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Sample records for tannins cardiac glycosides

  1. 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 ...

  2. 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

  3. Evaluating the Cancer Therapeutic Potential of Cardiac Glycosides

    PubMed Central

    Calderón-Montaño, José Manuel; Burgos-Morón, Estefanía; Orta, Manuel Luis; Maldonado-Navas, Dolores; García-Domínguez, Irene; López-Lázaro, Miguel

    2014-01-01

    Cardiac glycosides, also known as cardiotonic steroids, are a group of natural products that share a steroid-like structure with an unsaturated lactone ring and the ability to induce cardiotonic effects mediated by a selective inhibition of the Na+/K+-ATPase. Cardiac glycosides have been used for many years in the treatment of cardiac congestion and some types of cardiac arrhythmias. Recent data suggest that cardiac glycosides may also be useful in the treatment of cancer. These compounds typically inhibit cancer cell proliferation at nanomolar concentrations, and recent high-throughput screenings of drug libraries have therefore identified cardiac glycosides as potent inhibitors of cancer cell growth. Cardiac glycosides can also block tumor growth in rodent models, which further supports the idea that they have potential for cancer therapy. Evidence also suggests, however, that cardiac glycosides may not inhibit cancer cell proliferation selectively and the potent inhibition of tumor growth induced by cardiac glycosides in mice xenografted with human cancer cells is probably an experimental artifact caused by their ability to selectively kill human cells versus rodent cells. This paper reviews such evidence and discusses experimental approaches that could be used to reveal the cancer therapeutic potential of cardiac glycosides in preclinical studies. PMID:24895612

  4. Cardiac glycosides from Yellow Oleander (Thevetia peruviana) seeds.

    PubMed

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

    2012-03-01

    Thevetia cardiac glycosides can lead to intoxication, thus they are important indicators for forensic and pharmacologic surveys. Six thevetia cardiac glycosides, including two with unknown structures, were isolated from the seeds of the Yellow Oleander (Thevetia peruviana (Pers.) K. Shum., Apocynaceae). LC-ESI⁺-MS(/MS) analysis under high-resolution conditions used as a qualitative survey of the primary glycosides did not lead to fragmentation of the aglycones. Acid hydrolysis of the polar and non-volatile thevetia glycosides under severe conditions yielded the aglycones of the thevetia glycosides and made them amenable to GC-MS analysis. Comparison of mass spectral fragmentation patterns of the aglycones, as well as high-resolution mass spectrometric and NMR data of four of the primary thevetia glycosides including the two unknowns, revealed the structures of the complete set of six thevetia glycosides. The identified compounds are termed thevetin C and acetylthevetin C and differ by an 18,20-oxido-20,22-dihydro functionality from thevetin B and acetylthevetin B, respectively. The absence of an unsaturated lactone ring renders the glycosides cardio-inactive. The procedures developed in this study and the sets of analytical data obtained will be useful for screening and structure assessment of other, particularly polar, cardiac glycosides.

  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.

  6. Studies on the localization of the cardiac glycoside receptor

    PubMed Central

    Smith, Thomas W.; Wagner, Henry; Markis, John E.; Young, Michael

    1972-01-01

    The purpose of this study was to see whether the receptor for cardiac glycosides might be localized upon or within the plasma membrane of digitalis-sensitive cells. Ouabain and digoxin were joined covalently to several large protein molecules. These macromolecular conjugates are too large to enter intact cells; consequently, any pharmacologic or biochemical effects which they display should arise from interaction with a cell surface receptor. Conjugates were tested in several cardiac glycoside-sensitive systems: (a), contractility response of isolated cardiac muscle; (b), active 86Rb+ uptake by red cells; (c), enzymatic activity of isolated myocardial microsomal (Na+ + K+)-activated adenosine triphosphatase (ATPase); and (d), enzymatic activity of solubilized red cell (Na+ + K+)-activated ATPase. Results demonstrated that in all of these systems, the macromolecular-glycoside conjugates were 100- to 1000-fold less active than the free glycosides. Careful chromatographic examination of the various conjugates revealed that they contained a small but persistent free cardiac glycoside contaminant. The amount of this species ranged from 0.1 to 1.0% of the total macromolecule-bound glycoside, and its presence fully explains the levels of biologic activity observed with the conjugates. To try to minimize steric factors which could interfere with glycoside-receptor interaction, digoxin and ouabain were also coupled to macromolecule via long, flexible polyamide side-chains. These extended chain conjugates, in which the cardiac glycoside potentially lay some 30 A removed from the surface of the macromolecule, also exhibited negligible digitalis-like effects when tested upon isolated cardiac muscle, red cell 86Rb+ uptake, and enzymatic activity of cardiac microsomal (Na+ + K+)-ATPase. However, the extended chain conjugates were fully active when examined with the solubilized red cell (Na+ + K+)-ATPase system. To further ensure that the chemical reactions used to couple

  7. Cardiac glycosides and pregnanes from Adenium obesum (studies on the constituents of Adenium. I).

    PubMed

    Yamauchi, T; Abe, F

    1990-03-01

    Cardiac glycosides and pregnanes from the roots and the stems of Adenium obesum Roem. et Schult. were investigated. Among 30 cardiac glycosides including 15 known glycosides and 15 new combinations of the known aglycones and sugars, the structures of 11 glycosides were elucidated. Oleandrigenin beta-gentiobiosyl-beta-D-thevetoside was the main glycoside. Neridienone A and 16,17-dihydroneridienone A, common pregnanes in Apocynaceae, were also isolated.

  8. The cardiac glycoside-receptor system in the human heart.

    PubMed

    Erdmann, E; Brown, L

    1983-01-01

    Specific binding sites have been demonstrated to exist in the heart for several drugs and hormones such as beta-blocking agents, cardiac glycosides, catecholamines, insulin, glucagon and acetylcholine. The specific binding sites for cardiac glycosides in the human heart have certain properties which make it likely that they are the pharmacological receptors for the therapeutic and toxic actions of digitalis glycosides: they are located in the cell membrane and bind cardioactive steroids reversibly with high affinity: half-maximal receptor binding occurs at approximately 2 nM (approximately 1.5 ng/ml) for digoxin; potassium decreases receptor affinity, calcium increases it; specific binding of ouabain, digoxin or digitoxin is related to inhibition of (Na+ + K+)-ATPase activity--which is supposed to be the receptor enzyme for cardiac glycosides. Human left ventricle contains approximately 1.5 x 10(14) binding sites/g wet weight, right ventricle approximately 0.9 x 10(14). In disease the number of receptors may decrease (hypothyroid states, myocardial infarction) or increase (hyperthyroidism, chronic hypokalaemia). Certain drugs (such as phenytoin) or different temperatures or pH changes cause a change in digitalis-receptor affinity. Thus, the number of receptors and possibly their properties are subject to regulation in clinically relevant situations. Further investigations will probably reveal those pathophysiological states, which allow the explanation of toxicity or digitalis refractoriness.

  9. Cytotoxic cardiac glycosides and other compounds from Asclepias syriaca.

    PubMed

    Araya, Juan J; Kindscher, Kelly; Timmermann, Barbara N

    2012-03-23

    Phytochemical investigation of the dried biomass of Asclepias syriaca afforded five new compounds (1-5), along with 19 known structures. Overall, the secondary metabolites isolated and identified from this plant showed a wide structural diversity including pentacyclic triterpenes, cardiac glycosides, flavonoid glycosides, lignans, a phenylethanoid, and a glycosylated megastigmane. In addition, the isolates were tested against the cancer breast cell line Hs578T, and those showing IC(50) values lower than 50 μM (1 and 6-9) were further investigated in three additional breast cancer cell lines (MCF-7, T47D, and Sk-Br-3) and the normal breast cell line Hs578Bst.

  10. Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin.

    PubMed

    Beale, Thomas M; Taylor, Mark S

    2013-03-15

    The cardiac glycoside natural product digitoxin was selectively glycosylated at one of its five hydroxyl groups using a borinic acid derived catalyst. This method provided access to the glycosylation pattern characteristic of a subclass of natural products from Digitalis purpurea. Variation of the glycosyl donor was tolerated, enabling the synthesis of novel cardiac glycoside analogs from readily available materials.

  11. New Knowledge About Old Drugs: The Anti-Inflammatory Properties of Cardiac Glycosides.

    PubMed

    Fürst, Robert; Zündorf, Ilse; Dingermann, Theo

    2017-03-15

    In the 19th century, cardio-active steroid glycosides, shortly cardiac glycosides, were scientifically established as drugs against heart failure. Their in vivo, cellular, and molecular actions as well as their predominant target, Na(+)-K(+)-ATPase, have been comprehensively investigated in the 20th century and the discovery of endogenous cardiac glycosides has fostered this research field. In the last years, however, results from clinical trials and meta-analyses have questioned their therapeutic value due to efficacy and safety issues. This has led to a considerable decline of their usage. Beyond the cardiovascular system, cardiac glycosides have been increasingly recognized as antitumor compounds and Na(+)-K(+)-ATPase has evolved into a promising drug target in oncology. A wealth of review articles exists that intensively discuss these topics. Surprisingly, the anti-inflammatory actions of cardiac glycosides, which were discovered in the 1960s, have so far hardly been perceived and have not yet been summarized. This review provides an overview of the in vivo and in vitro actions of cardiac glycosides on inflammatory processes and of the signaling mechanisms responsible for these effects: cardiac glycosides have been found to decrease inflammatory symptoms in different animal models of acute and chronic inflammation. Regarding the underlying mechanisms most research has focused on leukocytes. In these cells, cardiac glycosides primarily inhibit cell proliferation and the secretion of proinflammatory cytokines.

  12. 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.

  13. Targeting FXYD2 by cardiac glycosides potently blocks tumor growth in ovarian clear cell carcinoma

    PubMed Central

    Hsu, I-Ling; Chou, Cheng-Yang; Wu, Yi-Ying; Wu, Jia-En; Liang, Chen-Hsien; Tsai, Yao-Tsung; Ke, Jhen-Yu; Chen, Yuh-Ling; Hsu, Keng-Fu; Hong, Tse-Ming

    2016-01-01

    Ovarian clear cell carcinoma (OCCC) is an aggressive neoplasm with a high recurrence rate that frequently develops resistance to platinum-based chemotherapy. There are few prognostic biomarkers or targeted therapies exist for patients with OCCC. Here, we identified that FXYD2, the modulating subunit of Na+/K+-ATPases, was highly and specifically expressed in clinical OCCC tissues. The expression levels of FXYD2 were significantly higher in advanced-stage of OCCC and positively correlated with patients' prognoses. Silencing of FXYD2 expression in OCCC cells inhibited Na+/K+-ATPase enzyme activity and suppressed tumor growth via induction of autophagy-mediated cell death. We found that high FXYD2 expression in OCCC was transcriptionally regulated by the transcriptional factor HNF1B. Furthermore, up-regulation of FXYD2 expression significantly increased the sensitivity of OCCC cells to cardiac glycosides, the Na+/K+-ATPase inhibitors. Two cardiac glycosides, digoxin and digitoxin, had a great therapeutic efficacy in OCCC cells in vitro and in vivo. Taken together, our results demonstrate that FXYD2 is functionally upregulated in OCCC and may serve as a promising prognostic biomarker and therapeutic target of cardiac glycosides in OCCC. PMID:26910837

  14. (+)-Strebloside-Induced Cytotoxicity in Ovarian Cancer Cells Is Mediated through Cardiac Glycoside Signaling Networks.

    PubMed

    Chen, Wei-Lun; Ren, Yulin; Ren, Jinhong; Erxleben, Christian; Johnson, Michael E; Gentile, Saverio; Kinghorn, A Douglas; Swanson, Steven M; Burdette, Joanna E

    2017-03-24

    (+)-Strebloside, a cardiac glycoside isolated from the stem bark of Streblus asper collected in Vietnam, has shown some potential for further investigation as an antineoplastic agent. A mechanistic study using an in vitro assay and molecular docking analysis indicated that (+)-strebloside binds and inhibits Na(+)/K(+)-ATPase in a similar manner to digitoxin. Inhibition of growth of different high-grade serous ovarian cancer cells including OVCAR3, OVSAHO, Kuramochi, OVCAR4, OVCAR5, and OVCAR8 resulted from treatment with (+)-strebloside. Furthermore, this compound blocked cell cycle progression at the G2 phase and induced PARP cleavage, indicating apoptosis activation in OVCAR3 cells. (+)-Strebloside potently inhibited mutant p53 expression through the induction of ERK pathways and inhibited NF-κB activity in human ovarian cancer cells. However, in spite of its antitumor potential, the overall biological activity of (+)-strebloside must be regarded as being typical of better-known cardiac glycosides such as digoxin and ouabain. Further chemical alteration of cardiac glycosides might help to reduce negative side effects while increasing cancer cell cytotoxicity.

  15. Cytotoxic cardiac glycosides from the fruit (pods) of Adenium obesum (Forssk.) Roem. & Schult.

    PubMed

    Ahmed, Salman Khalid; Versiani, Muhammad Ali; Ikram, Ambreen; Sattar, Samina Abdul; Faizi, Shaheen

    2017-05-01

    Phytochemical investigation of methanolic extract of Adenium obesum led to the isolation of 42 (1-42) compounds belongs to cardiac glycosides, triterpenoids and steroids. The chemical structures of isolated compounds were elucidated by spectral techniques UV, IR, NMR and FAB MS. The cardiac glycosides were tested against three human cell lines, 3T3 (normal cells), HeLa (Human cervical cancer cell lines) and PC-3 (Human prostate cancer cell lines). The cardiac glycoside, honghelin (4), obeside B (5) and obeside C (6) showed significant effects against cell lines Hela, 3T3 and PC-3 compared to standard drug doxorubicin. Compounds 4, 5 and 6 exhibited very low IC50 (μM) against the PC3 human cell line. 4 and 6 also showed least IC50 against the HeLa human cell lines as compared to the standard drug doxorubicin whereas these three compounds showed effect on 3T3 cell line with high IC50 values compared to drug cycloheximide.

  16. Cardiac glycoside activities link Na(+)/K(+) ATPase ion-transport to breast cancer cell migration via correlative SAR.

    PubMed

    Magpusao, Anniefer N; Omolloh, George; Johnson, Joshua; Gascón, José; Peczuh, Mark W; Fenteany, Gabriel

    2015-02-20

    The cardiac glycosides ouabain and digitoxin, established Na(+)/K(+) ATPase inhibitors, were found to inhibit MDA-MB-231 breast cancer cell migration through an unbiased chemical genetics screen for cell motility. The Na(+)/K(+) ATPase acts both as an ion-transporter and as a receptor for cardiac glycosides. To delineate which function is related to breast cancer cell migration, structure-activity relationship (SAR) profiles of cardiac glycosides were established at the cellular (cell migration inhibition), molecular (Na(+)/K(+) ATPase inhibition), and atomic (computational docking) levels. The SAR of cardiac glycosides and their analogs revealed a similar profile, a decrease in potency when the parent cardiac glycoside structure was modified, for each activity investigated. Since assays were done at the cellular, molecular, and atomic levels, correlation of SAR profiles across these multiple assays established links between cellular activity and specific protein-small molecule interactions. The observed antimigratory effects in breast cancer cells are directly related to the inhibition of Na(+)/K(+) transport. Specifically, the orientation of cardiac glycosides at the putative cation permeation path formed by transmembrane helices αM1-M6 correlates with the Na(+) pump activity and cell migration. Other Na(+)/K(+) ATPase inhibitors that are structurally distinct from cardiac glycosides also exhibit antimigratory activity, corroborating the conclusion that the antiport function of Na(+)/K(+) ATPase and not the receptor function is important for supporting the motility of MDA-MB-231 breast cancer cells. Correlative SAR can establish new relationships between specific biochemical functions and higher-level cellular processes, particularly for proteins with multiple functions and small molecules with unknown or various modes of action.

  17. Molluscicidal activity of cardiac glycosides from Nerium indicum against Pomacea canaliculata and its implications for the mechanisms of toxicity.

    PubMed

    Dai, Lingpeng; Wang, Wanxian; Dong, Xinjiao; Hu, Renyong; Nan, Xuyang

    2011-09-01

    Cardiac glycosides from fresh leaves of Nerium indicum were evaluated for its molluscicidal activity against Pomacea canaliculata (golden apple snail: GAS) under laboratory conditions. The results showed that LC(50) value of cardiac glycosides against GAS was time dependent and the LC(50) value at 96 h was as low as 3.71 mg/L, which was comparable with that of metaldehyde at 72 h (3.88 mg/L). These results indicate that cardiac glycosides could be an effective molluscicide against GAS. The toxicological mechanism of cardiac glucosides on GAS was also evaluated through changes of selected biochemical parameters, including cholinesterase (ChE) and esterase (EST) activities, glycogen and protein contents in hepatopancreas tissues of GAS. Exposure to sublethal concentrations of cardiac glycosides, GAS showed lower activities of EST isozyme in the later stages of the exposure period as well as drastically decreased glycogen content, although total protein content was not affected at the end of 24 and 48 h followed by a significant depletion at the end of 72 and 96 h. The initial increase followed by a decline of ChE activity was also observed during the experiment. These results suggest that cardiac glycosides seriously impair normal physiological metabolism, resulting in fatal alterations in major biochemical constituents of hepatopancreas tissues of P. canaliculata.

  18. 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.

  19. Transcriptome and Metabolite analysis reveal candidate genes of the cardiac glycoside biosynthetic pathway from Calotropis procera

    PubMed Central

    Pandey, Akansha; Swarnkar, Vishakha; Pandey, Tushar; Srivastava, Piush; Kanojiya, Sanjeev; Mishra, Dipak Kumar; Tripathi, Vineeta

    2016-01-01

    Calotropis procera is a medicinal plant of immense importance due to its pharmaceutical active components, especially cardiac glycosides (CG). As genomic resources for this plant are limited, the genes involved in CG biosynthetic pathway remain largely unknown till date. Our study on stage and tissue specific metabolite accumulation showed that CG’s were maximally accumulated in stems of 3 month old seedlings. De novo transcriptome sequencing of same was done using high throughput Illumina HiSeq platform generating 44074 unigenes with average mean length of 1785 base pair. Around 66.6% of unigenes were annotated by using various public databases and 5324 unigenes showed significant match in the KEGG database involved in 133 different pathways of plant metabolism. Further KEGG analysis resulted in identification of 336 unigenes involved in cardenolide biosynthesis. Tissue specific expression analysis of 30 putative transcripts involved in terpenoid, steroid and cardenolide pathways showed a positive correlation between metabolite and transcript accumulation. Wound stress elevated CG levels as well the levels of the putative transcripts involved in its biosynthetic pathways. This result further validated the involvement of identified transcripts in CGs biosynthesis. The identified transcripts will lay a substantial foundation for further research on metabolic engineering and regulation of cardiac glycosides biosynthesis pathway genes. PMID:27703261

  20. BDNF mediates neuroprotection against oxygen-glucose deprivation by the cardiac glycoside oleandrin.

    PubMed

    Van Kanegan, Michael J; He, Dong Ning; Dunn, Denise E; Yang, Peiying; Newman, Robert A; West, Anne E; Lo, Donald C

    2014-01-15

    We have previously shown that the botanical drug candidate PBI-05204, a supercritical CO2 extract of Nerium oleander, provides neuroprotection in both in vitro and in vivo brain slice-based models for focal ischemia (Dunn et al., 2011). Intriguingly, plasma levels of the neurotrophin BDNF were increased in patients treated with PBI-05204 in a phase I clinical trial (Bidyasar et al., 2009). We thus tested the hypothesis that neuroprotection provided by PBI-05204 to rat brain slices damaged by oxygen-glucose deprivation (OGD) is mediated by BDNF. We found, in fact, that exogenous BDNF protein itself is sufficient to protect brain slices against OGD, whereas downstream activation of TrkB receptors for BDNF is necessary for neuroprotection provided by PBI-05204, using three independent methods. Finally, we provide evidence that oleandrin, the principal cardiac glycoside component of PBI-05204, can quantitatively account for regulation of BDNF at both the protein and transcriptional levels. Together, these findings support further investigation of cardiac glycosides in providing neuroprotection in the context of ischemic stroke.

  1. Cardiac glycosides are potent inhibitors of interferon-β gene expression

    PubMed Central

    Ye, Junqiang; Chen, Shuibing; Maniatis, Tom

    2011-01-01

    We report that bufalin and other cardiac glycoside inhibitors of the sodium-potassium ATPase (sodium pump) potently inhibit the induction of the interferon-β (IFNβ) gene by virus, dsRNA or dsDNA. Cardiac glycosides increase the intracellular sodium concentration, which appears to inhibit the ATPase activity of the RNA sensor RIG-I, an essential and early component in the IFNβ activation pathway. This, in turn, prevents the activation of the critical transcription factors IRF3 and NFκB. Bufalin inhibition can be overcome by expressing a drug-resistant variant of the sodium pump, and knocking down the pump by shRNA inhibits IFNβ expression. Thus, bufalin acts exclusively through the sodium pump. We also show that bufalin inhibits tumor necrosis factor (TNF) signaling, at least in part by interfering with the nuclear translocation of NFκB. These findings suggest that bufalin could be used to treat inflammatory and autoimmune diseases where IFN or TNF are hyperactivated. PMID:21076398

  2. 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.

  3. Cardiac glycosides induce autophagy in human non-small cell lung cancer cells through regulation of dual signaling pathways.

    PubMed

    Wang, Yan; Qiu, Qiang; Shen, Jia-Jia; Li, Dian-Dong; Jiang, Xue-Jun; Si, Shu-Yi; Shao, Rong-Guang; Wang, Zhen

    2012-11-01

    Na(+)/K(+)-ATPase targeted cancer therapy has attracted increasing interests of oncologists in lung cancer field. Although multiple anti-cancer mechanisms of cardiac glycosides as Na(+)/K(+)-ATPase inhibitors are revealed, the role of autophagy and related molecular signaling pathway for the class of compounds in human non-small cell lung cancer (NSCLC) cells has not been systematically examined. We herein investigated the anti-cancer effects of two representative cardiac glycosides, digoxin and ouabain, in A549 and H460 cell lines. Both agents caused significant growth inhibition at nanomolar level. The cardiac glycosides were found to induce moderate G(2)/M arrest but not apoptosis at IC(50) level in the NSCLC cell lines. Moreover, autophagy was markedly induced by both agents, as evidenced by the time- and dose-dependent increase of LC3-II, up-regulation of Atg5 and Beclin1, as well as by the observations through acridine orange staining, transmission electron microscopy and quantification of GFP-LC3 fluorescence. Importantly, AMP-activated protein kinase (AMPK) pathway was activated, resulting in mammalian target of rapamycin (mTOR) deactivation during autophagy induction. Moreover, extracellular-signal-regulated kinase 1/2 (ERK1/2) activation was simultaneously found to be involved in the autophagy regulation. Co-treatment with respective inhibitors or siRNAs could either block the autophagic phenotypes and signals, or significantly increase the cellular viability, indicating the drugs-induced autophagy plays tumor-suppressing role. This work provides first evidence showing that the cardiac glycosides induce autophagy in human NSCLC cells through regulation of both mTOR and ERK1/2 signaling pathways. The autophagy may at least partially account for the growth inhibitory effects of the compounds in human NSCLC cells.

  4. Ischemia-induced alterations in myocardial (Na+ + K+)-ATPase and cardiac glycoside binding.

    PubMed Central

    Beller, G A; Conroy, J; Smith, T W

    1976-01-01

    The effects of ischemia on the canine myocardial (Na+ + K+)-ATPase complex were examined in terms of alterations in cardiac glycoside binding and enzymatic activity. Ability of the myocardial cell to bind tritiated ouabain in vivo was assessed after 1, 2, and 6 h of coronary occlusion followed by 45 min of reperfusion, and correlated with measurements of in vitro (Na+ + K+)-ATPase activity and in vitro [3H]ouabain binding after similar periods of ischemia. Regional blood flow alterations during occlusion and reperfusion were simultaneously determined utilizing 15 mum radioactive microspheres to determine the degree to which altered binding of ouabain might be flow related. Anterior wall infarction was produced in 34 dogs by snaring of confluent branches of the left coronary system. Epicardial electrograms delineated ischemic and border zone areas. Coronary reperfusion after 2 and 6 h of occlusion was associated with impaired reflow of blood and markedly impaired uptake of [3H]ouabain in ischemic myocardium. In both groups, in vivo [3H]ouabain binding by ischemic tissue was reduced out of proportion to the reduction in flow. Despite near-complete restoration of flow in seven dogs occluded for 1 h and reperfused, [3H]ouabain remained significantly reduced to 58 +/- 9% of nonischemic uptake in subendocardial layers of the central zone of ischemia. Thus, when coronary flow was restored to areas of myocardium rendered acutely ischemia for 1 or more hours, ischemic zones demonstrated progressively diminished ability to bind ouabain. To determine whether ischemia-induced alteration in myocardial (Na+ + K+)-ATPase might underlie these changes, (Na+ + K+)-ATPase activity and [3H]ouabain binding were measured in microsomal fractions from ischemic myocardium after 1, 2, and 6 h of coronary occlusion. In animals occluded for 6 h, (Na+ + K+)-ATPase activity was significantly reduced by 40% in epicardial and by 35% in endocardial layers compared with nonischemic myocardium

  5. 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

  6. L30A Mutation of Phospholemman Mimics Effects of Cardiac Glycosides in Isolated Cardiomyocytes.

    PubMed

    Himes, Ryan D; Smolin, Nikolai; Kukol, Andreas; Bossuyt, Julie; Bers, Donald M; Robia, Seth L

    2016-11-08

    To determine if mutations introduced into phospholemman (PLM) could increase the level of PLM-Na,K-ATPase (NKA) binding, we performed scanning mutagenesis of the transmembrane domain of PLM and measured Förster resonance energy transfer (FRET) between each mutant and NKA. We observed an increased level of binding to NKA for several PLM mutants compared to that of the wild type (WT), including L27A, L30A, and I32A. In isolated cardiomyocytes, overexpression of WT PLM increased the amplitude of the Ca(2+) transient compared to the GFP control. The Ca(2+) transient amplitude was further increased by L30A PLM overexpression. The L30A mutation also delayed Ca(2+) extrusion and increased the duration of cardiomyocyte contraction. This mimics aspects of the effect of cardiac glycosides, which are known to increase contractility through inhibition of NKA. No significant differences between WT and L30A PLM-expressing myocytes were observed after treatment with isoproterenol, suggesting that the superinhibitory effects of L30A are reversible with β-adrenergic stimulation. We also observed a decrease in the extent of PLM tetramerization with L30A compared to WT using FRET, suggesting that L30 is an important residue for mediating PLM-PLM binding. Molecular dynamics simulations revealed that the potential energy of the L30A tetramer is greater than that of the WT, and that the transmembrane α helix is distorted by the mutation. The results identify PLM residue L30 as an important determinant of PLM tetramerization and of functional inhibition of NKA by PLM.

  7. Ryanodine receptor phosphorylation by oxidized CaMKII contributes to the cardiotoxic effects of cardiac glycosides

    PubMed Central

    Ho, Hsiang-Ting; Liu, Bin; Snyder, Jedidiah S.; Lou, Qing; Brundage, Elizabeth A.; Velez-Cortes, Florencia; Wang, Honglan; Ziolo, Mark T.; Anderson, Mark E.; Sen, Chandan K.; Wehrens, Xander H.T.; Fedorov, Vadim V.; Biesiadecki, Brandon J.; Hund, Thomas J.; Györke, Sándor

    2014-01-01

    Aims Recent studies suggest that proarrhythmic effects of cardiac glycosides (CGs) on cardiomyocyte Ca2+ handling involve generation of reactive oxygen species (ROS). However, the specific pathway(s) of ROS production and the subsequent downstream molecular events that mediate CG-dependent arrhythmogenesis remain to be defined. Methods and results We examined the effects of digitoxin (DGT) on Ca2+ handling and ROS production in cardiomyocytes using a combination of pharmacological approaches and genetic mouse models. Myocytes isolated from mice deficient in NADPH oxidase type 2 (NOX2KO) and mice transgenically overexpressing mitochondrial superoxide dismutase displayed markedly increased tolerance to the proarrhythmic action of DGT as manifested by the inhibition of DGT-dependent ROS and spontaneous Ca2+ waves (SCW). Additionally, DGT-induced mitochondrial membrane potential depolarization was abolished in NOX2KO cells. DGT-dependent ROS was suppressed by the inhibition of PI3K, PKC, and the mitochondrial KATP channel, suggesting roles for these proteins, respectively, in activation of NOX2 and in mitochondrial ROS generation. Western blot analysis revealed increased levels of oxidized CaMKII in WT but not in NOX2KO hearts treated with DGT. The DGT-induced increase in SCW frequency was abolished in myocytes isolated from mice in which the Ser 2814 CaMKII phosphorylation site on RyR2 is constitutively inactivated. Conclusion These results suggest that the arrhythmogenic adverse effects of CGs on Ca2+ handling involve PI3K- and PKC-mediated stimulation of NOX2 and subsequent NOX2-dependent ROS release from the mitochondria; mitochondria-derived ROS then activate CaMKII with consequent phosphorylation of RyR2 at Ser 2814. PMID:24104877

  8. Cardiac glycosides in the treatment of experimental overdose with calcium-blocking agents.

    PubMed

    Ramo, M P; Grupp, I; Pesola, M K; Heikkila, J; Luomanmaki, K; Schroder, T; Grupp, G

    1992-01-01

    The ability of digitalis compounds to counteract calcium antagonist overdose was studied in anesthetized dogs (n = 6, 13.5 +/- 0.7 kg) and isolated trabeculae from human hearts (n = 7). Digitalis caused by increasing intracellular cytosolic Ca2+ concentration through Na+/Ca(2+)-exchange across the cell membrane, was postulated to overcome the detrimental effects of excessive slow calcium-channel blockade. In anesthetized dogs, an infusion of verapamil (40 mg/30 min, i.v.) decreased mean arterial pressure from 88 +/- 6 to 66 +/- 6 mm Hg (P < 0.05), reduced systemic vascular resistance (SVR) from 3838 +/- 916 to 2200 +/- 669 dyne.s/cm5 (P < 0.05), and induced total atrio-ventricular (A-V) block in three animals. Stroke volume (SV) remained unchanged. Administration (i.v.) of NaCl (0.9%, 200 ml) and calcium gluconate (100 mg)--to increase the availability of Na+ and Ca(2+)--together with atropine (0.2 mg)--to block the parasympathetic effects of digoxin on A-V conduction--increased left ventricular contractility (15%) but had no significant effects on blood pressure, SV, or A-V block. Digoxin (0.125 mg) returned sinus rhythm in all dogs and, by increasing SVR (P < 0.05) and left ventricular contractility (P < 0.05), returned arterial pressures to baseline. Because of increased afterload, SV decreased slightly (15%) despite increased cardiac contractility. In experiments with isolated trabeculae from diseased human hearts, TA 3090 (Clentiazem) depressed contractile force and ouabain, another glycoside, restored contractile force within 30 min.(ABSTRACT TRUNCATED AT 250 WORDS)

  9. Optimization and validation of a high-performance liquid chromatography method for the analysis of cardiac glycosides in Digitalis lanata.

    PubMed

    Pellati, Federica; Bruni, Renato; Bellardi, Maria Grazia; Bertaccini, Assunta; Benvenuti, Stefania

    2009-04-10

    In this study, a simple and reliable HPLC method for the qualitative and quantitative analysis of cardiac glycosides in Digitalis lanata Ehrh. raw material was developed and applied to healthy and phytoplasma-infected plants. The target analytes cover a broad range of secondary metabolites, including primary, secondary and tertiary glycosides and the corresponding aglycones. The sample preparation was carried out by sonication of the plant material with 70% (v/v) aqueous methanol at room temperature, followed by reversed-phase solid-phase extraction purification from interfering pigments. The HPLC analyses were performed on a Symmetry C(18) column (75 mm x 4.6mm I.D., 3.5 microm), with a gradient elution composed of water and acetonitrile, at a flow rate of 1.0 mL/min. The column temperature was set at 20 degrees C and the photodiode array detector monitored the eluent at 220 nm. The method was validated with respect to ICH guidelines and the validation parameters were found to be highly satisfactory. The application of the method to the analysis of D. lanata leaves indicated that air-drying was the optimum method for raw material processing when compared with freeze-drying. The analysis of healthy and phytoplasma-infected plants demonstrated that the secondary metabolite mainly affected by the pathogen presence was lanatoside C (153.2 microg/100mg versus 76.1 microg/100mg). Considering the importance of D. lanata plant material as source of cardiac glycosides, the developed method can be considered suitable for the phytochemical analysis and for the quality assurance of D. lanata used for pharmaceutical purpose.

  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. Delivery of acetylthevetin B, an antitumor cardiac glycoside, using polymeric micelles for enhanced therapeutic efficacy against lung cancer cells

    PubMed Central

    Zhu, Jing-jing; Zhang, Xin-xin; Miao, Yun-qiu; He, Shu-fang; Tian, Dan-mei; Yao, Xin-sheng; Tang, Jin-shan; Gan, Yong

    2017-01-01

    Acetylthevetin B (ATB), a cardiac glycoside from the seed of Thevetia peruviana (Pers) K Schum (yellow oleander), exhibits not only antitumor activity but also potential cardiac toxicity. In the present study, we attempted to enhance its antitumor action and decrease its adverse effects via chitosan-Pluronic P123 (CP) micelle encapsulation. Two ATB-loaded CP micelles (ATB-CP1, ATB-CP2) were prepared using an emulsion/solvent evaporation technique. They were spherical in shape with a particle size of 40–50 nm, showed a neutral zeta potential, and had acceptable encapsulation efficiency (>90%). Compared to the free ATB (IC50=2.94 μmol/L), ATB-loaded CP micelles exerted much stronger cytotoxicity against human lung cancer A549 cells with lower IC50 values (0.76 and 1.44 μmol/L for ATB-CP1 and ATB-CP2, respectively). After administration of a single dose in mice, the accumulation of ATB-loaded CP1 micelles in the tumor and lungs, respectively, was 15.31-fold and 9.49-fold as high as that of free ATB. A549 xenograft tumor mice treated with ATB-loaded CP1 micelles for 21 d showed the smallest tumor volume (one-fourth of that in the control group) and the highest inhibition rate (85.6%) among all the treatment groups. After 21-d treatment, no significant pathological changes were observed in hearts and other main tissues. In summary, ATB may serve as a promising antitumor chemotherapeutic agent for lung cancer, and its antitumor efficacy was significantly improved by CP micelles, with lower adverse effects. PMID:27917871

  12. Lanatoside C, a cardiac glycoside, acts through protein kinase Cδ to cause apoptosis of human hepatocellular carcinoma cells

    PubMed Central

    Chao, Min-Wu; Chen, Tzu-Hsuan; Huang, Han-Li; Chang, Yu-Wei; HuangFu, Wei-Chun; Lee, Yu-Ching; Teng, Che-Ming; Pan, Shiow-Lin

    2017-01-01

    Recent studies have revealed that cardiac glycosides, such as digitalis and digoxin, have anticancer activity and may serve as lead compounds for the development of cancer treatments. The poor prognosis of hepatocellular carcinoma (HCC) patients reflects the development of resistance to current chemotherapeutic agents, highlighting the need for discovering new small-molecule therapeutics. Here, we found that lanatoside C, an anti-arrhythmic agent extracted from Digitalis lanata, inhibited the growth of HCC cells and dramatically decreased tumor volume as well as delayed tumor growth without obvious body weight loss. Moreover, lanatoside C triggered mitochondrial membrane potential (MMP) loss, activation of caspases and translocation of apoptosis-inducing factor (AIF) into the nucleus, which suggests that lanatoside C induced apoptosis through both caspase-dependent and -independent pathways. Furthermore, we discovered that lanatoside C activated protein kinase delta (PKCδ) via Thr505 phosphorylation and subsequent membrane translocation. Inhibition of PKCδ reversed lanatoside C-induced MMP loss and apoptosis, confirming that lanatoside C caused apoptosis through PKCδ activation. We also found that the AKT/mTOR pathway was negatively regulated by lanatoside C through PKCδ activation. In conclusion, we provide the first demonstration that the anticancer effects of lanatoside C are mainly attributable to PKCδ activation. PMID:28387249

  13. Thyroid-induced alterations in myocardial sodium-potassium-activated adenosine triphosphatase, monovalent cation active transport, and cardiac glycoside binding.

    PubMed Central

    Curfman, G D; Crowley, T J; Smith, T W

    1977-01-01

    The effects of thyroid hormone on guinea pig myocardial NaK-ATPase activity, transmembrane monovalent cation active transport, and cardiac glycoside binding were were examined. NaK-ATPase activities of left atrial and left ventricular homogenates of control and triiodothyronine (T3)-treated animals were determined, and compared to activities of skeletal muscle and liver. T3 administration was associated with a significant increase of 18% in left atrial and left ventricular NaK-ATPase specific activities. This increment was less than that noted in skeletal muscle (+42%) and liver (+30%). To determine if enhanced NaK-ATPase activity was accompanied by increased monovalent cation active transport, in vitro 86Rb+ uptake by left atrial strips and hemidiaphragms was measured. Transition from the euthyroid to the hyperthyroid state resulted in a 68% increase in active 86Rb+ uptake by left atrium, and a 62% increase in active uptake by diaphragm. Passive 86Rb+ uptake was not affected in either tissue. Ouabain binding by atrial and ventricular homogenates of T3-treated animals was increased by 19 and 17%, respectively, compared to controls, in close agreement with thyroid-induced increments in NaK-ATPase activiey. Taken together, these results are consistent with enhanced myocardial NaK-ATPase activity and monovalent cation activt transport due to an increase in the number of functional enzyme complexes. PMID:138689

  14. Characterization of Cardiac Glycoside Natural Products as Potent Inhibitors of DNA Double-Strand Break Repair by a Whole-Cell Double Immunofluorescence Assay.

    PubMed

    Surovtseva, Yulia V; Jairam, Vikram; Salem, Ahmed F; Sundaram, Ranjini K; Bindra, Ranjit S; Herzon, Seth B

    2016-03-23

    Small-molecule inhibitors of DNA repair pathways are being intensively investigated as primary and adjuvant chemotherapies. We report the discovery that cardiac glycosides, natural products in clinical use for the treatment of heart failure and atrial arrhythmia, are potent inhibitors of DNA double-strand break (DSB) repair. Our data suggest that cardiac glycosides interact with phosphorylated mediator of DNA damage checkpoint protein 1 (phospho-MDC1) or E3 ubiquitin-protein ligase ring finger protein 8 (RNF8), two factors involved in DSB repair, and inhibit the retention of p53 binding protein 1 (53BP1) at the site of DSBs. These observations provide an explanation for the anticancer activity of this class of compounds, which has remained poorly understood for decades, and provide guidance for their clinical applications. This discovery was enabled by the development of the first high-throughput unbiased cellular assay to identify new small-molecule inhibitors of DSB repair. Our assay is based on the fully automated, time-resolved quantification of phospho-SER139-H2AX (γH2AX) and 53BP1 foci, two factors involved in the DNA damage response network, in cells treated with small molecules and ionizing radiation (IR). This primary assay is supplemented by robust secondary assays that establish lead compound potencies and provide further insights into their mechanisms of action. Although the cardiac glycosides were identified in an evaluation of 2366 small molecules, the assay is envisioned to be adaptable to larger compound libraries. The assay is shown to be compatible with small-molecule DNA cleaving agents, such as bleomycin, neocarzinostatin chromophore, and lomaiviticin A, in place of IR.

  15. Antitumor effects of naturally occurring cardiac glycosides convallatoxin and peruvoside on human ER+ and triple-negative breast cancers

    PubMed Central

    Kaushik, Vivek; Azad, Neelam; Yakisich, Juan Sebastian; Iyer, Anand Krishnan V

    2017-01-01

    Breast cancer is second most prevalent cancer in women, and the second only to lung cancer in cancer-related deaths. It is a heterogeneous disease and has several subtypes based on the presence or absence of hormone receptors and/or human epidermal growth factor receptor 2 (HER2). Hormone receptor-positive and HER2-enriched cancers can be targeted using hormone and HER2-targeting therapies such as trastuzumab or lapatinib. However, triple-negative breast cancers (TNBCs) do not express any of the receptors and therefore are resistant to most targeted therapies, and cytotoxic chemotherapies are the only viable option available for the treatment of TNBCs. Recently, cardiac glycosides (CGs) have emerged as potential anticancer agents that impart their antiproliferative effect by targeting multiple pathways. In this study our aim was to evaluate anticancer effects of two naturally occurring CGs, Convallatoxin (CT) and Peruvoside (PS), on ER+ and TNBCs cells. CT and PS demonstrated dose- and time-dependent cytotoxic effect on MCF-7 cells, which was further supported by loss of colony formation on drug treatment. CT and PS arrested MCF-7 cells in the G0/G1 phase and reduced the viability of MCF-7-derived mammospheres (MMs). Interestingly, while CT and PS imparted cell death in TNBCs cells from both Caucasians (MDA-MB-231 cells) and African Americans (MDA-MB-468 cells) in a dose- and time-dependent manner, the drugs were much more potent in MDA-MB-468 as compared with TNBC MDA-MB-231 cells. Both drugs significantly inhibited migration and invasion of both MCF-7 and MDA-MB-468 cells. An assessment of intracellular pathways indicated that both drugs were able to modulate several key cellular pathways such as EMT, cell cycle, proliferation and cell death in both cell types. Our data suggest a promising role for CGs in breast cancer treatment specifically in targeting TNBCs derived from African Americans, and provides impetus for further investigation of the anticancer

  16. Kinetics of active sodium transport in rat proximal tubules and its variation by cardiac glycosides at zero net volume and ion fluxes. Evidence for a multisite sodium transport system.

    PubMed Central

    Györy, A Z; Lingard, J M

    1976-01-01

    1. Transepithelial Na concentration difference, deltaCNa, across proximal tubules of rat kidney was measured at varying intraluminal Na concentrations (CNainfinity) under conditions of zero net volume and Na flux. Simultaneous stopped-flow intratubular and artificial peritubular capillary perfusion techniques were used together with intratubular raffinose to achieve zero net fluxes. Under these conditions in rat proximal tubules, deltaCNa represents active transport, JactNa, factored by permeability, PNa, plus an electrical factor depending on transepithelial potential difference. 2. The relationship between CNainfinity and deltaCNa appeared sigmoidal with saturation being reached when intratubular Na was above 80 m-mole/kg. In the presence of ouabain (10(-2)M) and scilliroside (10(-3)M) the relationship remained the same. The maximum deltaCNa was reduced by approximately 50% by cardiac glycoside inhibition whereas the half-saturation constant was essentially unchanged. These changes from the control represent simple non-competitive inhibition by the cardiac glycosides. 3. Absence of potential difference (p.d.) measurements precludes exact description of the relation between true active transport and substrate concentration but much evidence indicates that the apparently sigmoid relation in the presence and absence of cardiac glycoside inhibition, would be retained if correction of deltaCNa values were possible. Such results could then be explained if there are at least three or more sites for Na on the pump system, of which at least two are not cardiac glycoside sensitive. They would also unequivocally exclude the presence of a single-site single-pump system or the simple algebraic addition of two such units since the kinetic curves for both would be hyperbolic rather than sigmoidal. PMID:950594

  17. Simultaneous determination of various cardiac glycosides by liquid chromatography-hybrid mass spectrometry for the purity assessment of the therapeutic monitored drug digoxin.

    PubMed

    Josephs, Ralf Dieter; Daireaux, Adeline; Westwood, Steven; Wielgosz, Robert Ian

    2010-07-02

    A high performance liquid chromatography-hybrid tandem mass spectrometry (LC-MS(n)) method utilising electrospray ionisation has been developed and implemented for the simultaneous determination of several cardiac glycosides (CGs) as well as their corresponding aglycones formed by and extracted from herbaceous plants of the genus Digitalis. The method has been validated in-house and its performance characteristics (linearity, repeatability, limits of detection, etc.) were assessed for use in the quantification of CGs and their corresponding aglycones. LODs from 38 to 936pgg(-1) in solution, corresponding to mass fraction impurity levels from 0.0009 (or 0.00008%) to 0.019mgg(-1) (or 0.0019%) detectable in the pure materials have been realized. Moreover, the method was used to characterize and to determine the inherent CG impurities in batches of the therapeutic monitored drug digoxin which served as candidate reference material for an organic purity assessment inter-laboratory study (CCQM-P20.f) organised by the BIPM Chemistry Section and carried out within the framework of the Organic Analysis Working Group (OAWG) of the Consultative Committee for Amount of Substance - Metrology in Chemistry (CCQM). Digoxin was selected from materials required for the establishment of reference measurement systems for clinical chemistry and laboratory medicine.

  18. 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

  19. 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.

  20. Oleic and linoleic acids are active principles in Nigella sativa and stabilize an E(2)P conformation of the Na,K-ATPase. Fatty acids differentially regulate cardiac glycoside interaction with the pump.

    PubMed

    Mahmmoud, Yasser A; Christensen, S Brøgger

    2011-10-01

    Nigella sativa seed oil was found to contain a modulator of Na,K-ATPase. Separation analyses combined with (1)H NMR and GCMS identified the inhibitory fraction as a mixture of oleic and linoleic acids. These two fatty acids are specifically concentrated in several medicinal plant oils, and have particularly been implicated in decreasing high blood pressure. The ouabain binding site on Na,K-ATPase has also been implicated in blood pressure regulation. Thus, we aimed to determine how these two molecules modify pig kidney Na,K-ATPase. Oleic and linoleic acids did not modify reactions involving the E(1) (Na(+)) conformations of the Na,K-ATPase. In contrast, K(+) dependent reactions were strongly modified after treatment. Oleic and linoleic acids were found to stabilize a pump conformation that binds ouabain with high affinity, i.e., an ion free E(2)P form. Time-resolved binding assays using anthroylouabain, a fluorescent ouabain analog, revealed that the increased ouabain affinity is unique to oleic and linoleic acids, as compared with γ-linolenic acid, which decreased pump-mediated ATP hydrolysis but did not equally increase ouabain interaction with the pump. Thus, the dynamic changes in plasma levels of oleic and linoleic acids are important in the modulation of the sensitivity of the sodium pump to cardiac glycosides. Given the possible involvement of the cardiac glycoside binding site on Na,K-ATPase in the regulation of hypertension, we suggest oleic acid to be a specific chaperon that modulates interaction of cardiac glycosides with the sodium pump.

  1. Cardiotonic action of two tannins

    PubMed Central

    Broadbent, J. L.

    1962-01-01

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

  2. [Cardiac glycosides and metabolites--problems of recovery in tissue extracts. Separation of visible substance spots in the nanogram range (author's transl)].

    PubMed

    Aderjan, R; Doster, S; Petri, H; Schmidt, G

    1979-08-01

    The recovery measurements in rat tissues performed via i.p. injected radioactive digoxin derivates (3H-digoxin, 125J-digoxin derivative) showed that approximately 50% of the total glycoside content will be extracted. Thus, an addition of digoxin standards to drug-free tissues may lead to false negative determinations. By comparison of the radioactivity before and after extraction the following results were obtained: Recovery from tissues 3H-digoxin 50% 125J-digoxin 40% from serum 3H-digoxin 60% added to drug free tissue homogenates 3H-digoxin 85% After i.p. application of 15 mg/kg of beta-methyldigoxin to BD9 (Berlin)-rats the resulting tissue concentrations were extracted by Amberlite XAD-2. beta-Methyldigoxin and its metabolites digoxin and digoxinbisdigitoxide could be separated and distinguished from artifacts by fluorescence detection on HPTLC-plates with a detection limit of 60 ng/spot. Concentration determined by radioimmunoassay are in satisfactory agreement with HPTLC results.

  3. Tannins in plant-herbivore interactions.

    PubMed

    Barbehenn, Raymond V; Peter Constabel, C

    2011-09-01

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

  4. Iridoid glycosides from Globularia trichosantha.

    PubMed

    Caliş, I; Kirmizibekmez, H; Sticher, O

    2001-01-01

    A new iridoid glycoside, deacetylalpinoside (2), was isolated from the aerial parts of Globularia trichosantha together with nine known iridoid glycosides: catalpol, 10-O-benzoyl-catalpol, aucubin, asperuloside, deacetylasperuloside, asperulosidic acid, scandoside, geniposidic acid, and alpinoside (1). From the underground parts of the same plant, two new bisiridoid glycosides, globulosides A (3) and B (4); a known iridoid glycoside, globularidin; a lignan glycoside, liriodendrin; and seven phenylethanoid glycosides, arenarioside, verbascoside (= acteoside), isoacteoside, crenatoside, isocrenatoside, and trichosanthosides A and B, were isolated. Compounds 2-4 are new iridoids containing an 8,9 double bond representing a rare carbon skeleton. Their structures were established by spectroscopic methods.

  5. 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.

  6. Tannins and human health: a review.

    PubMed

    Chung, K T; Wong, T Y; Wei, C I; Huang, Y W; Lin, Y

    1998-08-01

    Tannins (commonly referred to as tannic acid) are water-soluble polyphenols that are present in many plant foods. They have been reported to be responsible for decreases in feed intake, growth rate, feed efficiency, net metabolizable energy, and protein digestibility in experimental animals. Therefore, foods rich in tannins are considered to be of low nutritional value. However, recent findings indicate that the major effect of tannins was not due to their inhibition on food consumption or digestion but rather the decreased efficiency in converting the absorbed nutrients to new body substances. Incidences of certain cancers, such as esophageal cancer, have been reported to be related to consumption of tannins-rich foods such as betel nuts and herbal teas, suggesting that tannins might be carcinogenic. However, other reports indicated that the carcinogenic activity of tannins might be related to components associated with tannins rather than tannins themselves. Interestingly, many reports indicated negative association between tea consumption and incidences of cancers. Tea polyphenols and many tannin components were suggested to be anticarcinogenic. Many tannin molecules have also been shown to reduce the mutagenic activity of a number of mutagens. Many carcinogens and/or mutagens produce oxygen-free radicals for interaction with cellular macromolecules. The anticarcinogenic and antimutagenic potentials of tannins may be related to their antioxidative property, which is important in protecting cellular oxidative damage, including lipid peroxidation. The generation of superoxide radicals was reported to be inhibited by tannins and related compounds. The antimicrobial activities of tannins are well documented. The growth of many fungi, yeasts, bacteria, and viruses was inhibited by tannins. We have also found that tannic acid and propyl gallate, but not gallic acid, were inhibitory to foodborne bacteria, aquatic bacteria, and off-flavor-producing microorganisms. Their

  7. Steviol glycoside biosynthesis.

    PubMed

    Brandle, J E; Telmer, P G

    2007-07-01

    Steviol glycosides are found in high concentrations in the leaves of the Paraguayan perennial herb Stevia rebaudiana and their intense sweetness, as well as high concentration in Stevia leaf tissue, has made them the subject of research interest for over 100 years. Steviol glycosides are diterpenoids whose biosynthetic pathways share four steps in common with gibberellic acid formation. The convergence of genomics and plant biochemistry has led to the rapid elucidation of the genes coding for the various enzymes in the biosynthetic pathway. Functional characterization of the enzymes coded for by those genes is on-going. The first committed step in the pathway is the synthesis of the aglycone steviol and the various glycosides found in the leaf tissue result from the elaboration of steviol by a number of glucosyltransferases.

  8. 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

  9. Tannins, peptic ulcers and related mechanisms.

    PubMed

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

    2012-01-01

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

  10. Factors affecting skin tannin extractability in ripening grapes.

    PubMed

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

    2014-02-05

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

  11. Variants of glycoside hydrolases

    DOEpatents

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

    2013-02-26

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

  12. 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.

  13. 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...

  14. 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.

  15. Quinoid glycosides from Forsythia suspensa.

    PubMed

    Li, Chang; Dai, Yi; Zhang, Shu-Xiang; Duan, Ying-Hui; Liu, Ming-Li; Chen, Liu-Yuan; Yao, Xin-Sheng

    2014-08-01

    Phytochemical investigation on Forsythia suspensa (Thunb.) Vahl afforded 10 compounds, including quinoid glycosides, lignan glycosides, phenylethanoid glycoside and allylbenzene glycoside together with 13 known ones. Their structures were established based on extensive spectroscopic data analyses, including IR, UV, HRESIMS, 1D NMR and 2D NMR. Absolute configurations were determined by ECD calculation method and chemical degradation. In addition, all compounds were evaluated for their antiviral activity against influenza A (H1N1) virus and several were further evaluated against respiratory syncytial virus (RSV) in vitro. Among them, two previously known compounds showed significant activities against RSV with EC50 values of 3.43 and 6.72 μM.

  16. 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.

  17. 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.

  18. 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...

  19. Cytotoxicity of pregnane glycosides of Cynanchum otophyllum.

    PubMed

    Zhang, Mi; Li, Xiang; Xiang, Cheng; Qin, Yi; He, Jing; Li, Bao-Cai; Li, Peng

    2015-12-01

    Fourteen new pregnane glycosides, including nine caudatin glycosides (1-9), three qinyangshengenin glycosides (10-12), one kidjoranin glycosides (13) and one gagaminin glycosides (14), along with twelve known analogs (15-26) were isolated from roots of Cynanchum otophyllum Schneid. Their structures were deduced by detailed analysis of 1D and 2D NMR spectra, as well as HRESIMS. In this study, all pregnane glycosides obtained (1-26) were evaluated for their cytotoxic activities using three cancer cell lines (HepG2, Hela, U251). As results, except 6 and 10, other twenty-four pregnane glycosides showed cytotoxicities at different degrees against three cell lines.

  20. 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.

  1. Anticancer and antioxidant tannins from Pimenta dioica leaves.

    PubMed

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

    2007-01-01

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

  2. Cardiac catheterization

    MedlinePlus

    Catheterization - cardiac; Heart catheterization; Angina - cardiac catheterization; CAD - cardiac catheterization; Coronary artery disease - cardiac catheterization; Heart valve - cardiac catheterization; Heart failure - ...

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

    PubMed

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

    2013-11-01

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

  4. On the differences between ouabain and digitalis glycosides.

    PubMed

    Fuerstenwerth, Hauke

    2014-01-01

    Digoxin and digitoxin are widely used in the treatment of heart diseases. The exact mechanism of action of these drugs has remained an enigma. Ouabain has become the standard tool to investigate the mode of action of cardiotonic steroids, and results with ouabain are regarded as generally valid for all cardiac glycosides. However, there are marked differences between the effects of ouabain and digitalis glycosides. Ouabain has a different therapeutic profile from digitalis derivatives. Unlike digitalis glycosides, ouabain has a fast onset of action and stimulates myocardial metabolism. The inotropic effect of cardiotonic steroids is not related to inhibition of the Na-K-ATPase. Ouabain and digitalis derivatives develop their effects in different cellular spaces. Digitalis glycosides increase the intracellular calcium concentration by entering the cell interior and acting on the ryanodine receptors and by forming transmembrane calcium channels. Ouabain, by activation of the Na-K-ATPase from the extracellular side, triggers release of calcium from intracellular stores via signal transduction pathways and activates myocardial metabolism. These data no longer support the concept that all cardiotonic steroids exhibit their therapeutic effects by partial inhibition of the ion-pumping function of the Na-K-ATPase. Hence, it is suggested that this deeply rooted dogma be revised.

  5. 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.

  6. 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

  7. 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.

  8. Mechanisms of gold recovery from aqueous solutions using a novel tannin gel adsorbent synthesized from natural condensed tannin.

    PubMed

    Ogata, Takeshi; Nakano, Yoshio

    2005-11-01

    We report a novel recovery system for gold (Au), which is one of the precious metals contained in electronic scrap, utilizing tannin gel particles. Tannin gel particles were prepared by a process of cross-linking of condensed tannin (wattle tannin), which is a ubiquitous and inexpensive natural material having many hydroxyl groups. The adsorption mechanism of gold onto tannin gel particles was elucidated: the adsorption of gold takes place through the reduction of trivalent gold ions to metallic gold on the surface of tannin gel particles, which is accompanied by the simultaneous oxidization of the hydroxyl groups of tannin gel. Additionally, the adsorption capacity of gold was found to be extremely high, 8000 mg-Au/g-dry gel. The outstanding characteristics of tannin gel particles for gold offers the possibility of efficient recovery of other precious metals.

  9. 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...

  10. 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…

  11. 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 ...

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

    PubMed

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

    2017-04-03

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

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

    PubMed

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

    2015-09-02

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

  14. Lead chelation to immobilised Symphytum officinale L. (comfrey) root tannins.

    PubMed

    Chin, Lily; Leung, David W M; Harry Taylor, H

    2009-07-01

    Reported correlations between tannin level and metal accumulation within plant tissues suggest that metal-chelating tannins may help plants to tolerate toxic levels of heavy metal contaminants. This paper supports such correlations using a new method that demonstrated the ability of plant tannins to chelate heavy metals, and showed that the relative levels of tannins in tissues were quantitatively related to lead chelation in vitro. Using this in vitro metal chelation method, we showed that immobilised tannins prepared from lateral roots of Symphytum officinale L., that contained high tannin levels, chelated 3.5 times more lead than those from main roots with lower tannin levels. This trend was confirmed using increasing concentrations of tannins from a single root type, and using purified tannins (tannic acid) from Chinese gallnuts. This study presents a new, simple, and reliable method that demonstrates direct lead-tannin chelation. In relation to phytoremediation, it also suggests that plant roots with more 'built-in' tannins may advantageously accumulate more lead.

  15. 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.

  16. 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...

  17. 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.

  18. Steroidal glycosides from Reineckia carnea.

    PubMed

    Song, Xiaomei; Zhang, Dongdong; He, Hao; Li, Yuze; Yang, Xinjie; Deng, Chong; Tang, Zhishu; Cui, Jiucheng; Yue, Zhenggang

    2015-09-01

    Three new steroidal glycosides (1-3) and a novel natural product 4 firstly obtained from a plant source, together with two known steroidal glycosides (5-6) have been isolated from the whole plant of Reineckia carnea. Their structures were determined by physicochemical properties and spectroscopic methods, and their cytotoxic activities against human 1299 tumor cells were evaluated by the MTT method. Compounds 4, 5 and 6 exhibited cytotoxicity with IC50 values of 50.3 μmol·L(-1), 67.2 μmol·L(-1) and 61.8 μmol·L(-1), while compounds 1, 2, and 3 showed no cytotoxicity with the cells.

  19. 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.

  20. 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.

  1. Microbial hydrolysis of steviol glycosides.

    PubMed

    Renwick, A G; Tarka, S M

    2008-07-01

    A review of the role of gut microbiota in the metabolism of the steviol glycosides, stevioside and rebaudioside A, indicates that they are not absorbed intact but undergo hydrolysis by the intestinal microflora to steviol. Steviol is not metabolized by the intestinal flora and is absorbed from the intestine. The rate of hydrolysis for stevioside is greater than for rebaudioside A. Recent studies using mass spectrometry have shown that steviol-16,17-epoxide is not a microbial metabolite of steviol glycosides. Bacteroides species are primarily responsible for hydrolysis via their beta-glucosidase activity. Fecal incubation studies with both human and animal mixed flora provide similar results, and this indicates that the rat is an appropriate model for studies on steviol glycosides. Given the similarity in the microbial metabolism of stevioside and rebaudioside A with the formation of steviol as the single hydrolysis product that is absorbed from the intestinal tract, the toxicological data on stevioside are relevant to the risk assessment of rebaudioside A.

  2. The chemical synthesis of aryltetralin glycosides.

    PubMed

    Sun, Jian-Song; Liu, Hui; Guo, Xiao-Hong; Liao, Jin-Xi

    2016-01-28

    Led by etoposide and teniposide, the synthesis of aryltetralin glycosides has been experiencing flourishing development in the past five decades. Herein, a review focusing on the total synthesis of aryltetralin glycosides is provided. The main body of this review is composed of two parts, one is the enantioselective synthesis of aryltetralin derivatives and the other one is the construction of key glycosidic linkages. In each part the contents are organised based on the different strategies or protocols applied in the original documents. The total synthesis of aryltetralin glycosides represents the developing direction of this field, and sooner or later will replace the currently applied semi-total synthesis method, using the aglycon residue acquired directly from natural sources. This account provides a comprehensive and deep insight into the field of aryltetralin glycoside synthesis for chemists who have the intention of committing themselves to the development of aryltetralin glycoside medicine.

  3. Aroma Glycosides in Grapes and Wine.

    PubMed

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

    2017-02-01

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

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

    PubMed

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

    2013-10-02

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

  5. 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.

  6. New lignan glycosides from Justicia procumbens.

    PubMed

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

    2017-01-01

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

  7. 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.

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

    PubMed

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

    2015-01-01

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

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

    PubMed

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

    2014-01-01

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

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

    PubMed

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

    2016-02-03

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

  11. HPLC retention thermodynamics of grape and wine tannins.

    PubMed

    Barak, Jennifer A; Kennedy, James A

    2013-05-08

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

  12. 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...

  13. Toxic levels of glycosides in herbal medication: a potential cause of hyperkalaemia.

    PubMed

    Haden, M; Marshall, D A S; Murphy, B

    2011-11-01

    We report a previously healthy man presenting with life-threatening hyperkalaemia and heart failure. The only possible cause was thought to be the long list of herbal medications he was taking, several of which contained significant amounts of cardiac glycosides. Hyperkalaemia is known to be associated with digoxin toxicity and we present this as the likely cause in this case, and emphasize the importance of a thorough drug history in forming a differential diagnosis.

  14. [Tannins, a new family of bio-active natural organic compounds (questions and answers)].

    PubMed

    Okuda, T

    1995-02-01

    Twelve questions concerning tannin selected from questions raised by other workers on the author's research were picked up. The answers of each question are as follows. 1. What is tannin?--the differences between the old concept and the new definition of tannin. 2. Is tannic acid the same as tannin? 3. How could each tannin be analyzed as a pure compound? 4. Which tannin found in recent years is implicated with the change of the concept of tannin in medicinal plants? 5. Is it possible that one to several chemical structures represent tannins contained in each plant species? 6. Which tannin-containing plants met in the human life are rich in tannins? 7. Is tannin produced by all species of plants?--a correlation between the occurrence of hydrolyzable tannins and the plant evolution system. 8. When and where are the hydrolyzable tannin oligomers produced, in the plant or after extraction? 9. Are tannins bound to other substances in the plants? 10. Is it appropriate to call tannins "plant polyphenols"? 11. Is it true that tannins are inhibitors of enzymes? 12. What kind of biological activities have been found for tannins.

  15. Steroidal glycosides with antiproliferative activities from Digitalis trojana.

    PubMed

    Kirmizibekmez, Hasan; Masullo, Milena; Festa, Michela; Capasso, Anna; Piacente, Sonia

    2014-04-01

    The phytochemical investigation of Digitalis trojana led to the isolation of two cardiac glycosides (1, 2), one pregnane glycoside (3), three furostanol type saponins (4-6), along with three cleroindicins (7-9), four phenylethanoid glycosides (10-13), two flavonoids (14, 15) and two phenolic acid derivatives (16, 17). The structure elucidation of the isolates was carried out by NMR experiments as well as ESI-MS. The cytotoxic activity of compounds 1-13 against a small panel of cancer cell lines, namely MCF-7, T98G, HT-29, PC-3, A375 and SH-SY5Y, was investigated. Compounds 1-6 showed antiproliferative activity against human breast MCF-7 and colon HT-29 cancer cell lines with IC50 values ranging from 8.3 to 50 μM. In order to understand the mechanism involved in the cell death, the active compounds were tested as pro-apoptotic agents using propidium iodide staining by flow cytometry method. No significant increase was observed in the apoptosis of the MCF-7 and HT-29 cancer cells. Moreover, the effects of the active compounds on cell proliferation were assessed on the same cancer cell lines by cell cycle analysis of DNA content using flow cytometry. No significative changes were observed in the cell cycle of MCF-7, while significant changes in G2 /M cell cycle phase of HT-29 cells were observed after treatment with digitalin (1), cariensoside (3) and 22-O-methylparvispinoside B (6) at 10 μM.

  16. A new acetophenone glycoside from the flower buds of Syzygium aromaticum (cloves).

    PubMed

    Ryu, Byeol; Kim, Hye Mi; Woo, Jeong-Hwa; Choi, Jung-Hye; Jang, Dae Sik

    2016-12-01

    A new acetophenone, 2,4,6-trihydroxy-3-methylacetophenone-2-O-β-d-glucoside (1), together with 21 known compounds; one acetophenone (2), four chromone glycosides (3-6), six phenylpropanoids (7-12), six sesquiterpenoids (13-18), two triterpenoids (19 and 20), one sterol (21), and one tannin (22) were isolated from the flower buds of Syzygium aromaticum (cloves). The structure of the new compound 1 was determined by spectroscopic analyses including 1D-, 2D-NMR and HRMS interpretation. Among the isolates, one acetophenone (2), three phenylpropanoids (10-12), and one sesquiterpenoid (13) were isolated from the flower buds of S. aromaticum for the first time in this study. All the isolates (1-22) were evaluated for their cytotoxicity against human ovarian cancer cells (A2780) using MTT assays. Some of the isolates (5, 6, 9, 15, 17, 19, 20, and 21) showed either moderate or weak cytotoxicity on A2780 cells.

  17. 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

  18. Triterpenoidal glycosides from Justicia betonica.

    PubMed

    Kanchanapoom, Tripetch; Noiarsa, Pawadee; Ruchirawat, Somsak; Kasai, Ryoji; Otsuka, Hideaki

    2004-09-01

    dFrom the aerial portion of Justicia betonica L., four triterpenoidal glycosides (justiciosides A-D) were isolated. Their structures were established through chemical and NMR spectroscopic analyses as olean-12-ene-1beta,3beta,11alpha,28-tetraol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, olean-12-ene-1beta,3beta,11alpha,28-tetraol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, 11alpha-methoxy-olean-12-ene-1beta,3beta,28-triol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, 11alpha-methoxy-olean-12-ene-1beta,3beta,28-triol 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside, respectively.

  19. Glycosides from the root of Iodes cirrhosa.

    PubMed

    Gan, Maoluo; Zhang, Yanling; Lin, Sheng; Liu, Mingtao; Song, Weixia; Zi, Jiachen; Yang, Yongchun; Fan, Xiaona; Shi, Jiangong; Hu, Jinfeng; Sun, Jiandong; Chen, Naihong

    2008-04-01

    Seven new neolignan glycosides ( 1- 7), two arylglycerol glycosides ( 8, 9), and 18 known glycosides have been isolated from an ethanolic extract of the root of Iodes cirrhosa. Their structures including absolute configurations were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo and erythro 8-4'-oxyneolignans and arylglycerols in different solvents, the validity of J 7,8 and Deltadelta C8-C7 values to distinguish threo and erythro derivatives was discussed. In the in vitro assays, compound 4 and liriodendrin ( 17) both showed activity against glutamate-induced PC12 cell damage at 10 (-5) M.

  20. Four new phenolic glycosides from Baoyuan decoction.

    PubMed

    Ma, Xiaoli; Guo, Xiaoyu; Zhao, Mingbo; Tu, Pengfei; Jiang, Yong

    2017-03-01

    Four new phenolic glycosides, including two flavonoid glycosides (1 and 2) and two lignan glycosides (3 and 4), were isolated from the traditional Chinese medicine formula, Baoyuan decoction. Their structures were established by detailed analysis of the NMR and HR-ESI-MS spectroscopic data and their absolute configurations were determined by the experimental electronic circular dichroism data as well as chemical methods. Furthermore, the sources of the four new compounds were determined by the UPLC-Qtrap-MS method, which proved that 1 and 2 are originated from Glycyrrhiza uralensis, and 3 and 4 are from Cinnamomum cassia.

  1. 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

  2. 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.

  3. 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.

  4. Electrochemical removal of tannins from aqueous solutions

    SciTech Connect

    Buso, A.; Balbo, L.; Giomo, M.; Farnia, G.; Sandona, G.

    2000-02-01

    The application of electrochemical methods to remove tannins from wastewater was investigated. Gallotannic acid was used as the reference substance. Electrochemical experiments were performed using platinum electrodes. Macroscale potentiostatic or galvanostatic electrolyses were carried out with sodium sulfate or sodium chloride as supporting electrolytes, to analyze direct and indirect oxidation processes. Operating variables such as pH and chloride concentration were considered to determine their influence on the efficiency and energy consumption of the process. The simulation of a pilot plant was carried out with a mathematical model, the parameters of which were determined by fitting of experimental profiles. The results of a preliminary investigation on the oxidation-coagulation process using sacrificial electrodes are also reported.

  5. Recent developments in β-C-glycosides: synthesis and applications.

    PubMed

    Lalitha, Krishnamoorthy; Muthusamy, Kumarasamy; Prasad, Y Siva; Vemula, Praveen Kumar; Nagarajan, Subbiah

    2015-01-30

    In the last few years, considerable progress has been made in the synthesis of C-glycosides. Despite its challenging chemistry, due to its versatility, C-glycosides play a pivotal role in developing novel materials, surfactants and bioactive molecules. In this review, we present snapshots of various synthetic methodologies developed for C-glycosides in the recent years and the potential application of C-glycosides derived from β-C-glycosidic ketones.

  6. Stereoselective Synthesis of β-manno-Glycosides

    NASA Astrophysics Data System (ADS)

    Ishiwata, Akihiro; Ito, Yukishige

    Among the various types of O-glycosides with biological relevance, the β-glycoside of D-mannose (β-manno-glycoside) has been considered as one of the most challenging targets from a synthetic point of view. The majority of synthetic approaches to β-manno-glycoside can be put into two categories (the direct glycosylation and the glycosylation-inversion approaches). Additionally, a variety of intriguing approaches have been investigated with substantial success (alkylative glycosylation of 1,2-stannylene acetal, reductive manipulation of orthoester, intramolecular aglycon delivery, and enzymatic glycosylation). In this chapter, progress in the conceptually demanding β-mannosylation technology will be discussed, including current state of the art, with particular focus upon applications related to the synthesis of glycoprotein-related oligosaccharides.

  7. Two new coumarin glycosides from Peucedanum praeruptorum.

    PubMed

    Chang, Hai-Tao; Okada, Yoshihito; Ma, Ting-Jun; Okuyama, Toru; Tu, Peng-Fei

    2008-01-01

    Two new coumarin glycosides, praerosides VI (1) and VII (2), were isolated from the roots of Peucedanum praeruptorum Dunn. Their structures were elucidated by chemical reaction and NMR spectroscopic methods.

  8. Three new glycosides from Hylocereus undatus.

    PubMed

    Wu, Xin; Wang, Ying; Huang, Xiao-Jun; Fan, Chun-Lin; Wang, Guo-Cai; Zhang, Xiao-Qi; Zhang, Qin-Wen; Ye, Wen-Cai

    2011-08-01

    Three new glycosides, undatusides A-C (1-3), and 11 known compounds (4-14) were isolated from the flowers of Hylocereus undatus. Their structures were elucidated on the basis of spectroscopic data and chemical method.

  9. 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.

  10. Triterpenoid glycosides from Ladenbergia hexandra Klotzsch.

    PubMed

    Furukawa, Megumi; Kamo, Satoshi; Makino, Mitsuko; Kurita, Masahiro; Tabata, Keiichi; Matsuzaki, Keiichi; Suzuki, Takashi; Uchiyama, Taketo

    2017-04-01

    From the bark of Ladenbergia hexandra Klotzsch, ten triterpenoid glycosides were isolated along with five known compounds, and their structures were determined based on extensive NMR and mass spectroscopic, GC and HPLC analyses. Some triterpenoid glycosides contained 6-deoxy-D-allose or D-allose as a sugar moiety. The absolute stereochemical assignment of the sugars was determined by comparison with synthetic samples, as well as by GC and HPLC analysis.

  11. Pregnane glycosides from Caralluma adscendens var. fimbriata.

    PubMed

    Kunert, Olaf; Rao, Vijayalakshmi Gurunath; Babu, Gummadi Sridhar; Sujatha, Palatheeya; Sivagamy, Malayalam; Anuradha, Sandala; Rao, Belvotagi Venkatrao Adavi; Kumar, Bobbala Ravi; Alex, Robert Michael; Schühly, Wolfgang; Kühnelt, Doris; Rao, Ghanakota Venkateshwara; Rao, Achanta Venkata Narasimha Appa

    2008-02-01

    Eleven novel pregnane glycosides, 2-7 and 9-13, of which four, i.e., 10-13, comprised a new pregnane-type genin exhibiting a hydroxymethylene instead of a Me group at C(19), and the known pregnane glycoside stalagmoside V (8) were isolated from whole plants of Caralluma adscendens var. fimbriata, a native Indian succulent plant. Their structures were elucidated by extensive 2D-NMR spectroscopic studies.

  12. New pregnane glycosides from Caralluma dalzielii.

    PubMed

    De Leo, Marinella; De Tommasi, Nunziatina; Sanogo, Rokia; Autore, Giuseppina; Marzocco, Stefania; Pizza, Cosimo; Morelli, Ivano; Braca, Alessandra

    2005-08-01

    Twenty-seven new pregnane glycosides were isolated from the whole plant of Caralluma dalzielii, and their structures elucidated from extensive 2D NMR analysis as well as ESI-MS experiments. All isolated compounds were tested for their antiproliferative activity on J774.A1, HEK-293, and WEHI-164 cell lines. Moderate to high potency of cytotoxicities were found in almost all tested compounds, confirming the significant cytotoxic activity of pregnane glycosides.

  13. 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.

  14. 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.

  15. 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.

  16. 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.

  17. 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

  18. Steroidal glycosides from the leaves of Cestrum nocturnum.

    PubMed

    Mimaki, Yoshihiro; Watanabe, Kazuki; Sakagami, Hiroshi; Sashida, Yutaka

    2002-12-01

    Further phytochemical analysis aimed at the steroidal glycoside constituents of the leaves of Cestrum nocturnum has resulted in the isolation of eight new steroidal glycosides (1-8), which were classified into a spirostanol saponin (1), a furostanol saponin (2), a pseudo-furostanol saponin (3), two pregnane glycosides (4, 5), two cholestane glycosides (6, 7), and pregnane-carboxylic acid gamma-lactone glycoside (8), and of two known spirostanol glycosides (9, 10). The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.

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

    PubMed

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

    2009-04-01

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

  20. 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.

  1. Cardiac catheterization - discharge

    MedlinePlus

    Catheterization - cardiac - discharge; Heart catheterization - discharge: Catheterization - cardiac; Heart catheterization; Angina - cardiac catheterization discharge; CAD - cardiac catheterization discharge; Coronary artery disease - cardiac catheterization ...

  2. New triterpenoid glycosides from the roots of Ilex asprella.

    PubMed

    Wang, Lei; Cai, Yan; Zhang, Xiao-Qi; Fan, Chun-Lin; Zhang, Qing-Wen; Lai, Xiao-Ping; Ye, Wen-Cai

    2012-02-15

    Eight new triterpenoid glycosides, named ilexasosides A-H, were isolated from the roots of Ilex asprella. Their structures were elucidated by spectroscopic and chemical analyses. Ilexasosides B and D are rare sulfated derivatives of ursane-type triterpenoid glycosides.

  3. Iridoid and megastigmane glycosides from Phlomis aurea.

    PubMed

    Kamel, M S; Mohamed, K M; Hassanean, H A; Ohtani, K; Kasai, R; Yamasaki, K

    2000-10-01

    From the leaves of Phlomis aurea, two new iridoids of unique structures named 3-epiphlomurin (1) and phlomurin (2), a new megastigmane glucoside phlomuroside (3) and a new benzyl alcohol glycoside having the structure benzyl alcohol-O-beta-xylopyranosyl-(1-->2)-beta-glucopyranoside (4) have been isolated together with four known iridoids auroside, lamiide, 8-epiloganin and ipolamiide, two known phenolic glycosides acteoside (verbascoside) and syringin, one known phenylethanoid glycoside 2-phenylethyl-O-beta-xylopyranosyl-(1-->2)-beta-glucopyranoside, one known lignan liriodendrin and three known flavonoids chrysoeriol-7-O-beta-glucopyranoside, acacetin-7-O-beta-glucopyranoside and luteolin-7-O-beta-glucopyranoside. The structures of the isolated compounds were verified by means of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectral analyses.

  4. Bioactive spirostane glycosides from Tacca plantaginea.

    PubMed

    Liu, Zhen-Hua; Yan, Huan; Si, Yong-Ai; Ni, Wei; Chen, Yu; He, Li; Liu, Hai-Yang

    2016-02-01

    Eight new spirostane glycosides, taccaosides E-L (2-7, 11, and 14), along with 7 known spirostane glycosides were isolated from the extract of the whole plants of Tacca plantaginea (Hance) Drenth. Their structures were established on the basis of physical data, spectroscopic analysis (MS, 1D and 2D NMR), and chemical methods. The cytotoxicities of the isolates were evaluated in vitro against two human cancer cell lines (HEK293 and HepG2). The results showed that compound 1 had the strongest cytotoxic activity with IC50 values of 1.7 μM and 1.2 μM against the two cancer cell lines, respectively. Furthermore, the spirostane glycosides with 17α-hydroxyl group at their aglycones (10, 12, and 15) were tested for the induced platelet aggregation activity.

  5. 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.

  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.

  7. Inhibitory effects of tannin on human salivary alpha-amylase.

    PubMed

    Kandra, Lili; Gyémánt, Gyöngyi; Zajácz, Agnes; Batta, Gyula

    2004-07-09

    Here, we first report on the effectiveness and specificity of tannin inhibition of 2-chloro-4-nitrophenyl-4-O-beta-d-galactopyranosylmaltoside hydrolysis that is catalyzed by human salivary alpha-amylase (HSA). Tannin was gallotannin in which quinic acid was esterified with 2-7 units of gallic acid. A number of studies establish that polyphenols-like tannins-may prevent oral diseases, e.g., dental caries. Kinetic analyses confirmed that the inhibition of hydrolysis is a mixed non-competitive type and only one molecule of tannin binds to the active site or the secondary site of the enzyme. Since Dixon plots were linear, product formation could be excluded from the enzyme-substrate-inhibitor complex (ESI). Kinetic constants calculated from secondary plots and non-linear regression are almost identical, thereby confirming the suggested model. Kinetic constants (K(EI) = 9.03 microgmL(-1), K(ESI) = 47.84 microgmL(-1)) show that tannin is as an effective inhibitor of HSA as acarbose and indicate a higher stability for the enzyme-inhibitor complex than ESI.

  8. Genetic Manipulation of Condensed Tannins in Higher Plants1

    PubMed Central

    Robbins, Mark P.; Bavage, Adrian D.; Strudwicke, Catherine; Morris, Phillip

    1998-01-01

    We have produced and analyzed transgenic birdsfoot trefoil (Lotus corniculatus L.) plants harboring antisense dihydroflavonol reductase (AS-DFR) sequences. In initial experiments the effect of introducing three different antisense Antirrhinum majus L. DFR constructs into a single recipient genotype (S50) was assessed. There were no obvious effects on plant biomass, but levels of condensed tannins showed a statistical reduction in leaf, stem, and root tissues of some of the antisense lines. Transformation events were also found, which resulted in increased levels of condensed tannins. In subsequent experiments a detailed study of AS-DFR phenotypes was carried out in genotype S33 using pMAJ2 (an antisense construct comprising the 5′ half of the A. majus cDNA). In this case, reduced tannin levels were found in leaf and stem tissues and in juvenile shoot tissues. Analysis of soluble flavonoids and isoflavonoids in tannin down-regulated shoot tissues indicated few obvious default products. When two S33 AS-DFR lines were outcrossed, there was an underrepresentation of transgene sequences in progeny plants and no examples of inheritance of an antisense phenotype were observed. To our knowledge, this is the first report of the genetic manipulation of condensed tannin biosynthesis in higher plants. PMID:9501146

  9. Cytotoxic phenylpropanoid glycosides from Cirsium japonicum.

    PubMed

    Shang, Dong-Li; Ma, Qin-Ge; Wei, Rong-Rui

    2016-12-01

    Three new phenylpropanoid glycosides 1-3, along with nine known phenylpropanoid glycosides 4-12, were isolated from the aerial parts of Cirsium japonicum. The structures of isolated compounds were elucidated by chemical and spectroscopic methods. Compounds 1, 3, 6, 8, and 11 showed moderate cytotoxicities against MCF-7, U87, HCT116, and A549 cell lines with IC50 values in the range of 1.35-11.32 μM. The known compounds 4-12 were obtained from this plant for the first time.

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

    PubMed

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

    2010-03-24

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

  11. 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.

  12. 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.

  13. Polyoxypregnane glycosides from Caralluma retrospiciens.

    PubMed

    Halaweish, Fathi T; Huntimer, Eric; Khalil, Ashaf T

    2004-01-01

    Six related polyoxypregnane glycosides were isolated and characterised from Caralluma retrospiciens leaves. The compounds were identified as 12beta-benzoyloxy-8beta,14beta-dihydroxypregn-20-one-3-O-[3-O-methyl-6-deoxy-beta-D-allopyranosyl-(1 --> 4)-beta-D-cymaropyranosyl-(1 --> 4)-]-beta-D-cymaropyranoside], 12beta-benzoyloxy-8beta,14beta-dihydroxypregn-20-one-3-O-[beta-D-glucopyranosyl-(1 --> 4)-3-O-methyl-6-deoxy-beta-D-allopyranosyl-(1 --> 4)-beta-D-cymaropyranosyl-(1 --> 4)-beta-D-cymaropyranoside], 12beta-benzoyloxy-8beta,14beta-dihydroxypregn-20-one-3-O-[beta-D-glucopyranosyl-(1 --> 4)-3-O-methyl-6-deoxy-beta-D-galactopyranosyl-(1 --> 4)-3-O-methyl-6-deoxy-beta-D-galactopyranoside], 12beta-benzoyloxy-8beta,14beta-dihydroxypregn-20-one-3-O-[beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl-(1 --> 4)-3-O-methyl-6-deoxy-beta-D-galactopyranosyl-(1 --> 4)-3-O-methyl-6-deoxy-beta-D-galactopyranoside], 12beta-benzoyloxy-11alpha-isovaleroyloxy-8beta,14beta-dihydroxypregn-20-one-3-O-[beta-D-glucopyranosyl-(1 --> 4)-3-O-methyl-6-deoxy-beta-D-galactopyranosyl-(1 --> 4)-3-O-methyl-6-deoxy-beta-D-galactopyranoside], and 12beta-benzoyloxy-11alpha-isovaleroyloxy-8beta,14beta-dihydroxypregn-20-one-3-O-[beta-D-glucopyranosyl (1 --> 4)-3-O-methyl-6-deoxy-beta-D-allopyranosyl-(1 --> 4)-beta-D-cymaropyranosyl-(1 --> 4)-beta-D-cymaropyranoside]. The structures were determined by detailed analysis of one- and two-dimensional NMR spectra as well as by chemical means. The compounds showed cytotoxic activities towards brine shrimp having IC50 values of 1.19 x 10(-4), 8.83 x 10(-5), 2.64 x 10(-4), 2.26 x 10(-4), 2.39 x 10(-4) and 1.70 x 10(-4) M, respectively. This is the first report of the isolation of these compounds from a natural source.

  14. 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.

  15. Aleppo tannin: structural analysis and salivary amylase inhibition.

    PubMed

    Zajácz, Agnes; Gyémánt, Gyöngyi; Vittori, Natale; Kandra, Lili

    2007-04-09

    The effectiveness and specificity of a tannin inhibition on human salivary amylase (HSA) catalyzed hydrolysis was studied using 2-chloro-4-nitrophenyl 4-O-beta-D-galactopyranosyl-alpha-maltoside (GalG(2)-CNP) and amylose substrates. Aleppo tannin was isolated from the gall nut of Aleppo oak. This tannin is a gallotannin, in which glucose is esterified with gallic acids. This is the first kinetic report, which details the inhibitory effects of this compound on HSA. A mixed non-competitive type inhibition has been observed on both substrates. The extent of inhibition is markedly dependent on the substrate-type. Kinetic constants were calculated from Lineweaver-Burk secondary plots for GalG(2)-CNP (K(EI) 0.82 microg mL(-1), K(ESI) 3.3 microg mL(-1)). This indicates a 1:1 binding ratio of inhibitor-enzyme and/or inhibitor-enzyme-substrate complex. When amylose was the substrate the binding ratio of inhibitor to enzyme-substrate complex was found to be 2:1, with the binding constants of K(EI) 17.4 microg mL(-1), K(ESI) 14.9 microg mL(-1), K(ESI(2)) 9.6 microg mL(-1). Presumably, the tannin inhibitor can bind not only to HSA, but to the amylose substrate, as well. Kinetic data suggest that Aleppo tannin is a more efficient amylase inhibitor than the recently studied other tannin with quinic acid core (GalG(2)-CNP: K(EI) 9.0 microg mL(-1), K(ESI) 47.9 microg mL(-1)).

  16. 40 CFR 721.10666 - Quaternary ammonium compounds, bis(fattyalkyl) dimethyl, salts with tannins (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

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

  17. 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.

  18. 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...

  19. Anticancer activity of sea cucumber triterpene glycosides.

    PubMed

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

    2015-03-06

    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.

  20. 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

  1. Antiproliferative steroidal glycosides from Digitalis ciliata.

    PubMed

    Perrone, Angela; Capasso, Anna; Festa, Michela; Kemertelidze, Ether; Pizza, Cosimo; Skhirtladze, Alexandre; Piacente, Sonia

    2012-04-01

    Two new compounds, a furostanol glycoside (1) and a pregnane glycoside (4), along with eight known compounds, belonging to the classes of spirostane (2,3), pregnane (5-7) and cardenolide (8-10) glycosides, were isolated from the seeds of Digitalis ciliata. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. For the first time pregnane glycosides of the diginigenin series have been isolated from D. ciliata. The cytotoxic effects of compounds 1-10 on cell viability of several cancer cell lines, namely human breast cancer (MCF-7), human glioblastoma (T98G), human lung adenocarcinoma (A549), human colon carcinoma (HT-29), and human prostate cancer (PC-3) cell lines were evaluated. Compounds 1, 4, 7 and 8 showed antiproliferative effects against MCF-7, HT-29 and A549 cancer cells with IC₅₀ values ranging from 8.3 to 20 μM. The effects of compounds 1-10 on cell proliferation were evaluated on these three cancer cell lines by cell cycle analysis of DNA content using flow cytometry. Compounds 7, 8 and 10 induced significant changes in G₂/M cell cycle phase of all analyzed cells. The obtained results indicate that compounds 7, 8 and 10 are cytostatic compounds effective in reducing cell proliferation by inducing accumulation of the cells in the G₂/M phase of the cell cycle.

  2. Glycosides of the Magydaris pastinacea L.

    PubMed

    Cerri, R; Dessì, G; Manconi, P M; Serra, D; Pau, A

    1988-12-01

    From the alcoholic extract of fresh rhizomes from Magydaris pastinacea the glycosidic fraction was separated: it appears to be made up of seven different constituents one of which, 7-0-beta-D-glucopyranosil-8(2',3'-dihydroxy-3'methyl)-butylcoum arin isolated and identified by us, is relatively more abundant.

  3. 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.

  4. Acylated pregnane glycosides from Caralluma russeliana.

    PubMed

    Abdel-Sattar, Essam; Ahmed, Ahmed A; Hegazy, Mohamed-Elamir F; Farag, Mohamed A; Al-Yahya, Mohammad Abdul-Aziz

    2007-05-01

    The chloroform extract of the aerial parts of Caralluma russeliana yielded four acylated pregnane glycosides, namely russeliosides E-H, three were found now. The structures of the compounds were elucidated using MS, 1H NMR, 13C NMR, 1H-1H COSY, HMQC, NOESY and HMBC experiments.

  5. New oxypregnane glycosides from Caralluma penicillata.

    PubMed

    Abdel-Sattar, Essam; Meselhy, Meselhy R; Al-Yahya, Mohammed Abdul-Aziz

    2002-05-01

    The ether fraction of the defatted ethanol extract of the aerial parts of Caralluma penicillata (defl) M. E. Br. (Asclepiadaceae) yielded four new oxypregnane glycosides, penicillosides D-G. The structures of the isolated compounds were established by different spectroscopic methods.

  6. Triterpene glycosides of sea cucumbers (Holothuroidea, Echinodermata) as taxonomic markers.

    PubMed

    Kalinin, Vladimir I; Avilov, Sergey A; Silchenko, Alexandra S; Stonik, Valentin A

    2015-01-01

    Triterpene glycosides are characteristic metabolites of sea cucumbers (Holothurioidea, Echinodermata). The majority of the glycosides belong to the holostane type {lanostane derivatives with an 18(20)-lactone}. Carbohydrate chains of these glycosides contain xylose, glucose, quinovose, 3-O-methylglucose, and, rarely, 3-O-methylxylose, 3-O-methylglucuronic acid, 3-O-methylquinovose, and 6-O-acetyl-glucose. The glycosides are specific for genera, groups of genera and even for species. The advantages and problems in the use of triterpene glycosides as taxonomic markers in the systematics of sea cucumbers are discussed.

  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. 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.

  9. Genetics and Biochemistry of Zero-Tannin Lentils

    PubMed Central

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

    2016-01-01

    The zero-tannin trait in lentil is controlled by a single recessive gene (tan) that results in a phenotype characterized by green stems, white flowers, and thin, transparent, or translucent seed coats. Genes that result in zero-tannin characteristics are useful for studies of seed coat pigmentation and biochemical characters because they have altered pigmentation. In this study, one of the major groups of plant pigments, phenolic compounds, was compared among zero-tannin and normal phenotypes and genotypes of lentil. Biochemical data were obtained by liquid chromatography-mass spectrometry (LC-MS). Genomic sequencing was used to identify a candidate gene for the tan locus. Phenolic compound profiling revealed that myricetin, dihydromyricetin, flavan-3-ols, and proanthocyanidins are only detected in normal lentil phenotypes and not in zero-tannin types. The molecular analysis showed that the tan gene encodes a bHLH transcription factor, homologous to the A gene in pea. The results of this study suggest that tan as a bHLH transcription factor interacts with the regulatory genes in the biochemical pathway of phenolic compounds starting from flavonoid-3’,5’-hydroxylase (F3’5’H) and dihydroflavonol reductase (DFR). PMID:27788158

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

    PubMed

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

    2012-12-01

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

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

    PubMed

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

    2011-07-01

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

  12. 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.

  13. 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.

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

    PubMed

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

    2014-07-16

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

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

    PubMed

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

    2009-09-01

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

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

    PubMed

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

    2013-10-02

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

  17. 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

  18. 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

  19. 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...

  20. A novel glycoside from Acanthus hirsutus (Acanthaceae).

    PubMed

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

    2010-04-01

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

  1. Phenolic glycosides from berries of Pimenta dioica.

    PubMed

    Kikuzaki, Hiroe; Miyajima, Yoshiko; Nakatani, Nobuji

    2008-05-01

    Four new phenolic glycosides, (2-hydroxy-3-methoxy-5-allyl)phenyl beta- d-(6-O-E-sinapoyl)glucopyranoside (1), (1' R,5' R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3 Z-pentenyl beta-D-(6-O-galloyl)glucopyranoside (2), (S)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (3), and (R)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (4), were isolated from the berries of Pimenta dioica together with eight known flavonoids. The structures of 1-4 were elucidated on the basis of MS and NMR data and enzymatic hydrolysis. All four glycosides showed radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals.

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

    PubMed

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

    2015-06-01

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

  3. Iridoid and aromatic glycosides from Scrophularia ningpoensis Hemsl. and their inhibition of [Ca2+](i) increase induced by KCl.

    PubMed

    Chen, Bin; Liu, Yan; Liu, Hong-Wei; Wang, Nai-Li; Yang, Bao-Feng; Yao, Xin-Sheng

    2008-09-01

    Bioassay-guided fractionation of EtOH extract of the roots of Scrophularia ningpoensis Hemsl. resulted in the isolation of three new iridoid glycosides, i.e., 6''-O-caffeoylharpagide (1), 6''-O-feruloylharpagide (2), and 6''-O-beta-glucopyranosylharpagoside (3), and five new aromatic glycosides, i.e., 2-(3-hydroxy-4-methoxyphenyl)ethyl O-alpha-arabinopyranosyl-(1-->6)-O-alpha-rhamnopyranosyl-(1-->3)-O-beta-glucopyranoside (4), phenyl O-beta-xylopyranosyl-(1-->6)-O-beta-glucopyranoside (5), 3-methylphenyl O-beta-xylopyranosyl-(1-->6)-O-beta-glucopyranoside (6), 6-O-cinnamoyl beta-fructofuranosyl-(2-->1)-O-alpha-glucopyranosyl-(6-->1)-O-alpha-glucopyranoside (7), and 6-O-feruloyl beta-fructofuranosyl-(2-->1)-O-alpha-glucopyranosyl-(6-->1)-O-alpha-glucopyranoside (8), together with four known compounds, i.e., 6''-O-alpha-D-galactopyranosyl harpagoside (9), 6''-O-(p-coumaroyl) harpagide (10), harpagoside (11), and angoroside C (12). Activity of the isolated compounds on [Ca2+](i) increase induced by KCl was evaluated on rat cardiac myocytes using confocal laser scanning microscopy. Iridoid glycosides 1, 10, and 11, and aromatic glycosides 5 and 6 significantly inhibited the increase of [Ca2+](i) induced by KCl at 100 microM.

  4. New pregnane glycosides from Gymnema sylvestre.

    PubMed

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

    2015-02-12

    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.

  5. A new phenol glycoside from Physalis angulata.

    PubMed

    Sun, Cheng-Peng; Nie, Xiu-Fang; Kang, Ning; Zhao, Feng; Chen, Li-Xia; Qiu, Feng

    2017-05-01

    A new phenol glycoside, physanguloside A (1), was isolated from Physalis angulata together with four known compounds. We report herein, for the first time, the presence of compounds 2-5 in the genus Physalis. The structures of all the compounds were established by NMR, IR, UV and HRESIMS spectroscopic analyses, and comparison with the literature data. All isolated compounds were assayed for inhibitory activity on nitric oxide production by LPS-induced in RAW 264.7 macrophages.

  6. Triterpenoid glycosides from bark of Meliosma lanceolata.

    PubMed

    Abe, F; Yamauchi, T; Shibuya, H; Kitagawa, I

    1996-06-01

    From the bark of Meliosma lanceolate, nine triterpenoid glycosides including the 28-O-beta-D-glucopyranosyl ester of bayogenin-3-O-beta-D-glucuronopyranoside, its 4'-O-beta-D-galactopyranoside and 4'-O-alpha-L-arabinopyranoside were isolated and the structures characterized along with that of 28-O-beta-D-glucopyranosyl-bayogenin-3-O-beta-D-4'-anhydro-4', 5'-didehydroglucuronopyranoside. Bisdesmosidic triosides of hederagenin were obtained as minor components.

  7. Four Pentasaccharide Resin Glycosides from Argyreia acuta.

    PubMed

    Yu, Bang-Wei; Sun, Jing-Jing; Pan, Jie-Tao; Wu, Xiu-Hong; Yin, Yong-Qin; Yan, You-Shao; Hu, Jia-Yan

    2017-03-11

    Four pentasaccharide resin glycosides, acutacoside F-I (1-4), were isolated from the aerial parts of Argyreia acuta. These compounds were characterized as a group of macrolactones of operculinic acid A, and their lactonization site of 11S-hydroxyhexadecanoic acid was esterified at the second saccharide moiety (Rhamnose) at C-2. The absolute configuration of the aglycone was S. Their structures were elucidated by established spectroscopic and chemical methods.

  8. ent-Kaurene Glycosides from Ageratina cylindrica.

    PubMed

    Bustos-Brito, Celia; Sánchez-Castellanos, Mariano; Esquivel, Baldomero; Calderón, José S; Calzada, Fernando; Yépez-Mulia, Lilian; Joseph-Nathan, Pedro; Cuevas, Gabriel; Quijano, Leovigildo

    2015-11-25

    The aqueous extract of the leaves of Ageratina cylindrica afforded six new ent-kaurenoic acid glycosides together with the known diterpenoid paniculoside V, the flavonoid astragalin, chlorogenic acid, and L-chiro-inositol. The structures were elucidated mainly by NMR and MS methods, and the absolute configuration was established by vibrational circular dichroism spectroscopy. The new compounds showed moderate antiprotozoal activity against Entamoeba histolytica and Giardia lamblia trophozoites.

  9. A new lignan glycoside from Eleutherococcus senticosus.

    PubMed

    Li, X C; Barnes, D L; Khan, I A

    2001-11-01

    A new lignan glycoside, named eleutheroside E(2) (1), has been isolated from the roots of Eleutherococcus senticosus (known as "Siberian ginseng"), along with isomaltol 3-O-alpha-D-glucopyranoside (2), eleutherosides B, E and E(1), and thymidine. The structure of 1 was established by spectral interpretations as episyringaresinol 4"-O-beta-D-glucopyranoside. Compound 2 is described here for the first time as a naturally occurring compound.

  10. Cardiac Sarcoidosis.

    PubMed

    Birnie, David; Ha, Andrew C T; Gula, Lorne J; Chakrabarti, Santabhanu; Beanlands, Rob S B; Nery, Pablo

    2015-12-01

    Studies suggest clinically manifest cardiac involvement occurs in 5% of patients with pulmonary/systemic sarcoidosis. The principal manifestations of cardiac sarcoidosis (CS) are conduction abnormalities, ventricular arrhythmias, and heart failure. Data indicate that an 20% to 25% of patients with pulmonary/systemic sarcoidosis have asymptomatic (clinically silent) cardiac involvement. An international guideline for the diagnosis and management of CS recommends that patients be screened for cardiac involvement. Most studies suggest a benign prognosis for patients with clinically silent CS. Immunosuppression therapy is advocated for clinically manifest CS. Device therapy, with implantable cardioverter defibrillators, is recommended for some patients.

  11. 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.

  12. 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.

  13. Appetite suppressing pregnane glycosides from the roots of Cynanchum auriculatum.

    PubMed

    Liu, Shuangzhu; Chen, Zhenhua; Wu, Jian; Wang, Luoyi; Wang, Hongmin; Zhao, Weimin

    2013-09-01

    In the search for plant alternatives to Hoodia gordonii containing P57, a pregnane glycoside with potential appetite suppressant effect, the roots of Cynanchum auriculatum were investigated. As a result, 15 pregnane glycosides including nine never previously reported were isolated. Their structures were elucidated on the basis of extensive spectroscopic analyses and chemical methods. Appetite suppressant effect and body weight loss were observed when tested with the most abundant pregnane glycoside, wilfoside K1N, in an in vivo test with rats.

  14. New oxypregnane glycosides from appetite suppressant herbal supplement Hoodia gordonii.

    PubMed

    Pawar, Rahul S; Shukla, Yatin J; Khan, Shabana I; Avula, Bharathi; Khan, Ikhlas A

    2007-06-01

    Hoodigosides A-K (1-11), eleven new oxypregnane glycosides and a previously reported oxypregnane glycoside P57AS3 were isolated from the aerial parts of Hoodia gordonii. The structures of these 12-O-beta-tigloyl isoramanone glycosides were determined on the basis of chemical evidence and extensive spectroscopic methods that include one-dimensional and two-dimensional NMR. Cytotoxicity and antioxidant activities of these compounds were tested in cell based assays where they were found to be inactive.

  15. 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

  16. Antifungal active triterpene glycosides from sea cucumber Holothuria scabra.

    PubMed

    Han, Hua; Yi, Yang-Hua; Li, Ling; Liu, Bao-Shu; La, Ming-Ping; Zhang, Hong-Wei

    2009-06-01

    To study the new antifungal active triterpene glycosides of sea cucumber Holothuria scabra. Triterpene glycosides from Holothuria scabra were separated and purified by silica gel chromatography, reversed-phase silica gel chromatography and RP-HPLC. Their structures were elucidated on the basis of spectral data and chemical evidence. Three triterpene glycosides were identified as scabraside A (1), echinoidea A (2) and holothurin A1 (3). Scabraside A (1) is a new triterpene glycoside, and compounds 2 and 3 were isolated from Holothuria scabra for the first time. They showed antifungal activities (1 < or = MIC80 < or = 16 microg mL(-1)).

  17. Effective removal of cadmium from fish sauce using tannin.

    PubMed

    Sasaki, Tetsuya; Michihata, Toshihide; Katsuyama, Yoko; Take, Harumi; Nakamura, Shizuo; Aburatani, Miyuki; Tokuda, Kouji; Koyanagi, Takashi; Taniguchi, Hajime; Enomoto, Toshiki

    2013-02-13

    Fish sauce prepared from squid organs contains cadmium (Cd), which may be present at hazardous concentrations. In this study, we report a new, inexpensive, and acceptable method for removing Cd from fish sauce using tannin, which is an approved food additive in Japan. Decreases in Cd concentrations of 13-fold were observed (0.39-0.03 mg/100 mL) by incorporating the soluble Cd into a precipitate generated by tannin treatment. The total nitrogen content, free amino acid content, 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity, and angiotensin I-converting enzyme inhibitory activity of the treated fish sauce were the same as those of the untreated fish sauce.

  18. 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.

  19. Condensed tannins in the tissue culture of sainfoin (Onobrychis viciifolia Scop.) and birdsfoot trefoil (Lotus corniculatus L.).

    PubMed

    Lees, G L

    1986-08-01

    Two forage legumes, birdsfoot trefoil (Lotus corniculatus L.) and sainfoin (Onobrychis viciifolia Scop.), containing condensed tannins in their leaves and stems were used as source material to study condensed tannins in tissue culture. More protoplasts were isolated from mesophyll tissue of a low tannin-containing strain of birdsfoot trefoil than from a high tannin-containing strain, but more tannin-filled protoplasts were observed in the latter. Growth rates of leaf explant-derived callus tissue were greater for the high-tannin than for the low-tannin strain. In sainfoin, callus cultures from leaf explants produced numerous tannin-filled cells by 21 days. Explants from sainfoin cotyledons and roots, tissues which normally do not contain tannins, also formed callus with tannin-filled cells in 21 days but in almost every case, a cytokinin was required for tannin formation to occur. The occurrence of tannin-filled cells in callus from root and cotyledon explants was variable and genotype specific. These results show that endogenous tannins can affect protoplast isolation and possibly callus growth in birds-foot trefoil, and that the formation of condensed tannins in sainfoin callus culture can be influenced by a growth regulator.

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

    PubMed

    Duval, Antoine; Avérous, Luc

    2016-03-02

    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.

  1. Triterpene glycosides from the deep-water North-Pacific sea cucumber Synallactes nozawai Mitsukuri.

    PubMed

    Silchenko, Alexandra S; Avilov, Sergey A; Antonov, Alexandr A; Kalinin, Vladimir I; Kalinovsky, Anatoly I; Smirnov, Alexey V; Riguera, Ricardo; Jiménez, Carlos

    2002-12-01

    Five non-sulfated triterpene glycosides, synallactosides A(1) (1), A(2) (2), B(1) (3), B(2) (4), and C (5), have been isolated from the sea cucumber Synallactes nozawai. Their structures have been deduced by extensive analysis of NMR and mass spectra. The glycosides 2-5 are new glycosides. Glycosides 2-4 have carbohydrate chains without precedent in the glycosides from sea cucumbers. This is the first time glycosides are found in members of the family Synallactidae.

  2. 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.

  3. 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.

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

    PubMed

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

    2014-01-01

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

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

    PubMed

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

    2014-08-01

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

  6. 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.

  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.

  8. 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.

  9. 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.

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

    PubMed

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

    2013-01-23

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

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

    PubMed

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

    2009-04-01

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

  12. 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.

  13. A new iridoid glycoside from Scrophularia ningpoensis.

    PubMed

    Niu, Zheng-Rui; Wang, Ru-Feng; Shang, Ming-Ying; Cai, Shao-Qing

    2009-01-01

    A new iridoid glycoside, named 6'-O-cinnamoylharpagide (1), has been isolated from the roots of Scrophularia ningpoensis (Scrophulariaceae) together with nine known compounds, harpagide (2), harpagoside (3), 8-O-feruloylharpagide (4), 8-O-(p-coumaroyl)harpagide (5), 6-O-methylcatalpol (6), aucubin (7), buergerinin B (8), teuhircoside (9) and 6-O-cinnamoyl-D-glucopyranose (10). Compound 10 was obtained as an inseparable mixture of 6-O-cinnamoyl-alpha-D-glucopyranose and 6-O-cinnamoyl-beta-D-glucopyranose at a ratio of 1 : 1, which is presumably formed by cleavage of compound 1. Their structures were elucidated on the basis of chemical and spectral analysis.

  14. Acylated flavonol glycoside from Platanus orientalis.

    PubMed

    Tantry, Mudasir A; Akbar, Seema; Dar, Javid A; Irtiza, Syed; Galal, Ahmed; Khuroo, Mohammad A; Ghazanfar, Khalid

    2012-03-01

    The ethylacetate and n-butanol fractions of ethanolic extract of Platanus orientalis leaves led to the isolation of new acylated flavonol glycoside as 3',5,7-trihydroxy-4'-methoxyflavonol 3-[O-2-O-(2,4-Dihydroxy)-E-cinnamoyl-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl (1→2)]-β-D-glucopyranoside, along with seven known compounds. All the compounds were characterized by NMR including 2D NMR techniques. The isolates were evaluated for NF-κB, nitric oxide (NO), aromatase and QR2 chemoprevention activities and some of them appeared to be modestly active.

  15. Three new triterpene glycosides from Ilex asprella.

    PubMed

    Zhang, Zhen-Xia; Fu, Qiang; Zheng, Ken Yu-Zhong

    2013-01-01

    Three new sulfated triterpene glycosides, asprellanosides C-E (1-3), were isolated from the roots of Ilex asprella. Their structures were elucidated as 3β-[(2-O-sulfo-β-d-xylopyranosyl)oxy]urs-12,19(29)-diene-28-oic acid 28-β-d-glucopyranoside (1), 3β-[(2-O-sulfo-β-d-xylopyranosyl)oxy]urs-12,19-diene-28-oic acid 28-β-d-glucopyranoside (2), and 3β-[(2-O-sulfo-β-d-xylopyranosyl)oxy]urs-12,19-diene-28-oic acid (3) on the basis of the spectral and chemical methods.

  16. 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.

  17. 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.

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

    PubMed

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

    2014-11-01

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

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

    PubMed

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

    2016-10-01

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

  20. Enhancing water repellence and mechanical properties of gelatin films by tannin addition.

    PubMed

    Peña, Cristina; de la Caba, Koro; Eceiza, Arantxa; Ruseckaite, Roxana; Mondragon, Iñaki

    2010-09-01

    In order to reduce pollution caused by traditional non-biodegradable plastic films, renewable raw materials from plants and wastes of meat industries have been employed in this work. A hydrolysable chestnut-tree tannin was used for gelatin modification. Films of gelatin and gelatin-tannin were obtained by casting at room conditions. Transition temperatures of both gelatin and gelatin-tannin systems were determined by differential scanning calorimetry (DSC). Glass transition temperatures of modified gelatin occurred at higher temperatures than for neat gelatin. Enthalpy and temperature of helix-coil transition decreased when tannin content increased due to variations in the helical structure of gelatin as a consequence of tannin presence in agreement with X-ray analysis. Mechanical and thermal behaviour varied as a function of the content of tannin, showing optimum values for films modified with 10 wt% tannin. The transparency of films was maintained after modification with tannin. Solubility and swelling tests of the films revealed that the presence of tannin reduced the water affinity of gelatin.

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

    PubMed

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

    2010-04-01

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

  2. 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.

  3. 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.

  4. 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

  5. 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.

  6. 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

  7. Cardiac Cephalgia

    PubMed Central

    Wassef, Nancy; Ali, Ali Turab; Katsanevaki, Alexia-Zacharoula; Nishtar, Salman

    2014-01-01

    Although most of the patients presenting with ischemic heart disease have chest pains, there are other rare presenting symptoms like cardiac cephalgia. In this report, we present a case of acute coronary syndrome with an only presentation of exertional headache. It was postulated as acute presentation of coronary artery disease, due to previous history of similar presentation associated with some chest pains with previous left coronary artery stenting. We present an unusual case with cardiac cephalgia in a young patient under the age of 50 which was not reported at that age before. There are four suggested mechanisms for this cardiac presentation. PMID:28352454

  8. Enzymatic hydrolysis of steryl ferulates and steryl glycosides

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Steryl ferulates and steryl glycosides are phytosterol conjugates found characteristically in cereals. Their properties in enzymatic hydrolysis are, however, not yet well known. Steryl ferulates and steryl glycosides were extracted and purified from rye and wheat bran. Their rates of hydrolysis with...

  9. 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...

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

    PubMed

    Mouls, Laetitia; Fulcrand, Hélène

    2012-11-01

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

  11. Hydrolysis of soybean isoflavonoid glycosides by Dalbergia beta-glucosidases.

    PubMed

    Chuankhayan, Phimonphan; Rimlumduan, Thipwarin; Svasti, Jisnuson; Cairns, James R Ketudat

    2007-03-21

    Two beta-glucosidases from the legumes Dalbergia cochinchinensis and Dalbergia nigrescens were compared for their ability to hydrolyze isoflavonoid glycosides from soybean. Both D. nigrescens and D. cochinchinensis beta-glucosidases could hydrolyze conjugated soybean glycosides, but D. nigrescens beta-glucosidase hydrolyzed both conjugated and nonconjugated glycosides in crude soybean extract more rapidly. The kinetic properties Km, kcat, and kcat/Km of the Dalbergia beta-glucosidases toward conjugated isoflavonoid glycosides, determined using high-performance liquid chromatography, confirmed the higher efficiency of the D. nigrescens beta-glucosidase in hydrolyzing these substrates. The D. nigrescens beta-glucosidase could also efficiently hydrolyze isoflavone glycosides in soy flour suspensions, suggesting its application to increase free isoflavones in soy products.

  12. Nuclear cardiac

    SciTech Connect

    Slutsky, R.; Ashburn, W.L.

    1982-01-01

    The relationship between nuclear medicine and cardiology has continued to produce a surfeit of interesting, illuminating, and important reports involving the analysis of cardiac function, perfusion, and metabolism. To simplify the presentation, this review is broken down into three major subheadings: analysis of myocardial perfusion; imaging of the recent myocardial infarction; and the evaluation of myocardial function. There appears to be an increasingly important relationship between cardiology, particularly cardiac physiology, and nuclear imaging techniques. (KRM)

  13. Cardiac cameras.

    PubMed

    Travin, Mark I

    2011-05-01

    Cardiac imaging with radiotracers plays an important role in patient evaluation, and the development of suitable imaging instruments has been crucial. While initially performed with the rectilinear scanner that slowly transmitted, in a row-by-row fashion, cardiac count distributions onto various printing media, the Anger scintillation camera allowed electronic determination of tracer energies and of the distribution of radioactive counts in 2D space. Increased sophistication of cardiac cameras and development of powerful computers to analyze, display, and quantify data has been essential to making radionuclide cardiac imaging a key component of the cardiac work-up. Newer processing algorithms and solid state cameras, fundamentally different from the Anger camera, show promise to provide higher counting efficiency and resolution, leading to better image quality, more patient comfort and potentially lower radiation exposure. While the focus has been on myocardial perfusion imaging with single-photon emission computed tomography, increased use of positron emission tomography is broadening the field to include molecular imaging of the myocardium and of the coronary vasculature. Further advances may require integrating cardiac nuclear cameras with other imaging devices, ie, hybrid imaging cameras. The goal is to image the heart and its physiological processes as accurately as possible, to prevent and cure disease processes.

  14. 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.

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

    PubMed

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

    2007-07-11

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

  16. 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...

  17. 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.

  18. Tannins and Antioxidant Activities of the Walnut (Juglans regia) Pellicle.

    PubMed

    Yin, Tian-Peng; Cai, Le; Chen, Yang; Li, Ying; Wang, Ya-Rong; Liu, Chuan-Shui; Ding, Zhong-Tao

    2015-12-01

    The total phenolic content and antioxidant activities of the acetone extract and derived fractions from the walnut (Juglans regia) pellicle were estimated. The BuOH fraction exhibited the strongest antioxidant activity with the highest phenolic content. A phytochemical investigation of this fraction led to the isolation of three tannins, 2,3-hexahydroxydiphenoylglucose (1), pedunculagin (2) and 2,3,4,6-tetragalloylglucose (3). Pedunculagin showed high content and powerful activity, which implied that this compound plays an important role in the antioxidant activity of the walnut pellicle.

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

    PubMed

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

    2013-02-20

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

  20. Tannin content and rate of ruminal protein degradation of legume hays

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

  1. 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.

  2. 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.

  3. 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

  4. [Optimizing the ultrasonic extraction of tannin in Elaeagnus angustifolia L. by uniform design].

    PubMed

    Jiang, Fashou; Dan, Jianming; Wang, Hangyu; Wang, Jin

    2002-11-01

    The influences of ultrasonic frequency and ultrasonic time on the extraction rate of Tannin in Elaeagnus angustifolia L. were studied. The optimizing had been got. Results showed that the ultrasonic extraction method of Tannin in Elaeagnus angustifolia L. could save time, improve extraction rates, and need not be hot. Compared with traditional extraction, the ultrasonic extraction method is a good way.

  5. 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...

  6. 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...

  7. 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 ...

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

    PubMed

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

    2016-12-22

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

  9. 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...

  10. 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 ...

  11. 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...

  12. 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.

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

    PubMed

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

    2014-05-01

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

  14. 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

  15. 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.

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

    PubMed

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

    2015-01-01

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

  17. 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.

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

    PubMed

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

    2013-10-16

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

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

    PubMed

    Karamać, Magdalena

    2009-12-22

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

  20. Glycoside Hydrolases across Environmental Microbial Communities

    PubMed Central

    Berlemont, Renaud

    2016-01-01

    Across many environments microbial glycoside hydrolases support the enzymatic processing of carbohydrates, a critical function in many ecosystems. Little is known about how the microbial composition of a community and the potential for carbohydrate processing relate to each other. Here, using 1,934 metagenomic datasets, we linked changes in community composition to variation of potential for carbohydrate processing across environments. We were able to show that each ecosystem-type displays a specific potential for carbohydrate utilization. Most of this potential was associated with just 77 bacterial genera. The GH content in bacterial genera is best described by their taxonomic affiliation. Across metagenomes, fluctuations of the microbial community structure and GH potential for carbohydrate utilization were correlated. Our analysis reveals that both deterministic and stochastic processes contribute to the assembly of complex microbial communities. PMID:27992426

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

    PubMed

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

    2012-07-26

    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.

  2. Genetic modification of condensed tannin biosynthesis in Lotus corniculatus. 1. Heterologous antisense dihydroflavonol reductase down-regulates tannin accumulation in "hairy root" cultures.

    PubMed

    Carron, T R; Robbins, M P; Morris, P

    1994-03-01

    An antisense dihydroflavonol reductase (DFR) gene-construct made using the cDNA for DFR from Antirrhinum majus was introduced into the genome of a series of clonal genotypes of Lotus corniculatus via Agrobacterium rhizogenes. After initial screening, 17 antisense and 11 control transformation events were analysed and tannin levels found to be reduced in antisense root cultures. The effect of this antisense construct, (pMAJ2), which consisted of the 5' half of the DFR cDNA sequence, was compared in three different recipient Lotus genotypes. This construct effectively down-regulated tannin biosynthesis in two of the recepient genotypes (s33 and s50); however, this construct was relatively ineffective in a third genotype (s41) which accumulated high levels of condensed tannins in derived transgenic root cultures. Four pMAJ2 antisense and three control lines derived from clonal genotypes s33 and s50 were selected and studied in greater detail. The antisense DFR construct was found to be integrated into the genome of the antisense "hairy root" cultures, and the antisense RNA was shown to be expressed. Tannin levels were much lower in antisense roots compared to the controls and this reduction in tannin levels was accompanied by a change in condensed tannin subunit composition.

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

    PubMed

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

    2013-01-01

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

  4. 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.

  5. New benzophenone and quercetin galloyl glycosides from Psidium guajava L.

    PubMed Central

    Matsuzaki, Keiichi; Ishii, Rie; Kobiyama, Kaori

    2010-01-01

    New benzophenone and flavonol galloyl glycosides were isolated from an 80% MeOH extract of Psidium guajava L. (Myrtaceae) together with five known quercetin glycosides. The structures of the novel glycosides were elucidated to be 2,4,6-trihydroxybenzophenone 4-O-(6″-O-galloyl)-β-d-glucopyranoside (1, guavinoside A), 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6″-O-galloyl)-β-d-glucopyranoside (2, guavinoside B), and quercetin 3-O-(5″-O-galloyl)-α-l-arabinofuranoside (3, guavinoside C) by NMR, MS, UV, and IR spectroscopies. Isolated phenolic glycosides showed significant inhibitory activities against histamine release from rat peritoneal mast cells, and nitric oxide production from a murine macrophage-like cell line, RAW 264.7. PMID:20354804

  6. Chrysophanol glycosides from callus cultures of monocotyledonous Kniphofia spp. (Asphodelaceae).

    PubMed

    Ito, Hideyuki; Nishida, Yasuko; Yamazaki, Mie; Nakahara, Keisuke; Michalska-Hartwich, Malgorzata; Furmanowa, Miroslawa; Leistner, Eckhard; Yoshida, Takashi

    2004-10-01

    We established callus cultures of the monocotyledonous plants Kniphofia foliosa and K. tuckii (Asphodelaceae), which produce the anthraquinone derivatives chrysophanol and its glycosides. The minor product chrysophanol 8-O-beta-gentiobioside was fully characterized by spectroscopic analysis and synthesis.

  7. Cardiac Rehabilitation

    MedlinePlus

    ... your risk of future heart problems, and to improve your health and quality of life. Cardiac rehabilitation programs increase ... exercise routine at home or at a local gym. You may also continue to ... health concerns. Education about nutrition, lifestyle and weight loss ...

  8. Differential effects of quercetin glycosides on GABAC receptor channel activity.

    PubMed

    Kim, Hyeon-Joong; Lee, Byung-Hwan; Choi, Sun-Hye; Jung, Seok-Won; Kim, Hyun-Sook; Lee, Joon-Hee; Hwang, Sung-Hee; Pyo, Mi-Kyung; Kim, Hyoung-Chun; Nah, Seung-Yeol

    2015-01-01

    Quercetin, a representative flavonoid, is a compound of low molecular weight found in various colored plants and vegetables. Quercetin shows a wide range of neuropharmacological activities. In fact, quercetin naturally exists as monomer-(quercetin-3-O-rhamnoside) (Rham1), dimer-(Rutin), or trimer-glycosides [quercetin-3-(2(G)-rhamnosylrutinoside)] (Rham2) at carbon-3 in fruits and vegetables. The carbohydrate components are removed after ingestion into gastrointestinal systems. The role of the glycosides attached to quercetin in the regulation of γ-aminobutyric acid class C (GABAC) receptor channel activity has not been determined. In the present study, we examined the effects of quercetin glycosides on GABAC receptor channel activity by expressing human GABAC alone in Xenopus oocytes using a two-electrode voltage clamp technique and also compared the effects of quercetin glycosides with quercetin. We found that GABA-induced inward current (I GABA ) was inhibited by quercetin or quercetin glycosides. The inhibitory effects of quercetin and its glycosides on I GABA were concentration-dependent and reversible in the order of Rutin ≈ quercetin ≈ Rham 1 > Rham 2. The inhibitory effects of quercetin and its glycosides on I GABA were noncompetitive and membrane voltage-insensitive. These results indicate that quercetin and its glycosides regulate GABAC receptor channel activity through interaction with a different site from that of GABA, and that the number of carbohydrate attached to quercetin might play an important role in the regulation of GABAC receptor channel activity.

  9. 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.

  10. Steroidal saponins and pregnane glycosides from Smilax microphylla.

    PubMed

    Lin, Tao; Huang, Hui-Lian; Liu, Rong-Hua; Shu, Ji-Cheng; Ren, Gang; Shao, Feng; Liu, Li-sha

    2012-12-01

    Six steroidal saponins and two pregnane glycosides were isolated from the BuOH subfraction of 70% EtOH extract of Smilax microphylla C.H.Wright, among them two were new compounds (1 and 7). Pregnane glycosides were firstly isolated from the genus Smilax (Smilacaceae). Structures of the new compounds were determined on the basis of HR-ESI-MS, 1D and 2D NMR spectroscopic analysis.

  11. 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.

  12. Three New Steroidal Glycosides from the Roots of Cynanchum stauntonii

    PubMed Central

    Yu, Jin-Qian; Zhang, Zhi-Hui; Deng, An-Jun; Qin, Hai-Lin

    2013-01-01

    Three new steroidal glycosides, named as stauntosides L, M, and N (1–3), along with one known C21 steroidal glycoside, anhydrohirundigenin monothevetoside (4), were isolated from the 95% ethanol extract of the roots of Cynanchum stauntonii. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses, mainly 1D and 2D NMR, HRESI-MS, and chemical methods. PMID:23555098

  13. 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.

  14. 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.

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

    PubMed

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

    2013-11-01

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

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

    PubMed

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

    2016-10-31

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

  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

    2016-07-12

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

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

    PubMed

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

    2014-12-15

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

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

    PubMed

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

    2016-12-01

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

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

    PubMed

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

    2011-01-01

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

  2. 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.

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

    PubMed

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

    2013-12-01

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

  4. Specific polyphenols and tannins are associated with defense against insect herbivores in the tropical oak Quercus oleoides.

    PubMed

    Moctezuma, Coral; Hammerbacher, Almuth; Heil, Martin; Gershenzon, Jonathan; Méndez-Alonzo, Rodrigo; Oyama, Ken

    2014-05-01

    The role of plant polyphenols as defenses against insect herbivores is controversial. We combined correlative field studies across three geographic regions (Northern Mexico, Southern Mexico, and Costa Rica) with induction experiments under controlled conditions to search for candidate compounds that might play a defensive role in the foliage of the tropical oak, Quercus oleoides. We quantified leaf damage caused by four herbivore guilds (chewers, skeletonizers, leaf miners, and gall forming insects) and analyzed the content of 18 polyphenols (including hydrolyzable tannins, flavan-3-ols, and flavonol glycosides) in the same set of leaves using high performance liquid chromatography and mass spectrometry. Foliar damage ranged from two to eight percent per region, and nearly 90% of all the damage was caused by chewing herbivores. Damage due to chewing herbivores was positively correlated with acutissimin B, catechin, and catechin dimer, and damage by mining herbivores was positively correlated with mongolinin A. By contrast, gall presence was negatively correlated with vescalagin and acutissimin B. By using redundancy analysis, we searched for the combinations of polyphenols that were associated to natural herbivory: the combination of mongolinin A and acutissimin B had the highest association to herbivory. In a common garden experiment with oak saplings, artificial damage increased the content of acutissimin B, mongolinin A, and vescalagin, whereas the content of catechin decreased. Specific polyphenols, either individually or in combination, rather than total polyphenols, were associated with standing leaf damage in this tropical oak. Future studies aimed at understanding the ecological role of polyphenols can use similar correlative studies to identify candidate compounds that could be used individually and in biologically meaningful combinations in tests with herbivores and pathogens.

  5. Monomeric and dimeric hydrolysable tannins of Tamarix nilotica.

    PubMed

    Orabi, Mohamed A A; Taniguchi, Shoko; Hatano, Tsutomu

    2009-07-01

    An ellagitannin monomer, nilotinin M1 (1), and three dimers, nilotinins D1 (2), D2 (3), and D3 (4), were isolated from leaves of Tamarix nilotica (Ehrenb.) Bunge. Structures were elucidated based on analysis of spectroscopic data and chemical correlations with known compounds. In addition, six known tannins, hirtellin A (5) (dimer), remurin A (6), remurin B (7), 1,3-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-beta-D-glucose (8), gemin D (9), and hippomanin A (10) (monomers), were isolated for the first time from this plant species. The reported (13)C NMR assignments of the dehydrodigalloyl moiety and glucose cores of 5 are revised, and the (13)C NMR spectroscopic data for 6 and 7 are also reported for the first time.

  6. 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.

  7. A new lignan glycoside from Juniperus rigida.

    PubMed

    Woo, Kyeong Wan; Choi, Sang Un; Park, Jong Cheol; Lee, Kang Ro

    2011-12-01

    A new lignan glycoside, named juniperigiside (1) was isolated from the CHCl(3) soluble fraction of the MeOH extract of stems and leaves of Juniperus rigida S.et Z. Compound 1 was identified by 1D- and 2D-NMR spectroscopy as well as CD analysis as (2R,3S)-2,3-dihydro-7-methoxy-2-(4'-hydroxy-3'-methoxyphenyl)-3-hydroxymethyl-5-benzofuranpropanol 4'-O-(3-O-methyl)-α-L-rhamnopyranoside. Five known lignans, icariside E4 (2), desoxypodophyllotoxin (3), savinin (4), thujastandin (5), and (-)-nortrachelogenin (6) in addition to five known labdane diterpenes including trans-communic acid (7), 13-epi-torulosal (8), 13-epi-cupressic acid (9), imbricatoric acid (10), and isocupressic acid (11) were also isolated and their structures were characterized by comparing their spectroscopic data with those in the literature. All compounds were isolated for the first time from this plant, and 5 and 6 were first reported from the genus Juniperus. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay. Compounds 3, 4, 7, and 8 showed considerable cytotoxicity against four human cancer cell lines in vitro.

  8. 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.

  9. Three new flavonol glycosides from Suaeda maritima.

    PubMed

    Abd El-Latif, Rasha R; Mansour, Ragaa M A; Sharaf, Mohamed; Farag, Ahmad

    2014-01-01

    Three new flavonol glycosides isolated from the 70% methanol extract of Suaeda maritima (Chenopodiaceae) were characterized based on spectroscopic and chemical methods as quercetin 3-O-α-l-rhamnopyranosyl(1″' → 6″)-β-d-galactopyranoside-7-O-β-d-glucopyranosyl(1″″' → 2″″)-glucopyranoside, kaempferol 3-O-α-l-rhamnopyranosyl(1″' → 6″)-β-d-galactopyranoside-7-O-β-d-glucopyranosyl(1″″' → 2″″)-glucopyranoside, and kaempferol 3-O-α-l-rhamnopyranosyl(1″' → 6″)-β-d-galactopyranoside-7-O-(2″″'-O-trans-feruloyl)-β-d-glucopyranosyl-(1″″' → 2″″)-β-d-glucopyranoside. In addition, four known compounds, namely, quercetin and kaempferol, methyl cis, trans-ferulate, and methyl trans-ferulate were identified. The plant extract and these compounds showed cytotoxic activity against the human tumor cell lines MCF7, HCT116, and HEPG2.

  10. Acylated pregnane glycosides from Caralluma quadrangula.

    PubMed

    Abdallah, Hossam M; Osman, Abdel-Moneim M; Almehdar, Hussein; Abdel-Sattar, Essam

    2013-04-01

    In a previous study, the methanolic extract as well as the chloroform fraction of the aerial parts of Caralluma quadrangula (Forssk.) N.E.Br. indigenous to Saudi Arabia showed significant in vitro cytotoxic activity against breast cancer (MCF7) cell line. In a biologically-guided fractionation approach, four acylated pregnane glycosides were isolated from the chloroform fraction of C. quadrangula. The structures of the isolated compounds were elucidated by the analysis of their MS and NMR data. The compounds were identified as 12,20-di-O-benzoylboucerin 3-O-β-D-digitoxopyranosyl-(1→4)-β-D-canaropyranosyl-(1→4)-β-D-cymaropyranoside (1), 12,20-di-O-benzoylboucerin 3-O-β-D-cymaropyranosyl-(1→4)-β-D-canaropyranosyl-(1→4)-β-D-cymaropyranoside (2), 12,20-di-O-benzoylboucerin 3-O-β-D-glucopyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-canaropyranosyl-(1→4)-β-D-cymaropyranoside (3) and 12,20-di-O-benzoyl-3β,5α,12β,14β,20-pentahydroxy-(20R)-pregn-6-ene 3-O-β-D-glucopyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-canaropyranosyl-(1→4)-β-D-cymaropyranoside (4). The isolated compounds were tested for their cytotoxic activity against breast cancer (MCF7) cell line.

  11. 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

  12. 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

  13. Glycosidic inhibitors of melanogenesis from leaves of Passiflora edulis.

    PubMed

    Zhang, Jie; Koike, Ryosuke; Yamamoto, Ayako; Ukiya, Motohiko; Fukatsu, Makoto; Banno, Norihiro; Miura, Motofumi; Motohashi, Shigeyasu; Tokuda, Harukuni; Akihisa, Toshihiro

    2013-10-01

    A new flavonoid glycoside, chrysin 6-C-β-rutinoside (chrysin α-L-rhamnopyranosyl-(1→6)-C-β-glucopyranoside; 2), and two new triterpene glycosides, (31R)-31-O-methylpassiflorine (7) and (31S)-31-O-methylpassiflorine (8), along with 14 known glycosides, including three flavonoid glycosides, 1, 3, and 4, six triterpene glycosides, 5, 6, and 9-12, three cyano glycosides, 13-15, and two other glycosides, 16 and 17, were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1-17 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, isoorientin (1), 2, and (6S,9R)-roseoside (17), exhibited inhibitory effects with 37.3-47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8-100.2% cell viability) at 100 μM. Western blot analysis showed that compound 2 reduced the protein levels of MITF, TRP-1, and tyrosinase, in a concentration-dependent manner while exerted almost no influence on the level of TRP-2, suggesting that this compound inhibits melanogenesis on the α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP-1 and tyrosinase. In addition, compounds 1-17 were evaluated for their inhibitory effects against the EpsteinBarr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells.

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

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2014-12-04

    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.

  15. 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.

  16. 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...

  17. 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

  18. 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.

  19. 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.

  20. Ability of a salivary intrinsically unstructured protein to bind different tannin targets revealed by mass spectrometry.

    PubMed

    Canon, Francis; Giuliani, Alexandre; Paté, Franck; Sarni-Manchado, Pascale

    2010-09-01

    Astringency is thought to result from the interaction between salivary proline-rich proteins (PRP) that belong to the intrinsically unstructured protein group (IUP), and tannins, which are phenolic compounds. IUPs have the ability to bind several and/or different targets. At the same time, tannins have different chemical features reported to contribute to the sensation of astringency. The ability of both electrospray ionization mass spectrometry and tandem mass spectrometry to investigate the noncovalent interaction occurring between a human salivary PRP, IB5, and a model tannin, epigallocatechin 3-O-gallate (EgCG), has been reported. Herein, we extend this method to study the effect of tannin chemical features on their interaction with IB5. We used five model tannins, epigallocatechin (EgC), epicatechin 3-O-gallate (ECG), epigallocatechin 3-O-gallate (EgCG), procyanidin dimer B2 and B2 3'-O-gallate, which cover the main tannin chemical features: presence of a gallate moiety (galloylation), the degree of polymerization, and the degree of B ring hydroxylation. We show the ability of IB5 to bind these tannins. We report differences in stoichiometries and in stability of the IB5•1 tannin complexes. These results demonstrate the main role of hydroxyl groups in these interactions and show the involvement of hydrogen bonds. Finally, these results are in line with sensory analysis, by Vidal et al. (J Sci Food Agric 83:564-573, 2003) pointing out that the chain length and the level of galloylation are the main factors affecting astringency perception.

  1. Effects of fat and protein levels on foraging preferences of tannin in scatter-hoarding rodents.

    PubMed

    Wang, Bo; Chen, Jin

    2012-01-01

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

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

    PubMed

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

    2002-03-01

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

  3. Role of tannin-binding salivary proteins and tannase-producing bacteria in the acclimation of the Japanese wood mouse to acorn tannins.

    PubMed

    Shimada, Takuya; Saitoh, Takashi; Sasaki, Eiki; Nishitani, Yosuke; Osawa, Ro

    2006-06-01

    We studied the defense mechanisms against the negative effects of tannins in acorns by using the Japanese wood mouse (Apodemus speciosus) and acorns of a Japanese deciduous oak Quercus crispula, which contain 9.9% tannins on a dry weight basis. For the experiment, we allocated 26 wood mice into two groups: acclimated (N = 12) and nonacclimated (N = 14). Mice in the nonacclimated group were fed only acorns for 10 d after 4 wk of receiving a tannin-free diet. In contrast, mice in the acclimated group received ca. 3 g acorns daily in addition to the tannin-free diet for the first 4 wk, then they were fed only acorns for 10 d. Body weight, food intake, and digestibility were monitored. In addition, the amount of salivary proline-rich proteins (PRPs) and abundance of tannase-producing bacteria (TPB) in the feces of mice were measured. Of the 14 mice in the nonacclimated group, 8 died, whereas only 1 of the 12 in the acclimated group died. During the first 5 d of feeding acorns only, mice in the nonacclimated group lost, on average, 17.5% of their body mass, while those in the acclimated group lost only 2.5%. Food intake, dry matter digestibility, and nitrogen digestibility were higher in the acclimated group than in the nonacclimated group. The results indicate that wood mice can mitigate the negative effects of tannins by acclimation. Path analysis revealed that increased secretion of PRPs and abundance of Lactobacillus type of TPB might explain the acclimation to tannins.

  4. Steviol glycoside safety: is the genotoxicity database sufficient?

    PubMed

    Urban, J D; Carakostas, M C; Brusick, D J

    2013-01-01

    The safety of steviol glycoside sweeteners has been extensively reviewed in the literature. National and international food safety agencies and approximately 20 expert panels have concluded that steviol glycosides, including the widely used sweeteners stevioside and rebaudioside A, are not genotoxic. However, concern has been expressed in recent publications that steviol glycosides may be mutagenic based on select studies representing a small fraction of the overall database, and it has been suggested that further in vivo genotoxicity studies are required to complete their safety profiles. To address the utility of conducting additional in vivo genotoxicity studies, this review evaluates the specific genotoxicity studies that are the sources of concern, and evaluates the adequacy of the database including more recent genotoxicity data not mentioned in those publications. The current database of in vitro and in vivo studies for steviol glycosides is robust and does not indicate that either stevioside or rebaudioside A are genotoxic. This, combined with a lack of evidence for neoplasm development in rat bioassays, establish the safety of all steviol glycosides with respect to their genotoxic/carcinogenic potential.

  5. Human psychometric and taste receptor responses to steviol glycosides.

    PubMed

    Hellfritsch, Caroline; Brockhoff, Anne; Stähler, Frauke; Meyerhof, Wolfgang; Hofmann, Thomas

    2012-07-11

    Steviol glycosides, the sweet principle of Stevia Rebaudiana (Bertoni) Bertoni, have recently been approved as a food additive in the EU. The herbal non-nutritive high-potency sweeteners perfectly meet the rising consumer demand for natural food ingredients in Europe. We have characterized the organoleptic properties of the most common steviol glycosides by an experimental approach combining human sensory studies and cell-based functional taste receptor expression assays. On the basis of their potency to elicit sweet and bitter taste sensations, we identified glycone chain length, pyranose substitution, and the C16 double bond as the structural features giving distinction to the gustatory profile of steviol glycosides. A comprehensive screening of 25 human bitter taste receptors revealed that two receptors, hTAS2R4 and hTAS2R14, mediate the bitter off-taste of steviol glycosides. For some test substances, e.g., stevioside, we observed a decline in sweet intensity at supra-maximum concentrations. This effect did not arise from allosteric modulation of the hTAS1R2/R3 sweet taste receptor but might be explained by intramolecular cross-modal suppression between the sweet and bitter taste component of steviol glycosides. These results might contribute to the production of preferentially sweet and least bitter tasting Stevia extracts by an optimization of breeding and postharvest downstream processing.

  6. Acylated pregnane glycosides from Caralluma sinaica.

    PubMed

    Al-Massarani, Shaza M; Bertrand, Samuel; Nievergelt, Andreas; El-Shafae, Azza M; Al-Howiriny, Tawfeq A; Al-Musayeib, Nawal M; Cuendet, Muriel; Wolfender, Jean-Luc

    2012-07-01

    Caralluma sinaica is sold on local markets of Saudi Arabia for various health benefits however no phytochemical study has specifically been performed on this species. NMR and UHPLC-ESI-TOF-MS profilings of the ethanolic extract of the whole plant reveal a very complex phytochemical composition dominated by pregnanes. Detailed information on its constituents was obtained after isolation. Six pregnane glycosides were obtained and characterized based on the extensive spectroscopic analysis (including IR, ¹H NMR, ¹³C NMR and MS data), in addition to ten known compounds (seven pregnanes and three flavonoids). The compounds were identified as 12β-O-benzoyl-20-O-acetyl boucerin-3-O-6-deoxy-3-O-methyl-β-D-glucopyranosyl-(1-->4)-β-D-cymaropyranosyl-(1-->4)-β-D-cymaropyranoside, 12β-O-tigloyl-20-O-acetyl boucerin-3-O-β-D-glucopyranosyl-(1-->4)-β-D-cymaropyranoside, 12β-O-benzoyl-20-O-acetyl boucerin-3-O-β-D-glucopyranosyl-(1-->4)-β-D-digitalopyranosyl-(1-->4)-β-D-cymaropyranosyl-(1-->4)-β-D-cymaropyranoside, 12β-O-benzoyl-20-O-acetyl boucerin-3-O-β-D-glucopyranosyl-(1-->4)-hevetopyranosyl-(1-->4)-β-D-cymaropyranosyl-(1-->4)-β-D-cymaropyranoside, 12β-O-benzoyl-20-O-tigloyl boucerin-3-O-β-D-glucopyranosyl-(1-->4)-β-D-cymaropyranoside, 12β-20-O-dibenzoyl boucerin-3-O-β-D-glucopyranosyl-(1-->4)-β-D-cymaropyranosyl-(1-->4)-β-D-cymaropyranoside. Finally, the isolated compounds were evaluated for their quinone reductase induction.

  7. 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.

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

    PubMed

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

    2015-06-24

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

  9. 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.

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

    PubMed

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

    2010-05-28

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

  11. Sn, a maize bHLH gene, modulates anthocyanin and condensed tannin pathways in Lotus corniculatus.

    PubMed

    Robbins, Mark Paske; Paolocci, Francesco; Hughes, John-Wayne; Turchetti, Valentina; Allison, Gordon; Arcioni, Sergio; Morris, Phillip; Damiani, Francesco

    2003-01-01

    Anthocyanins and condensed tannins are major flavonoid end-products in higher plants. While the transactivation of anthocyanins by basic helix-loop-helix (bHLH) transcription factors is well documented, very little is known about the transregulation of the pathway to condensed tannins. The present study analyses the effect of over-expressing an Sn transgene in Lotus corniculatus, a model legume, with the aim of studying the regulation of anthocyanin and tannin end-products. Contrary to expectation, effects on anthocyanin accumulation were subtle and restricted to the leaf midrib, leaf base and petiole tissues. However, the accumulation of condensed tannin polymers was dramatically enhanced in the leaf blade and this increase was accompanied by a 50-fold increase in the number of tannin-containing cells in this tissue. A detailed analysis of selected lines indicated that this transactivational phenotype correlated with high steady-state transcript levels of the introduced transgene and the introduction of a single copy of the CaMV35S-Sn construct into these clonal genotypes. While the levels of condensed tannins in leaves were increased by up to 1% of the dry weight, other major secondary end-products (flavonols, lignins and inducible phytoalexins) were unaltered in transactivated lines. These results give an initial insight into the developmental and higher-order regulation of polyphenolic metabolism in Lotus and other higher plant species.

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

    PubMed

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

    2011-10-12

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

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

    PubMed

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

    2016-09-01

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

  14. About Cardiac Arrest

    MedlinePlus

    ... Thromboembolism Aortic Aneurysm More About Cardiac Arrest Updated:Mar 10,2017 What is cardiac arrest? Cardiac arrest is the abrupt loss of heart function in a person who may or may not have diagnosed heart ...

  15. 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...

  16. Cytotoxic Steroidal Glycosides from the Whole Plant of Calamus acanthophyllus.

    PubMed

    Prawat, Hunsa; Mahidol, Chulabhorn; Kaweetripob, Wirongrong; Intachote, Pakamas; Pisutjaroenpong, Somchai; Ruchirawat, Somsak

    2016-07-01

    A new steroidal glycoside, callaphylloside (1), together with seven known glycosides (2-8), was isolated from the whole plant of Calamus acanthophyllus. The structure of the new compound was elucidated by spectral data analyses and chemical transformations. Compounds 5 and 8 exhibited strong cytotoxic activity against four cancer cell lines (0.7 ≤ IC50 ≤ 3.4 µM). Evaluation of the structure-activity relationship among steroidal glycosides revealed that the structure of spirostanol with an α-L-rhamnopyranosyl linked to C-2 of the inner glucopyranosyl residue both play a critical role in the effects of these compounds on the cancer cell lines.

  17. [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.

  18. 2-methyl-L-erythritol glycosides from Gardenia jasminoides.

    PubMed

    Yang, Liguo; Peng, Kaifeng; Zhao, Shizhe; Zhao, Feng; Chen, Lixia; Qiu, Feng

    2013-09-01

    Two new glycosides, 2-methyl-L-erythritol-4-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside (1) and 2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside (2), along with two known triterpenoids (3-4), four quinic acid derivatives (5-8) and one flavonoid (9) were isolated from the fruit of Gardenia jasminoides. Their structures were elucidated through MS and 2D NMR experiments (HMQC and HMBC). Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. Though 2-methyl-D-erythritol and its glycosides have been reported in a few references, this is the first report about 2-methyl-L-erythritol glycosides. Based on this finding, we propose that 2-methyl-L-erythritol might be a new intermediate in the non-mevalonate biosynthesis of terpenoids.

  19. 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

  20. Chemical and biological properties of quinochalcone C-glycosides from the florets of Carthamus tinctorius.

    PubMed

    Yue, Shijun; Tang, Yuping; Li, Shujiao; Duan, Jin-Ao

    2013-12-10

    Quinochalcone C-glycosides are regarded as characteristic components that have only been isolated from the florets of Carthamus tinctorius. Recently, quinochalcone C-glycosides were found to have multiple pharmacological activities, which has attracted the attention of many researchers to explore these compounds. This review aims to summarize quinochalcone C-glycosides' physicochemical properties, chromatographic behavior, spectroscopic characteristics, as well as their biological activities, which will be helpful for further study and development of quinochalcone C-glycosides.

  1. A glycoside of Nicotina tabacum affects mouse dopaminergic behavior.

    PubMed

    Masuda, Y; Ohnuma, S; Kawagoe, M; Sugiyama, T

    2003-01-01

    Climbing in the forced swimming test is considered a dopaminergic-specific behavior. A substance of Nicotina tabacum affecting dopamine neuronal activity was investigated using the mouse behavioral system. The substance was found to be a glycoside with the peripheral sugar chain structures Fuc alpha 1-2Gal, Gal beta 1-4GlcNAc and GalNAc alpha 1-3GalNAc and with basic polymannoses. The glycoside dose-dependently increased behavior via D2 neuronal activity, but not D1 activity. This suggests that smoking can affect human brain function not only via the nicotinic cholinergic neuron, but also via the D2 neuron.

  2. Bioactive glycosides from the African medicinal plant Boerhavia erecta L.

    PubMed

    Nugraha, Ari S; Hilou, Adama; Vandegraaff, Nicholas; Rhodes, David I; Haritakun, Rachada; Keller, Paul A

    2015-01-01

    Phytochemical studies of the previously unexplored stem of Boerhavia erecta from Burkina Faso, resulted in the isolation of an unreported glycoside 4, 2,3-dihydroxypropylbenzoate-3-O-β-[4″-methoxy] glucuronide as well as seven known glycosides (1-3, 5-8). The major isolate 5 and 8 indicated a significant inhibition against HIV integrase (IC50 10 and 22 μg/mL, respectively). The extracts and isolates were also tested for anti-malarial activity, but insignificant activity was observed.

  3. New flavonol glycosides from the leaves of Caragana brachyantha.

    PubMed

    Perveen, Shagufta; Al-Taweel, Areej Mohammad; Al-Musayeib, Nawal; Fawzy, Ghada Ahmed; Khan, Afsar; Mehmood, Rashad; Malik, Abdul

    2015-01-01

    Two new flavonol glycosides, brachysides C and D, together with three known flavonol glycosides, were isolated from the leaves of Caragana brachyantha. The structures of brachysides C and D were elucidated on the basis of detailed spectroscopic analysis as quercetin 5-O-[α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranoside]-7-O-[α-L-rhamnopyranoside] and quercetin 5-O-[α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranoside]-7-O-[α-L-rhamnopyranoside]-4'-O-[α-L-rhamnopyranoside], respectively. The presence of flavonol tetra- and triglycosides bearing a sugar moiety at position 5 was the first report from this genus Caragana.

  4. 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.

  5. 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.

  6. 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.

  7. 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.

  8. 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.

  9. In vitro propagation and production of cardiotonic glycosides in shoot cultures of Digitalis purpurea L. by elicitation and precursor feeding.

    PubMed

    Patil, Jitendra Gopichand; Ahire, Mahendra Laxman; Nitnaware, Kirti Manik; Panda, Sayantan; Bhatt, Vijay P; Kishor, Polavarapu B Kavi; Nikam, Tukaram Dayaram

    2013-03-01

    Digitalis purpurea L. (Scrophulariaceae; Foxglove) is a source of cardiotonic glycosides such as digitoxin and digoxin which are commercially applied in the treatment to strengthen cardiac diffusion and to regulate heart rhythm. This investigation deals with in vitro propagation and elicited production of cardiotonic glycosides digitoxin and digoxin in shoot cultures of D. purpurea L. In vitro germinated seedlings were used as a primary source of explants. Multiple shoot formation was achieved for three explant types (nodal, internodal, and leaf) cultured on Murashige and Skoog (MS) medium with several treatments of cytokinins (6-benzyladenine-BA; kinetin-Kin; and thidiazuron-TDZ) and auxins (indole-3-acetic acid-IAA; α-naphthaleneacetic acid-NAA; and 2,4-dichlorophenoxy acetic acid-2,4-D). Maximum multiple shoots (12.7 ± 0.6) were produced from nodal explants on MS + 7.5 μM BA. Shoots were rooted in vitro on MS containing 15 μM IAA. Rooted plantlets were successfully acclimatized. To further maintain the multiple shoot induction, mother tissue was cut into four equal parts and repeatedly sub-cultured on fresh shoot induction liquid medium after each harvest. On adaptation of this strategy, an average of 18 shoots per explant could be produced. This strategy was applied for the production of biomass and glycosides digitoxin and digoxin in shoot cultures on MS medium supplemented with 7.5 μM BA and several treatments with plant growth regulators, incubation period, abiotic (salicylic acid, mannitol, sorbitol, PEG-6000, NaCl, and KCl), biotic (Aspergillus niger, Helminthosporium sp., Alternaria sp., chitin, and yeast extract) elicitors, and precursors (progesterone, cholesterol, and squalene). The treatment of KCl, mycelial mass of Helminthosporium sp., and progesterone were highly effective for the production of cardenolides. In the presence of progesterone (200 to 300 mg/l), digitoxin and digoxin accumulation was enhanced by 9.1- and 11.9-folds

  10. 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…

  11. Two new indolopyridoquinazoline alkaloidal glycosides from Ranunculus ternatus.

    PubMed

    Zhang, Lin; Yang, Zhuang; Tian, Jing-Kui

    2007-08-01

    Two new indolopyridoquinazoline alkaloidal glycosides, 11-O-beta-D-glucopyranosyl rutaecarpine (ternatoside C) and 11-O-alpha-L-rhamnosyl-(1-->6)-beta-D-glucopyranosyl rutaecarpine (ternatoside D) were isolated from the roots of Ranunculus ternatus. Their structures were determined on the basis of spectroscopic and chemical methods.

  12. Spirostanol glycosides with hemostatic and antimicrobial activities from Trillium kamtschaticum.

    PubMed

    Chen, Yu; Ni, Wei; Yan, Huan; Qin, Xu-Jie; Khan, Afsar; Liu, Hui; Shu, Tong; Jin, Ling-Yu; Liu, Hai-Yang

    2016-11-01

    Ten spirostanol glycosides, trillikamtosides A-J, together with eleven known analogues, were isolated from the hemostatic fraction of the 75% aqueous EtOH extract of the whole herbs of Trillium kamtschaticum. Their structures were established by extensive spectroscopic data analysis and chemical methods. The aglycones of three of these compounds had unique 3β,17α-dihydroxy-spirostanes featuring a double bond between C-4 and C-5, while two others represent a rare class of spirostanol glycosides which possess a 5(6 → 7) abeo-steroidal aglycone. All the compounds were evaluated for their hemostatic and antimicrobial activities. Three of the spirostanol glycosides exhibited induced-platelet aggregation at a concentration of 300 μg/mL with maximal induced-platelet aggregation rates of 72%, 71%, and 62% in rabbits, respectively, and their EC50 values were 492.7, 203.3, and 109.8 μM. Five of the spirostanol glycosides showed an anti-Candida albicans effect with MIC values of 21.1, 10.6, 8.8, 21.6, and 11.0 μM, respectively.

  13. New glycosides of acetophenone derivatives and phenylpropanoids from Juniperus occidentalis.

    PubMed

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

    2013-04-01

    New glycosides of seven acetophenone derivatives (1-7) and two phenylpropanoids (8, 9), named juniperosides III-XI, have been isolated from the MeOH extract of the leaves and stems of Juniperus occidentalis Hook. (Cupressaceae), together with eleven other known compounds. The structures of these compounds have been successfully elucidated using a variety of spectroscopic techniques.

  14. A New Flavanonol Glycoside from Adansonia digitata Roots.

    PubMed

    Chauhan, J S; Kumar, S; Chaturvedi, R

    1984-02-01

    A new flavanonol glycoside isolated from the roots of Adansonia digitata has been characterised as 3,7-dihydroxy flavan-4-one-5-O-beta- D-galactopyranosyl (1 --> 4)-beta- D-glucopyranoside on the basis of degradation, spectral and chemical studies.

  15. 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.

  16. Three new hecogenin glycosides from fermented leaves of Agave americana.

    PubMed

    Jin, Jian-Ming; Liu, Xi-Kui; Yang, Chong-Ren

    2003-06-01

    Eight steroidal compounds, including three new hecogenin glycosides, agamenosides D-F, were isolated from the fermented leaves of Agave americana. The structures of the new steroidal saponins were elucidated by spectroscopic data and chemical methods. The activity of the isolated compounds on deformations of mycelia germinated from conidia of Pyricularia oaryzae P-2b was evaluated.

  17. 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.

  18. 4'-Methoxyphenacyl-Assisted Synthesis of β-Kdo Glycosides.

    PubMed

    Mazur, Marcelina; Barycza, Barbara; Andriamboavonjy, Hanitra; Lavoie, Serge; Tamigney Kenfack, Marielle; Laroussarie, Anaïs; Blériot, Yves; Gauthier, Charles

    2016-11-18

    3-Deoxy-β-d-manno-oct-2-ulosonic acid (β-Kdo) glycosides are mainly found in capsular polysaccharides and extracellular exopolysaccharides from Gram-negative bacteria. These compounds have profound biological implications in immune response and act as virulence factors. We have developed a novel methodology for the stereoselective synthesis of β-Kdo glycosides via the use of a 4'-methoxyphenacyl (Phen) auxiliary group at the C1 position of a peracetylated β-Kdo thioglycoside. Under the promotion of NIS/AgOTf in acetonitrile, a series of Kdo glycosides was synthesized in good yield and β-selectivity while minimizing the formation of undesirable glycals. Stereoselectivity of the glycosylation was shown to be modulated by various factors such as promotor, solvent, anomeric ratio of donor, nature of acceptor, and Phen substitution. Chemoselective cleavage of the Phen group was performed under the action of Zn/HOAc. DFT calculations together with experimental results suggested that α-triflate and a six-membered α-spiroPhen are plausible intermediates of the reaction, accounting for the enhanced formation of β-Kdo glycosides. The developed methodology could be applied to the synthesis of β-Kdo-containing glycans from pathogenic bacteria.

  19. Structural revision of two flavanonol glycosides from Smilax glabra.

    PubMed

    Zhou, Xiang; Xu, Qiang; Li, Jian-Xin; Chen, Ting

    2009-05-01

    The structures of two flavanonol glycosides isolated from Smilax glabra, named smitilbin and neosmitilbin, have been revised to isoastilbin and neoastilbin, respectively. The revised structures were determined based on intensive studies of chemical interconversion, NMR spectroscopy, and X-ray crystallographic analysis. The latest NMR data were also summarized.

  20. 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

  1. A new C-methylated flavonoid glycoside from Pinus densiflora.

    PubMed

    Jung, M J; Choi, J H; Chung, H Y; Jung, J H; Choi, J S

    2001-12-01

    A new C-methyl flavonol glycoside, 5,7,8,4'-tetrahydroxy-3-methoxy-6-methylflavone 8-O-beta-D-glucopyranoside (1), has been isolated from the needles of Pinus densiflora, together with kaempferol 3-O-beta-(6"-acetyl)-galactopyranoside.

  2. A new phenylpropanoid glycoside from Jasminum subtriplinerve Blume.

    PubMed

    Huong, Nguyen Thi Hong; Cu, Nguyen Khac Quynh; Quy, Trinh Van; Zidorn, Christian; Ganzera, Markus; Stuppner, Hermann

    2008-01-01

    From the ethyl acetate extract of the aerial parts of Jasminum subtriplinerve Blume (Oleaceae), 6'-O-menthiafoloylverbascoside (1), rutin (2), isoverbascoside (4), isooleoverbascoside (6), apiosylverbascoside (7), astragalin (9), isoquercitrin (10), and verbascoside (11) were isolated. Their structures were elucidated by extensive MS and NMR spectroscopy. Amongst 6'-O-menthiafoloylverbascoside (1) is a new phenylpropanoid glycoside.

  3. Acylated pregnane glycosides from Caralluma tuberculata and their antiparasitic activity.

    PubMed

    Abdel-Sattar, Essam; Harraz, Fathalla M; Al-ansari, Soliman Mohammed Abdullah; El-Mekkawy, Sahar; Ichino, Chikara; Kiyohara, Hiroaki; Ishiyama, Aki; Otoguro, Kazuhiko; Omura, Satoshi; Yamada, Haruki

    2008-08-01

    Five pregnane glycosides were isolated from Caralluma tuberculata (1-5), in addition to a known one (russelioside E, 6). The structures of the isolated compounds were elucidated by the analysis of NMR data and FAB-MS experiments. All the isolated compounds were tested for their antimalarial and antitrypanosomal activities as well as their cytotoxicity against human diploid embryonic cell line (MRC5).

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

    PubMed

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

    2016-10-01

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

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

    PubMed Central

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

    2017-01-01

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

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

    PubMed

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

    2015-05-15

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

  7. 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.

  8. Kinetics of the hydrothermal treatment of tannin for producing carbonaceous microspheres.

    PubMed

    Braghiroli, F L; Fierro, V; Izquierdo, M T; Parmentier, J; Pizzi, A; Celzard, A

    2014-01-01

    Aqueous solutions of condensed tannins were submitted to hydrothermal carbonization (HTC) in a stainless steel autoclave, and the kinetics of hydrothermal carbon formation was investigated by changing several parameters: amount of tannin (0.5; 1.0; 1.5; 2.0 g in 16 mL of water), HTC temperature (130, 160, 180 and 200°C) and reaction times (from 1 to 720 h). The morphology and the structure of the tannin-based hydrothermal carbons were studied by TEM, krypton adsorption at -196°C and helium pycnometry. These materials presented agglomerated spherical particles, having surface areas ranging from 0.6 to 10.0 m(2) g(-1). The chemical composition of the hydrothermal carbons was found to be constant and independent of reaction time. HTC kinetics of tannin were determined and shown to correspond to first-order reaction. Temperature-dependent measurements led to an activation energy of 91 kJ mol(-1) for hydrothermal conversion of tannin into carbonaceous microspheres separable by centrifugation.

  9. 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).

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

    PubMed

    Schnabel, Thomas; Musso, Maurizio; Tondi, Gianluca

    2014-01-01

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

  11. Immunocytochemical studies on the origin and deposition sites of hydrolyzable tannins.

    PubMed

    Grundhöfer, P; Gross, G G.

    2001-04-01

    Two specific antibodies, directed toward hydrolyzable tannins, i.e. polygalloylated or oxidized derivatives of 1,2,3,4,6-penta-O-galloylglucose, and toward an acyltransferase from oak leaves that catalyzes the biosynthesis of this principal precursor, were used in immunocytochemical studies to determine the intracellular sites of origin and deposition of these polyphenolic plant constituents. Immunostaining of semi-thin sections from leaves and roots of young pedunculate oak (Quercus robur, syn. Quercus pedunculata) plants with marker enzymes and immunogold labeling of ultra-thin sections revealed immunoreactive sites for both enzyme and hydrolyzable tannins in chloroplasts, cell walls and intercellular spaces. The latter non-cytoplasmic (apoplast) compartments displayed characteristic aggregations of these two epitopes, thus indicating an intimate association of the biocatalyst and its products. Identical distribution patterns for hydrolyzable tannins were observed in leaves of Rhus typhina (sumac) and Tellima grandiflora (fringe cups) which, however, displayed no affinity toward the galloyltransferase antibody that had been raised against enzyme from oak. Controls with spinach leaves, known to be devoid of tannins, were inactive in all cases. The conclusion that, besides chloroplasts, cell walls and intercellular space serve as sites for the biosynthesis and deposition of hydrolyzable tannins was confirmed by analyzing extracts from these non-cytoplasmic compartments.

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

    PubMed

    Yang, Baoru; Liu, Pengzhan

    2014-01-22

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

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

    PubMed

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

    2014-10-15

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

  15. Cardiac xenotransplantation.

    PubMed

    DiSesa, V J

    1997-12-01

    Heart failure is an important medical and public health problem. Although medical therapy is effective for many people, the only definitive therapy is heart transplantation, which is limited severely by the number of donors. Mechanical devices presently are used as "bridges" to transplantation. Their widespread use may solve the donor shortage problem, but at present, mechanical devices are limited by problems related to blood clotting, power supply, and foreign body infection. Cardiac xenotransplantation using animal donors is a potential biologic solution to the donor organ shortage. The immune response, consisting of hyperacute rejection, acute vascular rejection, and cellular rejection, currently prevents clinical xenotransplantation. Advances in the solution of these problems have been made using conventional immunosuppressive drugs and newer agents whose use is based on an understanding of important steps in xenoimmunity. The most exciting approaches use tools of molecular biology to create genetically engineered donors and to induce states of donor and recipient bone marrow chimerism and tolerance in xenogeneic organ recipients. The successful future strategy may use a combination of a genetically engineered donor and a chimeric recipient with or without nonspecific immunosuppressive drugs.

  16. 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

  17. Platelet 5-hydroxytryptamine release and aggregation promoted by cotton bracts tannin.

    PubMed

    Rohrbach, M S; Rolstad, R A; Tracy, P B; Russell, J A

    1984-01-01

    The effect of aqueous extracts of cotton bract (CBE) on platelet secretion and aggregation was examined by using washed bovine and human platelets. The CBE promoted the release of 75% to 90% of the 5-hydroxytryptamine (5-HT) stored in both human and bovine platelets in a dose-dependent manner. This release reaction occurred without the lysis of the platelets and was not inhibited by indomethacin, 2-deoxyglucose, or KCN. Fractionation of the CBE indicated that the platelet secretagogue present in the CBE was the condensed polyphenol, tannin. In addition to promoting the secretion of 5-HT, tannin also aggregated the platelets in a dose-dependent manner. We conclude that the secretion of platelet 5-HT and the aggregation of platelets by tannin could potentially contribute to the pulmonary symptoms associated with byssinosis.

  18. Inhibition of constitutive endothelial NO-synthase activity by tannin and quercetin.

    PubMed

    Chiesi, M; Schwaller, R

    1995-02-14

    The effect of natural polyphenols on three isoforms of NO-synthase was investigated. Among the compounds tested, tannin was the most potent, inhibiting endothelial constitutive NO synthase (eNOS) with an IC50 of 2.2 microM. Other NOS isoforms (i.e. neuronal constitutive NOS and smooth muscle inducible NOS) were also inhibited but at much higher concentrations (selectivity ratio of approx. 20-30). Quercetin was also an effective but less potent inhibitor of eNOS (IC50 = 220 microM). The kinetics of tannin inhibition were investigated to gather information on the mechanism of action. Tannin did not interfere with the interaction of the enzyme with the co-substrates L-arginine and NADPH nor with the cofactor tetrahydrobiopterin. The inhibition level was also independent of free Ca2+ concentration as well as of the presence of high exogenous calmodulin concentrations.

  19. 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.

  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.

  1. Antimicrobial activity of tannin components from Vaccinium vitis-idaea L.

    PubMed

    Ho, K Y; Tsai, C C; Huang, J S; Chen, C P; Lin, T C; Lin, C C

    2001-02-01

    Reactive oxygen species have been implicated as important pathological mediators in many clinical disorders, including periodontal disease. As a possible alternative for the treatment of periodontal disease, the antimicrobial activity of six tannins isolated from Vaccinium vitis-idaea L., with confirmed antioxidant activity, were assayed by the agar dilution method against selected periodontal pathogens, Actinobacillus actinomycetemcomitans, Porphyromonas gingivalis and Prevotella intermedia. The results showed that epicatechin-(4beta-->8)-epicatechin-(4beta-->8, 2beta-->O-->7)-catechin had strong antimicrobial activity against P. gingivalis and P. intermedia, but not A. actinomycetemcomitans. The other tannins tested did not show antimicrobial activity. We conclude that tannins isolated from V. vitis-idaea L. with antimicrobial activity could potentially be used for the treatment of periodontal disease.

  2. 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...

  3. 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...

  4. 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 ...

  5. 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...

  6. 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

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

    PubMed

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

    2014-01-01

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

  8. 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.

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

    PubMed

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

    2014-01-01

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

  10. 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.

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

    PubMed Central

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

    2014-01-01

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

  12. Sweet antibiotics - the role of glycosidic residues in antibiotic and antitumor activity and their randomization.

    PubMed

    Kren, Vladimír; Rezanka, Tomás

    2008-08-01

    A large number of antibiotics are glycosides. In numerous cases the glycosidic residues are crucial to their activity; sometimes, glycosylation only improves their pharmacokinetic parameters. Recent developments in molecular glycobiology have improved our understanding of aglycone vs. glycoside activities and made it possible to develop new, more active or more effective glycodrugs based on these findings - a very illustrative recent example is vancomycin. The majority of attention has been devoted to glycosidic antibiotics including their past, present, and probably future position in antimicrobial therapy. The role of the glycosidic residue in the biological activity of glycosidic antibiotics, and the attendant targeting and antibiotic selectivity mediated by glycone and aglycone in antibiotics some antitumor agents is discussed here in detail. Chemical and enzymatic modifications of aglycones in antibiotics, including their synthesis, are demonstrated on various examples, with particular emphasis on the role of specific and mutant glycosyltransferases and glycorandomization in the preparation of these compounds. The last section of this review describes and explains the interactions of the glycone moiety of the antibiotics with DNA and especially the design and structure-activity relationship of glycosidic antibiotics, including their classification based on their aglycone and glycosidic moiety. The new enzymatic methodology 'glycorandomization' enabled the preparation of glycoside libraries and opened up new ways to prepare optimized or entirely novel glycoside antibiotics.

  13. New pregnane and phenolic glycosides from Solenostemma argel.

    PubMed

    Ounaissia, Karima; Pertuit, David; Mitaine-Offer, Anne-Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Delemasure, Stéphanie; Dutartre, Patrick; Smati, Dalila; Lacaille-Dubois, Marie-Aleth

    2016-10-01

    From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1-3) with two known ones and a new phenolic glycoside (4) have been isolated. Their structures were established by extensive 1D - and 2D NMR and mass spectroscopic analysis. The cytotoxicity of all compounds was evaluated against two human tumor cell lines (SW 480, MCF-7), but none of them was active in the concentration range 0.9-59.0μM. Compounds 2 and the known argeloside F at non toxic concentrations for the PBMCs (27.3μM and 27.6μM, respectively) significantly decreased the Il-1β production by LPS-stimulated PBMCs. All isolated compounds showed a significant antioxidant potential with ORAC values in the concentration range 3481-9617μmoleq. Trolox/100g.

  14. Determination of catechins and flavonol glycosides in Chinese tea varieties.

    PubMed

    Wu, Chunyan; Xu, Hairong; Héritier, Julien; Andlauer, Wilfried

    2012-05-01

    A standardised profiling method based on high performance liquid chromatography combined with ultraviolet (UV) and mass spectrometric detection (MS) was established to analyse the phenolic compounds of selected tea varieties used for manufacturing of green, black and oolong teas. The composition and content of 24 tea constituents were analysed, including catechins, flavonol and flavones glycosides, phenolic acids and purine alkaloids. Each tea variety had a unique chemical profile. The compositions of catechins were lower in the tea varieties for green tea manufacturing, while the content of myricetin glycosides was the lowest in the tea variety for oolong tea manufacturing. The content of individual phenolic compounds in the selected tea varieties is highly variable. However, the content of total catechins is proposed to be helpful to classify tea according to the future application as non fermented green and fermented oolong or black tea.

  15. Four new neuroprotective iridoid glycosides from Scrophularia buergeriana roots.

    PubMed

    Kim, So Ra; Lee, Ki Yong; Koo, Kyung Ah; Sung, Sang Hyun; Lee, Na-Gyong; Kim, Jinwoong; Kim, Young Choong

    2002-11-01

    Four new iridoid glycosides were isolated from a 90% MeOH extract of Scrophularia buergeriana roots and characterized as 8-O-E-p-methoxycinnamoylharpagide (1), 8-O-Z-p-methoxycinnamoylharpagide (2), 6'-O-E-p-methoxycinnamoylharpagide (3), and 6'-O-Z-p-methoxycinnamoylharpagide (4), respectively. In addition, three known iridoids were identified as E-harpagoside (5), Z-harpagoside (6), and harpagide (7). Compounds 1-7 significantly attenuated glutamate-induced neurotoxicity when added to primary cultures of rat cortical cells at concentrations ranging from 100 nM to 10 microM. The results obtained indicate that the iridoid glycosides isolated from S. buergeriana have significant protective effects against glutamate-induced neurodegeneration in primary cultures of rat cortical neurons.

  16. Synthetic Glycosides and Glycoconjugates of Low Molecular Weight Natural Products.

    PubMed

    Grynkiewicz, G; Szeja, W

    2016-01-01

    Enzymatically controlled transfer of saccharide moieties constitutes a fundamental biological process, essential for both primary and secondary metabolism. Natural products, including countless glycosides, with a rich tradition of use in ethnopharmacology, remain a prime source of inspiration for medicinal chemistry and molecular pharmacology, but their availability from biological sources is usually scarce, hampering attempts at application for new drug discovery and development. Chemical glycosylation on the other hand, although continuously undergoing sophisticated mechanistic studies, has nevertheless already matured as a set of methods which are able to provide substantial amounts of pure chemical entities: natural glycosides, as well as their congeners and mimics, necessary for the study of biological activity in quality assurance systems and required for drug development by pharmaceutical regulations. The paper presents a review of natural products and their analogues glycosylation, in a set of arbitrary selected examples, supplemented with comments on general advances in chemical glycosylation methodology and their applicability for particular categories of secondary metabolites.

  17. 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.

  18. 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.

  19. Coumarins of Matricaria chamomilla L.: aglycones and glycosides.

    PubMed

    Petruľová-Poracká, Veronika; Repčák, Miroslav; Vilková, Mária; Imrich, Ján

    2013-11-01

    The identity and quantity of coumarin-like compounds in leaves and anthodia of Matricaria chamomilla L. were studied by LC-DAD and NMR. So far, two monosubstituted coumarins, herniarin and umbelliferone, and two herniarin precursors were identified therein. In this paper, two other coumarin glycosides and one aglycone were confirmed. Skimmin (umbelliferone-7-O-β-d-glucoside), daphnin (daphnetin-7-O-β-d-glucoside) and daphnetin (7,8-dihydroxycoumarin) were found for the first time in diploid and tetraploid leaves and anthodia of M. chamomilla L. Daphnetin is known as a strong sensitizer, so this compound and its glycosidic derivative can contribute to the allergic potential of chamomile. Commercial chamomile preparations were tested for their presence.

  20. Capillary electrophoresis of neutral carbohydrates: mono-, oligosaccharides, glycosides.

    PubMed

    Campa, Cristiana; Rossi, Marco

    2008-01-01

    This chapter reports an overview of the recent advances in the analysis of neutral sugars by capillary electrophoresis (CE); furthermore, some relevant reviews and research articles in the field are tabulated. Comparison of CE with chromatography is also presented, with special attention to separation efficiency and sensitivity. The main routes aimed at pretreatment and CE analysis of uncharged mono-, oligosaccharides, and glycosides are described. Representative examples of such procedures are reported in detail, upon describing robust methodologies for the study of (1) neutral mono- and oligosaccharides derivatized by reductive amination and by formation of glycosylamines; (2) underivatized mono- and di-saccharides analyzed using highly alkaline buffers; and (3) anomeric couples of glycosides separated using borate-based buffers.

  1. Two new pregnane glycoside diesters from Caralluma russeliana.

    PubMed

    Abdel-Mogib, Mamdouh; Raghib, Hanaa M

    2013-01-01

    Two new pregnane glycoside diesters, 1 and 2, in addition to two triterpenoids, 3 and 4, and two sterols, 5 and 6 were isolated and identified from Caralluma russeliana (family Asclepiadaceae). The new pregnane glycosides, 14β-benzoyloxy-15β-isovaleroyloxy-16α-hydroxypregn-20-on-3-O-[β-D-3-O-methyl-6-deoxyoleandrosopyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside] (1) and 14β-isovaleroyloxy-15β-benzoyloxy-16α-hydroxypregn-20-on-3-O-[β-D-3-O-methyl-6-deoxyoleandrosopyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside] (2), are different from those isolated previously from the same species in the sugar moiety, in being diester, in being 20-one and in being 5,6 saturated by hydrogen. The isolated compounds were identified on the basis of spectral data.

  2. Acylated quercetagetin glycosides with antioxidant activity from Tagetes maxima.

    PubMed

    Parejo, Irene; Bastida, Jaume; Viladomat, Francesc; Codina, Carles

    2005-10-01

    The fractionation of a methanolic extract of Tagetes maxima guided for antioxidant activity resulted in the isolation of three acylated quercetagetin glycosides, quercetagetin-7-O-(6-O-caffeoyl-beta-D-glucopyranoside), quercetagetin-7-O-(6-O-p-coumaroyl-beta-D-glucopyranoside) and quercetagetin-7-O-(6-O-galloyl-beta-D-glucopyranoside), as well as four known flavonoid glycosides. The structural elucidation was accomplished by spectroscopic methods (ESI-MS/MS and NMR). The antioxidant activity of fractions and isolated compounds was determined by checking the scavenging activity against three different radicals: 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH*), hydroxyl (*OH), and superoxide (O2*-). The three isolated compounds exhibited a high radical scavenging activity in comparison with reference compounds.

  3. Two new flavonol glycosides from Gymnema sylvestre and Euphorbia ebracteolata.

    PubMed

    Liu, Xin; Ye, Wencai; Yu, Biao; Zhao, Shouxun; Wu, Houming; Che, Chuntao

    2004-03-15

    Two new flavonol glycosides, namely kaempferol 3-O-beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-galactopyranoside (1) and quercetin 3-O-6"-(3-hydroxyl-3-methylglutaryl)-beta-D-glucopyranoside (2), have been isolated from the aerial parts of Gymnema sylvestre and Euphorbia ebracteolata, respectively. Their structures were determined on the basis of chemical and spectroscopic methods.

  4. Two new lignan glycosides from the fruits of Pyrus ussuriensis.

    PubMed

    Zhao, Ze-Qing; Su, Yan-Fang; Yang, Fei; Gao, Xiu-Mei; Li, Tian-Xiang

    2016-12-01

    Two new lignan glycosides, ussuriensislignan A (1) and ussuriensislignan B (2), together with seventeen known compounds (3-19), were isolated from the fruits of Pyrus ussuriensis. Their structures were determined by various spectroscopic methods. This is the first report of the isolation of lignans (compounds 1-3) from the genus Pyrus, and compounds 3-6, 12-16 were reported from Pyrus for the first time.

  5. 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).

  6. A novel cytotoxic flavonoid glycoside from Physalis angulata.

    PubMed

    Ismail, N; Alam, M

    2001-08-01

    A new flavonol glycoside, myricetin 3-O-neohesperidoside (1) was isolated from a cytotoxic MeOH extract of the leaves of Physalis angulata. Compound 1 showed remarkable cytotoxicity in vitro against murine leukemia cell line P-388, epidermoid carcinoma of the nasopharynx KB-16 cells, and lung adenocarcinoma A-549 with ED(50) values of 0.048, 0.50 and 0.55 microg ml(-1), respectively.

  7. Two new monoterpenoid glycosides from Mentha spicata L.

    PubMed

    Zheng, Jian; Wu, Li-Jun; Zheng, Lu; Wu, Bin; Song, Ai-Hua

    2003-03-01

    Two new monoterpenoid glycosides, spicatoside A and spicatoside B, were isolated from the whole herbs of Mentha spicata L. which have anti-inflammatory and hemostatic activities. Their structures have been determined on the basis of spectral and chemical analysis. They are (+)-5-[1-(beta-D-glucopyranosyloxymethyl)ethenyl]-2-methyl-2-cyclohexen-1-one (1), and (-)-5-[[2-(beta-D-glucopyranosyloxy)-1-hydroxy-l-methyl]ethyl]-2-methyl-2-cyclohexen-1-one (2).

  8. New phenolic glycosides from the seeds of Cucurbita moschata.

    PubMed

    Li, Fa-Sheng; Dou, De-Qiang; Xu, Liang; Chi, Xiao-Feng; Kang, Ting-Guo; Kuang, Hai-Xue

    2009-07-01

    Two new phenolic glycosides were isolated from the seeds of Cucurbita moschata. Their structures were elucidated as (2-hydroxy)phenylcarbinyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (1) and 4-beta-D-(glucopyranosyl hydroxymethyl)phenyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence.

  9. Antitrypanosomal activity of some pregnane glycosides isolated from Caralluma species.

    PubMed

    Abdel-Sattar, Essam; Shehab, Naglaa G; Ichino, Chikara; Kiyohara, Hiroaki; Ishiyama, Aki; Otoguro, Kazuhiko; Omura, Satoshi; Yamada, Haruki

    2009-06-01

    Pregnane glycosides previously isolated from genus Caralluma (C. Penicillata, C. tuberculata and C. russelliana) were tested for their antitrypanosomal activity. Penicilloside E showed the highest antitrypanosomal activity (IC(50) 1.01 microg/ml) followed by caratuberside C (IC(50) 1.85 microg/ml), which exhibited the highest selectivity index (SI 12.04). It was noticed that acylation is required for the antitrypanosomal activity while glycosylation at C-20 has no significant effect on the activity.

  10. Cardiac tamponade (image)

    MedlinePlus

    Cardiac tamponade is a condition involving compression of the heart caused by blood or fluid accumulation in the space ... they cannot adequately fill or pump blood. Cardiac tamponade is an emergency condition that requires hospitalization.

  11. 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.

  12. 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 ( ...

  13. 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 ...

  14. Effects of purified persimmon tannin and tannic acid on survival and reproduction of bean bug, Riptortus clavatus.

    PubMed

    Park, Chung Gyoo; Lee, Kyu Chul; Lee, Dong Woon; Choo, Ho Yul; Albert, P J

    2004-11-01

    We evaluated the effects of tannic acid and purified perrsimmon tannin on survival and reproduction of bean bugs, Riptortus clavatus.Feeding behavior of R. clavatus was also examined on sweet (cv. Fuyu) and astringent (cv. Chongdosi) persimmon fruits. Soluble tannin in sweet persimmon fruits decreased from 3% in early June to 0.5% in late September, but it increased from 2 to 8% during the same period in astringent persimmon fruits. More bugs visited sweet than astringent persimmon. Numbers of piercing/sucking spots were higher on sweet than on astringent persimmon. When fed 1 and 3% solutions of persimmon tannin, adult bugs ingested only 64.1 and 9.5% of the amount of water ingested by those offered the control (distilled water). Amounts of persimmon tannin ingested by the adult bugs were 6.5 and 2.8 times higher at 1 and 3% tannin solutions compared to a 0.1% solution. Persimmon tannin exerted negative effects on survival and reproduction of R. clavatus at higher concentrations (1 and 3% solutions). Feeding of R. clavatus adults decreased with increasing tannin concentrations. When results from both sexes were pooled, 50% mortality was achieved at 11 and 4 days after treatment with the 1 and 3% tannin solutions, respectively. Reproduction decreased with 1% tannin, and no eggs were produced with 3% tannin solution. Tannic acid was similar in its effects on R. clavatus. All nymphs died 14, 12, and 7 days after feeding on 0.1, 1, and 3% tannic acid, respectively. Adults were less sensitive than nymphs, and their survival was not affected by 0.1% tannic acid. However. 1 and 3% tannic acid solutions were fatal. Survivorship decreased to 50% at 11 and 6 days after supplying tannin solutions of 1 and 3% concentrations. Higher concentrations (1 and 3%) resulted in reduced reproduction, as was seen with persimmon tannin. Our data may explain why R. clavatus does not invade sweet persimmon orchards until late July, when concentrations of soluble tannin are low enough to

  15. Antifungal activity of steroidal glycosides from Yucca gloriosa L.

    PubMed

    Favel, A; Kemertelidze, E; Benidze, M; Fallague, K; Regli, P

    2005-02-01

    The antifungal activity of a crude steroidal glycoside extract from Yucca gloriosa flowers, named alexin, was investigated in vitro against a panel of human pathogenic fungi, yeasts as well as dermatophytes and filamentous species. The minimal inhibitory concentration (MIC) was determined by an agar dilution method. Alexin had a broad spectrum of antifungal activity, found to reside entirely in the spirostanoid fraction. The major tigogenyl glycosides, yuccaloeside B and yuccaloeside C, exhibited MICs between 0.39 and 6.25 microg[sol ]mL for all the tested yeast strains except for two (C. lusitaniae and C. kefyr). They were also active against several clinical Candida isolates known to be resistant to the usual antifungal agents. The MICs for the dermatophytes were between 0.78 and 12.5 microg[sol ]mL. The most sensitive filamentous species was A. fumigatus (MIC = 1.56 microg[sol ]mL). For most of the strains, the MICs of both glycosides were similar to those of the reference antifungal agent.

  16. Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives

    PubMed Central

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

    2014-01-01

    A UDP glucosyltransferase from Bacillus licheniformis was overexpressed, purified, and incubated with nucleotide diphosphate (NDP) d- and l-sugars to produce glucose, galactose, 2-deoxyglucose, viosamine, rhamnose, and fucose sugar-conjugated resveratrol glycosides. Significantly higher (90%) bioconversion of resveratrol was achieved with α-d-glucose as the sugar donor to produce four different glucosides of resveratrol: resveratrol 3-O-β-d-glucoside, resveratrol 4′-O-β-d-glucoside, resveratrol 3,5-O-β-d-diglucoside, and resveratrol 3,5,4′-O-β-d-triglucoside. The conversion rates and numbers of products formed were found to vary with the other NDP sugar donors. Resveratrol 3-O-β-d-2-deoxyglucoside and resveratrol 3,5-O-β-d-di-2-deoxyglucoside were found to be produced using TDP-2-deoxyglucose as a donor; however, the monoglycosides resveratrol 4′-O-β-d-galactoside, resveratrol 4′-O-β-d-viosaminoside, resveratrol 3-O-β-l-rhamnoside, and resveratrol 3-O-β-l-fucoside were produced from the respective sugar donors. Altogether, 10 diverse glycoside derivatives of the medically important resveratrol were generated, demonstrating the capacity of YjiC to produce structurally diverse resveratrol glycosides. PMID:25239890

  17. 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.

  18. 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.

  19. 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...

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

    PubMed

    Banu, Khaleda; Shimura, Takayoshi; Sadeghi, Saman

    2015-01-01

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

  1. Seasonal changes in tannin and nitrogen contents of Casuarina equisetifolia branchlets*

    PubMed Central

    Zhang, Li-hua; Ye, Gong-fu; Lin, Yi-ming; Zhou, Hai-chao; Zeng, Qi

    2009-01-01

    Seasonal dynamics of total phenolics (TP), extractable condensed tannins (ECT), protein-bound condensed tannins (PBCT), fiber-bound condensed tannins (FBCT), total condensed tannins (TCT), and protein precipitation capacity (PPC) in young, mature and senescent branchlets of Casuarina equisetifolia were studied at Chishan Forestry Center of Dongshan County, Fujian Province, China. In addition, nitrogen contents of branchlets at the different developmental stages were also determined. The contents of TP and ECT, and PPC in young branchlets were significantly higher than those in mature and senescent branchlets through the season. However, PBCT contents were significantly higher in senescent branchlets than those in young and mature branchlets; FBCT fluctuated with season. Young branchlets had the highest N content, which decreased during branch maturity and senescence. The highest contents of TP and the lowest contents of TCT and N in young and mature branchlets were observed in summer. There was a significant negative correlation between TP and N contents. In contrast, TCT contents were positively correlated to N contents. Nutrient resorption during senescence and high TCT:N ratios in senescent branchlets are the important nutrient conservation strategies for C. equisetifolia. PMID:19235268

  2. Determination of flavonoids, tannins and ellagic acid in leaves from Rubus L. species.

    PubMed

    Gudej, Jan; Tomczyk, Michal

    2004-11-01

    This paper describes the quantitative determination of flavonoids, tannins and ellagic acid in the leaves from wild and cultivated variations of Rubus L. species (Rosaceae): raspberry (2 wild and 13 cultivars) and blackberry (3 wild and 3 cultivars). The content of flavonoids was analyzed using spectrophotometric (the Christ-Mullers method) and HPLC analysis after acid hydrolysis. The content of tannins was determined by the weight method, with hide powder, described by German Pharmacopoeia 10 (DAB 10). Ellagic acid content was examined using the HPLC method after acid hydrolysis. Flavonoid content, determined using the Christ-Muller's method was higher for the blackberry leaves than for the raspberry leaves and varied between 0.46% and 1.05%. Quercetin and kaempferol were predominant in all samples analyzed using the HPLC method. The highest flavonoid content was found in the leaves of R. nessensis (1.06%); with results in all of the examined samples varying between 0.27% and 1.06%. The concentration of ellagic acid in all species was determined after acid hydrolysis and ranged from 2.06% to 6.89%. The leaves of raspberries are characterized by greater amounts of tannins (varying between 2.62% and 6.87%) than the leaves of other species. The results from this study indicate that the analyzed species are a rich source of flavonoids, ellagic acid and tannins, which may be used for the quality assessment of Rubus L. species leaves.

  3. 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...

  4. 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...

  5. 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.

  6. 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...

  7. Impacts of flavanoid monomers and simple hydrolyzable tannins on ammonia emissions from dairy manure

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Inhibition of ammonia production in manure provides for a healthier environment for dairy farmers working in confined quarters. The resulting conservation of urea provides for an enhanced nitrogen concentration, and thus, fertilizing capacity, of the manure. The use of a mixture of tannins from queb...

  8. Harvest Regimens to Maximize Sericea Lespedeza Crude Protein and Condensed Tannins

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Sericea lespedeza (SL; Lespedeza cuneata) is sold as hay or pellets for its crude protein (CP) and condensed tannin (CT) content, the latter to promote rumen bypass protein, depress methane emissions in livestock, and suppress gastro-intestinal parasites in small ruminants. Maximizing these forage c...

  9. 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 (...

  10. 40 CFR 721.10666 - Quaternary ammonium compounds, bis(fattyalkyl) dimethyl, salts with tannins (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10666 Quaternary ammonium compounds, bis(fattyalkyl) dimethyl, salts with tannins (generic). (a) Chemical substance and significant...

  11. 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

  12. 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...

  13. [HPLC-fingerprint-based quality evaluation on a Tibetan medicine Phyllanthus emblica and its tannin parts].

    PubMed

    Sun, Xue-Fei; Zhang, Hong-Yan; Xia, Qing; Zhao, Hai-Juan; Wu, Ling-Fang; Zhang, Lan-Zhen; Shi, Ren-Bing

    2014-04-01

    This study is to establish the fingerprint for Phyllanthus emblica and their tannin parts from different habitats by HPLC for its quality control. The determination was carried out on a Diamonsil C18 (4.6 mm x 250 mm, 5 microm) column, with methanol-0.2% glacial acetic acid as mobile phase with gradient elution at a flow rate of 1 mL x min(-1). The temperature was maintained at 30 degrees C and the detected wavelength is 260 nm, Thirteen chromatographic peaks were extracted as the common peaks of the fingerprint of P. emblica, and eleven as the common peaks of P. emblica tannin parts, and five peaks were identified by comparing with referent samples. The fingerprints of 8 samples were compared and classified by similarity evaluation, cluster analysis and principal component analysis (PCA). The similarity degrees of eight P. emblica were between 0.763 and 0.993, while tannin parts were between 0.903 and 0.991. All the samples of P. emblica and their tannin parts were classified into 3 categories. The method was so highly reproducible, simple and reliable that it could provide basis for quality control and evaluation of P. emblica from different habitats.

  14. A comparison of flavonoid glycosides by electrospray tandem mass spectrometry

    NASA Astrophysics Data System (ADS)

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

    2006-01-01

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

  15. 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

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

    PubMed

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

    2010-11-01

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

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

    PubMed

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

    2015-05-06

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

  18. Effects of sorghum (Sorghum bicolor (L.) Moench) tannins on α-amylase activity and in vitro digestibility of starch in raw and processed flours.

    PubMed

    Mkandawire, Nyambe L; Kaufman, Rhett C; Bean, Scott R; Weller, Curtis L; Jackson, David S; Rose, Devin J

    2013-05-08

    The purpose of this study was to investigate the effects of tannins on starch digestion in tannin-containing sorghum extracts and wholegrain flours from 12 sorghum varieties. Extracts reduced amylase activity in a tannin concentration-dependent manner when the extract was mixed with the enzyme before substrate (amylopectin) addition, with higher molecular weight tannins showing greater reduction. Conversely, when the extract and substrate were combined before enzyme addition an enhancement in amylase activity was experienced. In uncooked, cooked, and cooked and stored wholegrain sorghum flours, rapidly digestible, slowly digestible, and resistant starches were not correlated with tannin content or molecular weight distribution. Resistant starch increased from 6.5% to 22-26% when tannins were added to starch up to 50% (starch weight). Tannin extracts both reduced and enhanced amylase activity depending on conditions, and, while these trends were clear in extracts, the effects on starch digestion in wholegrain flours was more complex.

  19. 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.

  20. 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

  1. 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.

  2. Cardiac ion channels

    PubMed Central

    Priest, Birgit T; McDermott, Jeff S

    2015-01-01

    Ion channels are critical for all aspects of cardiac function, including rhythmicity and contractility. Consequently, ion channels are key targets for therapeutics aimed at cardiac pathophysiologies such as atrial fibrillation or angina. At the same time, off-target interactions of drugs with cardiac ion channels can be the cause of unwanted side effects. This manuscript aims to review the physiology and pharmacology of key cardiac ion channels. The intent is to highlight recent developments for therapeutic development, as well as elucidate potential mechanisms for drug-induced cardiac side effects, rather than present an in-depth review of each channel subtype. PMID:26556552

  3. 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.

  4. 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.

  5. Selective separation of flavonoid glycosides in Dalbergia odorifera by matrix solid-phase dispersion using titania.

    PubMed

    Xu, Lingyan; Shi, Hui; Liang, Tu; Feng, Jiatao; Jin, Yu; Ke, Yanxiong; Liang, Xinmiao

    2011-06-01

    Dalbergia odorifera contains high concentrations of flavonoid aglycones and trace flavonoid glycosides. In this study, trace flavonoid glycosides were separated from D. odorifera by titania with matrix solid-phase dispersion (MSPD). Before the MSPD experiment, four standards, including two isoflavone glycosides (genistin and formononetin-8-C-apiosyl (1-6)-glucoside) and their aglycones (genistein and formononetin), were used to compare their retention on a titania column. The effect of acetonitrile concentration and pH on their retention was investigated and a conclusion was drawn that high acetonitrile concentration and pH lead to the greatest difference in the retention of flavonoid as glycosides and aglycones. Besides hydrophilic interaction and ligand-exchange interaction may exist between sugar moiety of flavonoid glycoside and titania, so that flavonoid glycosides have stronger retention than that of aglycones. Based on the chromatographic rule of flavonoid as glycosides and aglycones on the titania column, the MSPD method was optimized to elute high concentration flavonoid aglycones first with 90% acetonitrile and 10% water containing 100 mM ammonium acetate buffer, and then to elute trace flavonoid glycosides with 20% acetonitrile and 80% water containing 1% trifluoroacetate (TFA). Isolated flavonoid glycosides were further analyzed by UPLC-MS/MS, and their fragmentation in MS(2) showed they are C-glycosyl flavonoids.

  6. 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.

  7. Controlled Cardiac Computed Tomography

    PubMed Central

    Wang, Chenglin; Liu, Ying; Wang, Ge

    2006-01-01

    Cardiac computed tomography (CT) has been a hot topic for years because of the clinical importance of cardiac diseases and the rapid evolution of CT systems. In this paper, we propose a novel strategy for controlled cardiac CT that may effectively reduce image artifacts due to cardiac and respiratory motions. Our approach is radically different from existing ones and is based on controlling the X-ray source rotation velocity and powering status in reference to the cardiac motion. We theoretically show that by such a control-based intervention the data acquisition process can be optimized for cardiac CT in the cases of periodic and quasiperiodic cardiac motions. Specifically, we formulate the corresponding coordination/control schemes for either exact or approximate matches between the ideal and actual source positions, and report representative simulation results that support our analytic findings. PMID:23165017

  8. 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

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

    PubMed

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

    2014-11-01

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

  10. 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

  11. 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

  12. Determination of flavone C-glycosides in tea.

    PubMed

    Engelhardt, U H; Finger, A; Kuhr, S

    1993-09-01

    An HPLC method for the determination of flavone C-glycosides (FCG) from black tea has been developed. Sample clean-up was accomplished by means of polyamide column chromatography, followed by enzyme hydrolysis of interfering compounds such was flavonol glycosides and a second polyamide column chromatographic step. Using HPLC with gradient elution and photodiode array detection eight FCG were separated. Seven FCG were isolated by means of preparative HPLC. Identification was carried out using co-chromatography, FAB(Fast Atom Bombardment)-mass spectrometry and various nuclear magnetic resonance techniques. Apigenin 6-C-glucosyl-8-arabinoside (schaftoside) and apigenin 6-C-arabinosyl-8-C-glucoside (isoschaftoside) as well as luteolin 8-C-glucoside (orientin) and luteolin 6-C-glucoside (isoorientin) have been detected in tea for the first time. Three of the other compounds have been identified as apigenin 8-C-glucoside (vitexin), apigenin 6-C-glucoside (isovitexin) and apigenin 6,8-di-C-glucoside (vicenin-2). Their occurrence in tea has been previously reported. From its UV spectrum another compound was concluded to be an apigenin glycoside. The FCG were quantified in a variety of teas of different origins (16 black, two green and one oolong). The total amounts of the FCG were 0.48-2.69 g/kg dry weight. The FCG pattern of teas of different origins were similar to each other and no origin-dependent characteristics have yet been observed. Small amounts of FCG (1.2-2.2 mg/kg) were detected in hydrolysates of high relative molecular mass fractions (Mr > 5000) of a black tea liquor.

  13. 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.

  14. Pre-ozonation of commercial textile tannins: effects on biodegradability and toxicity.

    PubMed

    Koyunluoglu, Sebnem; Arslan-Alaton, Idil; Eremektar, Gulen; Germirli-Babuna, Fatos

    2006-01-01

    The effect of ozonation on the biodegradability and acute toxicity of two frequently used textile dye assisting chemicals, namely natural tannin (NT) having an initial chemical oxygen demand (COD0) of 1195 mg L-1; initial total organic carbon (TOC0) of 342 mg L-1; initial 5th-day biochemical oxygen demand (BOD5,0) of 86 mg L-1; initial ultraviolet absorbance at 280 nm wavelength (UV280,0) of 32.2 cm-1; initial ultraviolet absorbance at 254 nm wavelength (UV254,0) of 19.35 cm-1 and synthetic tannin (ST); with a COD0 of 465 mg L-1; TOC0 of 155 mg L-1; BOD5,0 of 6 mg L-1; UV280,0 of 11.78 cm-1; UV254,0 of 13.74 cm-1 was investigated. Synthetic wastewater bearing these tannin formulations was individually prepared and subjected to ozonation at varying doses (500 and 1000 mg h-1), and pHs (3.5 and 7.0) to elucidate the effect of ozone dose and pH on oxidation efficiency. Changes in the environmental sum parameters chemical oxygen demand (COD), total organic carbon (TOC), 5th-day biochemical oxygen demand (BOD5), ultraviolet absorbance at 280 nm wavelength (UV280) and ultraviolet absorbance at 254 nm wavelength (UV254), the latter two representing the aromaticity and double bonds of the studied textile tannins, respectively, were monitored during the course of ozonation. In the second part of the study, the biodegradability and acute toxicity of the raw and pre-ozonated textile tannins were evaluated in terms of the BOD5 parameter and an activated sludge inhibition test, respectively. Results indicated no significant changes in acute toxicity for NT, whereas the inhibitory effect of ST could be completely eliminated after 40 min ozonation at a rate of 1000 mg h-1 (i.e., at a specific ozone dose of 1.4 mg (O)3 (mg COD0)-1 and a pH of 3.5. In conclusion, pre-ozonation appeared to be potential pretreatment option to achieve complete detoxification and a fair biodegradability improvement of the otherwise refractory synthetic tannin.

  15. Structural, textural and morphological characteristics of tannins from Acacia mearnsii encapsulated using sol-gel methods: Applications as antimicrobial agents.

    PubMed

    Dos Santos, Cristiane; Vargas, Álvaro; Fronza, Ney; Dos Santos, João Henrique Zimnoch

    2017-03-01

    Tannins from Acacia mearnsii were encapsulated using four different sol-gel methods acid (SGAR), basic (SGBR), silicate (SGSR) and non-hydrolytic (SGNHR) routes. The hybrid materials were analyzed using a set of techniques to characterize their structure, texture and morphology. The antimicrobial performance of the encapsulated materials was evaluated against different microorganisms (Staphylococcus aureus, Escherichia coli, Aspergillus niger and Candida sp.). The data showed that the encapsulation route significantly affects the characteristics of the resulting hybrid materials. Better functional performances were obtained using the silicate route, which produced mesoporous materials with a small surface area (0.96m(2)g(-1)) and small particle size (<1nm). These characteristics promoted the gradual release of tannins in an aqueous medium and improved their interactions with microorganisms. Furthermore, the process demonstrated the preservation of tannins after synthesis and increased antimicrobial activity (via a controlled tannin release), as demonstrated by the moderate activity against filamentous fungi and yeast.

  16. 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.

  17. 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.

  18. 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.

  19. The effect of feed moisture and temperature on tannin content, antioxidant and antimicrobial activities of extruded chestnuts.

    PubMed

    Obiang-Obounou, Brice Wilfried; Ryu, Gi Hyung

    2013-12-15

    This study focuses on the effect of extrusion processing on tannin reduction, phenolic content, flavonoid content, antioxidant and anitimicrobial activity. Extrusion temperature (120 and 140 °C) and feed moisture (25% and 28%) were used on the tannin content, antioxidant and antimicrobial activities. Extrusion cooking reduced tannin content up to 78%, and improved antioxidant activity from 12.89% to 21.17% in a concentration dependant manner without affecting its antimicrobial activity that varied from 250 to 500 mg. The time-kill assay confirmed the ability of extruded chestnut to reduce Pseudomonas aeruginosa count below detectable limit that reduced the original inoculum by 3log10 CFU/mL. Overall, the results showed that extrusion cooking might serve as a tool for tannin reduction and could improve the antioxidant and antimicrobial properties of chestnut, which might be helpful for chestnut related products in the food industry.

  20. C21 steroidal glycosides from the roots of Cynanchum saccatum.

    PubMed

    Zhang, Mi; Rao, Li-Li; Xiang, Cheng; Li, Bao-Cai; Li, Peng

    2015-09-01

    Eight new C21 steroidal glycosides, named cynsaccatols A-H (1-8), along with two known analogs (9-10), were isolated from the roots of Cynanchum saccatum. Their structures were determined on the basis of detailed spectroscopic analysis, as well as HRESIMS. All compounds (1-10) were tested for their cytotoxicity in vitro using three human cancer cell lines (HepG2, Hela and U251), and compounds 1, 4, 5, 9, 10 showed weak inhibitory activities against different cell lines, respectively.

  1. 7-O-Methylated anthocyanidin glycosides from Catharanthus roseus.

    PubMed

    Toki, Kenjiro; Saito, Norio; Irie, Yuki; Tatsuzawa, Fumi; Shigihara, Atsushi; Honda, Toshio

    2008-03-01

    Anthocyanins were isolated from orange-red flowers of Catharanthus roseus cv 'Equator Deep Apricot', and identified as rosinidin 3-O-[6-O-(alpha-rhamnopyranosyl)-beta-galactopyranoside] (1), and also 7-O-methylcyanidin 3-O-[6-O-(alpha-rhamnopyranosyl)-beta-galactopyranoside] (2) by chemical and spectroscopic methods. Pigment 1 was found to be a major anthocyanin in the flowers of this cultivar. By contrast, the distribution of rosinidin glycosides is very limited in plants, and reported only in the flowers of Primula. Pigment 2 was found in smaller concentrations, but its aglycone, 7-O-methylcyanidin, has been reported only once before, from the fruit of mango.

  2. Acylated flavonol glycosides from the flower of Elaeagnus angustifolia L.

    PubMed

    Bendaikha, Sarah; Gadaut, Méredith; Harakat, Dominique; Magid, Alabdul

    2014-07-01

    Seven acylated flavonol glycosides named elaeagnosides A-G, in addition to seven known flavonoids were isolated from the flowers of Elaeagnus angustifolia. Their structures were elucidated by different spectroscopic methods including 1D, 2D NMR experiments and HR-ESI-MS analysis. In order to identify natural antioxidant and tyrosinase inhibitor agents, the abilities of these flavonoids to scavenge the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and to inhibit tyrosinase activity were evaluated. Results revealed that two of these compounds had significant anti-oxidant effect and one compound showed weak tyrosinase-inhibitory activity compared with kojic acid, quercetin, or ascorbic acid, which were used as positive control.

  3. Flavonoid glycosides in bergamot juice (Citrus bergamia Risso).

    PubMed

    Gattuso, Giuseppe; Caristi, Corrado; Gargiulli, Claudia; Bellocco, Ersilia; Toscano, Giovanni; Leuzzi, Ugo

    2006-05-31

    A comprehensive profile of flavonoids in bergamot juice was obtained by a single DAD-ESI-LC-MS-MS course. Eight flavonoids were found for the first time, five of these are C-glucosides (lucenin-2, stellarin-2, isovitexin, scoparin, and orientin 4'-methyl ether), and three are O-glycosides (rhoifolin 4'-O-glucoside, chrysoeriol 7-O-neohesperidoside-4'-O-glucoside, and chrysoeriol 7-O-neohesperidoside). A method is proposed to differentiate chrysoeriol and diosmetin derivatives, which are often indistinguishable by LC-MS-MS. In-depth knowledge of the flavonoid content is the starting point for bergamot juice exploitation in food industry applications.

  4. New isoflavone glycosides from the stems of Dalbergia vietnamensis.

    PubMed

    Loan, Pham Thanh; Le Anh, Hoang Tuan; Cuc, Nguyen Thi; Yen, Duong Thi Hai; Hang, Dan Thi Thuy; Ha, Tran Minh; Nhiem, Nguyen Xuan; Van Du, Nguyen; Thai, Tran Huy; Van Minh, Chau; Van Kiem, Phan

    2014-06-01

    Two new isoflavone glycosides, dalspinosin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1) and caviunin 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), and two known compounds, caviunin 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3) and caviunin (4) were isolated from the stems of Dalbergia vietnamensis. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparing with the NMR data reported in the literature.

  5. A new benzophenone glycoside from the leaves of Mitracarpus villosus.

    PubMed

    Ngwoke, Kenneth G; Orame, Njideka; Liu, Shuai; Okoye, Festus B C; Daletos, Georgios; Proksch, Peter

    2017-03-22

    A new benzophenone glycoside, mitraphenone A (1), together with three known compounds (2-4) were isolated from the leaves of the traditionally used medicinal plant Mitracarpus villosus (Rubiaceae) collected in Nigeria. A combination of one- and two-dimensional NMR spectroscopic and mass spectrometric measurements were carried out to identify the structure of 1. All isolated compounds (1-4) were screened for their antibacterial activity against several Gram-positive and Gram-negative bacteria. Compound 1 exhibited moderate activity against Enterococcus faecium (strains ATCC 35667 and ATCC 700221) and Staphylococcus aureus ATCC 25923 with MIC values ranging from 25 to 50 μM.

  6. [Iridoid glycosides from buds of Jasminum officinale L. var. grandiflorum].

    PubMed

    Zhao, Gui-qin; Yin, Zhi-feng; Liu, Yu-cui; Li, Hong-bo

    2011-10-01

    The study on the buds of Jasminum officinale L. var. grandiflorum was carried out to look for anti-HBV constituents. The isolation and purification were performed by HPLC and chromatography on silica gel, polyamide and Sephadex LH-20 column. The structures were elucidated on the basis of physicochemical properties and spectral analysis. Six iridoid glycosides were identified as jasgranoside B (1), 6-O-methy-catalpol (2), deacetyl asperulosidic acid (3), aucubin (4), 8-dehydroxy shanzhiside (5), and loganin (6). Jasgranoside B (1) is a new compound. Compounds 2-6 were isolated from Jasminum officinale L. var. grandiflorum for the first time.

  7. New cyclopeptide alkaloid and lignan glycoside from Justicia procumbens.

    PubMed

    Jin, Hong; Chen, Li; Tian, Ying; Li, Bin; Dong, Jun-Xing

    2015-01-01

    This study reported a new cyclopeptide alkaloid, justicianene A (1), and a new lignan glycoside, procumbenoside H (2), isolated from Justicia procumbens. The structures of the new compounds were elucidated by means of spectroscopic analysis, including extensive 2D NMR studies and mass spectrometry. Cyclopeptide alkaloids were first observed from the genus Justicia. Compound 2 was cytotoxic against human LoVo colon carcinoma cells with an IC50 value of 17.908 ± 1.949 μM.

  8. Three New Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Craspidaster hesperus

    PubMed Central

    Kang, Jun-Xia; Kang, Yong-Feng; Han, Hua

    2016-01-01

    Three new polyhydroxysteroidal glycosides, hesperuside A (1), B (2), and C (3), as well as a known novaeguinoside A (4), were isolated from the ethanol extract of starfish Craspidaster hesperus collected from the South China Sea. Their structures were elucidated by extensive spectroscopic methods and chemical evidence. The compounds 1–3 present unprecedented carbohydrate chain 3-O-methyl-β-d-galactopyranose, which differ from each other in the side chains. These compounds exhibited cytotoxicity against human tumor cells BEL-7402, MOLT-4, and A-549 in vitro. PMID:27775561

  9. Additional new minor cucurbitane glycosides from Siraitia grosvenorii.

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2014-03-24

    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.

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

    PubMed

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

    2016-01-01

    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.

  11. New pregnane glycoside derivative from Caralluma retrospiciens (Ehrenb).

    PubMed

    Elsebai, Mahmoud Fahmi; Mohamed, Ietidal El-Tahir

    2015-01-01

    Retrospinoside (1) is a new polyoxy pregnane glycoside which was isolated and characterised from the aerial parts of Caralluma retrospiciens (Ehrenb.) N. E. Br., family Apocynaceae. The structure was established as 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-(3-O-methyl-6-desoxygalactopyranosy)]-14,15,20-trihydroxy-4β-pregnane. Its structural elucidation was performed through extensive spectroscopic measurements including 1D- and 2D-NMR, and HRMS, in addition to chemical methods.

  12. 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.

  13. 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.

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

    PubMed

    Shimada, Takuya; Nishii, Eriko; Saitoh, Takashi

    2011-12-01

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

  15. Sequestration of soil nitrogen as tannin-protein complexes may improve the competitive ability of sheep laurel (Kalmia angustifolia) relative to black spruce (Picea mariana).

    PubMed

    Joanisse, G D; Bradley, R L; Preston, C M; Bending, G D

    2009-01-01

    The role of litter tannins in controlling soil nitrogen (N) cycling may explain the competitive ability of Kalmia relative to black spruce (Picea mariana), although this has not been demonstrated experimentally. Here, the protein-precipitation capacities of purified tannins and leaf extracts from Kalmia and black spruce were compared. The resistance to degradation of tannin-protein precipitates from both species were compared by monitoring carbon (C) and N dynamics in humus amended with protein, purified tannins or protein-tannin precipitates. The purity of the precipitates was verified using solid-state (13)C nuclear magnetic resonance (NMR) spectra. The ability of mycorrhizal fungi associated with both species to grow on media amended with tannin-protein complexes as the principal N source was also compared. The protein precipitation capacity of Kalmia tannins was superior to those of black spruce. Humus amended with protein increased both mineral and microbial N, whereas humus amended with tannin-protein precipitates increased dissolved organic N. Mycorrhizal fungi associated with Kalmia showed better growth than those associated with black spruce when N was provided as tannin-protein precipitates. These data suggest that Kalmia litter increases the amount of soil N sequestered as tannin-protein complexes, which may improve the competitive ability of Kalmia relative to black spruce by favouring N uptake by mycorrhizas associated with the former.

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

    PubMed

    O'May, Che; Tufenkji, Nathalie

    2011-05-01

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

  17. 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.

  18. 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.

  19. A new cembrane glycoside in Asterothamnus centrali-asiaticus from Gobi Desert.

    PubMed

    Todorova, Milka; Trendafilova, Antoaneta; Javsmaa, Namshir; Altantsetseg, Shatarin; Shatar, Sanduin

    2013-09-01

    A new cembrane glycoside, nephthenol 15-O-β-d-quinovoside, was isolated from the aerial parts of Asterothamnus centrali-asiaticus. Its structure was elucidated by 1D and 2D NMR spectroscopic analysis, as well as by mass spectrometry. This is the first report of the occurrence of a cembrane glycoside in vascular plants.

  20. 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...

  1. 2-C-branched glycosides from 2'-carbonylalkyl 2-O-Ms(Ts)-C-glycosides. A tandem SN2-SN2 reaction via 1,2-cyclopropanated sugars.

    PubMed

    Shao, Huawu; Ekthawatchai, Sanchai; Wu, Shih-Hsiung; Zou, Wei

    2004-09-30

    [reaction: see text] Under basic conditions, 2'-aldehydo (acetonyl) 2-O-Ms(Ts)-alpha-C-glycosides undergo an intramolecular S(N)2 reaction to form 1,2-cyclopropanated sugars, which react with nucleophiles (alcohols, thiols, and azide) at the anomeric carbon to give 2-C-branched glycosides. By way of contrast, the 1,2-cyclopropanes derived from 2'-ketones only react with thiols to give 2-C-branched thioglycosides.

  2. Extraordinary efficacy of 16 alpha-gitoxin, an ultra-short acting semi-synthetic digitalis glycoside.

    PubMed

    Haustein, K O; Bauer, R

    1994-06-01

    The positive inotropic effect of 16 alpha-gitoxin was studied in 52 female and male healthy volunteers between the ages of 21 and 27 years and a body weight between 55 and 76 kg after the single i.v. injection or oral administration in doses between 2.5 and 15 mg. The inotropic effect was evaluated by the use of the systolic time intervals (left ventricular ejection time, LVET, and electromechanic systole, QS2) and by the QT-Interval of the ECG. The glycoside plasma level was measured simultaneously to the pharmacodynamic parameters by a radioimmunoassay, 16 alpha-gitoxin abbreviated dose-dependently the STI (LVET and QS2) for 30 (i.v.) or 15 ms (per os) and the QT interval for 35 ms. A mean plasma concentration of 401 ng/ml was measured 15 minutes after the i.v. injection of 5 mg and a mean plasma level of 402 ng/ml was measured 1 hour after the oral intake of 10 mg 16 alpha-gitoxin as an aqueous-ethanolic solution. The shortening of the STI-values and of the QT-interval correlated with the administered glycoside dose and with the AUC0-6-value. The AUC-values increased linearly with the administered dose. The ratio of the AUC0-6-values after i.v. or oral administration of 7.5 mg 16 alpha-gitoxin amounted to 0.673. Doses of 16 alpha-gitoxin which induce a maximum abbreviation of STI or QT did neither provoke a distinct decrease in heart rate nor cardiac disturbances. Sixteen-alpha-gitoxin develops a positive inotropic effect within a few minutes after i.v. injection and also after oral intake.(ABSTRACT TRUNCATED AT 250 WORDS)

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

    PubMed

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

    2016-02-01

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

  4. A comparison of two strategies to modify the hydroxylation of condensed tannin polymers in Lotus corniculatus L.

    PubMed

    Robbins, Mark P; Bavage, Adrian D; Allison, Gordon; Davies, Teri; Hauck, Barbara; Morris, Phillip

    2005-05-01

    A full-length sense Antirrhinum majus dihydroflavonol reductase (DFR) sequence was introduced into birdsfoot trefoil (Lotus corniculatus L.) in experiments aimed at modifying condensed tannin content and polymer hydroxylation in a predictable manner. Analysis of transgenic plants indicated lines that showed enhanced tannin content in leaf and stem tissues. In contrast to previous data from root cultures, levels of propelargonidin units were not markedly elevated in lines with enhanced tannin content. RT-PCR analysis of four selected lines indicated a correlation between enhanced tannin content and expression of the introduced DFR transgene. Using a contrasting approach we introduced a flavonoid 3'5' hydroxylase (F3'5'H) sequence derived from Eustoma grandiflorum into Lotus root cultures. Expression of the transgene was associated with increased levels of condensed tannins and in this case there was also no alteration in polymer hydroxylation. These results suggest that additional mechanisms may exist that control the hydroxylation state of condensed tannins in this model species.

  5. Studies on Emblica officinalis derived tannins for their immunostimulatory and protective activities against coccidiosis in industrial broiler chickens.

    PubMed

    Kaleem, Qari Muhammad; Akhtar, Masood; Awais, Mian Muhammad; Saleem, Muhammad; Zafar, Muddassar; Iqbal, Zafar; Muhammad, Faqir; Anwar, Muhammad Irfan

    2014-01-01

    The present study reports the effect of Emblica officinalis (EO) derived tannins on humoral immune responses and their protective efficacy against Eimeria infection in chickens. Tannins were extracted from EO and characterized by HPLC. EO derived tannins (EOT) and commercial tannins (CT) were orally administered in broiler chicks in graded doses for three consecutive days, that is, 5th-7th days of age. On day 14 after administration of tannins, humoral immune response was detected against sheep red blood cells (SRBCs) by haemagglutination assay. Protective efficacy of tannins was measured against coccidial infection, induced by Eimeria species. Results revealed higher geomean titers against SRBCs in chickens administered with EOT as compared to those administered with CT and control group. Mean oocysts per gram of droppings were significantly lower (P < 0.05) in EOT administered chickens as compared to control group. Lesion scoring also showed the lowest caecal and intestinal lesion score of mild to moderate intensity in chickens administered with EOT. Further, significantly higher (P < 0.05) daily body weight gains and antibody titers were detected in EOT administered chickens as compared to those of CT administered and control groups. EOT showed the immunostimulatory properties in broilers and their administration in chickens boost the protective immunity against coccidiosis.

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

    PubMed

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

    2014-05-20

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

  7. 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

  8. 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.

  9. Merremins A-G, resin glycosides from Merremia hederacea with multidrug resistance reversal activity.

    PubMed

    Wang, Wen-qiong; Song, Wei-bin; Lan, Xiao-jing; Huang, Min; Xuan, Li-jiang

    2014-10-24

    Five new pentasaccharide resin glycosides, named merremins A-E (1-5), two new pentasaccharide resin glycoside methyl esters, named merremins F and G (6, 7), and four known resin glycosides, murucoidin IV, murucoidin V, stoloniferin IV, and murucoidin XVII, were obtained from the aerial parts of Merremia hederacea. This is the first report of resin glycosides obtained from M. hederacea. In addition, the new compounds can be divided into three types: those possessing an 18-membered ring (1-4), compound 5 with a 20-membered ring, and those with an acyclic core (6, 7). Furthermore, the different types of resin glycosides were evaluated for their multidrug resistance reversal activities. Compounds 1, 5, 6, and murucoidin V were noncytotoxic and enhanced the cytotoxicity of vinblastine by 2.3-142.5-fold at 25 μM. Compound 5 and murucoidin V, with 20-membered rings, were more active than compound 1, with an 18-membered ring.

  10. Synthesis of gold nanoparticles with glycosides: synthetic trends based on the structures of glycones and aglycones.

    PubMed

    Jung, Jisung; Park, Suryeon; Hong, Suckchang; Ha, Min Woo; Park, Hyeung-geun; Park, Youmie; Lee, Hyo-Jong; Park, Yohan

    2014-03-11

    A new, room temperature synthetic method for gold nanoparticles from auric acid with glycosides as reducing agents in aqueous NaOH is presented. As a mechanistic study of the oxidation sites on the glycosides, eight sugar-containing reductants (glycoside, glucose, glucuronic acid) have been tested in the synthesis of gold nanoparticles to determine their trends based on the structures of glycones and aglycones. As a result of the comparison among the eight sugar-containing reductants, it was determined that C-6 of glycosides is oxidized to a carboxylic acid during the reduction of auric acid. To detect the oxidized compounds of the glycosides, the reaction mixtures were monitored by (13)C NMR. Among the eight sugar-containing reductants, phenyl β-D-glucoside generated the highest synthetic yield of mono-dispersed, round gold nanoparticles (13.15±1.30 nm, 99.7% yield).

  11. Hydration of vinyl ether groups by unsaturated glycoside hydrolases and their role in bacterial pathogenesis.

    PubMed

    Hashimoto, Wataru; Itoh, Takafumi; Maruyama, Yukie; Mikami, Bunzo; Murata, Kousaku

    2007-12-01

    Many pathogenic microorganisms invade mammalian and/or plant cells by producing polysaccharide-degrading enzymes (lyases and hydrolases). Mammalian glycosaminoglycans and plant pectins that form part of the cell surface matrix are typical targets for these microbial enzymes. Unsaturated glycoside hydrolase catalyzes the hydrolytic release of an unsaturated uronic acid from oligosaccharides, which are produced through the reaction of matrix-degrading polysaccharide lyase. This enzymatic ability suggests that unsaturated glycoside hydrolases function as virulence factors in microbial infection. This review focuses on the molecular identification, bacterial distribution, and structure/function relationships of these enzymes. In contrast to general glycoside hydrolases, in which the catalytic mechanism involves the retention or inversion of an anomeric configuration, unsaturated glycoside hydrolases uniquely trigger the hydrolysis of vinyl ether groups in unsaturated saccharides but not of their glycosidic bonds.

  12. Stimulation of steviol glycoside accumulation in Stevia rebaudiana by red LED light.

    PubMed

    Ceunen, Stijn; Werbrouck, Stefaan; Geuns, Jan M C

    2012-05-01

    The aim of this study was to determine whether steviol glycoside accumulation is under phytochrome control. The results indicate that Stevia rebaudiana Bertoni plants grown under short-day conditions showed precocious flowering and stagnation of steviol glycoside accumulation. Long night interruption by red LED light stimulated and sustained the vegetative growth as well as the accumulation of steviol glycosides in the leaves. After 7 weeks of treatment, steviol glycoside content was about two-fold higher in LED-treated plants than in the short-day control group. The effects of red LED light were measured both in a greenhouse and in a phytotron, irrespective of cultivar-specific differences. Therefore, it can be concluded that a mid-night interruption by red LED light during short photoperiods provides an easy and inexpensive method to increase vegetative leaf biomass production with an increased steviol glycoside yield.

  13. 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.

  14. First evidence of the presence of S-cysteinylated and S-glutathionylated precursors in tannins.

    PubMed

    Larcher, Roberto; Tonidandel, Loris; Nicolini, Giorgio; Fedrizzi, Bruno

    2013-11-15

    Tannins are widely used in winemaking and food and beverage preparation for the many different contributions they can give to the overall characteristics of the product (e.g., colour stability, mouthfeel and aromatic composition). Varietal thiols and their precursors are one of the most interesting research areas in food science and a lot of effort has been put to further the current understanding on their formation and on the impact of different production strategies on their concentration in the final product. This paper reports the identification of two important thiol precursors (Cys-3MH and GSH-3MH) in commercial grape oenological tannins and, to the best of our knowledge, this information is reported here for the first time. This finding allows potential new perspectives in the winemaking and the food industry, offering the possibility of controlled additions of thiol precursors in pre-fermentative stages in order to tune the aroma profile of fermented products.

  15. 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.

  16. 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.

  17. 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.

  18. Antioxidant activity of tannin components from Vaccinium vitis-idaea L.

    PubMed

    Ho, K Y; Huang, J S; Tsai, C C; Lin, T C; Hsu, Y F; Lin, C C

    1999-09-01

    Reactive oxygen molecules have been implicated as important pathological mediators in many clinical disorders and periodontal disease. To provide possible alternative treatment of periodontal disease, six tannins isolated from Vaccinium vitis-idaea L. were evaluated for anti-lipid peroxidation, anti-superoxide formation and free radical scavenging activity. The results showed that cinnamtannin B1 displayed the strongest anti-lipid peroxidation activity, proanthocyanidin A-1 displayed the strongest superoxide scavenging activity, and epicatechin-(4beta--> 6)-epicatechin-(4beta-->8, 2beta-->O--> 7)-catechin had the strongest anti-superoxide formation effect. We conclude that tannins isolated from V. vitis-idaea L. exhibited multiple antioxidant activity, and could be used for the treatment of periodontal disease.

  19. Return of Viable Cardiac Function After Sonographic Cardiac Standstill in Pediatric Cardiac Arrest.

    PubMed

    Steffen, Katherine; Thompson, W Reid; Pustavoitau, Aliaksei; Su, Erik

    2017-01-01

    Sonographic cardiac standstill during adult cardiac arrest is associated with failure to get return to spontaneous circulation. This report documents 3 children whose cardiac function returned after standstill with extracorporeal membranous oxygenation. Sonographic cardiac standstill may not predict cardiac death in children.

  20. Anti-HIV diphyllin glycosides from Justicia gendarussa.

    PubMed

    Zhang, Hong-Jie; Rumschlag-Booms, Emily; Guan, Yi-Fu; Liu, Kang-Lun; Wang, Dong-Ying; Li, Wan-Fei; Nguyen, Van Hung; Cuong, Nguyen Manh; Soejarto, Djaja Doel; Fong, Harry H S; Rong, Lijun

    2017-04-01

    In a search for new anti-HIV active leads from over several thousands of plant extracts, we have identified a potent plant lead. The active plant is determined as Justicia gendarussa (Acanthaceae), a medicinal plant that has been used for the treatment of injury, arthritis and rheumatism in Asia including China. Our bioassay-guided fractionation of the methanol extract of the stems and barks of the plant led to the isolation of two anti-HIV compounds, justiprocumins A and B. The compounds are identified as new arylnaphthalide lignans (ANL) glycosides. We further determined that the ANL glycosides are the chemical constituents that contribute to the anti-HIV activity of this plant. Justiprocumin B displayed potent activity against a broad spectrum of HIV strains with IC50 values in the range of 15-21 nM (AZT, IC50 77-95 nM). The compound also displayed potent inhibitory activity against the NRTI (nucleoside reverse transcriptase inhibitor)-resistant isolate (HIV-11617-1) of the analogue (AZT) as well as the NNRTI (non-nucleoside reverse transcriptase inhibitor)-resistant isolate (HIV-1N119) of the analogue (nevaripine).

  1. Glycosides from edible sea cucumbers stimulate macrophages via purinergic receptors

    PubMed Central

    Aminin, Dmitry; Pislyagin, Evgeny; Astashev, Maxim; Es’kov, Andrey; Kozhemyako, Valery; Avilov, Sergei; Zelepuga, Elena; Yurchenko, Ekaterina; Kaluzhskiy, Leonid; Kozlovskaya, Emma; Ivanov, Alexis; Stonik, Valentin

    2016-01-01

    Since ancient times, edible sea cucumbers have been considered a jewel of the seabed and used in Asian folk medicine for stimulation of resistance against different diseases. However, the power of this sea food has not been established on a molecular level. A particular group of triterpene glycosides was found to be characteristic metabolites of the animals, responsible for this biological action. Using one of them, cucumarioside A2-2 (CA2-2) from the edible Cucumaria japonica species as an example as well as inhibitory analysis, patch-clamp on single macrophages, small interfering RNA technique, immunoblotting, SPR analysis, computer modeling and other methods, we demonstrate low doses of CA2-2 specifically to interact with P2X receptors (predominantly P2X4) on membranes of mature macrophages, enhancing the reversible ATP-dependent Ca2+ intake and recovering Ca2+ transport at inactivation of these receptors. As result, interaction of glycosides of this type with P2X receptors leads to activation of cellular immunity. PMID:28004778

  2. 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.

  3. 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

  4. Recovering glycoside hydrolase genes from active tundra cellulolytic bacteria.

    PubMed

    Pinnell, Lee J; Dunford, Eric; Ronan, Patrick; Hausner, Martina; Neufeld, Josh D

    2014-07-01

    Bacteria responsible for cellulose hydrolysis in situ are poorly understood, largely because of the relatively recent development of cultivation-independent methods for their detection and characterization. This study combined DNA stable-isotope probing (DNA-SIP) and metagenomics for identifying active bacterial communities that assimilated carbon from glucose and cellulose in Arctic tundra microcosms. Following DNA-SIP, bacterial fingerprint analysis of gradient fractions confirmed isotopic enrichment. Sequenced fingerprint bands and clone library analysis of 16S rRNA genes identified active bacterial taxa associated with cellulose-associated labelled DNA, including Bacteroidetes (Sphingobacteriales), Betaproteobacteria (Burkholderiales), Alphaproteobacteria (Caulobacteraceae), and Chloroflexi (Anaerolineaceae). We also compared glycoside hydrolase metagenomic profiles from bulk soil and heavy DNA recovered from DNA-SIP incubations. Active populations consuming [(13)C]glucose and [(13)C]cellulose were distinct, based on ordinations of light and heavy DNA. Metagenomic analysis demonstrated a ∼3-fold increase in the relative abundance of glycoside hydrolases in DNA-SIP libraries over bulk-soil libraries. The data also indicate that multiple displacement amplification introduced bias into the resulting metagenomic analysis. This research identified DNA-SIP incubation conditions for glucose and cellulose that were suitable for Arctic tundra soil and confirmed that DNA-SIP enrichment can increase target gene frequencies in metagenomic libraries.

  5. Steviol glycosides modulate glucose transport in different cell types.

    PubMed

    Rizzo, Benedetta; Zambonin, Laura; Angeloni, Cristina; Leoncini, Emanuela; Dalla Sega, Francesco Vieceli; 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.

  6. 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

  7. 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).

  8. 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

  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. 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

  11. Towards high resolution ^1H NMR spectra of tannin colloidal aggregates

    NASA Astrophysics Data System (ADS)

    Mirabel, M.; Glories, Y.; Pianet, I.; Dufourc, E. J.

    1999-10-01

    The time dependent colloidal formation of tannins in hydro-alcoholic medium has been studied by 1H-NMR. Line broadening observed with time can be cancelled by making use of magic angle sample spinning (MASS) thus yielding sharp lines that allow structural studies. We used as an example catechin, a constitutive monomer of Bordeaux young red wine tannins. Chemical shift variations of polyphenol protons allow monitoring the time course of aggregation. La formation de tanins colloïdaux au cours du temps, en milieu hydroalcoolique, a été suivie par RMN-^1H. Un élargissement marqué des résonances est observé et peut être supprimé par la rotation de l'échantillon à l'angle magique ce qui ouvre tout un champ d'études structurales sur ces composés colloïdaux. L'exemple proposé est celui de la catéchine, monomère constitutif de tannins présents en grande quantité dans les vins rouges jeunes de Bordeaux. Des variations du déplacement chimique de certains protons polyphénoliques permettent de suivre l'évolution temporelle de l'agrégation.

  12. Hydrolyzable tannins of tamaricaceous plants. IV: Micropropagation and ellagitannin production in shoot cultures of Tamarix tetrandra.

    PubMed

    Orabi, Mohamed A A; Taniguchi, Shoko; Terabayashi, Susumu; Hatano, Tsutomu

    2011-11-01

    Shoot cultures of Tamarix tetrandra on Linsmaier-Skoog (LS) agar medium with 30 g l(-1) sucrose, 2.13 mg l(-1) indoleacetic acid and 2.25 mg l(-1) benzyl adenine produced ellagitannins found in intact plants of the Tamaricaceae. This was demonstrated by the isolation of 14 monomeric-tetrameric ellagitannins from the aq. Me2CO extract of the cultured tissues. This is the first report on the production of ellagitannin tetramers by plant tissue culture. The effects of light and certain medium constituents on tissue growth and ellagitannin production were examined. The contents of representative tannins of different types [i.e., tellimagrandin II (monomer), hirtellin A (linear GOG-type dimer), hirtellin B (hellinoyl-type dimer), hirtellin C (macrocyclic-type dimer), and hirtellin T1 (linear GOG-type trimer)] in the resultant tissues in response to these factors were estimated by HPLC, and the optimal condition for production of these tannins were established. Shoots cultured on LS hormone-free medium promoted root development, and regenerated plants could adapt to ordinary soil and climate. Acclimatized and intact T. tetrandra plants that were collected in November and May, respectively, demonstrated seasonal differences in individual ellagitannin contents. HPLC comparison of individual ellagitannin contents in different plant materials (i.e., leaves, stems, and roots) of intact T. tetrandra plants is also reported. The results are discussed with respect to cellular deposition and biosynthetic relationship of tannins.

  13. 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.

  14. Membrane treatment by nanofiltration of exhausted vegetable tannin liquors from the leather industry.

    PubMed

    Cassano, A; Adzet, J; Molinari, R; Buonomenna, M G; Roig, J; Drioli, E

    2003-05-01

    A rational use of water in the leather industry is described by applying the criteria of "clean technologies" by means of membrane processes. A nanofiltration (NF) process was used for recovering tannins and water from exhausted baths and reusing them as tanning agents and washings. Results of experiments performed on laboratory and semi-industrial pilot scale plants, operating and fluid-dynamic conditions and mass balance of the NF process are reported and discussed. Chemical and physical analytical values measured on skins treated with the recovered solutions were very similar to those measured on control skins tanned with standard solutions. According to the obtained results, a process scheme is suggested. It permits both to recover water and to increase the tannin/non tannin (T/NT) ratio in the retentate solution, starting from exhausted tanning baths and by using a NF membrane purification/concentration. The final volume reduction factor of tested exhausted baths was 5.25, the increase of T/NT ratio was from 1.1 to 2.3 and the average permeate flux was 12.5l/m(2)h. Advantages are in terms of: reduction of environmental impact (up to 75% of COD reduction of the global effluent), simplification of cleaning-up processes of wastewaters, decrease of disposal costs, saving of chemicals and water.

  15. Tannins of tamarind seed husk: preparation, structural characterization, and antioxidant activities.

    PubMed

    Sinchaiyakit, Puksiri; Ezure, Yohji; Sriprang, Sarin; Pongbangpho, Supakorn; Povichit, Nasapon; Suttajit, Maitree

    2011-06-01

    The high content (about 39%) of polymeric tannins in tamarind (Tamarindus indica L.) seed husk (TSH) was demonstrated, and an extract (crude TSE) with a high content (about 94%) of polymeric tannins was prepared from TSH with a one pot extraction using ethanol/water (3:2, v/v). The crude TSE was further purified with Sephadex LH20 to give one fraction (metTSE) eluted with methanol/water (3:2, v/v) and another (acTSE) eluted with acetone/water (3:2, v/v). The tannins of acTSE were established as polymeric proanthocyanidins (PA) by 13C NMR spectroscopy; this was further confirmed by IR and UV spectroscopy, n-BuOH/HCl and vanillin assays, and from HPLC pattern. The ratio of procyanidins to prodelphinidins was 2:3, and the average degree of polymerization of acTSE was 7. Galloylated flavan-3-ols were not detected in acTSE. The main ingredients of metTSE were confirmed to be polymeric PA by 13C NMR spectroscopy. The antioxidant activities using DPPH and ABTS assays were investigated. The IC50 values of acTSE were 4.2 +/- 0.2 (DPPH assay) and 6.2 +/- 0.3 microg/mL (ABTS assay).

  16. 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.

  17. Evaluation of the content variation of anthraquinone glycosides in rhubarb by UPLC-PDA

    PubMed Central

    2013-01-01

    Background Rhubarb is an important Chinese medicinal herb with a long history of over 2000 years and has been commonly used as a laxative. It is the radix and rhizome of Rheum officinale Baill., R. palmatum L. and R. tanguticum Maxim, all of which are mainly distributed in a broad region in the Tibetan plateau. Anthraquinone glycosides are a series of major active ingredients found in all three species. They are key intermediates in the anthraquinone secondary metabolism and the sennnoside biosynthesis. The variation of the anthraquinone glycoside content in rhubarb in response to specific factors remains an attractive topic. Results A simple and sensitive Ultra Performance Liquid Chromatography with Photo-Diode Array (UPLC-PDA) detector was developed for the simultaneous determination of six anthraquinone glycosides in rhubarb, i.e., aloeemodin-8-O-glucoside, rhein-8-O-glucoside, chrysophanol-1-O-glucoside, emodin-1-O-glucoside, chrysophanol-8-O-glucoside, emodin-8-O-glucoside. Twenty-seven batches from three species were submitted to the multi-component analysis. The results showed that the anthraquinone glycoside content varied significantly even within the same species. The results showed that the anthraquinone glycoside content varied significantly within the same species but not between different species. The PCA and content analysis results confirmed that the plant species has no obvious effect on the content variation. Neither was any significant correlation observed between the anthraquinone glycoside content and the geographic distribution of the rhubarb. Through correlational analysis, altitude was found to be the main factor that affects the anthraquinone glycoside content in rhubarb. Rhubarb grown at higher altitude has higher anthraquinone glycoside content. Conclusions This work provides a rapid, sensitive and accurate UPLC-PDA method for the simultaneous determination of six anthraquinone glycosides in rhubarb. The anthraquinone glycoside content

  18. 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

  19. Measuring the molecular dimensions of wine tannins: comparison of small-angle X-ray scattering, gel-permeation chromatography and mean degree of polymerization.

    PubMed

    McRae, Jacqui M; Kirby, Nigel; Mertens, Haydyn D T; Kassara, Stella; Smith, Paul A

    2014-07-23

    The molecular size of wine tannins can influence astringency, and yet it has been unclear as to whether the standard methods for determining average tannin molecular weight (MW), including gel-permeation chromatography (GPC) and depolymerization reactions, are actually related to the size of the tannin in wine-like conditions. Small-angle X-ray scattering (SAXS) was therefore used to determine the molecular sizes and corresponding MWs of wine tannin samples from 3 and 7 year old Cabernet Sauvignon wine in a variety of wine-like matrixes: 5-15% and 100% ethanol; 0-200 mM NaCl and pH 3.0-4.0, and compared to those measured using the standard methods. The SAXS results indicated that the tannin samples from the older wine were larger than those of the younger wine and that wine composition did not greatly impact on tannin molecular size. The average tannin MWs as determined by GPC correlated strongly with the SAXS results, suggesting that this method does give a good indication of tannin molecular size in wine-like conditions. The MW as determined from the depolymerization reactions did not correlate as strongly with the SAXS results. To our knowledge, SAXS measurements have not previously been attempted for wine tannins.

  20. In vitro acaricidal effect of tannin-rich plants against the cattle tick Rhipicephalus (Boophilus) microplus (Acari: Ixodidae).

    PubMed

    Fernández-Salas, A; Alonso-Díaz, M A; Acosta-Rodríguez, R; Torres-Acosta, J F J; Sandoval-Castro, C A; Rodríguez-Vivas, R I

    2011-01-10

    The objectives of this study were to evaluate the in vitro acaricidal effects of lyophilized extracts of four tannin rich plants (Acacia pennatula, Piscidia piscipula, Leucaena leucocephala and Lysiloma latisiliquum) against diverse stages of Rhipicephalus (Boophilus) microplus, and to asses whether tannins were involved in the acaricidal effect using polyethylene glycol (PEG) to block tannins. Larval immersion (LIT) and adult immersion (AIT) tests were used to evaluate the acaricidal effect of each of the lyophilized extracts against larval and adult stages of R. microplus respectively. Larvae and adult ticks were exposed to increasing concentrations of each plant extract (0, 1200, 2400, 4800, 9600 and 19,200 μg ml(-1)) for 10 min. Larval mortality was recorded at 48 h post-incubation. Adult mortality was recorded daily over 14 days, at which point their reproductive efficiency was evaluated. PEG was added to the extracts to verify whether tannins were involved in the acaricidal effect. The effect on egg laying inhibition and larval mortality was analyzed using the GLM procedure in SAS. A Kruskal-Wallis test was used to assess the effect of PEG on LIT results. Calculation of the lethal concentration 50 (LC50) was performed using a probit analysis. All extracts reduced the viability of R. microplus larval stages (P<0.001), and viability was restored with the addition of PEG suggesting an important role of tannins in the acaricidal effect (P<0.001). The LC50 values of L. latisiliquum and P. piscipula plant extracts were 6.402 and 2.466 μg ml(-1). None of the tannin-rich plant extracts affected adult mortality (P>0.05). Lysiloma latisiliquum extract inhibited egg hatching of R. microplus (P<0.01). Tannin-rich plant extracts from A. pennatula, P. piscipula, L. leucocephala and L. latisiliquum showed potential acaricidal activity. Further in vivo studies are needed to confirm this finding.

  1. N cycling and the composition of terpenes and tannins in boreal forest soils: Effects of logging residues

    NASA Astrophysics Data System (ADS)

    Smolander, Aino; Kitunen, Veikko; Kukkola, Mikko; Tamminen, Pekka

    2014-05-01

    There is increasing evidence available that certain terpenes and tannins may mediate substantial changes in nitrogen cycling processes in boreal forest soils. Terpenes and tannins are two important groups of plant secondary metabolites: Terpenes are hydrocarbons having different number of isoprene-derived units and tannins are complex polyphenolic compounds able to interact with proteins. Logging residues, consisting of fresh tree tops and branches with needles contain large amounts of terpenes and tannins. Currently there is increasing demand for forest biomass for bioenergy production. Therefore, harvesting of logging residues has become more common from both clear-cutting and thinning stands, instead of conventional stem-only harvest where logging residues are retained on the site. Our aim was to determine how logging residues affect soil N cycling processes in Scots pine and Norway spruce thinning stands in long-term, and how these processes are related to the composition of terpenes and tannins in the soil. Samples were taken from the humus layer of pine and spruce experiments which had been thinned 4-to-19 years before; in the thinning different amounts of logging residues had been distributed on the plots. Logging residues had only little effect on soil microbial biomass N or C. However, in several sites logging residues increased the rate of net N mineralization and the ratios net N mineralization/ C mineralization and net N mineralization/microbial biomass N, and these positive effects were very long-lasting. Logging residues also changed the composition of different terpenes and condensed tannins in soil. In general, with regard to the processes and ratios indicating N availability, stem-only harvest seems to be more favorable than whole-tree harvest. The results from long-term field experiments will be discussed in relation to the effects of different terpenes and tannins, observed in short-term laboratory experiments, on N cycling processes.

  2. 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.

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

    PubMed Central

    Guleria, Praveen; Yadav, Sudesh Kumar

    2013-01-01

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

  4. 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

  5. Biochemical ecology of the forest tent caterpillar: responses to dietary protein and phenolic glycosides.

    PubMed

    Lindroth, Richard L; Bloomer, Mark S

    1991-05-01

    Interactions between quaking aspen (Populus tremuloides) and the forest tent caterpillar (Malacosoma disstria) are likely to be influenced by leaf protein and phenolic glycoside levels, and insect detoxication activity. We investigated the direct and interactive effects of dietary protein and phenolic glycosides on larval performance and midgut enzyme activity of forest tent caterpillars. We conducted bioassays with six artificial diets, using both first and fourth stadium larvae. Four of the diets comprised a 2×2 factorial design-two levels of protein, each with and without phenolic glycosides. Additionally, we assayed high protein diets containing S,S,S-tributylphosphorotrithioate (DEF, an esterase inhibitor) and DEF plus phenolic glycosides. Enzyme solutions were prepared from midguts of sixth instars and assayed for β-glucosidase, esterase and glutathione transferase activities. First instar mortality and development times were higher for larvae on diets low in protein or containing phenolic glycosides. Effects of phenolic glycosides were especially pronounced at low protein levels and when administered with DEF. Fourth instar development times were prolonged, and growth rates reduced, in response to consumption of low protein diets. Effects of phenolic glycosides on growth were less pronounced, although the effect for larvae on the low protein diet was nearly significant. Activity of each of the enzyme systems was reduced in larvae reared on low protein diets, and esterase activity was induced in larvae fed phenolic glycosides. Our results suggest that larval performance may be strongly affected by levels of protein and phenolic glycosides commonly occurring in aspen foliage, and that these factors may play a role in differential defoliation of aspen by forest tent caterpillars.

  6. 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

  7. Antioxidant phenylethanoid glycosides and a neolignan from Jacaranda caucana.

    PubMed

    Martin, Frédéric; Hay, Anne-Emmanuelle; Quinteros Condoretty, Valentin R; Cressend, Delphine; Reist, Marianne; Gupta, Mahabir P; Carrupt, Pierre-Alain; Hostettmann, Kurt

    2009-05-22

    Extracts from several plants of the family Bignoniaceae from Panama were submitted to a rapid DPPH TLC test for the detection of radical-scavenging activity. The MeOH extract of the stems of Jacaranda caucana, a tree that grows from Costa Rica to Colombia, was selected due to its interesting activity and the lack of phytochemical studies on the polar extract. This extract was partitioned between ethyl acetate, butanol, and water. The EtOAc fraction afforded two new phenylethanoid glycosides (1, 2), along with protocatechuic acid, acteoside, and jionoside D. Further purifications yielded isoacteoside and martynoside. The BuOH fraction afforded a new rhamnosyl derivative of sisymbrifolin (8), a neolignan. The structures were determined by means of spectrometric methods, including 1D and 2D NMR experiments and MS analysis.

  8. Two new lignan glycosides from the seeds of Cuscuta chinensis.

    PubMed

    He, Xiang-Hui; Yang, Wen-Zhi; Meng, A-Hui; He, Wen-Ni; Guo, De-An; Ye, Min

    2010-11-01

    Two new lignan glycosides, 2'-hydroxyl asarinin 2'-O-β-D-glucopyranoside (cuscutoside C, 1) and 2'-hydroxyl asarinin 2'-O-β-D-apiofuranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranoside (cuscutoside D, 2), were isolated from the seeds of Cuscuta chinensis Lam., along with six known compounds, 2'-hydroxyl asarinin 2'-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside (3), 2'-hydroxyl asarinin 2'-O-β-D-apiofuranosyl-(1 → 2)-β-D-glucopyranoside (cuscutoside A, 4), kaempferol 3,7-di-O-β-D-glucopyranoside (5), 5-caffeoyl quinic acid (6), 4-caffeoyl quinic acid (7), and cinnamic acid (8). Their structures were elucidated on the basis of spectroscopic analyses including HR-ESI-MS, ESI-MS/MS, (1)H and (13)C NMR, HSQC, HMBC, and TOCSY.

  9. C21 steroidal glycosides from the roots of Cynanchum paniculatum.

    PubMed

    Zhao, Dan; Feng, Baomin; Chen, Shaofei; Chen, Gang; Li, Zhifeng; Lu, Xiaojie; Sang, Xianan; An, Xiao; Wang, Haifeng; Pei, Yuehu

    2016-09-01

    As a part of our continuing research for bioactive constituents from Cynanchum plants, four new C21 steroidal glycosides, cynapanoside D-G (1-4), together with six known compounds (5-10) were isolated from the roots of Cynanchum paniculatum (Bge.) Kitag. Their structures were elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. Compound 8 exhibited potent inhibitory activities against HL-60, HT-29, PC-3 and MCF-7 cell lines with IC50 values of 8.3, 7.5, 34.3 and 19.4μM, respectively and compounds 1-4 and 9 displayed moderate cytotoxicity against the four cell lines. The in vitro antioxidant activities of compounds 1-4, 8 and 9 were assayed by DPPH radical scavenging activity. Antibacterial and antifungal activities of compounds 1-4, 8 and 9 were also tested.

  10. 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.

  11. 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.

  12. Cerebrosides and terpene glycosides from the root of Aster scaber.

    PubMed

    Kwon, Hak Cheol; Cho, Ock Ryun; Lee, Kang Choon; Lee, Kang Ro

    2003-02-01

    Three cerebrosides 2, 3, and 5 and two terpene glycosides 1 and 4 have been isolated from the methanol extract of the root of Aster scaber. Their structures were determined as 3-O-beta-D-glucuronopyranosyl-oleanolic acid methyl ester (1), (2S, 3S, 4R, 2'R, 8Z, 15'Z)-N-2'-hydroxy-15'-tetracosenoyl-1-O-beta-D-glucopyranosyl-4-hydroxy-8-sphingenine (2), (2S, 3S, 4R, 8Z)-N-octadecanoyl-1-O-beta-D-glucopyranosyl-4-hydroxy-8-sphingenine (3), 1alpha-hydroxy-6beta-O-beta-D-glucosyl-eudesm-3-ene (4), and (2S, 3S, 4R, 2'R, 8Z)-N-2'-hydroxy-hexadecanoyl-1-O-beta-D-glucopyranosyl-4-hydroxy-8-sphingenine (5) on the basis of spectroscopic methods.

  13. Flavanone Glycosides as Acetylcholinesterase Inhibitors: Computational and Experimental Evidence

    PubMed Central

    Remya, C.; Dileep, K. V.; Tintu, I.; Variyar, E. J.; Sadasivan, C.

    2014-01-01

    Acetylcholinesterase hydrolyzes the neurotransmitter called acetylcholine and is crucially involved in the regulation of neurotransmission. One of the observable facts in the neurodegenerative disorders like Alzheimer's disease is the decrease in the level of acetylcholine. Available drugs that are used for the treatment of Alzheimer's disease are primarily acetylcholinesterase inhibitors with multiple activities. They maintain the level of acetylcholine in the brain by inhibiting the acetylcholinesterase function. Hence acetylcholinesterase inhibitors can be used as lead compounds for the development of drugs against AD. In the present study, the binding potential of four flavanone glycosides such as naringin, hesperidin, poncirin and sakuranin against acetylcholinesterase was analysed by using the method of molecular modeling and docking. The activity of the top scored compound, naringin was further investigated by enzyme inhibition studies and its inhibitory concentration (IC50) towards acetylcholinesterase was also determined. PMID:25593395

  14. [Glycosides from flowers of Jasminum officinale L. var. grandiflorum].

    PubMed

    Zhao, Gui-qin; Xia, Jing-jing; Dong, Jun-xing

    2007-10-01

    To study the chemical constituents of the flower of Jasminum officinale L. var. grandiflorum. The compounds were isolated and purified by re-crystallization and chromatography on silica gel and Sephadex LH-20 column. Their structures were elucidated on the physicochemical properties and spectral analysis. Seven glycosides were identified as kaempferol-3-O-alpha-L-rhamnopyranosyl (1-->3)-[alpha-L-rhamnopyranosyl (1-->6)]-beta-D-galactopyranoside (I), kaempferol-3-O-rutinoside (II), 7-ketologanin (III), oleoside-11-methyl ester (IV), 7-glucosyl-l1-methyl oleoside (V), ligstroside (VI), oleuropein (VII). Compound I is a new compound. Compounds III and V were isolated from the family of Jasminum for the first time and compounds II, IV and VI were isolated from Jasminum officinale L. var. grandiflorum for the first time.

  15. 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.

  16. Additional minor diterpene glycosides from Stevia rebaudiana Bertoni.

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2013-10-31

    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.

  17. [Studies on triterpenoids and their glycosides from Aralia dasyphylla Miq].

    PubMed

    Yi, Y H; Gu, J Q; Xiao, K; Wang, Z Z; Lin, H W

    1997-10-01

    The structures of two triterpenoids and their glycosides were isolated from Aralia dasyphylla Miq. Their structures have been identified to be oleanoic acid(I), 16 beta-hydroxy-18 beta-H-oleanoic acid(II), oleanoic acid-28-O-beta-D-glucopyranoside(III) and 16 beta-hydroxy-18 beta-H-oleanoic acid-28-O-beta-D-glucopyranoside(IV), respectively, mainly through interpretation of UV, IR, MS, 1H and 13CNMR, DEPT, HMQC and HMBC spectra data. The stereochemistry of II has been confirmed by NOESY. Pharmacological experiments showed that the total saponins exerted preventative effect on CCl4-induced liver injury of male mice and hypoglycemic effect on a model of alloxan-induced diabetes in rats.

  18. Neuroactive flavonoid glycosides from Tilia petiolaris DC. extracts.

    PubMed

    Loscalzo, Leonardo M; Wasowski, Cristina; Marder, Mariel

    2009-10-01

    Pharmacological assay guided purification of an ethanol extract of Tilia petiolaris DC. inflorescences resulted in the isolation and identification of isoquercitrin (ISO), quercetin 3-O-glucoside-7-O-rhamnoside (QUE) and kaempferol 3-O-glucoside-7-O-rhamnoside (KAE). The behavioral actions of these glycosylated flavonoids were examined in the hole board, locomotor activity and thiopental-induced loss of righting reflex tests in mice. QUE (10 and 30 mg/kg) and KAE (30 mg/kg), intraperitoneally (i.p.) administered to mice, reduced all the parameters measured in the hole board test, but ISO (30 mg/kg) only reduced the number of rearings. Meanwhile QUE at 30 mg/kg i.p. also decreased the ambulatory locomotor activity and increased the sodium thiopental-induced time of loss of the righting reflex suggesting a clear depressant action. The above results demonstrate the occurrence of neuroactive flavonoid glycosides in Tilia.

  19. 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.

  20. Allimacrosides A-E, new steroidal glycosides from Allium macrostemon Bunge.

    PubMed

    Kim, Yun Sik; Suh, Won Se; Park, Kyoung Jin; Choi, Sang Un; Lee, Kang Ro

    2017-02-01

    A new pregnane-type steroidal glycoside (1), two new spirostane-type steroidal glycosides (2, 3), and two new furostane-type steroidal glycosides (4, 5), named allimacrosides A-E, together with four known compounds (6-9) were isolated from a 80% MeOH extract of Allium macrostemon Bunge. The identification and structural elucidation of these compounds were based on their 1D- and 2D-NMR spectra, and HR-FAB-MS data analysis. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using the sulforhodamine B bioassay.