had >4-fold lower tannin concentrations than vinifera wines. To elucidate factors responsible for differences in wine tannin, 24 wines were produced from both red hybrid and vinifera cultivars under identical conditions. Lower wine tannin in French-American hybrid- than vinifera-based wines could be partially explained by lower grape tannin. However, experiments in which cell wall material was incubated with tannin indicated that cell wall binding may be of equal or greater importance in explaining lower wine tannin concentrations in hybrid-based wines. Subsequent characterization of cell wall material revealed that protein in flesh cell walls and, to a lesser extent, pectin in skin cell walls were correlated with cell wall binding.

Glycosidically bound flavor compounds of cape gooseberry (Physalis peruviana L.).

PubMed

Mayorga, H; Knapp, H; Winterhalter, P; Duque, C

2001-04-01

The bound volatile fraction of cape gooseberry (Physalis peruviana L.) fruit harvested in Colombia has been examined by HRGC and HRGC-MS after enzymatic hydrolysis using a nonselective pectinase (Rohapect D5L). Forty bound volatiles could be identified, with 21 of them being reported for the first time in cape gooseberry. After preparative isolation of the glycosidic precursors on XAD-2 resin, purification by multilayer coil countercurrent chromatography and HPLC of the peracetylated glycosides were carried out. Structure elucidation by NMR, ESI-MS/MS, and optical rotation enabled the identification of (1S,2S)-1-phenylpropane-1,2-diol 2-O-beta-D-glucopyranoside (1) and p-menth-4(8)-ene-1,2-diol 1-O-alpha-L-arabinopyranosyl-(1-6)-beta-D-glucopyranoside (2). Both glycosides have been identified for the first time in nature. They could be considered as immediate precursors of 1-phenylpropane-1,2-diol and p-menth-4(8)-ene-1,2-diol, typical volatiles found in the fruit of cape gooseberry.

Up-scaling of tannin-based coagulants for wastewater treatment: performance in a water treatment plant.

PubMed

Grenda, Kinga; Arnold, Julien; Gamelas, José A F; Rasteiro, Maria G

2018-06-21

Tannin extracts from the bark of Acacia mearnsii and wood of Schinopsis balansae, commonly known as Quebracho, were employed. These were modified at laboratory sale via the Mannich aminomethylation with formaldehyde and dimethylamine hydrochloride. Some reaction conditions were varied, namely the formaldehyde dosage and reaction time, while keeping the Mannich solution activation time constant, and their influence on the shear viscosity of the created bio-coagulants was evaluated. The effect of the final pH of the products on their shear viscosity was also analyzed. Up-scaling of the Mannich reaction for tannin from South Africa was performed and the procedure developed at 1-L scale was reproducible in upscaled conditions. One example of a modified South Africa tannin and the modified Quebracho tannin was subsequently selected for the treatment of an industrial wastewater and tested for color and turbidity reduction in jar tests. The effluent treatment was carried out in a single and dual system with cationic synthetic flocculation agents of different charge degree. Good turbidity and decoloration results (93 and 89% reduction, respectively) were obtained with the simultaneous introduction of a cationic, 40% charged polyacrylamide, with minimal dosage (5 ppm) of the latter additive. The tannin-based coagulant from Acacia mearnsii was successfully applied in dual system with cationic polyacrylamide flocculant for industrial wastewater treatment at pilot plant scale. It was shown to satisfactorily treat the water and generate less sludge.

Glycoside hydrolase gene transcription by Alicyclobacillus acidocaldarius during growth on wheat arabinoxylan and monosaccharides: a proposed xylan hydrolysis mechanism

DOE Office of Scientific and Technical Information (OSTI.GOV)

Lee, Brady D.; Apel, William A.; Sheridan, Peter P.

Background Metabolism of carbon bound in wheat arabinoxylan (WAX) polysaccharides by bacteria requires a number of glycoside hydrolases active toward different bonds between sugars and other molecules. Alicyclobacillus acidocaldarius is a Gram-positive thermoacidophilic bacterium capable of growth on a variety of mono-, di-, oligo-, and polysaccharides. Nineteen proposed glycoside hydrolases have been annotated in the A. acidocaldarius Type Strain ATCC27009/DSM 446 genome. Results Molecular analysis using high-density oligonucleotide microarrays was performed on A. acidocaldarius strain ATCC27009 when growing on WAX. When a culture growing exponentially at the expense of arabinoxylan saccharides was challenged with glucose or xylose, most glycoside hydrolasesmore » were down-regulated. Interestingly, regulation was more intense when xylose was added to the culture than when glucose was added, a clear departure from classical carbon catabolite repression demonstrated by many Gram-positive bacteria. In silico analyses of the regulated glycoside hydrolases, along with the results from the microarray analyses, yielded a potential mechanism for arabinoxylan metabolism by A. acidocaldarius. Glycoside hydrolases expressed by this strain may have broad substrate specificity, and initial hydrolysis is catalyzed by an extracellular xylanase, while subsequent steps are likely performed inside the growing cell. Conclusions Glycoside hydrolases, for the most part, appear to be found in clusters, throughout the A. acidocaldarius genome. Not all of the glycoside hydrolase genes found at loci within these clusters were regulated during the experiment, indicating that a specific subset of the 19 glycoside hydrolase genes found in A. acidocaldarius were used during metabolism of WAX. While specific functions of the glycoside hydrolases was not tested as part of the research discussed, many of the glycoside hydrolases found in the A. acidocaldarius Type Strain appear to have a

Cytotoxic hydrolyzable tannins from Balanophora japonica.

PubMed

Jiang, Zhi-Hong; Wen, Xiao-Yun; Tanaka, Takashi; Wu, Shao-Yu; Liu, Zhongqiu; Iwata, Hiromi; Hirose, Yoko; Wu, Shuguang; Kouno, Isao

2008-04-01

Four hydrolyzable tannins named balanophotannins D-G ( 1- 4) were isolated from the aerial parts of the parasitic plant Balanophora japonica. Their structures were characterized on the basis of spectroscopic and chemical evidence. Balanophotannins D-G contain an oxidized hexahydroxydiphenoyl (HHDP) group. The absolute configurations of balanophotannins D ( 1) and F ( 3) were determined via the PGME method. Balanophotannin E ( 2) showed cytotoxicity to Hep G2 cancer cells with an IC 50 value of 4.22 microM.

Understanding the native Californian diet: Identification of condensed and hydrolyzable tannins in tanoak acorns (Lithocarpus densiflorus).

PubMed

Meyers, Katherine J; Swiecki, Tedmund J; Mitchell, Alyson E

2006-10-04

The tanoak (Lithocarpus densiflorus) acorn was a staple food in the Native American diet and is still used in traditional dishes. Acorns from the genus Quercus have been shown to contain a large range of hydrolyzable tannins. However, neither hydrolyzable nor condensed tannins have been characterized in tanoak acorns. The aim of this study was to identify the full range of hydrolyzable and condensed tannins in extracts of tanoak acorns using liquid chromatography/electrospray ionization-mass spectrometry/mass spectrometry. Condensed tannins were identified as B type oligomers of (epi)-catechin (procyanidins) with a degree of polymerization up to six. Oligomers up to and including tetramers were identified by UV spectra and MS detection whereas pentamers and hexamers were detected only by MS. The total concentration of condensed tannins was 464 mg/100 g acorn pericarp. The concentration of propocyanidin monomers, dimers, trimers, and tetramers in acorn pericarp (mg/100 g acorn pericarp) were 95 +/- 10.9, 148 +/- 35.0, 90 +/- 17.9, and 131 +/- 1.9, respectively. No procyanidins were found in the acorn cotyledon tissue. A total of 22 hydrolyzable tannins were identified in methanolic extracts of acorn cotyledon tissue. Gallic acid derivatives predominated and included galloylated esters of glucose, hexahydrodiphenoyl esters of glucose, and methylated gallates. Galloylated esters of glucose were present as isomers of galloyl glucose, digalloyl glucose, and trigalloyl glucose. Mass spectral fragmentation patterns indicate the presence of one gallic acid-galloyl glucose isomer and two gallic acid-digalloyl-glucose isomers. No isomers of tetragalloyl glucose and pentagalloyl glucose were identified. Ellagic acid and ellagic acid pentoside were also identified.

Effects of sorghum (Sorghum bicolor (L.) Moench) tannins on α-amylase activity and in vitro digestibility of starch in raw and processed flours.

PubMed

Mkandawire, Nyambe L; Kaufman, Rhett C; Bean, Scott R; Weller, Curtis L; Jackson, David S; Rose, Devin J

2013-05-08

The purpose of this study was to investigate the effects of tannins on starch digestion in tannin-containing sorghum extracts and wholegrain flours from 12 sorghum varieties. Extracts reduced amylase activity in a tannin concentration-dependent manner when the extract was mixed with the enzyme before substrate (amylopectin) addition, with higher molecular weight tannins showing greater reduction. Conversely, when the extract and substrate were combined before enzyme addition an enhancement in amylase activity was experienced. In uncooked, cooked, and cooked and stored wholegrain sorghum flours, rapidly digestible, slowly digestible, and resistant starches were not correlated with tannin content or molecular weight distribution. Resistant starch increased from 6.5% to 22-26% when tannins were added to starch up to 50% (starch weight). Tannin extracts both reduced and enhanced amylase activity depending on conditions, and, while these trends were clear in extracts, the effects on starch digestion in wholegrain flours was more complex.

New megastigmane glycoside and aromadendrane derivative from the aerial part of Piper elongatum.

PubMed

Masuoka, Chikako; Ono, Masateru; Ito, Yasuyuki; Okawa, Masafumi; Nohara, Toshihiro

2002-10-01

A new megastigmane glycoside, called pipeloside A, and a new aromadendrane type sesquiterpenoid, pipelol A, were isolated from the MeOH extract of the aerial part of Piper elongatum VAHL. along with a known megastigmane glycoside, byzantionoside B. The structures of these compounds were elucidated on the basis of spectroscopic data and chemical evidence.

New insight into the unresolved HPLC broad peak of Cabernet Sauvignon grape seed polymeric tannins by combining CPC and Q-ToF approaches.

PubMed

Ma, Wen; Waffo-Téguo, Pierre; Alessandra Paissoni, Maria; Jourdes, Michäel; Teissedre, Pierre-Louis

2018-05-30

Polymeric tannins from grapes have always been reported as an unresolved broad peak in HPLC chromatograms, and this has severely limited their identification to date. This study aimed to disassemble this broad peak and explore the polymeric tannin molecules inside. By applying centrifugal partition chromatography (CPC), an efficient separation approach was developed to split the broad peak of grape seed tannins into fractions. Then, the fractions were analyzed by Q-ToF (quadrupole time-of-flight mass spectrometry) to determine the corresponding structures of the tannins. The results suggest that grape seed polymeric tannins were eluted consecutively according to their degree of polymerization (DP). Condensed tannins identified in wine grape seed have a range of DP and degree of galloylation (DG) up to 20 and 11, respectively. The molecular mass of the largest molecule detected was 6067. To our knowledge, this is the first report to offer an insight into the broad peak of polymeric tannins found with HPLC and to characterize the tannins with a DP up to 20 as shown by HRMS and MS/MS data. Copyright © 2018 Elsevier Ltd. All rights reserved.

Simultaneous quantitative assessment of nine glycosides in tobacco by liquid chromatography-tandem mass spectrometry.

PubMed

Yuan, Yue; Zhou, Rong; Li, Dongliang; Luo, Cheng; Li, Guoyou

2018-03-01

A simple and efficient method combining ultrasound-assisted extraction, the conditions of which were optimized by response surface methodology, with liquid chromatography and tandem mass spectrometry was established and validated for the absolute quantification of nine non-volatile neutral glycosides originating from tobacco (Nicotiana tobaccum L.) leaves, comprising three phenolic glycosides, one benzanoid glycoside, and five sesquiterpene glycosides within three isomers, originating from tobacco leaves. Factors of extraction time, sample quantity, extraction solvent, liquid chromatographic conditions, and electrospray ionization parameters were carefully investigated to ensure the selectivity and sensitivity of the method. All calibration curves showed excellent coefficients of determination ranging from 0.9940 to 0.9996, within the range of tested concentrations. The limits of detection and quantification were 2.33-25.9 and 7.06-78.5 ng/mL, respectively. Satisfactory values of accuracy were between 80.1 to 107.9% among different sample matrixes. The relative standard deviations of intra- and inter-day analysis were less than 13.7 and 13.0% respectively. The developed method was successfully applied in a pilot study to determine the amounts of the nine endogenous glycosides in real flue-cured tobacco samples obtained from different habitats in China. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Effects of condensed tannin from Acacia mearnsii on sheep infected naturally with gastrointestinal helminthes.

PubMed

Cenci, F B; Louvandini, H; McManus, C M; Dell'Porto, A; Costa, D M; Araújo, S C; Minho, A P; Abdalla, A L

2007-03-15

The effect of tannins on endoparasite control in hair sheep was investigated using 20 entire lambs of the Santa Inês breed. At the beginning of the experiment these animals were 6-months old and weighed 22.5kg+/-4.7. The treatments used were (10 animals each): GT (animals receiving 18g of Acácia negra containing 18% of condensed tannin/animal/week) and GC (animals not receiving tannin). The experiment lasted 84 days, with animals kept on an Andropogon gayanus pasture. Faeces were collected weekly, with weighing and blood collection carried out fortnightly. At slaughter, the adult worms were harvested for identification and counting. Although the GT animals weighed more than the GC lambs at slaughter, these differences were not significant (P>0.05). In general, the values for haemoglobin, hematocrit, total protein, urea, phosphorus and calcium in the serum were within normal levels and no significant differences between groups were observed. For faecal egg count (FEC), lower values were observed throughout the experiment in the group receiving tannin, but these differences were only significant in the eighth week. There was a lower output of eggs by regression for GT compared with GC (P<0.05). The species identified, in decreasing order of worm count, were: Trichostrongylus colubriformis, Haemonchus contortus, Oesophagostomum columbianum, Cooperia sp., Strongyloides papillosus, Trichuris globulosa and Moniezia expansa. The total worm count and number of each species of worm were lower for GT compared with GC for T. colubriformis and Cooperia sp. (P<0.05). Condensed tannin (CT) from A. negra had an antiparasitic effect, thereby representing an alternative for worm control in sheep.

Verifying the botanical authenticity of commercial tannins through sugars and simple phenols profiles.

PubMed

Malacarne, Mario; Nardin, Tiziana; Bertoldi, Daniela; Nicolini, Giorgio; Larcher, Roberto

2016-09-01

Commercial tannins from several botanical sources and with different chemical and technological characteristics are used in the food and winemaking industries. Different ways to check their botanical authenticity have been studied in the last few years, through investigation of different analytical parameters. This work proposes a new, effective approach based on the quantification of 6 carbohydrates, 7 polyalcohols, and 55 phenols. 87 tannins from 12 different botanical sources were analysed following a very simple sample preparation procedure. Using Forward Stepwise Discriminant Analysis, 3 statistical models were created based on sugars content, phenols concentration and combination of the two classes of compounds for the 8 most abundant categories (i.e. oak, grape seed, grape skin, gall, chestnut, quebracho, tea and acacia). The last approach provided good results in attributing tannins to the correct botanical origin. Validation, repeated 3 times on subsets of 10% of samples, confirmed the reliability of this model. Copyright © 2016 Elsevier Ltd. All rights reserved.

Effect of tannin from Rhizophora apiculate as corrosion inhibitor for epoxy paint on mild steel

NASA Astrophysics Data System (ADS)

Idora, M. S. Noor; Quen, L. K.; Kang, H. S.

2017-09-01

There is a great concern to protect the steel surfaces from corrosion phenomenon in seawater environment. Several approaches have been proposed to introduce alternative new compounds in the paint which are green sources that can reduce environmental risks. The aim of this investigation was to enhance the protection properties of epoxy paint by providing an anticorrosive inhibitor for the paint. In this approach, the abilities of mangrove tannins, extracted from Rhizophora apiculata bark were studied. The inhibitive properties of mangrove tannins were evaluated by weight loss measurement, electrochemical impedance spectroscopy (EIS) and scanning electron microscope (SEM). Results shows the addition of mangrove tannin in the coating boosted the anticorrosive properties of the paint and represents valuable environmentally friendly of inhibitor.

Strategies to reduce end-product inhibition in family 48 glycoside hydrolases

DOE PAGES

Chen, Mo; Bu, Lintao; Alahuhta, Markus; ...

2016-02-01

Family 48 cellobiohydrolases are some of the most abundant glycoside hydrolases in nature. They are able to degrade cellulosic biomass and therefore serve as good enzyme candidates for biofuel production. Family 48 cellulases hydrolyze cellulose chains via a processive mechanism, and produce end products composed primarily of cellobiose as well as other cellooligomers (dp ≤ 4). The challenge of utilizing cellulases in biofuel production lies in their extremely slow turnover rate. A factor contributing to the low enzyme activity is suggested to be product binding to enzyme and the resulting performance inhibition. In this study, we quantitatively evaluated the productmore » inhibitory effect of four family 48 glycoside hydrolases using molecular dynamics simulations and product expulsion free-energy calculations. We also suggested a series of single mutants of the four family 48 glycoside hydrolases with theoretically reduced level of product inhibition. As a result, the theoretical calculations provide a guide for future experimental studies designed to produce mutant cellulases with enhanced activity.« less

Strategies to reduce end-product inhibition in family 48 glycoside hydrolases

DOE Office of Scientific and Technical Information (OSTI.GOV)

Chen, Mo; Bu, Lintao; Alahuhta, Markus

Family 48 cellobiohydrolases are some of the most abundant glycoside hydrolases in nature. They are able to degrade cellulosic biomass and therefore serve as good enzyme candidates for biofuel production. Family 48 cellulases hydrolyze cellulose chains via a processive mechanism, and produce end products composed primarily of cellobiose as well as other cellooligomers (dp ≤ 4). The challenge of utilizing cellulases in biofuel production lies in their extremely slow turnover rate. A factor contributing to the low enzyme activity is suggested to be product binding to enzyme and the resulting performance inhibition. In this study, we quantitatively evaluated the productmore » inhibitory effect of four family 48 glycoside hydrolases using molecular dynamics simulations and product expulsion free-energy calculations. We also suggested a series of single mutants of the four family 48 glycoside hydrolases with theoretically reduced level of product inhibition. As a result, the theoretical calculations provide a guide for future experimental studies designed to produce mutant cellulases with enhanced activity.« less

New phenylpropanoid glycosides from Juniperus communis var. depressa.

PubMed

Iida, Naoki; Inatomi, Yuka; Murata, Hiroko; Murata, Jin; Lang, Frank A; Tanaka, Toshiyuki; Nakanishi, Tsutomu; Inada, Akira

2010-05-01

Two new phenylpropanoid glycosides were isolated from the leaves and stems of Juniperus communis var. depressa (Cupressaceae) along with 14 known compounds. Their structures were determined by spectral analyses, in particular by 2D-NMR spectral evidence.

Glycosides from Medicinal Plants as Potential Anticancer Agents: Emerging Trends towards Future Drugs.

PubMed

Khan, Haroon; Saeedi, Mina; Nabavi, Seyed Mohammad; Mubarak, Mohammad S; Bishayee, Anupam

2018-04-03

Cancer continues to be a global burden, despite the advancement of various technological and pharmaceutical improvements over the past two decades. Methods for treating cancer include surgery, radiotherapy and chemotherapy in addition to other specialized techniques. On the other hand, medicinal plants have been traditionally employed either as the complementary medicine or dietary agents in the treatment and management of cancer. Medicinal plants are a rich source of secondary metabolites with interesting biological and pharmacological activities. Among these metabolites, glycosides are naturally occurring substances and have outstanding therapeutic potential and clinical utility. Different medical research engines such GoogleScholar, PubMed, SpringerLink, ScienceDirect were used to collect related literature on the subject matter. In this regard, only peer reviewed journals were considered. Emerging results showed that numerous glycosides isolated from various plants possessed marked anticancer activity against a variety of cancer cell lines. Accordingly, the aim of the present review is to shed light on the anticancer effects of glycosides, analyze possible mechanisms of action, and highlight the role of these natural agents as complementary and alternative medicine in combating and managing cancer. The glycosides isolated from different plants demonstrated potent cytotoxic effects against various cancer cell lines in initial preclinical studies. The anticancer effect was mediated through multiple mechanisms; however further detail studies are needed to understand the full potential of glycosides for clinical utility. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Isolation and Characterization of Proteolytic Ruminal Bacteria from Sheep and Goats Fed the Tannin-Containing Shrub Legume Calliandra calothyrsus

PubMed Central

McSweeney, Christopher S.; Palmer, Brian; Bunch, Rowan; Krause, Denis O.

1999-01-01

Tannins in forages complex with protein and reduce the availability of nitrogen to ruminants. Ruminal bacteria that ferment protein or peptides in the presence of tannins may benefit digestion of these diets. Bacteria from the rumina of sheep and goats fed Calliandra calothyrsus (3.6% N and 6% condensed tannin) were isolated on proteinaceous agar medium overlaid with either condensed (calliandra tannin) or hydrolyzable (tannic acid) tannin. Fifteen genotypes were identified, based on 16S ribosomal DNA-restriction fragment length polymorphism analysis, and all were proteolytic and fermented peptides to ammonia. Ten of the isolates grew to high optical density (OD) on carbohydrates (glucose, cellobiose, xylose, xylan, starch, and maltose), while the other isolates did not utilize or had low growth on these substrates. In pure culture, representative isolates were unable to ferment protein that was present in calliandra or had been complexed with tannin. One isolate, Lp1284, had high protease activity (80 U), a high specific growth rate (0.28), and a high rate of ammonia production (734 nmol/min/ml/OD unit) on Casamino Acids and Trypticase Peptone. Phylogenetic analysis of the 16S ribosomal DNA sequence showed that Lp1284 was related (97.6%) to Clostridium botulinum NCTC 7273. Purified plant protein and casein also supported growth of Lp1284 and were fermented to ammonia. This is the first report of a proteolytic, ammonia-hyperproducing bacterium from the rumen. In conclusion, a diverse group of proteolytic and peptidolytic bacteria were present in the rumen, but the isolates could not digest protein that was complexed with condensed tannin. PMID:10388706

Monoterpenyl Glycosyltransferases Differentially Contribute to Production of Monoterpenyl Glycosides in Two Aromatic Vitis vinifera Varieties.

PubMed

Li, Xiang-Yi; Wen, Ya-Qin; Meng, Nan; Qian, Xu; Pan, Qiu-Hong

2017-01-01

HIGHLIGHTS A similar trend on accumulation of glycosidically bound monoterpenes was observed in both varietiesTwo VvGT7 alleles mutations occurred at key sites in Muscat blanc à Petit VvGT14 exerted a major role in production of monoterpenyl glycosides in both varieties Terpenoids are the major aroma components and generally exist as both free and glycosidically-bound forms, of which nonvolatile glycosides account for a large fraction in grape berries. Our previous study has indicated that differential accumulation of monoterpenyl glycosides in Vitis vinifera "Muscat blanc à Petit" between two regions is closely correlated to monoterpenyl glucosyltransferase ( VvGT14 , XM_002285734.2) transcript abundance. However, it has not been determined yet whether this correlation also exists in other Vitis vinifera varieties. This study investigated the evolution of free and glycosidically bound monoterpenes in two Vitis vinifera variety "Muscat blanc à Petit" and "Gewurztraminer" under two vintages, and further assessed the relation between the accumulation of bound monoterpenes and two monoterpenyl glycosyltransferase transcript levels. Results showed that free monoterpenes exhibited three evolution patterns in both varieties during berry development of two vintages, whereas glycosidically bound monoterpenes showed a concentration elevation with berry maturation. The Cis -rose oxide and geraniol were major components contributing to the aroma odors of "Gewürztraminer" grapes while linalool was major aroma contributor to the "Muscat blanc à Petit grain" grapes. The accumulation of glycosidically bound monoterpenes in both varieties was accompanied with the high expression of VvGT7 (XM_002276510.2) and VvGT14 . Only one allele of VvGT7 was found in the variety "Gewürztraminer" and no mutation was observed in its enzyme active sites. XB-VvGT7-4 and XB-VvGT7-5 were two alleles of VvGT7 detected in "Muscat blanc à Petit grain." The mutation on its enzyme active site

Condensed tannins in some forage legumes: their role in the prevention of ruminant pasture bloat.

PubMed

Lees, G L

1992-01-01

For the past 20 years, the focus in our laboratory has been on finding the causes of ruminant pasture bloat and eventually breeding a bloat-safe alfalfa (Medicago sativa L.); i.e., with bloat potential reduced to the economic threshold. In the mid-seventies, the mechanisms of bloat were explored and found to be more physical than chemical. Characteristic of all bloating legumes after ingestion was a very rapid initial rate of ingestion by rumen microbes. Through the study of bloating and non-bloating legumes, factors were elucidated in the plant that would slow this process. One of these factors was the presence of condensed tannins in the herbage. Some of the non-bloating legumes contained these secondary metabolites, but no condensed tannins were found in any of the bloating legumes. Therefore, species containing an appreciable amount of condensed tannins in their leaves and stems are considered to be non-bloating. Conventional breeding methods have not been successful in producing an alfalfa with condensed tannins in its herbage. New approaches using tissue culture techniques are being attempted, but genetic engineering has the greatest potential for success.

Assessment of Anti-nutritive Activity of Tannins in Tea By-products Based on In vitro Rumen Fermentation

PubMed Central

Kondo, Makoto; Hirano, Yoshiaki; Ikai, Noriyuki; Kita, Kazumi; Jayanegara, Anuraga; Yokota, Hiro-omi

2014-01-01

Nutritive values of green and black tea by-products and anti-nutritive activity of their tannins were evaluated in an in vitro rumen fermentation using various molecular weights of polyethylene glycols (PEG), polyvinyl pyrrolidone (PVP) and polyvinyl polypyrrolidone as tannin-binding agents. Significant improvement in gas production by addition of PEG4000, 6000 and 20000 and PVP was observed only from black tea by-product, but not from green tea by-product. All tannin binding agents increased NH3-N concentration from both green and black tea by-products in the fermentation medium, and the PEG6000 and 20000 showed relatively higher improvement in the NH3-N concentration. The PEG6000 and 20000 also improved in vitro organic matter digestibility and metabolizable energy contents of both tea by-products. It was concluded that high molecular PEG would be suitable to assess the suppressive activity of tannins in tea by-products by in vitro fermentation. Higher responses to gas production and NH3-N concentration from black tea by-product than green tea by-product due to PEG indicate that tannins in black tea by-product could suppress rumen fermentation more strongly than that in green tea by-product. PMID:25358316

Glycosides from Bougainvillea glabra.

PubMed

Simon, András; Tóth, Gábor; Duddeck, Helmut; Soliman, Hesham S M; Mahmoud, Ibrahim I; Samir, Hanan

2006-01-01

Three glycosides were isolated from Bougainvillea glabra and their structures were determined by extensive use of 1D and 2D NMR spectroscopy ((1)H and (13)C). First compound was identical to momordin IIc (quinoside D) [beta-D-glucopyranosyl 3-O-[beta-D-xylopyranosyl-(1 --> 3)-O-(beta-D-glucopyranosyluronic acid)] oleanolate], second compound was quercetin 3-O-alpha-L-(rhamnopyranosyl)(1 --> 6)-[alpha-L-rhamnopy-ranosyl(1 --> 2)]-beta-D-galactopyranoside and third compound was its derivative quercetin 3-O-alpha-L-(4-caffeoylrhamnopyranosyl)(1 --> 6)-[alpha-L-rhamnopyranosyl (1 --> 2)]-beta-D-galactopyranoside, a new natural product.

Stabilization of erythrocytes against oxidative and hypotonic stress by tannins isolated from sumac leaves (Rhus typhina L.) and grape seeds (Vitis vinifera L.).

PubMed

Olchowik, Ewa; Lotkowski, Karol; Mavlyanov, Saidmukhtar; Abdullajanova, Nodira; Ionov, Maksim; Bryszewska, Maria; Zamaraeva, Maria

2012-09-01

Erythrocytes are constantly exposed to ROS due to their function in the organism. High tension of oxygen, presence of hemoglobin iron and high concentration of polyunsaturated fatty acids in membrane make erythrocytes especially susceptible to oxidative stress. A comparison of the antioxidant activities of polyphenol-rich plant extracts containing hydrolysable tannins from sumac leaves (Rhus typhina L.) and condensed tannins from grape seeds (Vitis vinifera L.) showed that at the 5-50 μg/ml concentration range they reduced to the same extent hemolysis and glutathione, lipid and hemoglobin oxidation induced by erythrocyte treatment with 400 μM ONOO(-) or 1 mM HClO. However, extract (condensed tannins) from grape seeds in comparison with extract (hydrolysable tannins) from sumac leaves stabilized erythrocytes in hypotonic NaCl solutions weakly. Our data indicate that both hydrolysable and condensed tannins significantly decrease the fluidity of the surface of erythrocyte membranes but the effect of hydrolysable ones was more profound. In conclusion, our results indicate that extracts from sumac leaves (hydrolysable tannins) and grape seeds (condensed tannins) are very effective protectors against oxidative damage in erythrocytes.

Tannins of tamarind seed husk: preparation, structural characterization, and antioxidant activities.

PubMed

Sinchaiyakit, Puksiri; Ezure, Yohji; Sriprang, Sarin; Pongbangpho, Supakorn; Povichit, Nasapon; Suttajit, Maitree

2011-06-01

The high content (about 39%) of polymeric tannins in tamarind (Tamarindus indica L.) seed husk (TSH) was demonstrated, and an extract (crude TSE) with a high content (about 94%) of polymeric tannins was prepared from TSH with a one pot extraction using ethanol/water (3:2, v/v). The crude TSE was further purified with Sephadex LH20 to give one fraction (metTSE) eluted with methanol/water (3:2, v/v) and another (acTSE) eluted with acetone/water (3:2, v/v). The tannins of acTSE were established as polymeric proanthocyanidins (PA) by 13C NMR spectroscopy; this was further confirmed by IR and UV spectroscopy, n-BuOH/HCl and vanillin assays, and from HPLC pattern. The ratio of procyanidins to prodelphinidins was 2:3, and the average degree of polymerization of acTSE was 7. Galloylated flavan-3-ols were not detected in acTSE. The main ingredients of metTSE were confirmed to be polymeric PA by 13C NMR spectroscopy. The antioxidant activities using DPPH and ABTS assays were investigated. The IC50 values of acTSE were 4.2 +/- 0.2 (DPPH assay) and 6.2 +/- 0.3 microg/mL (ABTS assay).

Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla.

PubMed

Barnes, Curtis C; Smalley, Mary K; Manfredi, Kirk P; Kindscher, Kelly; Loring, Hillary; Sheeley, Douglas M

2003-11-01

The organic soluble extract from the leaves of the native North American prairie plant Ipomoea leptophylla (big root morning glory) showed in vitro activity against M. tuberculosis. Bioassay-guided fractionation of this extract resulted in the identification of two new resin glycosides (6, 7). Base-catalyzed hydrolysis of these glycosides gave operculinic acid (1) as the glycosidic acid component as well as trans-cinnamic acid, propanoic acid, and lauric acid. The complete structure elucidation was accomplished through derivatization, 1D and 2D NMR spectroscopy (TOCSY, ROESY, HSQC, HMBC), and MS/MS experiments on 6 and 7 as well as the permethylated derivative 8.

Removing tannins from medicinal plant extracts using an alkaline ethanol precipitation process: a case study of Danshen injection.

PubMed

Gong, Xingchu; Li, Yao; Qu, Haibin

2014-11-14

The alkaline ethanol precipitation process is investigated as an example of a technique for the removal of tannins extracted from Salviae miltiorrhizae Radix et Rhizoma for the manufacture of Danshen injection. More than 90% of the tannins can be removed. However, the recoveries of danshensu, rosmarinic acid, and salvianolic acid B were less than 60%. Total tannin removal increased as the refrigeration temperature decreased or the amount of NaOH solution added increased. Phenolic compound recoveries increased as refrigeration temperature increased or the amount of NaOH solution added decreased. When operated at a low refrigeration temperature, a relative high separation selectivity can be realized. Phenolic compound losses and tannin removal were mainly caused by precipitation. The formation of phenol salts, whose solubility is small in the mixture of ethanol and water used, is probably the reason for the precipitation. A model considering dissociation equilibrium and dissolution equilibrium was established. Satisfactory correlation results were obtained for phenolic compound recoveries and total tannin removal. Two important parameters in the model, which are the water content and pH value of alkaline supernatant, are suggested to be monitored and controlled to obtain high batch-to-batch consistency.

The effect of feed moisture and temperature on tannin content, antioxidant and antimicrobial activities of extruded chestnuts.

PubMed

Obiang-Obounou, Brice Wilfried; Ryu, Gi Hyung

2013-12-15

This study focuses on the effect of extrusion processing on tannin reduction, phenolic content, flavonoid content, antioxidant and anitimicrobial activity. Extrusion temperature (120 and 140 °C) and feed moisture (25% and 28%) were used on the tannin content, antioxidant and antimicrobial activities. Extrusion cooking reduced tannin content up to 78%, and improved antioxidant activity from 12.89% to 21.17% in a concentration dependant manner without affecting its antimicrobial activity that varied from 250 to 500 mg. The time-kill assay confirmed the ability of extruded chestnut to reduce Pseudomonas aeruginosa count below detectable limit that reduced the original inoculum by 3log10 CFU/mL. Overall, the results showed that extrusion cooking might serve as a tool for tannin reduction and could improve the antioxidant and antimicrobial properties of chestnut, which might be helpful for chestnut related products in the food industry. Copyright © 2013 Elsevier Ltd. All rights reserved.

Profiling of iridoid glycosides in Vaccinium species by UHPLC-MS.

PubMed

Heffels, Peter; Müller, Laura; Schieber, Andreas; Weber, Fabian

2017-10-01

The iridoid profile of four Vaccinium species was investigated using UHPLC-MS to obtain further information about this group of species for phytochemical characterization. Fruits of bog bilberry (Vaccinium uliginosum L.) showed 14 different iridoid glycosides with a total amount of 20mg/kg fresh weight (FW), whereas bilberry (Vaccinium myrtillus L.) contained 11 iridoid glycosides and a total amount of 127mg/kg FW. Highbush blueberry (Vaccinium corymbosum L.) and lowbush blueberry (Vaccinium angustifolium L.) contained none of the investigated iridoid glycosides. Among the different iridoids, the isomers scandoside and deacetylasperulosidic acid as well as a dihydro derivative thereof were described for the first time in the Ericaceae family. The p-coumaroyl isomers of scandoside, deacetylasperulosidic acid and dihydromonotropein are reported for the first time in V. myrtillus and V. uliginosum. Monotropein and its p-coumaroyl isomers were found for the first time in V. uliginosum. The comparison of iridoid profiles in bilberry fruit and juice samples revealed constant proportions throughout the juice processing. Quantification and profile determination of iridoids may be used for species differentiation and thus for authentication purposes. Copyright © 2016 Elsevier Ltd. All rights reserved.

Sweet Poisons: Honeys Contaminated with Glycosides of the Neurotoxin Tutin.

PubMed

Larsen, Lesley; Joyce, Nigel I; Sansom, Catherine E; Cooney, Janine M; Jensen, Dwayne J; Perry, Nigel B

2015-06-26

Poisonings due to consumption of honeys containing plant toxins have been reported widely. One cause is the neurotoxin tutin, an oxygenated sesquiterpene picrotoxane, traced back to honeybees (Apis mellifera) collecting honeydew produced by passionvine hoppers (Scolypopa australis) feeding on sap of the poisonous shrub tutu (Coriaria spp.). However, a pharmacokinetic study suggested that unidentified conjugates of tutin were also present in such honeys. We now report the discovery, using ion trap LC-MS, of two tutin glycosides and their purification and structure determination as 2-(β-d-glucopyranosyl)tutin (4) and 2-[6'-(α-d-glucopyranosyl)-β-d-glucopyranosyl]tutin (5). These compounds were used to develop a quantitative triple quadrupole LC-MS method for honey analysis, which showed the presence of tutin (3.6 ± 0.1 μg/g honey), hyenanchin (19.3 ± 0.5), tutin glycoside (4) (4.9 ± 0.4), and tutin diglycoside (5) (4.9 ± 0.1) in one toxic honey. The ratios of 4 and 5 to tutin varied widely in other tutin-containing honeys. The glycosidation of tutin may represent detoxification by one or both of the insects involved in the food chain from plant to honey.

Phenylethanoid Glycosides: Research Advances in Their Phytochemistry, Pharmacological Activity and Pharmacokinetics.

PubMed

Xue, Zhenzhen; Yang, Bin

2016-07-29

Phenylethanoid glycosides (PhGs) are widely distributed in traditional Chinese medicines as well as in other medicinal plants, and they were characterized by a phenethyl alcohol (C₆-C₂) moiety attached to a β-glucopyranose/β-allopyranose via a glycosidic bond. The outstanding activity of PhGs in diverse diseases proves their importance in medicinal chemistry research. This review summarizes new findings on PhGs over the past 10 years, concerning the new structures, their bioactivities, including neuroprotective, anti-inflammatory, antioxidant, antibacterial and antivirus, cytotoxic, immunomodulatory, and enzyme inhibitory effects, and pharmacokinetic properties.

Enhanced profiling of flavonol glycosides in the fruits of sea buckthorn (Hippophae rhamnoides).

PubMed

Fang, Rui; Veitch, Nigel C; Kite, Geoffrey C; Porter, Elaine A; Simmonds, Monique S J

2013-04-24

Use of enhanced LC-MS/MS methods to identify common glycosyl groups of flavonoid glycosides enabled better characterization of the flavonoids in fruits of sea buckthorn (Hippophae rhamnoides). The saccharide moieties of 48 flavonol O-glycosides detected in a methanol extract were identified by these methods. Several of the flavonol glycosides were acylated, two of which were isolated and found to be new compounds. Their structures were determined using spectroscopic and chemical methods as isorhamnetin 3-O-(6-O-E-sinapoyl-β-D-glucopyranosyl)-(1→2)-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside (24) and isorhamnetin 3-O-(6-O-E-feruloyl-β-D-glucopyranosyl)-(1→2)-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside (30). Analysis of the acylated glycosyl groups of 24 and 30 by serial mass spectrometry provided evidence to suggest the acylation position of 11 other minor flavonol glycosides acylated with hydroxycinnamic or hydroxybenzoic acids. The nitric oxide scavenging activities of 24 and 30 were compared with those of other flavonoids and with ascorbic acid and the potassium salt of 2-(4-carboxyphenyl)-4,5-dihydro-4,4,5,5-tetramethyl-1H-imidazolyl-1-oxy-3-oxide (carboxy-PTIO).

A new withanolide glycoside from physalis peruviana

PubMed

Ahmad; Malik; Afza; Yasmin

1999-03-01

A new withanolide glycoside, 17beta-hydroxy-14, 20-epoxy-1-oxo-[22R]-3beta-[O-beta-D-glucopyranosyl]-witha-5, 24-dienolide (1), has been isolated from the whole plant of Physalis peruviana. Its identity was determined using a combination of spectroscopic data including 2D NMR techniques and chemical transformations.

Absorption of mercuric cation by tannins in agricultural residues

DOE Office of Scientific and Technical Information (OSTI.GOV)

Waiss, A.C. Jr.; Wiley, M.E.; Kuhnle, J.A.

1973-01-01

Two common environmental pollutants are agricultural residues (skins, pits, husks, tannin bark, grape pomace) and waste streams of water containing only traces of heavy metals (such as mercury at 10 or more ppb) from mining or manufacturing operations. Agricultural residues contain tannins, polyphenolic substances, pectin, and other polymers-all with chemically reactive groups that can chelate, reduce, oxidize, demonstrate ion exchange properties, and aid in removing traces of heavy metals from dilute waste water streams at low cost. Finely ground and water-washed agricultural residues were slurried in water and packed into columns for absorption tests with heavy metals. Solutions of knownmore » concentrations of heavy metals were passed through the packed columns which were then eluted with water or with alkaline or acidic solutions. The fractions and the column absorbents were then analyzed by standard atomic absorption methods. The nature of the physical and chemical forces that are effective in metal absorption from agricultural residues is not clear.« less

Systematic studies of tannin-formaldehyde aerogels: preparation and properties

NASA Astrophysics Data System (ADS)

Amaral-Labat, Gisele; Szczurek, Andrzej; Fierro, Vanessa; Pizzi, Antonio; Celzard, Alain

2013-02-01

Gelation of tannin-formaldehyde (TF) solutions was systematically investigated by changing pH and concentration of TF resin in water. In this way we constructed the TF phase diagram, from which chemical hydrogels could be described, and also synthesized thermoreversible tannin-based hydrogels. Conditions of non-gelation were also determined. Hydrogels were dried in supercritical CO2, leading to a broad range of TF aerogels. The latter were investigated for volume shrinkage, total porosity, micro-, meso- and macropore volumes, Brunauer-Emmett-Teller (BET) surface area, microscopic texture, mechanical and thermal properties. All these properties are discussed in relation to each other, leading to an accurate and self-consistent description of these bioresource-based highly porous materials. The conditions for obtaining the highest BET surface area or mesopore volume were determined and explained in relation to the preparation conditions. The highest BET surface area, 880 m2 g-1, is remarkably high for organic aerogels derived from a natural resource.

Two new chalcone glycosides from the stems of Entada phaseoloides.

PubMed

Zhao, Zhong-xiang; Jin, Jing; Lin, Chao-zhan; Zhu, Chen-chen; Liu, Yi-ming; Lin, Ai-hua; Liu, Ying-xiang; Zhang, Li; Luo, Hua-feng

2011-10-01

Two new chalcone glycosides 4'-O-(6″-O-galloyl-β-d-glucopyranosyl)-2',4-dihydroxychalcone (1) and 4'-O-(6″-O-galloyl-β-d-glucopyranosyl)-2'-hydroxy-4-methoxychalcone (2) together with one known chalcone glycoside 4'-O-β-d-glucopyranosyl-2'-hydroxy-4-methoxychalcone (3) were isolated from the stems of Entada phaseoloides. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC, (1)H-(1)H COSY, and chemical evidences. This is the first report of chalcone-type compounds isolated from the genus Entada. Copyright © 2011 Elsevier B.V. All rights reserved.

Domestication and defence: Foliar tannins and C/N ratios in cassava and a close wild relative

NASA Astrophysics Data System (ADS)

Mondolot, Laurence; Marlas, Amandine; Barbeau, Damien; Gargadennec, Annick; Pujol, Benoît; McKey, Doyle

2008-09-01

Plant domestication is accompanied by shifts in resource allocation, as a result of farmer selection for genotypes that give high yields in agricultural habitats. Relaxed natural selection for chemical and physical defences in these habitats could facilitate resource allocation to yield. We compared the concentrations of tannins, and C/N ratios, which are often correlated with investment in cell-wall compounds, in leaves of landraces of domesticated cassava ( Manihot esculenta) and a close wild relative in French Guiana. Foliar concentrations of tannins were about 1.9 times higher in the wild relative than in domesticated cassava. Histochemical analyses showed that tannins were present in nearly all palisade and spongy parenchyma cells of the wild taxon, but in only some cells of these tissues in M. esculenta. C/N ratios were also 1.9 times higher in leaves of the wild relative than in those of domesticated cassava. Tannins accounted for only a small proportion of total carbon, and the higher C/N ratio in wild than in domesticated cassava may reflect higher investment in carbon-containing compounds additional to tannins, such as cell-wall compounds. The divergence in these traits between cassava and this close wild relative mirrors a broad pattern observed in wild plant species across habitats varying in resource availability. One explanation for our results is that domestication in cassava may have favoured a shift from a resource conservation strategy to a resource acquisition strategy.

Properties of wine polymeric pigments formed from anthocyanin and tannins differing in size distribution and subunit composition.

PubMed

Bindon, Keren; Kassara, Stella; Hayasaka, Yoji; Schulkin, Alex; Smith, Paul

2014-11-26

To explore the effect of tannin composition on pigment formation, model ferments of purified 3-O-monoglucoside anthocyanins (ACN) were conducted either alone or in the presence of two different tannins. Tannins were isolated from grape seeds (Sd) or skins (Sk) following exhaustive extraction in 70% v/v acetone. The Sd and Sk tannin fractions had a mean degree of polymerization of 5.2 and 25.6, respectively. The Sd fraction was highly galloylated, at 22%, but galloylation was <2% in the Sk fraction. The Sk fraction was distinguished by a high proportion of prodelphinidin, at 58%. After a 6 month aging period, polymeric pigments were quantified and their color properties determined following isolation by solid-phase extraction. Wine color and polymeric pigment were highest in the treatment containing ACN+Sd and similar in the ACN+Sk and ACN treatments. The same trend between treatments was observed for total and polymeric nonbleachable pigments. Only minor changes in tannin subunit composition were found following ACN incorporation, but the size distribution of polymeric pigments determined by gel permeation chromatography decreased, in particular for the ACN+Sk treatment. Color incorporation in the higher molecular mass range was lower for ACN+Sk wines than for ACN+Sd wines. Compositional differences between the two tannin fractions may therefore limit the incorporation of ACNs in the colored form. The results suggest that in the ACN+Sk and ACN treatments, the formation of lower molecular mass oligomeric pigments was favored. In polymeric pigments derived from ACNs, the presence of ethyl- and vinyl-linked ACNs to the level of trimers was identified using mass spectrometry.

Effect of condensed tannins on bovine rumen protist diversity based on 18S rRNA gene sequences.

PubMed

Tan, Hui Yin; Sieo, Chin Chin; Abdullah, Norhani; Liang, Juan Boo; Huang, Xiao Dan; Ho, Yin Wan

2013-01-01

Molecular diversity of protists from bovine rumen fluid incubated with condensed tannins of Leucaena leucocephala hybrid-Rendang at 20 mg/500 mg dry matter (treatment) or without condensed tannins (control) was investigated using 18S rRNA gene library. Clones from the control library were distributed within nine genera, but clones from the condensed tannin treatment clone library were related to only six genera. Diversity estimators such as abundance-based coverage estimation and Chao1 showed significant differences between the two libraries, although no differences were found based on Shannon-Weaver index and Libshuff. © 2012 The Author(s) Journal of Eukaryotic Microbiology © 2012 International Society of Protistologists.

The colloidal state of tannins impacts the nature of their interaction with proteins: the case of salivary proline-rich protein/procyanidins binding.

PubMed

Cala, Olivier; Dufourc, Erick J; Fouquet, Eric; Manigand, Claude; Laguerre, Michel; Pianet, Isabelle

2012-12-18

While the definition of tannins has been historically associated with its propensity to bind proteins in a nonspecific way, it is now admitted that specific interaction also occurs. The case of the astringency perception is a good example to illustrate this phenomenon: astringency is commonly described as a tactile sensation induced by the precipitation of a complex composed of proline-rich proteins present in the human saliva and tannins present in beverages such as tea or red wines. In the present work, the interactions between a human saliva protein segment and three different procyanidins (B1, B3, and C2) were investigated at the atomic level by NMR and molecular dynamics. The data provided evidence for (i) an increase in affinity compared to shortest human saliva peptides, which is accounted for by protein "wraping around" the tannin, (ii) a specificity in the interaction below tannin critical micelle concentration (CMC) of ca. 10 mM, with an affinity scale such that C2 > B1 > B3, and (iii) a nonspecific binding above tannin CMC that conducts irremediably to the precipitation of the tannins/protein complex. Such physicochemical findings describe in accurate terms saliva protein-tannin interactions and provide support for a more subtle description by oenologists of wine astringency perception in the mouth.

Non-targeted glycosidic profiling of international wines using neutral loss-high resolution mass spectrometry.

PubMed

Barnaba, C; Dellacassa, E; Nicolini, G; Nardin, T; Serra, M; Larcher, R

2018-07-06

Many metabolites naturally occur as glycosides, since sugar moieties can be crucial for their biological activity and increase their water solubility. In the plant kingdom they may occur as glycosides or sugar esters, depending on precursor chemical structure, and in wine they have traditionally attracted attention due to their organoleptic properties, such as astringency and bitterness, and because they affect the colour and aroma of wines. A new approach directed at detailed description of glycosides in a large selection of monovarietal wines (8 samples each of Pinot Blanc, Muller Thurgau, Riesling, Traminer, Merlot, Pinot Noir and Cabernet Sauvignon) was developed by combining high performance liquid chromatography with high resolution tandem mass spectrometry. Analytical separation was performed on an Accucore™ Polar Premium LC column, while mass analysis was performed in negative ion mode with an non-targeted screening approach, using a Full MS/AIF/NL dd-MS 2 experiment at a resolving power of 140,000 FWHM. Over 280 glycoside-like compounds were detected, of which 133 (including low-molecular weight phenols, flavonoids and monoterpenols) were tentatively identified in the form of pentose (6), deoxyhexose (17), hexose (73), hexose-pentose (16), hexose-deoxyhexose (7), dihexose (5) and hexose ester (9) derivatives. It was not possible to univocally define the corresponding chemical structure for the remaining 149 glycosides. Non-parametric statistical analysis showed it was possible to well characterise the glycosylated profile of all red and Traminer wines, while the identified glycosides were almost entirely lacking in Pinot Blanc, Riesling and Muller Thurgau wines. Also Tukey's Honestly Significant Difference test (p < 0.05) and Principal Component Analysis confirmed that it was possible to almost entirely distinguish the selected red wines from each other according to their glycosylated profile. Copyright © 2018 Elsevier B.V. All rights reserved.

Tannase enhances the anti-inflammatory effect of grape pomace in Caco-2 cells treated with IL-1beta

USDA-ARS?s Scientific Manuscript database

Grape pomace (GP) is rich in polymeric polyphenolics and glycosides which have lower bioefficacy than monomeric and aglycone counterparts. The aim of this study was to determine whether tannin acyl hydrolase [tannase (TNS)] can improve the antioxidant and anti-inflammatory actions of GP in Caco-2 ce...

Monoterpenyl Glycosyltransferases Differentially Contribute to Production of Monoterpenyl Glycosides in Two Aromatic Vitis vinifera Varieties

PubMed Central

Li, Xiang-Yi; Wen, Ya-Qin; Meng, Nan; Qian, Xu; Pan, Qiu-Hong

2017-01-01

HIGHLIGHTS A similar trend on accumulation of glycosidically bound monoterpenes was observed in both varietiesTwo VvGT7 alleles mutations occurred at key sites in Muscat blanc à PetitVvGT14 exerted a major role in production of monoterpenyl glycosides in both varieties Terpenoids are the major aroma components and generally exist as both free and glycosidically-bound forms, of which nonvolatile glycosides account for a large fraction in grape berries. Our previous study has indicated that differential accumulation of monoterpenyl glycosides in Vitis vinifera “Muscat blanc à Petit” between two regions is closely correlated to monoterpenyl glucosyltransferase (VvGT14, XM_002285734.2) transcript abundance. However, it has not been determined yet whether this correlation also exists in other Vitis vinifera varieties. This study investigated the evolution of free and glycosidically bound monoterpenes in two Vitis vinifera variety “Muscat blanc à Petit” and “Gewurztraminer” under two vintages, and further assessed the relation between the accumulation of bound monoterpenes and two monoterpenyl glycosyltransferase transcript levels. Results showed that free monoterpenes exhibited three evolution patterns in both varieties during berry development of two vintages, whereas glycosidically bound monoterpenes showed a concentration elevation with berry maturation. The Cis-rose oxide and geraniol were major components contributing to the aroma odors of “Gewürztraminer” grapes while linalool was major aroma contributor to the “Muscat blanc à Petit grain” grapes. The accumulation of glycosidically bound monoterpenes in both varieties was accompanied with the high expression of VvGT7 (XM_002276510.2) and VvGT14. Only one allele of VvGT7 was found in the variety “Gewürztraminer” and no mutation was observed in its enzyme active sites. XB-VvGT7-4 and XB-VvGT7-5 were two alleles of VvGT7 detected in “Muscat blanc à Petit grain.” The mutation on its

In silico analysis and expression profiling of miRNAs targeting genes of steviol glycosides biosynthetic pathway and their relationship with steviol glycosides content in different tissues of Stevia rebaudiana.

PubMed

Saifi, Monica; Nasrullah, Nazima; Ahmad, Malik Mobeen; Ali, Athar; Khan, Jawaid A; Abdin, M Z

2015-09-01

miRNAs are emerging as potential regulators of the gene expression. Their proven promising role in regulating biosynthetic pathways related gene networks may hold the key to understand the genetic regulation of these pathways which may assist in selection and manipulation to get high performing plant genotypes with better secondary metabolites yields and increased biomass. miRNAs associated with genes of steviol glycosides biosynthetic pathway, however, have not been identified so far. In this study miRNAs targeting genes of steviol glycosides biosynthetic pathway were identified for the first time whose precursors were potentially generated from ESTs and nucleotide sequences of Stevia rebaudiana. Thereafter, stem-loop coupled real time PCR based expressions of these miRNAs in different tissues of Stevia rebaudiana were investigated and their relationship pattern was analysed with the expression levels of their target mRNAs as well as steviol glycoside contents. All the miRNAs investigated showed differential expressions in all the three tissues studied, viz. leaves, flowers and stems. Out of the eleven miRNAs validated, the expression levels of nine miRNAs (miR319a, miR319b, miR319c, miR319d, miR319e, miR319f, miR319h, miRstv_7, miRstv_9) were found to be inversely related, while expression levels of the two, i.e. miR319g and miRstv_11 on the contrary, showed direct relation with the expression levels of their target mRNAs and steviol glycoside contents in the leaves, flowers and stems. This study provides a platform for better understanding of the steviol glycosides biosynthetic pathway and these miRNAs can further be employed to manipulate the biosynthesis of these metabolites to enhance their contents and yield in S. rebaudiana. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

[Contents of tannins and oxalic acid in the selected forest fruits depending on the harvest site].

PubMed

Sembratowicz, Iwona; Ognik, Katarzyna; Rusinek, Elzbieta; Truchliński, Jerzy

2008-01-01

Contents of anti-nutritional components (tannins and oxalic acid) were determined in samples of forest fruits: blueberry, raspberry and wild strawberry harvested in Lublin region from areas considered as potentially not exposed to pollution (Skierbieszów Landscape Park) and potentially polluted areas (Cement Factory Rejowiec S.A.). Study revealed that blueberry and raspberry fruits collected on potentially polluted area were characterized by higher tannins contents than those harvested on potentially not polluted area. Oxalic acid level in studied material indicated its significantly higher concentration in wild strawberry fruits collected both from not exposed and polluted areas as compared to raspberry and blueberry. Tannins and oxalic acid contents in analyzed berries may be accepted as low and safe for human's health.

The gastroprotective effects of Eugenia dysenterica (Myrtaceae) leaf extract: the possible role of condensed tannins.

PubMed

Prado, Ligia Carolina da Silva; Silva, Denise Brentan; de Oliveira-Silva, Grasielle Lopes; Hiraki, Karen Renata Nakamura; Canabrava, Hudson Armando Nunes; Bispo-da-Silva, Luiz Borges

2014-01-01

We applied a taxonomic approach to select the Eugenia dysenterica (Myrtaceae) leaf extract, known in Brazil as "cagaita," and evaluated its gastroprotective effect. The ability of the extract or carbenoxolone to protect the gastric mucosa from ethanol/HCl-induced lesions was evaluated in mice. The contributions of nitric oxide (NO), endogenous sulfhydryl (SH) groups and alterations in HCl production to the extract's gastroprotective effect were investigated. We also determined the antioxidant activity of the extract and the possible contribution of tannins to the cytoprotective effect. The extract and carbenoxolone protected the gastric mucosa from ethanol/HCl-induced ulcers, and the former also decreased HCl production. The blockage of SH groups but not the inhibition of NO synthesis abolished the gastroprotective action of the extract. Tannins are present in the extract, which was analyzed by matrix assisted laser desorption/ionization (MALDI); the tannins identified by fragmentation pattern (MS/MS) were condensed type-B, coupled up to eleven flavan-3-ol units and were predominantly procyanidin and prodelphinidin units. Partial removal of tannins from the extract abolished the cytoprotective actions of the extract. The extract exhibits free-radical-scavenging activity in vitro, and the extract/FeCl3 sequence stained gastric surface epithelial cells dark-gray. Therefore, E. dysenterica leaf extract has gastroprotective effects that appear to be linked to the inhibition of HCl production, the antioxidant activity and the endogenous SH-containing compounds. These pleiotropic actions appear to be dependent on the condensed tannins contained in the extract, which bind to mucins in the gastric mucosa forming a protective coating against damaging agents. Our study highlights the biopharmaceutical potential of E. dysenterica.

[HPLC-fingerprint-based quality evaluation on a Tibetan medicine Phyllanthus emblica and its tannin parts].

PubMed

Sun, Xue-Fei; Zhang, Hong-Yan; Xia, Qing; Zhao, Hai-Juan; Wu, Ling-Fang; Zhang, Lan-Zhen; Shi, Ren-Bing

2014-04-01

This study is to establish the fingerprint for Phyllanthus emblica and their tannin parts from different habitats by HPLC for its quality control. The determination was carried out on a Diamonsil C18 (4.6 mm x 250 mm, 5 microm) column, with methanol-0.2% glacial acetic acid as mobile phase with gradient elution at a flow rate of 1 mL x min(-1). The temperature was maintained at 30 degrees C and the detected wavelength is 260 nm, Thirteen chromatographic peaks were extracted as the common peaks of the fingerprint of P. emblica, and eleven as the common peaks of P. emblica tannin parts, and five peaks were identified by comparing with referent samples. The fingerprints of 8 samples were compared and classified by similarity evaluation, cluster analysis and principal component analysis (PCA). The similarity degrees of eight P. emblica were between 0.763 and 0.993, while tannin parts were between 0.903 and 0.991. All the samples of P. emblica and their tannin parts were classified into 3 categories. The method was so highly reproducible, simple and reliable that it could provide basis for quality control and evaluation of P. emblica from different habitats.

Relationship of Soluble Grape-Derived Proteins to Condensed Tannin Extractability during Red Wine Fermentation.

PubMed

Springer, Lindsay F; Chen, Lei-An; Stahlecker, Avery C; Cousins, Peter; Sacks, Gavin L

2016-11-02

In red winemaking, the extractability of condensed tannins (CT) can vary considerably even under identical fermentation conditions, and several explanations for this phenomenon have been proposed. Recent work has demonstrated that grape pathogenesis-related proteins (PRPs) may limit retention of CT added to finished wines, but their relevance to CT extractability has not been evaluated. In this work, Vitis vinifera and interspecific hybrids (Vitis ssp.) from both hot and cool climates were vinified under small-scale, controlled conditions. The final CT concentration in wine was well modeled from initial grape tannin and juice protein concentrations using the Freundlich equation (r 2 = 0.686). In follow-up experiments, separation and pretreatment of juice by bentonite, heating, freezing, or exogenous tannin addition reduced protein concentrations in juices from two grape varieties. The bentonite treatment also led to greater wine CT for one of the varieties, indicating that prefermentation removal of grape protein may be a viable approach to increasing wine CT.

Three-dimensional structure and dynamics of wine tannin-saliva protein complexes. A multitechnique approach.

PubMed

Simon, Cécile; Barathieu, Karine; Laguerre, Michel; Schmitter, Jean-Marie; Fouquet, Eric; Pianet, Isabelle; Dufourc, Erick J

2003-09-09

The interactions between the B3 (catechin-4alpha,8-catechin) red wine tannin and the human salivary protein fragment IB7(14) (SPPGKPQGPPPQGG) were monitored by (1)H magic angle spinning NMR, circular dichroism, electrospray ionization mass spectrometry, and molecular modeling. It is found that the secondary structure of IB7(14) is made of a type II helix (collagen helix) and random coil. The central glycine 8 appears to act as a flexible rotula separating two helix II regions. Three tannin molecules tightly complex the peptide, without modifying its secondary structure, but seem to reduce its conformational dynamics. The binding dissociation constant is in the millimolar range. B3 tannins with a "tweezers" conformation bind to the hydrophilic side of the saliva peptide, suggesting that the principal driving forces toward association are governed by hydrogen bonding between the carbonyl functions of proline residues and both the phenol and catechol OH groups. These findings are further discussed in the frame of an astringency phenomenon.

Condensed tannins: Quinone methide intermediates in procyanidin synthesis

Treesearch

Richard W. Hemingway; L. Y. Foo

1983-01-01

Proanthocyanidins (condensed tanruns) are widely distributed in plants and are found in sufficiently high concentration in some tree barks to encourage their industrial utilization. These polymers consist of flavanoid units linked through the C-4 of the pyran ring to the C-6 or C-8 carbons of the aromatic A-ring. Recent advances in the chemistry of condensed tannins...

Effects of plant tannin extracts supplementation on animal performance and gastrointestinal parasites infestation in steers grazing winter wheat

USDA-ARS?s Scientific Manuscript database

Twenty-six stocker cattle (286.1 ± 25.7 kg) were used to quantify the effect of commercial plant tannin extracts (control vs. mimosa and chestnut tannins) on animal performance, gastrointestinal parasites control, and plasma metabolite changes in heifers grazing winter wheat forage (Triticum aestivu...

Effects of hydrolyzable and condensed tannin on growth and development of two species of polyphagous lepidoptera: Spodoptera eridania and Callosamia promethea.

PubMed

Manuwoto, Svafrida; Scriber, J Mark

1986-05-01

The effects of tannins on survival, growth, and digestion were compared in two polyphagous species of Lepidoptera (one, the southern armyworm, a forb-feeder; and the other, the promethea silkmoth, a tree-feeder). Two different types of tannins (hydrolyzable and condensed) were incorporated into artificial basal diets in order to determine whether or not differential survival and growth would result between the forb feeder, which normally does not encounter tannins in its natural diet, and the tree-feeder, whose host species include many tanniniferous plants from several different families.Neonate larvae of the forb-feeding armyworms exhibited significantly suppressed 10-day growth rates at all tannin concentrations tested (0.5, 1.0, 1.5, 2.0, 2.5, and 3.0% of wet weight) for both the hydrolyzable and the condensed tannin compared to the control diet, however no dose-effect was detectable. In contrast, there were no detectable differences in neonate survival or growth through the first 10 days for the tree-feeding promethea silkmoth larvae fed diets with either tannic acid or quebracho tree condensed tannin.In order to determine the physiological mechanisms of action of these tannins against armyworms, we conducted detailed physiological bioassays of biomass and nitrogen utilization by penultimate instar larvae. Standard gravimetric feeding studies with both tannic acid and the quebracho tree condensed tannin demonstrated that reduced relative growth rates (RGR's) of Spodoptera eridania Cram. were due to the suppressed relative consumption rates (RCR's) and decreased conversion efficiencies (ECD's) rather than due to digestibility-reduction (as reflected by approximate digestibility, AD). As with the neonate larval growth rate suppression, there were no detectable dose responses at the different concentrations of tannic acid (0.25, 0.50, 0.75, 1.00, 2.50, and 5.0 percent) and condensed tannins from quebracho (0.25, 0.50, 0.75, 1.0, and 2.5 percent) in our

Glucose, fructose and sucrose increase the solubility of protein-tannin complexes and at high concentration, glucose and sucrose interfere with bisulphite bleaching of wine pigments.

PubMed

Harbertson, James F; Yuan, Chunlong; Mireles, Maria S; Hanlin, Rachel L; Downey, Mark O

2013-05-01

Wines were modified with increasing sugar concentrations and decreasing tannin concentrations and analysed by a combination of protein precipitation and bisulphite bleaching. Increasing sugar concentration decreased the precipitation of tannin and protein-precipitable polymeric pigments (PPP). The use of a hydrogen bond disruptor (urea) to reduce protein-tannin and protein-pigment complex formation showed that the effect of sugar concentration occurred by increasing the solubility of the tannin-protein complex, not by interfering with protein-tannin complex formation. By increasing the solubility of pigment-protein complexes, non-protein-precipitable polymeric pigments (nPPP) appeared to increase. There was also an increase in total polymeric pigments at each tannin concentration with increasing glucose and sucrose concentration, indicating that sugar concentration might also affect bisulphite bleaching of wine pigments. While a significant effect of sugar concentration on tannin-protein complex solubility was observed, these effects were greatest at sugar concentrations far in excess of normal wine making conditions. Under normal wine making conditions, sugar concentration will have a negligible effect on protein-precipitable tannin, PPP and nPPP concentrations. Copyright © 2012 Elsevier Ltd. All rights reserved.

C-glycosides from the stems of Calophyllum membranaceum.

PubMed

Zhu, Ling-Juan; Yi, Sen; Li, Xue; Chen, Hai-Feng; Ming, Meng; Zhang, Xue; Yao, Xin-Sheng

2018-01-01

Three new C-glycosides, calophymembransides D-F (1-3), were isolated from the stems of Calophyllum membranaceum Gardn. et Champ.. The structures were assigned on the basis of spectroscopic data. RXRα transcriptional inhibition and α-glucosidase inhibition assays indicated that all the isolates were inactive.

Force-field parameters of the Psi and Phi around glycosidic bonds to oxygen and sulfur atoms.

PubMed

Saito, Minoru; Okazaki, Isao

2009-12-01

The Psi and Phi torsion angles around glycosidic bonds in a glycoside chain are the most important determinants of the conformation of a glycoside chain. We determined force-field parameters for Psi and Phi torsion angles around a glycosidic bond bridged by a sulfur atom, as well as a bond bridged by an oxygen atom as a preparation for the next study, i.e., molecular dynamics free energy calculations for protein-sugar and protein-inhibitor complexes. First, we extracted the Psi or Phi torsion energy component from a quantum mechanics (QM) total energy by subtracting all the molecular mechanics (MM) force-field components except for the Psi or Phi torsion angle. The Psi and Phi energy components extracted (hereafter called "the remaining energy components") were calculated for simple sugar models and plotted as functions of the Psi and Phi angles. The remaining energy component curves of Psi and Phi were well represented by the torsion force-field functions consisting of four and three cosine functions, respectively. To confirm the reliability of the force-field parameters and to confirm its compatibility with other force-fields, we calculated adiabatic potential curves as functions of Psi and Phi for the model glycosides by adopting the Psi and Phi force-field parameters obtained and by energetically optimizing other degrees of freedom. The MM potential energy curves obtained for Psi and Phi well represented the QM adiabatic curves and also these curves' differences with regard to the glycosidic oxygen and sulfur atoms. Our Psi and Phi force-fields of glycosidic oxygen gave MM potential energy curves that more closely represented the respective QM curves than did those of the recently developed GLYCAM force-field. (c) 2009 Wiley Periodicals, Inc.

Active compounds in Chinese herbs and medicinal animal products which promote blood circulation via inhibition of Na+, K+-ATPase.

PubMed

Tzen, Jason Tc; Chen, Ronald Jy; Chung, Tse-Yu; Chen, Yi-Ching; Lin, Nan-Hei

2010-01-01

The therapeutic effect of cardiac glycosides for congestive heart failure lies in their reversible inhibition on Na+, K+-ATPase located in human myocardium. Several steroid-like compounds containing a core structure similar to cardiac glycosides have been found in many Chinese herbs and medicinal animal products conventionally used to promote blood circulation. They are putatively responsible for the therapeutic effect of those medicinal products via the same mechanism of inhibiting Na+, K+-ATPase. Inhibitory potency on Na+, K+-ATPase by ginsenosides, one of the identified steroid-like compounds, is significantly affected by sugar attachment that might cause steric hindrance of their binding to Na+, K+-ATPase. Ginsenosides with sugar moieties attached only to the C-3 position of the steroid-like structure, equivalent to the sugar position in cardiac glycosides, substantially inhibit Na+, K+-ATPase. However, their inhibitory potency is abolished when sugar moieties are linked to the C-6 or C-20 position of the steroid-like structure. In contrast, no appreciable contents of steroid-like compounds are found in danshen, a well-known Chinese herb traditionally regarded as an effective medicine promoting blood circulation. Instead, magnesium lithospermate B (MLB), the major soluble ingredient in danshen, is assumed to be responsible for the therapeutic effect by inhibiting Na+, K+-ATPase in a manner comparable to cardiac glycosides. Neuroprotective effects of cardiac glycosides, ginsenosides and MLB against ischemic stroke were accordingly observed in a cortical brain slice-based assay model. Whether the neuroprotection is also triggered by inhibition of Na+, K+-ATPase remains to be investigated. Molecular modeling suggests that cardiac glycosides, ginsenosides and MLB presumably bind to the same extracellular pocket of the Na+, K+-ATPase alpha subunit.

Accumulation of hydrolyzable tannins by Aleurites fordii callus culture.

PubMed

Taniguchi, Shoko; Uechi, Kyoko; Kato, Reiko; Ito, Hideyuki; Hatano, Tsutomu; Yazaki, Kazufumi; Yoshida, Takashi

2002-12-01

A callus culture of Aleurites fordii Hemsley (Euphorbiaceae) producing five galloylglucoses and an ellagitannin, geraniin, was established. The production of pentagalloylglucose was remarkably enhanced under light irradiation compared with that in the dark. Cell growth and tannin production were also greatly affected by changing the concentrations and composition of nitrogen sources.

Induction of apoptosis in colon cancer cells treated with isorhamnetin glycosides from Opuntia ficus-indica pads.

PubMed

Antunes-Ricardo, Marilena; Moreno-García, Beatriz E; Gutiérrez-Uribe, Janet A; Aráiz-Hernández, Diana; Alvarez, Mario M; Serna-Saldivar, Sergio O

2014-12-01

(OFI) contains health-promoting compounds like flavonoids, being the isorhamnetin glycosides the most abundant. We evaluated the effect of OFI extracts with different isorhamnetin glycosides against two different human colon cancer cells (HT-29 and Caco2). The extracts were obtained by alkaline hydrolysis with NaOH at 40 °C during 15, 30 or 60 min. Tri and diglycosides were the most abundant isorhamnetin glycosides, therefore these compounds were isolated to compare their cytotoxic effect with the obtained from the extracts. The OFI extracts and purified isorhamnetin glycosides were more cytotoxic against HT-29 cells than Caco2 cells. OFI-30 exhibited the lowest IC50 value against HT-29 (4.9 ± 0.5 μg/mL) and against Caco2 (8.2 ± 0.3 μg/mL). Isorhamnetin diglycosides IG5 and IG6 were more cytotoxic than pure isorhamnetin aglycone or triglycosides when they were tested in HT-29 cells. Bioluminescent analysis revealed increased activity of caspase 3/7 in OFI extracts-treated cells, particularly for the extract with the highest concentration of isorhamnetin triglycosides. Flow cytometry analysis confirmed that OFI extract and isorhamnetin glycosides induced a higher percentage of apoptosis in HT-29 than in Caco2, while isorhamnetin was more apoptotic in Caco2. This research demonstrated that glycosilation affected antiproliferative effect of pure isorhamnetin glycosides or when they are mixed with other phytochemicals in an extract obtained from OFI.

Stability and oxidation products of hydrolysable tannins in basic conditions detected by HPLC/DAD-ESI/QTOF/MS.

PubMed

Tuominen, Anu; Sundman, Terhi

2013-01-01

Hydrolysable tannins occur in plants that are used for food or medicine by humans or herbivores. Basic conditions can alter the structures of tannins, that is, the oxidation of phenolic groups can lead to the formation of toxic quinones. Previously, these labile quinones and other oxidation products have been studied with colorimetric or electron paramagnetic resonance methods, which give limited information about products. To study the stability and oxidation products of hydrolysable tannins in basic conditions using HPLC with a diode-array detector (DAD) combined with electrospray ionisation (ESI) and quadrupole time-of-flight (QTOF) MS. Three galloyl glucoses, four galloyl derivatives with different polyols and three ellagitannins were purified from plants. The incubation reactions of tannins were monitored by HPLC/DAD at five pH values and in reduced oxygen conditions. Reaction products were identified based on UV spectra and mass spectral fragmentation obtained with the high-resolution HPLC/DAD-ESI/QTOF/MS. The use of a base-resistant HPLC column enabled injections without the sample pre-treatment and thus detection of short-lived products. Hydrolysable tannins were unstable in basic conditions and half-lives were mostly less than 10 min at pH 10. Degradation rates were faster at pH 11 but slower at milder pH. The HPLC analyses revealed that various products were formed and identified to be the result of hydrolysis, deprotonation and oxidation. Interestingly, the main hydrolysis product was ellagic acid; it was also formed from galloyl glucoses that do not contain oxidatively coupled galloyl groups in their initial structures. HPLD/DAD-ESI/QTOF/MS was an efficient method for the identification of polyphenol oxidation products and showed how different pH conditions determine the fate of hydrolysable tannins. Copyright © 2013 John Wiley & Sons, Ltd.