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Sample records for tannins cardiac glycosides

  1. Naturally occurring cardiac glycosides.

    PubMed

    Radford, D J; Gillies, A D; Hinds, J A; Duffy, P

    1986-05-12

    Cardiac glycoside poisoning from the ingestion of plants, particularly of oleanders, occurs with reasonable frequency in tropical and subtropical areas. We have assessed a variety of plant specimens for their cardiac glycoside content by means of radioimmunoassays with antibodies that differ in their specificity for cardiac glycosides. Significant amounts of immunoreactive cardiac glycoside were found to be present in the ornamental shrubs: yellow oleander (Thevetia peruviana); oleander (Nerium oleander); wintersweet (Carissa spectabilis); bushman's poison (Carissa acokanthera); sea-mango (Cerbera manghas); and frangipani (Plumeria rubra); and in the milkweeds: redheaded cotton-bush (Asclepias curassavica); balloon cotton (Asclepias fruiticosa); king's crown (Calotropis procera); and rubber vine (Cryptostegia grandifolia). The venom gland of the cane toad (Bufo marinus) also contained large quantities of cardiac glycosides. The competitive immunoassay method permits the rapid screening of specimens that are suspected to contain cardiac glycosides. Awareness of the existence of these plant and animal toxins and their dangers allows them to be avoided and poisoning prevented. The method is also useful for the confirmation of the presence of cardiac glycosides in serum in cases of poisoning. PMID:3086679

  2. Cardiac glycoside overdose

    MedlinePlus

    ... found in the leaves of the digitalis (foxglove) plant. This plant is the original source of this medicine. People ... Digitoxin (Crystodigin) Digoxin (Lanoxicaps, Lanoxin) Besides the foxglove plant, cardiac glycosides also occur naturally in plants such ...

  3. Oleandrin: A cardiac glycosides with potent cytotoxicity

    PubMed Central

    Kumar, Arvind; De, Tanmoy; Mishra, Amrita; Mishra, Arun K.

    2013-01-01

    Cardiac glycosides are used in the treatment of congestive heart failure and arrhythmia. Current trend shows use of some cardiac glycosides in the treatment of proliferative diseases, which includes cancer. Nerium oleander L. is an important Chinese folk medicine having well proven cardio protective and cytotoxic effect. Oleandrin (a toxic cardiac glycoside of N. oleander L.) inhibits the activity of nuclear factor kappa-light-chain-enhancer of activated B chain (NF-κB) in various cultured cell lines (U937, CaOV3, human epithelial cells and T cells) as well as it induces programmed cell death in PC3 cell line culture. The mechanism of action includes improved cellular export of fibroblast growth factor-2, induction of apoptosis through Fas gene expression in tumor cells, formation of superoxide radicals that cause tumor cell injury through mitochondrial disruption, inhibition of interleukin-8 that mediates tumorigenesis and induction of tumor cell autophagy. The present review focuses the applicability of oleandrin in cancer treatment and concerned future perspective in the area. PMID:24347921

  4. Pharmacological treatment of cardiac glycoside poisoning.

    PubMed

    Roberts, Darren M; Gallapatthy, Gamini; Dunuwille, Asunga; Chan, Betty S

    2016-03-01

    Cardiac glycosides are an important cause of poisoning, reflecting their widespread clinical usage and presence in natural sources. Poisoning can manifest as varying degrees of toxicity. Predominant clinical features include gastrointestinal signs, bradycardia and heart block. Death occurs from ventricular fibrillation or tachycardia. A wide range of treatments have been used, the more common including activated charcoal, atropine, β-adrenoceptor agonists, temporary pacing, anti-digoxin Fab and magnesium, and more novel agents include fructose-1,6-diphosphate (clinical trial in progress) and anticalin. However, even in the case of those treatments that have been in use for decades, there is debate regarding their efficacy, the indications and dosage that optimizes outcomes. This contributes to variability in use across the world. Another factor influencing usage is access. Barriers to access include the requirement for transfer to a specialized centre (for example, to receive temporary pacing) or financial resources (for example, anti-digoxin Fab in resource poor countries). Recent data suggest that existing methods for calculating the dose of anti-digoxin Fab in digoxin poisoning overstate the dose required, and that its efficacy may be minimal in patients with chronic digoxin poisoning. Cheaper and effective medicines are required, in particular for the treatment of yellow oleander poisoning which is problematic in resource poor countries. PMID:26505271

  5. Use of cardiac glycosides and risk of glioma.

    PubMed

    Seliger, Corinna; Meier, Christoph R; Jick, Susan S; Uhl, Martin; Bogdahn, Ulrich; Hau, Peter; Leitzmann, M F

    2016-04-01

    Cardiac glycosides induce apoptotic effects on glioma cells, but whether cardiac glycosides protect against risk for glioma is unknown. We therefore explored the relation between glycoside use and glioma risk using a large and validated database. We performed a case-control analysis using the Clinical Practice Research Datalink involving 2005 glioma cases diagnosed between 1995 and 2012 that were individually matched to 20,050 controls on age, gender, general practice, and number of years of active history in the database. Conditional logistic regression analysis was used to evaluate the association between cardiac glycosides and the risk of glioma adjusting for body mass index and smoking. We also examined use of common heart failure and arrhythmia medications to differentiate between a specific glycoside effect and a generic effect of treatment for congestive heart failure or arrhythmia. Cardiac glycoside use was inversely related to glioma incidence. After adjustment for congestive heart failure, arrhythmia, diabetes, and common medications used to treat those conditions, the OR of glioma was 0.47 (95 % CI 0.27-0.81, Bonferroni-corrected p value = 0.024) for use versus non-use of cardiac glycosides, based on 17 exposed cases. In contrast, no associations were noted for other medications used to treat congestive heart failure or arrhythmias. The OR of glioma in people with congestive heart failure was 0.65 (95 % CI 0.40-1.04), and for arrhythmia it was 1.01 (95 % CI 0.78-1.31). These data indicate that cardiac glycoside use is independently associated with reduced glioma risk. PMID:26721242

  6. Variation in cardiac glycoside content of monarch butterflies from natural populations in eastern North America.

    PubMed

    Brower, L P; McEvoy, P B; Williamson, K L; Flannery, M A

    1972-08-01

    A new spectrophotometric assay has been used to determine the gross concentration of cardiac glycoside in individual monarch butterflies. Adults sampled during the fall migration in four areas of eastern North America exhibited a wide variation in cardiac glycoside concentration. The correlation between spectrophotometrically measured concentrations and emetic dose determinations supports the existence of a broad palatability spectrum in wild monarch butterflies. The cardiac gylcoside concentration is greater in females than in males and is independent of the dry weight of the butterflies; contrary to prediction, both the concentration mean and variance decrease southward. The defensive advantage of incorporating cardiac glycosides may be balanced by detrimental effects on individual viability. PMID:5043141

  7. Peruvoside, a Cardiac Glycoside, Induces Primitive Myeloid Leukemia Cell Death.

    PubMed

    Feng, Qian; Leong, Wa Seng; Liu, Liang; Chan, Wai-In

    2016-01-01

    Despite the available chemotherapy and treatment, leukemia remains a difficult disease to cure due to frequent relapses after treatment. Among the heterogeneous leukemic cells, a rare population referred as the leukemic stem cell (LSC), is thought to be responsible for relapses and drug resistance. Cardiac glycosides (CGs) have been used in treating heart failure despite its toxicity. Recently, increasing evidence has demonstrated its new usage as a potential anti-cancer drug. Ouabain, one of the CGs, specifically targeted CD34⁺CD38(-) leukemic stem-like cells, but not the more mature CD34⁺CD38⁺ leukemic cells, making this type of compounds a potential treatment for leukemia. In search of other potential anti-leukemia CGs, we found that Peruvoside, a less studied CG, is more effective than Ouabain and Digitoxin at inducing cell death in primitive myeloid leukemia cells without obvious cytotoxicity on normal blood cells. Similar to Ouabain and Digitoxin, Peruvoside also caused cell cycle arrest at G₂/M stage. It up-regulates CDKN1A expression and activated the cleavage of Caspase 3, 8 and PARP, resulting in apoptosis. Thus, Peruvoside showed potent anti-leukemia effect, which may serve as a new anti-leukemia agent in the future. PMID:27110755

  8. The uptake of cardiac glycosides in relation to their actions in isolated cardiac muscle

    PubMed Central

    Godfraind, T.; Lesne, M.

    1972-01-01

    1. The uptake of 3H-digitoxin, 3H-ouabain and 3H-dihydro-ouabain by isolated guinea-pig atria has been studied and compared with the inhibition of the sodium pump and with the inotropic effect. 2. Analysis of the curve relating the uptake of digitoxin and ouabain at equilibrium to the bath concentration enabled a non-saturable and a saturable binding site to be distinguished. 3. The uptake of inactive doses of dihydro-ouabain was only by a non-saturable mechanism. 4. The uptake of labelled digitoxin and ouabain was reduced in the presence of another glycoside. The amount of bound glycoside was nearly equivalent to the estimated non-saturable uptake. 5. The uptake was reduced at 4° C to the clearance of the non-saturable site. 6. ED50 of digitoxin and of ouabain for inhibition of the sodium pump were measured and compared to the ED50 for inotropic effect and to the concentrations producing a half-saturation of the saturable binding site. 7. It is concluded that binding to the saturable site may be responsible for the cardiac actions of the glycosides. PMID:4656610

  9. Effect of bioactive compounds from Sainfoin ( Onobrychis viciifolia Scop.) on the in vitro larval migration of Haemonchus contortus: role of tannins and flavonol glycosides.

    PubMed

    Barrau, E; Fabre, N; Fouraste, I; Hoste, H

    2005-10-01

    Anthelmintic bioactivity against gastrointestinal nematodes has been associated with leguminous forages supporting the hypothesis of a role of condensed tannins. However, the possibility that other compounds might also been involved has received less consideration. Using bio-guided fractionation, the current study aimed at characterizing the biochemical nature of the active compounds present in sainfoin (Onobrychis viciifolia ), previously identified as an anthelmintic leguminous forage. The effects of sainfoin extracts were evaluated on 3rd-stage larvae (L3) of Haemonchus contortus by using a larval migration inhibition (LMI) assay. Comparison of extracts obtained with several solvent systems showed that the bioactivity was associated with the 70ratio30 acetone/water extract. Further fractionation of the later allowed the separation of phenolic compounds. By use of a dialysis method, compounds were separated with a molecular weight cut-off of 2000 Da. The in vitro anthelmintic effect of the fraction with condensed tannins was confirmed. In the fraction containing molecules of MW <2000 Da, 3 flavonol glycosides were identified as rutin, nicotiflorin and narcissin. At 1200 mug/ml, each inhibited significantly the migration of larvae. Addition of polyvinyl pyrrolidone (PVPP) to both fractions before incubation restored larval migration. These results confirmed the role of both tannins and flavonol glycosides in the anthelmintic properties of sainfoin. PMID:16174418

  10. Cardiac glycosides induce resistance to tubulin-dependent anticancer drugs in androgen-independent human prostate cancer.

    PubMed

    Huang, Dong-Ming; Guh, Jih-Hwa; Huang, Yao-Ting; Chueh, Shih-Chieh; Wang, Hui-Po; Teng, Che-Ming

    2002-01-01

    Due to high prevalence and mortality and the lack of effective therapies, prostate cancer is one of the most crucial health problems in men. Drug resistance aggravates the situation, not only in human prostate cancer but also in other cancers. In this study, we report for the first time that cardiac glycosides (e.g. ouabain and digitoxin) induced resistance of human prostate cancer cells (PC-3) in vitro to tubulin-binding anticancer drugs, such as paclitaxel, colchicine, vincristine and vinblastine. Cardiac glycosides exhibited amazing ability to reverse the G2/M arrest of the cell cycle and cell apoptosis induced by tubulin-binding agents. However, neither ionomycin (a Ca(2+) ionophore) nor veratridine (a Na(+) ionophore) mimicked the preventive action of cardiac glycosides, indicating that elevation of the intracellular Ca(2+) concentration and Na(+) accumulation were not involved in the cardiac glycoside action. Furthermore, cardiac glycosides showed little influence on the effects induced by actinomycin D, anisomycin and doxorubicin, suggesting selectivity for microtubule-targeted anticancer drugs. Using in situ immunofluorescent detection of mitotic spindles, our data showed that cardiac glycosides diminished paclitaxel-induced accumulation of microtubule spindles; however, in a non-cell assay system, cardiac glycosides had little influence on colchicine- and paclitaxel-induced microtubule dynamics. Using an isotope-labeled assay method, we found that ouabain modestly but significantly inhibited the transport of [(14)C]paclitaxel from the cytosol into the nucleus. It is suggested that cardiac glycosides inhibit the G2/M arrest induced by tubulin-binding anticancer drugs via an indirect blockade on microtubule function. The decline in transport of these drugs into the nucleus may partly explain the action of cardiac glycosides. PMID:12218360

  11. Method validation of a survey of thevetia cardiac glycosides in serum samples.

    PubMed

    Kohls, Sarah; Scholz-Böttcher, Barbara; Rullkötter, Jürgen; Teske, Jörg

    2012-02-10

    A sensitive and specific liquid chromatography tandem mass spectrometry (HPLC-ESI(+)-MS/MS) procedure was developed and validated for the identification and quantification of thevetin B and further cardiac glycosides in human serum. The seeds of Yellow Oleander (Thevetia peruviana) contain cardiac glycosides that can cause serious intoxication. A mixture of six thevetia glycosides was extracted from these seeds and characterized. Thevetin B, isolated and efficiently purified from that mixture, is the main component and can be used as evidence. Solid phase extraction (SPE) proved to be an effective sample preparation method. Digoxin-d3 was used as the internal standard. Although ion suppression occurs, the limit of detection (LOD) is 0.27 ng/ml serum for thevetin B. Recovery is higher than 94%, and accuracy and precision were proficient. Method refinement was carried out with regard to developing a general screening method for cardiac glycosides. The assay is linear over the range of 0.5-8 ng/ml serum. Finally, the method was applied to a case of thevetia seed ingestion. PMID:21376490

  12. Release of adenine nucleotide metabolites by toxic concentrations of cardiac glycosides.

    PubMed

    Bernauer, W

    1994-01-01

    In isolated perfused guinea-pig hearts the effect of toxic concentrations of cardiac glycosides on the release of the adenine nucleotide metabolites adenosine, inosine, hypoxanthine, xanthine, and uric acid was investigated. Digoxin concentrations of 0.03-1 mumol.l-1 produced moderate to severe tachyarrhythmias. Large amounts of metabolites were released by concentrations of 0.1 mumol.l-1, and higher. Occurrence of glycoside-induced ventricular fibrillation was associated with a particularly high release. Metabolite release was also obtained when fibrillation was elicited electrically in normal control hearts, or in hearts receiving simultaneously a marginally toxic digoxin concentration (0.03 mumol.l-1). Digoxin-induced tachyarrhythmias and metabolite release were almost completely prevented by a high potassium concentration in the coronary perfusion fluid (8.1 mmol.l-1). The antiarrhythmic effect was also obtained with lidocaine (60 mumol.l-1), but the release was only partially antagonized. Similar results concerning arrhythmias and metabolite release as with digoxin were obtained with ouabain. The findings suggest that the decrease in myocardial ATP observed in glycoside-intoxicated heart preparations is partly due to the loss of nucleotide precursor substances. Moreover, it appears likely that liberated adenosine in the interstitium of severely intoxicated heart preparations reaches pharmacologically effective concentrations. PMID:7826306

  13. Metabolic fate of cardiac glycosides and flavonoids upon fermentation of aqueous sea squill (Drimia maritima L.) extracts.

    PubMed

    Knittel, Diana N; Stintzing, Florian C; Kammerer, Dietmar R

    2015-06-10

    Sea squill (Drimia maritima L.) extracts have been used for centuries for the medical treatment of heart diseases. A procedure for the preparation of Drimia extracts applied for such purposes comprising a fermentation step is described in the German Homoeopathic Pharmacopoeia (GHP). However, little is known about the secondary metabolite profile of such extracts and the fate of these components upon processing and storage. Thus, in the present study sea squill extracts were monitored during fermentation and storage by HPLC-DAD-MS(n) and GC-MS to characterise and quantitate individual cardiac glycosides and phenolic compounds. For this purpose, a previously established HPLC method for the separation and quantitation of pharmacologically relevant cardiac glycosides (bufadienolides) was validated. Within 12 months of storage, total bufadienolide contents decreased by about 50%, which was attributed to microbial and plant enzyme activities. The metabolisation and degradation rates of individual bufadienolide glycosides significantly differed, which was attributed to differing structures of the aglycones. Further degradation of bufadienolide aglycones was also observed. Besides reactions well known from human metabolism studies, dehydration of individual compounds was monitored. Quantitatively predominating flavonoids were also metabolised throughout the fermentation process. The present study provides valuable information about the profile and stability of individual cardiac glycosides and phenolic compounds in fermented Drimia extracts prepared for medical applications, and expands the knowledge of cardiac glycoside conversion upon microbial fermentation. PMID:25841205

  14. UNBS1450, a steroid cardiac glycoside inducing apoptotic cell death in human leukemia cells.

    PubMed

    Juncker, Tom; Cerella, Claudia; Teiten, Marie-Hélène; Morceau, Franck; Schumacher, Marc; Ghelfi, Jenny; Gaascht, François; Schnekenburger, Michael; Henry, Estelle; Dicato, Mario; Diederich, Marc

    2011-01-01

    Cardiac steroids are used to treat various diseases including congestive heart failure and cancer. The aim of this study was to investigate the anti-leukemic activity of UNBS1450, a hemi-synthetic cardenolide belonging to the cardiac steroid glycoside family. Here, we report that, at low nanomolar concentrations, UNBS1450 induces apoptotic cell death. Subsequently, we have investigated the molecular mechanisms leading to apoptosis activation. Our results show that UNBS1450 inhibits NF-κB transactivation and triggers apoptosis by cleavage of pro-caspases 8, 9 and 3/7, by decreasing expression of anti-apoptotic Mcl-1 and by recruitment of pro-apoptotic Bak and Bax protein eventually resulting in cell death. PMID:20849830

  15. Contrasting effects of cardiac glycosides on cisplatin- and etoposide-induced cell death.

    PubMed

    Kulikov, Andrey V; Slobodkina, Ekaterina A; Alekseev, Andrey V; Gogvadze, Vladimir; Zhivotovsky, Boris

    2016-07-01

    Cardiac glycosides (CGs) or cardiotonic steroids, which constitute a group of naturally occurring compounds with a steroid-like structure, can act on Na+/K+-ATPase as a receptor and activate intracellular signaling messengers leading to a variety of cellular responses. Epidemiological studies have revealed that CGs, used for the treatment of cardiac disorders, may also be beneficial as anti-cancer agents. CGs, acting in combination with other chemotherapeutic agents, may significantly alter their efficiency in relation to cancer cell elimination, causing both sensitization and an increase in cancer cell death, and in some cases resistance to chemotherapy. Here we show the ability of CGs to modulate apoptotic response to conventionally used anti-cancer drugs. In combination with etoposide, CGs digoxin may enhance cytotoxic potential, thereby allowing the chemotherapeutic dose to be decreased and minimizing toxicity and adverse reactions. Mechanisms behind this event are discussed. PMID:26854291

  16. Metabolism of cardiac glycosides studied in the isolated perfused guinea-pig liver

    PubMed Central

    Kolenda, K.-D.; Lüllmann, H.; Peters, T.

    1971-01-01

    1. Metabolic degradation of tritiated ouabain, digoxin, and digitoxin has been investigated quantitatively using the isolated perfused guinea-pig liver. The cardiac glycosides and their metabolites have been extracted from the plasma, liver, and bile by different solvents and identified as far as possible by radio-chromatographic analysis. 2. The total metabolic activity in the experimental system was localized in the liver. 3. The hydrophilic glycoside ouabain could not penetrate into the metabolically active compartment of the liver and was, therefore, not degraded. The more lipophilic compound digitoxin, however, was completely degraded due to its high affinity for the metabolically active sites. The unchanged digitoxin cannot enter the aqueous bile fluid in contrast to its more hydrophilic metabolites. 4. The only detectable metabolic degradation of digoxin was a conjugation with glucuronic and/or sulphuric acid, but a cleavage of sugar molecules seemed not to occur. 5. In the case of digitoxin the metabolic processes are more complicated: sugar cleavage, conjugation, and C-12 hydroxylation take place simultaneously. An immediate hydroxylation of digitoxin leading to digoxin was not observed. After administration of digitoxin conjugation products as well as digoxigenin-bis-and digoxigenin-mono-digitoxosides were present in each of the compartments investigated, but the digitoxosides of digitoxigenin were intermediates in concentrations too low to be determined indicating a very high rate of conjugation and/or C-12 hydroxylation as compared with the cleavage of the digitoxoses. 6. A scheme for the metabolic pathways of the cardiac glycosides based on experimental results is presented. The metabolic behaviour of each of the three compounds involved is closely related to their physicochemical properties, especially the lipid solubility. PMID:5579464

  17. Alteration of cardiac glycoside positive inotropic action by modulators of protein synthesis and degradation

    SciTech Connect

    Nosek, T.M.; Adams, R.J.

    1986-03-05

    Numerous membrane bound and cytoplasmic proteins participate in the cardiac expression of the positive inotropic action (PIA) of digitalis glycosides including the Na,K-ATPase (NKA). Exposure of the myocardium to an inhibitor of protein synthesis (cycloheximide, CYC) or of protein degradation (leupeptin, LEU) alters the PIA of ouabain in isolated, paced guinea pig papillary muscles (PM) in opposite ways. In vivo exposure to CYC for 3 hr resulted in a 30% depression of the in vitro PIA of ouabain at 1.7..mu..M compared to control. In vivo exposure to LEU for 1 hr resulted in a 47% enhancement of the in vitro PIA of 1.7..mu..M ouabain. Neither drug had an apparent effect on the ouabain PIA ED50. Neither CYC nor LEU exposure to PM in vitro affect resting or developed tension or the response of skinned PM to calcium. The mechanisms of the PIA alterations by CYC or LEU do not involve a direct effect on the digitalis receptor. Exposure of isolated cardiac sarcolemma enriched in NKA to 10-100..mu..M CYC or LEU did not affect NKA activity or /sup 3/H-ouabain binding. Although direct physicochemical effects of CYC or LEU may be involved in the alterations of the ouabain PIA, it is possible that modulation of the cellular levels or turnover rate of short-lived proteins may affect cardiac regulation of the digitalis PIA.

  18. Inhibition of epidermal growth factor signaling by the cardiac glycoside ouabain in medulloblastoma.

    PubMed

    Wolle, Daniel; Lee, Seung Joon; Li, Zhiqin; Litan, Alisa; Barwe, Sonali P; Langhans, Sigrid A

    2014-10-01

    Epidermal growth factor (EGF) signaling regulates cell growth, proliferation, and differentiation. Upon receptor binding, EGF triggers cascades of downstream signaling, including the MAPK and phosphoinositide-3-kinase (PI3K)/Akt signaling pathways. Aberrant expression/activation of EGFR is found in multiple human cancers, including medulloblastoma, the most prevalent pediatric brain cancer, and often has been associated with metastasis, poor prognosis, and resistance to chemotherapy. Na,K-ATPase is an ion pump well known for its role in intracellular ion homeostasis. Recent studies showed that Na,K-ATPase also functions as a signaling platform and revealed a role in EGFR, MAPK, and PI3K signaling. While both EGFR and Na,K-ATPase seem to modulate similar signaling pathways, cardiac glycosides that are steroid-like inhibitors of Na,K-ATPase, exhibit antiproliferative and proapoptotic properties in cancer cells. Thus, we sought to better understand the relationship between EGF and cardiac glycoside signaling. Here, we show that in medulloblastoma cells, both EGF and ouabain activate Erk1/2 and PI3K/Akt signaling. Nevertheless, in medulloblastoma cells ouabain did not transactivate EGFR as has been reported in various other cell lines. Indeed, ouabain inhibited EGF-induced Erk1/2 and Akt activation and, moreover, prevented EGF-induced formation of actin stress fibers and cell motility, probably by activating a stress signaling response. Na,K-ATPase has been proposed to act as a signaling scaffold and our studies suggest that in medulloblastoma cells Na,K-ATPase might act as a check point to integrate EGF-associated signaling pathways. Thus, Na,K-ATPase might serve as a valid target to develop novel therapeutic approaches in tumors with aberrant activation of the EGFR signaling cascades. PMID:25052069

  19. Cardiac glycosides inhibit p53 synthesis by a mechanism relieved by Src or MAPK inhibition

    PubMed Central

    Wang, Zhen; Zheng, Min; Li, Zhichuan; Li, Ruiguo; Jia, Lijun; Xiong, Xiufang; Southall, Noel; Wang, Shaomeng; Xia, Menghang; Austin, Christopher P.; Zheng, Wei; Xie, Zijian; Sun, Yi

    2009-01-01

    p53 is regulated at the multiple levels. We report here that p53 in multiple lines of human cancer cells is down-regulated by cardiac glycoside drugs, digoxin or ouabain, the potent inhibitors of Na+/K+-ATPase. These drugs reduced the basal levels of p53 protein at nanomolar concentrations in a dose-, time- and cancer cell line-dependent manner, but independent of p53 status of wild type (wt) or mutant. The drugs also reduced the levels of p53 induced by its activators as well as p53 transfected into human cancer cells, regardless of its status. Interestingly, the drugs had no effect on endogenous p53 in two immortalized human cell lines. Mechanistically, p53 reduction did not occur at the mRNA levels, but at the protein levels, as a result of reduced protein synthesis rather than enhanced degradation. The cellular sensitivity to drug-induced p53 reduction was not associated with the levels of α subunits of Na+/K+-ATPase in different cell lines. While lowering extracellular K+ did not reduce p53 as did ouabain and digoxin, it did potentiate both digoxin and ouabain-induced p53 reduction in sensitive lines. Finally, p53 reduction appears to be triggered by activation of Src/MAPK signaling pathways upon drug binding to the Na+/K+-ATPase and can be completely blocked by the inhibitors of Src or MEK. This is the first report that cardiac glycoside drugs, by initiating the Src/MAPK signaling pathways, reduce the p53 levels via inhibition of p53 protein synthesis. The drugs may be useful in the treatment of human cancers with a gain-of-function p53 mutation. PMID:19679550

  20. Cardiac glycoside-induced cell death and Rho/Rho kinase pathway: Implication of different regulation in cancer cell lines.

    PubMed

    Özdemir, Aysun; Şimay, Yaprak Dilber; İbişoğlu, Burçin; Yaren, Biljana; Bülbül, Döne; Ark, Mustafa

    2016-05-01

    Previously, we demonstrated that the Rho/ROCK pathway is involved in ouabain-induced apoptosis in HUVEC. In the current work, we investigated whether the Rho/ROCK pathway is functional during cardiac glycosides-induced cytotoxic effects in cancer cell lines, as well as in non-tumor cells. For that purpose, we evaluated the role of ROCK activation in bleb formation and cell migration over upstream and downstream effectors in addition to ROCK cleavage after cardiac glycosides treatment. All three cardiac glycosides (ouabain, digoxin and bufalin) induced cell death in HeLa and HepG2 cells and increased the formation of blebbing in HeLa cells. In contrast to our previous study, ROCK inhibitor Y27632 did not prevent bleb formation. Observation of ROCK II cleavage after ouabain, digoxin and oxaliplatin treatments in HeLa and/or HepG2 cells suggested that cleavage is independent of cell type and cell death induction. While inhibiting cleavage of ROCK II by the caspase inhibitors z-VAD-fmk, z-VDVAD-fmk and z-DEVD-fmk, evaluation of caspase 2 siRNA ineffectiveness on this truncation indicated that caspase-dependent ROCK II cleavage is differentially regulated in cancer cell lines. In HeLa cells, ouabain induced the activation of ROCK, although it did not induce phosphorylation of ERM, an upstream effector. While Y27632 inhibited the migration of HeLa cells, 10nM ouabain had no effect on cell migration. In conclusion, these findings indicate that the Rho/ROCK pathway is regulated differently in cancer cell lines compared to normal cells during cardiac glycosides-induced cell death. PMID:27017918

  1. Human Cytomegalovirus Inhibition by Cardiac Glycosides: Evidence for Involvement of the hERG Gene

    PubMed Central

    Kapoor, Arun; Cai, Hongyi; Forman, Michael; He, Ran; Shamay, Meir

    2012-01-01

    Infection with human cytomegalovirus (HCMV) continues to be a major threat for pregnant women and the immunocompromised population. Although several anti-HCMV therapies are available, the development of new anti-HCMV agents is highly desired. There is growing interest in identifying compounds that might inhibit HCMV by modulating the cellular milieu. Interest in cardiac glycosides (CG), used in patients with congestive heart failure, has increased because of their established anticancer and their suggested antiviral activities. We report that the several CG—digoxin, digitoxin, and ouabain—are potent inhibitors of HCMV at nM concentrations. HCMV inhibition occurred prior to DNA replication, but following binding to its cellular receptors. The levels of immediate early, early, and late viral proteins and cellular NF-κB were significantly reduced in CG-treated cells. The activity of CG in infected cells correlated with the expression of the potassium channel gene, hERG. CMV infection upregulated hERG, whereas CG significantly downregulated its expression. Infection with mouse CMV upregulated mouse ERG (mERG), but treatment with CG did not inhibit virus replication or mERG transcription. These findings suggest that CG may inhibit HCMV by modulating human cellular targets associated with hERG and that these compounds should be studied for their antiviral activities. PMID:22777050

  2. Cardiac Glycosides Activate the Tumor Suppressor and Viral Restriction Factor Promyelocytic Leukemia Protein (PML)

    PubMed Central

    Milutinovic, Snezana; Heynen-Genel, Susanne; Chao, Elizabeth; Dewing, Antimone; Solano, Ricardo; Milan, Loribelle; Barron, Nikki; He, Min; Diaz, Paul W.; Matsuzawa, Shu-ichi; Reed, John C.; Hassig, Christian A.

    2016-01-01

    Cardiac glycosides (CGs), inhibitors of Na+/K+-ATPase (NKA), used clinically to treat heart failure, have garnered recent attention as potential anti-cancer and anti-viral agents. A high-throughput phenotypic screen designed to identify modulators of promyelocytic leukemia protein (PML) nuclear body (NB) formation revealed the CG gitoxigenin as a potent activator of PML. We demonstrate that multiple structurally distinct CGs activate the formation of PML NBs and induce PML protein SUMOylation in an NKA-dependent fashion. CG effects on PML occur at the post-transcriptional level, mechanistically distinct from previously described PML activators and are mediated through signaling events downstream of NKA. Curiously, genomic deletion of PML in human cancer cells failed to abrogate the cytotoxic effects of CGs and other apoptotic stimuli such as ceramide and arsenic trioxide that were previously shown to function through PML in mice. These findings suggest that alternative pathways can compensate for PML loss to mediate apoptosis in response to CGs and other apoptotic stimuli. PMID:27031987

  3. Cardiac glycosides display selective efficacy for STK11 mutant lung cancer

    PubMed Central

    Kim, Nayoung; Yim, Hwa Young; He, Ningning; Lee, Cheol-Jung; Kim, Ju Hyun; Choi, Jin-Sung; Lee, Hye Suk; Kim, Somin; Jeong, Euna; Song, Mee; Jeon, Sang-Min; Kim, Woo-Young; Mills, Gordon B.; Cho, Yong-Yeon; Yoon, Sukjoon

    2016-01-01

    Although STK11 (LKB1) mutation is a major mediator of lung cancer progression, targeted therapy has not been implemented due to STK11 mutations being loss-of-function. Here, we report that targeting the Na+/K+-ATPase (ATP1A1) is synthetic lethal with STK11 mutations in lung cancer. The cardiac glycosides (CGs) digoxin, digitoxin and ouabain, which directly inhibit ATP1A1 function, exhibited selective anticancer effects on STK11 mutant lung cancer cell lines. Restoring STK11 function reduced the efficacy of CGs. Clinically relevant doses of digoxin decreased the growth of STK11 mutant xenografts compared to wild type STK11 xenografts. Increased cellular stress was associated with the STK11-specific efficacy of CGs. Inhibiting ROS production attenuated the efficacy of CGs, and STK11-AMPK signaling was important in overcoming the stress induced by CGs. Taken together, these results show that STK11 mutation is a novel biomarker for responsiveness to CGs. Inhibition of ATP1A1 using CGs warrants exploration as a targeted therapy for STK11 mutant lung cancer. PMID:27431571

  4. Cardiac Glycosides Activate the Tumor Suppressor and Viral Restriction Factor Promyelocytic Leukemia Protein (PML).

    PubMed

    Milutinovic, Snezana; Heynen-Genel, Susanne; Chao, Elizabeth; Dewing, Antimone; Solano, Ricardo; Milan, Loribelle; Barron, Nikki; He, Min; Diaz, Paul W; Matsuzawa, Shu-ichi; Reed, John C; Hassig, Christian A

    2016-01-01

    Cardiac glycosides (CGs), inhibitors of Na+/K+-ATPase (NKA), used clinically to treat heart failure, have garnered recent attention as potential anti-cancer and anti-viral agents. A high-throughput phenotypic screen designed to identify modulators of promyelocytic leukemia protein (PML) nuclear body (NB) formation revealed the CG gitoxigenin as a potent activator of PML. We demonstrate that multiple structurally distinct CGs activate the formation of PML NBs and induce PML protein SUMOylation in an NKA-dependent fashion. CG effects on PML occur at the post-transcriptional level, mechanistically distinct from previously described PML activators and are mediated through signaling events downstream of NKA. Curiously, genomic deletion of PML in human cancer cells failed to abrogate the cytotoxic effects of CGs and other apoptotic stimuli such as ceramide and arsenic trioxide that were previously shown to function through PML in mice. These findings suggest that alternative pathways can compensate for PML loss to mediate apoptosis in response to CGs and other apoptotic stimuli. PMID:27031987

  5. Skeletal muscle Na,K-pump concentration in children and its relationship to cardiac glycoside distribution.

    PubMed

    Kjeldsen, K; Grøn, P

    1989-08-01

    Skeletal muscle Na,K-pump (cardiac glycoside receptor) concentration was quantified in 18 0- to 8-year-old human subjects by vanadate facilitated [3H]ouabain binding to intact vastus lateralis samples obtained at autopsy. No age-dependent change in [3H]ouabain binding site concentration was observed. Mean value +/- S.E.M. was 268 +/- 17 pmol/g wet wt. (n = 18), range 182 to 433 pmol/g wet wt. At the age of 1 day, 3.5 month and 8 years and 8 months, unspecific uptake and retention of [3H]ouabain was 1.6, 1.4 and 1.5% of the total uptake and retention; release of specifically bound [3H]ouabain during the washout procedure took place with T 1/2 of 97, 90 and 73 hr; and apparent affinity constants for [3H]ouabain binding (KD) was 1.3 x 10(-8), 0.9 x 10(-8) and 1.2 x 10(-8) mol/l. [3H]Ouabain binding site concentrations and kinetics were in agreement with values from adults except that in children apparent affinity constant (KD) was 1.7 times the value in adults. The observation of no age-dependent changes in human skeletal muscle Na,K-adenosine triphosphatase concentration was at variance with the observations of such changes in animals. The total number of Na,K-pumps in the pool of skeletal muscles increased from 10 to 50 times that in the heart from birth to old age. The skeletal muscle pool of Na,K-pumps seems to constitute a distribution volume of importance during digitalization in children as well as adults.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:2547946

  6. Cardiac glycosides induced toxicity in human cells expressing α1-, α2-, or α3-isoforms of Na-K-ATPase.

    PubMed

    Cherniavsky Lev, Marina; Karlish, Steven J D; Garty, Haim

    2015-07-15

    The Na+-K+-ATPase is specifically inhibited by cardiac glycosides, some of which may also function as endogenous mammalian hormones. Previous studies using Xenopus oocytes, yeast cells, or purified isoforms demonstrated that affinities of various cardiac glycosides for three isoforms of the Na+-K+-ATPase (α1-α3β1) may differ, a finding with potential clinical implication. The present study investigates isoform selectivity and effects of cardiac glycosides on cultured mammalian cells under more physiological conditions. H1299 cells (non-small cell lung carcinoma) were engineered to express only one α-isoform (α1, α2, or α3) by combining stable transfection of isoforms and silencing endogenous α1. Cardiac glycoside binding was measured by displacement of bound 3H-ouabain. The experiments confirm moderate α1/α3:α2 selectivity of ouabain, moderate α2:α1 selectivity of digoxin, and enhanced α2:α1 selectivity of synthetic derivatives (Katz A, Tal DM, Heller D, Haviv H, Rabah B, Barkana Y, Marcovich AL, Karlish SJD. J Biol Chem 289: 21153-21162, 2014). Relative α2:α1 selectivity of digoxin vs. ouabain was also manifested by enhanced internalization of α2 in response to digoxin. Cellular proliferation assays of H1299 cells confirmed the patterns of α2:α1 selectivity for ouabain, digoxin, and a synthetic derivative and reveal a crucial role of surface pump density on sensitivity to cardiac glycosides. Because cardiac glycosides are being considered as drugs for treatment of cancer, effects of ouabain on proliferation of 12 cancer and noncancer cell lines, with variable plasma membrane expression of α1, have been tested. These demonstrated that sensitivity to ouabain indeed depends linearly on the plasma membrane surface density of Na+-K+-ATPase irrespective of status, malignant or nonmalignant. PMID:25994790

  7. Isoform specificity of cardiac glycosides binding to human Na+,K+-ATPase α1β1, α2β1 and α3β1

    PubMed Central

    Hauck, Christian; Potter, Tatjana; Bartz, Michaela; Wittwer, Thorsten; Wahlers, Thorsten; Mehlhorn, Uwe; Scheiner-Bobis, Georgios; McDonough, Alicia A.; Bloch, Wilhelm; Schwinger, Robert H.G.; Müller-Ehmsen, Jochen

    2016-01-01

    Cardiac glycosides inhibit the Na+,K+-ATPase and are used for the treatment of symptomatic heart failure and atrial fibrillation. In human heart three isoforms of Na+,K+-ATPase are expressed: α1β1, α2β1 and α3β1. It is unknown, if clinically used cardiac glycosides differ in isoform specific affinities, and if the isoforms have specific subcellular localization in human cardiac myocytes. Human Na+,K+-ATPase isoforms α1β1, α2β1 and α3β1 were expressed in yeast which has no endogenous Na+,K+-ATPase. Isoform specific affinities of digoxin, digitoxin, β-acetyldigoxin, methyldigoxin and ouabain were assessed in [3H]-ouabain binding assays in the absence or presence of K+ (each n=5). The subcellular localizations of the Na+,K+-ATPase isoforms were investigated in isolated human atrial cardiomyocytes by immunohistochemistry. In the absence of K+, methyldigoxin (α1>α3>α2) and ouabain (α1=α3>α2) showed distinct isoform specific affinities, while for digoxin, digitoxin and β-acetyldigoxin no differences were found. In the presence of K+, also digoxin (α2=α3>α1) and β-acetyldigoxin (α1>α3) had isoform specificities. A comparison between the cardiac glycosides demonstrated highly different affinity profiles for the isoforms. Immunohistochemistry showed that all three isoforms are located in the plasma membrane and in intracellular membranes, but only α1β1 and α2β1 are located in the T-tubuli. Cardiac glycosides show distinct isoform specific affinities and different affinity profiles to Na+,K+-ATPase isoforms which have different subcellular localizations in human cardiomyocytes. Thus, in contrast to current notion, different cardiac glycoside agents may significantly differ in their pharmacological profile which could be of hitherto unknown clinical relevance. PMID:19751721

  8. The alpha-synuclein 5'untranslated region targeted translation blockers: anti-alpha synuclein efficacy of cardiac glycosides and Posiphen.

    PubMed

    Rogers, Jack T; Mikkilineni, Sohan; Cantuti-Castelvetri, Ippolita; Smith, Deborah H; Huang, Xudong; Bandyopadhyay, Sanghamitra; Cahill, Catherine M; Maccecchini, Maria L; Lahiri, Debomoy K; Greig, Nigel H

    2011-03-01

    Increased brain α-synuclein (SNCA) protein expression resulting from gene duplication and triplication can cause a familial form of Parkinson's disease (PD). Dopaminergic neurons exhibit elevated iron levels that can accelerate toxic SNCA fibril formation. Examinations of human post mortem brain have shown that while mRNA levels for SNCA in PD have been shown to be either unchanged or decreased with respect to healthy controls, higher levels of insoluble protein occurs during PD progression. We show evidence that SNCA can be regulated via the 5'untranslated region (5'UTR) of its transcript, which we modeled to fold into a unique RNA stem loop with a CAGUGN apical loop similar to that encoded in the canonical iron-responsive element (IRE) of L- and H-ferritin mRNAs. The SNCA IRE-like stem loop spans the two exons that encode its 5'UTR, whereas, by contrast, the H-ferritin 5'UTR is encoded by a single first exon. We screened a library of 720 natural products (NPs) for their capacity to inhibit SNCA 5'UTR driven luciferase expression. This screen identified several classes of NPs, including the plant cardiac glycosides, mycophenolic acid (an immunosuppressant and Fe chelator), and, additionally, posiphen was identified to repress SNCA 5'UTR conferred translation. Western blotting confirmed that Posiphen and the cardiac glycoside, strophanthidine, selectively blocked SNCA expression (~1 μM IC(50)) in neural cells. For Posiphen this inhibition was accelerated in the presence of iron, thus providing a known APP-directed lead with potential for use as a SNCA blocker for PD therapy. These are candidate drugs with the potential to limit toxic SNCA expression in the brains of PD patients and animal models in vivo. PMID:21221670

  9. [Cardiac effects and glycoside concentrations in serum and urine after oral administration of beta-methy-digoxin to healthy individuals (author's transl)].

    PubMed

    Haasis, R; Larbig, D; Klenk, K O

    1975-06-01

    Six healthy individuals were digitalized orally with beta-methyl-digoxin. The serum glycoside concentration, determined radioimmunologically at the end of the digitalization period was 1.2 +/- 0.22 ng/ml. At this period of time renal excretion attained 55.9% of the daily administered oral dose. The calculated renal clearance of beta-methyl-digoxin was 63 +/- 8.1 ml/min e. g. 57.5 +/- 8.3 ml/min/1.73 m2. After discontinuation of the glycoside the serum half life was 54 h. During the digitalization period the cardiac glycoside effects could be measured by ECG changes, especially a shortening of the QT interval as well as a shortening of the left ventricular ejection time and the pre ejection period, corrected for the heart rate. PMID:1152344

  10. Glycoside vs. Aglycon: The Role of Glycosidic Residue in Biological Activity

    NASA Astrophysics Data System (ADS)

    Křen, Vladimír

    A large number of biologically active compounds are glycosides. Sometimes the glycosidic residue is crucial for their activity, in other cases glycosylation only improves pharmacokinetic parameters. Recent developments in molecular glycobiology brought better understanding of aglycon vs. glycoside activities, and made possible the development of new, more active or more effective glycodrugs based on these findings - a very illustrative recent example is vancomycin. The new enzymatic methodology "glycorandomization" enabled preparation of glycoside libraries and opened up paths to the preparation of optimized or entirely novel glycoside antibiotics. This chapter deals with an array of glycosidic compounds currently used in medicine but also covers the biological activity of some glycosidic metabolites of known drugs. The chapter discusses glycosides of vitamins, polyphenolic glycosides (flavonoids), alkaloid glycosides, glycosides of antibiotics, glycopeptides, cardiac glycosides, steroid and terpenoid glycosides etc. The physiological role of the glycosyl moiety and structure-activity relations (SAR) in the glycosidic moiety (-ies) are also discussed.

  11. Cardiac glycosides from the seeds of Thevetia peruviana and their pro-apoptotic activity toward cancer cells.

    PubMed

    Cheng, Huo-Yun; Tian, Dan-Mei; Tang, Jin-Shan; Shen, Wei-Zai; Yao, Xin-Sheng

    2016-09-01

    Phytochemical investigation of the seeds of Thevetia peruviana resulted in the isolation of seven cardiac glycosides (1-7), including two new compounds (1 and 2). Cytotoxicity of them toward cancer cell lines P15 (human lung cancer cell), MGC-803 (human gastric cancer cells), SW1990 (human pancreatic cancer cells), and normal hepatocyte cell LO2 suggested that compound 1 could selectively inhibit the proliferation of cancer cell lines with IC50 from 0.05 to 0.15 μM. Pro-apoptotic activity revealed that it induced the apoptosis of MGC-803 cancer cells in a dose-dependent manner. Meanwhile, treatment of MGC-803 cancer cells with 1 resulted in diminution of pro-caspases 3 and 9 and activation of caspases 3 and 9, while it increased the Bax/Bcl-2 ratio in a dose-dependent manner. These meant that 1 induced the apoptosis of cancer cells by involving the intrinsic apoptotic pathway. In addition, the cell cycle distribution of MGC-803 cancer cells treated by 1 revealed that it could lead to cell cycle arrest at the G2/M phase. Altogether, this study suggested that compound 1 may exhibit anticancer activity by its capability of induction of intrinsic apoptosis and cell cycle arrest at G2/M phase. PMID:27086856

  12. The effect of cardiac glycosides on the Na+ pump current-voltage relationship of isolated rat and guinea-pig heart cells.

    PubMed Central

    Hermans, A N; Glitsch, H G; Verdonck, F

    1994-01-01

    1. Whole-cell recording from isolated rat and guinea-pig ventricular myocytes revealed a change of the cardiac Na+ pump current (Ip)-voltage (V) relationship by cardiac glycosides, specific inhibitors of the Na(+)-K+ pump. 2. Dihydro-ouabain (DHO) diminished Ip in rat ventricular cells at 0 mV in a concentration-dependent manner. 3. The concentration-response curve of Ip inhibition caused by DHO was shifted to higher [DHO] at higher extracellular K+ concentrations ([K+]o) or at more negative membrane potentials. 4. In rat myocytes, DHO immediately flattened the normalized cardiac Ip-V curve and evoked or enhanced a region of negative slope. 5. Ouabain, at concentrations which caused a comparable inhibition of Ip, exerted DHO-like effects on the Ip-V relationship of rat ventricular myocytes. However, the effects developed more slowly. 6. A slowly developing alteration of the Ip-V curve was also observed upon application of DHO to guinea-pig ventricular cells. The range of [DHO] used was about 100-fold lower than that applied to rat ventricular cells, but was equally effective for Ip inhibition. 7. Increasing the K+ concentration of DHO-containing media affected the existing equilibrium of DHO binding to the cardiac Na(+)-K+ pump. A new equilibrium was reached within about 3 s in rat ventricular myocytes, but only within about 50 s in guinea-pig ventricular cells under the experimental conditions chosen. 8. It is concluded that the changes of the cardiac Ip-V curve induced by cardiac glycosides are mediated by voltage-dependent variations of the local [K+]o at the K+ binding sites of the Na(+)-K+ pump in an 'access channel'. The variations were estimated by means of the Boltzmann equation. The estimations agreed with those derived from the measured DHO binding to the Na(+)-K+ pump at various [K+]o. A new equilibrium of glycoside binding to the pump is established at the altered [K+]o. The time necessary to reach the new binding equilibrium varies with the

  13. Cardiac glycosides and the risk of breast cancer in women with chronic heart failure and supraventricular arrhythmia.

    PubMed

    Couraud, Sébastien; Dell'Aniello, Sophie; Bouganim, Nathaniel; Azoulay, Laurent

    2014-08-01

    The aim of this study is to determine whether the use of cardiac glycosides (CGs), drugs used in the treatment of congestive heart failure (CHF) and supra-ventricular arrhythmia, is associated with an increased risk of breast cancer. A cohort of 53,454 women newly diagnosed with CHF or supra-ventricular arrhythmia between January 1, 1988 and December 31, 2010, followed until December 31, 2012, was identified using the United Kingdom Clinical Practice Research Datalink. A nested case-control analysis was performed, where all incident cases of breast cancer occurring during follow-up were identified and matched with up to 10 controls on age, cohort entry date, and duration of follow-up. Conditional logistic regression models were used to estimate adjusted odds ratios (ORs) with 95 % confidence intervals (CIs) of incident breast cancer associated with the use of CGs, along with measures of cumulative duration of use and dose. All analyses considered a one year lag period prior to the event, necessary for latency considerations and to minimize detection bias. The 898 breast cancer cases diagnosed beyond one year of follow-up were matched to 8,940 controls. Overall, use of CGs was not associated with an increased risk of breast cancer when compared to non-use (OR 1.07, 95 % CI 0.90-1.26). Furthermore, the risk did not vary with cumulative duration of use or cumulative dose. The findings of this large population-based study indicate that the use of CGs is not associated with an increased risk of breast cancer. This should provide reassurance to physicians and patients using these drugs. PMID:25038879

  14. Cardiac glycoside overdose

    MedlinePlus

    ... usually occur only in chronic overdoses. EYES, EARS, NOSE, AND THROAT Blurred vision Halos around objects (yellow, green, white) * SKIN Allergic reaction, including possible Stevens-Johnson syndrome Hives Rash STOMACH AND INTESTINES Diarrhea Loss of ...

  15. Potassium changes the relationship between receptor occupancy and the inotropic effect of cardiac glycosides in guinea-pig myocardium.

    PubMed Central

    Bachmaier, A.; Ebner, F.; Reiter, M.

    1985-01-01

    K+ (2.4-15.6 mmol l-1) antagonized the positive inotropic effect of dihydro-ouabain. The concentration-effect curves became steeper with the shift to higher concentrations of the glycoside. At 1.2 mmol l-1 Ca2+, an increase in K+ from 2.4 to 12 mmol l-1 required tenfold higher concentrations of dihydro-ouabain to produce equal inotropic effects. This factor was reduced to four at 3.2 mmol l-1 Ca2+. The same change in K+ concentration, at 1.2 mmol l-1 Ca2+, diminished the inotropic effect of ouabain on rested-state contractions by a factor of six. The positive inotropic effect of Ca2+ was also antagonized by K+ (1.2-12 mmol l-1). Reduction of Na+ from 140 to 70 mmol l-1 abolished the antagonistic action of K+ (1.2-8.0 mmol l-1). Moreover the inotropic effect of Ca2+ was enhanced. Reduction of Na+, from 140 to 70 mmol l-1, antagonized the positive inotropic effect of dihydro-ouabain more at low (2.4 mmol l-1) than at high (8.0 mmol l-1) K+. Accordingly, the extent of the dihydro-ouabain-K+ antagonism was reduced. When the K+ concentration was increased from 2.4 to 12 mmol l-1, [3H]-ouabain binding was reduced by a factor of three. This is less than the reduction in the inotropic effectiveness of ouabain or dihydro-ouabain. Reduction of stimulation frequency from 1 to 0.1215 Hz did not significantly alter the antagonistic effect of K+. Diminution of Vmax of the action potential was observed only at K+ concentrations greater than 5.9 mmol l-1, whereas the resting membrane potential was continuously depolarized over the entire range of K+ concentrations. The results support the view that the reduction in receptor affinity cannot be the sole cause of the antagonism between the glycoside and K+. Impairment of passive Na+ influx during diastole, due to the K+-dependent depolarization of the resting membrane potential, contributed to about one half of the glycoside-K+ antagonism. PMID:4041678

  16. The carbohydrate moieties of the beta-subunit of Na+, K(+)-ATPase: their lateral motions and proximity to the cardiac glycoside site.

    PubMed Central

    Amler, E; Abbott, A; Malak, H; Lakowicz, J; Ball, W J

    1996-01-01

    The beta-subunit associated with the catalytic (alpha) subunit of the mammalian Na+, K(+) -ATPase is a transmembrane glycoprotein with three extracellularly located N-glycosylation sites. Although beta appears to be essential for a functional enzyme, the role of beta and its sugars remains unknown. In these studies, steady-state and dynamic fluorescence measurements of the fluorophore lucifer yellow (LY) covalently linked to the carbohydrate chains of beta have demonstrated that the bound probes are highly solvent exposed but restricted in their diffusional motions. Furthermore, the probes' environments on beta were not altered by Na+ or K+ or ouabain-induced enzyme conformational changes, but both divalent cation and oligomycin addition evoked modest changes in LY fluorescence. Frequency domain measurements reflecting the Förster fluorescence energy transfer (FET) occurring between anthroylouabain (AO) bound to the cardiac glycoside receptor site on alpha and the carbohydrate-linked LY demonstrated their close proximity (18 A). Additional FET determinations made between LY as donor and erythrosin-5-isothiocyanate, covalently bound at the enzyme's putative ATP binding site domain, indicated that a distance of about 85 A separates these two regions and that this distance is reduced upon divalent cation binding and increased upon the Na+E1-->K+E2 conformational transition. These data suggest a model for the localization of the terminal moieties of the oligosaccharides that places them, on average, about 18 A from the AO binding site and this distance or less from the extracellular membrane surface. Images FIGURE 5 PMID:8770197

  17. Differential photoaffinity labeling of catalytic subunits of NaK-ATPase with carrier-free /sup 125/I-cardiac glycosides

    SciTech Connect

    Lowndes, J.; Hokin-Neaverson, M.; Ruoho, A.

    1986-05-01

    The authors have obtained evidence for structural differences in the cardiac glycoside binding site between the ..cap alpha.. and ..cap alpha..(+) forms of the catalytic subunit of NaK-ATPase, using three closely related photoaffinity derivatives of the cardiotonic steroid, digitoxigenin. (/sup 125/I)N-(p-azido-m-iodo-o-hydroxybenzoyl)-4-amino-4,6-dideoxy-galactosyl digitoxigenin (IA-GaD), (/sup 125/I)N-(3-(p-azido-m-iodophenyl)-propionyl)-4-amino-4,6-dideoxy-ga-lactosyl digitoxigenin (AIPP-GaD) and (/sup 125/I)N-(3-(p-azido-m-iodophenyl)-propionyl)-4-amino-4,6-dideoxy-glucosyl digitoxi-genin (AIPP-GluD) were synthesized. AIPP-GaD and AIPP-GluD are stereoisomers. Eel electroplax and dog kidney NaK-ATPase (..cap alpha.. form) and rat brain synaptosomes (rich in ..cap alpha..(+) form) were photolabelled and then analyzed by SDS-PAGE and autoradiography. Photolysis with either carrier-free IA-GaD or AIPP-GluD gave ouabain-protectable labelling of NaK-ATPase catalytic subunit from all three tissues. However, photolysis with AIPP-GaD showed protectable labelling of the enzyme from eel and kidney but not from brain. This suggests a structural difference in the ..cap alpha..(+) form which results in either an inability to bind AIPP-GaD, or, perhaps more likely, an absence of a photoinsertion site in the correct location in the ..cap alpha..(+) form, as compared with the ..cap alpha.. form. It is of interest that the labelling pattern of the enzyme in the human erythrocyte resembles that of the brain enzyme.

  18. Does Propolis Contain Tannins?

    PubMed Central

    Mayworm, Marco A. S.; Lima, Carolina A.; Tomba, Augusto C. B.; Fernandes-Silva, Caroline C.; Salatino, Maria L. F.

    2014-01-01

    Although polyphenols have been reported as common constituents of propolis, tannins have rarely been mentioned as its constituents. Propolis samples from seven localities in Brazil were analyzed for detection of proanthocyanidins (condensed tannins) and determination of the tannin content. Positive reaction for proanthocyanidins was observed for all samples tested. The contents of tannins varied in the range 0.6–4.1%. A high degree of correlation was noted between total phenols and tannin content. Red and green propolis contained high contents of tannins, while in brown propolis the content was lower. It is suggested that the contents of tannins should be a parameter to be considered in propolis characterization. PMID:24959188

  19. The origins of tannins and flavonoids in black-wattle barks and heartwoods, and their associated `non-tannin' components

    PubMed Central

    Saayman, H. M.; Roux, D. G.

    1965-01-01

    1. The distributions of flavonoid, carbohydrate, amino acid and imino acid components in the leaves, twig bark, stem bark, root bark and heartwoods of the black-wattle tree were compared by paper chromatography after their isolation from specific portions of the tree. 2. Wattle leaves contain mainly myricitrin, (+)-gallocatechin, an unknown myricetin glycoside and leuco-delphinidin tannins, together with smaller amounts of (+)-catechin, quercitrin and other flavonol glycosides. These are prominent in the twig bark, but decline progressively with age in the stem bark and are absent from root bark. 3. The non-phenolic components of the mature stem bark were shown to be (+)-pinitol, sucrose, glucose, fructose, l(−)-pipecolic acid, trans-4-hydroxy-l(−)-pipecolic acid, α-alanine, arginine, aspartic acid, glutamic acid, l(−)-proline, serine, a `steroid' alcohol and a long-chain β-diketone. 4. Wattle bark and heartwood `tannins' consist of the analogues of closely related prototypes with common origins in the vascular tissues of the bark. Leaf `tannins' are superimposed on the bark components mainly during the initial stages of bark growth. 5. Origins of the pipecolic acids and the transformations of carbohydrates in the sap- and heart-woods are discussed. PMID:5881667

  20. Iridoid glycosides and cucurbitacin glycoside from Neopicrorhiza scrophulariiflora.

    PubMed

    Kim, Ik Hwi; Uchiyama, Nahoko; Kawahara, Nobuo; Goda, Yukihiro

    2006-12-01

    Three iridoid glycosides, picrorosides A (1), B (2) and C (3), and a cucurbitacin glycoside, scrophoside A (4), were isolated from the rhizomes of Neopicrorhiza scrophulariiflora (Scrophulariaceae), along with two known iridoid glycosides, picrosides I (5) and II (6), and three known cucurbitacin glycosides (7-9). Their structures were elucidated on the basis of both chemical and spectroscopic data. PMID:17070880

  1. Tannins as Gibberellin Antagonists 1

    PubMed Central

    Corcoran, Mary Ritzel; Geissman, T. A.; Phinney, Bernard O.

    1972-01-01

    Fourteen chemically defined hydrolyzable tannins and six impure mixtures of either condensed or hydrolyzable tannins were found to inhibit the gibberellin-induced growth of light-grown dwarf pea seedlings. The highest ratio of tannins to gibberellic acid tested (1000: 1 by weight) inhibited from 80 to 95% of the induced growth for all tannins tested except for two monogalloyl glucose tannins which inhibited only 50% of the induced growth. The lowest ratio tested (10: 1) inhibited the induced growth by less than 25% except for the case of terchebin where 50% inhibition was found. The inhibition of gibberellin-induced growth was found to be completely reversed by increasing the amount of gibberellin in three cases tested. Tannins alone did not inhibit endogenous growth of either dwarf or nondwarf pea seedlings. Eight compounds related to tannins, including coumarin, trans-cinnamic acid, and a number of phenolic compounds were also tested as gibberellin antagonists. Most of these compounds showed some inhibition of gibberellin-induced growth, but less than that of the tannins. At the highest ratio (1000: 1) the greatest inhibition was 55%; at the lowest ratio (10: 1) no more than 17% was observed. These compounds did not inhibit endogenous growth, and the inhibition of gibberellin-induced growth could be reversed by increasing the amount of gibberellin in two cases tested. Six chemically defined tannins were found to inhibit hypocotyl growth induced by gibberellic acid in cucumber seedlings. Growth induced by indoleacetic acid in the same test was not inhibited. The highest ratio of tannin to promotor tested gave strong inhibition of gibberellic acid-induced growth, but actually enhanced the growth induced by indoleacetic acid. This difference in action suggests a specificity between the tannins and gibberellic acid. PMID:16657953

  2. Cytotoxic cardenolide glycosides from the seeds of Antiaris toxicaria.

    PubMed

    Dong, Wen-Hua; Mei, Wen-Li; Zhao, You-Xing; Zeng, Yan-Bo; Zuo, Wen-Jian; Wang, Hui; Li, Xiao-Na; Dai, Hao-Fu

    2011-10-01

    Bioassay-guided fractionation of the ethanolic extract from the seeds of Antiaris toxicaria led to the isolation of three new cardiac glycosides named toxicarioside J, toxicarioside K, and toxicarioside L, together with a known glucostrophalloside. The structures of the new compounds were elucidated by spectroscopic methods including HRESIMS, UV, IR, and 1D, 2D NMR techniques. The cytotoxic activities of these cardiac glycosides against human gastric (SGC-7901) and human hepatoma (SMMC-7721) cell lines were evaluated, and all of them exhibited significant cytotoxicity. PMID:21509716

  3. Tannin (Polyphenol) Stability in Aqueous Solutions

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Understanding the chemical stability of tannins (polyphenolics) in soils is critical to understanding their biological activities and fate. We examined the stability of chemically defined tannins in aqueous solutions under conditions simulating natural and laboratory conditions. We evaluated tanni...

  4. Variants of glycoside hydrolases

    SciTech Connect

    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.

  5. Variants of glycoside hydrolases

    DOEpatents

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

    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.

  6. 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. PMID:27041322

  7. 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

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins are large polyphenolic polymers and are known to bind proteins, limiting their digestibility. Tannins are also known for having excellent antioxidant potential. To examine the precise impact of tannin content and composition on the biological activities (protein binding, protein digestibil...

  9. Monoterpene glycosides from Paeonia delavayi.

    PubMed

    Wu, Shao-Hua; Chen, You-Wei; Yang, Li-Yuan; Li, Shao-Lan; Li, Zhi-Ying

    2007-01-01

    A new monoterpene glycoside, 4-O-methyl-4''-hydroxy-3''-methoxy-paeoniflorin (1), was isolated from the root cortex of Paeonia delavayi along with the known paeoniflorin, oxypaeoniflorin, benzoylpaeoniflorin, benzoyloxypaeoniflorin, albiflorin and a paeonilactone-A. PMID:17067761

  10. Sorption of polyphenolics (tannins) to natural soils

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The plant secondary metabolites known as tannins (polyphenolics) comprise up to 40% of the dry mass of plant tissue. Tannins have potent bioactivities ranging from protein precipitation to metal binding and radical quenching, and can affect nutrient metal availability, nitrogen availability, and so...

  11. Sorption of polyphenolics (tannins) to natural soils

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  12. 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.

  13. A new glycosidic flavonoid from Jwarhar mahakashay (antipyretic) Ayurvedic preparation

    PubMed Central

    Gupta, Mradu; Shaw, B. P.; Mukherjee, A.

    2010-01-01

    The aqueous extract of Jwarhar mahakashay Ayurvedic preparation (from the roots of Hemidesmus indicus R. Br., Rubia cordifolia L., Cissampelos pareira L.; fruits of Terminalia chebula Retz., Emblica officinalis Gaertn., Terminalia bellirica Roxb., Vitis vinifera L., Grewia asiatica L., Salvadora persica L. and granules of Saccharum officinarum L.) has been used as a traditional antipyretic. Experimental studies confirmed its antipyretic–analgesic effect with very low ulcerogenicity and toxicity. Flavonoids, glycosides and tannins were later found to be present in the extract. Detailed chemical investigations were undertaken after hydrolysis of extract using spectroscopic and chromatography methods to determine its active chemical constituent. UV-Visible spectroscopy showed absorbance maxima at 220 and 276 nm, while fourier transform infra-red investigations indicated an end carboxylic O–H structure at 2940 cm−1 suggesting the presence of glycoside-linked flavonoids. Thin layer chromatography and high performance liquid chromatography also confirmed the possibility of at least one major and two minor compounds in this abstract. Detailed examination using gas chromatography-mass spectrometry led to the identification of the principal component as 2-(1-oxopropyl)-benzoic acid, which is quite similar to the active compound found in the standard drug Aspirin (2-acetyl-oxybenzoic acid). PMID:20814525

  14. Transgenic upregulation of the condensed tannin pathway in poplar leads to a dramatic shift in leaf palatability for two tree-feeding Lepidoptera.

    PubMed

    Boeckler, G Andreas; Towns, Megan; Unsicker, Sybille B; Mellway, Robin D; Yip, Lynn; Hilke, Ines; Gershenzon, Jonathan; Constabel, C Peter

    2014-02-01

    Transgenic hybrid aspen (Populus tremula x tremuloides) overexpressing the MYB134 tannin regulatory gene show dramatically enhanced condensed tannin (proanthocyanidin) levels, as well as shifts in other phenolic metabolites. A series of insect bioassays with forest tent caterpillars (Malacosoma disstria) and gypsy moth (Lymantria dispar) caterpillars was carried out to determine how this metabolic shift affects food preference and performance of generalist tree-feeding lepidopterans. Both species showed a distinct preference for the high-tannin MYB134 overexpressor plants, and L. dispar performance was enhanced relative to controls. L. dispar reached greater pupal weight and showed reduced time to pupation when reared on the MYB134 overexpressing poplar. These results were unexpected since enhanced condensed tannin levels were predicted to act as feeding deterrents. However, the data may be explained by the observed decrease in the salicinoids (phenolic glycosides) salicortin and tremulacin that accompanied the upregulation of the condensed tannins in the transgenics. We conclude that for these two lepidopteran species, condensed tannin levels are unlikely to be a major determinant of caterpillar food preference or performance. However, our experiments show that overexpression of a single regulatory gene in transgenic aspen can have a significant impact on herbivorous insects. PMID:24496605

  15. 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. PMID:18253799

  16. Monoterpene glycosides, phenylpropanoids, and acacetin glycosides from Dracocephalum foetidum.

    PubMed

    Selenge, Erdenechimeg; Murata, Toshihiro; Tanaka, Shiho; Sasaki, Kenroh; Batkhuu, Javzan; Yoshizaki, Fumihiko

    2014-05-01

    Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox. PMID:24582463

  17. Tannin rich peanut skins lack anthelmintic properties

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Gastrointestinal nematode (GIN) resistance to synthetic anthelmintics in small ruminants has led to the evaluation of feed sources containing naturally occurring bioactive secondary metabolites that lessen parasite activity. Plants rich in condensed tannins (CT) can have beneficial anthelmintic pro...

  18. Antimicrobial activity of tannins from Terminalia citrina.

    PubMed

    Burapadaja, S; Bunchoo, A

    1995-08-01

    Isolation of the fruit CH3OH extract of Terminalia citrina yielded five known tannins identified as corilagin (1) (3), punicalagin (2) (4), 1,3,6-tri-O-galloyl-beta-D-glucopyranose (3) (5), chebulagic acid (4) (6), and 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose (5) (7) by comparison of their physical and spectral data with those of authentic samples. These tannins were tested for antimicrobial action. PMID:7480186

  19. Hierarchical classification of glycoside hydrolases.

    PubMed

    Naumoff, D G

    2011-06-01

    This review deals with structural and functional features of glycoside hydrolases, a widespread group of enzymes present in almost all living organisms. Their catalytic domains are grouped into 120 amino acid sequence-based families in the international classification of the carbohydrate-active enzymes (CAZy database). At a higher hierarchical level some of these families are combined in 14 clans. Enzymes of the same clan have common evolutionary origin of their genes and share the most important functional characteristics such as composition of the active center, anomeric configuration of cleaved glycosidic bonds, and molecular mechanism of the catalyzed reaction (either inverting, or retaining). There are now extensive data in the literature concerning the relationship between glycoside hydrolase families belonging to different clans and/or included in none of them, as well as information on phylogenetic protein relationship within particular families. Summarizing these data allows us to propose a multilevel hierarchical classification of glycoside hydrolases and their homologs. It is shown that almost the whole variety of the enzyme catalytic domains can be brought into six main folds, large groups of proteins having the same three-dimensional structure and the supposed common evolutionary origin. PMID:21639842

  20. Flavonol Glycosides from Gaura Biennis

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  1. 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.

  2. Chestnut bark tannin assays and growth of chestnut blight fungus on extracted tannin.

    PubMed

    Anagnostakis, S L

    1992-08-01

    Tannins extracted from the green bark of each of two Chinese, Japanese, and American chestnut trees were assayed in a protein-binding test. Four levels of tannins were added to a buffered, minimal growth medium, and a standard, virulent strain of the chestnut blight fungus was grown. There were only slight differences in protein binding between the extracts from different species. Fungal growth was better with tannin than without, but there was no difference between species extracts in their ability to improve fungal growth rate. There was also no inhibition of blight fungus growth by any of the tree tannins, so tannin toxicity is not the reason for Asian chestnut tree resistance. PMID:24254212

  3. Cyanogenetic glycosides and simple glycosides from the linseed meal.

    PubMed

    Yang, Qing-Yun; Song, Li; Zhang, Ji-Fa; Shen, Zhu-Fang; Liu, Quan; Liu, Shuai-Nan; Zheng, Wen-Sheng; Yao, Chun-Suo

    2015-10-01

    Three new cyanogenetic triglycosides linustatins A-C (1-3), and two new simple glycosides linustatins D and E (4 and 5) were isolated from the 70% ethanol extract of flaxseed meal (Linum usitatissimum L.). Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates showed moderate activities against aldose reductase and weak activities against α-glucosidase, DPP-IV, and FBPase at the same concentrations as the positive control drugs. PMID:26307006

  4. Diterpene glycosides from Stevia rebaudiana.

    PubMed

    Chaturvedula, Venkata Sai Prakash; Upreti, Mani; Prakash, Indra

    2011-01-01

    Three novel diterpene glycosides were isolated for the first time from the commercial extract of the leaves of Stevia rebaudiana, along with several known steviol glycosides, namely stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compounds were identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-15-en-19-oic acid, 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-16β-hydroxy-ent-kauran-19-oic acid and 13-methyl-16-oxo-17-nor-ent-kauran-19-oic acid-β-D-glucopyranosyl ester on the basis of extensive 2D NMR and MS spectroscopic data as well as chemical studies. PMID:21527882

  5. Iridoid glycosides from Barleria lupulina.

    PubMed

    Kim, Ki Hyun; Park, Yong Joo; Chung, Kyu Hyuck; Yip, M L Richard; Clardy, Jon; Senger, Donald; Cao, Shugeng

    2015-02-27

    Phytochemical investigation of an extract of the aerial part of Barleria lupulina resulted in the identification of four new iridoid glycosides (1-4), together with 14 known analogues (5-18). The structures of 1-4 were determined through 1D and 2D NMR spectroscopic data analysis, HRMS, and acid hydrolysis. This is the first report of iridoid glycosides with a formate group. The free-radical scavenging activity of compounds 9, 12, and 15-17 was assessed using the DPPH assay. Compounds 16 and 17 scavenged DPPH radicals weakly with IC50 values of 97.5 and 78.6 μg/mL, respectively. PMID:25611215

  6. Accumulation of uranium by immobilized persimmon tannin

    SciTech Connect

    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, 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.

  7. Steroidal glycosides from Ruscus ponticus.

    PubMed

    Napolitano, Assunta; Muzashvili, Tamar; Perrone, Angela; Pizza, Cosimo; Kemertelidze, Ether; Piacente, Sonia

    2011-05-01

    A comparative metabolite profiling of the underground parts and leaves of Ruscus ponticus was obtained by an HPLC-ESIMS(n) method, based on high-performance liquid chromatography coupled to electrospray positive ionization multistage ion trap mass spectrometry. The careful study of HPLC-ESIMS(n) fragmentation pattern of each chromatographic peak, in particular the identification of diagnostic product ions, allowed us to get a rapid screening of saponins belonging to different classes, such as dehydrated/or not furostanol, spirostanol and pregnane glycosides, and to promptly highlight similarities and differences between the two plant parts. This approach, followed by isolation and structure elucidation by 1D- and 2D-NMR experiments, led to the identification of eleven saponins from the underground parts, of which two dehydrated furostanol glycosides and one new vespertilin derivative, and nine saponins from R. ponticus leaves, never reported previously. The achieved results highlighted a clean prevalence of furostanol glycoside derivatives in R. ponticus leaves rather in the underground parts of the plant, which showed a wider structure variety. In particular, the occurrence of dehydrated furostanol derivatives, for the first time isolated from a Ruscus species, is an unusual finding which makes unique the saponins profile of R. ponticus. PMID:21354581

  8. 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

  9. 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.

  10. Synthesis and characterization of tannin grafted polycaprolactone.

    PubMed

    Song, Ping; Jiang, Suchen; Ren, Yajun; Zhang, Xue; Qiao, Tiankui; Song, Xiaofeng; Liu, Qimin; Chen, Xuesi

    2016-10-01

    Tannin and biodegradable polyester have attracted increasing interest for biomedical applications. To improve their compatibility, a novel tannin grafted polycaprolactone (TA-g-PCL) has been synthesized via ring-opening polymerization reaction. The structure of the product is characterized with FTIR, (1)H NMR and GPC. GPC results show that the experimental molecular weight is far less than the theoretical due to complicated stereo structure and large steric hindrance of tannic molecule, but the polydispersity of the product is narrow. At 115.76:1 of molar ratio of CL to tannin, molecular weight of the product reaches the maximum. Thermodynamics properties and dissolubility of TA-g-PCL are closely related to its molecular weight. With PCL molecular chain grows, TA-g-PCL changes from amorphous form to crystalline structure, and its dissolubility in chloroform is also enhanced significantly. PMID:27388129

  11. Ethanol production performance of ozone treated tannin grain sorghum flour

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Grain sorghum lines containing tannins have been reported to exhibit increased resistance to drought, birds, mold, preharvest germination, and higher grain yield than non-tannin grain sorghum lines, but tannins have been considered an adverse factor in the utilization of sorghum as a feedstock for b...

  12. Tannin extracts abate ammonia emissions from dairy barn floors

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Feeding more tannin and less crude protein (CP) to dairy cows may have compound positive impacts on reducing NH3 emissions from dairy barns. Mixtures of feces-urine from lactating Holstein dairy cows (Bos taurus) fed four levels (g kg-1) of dietary tannin extract: 0 (0T), 4.5 (low tannin, LT), 9.0 (...

  13. Powdered hide model for vegetable tanning II. hydrolyzable tannin

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  14. Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation.

    PubMed

    Thadke, Shivaji A; Neralkar, Mahesh; Hotha, Srinivas

    2016-07-22

    The O-glycosidation of hydroxysuccinimides and hydroxyphthalimides with a variety of aldose derived propargyl 1,2-orthoesters under the gold(III)-catalyzed glycosidation conditions is reported. A wide range of hydroxysuccinimidyl and hydroxyphthalimidyl glycosides were synthesized from corresponding glycosyl orthoesters including glucosyl, mannosyl, galactosyl, ribofuranosyl, arabinofuranosyl, lyxofuranosyl and xylofuranosyl using gold catalysis repertoire. The protocol is identified to be compatible for the synthesis of aminooxy glycosides of higher oligosaccharides as well. PMID:27162194

  15. Bioconversion of steroid glycosides by Nocardia restricta.

    PubMed

    Belic, I; Kastelic-Suhadolc, T; Kralj, B

    1985-09-01

    The bioconversion of steroid alkaloid tomatine by Nocardia restricta yields the conjugate with lactic acid. We studied the bioconversion of some steroid glycosides without a nitrogen atom in the molecule to determine the effect of the nitrogen atom. The glycosides were of three different types: sterol glycosides, bufadienolide rhamnoside and steroid saponine. The results of bioconversions showed that Nocardia restricta converts steroid glycosides differently according to the sugar bound to the steroid aglycone. It can be concluded that in the absence of a nitrogen atom in the steroid molecule no conjugation with lactic acid by Nocardia restricta occurs. PMID:4046605

  16. A new phenolic constituent and a cyanogenic glycoside from Balanophora involucrata (Balanophoraceae).

    PubMed

    She, Gai-Mei; Zhang, Ying-Jun; Yang, Chong-Ren

    2013-06-01

    Balanophora involucrata HOOK.f. & THOMSON (Balanophoraceae) is a parasite plant often growing on the roots of leguminous plants. The whole herb has been used medicinally for the treatment of irregular menstruation, cough, hemoptysis, traumatic injury and bleeding, dizziness and gastralgia in Yunnan Province, China. The 2,2-diphenyl-2-picrylhydrazyl (DPPH) assay on the 60% aq. acetone extract of the fresh whole plant of B. involucrata showed considerable radical-scavenging activity (SC₅₀ 15.3 μg/ml). Further purification on the extract led to the isolation of one new phenolic glycoside, sieboldin-3'-ketocarboxylic acid (1), and one new cyanogenic glycoside, proacacipetalin 6'-O-β-D-glucopyranoside (2), together with 26 known compounds including three 4"-O-galloyl and 2",3"-O-(S)-hexahydroxydiphenoyl (HHDP) derivatives of dihydrochalcone glucosides, seven hydrolyzable tannins, and alkane glycosides. The cyanogenic compound isolated from the Balanophoraceae family for the first time might be a signal molecule between B. involucrata and its hosts. The free-radical-scavenging activity of the isolated compounds was also examined by DPPH assay. PMID:23776023

  17. Activity, purification, and analysis of condensed tannins

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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 ...

  18. 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…

  19. 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. PMID:25753857

  20. 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

    2015-09-01

    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. PMID:26223789

  1. 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.

  2. Neuroprotective bibenzyl glycosides of Stemona tuberosa roots.

    PubMed

    Lee, Ki Yong; Sung, Sang Hyun; Kim, Young Choong

    2006-04-01

    Three new bibenzyl glycosides characterized as stilbostemin B 3'-beta-D-glucopyranoside (1), stilbostemin H 3'-beta-D-glucopyranoside (2), and stilbostemin I 2"-beta-D-glucopyranoside (3) were isolated from the roots of Stemona tuberosa. All three bibenzyl glycosides significantly protected human neuroblastoma SH-SY5Y cells from 6-hydroxydopamine-induced neurotoxicity. PMID:16643052

  3. Two New Triterpene Glycosides from Centella asiatica

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phytochemical investigation of the leaves of Centella asiatica resulted in the isolation and characterization of one new ursane type triterpene glycoside; asiaticoside G along with nine known compounds, that were characterized as ursane type triterpenes and /or their glycoside; asiatic acid (2), mad...

  4. Phenylpropanoid glycosides from Orobanche caerulescens.

    PubMed

    Lin, Lie-Chwen; Chiou, Wen-Fei; Chou, Cheng-Jen

    2004-01-01

    Two new phenylpropanoid glycosides, caerulescenoside ( 1), and 3'-methyl crenatoside ( 2), as well as five known phenylpropanoid glycosides [acteoside ( 3), isoacteoside ( 4), campneoside II ( 5), crenatoside ( 6), and desrhamnosyl acteoside ( 7)] were isolated from the whole plant of Orobanche caerulescens. The antioxidative effects of compounds 1 - 7 on human low-density lipoprotein were evaluated. All these compounds suppress concentration-dependently conjugated diene formation with IC (50) values of 1.25 +/- 0.06, 2.97 +/- 0.31, 0.31 +/- 0.01, 1.01 +/- 0.05, 1.15 +/- 0.04, 1.69 +/- 0.15, and 0.64 +/- 0.03 microM, respectively. Comparison of their antioxidative activities with that of resveratrol (IC (50) : 6.75 +/- 1.05 microM), a natural phenolic antioxidant isolated from grape, demonstrated that the prolonged effect on lag-time and the damping effect on oxidative rate by compounds 1 - 7 were all more potent. PMID:14765293

  5. Phenolic glycosides from Kaempferia parviflora.

    PubMed

    Azuma, Toshiaki; Tanaka, Yasuo; Kikuzaki, Hiroe

    2008-11-01

    Three phenolic glycosides were isolated together with two known flavonol glycosides from the H2O-soluble fraction of rhizomes of Kaempferia parviflora. Their structures were determined to be rel-(5aS,10bS)-5a,10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]indeno[1,2-d]furan-6-one 5a-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-d-glucopyranoside] (1), its rel-5aS,10bR isomer (2), and (2R,3S,4S)-3-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-d-glucopyranosyl]-3'-O-methyl-ent-epicatechin-(2alpha-->O-->3,4alpha-->4)-(5aS,10bS)-5a,10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]indeno[1,2-d]furan-6-one 5a-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside] (3). The structures were elucidated on the basis of analyses of chemical and spectroscopic evidence. PMID:18922550

  6. Cardiac Rehabilitation

    MedlinePlus

    ... from the NHLBI on Twitter. What Is Cardiac Rehabilitation? Cardiac rehabilitation (rehab) is a medically supervised program ... be designed to meet your needs. The Cardiac Rehabilitation Team Cardiac rehab involves a long-term commitment ...

  7. 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.

  8. Intoxication of sheep with quebracho tannin extract.

    PubMed

    Hervás, G; Pérez, V; Giráldez, F J; Mantecón, A R; Almar, M M; Frutos, P

    2003-07-01

    This experiment was carried out to study the toxicity of quebracho tannin extract (containing 760 g of condensed tannins [CTs] per kg), with the aim of validating its use as a feed additive for improving the digestive utilization of protein-rich feeds. Four groups (Q(0), Q(1), Q(2) and Q(3)) of four sheep were dosed intra-ruminally once daily, for up to 21 days with, respectively, 0, 0.5, 1.5 or 3.0 g quebracho tannin extract/kg live-weight (LW). Feed intake, live-weight changes, plasma biochemistry, indicators of hepatic detoxification function, gross lesions and histopathology were examined. Animals in groups Q(0), Q(1) and Q(2) consumed all the offered feed. In contrast, feed intake was practically nil after 6 days of quebracho dosing in group Q(3), this being associated with a loss of 4.7+/-1.30 kg LW in 10 days (P<0.05). Sheep from groups Q(0), Q(1) and Q(2) remained healthy throughout the experiment. Ewes from group Q(3) became weak and depressed on day 5 and after 8 days of dosing remained recumbent. They were humanely killed after 10 days to avoid suffering. In general, neither gross lesions nor microscopical changes were observed in animals from groups Q(0), Q(1) and Q(2). However, Q(3) sheep showed striking lesions in the digestive tract (well-demarcated ulcers filled with necrotic material in the mucosa of the rumen and reticulum, distension of abomasum and small intestine, and dense mucous material in the caecum), and changes in plasma biochemistry. Cytochrome P-450 and glutathione concentrations were significantly reduced in Q(3) sheep (P<0.05). It is concluded that quebracho tannin extract is not toxic for ruminants, except in concentrations too high to be encountered under practical conditions. PMID:12859907

  9. Two new glycosides from Conyza bonariensis.

    PubMed

    Zahoor, Aqib; Siddiqui, Imran Nafees; Khan, Afsar; Ahmad, Viqar Uddin; Ahmed, Amir; Hassan, Zahid; Khan, Saleha Suleman; Iqbal, Shazia

    2010-07-01

    Studies on Conyza bonariensis (L.) Cronq. led to the isolation of two new glycosides trivially named as erigeside E and F (1-2), along with two new source compounds; benzyl-beta-D-glucopyranoside (3) and 2-phenylethyl-beta-D-glucopyranoside (4). Compounds 1, 3, and 4 are aromatic glycosides, while compound 2 is an alkyl glycoside. Their structures were elucidated through mass spectrometric, and 1D- and 2D-NMR spectroscopic techniques, including 1H NMR, 13C NMR, HMQC, HSQC and HMBC. PMID:20734949

  10. Recovery of uranium from seawater by immobilized tannin

    SciTech Connect

    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 of 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.

  11. 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. PMID:25704681

  12. Dietary tannins improve lamb meat colour stability.

    PubMed

    Luciano, G; Monahan, F J; Vasta, V; Biondi, L; Lanza, M; Priolo, A

    2009-01-01

    Fourteen male Comisana lambs were divided into two groups at 45days of age: lambs fed a concentrate diet (C), or lambs fed the same concentrate with the addition of quebracho (Schinopsis lorentzii) tannins (T). Sheep were slaughtered at 105days of age. Lipid oxidation, colour coordinates, haem pigment concentration, and metmyoglobin percentages were measured on minced semimembranosus muscle (SM) over 14days of refrigerated storage in a high oxygen modified atmosphere. Tannin supplementation increased (P<0.01) a(∗) values and reduced (P<0.01) b(∗) values of the SM when compared to C. Lower hue angles (P<0.001) and metmyoglobin formation (P=0.07) were observed in lamb from T-fed compared to C-fed sheep during the 14-days storage period. Furthermore, feeding T resulted in greater (P<0.001) haem pigment concentrations in the SM during refrigerated storage; however, diet had no (P=0.28) effect on lipid oxidation. Therefore, including quebracho tannins in sheep diets can improve meat colour stability of fresh lamb during extended refrigerated storage. PMID:22063971

  13. 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. PMID:19063768

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

    PubMed

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

    2016-02-01

    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. PMID:26766301

  15. Triterpene glycosides from the Far Eastern sea cucumber Cucumaria conicospermium.

    PubMed

    Avilov, Sergey A; Antonov, Alexandr S; Silchenko, Alexandra S; Kalinin, Vladimir I; Kalinovsky, Anatoly I; Dmitrenok, Pavel S; Stonik, Valentin A; Riguera, Ricardo; Jimenez, Carlos

    2003-07-01

    Four new triterpene glycosides, cucumariosides A(2)-5 (1), A(3)-2 (2), A(3)-3 (3), and isokoreoside A (4), along with the previously isolated koreoside A (5), have been found in the sea cucumber Cucumariaconicospermium. Glycoside 1 was isolated as a native substance, while glycosides 2-5 were identified through their desulfated derivatives. Their structures have been deduced by extensive spectral analysis (NMR and MS) and chemical evidence. All the glycosides contain the same branched pentasaccharide carbohydrate chain but differ in the number and positions of the sulfate groups. Glycoside 1 has one, glycosides 2 and 3 have two, and glycosides 4 and 5 have three sulfate groups. Glycosides 2-5 are non-holostane derivatives; their aglycons lack the 18(20)-lactone and are characterized by shortened side chains, which is a very rare feature among the sea cucumber glycosides. PMID:12880305

  16. Sheep Ingestion of Water Containing Quebracho or Black Wattle Tannin

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ingestion of small amounts of condensed tannin by ruminants can produce valuable outcomes such as improved nitrogen use, reduced bloating and methane output, and internal parasite reduction. Many grasses and forbs have little if any condensed tannin in them. Not all livestock will consistently con...

  17. Wheat Forages Contain Variable Levels of Condensed Tannin Reactive Substances

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Even though winter wheat pasture in the southern Great Plains is considered excellent forage, devastating losses of stocker cattle can occur due to pasture bloat. Tannins are known to reduce the incidence and severity of bloat. We examined tannins in adapted wheat varieties that are commonly grazed ...

  18. Improved Characterization of Sorghum Tannins Using Size-Exclusion Chromatography

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins are large polyphenolic polymers consisting of flavan-3-ol subunits that are deposited in the pigmented testa layer of sorghum kernels. Tannins have been characterized in several different species of plants using a multitude of techniques. Most of the methods are very time and resource consum...

  19. HPLC retention thermodynamics of grape and wine tannins.

    PubMed

    Barak, Jennifer A; Kennedy, James A

    2013-05-01

    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. PMID:23565723

  20. A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides

    PubMed Central

    2010-01-01

    Digitoxin is a cardiac glycoside currently being investigated for potential use in oncology; however, an investigation of anticancer activity as a function of oligosaccharide chain length has not yet been performed. We generated mono-, di-, and tri-O-digitoxoside derivatives of digitoxin and compared their activities to the corresponding MeON-neoglycosides. Both classes of cardenolide derivatives display comparable oligosaccharide chain length-dependent cytotoxicity toward human cancer cell lines. Further investigation revealed that both classes of compounds induce caspase-9-mediated apoptosis in non-small cell lung cancer cells (NCI-H460). Because O-glycosides and MeON-neoglycosides share a similar mode of action, the convenience of MeON-neoglycosylation could be exploited in future SAR work to rapidly survey large numbers of carbohydrates to prioritize selected O-glycoside candidates for traditional synthesis. PMID:21103068

  1. Tannin extracts abate ammonia emissions from simulated dairy barn floors.

    PubMed

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

    2011-01-01

    Feeding more tannin and less crude protein (CP) to dairy cows may have synergistic impacts on reducing NH emissions from dairy barns. Three trials using lab-scale ventilated chambers with concrete floors were conducted to determine the impacts on NH emission of tannin and CP feeding, tannin feeding on urease activity in feces, and tannin application directly to the barn floor. For Trial 1, mixtures of feces and urine from lactating Holstein dairy cows () fed four levels (g kg) of dietary tannin extract [a mixture from red quebracho () and chestnut () trees]: 0 tannin (0T), 4.5 (low tannin [LT]), 9.0 (medium tannin [MT]), and 18.0 (high tannin [HT]); each fed at two levels (g kg) of dietary CP: 155 low CP (LCP) and 168 high CP (HCP) were applied to chambers. For Trial 2, urea solution was added to feces obtained from cows fed 0T, MT, and HT at HCP. For Trial 3, tannin amounts equivalent to those fed at 0T, MT, and HT were applied directly to feces-urine mixtures from 0T-HCP. For all trials, NH emissions were measured 1, 3, 6, 12, 24, 36, and 48 h after treatment application. For Trial 1, reductions in NH emission due to tannin feeding were greatest when fed at LCP: The LCP-LT and LCP-HT treatments emitted 30.6% less NH than LCP-0T, and the HCP-LT and HCP-HT treatments emitted 16.3% less NH than HCP-0T. For Trial 2, feeding tannin decreased urease activity in feces, resulting in an 11.5% reduction in cumulative NH loss. For Trial 3, the application of tannin directly to simulated barn floors also apparently decreased urease activity, resulting in an average reduction in cumulative NH emissions of 19.0%. Larger-scale trails are required to ascertain the effectiveness of tannin extracts in abating NH loss from dairy barn floors. PMID:21546676

  2. Vegetable oil thermosets reinforced by tannin-lipid formulations.

    PubMed

    Luo, Chunhua; Grigsby, Warren J; Edmonds, Neil R; Al-Hakkak, Jafar

    2013-02-01

    Totally bio-based thermosetting polymers which are comparable to synthetic polyester thermosets have been prepared from copolymerization of condensed tannin-fatty acid esters with vegetable oils. Oxidative copolymerization of tannin linoleate/acetate mixed esters with linseed oil and tung oil produced polymer films ranging from soft rubbers to rigid thermosets. Tannin incorporation into the formulations was essential for the final product to achieve necessary mechanical strength. Films had ambient modulus values between 0.12 and 1.6 GPa, with glass transition temperatures ranging from 32 to 72 °C and calculated crosslink densities of 1020-57,700 mol m⁻³. Film stiffness, T(g) and crosslink density increase with greater tannin linoeate/acetate content due mainly to this tannin component providing rigidity through polyphenolic aromatic rings and unsaturated chains as crosslinking sites. PMID:22975626

  3. Tannin-binding salivary proteins in three captive rhinoceros species.

    PubMed

    Clauss, Marcus; Gehrke, Janin; Hatt, Jean-Michel; Dierenfeld, Ellen S; Flach, Edmund J; Hermes, Robert; Castell, Johanna; Streich, W Juergen; Fickel, Joerns

    2005-01-01

    Tannin-binding salivary proteins (TBSP) are considered to be counter-defences acquired in the course of evolution by animals whose natural forage contains such tannins. As tannins mostly occur in browse material but not in grasses, it is assumed that grazers do not have a need for TBSP. Whereas it has been shown in several non-ungulate species that TBSP can be induced by dietary tannins, their presence or absence in ungulates has, so far, been shown to be a species-specific characteristic independent of dietary manipulations. We investigated saliva from three rhinoceros species from zoological gardens fed comparable, conventional zoo diets. As expected, saliva from white rhinoceroses (Ceratotherum simum, grazer) had lower tannin-binding capacities than that from black rhinoceroses (Diceros bicornis, browser). Surprisingly, however, Indian rhinoceroses (Rhinoceros unicornis), commonly regarded as grazers as well, displayed the highest tannin-binding capacities of the three species investigated. It is speculated that this discrepancy might be a result of an evolutionarily recent switch to a grass-dominated diet in Indian rhinoceroses, and that the black rhinoceros, which is closer related to the white rhinoceros than the Indian species, has evolved an inducible mechanism of TBSP production. In separate trials during which the tannin content of the diets of black rhinoceroses was increased by the addition of either tannic acid or quebracho, the tannin-binding capacity of black rhinoceros saliva was increased to levels within the same range as that of Indian rhinoceroses on the conventional diets. While induction trials in white and Indian rhinoceroses remain to be performed for a full understanding of salivary anti-tannin defence in rhinoceroses, these results are the first report of an induced salivary response to increased dietary tannin levels in an ungulate species. PMID:15664314

  4. Cardiac Catheterization

    MedlinePlus

    ... from the NHLBI on Twitter. What Is Cardiac Catheterization? Cardiac catheterization (KATH-eh-ter-ih-ZA-shun) is a ... disease. Doctors also can use ultrasound during cardiac catheterization to see blockages in the coronary arteries. Ultrasound ...

  5. Diterpene glycosides from Stevia phlebophylla A. Gray.

    PubMed

    Ceunen, Stijn; Wim, De Borggraeve; Compernolle, Frans; Mai, Anh Hung; Geuns, Jan M C

    2013-09-20

    The rare Mexican species Stevia phlebophylla A. Gray was long considered to be the only known Stevia species, beside the well-known S. rebaudiana, containing the highly sweet diterpenoid steviol glycosides. We report a re-evaluation of this claim after phytochemically screening leaves obtained from two herbarium specimens of S. phlebophylla for the presence of steviol glycosides. Despite extensive MS analyses, no steviol glycosides could be unambiguously verified. Instead, the main chromatographic peak eluting at retention times similar to those of steviol glycosides was identified as a new compound, namely 16β-hydroxy-17-acetoxy-ent-kauran-19-oic acid-(6-O-β-D-xylopyranosyl-β-D-glucopyranosyl) ester (1) on the basis of extensive NMR and MS data as well as the characterization of its acid hydrolysate. Seven more compounds were detected by ESIMS which are possibly structurally related to 1. It can therefore be concluded that S. phlebophylla is unlikely to contain significant amounts of steviol glycosides, if any. PMID:23831634

  6. New kaurene diterpenoid glycosides from fenugreek seeds.

    PubMed

    Pang, Xu; Kang, Li-Ping; Yu, He-Shui; Zhao, Yang; Xiong, Cheng-Qi; Zhang, Jie; Ma, Bai-Ping

    2013-01-01

    Two new kaurene diterpenoid glycosides, named Graecumoside A (1) and B (2), were isolated from fenugreek seeds, along with three known flavonoid-C-glycosides, isoorientin (3), isovitexin (4) and vitexin (5). By combined analyses of 1D- and 2D-NMR, and MS spectroscopy, the structures of two new compounds were elucidated as 3-O-β- D-glucopyranosyl kaur-5, 16-dien-3β, 6, 13β-trihydroxy-7-oxo-18-oic acid methyl ester and 3-O-β-neohesperidosyl kaur-5, 16-dien-3β, 6, 13β-trihydroxy-7-oxo-18-oic acid methyl ester, respectively. The kaurene diterpenoid glycosides were first isolated and identified from fenugreek seeds. PMID:22950814

  7. Steviol glycosides: chemical diversity, metabolism, and function.

    PubMed

    Ceunen, Stijn; Geuns, Jan M C

    2013-06-28

    Steviol glycosides are a group of highly sweet diterpene glycosides discovered in only a few plant species, most notably the Paraguayan shrub Stevia rebaudiana. During the past few decades, the nutritional and pharmacological benefits of these secondary metabolites have become increasingly apparent. While these properties are now widely recognized, many aspects related to their in vivo biochemistry and metabolism and their relationship to the overall plant physiology of S. rebaudiana are not yet understood. Furthermore, the large size of the steviol glycoside pool commonly found within S. rebaudiana leaves implies a significant metabolic investment and poses questions regarding the benefits S. rebaudiana might gain from their accumulation. The current review intends to thoroughly discuss the available knowledge on these issues. PMID:23713723

  8. Condensed tannins increase nitrogen recovery by trees following insect defoliation.

    PubMed

    Madritch, Michael D; Lindroth, Richard L

    2015-10-01

    While the importance of plant secondary metabolites to belowground functioning is gaining recognition, the perception remains that secondary metabolites are produced for herbivore defense, whereas their belowground impacts are ecological by-products, or 'afterlife' effects. However, plants invest a significant amount of resources into production of secondary metabolites that have minimal effects on herbivore resistance (e.g. condensed tannins and insect herbivores). We show that genetically mediated variation in condensed tannin concentration is correlated with plant nitrogen recovery following a severe defoliation event. We used single-tree mesocosms labeled with (15) N to track nitrogen through both the frass and litter cycling pathways. High concentrations of leaf tannins in Populus tremuloides were correlated with (15) N recovery from frass within the same growing season and in the following growing season. Likewise, leaf tannin concentrations were also correlated with (15) N recovery from the litter of defoliated trees in the growing season following the defoliation event. Conversely, tannins were not well correlated with nitrogen uptake under conditions of nominal herbivory. Our results suggest that tannins may confer benefits in response to herbivore pressure through conserved belowground nitrogen cycling, rather than via defensive properties. Consequently, tannins may be considered as chemical mediators of tolerance rather than resistance. PMID:25952793

  9. Five new phenolic glycosides from Hedyotis scandens.

    PubMed

    Wang, Guo-Cai; Li, Tao; Deng, Fang-Ye; Li, Yao-Lan; Ye, Wen-Cai

    2013-03-01

    Five new phenolic glycosides, hedyotosides A-E (1-5), including a new cyanogenic glycoside (1), along with 10 known compounds (6-15) were isolated from the whole plants of Hedyotis scandens. The structures of compounds 1-5 were established by extensive spectroscopic analyses and acid hydrolysis. All the isolated compounds were evaluated for their in vitro antiviral activity against respiratory syncytial virus (RSV) with cytopathic effect (CPE) reduction assay. Compounds 6 and 15 showed anti-RSV effects with IC(50) values of 20 and 25 μg/mL, respectively. PMID:23333151

  10. A new diterpene glycoside from Stevia rebaudiana.

    PubMed

    Chaturvedula, Venkata Sai Prakash; Prakash, Indra

    2011-01-01

    From the commercial extract of the leaves of Stevia rebaudiana, a new diterpene glycoside was isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compound was identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl) ester (1) on the basis of extensive spectroscopic (NMR and MS) and chemical studies. PMID:21464800

  11. A New Flavonoid Glycoside from Lysionotus pauciflorus.

    PubMed

    Luo, Wei; Wen, Yaya; Tu, Yanbei; Du, Hongjian; Li, Qin; Zhu, Chao; Li, Yanfang

    2016-05-01

    Ten flavonoids (1-10), including a new glycoside (nevadensin-7-sambubioside, 7), together with a phenylpropanoid glycoside (11) were isolated from Lysionotus pauciflorus. Their structures were elucidated by a combination of spectroscopic methods and comparing with literature data. Five compounds (1, 3, 4, 8, and 9) were obtained from the family Gesneriaceae for the first time. The new compound was evaluated in vitro for anticholinesterase activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), but was found to be inactive. PMID:27319133

  12. 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

  13. Tannin signatures of barks, needles, leaves, cones, and wood at the molecular level

    NASA Astrophysics Data System (ADS)

    Hernes, Peter J.; Hedges, John I.

    2004-03-01

    We analyzed 117 tissues from 77 different plant species for molecular tannin. Tannin was measured in 89 tissues (as high as 10.5 wt.% total tannin), including procyanidin (PC) tannin in 88 tissues, prodelphinidin (PD) tannin in 50, and propelargonidin (PP) tannin in 24. In addition to tannin, several flavones, flavanones, and triterpenoids were measured, the latter which yielded as much as 4.5 wt.%. Compositions varied considerably between species, including several that yielded comparatively rare tannin or triterpenoids. Conifer needles were distinguished by high yields of PD tannin overall and relative to PC tannin. Dicotyledon leaves were characterized by the presence of flavones and triterpenoids. Barks were marked by flavanones and tetracosanoic acid. Based on these trends, relationships that could be useful as geochemical parameters were developed for distinguishing needles, leaves, and barks as possible components of litter, soil, or sedimentary mixtures.

  14. Increasing the Oxidative Stress Response Allows Escherichia coli To Overcome Inhibitory Effects of Condensed Tannins

    PubMed Central

    Smith, Alexandra H.; Imlay, James A.; Mackie, Roderick I.

    2003-01-01

    Tannins are plant-derived polyphenols with antimicrobial effects. The mechanism of tannin toxicity towards Escherichia coli was determined by using an extract from Acacia mearnsii (Black wattle) as a source of condensed tannins (proanthocyanidins). E. coli growth was inhibited by tannins only when tannins were exposed to oxygen. Tannins auto-oxidize, and substantial hydrogen peroxide was generated when they were added to aerobic media. The addition of exogenous catalase permitted growth in tannin medium. E. coli mutants that lacked HPI, the major catalase, were especially sensitive to tannins, while oxyR mutants that constitutively overexpress antioxidant enzymes were resistant. A tannin-resistant mutant was isolated in which a promoter-region point mutation increased the level of HPI by 10-fold. Our results indicate that wattle condensed tannins are toxic to E. coli in aerobic medium primarily because they generate H2O2. The oxidative stress response helps E. coli strains to overcome their inhibitory effect. PMID:12788743

  15. Elemanolide sesquiterpenes and eudesmane sesquiterpene glycosides from Centaurea hierapolitana.

    PubMed

    Karamenderes, Canan; Bedir, Erdal; Pawar, Rahul; Baykan, Sura; Khan, Ikhlas A

    2007-03-01

    Two elemanolide sesquiterpenes and two eudesmane-type sesquiterpene glycosides named hierapolitanins A-D, were isolated, together with five known compounds, two flavones; hispidulin and jaceosidin, a flavon-C-glycoside, shaftoside, a flavonol glycoside, kaempferol-3-O-rutinoside and a neolignan, dehydrodiconiferyl alcohol from the aerial parts of Centaurea hierapolitana Boiss. (Asteraceae). Structure elucidations were based on spectroscopic evidence. PMID:17126864

  16. Extraction of condensed tannins from Mexican plant sources.

    PubMed

    Garcíaa, Ramiro; Aguilera, Antonio; Contreras-Esquivel, Juan C; Rodríguez, Raúl; Aguilar, Cristóbal N

    2008-01-01

    Contents of total polyphenols, condensed tannins and proanthocyanidins, and their stability to various pH values and temperatures were studied in Mexican blueberry, cuautecomate fruit, garambullo fruit, aubergine, coffee pulp and residues of black grapes. Several aqueous extracts, obtained through a one-pass-extraction process, were analyzed using liquid chromatography in order to quantify the condensed tannin (proanthocyanidin) content responsible for their antioxidant activity and colour. All tested samples included high proanthocyanidin contents demonstrating that these Mexican fruits and vegetables are good sources of natural antioxidants, and they all could be considered as excellent functional foods due to their bioactivity measured as the condensed tannin level. PMID:18386482

  17. 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. PMID:23744121

  18. Two new secoiridoid glycosides from Verbena officinalis.

    PubMed

    Xu, Wei; Xin, Fei; Sha, Yi; Fang, Jin; Li, Yu-Shan

    2010-08-01

    Two new secoiridoid glycosides, verbenoside A (1) and verbenoside B (2), have been isolated from the ethanol extract of the aerial parts of Verbena officinalis L. Their structures were elucidated on the basis of spectroscopic evidences, especially 1D, 2D NMR, and MS experiments. PMID:20706899

  19. Twisting of glycosidic bonds by hydrolases

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Patterns of scissile bond twisting have been found in crystal structures of glycoside hydrolases (GHs) that are complexed with substrates and inhibitors. To estimate the increased potential energy in the substrates that results from this twisting, we have plotted torsion angles for the scissile bond...

  20. New triterpene glycosides from Ziziphi Spinosae Semen.

    PubMed

    Wang, Yu; Ding, Bo; Luo, Dan; Chen, Liu-Yuan; Hou, Yun-Long; Dai, Yi; Yao, Xin-Sheng

    2013-10-01

    Four new dammarane-type triterpene glycosides, named jujubosides I-IV (1-4), were isolated from Ziziphi Spinosae Semen, along with seven known saponins (5-11). The structures of new compounds were established on the basis of extensive spectroscopic analysis. All compounds were evaluated for the effects on neonatal rat cardiomyocyte injury induced by hydrogen peroxide in vitro. PMID:23912064

  1. A new isoflavone glycoside from Pueraria alopecuroides.

    PubMed

    Yang, Junlin; Fan, Qingfei; Zhang, Huanli; Song, Qishi

    2016-01-01

    A new isoflavone glycoside, (-)-tuberosin-3-O-β-D-glucopyranoside (1), along with 10 known compounds 1a-10, was isolated from Pueraria alopecuroides. Their structures were determined on the basis of spectral data including 1D and 2D NMR and HREIMS. These compounds were isolated from this plant for the first time. PMID:26525177

  2. New xanthone glycosides from Securidaca inappendiculata.

    PubMed

    Yang, Xue-Dong; An, Ning; Xu, Li-Zhen; Yang, Shi-Lin

    2002-06-01

    Three new xanthone glycosides, securixanside A (1), securixanside B (2), and securixanside C (3) were isolated from the stems of Securidaca inappendiculata. These compounds were characterized by spectrometric and chemical methods, including FABMS and one- and two-dimensional NMR experiments. PMID:12067160

  3. A new sterol glycoside from Securidaca inappendiculata.

    PubMed

    Zhang, Li-Jie; Yang, Xue-Dong; Xu, Li-Zhen; Zou, Zhong-Mei; Yang, Shi-Lin

    2005-08-01

    From the roots of Securidaca inappendiculata, one new sterol glycoside securisteroside (1) has been isolated, along with two known sterols, spinasterol (2) and 3-O-beta-D-glucopyranosyl-spinasterol (3). The new sterol was characterized by chemical and spectrometric methods, including EIMS, FABMS and one- and two-dimensional NMR experiments. PMID:16087640

  4. [Determination of phenylethanoid glycosides in Orobanche coerulescens].

    PubMed

    Han, Guo-qing; Li, Cai-feng; Wang, Xiao-qin; Li, Min-hui; Li, Jing

    2015-11-01

    Orobanche caerulescens is an important medicinal resource in Orobanchaceae. The present study aims to establish methods for determination of acteoside, crenatoside, and total phenylethanoid glycosides in O. caerulescens, and determine the content in 15 samples to evaluate the resource utilization of this medicinal plant. The content of acteoside and crenatoside were quantitatively determined by HPLC, while total phenylpropanoid glycosides was estimated by UV-VIS spectrophotometry. According to the results, the content of acteoside was the highest in O. caerulescens, followed by crenatoside. The contents of acteoside, crenatoside, and total phenylethanoid glycosides were between 1.15% - 15.60%, 0.83% - 4.47%, and 6.78% - 27.43%, respectively, which had significant differences. The acquisition time has great influence on the content of main components of O. caerulescens. The content of phenylethanoid glycosides is higher in the samples which were collected at the flowering stage. The two determination methods were proved to be simple, accurate and reliable, and can be used to evaluate the quality and resource utilization of O. caerulescens. PMID:27071260

  5. 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. PMID:10096867

  6. Anticancer Activity of Sea Cucumber Triterpene Glycosides

    PubMed Central

    Aminin, Dmitry L.; Menchinskaya, Ekaterina S.; Pisliagin, Evgeny A.; Silchenko, Alexandra S.; Avilov, Sergey A.; Kalinin, Vladimir I.

    2015-01-01

    Triterpene glycosides are characteristic secondary metabolites of sea cucumbers (Holothurioidea, Echinodermata). They have hemolytic, cytotoxic, antifungal, and other biological activities caused by membranotropic action. These natural products suppress the proliferation of various human tumor cell lines in vitro and, more importantly, intraperitoneal administration in rodents of solutions of some sea cucumber triterpene glycosides significantly reduces both tumor burden and metastasis. The anticancer molecular mechanisms include the induction of tumor cell apoptosis through the activation of intracellular caspase cell death pathways, arrest of the cell cycle at S or G2/M phases, influence on nuclear factors, NF-κB, and up-down regulation of certain cellular receptors and enzymes participating in cancerogenesis, such as EGFR (epidermal growth factor receptor), Akt (protein kinase B), ERK (extracellular signal-regulated kinases), FAK (focal adhesion kinase), MMP-9 (matrix metalloproteinase-9) and others. Administration of some glycosides leads to a reduction of cancer cell adhesion, suppression of cell migration and tube formation in those cells, suppression of angiogenesis, inhibition of cell proliferation, colony formation and tumor invasion. As a result, marked growth inhibition of tumors occurs in vitro and in vivo. Some holothurian triterpene glycosides have the potential to be used as P-gp mediated MDR reversal agents in combined therapy with standard cytostatics. PMID:25756523

  7. Enzymatic Processing of Bioactive Glycosides from Natural Sources

    NASA Astrophysics Data System (ADS)

    Weignerová, Lenka; Křen, Vladimír

    A number of biologically active natural products are glycosides. Often, the glycosidic residue is crucial for their activity. In other cases, glycosylation only improves their pharmacokinetic parameters. Enzymatic modification of these glycosides - both extension of the glycoside moiety and its selective trimming - is advantageous due to their selectivity and mildness of the reaction conditions in the presence of reactive and sensitive complex aglycones. Enzymatic reactions enable the resulting products to be used as "natural products", e.g., in nutraceuticals. This chapter concentrates on naturally occurring glycosides used in medicine but also in the food and flavor industry (e.g., sweeteners). Both "classical" and modern methods will be discussed.

  8. 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. PMID:20471759

  9. Sealing and anti-corrosive action of tannin rust converters

    SciTech Connect

    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.

  10. 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. PMID:26037239

  11. 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. PMID:26462718

  12. Anaerobic treatment of natural tannin extracts in UASB reactors.

    PubMed

    López-Fluza, J; Omil, F; Méndez, R

    2003-01-01

    Tannin extracts are substances commonly used in leather production processes. Since most of the steps of tannery manufacturing processes are carried out in aqueous environments, the presence of these compounds in the wastewaters is important. The aim of this work is to study the feasibility of the anaerobic degradation of three natural tannin extracts in three Upflow Anaerobic Sludge Blanket (UASB) reactors, which were fed with increasing concentrations of two condensed (quebracho and wattle) and one hydrolysable tannin extract (chestnut). Concentrations of applied extracts were 100, 200, 400, 800 and 1,000 mg/l, and 5 g/l of glucose was used as cosubstrate. Reactors were operated during 210 days and their performance was evaluated from the values of total and soluble COD, total and intermediate alkalinity, volatile fatty acids, pH and UV absorption at 280 nm. COD removal efficiencies higher than 85% were achieved in all cases. However, tannin extract removal efficiencies (based on UV-280 nm absorption measurements) were significantly lower, around 20% for condensed extracts and 60% for the hydrolysable one, when the reactors operated with the highest tannin extract concentration. The operation of the reactors was stable, commonly with alkalinity ratios below 0.30. Mass balances carried out indicate that most of the COD removal efficiencies are due to the removal of the readily biodegradable organic matter (glucose), whereas the tannin extracts are hardly anaerobically biodegradable, especially condensed extracts (wattle and quebracho). PMID:14640213

  13. 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. PMID:23675651

  14. 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

  15. Isolation and Characterization of Flavanone Glycoside 4I,5, 7-Trihydroxy Flavanone Rhamnoglucose from Garcinia kola Seed

    NASA Astrophysics Data System (ADS)

    Okwu, D. E.; Morah, F. N. I.

    The ethanolic extract of Garcinia kola, Heckel (Guttiferae), which had previously been shown to have biological activity were studied. Preliminary phytochemical screening of the plants showed the presence of flavonoids, phenolic compounds, tannins and saponins. The ethanolic extract of Garcinia kola seeds resulted in the isolation and characterization of flavanone glycoside 4I, 5, 7-trihydroxyflavonone rhamnoglucose (that is naringin-7-rharmnoglucoseside) from its spectral data. IHNMR spin system analysis and acid hydrolysis were performed to characterize the higher order rhamnoglucosyl moiety comprising glucose and rhamnose linked to carbon 7 of the flavanone ring system of the isolate. It is concluded that 4I, 5, 7-trihydroxyflavanone rhamnoglucose may be a contributor to the antioxidants, anti-inflammatory, anti-microbial, anti-tumor and anti-hepatotoxic properties exhibited by Garcinia kola seed.

  16. 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

  17. New pregnane glycosides from Gymnema sylvestre.

    PubMed

    Xu, Rui; Yang, Yu; Zhang, Yang; Ren, Fengxia; Xu, Jinlong; Yu, Nengjiang; Zhao, Yimin

    2015-01-01

    Four new pregnane glycosides 1-4 were isolated from the ethanol extract of the stem of Gymnema sylvestre and named gymsylvestrosides A-D. Hydrolysis of compound 1 under the catalysis of Aspergilus niger β-glucosidase afforded compound 5 (gymsylvestroside E). Their structures were determined by spectroscopic methods such as HRESIMS, 1D and 2D NMR, as well as HMQC-TOCSY experiment. Compounds 1-4 were screened for Saccharomyces cerevisiae α-glucosidase inhibitory activity. PMID:25685911

  18. A New Cucurbitane Glycoside from Siraitia grosvenorii.

    PubMed

    Chaturvedula, Venkata Sai Prakash; Meneni, Srinivasa Rao

    2015-09-01

    A systematic phytochemical study of the commercial extract of Luo Han Guo (Siraitia grosvenorii) resulted in the isolation of an additional minor new cucurbitane glycoside, mogroside V Al (1). The structure of the new compound was characterized on the basis of 1D (1H and 13C NMR) and 2D (COSY, HMQC, HMBC and NOESY) NMR and high resolution mass spectral (HRMS) data, as well as hydrolysis studies. PMID:26594748

  19. Alkyl and phenolic glycosides from Saussurea stella.

    PubMed

    Wang, Tian-Min; Wang, Ru-Feng; Chen, Hu-Biao; Shang, Ming-Ying; Cai, Shao-Qing

    2013-07-01

    One alkyl glycoside, saussurostelloside A (1), two phenolic glycosides, saussurostellosides B1 (2) and B2 (3), and 27 known compounds, including eleven flavonoids, seven phenolics, six lignans, one neolignan, one phenethyl glucoside and one fatty acid, were isolated from an ethanol extract of Saussurea stella (Asteraceae). Their structures were elucidated by NMR, MS, UV, and IR spectroscopic analysis. Of the known compounds, (+)-medioresinol-di-O-β-D-glucoside (7), picraquassioside C (10), and diosmetin-3'-O-β-D-glucoside (27) were isolated from the Asteraceae family for the first time, while (+)-pinoresinol-di-O-β-D-glucoside (6), di-O-methylcrenatin (11), protocatechuic acid (14), 1,5-di-O-caffeoylquinic acid (17), formononetin (28), and phenethyl glucoside (29) were isolated from the Saussurea genus for the first time. The anti-inflammatory activities of three new compounds (1-3), five lignans ((-)-arctiin (4), (+)-pinoresinol-4-O-β-D-glucoside (5), (+)-pinoresinol-di-O-β-D-glucoside (6), (+)-medioresinol-di-O-β-D-glucoside (7) and (+)-syringaresinol-4-O-β-D-glucoside (8)), one neolignan (picraquassioside C (10)), and one phenolic glycoside (di-O-methylcrenatin (11)) were evaluated by testing their inhibition of the release of β-glucuronidase from PAF-stimulated neutrophils. Only compound 5 showed moderate inhibition of the release of β-glucuronidase, with an inhibition ratio of 39.1%. PMID:23567860

  20. The Identification of Perillyl Alcohol Glycosides with Improved Antiproliferative Activity

    PubMed Central

    2015-01-01

    A facile route to perillyl alcohol (POH) differential glycosylation and the corresponding synthesis of a set of 34 POH glycosides is reported. Subsequent in vitro studies revealed a sugar dependent antiproliferative activity and the inhibition of S6 ribosomal protein phosphorylation as a putative mechanism of representative POH glycosides. The most active glycoside from this cumulative study (4′-azido-d-glucoside, PG9) represents one of the most cytotoxic POH analogues reported to date. PMID:25121720

  1. 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.

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

    SciTech Connect

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

    2014-09-03

    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.

  3. Assembly of naturally occurring glycosides, evolved tactics, and glycosylation methods.

    PubMed

    Yu, Biao; Sun, Jiansong; Yang, Xiaoyu

    2012-08-21

    Glycosylation of proteins and lipids is critical to many life processes. Secondary metabolites (or natural products), such as flavonoids, steroids, triterpenes, and antibiotics, are also frequently modified with saccharides. The resulting glycosides include diverse structures and functions, and some of them have pharmacological significance. The saccharide portions of the glycosides often have specific structural characteristics that depend on the aglycones. These molecules also form heterogeneous "glycoform" mixtures where molecules have similar glycosidic linkages but the saccharides vary in the length and type of monosaccharide unit. Thus, it is difficult to purify homogeneous glycosides in appreciable amounts from natural sources. Chemical synthesis provides a feasible access to the homogeneous glycosides and their congeners. Synthesis of a glycoside involves the synthesis of the aglycone, the saccharide, the connection of these two parts, and the overall manipulation of protecting groups. However, most synthetic efforts to date have focused on the aglycones, treating the attachment of saccharides onto the aglycones as a dispensable topic. The synthesis of the aglycone and the synthesis of the saccharide belong to two independent categories of chemistry, and different types of the aglycones and saccharides pose as specific synthetic subjects in their own disciplines. The only reaction that integrates the broad chemistry of glycoside synthesis is the glycosidic bond formation between the saccharide and the aglycone. Focusing on this glycosylation reaction in this Account, we string together our experience with the synthesis of the naturally occurring glycosides. We briefly describe the synthesis of 18 glycosides, including glycolipids, phenolic glycosides, steroid glycosides, and triterpene glycosides. Each molecule represents a prototypical structure of a family of the natural glycosides with interesting biological activities, and we emphasize the general

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

    NASA Astrophysics Data System (ADS)

    Hernes, Peter J.; Benner, Ronald; Cowie, Gregory L.; Goñi, Miguel A.; Bergamaschi, Brian A.; Hedges, John I.

    2001-09-01

    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 (<1 week in the water). Total tannin exhibits an intermediate lability in these leaves relative to other measured biochemicals. Leaching is an important mechanism in tannin removal from leaves as indicated by the 30% loss of measurable tannin during a leaching experiment. Condensed tannin was >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.

  5. Preference for polyethylene glycol by sheep fed a quebracho tannin diet.

    PubMed

    Villalba, J J; Provenza, F D

    2001-08-01

    Tannins decrease food intake by reducing digestion and by causing illness, whereas polyethylene glycol (PEG) attenuates the aversive effects of tannins. Our objective was to determine whether sheep recognize the benefits of ingesting substances such as PEG when consuming tannins. If so, then ingestion of PEG should be 1) PEG-specific, 2) a function of previous experience with recovery from tannin-toxicosis, and 3) dependent on the presence/absence of tannins. During conditioning, lambs in Group 1 (n = 10) were offered a meal of high-tannin food, which presumably caused malaise, and then offered PEG (molecular weight, 3,350), which presumably led to recovery from malaise. Subsequently, lambs ingested a control food (wheat straw) that did not have the "medicinal" effects of PEG in the absence of the tannin diet. In contrast, lambs in Group 2 (n = 10) ingested PEG in the absence of the tannin diet, and they ingested the tannin diet only in association with wheat straw. Ingestion of PEG and straw by both groups of lambs increased as a function of the presence of tannins in the diet (P < 0.05). However, when offered a choice among the tannin diet, PEG and straw, or when given the tannin diet and then offered a choice between PEG and straw, lambs trained to associate PEG with tannins ate more PEG than lambs that ingested PEG without tannins (P < 0.05). The responses were apparently PEG-specific; straw intake did not differ between groups of lambs during testing (P > 0.05), and differences in PEG intake disappeared in the absence of tannins (P > 0.05). In summary, our results suggest that lambs fed high-tannin diets discriminated the effects of PEG from those provided by a "nonmedicinal" food (straw). Thus, it may be possible to formulate PEG supplements that allow herbivores to self-regulate intake of PEG under extensive management conditions. PMID:11518214

  6. Bactericidal effect of hydrolysable and condensed tannin extracts on Campylobacter jejuni in vitro.

    PubMed

    Anderson, Robin C; Vodovnik, Maša; Min, Byeng R; Pinchak, William E; Krueger, Nathan A; Harvey, Roger B; Nisbet, David J

    2012-07-01

    Strategies are sought to reduce intestinal colonisation of food-producing animals by Campylobacter jejuni, a leading bacterial cause of human foodborne illness worldwide. Presently, we tested the antimicrobial activity of hydrolysable-rich blackberry, cranberry and chestnut tannin extracts and condensed tannin-rich mimosa, quebracho and sorghum tannins (each at 100 mg/mL) against C. jejuni via disc diffusion assay in the presence of supplemental casamino acids. We found that when compared to non-tannin-treated controls, all tested tannins inhibited the growth of C. jejuni and that inhibition by the condensed tannin-rich mimosa and quebracho extracts was mitigated in nutrient-limited medium supplemented with casamino acids. When tested in broth culture, both chestnut and mimosa extracts inhibited growth of C. jejuni and this inhibition was much greater in nutrient-limited than in full-strength medium. Consistent with observations from the disc diffusion assay, the inhibitory activity of the condensed tannin-rich mimosa extracts but not the hydrolysable tannin-rich chestnut extracts was mitigated by casamino acid supplementation to the nutrient-limited medium, likely because the added amino acids saturated the binding potential of the condensed tannins. These results demonstrate the antimicrobial activity of various hydrolysable and condensed tannin-rich extracts against C. jejuni and reveal that condensed tannins may be less efficient than hydrolysable tannins in controlling C. jejuni in gut environments containing high concentrations of amino acids and soluble proteins. PMID:22528299

  7. Phenylethanoid glycosides and phenolic glycosides from stem bark of Magnolia officinalis.

    PubMed

    Xue, Zhenzhen; Yan, Renyi; Yang, Bin

    2016-07-01

    An investigation of the hydrophilic constituents of the stem bark of Magnolia officinalis was performed and which led to isolation and identification of twenty-one previously unreported glycosides. These included eleven phenylethanoid glycosides, magnolosides F-P, and ten phenolic glycosides, magnolosides Q-Z, along with eight known compounds. Their structures were elucidated on the basis of extensive spectroscopic analyses and chemical hydrolysis methods, as well as by comparison with literature data. Most of the phenylethanoid glycosides contained an allopyranose moiety, which is rare in the plant kingdom. Magnolosides I and K as well as 2-(3,4-dihydroxyphenyl) ethanol 1-O-[4-O-caffeoyl-2-O-α-l-rhamnopyranosyl-3-O-α-l-rhamnopyranosyl-6-O-β-d-glucopyranosyl]-β-d-glucopyranoside showed more potent α-glucosidase inhibitory effects (IC50 values of 0.13, 0.27, and 0.29mM, respectively) than the positive control, acarbose (IC50 value of 1.09mM) in vitro. Magnolosides H, E and D also showed moderate cytotoxicity against MGC-803 and HepG2 cells with IC50 values of 13.59-17.16μM and 29.53-32.46μM, respectively. PMID:27086163

  8. Glycosidic constituents from in vitro Anoectochilus formosanus.

    PubMed

    Du, X M; Sun, N Y; Irino, N; Shoyama, Y

    2000-11-01

    The glycosidic constituents of whole plants of Anoectochilus formosanus propagated by tissue culture were investigated. A new compound, 2-(beta-D-glucopyranosyloxymethyl)-5-hydroxymethylfuran, along with the known compounds, 3-(R)-3-beta-D-glucopyranosyloxybutanolide (kinsenoside), 3-(R)-3-beta-D-glucopyranosyloxy-4-hydroxybutanoic acid, 1-O-isopropyl-beta-D-glucopyranoside, (R)-(+)-3,4-dihydroxy-butanoic acid y-lactone, 4-(beta-D-glucopyranosyloxy)benzyl alcohol, (6R,9S)-9-hydroxy-megastigma-4,7-dien-3-one-9-O-beta-glucopy ranoside, and corchoionoside C were isolated. PMID:11086921

  9. Syntheses of dopa glycosides using glucosidases.

    PubMed

    Sivakumar, Ramaiah; Ponrasu, Thangavel; Divakar, Soundar

    2009-02-01

    Syntheses of L: -dopa 1a glucoside 10a,b and DL: -dopa 1b glycosides 10-18 with D: -glucose 2, D: -galactose 3, D: -mannose 4, D: -fructose 5, D: -arabinose 6, lactose 7, D: -sorbitol 8 and D: -mannitol 9 were carried out using amyloglucosidase from Rhizopus mold, beta-glucosidase isolated from sweet almond and immobilized beta-glucosidase. Invariably, L: -dopa and DL: -dopa gave low to good yields of glycosides 10-18 at 12-49% range and only mono glycosylated products were detected through glycosylation/arylation at the third or fourth OH positions of L: -dopa 1a and DL: -dopa 1b. Amyloglucosidase showed selectivity with D: -mannose 4 to give 4-O-C1beta and D: -sorbitol 8 to give 4-O-C6-O-arylated product. beta-Glucosidase exhibited selectivity with D: -mannose 4 to give 4-O-C1beta and lactose 7 to give 4-O-C1beta product. Immobilized beta-glucosidase did not show any selectivity. Antioxidant and angiotensin converting enzyme inhibition (ACE) activities of the glycosides were evaluated glycosides, out of which L: -3-hydroxy-4-O-(beta-D: -galactopyranosyl-(1'-->4)beta-D: -glucopyranosyl) phenylalanine 16 at 0.9 +/- 0.05 mM and DL: -3-hydroxy-4-O-(beta-D: -glucopyranosyl) phenylalanine 11b,c at 0.98 +/- 0.05 mM showed the best IC(50) values for antioxidant activity and DL: -3-hydroxy-4-O-(6-D: -sorbitol)phenylalanine 17 at 0.56 +/- 0.03 mM, L: -dopa-D: -glucoside 10a,b at 1.1 +/- 0.06 mM and DL: -3-hydroxy-4-O-(D: -glucopyranosyl)phenylalanine 11a-d at 1.2 +/- 0.06 mM exhibited the best IC(50) values for ACE inhibition. PMID:18712474

  10. Additional minor diterpene glycosides from Stevia rebaudiana.

    PubMed

    Chaturvedula, Venkata Sai Prakash; Prakash, Indra

    2011-08-01

    From the commercial extract of the leaves of Stevia rebaudiana, two additional new diterpenoid glycosides were isolated and their structures were characterized as 13-[(2-O-beta-glucopyranosyl-3-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid beta-D-glucopyranosyl ester (1) and 13-[(2-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid beta-D-glucopyranosyl ester (2) on the basis of extensive spectral data (NMR and MS) and chemical studies. PMID:21922898

  11. Phenolic glycosides of forage legume Onobrychis viciifolia.

    PubMed

    Lu, Y; Sun, Y; Foo, L Y; McNabb, W C; Molan, A L

    2000-09-01

    A chemical examination of the extractives of the leaves of sainfoin was undertaken as part of a programme directed at understanding the factors which may contribute to its nutritive value as animal feed. Among the low molecular weight phenolic compounds characterized were seven cinnamic acid derivatives and nine flavonoid glycosides all of which were identified by NMR spectroscopy. Included among these compounds were two new natural hydroxycinnamic esters namely methyl 6-O-p-trans-coumaroyl-beta-D-glucopyranoside and methyl 6-O-p-cis-coumaroyl-beta-D-glucopyranoside and a novel flavonoid chrysoeriol-4'-O-(6''-O-acetyl)-beta-D-glucopyranoside. PMID:11021646

  12. Two new sesquiterpenoid glycosides from Nicotiana tabacum.

    PubMed

    Yang, Cai-Yan; Geng, Chang-An; Ma, Yun-Bao; Huang, Xiao-Yan; Zhang, Xue-Mei; Zhou, Jun; Chen, Ji-Jun

    2014-01-01

    Two new sesquiterpenoid glycosides, nicotabalactonecoside (1) and nicotabadiolcoside (2), along with four known terpenoids (3-6) were isolated from the leaves of Nicotiana tabacum. The structures of compounds 1 and 2 were determined as dihydrodeacetylphytuberin-2-one 11-O-β-D-glucopyranoside and 1,2-dehydro-4-epieremophil-9-ene-11,12-diol 12-O-β-D-glucopyranoside by extensive spectroscopic analyses (HR-ESI-MS, UV, IR, 1D, and 2D NMR) and chemical method. Compound 1 is an unusual phytuberin-type sesquiterpenoid with a 6/5/5 tricyclic system. PMID:24911395

  13. Analysis of Stevia glycosides by capillary electrophoresis.

    PubMed

    Mauri, P; Catalano, G; Gardana, C; Pietta, P

    1996-02-01

    The determination of diterpene glycosides from Stevia rebaudiana leaves using capillary electrophoresis is described. Analyses were performed on fused silica capillaries with 20 mM sodium tetraborate buffer, pH 8.3, and 30 mM sodium dodecyl sulfate. The effect of the organic solvent injected with the sample solution on the electrophoretic solution has been confirmed, and an absolute amount of 1.6 nL per injected sample was optimal. Rebaudioside A and steviolbioside were isolated by semipreparative high performance liquid chromatography (HPLC), and their structure was assessed by mass spectrometry. PMID:8900944

  14. Sesquiterpenoid tropolone glycosides from Liriosma ovata.

    PubMed

    Ma, Jun; Pawar, Rahul S; Grundel, Erich; Mazzola, Eugene P; Ridge, Clark D; Masaoka, Takashi; Le Grice, Stuart F J; Wilson, Jennifer; Beutler, John A; Krynitsky, Alexander J

    2015-02-27

    Two new sesquiterpenoid tropolone glycosides, liriosmasides A (1) and B (2), along with two known compounds, secoxyloganin and oplopanpheside C, were isolated from a methanol extract of the roots of Liriosma ovata. The structures of 1 and 2 were elucidated by spectroscopic methods including 1D and 2D NMR and by high-resolution mass spectrometry involving an ultra-high-performance liquid chromatography-quadrupole-orbital ion trap mass spectrometric (UHPLC-Q-Orbitrap MS) method. Compound 1 showed weak inhibitory activity against HIV RNase H. PMID:25587934

  15. A new phenylethanoid glycoside from Incarvillea compacta.

    PubMed

    Wu, Hai-Feng; Zhu, Yin-Di; Zhang, Li-Jing; Zou, Qiong-Yu; Chen, Li; Shen, Ting; Wang, Xin-Feng; Ma, Guo-Xu; Hu, Bo-Ran; Hu, Wei-Cheng; Xu, Xu-Dong

    2016-06-01

    A new phenylethanoid glycoside, 3'''-O-methylcampneoside I (1), was isolated from the 90% ethanolic extract of the roots of Incarvillea compacta, together with three known compounds, campneoside I (2), ilicifolioside A (3), and campneoside II (4). Their structures were determined spectroscopically and compared with previously reported spectral data. Compound 1 existed as epimers and displayed better 1,1-diphenyl-2-picrylhydrazyl (DPPH)-free radical scavenging activity using di-tert-butyl-4-methylphenol (BHT) as the positive control. In addition, pretreatment of human HepG2 cells with compound 1 significantly increased the viability on CCl4-induced cell death. PMID:26630368

  16. Monoterpenoids and their glycosides from the leaf of thyme.

    PubMed

    Kitajima, Junichi; Ishikawa, Toru; Urabe, Atushi; Satoh, Mitsuru

    2004-12-01

    From the polar portion of the methanol extract of thyme (leaf of Thymus vulgaris; Labiatae), which has been used as an important stomachic, carminative, a component of prepared cough tea, and a spice, seven monoterpenoid glycosides were isolated together with two known monoterpenoids and three known monoterpenoid glucosides. Structures of the seven monoterpenoid glycosides were determined by spectral analysis. PMID:15561194

  17. Phytosteryl glycosides reduce cholesterol absorption: mechanisms in mice

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  18. New cucurbitacin glycosides from Picrorhiza kurrooa.

    PubMed

    Stuppner, H; Wagner, H

    1989-12-01

    From the roots of Picrorhiza kurrooa Royle and Benth., seven cucurbitacin glycosides have been isolated and structurally elucidated mainly by NMR and mass spectroscopy. Four of them (4, 5, 6, 7) are new and two, the 2-O-glycoside of cucurbitacin B (25-acetoxy-2-beta-glucosyloxy-16,20-dihydroxy-9-methyl-19-norl anosta-5, 23-diene-3,11,22-trione) and the 2-O-glucoside of 23,24 didydrocucurbitacin B (25-acetoxy-2-beta-glucosyloxy-16,20-dihydroxy-9-methyl-19-norl anost-5-ene-3, 11-22-trione) were so far not reported as constituents of this plant. The four new cucurbitacins could be identified as 2-beta-glucosyloxy-3,16,20,25-tetrahydroxy-9-methyl-19-norlanos ta-5, 23-diene-22-one, 2-beta-glucosyloxy-3,16,20,25-tetrahydroxy-9-methyl-19-norlanos t-5-ene-22-one, the 2-O-glucoside of cucurbitacin Q (25-acetoxy-2-beta-glucosyloxy-3,16,20-trihydroxy-9-methyl-19-n orlanosta-5, 23-diene-11,22-dione), and the 2-O-glucoside of deacetoxycucurbitacin B (2-beta-glucosyloxy-16,20-dihydroxy-9-methyl-19-norlanosta-5 , 24-diene-3,11,22-trione). PMID:2616673

  19. Methane emission by goats consuming different sources of condensed tannins

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Twenty-four yearling Boer x Spanish wethers (7/8 Boer; initial body weight [BW] of 37.5 plus/minus 0.91 kg) were used to assess effects of different condensed tannin (CT) sources on methane emission. Diets were Kobe lespedeza (Lespedeza striata; K), K plus quebracho providing CT at 5% of dry matter...

  20. 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. PMID:21340461

  1. Effects of large mammalian herbivores and ant symbionts on condensed tannins of Acacia drepanolobium in Kenya.

    PubMed

    Ward, David; Young, Truman P

    2002-05-01

    Condensed tannins have been considered to be important inducible defenses against mammalian herbivory. We tested for differences in condensed tannin defenses in Acacia drepanolobium in Kenya over two years among different large mammalian herbivore treatments [total exclusion, antelope only, and megaherbivore (elephants and giraffes) + antelope] and with four different ant symbiont species on the trees. We predicted that (1) condensed tannin concentrations would be lowest in the mammal treatment with the lowest level of herbivory (total exclusion), (2) trees occupied by mutualist ants that protect the trees most aggressively would have lower levels of tannins, and (3) if chemical defense production is costly, there would be a trade-off between tannin concentrations, growth, and mechanical defenses. Mean tannin concentrations increased from total exclusion treatments to wildlife-only treatments to megaherbivore + antelope treatments. In 1997, condensed tannin concentrations were significantly lower in trees occupied by the ant Crematogaster nigriceps, the only ant species that actively removed axillary buds. Contrary to our prediction, trees occupied by ant species that protect the trees more aggressively against mammalian herbivores did not have lower overall levels of condensed tannins. There was no consistent evidence of a trade-off between tannin concentrations and growth rate, but there was a positive correlation between mean thorn length and mean tannin concentrations across species of ant inhabitants and across herbivore treatments in 1997. Contrary to our expectation, trees had higher tannin concentrations in the upper parts of the canopy where there is little herbivory by mammals. PMID:12049231

  2. Condensed tannin biosynthesis and polymerization synergistically condition carbon use, defense, sink strength and growth in Populus.

    PubMed

    Harding, Scott A; Xue, Liang-Jiao; Du, Lei; Nyamdari, Batbayar; Lindroth, Richard L; Sykes, Robert; Davis, Mark F; Tsai, Chung-Jui

    2014-11-01

    The partitioning of carbon for growth, storage and constitutive chemical defenses is widely framed in terms of a hypothetical sink-source differential that varies with nutrient supply. According to this framework, phenolics accrual is passive and occurs in source leaves when normal sink growth is not sustainable due to a nutrient limitation. In assessing this framework, we present gene and metabolite evidence that condensed tannin (CT) accrual is strongest in sink leaves and sequesters carbon in a way that impinges upon foliar sink strength and upon phenolic glycoside (PG) accrual in Populus. The work was based on two Populus fremontii × angustifolia backcross lines with contrasting rates of CT accrual and growth, and equally large foliar PG reserves. However, foliar PG accrual was developmentally delayed in the high-CT, slow-growth line (SG), and nitrogen-limitation led to increased foliar PG accrual only in the low-CT, fast-growth line (FG). Metabolite profiling of developing leaves indicated comparatively carbon-limited amino acid metabolism, depletion of several Krebs cycle intermediates and reduced organ sink strength in SG. Gene profiling indicated that CT synthesis decreased as leaves expanded and PGs increased. A most striking finding was that the nitrogenous monoamine phenylethylamine accumulated only in leaves of SG plants. The potential negative impact of CT hyper-accumulation on foliar sink strength, as well as a mechanism for phenylethylamine involvement in CT polymerization in Populus are discussed. Starch accrual in source leaves and CT accrual in sink leaves of SG may both contribute to the maintenance of a slow-growth phenotype suited to survival in nutrient-poor habitats. PMID:24336515

  3. Cardiac metastases

    PubMed Central

    Bussani, R; De‐Giorgio, F; Abbate, A; Silvestri, F

    2007-01-01

    Tumours metastatic to the heart (cardiac metastases) are among the least known and highly debated issues in oncology, and few systematic studies are devoted to this topic. Although primary cardiac tumours are extremely uncommon (various postmortem studies report rates between 0.001% and 0.28%), secondary tumours are not, and at least in theory, the heart can be metastasised by any malignant neoplasm able to spread to distant sites. In general, cardiac metastases are considered to be rare; however, when sought for, the incidence seems to be not as low as expected, ranging from 2.3% and 18.3%. Although no malignant tumours are known that diffuse preferentially to the heart, some do involve the heart more often than others—for example, melanoma and mediastinal primary tumours. This paper attempts to review the pathophysiology of cardiac metastatic disease, epidemiology and clinical presentation of cardiac metastases, and pathological characterisation of the lesions. PMID:17098886

  4. 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

  5. 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. PMID:9758806

  6. 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

  7. Identification of histatins as tannin-binding proteins in human saliva.

    PubMed Central

    Yan, Q; Bennick, A

    1995-01-01

    Tannins have a number of detrimental biological effects and these include interference with normal growth and metabolism if they are present in the feed of various animals. Proline-rich proteins (PRPs) in saliva have been shown to provide protection against tannin, but little is known about the mechanism of protection and interaction of other salivary proteins with tannin. To identify tannin-binding human salivary proteins, parotid and submandibular/sublingual saliva samples were adsorbed with tannin. PRPs, and in particular a group of low-M(r) proteins, were readily precipitated by tannin. The low-M(r) proteins were purified from parotid saliva and demonstrated to be histatins, a family of well-characterized histidine-rich salivary proteins. The ability of synthetic histatin 5, as well as an acidic PRP (PRP-1) and gelatin to precipitate quebracho condensed tannin and tannic acid was determined. At pH 7.4 histatin 5 was the most effective precipitant of both condensed tannin and tannic acid and it also precipitated the largest amount of condensed tannin at pH 3.0, but the smallest amount of tannic acid at that pH. In contrast PRP-1 showed a greater ability to precipitate both condensed tannin and tannic acid at pH 3.0 than at pH 7.4. Under most circumstances histatin 5 was therefore more effective in precipitating tannins than proteins with high proline content which generally have been recognized as strong precipitants of tannin. Pre-incubation of tannic acid with alpha-amylase inhibited the enzyme, but addition of histatin 5 or the acidic PRP PIF-s protected amylase from inhibition by tannin. Similarly salivary proteins may protect other biological activities in the digestive tract from inhibition by dietary tannin. Images Figure 1 Figure 2 Figure 3 PMID:7575474

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  9. Effects of tripterygium glycosides on restenosis following endovascular treatment

    PubMed Central

    HAN, BING; GE, CHANG-QING; ZHANG, HONG-GUANG; ZHOU, CHEN-GUANG; JI, GUO-HUI; YANG, ZHENG; ZHANG, LIANG

    2016-01-01

    The mechanism and associated factors of restenosis following intravascular stent implantation remain to be elucidated. The present two-part experimental and clinical study aimed to investigate the effects of tripterygium glycosides on in-stent restenosis subsequent to intra-arterial therapy. Following endovascular stent implantation in rabbit iliac arteries, post-stent outcomes were evaluated in cyclosporine groups, low-dose and high-dose tripterygium glycosides groups and controls. Post-operative angiography indicated that vessel diameters were similar between groups; however, at 28 days after receiving the therapeutic agents, vessels of the cyclosporine and tripterygium glycosides groups were significantly larger than those of the controls. Furthermore, three groups of patients had comparable baseline levels of interleukin (IL)-10, IL-18 and C-reactive protein, and intima-media thickness. However, 1 month after stent implantation, levels of IL-10 and IL-18 were markedly reduced in the high- and low-dose tripterygium glycosides groups compared with controls. At 6 months after surgery, the stent patency rate in patients with bare stents was significantly lower than in patients receiving tripterygium glycosides (P≤0.009). In addition, the ankle-brachial index was also higher than in those without tripterygium glycosides (P<0.001). Results of the experimental and clinical studies suggest that tripterygium glycosides may inhibit and possibly aid in the prevention of in-stent restenosis formation following endovascular treatment of lower-extremity artery disease. PMID:27108914

  10. Effects of tripterygium glycosides on restenosis following endovascular treatment.

    PubMed

    Han, Bing; Ge, Chang-Qing; Zhang, Hong-Guang; Zhou, Chen-Guang; Ji, Guo-Hui; Yang, Zheng; Zhang, Liang

    2016-06-01

    The mechanism and associated factors of restenosis following intravascular stent implantation remain to be elucidated. The present two‑part experimental and clinical study aimed to investigate the effects of tripterygium glycosides on in‑stent restenosis subsequent to intra‑arterial therapy. Following endovascular stent implantation in rabbit iliac arteries, post‑stent outcomes were evaluated in cyclosporine groups, low‑dose and high‑dose tripterygium glycosides groups and controls. Post‑operative angiography indicated that vessel diameters were similar between groups; however, at 28 days after receiving the therapeutic agents, vessels of the cyclosporine and tripterygium glycosides groups were significantly larger than those of the controls. Furthermore, three groups of patients had comparable baseline levels of interleukin (IL)‑10, IL‑18 and C‑reactive protein, and intima‑media thickness. However, 1 month after stent implantation, levels of IL‑10 and IL‑18 were markedly reduced in the high‑ and low‑dose tripterygium glycosides groups compared with controls. At 6 months after surgery, the stent patency rate in patients with bare stents was significantly lower than in patients receiving tripterygium glycosides (P≤0.009). In addition, the ankle‑brachial index was also higher than in those without tripterygium glycosides (P<0.001). Results of the experimental and clinical studies suggest that tripterygium glycosides may inhibit and possibly aid in the prevention of in‑stent restenosis formation following endovascular treatment of lower‑extremity artery disease. PMID:27108914

  11. [Membranotropic effect of some triterpene glycosides possessing immunostimulating properties].

    PubMed

    Lee, I A; Popov, A M; Kostetskiĭ, E Ia; Sanina, N M; Mazeĭka, A N; Boguslavskiĭ, V M

    2008-01-01

    The peculiarities of the interaction between cell membrane lipids and triterpene glycosides from holothurians Apostichopus japonicus S. and Cucumaria japonica (holotoxin A1 and cucumarioside A2-2, respectively) were studied in comparison with plant saponins from Quillaja saponaria, known as hemolytic, adjuvant, and structure-forming components of immunostimulating complexes. Similar to Quillaja saponins, the sea glycosides, holotoxin A1 and cucumarioside A2-2 were shown to possess a high hemolytic activity (2.6 and 3 microg/ml, respectively) and sterol-depending membranotropic effect mediated by the formation of nonbilayer sterol-lipid-glycoside complexes. At the same time, cucumarioside A2-2 bound exogenic cholesterol only in the presence of membrane lipids, such as phosphatidylcholine or monogalactosyldiacylglycerol, in contrast to Quillaja saponins and holotoxin A1, which bound cholesterol in the molar ratios 1:2 and 1:8, respectively. Moreover, in all cases, tree-component complexes containing cholesterol, lipid, and glycoside exhibited a lower hemolytic activity compared with two-component sterol-glycoside complexes. It was concluded that the hydrophobic medium of cell membranes performs a potentiative role in the effective interaction between triterpene glycosides and "sterol receptors". A method for decreasing the toxicity of membranotropic holothurian glycosides possessing the immunomodulating properties was suggested. PMID:18634319

  12. Steviol glycoside safety: are highly purified steviol glycoside sweeteners food allergens?

    PubMed

    Urban, Jonathan D; Carakostas, Michael C; Taylor, Steve L

    2015-01-01

    Steviol glycoside sweeteners are extracted from the plant Stevia rebaudiana (Bertoni), a member of the Asteraceae (Compositae) family. Many plants from this family can induce hypersensitivity reactions via multiple routes of exposure (e.g., ragweed, goldenrod, chrysanthemum, echinacea, chamomile, lettuce, sunflower and chicory). Based on this common taxonomy, some popular media reports and resources have issued food warnings alleging the potential for stevia allergy. To determine if such allergy warnings are warranted on stevia-based sweeteners, a comprehensive literature search was conducted to identify all available data related to allergic responses following the consumption of stevia extracts or highly purified steviol glycosides. Hypersensitivity reactions to stevia in any form are rare. The few cases documented in the peer-reviewed literature were reported prior to the introduction of high-purity products to the market in 2008 when many global regulatory authorities began to affirm the safety of steviol glycosides. Neither stevia manufacturers nor food allergy networks have reported significant numbers of any adverse events related to ingestion of stevia-based sweeteners, and there have been no reports of stevia-related allergy in the literature since 2008. Therefore, there is little substantiated scientific evidence to support warning statements to consumers about allergy to highly purified stevia extracts. PMID:25449199

  13. Determination of phenylethanoid glycosides and iridoid glycosides from therapeutically used Plantago species by CE-MEKC.

    PubMed

    Gonda, Sándor; Nguyen, Nhat Minh; Batta, Gyula; Gyémánt, Gyöngyi; Máthé, Csaba; Vasas, Gábor

    2013-09-01

    CE methods are valuable tools for medicinal plant quality management, screening, and analysis. Therefore, the aim of the current study was to optimize and validate a CE-MEKC method for simultaneous quantification of four chief bioactive metabolites from Plantago species. The two most important secondary metabolite groups were aimed to be separated. Different electrolyte and surfactant types were tested. Surfactant concentration, BGE pH, electrolyte concentration, and buffering capacity were optimized. The final BGE consisted of 15 mM sodium tetraborate, 20 mM TAPS, and 250 mM DOC at pH 8.50. Acceptable precision, good stability, and accuracy were achieved, with high resolution for phenylethanoid glycosides. Analytes were separated within 20 min. The method was shown to be suitable for the quantification of the iridoid glycosides aucubin and catalpol, and the phenylethanoid glycosides acteoside (verbascoside) and plantamajoside from water extracts of different samples. The method was shown to be applicable to leaf extracts of Plantago lanceolata, Plantago major, and Plantago asiatica, the main species with therapeutic applications, and a biotechnological product, plant tissue cultures (calli) of P. lanceolata. Baseline separation of the main constituents from minor peaks was achieved, regardless of the matrix type. PMID:23784714

  14. Cardiac Lymphoma.

    PubMed

    Jeudy, Jean; Burke, Allen P; Frazier, Aletta Ann

    2016-07-01

    Lymphoma of the heart and pericardium may develop in up to 25% of patients with disseminated nodal disease, but primary cardiac lymphoma is rare. The majority are diffuse large B-cell lymphomas, which arise in immunocompetent older individuals, men twice as often as women. Subsets are found in immunocompromised patients, including those with HIV-AIDS or allograft recipients. Cardiac lymphomas tend to arise in the wall of the right heart, especially right atrium, with contiguous infiltration of epicardium and pericardium. Pericardial implants and effusions are common. The disease is often multifocal in the heart, but cardiac valves are usually spared. PMID:27265603

  15. New steroidal glycosides from Tribulus terrestris L.

    PubMed

    Chen, Gang; Liu, Tao; Lu, Xuan; Wang, Hai-Feng; Hua, Hui-Ming; Pei, Yue-Hu

    2012-01-01

    Two new steroidal glycosides were isolated from Tribulus terrestris L. Their structures were elucidated as 26-O-β-D-glucopyranosyl-5α-furostan-12-one-20(22)-ene-3β,23,26-triol-3-O-β-D-xylopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-galactopyranoside (1) and 26-O-β-D-glucopyranosyl-5α-furostan-20(22)-ene-3β,23,26-triol-3-O-β-D-xylopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-galactopyranoside (2) by spectroscopic methods including 1D and 2D NMR experiments. PMID:22694659

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

    SciTech Connect

    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. This 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.

  17. 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. PMID:20815041

  18. Synthesis and sensory evaluation of ent-kaurane diterpene glycosides.

    PubMed

    Prakash, Indra; Campbell, Mary; San Miguel, Rafael Ignacio; Chaturvedula, Venkata Sai Prakash

    2012-01-01

    Catalytic hydrogenation of the three ent-kaurane diterpene glycosides isolated from Stevia rebaudiana, namely rubusoside, stevioside, and rebaudioside-A has been carried out using Pd(OH)₂ and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR spectral data and chemical studies. Also, we report herewith the sensory evaluation of all the reduced compounds against their corresponding original steviol glycosides and sucrose for the sweetness property of these molecules. PMID:22836210

  19. Preferences for foods varying in macronutrients and tannins by lambs supplemented with polyethylene glycol.

    PubMed

    Titus, C H; Provenza, F D; Perevolotsky, A; Silanikove, N

    2000-06-01

    Supplemental polyethylene glycol (PEG) increases intake when animals eat foods high in tannins, but little is known about how PEG affects preference for foods that vary in concentrations of macronutrients and tannin. We investigated how varying macronutrients and tannins (commercially available extracts from quebracho trees) affected food intake, and we assessed the degree to which PEG (MW 3350) affected intake of tannin-rich foods by sheep. From 0715 to 1800 daily, lambs were offered diets that varied in concentrations of macronutrients: high energy/low protein (75% barley/25% alfalfa), medium energy/medium protein (35% barley/65% alfalfa), and low energy/high protein (100% alfalfa). Preference for these diets was determined in the absence of tannin, and then, in Trials 1 to 3, tannin was added in increasing concentrations (from 5 to 20%) to the diets with high and medium levels of energy. In Trial 4, tannin (10%) also was added to the low-energy diet. Lambs were supplemented with either 50 g of PEG mixed with 50 g of ground barley or 50 g of ground barley alone from 0700 to 1715 daily; lambs always consumed all of these supplements. In the absence of added tannins, all lambs preferred high energy/low protein > medium energy/medium protein > low energy/high protein. As tannin levels increased, preference for the high- and medium-energy foods decreased, and all lambs preferred foods that were lower in tannins and higher in protein. Lambs supplemented with PEG ate more macronutrients and tannins than unsupplemented lambs, and the effect became increasingly apparent as tannin levels increased from Trials 1 to 4. We conclude that the effectiveness of supplemental PEG may be low if alternative forages are equal or superior in nutritional quality and contain fewer metabolites with adverse effects. In such cases, animals would likely prefer alternatives to high-tannin foods. PMID:10875625

  20. Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides.

    PubMed

    Dembitsky, Valery M

    2005-11-01

    This review article presents 209 alkaloid glycosides isolated and identified from plants, microorganisms, and marine invertebrates that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active glycosides have good potential for future chemical preparation of compounds useful as antioxidants, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been subdivided into several groups, including: acridone; aporphine; benzoxazinoid; ergot; indole; enediyne alkaloidal antibiotics; glycosidic lupine alkaloids; piperidine, pyridine, pyrrolidine, and pyrrolizidine alkaloid glycosides; glycosidic quinoline and isoquinoline alkaloids; steroidal glycoalkaloids; and miscellaneous alkaloid glycosides. PMID:16459921

  1. Cardiac arrest

    MedlinePlus

    ... treatment for cardiac arrest. It is a medical device that gives an electrical shock to the heart. The shock can get the heart beating normally again. Small, portable defibrillators are often available in public areas for ...

  2. Cardiac amyloidosis

    MedlinePlus

    ... the way electrical signals move through the heart (conduction system). This can lead to abnormal heart beats ( ... due to medication) Sick sinus syndrome Symptomatic cardiac conduction system disease (arrhythmias related to abnormal conduction of ...

  3. Cardiac rehabilitation

    MedlinePlus

    ... 123-210. Thomas PD. Exercise-Based, Comprehensive Cardiac Rehabilitation. In: Bonow RO, Mann DL, Zipes DP, Libby P, eds. Braunwald's Heart Disease: A Textbook of Cardiovascular Medicine . 9th ed. Philadelphia, PA: Saunders Elsevier; 2011: ...

  4. Cardiac rehabilitation

    MedlinePlus

    ... goal of cardiac rehab is to: Improve your cardiovascular function Improve your overall health and quality of ... E, eds. Braunwald's Heart Disease: A Textbook of Cardiovascular Medicine . 10th ed. Philadelphia, PA: Elsevier Saunders; 2015: ...

  5. Cardiac Sarcoidosis

    MedlinePlus

    ... is Cardiac Sarcoidosis? Sarcoidosis is a poorly understood disease that commonly affects the lungs. It can also involve the lymph nodes, liver, spleen, eyes, skin, bones, salivary glands and heart. ...

  6. 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.

  7. Scope of Hydrolysable Tannins as Possible Antimicrobial Agent.

    PubMed

    Ekambaram, Sanmuga Priya; Perumal, Senthamil Selvan; Balakrishnan, Ajay

    2016-07-01

    Hydrolysable tannins (HTs) are secondary metabolites from plants, which are roughly classified into gallotannins and ellagitannins having gallic acid and ellagic acid residues respectively attached to the hydroxyl group of glucose by ester linkage. The presence of hexahydroxydiphenoyl and nonahydroxyterphenoyl moieties is considered to render antimicrobial property to HTs. HTs also show considerable synergy with antibiotics. Nevertheless, they have low pharmacokinetic property. The present review presents the scope of HTs as future antimicrobial agent. Copyright © 2016 John Wiley & Sons, Ltd. PMID:27062587

  8. α-Glucosidase inhibitory hydrolyzable tannins from Eugenia jambolana seeds.

    PubMed

    Omar, Raed; Li, Liya; Yuan, Tao; Seeram, Navindra P

    2012-08-24

    Three new hydrolyzable tannins including two gallotannins, jamutannins A (1) and B (2), and an ellagitannin, iso-oenothein C (3), along with eight known phenolic compounds were isolated from the seeds of Eugenia jambolana fruit. The structures were elucidated on the basis of spectroscopic data analysis. All compounds isolated were evaluated for α-glucosidase inhibitory effects compared to the clinical drug acarbose. PMID:22867049

  9. 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. PMID:24799203

  10. 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. PMID:26988530

  11. 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. PMID:20559693

  12. Differentiation of tannin-containing herbal drugs by HPLC fingerprints.

    PubMed

    He, Yu; Wu, Qiaofeng; Hansen, S H; Cornett, C; Møller, C; Lai, Pingfan

    2013-03-01

    A new HPLC system coupled with multiple detectors - Diode array detector (DAD), fluorescence detector (FLD), electrochemical amperometric detector (ADC) and mass spectrometry detector (MSD) was developed for the characterization and differentiation of tannin-containing herbal drugs included in The European Pharmacopoeia. The HPLC separation system consisted of an Agilent ZORBAX Eclipse XDB C18 column and a gradient water and methanol as the mobile phase which was kept at a flow rate of 0.3 mL x min(-1). Four kinds of detectors were connected by a micro-splitter valve and simultaneously recorded the response of each analytical sample. Thirty-one samples from eight kinds of tannin-containing drugs were measured using this HPLC system and their signals from all detectors were comprehensively processed via principal component analysis (PCA). The statistic result demonstrates that thirty-one batches from different herbal drugs can be reasonably identified and systematically classified by their chemical fingerprints. The proposed multi-detector HPLC method aided by chemometrics not only offers a new pattern for the study of tannin-containing herbs, but also provides a useful foundation for quality control of herbal medicines. PMID:23556331

  13. 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. PMID:26621636

  14. 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). PMID:25918997

  15. Characterization and Physicochemical Properties of Condensed Tannins from Acacia catechu.

    PubMed

    Duval, Antoine; Avérous, Luc

    2016-03-01

    Condensed tannins from Acacia catechu were carefully studied to determine their chemical structure and physicochemical properties. The combined use of MALDI-TOF-MS and (13)C NMR revealed that catechin and epicatechin are the predominant monomers. Most of the compounds were dimers, as confirmed by size exclusion chromatography measurements. To evaluate their potential as aromatic building block in polymer synthesis, special care was given to the characterization and quantification of the different OH groups. A detailed (31)P NMR analysis showed the predominance of catechin, with a catechin/epicatechin ratio of 4.2:1. Two distinct (1)H NMR measurements confirmed the quantification. The thermal properties were also determined: the tannins showed a high temperature of degradation (ca. 190 °C) and a high glass transition temperature (ca. 140 °C), allowing for thermal processing or chemical reactions at relatively high temperature. A. catechu tannins thus present interesting features to be used as aromatic building blocks in polymer materials. PMID:26853705

  16. Three new sulphur glycosides from the seeds of Descurainia sophia.

    PubMed

    Feng, Wei-Sheng; Li, Chun-Ge; Zheng, Xiao-Ke; Li, Ling-Ling; Chen, Wen-Jing; Zhang, Yan-Li; Cao, Yan-Gang; Gong, Jian-Hong; Kuang, Hai-Xue

    2016-08-01

    Three new sulphur glycosides, raphanuside B-D (1-3), together with a known sulphur glycoside, raphanuside (4) were isolated from the decoction of the seeds of Descurainia sophia (L.) Webb ex Prantl, and the compound 4 was reported for the first time from this plant. Their structures were identified by means of UV, IR, 1D, 2D NMR (HSQC, HMBC and NOESY) and HR-ESI-MS spectroscopic data. PMID:26795632

  17. 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. PMID:18310942

  18. 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. PMID:22032697

  19. 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. PMID:24263826

  20. 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. PMID:26749816

  1. 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.

  2. 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. PMID:23020306

  3. Pyrolysis-GC/MS of charred purified condensed tannin: towards identification of tannin-derived black carbon in environmental samples

    NASA Astrophysics Data System (ADS)

    Kaal, Joeri; Nierop, Klaas G. J.; Kraal, Peter; Preston, Caroline M.

    2010-05-01

    Tannins account for a significant proportion of plant biomass and are therefore a possible source of Black C in the charred remains from wildfires. Nonetheless, in contrast with other major biocomponents such as lignin and cellulose, the thermal degradation of tannins has not been investigated in laboratory charring experiments. We used pyrolysis-GC/MS to investigate the effects of furnace charring (30 min at fixed temperatures up to 600 °C under limited oxygen supply) on the degradation of pure condensed tannin (CT) isolated from Corsican pine (Pinus nigra) needles. The experiments showed a rapid loss (at 300 °C and higher) of the pyrogallol moieties of the B-ring of prodelphinidin-type CT, due to dehydroxylation. The relative abundance of catechols (from procyanidin-type CT) decreased at 350 °C and higher temperatures. This led to the formation of phenols that were strongly enriched between 300 and 400 °C. At higher temperatures, further dehydroxylation caused a decline in contributions of phenols producing a series of monocyclic aromatics ((alkyl)benzenes) and condensation of aromatics produced polycyclic aromatic hydrocarbons (PAHs), i.e. the typical pyrolysis fingerprint of strongly charred biomass. We conclude that (i) the thermal degradation of CT can be successfully monitored by pyrolysis-GC/MS, (ii) thermal degradation of CT is characterized by dehydroxylation of phenolic groups and condensation of aromatics that increase with temperature and (iii) CT-derived Black C may be recognized by catechol enrichments at low temperatures and possibly (relative) abundance of phenol and biphenyl at higher levels of thermal breakdown. Applying the same method to natural charcoal from gorse bushfires indicated that pyrolysis-GC/MS fingerprinting may allow for tannin identification in environmental Black C samples.

  4. 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.

  5. 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. PMID:25319714

  6. Effects of tannins on digestion and detoxification activity in gray squirrels (Sciurus carolinensis).

    PubMed

    Chung-MacCoubrey, A L; Hagerman, A E; Kirkpatrick, R L

    1997-01-01

    Acorn tannins may affect food preferences and foraging strategies of squirrels through effects on acorn palatability and digestibility and squirrel physiology. Captive eastern gray squirrels (Sciurus carolinensis) were fed 100% red oak (Quercus rubra) or white oak (Quercus alba) acorn diets to determine effects on intake, digestion, and detoxification activity. Red oak acorns had higher phenol and tannin levels, which may explain the lower dry matter intakes and apparent protein digestibilities and the higher glucuronidation activities observed in squirrels. Although the white oak acorn diet had lower apparent protein digestibilities than the reference diet, it did not suppress dry matter intake for a prolonged period or stimulate glucuronidation. Negative physiological effects of a 100% red oak acorn diet suggest gray squirrels may require other foods to dilute tannin intake and provide additional nutrients. To distinguish the roles of different tannin types in the observed effects of acorn diets on squirrels, squirrels were fed rat chow containing no tannins, 4% or 8% tannic acid (hydrolyzable tannin), or 3% or 6% quebracho (condensed tannin). Apparent protein digestibilities were reduced by tannic acid and quebracho diets. Only the 8% tannic acid diet tended to increase glucuronidation. Specific effects of tannins may largely depend on tannin type, composition, and source and on other nutritional and physiological factors. PMID:9231400

  7. 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

  8. 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

  9. 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.

  10. 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. PMID:27132818

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

    PubMed

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

    2015-12-01

    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

  12. Cardiac Sarcoidosis.

    PubMed

    Birnie, David H; Nery, Pablo B; Ha, Andrew C; Beanlands, Rob S B

    2016-07-26

    Clinically manifest cardiac involvement occurs in perhaps 5% of patients with sarcoidosis. The 3 principal manifestations of cardiac sarcoidosis (CS) are conduction abnormalities, ventricular arrhythmias, and heart failure. An estimated 20% to 25% of patients with pulmonary/systemic sarcoidosis have asymptomatic cardiac involvement (clinically silent disease). In 2014, the first international guideline for the diagnosis and management of CS was published. In patients with clinically manifest CS, the extent of left ventricular dysfunction seems to be the most important predictor of prognosis. There is controversy in published reports as to the outcome of patients with clinically silent CS. Despite a paucity of data, immunosuppression therapy (primarily with corticosteroids) has been advocated for the treatment of clinically manifest CS. Device therapy, primarily with implantable cardioverter-defibrillators, is often recommended for patients with clinically manifest disease. PMID:27443438

  13. Antioxidant flavonol glycosides from Schinus molle.

    PubMed

    Marzouk, Mohamed S; Moharram, Fatma A; Haggag, Eman G; Ibrahim, Magda T; Badary, Osama A

    2006-03-01

    Chromatographic separation of aqueous MeOH extract of the leaves of Schinus molle L. has yielded two new acylated quercetin glycosides, named isoquercitrin 6''-O-p-hydroxybenzoate (12) and 2''-O-alpha-L-rhamnopyranosyl-hyperin 6''-O-gallate (13), together with 12 known polyphenolic metabolites for the first time from this species, namely gallic acid (1), methyl gallate (2), chlorogenic acid (3), 2''-alpha-L-rhamnopyranosyl-hyperin (4), quercetin 3-O-beta-D-neohesperidoside (5), miquelianin (6), quercetin 3-O-beta-D-galacturonopyranoside (7), isoquercitrin (8), hyperin (9), isoquercitrin 6''-gallate (10), hyperin 6''-O-gallate (11) and (+)-catechin (14). Their structures were established on the basis of chromatographic properties, chemical, spectroscopic (UV, 1H, 13C NMR) and ESI-MS (positive and negative modes) analyses. Compounds 4-9 and 11 exhibited moderate to strong radical scavenging properties on lipid peroxidation, hydroxyl radical and superoxide anion generations with the highest activities shown by 6 and 7 in comparison with that of quercetin as a positive control in vitro. PMID:16521111

  14. Resin Glycosides from the Morning Glory Family

    NASA Astrophysics Data System (ADS)

    Pereda-Miranda, Rogelio; Rosas-Ramírez, Daniel; Castañeda-Gómez, Jhon

    Resin glycosides are part of a very extensive family of secondary metabolites known as glycolipids or lipo-oligosaccharides and are constituents of complex resins (glycoresins) (1) unique to the morning glory family, Convolvulaceae (2). These active principles are responsible for the drastic purgative action of all the important Convolvulaceous species used in traditional medicine throughout the world since ancient times. Several commercial purgative crude drugs can be prepared from the roots of different species of Mexican morning glories. Their incorporation as therapeutic agents in Europe is an outstanding example of the assimilation of botanical drugs from the Americas as substitutes for traditional Old World remedies (3). Even though phytochemical investigations on the constituents of these drugs were initiated during the second half of the nineteenth century, the structure of their active ingredients still remains poorly known for some examples of these purgative roots. During the last two decades, the higher resolution capabilities of modern analytical isolation techniques used in conjunction with powerful spectroscopic methods have facilitated the elucidation of the active principles of these relevant herbal products.

  15. Cyanogenic glycosides: synthesis, physiology, and phenotypic plasticity.

    PubMed

    Gleadow, Roslyn M; Møller, Birger Lindberg

    2014-01-01

    Cyanogenic glycosides (CNglcs) are bioactive plant products derived from amino acids. Structurally, these specialized plant compounds are characterized as α-hydroxynitriles (cyanohydrins) that are stabilized by glucosylation. In recent years, improved tools within analytical chemistry have greatly increased the number of known CNglcs by enabling the discovery of less abundant CNglcs formed by additional hydroxylation, glycosylation, and acylation reactions. Cyanogenesis--the release of toxic hydrogen cyanide from endogenous CNglcs--is an effective defense against generalist herbivores but less effective against fungal pathogens. In the course of evolution, CNglcs have acquired additional roles to improve plant plasticity, i.e., establishment, robustness, and viability in response to environmental challenges. CNglc concentration is usually higher in young plants, when nitrogen is in ready supply, or when growth is constrained by nonoptimal growth conditions. Efforts are under way to engineer CNglcs into some crops as a pest control measure, whereas in other crops efforts are directed toward their removal to improve food safety. Given that many food crops are cyanogenic, it is important to understand the molecular mechanisms regulating cyanogenesis so that the impact of future environmental challenges can be anticipated. PMID:24579992

  16. Cardiac sarcoidosis

    PubMed Central

    Smedema, J.P.; Zondervan, P.E.; van Hagen, P.; ten Cate, F.J.; Bresser, P.; Doubell, A.F.; Pattynama, P.; Hoogsteden, H.C.; Balk, A.H.M.M.

    2002-01-01

    Sarcoidosis is a multi-system granulomatous disorder of unknown aetiology. Symptomatic cardiac involvement occurs in approximately 5% of patients. The prevalence of sarcoidosis in the Netherlands is unknown, but estimated to be approximately 20 per 100,000 population (3200 patients). We report on five patients who presented with different manifestations of cardiac sarcoidosis, and give a brief review on the current management of this condition. Magnetic Resonance Imaging (MRI) can be of great help in diagnosing this condition as well as in the follow-up of the response to therapy. ImagesFigure 1Figure 2Figure 3Figure 4Figure 5Figure 6 PMID:25696121

  17. Structures of some novel α-glucosyl diterpene glycosides from the glycosylation of steviol glycosides.

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2014-01-01

    Four new minor diterpene glycosides with a rare α-glucosyl linkage were isolated from a cyclodextrin glycosyltransferase glucosylated stevia extract containing more than 98% steviol glycosides. The new compounds were identified as 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-α-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl) ester] (1), 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-(4-O-(4-O-α-D-glucopyranosyl)-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl ester] (2), 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-α-D-glucopyranosyl)-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester (3), and 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-α-D-glucopyranosyl)-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl- β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl) ester] (4) on the basis of extensive NMR and mass spectral (MS) data as well as hydrolysis studies. PMID:25486243

  18. Preference for condensed tannins by sheep in response to challenge infection with Haemonchus contortus.

    PubMed

    Juhnke, J; Miller, J; Hall, J O; Provenza, F D; Villalba, J J

    2012-08-13

    Herbivores prefer feeds that supply required nutrients and avoid those with excess nutrients and plant secondary compounds (PSC). Nevertheless, PSC such as condensed tannins can provide beneficial medicinal effects to herbivores as they act against infective diseases such as parasitism. The objectives of this study were to determine: (1) if parasitized lambs increased preference for a tannin-rich feed after they experienced the beneficial antiparasitic effects of condensed tannins relative to parasitized lambs that did not experience such benefits, and (2) if preference for the tannin-rich feed in the former group decreased when parasite burdens subsided. Twenty two lambs were familiarized with beet pulp and beet pulp+8% quebracho tannins (beet pulp+tannins) and choices were given between the two feeds (initial preference tests). Subsequently, all animals were dosed with 10,000 L(3) stage larvae of Haemonchus contortus. Twenty-two days later, animals were exposed to beet pulp (Control group; n=11) or beet pulp+tannins (Treatment group; n=11) during 24 d. After exposure (during a parasitic infection) animals in both groups were given choices between the two feeds. Lastly, animals in both groups received an antiparasitic drench and were again given a choice between both feeds (after a parasitic infection). Lambs preferred beet pulp to beet pulp+tannins throughout the study (P<0.001) and no difference in preference for the tannin-rich feed was detected between groups during initial preference tests (P>0.05). However, during a parasitic infection, intake of and preference for the tannin-rich feed was higher for lambs that experienced the beneficial effects of condensed tannins while parasitized (Treatment) than for lambs that did not (Control) (P<0.05). When parasitic infections were terminated by chemotherapy, differences between groups disappeared (P>0.05). Preference by the Treatment group for the tannin-rich feed was lower after than during a parasite infection (P

  19. Selection of tannins by sheep in response to gastrointestinal nematode infection.

    PubMed

    Villalba, J J; Provenza, F D; Hall, J O; Lisonbee, L D

    2010-06-01

    Herbivores learn to select compounds that attenuate the aversive effects of plant secondary metabolites (PSM), but can they increase intake of PSM they typically avoid when these PSM provide medicinal effects? We hypothesized that herbivores learn to increase intake of PSM-containing feeds when experiencing a gastrointestinal parasitic infection. Ten lambs with natural gastrointestinal parasitic burdens (PB) and 10 nonparasitized lambs (NP) were offered a choice of alfalfa (Medicago sativa) and alfalfa mixed with 10% quebracho tannin (Schinopsis quebracho-colorado; alfalfa:tannins) before and after they were conditioned with the postingestive effects of tannins. Preference for alfalfa:tannins did not differ between groups before experiencing the postingestive effects of tannins (P = 0.85) or when parasite loads were terminated due to the administration of ivermectin (P = 0.18). In contrast, when tested with a parasite burden, lambs in PB consumed more alfalfa:tannins (P = 0.08), showed greater preference for alfalfa:tannins (P = 0.07), and consumed less alfalfa than lambs in NP (P = 0.06). Ingestion of tannins by lambs in PB was followed by reduced fecal egg counts (FEC; P = 0.006), and there was a direct proportional relationship between preference for alfalfa:tannins and FEC (P = 0.07). In summary, parasitized lambs increased their intake of alfalfa:tannins when they experienced a parasite burden, which suggests they self-medicated with tannins against parasites. Self-selection of PSM has implications for the quest for alternatives to chemoprophylaxis in the treatment and well-being of parasitized wild and domestic animals grazing in pasturelands and in confinement. PMID:20190171

  20. Anthelmintic effect of plant extracts containing condensed and hydrolyzable tannins on Caenorhabditis elegans and their antioxidant capacity

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  1. Pregnane steroidal glycosides and their cytostatic activities.

    PubMed

    García, Víctor P; Bermejo, Jaime; Rubio, Sara; Quintana, José; Estévez, Francisco

    2011-05-01

    Four new steroidal glycosides such as 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1 → 4)-β-D-oleandropyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside-12-β-tigloyl-14-β-hydroxy-17-β-pregnane (1), 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1 → 4)-β-D-oleandropyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside-12-β-(2'-amino)-benzoyl-14-β-hydroxy-17-β-pregnane (2), 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1 → 4)-β-D-oleandropyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside-12-β-14-β-dihydroxy-17-α-pregnane (3) and 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1 → 4)-β-D-oleandropyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside-12-β-14-β-dihydroxy-17-β-pregnane (4) were isolated from the aerial parts of Ceropegia fusca Bolle (Asclepiadaceae), a crassulacean acid metabolism plant, an endemic species to the Canary Islands that has been used in traditional medicine as a cicatrizant, vulnerary and disinfectant. The dichloromethane extract exhibited significant cytostatic activity against HL-60, A-431 and SK-MEL-1 cells, human leukemic, epidermoid carcinoma and melanoma cells, respectively. As shown in Table I, compounds 1 and 2 showed very similar IC(50) values. The acetylation of 1 to give the diacetate 5 increases 5-fold the cytotoxicity against HL-60 cells. Compounds 3 and 4 did not show cytotoxicity at the assayed concentrations. With respect to the compounds containing only the steroid ring (6-8), the presence of a charged O-amino-benzoyl but not a tigloyl group improved the cytotoxicity. PMID:21147757

  2. 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

  3. High-throughput micro plate vanillin assay for determination of tannin in sorghum grain

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Sorghum tannins are phenolic compounds that offer health promoting antioxidant properties. The conventional HCl-vanillin assay for determining tannin content is a time-consuming method for screening large sample sets as seen in association mapping panels or breeder nursery samples. The objective of ...

  4. 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. PMID:26547588

  5. 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. PMID:24425201

  6. 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.

  7. 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.

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  9. Influence of high tannin grain sorghum on gastrointestinal nematode infection in goats

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Previous studies have demonstrated that condensed tannin-rich forages such as sericea lespedeza can control gastrointestinal nematode infection (GIN) in goats. The objective of three experiments (EXP) was to determine the influence of high tannin grain sorghum on GIN in goats. Naturally infected B...

  10. TANNIN-CONTAINING ALFALFA: A WAY TO IMPROVE NITROGEN-USE AND PROFITABILITY OF DAIRY FARMS?

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Binding of condensed tannins to protein can prevent excessive proteolysis in forages during ensiling, ruminal digestion, and decay of residues in soil. Plant breeding and biotechnology efforts are underway in the U.S. and abroad to develop alfalfa and other forages with adequate levels of tannin for...

  11. EFFECTS OF TANNINS ON SOIL CARBON, CATION EXCHANGE CAPACITY, AND METAL SOLUBILITY

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins sorb to soil, affect the solubility of soil nitrogen, and soil chemical processes that may be important for the formation of soil organic matter and nutrient cycling. However, studies are needed, comparing different classes of tannins and related compounds, to determine if soils have a maxi...

  12. Characterization of tannin-metal complexes by UV-visible spectrophotometry

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  13. Sorption of tannin-C by soils affects soil cation exchange capacity

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Some tannins, produced by plants, are able to sorb to soil, and thus influence soil organic matter and nutrient cycling. However, studies are needed that compare sorption of tannins to other related phenolic compounds, evaluate their effects across a broad range of soils, and determine if sorption ...

  14. [Separation of tannins in Rhubarb and its analysis by high performance liquid chromatography-mass spectrometry].

    PubMed

    Ding, Mingyu; Ni, Weiwei

    2004-11-01

    In order to investigate the pharmaceutical actions of rhubarb, a method for extracting, separating and analyzing the tannin components in rhubarb was studied. At first, a procedure for the group separation of tannins from the water-ethanol extract of rhubarb was established based on the formation of tannins-caffein precipitation. Then, a high performance liquid chromatographic (HPLC) method for the analysis of tannins in rhubarb was developed. This HPLC method is based on a reversed-phase C18 column and polar mobile-phase such as water and methanol with gradient elution, and the tannins can be well separated. Finally, the identification of the tannin components in rhubarb was carried out by high performance liquid chromatography-mass spectrometry (HPLC-MS). The structures of the main tannin components (gallic acid, catechin, the dimer, trimer, tetramer and pentamer of catechin) in rhubarb are suggested. The fragmentation laws of the tannin components are summarized. In comparing with previous methods, it is simple and without the interference of co-existed compounds. PMID:15807111

  15. SORPTION OF TANNIN AND RELATED PHENOLIC COMPOUNDS AND EFFECTS ON SOLUBLE-N IN SOIL

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Some tannins, plant-derived polyphenolic compounds, can rapidly affix to soil and affect the solubility of labile soil-N but a more complete understanding of the nature and persistence of tannin-soil interactions is needed. Forest and pasture soils from two depths were treated for 1 h with cool (23...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ingestion of small amounts of some types of condensed tannins by ruminant livestock can provide benefits to the animals, their producers and the environment. However, practical methods are needed to make these tannin more available to livestock. Results from previous trials with crude quebracho an...

  17. 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. PMID:17468433

  18. Spectral Study of the Interaction of Myoglobin with Tannin

    NASA Astrophysics Data System (ADS)

    Grigoryan, K. R.; Sargsyan, L. S.

    2016-07-01

    The interaction of myoglobin with tannin (tannic acid) at 298.15 and 303.15 K was studied by fluorescence and absorption spectroscopy in the UV region. The physicochemical and thermodynamic binding parameters (the fluorescence quenching mechanism, the bonding constant, the number of binding sites, the type of interaction) and parameters of the formed complex were determined. It was found that binding of myoglobin with tannic acid does not lead to significant changes in the electronic state of the heme ring of myoglobin.

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

    SciTech Connect

    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 cells 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.

  20. Sesquiterpene glycosides from the roots of Codonopsis pilosula

    PubMed Central

    Jiang, Yueping; Liu, Yufeng; Guo, Qinglan; Xu, Chengbo; Zhu, Chenggen; Shi, Jiangong

    2015-01-01

    Three new sesquiterpene glycosides, named codonopsesquilosides A−C (1−3), were isolated from an aqueous extract of the dried roots of Codonopsis pilosula. Their structures including absolute configurations were determined by spectroscopic and chemical methods. These glycosides are categorized as C15 carotenoid (1), gymnomitrane (2), and eudesmane (3) types of sesquiterpenoids, respectively. Compound 1 is the first diglycoside of C15 carotenoids to be reported. Compound 2 represents the second reported example of gymnomitrane-type sesquiterpenoids from higher plants. The absolute configurations were supported by comparison of the experimental circular dichroism (CD) spectra with the calculated electronic CD (ECD) spectra of 1−3, their aglycones, and model compounds based on quantum-mechanical time-dependent density functional theory. The influences of the glycosyls on the calculated ECD spectra of the glycosidic sesquiterpenoids, as well as some nomenclature and descriptive problems with gymnomitrane-type sesquiterpenoids are discussed. PMID:26904398

  1. Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages.

    PubMed

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

    2016-01-01

    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. PMID:27580973

  2. [Hypoglycemic and hypolipidemic effects of quercetin and its glycosides].

    PubMed

    Yan, Shu-xia; Li, Xian; Sun, Chong-de; Chen, Kun-song

    2015-12-01

    Quercetin and its glycosides are important flavonols in traditional herbal drugs and plant-derived food, and they have diverse hiological activities such as antioxidant, anticarcinogenic, anti-inflammatory, hypoglycemic and hypolipidemic activities. Numerous studies have demonstrated that quercetin and its glycosides were effective in the prevention and treatment of non-infectious chronic disease such as diabetes, obesity, and hyperlipidemia. They can regulate glucose and lipid metaholism through different mechanisms. They can decrease blood glucose via protecting pancreatic/p cells or/and improving insulin sensitivity. Also, they have lipid-lowering effects, which may be the result of regulation of lipid catabolism or/and anabolism. Their distributions, as well as the hypoglycemic and hypolipidemic effects are reviewed in this paper. In addition, further bioactivities as well as their dose-activity relationship, structure-activity relationship, bioavailability, and future clinical application of quercetin and its glycosides are discussed and proposed. PMID:27141664

  3. Polyethylene glycol influences selection of foraging location by sheep consuming quebracho tannin.

    PubMed

    Villalba, J J; Provenza, F D

    2002-07-01

    Tannins are a heterogeneous group of phenolic polymers that can induce detrimental effects when consumed by herbivores. Polyethylene glycol (PEG) binds to tannins and thus attenuates their negative effects. Our objective was to determine whether sheep actively seek PEG when fed tannins and thus modify their foraging location as a function of the spatial distribution of PEG. Lambs were first trained to recognize the beneficial effects of PEG by offering a meal high in quebracho tannin (QT), which presumably caused malaise, and then PEG (MW, 3,350), which presumably led to recovery from malaise. Animals were then tested in an experimental area where they could forage at two different locations that contained in Trial 1 1) PEG and QT in adjacent food boxes (PEG+QT) or 2) QT and in Trial 2 1) PEG or 2) QT. Preference for foraging locations was tested under three conditions: 1) no preload meal, 2) a meal high in quebracho tannin 1 h before testing, and 3) a basal diet high in quebracho tannin. Lambs spent more time (P = 0.012) and ate more tannin-containing food (P = 0.022) at locations where PEG was present (PEG+QT) than where it was absent (QT; Trial 1). Lambs responded to increased tannins in their bodies (Conditions 2 and 3) by reducing intake (P = 0.0001; Trial 2) at sites containing only QT and by increasing intake (P = 0.0001, Trial 1; P = 0.001, Trial 2) and foraging time (P = 0.072, Trial 1; P = 0.0001, Trial 2) at locations where PEG was available. Thus, PEG influenced foraging location by sheep consuming quebracho tannin. Accordingly, it may be possible to formulate range blocks that enable herbivores to ingest PEG in tannin-rich habitats. Strategic distribution of PEG in those habitats may attract animals to underutilized feeding sites. PMID:12162651

  4. Nickel-catalyzed proton-deuterium exchange (HDX) procedures for glycosidic linkage analysis of complex carbohydrates

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  5. Cardiac optogenetics

    PubMed Central

    2013-01-01

    Optogenetics is an emerging technology for optical interrogation and control of biological function with high specificity and high spatiotemporal resolution. Mammalian cells and tissues can be sensitized to respond to light by a relatively simple and well-tolerated genetic modification using microbial opsins (light-gated ion channels and pumps). These can achieve fast and specific excitatory or inhibitory response, offering distinct advantages over traditional pharmacological or electrical means of perturbation. Since the first demonstrations of utility in mammalian cells (neurons) in 2005, optogenetics has spurred immense research activity and has inspired numerous applications for dissection of neural circuitry and understanding of brain function in health and disease, applications ranging from in vitro to work in behaving animals. Only recently (since 2010), the field has extended to cardiac applications with less than a dozen publications to date. In consideration of the early phase of work on cardiac optogenetics and the impact of the technique in understanding another excitable tissue, the brain, this review is largely a perspective of possibilities in the heart. It covers the basic principles of operation of light-sensitive ion channels and pumps, the available tools and ongoing efforts in optimizing them, overview of neuroscience use, as well as cardiac-specific questions of implementation and ideas for best use of this emerging technology in the heart. PMID:23457014

  6. Cardiac Surgery

    PubMed Central

    Weisse, Allen B.

    2011-01-01

    Well into the first decades of the 20th century, medical opinion held that any surgical attempts to treat heart disease were not only misguided, but unethical. Despite such reservations, innovative surgeons showed that heart wounds could be successfully repaired. Then, extracardiac procedures were performed to correct patent ductus arteriosus, coarctation of the aorta, and tetralogy of Fallot. Direct surgery on the heart was accomplished with closed commissurotomy for mitral stenosis. The introduction of the heart-lung machine and cardiopulmonary bypass enabled the surgical treatment of other congenital and acquired heart diseases. Advances in aortic surgery paralleled these successes. The development of coronary artery bypass grafting greatly aided the treatment of coronary heart disease. Cardiac transplantation, attempts to use the total artificial heart, and the application of ventricular assist devices have brought us to the present day. Although progress in the field of cardiovascular surgery appears to have slowed when compared with the halcyon times of the past, substantial challenges still face cardiac surgeons. It can only be hoped that sufficient resources and incentive can carry the triumphs of the 20th century into the 21st. This review covers past developments and future opportunities in cardiac surgery. PMID:22163121

  7. 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

  8. One new cycloartane triterpene glycoside from Beesia calthaefolia.

    PubMed

    Zhao, Jin-Yuan; Mu, Li-Hua; Dong, Xian-zhe; Hu, Yuan; Liu, Ping

    2016-01-01

    One new cycloartane triterpene glycoside (1) was isolated from the whole plant of Beesia calthaefolia. Its structure was elucidated on the basis of extensive spectroscopic data analysis. Its inhibitory effect was measured by the classical pathway of the complement system, and compared with those of known related cycloartane glycosides 2 and 3, previously isolated by us from the same plant. Compounds 1 and 2 exhibited inhibitory activity of complement system with IC50 of 395.3 and 214 μM, respectively. The results suggested that OH at C-12, C-18 and C-15 along with the polarity could affect the inhibitory activity. PMID:26305784

  9. Structural investigation of resin glycosides from Ipomoea lonchophylla.

    PubMed

    MacLeod, J K; Ward, A; Oelrichs, P B

    1997-05-01

    A fraction from Ipomoea lonchophylla, which was toxic to mice, contained an inseparable mixture of resin glycosides with differing numbers of C5 ester groups on the hexasaccharide chain. After alkaline hydrolysis of the esters, the structure of the major component (1) was elucidated using high-field NMR spectroscopy, mass spectrometry, chemical studies, and comparison with known resin glycosides. Compound 1 was identified as 3,11-dihydroxytetradecanoic acid 11-O-beta-quinovopyranosyl-(1-->2)-beta-glucopyranosyl-(1-->3)- [alpha-rhamnopyranosyl- (1-->4)]-quinovopyranosyl-(1-->2)-beta-glucopyranosyl-(1-->2)-beta -fucopyranoside. PMID:9170289

  10. Fractionation of glycoside precursors of aroma in grapes and wine.

    PubMed

    Mateo, J J; Gentilini, N; Huerta, T; Jiménez, M; Di Stefano, R

    1997-08-22

    The glycosides in mono-, di- and trihydroxylated terpene and norisoprenoid alcohols and also those in the related shikimate pathway have been isolated on C18 reversed-phase cartridges and then fractionated into classes of different polarity at increasing percentages of methanol. The benzyl alcohol glycosides are the most polar, while those of terpene monohydroxylated alcohols and geranic acid are the least polar. The terpene diols, linalool furanoid and pyranoid oxides and also norisoprenoid precursors show intermediate polarity and separate into well defined fractions according to their polarity. PMID:9299735

  11. Flavonol Glycosides from the Leaves of Allium macrostemon.

    PubMed

    Nakane, Risa; Iwashina, Tsukasa

    2015-08-01

    Twelve flavonoids were isolated from Allium macrostemon leaves. Five compounds were identified as kaempferol 3,7-di-O-glucoside (1), kaempferol 3,4'-di-O-glucoside (2), quercetin 3-O-glucoside (3), kaempferol 3-0-glucoside (4) and isorhamnetin 3-O-glucoside (5) by UV spectra, LC-MS, acid hydrolysis and HPLC comparisons with authentic standards. Other flavonoids were characterized as kaempferol glycosides (6-8, 10 and 11) and quercetin glycosides (9 and 12). Other compounds, such as steroidal saponins, have been already found from the bulbs of A. macrostemon. However, flavonoids were reported for the first time from the leaves. PMID:26434122

  12. 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.

  13. Analytical methods for monoterpene glycosides in grape and wine. II. Qualitative and quantitative determination of monoterpene glycosides in grape.

    PubMed

    Voirin, S G; Baumes, R L; Sapis, J C; Bayonove, C L

    1992-03-20

    Free and glycosidically bound terpenes of five Vitis vinifera grape cultivars (muscat of Alexandria, muscat of Frontignan, muscat of Hamburg, muscat Ottonel and Gewürztraminer) were investigated. The free and bound fractions were separated by selective retention on Amberlite XAD-2 resin. The glycosidic fractions were analysed by gas chromatography and gas chromatography-mass spectrometry using either enzymic hydrolysis and subsequent analysis of the released aglycones or trimethylsilyl (TMS) and trifluoroacetyl derivatives. The known monoterpenyl, benzyl and 2-phenylethyl beta-D-glucopyranosides, beta-rutinosides, 6-O-alpha-L-arabinofuranosyl-beta-D-glucopyranosides and 6-O-beta-D-apiofuranosyl-beta-D-glucopyranosides were determined. A number of other glycosides were detected and the structures of some of them, mainly apiosylglucosides and glucosides with aglycones in higher oxidation state than linalol, were tentatively identified using the mass spectra of their TMS and TFA derivatives and the results obtained from the analysis of their aglycones. PMID:1577909

  14. 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. PMID:26924787

  15. Tannin concentration enhances seed caching by scatter-hoarding rodents: An experiment using artificial ‘seeds’

    NASA Astrophysics Data System (ADS)

    Wang, Bo; Chen, Jin

    2008-11-01

    Tannins are very common among plant seeds but their effects on the fate of seeds, for example, via mediation of the feeding preferences of scatter-hoarding rodents, are poorly understood. In this study, we created a series of artificial 'seeds' that only differed in tannin concentration and the type of tannin, and placed them in a pine forest in the Shangri-La Alpine Botanical Garden, Yunnan Province of China. Two rodent species ( Apodemus latronum and A. chevrieri) showed significant preferences for 'seeds' with different tannin concentrations. A significantly higher proportion of seeds with low tannin concentration were consumed in situ compared with seeds with a higher tannin concentration. Meanwhile, the tannin concentration was significantly positively correlated with the proportion of seeds cached. The different types of tannin (hydrolysable tannin vs condensed tannin) did not differ significantly in their effect on the proportion of seeds eaten in situ vs seeds cached. Tannin concentrations had no significant effect on the distance that cached seeds were carried, which suggests that rodents may respond to different seed traits in deciding whether or not to cache seeds and how far they will transport seeds.

  16. 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. PMID:20103151

  17. 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

    2016-01-01

    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

  18. 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. PMID:18841900

  19. 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. PMID:18835658

  20. 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

  1. Condensed tannins in the diets of primates: a matter of methods?

    PubMed

    Rothman, Jessica M; Dusinberre, Kathy; Pell, Alice N

    2009-01-01

    To understand the ways in which condensed tannins (CT) affect primate diet selection and nutritional status, correct measurements are essential. In the majority of studies of the CT contents of primate foods, a tannin source such as "quebracho" is used to standardize CT assays, but the CT in quebracho tannin may not be similar to those in the plants of interest. We investigated how the choice of standard to calibrate CT assays affects the estimation of CT in the diets of mountain gorillas (Gorilla beringei). We purified the CT from gorilla foods and compared the actual amounts of CT in the foods with estimates produced by using the quebracho tannin. When quebracho was used, the estimates of CT contents of gorilla foods were, on average, 3.6 times the actual content of CT so that the amounts in frequently eaten gorilla foods were substantially overestimated. The overestimation for a given plant could not be predicted reliably and the ranking of plants by tannin content differed according to the standard used. Our results demonstrate that accurate measurements of CT necessitate the use of tannins purified from the plant species of interest. A reevaluation of primatology studies using interspecific comparisons of tannin content will provide new insights into primate food selection and nutritional ecology. PMID:18925644

  2. 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. PMID:16901277

  3. 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. PMID:27465726

  4. Flavonol glycosides from distilled petals of Rosa damascena Mill.

    PubMed

    Schiber, Andreas; Mihalev, Kiril; Berardini, Nicolai; Mollov, Plamen; Carle, Reinhold

    2005-01-01

    Flavonol glycosides were extracted from petals of Rosa damascena Mill. after industrial distillation for essential oil recovery and characterized by high-performance liquid chromatography-electrospray ionization mass spectrometry. Among the 22 major compounds analyzed, only kaempferol and quercetin glycosides were detected. To the best of our knowledge, the presence of quercetin 3-O-galactoside and quercetin 3-O-xyloside has so far not been reported within the genus Rosa. In addition, based on their fragmentation patterns, several acylated quercetin and kaempferol glycosides, some of them being disaccharides, were identified for the first time. The kaempferol glycosides, along with the kaempferol aglycone, accounted for 80% of the total compounds that were quantified, with kaempferol 3-O-glucoside being the predominant component. The high flavonol content of approximately 16 g/kg on a dry weight basis revealed that distilled rose petals represent a promising source of phenolic compounds which might be used as functional food ingredients, as natural antioxidants or as color enhancers. PMID:16042335

  5. Curation of characterized glycoside hydrolases of fungal origin.

    PubMed

    Murphy, Caitlin; Powlowski, Justin; Wu, Min; Butler, Greg; Tsang, Adrian

    2011-01-01

    Fungi produce a wide range of extracellular enzymes to break down plant cell walls, which are composed mainly of cellulose, lignin and hemicellulose. Among them are the glycoside hydrolases (GH), the largest and most diverse family of enzymes active on these substrates. To facilitate research and development of enzymes for the conversion of cell-wall polysaccharides into fermentable sugars, we have manually curated a comprehensive set of characterized fungal glycoside hydrolases. Characterized glycoside hydrolases were retrieved from protein and enzyme databases, as well as literature repositories. A total of 453 characterized glycoside hydrolases have been cataloged. They come from 131 different fungal species, most of which belong to the phylum Ascomycota. These enzymes represent 46 different GH activities and cover 44 of the 115 CAZy GH families. In addition to enzyme source and enzyme family, available biochemical properties such as temperature and pH optima, specific activity, kinetic parameters and substrate specificities were recorded. To simplify comparative studies, enzyme and species abbreviations have been standardized, Gene Ontology terms assigned and reference to supporting evidence provided. The annotated genes have been organized in a searchable, online database called mycoCLAP (Characterized Lignocellulose-Active Proteins of fungal origin). It is anticipated that this manually curated collection of biochemically characterized fungal proteins will be used to enhance functional annotation of novel GH genes. Database URL: http://mycoCLAP.fungalgenomics.ca/. PMID:21622642

  6. Radioimmunoassay of aescine, a mixture of triterpene glycosides.

    PubMed

    Lehtola, T; Huhtikangas, A

    1990-01-01

    A radioimmunoassay (RIA) has been developed for the determination of picogram amounts of aescine, an anti-inflammatory and anti-oedematous glycoside mixture from unpurified extracts of Aesculus hippocastanum. Practically no interference is observed for various potentially crossreacting compounds. This RIA covers the range 100 pg-50 ng, within which acceptable accuracy and precision are obtained. PMID:2332511

  7. Triterpenoid glycosides from the leaves of Meliosma henryi.

    PubMed

    Alabdul Magid, Abdulmagid; Morjani, Hamid; Harakat, Dominique; Madoulet, Claudie; Dumontet, Vincent; Lavaud, Catherine

    2015-01-01

    Seven triterpenoid glycosides, named meliosmosides A-G, were isolated from the leaves of Meliosma henryi Diels (Sabiaceae). Their structures were elucidated by different spectroscopic methods including 1D and 2D NMR experiments as well as HRESIMS analysis. Isolated compounds were evaluated for their cytotoxic activity against KB cell line. PMID:25468712

  8. [Pharmacological properties od steroid glycosides from Ruscus ponticus].

    PubMed

    Abuladze, G V; Mulkidzhanian, K G; Novikova, Zh N

    2002-01-01

    Some pharmacological properties of the sum of steroidal glycosides (ruscoponin preparation) extracted from underground parts of Ruscus ponticus were studied. The drug exhibits a pronounced antiexudative effect (related to the alpha 1-adrenergic activity) on the models of formalin edema and pouch granuloma in rats and a thermal rectum inflammation in mice. The drug exhibited no hepato-, nephro-, and gastrotoxicity. PMID:12227103

  9. Marruboside, a new phenylethanoid glycoside from Marrubium vulgare L.

    PubMed

    Sahpaz, Sevser; Hennebelle, Thierry; Bailleul, François

    2002-06-01

    A new phenylethanoid glycoside, marruboside, has been isolated from the aerial parts of Marrubium vulgare L. Its structure was established as 3,4-dihydroxy-beta-phenylethoxy-O-[beta-D-apiofuranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)]-[beta-D-apiofuranosyl-(1-->6)]-4-O-caffeoyl-beta-D-glucopyranoside, on the basis of spectroscopic evidence. PMID:12049220

  10. Curation of characterized glycoside hydrolases of Fungal origin

    PubMed Central

    Murphy, Caitlin; Powlowski, Justin; Wu, Min; Butler, Greg; Tsang, Adrian

    2011-01-01

    Fungi produce a wide range of extracellular enzymes to break down plant cell walls, which are composed mainly of cellulose, lignin and hemicellulose. Among them are the glycoside hydrolases (GH), the largest and most diverse family of enzymes active on these substrates. To facilitate research and development of enzymes for the conversion of cell-wall polysaccharides into fermentable sugars, we have manually curated a comprehensive set of characterized fungal glycoside hydrolases. Characterized glycoside hydrolases were retrieved from protein and enzyme databases, as well as literature repositories. A total of 453 characterized glycoside hydrolases have been cataloged. They come from 131 different fungal species, most of which belong to the phylum Ascomycota. These enzymes represent 46 different GH activities and cover 44 of the 115 CAZy GH families. In addition to enzyme source and enzyme family, available biochemical properties such as temperature and pH optima, specific activity, kinetic parameters and substrate specificities were recorded. To simplify comparative studies, enzyme and species abbreviations have been standardized, Gene Ontology terms assigned and reference to supporting evidence provided. The annotated genes have been organized in a searchable, online database called mycoCLAP (Characterized Lignocellulose-Active Proteins of fungal origin). It is anticipated that this manually curated collection of biochemically characterized fungal proteins will be used to enhance functional annotation of novel GH genes. Database URL: http://mycoCLAP.fungalgenomics.ca/ PMID:21622642

  11. Glycosidation of Methanol with Ribose: An Interdisciplinary Undergraduate Laboratory Experiment

    ERIC Educational Resources Information Center

    Simon, Erin; Cook, Katie; Pritchard, Meredith R.; Stripe, Wayne; Bruch, Martha; Bendinskas, Kestutis

    2010-01-01

    This exercise provides students hands-on experience with the topics of glycosidation, hemiacetal and acetal formation, proton nuclear magnetic resonance ([superscript 1]H NMR) spectroscopy, and kinetic and thermodynamic product formation. In this laboratory experiment, the methyl acetal of ribose is synthesized, and the kinetic and thermodynamic…

  12. Isoflavonoid glycosides from the roots of Baphia bancoensis.

    PubMed

    Yao-Kouassi, Philomène A; Magid, Abdulmagid Alabdul; Richard, Bernard; Martinez, Agathe; Jacquier, Marie-José; Caron, Catherine; Debar, Elisabeth Le Magrex; Gangloff, Sophie C; Coffy, Antoine A; Zèches-Hanrot, Monique

    2008-12-01

    Chemical investigation of the methanol extract of the roots of Baphia bancoensis led to the isolation and characterization of three new isoflavonoid glycosides (1-3). Their structures were determined on the basis of spectroscopic studies andchemical evidence. Antibacterial activity of isolated compounds was evaluated against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa. PMID:19007285

  13. The influence of dietary tannin supplementation on digestive performance in captive black rhinoceros (Diceros bicornis).

    PubMed

    Clauss, M; Castell, J C; Kienzle, E; Dierenfeld, E S; Flach, E J; Behlert, O; Ortmann, S; Streich, W J; Hummel, J; Hatt, J-M

    2007-12-01

    Free-ranging browsers such as the black rhinoceros (Diceros bicornis) consume a diet that contains tannins, whereas the diets offered to them in captivity consist mostly of items known to contain hardly any such secondary plant compounds. Tannins could have potentially beneficial effects, including the chelation of dietary iron (iron storage disease is a common problem in black rhinos). Here, we tested the acceptance, and the consequences on digestion variables, of a low-dose tannin supplementation in captive animals. Eight black rhinoceroses from three zoological institutions were used. Faecal output was quantified by total faecal collection. Diets fed were regular zoo diets supplemented with either tannic acid (T, hydrolysable tannin) or quebracho (Q, condensed tannins); overall tannin source intake increased at 5-15 g/kg dry matter (DM) in relation to regular zoo diets. Adaptation periods to the new diets were >2 months. Additional data were taken from one hitherto unpublished study. Data were compared to measurements in the same animals on their regular zoo diets. All animals accepted the new diets without hesitation. There was no influence of tannin supplementation on digestion coefficients of DM and its constituents, or faecal concentrations of short-chain fatty acids or lactate. Water intake did not increase during tannin supplementation. Should the inclusion of dietary tannin sources be an objective in the development of diets for captive rhinoceroses, moderate doses such as used in this study are unlikely to cause relevant depressions of digestive efficiency and will not interfere with bacterial fermentation in a relevant way. PMID:17988348

  14. Differential Expression of Two Distinct Phenylalanine Ammonia-Lyase Genes in Condensed Tannin-Accumulating and Lignifying Cells of Quaking Aspen

    PubMed Central

    Kao, Yu-Ying; Harding, Scott A.; Tsai, Chung-Jui

    2002-01-01

    Lignins, along with condensed tannins (CTs) and salicylate-derived phenolic glycosides, constitute potentially large phenylpropanoid carbon sinks in tissues of quaking aspen (Populus tremuloides Michx.). Metabolic commitment to each of these sinks varies during development and adaptation, and depends on l-phenylalanine ammonia-lyase (PAL), an enzyme catalyzing the deamination of l-phenylalanine to initiate phenylpropanoid metabolism. In Populus spp., PAL is encoded by multiple genes whose expression has been associated with lignification in primary and secondary tissues. We now report cloning two differentially expressed PAL cDNAs that exhibit distinct spatial associations with CT and lignin biosynthesis in developing shoot and root tissues of aspen. PtPAL1 was expressed in certain CT-accumulating, non-lignifying cells of stems, leaves, and roots, and the pattern of PtPAL1 expression varied coordinately with that of CT accumulation along the primary to secondary growth transition in stems. PtPAL2 was expressed in heavily lignified structural cells of shoots, but was also expressed in non-lignifying cells of root tips. Evidence of a role for Pt4CL2, encoding 4-coumarate:coenzyme A ligase, in determining CT sink strength was gained from cellular co-expression analysis with PAL1 and CTs, and from experiments in which leaf wounding increased PAL1 and 4CL2 expression as well as the relative allocation of carbon to CT with respect to phenolic glycoside, the dominant phenolic sink in aspen leaves. Leaf wounding also increased PAL2 and lignin pathway gene expression, but to a smaller extent. The absence of PAL2 in most CT-accumulating cells provides in situ support for the idea that PAL isoforms function in specific metabolic milieus. PMID:12376645

  15. Processing conditions analysis of Eucalyptus globulus plywood bonded with resol-tannin adhesives.

    PubMed

    Stefani, P M; Peña, C; Ruseckaite, R A; Piter, J C; Mondragon, I

    2008-09-01

    Phenol-formaldehyde resol containing mimosa tannin extract was employed to produce plywood panels with two plies from Eucalyptus globulus veneers. The effect of processing conditions and tannin content on the gelation time of the adhesive in the glue line was evaluated by dynamic-mechanical analysis (DMA). These results were related with shear strength and wood failure of glue line in the final panels. Hazardous petrochemical phenol could be partially substituted in resols in industrial applications by addition of mimosa tannin extracts. PMID:18024109

  16. Cardiac rehabilitation.

    PubMed

    Ehsani, A A

    1984-02-01

    Exercise training is a major, and the most important, component of cardiac rehabilitation. Besides providing psychological benefits and promoting a "sense of well being," it elicits a number of adaptations in patients with ischemic heart disease. Among the clinically important adaptations are changes in the trained skeletal muscles and autonomic nervous system, resulting not only in increased maximum exercise capacity but also a slower heart rate and, at times, a lower systolic blood pressure during submaximal exercise. The reduction in the rate pressure product decreases myocardial O2 demand at any given submaximal exercise intensity and may thus alleviate myocardial ischemia and angina in patients with coronary artery disease. These adaptive responses occur even with a relatively modest exercise intensity. Although short-term exercise training of moderate intensity has not been reported to result in improvement in left ventricular performance, recent data suggest that exercise training of higher intensity and longer duration (12 months or longer) than has conventionally been used in cardiac rehabilitation programs may favorably affect the heart. This is characterized by improvements in left ventricular function, diminished electrocardiographic criteria of myocardial ischemia and increased stroke volume during exercise. Modest weight reduction accompanies regularly performed prolonged exercise training. It is important, however, to recognize that high-intensity exercise programs are suitable for only some patients with coronary artery disease who are stable and should be used only under strict medical supervision. PMID:6400004

  17. Application of Ultrasound and Ozone for the Removal of Aqueous Tannin

    NASA Astrophysics Data System (ADS)

    Son, Younggyu; Lim, Junghyun; Cui, Mingcan; Lim, Myunghee; Kweon, Bo-Youn; Khim, Jeehyeong

    2009-07-01

    In order to investigate the enhancement of combination of ultrasound process and ozonation for the removal of aqueous tannin, tannin concentration, chemical oxygen demand (COD), and total organic carbon (TOC) were analyzed in ultrasound process, ozonation, and ultrasound/ozone process. Even though ultrasound process was not effective for the removal of aqueous in terms of tannin concentration, COD, and TOC, ultrasound process could enhance the removal efficiency significantly when it was combined with ozonation. It was also revealed that COD removal resulted in partly mineralization due to insufficient oxidation power, which was induced by ultrasound and ozone. However average oxidation state of all organics in the solution was increased cogently and as a result, biodegradability could be increased meaningfully. Therefore ultrasound/ozone process could be effective pre-treatment process to biological process for the removal of aqueous tannin.

  18. Purity assessment of condensed tannin fractions by nuclear magnetic resonance (NMR) spectroscopy

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Unambiguous investigation of condensed tannin (CT) structure-activity relationships in biological systems requires the use of highly enriched CT fractions of defined chemical purity. Purification of CTs from Sorghum bicolor, Trifolium repens, Theobroma cacao, Lespedeza cuneata, Lotus pedunculatus, a...

  19. Polyphenols, condensed tannins, and other natural products in Onobrychis viciifolia (Sainfoin).

    PubMed

    Marais, J P; Mueller-Harvey, I; Brandt, E V; Ferreira, D

    2000-08-01

    An acetone/water extract of the fodder legume Onobrychis viciifolia afforded arbutin, kaempferol, quercetin, rutin, afzelin, the branched quercetin-3-(2(G)-rhamnosylrutinoside), the amino acid L-tryptophan, the inositol (+)-pinitol, and relatively high concentrations of sucrose (ca. 35% of extractable material). Acid-catalyzed cleavage of the condensed tannins with phloroglucinol afforded catechin, epicatechin and gallocatechin as the terminal and extender units, but epigallocatechin was only present in extender units. The condensed tannins in O. viciifolia presumably consist of hetero- and homopolymers containing both procyanidin and prodelphinidin units. Comparison of data from the present study and the literature suggests that sainfoin tannins have a highly variable composition with cis:trans ratios ranging from 47:53 to 90:10 and delphinidin:cyanidin ratios from 36:64 to 93:7. The composition of terminal and extender units in sainfoin tannins seems to be cultivar specific. PMID:10956131

  20. 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

  1. Acceleration of the rate of ethanol fermentation by addition of nitrogen in high tannin grain sorghum

    SciTech Connect

    Mullins, J.T.; NeSmith, C.C.

    1987-01-01

    In this communication, the authors show that accelerated rates of ethanol production, comparable to sorghum varieties containing low levels of tannins and to corn, can occur without the removal of the tannins. The basis of the inhibition appears to be a lack of sufficient nitrogen in the mash for protein synthesis required to support an accelerated fermentative metabolism in Saccharomyces. No inhibition of the enzymes used for starch hydrolysis was found.

  2. 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

  3. 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. PMID:25625425

  4. [Biologically active food supplements as sources of flavonoids, tannins and dietary fibers].

    PubMed

    Kosheleva, O V; Berketova, L V

    2011-01-01

    The content of some biologically active substances such as bioflavonoids, tannins and dietary fiber in various type of biologically active additive was analyzed. The results are shown that the content of bioflavonoids ranger from 26.0 to 3970.0 mg%, tannins--from 1.19 to 857.0 mg%, insoluble dietary fiber--from 4.56 to 67.89% and soluble dietary fiber from 1.0 to 66.8%. PMID:22238949

  5. 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. PMID:25639718

  6. 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. PMID:27434497

  7. Effect of condensed tannin ingestion in sheep and goat parotid saliva proteome.

    PubMed

    Lamy, E; da Costa, G; Santos, R; Capela e Silva, F; Potes, J; Pereira, A; Coelho, A V; Baptista, E Sales

    2011-06-01

    Saliva appears as a defence mechanism, against potential negative effects of tannins, in some species of animals which have to deal with these plant secondary metabolites in their regular diets. This study was carried out to investigate changes in parotid saliva protein profiles of sheep (Ovis aries) and goats (Capra hircus), induced by condensed tannin ingestion. Five Merino sheep and five Serpentina goats were maintained on a quebracho tannin enriched diet for 10 days. Saliva was collected through catheters inserted on parotid ducts and salivary proteins were separated by two-dimensional gel electrophoresis. Matrix-assisted Laser desorption ionization - time of flight (MALDI-TOF) and liquid chromatography tandem mass spectrometry (LC-MS/MS) were used to identify the proteins whose expression levels changed after tannin consumption. Although no new proteins appeared, quebracho tannin consumption increased saliva total protein concentration and produced changes in the proteome of both species. While some proteins were similarly altered in both species parotid salivary protein profile, sheep and goats also presented species-specific differences in response to tannin consumption. PMID:20880287

  8. The Cardenolide Glycoside Acovenoside A Affords Protective Activity in Doxorubicin-Induced Cardiotoxicity in Mice.

    PubMed

    Ezzat, Shahira M; El Gaafary, Menna; El Sayed, Abeer M; Sabry, Omar M; Ali, Zeinab Y; Hafner, Susanne; Schmiech, Michael; Jin, Lu; Syrovets, Tatiana; Simmet, Thomas

    2016-08-01

    The current study aimed to investigate the protective effect of the cardenolide glycoside acovenoside A (AcoA) against doxorubicin-induced cardiotoxicity in mice. AcoA was isolated from the pericarps of Acokanthera oppositifolia to chemical homogeneity and characterized by means of one- and two-dimensional nuclear magnetic resonance spectroscopy. AcoA exhibited relatively low toxicity in mice (LD50 = 223.3 mg/kg bw). Repeated administration of doxorubicin induced cardiotoxicity manifested by reduced activity of myocardial membrane-bound ion pumps and elevated serum biomarkers of myocardial dysfunction, oxidative stress, and inflammation. Pretreatment of doxorubicin-exposed mice with AcoA (11.16 or 22.33 mg/kg bw, i.p.) for 2 weeks after 2 weeks of combined administration of AcoA and doxorubicin protected the animals dose dependently against doxorubicin-induced cardiotoxicity as indicated by normalization of the levels of different myocardial markers of oxidative stress (malondialdehyde, nitric oxide, total antioxidant capacity, and cardiac glutathione), serum myocardial diagnostic marker enzymes (serum cardiac troponin T, creatine kinase isoenzyme MB, aspartate aminotransferase, and lactate dehydrogenase), and inflammatory markers (c-reactive protein, tumor necrosis factor-α, and interleukin-6), as well as myocardial Na(+)/K(+)-ATPase activity. These effects were attributed to the negative impact of AcoA on transcription factors nuclear factor κB and interferon regulatory factor 3/7. Thus acovenoside A might act as a cardioprotective agent to prevent doxorubicin-induced cardiotoxicity. PMID:27247000

  9. Imaging of cardiac sarcoidosis.

    PubMed

    Erthal, Fernanda; Juneau, Daniel; Lim, Siok P; Dwivedi, Girish; Nery, Pablo B; Birnie, David; Beanlands, Rob S

    2016-09-01

    Sarcoidosis is a multisystem inflammatory disease. Cardiac involvement is described in up to 50% of the cases. The disease spectrum is wide and cardiac manifestations ranges from being asymptomatic to heart failure, arrhythmias and sudden cardiac death. The diagnosis of cardiac sarcoidosis can be challenging due to its non-specific nature and the focal involvement of the heart. In this review, we discuss the utility of a stepwise approach with multimodality cardiac imaging in the diagnosis and management of CS. PMID:27225318

  10. New flav-3-en-3-ol glycosides, kaempferiaosides C and D, and acetophenone glycosides, kaempferiaosides E and F, from the rhizomes of Kaempferia parviflora.

    PubMed

    Chaipech, Saowanee; Morikawa, Toshio; Ninomiya, Kiyofumi; Yoshikawa, Masayuki; Pongpiriyadacha, Yutana; Hayakawa, Takao; Muraoka, Osamu

    2012-07-01

    Two new flav-3-en-3-ol glycosides, kaempferiaosides C (3) and D(4), and two new acetophenone glycosides, kaempferiaosides E (5) and F (6), were isolated from the Thai natural medicine Krachai Dum, the rhizomes of Kaempferia parviflora Wall. ex Baker. Their structures were established mainly on the basis of 1D and 2D NMR spectral data. PMID:22101441

  11. Glycosides and xanthine oxidase inhibitors from Conyza bonariensis.

    PubMed

    Kong, L D; Abliz, Z; Zhou, C X; Li, L J; Cheng, C H; Tan, R X

    2001-10-01

    Fractionation of the xanthine oxidase inhibitory methanol extract of Conyza bonariensis afforded three glycosides, in addition to nine known compounds including amyrin, beta-sitostero1 daucosterol, syringic acid 3-hydroxy-5-methoxybenzoic acid, eugenol 4-O-glucopyranoside, and luteolin, apigenin and takakin 8-O-glucuronide. The structures of the glycosides were established by a combination of spectroscopic methods (IR, MS, 1H and 13C NMR, DEPT, COSY, HMQC and HMBC) as 4-hydroxypyridin-3-carboxylic acid 4-O-glucopyranoside, 8-hydroxy-6,7-dihydrolinalool 8-O-glucopyranoside and bonaroside [viz. 1,3,4,12-tetrahydroxy-2-(9-hexadecenoylamino)octadecane 1-O-glucopyranoside]. The in vitro enzyme assay showed that syringic acid and takakin 8-O-glucuronide displayed weak inhibitory activity against xanthine oxidase with IC50 values of 500+/-41 microM and 170+/-12 microM, respectively. PMID:11576616

  12. [GH10 Family of Glycoside Hydrolases: Structure and Evolutionary Connections].

    PubMed

    Naumoff, D G

    2016-01-01

    Evolutionary connections were analyzed for endo-β-xylanases, which possess the GH10 family catalytic domains. A homology search yielded thrice as many proteins as are available from the Carbohydrate-Active Enzymes (CAZy) database. Lateral gene transfer was shown to play an important role in evolution of bacterial proteins of the family, especially in the phyla Acidobacteria, Cyanobacteria, Planctomycetes, Spirochaetes, and Verrucomicrobia. In the case of Verrucomicrobia, 23 lateral transfers from organisms of other phyla were detected. Evolutionary relationships were observed between the GH10 family domains and domains with the TIM-barrel tertiary structure from several other glycosidase families. The GH39 family of glycoside hydrolases showed the closest relationship. Unclassified homologs were grouped into 12 novel families of putative glycoside hydrolases (GHL51-GHL62). PMID:27028821

  13. Malonylated flavonol glycosides from the petals of Clitoria ternatea.

    PubMed

    Kazuma, Kohei; Noda, Naonobu; Suzuki, Masahiko

    2003-01-01

    Three flavonol glycosides, kaempferol 3-O-(2"-O-alpha-rhamnosyl-6"-O-malonyl)-beta-glucoside, quercetin 3-O-(2"-O-alpha-rhamnosyl-6"-O-malonyl)-beta-glucoside, and myricetin 3-O-(2",6"-di-O-alpha-rhamnosyl)-beta-glucoside were isolated from the petals of Clitoria ternatea cv. Double Blue, together with eleven known flavonol glycosides. Their structures were identified using UV, MS, and NMR spectroscopy. They were characterized as kaempferol and quercetin 3-(2(G)- rhamnosylrutinoside)s, kaempferol, quercetin, and myricetin 3-neohesperidosides, 3-rutinosides, and 3-glucosides in the same tissue. In addition, the presence of myricetin 3-O-(2"-O-alpha-rhamnosyl-6"-O-malonyl)-beta-glucoside was inferred from LC/MS/MS data for crude petal extracts. The flavonol compounds identified in the petals of C. ternatea differed from those reported in previous studies. PMID:12482461

  14. Two minor diterpene glycosides from the leaves of Stevia rebaudiana.

    PubMed

    Chaturvedula, Venkata Sai Prakash; Rhea, Joshua; Milanowski, Dennis; Mocek, Ulla; Prakash, Indra

    2011-02-01

    Two new new diterpene glycosides, 13-[(2-O-(6-O-beta-D-glucopyranosyl)-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid beta-D-glucopyranosyl ester (1) and 13-[(2-O-beta-D-glucopyranosyl-3-O-beta-D-fructofuranosyl-beta-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid beta-D-glucopyranosyl ester (2) were isolated from the leaves of Stevia rebaudiana, along with the known steviol glycosides stevioside, rebaudiosides A-F and dulcoside A. The structures of the two new compounds were established on the basis of extensive 2D NMR (COSY, HSQC, and HMBC), MS and chemical studies. PMID:21425668

  15. Structures of the novel diterpene glycosides from Stevia rebaudiana.

    PubMed

    Chaturvedula, Venkata Sai Prakash; Prakash, Indra

    2011-06-01

    From the commercial extract of the leaves of Stevia rebaudiana, two new diterpenoid glycosides were isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside, and dulcoside A. The structures of the two new compounds were identified as 13-[(2-O-6-deoxy-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester (1), and 13-[(2-O-6-deoxy-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester (2), on the basis of extensive NMR and MS spectral data as well as chemical studies. PMID:21489412

  16. New terpenoid glycosides obtained from Rosmarinus officinalis L. aerial parts.

    PubMed

    Zhang, Yi; Adelakun, Tiwalade Adegoke; Qu, Lu; Li, Xiaoxia; Li, Jian; Han, Lifeng; Wang, Tao

    2014-12-01

    Five new terpenoid glycosides, named as officinoterpenosides A₁ (1), A₂ (2), B (3), C (4), and D (5), together with 11 known ones, (1S,4S,5S)-5-exo-hydrocamphor 5-O-β-D-glucopyranoside (6), isorosmanol (7), rosmanol (8), 7-methoxyrosmanol (9), epirosmanol (10), ursolic acid (11), micromeric acid (12), oleanolic acid (13), niga-ichigoside F₁ (14), glucosyl tormentate (15), and asteryunnanoside B (16), were obtained from the aerial parts of Rosmarinus officinalis L. Their structures were elucidated by chemical and spectroscopic methods (UV, IR, HRESI-TOF-MS, 1D and 2D NMR). Among the new ones, 1 and 2, 3 and 4 are diterpenoid and triterpenoid glycosides, respectively; and 5 is a normonoterpenoid. For the known ones, 6 was isolated from the Rosmarinus genus first, and 15, 16 were obtained from this species for the first time. PMID:25200369

  17. A new phenolic glycoside and cytotoxic constituents from Celosia argentea.

    PubMed

    Shen, Shuo; Ding, Xiao; Ouyang, Ming-An; Wu, Zu-Jian; Xie, Lian-Hui

    2010-09-01

    A new phenolic glycoside, 4-O-β-D-apifuranosyl-(1→2)-β-D-glucopyranosyl-2-hydroxy-6-methoxyacetophenone (2) and 11 known compounds were isolated from the MeOH extract of the plant Celosia argentea. The structures of the compounds were elucidated on the basis of spectroscopic analysis and chemical methods. Among the isolated compounds, stigmasterol (10) showed moderate inhibitory activities against SGC-7901 and BEL-7404 cells. PMID:20839132

  18. Vina-Carb: Improving Glycosidic Angles during Carbohydrate Docking.

    PubMed

    Nivedha, Anita K; Thieker, David F; Makeneni, Spandana; Hu, Huimin; Woods, Robert J

    2016-02-01

    Molecular docking programs are primarily designed to align rigid, drug-like fragments into the binding sites of macromolecules and frequently display poor performance when applied to flexible carbohydrate molecules. A critical source of flexibility within an oligosaccharide is the glycosidic linkages. Recently, Carbohydrate Intrinsic (CHI) energy functions were reported that attempt to quantify the glycosidic torsion angle preferences. In the present work, the CHI-energy functions have been incorporated into the AutoDock Vina (ADV) scoring function, subsequently termed Vina-Carb (VC). Two user-adjustable parameters have been introduced, namely, a CHI- energy weight term (chi_coeff) that affects the magnitude of the CHI-energy penalty and a CHI-cutoff term (chi_cutoff) that negates CHI-energy penalties below a specified value. A data set consisting of 101 protein-carbohydrate complexes and 29 apoprotein structures was used in the development and testing of VC, including antibodies, lectins, and carbohydrate binding modules. Accounting for the intramolecular energies of the glycosidic linkages in the oligosaccharides during docking led VC to produce acceptable structures within the top five ranked poses in 74% of the systems tested, compared to a success rate of 55% for ADV. An enzyme system was employed in order to illustrate the potential application of VC to proteins that may distort glycosidic linkages of carbohydrate ligands upon binding. VC represents a significant step toward accurately predicting the structures of protein-carbohydrate complexes. Furthermore, the described approach is conceptually applicable to any class of ligands that populate well-defined conformational states. PMID:26744922

  19. β-cyclodextrin assistant flavonoid glycosides enzymatic hydrolysis

    PubMed Central

    Jin, Xin; Zhang, Zhen-hai; Sun, E.; Jia, Xiao-Bin

    2013-01-01

    Background: The content of icaritin and genistein in herba is very low, preparation with relatively large quantities is an important issue for extensive pharmacological studies. Objective: This study focuses on preparing and enzymic hydrolysis of flavonoid glycosides /β-cyclodextrin inclusion complex to increase the hydrolysis rate. Materials and Methods: The physical property of newly prepared inclusion complex was tested by differential scanning calorimetry (DSC). The conditions of enzymatic hydrolysis were optimized for the bioconversion of flavonoid glycosides /β-cyclodextrin inclusion complex by mono-factor experimental design. The experiments are using the icariin and genistein as the model drugs. Results: The solubility of icariin and genistein were increased almost 17 times from 29.2 μg/ml to 513.5 μg/ml at 60°C and 28 times from 7.78 μg/ml to 221.46 μg/ml at 50°C, respectively, demonstrating that the inclusion complex could significantly increase the solubility of flavonoid glycosides. Under the optimal conditions, the reaction time of icariin and genistin decreased by 68% and 145%, when compared with that without β-CD inclusion. By using this enzymatic condition, 473 mg icaritin (with the purity of 99.34%) and 567 mg genistein(with the purity of 99.46%), which was finally determined by melt point, ESI-MS, UV, IR, 1H NMR and 13C NMR, was obtained eventually by transforming the inclusion complex(contains 1.0 g substrates). Conclusion: This study can clearly indicate a new attempt to improve the speed of enzyme-hydrolysis of poorly water-soluble flavonoid glycosides and find a more superior condition which is used to prepare icaritin and genistein. PMID:24143039

  20. Two aurone glycosides from heartwood of Pterocarpus santalinus.

    PubMed

    Kesari, Achyut Narayan; Gupta, Rajesh Kumar; Watal, Geeta

    2004-12-01

    Two new aurone glycosides, 6 hydroxy 5 methyl 3',4',5' trimethoxy aurone 4-O-alpha-L-rhamnopyranoside and 6,4' dihydroxy aurone 4-O-rutinoside have been isolated from the ethanolic extract of the wood of Pterocarpus santalinus. Their structures were determined on the basis of chemical and spectroscopic analysis (UV, IR, EIMS, (1)H and (13)C NMR). PMID:15541741

  1. A new lignan glycoside from the rhizomes of Imperata cylindrica.

    PubMed

    Lee, Dae-Young; Han, Kyung-Min; Song, Myoung-Chong; Lee, Do-Gyeong; Rho, Yeong-Deok; Baek, Nam-In

    2008-01-01

    A new lignan glycoside, 6-acetyl-1-[1,3-(4,4'-dihydroxy-3,3'-dimethoxy-beta-truxinyl)-beta-d-fructofuranosyl]-alpha-d-glucopyranoside (1), named impecyloside, was isolated from the rhizomes of Imperata cylindrica. The structure of the compound was determined by spectroscopic data including FABMS, UV, IR, 1H NMR and 13C NMR (DEPT) and 2D NMR (COSY, HSQC, HMBC). PMID:18348057

  2. Evaluation of direct phloroglucinolysis and colorimetric depolymerization assays and their applicability for determining condensed tannins in grape marc.

    PubMed

    Hixson, Josh L; Bindon, Keren A; Smith, Paul A

    2015-11-18

    To determine the optimum methods for determining condensed tannin (CT) content in grape marc, butanol-hydrochloric acid assays and phloroglucinolysis were adapted for use, applied to a range of grape marc types, and the methods compared. Porter's assay (butanol-HCl) was found to give unreliable results due to nonlinear color responses to grape skin and seed tannin concentrations, whereas the modification to include acetone (Grabber's assay) overcame this. Differences between skin and seed tannin responses highlighted the need to adequately select the correct grape tannin standard, and the formation of pH-dependent color was accounted for through acidification of blank samples. For phloroglucinolysis, the inability to remove highly bound tannins from cell wall material was highlighted, although a measure of tannins remaining post-phloroglucinolysis (Grabber's assay) showed a trend with the level of exposure to oxidative storage or processing conditions. The comparison of CT concentrations from phloroglucinolysis and Grabber's assay gave poor correlation coefficients. PMID:26551987

  3. Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives.

    PubMed

    Pandey, Ramesh Prasad; Parajuli, Prakash; Shin, Ju Yong; Lee, Jisun; Lee, Seul; Hong, Young-Soo; Park, Yong Il; Kim, Joong Su; Sohng, Jae Kyung

    2014-12-01

    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

  4. 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. PMID:25993882

  5. Minor diterpene glycosides from the leaves of Stevia rebaudiana.

    PubMed

    Ibrahim, Mohamed A; Rodenburg, Douglas L; Alves, Kamilla; Fronczek, Frank R; McChesney, James D; Wu, Chongming; Nettles, Brian J; Venkataraman, Sylesh K; Jaksch, Frank

    2014-05-23

    Two new diterpene glycosides in addition to five known glycosides have been isolated from a commercial extract of the leaves of Stevia rebaudiana. Compound 1 (rebaudioside KA) was shown to be 13-[(O-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-β-d-glucopyranosyl-β-d-glucopyranosyl ester and compound 2, 12-α-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester. Five additional known compounds were identified, rebaudioside E, rebaudioside M, rebaudioside N, rebaudioside O, and stevioside, respectively. Enzymatic hydrolysis of stevioside afforded the known ent-kaurane aglycone 13-hydroxy-ent-kaur-16-en-19-oic acid (steviol) (3). The isolated metabolite 1 possesses the ent-kaurane aglycone steviol (3), while compound 2 represents the first example of the isomeric diterpene 12-α-hydroxy-ent-kaur-16-en-19-oic acid existing as a glycoside in S. rebaudiana. The structures of the isolated metabolites 1 and 2 were determined based on comprehensive 1D- and 2D-NMR (COSY, HSQC, and HMBC) studies. A high-quality crystal of compound 3 has formed, which allowed the acquisition of X-ray diffraction data that confirmed its structure. The structural similarities between the new metabolites and the commercially available stevioside sweeteners suggest the newly isolated metabolites should be examined for their organoleptic properties. Accordingly rebaudiosides E, M, N, O, and KA have been isolated in greater than gram quantities. PMID:24758242

  6. Acylated flavonol glycosides from the forage legume, Onobrychis viciifolia (sainfoin).

    PubMed

    Veitch, Nigel C; Regos, Ionela; Kite, Geoffrey C; Treutter, Dieter

    2011-04-01

    Ten acylated flavonol glycosides were isolated from aqueous acetone extracts of the aerial parts of the forage legume, Onobrychis viciifolia, and their structures determined using spectroscopic methods. Among these were eight previously unreported examples which comprised either feruloylated or sinapoylated derivatives of 3-O-di- and 3-O-triglycosides of kaempferol (3,5,7,4'-tetrahydroxyflavone) or quercetin (3,5,7,3',4'-pentahydroxyflavone). The diglycosides were acylated at the primary Glc residue of O-α-Rhap(1→6)-β-Glcp (rutinose), whereas the triglycosides were acylated at the terminal Rha residues of the branched trisaccharides, O-α-Rhap(1→2)[α-Rhap(1→6)]-β-Galp or O-α-Rhap(1→2)[α-Rhap(1→6)]-β-Glcp. Identification of the primary 3-O-linked hexose residues as either Gal or Glc was carried out by negative ion electrospray and serial MS, and cryoprobe NMR spectroscopy. Analysis of UV and MS spectra of the acylated flavonol glycosides provided additional diagnostic features relevant to direct characterisation of these compounds in hyphenated analyses. Quantitative analysis of the acylated flavonol glycosides present in different aerial parts of sainfoin revealed that the highest concentrations were in mature leaflets. PMID:21292287

  7. Two new phenolic glycosides from the stems of Clematis parviloba.

    PubMed

    Yan, Li-hua; Xu, Li-zhen; Wang, Zhi-min; Zhang, Qi-wei; Yang, Shi-lin

    2010-12-01

    To study the chemical constituents of the stems of Clematis parviloba, six compounds were isolated from a 95% ethanol extract by using a combination of various chromatographic techniques including column chromatography over silica gel, ODS, Sephadex LH-20, and semi-preparative HPLC. Two new phenolic glycosides, 2-((E)-3-carboxybut-2-en-yl)-4-hydroxy-3-methyl-phenyl-O-beta-D-glucopyranoside (1) and 4'-hydroxy-phenol-beta-D-[6-O-(4"-hydroxy-3", 5"-dimethoxy-benzoate)] glucopyranoside (2) were isolated, together with a known phenolic glycoside, 4'-hydroxy-3'-methoxy-phenol-beta-D-[6-O-(4"-hydroxy-3", 5"-dimethoxy-benzoate)] glucopyranoside (3) as well as three known megastigmane glycosides, linarionoside A (4), linarionoside C (5), and staphylionoside K (6). Their structures were determined on the basis of spectroscopic analysis and chemical evidence. Among them, compounds 1 and 2 were named as clemaparvilosides A (1) and B (2), respectively, and compounds 3-6 were obtained from Clematis genus for the first time. PMID:21348422

  8. 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. PMID:11308344

  9. Effects of Sainfoin (Onobrychis viciifolia Scop.) Condensed Tannins on Growth and Proteolysis by Four Strains of Ruminal Bacteria.

    PubMed

    Jones, G A; McAllister, T A; Muir, A D; Cheng, K J

    1994-04-01

    Sainfoin leaf condensed tannins inhibited growth and protease activity in Butyrivibrio fibrisolvens A38 and Streptococcus bovis 45S1 but had little effect on Prevotella ruminicola B(1)4 or Ruminobacter amylophilus WP225. Tannins bound to cell coat polymers in all strains. Morphological changes in B. fibrisolvens and S. bovis implicated the cell wall as a target of tannin toxicity. PMID:16349244

  10. Application of Mössbauer spectroscopy to the study of tannins inhibition of iron and steel corrosion

    NASA Astrophysics Data System (ADS)

    Jaén, Juan A.; de Obaldía, J.; Rodríguez, M. V.

    2011-11-01

    The inhibitory effect of tannins was investigated using, among others, potentiodynamic polarizations and Mössbauer spectroscopy. These techniques confirmed that the nature, pH and concentration of tannic solution are of upmost importance in the inhibitory properties of the solutions. It is observed that at low tannin concentration or pH, both, hydrolizable and condensed tannins, effectively inhibit iron corrosion, due to the redox properties of tannins. At pH ≈ 0, Mössbauer spectra of the frozen aqueous solutions of iron(III) with the tannin solutions showed that iron is in the form of a monomeric species [Fe(H2O)6]3 + , without coordination with the functional hydroxyl groups of the tannins. The suspended material consisted of amorphous ferric oxide and oxyhydroxides, though with quebracho tannin partly resulted in complex formation and in an iron (II) species from a redox process. Other tannins, such as chestnut hydrolysable tannins, do not complex iron at this low pH. Tannins react at high concentrations or pH (3 and 5) to form insoluble blue-black amorphous complexes of mono-and bis-type tannate complexes, with a relative amount of the bis-ferric tannate generally increasing with pH. Some Fe2 + in the form of hydrated polymeric ferrous tannate could be obtained. At pH 7, a partially hydrolyzed ferric tannate complex was also formed. The latter two phases do not provide corrosion protection. Tannin solutions at natural pH react with electrodeposited iron films (approx. 6 μm) to obtain products consisting only on the catecholate mono-complex of ferric tannate. Some aspects of the mechanism of tannins protection against corrosion are discussed.

  11. 4-Trifluoromethylumbelliferyl glycosides as new substrates for revealing diseases connected with hereditary deficiency of lysosome glycosidases.

    PubMed

    Karpova, E A; Voznyi YaV; Dudukina, T V; Tsvetkova, I V

    1991-08-01

    The following glycosides of 4-trifluoromethylumbelliferone: alpha-D-mannopyranoside, alpha-L-fucopyranoside, alpha-D-glucopyranoside, beta-D-glucopyranoside, alpha-D-galactopyranoside, beta-D-galactopyranoside, alpha-L-iduronide and beta-D-glucuronide were studied. 4-Trifluoromethylumbelliferyl glycosides were shown to be substrates for glycosidases. Some of them were cleaved even better than the corresponding methylumbelliferyl glycosides. 4-Trifluoromethylumbelliferyl glycosides were applied for revealing the corresponding enzyme deficiencies upon diagnosis of Gaucher and Hurler diseases as well as GM1 gangliosidosis and alpha-mannosidosis. 4-Trifluoromethylumbelliferone released after enzymatic hydrolysis of 4-trifluoromethylumbelliferyl glycosides exhibits more contrast yellow fluorescence in UV-light than the blue one of methylumbelliferone upon exposure of enzyme activity on solid supports. Therefore 4-trifluoromethylumbelliferyl glycosides are convenient substrates for revealing glycosidase activity directly in tissue samples, e.g. in placenta, and thus for fast prenatal diagnosis of lysosomal diseases. PMID:1781792

  12. 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. PMID:21175139

  13. Cardiac perception and cardiac control. A review.

    PubMed

    Carroll, D

    1977-12-01

    The evidence regarding specific cardiac perception and discrimination, and its relationship to voluntary cardiac control, is critically reviewed. Studies are considered in three sections, depending on the method used to assess cardiac perception: questionnaire assessment, discrimination procedures, and heartbeat tracking. The heartbeat tracking procedure would appear to suffer least from interpretative difficulties. Recommendations are made regarding the style of analysis used to assess heartbeat perception in such tracking tasks. PMID:348240

  14. 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

  15. EBV DNA polymerase inhibition of tannins from Eugenia uniflora.

    PubMed

    Lee, M H; Chiou, J F; Yen, K Y; Yang, L L

    2000-06-30

    Nasopharyngeal carcinoma (NPC) is one of the high population malignant tumors among Chinese in southern China and southeast Asia. Epstein-Barr virus (EBV) is a human B lymphotropic herpes virus which is known to be closely associated with NPC. EBV DNA polymerase is a key enzyme during EBV replication and is measured by its radioactivity. The addition of phorbol 12-myristate 13-acetate to Raji cell cultures led to a large increase in EBV DNA polymerase, which was purified by sequential DEAE-cellulose, phosphocellulose and DNA-cellulose column chromatography. Four tannins were isolated from the active fractions of Eugenia uniflora L., which were tested for the inhibition of EBV DNA polymerase. The results showed the 50% inhibitory concentration (IC(50)) values of gallocatechin, oenothein B, eugeniflorins D(1) and D(2) were 26.5 62.3, 3.0 and 3.5 microM, respectively. Furthermore, when compared with the positive control (phosphonoacetic acid), an inhibitor of EBV replication, the IC(50) value was 16.4 microM. In view of the results, eugeniflorins D(1) and D(2) are the potency principles in the inhibition of EBV DNA polymerase from E. uniflora. PMID:10806300

  16. Rigidity, conformation, and solvation of native and oxidized tannin macromolecules in water-ethanol solution

    NASA Astrophysics Data System (ADS)

    Zanchi, Dražen; Konarev, Petr V.; Tribet, Christophe; Baron, Alain; Svergun, Dmitri I.; Guyot, Sylvain

    2009-06-01

    We studied by light scattering and small angle x-rays scattering (SAXS) conformations and solvation of plant tannins (oligomers and polymers) in mixed water-ethanol solutions. Their structures are not simple linear chains but contain about 6% of branching. Ab initio reconstruction reveals that monomers within a branch are closely bound pairwise. The chains are rather rigid, with the Kuhn length b =13±3 nm, corresponding to about 35 linearly bound monomers. Contribution of solvation layer to SAXS intensity varies in a nonmonotonic way with ethanol content ϕA, which is an indication of amphipathic nature of tannin molecules. Best solvent composition ϕAB is a decreasing function of polymerization degree N, in agreement with increasing water solubility of tannins with N. Polymers longer than b present a power-law behavior I ˜Q-d in the SAXS profile at high momentum transfer Q. The monotonic decrease in d with increasing ϕA (from 2.4 in water to 1.9 in ethanol) points that the tannins are more compact in water than in ethanol, presumably due to attractive intramolecular interactions in water. Tannins were then oxidized in controlled conditions similar to real biological or food systems. Oxidation does not produce any intermolecular condensation, but generates additional intramolecular links. Some oxidation products are insoluble in water rich solvent. For that reason, we identify these species as a fraction of natural tannins called "T1" in the notation of Zanchi et al. [Langmuir 23, 9949 (2007)]. Within the fraction left soluble after oxidation, conformations of polymeric tannins, despite their higher rigidity, remain sensitive to solvent composition.

  17. Condensed tannins inhibit house fly (Diptera: Muscidae) development in livestock manure.

    PubMed

    Littlefield, Kimberly A; Muir, James P; Lambert, Barry D; Tomberlin, Jeffery K

    2011-12-01

    Reducing chemical use for suppressing internal and external parasites of livestock is essential for protecting environmental health. Although plant condensed tannins are known to suppress gastro-intestinal parasites in small ruminants, no research on the effects of tannins on external arthropod populations such as the house fly, Musca domestica L., have been conducted. We examined the impact of plant material containing condensed tannins on house fly development. Prairie acacia (Acacia angustissima (Mill.), Kuntze variety hirta (Nutt.) B.L. Rob.) herbage, panicled tick-clover (Desmodium paniculatum (L.) DC.) herbage, and quebracho (Shinopsis balansae Engl.) extracts were introduced at rates of 1, 3 or 5% condensed tannins/kg beef cattle, dairy cattle, and goat manure, respectively. In a second experiment, we also introduce purified catechin at 1 or 3% of dairy manure dry matter and measured its impact on house fly development. For the house flies used in these experiments, the following was recorded: percent fly emergence (PFE), average daily gain (ADG), and average fly weight (AFW). No effects (P>0.05) in house fly development were measured in the caprine manure. Prairie acacia (20.9% condensed tannins) had no effect on house flies developing in either bovine manures. Tick clover (4.9% condensed tannins) had a negative effect on all three quantifiable variables of house fly development in the bovine manures, whereas quebracho extract (64.0% condensed tannins) at the 3 and 5% rate reduced fly emergence in beef manure and average daily gain in dairy manure. The application of purified catechin at 3%, but not 1%, reduced fly PFE, ADG, and AFW. PMID:22217775

  18. 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. PMID:25230175

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

    SciTech Connect

    Tyler, Ludmila; Bragg, Jennifer; Wu, Jiajie; Yang, Xiaohan; Tuskan, Gerald A; Vogel, John

    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 hydrolase 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. Insights

  20. Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles.

    PubMed

    Kalinin, Vladimir I; Ivanchina, Natalia V; Krasokhin, Vladimir B; Makarieva, Tatyana N; Stonik, Valentin A

    2012-08-01

    Literature data about glycosides from sponges (Porifera, Demospongiae) are reviewed. Structural diversity, biological activities, taxonomic distribution and biological functions of these natural products are discussed. PMID:23015769

  1. Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities and Biological Roles

    PubMed Central

    Kalinin, Vladimir I.; Ivanchina, Natalia V.; Krasokhin, Vladimir B.; Makarieva, Tatyana N.; Stonik, Valentin A.

    2012-01-01

    Literature data about glycosides from sponges (Porifera, Demospongiae) are reviewed. Structural diversity, biological activities, taxonomic distribution and biological functions of these natural products are discussed. PMID:23015769

  2. Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis.

    PubMed

    Chludil, Hugo D; Muniain, Claudia C; Seldes, Alicia M; Maier, Marta S

    2002-06-01

    Two new sulfated triterpene glycosides, hemoiedemosides A (1) and B (2), have been isolated from the Patagonian sea cucumber Hemoiedema spectabilis. Their structures have been established by a combination of spectroscopic analysis (NMR and FABMS) and chemical transformations. Both glycosides present the same aglycon and differ in the degree of sulfation of the tetrasaccharide chain. Hemoiedemoside B (2) is a new example of a small number of trisulfated triterpene glycosides from sea cucumbers belonging to the family Cucumariidae. Glycosides 1 and 2 exhibit considerable antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum, while the semisynthetic desulfated derivative 1a is less active. PMID:12088428

  3. Tandem mass spectrometric fragmentation patterns of known and new steviol glycosides with structure proposals.

    PubMed

    Zimmermann, Benno F

    2011-06-15

    Stevia rebaudiana contains several steviol glycosides that have a sweet flavor. They are up to 450 times sweeter than sucrose, but some have an undesirable aftertaste. Up to 2010, ten different steviol glycosides have been described from the leaves or purified extracts of S. rebaudiana. In this paper, the tandem mass spectrometric fragmentation patterns of these ten compounds are compiled, along with a scheme for structural elucidation. This scheme is then applied to 12 steviol glycosides that have not yet been described. The proposed structures of five steviol glycosides have been confirmed by other authors. PMID:21594932

  4. Three new alkaloids and three new phenolic glycosides from Liparis odorata.

    PubMed

    Jiang, Piao; Liu, Hongdong; Xu, Xianghong; Liu, Bo; Zhang, Dongming; Lai, Xuewen; Zhu, Genghua; Xu, Peng; Li, Bin

    2015-12-01

    Three new alkaloids, liparis alkaloid A (1), B (2), C (3), and three new phenolic glycosides, liparis glycoside H (4), I (5), J (6), together with three known phenolic glycosides (7-9) were isolated from the whole plant of Liparis odorata. Their structures were characterized on the basis of extensive 1D-, 2D-NMR and HR-ESI-MS experiments. In addition, compounds 1-3 revealed hypolipidemic effects in the in vitro bioassays, and the ability to inhibit LPS-induced NO production of these isolated phenolic glycosides (4-9) was also evaluated. PMID:26481137

  5. 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. PMID:23149758

  6. 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. PMID:22031559

  7. Cardiac conduction system

    MedlinePlus Videos and Cool Tools

    ... cardiac muscle cells in the walls of the heart that send signals to the heart muscle causing it to contract. The main components ... the cardiac conduction system’s electrical activity in the heart.

  8. What Is Cardiac Rehabilitation?

    MedlinePlus

    ANSWERS by heart Treatments + Tests What Is Cardiac Rehabilitation? A cardiac rehabilitation (rehab) program takes place in a hospital or ... special help in making lifestyle changes. During your rehabilitation program you’ll… • Have a medical evaluation to ...

  9. Sudden Cardiac Arrest

    MedlinePlus

    ... from American Heart Association Aneurysms and Dissections Angina Arrhythmia Bundle Branch Block Cardiomyopathy Carotid Artery Disease Chronic ... terms: SCA, sudden cardiac death (SCD), sudden death, arrhythmias, ... ventricular fibrillation, defibrillator, automatic cardiac defibrillator ( ...

  10. Widespread tannin intake via stimulants and masticatories, especially guarana, kola nut, betel vine, and accessories.

    PubMed

    Morton, J F

    1992-01-01

    Tannins are increasingly recognized as dietary carcinogens and as antinutrients interfering with the system's full use of protein. Nevertheless, certain tannin-rich beverages, masticatories, and folk remedies, long utilized in African, Asiatic, Pacific, and Latin American countries, are now appearing in North American sundry shops and grocery stores. These include guarana (Paullinia cupana HBK.) from Brazil, kola nut (Cola nitida Schott & Endl. and C. acuminata Schott & Endl.) from West Africa, and betel nut (Areca catechu L.) from Malaya. The betel nut, or arecanut, has long been associated with oral and esophageal cancer because of its tannin content and the tannin contributed by the highly astringent cutch from Acacia catechu L. and Uncaria gambir Roxb. and the aromatic, astringent 'pan' (leaves of Piper betel L.) chewed with it. In addition to the constant recreational/social ingestion of these plant materials, they are much consumed as aphrodisiacs and medications. Guarana and kola nut enjoy great popularity in their native lands because they are also rich in caffeine, which serves as a stimulant. Research and popular education on the deleterious effects of excessive tannin intake could do much to reduce the heavy burden of early mortality and health care, especially in developing countries. PMID:1417698

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

    PubMed

    Stong, Rachel A; Kolodny, Eli; Kelsey, Rick G; González-Hernández, M P; Vivanco, Jorge M; Manter, Daniel K

    2013-06-01

    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 white oak) in order to evaluate the effect of differing sterol/tannin contents on Phytophthora ramorum growth. For all three species, high levels of foliage inhibited P. ramorum growth and sporulation, with a steeper concentration dependence for the two oak samples. Phytophthora ramorum growth and sporulation were inhibited by either phytosterols or tannin-enriched extracts. High levels of sterols diminished elicitin gene expression in P. ramorum; whereas the tannin-enriched extract decreased the amount of 'functional' or ELISA-detectable elicitin, but not gene expression. Across all treatment combinations, P. ramorum growth and sporulation correlated strongly with the amount of ELISA-detectable elicitin (R (2) = 0.791 and 0.961, respectively). PMID:23689874

  12. 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

  13. 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. PMID:25522953

  14. Zoosporicidal activity of polyflavonoid tannin identified in Lannea coromandelica stem bark against phytopathogenic oomycete Aphanomyces cochlioides.

    PubMed

    Islam, Md Tofazzal; Ito, Toshiaki; Sakasai, Mitsuyoshi; Tahara, Satoshi

    2002-11-01

    In a survey of nonhost plant secondary metabolites regulating motility and viability of zoospores of the Aphanomyces cochlioides, we found that stem bark extracts of Lannea coromandelica remarkably inhibited motility of zoospores followed by lysis. Bioassay-guided fractionation and chemical characterization of Lannea extracts by MALDI-TOF-MS revealed that the active constituents were angular type polyflavonoid tannins. Commercial polyflavonoid tannins, Quebracho and Mimosa, also showed identical zoosporicidal activity. Against zoospores, the motility-inhibiting and lytic activities were more pronounced in Lannea extracts (MIC 0.1 microg/mL) than in Quebracho (MIC 0.5 microg/mL) and Mimosa (MIC 0.5 microg/mL). Scanning electron microscopic observation visualized that both Lannea and commercial tannins caused lysis of cell membrane followed by fragmentation of cellular materials. Naturally occurring polyflavonoid tannin merits further study as potential zoospore regulating agent or as lead compound. To the best of our knowledge, this is the first report of zoosporicidal activity of natural polyflavonoid tannins against an oomycete phytopathogen. PMID:12405764

  15. Tannin and tannate from the quebracho tree: an eco-friendly alternative for controlling marine biofouling.

    PubMed

    Pérez, Miriam; García, Mónica; Blustein, Guillermo; Stupak, Mirta

    2007-01-01

    Current antifouling coatings are based on toxic compounds that can be harmful to the natural environment. A promising alternative to these compounds is the use of natural products that are non-toxic, but have antifouling properties. Tannins are natural, water-soluble, complex polyphenolic substances, which precipitate proteins and have anticorrosive and antimicrobial properties. In this study, the effect of quebracho tannin as a probable antifouling pigment in both laboratory and field trials is evaluated. As tannins have high solubility in aqueous media and consequently would leach rapidly, they were precipitated as aluminium tannate, which has an adequate solubility for use as a component in marine paints. In vitro exposure of Balanus amphitrite and Polydora ligni larvae to low concentrations of both quebracho tannin and saturated aluminium tannate solutions produced complete appendage immobilisation. In 28-d field trials of test gels, a significant decrease in micro- and macrofouling density and diversity in relation to the control gel was detected (p < 0.05). This study suggests that natural tannins could be employed as bioactive pigment for new antifouling technologies. PMID:17653926

  16. Cardiac Biomarkers: a Focus on Cardiac Regeneration

    PubMed Central

    Forough, Reza; Scarcello, Catherine; Perkins, Matthew

    2011-01-01

    Historically, biomarkers have been used in two major ways to maintain and improve better health status: first, for diagnostic purposes, and second, as specific targets to treat various diseases. A new era in treatment and even cure for the some diseases using reprograming of somatic cells is about to be born. In this approach, scientists are successfully taking human skin cells (previously considered terminally-differentiated cells) and re-programming them into functional cardiac myocytes and other cell types in vitro. A cell reprograming approach for treatment of cardiovascular diseases will revolutionize the field of medicine and significantly expand the human lifetime. Availability of a comprehensive catalogue for cardiac biomarkers is necessary for developing cell reprograming modalities to treat cardiac diseases, as well as for determining the progress of reprogrammed cells as they become cardiac cells. In this review, we present a comprehensive survey of the cardiac biomarkers currently known. PMID:23074366

  17. Active Site and Laminarin Binding in Glycoside Hydrolase Family 55*

    PubMed Central

    Bianchetti, Christopher M.; Takasuka, Taichi E.; Deutsch, Sam; Udell, Hannah S.; Yik, Eric J.; Bergeman, Lai F.; Fox, Brian G.

    2015-01-01

    The Carbohydrate Active Enzyme (CAZy) database indicates that glycoside hydrolase family 55 (GH55) contains both endo- and exo-β-1,3-glucanases. The founding structure in the GH55 is PcLam55A from the white rot fungus Phanerochaete chrysosporium (Ishida, T., Fushinobu, S., Kawai, R., Kitaoka, M., Igarashi, K., and Samejima, M. (2009) Crystal structure of glycoside hydrolase family 55 β-1,3-glucanase from the basidiomycete Phanerochaete chrysosporium. J. Biol. Chem. 284, 10100–10109). Here, we present high resolution crystal structures of bacterial SacteLam55A from the highly cellulolytic Streptomyces sp. SirexAA-E with bound substrates and product. These structures, along with mutagenesis and kinetic studies, implicate Glu-502 as the catalytic acid (as proposed earlier for Glu-663 in PcLam55A) and a proton relay network of four residues in activating water as the nucleophile. Further, a set of conserved aromatic residues that define the active site apparently enforce an exo-glucanase reactivity as demonstrated by exhaustive hydrolysis reactions with purified laminarioligosaccharides. Two additional aromatic residues that line the substrate-binding channel show substrate-dependent conformational flexibility that may promote processive reactivity of the bound oligosaccharide in the bacterial enzymes. Gene synthesis carried out on ∼30% of the GH55 family gave 34 active enzymes (19% functional coverage of the nonredundant members of GH55). These active enzymes reacted with only laminarin from a panel of 10 different soluble and insoluble polysaccharides and displayed a broad range of specific activities and optima for pH and temperature. Application of this experimental method provides a new, systematic way to annotate glycoside hydrolase phylogenetic space for functional properties. PMID:25752603

  18. Active site and laminarin binding in glycoside hydrolase family 55.

    PubMed

    Bianchetti, Christopher M; Takasuka, Taichi E; Deutsch, Sam; Udell, Hannah S; Yik, Eric J; Bergeman, Lai F; Fox, Brian G

    2015-05-01

    The Carbohydrate Active Enzyme (CAZy) database indicates that glycoside hydrolase family 55 (GH55) contains both endo- and exo-β-1,3-glucanases. The founding structure in the GH55 is PcLam55A from the white rot fungus Phanerochaete chrysosporium (Ishida, T., Fushinobu, S., Kawai, R., Kitaoka, M., Igarashi, K., and Samejima, M. (2009) Crystal structure of glycoside hydrolase family 55 β-1,3-glucanase from the basidiomycete Phanerochaete chrysosporium. J. Biol. Chem. 284, 10100-10109). Here, we present high resolution crystal structures of bacterial SacteLam55A from the highly cellulolytic Streptomyces sp. SirexAA-E with bound substrates and product. These structures, along with mutagenesis and kinetic studies, implicate Glu-502 as the catalytic acid (as proposed earlier for Glu-663 in PcLam55A) and a proton relay network of four residues in activating water as the nucleophile. Further, a set of conserved aromatic residues that define the active site apparently enforce an exo-glucanase reactivity as demonstrated by exhaustive hydrolysis reactions with purified laminarioligosaccharides. Two additional aromatic residues that line the substrate-binding channel show substrate-dependent conformational flexibility that may promote processive reactivity of the bound oligosaccharide in the bacterial enzymes. Gene synthesis carried out on ∼30% of the GH55 family gave 34 active enzymes (19% functional coverage of the nonredundant members of GH55). These active enzymes reacted with only laminarin from a panel of 10 different soluble and insoluble polysaccharides and displayed a broad range of specific activities and optima for pH and temperature. Application of this experimental method provides a new, systematic way to annotate glycoside hydrolase phylogenetic space for functional properties. PMID:25752603

  19. A new iridoid glycoside from the roots of Dipsacus asper.

    PubMed

    Ji, De; Zhang, Chunfeng; Li, Jingzhi; Yang, Haowei; Shen, Jingyang; Yang, Zhonglin

    2012-01-01

    A new iridoid glycoside, named loganic acid ethyl ester (1), together with five known compounds: chlorogenic acid (2), caffeic acid (3), loganin (4), cantleyoside (5) and syringaresinol-4',4''-O-bis-β-D-glucoside (6) were isolated from the roots of Dipsacus asper. The structure of compound 1 was elucidated on the basis of detailed spectroscopic analyses. Lignan is isolated from Dipsacaceae species for the first time. Compounds 1, 4 and 5 had moderate neuroprotective effects against the Aβ₂₅₋₃₅ induced cell death in PC12 cells. PMID:22306831

  20. New Lignans and Iridoid Glycosides from Dipsacus asper Wall.

    PubMed

    Sun, Xinguang; Ma, Guoxu; Zhang, Dawei; Huang, Wenhua; Ding, Gang; Hu, Huagang; Tu, Guangzhong; Guo, Baolin

    2015-01-01

    Six new compounds, including four new lignans, dipsalignan A (1), B-D (3-5), and two new bis-iridoid glycoside dimmers, dipsanosides M (7) and N (8), together with two known compounds (2) and (6), have been isolated from the roots of Dipsacus asper Wall. Their structures were established on the basis of spectroscopic data (MS, 1D, 2D NMR, and CD) and chemical methods. All the isolated compounds were tested against human immunodeficiency virus-1 (HIV-1) integrase inhibition activities, and only compounds 1, 2, 7, and 8 displayed weak activities. PMID:25635380

  1. A new cucurbitacin glycoside from Kageneckia oblonga (Rosaceae).

    PubMed

    Muñoz, O; Delporte, C; Backhouse, N; Erazo, S; Negrete, R; Maldonado, S; López-Pérez, J L; San Feliciano, A

    2000-01-01

    A novel cucurbitacin glycoside has been isolated from aerial parts of Kageneckia oblonga R. et P. and shown to be 3beta-(beta-D-glucosyloxy)-16alpha,23alpha-epoxycuc urbita-5,24-dien-11-one. The structure was established by usual spectroscopic and two-dimensional (2D) NMR techniques. This compound has found to be nontoxic when tested in-vivo cell culture assays. In previous investigations we reported 23,24-dihydrocucurbitacin F and prunasine. This was the first report on cucurbitacins from the genus Kageneckia (Rosaceae). PMID:10817201

  2. Synthesis and evaluation of bibenzyl glycosides as potent tyrosinase inhibitors.

    PubMed

    Tajima, Reiko; Oozeki, Hiromi; Muraoka, Seiichi; Tanaka, Saori; Motegi, Yukari; Nihei, Hiroyuki; Yamada, Yoichi; Masuoka, Noriyoshi; Nihei, Ken-ichi

    2011-04-01

    Bibenzyl glycosides 1-6 were synthesized from 2,4-dihydoxybenzaldehyde and xylose, glucose, cellobiose or maltose. The key steps in the synthesis were the Wittig reaction and trichloroacetimidate glycosylation. Tests for tyrosinase inhibitory activity showed that all were significantly active, indicating that they are unique hydrophilic tyrosinase inhibitors. Bibenzyl xyloside 2 is a particularly potent inhibitor (IC(50) = 0.43 μM, 17 times higher than that of kojic acid). These results suggest that the hydrophilic cavity of tyrosinase might accommodate the bulky carbohydrate on the bibenzyl scaffold. PMID:21334791

  3. A new pregnane glycoside from Gomphocarpus fruticosus growing in Egypt.

    PubMed

    Marzouk, Amani M; Osman, Samir M; Gohar, Ahmed A

    2016-05-01

    Phytochemical investigation of Gomphocarpus fruticosus (L.) Ait. of Egyptian origin afforded the new pregnane glycoside lineolon-3-O-[β-D-oleandropyranosyl-(1-4)-β-D-cymaropyranosyl-(1-4)-β-D-cymaropyranoside], along with six known compounds. The structures of the isolated compounds were elucidated on the basis of extensive spectroscopic evidences derived from 1D, 2D NMR experiments, mass spectrometry and by comparing their physical and spectroscopic data to literature. These included the triterpenoids 3β-taraxerol, 3β-taraxerol acetate and betulinic acid, which are identified for the first time in G. fruticosus and the cardenolides uzarigenin, gomphoside and calotropin. PMID:26595507

  4. Two new flavonoid glycosides from Semen Ziziphi Spinosae.

    PubMed

    Zhang, Lin; Xu, Zhi-Lin; Wu, Chun-Fu; Yang, Jing-Yu; Kano, Yoshihiro; Yuan, Dan

    2012-01-01

    Two novel flavonoid glycosides, 6"'-dihydrophaseoylspinosin (1) and 6″,6"'-diferuloylspinosin (2), were isolated from the MeOH extract of Semen Ziziphi Spinosae, together with six known flavonoids, isovitexin-2″-O-β-(6-O-E-feruloyl)glucopyranoside (3), spinosin (4), isospinosin (5), 6"'-feruloylspinosin (6), swertisin (7), and isovitexin-2″-O-β-d-glucopyranoside (8). The structures of 1 and 2 were elucidated by spectroscopic methods including UV, IR, ESI-TOF-MS, 1D NMR, and 2D NMR experiments. PMID:22296152

  5. Bioactive Iridoid Glycosides from the Whole Plants of Rehmannia chingii.

    PubMed

    Liu, Yan-Fei; Shi, Guo-Ru; Wang, Xin; Zhang, Chun-Lei; Wang, Yan; Chen, Ruo-Yun; Yu, De-Quan

    2016-02-26

    Nine new iridoid glycosides, rehmachingiiosides A-I (1-9), together with 16 known analogues, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of spectroscopic data analysis and from chemical evidence. Furthermore, in two vitro assays, compounds 5 and 10 showed an inhibitory effect on LPS-induced NO production with IC50 values of 2.5 and 7.3 μM, and compounds 4, 6, and 10-12 (when evaluated at 10 μM) exhibited evidence of hepatoprotective effects against APAP-induced HepG2 cell damage. PMID:26859776

  6. Two new glycosides from the fruits of Morinda citrifolia L.

    PubMed

    Hu, Ming-Xu; Zhang, Hong-Cai; Wang, Yu; Liu, Shu-Min; Liu, Li

    2012-01-01

    To study the chemical constituents of the fruits of noni (Morinda citrifolia L.), and find novel compounds, an n-butanol extract of the ethanol soluble fraction was subjected to repeated silica gel and ODS column chromatography and HPLC. Two new glycosides were isolated and their structures elucidated by NMR and HRFAB-MS spectrometry as (2E,4E,7Z)-deca-2,4,7-trienoate-2-O-β-D-glucopyranosyl-β-D-glucopyranoside and amyl-1-O-β-D-apio-furanosyl-1,6-O-β-D-glucopyranoside, respectively. PMID:23103531

  7. Flavonoid glycosides from Byrsocarpus coccineus leaves. Schum and Thonn (Connaraceae).

    PubMed

    Ahmadu, A A; Hassan, H S; Abubakar, M U; Akpulu, I N

    2007-01-01

    The bioactive ethyl acetate and N-butanol soluble parts of an ethanolic extract of Byrsocarpus coccineus leaves was subjected to column chromatography over silica gel G (60-120 microns) and repeated purification of the flavonoid rich fraction over sephadex LH-20 eluted with methanol led to the isolation of three flavonoid glycosides identified as quercetin 3-O-alpha-arabinoside (I), quercetin (II) and quercetin 3-beta-D-glucoside. Their structures were elucidated by (1)H and (13)C-NMR data and are reported here for the first time in this plant. PMID:20161886

  8. Additional new minor cucurbitane glycosides from Siraitia grosvenorii.

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2014-01-01

    Continuous phytochemical studies of the crude extract of Luo Han Guo (Siraitia grosvenorii) furnished three additional new cucurbitane triterpene glycosides, namely 11-deoxymogroside V, 11-deoxyisomogroside V, and 11-deoxymogroside VI. The structures of all the isolated compounds were characterized on the basis of extensive NMR and mass spectral data as well as hydrolysis studies. The complete ¹H- and ¹³C-NMR spectral assignments of the three unknown compounds are reported for the first time based on COSY, TOCSY, HSQC, and HMBC spectroscopic data. PMID:24662081

  9. Inhibition of amyloid β aggregation by acteoside, a phenylethanoid glycoside.

    PubMed

    Kurisu, Manami; Miyamae, Yusaku; Murakami, Kazuma; Han, Junkyu; Isoda, Hiroko; Irie, Kazuhiro; Shigemori, Hideyuki

    2013-01-01

    We examined the effects of acteoside (1a), which was isolated from Orobanche minor, and its derivatives on the aggregation of a 42-mer amyloid β protein (Aβ42) in our search for anti-amyloidogenic compounds for Alzheimer's disease (AD) therapy. Acteoside (1a) strongly inhibited the aggregation of Aβ42 in a dose-dependent manner. The structure-activity relationship for acteoside (1a) and related compounds suggests the catechol moiety of phenylethanoid glycosides to be essential for this inhibitory activity. PMID:23748773

  10. A first new antimalarial pregnane glycoside from Gongronema napalense

    PubMed Central

    Libman, Amey; Zhang, Hongjie; Ma, Cuiying; Southavong, Bounhong; Sydara, Kongmany; Bouamanivong, Somsanith; Tan, Ghee T.; Fong, Harry H. S.; Soejarto, D. Doel

    2010-01-01

    As a part of the UIC-based ICBG project in Laos, plants were collected based on ethnomedical interviews and evaluated for antimalarial activity. A CHCl3 extract from the vine of Gongronema napalense (Wall.) Decne. (Asclepiadaceae) showed promising anti-malarial activity while exhibiting low levels of cytotoxicity and was thus followed up with further fractionation and biological evaluation. Bioassay-guided fractionation led to the isolation of a new steroidal glycoside, gongroneside A, which showed antimalarial activity in vitro with an IC50 value of 1.60 and 1.39 μM against the Plasmodium falciparum D6 and W2 clones, respectively. PMID:23653676

  11. High-throughput micro-plate HCL-vanillin assay for screening tannin content in sorghum grain

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Sorghum contains tannin which is a phenolic compound that offers health promoting antioxidant capacity. The HCl-vanillin assay is a common and time consuming method for determining tannin content, but is not efficient for screening large sample sets as seen in association mapping panels or breeding ...

  12. Changes in Soluble-N in forest and pasture soils after repeated applications of tannins and related phenolic compounds

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins, reactive polyphenolic secondary metabolites produced by plants, can rapidly reduce the solubility of labile soil nitrogen (N). However, studies comparing the effects of different tannins to related compounds on different land uses are sparse. We compared soluble-N extracted from Appalachi...

  13. Effects of plant tannin extracts supplementation on animal performance and gastrointestinal parasites infestation in steers grazing winter wheat

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  14. Effects of condensed tannins on hydrogen sulfide production and the sulfate-reducing bacterial population of swine manure

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Condensed tannins are natural plant compounds that have antibacterial properties and have been used in studies to reduce methane emissions and frothy bloat in cattle. The objective of this study was to test the effects of condensed tannins on swine manure to target bacterial groups responsible for ...

  15. Kinetics and binding capacity of six soils for structurally defined hydrolyzable and condensed tannins and related phenols

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We investigated tannin-soil interactions by assessing the kinetics of sorption and sorption capacities, and their relationship to the chemical properties of six polyphenolic compounds and the textures of six soils. We developed a new extraction procedure for recovering tannins from soil samples by ...

  16. Interaction between a tannin-containing legume and endophyte-infected tall fescue seed on lambs’ feeding behavior and physiology

    Technology Transfer Automated Retrieval System (TEKTRAN)

    It was hypothesized that a tannin-rich legume like sainfoin reduces the negative postingestive effects of ergot alkaloids in tall fescue. Thirty-two 3-month-old lambs were individually penned and randomly assigned to a 2X2 factorial experimental design with two legume species (1-sainfoin [SF; tannin...

  17. 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. PMID:27041326

  18. 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

  19. Study on extraction process of tannins from Semen Cuscutae and their anti-papilloma activity.

    PubMed

    Wang, Jiangning; Li, Xiaorong; Gao, Lei

    2013-01-01

    The objective of this paper was to study the extraction methods of tannin constituents from Semen Cuscutae and their anti-papilloma effects. Single factor test and orthogonal design methods were used to determine the optimal extraction method; the mouse skin papilloma model induced by DMBA/croton oil was established, which was a classic two-stage carcinogenesis model being used to observe and evaluate the anti-carcinogenic effects of tannins extracted from Semen Cuscutae in different stages. The optimal extraction method of Semen Cuscutae was a 20-fold volume of solvent, a temperature of 50 °C, three times of extraction, with 20 min each, skin papilloma experiment revealed that the number of bearing tumors gradually reduced, and the inhibition rate gradually increased with the increase of dose, in the high-dose group, its inhibition rate reached 70.2%. Tannin extract from Semen Cuscutae has an obvious inhibitory effect on skin papilloma development. PMID:24146476

  20. Thermal properties of tannin extracted from Anacardium occidentale L. using TGA and FT-IR spectroscopy.

    PubMed

    Viswanath, Vinod; Leo, Vincent Vineeth; Prabha, S Sabna; Prabhakumari, C; Potty, V P; Jisha, M S

    2016-01-01

    The chemical nature of the polyphenols of cashew kernel testa has been determined. Testa contains tannins, which present large molecular complexity and has an ancient use as tanning agents. The use of tannins extracted from cashew testa, considered in many places as a waste, grants an extra value to the cashew. In this work we have analysed through high performance liquid chromatography, infrared spectroscopy (FT-IR) and thermo gravimetric analysis the average molecular weight, main functional groups and thermal properties of tannins extracted from Anacardium occidentale L. The results of these analyses are compared with the commercial grade tannic acid. The FT-IR spectra showed bands characteristic of C = C, C-C and OH bonds. This important bioactive compound present in the cashew nut kernel testa was suggested as an interesting economical source of antioxidants for use in the food and nutraceutical industry. PMID:26119693

  1. 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

  2. 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

  3. In vitro protein degradation of 38 sainfoin accessions and its relationship to tannin content by different assays.

    PubMed

    Lorenz, Martin M; Hayot Carbonero, Christine; Smith, Lydia; Udén, Peter

    2012-05-23

    This study compared 38 sainfoin and 2 Lotus accessions to their respective tannin contents, N buffer solubility, and in vitro protein degradation. Tannin contents were measured by a protein precipitation method using either bovine serum albumin or Rubisco and by the colorimetric HCl/butanol method. Precipitation of bovine serum albumin and Rubisco was highly correlated (R(2) = 0.939). Correlations between the protein precipitation variants and the HCl/butanol method were relatively low (R(2) < 0.6). Protein degradation was measured at 4 h of incubation in an inhibited in vitro system and could not be explained by any of the tannin assays (R(2) < 0.03) and only partially by N buffer solubility (R(2) ≤ 0.433). Decisive factors other than the quantity of tannins or their ability to precipitate proteins must be considered. Resistance of soluble protein toward degradation can possibly be caused by tannin protein binding. PMID:22494200

  4. Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl β-C-Glycosides.

    PubMed

    Guisot, Nicolas E S; Ella Obame, Idriss; Ireddy, Prathap; Nourry, Arnaud; Saluzzo, Christine; Dujardin, Gilles; Dubreuil, Didier; Pipelier, Muriel; Guillarme, Stéphane

    2016-03-18

    A new strategy for the synthesis of acyl β-C-glycosides is described. The reactivity of glyconitriles toward organometallic reagents such as organomagnesium or organolithium derivatives was studied, affording acyl β-C-glycosides in moderate to good yields. In this study, glycal formation was efficiently prevented by deprotonating the hydroxyl group in position 2 of the glyconitriles during the process. PMID:26926714

  5. Environment and Genotype Affect Sweetpotato Storage Root Periderm Resin Glycoside Content

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Resin glycosides are complex compounds composed primarily of fatty acids and sugars that contribute to allelopathic potential and pest resistance in sweetpotato. Total periderm resin glycoside (PRG) contents of 10 sweetpotato (Ipomoea batatas L.) clones grown in three different field trials was det...

  6. 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. PMID:18670118

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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 ann...

  8. Dalvelutinoside, a new isoflavone glycoside from the methanol extract of Dalbergia velutina roots.

    PubMed

    Kaennakam, Sutin; Siripong, Pongpun; Tip-Pyang, Santi

    2016-07-01

    A new isoflavone glycoside, dalvelutinoside (1), together with one known isoflavone (2) and five known isoflavone glycosides (3-7) were isolated from the methanol extract of the roots of Dalbergia velutina. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines. PMID:26594823

  9. Two new nor-triterpene glycosides from peruvian "Uña de Gato" (Uncaria tomentosa).

    PubMed

    Kitajima, Mariko; Hashimoto, Ken-Ichiro; Yokoya, Masashi; Takayama, Hiromitsu; Sandoval, Manuel; Aimi, Norio

    2003-02-01

    Two new 27-nor-triterpene glycosides, tomentosides A (1) and B (2), were isolated from Peruvian "Uña de Gato" (cat's claw, plant of origin: Uncaria tomentosa), a traditional herbal medicine in Peru. Their structures were determined by spectroscopic analysis and chemical interconversions. This is the first report of naturally occurring pyroquinovic acid glycosides. PMID:12608878

  10. Cardiac gated ventilation

    SciTech Connect

    Hanson, C.W. III; Hoffman, E.A.

    1995-12-31

    There are several theoretic advantages to synchronizing positive pressure breaths with the cardiac cycle, including the potential for improving distribution of pulmonary and myocardial blood flow and enhancing cardiac output. The authors evaluated the effects of synchronizing respiration to the cardiac cycle using a programmable ventilator and electron beam CT (EBCT) scanning. The hearts of anesthetized dogs were imaged during cardiac gated respiration with a 50 msec scan aperture. Multi slice, short axis, dynamic image data sets spanning the apex to base of the left ventricle were evaluated to determine the volume of the left ventricular chamber at end-diastole and end-systole during apnea, systolic and diastolic cardiac gating. The authors observed an increase in cardiac output of up to 30% with inspiration gated to the systolic phase of the cardiac cycle in a non-failing model of the heart.

  11. Cardiac gated ventilation

    NASA Astrophysics Data System (ADS)

    Hanson, C. William, III; Hoffman, Eric A.

    1995-05-01

    There are several theoretic advantages to synchronizing positive pressure breaths with the cardiac cycle, including the potential for improving distribution of pulmonary and myocardial blood flow and enhancing cardiac output. We evaluated the effects of synchronizing respiration to the cardiac cycle using a programmable ventilator and electron beam CT (EBCT) scanning. The hearts of anesthetized dogs were imaged during cardiac gated respiration with a 50msec scan aperture. Multislice, short axis, dynamic image data sets spanning the apex to base of the left ventricle were evaluated to determine the volume of the left ventricular chamber at end-diastole and end-systole during apnea, systolic and diastolic cardiac gating. We observed an increase in cardiac output of up to 30% with inspiration gated to the systolic phase of the cardiac cycle in a nonfailing model of the heart.

  12. Nano-porous solid-state photovoltaic cell sensitized with tannin

    NASA Astrophysics Data System (ADS)

    Tennakone, K.; Kumara, G. R. R. A.; Wijayantha, K. G. U.; Kottegoda, I. R. M.; Perera, V. P. S.; Aponsu, G. M. L. P.

    1998-01-01

    Tannin and related polyphenolic substances strongly surface chelate with 0268-1242/13/1/021/img1 sensitizing nano-porous films of 0268-1242/13/1/021/img1 to the visible spectrum. The photovoltaic cell nano-porous n-0268-1242/13/1/021/img3-CuI generates highly stable photovoltages. The result is explained as the effectiveness of the 0268-1242/13/1/021/img4-tannin complex on the surface of 0268-1242/13/1/021/img1 in preventing short-circuiting across the 0268-1242/13/1/021/img1/CuI barrier.

  13. Allosteric indicator displacement enzyme assay for a cyanogenic glycoside.

    PubMed

    Jose, D Amilan; Elstner, Martin; Schiller, Alexander

    2013-10-18

    Indicator displacement assays (IDAs) represent an elegant approach in supramolecular analytical chemistry. Herein, we report a chemical biosensor for the selective detection of the cyanogenic glycoside amygdalin in aqueous solution. The hybrid sensor consists of the enzyme β-glucosidase and a boronic acid appended viologen together with a fluorescent reporter dye. β-Glucosidase degrades the cyanogenic glycoside amygdalin into hydrogen cyanide, glucose, and benzaldehyde. Only the released cyanide binds at the allosteric site of the receptor (boronic acid) thereby inducing changes in the affinity of a formerly bound fluorescent indicator dye at the other side of the receptor. Thus, the sensing probe performs as allosteric indicator displacement assay (AIDA) for cyanide in water. Interference studies with inorganic anions and glucose revealed that cyanide is solely responsible for the change in the fluorescent signal. DFT calculations on a model compound revealed a 1:1 binding ratio of the boronic acid and cyanide ion. The fluorescent enzyme assay for β-glucosidase uses amygdalin as natural substrate and allows measuring Michaelis-Menten kinetics in microtiter plates. The allosteric indicator displacement assay (AIDA) probe can also be used to detect cyanide traces in commercial amygdalin samples. PMID:24123550

  14. Syntheses of alpha-tocopheryl glycosides by glucosidases.

    PubMed

    Ponrasu, Thangavel; Charles, Rajachristu Einstein; Sivakumar, Ramaiah; Divakar, Soundar

    2008-08-01

    Enzymatic syntheses of water-soluble alpha-tocopheryl glycosides were carried out in di-isopropyl ether using amyloglucosidase from Rhizopus mold or beta-glucosidase isolated from sweet almond. Optimum conditions for the amyloglucosidase were: alpha-tocopherol 0.5 mmol, D-glucose 0.5 mmol, 400 activity unit (AU) amyloglucosidase, 0.2 mM pH 7 phosphate buffer and 72 h; and for the beta-glucosidase: alpha-tocopherol 0.5 mmol, D: -glucose 0.5 mmol, 110 AU beta-glucosidase, 0.1 mM pH 6 phosphate buffer and 72 h. Out of 11 carbohydrates employed, amyloglucosidase reacted only with D-glucose to give 50% of 6-O-(alpha-D-glucopyranosyl)alpha-tocopherol. However, the beta-glucosidase gave 6-O-(beta-D-glucopyranosyl)alpha-tocopherol, 6-O-(alpha-D-galactopyranosyl)alpha-tocopherol, 6-O-(beta-D-galactopyranosyl)alpha-tocopherol, 6-O-(alpha-D-mannopyranosyl)alpha-tocopherol and 6-O-(beta-D-mannopyranosyl)alpha-tocopherol in yields ranging from 10-25%. Water solubility of 6-O-(alpha-D-glucopyranosyl)alpha-tocopherol was 26 g/l at 25 degrees C. alpha-Tocopheryl glycosides showed antioxidant activities with IC(50) values from 0.5 to 1 mM and angiotensin-converting enzyme (ACE) inhibitory activity with IC(50) values from 1.3 to 2.6 mM. PMID:18368294

  15. Cycloartane and oleanane-type glycosides from Astragalus pennatulus.

    PubMed

    Un, Rabia; Horo, Ibrahim; Masullo, Milena; Falco, Antonia; Senol, Serdar G; Piacente, Sonia; Alankuş-Çalıskan, Özgen

    2016-03-01

    Four new cycloartane and one new oleanane-type glycosides were isolated from Astragalus pennatulus along with five known cycloartane-type glycosides. The structures of the new compounds were established as 3-O-β-D-xylopyranosyl-6-O-β-D-glucopyranosyl-3β,6α,16β-trihydroxy-24-oxo-20(R),25-epoxycycloartane (1), 3-O-[β-D-glucuronopyranosyl-(1 → 2)-β-D-xylopyranosyl]-3β,16β,24α-trihydroxy-20(R),25-epoxycycloartane (2), 3-O-[β-D-glucuronopyranosyl-(1 → 2)-β-D-xylopyranosyl]-3β,16β,25-trihydroxy-20(R),24(S)-epoxycycloartane (3), 3,25-di-O-β-D-glucopyranosyl-6-O-β-D-xylopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),24(S)-epoxycycloartane (4), 29-O-α-L-rhamnopyranosyl-abrisapogenol B (5) by 1D and 2D-NMR experiments along with ESIMS and HRMS analyses. The aglycone of compound 1, 3β,6α,16β-trihydroxy-24-oxo-20(R),25-epoxycycloartane, is reported for the first time. The cytotoxic activity of the isolated compounds was evaluated against three cancer cell lines including A549 (human lung adenocarcinoma), A375 (human melanoma) and DeFew (human B lymphoma) cells. None of the tested compounds caused a significant reduction of the cell number. PMID:26804373

  16. New Glycosides and Trypanocidal Metabolites from Vangueria edulis

    PubMed Central

    Mohamed, Shaymaa M. M.; Elokely, Khaled M.; Bachkeet, Enaam Y.; Bayoumi, Soad A. L.; Carnevale, Vincenzo; Klein, Michael L.; Cutler, Stephen J.

    2016-01-01

    A new iridoid glucoside, 10-methoxy apodanthoside (1), and a new monoterpene glycoside, (3S,6S)-cis linalool-3,7-oxide O-β-D-glucopyranosyl-(1″→5′)-β-D-xylofuranoside (2), were isolated from V. edulis (Rubiaceae), along with eighteen known compounds (3–20), including monoterpenes, iridoid glycosides, and a lignin, which were encountered for the first time in the genus Vangueria,. The structural elucidation of the isolates was based on the analysis of spectroscopic (1D and 2D NMR) and HR-ESI-MS data. Detailed stereochemical studies of 1 and related iridoid glucosides (compounds 3, 4 and 8) were made by matching the calculated ECD peaks with the experimental ones. All isolates were tested for their antiprotozoal, antifungal, and antiplasmodial activities. Compounds 9, 15 and 16 showed good trypanocidal activities against Trypanosoma brucei brucei with IC50 values of 8.18, 9.02 and 7.80 μg/mL, respectively and IC90 values of >10, >10 and 9.76 μg/mL, respectively. Compound 16 showed a moderate activity against Candida glabrata with an IC50 value of 8.66 μg/mL. Compound 20 showed a weak antiplasmodial activity against chloroquine-sensitive (D6) and resistant (W2) Plasmodium falciparum with IC50 values of 3.29 (SI, >1.4) and 4.53 (SI, >1) μg/mL, respectively. PMID:26749819

  17. Angling for Uniqueness in Enzymatic Preparation of Glycosides

    PubMed Central

    Trincone, Antonio

    2013-01-01

    In the early days of biocatalysis, limitations of an enzyme modeled the enzymatic applications; nowadays the enzyme can be engineered to be suitable for the process requirements. This is a general bird’s-eye view and as such cannot be specific for articulated situations found in different classes of enzymes or for selected enzymatic processes. As far as the enzymatic preparation of glycosides is concerned, recent scientific literature is awash with examples of uniqueness related to the features of the biocatalyst (yield, substrate specificity, regioselectivity, and resistance to a particular reaction condition). The invention of glycosynthases is just one of the aspects that has thrust forward the research in this field. Protein engineering, metagenomics and reaction engineering have led to the discovery of an expanding number of novel enzymes and to the setting up of new bio-based processes for the preparation of glycosides. In this review, new examples from the last decade are compiled with attention both to cases in which naturally present, as well as genetically inserted, characteristics of the catalysts make them attractive for biocatalysis. PMID:24970171

  18. Steviol Glycosides Modulate Glucose Transport in Different Cell Types

    PubMed Central

    Rizzo, Benedetta; Zambonin, Laura; Leoncini, Emanuela; Vieceli Dalla Sega, Francesco; Prata, Cecilia; Fiorentini, Diana; Hrelia, Silvana

    2013-01-01

    Extracts from Stevia rebaudiana Bertoni, a plant native to Central and South America, have been used as a sweetener since ancient times. Currently, Stevia extracts are largely used as a noncaloric high-potency biosweetener alternative to sugar, due to the growing incidence of type 2 diabetes mellitus, obesity, and metabolic disorders worldwide. Despite the large number of studies on Stevia and steviol glycosides in vivo, little is reported concerning the cellular and molecular mechanisms underpinning the beneficial effects on human health. The effect of four commercial Stevia extracts on glucose transport activity was evaluated in HL-60 human leukaemia and in SH-SY5Y human neuroblastoma cells. The extracts were able to enhance glucose uptake in both cellular lines, as efficiently as insulin. Our data suggest that steviol glycosides could act by modulating GLUT translocation through the PI3K/Akt pathway since treatments with both insulin and Stevia extracts increased the phosphorylation of PI3K and Akt. Furthermore, Stevia extracts were able to revert the effect of the reduction of glucose uptake caused by methylglyoxal, an inhibitor of the insulin receptor/PI3K/Akt pathway. These results corroborate the hypothesis that Stevia extracts could mimic insulin effects modulating PI3K/Akt pathway. PMID:24327825

  19. Flacourtosides A-F, phenolic glycosides isolated from Flacourtia ramontchi.

    PubMed

    Bourjot, Mélanie; Leyssen, Pieter; Eydoux, Cécilia; Guillemot, Jean-Claude; Canard, Bruno; Rasoanaivo, Philippe; Guéritte, Françoise; Litaudon, Marc

    2012-04-27

    In an effort to identify novel inhibitors of chikungunya (CHIKV) and dengue (DENV) virus replication, a systematic study with 820 ethyl acetate extracts of madagascan plants was performed in a virus-cell-based assay for CHIKV, and a DENV NS5 RNA-dependent RNA polymerase (RdRp) assay. The extract obtained from the stem bark of Flacourtia ramontchi was selected for its significant activity in both assays. Six new phenolic glycosides, named flacourtosides A-F (1-6), phenolic glycosides itoside H, xylosmin, scolochinenoside D, and poliothrysoside, and betulinic acid 3β-caffeate were obtained using the bioassay-guided isolation process. Their structures were elucidated by comprehensive analyses of NMR spectroscopic and mass spectrometric data. Even though several extracts and fractions showed significant selective antiviral activity in the CHIKV virus-cell-based assay, none of the purified compounds did. However, in the DENV RNA polymerase assay, significant inhibition was observed with betulinic acid 3β-caffeate (IC(50) = 0.85 ± 0.1 μM) and to a lesser extent for the flacourtosides A and E (1 and 5, respectively), and scolochinenoside D (IC(50) values ~10 μM). PMID:22439591

  20. Glycosides from the stem bark of Fraxinus sieboldiana.

    PubMed

    Lin, Sheng; Wang, Sujuan; Liu, Mingtao; Gan, Maoluo; Li, Shuai; Yang, Yongchun; Wang, Yinghong; He, Wenyi; Shi, Jiangong

    2007-05-01

    A norditerpene glucopyranoside with a novel carbon skeleton (1), eight new aromatic glycosides (2-9), and 25 known glycosides have been isolated from a H2O-soluble portion of an ethanolic extract of the stem bark of Fraxinus sieboldiana. Their structures were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo- and erythro-arylglycerols in different solvents, an application of Delta delta C8-C7 values to distinguish threo-arylglycerol and erythro-arylglycerol isomers was proposed. In the in vitro assays, compound 5 displayed TNF-alpha secretion inhibitory activity with an IC50 value of 1.6 microM, compound 6 showed antioxidative activity inhibiting Fe+2-cystine-induced rat liver microsomal lipid peroxidation with an IC50 value of 0.9 microM, and plantasioside (10) showed selective activity against the human colon cancer cell line (HCT-8) with an IC50 value of 3.4 microM. PMID:17461599

  1. 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. PMID:24831641

  2. Effects of condensed tannins on established populations and on incoming larvae of Trichostrongylus colubriformis and Teladorsagia circumcincta in goats.

    PubMed

    Paolini, Virginie; Frayssines, Audrey; De La Farge, France; Dorchies, Philippe; Hoste, Hervé

    2003-01-01

    The use of tanniferous plants or tannins represents one alternative approach to the control of gastrointestinal parasites in ruminants but most data have been obtained in sheep. The current study was therefore performed in goats with two objectives: firstly, to investigate the effects of condensed tannins (CT) on adult populations of Trichostrongylus colubriformis and Teladorsagia circumcincta; secondly, to examine their effects on the establishment of infective larvae of these two species. In experiment 1, two groups of kids were infected with 6 000 L3 of T. colubriformis and 6 000 L3 of T. circumcincta. After 7 weeks, quebracho extracts were administered per os for 8 days to one group. A comparable group which did not receive tannins was included as the control. The kids were slaughtered on week 11. Parasitological and pathophysiological parameters were measured weekly. Worm counts were assessed and mast cells, globule leukocytes and eosinophils were counted in the abomasal and intestinal mucosae. Tannin administration was associated with a decrease in egg excretion, and a decrease in female fecundity, but with no changes in worm numbers. These changes were associated with an increased number of intestinal mast cells. In experiment 2, 24 goats were used according to a 2 x 2 factorial design, depending on infection and tannin administration. Two groups were either infected with 6 000 L3 of T. colubriformis or T. circumcincta. Within each group, the goats were either drenched or undrenched with tannin extracts. Pathophysiological parameters were measured weekly. Twelve days after the cessation of tannin administration, the goats were slaughtered. Worm counts and female worm fecundity were determined. Tannin consumption was associated with a significant reduction (P < 0.01) of Trichostrongylus populations and a close to significant reduction for Teladorsagia. No effect on fecundity was observed. Our results (1) confirm the consequences of condensed tannins on

  3. 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. PMID:27233155

  4. 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. PMID:24206531

  5. Application of an enyne metathesis/Diels-Alder cycloaddition sequence: a new versatile approach to the syntheses of C-aryl glycosides and spiro-C-aryl glycosides.

    PubMed

    Subrahmanyam, Ayyagari V; Palanichamy, Kalanidhi; Kaliappan, Krishna P

    2010-07-26

    An efficient approach for the synthesis of a variety of C-aryl and spiro-C-aryl glycosides is described. This diversity-oriented strategy employed here relies on a sequential enyne metathesis to generate the 1,3-diene moiety and Diels-Alder reaction with different dienophiles followed by aromatisation. Whereas cross-enyne metathesis with ethylene gas is used to install the 1,3-diene moiety at the anomeric centre for the synthesis of C-aryl glycosides, an intramolecular enyne metathesis on the sugar enyne is performed to generate the 1,3-diene moiety for the synthesis of spiro-C-aryl glycosides. Efforts to extend this strategy to the synthesis of the core structure of natural C-aryl glycoside gilvocarcin are also described. A combination of both C-aryl and spiro-C-aryl glycosides in the same moiety to combine the features thereof has also been accomplished. A tandem enyne metathesis/Diels-Alder reaction/aromatisation has also been attempted to directly access the C-aryl glycosides in one pot albeit in low yield. PMID:20549721

  6. Stimulating endogenous cardiac repair

    PubMed Central

    Finan, Amanda; Richard, Sylvain

    2015-01-01

    The healthy adult heart has a low turnover of cardiac myocytes. The renewal capacity, however, is augmented after cardiac injury. Participants in cardiac regeneration include cardiac myocytes themselves, cardiac progenitor cells, and peripheral stem cells, particularly from the bone marrow compartment. Cardiac progenitor cells and bone marrow stem cells are augmented after cardiac injury, migrate to the myocardium, and support regeneration. Depletion studies of these populations have demonstrated their necessary role in cardiac repair. However, the potential of these cells to completely regenerate the heart is limited. Efforts are now being focused on ways to augment these natural pathways to improve cardiac healing, primarily after ischemic injury but in other cardiac pathologies as well. Cell and gene therapy or pharmacological interventions are proposed mechanisms. Cell therapy has demonstrated modest results and has passed into clinical trials. However, the beneficial effects of cell therapy have primarily been their ability to produce paracrine effects on the cardiac tissue and recruit endogenous stem cell populations as opposed to direct cardiac regeneration. Gene therapy efforts have focused on prolonging or reactivating natural signaling pathways. Positive results have been demonstrated to activate the endogenous stem cell populations and are currently being tested in clinical trials. A potential new avenue may be to refine pharmacological treatments that are currently in place in the clinic. Evidence is mounting that drugs such as statins or beta blockers may alter endogenous stem cell activity. Understanding the effects of these drugs on stem cell repair while keeping in mind their primary function may strike a balance in myocardial healing. To maximize endogenous cardiac regeneration, a combination of these approaches could ameliorate the overall repair process to incorporate the participation of multiple cellular players. PMID:26484341

  7. Cardiac Innervation and Sudden Cardiac Death

    PubMed Central

    Fukuda, Keiichi; Kanazawa, Hideaki; Aizawa, Yoshiyasu; Ardell, Jeffrey L.; Shivkumar, Kalyanam

    2015-01-01

    Afferent and efferent cardiac neurotransmission via the cardiac nerves intricately modulates nearly all physiological functions of the heart (chronotropy, dromotropy, lusitropy and inotropy). Afferent information from the heart is transmitted to higher levels of the nervous system for processing (intrinsic cardiac nervous system, extracardiac-intrathoracic ganglia, spinal cord, brain stem and higher centers) which ultimately results in efferent cardiomotor neural impulses (via the sympathetic and parasympathetic nerves). This system forms interacting feedback loops that provide physiological stability for maintaining normal rhythm and life-sustaining circulation. This system also ensures that there is fine-tuned regulation of sympathetic-parasympathetic balance in the heart under normal and stressed states in the short (beat to beat), intermediate (minutes-hours) and long term (days-years). This important neurovisceral /autonomic nervous system also plays a major role in the pathophysiology and progression of heart disease, including heart failure and arrhythmias leading to sudden cardiac death (SCD). Transdifferentiation of neurons in heart failure, functional denervation, cardiac and extra-cardiac neural remodeling have also been identified and characterized during the progression of disease. Recent advances in understanding the cellular and molecular processes governing innervation and the functional control of the myocardium in health and disease provides a rational mechanistic basis for development of neuraxial therapies for preventing SCD and other arrhythmias. Advances in cellular, molecular, and bioengineering realms have underscored the emergence of this area as an important avenue of scientific inquiry and therapeutic intervention. PMID:26044253

  8. 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

  9. Occurrence of condensed tannins in wheat and feasibility for reducing pasture bloat

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Frothy bloat can be a serious problem with winter wheat (Triticum aestivum L.) pastures, the primary source of cool-season forage in the southern Great Plains. Some forage contains tannins that reduce the incidence and severity of bloat and promote better use of forage protein. The objective of our ...

  10. Condensed tannin in drinking water reduces greenhouse gas precursor urea in sheep and cattle urine

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ingestion of small amounts of naturally-occurring condensed tannin (CT) by ruminants can provide several benefits including potential reduction of ammonia and nitrous oxide emissions over the long-term by reducing their urine urea excretion. However, providing grazing ruminants with sufficient amou...

  11. 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. PMID:24195587

  12. 40 CFR 721.10666 - Quaternary ammonium compounds, bis(fattyalkyl) dimethyl, salts with tannins (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Quaternary ammonium compounds, bis... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10666 Quaternary ammonium compounds... compounds, bis(fattyalkyl) dimethyl, salts with tannins (PMN P-12-437) is subject to reporting under...

  13. 40 CFR 721.10666 - Quaternary ammonium compounds, bis(fattyalkyl) dimethyl, salts with tannins (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Quaternary ammonium compounds, bis... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10666 Quaternary ammonium compounds... compounds, bis(fattyalkyl) dimethyl, salts with tannins (PMN P-12-437) is subject to reporting under...

  14. Determining effects of multiple tannin manure applications on dairy forages and soil

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Dietary choices for dairy cows have direct implications to nutrient availability from land-applied manure because of alterations to manure chemistry. Tannin additions to a dairy cow’s diet protect feed protein through rumen fermentation and digestion, resulting in reduced concentrations of urea nitr...

  15. Impact by condensed tannins with different mean degrees of polymerization on protein precipitation

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Condensed tannins (CTs) isolated from white clover (Trifolium repens) flowers and big trefoil (Lotus pedunculatus) leaves were evaluated in precipitation studies with bovine serum albumin (BSA), lysozyme (LYS), and alfalfa leaf protein (ALF). The CTs were of similar compositions, but differed in the...

  16. [Factors which modify the nutritional state of iron: tannin content of herbal teas].

    PubMed

    Pizarro, F; Olivares, M; Hertrampf, E; Walter, T

    1994-12-01

    Tannins are natural compounds that abound in herbs, wood and fruits. Their numerous hydroxyl radicals confer them a strong avidity for metals such as Fe, Zn and Cu. This property makes them strong inhibitors for the gastrointestinal absorption of these metals. Our purpose was to determine the tannin content of herbal infusions commonly consumed in Chile and other Latino American countries. The determination was performed from dessicated herbs with the Folin-Denis technique. Yerba mate, tea and oregano had the highest tannin content (117, 100 and 84 mg of tannic acid/g dry herb respectively). An intermediate level (between 20 and 40 of tannic acid/g) was for coca, matico, boldo, palto, laurel, orange and binojo. The lowest level of tannin for paico, cedrón, apio and manzanilla (< 10 mg/g). We conclude that the consumption of herbal teas at or around meals may inhibit the absorption of metals such as Fe, Zn, or Cu by decreasing their bioavailability. PMID:8984970

  17. Methane Emission by Goats Consuming Condensed Tannin-containing Forage at Different Frequencies

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Twenty-four yearling Boer and Spanish wethers (33.5 ± 0.36 kg BW) were used in a 32-d experiment to assess effects of frequency of feeding condensed tannin (CT)-containing fresh sericea lespedeza (SL; Lespedeza cuneata) on ruminal methane (CH4) emission. Fresh SL (15.3% CT) was fed free-choice ever...

  18. Molecular diversity in phenolic and polyphenolic precursors of tannin-inspired nanocoatings

    PubMed Central

    Barrett, Devin G.; Sileika, Tadas S.; Messersmith, Phillip B.

    2014-01-01

    The strong interfacial properties of selected plant polyphenols were recently exploited in forming functionally versatile nanocoatings via dip-coating. Here, we screened a library of ~20 natural and synthetic phenols and polyphenols, identifying eight catechol-, gallol- and resorcinol-rich precursors capable of forming coatings. Several newly identified compounds expand the molecular diversity of tannin-inspired coatings. PMID:24871486

  19. Effect of high tannin grain sorghum on gastrointestinal parasite fecal egg counts in goats

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The objective of three experiments was to determine the influence of high condensed tannin (CT) grain sorghum on gastrointestinal parasite fecal egg counts (FEC) in goats. Sixteen naturally-infected Boer crossbred mixed sex goats were used at 124 plus minus 2.9 days of age in Experiment 1, 24 mixe...

  20. 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. PMID:25466016

  1. Bactericidal effect of hydrolysable and condensed tannin extracts on Campylobacter jejuni in vitro

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Strategies are sought to reduce intestinal colonization of food-producing animals by Campylobacter jejuni, a leading bacterial cause of human foodborne illness worldwide. Presently, we tested the antimicrobial activity of hydrolysable-rich blackberry, cranberry, chestnut tannin extracts, and conden...

  2. Tannins Alter Soil Organic Matter Extraction, Solubility of Metals, and Root Physiology

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins are common plant-derived polyphenolic compounds that precipitate proteins and react with other biomolecules but knowledge of their effects on soil organic matter, the solubility of metals, and root physiology is incomplete. Soil from forest and pasture systems was treated with tannic acid (...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The acquisition of plant sterols, mediated via elicitins, is required for growth and sporulation of Phytophthora spp. In this paper, we looked at the interaction between elicitins, sterols, and tannins. When ground leaf tissue was added to growth media, P. ramorum growth and sporulation was greates...

  4. Comparative antimicrobial activity of tannin extracts from perennial plants on mastitis pathogens

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Three strains of pathogenic bacteria were treated with condensed tannins (CT) purified from eight different woody plant species to investigate their inhibition effect on the growth of these bacteria in vitro. Escherichia coli, Klebsiella pneumoniae, and Staphylococcus aureus were tested against low...

  5. 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. PMID:1417702

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Excess crude protein (CP) in dairy cow diets is excreted mostly as urea nitrogen (N), which increases ammonia (NH3) 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 NH3 e...

  7. Methane emission by goats consuming diets with different levels of condensed tannins from lespedeza

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Twenty-four yearling Boer x Spanish wethers (7/8 Boer; initial body weight [BW] of 34.1 plus/minus 1.02 kg) were used to determine effects on methane emission of dietary levels of a condensed tannin (CT)-containing forage, Kobe lespedeza (Lespedeza striata; K), and a forage very low in CT, sorghum-s...

  8. Adsorptive recovery of Au3+ from aqueous solutions using bayberry tannin-immobilized mesoporous silica.

    PubMed

    Huang, Xin; Wang, Yanpin; Liao, Xuepin; Shi, Bi

    2010-11-15

    Tannin is well known to be an inexpensive and ubiquitous natural biomass, which has high chelating affinity towards many metal ions. In this study, bayberry tannin (BT) was immobilized on mesoporous silica matrix to prepare a novel adsorbent, which was subsequently used for the adsorptive recovery of Au(3+) from aqueous solutions. It was found that bayberry tannin-immobilized mesoporous silica (BT-SiO(2)) was able to effectively recover Au(3+) from acidic solutions (pH 2.0). The equilibrium adsorption capacity of Au(3+) on BT-SiO(2) was high up to 642.0 mg/g at 323 K. Due to its mesoporous structure, BT-SiO(2) exhibited an extremely fast adsorption rate to Au(3+) as compared with other tannin gel adsorbent. The presence of other coexisting metal ions, such as Pb(2+), Ni(2+), Cu(2+) and Zn(2+), did not decrease the adsorption capacity of Au(3+) on BT-SiO(2), and BT-SiO(2) had almost no adsorption capacity to these coexisting metal ions, which suggested the high adsorption selectivity of BT-SiO(2) to Au(3+). Additionally, about 73% of adsorbed Au(3+) can be desorbed using aqua regia, and the Au(3+) solution was concentrated about 18.0 times as compared with the original solution. Consequently, the outstanding characteristics of BT-SiO(2) provide the possibility of effective recovery and concentration of Au(3+) from diluted solutions. PMID:20728986

  9. Tannins--a dietary problem for hand-reared grey partridge Perdix perdix after release?

    PubMed

    Liukkonen-Anttila, T; Kentala, A; Hissa, R

    2001-10-01

    A 4-week feeding trial on 22 grey partridges Perdix perdix was conducted in this study. Seven birds were fed commercial poultry food, seven natural food and eight commercial poultry food containing 6% of quebracho-tannin. Our results suggest that 6% dietary tannin, when added to a commercial food with high protein content, effects the grey partridge only slightly. No difference was seen in food consumption and body mass remained stable. However, birds fed tannin had longer small intestines, which most probably indicate gastrointestinal detoxication. They also excreted a high amount of tannin in their faeces. In addition, no between-group variation was seen in cytochrome P450 enzymes. Birds fed natural food had high concentration of nitrogen in intestinal excreta and high plasma alanine concentrations. They also suffered a rapid decrease in body mass after the change in diet and their body mass remained low. This may indicate increased protein excretion and/or catabolism of endogenous nutrient reserves. Potential short-term effects of the change in diet were seen in plasma. These findings coincide with the high mortality period of birds released into the wild. PMID:11574293

  10. Effects of condensed tannins on goats experimentally infected with Haemonchus contortus.

    PubMed

    Paolini, V; Bergeaud, J P; Grisez, C; Prevot, F; Dorchies, Ph; Hoste, H

    2003-05-01

    Although the use of tanniferous plants or condensed tannins as an alternative to anthelmintics to control gastrointestinal nematodes has been largely documented in sheep, studies remain scarce in goats. The objective of this study was therefore to assess the possible impact of condensed tannins in goats infected with adult Haemonchus contortus. Two groups of cull goats were experimentally infected with 10.000 L3 of H. contortus. After 4 weeks, quebracho extracts, representing 5% of the diet DM, were administered for 8 days to one of the two groups. Goats of the second group remained as controls. One week after the end of quebracho administration, the goats were euthanised. Individual egg excretion and pathophysiological parameters were measured weekly during the study. At the end of the study, worm counts were assessed and histological samples from the abomasa were taken to count the numbers of mucosal mast cells, globule leukocytes and eosinophils. The administration of tannins was associated with a significant decrease in egg excretion, which persisted until the end of experiment. This reduction was not associated with any difference in worm number but with a significant decrease in female fecundity. No significant changes in the mucosal density of the three inflammatory cell types were detected between the two groups. These results indicate that the major consequence of tannin consumption in goats is a reduction in worm fecundity and egg output, which does not seem related to significant changes in the local mucosal response. PMID:12719140

  11. Persimmon fruit tannin-rich fiber reduces cholesterol levels in humans.

    PubMed

    Gato, Nobuki; Kadowaki, Akio; Hashimoto, Natsumi; Yokoyama, Shin-ichiro; Matsumoto, Kenji

    2013-01-01

    Bile acid-binding agents are known to lower blood cholesterol levels and have been clinically used for the treatment of hypercholesterolemia. We previously showed that tannin-rich fiber from young persimmon (Diospyros kaki) fruits had bile acid-binding properties. In this study, we performed a randomized, double-blind, placebo-controlled trial to investigate the hypocholesterolemic effects of tannin-rich fiber in humans. The subjects (n = 40, plasma total cholesterol levels 180-259 mg/dl) were divided into 3 groups and ingested cookie bars containing 0 g (placebo group, n = 14), 3 g (low-dose group, n = 13), or 5 g (high-dose group, n = 13) of tannin-rich fiber 3 times daily before meals for 12 weeks. Plasma total cholesterol levels decreased significantly in the low-dose (12 weeks, p < 0.005) and high-dose (6 weeks, p < 0.05; 12 weeks, p < 0.001) groups. In addition, plasma low-density lipoprotein cholesterol levels decreased significantly in the high-dose group (6 weeks, p < 0.05; 12 weeks, p < 0.001). These improvements were not accompanied by changes in plasma high-density lipoprotein cholesterol or plasma triglyceride levels. Our findings indicate that tannin-rich fiber from young persimmon fruits is a useful food material for treating hypercholesterolemia. PMID:23171573

  12. Dietary CP and Tannin Extracts Impact Ammonia Emissions From Manure Deposited On Dairy Barn Floors

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The impact of dietary CP and Quebracho-Chestnut tannin extracts on dairy cow performance and N partitioning are reported elsewhere at this meeting. Mixtures of feces/urine from these studies were applied to lab-scale ventilated chambers to measure ammonia-N emissions (ANE) from simulated concrete ba...

  13. 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. PMID:26937589

  14. Marketing cardiac CT programs.

    PubMed

    Scott, Jason

    2010-01-01

    There are two components of cardiac CT discussed in this article: coronary artery calcium scoring (CACS) and coronary computed tomography angiography (CCTA).The distinctive advantages of each CT examination are outlined. In order to ensure a successful cardiac CT program, it is imperative that imaging facilities market their cardiac CT practices effectively in order to gain a competitive advantage in this valuable market share. If patients receive quality care by competent individuals, they are more likely to recommend the facility's cardiac CT program. Satisfied patients will also be more willing to come back for any further testing. PMID:22276376

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

    PubMed Central

    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

  16. 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

  17. 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. PMID:20173064

  18. Hypotensive action of coumarin glycosides from Daucus carota.

    PubMed

    Gilani, A H; Shaheen, E; Saeed, S A; Bibi, S; Irfanullah; Sadiq, M; Faizi, S

    2000-10-01

    Daucus carota (carrot) has been used in traditional medicine to treat hypertension. Activity-directed fractionation of aerial parts of D. carota resulted in the isolation of two cumarin glycosides coded as DC-2 and DC-3. Intravenous administration of these compounds caused a dose-dependent (1-10 mg/kg) fall in arterial blood pressure in normotensive anaesthetised rats. In the in vitro studies, both compounds caused a dose-dependent (10-200 microg/ml) inhibitory effect on spontaneously beating guinea pig atria as well as on the K+ -induced contractions of rabbit aorta at similar concentrations. These results indicate that DC-2 and DC-3 may be acting through blockade of calcium channels and this effect may be responsible for the blood pressure lowering effect of the compounds observed in the in vivo studies. PMID:11081994

  19. Pregnane-type steroidal glycosides from Gymnema griffithii Craib.

    PubMed

    Srisurichan, Suphongphan; Puthong, Songchan; Pornpakakul, Surachai

    2014-10-01

    Eight pregnane-type steroidal glycosides substituted with ortho-acetate groups were isolated from the methanolic extract of the pericarp of Gymnema griffithii fruits, and named gymnemogriffithosides A-H. Their structures were determined by spectroscopic analysis (one and two dimensional nuclear magnetic resonance, high resolution electrospray ionization mass spectrometry and attenuated total reflectance-Fourier transformed infrared spectroscopy), while the absolute structure of the steroidal skeleton of one of these was additionally determined using Mosher's method. All compounds were evaluated for their in vitro (i) cytotoxic effects against five human tumor cell lines (BT 474, Chago, Hep-G2, KATO-III and SW620) and (ii) α-glucosidase inhibitory activity. PMID:25053002

  20. Uncommon Glycosidases for the Enzymatic Preparation of Glycosides

    PubMed Central

    Trincone, Antonio

    2015-01-01

    Most of the reports in literature dedicated to the use of glycosyl hydrolases for the preparation of glycosides are about gluco- (α- and β-form) and galacto-sidase (β-form), reflecting the high-availability of both anomers of glucosides and of β-galactosides and their wide-ranging applications. Hence, the idea of this review was to analyze the literature focusing on hardly-mentioned natural and engineered glycosyl hydrolases. Their performances in the synthetic mode and natural hydrolytic potential are examined. Both the choice of articles and their discussion are from a biomolecular and a biotechnological perspective of the biocatalytic process, shedding light on new applicative ideas and on the assortment of biomolecular diversity. The hope is to elicit new interest for the development of biocatalysis and to gather attention of biocatalyst practitioners for glycosynthesis. PMID:26404386

  1. A new triterpene glycoside from the stems of Lagerstroemia indica.

    PubMed

    Woo, Kyeong Wan; Cha, Joon Min; Choi, Sang Un; Lee, Kang Ro

    2016-05-01

    A bioassay-guided fractionation and chemical investigation of the stems of Lagerstroemia indica resulted in the isolation and identification of a new triterpene glycoside, lagerindiside (1), along with nine known triterpenes (2-10). The structure of this new compound was elucidated on the basis of 1D and 2D nuclear magnetic resonance spectroscopic data analysis as well as chemical method. The cytotoxic activities of the isolates (1-10) were evaluated by determining their inhibitory effects on four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15) using a sulforhodamine B bioassay. Compounds 3 and 4 showed potent cytotoxicity on the tumor cell lines with IC50 values ranging from 3.38 to 6.29 μM. PMID:27107863

  2. Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L.

    PubMed

    Inoue, Toshio; Sugimoto, Yukio; Masuda, Hideki; Kamei, Chiaki

    2002-02-01

    Six flavonoid glycosides, eriocitrin (1), narirutin (2), hesperidin (3), luteolin-7-O-rutinoside (4), isorhoifolin (5), diosmin (6), rosmarinic acid (7) and 5,7-dihydroxycromone-7-O-rutinoside (8), were isolated from the aerial part of Mentha piperita L. Among these compounds, compound 4 showed a potent inhibitory effect on histamine release induced by compound 48/80 and antigen-antibody reaction. This compound was more effective than luteolin and luteolin-7-O-glucoside in inhibiting histamine release from rat peritoneal mast cells. Compound 4 also caused a dose-related inhibition of the antigen-induced nasal response and significant effects were observed at doses of 100 and 300 mg/kg. These results indicate that compound 4 may be clinically useful in alleviating the nasal symptoms of allergic rhinitis. PMID:11853178

  3. New flavonolignan glycosides from the aerial parts of Zizania latifolia.

    PubMed

    Lee, Seung-Su; Baek, Nam-In; Baek, Yoon-Su; Chung, Dae-Kyun; Song, Myoung-Chong; Bang, Myun-Ho

    2015-01-01

    Two new flavonolignan glycosides, tricin-4'-O-(threo-β-guaiacylglyceryl) ether 7''-O-β-D-glucopyranose (4) and tricin-4'-O-(erythro-β-guaiacylglyceryl) ether 7''-O-β-D-glucopyranose (5) were isolated from the roots of Zizania latifolia, together with tricin-7-O-β-D-glucopyranose (1), tricin-4'-O-(threo-β-guaiacylglyceryl) ether 7-O-β-D-glucopyranose (2), and tricin-4'-O-(erythro-β-guaiacylglyceryl) ether 7-O-β-D-glucopyranose (3). Their structures were identified on the basis of spectroscopic techniques, including HR-ESI/MS, 1D-NMR (1H, 13C, DEPT), 2D-NMR (gCOSY, gHSQC, gHMBC), and IR spectroscopy. PMID:25830790

  4. A new antibacterial benzophenone glycoside from Psidium guajava (Linn.) leaves.

    PubMed

    Ukwueze, Stanley E; Osadebe, Patience O; Okoye, Festus B C

    2015-01-01

    Bioactivity-guided fractionation of methanol extract from the leaves of Psidium guajava L. (Myrtaceae) yielded a new benzophenone glycoside, Guajaphenone A (2) together with two known compounds, Garcimangosone D (1) and Guaijaverin (3). Their structures were elucidated by analysis of spectroscopic data including 1D and 2D NMR and electrospray ionisation mass spectrometry (ESI-MS). The isolated compounds were screened against standard strains of Gram-positive and Gram-negative bacteria using broth dilution assay method, and the MIC values determined and compared with reference antibiotic ceftriaxone. They were found to have significant antibacterial activities against Escherichia coli and Staphylococcus aureus with all of them showing better activities against S. aureus, but displaying weaker activities, in comparison to ceftriaxone. However, despite reduced effect of these compounds against the organisms, this work opens the perspective to use these molecules as 'leads' for the design of novel and selective drug candidates for some tropical infectious diseases. PMID:25631395

  5. Pregnane glycoside multidrug-resistance modulators from Cynanchum wilfordii.

    PubMed

    Hwang, B Y; Kim, S E; Kim, Y H; Kim, H S; Hong, Y S; Ro, J S; Lee, K S; Lee, J J

    1999-04-01

    The methanol-soluble extracts of the roots of Cynanchum wilfordii showed a significant multidrug-resistance-reversing activity, and four known pregnane glycosides were isolated by bioassay-directed fractionation and separation. Their structures were identified as gagaminin 3-O-beta-D-cymaropyranosyl-(1-->4)-beta-D-oleandropyranosyl- (1-->4)-b eta-D-cymaropyranosyl-(1-->4)-beta-D-cymaropyranoside (1), wilfoside K1N (2), wilfoside C1N (3), and cynauricuoside A (4). In particular, compound 1, at a concentration level of 1 microM, was found to completely reverse the multidrug-resistance of KB-V1 and MCF7/ADR cells to adriamycin, vinblastine, and colchicine. PMID:10217732

  6. Aromatic glycosides from the whole plants of Iris japonica.

    PubMed

    Shi, Guo-Ru; Wang, Xin; Liu, Yan-Fei; Zhang, Chun-Lei; Wang, Yan; Li, Li; Ni, Gang; Chen, Ruo-Yun; Yu, De-Quan

    2016-10-01

    Phytochemical investigation on the whole plants of Iris japonica led to the isolation of four new aromatic glycosides. Their structures including the absolute configurations were determined by spectroscopic and chemical methods as (-)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (1), (-)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (2), (-)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (3), (-)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (4), respectively. PMID:27310650

  7. Acutifoliside, a novel benzoic acid glycoside from Salix acutifolia.

    PubMed

    Wu, Yanqi; Dobermann, Darja; Beale, Michael H; Ward, Jane L

    2016-08-01

    Ultra high-performance liquid chromatography-mass spectrometry (UHPLC-MS) profiling of a polar solvent extract of juvenile stem tissue of Salix acutifolia Willd. identified a range of phenolic metabolites. Salicortin, 1, a well-known salicinoid, was the major compound present and the study identified young stem tissue of this species as a potential source of this compound for future studies. Three further known metabolites (salicin 2, catechin 3 and tremuloidin 4) were also present. The UHPLC-MS analysis also revealed the presence of a further, less polar, unknown compound, which was isolated via HPLC peak collection. The structure was elucidated by high-resolution mass spectroscopic analysis, 1- and 2-D NMR analysis and chemical derivatisation and was shown to be a novel benzoic acid glycoside 5, which we have named as acutifoliside. PMID:26820172

  8. Acetylated flavonoid glycosides potentiating NGF action from Scoparia dulcis.

    PubMed

    Li, Yushan; Chen, Xigui; Satake, Masayuki; Oshima, Yasukatsu; Ohizumi, Yasushi

    2004-04-01

    Three new acetylated flavonoid glycosides, 5,6,4'-trihydroxyflavone 7-O-alpha-L-2,3-di-O-acetylrhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (1), apigenin 7-O-alpha-L-3-O-acetylrhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (2), and apigenin 7-O-alpha-L-2,3-di-O-acetylrhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (3), were isolated from Scoparia dulcis together with the known compound eugenyl beta-D-glucopyranoside (4). Their structures were elucidated by spectroscopic analyses. Compounds 2 and 3 showed an enhancing activity of nerve growth factor-mediated neurite outgrowth in PC12D cells. PMID:15104516

  9. Four new glycosides from the fruit of Xanthium sibiricum Patr.

    PubMed

    Jiang, Hai; Yang, Liu; Liu, Chang; Hou, Hui; Wang, Qiuhong; Wang, Zhibin; Yang, Bingyou; Kuang, Haixue

    2013-01-01

    Four new glycosides, namely 3β-norpinan-2-one 3-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (1), (6Z)-3-hydroxymethyl-7-methylocta-1,6-dien-3-ol 8-O-β-d-glucopyranoside (2), (6E)-3-hydroxymethyl-7-methylocta-1,6-dien-3-ol 8-O-β-d-gluco-pyranoside (3), and 7-[(β-d-apiofuranosyl-(1→6)-β-d-glucopyranosyl)oxymethy]-8,8-dimethyl-4,8-dihydrobenzo[1,4]thiazine-3,5-dione (4), were isolated from the fruits of Xanthium sibiricum Patr together with three known compounds, xanthiside (5), adenosine (6), and 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one (7). The structures of the new compounds were determined on the basis of detailed spectroscopic analyses. PMID:24152669

  10. Two new sesquiterpenoid glycosides from the leaves of Lycium barbarum.

    PubMed

    Wang, Yan; Zhao, Bo; Ma, Hai-Rong; Aisa, Haji Akber

    2016-09-01

    Two new sesquiterpenoid glycosides, lyciumionosides A-B (1-2), together with four known compounds (3-6), were isolated from the leaves of Lycium barbarum. Their structures were mainly established on the basis of MS, 1D and 2D NMR spectroscopic techniques. The antiproliferative activities of compounds 1-5 were evaluated. Compound 1 showed highest inhibitory activity against A549 cells with IC50 value of 32.6 ± 2.6 μM, compound 3 showed highest inhibitory activity against PC-3 cells with IC50 value of 36.0 ± 2.9 μM, and compound 5 exhibited highest inhibitory activity against HeLa cells with IC50 value of 32.3 ± 4.2 μM. PMID:27176709

  11. Phenylpropanoid Glycosides from the Leaves of Ananas comosus.

    PubMed

    Chen, Wen-Hao; Huang, Xiao-Juan; Shu, Huo-Ming; Hui, Yang; Guo, Fei-Yan; Song, Xiao-Ping; Ji, Ming-Hui; Chen, Guang-Ying

    2015-12-01

    Two new phenylpropanoid glycosides, named β-D-(1-O-acetyl-3,6-O-diferuloyl) fructofuranosyl β-D-6'-O-acetylglucopyranoside (1) and β-D-(1-O-acetyl-3,6-O-diferuloyl) fructofuranosyl α-D-glucopyranoside (2), along with two known analogues (3-4) and four glycerides (5-8), were isolated from the EtOAc extract of the leaves of Ananas comosus. Their structures were elucidated on the basis of 1D- and 2D-NMR analyses, as well as HR-ESI-MS experiments. Compounds 1-4 showed significant antibacterial activities against Staphylococcus aureus and Escherichia coli. PMID:26882684

  12. Enzymatic hydrolysis of steryl glycosides for their analysis in foods.

    PubMed

    Münger, Linda H; Nyström, Laura

    2014-11-15

    Steryl glycosides (SG) contribute significantly to the total intake of phytosterols. The standard analytical procedure involving acid hydrolysis fails to reflect the correct sterol profile of SG due to isomerization of some of the labile sterols. Therefore, various glycosylases were evaluated for their ability to hydrolyse SG under milder conditions. Using a pure SG mixture in aqueous solution, the highest glycolytic activity, as demonstrated by the decrease in SG and increase in free sterols was achieved using inulinase preparations (decrease of >95%). High glycolytic activity was also demonstrated using hemicellulase (63%). The applicability of enzymatic hydrolysis using inulinase preparations was further verified on SG extracted from foods. For example in potato peel Δ(5)-avenasteryl glucoside, a labile SG, was well preserved and contributed 26.9% of the total SG. Therefore, enzymatic hydrolysis is suitable for replacing acid hydrolysis of SG in food lipid extracts to accurately determine the sterol profile of SG. PMID:24912717

  13. Neolignans and glycosides from the stem bark of Illicium difengpi.

    PubMed

    Fang, Lei; Du, Dan; Ding, Guang-Zhi; Si, Yi-Kang; Yu, Shi-Shan; Liu, Yang; Wang, Wen-Jie; Ma, Shuang-Gang; Xu, Song; Qu, Jing; Wang, Jia-Ming; Liu, Yu-Xi

    2010-05-28

    Five new neolignans (1-4 and 9), two pairs of neolignan epimers (5-8), and two new aromatic glycosides (10 and 11) have been isolated from the stem bark of Illicium difengpi. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRESIMS, CD experiments, and chemical methods. The absolute configurations of the 3,4-diol moiety in 1 and 1,3-diol moiety in 2 were confirmed by Snatzke's method, observing the induced circular dichroism after addition of dimolybdenum tetraacetate in DMSO. Compounds 3, 4, and 11 exhibited moderate anti-inflammatory activities with IC(50) values ranging from 1.62 to 24.4 microM, while compound 3 displayed antioxidant activity with an IC(50) value of 42.3 microM. PMID:20411974

  14. A new phenylethanoid glycoside from Orobanche cernua Loefling.

    PubMed

    Qu, Zheng-Yi; Zhang, Yu-Wei; Zheng, Si-Wen; Yao, Chun-Lin; Jin, Yin-Ping; Zheng, Pei-He; Sun, Cheng-He; Wang, Ying-Ping

    2016-04-01

    A novel phenylethanoid glycoside, 3'-O-methyl isocrenatoside (1), along with two known compounds, methyl caffeate (2) and protocatechuic aldehyde (3), were isolated from the fresh whole plant of Orobanche cernua Loefling. All the isolated compounds (1-3) were elucidated on the basis of spectroscopic analysis including IR, MS and NMR data. The cytotoxic activities of these compounds were evaluated. Results showed that 3'-O-methyl isocrenatoside (1) and methyl caffeate (2) exhibited significant cytotoxicity, with IC50 values of 71.89, 36.97 μg/mL and 32.32, 34.58 μg/mL against the B16F10 murine melanoma and Lewis lung carcinoma cell lines, respectively. PMID:26358786

  15. 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. PMID:24789995

  16. Adams-Harbertson protein precipitation-based wine tannin method found invalid.

    PubMed

    Brooks, Larry; McCloskey, Leo; McKesson, Doug; Sylvan, Marshall

    2008-01-01

    The poor precision of the Adams-Harbertson wine tannin assay which was proposed for commercial winemaking, thereby creating the real possibility of quality control problems, is documented. The method is a version of the Hagerman and Butler protein precipitation-based tannin method. An extensive invalidation of the assay results with luxury wine data shows that the assay cannot distinguish bottled wine with reasonable accuracy. Five laboratories used Adams-Harbertson to assay 9 replicates each, of 3 bottled wines (n = 135) found in California supermarkets, with tannin concentrations of nominally 500 and 1000 ppm by high-performance liquid chromatography (HPLC). Reliability exceeded the +/-5% industry requirement by nominally 5 times (z-score based on 5% distribution). Coefficient of variation was +/-27%, making the standard deviation range 54% for Pinot Noir, 34% for Merlot, and 44% for Cabernet Sauvignon. Validity exceeded the 100% requirement. Intralaboratory validity recovery was 55-63%. Interwinery validity was 71-178% of the mean for Pinot Noir, 81-144% for Merlot, and 83-164% for Cabernet Sauvignon. Range as a function of the mean was 89% for Pinot Noir, 55% for Merlot, and 67% for Cabernet Sauvignon. Expect intermethod validity to be nominally 50%, i.e., percent recovery to HPLC. These statistically significant errors were predicted by the literature. First-order error is related to the tannin-protein equilibrium constant (Ka), as suggested by the original author, Hagerman, and the protein equivalence point error as suggested by Silber. This does not obviate second-order errors for tannin-protein analytical chemistry. Winemakers using the measurements risk making wines that are relatively more tannic than the measurements report. PMID:18980123

  17. Effects of supplemental dietary tannins on the performance of white-tailed deer (Odocoileus virginianus).

    PubMed

    Chapman, G A; Bork, E W; Donkor, N T; Hudson, R J

    2010-02-01

    Tannins are natural and nutritionally significant components of the diets of browsing ungulates. In trials on supplemented pastures and in drylots, we estimated dry matter intake (DMI), weight gain, and urea N, potassium, cortisol and creatinine in urine of captive white-tailed deer fed pelleted diets that differed only in the respective quebracho tannin (QT) content. The low control, medium and high QT rations were 3.6, 63 and 152 g/kg DM respectively. There was no tannin-free pellet option. Trials were divided into winter pasture, restricted choice and spring growth. In winter pasture trial on pasture using QT, deer reduced QT intake relative to that expected under random foraging. This aversion was also apparent during the spring growth trial. While DMI in the winter pasture trial remained similar among treatments (p > 0.05), averaging 130 g/kg(0.75)/day, deer gained more weight (p < 0.05) when given a choice that included the high QT ration. During subsequent spring growth, DMI and weight gains generally exceeded those of the winter period. Unlike the winter pasture trial, weight gains in spring growth trial were higher (p < 0.05) in the low-control QT treatment. In the restricted choice trial, weight gain was again higher (p < 0.05) for deer fed a low-control QT diet. The urea N/creatinine ratio of deer fed the low-control QT diet (0.0357) was over three times that of deer fed the high QT diet (0.0107). Neither potassium/creatinine nor cortisol/creatinine ratios were affected by diet (p > 0.05). Collectively, these results suggest that although deer do not avoid tannins, and even ingested up to 5% under the choice options in these trials, the effect of tannins on deer performance may vary by season as well as by foraging opportunities. PMID:19364384

  18. Variations in human urinary O-hydroxylysyl glycoside levels and their relationship to collagen metabolism

    PubMed Central

    Segrest, Jere P.; Cunningham, Leon W.

    1970-01-01

    Two O-hydroxylysyl glycosides, Hyl-Gal-Glc and Hyl-Gal, have been isolated from normal human urine and shown to be identical to two glycosides isolated from alkaline hydrolysates of collagen. A relatively sample and reproducible analytical procedure has been devised to measure the levels of these glycosides in human urine. By the use of this procedure it was shown that a normal diet has only a small effect on 24-hr urinary excretion levels of these glycosides indicating an endogenous origin. Urinary glycoside levels appear to be highest in children, roughly paralleling collagen turnover as indicated by urinary hydroxyproline levels. Collagen turnover equivalents calculated from urinary hydroxylysyl glycoside levels were found to be significantly larger than collagen turnover equivalents calculated from urinary hydroxyproline levels. This suggests that urinary glycosides are more quantitative indicators of collagen metabolism than urinary hydroxyproline. The ratio of Hyl-Gal-Glc to Hyl-Gal was measured in urines of diseased as well as normal individuals and a bimodal distribution was found. Alkaline hydrolysates of different human connective tissue collagens showed that only bone collagen, of the collagens examined, had a low ratio of Hyl-Gal-Glc to Hyl-Gal compared to human urine. Other collagens examined had higher ratios than found in human urine. On the basis of these results it is postulated that the bimodal distribution of glycoside ratios represents two populations of collagen turnover, the lower ratio population having a high bone collagen turnover, the lower ratio population having a high bone collagen turnover relative to the second population. Examination of the types of subjects making up the two populations supports this hypothesis. These data suggest that urinary O-hydroxylysyl glycoside excretion, in addition to providing a more quantitative estimate of collagen turnover than urinary hydroxyproline, may prove to be of value as a specific means of

  19. 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. PMID:23205499

  20. Metabolic fate of fatty acids involved in ruminal biohydrogenation in sheep fed concentrate or herbage with or without tannins.

    PubMed

    Vasta, V; Mele, M; Serra, A; Scerra, M; Luciano, G; Lanza, M; Priolo, A

    2009-08-01

    A 2 x 2 factorial experiment was carried out to evaluate the effect of herbage or concentrate feeding and dietary tannin supplementation on fatty acid metabolism and composition in sheep ruminal fluid, plasma, and intramuscular fat. Twenty-eight male lambs were divided into 2 equal groups at 45 d of age and kept in individual pens. One group was given exclusively fresh herbage (vetch), and the other group was fed a concentrate-based diet. Within each treatment, one-half of the lambs received supplementation of quebracho powder, providing 4.0% of dietary DM as tannins. Before slaughter, blood samples were collected. The animals were slaughtered at 105 d of age, and ruminal contents and LM were collected. Blood plasma, ruminal fluid, and LM fatty acid composition was determined by gas chromatography. Tannin supplementation reduced (P < 0.05) the concentration of stearic acid (-49%) and increased the concentration of vaccenic acid (+97%) in ruminal fluid from concentrate-fed lambs. Within concentrate- and herbage-based diets, tannin supplementation reduced the accumulation of SFA in blood (P < 0.05) compared with lambs fed the tannin-free diets. When tannins were included in the concentrate, the LM contained 2-fold greater concentrations of rumenic acid compared with the LM of the lambs fed the tannin-free concentrate (0.96 vs. 0.46% of total extracted fatty acids, respectively; P < 0.05). The concentration of PUFA was greater (P < 0.05) and SFA (P < 0.01) less in the LM from lambs fed the tannin-containing diets as compared with the animals receiving the tannin-free diets. These results confirm, in vivo, that tannins reduce ruminal biohydrogenation, as previously reported in vitro. This implies that tannin supplementation could be a useful strategy to increase the rumenic acid and PUFA content and to reduce the SFA in ruminant meats. However, the correct dietary concentration of tannins should be carefully chosen to avoid negative effects on DMI and animal

  1. Steroidal glycosides from the underground parts of Yucca glauca and their cytotoxic activities.

    PubMed

    Yokosuka, Akihito; Suzuki, Tomoka; Tatsuno, Satoru; Mimaki, Yoshihiro

    2014-05-01

    Six steroidal glycosides and 14 known compounds were isolated from the underground parts of Yucca glauca (Agavaceae). Their structures were determined from extensive spectroscopic analysis, including analysis of two-dimensional NMR data, and from chemical transformations. The compounds were also evaluated for cytotoxic activities against HL-60 human leukemia cells and A549 human lung adenocarcinoma cells. Four spirostanol glycosides and three furostanol glycosides exhibited cytotoxic activities against both HL-60 and A549 cells. Two of the compounds induced apoptosis in HL-60 cells. PMID:24612536

  2. Blunt cardiac rupture.

    PubMed

    Martin, T D; Flynn, T C; Rowlands, B J; Ward, R E; Fischer, R P

    1984-04-01

    Blunt injury to the heart ranges from contusion to disruption. This report comprises 14 patients seen during a 6-year period with cardiac rupture secondary to blunt trauma. Eight patients were injured in automobile accidents, two patients were injured in auto-pedestrian accidents, two were kicked in the chest by ungulates, and two sustained falls. Cardiac tamponade was suspected in ten patients. Five patients presented with prehospital cardiac arrest or arrested shortly after arrival. All underwent emergency department thoracotomy without survival. Two patients expired in the operating room during attempted cardiac repair; both had significant extracardiac injury. Seven patients survived, three had right atrial injuries, three had right ventricular injuries, and one had a left atrial injury. Cardiopulmonary bypass was not required for repair of the surviving patients. There were no significant complications from the cardiac repair. The history of significant force dispersed over a relatively small area of the precordium as in a kicking injury from an animal or steering wheel impact should alert the physician to possible cardiac rupture. Cardiac rupture should be considered in patients who present with signs of cardiac tamponade or persistent thoracic bleeding after blunt trauma. PMID:6708151

  3. Sudden Cardiac Death

    PubMed Central

    Weinberg, Marc

    1978-01-01

    Over the past decade, there has been a significant decrease in the hospital mortality of patients with coronary artery disease. However, sudden cardiac death, which accounts for the majority of deaths from coronary artery disease, hasbeen little affected. This report reviews the pathology, electrophysiology, demographics and clinical presentation of sudden cardiac death. Emergency care and possible preventative measures are examined. PMID:356435

  4. Cardiac Hegemony of Senescence.

    PubMed

    Siddiqi, Sailay; Sussman, Mark A

    2013-12-01

    Cardiac senescence and age-related disease development have gained general attention and recognition in the past decades due to increased accessibility and quality of health care. The advancement in global civilization is complementary to concerns regarding population aging and development of chronic degenerative diseases. Cardiac degeneration has been rigorously studied. The molecular mechanisms of cardiac senescence are on multiple cellular levels and hold a multilayer complexity level, thereby hampering development of unambiguous treatment protocols. In particular, the synergistic exchange of the senescence phenotype through a senescence secretome between myocytes and stem cells appears complicated and is of great future therapeutic value. The current review article will highlight hallmarks of senescence, cardiac myocyte and stem cell senescence, and the mutual exchange of senescent secretome. Future cardiac cell therapy approaches require a comprehensive understanding of myocardial senescence to improve therapeutic efficiency as well as efficacy. PMID:24349878

  5. Cardiac Hegemony of Senescence

    PubMed Central

    Siddiqi, Sailay; Sussman, Mark A.

    2013-01-01

    Cardiac senescence and age-related disease development have gained general attention and recognition in the past decades due to increased accessibility and quality of health care. The advancement in global civilization is complementary to concerns regarding population aging and development of chronic degenerative diseases. Cardiac degeneration has been rigorously studied. The molecular mechanisms of cardiac senescence are on multiple cellular levels and hold a multilayer complexity level, thereby hampering development of unambiguous treatment protocols. In particular, the synergistic exchange of the senescence phenotype through a senescence secretome between myocytes and stem cells appears complicated and is of great future therapeutic value. The current review article will highlight hallmarks of senescence, cardiac myocyte and stem cell senescence, and the mutual exchange of senescent secretome. Future cardiac cell therapy approaches require a comprehensive understanding of myocardial senescence to improve therapeutic efficiency as well as efficacy. PMID:24349878

  6. 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. PMID:18710801

  7. 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

  8. Two new cycloartane glycosides from the underground parts of Aquilegia vulgaris.

    PubMed

    Yoshimitsu, Hitoshi; Nishida, Makiko; Nohara, Toshihiro

    2008-11-01

    Two new cycloartane glycosides, named aquilegiosides K and L, have been isolated from the dried underground parts of Aquilegia vulgaris. Their structures were determined by two dimensional (2D) NMR spectroscopic analysis and chemical evidence. PMID:18981620

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

    PubMed

    Khennouf, Seddik; Benabdallah, Hassiba; Gharzouli, Kamel; Amira, Smain; Ito, Hideyuki; Kim, Tae-Hoon; Yoshida, Takashi; Gharzouli, Akila

    2003-02-26

    The gastroprotective effects of 70% acetone extracts of Quercus suber and Quercus coccifera leaves and of tannins (pedunculagin, castalagin, phillyraeoidin A, and acutissimin B) purified from these extracts were examined in the mouse using the ethanol-induced gastric ulcer model. Both extracts (25, 50, and 100 mg/kg), given orally, prevented the formation of ethanol-induced lesions in the stomach. The percent protection varied between 68 and 91%. Purified tannins (50 mg/kg) were also effective in protecting the stomach against ethanol, and the percent protection varied from 66 to 83%. Castalagin was the most potent. Both extracts and all of the tannins tested (10, 25, and 50 microg/mL) strongly inhibited (55-65%) the lipid peroxidation of rabbit brain homogenate. These results suggest that the gastroprotective effects of extracts of Q. suber and Q. coccifera leaves and the purified tannins in this experimental model are related to their anti-lipoperoxidant properties. PMID:12590500

  10. 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. PMID:24987926

  11. 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. PMID:27211695

  12. Preference for tannin-containing supplements by sheep consuming endophyte-infected tall fescue hay.

    PubMed

    Bernard, M; Maughan, B; Villalba, J J

    2013-07-01

    Tannins may bind to alkaloids in endophyte-infected (E+) tall fescue and attenuate fescue toxicosis. To test this hypothesis, thirty-two 4-mo-old lambs were randomly assigned to 4 treatments (8 lambs/treatment) in a 2 by 2 factorial design that included a basal diet of tall fescue hay [E+ or endophyte-free (E-)] supplemented with (TS) or without (CS) bioactive Quebracho tannins. The concentration of ergovaline in E+ fed in 2 successive phases was 65 ± 21 µg/kg (Phase 1) and 128 ± 4 µg/kg (Phase 2). After exposure to hays and supplements, all lambs were offered choices between TS and CS and between E+ and E- hays. During Phase 1, lambs offered E+ consumed more hay than lambs offered E- (P = 0.03). Lambs on E+/TS displayed the greatest intake of hay and the least intake of TS (P < 0.05). During Phase 2, when the concentration of ergovaline increased, lambs offered E+ consumed less hay than lambs fed E- (P < 0.0001). Lambs on E+/CS consumed less hay than lambs on E-/CS (P = 0.02), but hay intake by lambs on E-/TS and E+/TS did not differ (P = 0.96). Lambs preferred CS to TS during preference tests (P < 0.0001) and lambs on E+/TS ingested the least amounts of supplement TS and the greatest amounts of supplement CS (P = 0.001). Lambs offered E+ displayed greater body temperatures than lambs offered E- in both phases (P < 0.05). When offered a choice among the 3 hays, lambs previously exposed to E+ preferred E+ (low content of ergovaline) > E- > E+ (greater content of ergovaline; P < 0.001). Thus, decreased concentrations of ergovaline increased rectal temperatures, and affected intake of and preference for tannins and fescue hay. Quebracho tannins did not attenuate the effects of E+ on body temperature and feed intake. Ingestion of E+ reduced intake of quebracho tannins, suggesting that alkaloids in E+ antagonized ingestion of condensed tannins. PMID:23658337

  13. Influence of macronutrients and polyethylene glycol on intake of a quebracho tannin diet by sheep and goats.

    PubMed

    Villalba, J J; Provenza, F D; Banner, R E

    2002-12-01

    We determined if supplemental macronutrients or polyethylene glycol (PEG) influenced intake of a tannin diet. Sheep (lambs 5 mo age, 36 kg) and goats (kids 7 mo age, 32 kg) were fed supplements high in either energy or protein or offered a choice between the two supplements before and after receiving a meal containing 15% quebracho tannin. The effect of PEG, a compound that attenuates the negative effects of tannins, was assessed by offering PEG while animals consumed the tannin diet for 4 h/d. Intake of the tannin diet was influenced by both macronutrients and PEG. Animals that chose their own supplements or that received the high-protein supplement, consumed more of the tannin diet than animals fed the high-energy supplement: 34 and 36 vs 31 g/kg(0.75) (lambs) and 41 and 39 vs 34 g/kg(0.75) (kids), respectively (P < 0.05). Animals supplemented with PEG ate much more of the tannin diet than unsupplemented animals: 70 vs 39 g/kg(0.75) (lambs) and 63 vs 34 g/kg(0.75) (kids), respectively (P < 0.001). Sheep and goats consumed more tannin food when given PEG than when supplemented with macronutrients (51 and 38 g/kg(0.75), P < 0.001). Sheep and goats offered a choice between supplements consumed more CP than animals fed the high-energy supplement and more ME than animals fed the high-protein supplement (P < 0.05). In so doing, they selected a combination of foods that yielded a more balanced intake of macronutrients, while achieving high levels of intake of the tannin food. Sheep and goats can be used as an environmentally safe and economically sound means to reduce the abundance of tannin-rich vegetation. Macronutrients and PEG enhance use of tannin-containing plants, which may increase production of alternate forages and create a more diverse mix of species in a plant community. PMID:12542156

  14. 6-Hydroxypelargonidin glycosides in the orange-red flowers of Alstroemeria.

    PubMed

    Tatsuzawa, Fumi; Saito, Norio; Murata, Naho; Shinoda, Koichi; Shigihara, Atsushi; Honda, Toshio

    2003-04-01

    Two 6-hydroxypelargonidin glycosides were isolated from the orange-red flowers of Alstroemeria cultivars, and determined to be 6-hydroxypelargonidin 3-O-(beta-D-glucopyranoside) and 3-O-[6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside], respectively, by chemical and spectroscopic methods. In addition, five known anthocyanidin glycosides, 6-hydroxycyanidin 3-malonylglucoside, 6-hydroxycyanidin 3-rutinoside, cyanidin 3-malonylglucoside, cyanidin 3-rutinoside and pelargonidin 3-rutinoside were identified in the flowers. PMID:12648544

  15. A new taraxastane-type triterpenoid glycoside from the roots of Clematis uncinata.

    PubMed

    Li, Shuo-Guo; Li, Man-Mei; Zhao, Bing-Xin; Wang, Ying; Ye, Wen-Cai

    2015-01-01

    A new taraxastane-type triterpenoid glycoside, clematiunicinoside I (1), together with four known ones (2-5), was isolated from the roots of Clematis uncinata. The structure of the new compound was elucidated on the basis of spectroscopic analyses and acid hydrolysis. The cytotoxic activities of all the compounds against caski cervical cancer (Caski) cells were evaluated. This is the first report of the presence of taraxastane-type triterpenoid glycoside in the genus Clematis. PMID:26651184

  16. O2 Protonation Controls Threshold Behavior for N-Glycosidic Bond Cleavage of Protonated Cytosine Nucleosides.

    PubMed

    Wu, R R; Rodgers, M T

    2016-06-01

    IRMPD action spectroscopy studies of protonated 2'-deoxycytidine and cytidine, [dCyd+H](+) and [Cyd+H](+), have established that both N3 and O2 protonated conformers coexist in the gas phase. Threshold collision-induced dissociation (CID) of [dCyd+H](+) and [Cyd+H](+) is investigated here using guided ion beam tandem mass spectrometry techniques to elucidate the mechanisms and energetics for N-glycosidic bond cleavage. N-Glycosidic bond cleavage is observed as the major dissociation pathways resulting in competitive elimination of either protonated or neutral cytosine for both protonated cytosine nucleosides. Electronic structure calculations are performed to map the potential energy surfaces (PESs) for both N-glycosidic bond cleavage pathways observed. The molecular parameters derived from theoretical calculations are employed for thermochemical analysis of the energy-dependent CID data to determine the minimum energies required to cleave the N-glycosidic bond along each pathway. B3LYP and MP2(full) computed activation energies for N-glycosidic bond cleavage associated with elimination of protonated and neutral cytosine, respectively, are compared to measured values to evaluate the efficacy of these theoretical methods in describing the dissociation mechanisms and PESs for N-glycosidic bond cleavage. The 2'-hydroxyl of [Cyd+H](+) is found to enhance the stability of the N-glycosidic bond vs that of [dCyd+H](+). O2 protonation is found to control the threshold energies for N-glycosidic bond cleavage as loss of neutral cytosine from the O2 protonated conformers is found to require ∼25 kJ/mol less energy than the N3 protonated analogues, and the activation energies and reaction enthalpies computed using B3LYP exhibit excellent agreement with the measured thresholds for the O2 protonated conformers. PMID:27159774

  17. Kaempferol 3,7,4'-glycosides from the flowers of Clematis cultivars.

    PubMed

    Sakaguchi, Keisuke; Kitajima, Junichi; Iwashina, Tsukasa

    2013-08-01

    A new kaempferol glycoside, kaempferol 3-O-alpha-rhamnopyranosyl-(1 --> 6)-beta-glucopyranoside-7,4'-di-O-beta-glucopyranoside (1) was isolated from the flowers of Clematis cultivars "Jackmanii Superba" and "Fujimusume", together with the known compound kaempferol 3,7,4'-tri-O-beta-glucopyranoside (2). The chemical structures of the isolated kaemferol glycosides were established by UV, 1H and 13C NMR spectroscopy, LC-MS, and characterization of acid hydrolysates. PMID:24079175

  18. A New Resin Glycoside, Muricatin IX, from the Seeds of Ipomoea muricata.

    PubMed

    Ono, Masateru; Taketomi, Saki; Kakiki, Yuichi; Yasuda, Shin; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

    2016-01-01

    A new resin glycoside, named muricatin IX (1), was isolated from the seeds of Ipomoea muricata (L.) JACQ. (Convolvulaceae). The structure of 1 was determined on the basis of spectroscopic data as well as chemical evidence. Compound 1 is the first representative of resin glycosides in which an organic acid connects the sugar moiety and the aglycone moiety to form macrocyclic ester ring. PMID:27581646

  19. 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.

  20. Effect of condensed tannins extracted from four forages on the viability of the larvae of deer lungworms and gastrointestinal nematodes.

    PubMed

    Molan, A L; Hoskin, S O; Barry, T N; McNabb, W C

    2000-07-01

    The inhibitory activity of condensed tannins extracted from four forage legume plants were evaluated by using a larval migration inhibition assay. The first (L1) and third (L3) stages of deer lungworm (Dictyocaulus viviparus), and the third stage (L3) of deer gastrointestinal nematodes were incubated with tannins extracted from Lotus pedunculatus, Lotus corniculatus, sulla (Hedysarum coronarium) and sainfoin (Onobrychus viciifolia). The tannins extracted from all the forages had inhibitory activity as measured by their ability to paralyse the larvae and inhibit them from passing through sieves. At the highest concentration used (1200 microg/ml) the tannins extracted from sainfoin had the highest activity against ensheathed L1 lungworm larvae (58 per cent), followed by L. pedunculatus (45 per cent), sulla (42 per cent) and L. comiculatus (35 per cent) when the larvae were incubated at 37 degrees C. The same trend, but with lower activities, was observed when the larvae were incubated at 22 degrees C. Anthelmintic activity against L3 lungworm larvae was evaluated by measuring the death rate of ensheathed L3 larvae after incubation with condensed tannins for two, 24 and 48 hours at room temperature (22 degrees C). The death rate was significantly higher (P<0.001) after 48 hours incubation than after two hours or 24 hours, and significantly higher (P<0.001) after 24 hours than after two hours incubation. Condensed tannins from sainfoin had the highest inhibitory activity followed by L. pedunculatus, sulla and L. comiculatus. The tannins from sainfoin also had the highest activity against L3 larvae of gastrointestinal nematodes, followed by L. pedunculatus, sulla and L. comiculatus. Exsheathed larvae of gastrointestinal nematodes were significantly more susceptible to the action of the tannins than ensheathed larvae. PMID:10955893

  1. Taming the Reactivity of Glycosyl Iodides To Achieve Stereoselective Glycosidation.

    PubMed

    Gervay-Hague, Jacquelyn

    2016-01-19

    that even highly functionalized aglycon acceptors add. Following the coupling event, the TMS ethers are readily removed by methanolysis, and since all of the byproducts are volatile, multiple reactions can be performed in a single reaction vessel without isolation of intermediates. In this fashion, per-O-TMS monosaccharides can be converted to biologically relevant α-linked glycolipids in one pot. The stereochemical outcome of these reactions can also be switched to β-glycoside formation by addition of silver to chelate the iodide, thus favoring SN2 displacement of the α-iodide. While iodides derived from benzyl and silyl ether-protected oligosaccharides are susceptible to interglycosidic bond cleavage when treated with TMSI, the introduction of a single acetate protecting group prevents this unwanted side reaction. Partial acetylation of armed glycosyl iodides also attenuates HI elimination side reactions. Conversely, fully acetylated glycosyl iodides are deactivated and require metal catalysis in order for glycosidation to occur. Recent findings indicate that I2 activation of per-O-acetylated mono-, di-, and trisaccharides promotes glycosidation of cyclic ethers to give β-linked iodoalkyl glycoconjugates in one step. Products of these reactions have been converted into multivalent carbohydrate displays. With these synthetic pathways elucidated, chemical reactivity can be exquisitely controlled by the judicious selection of protecting groups to achieve high stereocontrol in step-economical processes. PMID:26524481

  2. [Cardiac evaluation before non-cardiac surgery].

    PubMed

    Menzenbach, Jan; Boehm, Olaf

    2016-07-01

    Before non-cardiac surgery, evaluation of cardiac function is no frequent part of surgical treatment. European societies of anesthesiology and cardiology published consensus-guidelines in 2014 to present a reasonable approach for preoperative evaluation. This paper intends to differentiate the composite of perioperative risk and to display the guidelines methodical approach to handle it. Features to identify patients at risk from an ageing population with comorbidities, are the classification of surgical risk, functional capacity and risk indices. Application of diagnostic means, should be used adjusted to this risk estimation. Cardiac biomarkers are useful to discover risk of complications or mortality, that cannot be assessed by clinical signs. After preoperative optimization and perioperative cardiac protection, the observation of the postoperative period remains, to prohibit complications or even death. In consideration of limited resources of intensive care department, postoperative ward rounds beyond intensive care units are considered to be an appropriate instrument to avoid or recognize complications early to reduce postoperative mortality. PMID:27479258

  3. New oleyl glycoside as anti-cancer agent that targets on neutral sphingomyelinase.

    PubMed

    Romero-Ramírez, Lorenzo; García-Álvarez, Isabel; Casas, Josefina; Barreda-Manso, M Asunción; Yanguas-Casás, Natalia; Nieto-Sampedro, Manuel; Fernández-Mayoralas, Alfonso

    2015-09-15

    We designed and synthesized two anomeric oleyl glucosaminides as anti-cancer agents where the presence of a trifluoroacetyl group close to the anomeric center makes them resistant to hydrolysis by hexosaminidases. The oleyl glycosides share key structural features with synthetic and natural oleyl derivatives that have been reported to exhibit anti-cancer properties. While both glycosides showed antiproliferative activity on cancer cell lines, only the α-anomer caused endoplasmic reticulum (ER) stress and cell death on C6 glioma cells. Analysis of sphingolipids and glycosphingolipds in cells treated with the glycosides showed that the α-anomer caused a drastic accumulation of ceramide and glucosylceramide and reduction of lactosylceramide and GM3 ganglioside at concentrations above a threshold of 20 μM. In order to understand how ceramide levels increase in response to α-glycoside treatment, further investigations were done using specific inhibitors of sphingolipid metabolic pathways. The pretreatment with 3-O-methylsphingomyelin (a neutral sphingomyelinase inhibitor) restored sphingomyelin levels together with the lactosylceramide and GM3 ganglioside levels and prevented the ER stress and cell death caused by the α-glycoside. The results indicated that the activation of neutral sphingomyelinase is the main cause of the alterations in sphingolipids that eventually lead to cell death. The new oleyl glycoside targets a key enzyme in sphingolipid metabolism with potential applications in cancer therapy. PMID:26206186

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

    SciTech Connect

    Tamura, G.; Gold, C.; Ferro-Luzzi, A.; Ames, B.N.

    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 natural 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.

  5. Influence of steviol glycosides on the stability of vitamin C and anthocyanins.

    PubMed

    Woźniak, Łukasz; Marszałek, Krystian; Skąpska, Sylwia

    2014-11-19

    A high level of sweetness and health-promoting properties make steviol glycosides an interesting alternative to sugars or artificial sweeteners. The radical oxygen species scavenging activity of these compounds may influence the stability of labile particles present in food. Model buffer solutions containing steviol glycosides, a selected food antioxidant (vitamin C or anthocyanins), and preservative were analyzed during storage. The addition of steviol glycosides at concentrations of 50, 125, and 200 mg/L increased the stability of both ascorbic and dehydroascorbic acid (degradation rates decreased up to 3.4- and 4.5-fold, respectively); the effect was intensified by higher sweetener concentrations and higher acidity of the solutions. Glycosides used alone did not affect the stability of anthocyanins; however, they enhanced the protective effect of sugars; half-life times increased by ca. 33% in the presence of sucrose (100 g/L) and by ca. 52% when both sucrose (100 g/L) and glycosides (total 200 mg/L) were used. Steviol glycosides concentrations remained stable during experiments. PMID:25376304

  6. 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. PMID:26948641

  7. Direct analysis of Stevia leaves for diterpene glycosides by desorption electrospray ionization mass spectrometry.

    PubMed

    Jackson, Ayanna U; Tata, Alessandra; Wu, Chunping; Perry, Richard H; Haas, George; West, Leslie; Cooks, R Graham

    2009-05-01

    The analysis of Stevia leaves has been demonstrated without any sample preparation using desorption electrospray ionization (DESI) mass spectrometry. Direct rapid analysis was achieved using minimal amounts of sample ( approximately 0.15 cm x 0.15 cm leaf fragment). Characteristic constituents of the Stevia plant are observed in both the positive and negative ion modes including a series of diterpene 'sweet' glycosides. The presence of the glycosides was confirmed via tandem mass spectrometry analysis using collision-induced dissociation and further supported by exact mass measurements using an LTQ-Orbitrap. The analysis of both untreated and hexane-extracted dry leaves proved that DESI can be successfully used to analyze untreated leaf fragments as identical profiles were obtained from both types of samples. Characterization and semi-quantitative determination of the glycosides was achieved based on the glycoside profile within the full mass spectrum. In addition, the presence of characteristic glycosides in an all-natural commercial Stevia dietary supplement was confirmed. This study provides an example of the application of DESI to direct screening of plant materials, in this case diterpene glycosides. PMID:19381377

  8. 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

  9. A genomics investigation of partitioning into and among flavonoid-derived condensed tannins for carbon sequestration in Populus

    SciTech Connect

    Harding, Scott, A; Tsai, Chung-jui; Lindroth, Richard, L

    2013-03-24

    -structural carbohydrates contributed to the model presented. Harding SA, Xue L, Du L, Nyamdari B, Sykes R, Davis M, Lindroth RL, Tsai CJ (submitted March 2013) Condensed tannin biosynthesis in leaves conditions carbon use, defense and growth in Populus. (Invited submission to Tree Physiology) MS abstract: Condensed tannins (CT) are flavonoid end products that can comprise a large fraction of leaf, bark and root biomass in Populus species. CT accrual was investigated in relation to metabolic carbon and nitrogen use in young leaves and shoot tips (ST) where CT biosynthesis was most active. A slow-growing genotype (SG) and a fast-growing genotype (FG) were compared. Both genotypes exhibited the capacity to accrue similarly large reserves of salicortin a phenolic glycoside (PG), but the slow-growing line also produced CT. PG accrual was developmentally delayed in the slow-growing line, SG. Irrigation with low-N nutrients promoted PG accrual in FG plants, but PG accrual was suspended in CT-producing SG plants. In addition, the low C:N amide asparagine accumulated and glucose was depleted in ST and expanding leaves of SG plants. The monoamine phenylethylamine (PEA) was abundant in SG leaves and absent in FG leaves. Leaf metabolite and gene expression differences were observed between SG and FG that would be expected to impinge upon glycolysis, acetyl-CoA production and flavonoid production. A model that integrates PEA with those activities and CT accrual was developed. Briefly, the data support a model in which flavonoid biosynthesis depleted the acetyl-CoA pool, thereby promoting glycolytic and shikimic pathway fluxes in SG plants. PEA results from decarboxylation of the shikimic pathway end-product phenylalanine, and is proposed to have facilitated CT polymerization, thereby promoting the continued biosynthesis of flavonoid CT precursors in SG leaves. The leaf differentials described here were absent in young roots, as was PEA. The potential contribution of PEA to CT polymerization

  10. Influence of solvents on the composition of condensed tannins in grape pomace seed extracts.

    PubMed

    Bosso, Antonella; Guaita, Massimo; Petrozziello, Maurizio

    2016-09-15

    The extracting effectiveness of some solvents (water, ethanol, acetone, ethyl acetate), used as pure or in binary and ternary mixtures, was studied for the extraction of seeds from the fermented pomace of Nebbiolo cv. The aqueous mixtures of acetone provided the highest extraction yields in total polyphenols and total flavonoids. Polyphenolic extracts were also obtained with aqueous mixtures of ethanol or acetone at variable concentrations, and the condensed tannins were quantified with the phloroglucinolysis method. The aqueous mixtures of acetone were more effective than the corresponding aqueous mixtures of ethanol. The solvent influenced the extraction yield and the composition of the extracts: with the increase of the yield, the mean degree of polymerization (mDP) of the condensed tannins increased. A significant correlation was noticed between mDP and the molar percentages of (+)-catechin as terminal unit (negative correlation), and of (-)-epicatechin and (-)-epicatechin-3O-gallate as extension units (positive correlation). PMID:27080893

  11. Antioxidant and free radical scavenging effects of the tannins of Terminalia catappa L.

    PubMed

    Lin, C C; Hsu, Y F; Lin, T C

    2001-01-01

    Reactive oxygen species (ROS) react with biological molecules and destroy the structure of cells and eventually cause free radical-induced disease such as inflammation and cancer. Previous studies showed that an aqueus extract of Terminalia catappa L. exhibited superoxide radical scavenger activity and modification of mitomycin C-induced clasto-genicity. In order to investigate the multiple antioxidant effect of the tannin components of T. catappa L., their ability to prevent lipid peroxidation, superoxide formation and their free radical scavenging activity were evaluated. The results indicated that all of these components showed potent antioxidant activity. Punicalagin and punicalin were the most abundant components and had the strongest anti-oxidative effects of this group of tannins. PMID:11299741

  12. The complexity of condensed tannin binding to bovine serum albumin--An isothermal titration calorimetry study.

    PubMed

    Kilmister, Rachel L; Faulkner, Peta; Downey, Mark O; Darby, Samuel J; Falconer, Robert J

    2016-01-01

    Isothermal titration calorimetry was applied to study the binding of purified proanthocyanidin oligomers to bovine serum albumin (BSA). The molecular weight of the proanthocyanidin oligomer had a major impact on its binding to BSA. The calculated change in enthalpy (ΔH) and association constant (Ka) became greater as the oligomer size increased then plateaued at the heptameric oligomer. These results support a model for precipitation of proteins by proanthocyanidin where increased oligomer size enhanced the opportunity for cross linkages between proteins ultimately forming sediment-able complexes. The authors suggest tannin binding to proteins is opportunistic and involves multiple sites, each with a different Ka and ΔH of binding. The ΔH of binding comprises both an endothermic hydrophobic interaction and exothermic hydrogen bond component. This suggests the calculated entropy value (ΔS) for tannin-protein interactions is subject to a systematic error and should be interpreted with caution. PMID:26212957

  13. Chemical composition, dietary fibre, tannins and minerals of grain amaranth genotypes.

    PubMed

    Mustafa, Arif F; Seguin, Philippe; Gélinas, Bruce

    2011-11-01

    The objective of this study was to determine the chemical composition of 28 white and coloured grain amaranth (Amaranthus spp.) genotypes. Neutral detergent fibre (NDF) concentration was greater while strach concentration was lower for coloured seeds genotypes than white seeds genotypes. Total dietary fibre followed a similar trend to that observed for NDF. Total tannin concentrations ranged between 20.7 and 0 g/kg with total and hydrolysed tannin concentrations being higher for white than for coloured seeds genotypes. Coloured seeds genotypes contained higher Mg and Ca concentrations than white seeds genotypes. However, seed colour had no influence on K, Na and P concentrations. Copper and Fe were the most variable micro-minerals in the evaluated genotypes with no significant effect of seed colour on the concentration of either mineral. PMID:21599462

  14. 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

  15. [Cardiac Rehabilitation 2015].

    PubMed

    Hoffmann, Andreas

    2015-11-25

    The goals of cardiac rehabilitation are (re-)conditioning and secondary prevention in patients with heart disease or an elevated cardiovascular risk profile. Rehabilitation is based on motivation through education, on adapted physical activity, instruction of relaxation techniques, psychological support and optimized medication. It is performed preferably in groups either in outpatient or inpatient settings. The Swiss working group on cardiac rehabilitation provides a network of institutions with regular quality auditing. Positive effects of rehabilitation programs on mortality and morbidity have been established by numerous studies. Although a majority of patients after cardiac surgery are being referred to rehabilitation, these services are notoriously underused after catheter procedures. PMID:26602848

  16. Chemical Affinity between Tannin Size and Salivary Protein Binding Abilities: Implications for Wine Astringency.

    PubMed

    Ma, Wen; Waffo-Teguo, Pierre; Jourdes, Michael; Li, Hua; Teissedre, Pierre-Louis

    2016-01-01

    Astringency perception, as an essential parameter for high-quality red wine, is principally elicited by condensed tannins in diversified chemical structures. Condensed tannins, which are also known as proanthocyanidins (PAs), belong to the flavonoid class of polyphenols and are incorporated by multiple flavan-3-ols units according to their degree of polymerization (DP). However, the influence of DP size of PAs on astringency perception remains unclear for decades. This controversy was mainly attributed to the lack of efficient strategies to isolate the PAs in non-galloylated forms and with individual degree size from grape/wine. In the present study, the astringency intensity of purified and identified grape oligomeric tannins (DP ranged from 1 to 5) was firstly explored. A novel non-solid phase strategy was used to rapidly exclude the galloylated PAs from the non-galloylated PAs and fractionate the latter according to their DP size. Then, a series of PAs with individual DP size and galloylation were purified by an approach of preparative hydrophilic interaction chromatography. Furthermore, purified compounds were identified by both normal phase HPLC-FLD and reverse phase UHPLC-ESI-Q-TOF. Finally, the contribution of the astringency perception of the individual purified tannins was examined with a salivary protein binding ability test. The results were observed by HPLC-FLD and quantified by changes in PA concentration remaining in the filtrate. In summary, a new approach without a solid stationary phase was developed to isolate PAs according to their DP size. And a positive relationship between the DP of PAs and salivary protein affinity was revealed. PMID:27518822

  17. Effect of tannin extract against Pseudomonas aeruginosa producing metallo beta-lactamase.

    PubMed

    Ghafourian, S; Mohebi, R; Sekawi, Z; Raftari, M; Neela, V; Ghafourian, E; Aboualigalehdari, E; Rahbar, M; Sadeghifard, N

    2012-01-01

    Carbapenems are the most potent beta-lactam agents with a broad-spectrum activity against Gram-negative and Gram-positive bacteria. They are stable in the presence of penicillinases and cephalosporinases. This study was focused on frequency of metallo beta- lactamase (MBL) among Pesudomonas aeruginosa strains isolated in patients with urinary tract infection, effect of tannin against PA positive strains which produced blaVIM or blaIMP and both of these genes (Species). Detection of MBL was performed by phonotypic and genotypic methods. Tannin extract was tested against P. aeruginosa producing MBL. During the study period, 240 P. aeruginosa isolates were identified. Among them 64 (26.6 percent) isolates were imipenem non-susceptible and confirmed by imipenem/EDTA. Our results revealed that the growth of blaVIM positive P. aeruginosa inhibited at 15 microg/ml concentration. The experiment repeated for blaIMP-positive P. aeruginosa and P. aeruginosa which harbored blaIMP and blaVIM, the results showed 35 microg/ml was the best concentration for inhibition of P. aeruginosa-positive blaIMP and also P. aeruginosa blaIMP and blaVIM. In conclusion, tannin was effective against P. aeruginosa producing blaVIM and blaIMP and both of them so it can be substituted with common antibiotics. The result showed significantly P. aeruginosa-harbored blaIMP was more responsible for imipenem resistance than P. aeruginosa-positive blaVIM. Interestingly, tannin was more effective against MBL-P. aeruginosa in comparison with current antibiotics. PMID:22824750

  18. Effect of condensed tannins on egg hatching and larval development of Trichostrongylus colubriformis in vitro.

    PubMed

    Molan, A L; Waghorn, G C; McNabb, W C

    2002-01-19

    The effects of condensed tannins extracted from seven forages on the viability of the eggs and first stage (L1) larvae of the sheep nematode Trichostrongylus colubriformis were evaluated in in vitro assays. The extracts of condensed tannins were obtained from Lotus pedunculatus (LP), Lotus corniculatus (LC), sulla (Hedysarum coronarium), sainfoin (Onobrychus viciifolia), Dorycnium pentaphylum (DP), Dorycnium rectum (DR) and dock (Rumex obtusifolius). Extracts containing 200 to 500 microg/ml reduced the proportion of eggs that hatched. The larval development assay was used to evaluate the effect of the extracts on the development of either eggs or L1 larvae to L3 infective larvae. Development was allowed to proceed for seven days by which time the larvae in control incubations had reached the infective L3 stage. Extracts containing 200 microg/ml from LP, DP, DR or dock prevented egg development, and only 11, 8 and 2 per cent of the eggs developed to L3 larvae with extracts from LC, sulla and sainfoin, respectively. When the concentration was 400 microg/ml no eggs developed to L3 larvae. The addition of the extracts after hatching also inhibited the development of L1 to L3 larvae; 200 microg/ml extracted from LP, LC, sulla, sainfoin, DP, DR and dock resulted in only 14, 18, 17, 15, 14, 16 and 4 per cent of L1 larvae developing to the L3 stage compared with 85 per cent for controls, and 400 microg/ml further reduced the development of L1 larvae. Statistical analyses showed that when the extracts were added before hatching they were significantly (P<0.001) more effective at inhibiting the larval development than when they were added after hatching. The condensed tannins from dock had the greatest inhibitory effect on egg development followed by the tannins from DR, sainfoin, DP, LP, sulla and LC. PMID:11837588

  19. Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry.

    PubMed

    Mämmelä, P; Savolainen, H; Lindroos, L; Kangas, J; Vartiainen, T

    2000-09-01

    Extractable tannins were analysed by liquid chromatography-electrospray ionisation mass spectrometry in two oak species, North American white oak (Quercus alba) and European red oak (Quercus robur). They mainly included various glucose gallic and ellagic acid esters. The structures were partially determined, and they included grandinin/roburin E, castalagin/vescalagin, gallic acid, valoneic acid bilactone, monogalloyl glucose, digalloyl glucose, trigalloyl glucose, ellagic acid rhamnose, quercitrin and ellagic acid. PMID:10999626

  20. The tannin-degrading species Streptococcus gallolyticus and Streptococcus caprinus are subjective synonyms.

    PubMed

    Sly, L I; Cahill, M M; Osawa, R; Fujisawa, T

    1997-07-01

    The tannin-degrading species Streptococcus gallolyticus and Streptococcus caprinus have been shown to be subjective synonyms on the basis of their levels of 16S rRNA sequence similarity (98.3%) and DNA-DNA homology (> 70%) and the phenotypes of their type strains. S. gallolyticus has nomenclatural priority according to Rule 24b(2) of the International Code of Nomenclature of Bacteria. PMID:9226925

  1. Activity of tannins from Stryphnodendron adstringens on Cryptococcus neoformans: effects on growth, capsule size and pigmentation

    PubMed Central

    Ishida, Kelly; Rozental, Sonia; de Mello, João Carlos Palazzo; Nakamura, Celso Vataru

    2009-01-01

    Background Stryphnodendron adstringens (Mart.) Coville, Leguminosae, also known in Brazil as barbatimão, is rich in tannins and many flavan-3-ols and proanthocyanidins such as prodelphinidins and prorobinetinidins. Previous studies have demonstrated several pharmacological properties of tannins from barbatimão, including anti-candidal activity. Methods The antifungal activity of proanthocyanidin polymeric tannins from Stryphnodendron adstringens (subfraction F2.4) was evaluated against three strains of Cryptococcus neoformans with different capsule expressions, using the broth microdilution technique, light microscopy and transmission electron microscopy. The effect of subfraction F2.4 on C. neoformans and melanoma mammalian cells pigmentation was also evaluated. Results Although susceptibility assays revealed MIC values quite similar (between 2.5 and 5.0 μg/ml), analyses of MFC values revealing that the acapsular mutant Cap 67 was more susceptible to be killed by the subfraction F2.4 (MFC = 20 μg/ml) than the two tested capsular strains (T1-444 and ATCC 28957) (MFC > 160 μg/ml). Optical and electron microscopy experiments revealed relevant alterations in cell shape and size in all strains treated with 1 and 2.5 μg/ml of subfraction F2.4. Capsule size of the capsular strains decreased drastically after subfraction F2.4 treatment. In addition, ultrastructural alterations such as cell wall disruption, cytoplasm extraction, mitochondria swelling, increase in the number of cytoplasmic vacuoles and formation of membranous structures in the cytoplasm were also observed in treated yeasts. Incubation with subfraction F2.4 also decreased C. neoformans pigmentation, however, did not interfere in melanization of B16F10 mammalian cells. Conclusion Our data indicate that tannins extracted from S. adstringens interfered with growth, capsule size and pigmentation, all important virulence factors of C. neoformans, and may be considered as a putative candidate for the

  2. Chemical Affinity between Tannin Size and Salivary Protein Binding Abilities: Implications for Wine Astringency

    PubMed Central

    Ma, Wen; Waffo-Teguo, Pierre; Jourdes, Michael; Li, Hua

    2016-01-01

    Astringency perception, as an essential parameter for high-quality red wine, is principally elicited by condensed tannins in diversified chemical structures. Condensed tannins, which are also known as proanthocyanidins (PAs), belong to the flavonoid class of polyphenols and are incorporated by multiple flavan-3-ols units according to their degree of polymerization (DP). However, the influence of DP size of PAs on astringency perception remains unclear for decades. This controversy was mainly attributed to the lack of efficient strategies to isolate the PAs in non-galloylated forms and with individual degree size from grape/wine. In the present study, the astringency intensity of purified and identified grape oligomeric tannins (DP ranged from 1 to 5) was firstly explored. A novel non-solid phase strategy was used to rapidly exclude the galloylated PAs from the non-galloylated PAs and fractionate the latter according to their DP size. Then, a series of PAs with individual DP size and galloylation were purified by an approach of preparative hydrophilic interaction chromatography. Furthermore, purified compounds were identified by both normal phase HPLC-FLD and reverse phase UHPLC-ESI-Q-TOF. Finally, the contribution of the astringency perception of the individual purified tannins was examined with a salivary protein binding ability test. The results were observed by HPLC-FLD and quantified by changes in PA concentration remaining in the filtrate. In summary, a new approach without a solid stationary phase was developed to isolate PAs according to their DP size. And a positive relationship between the DP of PAs and salivary protein affinity was revealed. PMID:27518822

  3. Bile acid-binding ability of kaki-tannin from young fruits of persimmon (Diospyros kaki) in vitro and in vivo.

    PubMed

    Matsumoto, Kenji; Kadowaki, Akio; Ozaki, Natsumi; Takenaka, Makiko; Ono, Hiroshi; Yokoyama, Shin-ichiro; Gato, Nobuki

    2011-04-01

    The bile acid-binding ability of a highly polymerized tannin (kaki-tannin) extracted from dried-young fruits of persimmon (Diospyros kaki) was examined. The kaki-tannin was composed mainly of epicatechin, epigallocatechin, epicatechin-3-O-gallate and epigallocatechin-3-O-gallate. Bile acid-binding ability of kaki-tannin was examined against cholic acid, glycocholic acid, taurocholic acid and deoxycholic acid in vitro, and its effect on fecal bile acid excretion in mice was also examined. Although the bile acid-binding ability of kaki-tannin was weaker than that of cholestyramine, kaki-tannin adsorbed all the bile acids tested and significantly promoted fecal bile acid excretion in mice when supplied at 1% (w/w) in the diet. PMID:20922818

  4. [Determination of 7 flavonol glycosides in Ginkgo biloba reference extract].

    PubMed

    Wang, Jing-hui; Chen, Jing; Wang, Meng-meng; Fu, Xin-tong; Chen, You-gen; Guo, Hong-zhu

    2015-10-01

    Six flavonol glycosides were isolated and calibrated from Ginkgo biloba extract, and then used to calibrate the content in 2 baiches of G. biloba reference extract, so was rutin. RSD values of rutin, kaempferol-3-O-rutinoside, kaempferol-3-O-rhamnoside-2-glu- coside, quercetin-3-O-rhamnop-yranosyl-2-O-(6-O-p-coumaroyl)-glucoside, kaempferol-3-O-rhamnopyranosyl-2-O-(6-O-p-coum-aroyl) - glucoside were around 1.1%-4.6%, nevertheless, RSD values of quercetin-3-O-glucoside and isorhamnetin-3-O-rutinoside were more than 5%. According to the results, the reference extract of G. biloba can be used as the substitute to determine rutin, kaempferol-3-O- rutinoside, kaempferol-3-O-rhamnoside-2-glucoside, quercetin-3-O-rhamnopyranosyl-2-O-(6-O-p-coumaroyl)-glucoside and kaempferol-3-0-rhamnopyranosyl-2-O-(6-O-p-coumaroyl)-glucoside instead of corresponding reference substances. So reference extract in place of single component reference in assay is feasible. PMID:27062820

  5. New acylated triterpene glycosides from the roots of Polygala tenuifolia.

    PubMed

    Kuroda, Minpei; Shizume, Takaaki; Mimaki, Yoshihiro

    2014-03-01

    Two new and five known acylated triterpene glycosides were isolated from the MeOH extract of the roots of Polygala tenuifolia. Based on extensive spectroscopic analysis, including 2D NMR experiments, and the results of alkaline hydrolysis, the structures of the new compounds were assigned as 3beta-[(beta-D-glucopyranosyl)oxy]-2 beta,27-dihydroxyolean- 12-ene-23,28-dioic acid 28-O-beta-D-apiofuranosyl-( 1--3)-[beta-D-galactopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1 -4)]-alpha-L-rhamnopyranosyl-(1-2)-3-O-(E)-3,4,5-trimeth oxycinnamoyl-beta-D-fucopyranosyl ester (1) and 3beta-[(beta-D-glucopyranosyl)oxy]-2beta,27-dihydroxyolean-1 2-ene-23,28-dioic acid 28-O-beta-D-apiofuranosyl-(l---3)-[beta-D-galactopyranosyl-(1-->4)-beta-D-xylopyranosyl-( 1-->4)]-alpha-L-rhamnopyranosyl-(1 -2)-[alpha-L-rhamnopyranosyl-( 1 -3 )]-4-O-(E)-3,4-dimethoxycinnamoyl-beta-D-fucopyranosyl ester (2). PMID:24689222

  6. beta-glucosidase catalyzed syntheses of pyridoxine glycosides.

    PubMed

    Charles, Rajachristu Einstein; Divakar, Soundar

    2009-01-01

    Enzymatic syntheses of pyridoxine glycosides were carried out in di-isopropyl ether organic medium using beta-glucosidase isolated from sweet almond. Optimum conditions determined for the reaction with D-glucose were 40% (w/w D-glucose) beta-glucosidase at 0.18 mM (1.8 ml) of pH 5 acetate buffer over a 72 h incubation period. Of 11 carbohydrates employed, beta-glucosidase gave 7-O-(alpha-D-glucopyranosyl)pyridoxine 5a, 7-O-(beta-D-glucopyranosyl)pyridoxine 5b, 6-O-(alpha-D-glucopyranosyl)pyridoxine 5c, 7-O-(alpha-D-galactopyranosyl)pyridoxine 6a, 7-O-(beta-D-galactopyranosyl)pyridoxine 6b, 6-O-(alpha-D-galactopyranosyl)pyridoxine 6c, 7-O-(alpha-D-mannopyranosyl)pyridoxine 7a, 7-O-(beta-D-mannopyranosyl)pyridoxine 7b, and 6-O-(alpha-D-mannopyranosyl)pyridoxine 7c in yields ranging from 23 to 40%. PMID:19129657

  7. Effects of synthetic glycosides on steroid balance in Macaca fascicularis

    SciTech Connect

    Malinow, M.R.; Elliott, W.H.; McLaughlin, P.; Upson, B.

    1987-01-01

    The predominantly beta-anomer of diosgenin glucoside (DG) was synthesized and its effects on cholesterol homeostasis were tested in monkeys. Cynomolgus macaques (Macaca fascicularis) were fed, during two 3-week periods, a semipurified diet with 0.1% cholesterol and a similar ration containing 1% DG, respectively. A Chow diet was given for 5 weeks between the experimental periods. Cholesterol and bile acid balance were analyzed during the last week of each semipurified diet. Diosgenin glucoside reduced cholesterolemia from 292 mg/dl to 172 mg/dl, decreased intestinal absorption of exogenous cholesterol from 62.4% to 26.0%, and increased secretion of endogenous cholesterol from -0.8 to 93.5 mg/day. The fecal excretion of neutral steroids rose from 40.7 to 157.3 mg/day; that of bile acids changed, nonsignificantly, from 23.1 to 16.0 mg/day. The cholesterol balance was -44 mg/day in the control period, and 88 mg/day in the DG-fed animals. No toxic signs were observed. Thus, when long-term studies demonstrate that the glucoside is well tolerated, DG and other synthetic glycosides with similar activities may be of use in the management of hypercholesterolemia and atherosclerosis.

  8. Six new C21 steroidal glycosides from Asclepias curassavica L.

    PubMed

    Li, Jun-Zhu; Liu, Hai-Yang; Lin, Yi-Ju; Hao, Xiao-Jiang; Ni, Wei; Chen, Chang-Xiang

    2008-07-01

    Six new C(21) steroidal glycosides, named curassavosides A-F (3-8), were obtained from the aerial parts of Asclepias curassavica (Asclepiadaceae), along with two known oxypregnanes, 12-O-benzoyldeacylmetaplexigenin (1) and 12-O-benzoylsarcostin (2). By spectroscopic methods, the structures of the six new compounds were determined as 12-O-benzoyldeacylmetaplexigenin 3-O-beta-D-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (3), 12-O-benzoylsarcostin 3-O-beta-D-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (4), sarcostin 3-O-beta-D-oleandropyranosyl-(1-->4)-beta-D-canaropyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (5), sarcostin 3-O-beta-D-oleandropyranosyl-(1-->4)-beta-D-canaropyranosyl-(1-->4)-beta-D-canaropyranosyl-(1-->4)-beta-D-digitoxopyranoside (6), 12-O-benzoyldeacylmetaplexigenin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-D-canaropyranosyl-(1-->4)-beta-d-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (7), and 12-O-benzoylsarcostin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-d-canaropyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (8), respectively. All compounds (1-8) were tested for in vitro cytotoxicity; only compound 3 showed weak inhibitory activity against Raji and AGZY cell lines. PMID:18328519

  9. Cytotoxicity of cardenolides and cardenolide glycosides from Asclepias curassavica.

    PubMed

    Li, Jun-Zhu; Qing, Chen; Chen, Chang-Xiang; Hao, Xiao-Jiang; Liu, Hai-Yang

    2009-04-01

    A new cardenolide, 12beta,14beta-dihydroxy-3beta,19-epoxy-3alpha-methoxy-5alpha-card-20(22)-enolide (6), and a new doubly linked cardenolide glycoside, 12beta-hydroxycalotropin (13), together with eleven known compounds, coroglaucigenin (1), 12beta-hydroxycoroglaucigenin (2), calotropagenin (3), desglucouzarin (4), 6'-O-feruloyl-desglucouzarin (5), calotropin (7), uscharidin (8), asclepin (9), 16alpha-hydroxyasclepin (10), 16alpha-acetoxycalotropin (11), and 16alpha-acetoxyasclepin (12), were isolated from the aerial part of ornamental milkweed, Asclepias curassavica and chemically elucidated through spectral analyses. All the isolates were evaluated for their cytotoxic activity against HepG2 and Raji cell lines. The results showed that asclepin (9) had the strongest cytotoxic activity with an IC(50) value of 0.02 microM against the two cancer cell lines and the new compound 13 had significant cytotoxic activity with IC(50) values of 0.69 and 1.46 microM, respectively. PMID:19251412

  10. New approaches to enzymatic glycoside synthesis through directed evolution.

    PubMed

    Kittl, Roman; Withers, Stephen G

    2010-07-01

    The expanding field of glycobiology requires tools for the synthesis of structurally defined oligosaccharides and glycoconjugates, while any potential therapeutic applications of sugar-based derivates would require access to substantial quantities of such compounds. Classical chemical approaches are not well suited for such large-scale syntheses, thus enzymatic approaches are sought. Traditional routes to the enzymatic assembly of oligosaccharides have involved the use of either Nature's own biosynthetic enzymes, the glycosyl transferases, or glycosidases run in transglycosylation mode. However, each approach has drawbacks that have limited its application. Glycosynthases are mutant glycosidases in which the catalytic nucleophile has been replaced by mutation, inactivating them as hydrolases. When used in conjunction with glycosyl fluorides of the opposite anomeric configuration to that of the substrate, these enzymes function as highly efficient transferases, frequently giving stoichiometric yields of products. Further improvements can be obtained through directed evolution of the gene encoding the enzyme in question, but this requires the ability to screen very large libraries of catalysts. In this review we survey new screening methods for the formation of glycosidic linkages using high-throughput techniques, such as FACS, chemical complementation, and robot-assisted ELISA assays. Enzymes were evolved to have higher catalytic activity with their natural substrates, to show altered substrate specificities or to be promiscuous for efficient application in oligosaccharide, glycolipid, and glycoprotein synthesis. PMID:20427037

  11. Polyketide Glycosides from Bionectria ochroleuca Inhibit Candida albicans Biofilm Formation

    PubMed Central

    2015-01-01

    One of the challenges presented by Candida infections is that many of the isolates encountered in the clinic produce biofilms, which can decrease these pathogens’ susceptibilities to standard-of-care antibiotic therapies. Inhibitors of fungal biofilm formation offer a potential solution to counteracting some of the problems associated with Candida infections. A screening campaign utilizing samples from our fungal extract library revealed that a Bionectria ochroleuca isolate cultured on Cheerios breakfast cereal produced metabolites that blocked the in vitro formation of Candida albicans biofilms. A scale-up culture of the fungus was undertaken using mycobags (also known as mushroom bags or spawn bags), which afforded four known [TMC-151s C–F (1–4)] and three new [bionectriols B–D (5–7)] polyketide glycosides. All seven metabolites exhibited potent biofilm inhibition against C. albicans SC5314, as well as exerted synergistic antifungal activities in combination with amphotericin B. In this report, we describe the structure determination of the new metabolites, as well as compare the secondary metabolome profiles of fungi grown in flasks and mycobags. These studies demonstrate that mycobags offer a useful alternative to flask-based cultures for the preparative production of fungal secondary metabolites. PMID:25302529

  12. Antioxidant flavone glycosides from the leaves of Sasa borealis.

    PubMed

    Park, Hae-Suk; Lim, Ju Hee; Kim, Hyun Jung; Choi, Hyun Jin; Lee, Ik-Soo

    2007-02-01

    Sasa borealis (Poaceae) is a perennial medicinal plant which is a major source of bamboo leaves in Korea. The n-BuOH extract of S. borealis leaves exhibited significant antioxidant activity against the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and a cytoprotective effect against oxidative damage in HepG2 cells. Bioactivity-guided fractionation by column chromatography led to the isolation of two antioxidative flavonoid C-glycoside derivatives, isoorientin (2) and isoorientin 2"-O-alpha-L-rhamnoside (4) along with tricin 7-O-beta-D-glucopyranoside (1) and apigenin 6-C-beta-D-xylopyranosyl-8-C-beta-D-glucopyranoside (3). Their structures were identified on the basis of chemical and spectroscopic methods. The radical scavenging activity and cytoprotective effect against oxidative damage of all the isolated compounds were also evaluated. Isoorientin (2) and isoorientin 2-O-alpha-L-rhamnoside (4) showed potent free radical scavenging activity with IC50 values of 9.5 and 34.5 microM, respectively, and strong cytoprotective effects against t-BOOH-induced oxidative damage in HepG2 cells, at very low concentrations of 1.1 microM isoorientin and 0.8 microM isoorientin 2-O-alpha-L-rhamnoside. This is the first report of the isolation and antioxidant activity of compounds 2 and 4 from S. borealis. PMID:17366736

  13. Additional minor diterpene glycosides from Stevia rebaudiana Bertoni.

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2013-01-01

    Two additional novel minor diterpene glycosides were isolated from the commercial extract of the leaves of Stevia rebaudiana Bertoni. The structures of the new compounds were identified as 13-{β-D-glucopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucupyranosyl-ester} (1), and 13-{β-D-6-deoxy-glucopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {β-D-glucopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)-β-D-gluco-pyranosyl-ester} (2), on the basis of extensive 1D (1H- and 13C-) 2D NMR (COSY, HSQC and HMBC) and MS spectroscopic data as well as chemical studies. PMID:24184820

  14. A new indole glycoside from the seeds of Raphanus sativus.

    PubMed

    Jin, Hong-Guang; Ko, Hae Ju; Chowdhury, Md Anisuzzaman; Lee, Dong-Sung; Woo, Eun-Rhan

    2016-06-01

    A new indole glycoside, β-D-glucopyranosyl 2-(methylthio)-1H-indole-3-carboxylate, named raphanuside A (1), as well as eight known compounds, β-D-fructofuranosyl-(2 → 1)-(6-O-sinapoyl)-α-D-glucopyranoside (2), (3-O-sinapoyl)-β-D-fructofuranosyl-(2 → 1)-α-D-glucopyranoside (3), (3-O-sinapoyl)-β-D-fructofuranosyl-(2 → 1)-(6-O-sinapoyl)-α-D-glucopyranoside (4), (3,4-O-disinapoyl)-β-D-fructofuranosyl-(2 → 1)-(6-O-sinapoyl)-α-D-glucopyranoside (5), isorhamnetin 3,4'-di-O-β-D-glucoside (6), isorhamnetin 3-O-β-D-glucoside-7-O-α-L-rhamnoside (7), isorhamnetin 3-O-β-D-glucoside (8) and 3'-O-methyl-(-)-epicatechin 7-O-β-D-glucoside (9) were isolated from the seeds of Raphanus sativus. Furthermore, compounds 1-3 and 6-9, were isolated from this plant for the first time. The structures of compounds 1-9 were identified using 1D and 2D NMR, including (1)H-(1)H COSY, HSQC, HMBC and NOESY spectroscopic analyses. The inhibitory activity of these isolated compounds against interleukin-6 (IL-6) production in TNF-α stimulated MG-63 cells was also examined. PMID:27193305

  15. Extracellular Glycoside Hydrolase Activities in the Human Oral Cavity.

    PubMed

    Inui, Taichi; Walker, Lauren C; Dodds, Michael W J; Hanley, A Bryan

    2015-08-15

    Carbohydrate availability shifts when bacteria attach to a surface and form biofilm. When salivary planktonic bacteria form an oral biofilm, a variety of polysaccharides and glycoproteins are the primary carbon sources; however, simple sugar availabilities are limited due to low diffusion from saliva to biofilm. We hypothesized that bacterial glycoside hydrolase (GH) activities would be higher in a biofilm than in saliva in order to maintain metabolism in a low-sugar, high-glycoprotein environment. Salivary bacteria from 13 healthy individuals were used to grow in vitro biofilm using two separate media, one with sucrose and the other limiting carbon sources to a complex carbohydrate. All six GHs measured were higher in vitro when grown in the medium with complex carbohydrate as the sole carbon source. We then collected saliva and overnight dental plaque samples from the same individuals and measured ex vivo activities for the same six enzymes to determine how oral microbial utilization of glycoconjugates shifts between the planktonic phase in saliva and the biofilm phase in overnight dental plaque. Overall higher GH activities were observed in plaque samples, in agreement with in vitro observation. A similar pattern was observed in GH activity profiles between in vitro and ex vivo data. 16S rRNA gene analysis showed that plaque samples had a higher abundance of microorganisms with larger number of GH gene sequences. These results suggest differences in sugar catabolism between the oral bacteria located in the biofilm and those in saliva. PMID:26048943

  16. Host dependent iridoid glycoside sequestration patterns in Cionus hortulanus.

    PubMed

    Baden, Christian Ulrich; Franke, Stephan; Dobler, Susanne

    2013-08-01

    Weevils of the genus Cionus (Curculionidae, Mecininae) sequester the iridoid glycosides (IGs) aucubin and catalpol from their host plants Scrophularia or Verbascum (Scrophulariaceae). Cionus hortulanus is the only member of the genus that feeds on both plant genera. We previously showed that sequestration patterns in C. hortulanus depend on the local host. To investigate whether IG patterns are driven by their availability in the hosts or genetic differences between populations, we collected C. hortulanus from S. nodosa in the field and reared them either on S. nodosa or on V. nigrum. The differences in IG concentrations were specific for the host plant upon which the weevils developed. Similar to monophagous species of the Cionini, individuals from S. nodosa had more aucubin than catalpol and mirrored the concentrations of their host plants. Specimens from V. nigrum, on the other hand, had higher concentrations of aucubin and of catalpol than their host. On V. nigrum, the ratio of catalpol to aucubin differed significantly between plant and beetle samples due to much higher catalpol concentrations in the weevils. Our data thus contradict genetically fixed differences between populations living on either plant but rather document the host plants' influence on the beetles' metabolism. PMID:23846185

  17. Thermus thermophilus Glycoside Hydrolase Family 57 Branching Enzyme

    PubMed Central

    Palomo, Marta; Pijning, Tjaard; Booiman, Thijs; Dobruchowska, Justyna M.; van der Vlist, Jeroen; Kralj, Slavko; Planas, Antoni; Loos, Katja; Kamerling, Johannis P.; Dijkstra, Bauke W.; van der Maarel, Marc J. E. C.; Dijkhuizen, Lubbert; Leemhuis, Hans

    2011-01-01

    Branching enzyme (EC 2.4.1.18; glycogen branching enzyme; GBE) catalyzes the formation of α1,6-branching points in glycogen. Until recently it was believed that all GBEs belong to glycoside hydrolase family 13 (GH13). Here we describe the cloning and expression of the Thermus thermophilus family GH57-type GBE and report its biochemical properties and crystal structure at 1.35-Å resolution. The enzyme has a central (β/α)7-fold catalytic domain A with an inserted domain B between β2 and α5 and an α-helix-rich C-terminal domain, which is shown to be essential for substrate binding and catalysis. A maltotriose was modeled in the active site of the enzyme which suggests that there is insufficient space for simultaneously binding of donor and acceptor substrates, and that the donor substrate must be cleaved before acceptor substrate can bind. The biochemical assessment showed that the GH57 GBE possesses about 4% hydrolytic activity with amylose and in vitro forms a glucan product with a novel fine structure, demonstrating that the GH57 GBE is clearly different from the GH13 GBEs characterized to date. PMID:21097495

  18. Tannin Degradation by a Novel Tannase Enzyme Present in Some Lactobacillus plantarum Strains

    PubMed Central

    Jiménez, Natalia; Esteban-Torres, María; Mancheño, José Miguel; de las Rivas, Blanca

    2014-01-01

    Lactobacillus plantarum is frequently isolated from the fermentation of plant material where tannins are abundant. L. plantarum strains possess tannase activity to degrade plant tannins. An L. plantarum tannase (TanBLp, formerly called TanLp1) was previously identified and biochemically characterized. In this study, we report the identification and characterization of a novel tannase (TanALp). While all 29 L. plantarum strains analyzed in the study possess the tanBLp gene, the gene tanALp was present in only four strains. Upon methyl gallate exposure, the expression of tanBLp was induced, whereas tanALp expression was not affected. TanALp showed only 27% sequence identity to TanBLp, but the residues involved in tannase activity are conserved. Optimum activity for TanALp was observed at 30°C and pH 6 in the presence of Ca2+ ions. TanALp was able to hydrolyze gallate and protocatechuate esters with a short aliphatic alcohol substituent. Moreover, TanALp was able to fully hydrolyze complex gallotannins, such as tannic acid. The presence of the extracellular TanALp tannase in some L. plantarum strains provides them an advantage for the initial degradation of complex tannins present in plant environments. PMID:24610854

  19. Inhibitory effect of Pistia tannin on digestive enzymes of Indian major carps: an in vitro study.

    PubMed

    Mandal, Sudipta; Ghosh, Koushik

    2010-12-01

    Aquatic weeds are one of the major unconventional feed ingredients tested for aquafeed formulation. Tannin content in the water lettuce, Pistia, has been quantified (26.67 mg g(-1); dry weight) and graded levels of which (12.5-200 μg) have been incorporated in the reaction mixtures to evaluate any change in the in vitro activity of the principal digestive enzymes from the three Indian major carps (IMC), namely rohu (Labeo rohita), catla (Catla catla) and mrigala (Cirrhinus mrigala). Result of the experiment revealed that the Pistia tannin (PT) significantly inhibit/lower the activities of the digestive enzymes from three IMCs in a dose-dependent manner, even at very low concentration. Significant variation in the reduction of the enzyme activities was noticed between the three fish species, as well as between the three enzymes studied. Among the three species studied, digestive enzymes from L. rohita were found to be the most sensitive to the PT, whereas enzymes from C. catla were found to be comparatively least affected. On the other hand, protease and lipase activities were comparatively more affected than the amylase activity. The results of the study suggest that more stress should be given on the elimination of tannin while incorporating feed ingredients of plant origin in fish diets. PMID:20369287

  20. 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.