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Cardiac glycosides in traditional Chinese medicine  

Microsoft Academic Search

Summary  The effect of cardiac glycosides containing medicinal herbs, e.g. Ting Li Zi (Descurainia sophia), against heart failure was detected by traditional Chinese doctors at the beginning of the first century, more than 16 centuries\\u000a before Withering’s discovery of digitalis to promote diuresis. We ran infer the diagnosis from the description of the symptom\\u000a complex, for which the herb as the

Lu Fu-hua



Oleandrin: A cardiac glycosides with potent cytotoxicity.  


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-?B) 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

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



Oleandrin: A cardiac glycosides with potent cytotoxicity  

PubMed Central

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-?B) 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

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



Cardiac glycosides of Cheiranthus allioni. XIII. Glucoerycordin  

Microsoft Academic Search

From plains erysimum (Cheiranthus allioni) Hort., (Erysimum asperum) a new cardiac glycoside has been isolated which has been called glucoerycordin. Its chemical structure has been established mainly by stepwise hydrolysis and the identification of the hydrolysis products. Glucoerycordin C41H64 O19, mp 131–135°C, [a]D20 -22.2 ± 3° (c 0.65; methanol) is 3ß-[O-ß-D-glucopyranosyl-(1 ? 4)-O-ß-D-glycopyranosyl-(1 ? 4)-gulomethylopyranosyloxy]-14,19-dihydroxy-5ß, 14ß-card-20(22)-enolide.

I. F. Makarevich; A. I. Pavlii; S. I. Makarevich



Antiproliferative cardiac glycosides from the latex of Antiaris toxicaria.  


Phytochemical investigation of the latex of Antiaris toxicaria resulted in the isolation of 15 new [antiarosides J-X (1-15)] and 17 known cardiac glycosides. The effects of the cardiac glycosides on apoptosis and the expression of orphan nuclear receptor Nur77 were examined in human NIH-H460 lung cancer cells. Several of the cardiac glycosides induced apoptosis in lung cancer cells, which was accompanied by induction of Nur77 protein expression. Treatment of cancer cells with the cardiac glycosides resulted in translocation of the Nur77 protein from the nucleus to the cytoplasm and subsequent targeting to mitochondria. The results show that the cardiac glycosides exert their apoptotic effect through the Nur77-dependent apoptotic pathway. PMID:24033101

Liu, Qian; Tang, Jin-Shan; Hu, Meng-Jie; Liu, Jie; Chen, Hai-Feng; Gao, Hao; Wang, Guang-Hui; Li, Shun-Lin; Hao, Xiao-Jiang; Zhang, Xiao-Kun; Yao, Xin-Sheng



[Cardiac glycosides: From ancient history through Withering's foxglove to endogeneous cardiac glycosides].  


For centuries, drugs that increase the power of contraction of the failing heart have been used for the treatment of congestive heart failure (dropsy). The cardiac effect is due to the content of cardiac glycosides. Squill or sea onion, Urginea (Scilla) maritima, a seashore plant, was known by the ancient Romans and Syrians and possibly also by the ancient Egyptians. Squills were used erratically, but some prescriptions indicate that they may have been used for the treatment of oedematous states. The toxic effect of strophanthus species was known from poisoned arrows used by the natives in Africa. Digitalis, derived form the foxglove plant, Digitalis purpurea, is mentioned in writings as early as 1250; a Welsh family, known as the Physicians of Myddvai, collected different herbs and digitalis was included in their prescriptions. However, the druge was used erratically until the 18th century, when William Withering, an English physician and botanist, published a monograph describing the clinical effects of an extract of the foxglove plant. Later, in 1785, the indication and the toxicity of digitalis were reported in his book, "An account of the Foxglove and some of its medical uses with practical remarks on dropsy, and other diseases". In Denmark, the leaves of Digitalis purpurea or Digitalis lanata were tested for cardiac glycoside activity. The standardized digitalis powder was used in tinctures, infusions, and tablets. The preparations were included in successive editions of the Danish pharmacopoeia, some of the tinctures already in 1828, i.e. before the standardization of the drug. Isolation of cardiac glycosides from digitalis, strophanthus and squill and determination of their chemical structures initiated biochemical and pharmacological studies. The scientific advances led to an understanding of cardiac muscle contractility and the Na,K pump as the cellular receptor for the inotropic action of digitalis. Examination of putative endogenous ligands to the receptor revealed some endogenous cardiac glycosides of similar or identical structures as those found in digitalis, strophanthus and squill. Increased concentrations of these glycosides are found in patients with heart failure. Further investigations are needed to determine whether the secretion of glycosides might be a physiologic response to a diminished cardiac output. PMID:15685783

Norn, Svend; Kruse, Poul R



Secondary chemistry of hybrid and parental willows: Phenolic glycosides and condensed tannins in Salix sericea, S. eriocephala , and their hybrids  

Microsoft Academic Search

Salix sericea andS. eriocephala differ markedly in secondary chemistry.S. sericea produces phenolic glycosides, salicortin and 2?-cinnamoylsalicortin, and low concentrations of condensed tannin. In contrast,S. eriocephala produces no phenolic glycosides, but high concentrations of condensed tannins. Hybrid chemistry is intermediate for both types of chemicals, suggesting predominantly additive inheritance of these two defensive chemical systems from the parental species. However, there

Colin M. Orians; Robert S. Fritz



Trial watch: Cardiac glycosides and cancer therapy.  


Cardiac glycosides (CGs) are natural compounds sharing the ability to operate as potent inhibitors of the plasma membrane Na(+)/K(+)-ATPase, hence promoting-via an indirect mechanism-the intracellular accumulation of Ca(2+) ions. In cardiomyocytes, increased intracellular Ca(2+) concentrations exert prominent positive inotropic effects, that is, they increase myocardial contractility. Owing to this feature, two CGs, namely digoxin and digitoxin, have extensively been used in the past for the treatment of several cardiac conditions, including distinct types of arrhythmia as well as contractility disorders. Nowadays, digoxin is approved by the FDA and indicated for the treatment of congestive heart failure, atrial fibrillation and atrial flutter with rapid ventricular response, whereas the use of digitoxin has been discontinued in several Western countries. Recently, CGs have been suggested to exert potent antineoplastic effects, notably as they appear to increase the immunogenicity of dying cancer cells. In this Trial Watch, we summarize the mechanisms that underpin the unsuspected anticancer potential of CGs and discuss the progress of clinical studies that have evaluated/are evaluating the safety and efficacy of CGs for oncological indications. PMID:23525565

Menger, Laurie; Vacchelli, Erika; Kepp, Oliver; Eggermont, Alexander; Tartour, Eric; Zitvogel, Laurence; Kroemer, Guido; Galluzzi, Lorenzo



Quantitative HPLC analysis of cardiac glycosides in Digitalis purpurea leaves.  


An analytical method for the determination of cardiac glycosides in Digitalis purpurea leaves by hplc was developed. Quantitation was carried out by the incorporation of lanatoside A as an internal standard. The present method is sufficiently precise and relatively simple. PMID:7673934

Ikeda, Y; Fujii, Y; Nakaya, I; Yamazaki, M



Cardiac glycosides from the bark of Antiaris toxicaria.  


Five new cardiac glycosides (1-5, namely antiaroside Y-ZC) together with 19 known compounds were obtained from the bark of Antiaris toxicaria. Their chemical structures were determined by IR, HR-ESI-MS, 1D and 2D NMR (HSQC, (1)H-(1)H COSY, HMBC, ROESY). The absolute configuration of sugar unit was defined by acid hydrolysis and appropriate derivatization. Compound 1 was rare 5?-H-10?-H-19-nor-cardenolide, which might derive from decarboxylative derivative of 19-COOH cardenolide. The inhibitory effects of cardiac glycosides 1-11 on the viability of NIH-H460 lung cancer cells and their induction of Nur77 expression were evaluated and preliminary structure-activity relationship (SAR) was also discussed. PMID:24879902

Li, Xiao-San; Hu, Meng-Jie; Liu, Jie; Liu, Qian; Huang, Zhi-Xing; Li, Shun-Lin; Hao, Xiao-Jiang; Zhang, Xiao-Kun; Yao, Xin-Sheng; Tang, Jin-Shan



Phenolic glycosides and condensed tannins in Salix sericea, S. eriocephala and their F1 hybrids: not all hybrids are created equal  

Microsoft Academic Search

The performance of hybrids depends upon the inheritance and expression of resistance traits. Secondary chemicals are one such resistance trait. In this study, we measured the concentrations of phenolic glycosides and condensed tannins in parental and F1 hybrid willows to examine the sources of chemical variation among hybrids. S. sericea produces phenolic glycosides, salicortin and 2?-cinnamoylsalicortin, and low concentrations of

Colin M. Orians; Megan E Griffiths; Bernadette M. Roche; Robert S. Fritz



Phenolic glycosides and condensed tannins in Salix sericea, S. eriocephala and their F1 hybrids: not all hybrids are created equal.  


The performance of hybrids depends upon the inheritance and expression of resistance traits. Secondary chemicals are one such resistance trait. In this study, we measured the concentrations of phenolic glycosides and condensed tannins in parental and F1 hybrid willows to examine the sources of chemical variation among hybrids. S. sericea produces phenolic glycosides, salicortin and 2'-cinnamoylsalicortin, and low concentrations of condensed tannin in its leaves. In contrast, S. eriocephala produces no phenolic glycosides but high concentrations of condensed tannins in its leaves. These traits are inherited quantitatively in hybrids. On average, F1 hybrids are intermediate for condensed tannins, suggesting predominantly additive inheritance or balanced ambidirectional dominance of this defensive chemical from the parental species. In contrast, the concentration of phenolic glycosides is lower than the parental midpoint, indicating directional dominance. However, there is extensive variation among F1 hybrids. The concentration of tannin and phenolic glycosides in F1 hybrid families is either (1) lower than the midpoint, (2) higher than the midpoint, or (3) indistinguishable from the midpoint of the two parental taxa. It appears that the production of the phenolic glycosides, especially 2'-cinnamoylsalicortin, is controlled by one or more recessive alleles. We also observed a two-fold or greater difference in concentration between some hybrid families. We discuss how chemical variation may effect the relative susceptibility of hybrid willows to herbivores. PMID:10854738

Orians; Griffiths; Roche1b; Fritz



Herbivore avoidance of digitalis extracts is not mediated by cardiac glycosides.  


This study was conducted to determine whether avoidance of digitalis (Digitalis purpurea) by mountain beaver (Aplodontia rufa) is induced by toxic cardiac glycosides. High-performance liquid chromatography and behavioral assays were used to relate animal responses with the presence of common cardiac glycosides in several digitalis extracts. Statistical analyses of multiple-choice tests showed no correlation between cardiac glycoside content and mountain beaver avoidance of apple cubes treated with digitalis extracts. Therefore, we concluded that known toxic cardiac glycosides were not responsible for chemosensory cues that inhibited intake of food treated with digitalis extracts. These results suggest that digitalis is a source of an effective nontoxic herbivore repellent. PMID:24233675

Nolte, D L; Kelly, K L; Kimball, B A; Johnston, J J



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


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. PMID:23465047

Beale, Thomas M; Taylor, Mark S



Cardiac Glycosides Induce Cell Death in Human Cells by Inhibiting General Protein Synthesis  

Microsoft Academic Search

BackgroundCardiac glycosides are Na+\\/K+-pump inhibitors widely used to treat heart failure. They are also highly cytotoxic, and studies have suggested specific anti-tumor activity leading to current clinical trials in cancer patients. However, a definitive demonstration of this putative anti-cancer activity and the underlying molecular mechanism has remained elusive.Methodology\\/Principal FindingsUsing an unbiased transcriptomics approach, we found that cardiac glycosides inhibit general

Andrea Perne; Markus K. Muellner; Magdalena Steinrueck; Nils Craig-Mueller; Julia Mayerhofer; Ilse Schwarzinger; Mathew Sloane; Iris Z. Uras; Gregor Hoermann; Sebastian M. B. Nijman; Matthias Mayerhofer; Alfred Lewin



Secondary chemistry of hybrid and parental willows: Phenolic glycosides and condensed tannins inSalix sericea, S. eriocephala, and their hybrids.  


Salix sericea andS. eriocephala differ markedly in secondary chemistry.S. sericea produces phenolic glycosides, salicortin and 2'-cinnamoylsalicortin, and low concentrations of condensed tannin. In contrast,S. eriocephala produces no phenolic glycosides, but high concentrations of condensed tannins. Hybrid chemistry is intermediate for both types of chemicals, suggesting predominantly additive inheritance of these two defensive chemical systems from the parental species. However, there is extensive variation among hybrids. This variation may be due to genetic variation among parental genotypes, which genes were passed on, or to subsequent back-crossing. The differences in chemistry are likely to exert a strong effect on the relative susceptibility of hybrid and parental willows to herbivores. PMID:24234624

Orians, C M; Fritz, R S



Subchronic treatment with vanadate does not potentiate the toxicity of cardiac glycosides  

Microsoft Academic Search

Since it has been claimed that vanadate is an endogenous regulator of Na\\/K-ATPase activity and that it potentiates the toxicity\\u000a of cardiac glycosides, we were alarmed to discover that certain Finnish physicians were prescribing vanadate in combination\\u000a with other trace minerals to elderly patients for many different chronic diseases (e.g., cancer, rheumatism). To study the\\u000a interaction of vanadate and cardiac

E. MacDonald; H. Lihtamo; Kaisa Hellevuo; H. Komulainen



High-performance liquid chromatographic determination of secondary cardiac glycosides in Digitalis purpurea leaves.  


An analytical method for the determination of secondary cardiac glycosides in Digitalis purpurea leaves by high-performance liquid chromatography (HPLC) is described. The procedure consisted of extraction of dry leaf powder with ethanol-chloroform (2:1) and clean-up by Sep-Pak cartridges prior to HPLC analysis. HPLC was performed on an octylsilyl bonded silica column, using acetonitrile-methanol-water (4:4:5) for trisdigitoxosides and acetonitrile-methanol-water (8:30:43) for strospeside; the effluent was monitored by ultraviolet detection (at 220 nm). Quantitation of these cardiac glycosides was carried out by the internal standard method. The amounts of digitoxin, gitoxin, gitaloxin and strospeside per 100 mg of dry leaf powder were estimated to be 22.6, 14.0, 54.7 and 1.9 micrograms, respectively. The method is sufficiently sensitive and reproducible to assay secondary glycosides in Digitalis purpurea leaves. PMID:2808604

Fujii, Y; Ikeda, Y; Yamazaki, M



Preparation and evaluation of technetium-99m labeled cardiac glycoside derivatives as potential myocardial imaging agent.  


Three cardiac glycosides, two natural, cymarin and convallotoxin and one synthetic, strophanthidin-beta-D-glucoside were converted to their thiosemicarbazone and subsequently radiolabeled with 99mTc by chelation. The resulting radioactive chelate complexes were evaluated in animals to determine the suitability of this class of compounds for myocardial imaging. It was observed from the animal biodistribution data of the three radioactive compounds, there was a considerable variation in the heart to non-target organ uptake ratio. A possible explanation of this variation was offered in the light of their lipophilic character, protein binding ability and affinity towards non-target receptors. It is anticipated that this study may help to develop a 99mTc-cardiac glycoside complex with better distribution characteristics, and such a compound may offer a suitable alternative to 201Tl, which is at present used for myocardial imaging. PMID:3255737

Misra, M; Sarkar, H S; Chatterjee, M; Banerjee, S



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


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. PMID:21843803

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



Interaction of palytoxin and cardiac glycosides on erythrocyte membrane and (Na+ + K+) ATPase.  


Palytoxin (PTX), at extremely low concentrations (0.01-1 nM), caused K+ release from rabbit erythrocytes. Among the various chemical compounds tested, cardiac glycosides potently inhibited the PTX-induced K+ release. The order of inhibitory potency (IC50) was cymarin (0.42 microM) greater than convallatoxin (0.9 microM) greater than ouabain (2.3 microM) greater than digitoxin (88 microM) greater than digoxin (90 microM). Their corresponding aglycones, even at 10 microM, did not inhibit the K+ release, but competitively antagonized the inhibitory effect of the glycosides. All these cardiotonic steroids inhibited the activity of (Na+ + K+)-ATPase prepared from hog cerebral cortex in narrow concentration ranges (IC50 = 0.15-2.4 microM), suggesting that the inhibition of K+ release is not related to their inhibitory potency on the (Na+ + K+)-ATPase activity, and the sugar moiety of cardiac glycosides is involved in the inhibition. On the other hand PTX, at higher concentrations (greater than 0.1 microM), inhibited the (Na+ + K+)-ATPase activity. However, this inhibitory effect of PTX was not antagonized by ouabain. It is suggested that, compared with ouabain, PTX has additional binding site(s) on the (Na+ + K+)-ATPase. PMID:2865137

Ozaki, H; Nagase, H; Urakawa, N



BDNF Mediates Neuroprotection against Oxygen-Glucose Deprivation by the Cardiac Glycoside Oleandrin  

PubMed Central

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. PMID:24431454

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



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


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. PMID:24431454

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



The cytotoxic activities of cardiac glycosides from Streptocaulon juventas and the structure-activity relationships.  


A series of cardiac glycosides were isolated and identified from the anti-tumor fraction of the root of Streptocaulon juventas in previous studies. In the present research, the cytotoxic activities of the 43 cardiac glycosides on three cell lines, human lung A549 adenocarcinoma cell, large cell lung cancer NCI-H460 cell and normal human fetal lung fibroblast MRC-5 cell, were evaluated in vitro. Most of the tested compounds showed potent inhibitory activities toward the three cell lines. Then, the structure-activity relationships were discussed in detail. It was indicated that hydroxyl and acetyl groups at C-16 increased the activity, whereas hydroxyl group at C-1 and C-5 can both increase and decrease the activity. Two glucosyl groups which were connected by C1'?C6' showed better inhibitory activity against cancer cell lines, while the C1'?C4' connection showed stronger inhibitory activity against the normal cell line. Also, this is the first report that the activities of these compounds exhibited different variation trends between A549 and NCI-H460 cell lines, which indicated that these compounds could selectively inhibit the cell growth. The results would lay a foundation for further research on new anti-tumor drug development. PMID:25128424

Xue, Rui; Han, Na; Ye, Chun; Wang, Lihui; Yang, Jingyu; Wang, Yu; Yin, Jun



Acaricidal effects of cardiac glycosides, azadirachtin and neem oil against the camel tick, Hyalomma dromedarii (Acari: Ixodidae).  


The cardiac glycoside, digitoxin, from Digitalis purpurea L (Scrophulariaceae), a cardiac glycosidal (cardenolide) extract from Calotropis procera (Ait) R Br (Asclepiadaceae), azadirachtin and neem oil from Azadirachta indica A Juss (Meliaceae) were tested for their effects against larvae and adult stages of the camel tick, Hyalomma dromedarii Koch (Acari: Ixodidae). The contact LC50 values of the first three materials against adults were 4.08, 9.63 and >40.7 microg cm(-2), respectively, whereas the dipping LC50 values of the four materials were 409.9, 1096, >5000 and >5000 mg litre(-1), respectively. Contact and dipping LC50 values of the extract and azadirachtin against larvae were 6.16, >20.3 microg cm(-2) and 587.7 and >2500 mg litre(-1), respectively. Azadirachtin had no effects on egg production or feeding of adults up to 5000 mg litre(-1); however at 2500 mg litre(-1), it caused significant reduction in feeding activity of larve, prolonged the period for moulting to nymphal stage, and caused 60% reduction in moultability. Results of the two cardiac glycoside materials are comparable with those of several commercial acaricides. The risks and benefits associated with the use of cardiac glycosides are considered. PMID:14620053

Al-Rajhy, DiefAlla H; Alahmed, Azzam M; Hussein, Hamdy I; Kheir, Salah M



Cardiac glycosides provide neuroprotection against ischemic stroke: Discovery by a brain slice-based compound screening platform  

PubMed Central

We report here the results of a chemical genetic screen using small molecules with known pharmacologies coupled with a cortical brain slice-based model for ischemic stroke. We identified a small-molecule compound not previously appreciated to have neuroprotective action in ischemic stroke, the cardiac glycoside neriifolin, and demonstrated that its properties in the brain slice assay included delayed therapeutic potential exceeding 6 h. Neriifolin is structurally related to the digitalis class of cardiac glycosides, and its putative target is the Na+/K+-ATPase. Other cardiac glycoside compounds tested also showed neuroprotective activity, although with lower apparent potencies. In subsequent whole-animal studies, we found that neriifolin provided significant neuroprotection in a neonatal model of hypoxia/ischemia and in a middle cerebral artery occlusion model of transient focal ischemia. The neuroprotective potential of Na+/K+-ATPase is of particular interest because of its known “druggability”; indeed, Food and Drug Administration-approved, small-molecule compounds such as digitoxin and digoxin have been in clinical usage for congestive heart failure and arrhythmias for several decades. Thus, an existing cardiac glycoside or closely related compound could provide an accelerated path toward clinical trial testing for ischemic stroke. Our findings underscore the important role that hypothesis-neutral, high-content, tissue-based screens can play in the identification of new candidate drugs and drug targets for the treatment of diseases for which validated therapeutic pathways are not currently available. PMID:16793926

Wang, James K. T.; Portbury, Stuart; Thomas, Mary Beth; Barney, Shawn; Ricca, Daniel J.; Morris, Dexter L.; Warner, David S.; Lo, Donald C.



Nerium oleander derived cardiac glycoside oleandrin is a novel inhibitor of HIV infectivity.  


We evaluated the effectiveness of Anvirzel™, an aqueous extract of Nerium oleander on HIV infection of human peripheral blood mononuclear cells. Oleandrin, the principle cardiac glycoside (CG) in Anvirzel™ has been shown to exhibit anti-cancer properties but its efficacy against HIV is unknown. Treatment with Anvirzel™ significantly reduced the infectivity of virus produced from infected cells without any change in the total amount of virus produced. This is in contrast to treatment with AZT, a potent inhibitor of HIV replication that has been shown to significantly reduce virus production. Relative to untreated cultures, virus in cultures treated with oleandrin had significantly reduced expression of the envelope protein gp120, the sole determinant of virus infectivity, suggesting a novel mechanism underlying the impaired infectivity. These results support the potential utility of the Nerium oleander aqueous extract, containing the CG oleandrin as a novel candidate anti-HIV therapeutic. PMID:23127567

Singh, Shailbala; Shenoy, Sachin; Nehete, Pramod N; Yang, Peiying; Nehete, Bharti; Fontenot, Danielle; Yang, Guojun; Newman, Robert A; Sastry, K Jagannadha



Digoxin and other cardiac glycosides inhibit HIF-1? synthesis and block tumor growth  

PubMed Central

A library of drugs that are in clinical trials or use was screened for inhibitors of hypoxia-inducible factor 1 (HIF-1). Twenty drugs inhibited HIF-1-dependent gene transcription by >88% at a concentration of 0.4 ?M. Eleven of these drugs were cardiac glycosides, including digoxin, ouabain, and proscillaridin A, which inhibited HIF-1? protein synthesis and expression of HIF-1 target genes in cancer cells. Digoxin administration increased latency and decreased growth of tumor xenografts, whereas treatment of established tumors resulted in growth arrest within one week. Enforced expression of HIF-1? by transfection was not inhibited by digoxin, and xenografts derived from these cells were resistant to the anti-tumor effects of digoxin, demonstrating that HIF-1 is a critical target of digoxin for cancer therapy. PMID:19020076

Zhang, Huafeng; Qian, David Z.; Tan, Yee Sun; Lee, KangAe; Gao, Ping; Ren, Yunzhao R.; Rey, Sergio; Hammers, Hans; Chang, Daniel; Pili, Roberto; Dang, Chi V.; Liu, Jun O.; Semenza, Gregg L.



Structural complexes in the squid giant axon membrane sensitive to ionic concentrations and cardiac glycosides  

PubMed Central

Giant nerve fibers of squid Sepioteuthis sepiodea were incubated for 10 min in artificial sea water (ASW) under control conditions, in the absence of various ions, and in the presence of cardiac glycosides. The nerve fibers were fixed in OsO(4) and embedded in Epon, and structural complexes along the axolemma were studied. These complexes consist of a portion of axolemma exhibiting a three-layered substructure, an undercoating of a dense material (approximately 0.1?m in length and approximately 70-170 A in thickness), and a narrowing to disappearance of the axon-Schwann cell interspace. In the controls, the incidence of complexes per 1,000?m of axon perimeter was about 137. This number decreased to 10-25 percent when magnesium was not present in the incubating media, whatever the calcium concentration (88, 44, or 0 mM). In the presence of magnesium, the number and structural features of the complexes were preserved, though the number decreased to 65 percent when high calcium was simultaneously present. The complexes were also modified and decreased to 26-32 percent by incubating the nerves in solutions having low concentrations of sodium and potassium. The adding of 10(-5) M ouabain or strophanthoside to normal ASW incubating solution decreased them to 20-40 percent. Due to their sensitivity to changes in external ionic concentrations and to the presence of cardiac glycosides, the complexes are proposed to represent the structural correlate of specialized sites for active ion transport, although other factors may be involved. PMID:1254642

Villegas, GM; Villegas, J



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


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

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



Isolation of a multispecific organic anion and cardiac glycoside transporter from rat brain  

PubMed Central

A novel multispecific organic anion transporting polypeptide (oatp2) has been isolated from rat brain. The cloned cDNA contains 3,640 bp. The coding region extends over 1,983 nucleotides, thus encoding a polypeptide of 661 amino acids. Oatp2 is homologous to other members of the oatp gene family of membrane transporters with 12 predicted transmembrane domains, five potential glycosylation, and six potential protein kinase C phosphorylation sites. In functional expression studies in Xenopus laevis oocytes, oatp2 mediated uptake of the bile acids taurocholate (Km ? 35 ?M) and cholate (Km ? 46 ?M), the estrogen conjugates 17?-estradiol-glucuronide (Km ? 3 ?M) and estrone-3-sulfate (Km ? 11 ?M), and the cardiac gylcosides ouabain (Km ? 470 ?M) and digoxin (Km ? 0.24 ?M). Although most of the tested compounds are common substrates of several oatp-related transporters, high-affinity uptake of digoxin is a unique feature of the newly cloned oatp2. On the basis of Northern blot analysis under high-stringency conditions, oatp2 is highly expressed in brain, liver, and kidney but not in heart, spleen, lung, skeletal muscle, and testes. These results provide further support for the overall significance of oatps as a new family of multispecific organic anion transporters. They indicate that oatp2 may play an especially important role in the brain accumulation and toxicity of digoxin and in the hepatobiliary and renal excretion of cardiac glycosides from the body. PMID:9294213

Noe, Birgitta; Hagenbuch, Bruno; Stieger, Bruno; Meier, Peter J.



Arrhythmogenic adverse effects of cardiac glycosides are mediated by redox modification of ryanodine receptors  

PubMed Central

Abstract The therapeutic use of cardiac glycosides (CGs), agents commonly used in treating heart failure (HF), is limited by arrhythmic toxicity. The adverse effects of CGs have been attributed to excessive accumulation of intracellular Ca2+ resulting from inhibition of Na+/K+-ATPase ion transport activity. However, CGs are also known to increase intracellular reactive oxygen species (ROS), which could contribute to arrhythmogenesis through redox modification of cardiac ryanodine receptors (RyR2s). Here we sought to determine whether modification of RyR2s by ROS contributes to CG-dependent arrhythmogenesis and examine the relevant sources of ROS. In isolated rat ventricular myocytes, the CG digitoxin (DGT) increased the incidence of arrhythmogenic spontaneous Ca2+ waves, decreased the sarcoplasmic reticulum (SR) Ca2+ load, and increased both ROS and RyR2 thiol oxidation. Additionally, pretreatment with DGT increased spark frequency in permeabilized myocytes. These effects on Ca2+ waves and sparks were prevented by the antioxidant N-(2-mercaptopropionyl) glycine (MPG). The CG-dependent increases in ROS, RyR2 oxidation and arrhythmogenic propensity were reversed by inhibitors of NADPH oxidase, mitochondrial ATP-dependent K+ channels (mito-KATP) or permeability transition pore (PTP), but not by inhibition of xanthine oxidase. These results suggest that the arrhythmogenic adverse effects of CGs involve alterations in RyR2 function caused by oxidative changes in the channel structure by ROS. These CG-dependent effects probably involve release of ROS from mitochondria possibly mediated by NADPH oxidase. PMID:21807619

Ho, Hsiang-Ting; Stevens, Sarah C W; Terentyeva, Radmila; Carnes, Cynthia A; Terentyev, Dmitry; Gyorke, Sandor



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

PubMed Central

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. Comparable reductions in in vitro [3H]ouabain binding were also demonstrated. Reperfusion for 45 min after occlusion for 6 h resulted in no significant restoration of enzyme activity when compared to the nonreperfused animals. In six animals occluded for 2 h, a time at which myocardial creatine phosphokinase activity remains unchanged, (Na+ + K+)-ATPase activity was reduced by 25% compared with nonischemic enzyme activity. In five dogs occluded for 1 h, (Na+ + K+)-ATPase activity in ischemic myocardium was unchanged from control levels. We conclude that reduced regional myocardial blood flow, local alterations in cellular milieu, and altered glycoside-binding properties of (Na+ + K+)-ATPase all participate in the reduction of cardiac glycoside binding observed after reperfusion of ischemic myocardium. In addition, after 2 or more hours of severe ischemia, myocardial (Na+ + K+)-ATPase catalytic activity is significantly reduced despite incubation in the presence of optimal substrate concentrations. Images PMID:130383

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



Suppression of mouse lymphocytic mouse leukemia L1210 cells growth by cardiac glycosides  

SciTech Connect

The molecular mechanism of cytotoxic effect of cardiac glycosides is poorly understood, although their beneficial effects on certain types of tumor are well appreciated. Ouabain was tested against well characterized lymphocytic mouse leukemia L1210 cells in vitro. Logarithmically growing L1210 cells were harvested by centrifugation and incubated in a medium of RPMI 1640, 11% fetal bovine serum (pH 7.0) at 37/sup 0/C. In certain incubation bottles various doses of ouabain (10/sup -5/ M, 5 x 10/sup -5/ M and 10/sup -4/ M) were added to compare with control cell growth by counting cell number in a Coulter counter. Ouabain inhibited L1210 cell growth in drug dose dependently. The IC/sub 50/ is found to be 1 x 10/sup -5/ M. Incubation of L1210 cells with /sup 3/H-ouabain indicates that ouabain binds to the cells and diffuses into the cells, which caused cell deformation and subsequent cell death, as shown by scanning electron micrographic pictures. Ouabain also inhibited the uptake of /sup 3/H-thymidine, which will interfere with the synthesis of cell DNA. This study suggests that ouabain produces cellular cytotoxic effect by preventing the transport of thymidine or other essential ingredients for the survival of the L1210 cells.

Rhee, H.



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

PubMed Central

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

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



Identification of cardiac glycoside molecules as inhibitors of c-Myc IRES-mediated translation.  


Translation initiation is a fine-tuned process that plays a critical role in tumorigenesis. The use of small molecules that modulate mRNA translation provides tool compounds to explore the mechanism of translational initiation and to further validate protein synthesis as a potential pharmaceutical target for cancer therapeutics. This report describes the development and use of a click beetle, dual luciferase cell-based assay multiplexed with a measure of compound toxicity using resazurin to evaluate the differential effect of natural products on cap-dependent or internal ribosome entry site (IRES)-mediated translation initiation and cell viability. This screen identified a series of cardiac glycosides as inhibitors of IRES-mediated translation using, in particular, the oncogene mRNA c-Myc IRES. Treatment of c-Myc-dependent cancer cells with these compounds showed a decrease in c-Myc protein associated with a significant modulation of cell viability. These findings suggest that inhibition of IRES-mediated translation initiation may be a strategy to inhibit c-Myc-driven tumorigenesis. PMID:23150017

Didiot, Marie-Cecile; Hewett, Jeffrey; Varin, Thibault; Freuler, Felix; Selinger, Douglas; Nick, Hanspeter; Reinhardt, Juergen; Buckler, Alan; Myer, Vic; Schuffenhauer, Ansgar; Guy, Chantale T; Parker, Christian N



Systemic anticancer neural stem cells in combination with a cardiac glycoside for glioblastoma therapy.  


The tumor-tropic properties of neural stem cells (NSCs) have been shown to serve as a novel strategy to deliver therapeutic genes to tumors. Recently, we have reported that the cardiac glycoside lanatoside C (Lan C) sensitizes glioma cells to the anticancer agent tumor necrosis factor-related apoptosis-inducing ligand (TRAIL). Here, we engineered an FDA-approved human NSC line to synthesize and secrete TRAIL and the Gaussia luciferase (Gluc) blood reporter. We showed that upon systemic injection, these cells selectively migrate toward tumors in the mice brain across the blood-brain barrier, target invasive glioma stem-like cells, and induce tumor regression when combined with Lan C. Gluc blood assay revealed that 30% of NSCs survived 1 day postsystemic injection and around 0.5% of these cells remained viable after 5 weeks in glioma-bearing mice. This study demonstrates the potential of systemic injection of NSCs to deliver anticancer agents, such as TRAIL, which yields glioma regression when combined with Lan C. PMID:24801379

Teng, Jian; Hejazi, Seyedali; Badr, Christian E; Tannous, Bakhos A



Influence of derivation on the lipophilicity and inhibitory actions of cardiac glycosides on myocardial Na+-K+-ATPase.  

PubMed Central

Lipophilicity and inhibitory actions on guinea-pig heart Na+-K+-ATPase of twenty-six digitalis and six strophanthus glycosides comprising the aglycones, mono-, bis-, tris-sugar, alkylated (acylated) tris-sugar, acyl steroid derivatives and three cardanolides were investigated. Their octanol/water partition coefficients (P), reversed phase thin layer (r.t.l.c.) and reversed phase high performance liquid chromatography (r.h.p.l.c.) were determined and the viability of these methods as a measure of the lipophilicity of the cardiotonic steroids evaluated. The influence of lipophilicity and so also structural changes on the inhibitory effects of the cardiac glycosides on myocardial Na+-K+-ATPase was then examined. It is concluded that (a) r.t.l.c. and r.h.p.l.c. are just as effective as the conventional shake-flask method for estimation of the lipophilicity of cardiac glycosides and (b) the inhibitory potencies of cardiotonic steroids on the myocardial Na+-K+-ATPase increase with growing lipophilicity. The relationship between these two parameters is, however, governed by the influence of substitution or derivation of structural components on their inhibitory potencies on the myocardial Na+-K+-ATPase. PMID:3036289

Dzimiri, N.; Fricke, U.; Klaus, W.



Effect of cardiac glycosides from Nerium indicum on feeding rate, digestive enzymes activity and ultrastructural alterations of hepatopancreas in Pomacea canaliculata.  


Cardiac glycosides from Nerium indicum showed potent molluscicide activity against Pomacea canaliculata (GAS), but the toxicological mechanism is still far less understood. Effects of sublethal treatments of cardiac glycosides on feeding rate, digestive enzymes and ultrastructural alterations of the hepatopancreas in GAS were evaluated in this study. Exposure of GAS to sublethal concentrations of cardiac glycosides resulted in a significant reduction of feeding rate of GAS. The amylase, cellulose and protease activity were increase significantly at the end of 24 h followed by significant inhibition after 48 h of exposure while lipase activity was not affected significantly at the end of 24 h followed by a significant inhibition after 48 h of exposure during experimental period. The main ultrastructural alterations of hepatopancreas observed in snails under cardiac glycosides treatment comprised disruption of nuclear membrane, increased vesiculation and dilatation of endoplasmic reticulum, and vacuolization and swelling of mitochondrial compared to the untreated GAS. These results, for the first time, provide systematic evidences showing that cardiac glycosides seriously impairs the hepatopancreas tissues of GAS, resulting in inhibition of digestive enzymes activity and feeding rate and cause GAS death in the end. PMID:24361644

Dai, Lingpeng; Qian, Xiaowei; Nan, Xuyang; Zhang, Yejian



The cardiac glycoside binding site on the Na,K-ATPase alpha2 isoform plays a role in the dynamic regulation of active transport in skeletal muscle  

Microsoft Academic Search

The physiological significance of the cardiac glycoside-binding site on the Na,K-ATPase remains incompletely understood. This study used a gene-targeted mouse (alpha2R\\/R) which expresses a ouabain-insensitive alpha2 isoform of the Na,K-ATPase to investigate whether the cardiac glycoside-binding site plays any physiological role in active Na+\\/K+ transport in skeletal muscles or in exercise performance. Skeletal muscles express the Na,K-ATPase alpha2 isoform at

T. L. Radzyukevich; J. B. Lingrel; J. A. Heiny



Sugar moiety of cardiac glycosides is essential for the inhibitory action on the palytoxin-induced K+ release from red blood cells.  


Palytoxin (PTX), a highly toxic and sugar-containing substance isolated from Palythoa tuberculosa, caused K+ release from rabbit red blood cells. Cardiac glycosides, such as ouabain, convallatoxin, cymarin, digoxin and digitoxin, inhibited the PTX-induced K+ release. Their corresponding aglycones did not inhibit the K+ release, but antagonized the inhibitory effect of the glycosides. All these cardiotonic steroids equally inhibited the activity of (Na+ + K+)-ATPase prepared from hog cerebral cortex. These results suggest that the sugar moiety of the cardiac glycosides is important for the inhibitory effect on the K+ release induced by PTX and that the inhibition is not related to their inhibitory potency on the (Na+ + K+)-ATPase activity. PMID:6146536

Ozaki, H; Nagase, H; Urakawa, N



In vitro and in vivo neuroprotective activity of the cardiac glycoside oleandrin from Nerium oleander in brain slice-based stroke models.  


The principal active constituent of the botanical drug candidate PBI-05204, a supercritical CO(2) extract of Nerium oleander, is the cardiac glycoside oleandrin. PBI-05204 shows potent anticancer activity and is currently in phase I clinical trial as a treatment for patients with solid tumors. We have previously shown that neriifolin, which is structurally related to oleandrin, provides robust neuroprotection in brain slice and whole animal models of ischemic injury. However, neriifolin itself is not a suitable drug development candidate and the FDA-approved cardiac glycoside digoxin does not cross the blood-brain barrier. We report here that both oleandrin as well as the full PBI-05204 extract can also provide significant neuroprotection to neural tissues damaged by oxygen and glucose deprivation as occurs in ischemic stroke. Critically, we show that the neuroprotective activity of PBI-05204 is maintained for several hours of delay of administration after oxygen and glucose deprivation treatment. We provide evidence that the neuroprotective activity of PBI-05204 is mediated through oleandrin and/or other cardiac glycoside constituents, but that additional, non-cardiac glycoside components of PBI-05204 may also contribute to the observed neuroprotective activity. Finally, we show directly that both oleandrin and the protective activity of PBI-05204 are blood brain barrier penetrant in a novel model for in vivo neuroprotection. Together, these findings suggest clinical potential for PBI-05204 in the treatment of ischemic stroke and prevention of associated neuronal death. PMID:21950737

Dunn, Denise E; He, Dong Ning; Yang, Peiying; Johansen, Mary; Newman, Robert A; Lo, Donald C



Ouabain, a Cardiac Glycoside, Inhibits the Fanconi Anemia/BRCA Pathway Activated by DNA Interstrand Cross-Linking Agents  

PubMed Central

Modulation of the DNA repair pathway is an emerging target for the development of anticancer drugs. DNA interstrand cross-links (ICLs), one of the most severe forms of DNA damage caused by anticancer drugs such as cisplatin and mitomycin C (MMC), activates the Fanconi anemia (FA)/BRCA DNA repair pathway. Inhibition of the FA/BRCA pathway can enhance the cytotoxic effects of ICL-inducing anticancer drugs and can reduce anticancer drug resistance. To find FA/BRCA pathway inhibitory small molecules, we established a cell-based high-content screening method for quantitating the activation of the FA/BRCA pathway by measuring FANCD2 foci on DNA lesions and then applied our method to chemical screening. Using commercial LOPAC1280 chemical library screening, ouabain was identified as a competent FA/BRCA pathway inhibitory compound. Ouabain, a member of the cardiac glycoside family, binds to and inhibits Na+/K+-ATPase and has been used to treat heart disease for many years. We observed that ouabain, as well as other cardiac glycoside family members?digitoxin and digoxin?down-regulated FANCD2 and FANCI mRNA levels, reduced monoubiquitination of FANCD2, inhibited FANCD2 foci formation on DNA lesions, and abrogated cell cycle arrest induced by MMC treatment. These inhibitory activities of ouabain required p38 MAPK and were independent of cellular Ca2+ ion increase or the drug uptake-inhibition effect of ouabain. Furthermore, we found that ouabain potentiated the cytotoxic effects of MMC in tumor cells. Taken together, we identified an additional effect of ouabain as a FA/BRCA pathway-inhibiting chemosensitization compound. The results of this study suggest that ouabain may serve as a chemosensitizer to ICL-inducing anticancer drugs. PMID:24124520

Kim, Hyun Jung; Hwang, Soo Kyung; Kim, Sunshin; Lee, Chang-Hun



Cardiac glycoside ouabain induces autophagic cell death in non-small cell lung cancer cells via a JNK-dependent decrease of Bcl-2.  


Cardiac glycosides are Na/K-ATPase inhibitors, clinically used for congestive heart failure and cardiac arrhythmias. Epidemiological studies have reported that patients on cardiac glycosides treatment are protected from some types of cancers. This evidence together with the demonstration that cardiac glycosides show selective cytotoxicity against cancer cells has raised new interest on the anticancer properties of these drugs. This study examines the mechanism involved in the anticancer effect of ouabain in non-small cell lung cancer cells lines (A549 and H1975). Ouabain inhibited cell proliferation and induced cell death in a concentration-dependent manner. Cell death was caspase-independent and showed classical patterns of autophagic cell death: conversion of LC3-I to LC3-II, increase of LC3 puncta and increase of autophagic flux. Moreover, cell death was completely blocked by the class III phosphatidylinositol-3 kinase inhibitor 3-methyladenine. Here we show that ouabain caused the reduction of Bcl-2 protein levels, with no change in the expression of the autophagic protein Beclin 1. Early signalling events of ouabain exposure were ERK1/2 and JNK activation, however only JNK inhibition with SP600125 or JNK knockdown by shRNA were able to prevent Bcl-2 decrease, conversion of LC3-I to LC3-II and cell death. We propose that JNK activation by ouabain leads to a decrease of Bcl-2 levels, resulting in disruption of the inhibitory interaction of Bcl-2 with Beclin 1, that promotes autophagy. These findings indicate that pharmacological modulation of autophagy by cardiac glycosides could be exploited for anticancer therapy. PMID:24630927

Trenti, Annalisa; Grumati, Paolo; Cusinato, Federico; Orso, Genny; Bonaldo, Paolo; Trevisi, Lucia



Effects of Cardiac Glycosides on Electrical Activity in the Isolated Retina of the Frog  

PubMed Central

Ouabain added to physiological salt solutions bathing the isolated frog retina irreversibly abolishes the electrical response to light (the electroretinogram or ERG). The time course of abolition depends on the concentration of ouabain in the medium and the surface of the retina to which it is applied. When the glycoside is placed on the receptor surface, in 7 min the ERG is completely eliminated by 10-4 M ouabain and more than 90% inhibited by 3 x 10-5 M ouabain. The effect is slower at lower concentrations and when the solution is applied to the vitreous surface of the retina. The evidence suggests that abolition of the ERG by ouabain is due principally to inhibition of the active transport of sodium: (a) Structurally modified glycosides which are considerably less potent inhibitors of alkali cation-activated ATPase activity in preparations of frog retinal outer segments are also poorer inhibitors of electrical activity in isolated retinas. (b) Replacing much of the sodium in the medium bathing the retina by choline, Tris, or sucrose significantly protects the retina from ouabain. It is suggested that in a standard sodium environment essentially constant activity of the sodium pump is required to prevent rapid and irreversible change. The cellular sites most critically dependent on the sodium pump have not been identified. PMID:6034759

Frank, Robert N.; Goldsmith, Timothy H.



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

NASA Astrophysics Data System (ADS)

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.

K?en, Vladimír


Palytoxin induces a relatively non-selective cation permeability in frog sciatic nerve which can be inhibited by cardiac glycosides.  


The effect of palytoxin (PTX) on compound resting potential and compound action potential of frog sciatic nerve was studied using the sucrose-gap technique. PTX irreversibly depolarized the compound resting potential and reduced the amplitude of the compound action potential. PTX evoked a marked depolarization when extracellular Na+ was replaced by Li+, Cs+ and the organic cations methylammonium, hydroxylammonium, and methylhydroxylammonium but not by tetramethylammonium, tetraethylammonium, choline or the divalent cations, Ca2+ and Ba2+. The maintained depolarization was not sensitive to inhibition by saxitoxin (300 nM) or procaine (10 mM). The depolarization was inhibited by ouabain or cymarin but not by the aglycon, strophanthidin. However, strophanthidin did antagonize the inhibitory action of cymarin which suggests that PTX and cardiac glycosides do not share an identical binding site but there may be some overlap. We conclude that in frog sciatic nerve, PTX interacts with the (Na+-K+) pump to induce the opening or formation of a relatively non-selective cation pore within or near the pump protein. PMID:2904712

Castle, N A; Strichartz, G R



Joun~al r~fChemical Ecology. Vol. 21. No. 9, 1995 PRESERVING LEAVES FOR TANNIN AND PHENOLIC  

E-print Network

). Salix sericea Marshall and Salix eriocephala Michx. produce different sec- ondary chemicals. S. sericea) and very low concen- trations of condensed tannins. S. eriocephala produces high concentrations. eriocephala hybrids produce both tannins and phenolic glycosides at intermediate concentrations (Orians

Orians, Colin


Comprehensive transcriptome analysis reveals novel genes involved in cardiac glycoside biosynthesis and mlncRNAs associated with secondary metabolism and stress response in Digitalis purpurea  

PubMed Central

Abstract Background Digitalis purpurea is an important ornamental and medicinal plant. There is considerable interest in exploring its transcriptome. Results Through high-throughput 454 sequencing and subsequent assembly, we obtained 23532 genes, of which 15626 encode conserved proteins. We determined 140 unigenes to be candidates involved in cardiac glycoside biosynthesis. It could be grouped into 30 families, of which 29 were identified for the first time in D. purpurea. We identified 2660 mRNA-like npcRNA (mlncRNA) candidates, an emerging class of regulators, using a computational mlncRNA identification pipeline and 13 microRNA-producing unigenes based on sequence conservation and hairpin structure-forming capability. Twenty five protein-coding unigenes were predicted to be targets of these microRNAs. Among the mlncRNA candidates, only 320 could be grouped into 140 families with at least two members in a family. The majority of D. purpurea mlncRNAs were species-specific and many of them showed tissue-specific expression and responded to cold and dehydration stresses. We identified 417 protein-coding genes with regions significantly homologous or complementary to 375 mlncRNAs. It includes five genes involved in secondary metabolism. A positive correlation was found in gene expression between protein-coding genes and the homologous mlncRNAs in response to cold and dehydration stresses, while the correlation was negative when protein-coding genes and mlncRNAs were complementary to each other. Conclusions Through comprehensive transcriptome analysis, we not only identified 29 novel gene families potentially involved in the biosynthesis of cardiac glycosides but also characterized a large number of mlncRNAs. Our results suggest the importance of mlncRNAs in secondary metabolism and stress response in D. purpurea. PMID:22233149



Involvement of the sugar moiety in the inhibitory action of the cardiac glycosides on the palytoxin-induced responses in vascular smooth muscles.  


The effects of ouabain and other cardiotonic steroids were examined to investigate whether changes in Na,K-adenosine triphosphatase (ATPase) activity modified the actions of palytoxin (PTX) in rabbit aortic vascular smooth muscle. The effects of these agents on rabbit aorta were compared with those on rat aorta, as it is known that the concentration of cardiac glycosides required to inhibit Na,K-ATPase of rat aorta is markedly higher than that of other species. PTX induced contraction in rabbit and rat aortas in a similar concentration range (10(-11) to 10(-8) M). PTX rapidly decreased tissue K content of these preparations. Ouabain (2 X 10(-5) M) inhibited both the contraction and the loss of tissue K in rabbit aorta but not in rat aorta. In rabbit aorta, convallatoxin (2 X 10(-5) M), which has one rhamnose as a sugar moiety like ouabain, and cymarin (2 X 10(-5) M), which has one cymarose, inhibited the PTX-induced contraction and the loss of tissue K, although ouabagenin, convallatoxigenin and cymarigenin (strophanthidin) (2 X 10(-5) M) did not. Other cardiotonic steroids, digoxin and digitoxin, which have 3 U of digitoxose as a sugar component, or the corresponding aglycones failed to inhibit the PTX-responses. On the other hand, all the cardiotonic steroids at concentration of 2 X 10(-5) M equally inhibited the reuptake of K and relaxation of norepinephrine-induced contractions induced by the readdition of K. Inhibition of Na-K pump by K-free solution potentiated rather than inhibited the PTX-induced contraction. These results suggest that the specific sugar moiety of cardiac glycosides is important for the inhibitory effect exerted by these compounds on the PTX-induced responses and that the inhibition is not related to the activity of the Na,K-ATPase. PMID:6149301

Ozaki, H; Nagase, H; Urakawa, N



Influence of the cardiac glycoside digoxin on cardiac troponin I, acid-base and electrolyte balance, and haematobiochemical profiles in healthy donkeys (Equus asinus)  

PubMed Central

Background The effect of digoxin administration on the serum concentration of the cardiac troponin I (cTnI) has not been reported to date in equidae. This study was therefore designed to evaluate the effect of digoxin on cardiac cell damage in donkeys (Equus asinus) as assessed by cTnI, acid–base and electrolyte balance and haematobiochemical profiles. Ten clinically healthy donkeys were given an IV infusion of digoxin at a dose of 14 ?g/kg. Blood samples were collected from the donkeys up through 72 h post-injection. Results Three of the donkeys exhibited increased heart and respiratory rates post-injection. In the other seven animals, the heart and respiratory rates were lower 4 h post-injection. The serum digoxin concentration increased significantly at many time points after injection. The serum concentration of cTnI did not differ significantly between pre- and post-injection. An increase in blood pH was noted at 3 h after digoxin injection. There were also increases in PO2 and in oxygen saturation. Decreases in PCO2 at 2 to 48 h post-injection as well as a decrease in blood lactate at 4 h post-injection were observed. The serum concentration of glucose remained significantly elevated at all-time points after digoxin injection. Conclusions It is concluded that administration of digoxin to healthy donkeys (14 ?g/kg) did not result in elevations of serum cTnI concentration, signs of digoxin intoxication, ECG abnormalities and did not increase serum concentrations of blood urea nitrogen and creatinine. PMID:24621180



Human Breast Tumor Cells Are More Resistant to Cardiac Glycoside Toxicity Than Non-Tumorigenic Breast Cells  

PubMed Central

Cardiotonic steroids (CTS), specific inhibitors of Na,K-ATPase activity, have been widely used for treating cardiac insufficiency. Recent studies suggest that low levels of endogenous CTS do not inhibit Na,K-ATPase activity but play a role in regulating blood pressure, inducing cellular kinase activity, and promoting cell viability. Higher CTS concentrations inhibit Na,K-ATPase activity and can induce reactive oxygen species, growth arrest, and cell death. CTS are being considered as potential novel therapies in cancer treatment, as they have been shown to limit tumor cell growth. However, there is a lack of information on the relative toxicity of tumor cells and comparable non-tumor cells. We have investigated the effects of CTS compounds, ouabain, digitoxin, and bufalin, on cell growth and survival in cell lines exhibiting the full spectrum of non-cancerous to malignant phenotypes. We show that CTS inhibit membrane Na,K-ATPase activity equally well in all cell lines tested regardless of metastatic potential. In contrast, the cellular responses to the drugs are different in non-tumor and tumor cells. Ouabain causes greater inhibition of proliferation and more extensive apoptosis in non-tumor breast cells compared to malignant or oncogene-transfected cells. In tumor cells, the effects of ouabain are accompanied by activation of anti-apoptotic ERK1/2. However, ERK1/2 or Src inhibition does not sensitize tumor cells to CTS cytotoxicity, suggesting that other mechanisms provide protection to the tumor cells. Reduced CTS-sensitivity in breast tumor cells compared to non-tumor cells indicates that CTS are not good candidates as cancer therapies. PMID:24349570

Clifford, Rebecca J.; Kaplan, Jack H.



Tannin-chitosan composites  

US Patent & Trademark Office Database

The invention provides a composition comprising a matrix of chitosan and a tannin wherein the chitosan is electrostatically bonded to the tannin to form a chitosan-tannin composite material. The chitosan can be partially or fully deacetylated, and the tannin can be a monomeric or an oligomeric proanthocyanidin or a hydrolysable tannin. The chitosan-tannin composite material can be a nanoparticle, a hydrogel film, a bio-foam, or a biogel, or the chitosan-tannin composite material can coat a liposome. The composite materials can be used for drug delivery, for antibacterial and/or antifungal applications, for tissue engineering applications, for wound healing applications, or they can be used as adjuvants for vaccination, including oral vaccinations. The invention also provides methods of preparing the composite materials and their various forms.



Interactions of cardiac glycosides with cultured cardiac cells. II. Biochemical and electron microscopic studies on the effects of ouabain on muscle and non-muscle cells.  


Electron microscopic and biochemical studies revealed a salient difference in the response to toxic doses of ouabain by cultured cardiac muscle and non-muscle cells from neonatal rats. Progressive cellular injury in myocytes incubated with 1 . 10(-4)--1 . 10(-3) M ouabain ultimately leads to swelling and necrosis. The morphological damage in myocytes was accompanied by a drastic decrease in 14CO2 formation from 14C-labeled stearate or acetate but not glucose. Neither morphological nor biochemical impairments were observed in non-muscle cells. The interaction between ouabain and the cultured cells, using therapeutic doses of ouabain (i.e., less than 1 . 10(-7) M), was characterized. Two binding sites were described in both classes of cells, one site is a saturable K+-sensitive site whereas the other is non-saturable and K+-insensitive. The complexes formed between the sarcolemma receptor(s) and ouabain, at low concentrations of the drug (e.g., 7.52 . 10(-9) M), had Kd values of 8.9 . 10(-8) and 2.3 . 10(-8) M for muscle and non-muscle cells, respectively. The formation and dissociation of the complexes were affected by temperature and potassium ions. PMID:7378406

Friedman, I; Schwab, H; Hallaq, H; Pinson, A; Heller, M



Human cell mutants affected in the interaction of the 12 beta-OH group of cardiac glycosides with the digitalis receptor.  


The cross-resistance patterns of two different types of mutants of HeLa cells selected for resistance to the digoxin analog SC4453 (SCR mutants) in which the Na+/K+-ATPase is affected [A. Chopra and R. S. Gupta, J. biol. Chem. 261, 2034 (1986)], and towards numerous cardiac glycosides (CGs) and genins, were examined. One type of SCR mutant (designated as group C) was highly resistant to all CGs and genins investigated. In contrast, the other type of SCR mutant (group D) showed a high degree of cross-resistance towards selected CG derivatives (viz. digoxin, SC4453, digoxigenin, lanatoside C, alpha- and beta-methyldigoxin, dihydrodigoxin, alpha- and beta-acetyldigoxin, alpha,beta-diacetyldigoxin), all of which contained a free 12 beta-OH group in the steroid structure. Slight cross-resistance of the group D mutants was also observed for other compounds (viz. ouabain, ouabagenin, dihydroouabain) that contain a free 11 alpha-OH group in the molecule. However, these mutants exhibited no cross-resistance to other CG derivatives, which either lacked the above groups (viz. digitoxin, digitoxigenin, dihydrodigitoxin, digitoxigenin mono- and bisdigitoside, nerifolin, gitoxigenin, gitoxin, 16-acetylgitoxin, lanatosides A and B, cymarin, convallatoxin, oleandrin, strophanthidin, actodigin and bufalin) or in which the 12 beta-OH group was acetylated (viz. as in the case of 12-acetyldigoxin). Since the 12 beta-OH group is not required for CG-like activity, to account for these observations it is suggested that the genetic lesion in the group D mutant leads to the creation of a new binding site in the digitalis receptor, which specifically interacts with the 12 beta-OH group (the site presumably also interacts weakly with the 11 alpha-OH group) and either prevents or distorts the binding of the compounds to the drug binding site on the receptor. Further investigations with the different classes of CG-resistant mutants at the molecular level should prove very useful in identifying the drug receptor site and in understanding how these drugs interact with it. PMID:2825704

Gupta, R S; Chopra, A



Studies on cardioactive steroids. III. Characterization of different cardiac glycosides by their effects on contractility and rhythmicity at different extracellular potassium concentrations.  


In the present paper, the naturally occurring glycosides digitoxin, gitoxin, 16-acetyl-gitoxin, digoxin, cymarol, ouabain, and proscillaridin, and the semi-synthetic 16-epi-gitoxin and 16-acetyl-16-epi-gitoxin are investigated as to their inotropic action and their effects on rhythmicity at isolated spontaneously beating atria of the guinea-pig heart in dependence on the variation of the potassium concentration of the nutritive fluid ([K+]0: 1.34, 2.68, and 5.36 mM resp.). The major results are as follows. 1. Effects of raising [K+]0 from 1.34 to 2.68 mM: The range of the inotropically effective concentrations as well as the size of the maximum inotropic action are more or less strongly improved with all glycosides. The glycoside concentrations required to get inotropic maximum had to be increased to a high degree with proscillaridin and digoxin. The mean arrhythmia percentage occurring at the inotropic maximum is either decreased (gitoxin, 16-epi-gitoxin, digoxin, proscillaridin), unchanged (digitoxin, 16-acetyl-16-epi-gitoxin) or even increased (16-acetyl-gitoxin, cymarol, ouabain). The inotropic value is improved to a high extent with gitoxin only. 2. Effect of raising [K+]0 from 2.68 to 5.36 mM: The range of the inotropically effective concentrations is extended (digitoxin and cymarol) or diminished (proscillaridin), but remains essentially unchanged with most glycosides. The size of the maximum inotropic effect is increased with digoxin, ouabain and 16-epi-gitoxin, but decreased significantly with digitoxin and proscillaridin. The glycoside concentrations required to produce the inotropic maximum are essentially unchanged with the exception of 16-epi-gitoxin, 16-acetyl-gitoxin and ouabain. The mean arrhythmia percentage at the maximum inotropic effect is dramatically reduced with digoxin, cymarol and proscillaridin. The inotropic value is improved with all glycosides except digitoxin. 3. Evaluation of the various glycosides: When judged on the basis of the range of inotropically effective concentrations, the maximum inotropic effect, the mean arrhythmia percentage at the inotropic maximum and the inotropic value, the best first three glycosides include 16-epi-gitoxin and digoxin. 16-Epi-gitoxin and its 16-acetate show that most favourable relationship between the effect on contractility and rhythmicity. The cause of the differential actions of the structurally-different glycosides on contractility and rhythmicity is hypothesized to be due to divergences in structure and/or conformation of the receptor areas of (Na+ + K+)-ATPase of contractile and excitable cells. PMID:1199622

Haustein, K O; Graumann, G; Stephan, B



Cardiac glycoside induces cell death via FasL by activating calcineurin and NF-AT, but apoptosis initially proceeds through activation of caspases  

PubMed Central

Decrease in caspase activity is a common phenomenon in drug resistance. For effective therapeutic intervention, detection of such agents, which affects other pathway independent of caspases to promote cell death, might be important. Oleandrin, a polyphenolic glycoside induced cell death through activation of caspases in a variety of human tumour cells. In this report we provide evidence that besides caspases activation, oleandrin interacts with plasma membrane, changes fluidity of the membrane, disrupts Na+/K+-ATPase pump, enhances intracellular free Ca2+ and thereby activates calcineurin. Calcineurin, in turns, activates nuclear transcription factor NF-AT and its dependent genes such as FasL, which induces cell death as a late response of oleandrin. Cell death at early stages is mediated by caspases where inhibitors partially protected oleandrin-mediated cell death in vector-transfected cells, but almost completely in Bcl-xL-overexpressed cells. Overall, our data suggest that oleandrin might be important therapeutic molecule in case of tumors where cell death pathway occurs due to deregulation of caspase-mediated pathway PMID:17203245

Raghavendra, Pongali B.; Sreenivasan, Yashin; Ramesh, Govindarajan T.



Tannins as Gibberellin Antagonists 1  

PubMed Central

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

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



Iridoidal glycosides from Jasminum sambac  

Microsoft Academic Search

Besides a known trimeric iridoidal glycoside, sambacoside A, five new oligomeric iridoidal glycosides, molihuasides A-E were isolated from the flowers of Jasminum sambac. Their structures were determined by spectral and chemical evidence. Among them, molihuasides A and C-E are new dimeric iridoidal glycosides and molihuaside B is a new trimeric iridoidal glycoside.

Ying-Jun Zhang; Yu-Qing Liu; Xiang-Yu Pu; Chong-Ren Yang



Nutritional Toxicology of Tannins and Related Polyphenols in Forage Legumes  

Microsoft Academic Search

Proanthocyanidins (PA) (condensed tannins) and hydrolyzable tannins (HT) are the two major classes of tannins. Proanthocyanidins are flavo- noid polymers. Hydrolyzable tannins are polymers of gallic or ellagic acid esterified to a core molecule, commonly glucose or a polyphenol such as catechin. Proanthocyanidins are the most common type of tannin found in forage legumes. Problems in the analysis of tannins

Jess D. Reed



Implications of soluble tannin-protein complexes for tannin analysis and plant defense mechanisms  

Microsoft Academic Search

Factors which establish whether tannin and protein interact to form soluble complexes or precipitates were identified. The ratio of tannin to protein in the reaction mixture influenced solubility of the tannin-protein complexes. At protein-to-tannin ratios larger than the optimum ratio, or equivalence point, soluble tannin-protein complexes apparently formed instead of insoluble complexes. Several other factors influenced the amount of protein

Ann E. Hagerman; Charles T. Robbins



Effect of tannins on galliform cecal partitioning.  


Winter diets of ruffed grouse (Bonasa umbellus) and other galliformes are high in tannins. We fed quebracho, a condensed tannin, to ruffed grouse and found no effect on dry matter intake or body mass at levels up to 6% of the diet. However, a high-fiber diet with 8% quebracho resulted in reduced dry matter intake and body mass loss. Grouse could not tolerate a diet with 8% tannic acid, a hydrolyzable tannin, which caused a large reduction in dry matter intake and body mass. Northern bobwhite (Colinus virginianus) and ruffed grouse responded to dietary quebracho tannin by increasing the proportion of digesta that was excreted from the ceca. In the northern bobwhite, 59%-76% of the tannin recovered from the feces was in cecal feces. There was no difference in average passage rates of liquid and fiber digesta, although variation was high in tannin-fed birds. The role of the ceca in handling tannin requires further investigation. PMID:9231390

Hewitt, D G; Lafon, N W; Kirkpatrick, R L



Phenylethanoid and lignan glycosides from Verbascum thapsus.  


Verbascum thapsus afforded, in addition to three known phenylethanoid glycosides and four lignan ones, five new phenylethanoid glycosides and one new lignan glycoside. Structures of the compounds were elucidated by spectroscopic methods and chemical evidence. PMID:1373629

Warashina, T; Miyase, T; Ueno, A



Ecological implications of condensed tannin structure: A case study  

Microsoft Academic Search

Condensed tannins were isolated from bitterbnish (Purshia tridentata) and blackbrush (Coleogyne ramosissima). Structural analyses showed that both tannins were procyanidins of similar polymer length. The overall stereochemistries at C-3 and C-4, however, differed between the two tannins. These changes in stereochemistry resulted in blackbrush tannins being less preferred than bitterbrush tannins when offered to snowshoe hares (Lepus americanus). It is

T. P. Clausen; F. D. Provenza; E. A. Burritt; P. B. Reichardt; J. P. Bryant



Iridoid glycosides and glycosidic constituents from Eriophyton wallichii Benth.  


C?-iridoid glycosides, wallichiisides A-C, and four dimers, wallichiisides D-G, together with 13 known glycosidic compounds, were isolated from whole plants of Eriophyton wallichii Benth. Their structures were elucidated by spectroscopic methods and comparison with literature values. Four of these compounds showed moderate DPPH free radical scavenging activity. PMID:21601897

Fan, Qiu-Ling; Tan, Chang-Heng; Liu, Jing; Zhao, Ming-Ming; Han, Fu-Sen; Zhu, Da-Yuan



Tannins, Peptic Ulcers and Related Mechanisms  

PubMed Central

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

de Jesus, Neyres Zinia Taveira; de Souza Falcao, 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, Petronio Filgueiras; Batista, Leonia Maria



Phenylethanoid glycosides from Lippia javanica  

Microsoft Academic Search

Lippia javanica (N.L.Burm.) Spreng. is an aromatic, multipurpose medicinal plant from which a number of volatile compounds have been identified, together with toxic triterpenoids and iridoid glycosides. Two additional phenylethanoid glycosides, verbascoside and isoverbascoside, were isolated from L. javanica and characterized. High performance liquid chromatography analyses of polar extracts of three other Lippia species (L. scaberrima, L. rehmannii and L.

D. K. Olivier; E. A. Shikanga; S. Combrinck; R. W. M. Krause; T. Regnier; T. P. Dlamini



Triterpene glycosides from Saponaria officinalis  

Microsoft Academic Search

Conclusions  The roots ofSaponaria officinalis L. have yielded the known triterpene glycoside gypsoside and the first glycoside of gypsogenic acid, which has been named\\u000a saponaroside. Saponaroside is the 3-?-D-xylopyranoside of gypsogenic acid.

V. G. Bukharov; S. P. Shcherbak



Factors affecting skin tannin extractability in ripening grapes.  


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. PMID:24432763

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



Tannins and Human Health: A Review  

Microsoft Academic Search

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

King-Thom Chung; Tit Yee Wong; Cheng-I Wei; Yao-Wen Huang; Yuan Lin



Sulphited tannins for exterior wood adhesives  

Microsoft Academic Search

Summary Condensed tannins such as wattle (Mimosa) extract can be partially modified, through hydrolysis of a benzyl ether link and consequent opening of the flavonoid heterocyclic ring, through sulphitation. The introduction of a sulphonic group in the flavonoid structure and the heterocyclic ring opening produces tannin solutions of lower viscosity. While the sulphonic group introduced is deleterious to the strength

A. Pizzi



Acylated flavone glycosides from Veronica  

Microsoft Academic Search

A survey of the flavonoid glycosides of selected taxa in the genus Veronica yielded two new acylated 5,6,7,3?,4?-pentahydroxyflavone (6-hydroxyluteolin) glycosides and two unusual allose-containing acylated 5,7,8,4?-tetrahydroxyflavone (isoscutellarein) glycosides. The new compounds were isolated from V. liwanensis and V. longifolia and identified using NMR spectroscopy as 6-hydroxyluteolin 4?-methyl ether 7-O-?-rhamnopyranosyl(1??2?)[6?-O-acetyl-?-glucopyranoside] and 6-hydroxyluteolin 7-O-(6?-O-(E)-caffeoyl)-?-glucopyranoside, respectively. Isoscutellarein 7-O-(6?-O-acetyl)-?-allopyranosyl(1??2?)-?-glucopyranoside was obtained from both V.

Dirk C. Albach; Renée J. Grayer; Søren Rosendal Jensen; Fevzi Özgökce; Nigel C. Veitch



Colloidal stability of tannins: astringency, wine tasting and beyond  

NASA Astrophysics Data System (ADS)

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 ?-casein. Tannin-assisted micellization and compaction of proteins observed by SAXS are described quantitatively and discussed in the case of astringency.

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



Naturally occurring methyl salicylate glycosides.  


As an important part of non steroids anti-inflammation drug (NSAIDs), salicylate has developed from natural substance salicylic acid to natrium salicylicum, to aspirin. Now, methyl salicylate glycoside, a new derivative of salicylic acid, is modified with a -COOH group integrated one methyl radical into formic ether, and a -OH linked with a monosaccharide, a disaccharide or a trisaccharide unit by glycosidic linkage. It has the similar pharmacological activities, anti-inflammatory, analgesic, antipyretic and antithrombotic as the previous salicylates' without resulting in serious side effects, particularly the gastrointestinal toxicity. Owing to the superiority of those significant bioactivities, methyl salicylate glycosides have became a hot research area in NSAIDs for several years. This paper compiles all 9 naturally occurring methyl salicylate glycosides, their distribution of the resource and pharmacological mechanism, which could contribute to the new drug discovery. PMID:24329991

Mao, Ping; Liu, Zizhen; Xie, Meng; Jiang, Rui; Liu, Weirui; Wang, Xiaohong; Meng, Shen; She, Gaimei



Acylated flavone glycosides from Veronica.  


A survey of the flavonoid glycosides of selected taxa in the genus Veronica yielded two new acylated 5,6,7,3',4'-pentahydroxyflavone (6-hydroxyluteolin) glycosides and two unusual allose-containing acylated 5,7,8,4'-tetrahydroxyflavone (isoscutellarein) glycosides. The new compounds were isolated from V. liwanensis and V. longifolia and identified using NMR spectroscopy as 6-hydroxyluteolin 4'-methyl ether 7-O-alpha-rhamnopyranosyl(1"'-->2")[6"-O-acetyl-beta-glucopyranoside] and 6-hydroxyluteolin 7-O-(6"-O-(E)-caffeoyl)-beta-glucopyranoside, respectively. Isoscutellarein 7-O-(6"'-O-acetyl)-beta-allopyranosyl(1"'-->2")-beta-glucopyranoside was obtained from both V. intercedens and V. orientalis and its 4'-methyl ether from V. orientalis only. Complete 1H and 13C NMR spectral assignments are presented for both isoscutellarein glycosides. Two iridoid glucosides new to the genus Veronica (melittoside and globularifolin) were also isolated from V. intercedens. PMID:14599528

Albach, Dirk C; Grayer, Renée J; Jensen, Søren Rosendal; Ozgökce, Fevzi; Veitch, Nigel C



On the differences between ouabain and digitalis glycosides.  


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. PMID:21642827

Fuerstenwerth, Hauke



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


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

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



Antioxidant activity of crude tannins of canola and rapeseed hulls  

Microsoft Academic Search

The antioxidant activity of crude tannins of canola and rapeseed hulls was evaluated by ?-carotene-linoleate, ?,?-diphenyl-?-picrylhydrazyl\\u000a (DPPH) radical, and reducing power assays. Crude tannins were extracted from three samples of Cyclone canola (high-tannin)\\u000a hulls and Kolner, Ligaret, and Leo Polish rapeseed (low-tannin) hulls with 70% (vol\\/vol) acetone. The total phenolic content\\u000a in crude tannin extracts ranged between 128 and 296

R. Amarowicz; M. Naczk; F. Shahidi



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


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

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



Condensed tannins act against cattle nematodes.  


The use of natural plant anthelmintics was suggested as a possible alternative control of gastrointestinal nematodes (GIN) in ruminants. Direct anthelmintic effects of tannin-containing plants have already been shown in sheep and goat GIN. These anthelmintic properties are mainly associated with condensed tannins. In the present study, we evaluated possible in vitro effects of three tannin-containing plants against bovine GIN. Effects of Onobrychis viciifolia, Lotus pedunculatus and Lotus corniculatus condensed tannin (CT) extracts on Cooperia oncophora and Ostertagia ostertagi were determined by a larval feeding inhibition assay (LFIA) and a larval exsheathment assay (LEA). In the LFIA, all three plant extracts significantly inhibited larval feeding behaviour of both C. oncophora and O. ostertagi first stage larvae in a dose-dependent manner. The L. pedunculatus extract, based on EC(50) (effective concentration for 50% inhibition), was the most effective against both nematodes, followed by O. viciifolia and L. corniculatus. The effect of CT extracts upon larval feeding behaviour correlates with CT content and procyanidin/prodelphidin ratio. Larval exsheathment of C. oncophora and O. ostertagi L3 larvae (third stage larvae) was also affected by CT extracts from all three plants. In both in vitro assays, extracts with added polyvinylpolypyrrolidone, an inhibitor of tannins, generated almost the same values as the negative control; this confirms the role of CT in the anthelmintic effect of these plant extracts. Our results, therefore, indicated that tannin-containing plants could act against cattle nematodes. PMID:21726942

Novobilský, Adam; Mueller-Harvey, Irene; Thamsborg, Stig Milan



Interaction of gut microflora with tannins in feeds  

NASA Astrophysics Data System (ADS)

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.

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



Sesquiterpene Glycosides from Calendula persica.  


The polar fractions of the extract of the aerial parts of CALENDULA PERSICA afforded eight sesquiterpene glycosides, five derived from viridiflorol, two of beta-eudesmol, and one of 4alpha-hydroxygermacra-1(10) E,5E-diene. In addition to fucopyranosides, also chinovopyranosides were present. The structures were elucidated by high field NMR techniques. PMID:17265265

Jakupovic, J; Grenz, M; Bohlmann, F; Rustaiyan, A; Koussari, S



Iridoid glycosides of Cornus canadensis  

Microsoft Academic Search

The iridoid glycosides scandoside, scandoside methyl ester, monotropein, and galioside were found in Cornus canadensis from several widely distributed collection sites. Cornin and hastatoside were isolated from C. nuttallii. No iridoids were found in C. stolonifera, that instead yielded cornoside and halleridone, also independent of collection location. The results were compared with previous studies and current phylogenetic work on the

Frank R Stermitz; Robert E Krull



Accumulation of uranium by immobilized persimmon tannin  

SciTech Connect

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.

Sakaguchi, Takashi; Nakajima, Akira (Miyazaki Medical College (Japan))



Ecological implications of condensed tannin structure: A case study.  


Condensed tannins were isolated from bitterbnish (Purshia tridentata) and blackbrush (Coleogyne ramosissima). Structural analyses showed that both tannins were procyanidins of similar polymer length. The overall stereochemistries at C-3 and C-4, however, differed between the two tannins. These changes in stereochemistry resulted in blackbrush tannins being less preferred than bitterbrush tannins when offered to snowshoe hares (Lepus americanus). It is unlikely that differences in protein-precipitating abilities are the cause for the preference of the bitterbrush over the blackbrush tannins. Instead, we hypothesize that condensed tannins may be depolymerized and absorbed following ingestion. Differences in tannin structure can lead to different depolymerized products and rates of depolymerization, both of which may affect herbivore preferences. PMID:24264205

Clausen, T P; Provenza, F D; Burritt, E A; Reichardt, P B; Bryant, J P



Multifunctional porous solids derived from tannins  

NASA Astrophysics Data System (ADS)

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.

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



Mechanism of neurotoxicity of cardiotonic glycosides.  


1 In cats intracerebroventricular administration of 5, 10, 20 mug of peruvoside, a cardiac glycoside obtained from the plant, Thevetia neriifolia, and 10 and 20 mug of ouabain, produced marked neurotoxicity. This was dose-related. 2 Prior administration reserpine (2 mg/kg i.m., 500 mug i.c.v.) or tetrabenazine (25 mg/kg i.v., 50 mg/kg i.v. and 2 mg/,g i.c.v.) suppressed the neurotoxicity, but lithium carbonate (100 mg/,g i.p., 2 mg 2.c.v.) and haloperidol (200 mug i.c.v.) were ineffective. 3 Prior administration of 2-bromolysergic acid diethylamide (BOL-148, 200 mug i.c.v.) or p-chlorophenylalanine (PCPA) (400 mg/kg i.p.) suppressed the neurotoxicity induced by peruvoside and ouabain. 4 Perfusion of the lateral ventricles of cats with 10, 20 and 30 mug of peruvoside or ouqbain produced a massive release of 5-hydroxytryptamine (5-HT). This was dose-related. Prior administration PCPA suppressed the release of 5-HT. 5 The results of the findings indicate the involvement of 5-HT in the genesis of neurotoxicity induced by peruvoside or ouabain. PMID:13903

Gaitondé, B B; Joglekar, S N



Mechanism of neurotoxicity of cardiotonic glycosides.  

PubMed Central

1 In cats intracerebroventricular administration of 5, 10, 20 mug of peruvoside, a cardiac glycoside obtained from the plant, Thevetia neriifolia, and 10 and 20 mug of ouabain, produced marked neurotoxicity. This was dose-related. 2 Prior administration reserpine (2 mg/kg i.m., 500 mug i.c.v.) or tetrabenazine (25 mg/kg i.v., 50 mg/kg i.v. and 2 mg/,g i.c.v.) suppressed the neurotoxicity, but lithium carbonate (100 mg/,g i.p., 2 mg 2.c.v.) and haloperidol (200 mug i.c.v.) were ineffective. 3 Prior administration of 2-bromolysergic acid diethylamide (BOL-148, 200 mug i.c.v.) or p-chlorophenylalanine (PCPA) (400 mg/kg i.p.) suppressed the neurotoxicity induced by peruvoside and ouabain. 4 Perfusion of the lateral ventricles of cats with 10, 20 and 30 mug of peruvoside or ouqbain produced a massive release of 5-hydroxytryptamine (5-HT). This was dose-related. Prior administration PCPA suppressed the release of 5-HT. 5 The results of the findings indicate the involvement of 5-HT in the genesis of neurotoxicity induced by peruvoside or ouabain. PMID:13903

Gaitonde, B B; Joglekar, S N



Diterpene glycosides from Stevia rebaudiana.  


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

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



Myricetin glycosides from Licania densiflora.  


Dried leaves of Licania densiflora yielded five myricetin glycosides: myricetin 3'-methylether-3-O-glucoside (1), myricetin 3'-methylether-3-O-galactoside (2), myricetin 4'-methylether-3-O-rhamnoside (3), myricetin 3',5'-dimethylether-3-O-glucoside (4), and myricetin 3',5'-dimethylether-3-O-rhamnoside (5). Their structures were elucidated by spectroscopic methods including mono- and bi-dimensional NMR techniques. PMID:11223232

Braca, A; Bilia, A R; Mendez, J; Morelli, I



Dihydroflavonol glycosides from rhododendron ferrugineum  

Microsoft Academic Search

Chemical investigation of the leaves and the flowers of Rhododendron ferrugineum afforded six known flavonoids: hyperoside, myricetin 3-O-?-galactopyranoside, kaempferol 3-O-(6?-O-acetyl)-glucoside, quercetin 3-O-(6?-O-acetyl)-glucoside, quercetin 3-O-(6?-O-acetyl)-galactoside, quercetin 3-O-(3?,6?-O-diacetyl)-galactoside and two new dihydroflavonol glycosides: trans-taxifolin 3-O-?-arabinopyranoside and cis-taxifolin 3-O-?-arabinopyranoside.

E Chosson; A Chaboud; A. J Chulia; J Raynaud



Myricetin glycosides from Licania densiflora  

Microsoft Academic Search

Dried leaves of Licania densiflora yielded five myricetin glycosides: myricetin 3?-methylether-3-O-glucoside (1), myricetin 3?-methylether-3-O-galactoside (2), myricetin 4?-methylether-3-O-rhamnoside (3), myricetin 3?,5?-dimethylether-3-O-glucoside (4), and myricetin 3?,5?-dimethylether-3-O-rhamnoside (5). Their structures were elucidated by spectroscopic methods including mono- and bi-dimensional NMR techniques.

A. Braca; A. R. Bilia; J. Mendez; I. Morelli



Flavonol glycosides from Dryas octopetala.  


Six flavonol glycosides and ent-epicatechin were isolated from Dryas octopetala and their structures elucidated by chemical and spectroscopic methods. Two new flavonoids, 3-O-alpha-L-arabinofuranosyl-8-methoxyquercetin (2) and 3-O-beta-galactopyranosyl-8-methoxykaempferol (6), were identified along with 3-O-beta-D-galactopyranosylquercetin (hyperin) (3), 3-O-alpha-L-arabinofuranosylquercetin (avicularin) (5), 3-O-beta-L-arabinopyranosylquercetin (4), and 3-O-beta-D-galactopyranosyl-8-methoxyquercetin (1). PMID:6512533

Servettaz, O; Colombo, M L; De Bernardi, M; Uberti, E; Vidari, G; Vita-Finzi, P



Dietary tannins improve lamb meat colour stability  

Microsoft Academic Search

Fourteen male Comisana lambs were divided into two groups at 45days of age: lambs fed a concentrate diet (C), or lambs fed the same concentrate with the addition of quebracho (Schinopsis lorentzii) tannins (T). Sheep were slaughtered at 105days of age. Lipid oxidation, colour coordinates, haem pigment concentration, and metmyoglobin percentages were measured on minced semimembranosus muscle (SM) over 14days

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



Science Study Aids 5: Tannin - Nature's Filter.  

ERIC Educational Resources Information Center

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…

Boeschen, John; Randall, John M.


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


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. PMID:19477483

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



Tannin-assisted aggregation of natively unfolded proteins  

NASA Astrophysics Data System (ADS)

Tannin-protein interactions are essentially physical: hydrophobic and hydrogen-bond-mediated. We explored the tannin-assisted protein aggregation on the case of ?-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.

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



Glycoside hydrolases of rumen bacteria and protozoa  

Microsoft Academic Search

Sixteen strains of rumen bacteria and 21 protozoal preparations were screened for glycoside hydrolase and phosphatase activity, using 22 nitrophenyl glycoside substrates. The range and level of bacterial enzyme activities were species dependent, although, the glycosidases associated with plant cell wall breakdown were most active in the cellulolytic and hemicellulolytic species. Alkaline phosphatase occurred widely in the organisms examined, but

Alan G. Williams; Susan E. Withers; Geoffrey S. Coleman



Benzyl benzoate glycosides from Oligoneuron rigidum.  


Two new benzyl benzoate glycosides were isolated from the leaves and stems of the native North American prairie plant Oligoneuron rigidum (stiff goldenrod). The glycosides were isolated as a mixture of benzoate and acetate esters, which were subjected to mild base hydrolysis to facilitate full structural characterization using LCMSMS and 1D and 2D NMR data. PMID:23121124

Miesner, Sarah; Frosch, Holly; Kindscher, Kelly; Tichy, Shane; Manfredi, Kirk P



Bioavailability of genistein and its glycoside genistin  

Microsoft Academic Search

Genistein belongs to the class of isoflavones. The main sources of isofiavones in food are soybeans and soy-based products. Most isoflavones in plants are bound to sugars such as the glycosides genistin and daidzin. Understanding the various factors that influence absorption and metabolism of isoflavones and especially of their naturally occurring glycosides, is essential to fully elucidate and understand the

Aukje Steensma



[Effect of plant glycosides on resistance and capacitance vessels].  


In the anaesthetized cat, SCOA ( Miroton ), a product which contains extracts from Scilla , Convallaria , Oleander and Adonis , displays not only its well-known positive inotropic effect but has also constrictor effects on veins when applied in intravenous doses of 21.5-100 GPU /kg ( GPU = guinea-pig units, i.e. cardiotoxic equivalents related to 1 g body weight of guinea-pigs). The latter effect differs in that it is somewhat more prolonged. With intraduodenal administration the doses required to achieve equal peak effects as with intravenous injection are about 4 times larger and this suggests a relatively good enteral availability in the cat. SCOA constricts not only veins but also arteries. However, this latter effect is comparatively small and occurs only after intraarterial infusion of high doses (9.1 and 91 GPU /min, respectively).--The cardiac glycosides contained in the drug product primarily account for its vasoactive qualities. The venous constrictor effect correlates with the guinea-pig units. In qualitative respects, the pure glycosides cymarin , convallatoxin , proscillaridin , and scillaren exert equal effects. There is, however, evidence that the correlation between the effect on veins and on the heart differs for the glycosides tested. Based on equal guinea-pig units, the adonis extract, for instance, acts on capacitance vessels about twice as much as scilla , oleander and convallaria extracts. Cymarin , too, has a stronger effect on veins than would be expected from its cardiotoxic effect. The action on arteries and veins are based on different mechanism.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:6540100

Lehmann, H D



Steroidal glycosides with antiproliferative activities from Digitalis trojana.  


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??M. 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??M. PMID:23722601

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



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

Code of Federal Regulations, 2013 CFR

...bis(fattyalkyl) dimethyl, salts with tannins (generic...bis(fattyalkyl) dimethyl, salts with tannins (generic...bis(fattyalkyl) dimethyl, salts with tannins (PMN P-12-437...j). (ii) Release to water. Requirements as...



Pregnane glycosides from Leptadenia pyrotechnica.  


The whole plant of Leptadenia pyrotechnica afforded 18 new pregnane glycosides (1-18) with sarcostin, 11-hydroxysarcostin, and deacetylmetaplexigenin as the aglycon moieties and acetyl, benzoyl, cinnamoyl, p-coumaroyl, and nicotinoyl ester moieties linked at C-12 and/or C-20 of the aglycon and hexopyranose, 6-deoxy-3-O-methylhexopyranose, and 2,6-dideoxy-3-O-methylhexopyranose sugars linked at C-3 of their aglycon. The structures of these compounds were elucidated by spectroscopic data interpretation and from chemical evidence. The antiproliferative activity of all compounds was evaluated using three continuous murine and human culture cell lines, J774.A1, HEK-293, and WEHI-164. Compounds having deacethylmetaplexigenin as aglycon and a cinnamoyl ester moiety linked at C-12 were the most active constituents. PMID:16643040

Cioffi, Giuseppina; Sanogo, Rokia; Vassallo, Antonio; Dal Piaz, Fabrizio; Autore, Giuseppina; Marzocco, Stefania; De Tommasi, Nunziatina



Two new glycosides from Conyza bonariensis.  


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

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



Kaempferol glycosides and cardenolide glycosides, cytotoxic constituents from the seeds of Draba nemorosa (Brassicaceae)  

Microsoft Academic Search

Bioassay-directed fractionation of a methanolic extract from the seeds of Draba nemorosa (Brassicaceae) led to isolation of a new flavonol glycoside, drabanemoroside (5, kaempferol 3-O-?-L-rhamnopyranosyl-(1?2)-?-L-arabinopyranose) along with four known flavonoid derivatives (1–4), four cardenolide glycosides (6–9). Kaempferol glycosides 2 and 5 showed strong cytotoxicity against human small lung cancer cell line A549 and melanoma SK-Mel-2 with an IC50 of 0.5

Surk-Sik Moon; Aziz Abdur Rahman; Maniruzzaman Manir; V. S. Jamal Ahamed



Triterpene glycosides from the far eastern sea cucumber Pentamera calcigera II: disulfated glycosides.  


Three new triterpene glycosides, calcigerosides D(1) (1), D(2) (2), and E (3), have been isolated from the sea cucumber Pentamera calcigera. Their structures have been deduced from extensive spectral analysis (NMR and MS) and chemical evidence. All the compounds are disulfated pentaosides differing in aglycon structure and position of sulfate group, which were determined by the measurement of NT(1) values in the cases of glycosides 1 and 2. Glycoside 1 is a nonholostane derivative, that is, it lacks an 18(20)-lactone, which is very rare among the sea cucumber glycosides. PMID:11076550

Avilov, S A; Antonov, A S; Drozdova, O A; Kalinin, V I; Kalinovsky, A I; Riguera, R; Lenis, L A; Jiménez, C



A caffeoyl phenylethanoid glycoside from plantago myosuros  

Microsoft Academic Search

From Plantago myosuros, the iridoid glucoside, aucubin was isolated, together with the caffeoyl phenylethanoid glycosides, plantalloside and verbascoside. Plantalloside is a new verbascoside analogue with a ?-allopyranosyl moiety. The structure was elucidated by NMR spectroscopy.

Henrik Franzyk; Tommy Lykke Husum; Søren Rosendal Jensen



Immunomodulatory sesquiterpene glycosides from Dendrobium nobile  

Microsoft Academic Search

Four sesquiterpene glycosides with alloaromadendrane, emmotin, and picrotoxane type aglycones were isolated from the stems of Dendrobium nobile Lindl (Orchidaceae). Their structures were determined by spectroscopic methods and chemical reactions. Immunomodulatory activity of the isolates was evaluated in vitro.

Qinghua Ye; Guowei Qin; Weimin Zhao



A flavonol glycoside from Embelia schimperi leaves  

Microsoft Academic Search

A new flavonol glycoside, quercetin 3-galactosyl (1 ? 2) rhamnoside, has been isolated from the leaves of Embelia schimperi. The known compounds quercetin 3-rutinoside, quercetin 3-rhamnoside, quercetin 3-galactoside, myricetin and quercetin were also identified from this plant.

Lawrence O. Manguro Arot; Lawrence A. D. Williams



[Tannin content and inhibiting activity of elastase in Rosaceae].  


From 42 Rosaceae species, only the Rosoideae species exhibit high tannin content and elastase inhibiting activity such as Filipendula ulmaria, Geum montanum, G. rivale, Alchemilla xanthochlora and Sanguisorba minor. Other studied species from Spiraeoideae, Maloideae and Prunoideae subfamilies are less rich in tannin and also less active. PMID:2131766

Lamaison, J L; Carnat, A; Petitjean-Freytet, C



Adsorbent Derived from Pinus pinaster Tannin for Cationic Surfactant Removal  

Microsoft Academic Search

Pinus tannin gel (PTG) has proven to be an effective adsorbent for removing various cationic pollutants including heavy metals, dyes, and surfactants. The form of obtaining these condensed tannins from Pinus pinaster bark was conventional aqueous extraction using 5.0% ethanol as additive. The present study focused on the removal of the surfactant hexadecyltrimethylammonium bromide (CTAB) from aqueous solutions using PTG.

J. Sánchez-Martín; J. Beltrán-Heredia; I. J. Seabra; M. E. M. Braga; H. C. de Sousa



Acid corrosion inhibition of copper by mangrove tannin  

Microsoft Academic Search

Purpose – The purpose of this paper is to evaluate the corrosion inhibition potential of mangrove (Rhizopora apiculata) tannin in hydrochloric acid medium on copper with the view of developing a natural corrosion inhibitor. Design\\/methodology\\/approach – The mangrove tannin was extracted from the mangrove bark and its anticorrosion potential was studied by weight loss, electrochemical and scanning electron microscopy (SEM)

A. M. Shah; A. A. Rahim; S. Yahya; P. B. Raja; S. A. Hamid



Iridoid and megastigmane glycosides from Phlomis aurea  

Microsoft Academic Search

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-?-xylopyranosyl-(1?2)-?-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

Mohamed S. Kamel; Khaled M. Mohamed; Hashim A. Hassanean; Kazuhiro Ohtani; Ryoji Kasai; Kazuo Yamasaki



A new diterpene glycoside from Stevia rebaudiana.  


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

Chaturvedula, Venkata Sai Prakash; Prakash, Indra



Triterpene glycosides of Dianthus deltoides. I  

Microsoft Academic Search

Summary FromDianthus deltoides L. we have isolated three new triterpene glycosides: dianthosides A, B, and C. It has been shown that dianthoside A is the 3-O-ß-glucopyranoside and dianthoside B the 3-O-[O-ß-D-glucopyranosyl-(1 ? 6)-ß-glucopyranoside] of gypsogenic acid. Some information on the structure of dianthoside C — a new glycoside of gypsogenin — has been obtained.

V. G. Bukharov; S. P. Shcherbak; A. P. Beshchekova



Vegetable oil thermosets reinforced by tannin-lipid formulations.  


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

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



Tannin inhibits adenylate cyclase in airway epithelial cells.  


Tannin, isolated from cotton bracts extract and implicated in the pathogenesis of byssinosis, inhibits adenosine 3',5'-cyclic monophosphate (cAMP) production and Cl- secretion in bovine airway epithelial cells in part by inhibiting adrenergic receptor binding. The purpose of this study was to determine whether tannin affected other parts of the adrenergic-cAMP signal transduction pathway by examining the effect of tannin on guanosine 5'-triphosphate (GTP)-regulatory pathways (G proteins) and on adenylate cyclase activity. cAMP production in confluent airway epithelial cells was measured in the presence of cholera toxin (100 micrograms/ml), an activator of GS proteins, and forskolin (0.1-1,000 microM), a direct activator of adenylate cyclase. Cholera toxin stimulated cAMP production; this response, however, was inhibited in cells pretreated with 50 micrograms/ml tannin. Forskolin (100 microM) stimulated cAMP production 13-fold above baseline values. Tannin pretreatment inhibited the stimulatory effect of forskolin on cAMP release in a dose-dependent manner with a tannin concentration causing 50% inhibition of 7.5 micrograms/ml. The stimulatory effect of forskolin on cAMP release was completely inhibited in cells pretreated with 50 micrograms/ml tannin. The inhibition was reversible 3 h after removal of tannin from the solution. Tannin also inhibited forskolin-stimulated adenylate cyclase activity in a dose-dependent, noncompetitive manner. We conclude that forskolin and cholera toxin stimulate cAMP production in airway epithelial cells and that tannin inhibits the production of cAMP in airway epithelial cells by a direct effect on adenylate cyclase activity. PMID:7762688

Cloutier, M M; Guernsey, L



Triterpenoid glycosides from Anagallis arvensis.  


From the herb of Anagallis arvensis, we have isolated four novel oleanane glycosides, anagallosaponins VI-IX, and two artifact saponins, apoanagallosaponins III and IV, formed from anagallosaponins III and IV. The structures were elucidated by chemical and spectral methods, 2D NMR techniques being particularly helpful. The structures of anagallosaponins VI and VII were characterized as priverogenin B 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside and 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)]beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside), respectively. The structures of anagallosaponins VIII and IX were characterized as 23-hydroxypriverogenin B 22-acetate 3-O-(beta-D-xylopyranosyl (1-->2)-O-beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)]beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]- alpha-L-arabinopyranoside), respectively. The structures of apoanagallosaponins III and IV were characterized as camelliagenin A 16-acetate 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabnopyranoside, 3-O-(beta-D-xylopyranosyl (1-->2)-O-beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), respectively. PMID:7765757

Shoji, N; Umeyama, A; Yoshikawa, K; Arihara, S



Cardiac lipofibromatosis.  


We present a case of cardiac lipofibromatosis associated with atrial fibrillation and complete heart block requiring permanent pacemaker implantation. Multimodality cardiac imaging including transthoracic echocardiography and cardiac magnetic resonance were useful for tissue characterization of this rare cardiac diagnosis. PMID:23146562

Shen, Seeger; Rizkallah, Jacques; Kirkpatrick, Iain D C; Khadem, Ali; Jassal, Davinder S



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

NASA Astrophysics Data System (ADS)

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.

Hernes, Peter J.; Hedges, John I.



Diterpene glycosides from Stevia phlebophylla A. Gray.  


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 16?-hydroxy-17-acetoxy-ent-kauran-19-oic acid-(6-O-?-D-xylopyranosyl-?-D-glucopyranosyl) ester (1) on the basis of extensive NMR and MS data as well as the characterization of its acid hydrolysate. Seven more compounds were detected by ESIMS which are possibly structurally related to 1. It can therefore be concluded that S. phlebophylla is unlikely to contain significant amounts of steviol glycosides, if any. PMID:23831634

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



Tannin inhibition of protein kinase C in airway epithelium.  


Tannin, a polydisperse polyphenol extracted from cotton bracts (CBE), has been implicated in the pathogenesis of byssinosis, a lung disease of mill workers. CBE tannin inhibits chloride secretion in airway epithelial cells by means of an unknown mechanism(s). Activation of protein kinase C (PKC) by PMA (phorbol 12-myristate 13-acetate) in airway cells increases chloride secretion. The effect of tannin on this PKC pathway was examined, using canine tracheal epithelium mounted in Ussing chambers. PMA addition (10 nM) to the mucosal bath resulted in a 0.36 +/- 0.07 microEq/cm2.h (mean +/- SEM, n = 20) increase in short-circuit current (Isc) and a 0.38 +/- 0.17 microEq/cm2.h increase in net chloride secretion (Jnet). The inactive 4 alpha-phorbol had no effect. Tannin addition to the mucosal bath produced a dose-dependent decrease in Isc and Jnet. In tissues pretreated with 2-50 micrograms/ml tannin, and subsequently stimulated with PMA, tannin inhibited PMA stimulation of chloride secretion beginning at a tannin concentration of 10 micrograms/ml (0.09 +/- 0.05 microEq/cm2.h [n = 10] increase in Isc and 0.08 +/- 0.03 microEq/cm2.h increase in Jnet with PMA after tannin pretreatment). At 50 micrograms/ml tannin, the stimulatory effect of PMA was completely abolished. The known PKC inhibitor, H-7 (20 microM), inhibited PMA stimulation, while chelerythrine (2 microM) had not effect on PMA-stimulated Isc and Jnet, and calphostin C was toxic to the airway epithelium. In membrane fragments, 2.5 micrograms/ml tannin inhibited the rate of histone III phosphorylation by PMA from 32.1 +/- 4.4 nmol/mg protein per min to 20.1 +/- 2.7 nmol/mg protein per min (n = 7). In bovine airway cells, tannin pretreatment (2.5 micrograms/ml) decreased the cytosolic activity of PKC but had no effect on PKC translocation to the membrane. We conclude that tannin inhibits chloride secretion in airway epithelial cells in part by inhibiting PKC. PMID:7564489

Cloutier, M M; Guernsey, L



Glycoside of hypsogenic acid from Saponaria officinalis L  

Microsoft Academic Search

A glycoside of hypsogenic acid called saponaroside has been isolated for the first time from the roots ofSaponaria officinalis L. It was shown that the glycoside isß-D-xylopyranoside-3-hypsogenic acid.

V. G. Bukharov; S. P. Shcherbak



Phenylethanoid and iridoid glycosides from Veronica persica.  


A new phenylethanoid glycoside, persicoside (1) and three known phenylethanoid glycosides, acteoside (2), isoacteoside (3) and lavandulifolioside (4) were isolated from the aerial parts of Veronica persica. On the basis of spectral analyses, the structure of the new compound was elucidated to be 3,4-dihydroxy-beta-phenylethoxy-O-[beta-D-glucopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-4-O-caffeoyl-beta-D-glucopyranoside. Persicoside (1) and acteoside (2) exhibited radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Beside phenylethanoid glycosides, a hexitol, dulcitol (5) and seven known iridoid glucosides, aucubin (6), veronicoside (7), amphicoside (8), 6-O-veratroyl-catalpol (9), catalposide (10), verproside (11) and verminoside (12) were isolated. PMID:12045353

Harput, U Sebnem; Saracoglu, Iclal; Inoue, Makoto; Ogihara, Yukio



Steviol glycosides: chemical diversity, metabolism, and function.  


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

Ceunen, Stijn; Geuns, Jan M C



Tannins from Canarium album with potent antioxidant activity*  

PubMed Central

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

Zhang, Liang-liang; Lin, Yi-ming



Sesquiterpene lactone glycosides from Arnica longifolia.  


Flowers of ARNICA LONGIFOLIA were investigated for the occurrence of sesquiterpene lactone glycosides. A mixture containing the two isomeric 11alpha,13-dihydro- and 11beta,13-dihydro-4 H-tomentosin glucosides, previously isolated from A. AMPLEXICAULIS and A. MOLLIS, together with the two isomeric 11alpha,13-dihydro- and 11beta,13-dihydro-4 H-carabrone glucosides were found in A. LONGIFOLIA. All carbon and proton shifts of the glycosides could be assigned by their 2D-COSY and 2D-HETCOR spectra and spectroscopy of their respective aglycones, obtained via enzymatic hydrolysis. PMID:17260246

Passreiter, C M; De Carlo, M; Steigel, A



New minor glycoside components from saffron.  


Phytochemical investigation of the stigmas of Crocus sativus resulted in the isolation of eight glycosides (1-8) including a new safranal glycoside (2) and a new carotenoid pigment (6). The structures of the new compounds were identified as (4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde 4-O-[?-D-glucopyranosyl(1 ? 3)-?-D-glucopyranoside] (2) and trans-crocetin-1-al 1-O-?-gentiobiosyl ester (6) on the basis of extensive chemical and spectroscopic evidence. PMID:23179314

Tung, Nguyen Huu; Shoyama, Yukihiro



Neolignan and flavonoid glycosides in Juniperus communis var. depressa  

Microsoft Academic Search

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

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



Neolignan and flavonoid glycosides in Juniperus communis var. depressa.  


Two neolignan glycosides (junipercomnosides A and B) were isolated from aerial parts of Juniperus communis var. depressa along with two known neolignan glycosides and seven flavonoid glycosides. The structures of the isolated compounds were determined by spectral analysis, in particular by 2D-NMR analysis. The significance of distribution of flavonoids in the chemotaxonomy of genus Juniperus was also discussed. PMID:14732280

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



Elemanolide sesquiterpenes and eudesmane sesquiterpene glycosides from Centaurea hierapolitana.  


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

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



Sealing and anti-corrosive action of tannin rust converters  

SciTech Connect

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.

Gust, J.; Bobrowicz, J. (Building Research Inst., Warsaw (Poland))



Curing process of phenol-urea-formaldehyde-tannin (PUFT) adhesives  

Microsoft Academic Search

Summary  Phenol-urea-formaldehyde-tannin (PUFT) adhesives have been prepared by copolymerization at room temperature of pine bark tannins\\u000a with phenol-urea-formaldehyde (PUF) prepolymers prepared under varying operating conditions. Differential scanning calorimetry\\u000a (DSC) and dynamic mechanical analysis (DMA) have been used to analyse the curing of prepolymers and adhesives. DSC curves\\u000a were obtained at three different heating rates and, by means of the Model Free

G. Vázquez; F. López-Suevos; J. González-Alvarez; G. Antorrena



Kaempferol glycosides and cardenolide glycosides, cytotoxic constituents from the seeds of Draba nemorosa (Brassicaceae).  


Bioassay-directed fractionation of a methanolic extract from the seeds of Draba nemorosa (Brassicaceae) led to isolation of a new flavonol glycoside, drabanemoroside (5, kaempferol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranose) along with four known flavonoid derivatives (1-4), four cardenolide glycosides (6-9). Kaempferol glycosides 2 and 5 showed strong cytotoxicity against human small lung cancer cell line A549 and melanoma SK-Mel-2 with an IC(50) of 0.5 microg/mL and 1.9 microg/mL, respectively. Cardenolide glycosides 6-9 showed potent cytotoxicity (A549) in the range of 0.01-0.032 microg/mL. Their structures were characterized based on spectroscopic data (2D NMR, HRTOFMS, IR, and UV) and comparison of literature values. The carbohydrate units were also confirmed by comparing the hydrolysate of 5 with authentic monosaccharides. PMID:20803119

Moon, Surk-Sik; Rahman, Md Aziz Abdur; Manir, Md Maniruzzaman; Jamal Ahamed, V S



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

PubMed Central

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

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



Nivyaside — A new glycoside from Leucanthemum vulgare  

Microsoft Academic Search

From the ligulate flowers ofLeucanthemum vulgare Lam. growing on the territory of the Georgian SSR a new glycoside has been isolated which has been called nivyaside and has\\u000a the structure 8-(1-?-D-glucopyranosyl-5-deoxyquercit-5-yl)-4?,5,7-trihydroxyflavone.

T. G. Sagareishvili; M. D. Alaniya; V. S. Kikoladze; É. P. Kemertelidze



A flavonol glycoside from Myrsine africana leaves  

Microsoft Academic Search

Myricetin 3-(3?,4?-diacetylrhamnoside), a novel flavonol glycoside together with myricetin 3-rhamnoside, myricetin 7-rhamnoside, myricetin 3-xyloside, myricetin 3-arabinoside, quercetin 3-galactoside, 3?-O-methylquercetin 3-glucoside, myricetin, quercetin, kaempferol and gallic acid have been isolated from a methanolic extract of Myrsine africana leaves.

Lawrence O. Manguro Arot; Jacob Ogweno Midiwo; Wolfgang Kraus



Two new secoiridoid glycosides from Gentiana algida.  


Two new acylated secoiridoid glycosides were isolated from the aqueous acetone extract of the whole herb of Gentiana algida. The structures of these new products were established by spectral and chemical methods as 6'-(2,3-dihydroxybenzoyl)sweroside and 6'-(2,3-dihydroxybenzoyl)swertiamarin, respectively. PMID:17252380

Tan, R X; Hu, J; Dong, L D; Wolfender, J L; Hostettmann, K



A new aromatic glycoside from Glehnia littoralis.  


A new aromatic glycoside (1) was isolated from the roots of Glehnia littoralis Fr. Schmidtex Miq. Its structure was elucidated as vanillic acid 1-O-[?-D-apiofuranosyl-(1 ? 6)-?-D-glucopyranoside] ester mainly by analysing the NMR and MS spectral data. In the in vitro assays, compound 1 displayed some TNF-? secretion inhibitory activity. PMID:24547738

Feng, Zi-Jin; Zhang, Xiao-Hong; Zhang, Jian-Peng; Shang, Xiao-Hui; Gao, Yun; Lu, Xiao-Ling; Liu, Xiao-Yu; Jiao, Bing-Hua



Enzymatic Processing of Bioactive Glycosides from Natural Sources  

NASA Astrophysics Data System (ADS)

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.

Weignerová, Lenka; K?en, Vladimír


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


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. PMID:24444964

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



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

NASA Astrophysics Data System (ADS)

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.

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



New lupane glycosides from Pulsatilla chinensis.  


Two new lupane glycosides along with five known triterpenoids were isolated from the roots of Pulsatilla chinensis (Ranunculaceae). The structures of the new glycosides were determined to be 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-23-hydroxybetulinic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl ester (pulsatilloside D, 6) and 3-O-[beta-D-glucopyranosyl(1-->4)][alpha-L-rhamnopyranosyl(1-->2)]-alpha-L-arabinopyranosyl-23-hydroxybetulinic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl ester (pulsatilloside E, 7) by spectroscopic analysis and chemical methods. The compounds were evaluated for cytotoxic activities against K-562 human leukemia and HeLa cells. PMID:11859478

Ye, Wencai; Zhang, Qingwen; Hsiao, Wendy W; Zhao, Shouxun; Che, Chun-Tao



Cyanogenic glycosides: a case study for evolution and application of cytochromes P450  

Microsoft Academic Search

Cyanogenic glycosides are ancient biomolecules found in more than 2,650 higher plant species as well as in a few arthropod species. Cyanogenic glycosides are amino acid-derived ?-glycosides of ?-hydroxynitriles. In analogy to cyanogenic plants, cyanogenic arthropods may use cyanogenic glycosides as defence compounds. Many of these arthropod species have been shown to de novo synthesize cyanogenic glycosides by biochemical pathways

Søren Bak; Susanne Michelle Paquette; Marc Morant; Anne Vinther Morant; Shigeki Saito; Nanna Bjarnholt; Mika Zagrobelny; Kirsten Jørgensen; Sarah Osmani; Henrik Toft Simonsen; Raquel Sanchez Pérez; Torbjørn Bordier van Heeswijck; Bodil Jørgensen; Birger Lindberg Møller



Benzophenone O-glycosides from Hypericum elegans  

Microsoft Academic Search

Elegaphenonoside, a new benzophenone O-rhamnoside, together with two known benzophenone O-glycosides, namely hypericophenonoside and neoannulatophenonoside, were isolated from the aerial parts of Hypericum elegans Stephan ex Willd. The structure of the new compound was established as 3?,5?,6-trihydroxy-4-methoxybenzophenone-2-O-?-L-rhamnopyranoside by means of chemical and physical evidence. In addition, the presence of kaempferol, quercetin, isoquercitrin, norathyriol, I-3,II-8-biapigenin, quercitrin, hyperoside and rutin were established

Paraskev T. Nedialkov; Dimitrina Zheleva-Dimitrova; Ulrich Girreser; Gerassim M. Kitanov



?-cyclodextrin assistant flavonoid glycosides enzymatic hydrolysis  

PubMed Central

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

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



New xanthone glycosides from Comastoma pedunculatum.  


Five new xanthone glycosides, comastomasides A-E (1-5), were isolated from aqueous ethanol extracts of the aerial portions of Comastoma pedunculatum. The structures of these compounds were elucidated by spectroscopic analysis methods. Compounds 1-5 were evaluated for their hepatoprotective activity and cytotoxicity against four human cancer cell lines by in vitro assays. Among them, compounds 3 and 5 exhibited potent hepatoprotective activity. However, none of the compounds displayed cytotoxic activity. PMID:22814820

Qiao, Yongqi; Yuan, Yi; Cui, Baosong; Zhang, Ying; Chen, Hui; Li, Shuai; Li, Yan



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

NASA Astrophysics Data System (ADS)

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.

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



Cold-set tannin-resorcinol-formaldehyde adhesives of lower resorcinol content  

Microsoft Academic Search

Tannin-resorcinol-formaldehyde cold-setting adhesives for structural wood applications and with an additional resorcinol content\\u000a as low as 5%, have been prepared from standard tannin-based adhesive formulations in which the balance of needed resorcinol\\u000a was directly generated from the tannin extract. Encouraging results were also obtained with a different formulation in which\\u000a all resorcinol was gencrated from the tannin extract used in

A. Pizzi; E. Orovan; F. A. Cameron



Toxicity of the isolated tannin from Quercus havardi  

E-print Network

and gallic acid or some other compound(s). The period of time between 1940 and 1950 saw a great increase in the use of tannic acid ointments in burn therapy. Severdl people who had suffered extensive burns died while being treated with tannic acid... to isolate the tannin from guuerc s h~a ardi and to study the oral toxicity of the tannin and its hydro- lyzable constituents. EXPERIMENTAL f~~t, tt u~h ~fbg 1 d ~kd 1 b ~ ~d ~ f 0 k 1' 1 Gallic acid, pyrogallol and tannic acid (reagent grade) were fed...

Pigeon, Robert F



On the molluscicidal activity of tannin containing plants.  


The aqueous and methanolic extracts of a series of typical tannin containing plants exhibit strong molluscicidal properties against the freshwater snail biomphalaria glabrata, which is the intermediate host of schistosomiasis. The crude extracts of Krameria triandra (Krameriaceae) and Arctostaphylos uvaursi (Ericaceae) were active at concentrations of 50 ppm. Hydrolyzable and condensed tannins are responsable for the molluscicidal activity. This report indicates a new class of plant derived compounds which may have important practical application for the control of schistosomiasis in endemic areas. PMID:17404963

Schaufelberger, D; Hostettmann, K



Distinct signal transduction pathways for activation of rabbit alveolar macrophages in vitro by cotton bract tannin.  


These experiments were designed to study signal transduction pathways in alveolar macrophages stimulated by condensed tannin or zymosan. Condensed tannins, present in cotton mill dust, alter the host-defense function of alveolar macrophages and may contribute to the pathogenesis of byssinosis. We tried to determine the early steps in signal transduction mechanisms of cell activation by tannin. With the quantification of 51Cr release, we determined that tannin was cytotoxic for the cells after 30 min activation with 130 micrograms for 2 x 10(6) cells. 51Cr release was similar for control cells and zymosan- or 30 micrograms tannin-activated cells. Using the luciferine luciferase reaction, we showed that tannin markedly depleted ATP cell content. In inositol-labeled cells, tannin increased inositolphosphate release in a dose-dependent manner. In lysoPAF-labeled cells, tannin induced synthesis of phosphatidic acid and diglycerides. In the presence of ethanol, the level of tannin-induced phosphatidic acid was slightly reduced, and phosphatidylethanol was synthesized. No phosphatidylethanol was found in alveolar macrophages stimulated by zymosan in the presence of ethanol. GF 109203X, a specific inhibitor of protein kinase C decreased only tannin-induced phosphatidylethanol synthesis. In conclusion, tannin (at 30 or 130 micrograms/ml) activated an inositol phospholipase C in alveolar membranes. Phosphatidylcholine phospholipases C and D were found only at the higher concentration of tannin. PMID:8658514

Prévost, M C; Soulat, J M; Comminges, C; Maury, E; Aslane, R; Cohen-Jonathan, E; Cariven, C; Lauque, D; Chap, H



Condensed tannins in Trifolium species and their significance for taxonomy and plant breeding  

Microsoft Academic Search

Populations of 59 Trifolium taxa were screened for condensed tannin content using the vanillin-HC1 test. Eight species (T. arvense, T. aureum, T. badium, T. campestre, T. dubium, T. micranthum, T. patens and T. spadiceum) were shown to contain tannins. These species are all found in Section Chronosemium or Section Trifolium Subsection Arvensia of the genus, and thus presence of tannins

Michael F. Fay; Philip J. Dale



The influence of mangrove-derived tannins on intertidal meiobenthos in tropical estuaries  

Microsoft Academic Search

Mangrove-derived tannins negatively effected laboratory-reared nematode populations and natural communities of meiobenthos in tropical mangrove forests along the northeastern coast of Australia. In the low and mid intertidal zones of five mangrove estuaries, nearly all of the dominant meiofaunal taxa correlated negatively with concentrations of sediment tannins. Only nematodes correlated with low tannin concentrations in the high intertidal zones. The

D. M. Alongi



Effect of black bean tannins on in vitro carbohydrate digestion and absorption  

Microsoft Academic Search

Legume seeds are an important source of protein and carbohydrate for both human and animal consumption. Nevertheless the bioavailability of these nutrients is affected by several antinutritional factors present in edible pulses. Most of them, except tannins, are destroyed, at least partially, during cooking. Tannins impair macronutrient utilization by forming tannin-protein complexes with various digestive enzymes precluding the formation of

Andrés Carmona; Lars Borgudd; Gina Borges; Abraham Levy-Benshimol



[Phenylethanoid glycosides distribution in medicinal plants of Gesneriaceae].  


To investigate the role of distribution and phylogeny of phenylethanoid glycoside in medicinal plants of Gesneriaceae, five phenylpropanoid glycosides, acteoside, paraboside B, isonuomioside A, paraboside II, and paraboside III were quantitatively determined in 12 species of Gesneriaceae by HPLC. The existence and content of these compounds were analyzed. The results showed that phenylethanoid glycosides were found in the most of those plants, but the kind of phenylethanoid glycosides varied in different species. Acteoside distribute in most of this plant group, paraboside B, isonuomioside A, paraboside II, and paraboside III were rare in those plants. The results of this study support morphological viewpoint that Trib. Trichosporeae is more developmental than Trib. Didymocarpeae. PMID:24791528

Bai, Zhen-Fang; Wang, Xiao-Qin; Xiao, Pei-Gen; Liu, Yong



Cardiac metastases  

Microsoft Academic Search

Tumours metastatic to the heart (cardiac metastases) are among the least known and highly debated issues in oncology, and few systematic studies are devoted to this topic. Although primary cardiac tumours are extremely uncommon (various postmortem studies report rates between 0.001% and 0.28%), secondary tumours are not, and at least in theory, the heart can be metastasised by any malignant

R Bussani; F De-Giorgio; A Abbate; F Silvestri



Cardiac asthma.  


Cardiac dyspnea, especially if present only with exercise, is often confused with asthma and exercise-induced bronchospasm. Cardiac dyspnea or asthma is the consequence of pulmonary edema due to pulmonary venous hypertension and not due to asthmatic bronchoconstriction. In overt, acute congestive heart failure, the diagnosis may be readily made by history and physical examination and pertinent laboratory and imaging data. PMID:23337063

Buckner, Kern



Response of ?? T cells to plant-derived tannins  

PubMed Central

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 ?? T cells are described. These plant-derived agonists impart innate effector functions upon distinct ?? T cell subsets. Plant tannins represent one class of ?? T cell agonist and preferentially activate the mucosal population. Mucosal ?? T cells function to modulate tissue immune responses and induce epithelium repair. Select tannins, isolated from apple peel, rapidly induce immune gene transcription in ?? 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 ?? T cells. Procyanidin-induced responses described in this review likely account for the expansion of mucosal ?? 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

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



Phenotypic and Phylogenetic Characterization of Ruminal Tannin-Tolerant Bacteria  

PubMed Central

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

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



Cardiac rhabdomyosarcoma.  


Cardiac sarcoma is a very rare neoplasm and is difficult to diagnose. The case of a 51-year-old man with a left atrial tumour, locally recurrent three months after its surgical removal, is presented. Computed tomography showed metastatic spread to the lung parenchyma. On revised histology, the mass extirpated was a sarcoma. Because of the metastatic spread, further therapy was symptomatic only; the patient died 15 months after the first manifestation of his problems. Immunohistochemical staining confirmed cardiac rhabdomyosarcoma with metastatic spread to the lungs. Difficulty in diagnosing and treating cardiac tumours is discussed. PMID:20428274

Chlumský, J; Holá, D; Hlavácek, K; Michal, M; Svec, A; Spatenka, J; Dusek, J



A new flavonoid glycoside from Vaccaria hispanica.  


A profiling analysis for the methanol extract of the seeds of Vaccaria hispanica (Mill.) Rauschert was performed using a HPLC-ESI-MS technique. Five compounds were identified according to their retention times, UV spectroscopic and MS features, and by comparison with literature data. Among them, a new flavonoid glycoside, named vaccarin H, was isolated and the structure determined by spectral and chemical analysis as isovitexin 2"-O-alpha-L-arabinopyranosyl-4'-O-(6"-O-dihydroferuloyl)-3-beta-glucopyranoside. PMID:22224271

Zhang, Haijiang; Wang, Kuiwu; Wu, Jie; Chen, Yao; He, Peipei



[Caffeoyl phenylethanoid glycosides from Callicarpa kwangtungensis].  


Phytochemical investigation on the EtOH extract from the aerial part of Callicarpa kwangtungensis led to the isolation and characterization of 10 caffeoyl phenylethanoid glycosides, 2'-acetylacteoside (1), tubuloside E (2), acteoside (3), tubuloside B (4), isoacteoside (5), alyssonoside (6), 2'-acetylforsythoside B (7), brandioside (8), forsythoside B (9), and poliumoside (10). Compound 4 was isolated from the plants of Verbenaceae,and 6 was obtained from the Callicarpa genus, for the first time, while compounds 1, 2, 5 and 7 were firstly reported from the plant. PMID:25095374

Hu, Xiao; Li, Li; Yang, Yi-Fang; Huang, Chun-Yue; Huang, Guang-Lei



Acetophenone glycosides from thyme (Thymus vulgaris L.).  


Four acetophenone glycosides were isolated from the butanol-soluble fraction of thyme extracts. Their structures were determined by spectral methods (MS, NMR, and 2D-NMR). Among them, two new compounds, 4-hydroxyacetophenone 4-O-[5-O-(3, 5-dimethoxy-4-hydroxybenzoyl)-beta-D-apiofuranosyl]-(1-->2)-beta-D -gl ucopyranoside (1) and 4-hydroxyacetophenone 4-O-[5-O-(4-hydroxybenzoyl)-beta-D-apiofuranosyl]-(1-->2)-beta-D-+ ++gluc opyranoside (2), were determined. Compound 1 showed weak cytotoxicity, inhibiting DNA synthesis of human leukemia cells. PMID:10552470

Wang, M; Kikuzaki, H; Lin, C C; Kahyaoglu, A; Huang, M T; Nakatani, N; Ho, C T



Ergot alkaloid glycosides with immunomodulatory activities  

Microsoft Academic Search

New glycosides derived from ergot alkaloids elymoclavine and DH-lysergol were synthesized by chemoenzymatic methods. ?-Glucosides were obtained either by chemical method or by transglycosylation (glycosidase from Aspergillus oryzae), lactosides were prepared by further extension of carbohydrate chain using ?-1,4-galactosyltransferase (bovine milk) and ?-5-N-acetylneuraminyl-(2?6)-?-d-galactopyranosyl-(1?4)- 2-acetamido-2-deoxy-?-d-glucopyranosyl-(1?O)-elymoclavine was prepared using ?-2,6-sialyltransferase (rat liver). Immunomodulatory activity of elymoclavine and 9,10-dihydrolysergol and their glycosylated derivatives

Vladimír K?en; Anna Fišerová; Claudine Augé; Petr Sedmera; Vladimír Havlí?ek; Petr Šíma



Flavonol glycosides of Warburgia ugandensis leaves  

Microsoft Academic Search

Four new flavonol glycosides: kaempferide 3-O-?-xylosyl (1?2)-?-glucoside, kaempferol 3-O-?-rhamnoside-7,4?-di-O-?-galactoside, kaempferol 3,7,4?-tri-O-?-glucoside and quercetin 3-O-[?-rhamnosyl (1?6)] [?-glucosyl (1?2)]-?-glucoside-7-O-?-rhamnoside, were characterized from a methanolic leaf extract of Warburgia ugandensis. The known flavonols: kaempferol, kaempferol 3-rhamnoside, kaempferol 3-rutinoside, myricetin, quercetin 3-rhamnoside, kaempferol 3-arabinoside, quercetin 3-glucoside, quercetin, kaempferol 3-rhamnoside-4?-galactoside, myricetin 3-galactoside and kaempferol 3-glucoside were also isolated. Structures were established by spectroscopic and chemical

Lawrence O. Arot Manguro; Ivar Ugi; Peter Lemmen; Rudolf Hermann



Baccharane glycosides from seeds of Impatiens balsamina.  


From the seeds of Impatiens balsamina have been isolated four rare baccharane glycosides, hosenkosides L-O. The structures of all isolates were secured by the use of 2D NMR techniques (1H-1H COSY, HMQC, HMBC, ROESY) and chemical derivatization. Hosenkosides L and M are hosenkol A 3-O-sambubiosyl-28-O-glucoside and 3-O-sambubiosyl-26-O-glucosyl-28-O-glucoside, respectively. Hosenkoside N is hosenkol C 3-O-glucosyl-28-O-glucoside. Hosenkoside O is hosenkol D 3-O-sophorosyl-28-O-glucoside. PMID:7765763

Shoji, N; Umeyama, A; Yoshikawa, K; Nagai, M; Arihara, S



Deuterium NMR Investigation of the lyotropic phases of alkyl ?-glycoside/D2O systems.  


We have investigated the phase behavior of four glycosides (?C8OGlc, ?C8SGlc, ?C10OGlc, ?C8OGal) in water and D2O by optical polarizing microscopy and deuterium NMR. Previously published phase diagrams were evaluated by deuterium NMR, via monitoring D2O spectra, and confirmed the presence of the hexagonal, bicontinuous cubic, and lamellar phases in these glycosides. We have also shown the presence of the gel phase in (?C10OGlc) and observed the extensive supercooling of the lamellar phase to temperatures well below the Kraft line. While the main features of the phase diagrams were confirmed, some phase boundaries were found to be slightly different. Magnetically aligned spectra were also observed for relatively dilute samples for the hexagonal phase (?C8OGlc and ?C8OGal) and the lamellar phase (?C8SGlc and ?C10OGlc). The average number of bound water molecules per headgroup in the lamellar phase for the glycosides was determined by the systematic measurement of the quadrupolar splitting of D2O over a wide range of values of the (glycoside/water) molar ratio. The number of water molecules bound to the headgroup was found on average to be about 1.6-1.7 water molecules with no significant differences in this value for the different glycosides (and over the temperature range investigated), indicating that the bound water content is predominately influenced by the number of hydroxyl groups of the headgroup only. However, this bound water content of only 1.6-1.7 water molecules per sugar headgroup is surprisingly low, suggesting strong intermolecular interactions of the OH groups of headgroup sugars. The results are in line with computational results reported earlier for the octyl-?-glucoside and ?-galactoside, which show the presence of strong intralayer hydrogen bonding. PMID:23718628

Misran, Omar; Timimi, Bakir A; Heidelberg, Thorsten; Sugimura, Akihiko; Hashim, Rauzah



Multiple defensive roles for triterpene glycosides from two Caribbean sponges  

Microsoft Academic Search

Despite their high nutritional value and a lack of physical defenses, most marine sponges appear to be minimally affected by predators, competitors, and fouling organisms, possibly due to sponge chemical defenses. In the last 15 years, several triterpene glycosides have been isolated from sponges, but their ecological or physiological roles are largely unknown. We tested triterpene glycosides from Erylus formosus

Julia Kubanek; Kristen E. Whalen; Sebastian Engel; Sarah R. Kelly; Timothy P. Henkel; William Fenical; Joseph R. Pawlik



Fully acetylated carbamate and hypotensive thiocarbamate glycosides from Moringa oleifera  

Microsoft Academic Search

Six new and three synthetically known glycosides have been isolated from the leaves of Moringa oleifera, employing a bioassay-directed isolation method on the ethanolic extract. Most of these compounds, bearing thiocarbamate, carbamate or nitrile groups, are fully acetylated glycosides, which are very rare in nature. Elucidation of the structures was made using chemical and spectroscopic methods, including 2D NMR techniques.

Shaheen Faizi; Bina Shaheen Siddiqui; Rubeena Saleem; Salimuzzaman Siddiqui; Khalid Aftab; Anwar-Ul-Hassan Gilani



Verbascoside derivatives and iridoid glycosides from Penstemon crandallii  

Microsoft Academic Search

The new phenylethanoid glycosides 2-O-acetyl-3?-O-methylverbascoside and 2,4?-di-O-acetyl-3?-O-methylverbascoside were isolated and identified from Penstemon crandallii. The major iridoid glycoside was plantarenaloside and no aucubin type iridoids were found. This contrasted with a previous analysis of P. teucrioides, from the same Penstemon subsection, which was dominated by aucubin derivatives.

Lotfy D. Ismail; Mohamed M. El-Azizi; Taha I. Khalifa; Frank R. Stermitz



[Cardiac angiosarcoma].  


The paper outlines the authors'case of cardiac angiosarcoma. It provides the gross and microscopic characteristics of this tumor and procedures for its clinical and immunomorphological diagnosis. PMID:21695990

Kir'ianov, N A; Terekhov, M V; Sukhanov, S A; Lozhkin, E A; Nikolaeva, N B



Cardiac Cephalalgia  

Microsoft Academic Search

We report a patient with cardiac cephalalgia and review reported cases from the English-language literature based on the new diagnostic criteria published in the International Classification of Headache Disorders, ed 2. Twenty-two patients, including ours, with headaches of cardiac origin were reviewed. The cases fit three of the four new criteria well: Criteria B (acute myocardial ischemia has occurred, 100%),

Shih-Pin Chen; Jong-Ling Fuh; Wen-Chung Yu; Shuu-Jiun Wang



Resin glycosides from Ipomoea pes-caprae.  


Ipomoea pes-caprae (beach morning-glory; "riñonina" for the herbal drug in Mexico) is prescribed by traditional healers to moderate "heat" in an infected kidney. The hexane-soluble extract from the aerial parts of this medicinal plant, through preparative-scale recycling HPLC, yielded six new lipophilic oligosaccharides of jalapinolic acid: pescaproside B (1) and pescapreins V-IX (2-6). The previously known pescaproside A (7), pescapreins I-IV (8-11), and stoloniferin III (12) were also identified in the analyzed material by means of HPLC comparison with authentic samples. The glycosidic acid structure for all pentasaccharides was confirmed as simonic acid B. Pescaproside B (1), an acylated glycosidic acid methyl ester, is structurally related to pescaprein III (10). Pescapreins V (2) and VI (3) are diasteroisomeric tetraglycosidic lactones of operculinic acid C. Both of these compounds contain (2S)-methylbutyric and n-dodecanoic acids as their esterifying residues. Pescapreins VII (4) and IX (6) are pentasaccharides that contain an n-decanoyl group as their esterifying fatty acid residue instead of the n-dodecanoyl found in pescapreins I (8) and IV (11). Pescaprein VIII (5) represents an isomer of pescaprein II (9) containing an n-dodecanoyl unit as the esterifying residue at position C-4 of the third rhamnose moiety and a 2-methylpropanoyl at C-2 of the second rhamnose. High-field NMR spectroscopy and FAB mass spectrometry were used to characterize all new isolated compounds. PMID:17511505

Escobedo-Martínez, Carolina; Pereda-Miranda, Rogelio



Ergot alkaloid glycosides with immunomodulatory activities.  


New glycosides derived from ergot alkaloids elymoclavine and DH-lysergol were synthesized by chemoenzymatic methods. beta-Glucosides were obtained either by chemical method or by transglycosylation (glycosidase from Aspergillus oryzae), lactosides were prepared by further extension of carbohydrate chain using beta-1,4-galactosyltransferase (bovine milk) and alpha-5-N-acetylneuraminyl-(2-->6)-beta-D-galactopyranosyl-(l-->4)-2- acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->O)-elymoclavine was prepared using alpha-2,6-sialyltransferase (rat liver). Immunomodulatory activity of elymoclavine and 9,10-dihydrolysergol and their glycosylated derivatives on natural killer (NK) cell-mediated cytotoxicity of human resting and activated human peripheral blood mononuclear cells (PBMC) was investigated. Addition of ergot alkaloid glycosides to the mixtures of effector and target cells potentiated the PBMC cytotoxicity against both NK-sensitive and -resistant target cells. The glycoconjugates of elymoclavine enhanced cytotoxicity of PBMC against NK-resistant target cells. The glycoconjugates of DH-lysergol potentiated NK cytotoxicity of PBMC against NK-sensitive target cells. PMID:8818236

Kren, V; Fiserová, A; Augé, C; Sedmera, P; Havlícek, V; Síma, P



Enzymatic synthesis of epothilone A glycosides  

PubMed Central

Epothilones are extremely cytotoxic chemotherapeutic agents with epoxide, thiazole, and ketone groups that share equipotent kinetic similarity with taxol. The in vitro glycosylation catalyzed by uridine diphosphate glucosyltransferase (YjiC) from Bacillus licheniformis generated six novel epothilone A glycoside analouges including epothilone A 7-O-?-D-glucoside, epothilone A 7-O-?-D-galactoside, epothilone A 3,7-O-?-D-digalactoside, epothilone A 7-O-?-D-2-deoxyglucoside, epothilone A 7-O-?-L-rhamnoside, and epothilone A 7-O-?-L-fucoside. Epothilone A 7-O-?-D-glucoside was structurally elucidated by ultra-high performance liquid chromatography-photo diode array (UPLC-PDA) conjugated with high resolution quantitative time-of-flight-electrospray ionization mass spectroscopy (HR-QTOF ESI-MS/MS) supported by one-and two-dimensional nuclear magnetic resonance studies whereas other epothilone A glycosides were characterized by UPLC-PDA and HR-QTOF ESI-MS/MS analyses. The time dependent conversion study of epothilone A to epothilone A 7-O-?-D-glucoside found to be maximum (~26%) between 3 h to 5 h incubation. PMID:24949266



Performance and characterization of a new tannin-based coagulant  

NASA Astrophysics Data System (ADS)

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.

Beltrán-Heredia, J.; Sánchez-Martín, J.; Gómez-Muñoz, C.



About Cardiac Arrest  


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Identification of carcinogenic tannin isolated from Bracken fern (Pteridium aquilinum).  


We attempted to isolate a carcinogenic substance from bracken fern (Pteridium aquilinum), a naturally occurring toxicant responsible for the production of chronic enzootic hematuria and urinary bladder cancer of cattle and carcinogenic for various target organs of several species. Hot methanol extracts of bracken fern were solubilized in water and extracted with chloroform followed by a mixture of n-butanol-butanone (1:1). That fraction was dried and triturated with ether-methanol (4:1), n-butanol, and finally absolute ethanol. The insoluble residue was dissolved in 10% aqueous methanol and passed through Dowex 1 OH-, Dowex 50 H+, or Dowex 1 OH- and then Dowex 50 H+ ion exchange resins. A condensed tannin, isolated from one ot the fractions, was identical to that isolated from bracken fern by the caffeine procedure used for the separation of tannins from other plant constituents. Three systems were used for bioassay; induction of bladder carcinoma by implantation of cholesterol pellets containing bracken fern fractions into the bladder lumens of mice; acute toxicity by ip injection of brachen fern fraction into mice; and growth inhibition of Escherichia coli. The following fractions induced significantly greater incidences of bladder carcinoma than did cholesterol pellets only: tannin, Dowex 50 H+, residue, n-butanol, and methanol. Tiliroside, a component of bracken fern fractions into the bladder lumens of mice; acute genic acid, and quercetin were not carcinogenic. Tannin was the most toxic (mean lethal dose: 0.16 mg/g) and carcinogenic. None of the carcinogenic fractions inhibited growth of E. coli. PMID:768500

Wang, C Y; Chiu, C W; Pamukcu, A M; Bryan, G T



Determination of bioactive nitrile glycoside(s) in drumstick ( Moringa oleifera) by reverse phase HPLC  

Microsoft Academic Search

A high-performance liquid chromatographic method for the determination of novel bioactive nitrile glycosides niaziridin and niazirin in the leaves, pods and bark of Moringa oleifera is reported. Niaziridin is a bioenhancer for drugs and nutrients. The analytical conditions for reversed-phase HPLC with UV detection were as follows: column, Chromolith RP-18e, 4.6×100mm 0.5?m (Merck); column temperature, 25°C; mobile phase, a 20:80

Karuna Shanker; Madan M. Gupta; Santosh K. Srivastava; Dnyaneshwar U. Bawankule; Anirban Pal; Suman P. S. Khanuja



Condensed tannin changes induced by autoxidation: effect of the initial degree of polymerization and concentration.  


Condensed tannins are a major class of polyphenols and play an important part in organoleptic properties of beverages. Because of their structure, they are chemically reactive. During food processing, reactions take place, leading to structural changes of the native structures to give modified tannins and pigments. Average degrees of polymerization (DPs) determined by standard depolymerization methods become irrelevant, because bonds created from oxidation are uncleavable. Small-angle X-ray scattering was used to determine the conformation of native and autoxidized tannins and assess the impact of tannins initial DP and concentration on changes induced by autoxidation. Different behaviors were observed: (i) slight increase of the DP when tannins were oxidized in dilute solutions; (ii) increase of the DP with tannins in concentrated solutions, leading to the formation of longer linear chains or branched macromolecules depending on the initial DP. PMID:25025340

Vernhet, Aude; Carrillo, Stéphanie; Poncet-Legrand, Céline



Spectrophotometric estimation of individual flavone glycosides in three Euphorbia species.  


Two spectrophotometric methods (conventional and differential) are carried out for the estimation of flavone glycosides (hyperoside and/or kaempferol-3-beta-glucoside) in Euphorbia paralias L., and Euphorbia helioscopia L. The glycosides are extracted with methanol from the aerial parts of the different Euphorbia species, separated on silica gel chromatoplates, and eluted by refluxing with methanol (80%). The absorbance value (conventional method) and the delta absorbance value (differential method) of the prepared glycosidal solutions are measured. The results of both methods are of conveinent reproducibility. PMID:1161795

Abdel-Salam, N A; El-Sayed, M; Khafagy, S M



Synthesis and sensory evaluation of ent-kaurane diterpene glycosides.  


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)? and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR spectral data and chemical studies. Also, we report herewith the sensory evaluation of all the reduced compounds against their corresponding original steviol glycosides and sucrose for the sweetness property of these molecules. PMID:22836210

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



Cardiac Regeneration  

PubMed Central

The heart is a pump that is comprised of cardiac myocytes and other cell types and whose proper function is critical to quality of life. The ability to trigger regeneration of heart muscle following injury eludes adult mammals, a deficiency of great clinical impact. Major research efforts are attempting to change this through advances in cell therapy or activating endogenous regenerative mechanisms that exist only early in life. By contrast with mammals, lower vertebrates like zebrafish demonstrate an impressive natural capacity for cardiac regeneration throughout life. This review will cover recent progress in the field of heart regeneration with a focus on endogenous regenerative capacity and its potential manipulation. PMID:22449849

Choi, Wen-Yee; Poss, Kenneth D.



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

NASA Astrophysics Data System (ADS)

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.

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



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

USGS Publications Warehouse

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.

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



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

NASA Astrophysics Data System (ADS)

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 ?m) 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.

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



The formulation and commercialization of glulam pine tannin adhesives in Chile  

Microsoft Academic Search

The results of fingerjointing and glulam industrial trials in Chile using a “honeymoon” fast-set adhesive system manufactured\\u000a using commercially-produced mildly-sulphited pine tannin extract are reported. The results obtained satisfy the relevant international\\u000a standards specifications and constitute the first occasion that a commercially produced pine tannin adhesive has been used\\u000a succesfully in industrial productions runs. This pine tannin adhesive is now

E. von Leyser; A. Pizzi



Characterization of a formaldehyde-free cornstarch-tannin wood adhesive for interior plywood  

Microsoft Academic Search

This study investigated the physical properties (rheological and thermogravimetric analysis) of cornstarch-tannin adhesives\\u000a and the mechanical properties (dry tensile strength and 3-point bending strength) of plywood made using cornstarch-tannin\\u000a adhesives. This adhesive was evaluated for its utility in interior plywood manufacture. The optimum cure temperature and cure\\u000a time of cornstarch-tannin adhesives were 170°C and 4?min, respectively. Plywood bonded with formaldehyde-free

Amine Moubarik; Ahmed Allal; Antonio Pizzi; Fatima Charrier; Bertrand Charrier



Identification of the origin of commercial enological tannins by the analysis of monosaccharides and polyalcohols  

Microsoft Academic Search

The monosaccharide and polyalcohol composition of 28-samples of different commercial tannins, including oak wood, grape seed and skin, plant gall, chestnut, quebracho and gambier, has been evaluated by gas chromatography–mass spectrometry after derivatization into their trimethylsilyl ethers. Quercitol was found to be characteristic of oak tannins, whereas gall plant tannins could be differentiated by their content of pinitol. Myo-inositol and

M. Luz Sanz; Isabel Martínez-Castro; M. Victoria Moreno-Arribas



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


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. PMID:23289627

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



Characterisation of tannins and in vitro protein digestibility of several Lotus corniculatus varieties  

Microsoft Academic Search

Seven birdsfoot trefoil (BFT) varieties (Lotus corniculatus) grown in Sweden, were harvested at the 50% flowering stage and analysed for tannins by the radial diffusion and HCl–butanol methods. The flavan-3-ol composition of different BFT tannins was determined by HPLC. Tannins were isolated and examined for their molecular weight distributions by HPLC gel permeation chromatography (GPC) and MALDI-TOF mass spectrometry. Ruminal

Helena Hedqvist; Irene Mueller-Harvey; Jess D Reed; Christian G Krueger; Michael Murphy



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

NASA Astrophysics Data System (ADS)

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.

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



Assessment of tannin variation in Tamarisk foliage across a latitudinal gradient  

USGS Publications Warehouse

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.

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



Condensed tannins from Ficus virens as tyrosinase inhibitors: structure, inhibitory activity and molecular mechanism.  


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 ?g/ml on monophenolase activity, and 128.42, 43.07, and 74.27 ?g/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

Chen, Xiao-Xin; Shi, Yan; Chai, Wei-Ming; Feng, Hui-Ling; Zhuang, Jiang-Xing; Chen, Qing-Xi



Calcium influx is required for tannin-mediated arachidonic acid release from alveolar macrophages.  


The role of Ca2+ was investigated in the response of alveolar macrophages to cotton tannin, an agent implicated in the lung disease byssinosis in textile mill workers. A physiological concentration of extracellular Ca2+ was found to be required for tannin-mediated release of radiolabeled arachidonic acid (AA). Flow cytometry using indo 1 indicated that tannin caused a rapid and dose-dependent Ca2+ increase in macrophages that also required extracellular Ca2+. Ethylene glycol-bis(beta-aminoethyl ether)-N,N,N',N'-tetraacetic acid virtually abolished the Ca2+ influx mediated by tannin but had little effect on intracellular Ca2+ release induced by thapsigargin, N-formylmethionyl-leucylphenylalanine, or thimerosal. A mechanism for extracellular Ca2+ influx was demonstrated by rapid Mn2+ quenching of indo 1 by tannin. Verapamil inhibited tannin-mediated Ca2+ influx and AA release, but the effective concentration was 100 microM. 1,2-Bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid chelated all Ca2+ in the cells and effectively abolished the tannin response. Exposure to tannin was not associated with cytotoxicity, as judged by 51Cr release. The data suggest that tannin induces Ca2+ influx in alveolar macrophages, which represents an important prerequisite for a cell-signaling pathway resulting in the accumulation of free AA. PMID:7840226

Bates, P J; Ralston, N V; Vuk-Pavlovi?, Z; Rohrbach, M S



Tannin impacts on microbial diversity and the functioning of alpine soils: a multidisciplinary approach.  


In alpine ecosystems, tannin-rich-litter decomposition occurs mainly under snow. With global change, variations in snowfall might affect soil temperature and microbial diversity with biogeochemical consequences on ecosystem processes. However, the relationships linking soil temperature and tannin degradation with soil microorganisms and nutrients fluxes remain poorly understood. Here, we combined biogeochemical and molecular profiling approaches to monitor tannin degradation, nutrient cycling and microbial communities (Bacteria, Crenarcheotes, Fungi) in undisturbed winter time soil cores exposed to low temperature (0 degrees C/-6 degrees C), amended or not with tannins, extracted from Dryas octopetala. No toxic effect of tannins on microbial populations was found, indicating that they withstand phenolics from alpine vegetation litter. Additionally at -6 degrees C, higher carbon mineralization, higher protocatechuic acid concentration (intermediary metabolite of tannin catabolism), and changes in fungal phylogenetic composition showed that freezing temperatures may select fungi able to degrade D. octopetala's tannins. In contrast, negative net nitrogen mineralization rates were observed at -6 degrees C possibly due to a more efficient N immobilization by tannins than N production by microbial activities, and suggesting a decoupling between C and N mineralization. Our results confirmed tannins and soil temperatures as relevant controls of microbial catabolism which are crucial for alpine ecosystems functioning and carbon storage. PMID:18237312

Baptist, F; Zinger, L; Clement, J C; Gallet, C; Guillemin, R; Martins, J M F; Sage, L; Shahnavaz, B; Choler, Ph; Geremia, R



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


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

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



Cardiac Rehabilitation  


Cardiac rehabilitation (rehab) is a medically supervised program to help people who have A heart attack Angioplasty or coronary artery bypass grafting for coronary heart disease A heart valve repair or replacement A heart transplant or a lung transplant Angina Heart failure The ...


A new aryl glycoside from Euphorbia helioscopia L  

Microsoft Academic Search

A new aryl glycoside, 3?-O-galloyl-benzyl-O-?-l-rhamnopyranosyl-(1?6)-?-d-glucopyranoside, was isolated from Euphorbia helioscopia L., and its structure was elucidated on the basis of various spectroscopic data analysis.

Wei Sheng Feng; Li Gao; Xiao Ke Zheng; Yan Zhi Wang



A new lathyrane diterpene glycoside from Euphorbia helioscopia L  

Microsoft Academic Search

A new lathyrane diterpene glycoside, named 3?, 7?, 15?-trihydroxy-14-oxolathyra-5E, 12E-dienyl-16-O-?-d-glucopyranoside, was isolated from Euphorbia helioscopia L. Its structure was established by spectroscopic techniques including 2D NMR.

Wei Sheng Feng; Li Gao; Xiao Ke Zheng; Yan Zhi Wang; Hui Chen



Three new secoiridoid glycoside dimers from Swertia mileensis  

Microsoft Academic Search

Three new secoiridoid glycoside dimers named swerilactosides A–C (1–3) were isolated from Swertia mileensis. Their structures were elucidated based on extensive spectral analyses (1D and 2D NMR, MS, and IR spectroscopic means).

Chang-An Geng; Xue-Mei Zhang; Yun-Bao Ma; Zhi-Yong Jiang; Ji-Feng Liu; Jun Zhou; Ji-Jun Chen



New phenylpropanoid glycosides from Juniperus communis var. depressa.  


Two new phenylpropanoid glycosides were isolated from the leaves and stems of Juniperus communis var. depressa (Cupressaceae) along with 14 known compounds. Their structures were determined by spectral analyses, in particular by 2D-NMR spectral evidence. PMID:20460808

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



Flavone C-glycosides from Bryonia alba and B. dioica  

Microsoft Academic Search

Lutonarin was isolated from Bryonia alba and B. dioica. Five further C-glycosides: vitexin, isovitexin, isoorientin, saponarin were isolated from B. dioica together with saponarin caffeic ester, a new natural product.

Miroslawa Krauze-Baranowska; Wojciech Cisowski



Secoiridoid glycoside and alkaloid constituents of Hydrangea chinensis.  


A new secoiridoid glycoside, hydrachoside A (1), along with 14 known compounds, was isolated from the leaves of Hydrangea chinensis. The absolute stereochemistry of the side chain attached to C-15 on the secoiridoid glycoside hydrangenoside E (2) was determined by NMR spectral analysis. The structures of compounds 1 and 2 were elucidated on the basis of spectral data. The previously reported structure, hydrachine A (3), was revised as its epimer, (-)-neodichroine (4), a new compound. PMID:14510608

Chang, Fang-Rong; Lee, Yue-Han; Yang, Yu-Liang; Hsieh, Pei-Wen; Khalil, Ashraf T; Chen, Chung-Yi; Wu, Yang-Chang



Temporal and spatial variation in cyanogenic glycosides in Eucalyptus cladocalyx  

Microsoft Academic Search

Summary The release of hydrogen cyanide from endoge- nous cyanide-containing compounds in plants is an effective herbivore deterrent. We investigated temporal and spatial vari- ations in cyanogenic glycoside concentration in greenhouse- grown seedlings and 6-year-old plantation trees of Eucalyptus cladocalyx F. Muell., which allocates up to 20% of leaf nitro- gen to the cyanogenic glycoside, prunasin. The highest cyano- genic



Cardiac inotropes: current agents and future directions.  


Intrinsic inotropic stimulation of the heart is central to the regulation of cardiovascular function, and exogenous inotropic therapies have been used clinically for decades. Unfortunately, current inotropic drugs have consistently failed to show beneficial effects beyond short-term haemodynamic improvement in patients with heart failure. To address these limitations, new agents targeting novel mechanisms are being developed: (i) istaroxime has been developed as a non-glycoside inhibitor of the sodium-potassium-ATPase with additional stimulatory effects on the sarcoplasmic reticulum calcium pump (SERCA) and has shown lusitropic and inotropic properties in experimental and early clinical studies; (ii) from a mechanistic point of view, the cardiac myosin activators, directly activating the acto-myosin cross-bridges, are most appealing with improved cardiac performance in both animal and early clinical studies; (iii) gene therapy approaches have been successfully employed to increase myocardial SERCA2a; (iv) nitroxyl donors have been developed and have shown evidence of positive lusitropic and inotropic, as well as potent vasodilatory effects in early animal studies; (v) the ryanodine receptor stabilizers reduce pathological leak of calcium from the sarcoplasmic reticulum with initial promising pre-clinical results; and finally, (vi) metabolic energy modulation may represent a promising means to improve contractile performance of the heart. There is an urgent clinical need for agents that improve cardiac performance with a favourable safety profile. These current novel approaches to improving cardiac function provide the hope that such agents may soon be available. PMID:21388993

Hasenfuss, Gerd; Teerlink, John R



Cyanogenic glycosides: synthesis, physiology, and phenotypic plasticity.  


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

Gleadow, Roslyn M; Møller, Birger Lindberg



Antioxidant flavonol glycosides from Schinus molle.  


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

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



Cardiac optogenetics  

PubMed Central

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



Cardiac Surgery  

PubMed Central

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

Weisse, Allen B.



Oligomers distribution at the gel point of tannin–formaldehyde thermosetting adhesives for wood panels  

Microsoft Academic Search

Tannin–formaldehyde (TF) thermosetting wood adhesives for panel products for the building industry were examined to determine which oligomers were formed during the reaction between tannin and formaldehyde. The reaction products were examined by Matrix Assisted Laser Desorption\\/Ionization Time of Flight mass spectrometry. The analysis revealed that at the gel point, the adhesive was composed of unreacted flavonoid monomers and some

A. Pizzi; H. Pasch; A. Celzard; A. Szczurek



Polyflavonoid tannins — a main cause of soft-rot failure in CCA-treated timber  

Microsoft Academic Search

Polyflavonoid tannins are proven to be fast-reacting with CCA solutions and hence, to be strong competitors of the structural wood constituents for fixation of CCA preservatives. The consequence of this effect is that even relatively small amounts of tannin cause severe undertreatment of the structural wood constituents which in turn badly affects the long term durability of CCA treated timber.

A. Pizzi; A. Jansen



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

Microsoft Academic Search

A 4-week feeding trial on 22 grey partridges Perdix perdix was conducted in this study. Seven birds were fed commercial poultry food, seven natural food and eight commercial poultry food containing 6% of quebracho–tannin. Our results suggest that 6% dietary tannin, when added to a commercial food with high protein content, effects the grey partridge only slightly. No difference was

Tuija Liukkonen-Anttila; Airi Kentala; Raimo Hissa



Morphology and agronomic performance of white clover with increased flowering and condensed tannin concentration  

Microsoft Academic Search

High tannin (HT) white clover (Trifolium repens), bred for increased floral condensed tannin (CT) and flowering prolificacy, was assessed under dairy grazing in the Waikato region of New Zealand. HT and ‘Grasslands Huia’ white clover monocultures sown in April 2001 were monitored until November 2003. HT grew 1 t DM ha less than ‘Huia’ each year and both had similar

V. T. Burggraaf; S. L. Woodward; D. R. Woodfield; E. R. Thom; G. C. Waghorn; P. D. Kemp



A genetic polymorphism for tannin production in Lotus corniculatus and its relationship to cyanide polymorphism  

Microsoft Academic Search

A study of 172 unnamed populations and 22 cultivars of Lotus corniculatus showed: (1) that all plants of most strains of both categories contained leaf tannins (total 172 strains); (2) that 6 strains were tannin-negative; and (3) that 16 strains were polymorphic. Because of the small number of tested plants per strain, the above frequency of polymorphism is probably underestimated.

M. D. Ross; W. T. Jones



Insect grazing on Eucalyptus in response to variation in leaf tannins and nitrogen  

Microsoft Academic Search

Many species of Eucalyptus, one of the dominant genera in Australian forests and woodlands, contain high levels of tannins and other phenols and are also heavily damaged by grazing insects. These phenols do not appear to affect insect attack because a wide range of concentrations of condensed tannins and other phenols in leaves of 13 Eucalyptus sp. influenced neither feeding

Laurel R. Fox; B. J. Macauley



Glycosidic inhibitors of melanogenesis from leaves of Passiflora edulis.  


A new flavonoid glycoside, chrysin 6-C-?-rutinoside (chrysin ?-L-rhamnopyranosyl-(1?6)-C-?-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 ?-melanocyte-stimulating hormone (?-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??M. 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 ?-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. PMID:24130028

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



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


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. PMID:24011384

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



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


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. PMID:25053028

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



Steviol glycoside safety: is the genotoxicity database sufficient?  


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. PMID:23103588

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



Human psychometric and taste receptor responses to steviol glycosides.  


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. PMID:22616809

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



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

PubMed Central

Background and Aims Condensed tannins (also called proanthocyanidins) are widespread polymers of catechins and are essential for the defence mechanisms of vascular plants (Tracheophyta). A large body of evidence argues for the synthesis of monomeric epicatechin on the cytosolic face of the endoplasmic reticulum and its transport to the vacuole, although the site of its polymerization into tannins remains to be elucidated. The aim of the study was to re-examine the cellular frame of tannin polymerization in various representatives of the Tracheophyta. Methods Light microscopy epifluorescence, confocal microscopy, transmission electron microscopy (TEM), chemical analysis of tannins following cell fractionation, and immunocytochemistry were used as independent methods on tannin-rich samples from various organs from Cycadophyta, Ginkgophyta, Equisetophyta, Pteridophyta, Coniferophyta and Magnoliophyta. Tissues were fixed in a caffeine–glutaraldehyde mixture and examined by TEM. Other fresh samples were incubated with primary antibodies against proteins from both chloroplastic envelopes and a thylakoidal chlorophyll-carrying protein; they were also incubated with gelatin–Oregon Green, a fluorescent marker of condensed tannins. Coupled spectral analyses of chlorophyll and tannins were carried out by confocal microscopy on fresh tissues and tannin-rich accretions obtained through cell fractionation; chemical analyses of tannins and chlorophylls were also performed on the accretions. Key Results and Conclusions The presence of the three different chloroplast membranes inside vacuolar accretions that constitute the typical form of tannin storage in vascular plants was established in fresh tissues as well as in purified organelles, using several independent methods. Tannins are polymerized in a new chloroplast-derived organelle, the tannosome. These are formed by pearling of the thylakoids into 30 nm spheres, which are then encapsulated in a tannosome shuttle formed by budding from the chloroplast and bound by a membrane resulting from the fusion of both chloroplast envelopes. The shuttle conveys numerous tannosomes through the cytoplasm towards the vacuole in which it is then incorporated by invagination of the tonoplast. Finally, shuttles bound by a portion of tonoplast aggregate into tannin accretions which are stored in the vacuole. Polymerization of tannins occurs inside the tannosome regardless of the compartment being crossed. A complete sequence of events apparently valid in all studied Tracheophyta is described. PMID:24026439

Brillouet, Jean-Marc; Romieu, Charles; Schoefs, Benoit; Solymosi, Katalin; Cheynier, Veronique; Fulcrand, Helene; Verdeil, Jean-Luc; Conejero, Genevieve



Two new flavonol glycosides from Dimocarpus longan leaves.  


From the extracts of Dimocarpus longan Lour leaves, 2 unusual flavonol glycosides, quercetin 3-O-(3?-O-2?-methyl-2?-hydroxylethyl)-?-d-xyloside (1) and quercetin 3-O-(3?-O-2?-methyl-2?-hydroxylethyl)-?-l-rhamnopyranoside (2), as well as 10 known compounds including 2 flavonol glycosides, afzelin (3) and kaempferol-3-O-?-l-rhamnopyranoside (4), 2 flavans, ( - )-epicatechin (5) and proanthocyanidin A-2 (6), 3 triterpenoids, friedelin (7), epifriedelanol (8) and ?-amyrin (9), a peptide, N-benzoylphenylalanyl-N-benzoylphenylalaninate (10), and 2 sterols, ?-sitosterol (11) and daucosterol (12) were isolated and identified by using combination of mass spectrometry and various 1D and 2D NMR techniques. This is the first report of flavonoid glycosides possessing a 2-methyl-2-hydroxylethoxyl group in sugar moiety from D. longan. PMID:25325562

Xue, Yongmei; Wang, Wenjing; Liu, Yujiao; Zhan, Rui; Chen, Yegao



3-Hydroxy-3-methylglutaryl flavonol glycosides from Oxytropis falcata.  


Five new 3-hydroxy-3-methylglutaryl (HMG) flavonol 3-O-glycosides, named oxytroflavosides A-E (1-5), and two new rhamnocitrin 3-O-glycosides, oxytroflavosides F and G (6 and 7) were isolated from the n-BuOH-soluble fraction of an EtOH extract of Oxytropis falcata together with seven known kaempferol glycosides (8-14), of which six were isolated from the genus Oxytropis for the first time. The structures of these compounds were elucidated by spectroscopic techniques and chemical methods. The absolute configuration of HMG in compounds 1-5 was determined to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. Compounds 1-10 were evaluated for anti-inflammatory activities using lipopolysaccharide-induced RAW 264.7 cells, but none of them showed inhibitory effects on NO production. PMID:22775441

Wang, Shan-Shan; Zhang, Xiao-Jing; Que, Sheng; Tu, Guang-Zhong; Wan, Dan; Cheng, Wei; Liang, Hong; Ye, Jia; Zhang, Qing-Ying



Ecdysteroid glycosides: identification, chromatographic properties, and biological significance.  


Ecdysteroid glycosides are found in both animals and plants. The chromatographic behavior of these molecules is characteristic, as they appear much more polar than their corresponding free aglycones when analyzed by normal-phase high-performance liquid chromatography (HPLC), whereas the presence of glycosidic moieties has a very limited (if any) impact on polarity when using reversed-phase HPLC. Biological activity is greatly reduced because the presence of this bulky substituent probably impairs the interaction with ecdysteroid receptor(s). 2-Deoxy-20-hydroxyecdysone 22-O-beta-D-glucopyranoside, which has been isolated from the dried aerial parts of Silene nutans (Caryophyllaceae), is used as a model compound to describe the rationale of ecdysteroid glycoside purification and identification. PMID:15842754

Maria, Annick; Girault, Jean-Pierre; Saatov, Ziyadilla; Harmatha, Juraj; Dinan, Laurence; Lafont, René



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


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. PMID:24809533

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



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


During the storage, bottled white wines can manifest haziness due to the insolubilisation of the grape proteins that may 'survive' in the fermentation process. Although the exact mechanism of this occurrence is not fully understood, proteins and tannins are considered two of the key factors involved in wine hazing, since their aggregation leads to the formation of insoluble particles. To better understand this complex interaction, proteins and tannins from the same unfined Pinot grigio wine were separated. Wine proteins were then fractionated by hydrophobic interaction chromatography (HIC). A significant correlation between hydrophobicity of the wine protein fractions and the haze formed after reacting with wine tannins was found, with the most reactive fractions revealing (by SDS-PAGE and RP-HPLC analyses) the predominant presence of thaumatin-like proteins. Moreover, the effects of both protein heating and disulfide bonds reduction (with dithiotreithol) on haze formation in the presence of tannins were assessed. These treatments generally resulted in an improved reactivity with tannins, and this phenomenon was related to both the surface hydrophobicity and composition of the protein fractions. Therefore, haze formation in wines seems to be related to hydrophobic interactions occurring among proteins and tannins. These interactions should occur on hydrophobic tannin-binding sites, whose exposition on the proteins can depend on both protein heating and reduction. PMID:20103151

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



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


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. PMID:25038686

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



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


Legumes with high concentrations of condensed tannin (pinto bean [Phaseolus vulgaris L.], sainfoin [Onobrychis viciifolia Scop.], and big trefoil [Lotus uliginosus Hoff.]), were compared to a selection of forages, with low or zero condensed tannin (smooth bromegrass [ Bromus inermis Leyss], Lotus japonicus [Regel] K. Larsen, and alfalfa [Medicago sativa L.]), using four methods to estimate fiber or lignin. Protocols were validated by using semipurified condensed tannin polymers in adulteration assays that tested low-lignin tissue with polyphenolic-enriched samples. The effect on lignin assay methods by condensed tannin concentration was interpreted using a multivariate analysis. There was an overestimation of fiber or lignin in the presence of condensed tannin in the acid detergent fiber (ADF) and Klason lignin (KL) assays compared to that in the thioglycolic acid (TGA) and acid detergent lignin (ADL) methods. Sulfite reagents (present in TGA lignin method) or sequential acidic digests at high temperatures (ADF followed by ADL) were required to eliminate condensed tannin. The ADF (alone) and KL protocols are not recommended to screen nonwoody plants, such as forages, where condensed tannin has accumulated in the tissue. PMID:18841900

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



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


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. PMID:24161819

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



Cotton bract tannin: a novel human T-lymphocyte mitogen and a possible causative agent of byssinosis.  


Cotton bract tannin, a major organic component of cotton dust, was tested for mitogenic activity upon human T lymphocytes. Tannin caused polyclonal activation of human T lymphocytes in vitro. The pattern of T-cell response to tannin was similar to the pattern seen in lymphocytes stimulated with the well-known plant lectin T-cell mitogens, PHA and ConA. The response to tannin was shown to be dependent upon tannin dose and presence of monocytes. The maximum response occurred after 3-4 days in culture with the magnitude comparable to the one achieved by ConA. Lipopolysaccharide from Enterobacter agglomerans, a major contaminant of cotton dust, was shown not to be a mediator of tannin mitogenicity in vitro. A role for tannin as a polyclonal cell activator and, therefore, a possible etiologic agent of byssinosis is suggested by these observations. PMID:3262589

Vuk-Pavlovi?, Z; Russell, J A; Rohrbach, M S



Synthesis and photochromic properties of configurationally varied azobenzene glycosides.  


Spatial orientation of carbohydrates is a meaningful parameter in carbohydrate recognition processes. To vary orientation of sugars with temporal and spatial resolution, photosensitive glycoconjugates with favorable photochromic properties appear to be opportune. Here, a series of azobenzene glycosides were synthesized, employing glycoside synthesis and Mills reaction, to allow "switching" of carbohydrate orientation by reversible E/Z isomerization of the azobenzene N=N double bond. Their photochromic properties were tested and effects of azobenzene substitution as well as the effect of anomeric configuration and the orientation of the sugars 2-hydroxy group were evaluated. PMID:25050228

Chandrasekaran, Vijayanand; Johannes, Eugen; Kobarg, Hauke; Sönnichsen, Frank D; Lindhorst, Thisbe K



Phenylethanoid and flavone glycosides from Ruellia tuberosa L.  


A new phenylethanoid glycoside, isocassifolioside (8), and two new flavone glycosides, hispidulin 7-O-?-L-rhamnopyranosyl-(1'? ? 2?)-O-?-D-glucuronopyranoside (11) and pectolinaringenin 7-O-?-L-rhamnopyranosyl-(1'? ? 2?)-O-?-D-glucuronopyranoside (12) were isolated from the aerial portions of Ruellia tuberosa L., together with verbascoside (1), isoverbascoside (2), nuomioside (3), isonuomioside (4), forsythoside B (5), paucifloside (6), cassifolioside (7), hispidulin 7-O-?-D-glucuronopyranoside (9) and comanthoside B (10). The structure elucidations were based on analyses of chemical and spectroscopic data including 1D- and 2D-NMR. The isolated compounds 1-12 exhibited radical scavenging activity using ORAC assay. PMID:22447282

Phakeovilay, Chiobouaphong; Disadee, Wannaporn; Sahakitpichan, Poolsak; Sitthimonchai, Somkit; Kittakoop, Prasat; Ruchirawat, Somsak; Kanchanapoom, Tripetch



Three new steroid glycosides from the starfish Asterina pectinifera.  


Three new steroid glycosides, pectiniosides H-J (1-3), were isolated along with three known compounds (4-6) including a steroid glycoside and two polyhydroxysteroids, from the alcoholic extract of the starfish Asterina pectinifera. The structures of 1-3 were determined by extensive NMR and HR-ESI-MS experiments. Compounds 1-4 did not show cytostatic activity on HL-60 cells below 100 ?M, while compounds 5-6 showed moderate cytostatic activity, with IG50 values of 80.3 and 40.5 ?M, respectively. PMID:23339622

Li, Zhanqiang; Chen, Gang; Lu, Xuan; Wang, Haifeng; Feng, Baomin; Pei, Yuehu



Synthesis and Photochromic Properties of Configurationally Varied Azobenzene Glycosides  

PubMed Central

Spatial orientation of carbohydrates is a meaningful parameter in carbohydrate recognition processes. To vary orientation of sugars with temporal and spatial resolution, photosensitive glycoconjugates with favorable photochromic properties appear to be opportune. Here, a series of azobenzene glycosides were synthesized, employing glycoside synthesis and Mills reaction, to allow “switching” of carbohydrate orientation by reversible E/Z isomerization of the azobenzene N=N double bond. Their photochromic properties were tested and effects of azobenzene substitution as well as the effect of anomeric configuration and the orientation of the sugars 2-hydroxy group were evaluated. PMID:25050228

Chandrasekaran, Vijayanand; Johannes, Eugen; Kobarg, Hauke; Sonnichsen, Frank D; Lindhorst, Thisbe K



Further flavonol and iridoid glycosides from Ajuga remota aerial parts  

Microsoft Academic Search

Five new iridoid glycosides characterised as 6-keto-8-acetylharpagide (1), 6,7-dehydro-8-acetylharpagide (2), 7,8-dehydroharpagide (3), 8-acetylharpagide-6-O-?-glucoside (4), harpagide-6-O-?-glucoside (5) together with three flavonol glycosides, myricetin 3-O-rutinoside-4?-O-rutinoside (6), myricetin 3-O-rutinoside-3?-O-rutinoside (7) and isorhamnetin 3-O-rutinoside-7-O-rutinoside-4?-O-?-glucoside (8) have been isolated from the aerial parts of Ajuga remota. Also isolated were two known compounds ajugarin IV and ajugarin V. Their structures were established using spectroscopic methods including




Xanthone glycosides from Swertia bimaculata with ?-glucosidase inhibitory activity.  


Seven new xanthone glycosides (1-7) were isolated from the n-butanol extract of Swertia bimaculata, together with six known compounds (8-13). Their structures were elucidated on the basis of extensive spectroscopic analyses (1D- and 2D-NMR, HRESIMS, UV, and IR) and comparison with data reported in the literature. All the compounds were evaluated for their ?-glucosidase inhibitory activities in vitro, and compounds 3, 4, and 7 exhibited significant activities to inhibit ?-glucosidase. Meanwhile the effects of different substitutions on the ?-glucosidase inhibitory activity of xanthone glycosides from S. bimaculata are also discussed. PMID:24687743

Yue, Yao-Dong; Zhang, Yu-Tang; Liu, Zhao-Xia; Min, Qiu-Xia; Wan, Luo-Sheng; Wang, Yong-Long; Xiao, Zuo-Qi; Chen, Jia-Chun



Xanthone glycoside constituents of Swertia kouitchensis with ?-glucosidase inhibitory activity.  


Ten new xanthone glycosides, kouitchensides A-J (1-10), and 11 known analogues were isolated from an n-butanol fraction of Swertia kouitchensis. The structures of these glycosides were determined on the basis of extensive spectroscopic data interpretation and comparison with data reported in the literature. In an in vitro test, compounds 2, 4, 5, 6, 11, 12, and 13 (IC50 values in the range 126 to 451 ?M) displayed more potent inhibitory effects against ?-glucosidase activity than the positive control, acarbose (IC50 value of 627 ?M). PMID:23805995

Wan, Luo-Sheng; Min, Qiu-Xia; Wang, Yong-Long; Yue, Yao-Dong; Chen, Jia-Chun



A Comparison of Sample Preparation Techniques for Quantifying Iridoid Glycosides Sequestered by Lepidopteran Larvae  

Microsoft Academic Search

This study compared different methods of tissue preparation for extraction of iridoid glycosides sequestered by three species\\u000a of lepidopteran larvae. Junonia coenia is a specialist on plant species that produce iridoid glycosides, while the arctiids Estigmene acrea and Spilosoma congrua are both polyphagous and will eat plants that produce iridoid glycosides. Larvae of all three species were reared on leaves

Evan C. Lampert; M. Deane Bowers



Cooperative catalysis in glycosidation reactions with O-glycosyl trichloroacetimidates as glycosyl donors.  


Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N'-Diarylthiourea as cocatalyst enforces an SN2-type acid-catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O-(?-glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, ?-glycosides are preferentially or exclusively obtained. PMID:23893796

Geng, Yiqun; Kumar, Amit; Faidallah, Hassan M; Albar, Hassan A; Mhkalid, Ibrahim A; Schmidt, Richard R



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


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

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



Triterpene glycosides from the Far-Eastern sea cucumber Pentamera calcigera. 1. Monosulfated glycosides and cytotoxicity of their unsulfated derivatives.  


Three new monosulfated triterpene glycosides, calcigerosides B (2), C(1) (3), and C(2) (4), along with the known cucumarioside G(2) (1), have been isolated from the sea cucumber Pentamera calcigera. Their structures have been deduced from extensive spectral analysis (NMR and MS) and chemical evidence. Compounds 2-4 present a novel pentasacharide chain never reported before in sea cucumber triterpene glycosides. The desulfated derivatives of calcigerosides B, C(1), and C(2) (5, 7, and 9, respectively) showed moderate cytotoxicity (IC(50) = 5 microg/mL) against a selection of four human and mouse tumor cell lines. PMID:10650081

Avilov, S A; Antonov, A S; Drozdova, O A; Kalinin, V I; Kalinovsky, A I; Stonik, V A; Riguera, R; Lenis, L A; Jiménez, C



Bioactive saponins and glycosides. XXVII. Structures of new cucurbitane-type triterpene glycosides and antiallergic constituents from Citrullus colocynthis.  


The methanolic extract from the fruit of Citrullus colocynthis showed an inhibitory effect on ear passive cutaneous anaphylaxis reactions as a type I allergic model in mice. From the methanolic extract, two new cucurbitane-type triterpene glycosides, colocynthosides A and B, were isolated together with 17 known constituents. The structures of colocynthosides A and B were elucidated on the basis of chemical and physicochemical evidence. In addition, the principal cucurbitane-type triterpene glycoside, cucurbitacin E 2-O-beta-D-glucopyranoside, and its aglycon, cucurbitacin E, exhibited the antiallergic activity at a dose of 100 and 1.25 mg/kg, p.o., respectively. PMID:17329885

Yoshikawa, Masayuki; Morikawa, Toshio; Kobayashi, Hisanori; Nakamura, Akihiko; Matsuhira, Koudai; Nakamura, Seikou; Matsuda, Hisashi



Origins of Cardiac Fibroblasts  

PubMed Central

Cardiac fibroblasts play a critical role in maintenance of normal cardiac function. They are indispensable for damage control and tissue remodeling on myocardial injury and principal mediators of pathological cardiac remodeling and fibrosis. Despite their manyfold functions, cardiac fibroblasts remain poorly characterized in molecular terms. Evidence is evolving that cardiac fibroblasts are a heterogeneous population and likely derive from various distinct tissue niches in health and disease. Here, we review our emerging understanding of where cardiac fibroblasts come from, as well as how we can possibly use this knowledge to develop novel therapies for cardiac fibrosis. PMID:21106947

Zeisberg, Elisabeth M.; Kalluri, Raghu



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


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; ?-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 ?M BA. Shoots were rooted in vitro on MS containing 15 ?M 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 ?M 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 respectively. PMID:23081776

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



Pentasaccharide glycosides from the roots of Ipomoea murucoides.  


Five pentasaccharide glycosides, murucins 1-5 (1-5), were isolated from the roots of the arboreal species Ipomoea murucoides, and their structures were elucidated by spectroscopic and chemical methods. Compounds 1-5 were evaluated for cytotoxicity against a small panel of cancer cell lines. PMID:16124750

León, Ismael; Enríquez, Raúl G; Nieto, David A; Alonso, Daniel; Reynolds, William F; Aranda, Eduardo; Villa, Josué



Characterization of pentasaccharide glycosides from the roots of Ipomoea arborescens.  


Ten new pentasaccharide glycosides, arboresins 1-6 (1-6) and murucins 6-9 (8-11), along with five known glycolipids, were isolated from the roots of Ipomoea arborescens, and their structures were elucidated by spectroscopic and chemical methods. Compounds 1-6 and 8-11 were evaluated for cytotoxicity against a small panel of cancer cell lines. PMID:16792407

León, Ismael; Mirón, Gumersindo; Alonso, Daniel



Curation of characterized glycoside hydrolases of Fungal origin  

PubMed Central

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: PMID:21622642

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



The distribution of phenylpropanoid glycosides in Chilean calceolaria Spp  

Microsoft Academic Search

The distribution of phenylpropanoid glycosides in Chilean species of Calceolaria belonging to Reiche's section III was investigated by HPLC. Verbascoside, calceolariosides A-E, forsythoside A and isoarenarioside were detected. All species investigated contained verbascoside and\\/or calceolarioside A. The patterns of these phenolic constituents seem to be characteristic of species and groups of species rather than of higher infrageneric taxa.

Antonella Di Fabio; Alessandro Bruni; Ferruccio Poli; Juan A. Garbarino; Maria C. Chamy; Marisa Piovano; Marcello Nicoletti



Verbascoside Derivatives and Iridoid Glycosides from Verbascum Undulatum  

Microsoft Academic Search

On further phytochemical investigation of the aerial parts of Verbascum undulatum, a new iridoid glycoside, 6-O-[3-O-(trans-feruloyl)-?-L-rhamnopyranosyl] aucubin (1) and a new verbascoside derivative, 6-O-acetyl-martynoside (2) were isolated. These structures were determined by spectral methods, mainly by 1D and 2D NMR spectroscopy.

P. Magiatis; S. Mitaku; E. Tsitsa; A. L. Skaltsounis; C. Harvala



Flavones and flavonol glycosides from Eupatorium cannabinum L.  


The 6-methoxyflavones hispidulin and eupafolin have been identified for the first time from the aerial parts of Eupatorium cannabinum L. The presence of the previously known flavonol glycosides astragalin, kaempferol-3-rutinoside, hyperoside, isoquercitrin and rutin could be confirmed. Hispidulin, eupafolin and rutin were screened for cytotoxicity in vitro. PMID:2594467

Elema, E T; Schripsema, J; Malingré, T M



Steroidal glycosides from the aerial part of Asclepias incarnata  

Microsoft Academic Search

The aerial part of Asclepias incarnata afforded 34 pregnane glycosides. These were confirmed to have lineolon, isolineolon, ikemagenin, 12-O-nicotinoyllineolon, deacylmetaplexigenin, metaplexigenin, rostratamine, 12-O-acetyllineolon, 15?-hydroxylineolon and 15?-hydroxyisolineolon moieties as their aglycones, and 2,6-dideoxyhexopyranose, glucopyranose and allopyranose as the corresponding sugar constituents. Their structures were determined using both spectroscopic and chemical methods.

Tsutomu Warashina; Tadataka Noro



Three new hecogenin glycosides from fermented leaves of Agave americana  

Microsoft Academic Search

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.

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



Chemical analysis of phenolic glycosides: art, facts, and artifacts  

Microsoft Academic Search

Phenolic glycosides have been the subject of considerable interest in recent ecological and systematic studies, especially those involving the Salicaceae. But these compounds are markedly labile in aqueous media, and the consequences of spontaneous degradation for valid interpretation of results have been largely ignored by researchers. We found that freeze-drying and oven-drying of leaf samples from several Populus and Salix

R. L. Lindroth; M. S. Pajutee



A biflavonoid glycoside from Lomatogonium carinthiacum (Wulf) Reichb.  


A biflavonoid glycoside with a new carbon skeleton, named carinoside A, was isolated from the n-BuOH crude extract of the whole plant of Lomatogonium carinthiacum (Wulf) Reichb. The structure of the new compound was elucidated by using spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques. PMID:25260189

Wang, Qinghu; Han, Narenchaoketu; Wu, Xiaolan; Tai, Wenquan; Dai, Nayintai; Wu, Rongjun; Wu, Jiesi; Bao, Bagenna



Functional genomic analysis of Arabidopsis thaliana glycoside hydrolase family 1  

Microsoft Academic Search

In plants, Glycoside Hydrolase (GH) Family 1 ß-glycosidases are believed to play important roles in many diverse processes including chemical defense against herbivory, lignification, hydrolysis of cell wall-derived oligosaccharides during germination, and control of active phytohormone levels. Completion of the Arabidopsis thalianagenome sequencing project has enabled us, for the first time, to determine the total number of Family 1 members

Zhiwei Xu; Luis Escamilla-Treviño; Lihui Zeng; Mallikarjun Lalgondar; David Bevan; Brenda Winkel; Ali Mohamed; Chi-Lien Cheng; Ming-Che Shih; Jonathan Poulton; Asim Esen



Application of Ultrasound and Ozone for the Removal of Aqueous Tannin  

NASA Astrophysics Data System (ADS)

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.

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



Sorghum tannins: Interaction with Starch and its Effects on in vitro Starch Digestibility  

E-print Network

compounds with starch molecules and their effect on in vitro starch digestibility. High tannin (predominant in large molecular weight PA, 80%), black (monomeric polyphenols) and white (low in polyphenols) sorghum phenolic extracts were cooked with starches...

Ribeiro de Barros, Frederico



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


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 suggest that providing grape seed and perhaps other CTs via drinking water may be a practical way to introduce CTs into sheep and cattle diets. PMID:23880297

Kronberg, S L; Schauer, C S



Tannins from four common Acacia species of Texas and Northeastern Mexico  

Microsoft Academic Search

The amount of tannins present inAcacia berlandierii, A. farnesiana, A. greggii andA. rigidula, 4 common species of the southwestern United States and northern Mexico, was determined. Bark samples of the 4 species were\\u000a extracted with water, 80% methanol, and 70% acetone. Of these, 70% acetone proved to be the most efficient solvent. Tannins\\u000a were determined by Folin-Denis analysis for total

D. S. Seigler; S. Seilheimer; J. Keesy; H. F. Huang



Color reaction of hydrolyzable tannins with Bradford reagent, Coomassie brilliant blue  

Microsoft Academic Search

Bradford protein-binding dye, Coomassie brilliant blue G-250, formed intensively blue-colored complexes with hydrolyzable tannins. The tannin–dye aggregates displayed a broad absorption maximum around 700 nm, with a shoulder at 620 nm. Pronounced reactivities were observed with tetra- to nonagalloylglucoses. Gallic acid, ?-glucogallin and digalloylglucose were inactive and trigalloylglucose gave only a weak reaction. Moderate color formation (65% relative to pentagalloylglucose)

Wolfgang J Kilkowski; Georg G Gross



The Evaluation of High Tannin Cotton Lines for Resistance to Rhizoctonia solani and Pythium aphanidermatum  

E-print Network


Kennett, Raymond Matthew



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

Microsoft Academic Search

Anthocyanins and condensed tannins are major fla- vonoid end-products in higher plants. While the transactivation of anthocyanins by basic helix-loop- helix (bHLH) transcription factors is well docu- mented, 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

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



Behavioral adaptation of Pallas's squirrels to germination schedule and tannins in acorns  

Microsoft Academic Search

Using acorns from Castanea henryi (CH) and Quercus variabilis (QV) with contrasting germination schedule (related to food perishability) and tannin levels, we conducted field experiments in a subtropical forest in Southwest China to investigate how free-ranging Pallas's squirrels (Callosciurus erythraeus) utilize acorns as long-term storage based on the food perishability and high-tannin hypotheses. Though QV acorns germinated much earlier than

Zhishu Xiao; Xu Gao; Mingmin Jiang; Zhibin Zhang



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

PubMed Central

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

Wang, Bo; Chen, Jin



Effect of alkali treatment on physiological activity of cotton condensed tannin.  

PubMed Central

Cotton dusts contain condensed tannins and endotoxins, which are suspected of contributing to the development of acute and chronic biological responses in some cotton textile mill workers. Condensed tannin extracted from cotton dust was coated on to cellulose powder, and the tannin coated powder was treated with an alkali solvent system previously developed to reduce the endotoxin content and pulmonary toxicity of cotton dust. Physiological activities of the dusts and powders were compared by assaying the production of the arachidonic acid metabolites prostaglandin F2 alpha (PGF2 alpha), thromboxane A2 (TxA2) (the precursor to thromboxane B2 (TxB2], leukotriene C4 (LTC4), and prostaglandin E2 (PGE2) by guinea pig pulmonary cells obtained by lung lavage. Cotton dust stimulated the pulmonary cells to produce a total of 29 pg metabolites per 10(6) cells. Production of metabolites by cells stimulated with tannin coated cellulose powder was reduced to 8.3 pg/10(6) cells. Alkali treatment of the tannin coated cellulose powder resulted in a further decrease in its ability to stimulate the cells, producing 3.5 pg metabolites per 10(6) cells. The ability of the dusts and powders to stimulate production of metabolites of arachidonic acid by pulmonary cells from guinea pigs was highly correlated with tannin content of the materials, but not with endotoxin content as measured by the Limulus amoebocyte lysate (LAL) assay. PMID:2223662

Rousselle, M A; Elissalde, M H; Domelsmith, L N




PubMed Central

With light and electron microscopy a comparison has been made of the morphology of ventricular (V) and Purkinje (P) fibers of the hearts of guinea pig, rabbit, cat, dog, goat, and sheep. The criteria, previously established for the rabbit heart, that V fibers are distinguished from P fibers by the respective presence and absence of transverse tubules is shown to be true for all animals studied. No evidence was found of a permanent connection between the sarcoplasmic reticulum and the extracellular space. The sarcoplasmic reticulum (SR) of V fibers formed couplings with the sarcolemma of a transverse tubule (interior coupling) and with the peripheral sarcolemma (peripheral coupling), whereas in P fibers the SR formed only peripheral couplings. The forms of the couplings were identical. The significance, with respect to excitation-contraction coupling, of the difference in the form of the couplings in cardiac versus skeletal muscle is discussed together with the electrophysiological implications of the differing geometries of bundles of P fibers from different animals. PMID:5645545

Sommer, Joachim R.; Johnson, Edward A.



Cardiac glycosides inhibit detubulation in amphibian skeletal muscle fibres exposed to osmotic shock  

Microsoft Academic Search

It has recently been suggested that the ‘vacuolation’ of the transverse tubular system that follows the imposition of an osmotic shock is a component process in the eventual ‘detubulation’ of amphibian skeletal muscle. However, such a hypothesis requires net fluid transfers from the intracellular space into the lumina of the transverse tubules against the prevailing transmembrane osmotic gradients. The present

Serena Nik-Zainal; Jeremy N. Skepper; Austin Hockaday; Christopher L.-H. Huang



Iron interference on matrix-assisted laser desorption\\/ionisation time-of-flight mass spectra of condensed tannins  

Microsoft Academic Search

Matrix-assisted laser desorption\\/ionisation time-of-flight mass spectrometry (MALDI-TOF MS) was used to reveal the influence of iron on the detectability of condensed tannins extracted from Picea abies. Iron chloride mixed with condensed tannins suppresses the detection of tannins by MALDI-TOF MS in a dose-dependent manner. Total suppression is observed at concentrations of 250 and 500 mg FeCl 3 g –1 of sample. At

Clemens J. Engelke; Heike Knicker; Ingrid Kögel-Knabner



Inhibition of alveolar macrophage spreading and phagocytosis by cotton bract tannin. A potential mechanism in the pathogenesis of byssinosis.  


One of the major host-defense functions of alveolar macrophages is the phagocytosis and clearance of inhaled particles deposited in the lower airways and alveolar spaces. Recent studies have indicated that the condensed tannins present in cotton mill dust stimulate the secretion of neutrophil chemotactic factor and arachidonic acid from resident rabbit alveolar macrophages and that these responses may contribute to the acute pulmonary inflammatory reaction associated with byssinosis. To characterize further the effect of tannin on macrophage function, the ability of tannin to modulate alveolar macrophage spreading and phagocytosis in vitro was examined. Tannin caused a dose-dependent inhibition of alveolar macrophage spreading with nearly complete inhibition occurring at concentrations of 12.5 micrograms/ml. This inhibitory effect of tannin was not reversed with removal of tannin. Furthermore addition of tannin to previously spread macrophages actively caused the macrophages to round up. Examination of the structure of alveolar macrophages exposed to tannin by scanning and transmission electron microscopy revealed blebs on the surface of the cells and the loss of most of the cellular organelle structure, as compared to control macrophages. Tannin also modulated the ability of the alveolar macrophages to phagocytize unopsonized latex microspheres. The effect of tannin was biphasic. At the lowest concentration examined (3 micrograms/ml), tannin significantly enhanced phagocytosis of the latex microspheres. However, as the concentration was increased, phagocytosis decreased almost exponentially until at 50 micrograms/ml phagocytosis was significantly inhibited compared to control macrophages. These data indicate that tannin present in inhaled cotton mill dust could significantly decrease the ability of resident alveolar macrophages to phagocytize and thereby clear inhaled dust particles. This inhibitory effect would increase the time that particles remain exposed in the lower airway and alveolar spaces and thereby increase the time that potentially toxic compounds in the dust have to exert their biologic effect. This inhibition of macrophage function may therefore contribute to the pathogenesis of byssinosis. PMID:2117397

Kreofsky, T J; Russell, J A; Rohrbach, M S



Tannins and nitrogen dynamics in mangrove leaves at different age and decay stages (Jiulong River Estuary, China)  

Microsoft Academic Search

Changes in the total phenolics, condensed tannins (CT), protein-precipitable phenolics content and protein precipitation capacity\\u000a were determined on mangrove leaves representing a range of maturation and senescence in the Jiulong River Estuary, Fujian,\\u000a China. The results showed that the total phenolics, extractable condensed tannins, total condensed tannins, protein-precipitable\\u000a phenolics content and protein precipitation capacity in young leaves were higher than

Yi Ming Lin; Jin Wen Liu; Ping Xiang; Peng Lin; Zhen Hua Ding; Leonel da Silveira Lobo Sternberg



EBV DNA polymerase inhibition of tannins from Eugenia uniflora.  


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

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



Resin glycosides. XV. Simonins I-V, ether-soluble resin glycosides (jalapins) from the roots of Ipomoea batatas (cv. Simon).  


Five new ether-soluble resin glycosides (jalapins), simonins I-V, have been isolated from the roots of Ipomoea batatas and characterized on the bases of chemical and spectral data. Simonin I is the first example of resin glycoside with aromatic acid (trans-cinnamic acid) as a component organic acid. PMID:1294318

Noda, N; Yoda, S; Kawasaki, T; Miyahara, K



Cardiac Syndrome X  


Related terms: angina, microvascular angina Cardiac syndrome X patients have the pain of angina , but they do not have coronary artery disease ( CAD ). So even though patients with cardiac syndrome X ...


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


Commercial tannins are natural polyphenolic compounds extracted from different plant tissues such as gall, the wood of different species and fruit. In the food industry they are mainly used as flavourings and food ingredients, whereas in winemaking they are classified as clarification agents for wine protein stabilisation, although colour stabilisation, metal removal, unpleasant thiol removal and rheological correction are also well-known and desired effects. Due to their particular technical properties and very different costs, the possibility of correct identification of the real botanical origin of tannins can be considered a primary target in oenology research and in fulfilling the technical and economic requirements of the wine industry. For some categories of tannins encouraging results have already been achieved by considering sugar or polyphenolic composition. For the first time this work verifies the possibility of determining the botanical origin of tannins on the basis of the mineral element profile and analysis of the (13) C/(12) C isotopic ratio. One hundred two commercial tannins originating from 10 different botanical sources (grapes, oak, gall, chestnut, fruit trees, quebracho, tea, acacia, officinal plants and tara) were analysed to determine 57 elements and the (13) C/(12) C isotopic ratio, using inductively coupled plasma mass spectrometry and isotope-ratio mass spectrometry, respectively. Forward stepwise discriminant analysis provided good discrimination between the 8 most abundant groups, with 100% correct re-classification. The model was then validated five times on subsets of 10% of the overall samples, randomly extracted, achieving satisfactory results. With a similar approach it was also possible to distinguish toasted and untoasted oak tannins as well as tannins from grape skin and grape seeds. PMID:25230175

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



Condensed tannins and flavonoids from the forage legume sulla (Hedysarum coronarium).  


The condensed tannin concentrations and composition and the characterization of the phenolic constituents in the leaves of the forage legume sulla (Hedysarum coronarium), a biennial forage legume found in temperate agricultural regions, were studied. The colorimetric butanol-HCl assay was used for the quantitation of the seasonal condensed tannin concentrations in the leaves of sulla. Fractionation of extracts on Sephadex LH-20 using step elution with aqueous methanol, followed with aqueous acetone or gradient elution with water, aqueous methanol, and aqueous acetone, gave condensed tannin and flavonoid fractions. The chemical characteristics of the purified condensed tannin fractions were studied by acid-catalyzed degradation with benzyl mercaptan and electrospray ionization mass spectrometry (ESI-MS). Thiolysis revealed that epigallocatechin was the major extender unit (15-75%) while gallocatechin was the major terminal unit (50-66%), thus indicating the extractable sulla condensed tannin fraction as the prodelphinidin type. Condensed tannin oligomers to polymers obtained from Sephadex LH-20 gradient fractions ranged between 2.9 and 46 mDP. The homo- and heterogeneous oligomer ions in condensed tannin gradient fractions detected by ESI-MS ranged from 2 to 10 DP and are consistent with the values obtained by thiolysis (2.9-6.9 DP). Lower molecular weight phenolics, including flavonoids and phenolic acids, were characterized by liquid chromatography atmospheric pressure chemical ionization mass spectrometry (LC-APCI/MS) and ESI/MS/MS on a linear ion trap. The flavonoids extracted with aqueous acetone and methanol from sulla leaves and identified included kaempferol, rutin, quercetin-7-O-?-L-rhamnosyl-3-O-glucosylrhamnoside, quercetin-3-O-?-L-rhamnosyl-7-O-glucoside, kaempferol-3-O-?-D-glucoside-dirhamnoside, genistein-7-O-?-D-glucosyl-6?-O-malonate, formononetin-7-O-?-D-glucoside-6?-O-malonate, and afrormosin and the phenolic acid chlorogenic acid. PMID:21780793

Tibe, Olekile; Meagher, Lucy P; Fraser, Karl; Harding, David R K



Resin glycosides from the flowers of Ipomoea murucoides.  


The CHCl(3)-soluble extract from the flowers of the Mexican medicinal plant Ipomoea murucoides, through preparative-scale recycling HPLC, yielded murucoidins I-V (1-5), which are new pentasaccharides of jalapinolic acid, as well as the known stoloniferin I (6). Saponification of the crude resin glycoside mixture yielded two glycosidic acids, simonic acid B (9) and operculinic acid A (10), and their esterifying residues were composed of the two short-chain fatty acids, 2-methylpropanoic and (2S)-methylbutyric acids. All the isolated compounds (1-6) were characterized through high-field NMR spectroscopy. Compound 4 exhibited marginal cytotoxicity against Hep-2 cells (ED(50) 4 microg/mL). PMID:16643033

Chérigo, Lilia; Pereda-Miranda, Rogelio



Diterpene glycosides from the seeds of Pharbitis nil.  


Six new ent-kaurane diterpene glycosides, pharbosides A-F (1-6), and a new ent-gibbane diterpene glycoside, pharboside G (7), together with three known ent-kaurane diterpenoids, 7beta,16beta,17-trihydroxy-ent-kauran-6alpha,19-olide (8), 6beta,7beta,16alpha,17-tetrahydroxy-ent-kauranoic acid (9), and 6beta,7beta,16beta,17-tetrahydroxy-ent-kauranoic acid (10), were isolated from an ethanolic extract of the seeds of Pharbitis nil. The structures of the new compounds were determined by spectroscopic methods including 1D and 2D NMR analysis. The absolute configurations of the compounds were clarified by CD spectroscopic studies. Full NMR data assignments of the three known compounds (8-10) are reported. The isolated compounds were evaluated for their cytotoxic activities against four human cancer cell lines. PMID:19435339

Kim, Ki Hyun; Choi, Sang Un; Lee, Kang Ro



Glycosides and xanthine oxidase inhibitors from Conyza bonariensis.  


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

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



Structures of the novel diterpene glycosides from Stevia rebaudiana.  


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

Chaturvedula, Venkata Sai Prakash; Prakash, Indra



Two minor diterpene glycosides from the leaves of Stevia rebaudiana.  


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

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



Flavonol and iridoid glycosides of Ajuga remota aerial parts  

Microsoft Academic Search

Six flavonol glycosides characterised as myricetin 3-O-?-rhamnosyl-(1??2?)-?-rhamnoside-3?-O-?-rhamnoside, 5?-O-methylmyricetin 3-O-[?-rhamnosyl (1??2?)][?-rhamnosyl (1???4?)]-? -glucoside-3?-O-?-glucoside, 5?-O-methylmyricetin 3-O-?-rhamnosyl (1??2?)-?-rhamnoside 3?-O-?-galactoside, kaemferol 3-O-rutinoside-7-O-rutinoside, myricetin 3-O-rutinoside-3?-O-?-rhamnoside, myricetin 3-O-?-glucosyl (1??2?)-?-glucoside-4?-O-?-glucoside together with two iridoid glycosides identified as 6,8-diacetylharpagide and 6,8-diacetylharpagide-1-O-?-(3?,4?-di-O-acetylglucoside) have been isolated from extract of Ajuga remota aerial parts. Also isolated from the same extract were known compounds; kaempferol 3-O-?-rhamnoside, quercetin 3-O-?-glucoside, quercetin 3-O-rutinoside, 8-acetylharpagide, ajugarin

Lawrence O. Arot Manguro; Samuel Otieno Wagai; Peter Lemmen



Coumarins of Matricaria chamomilla L.: aglycones and glycosides.  


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-?-d-glucoside), daphnin (daphnetin-7-O-?-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. PMID:23768326

Petru?ová-Poracká, Veronika; Rep?ák, Miroslav; Vilková, Mária; Imrich, Ján



New phenolic glycosides from the seeds of Cucurbita moschata.  


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. PMID:20183300

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



Acacetin glycosides as taxonomic markers in Calamintha and Micromeria.  


A new acetylated flavone glycoside, acacetin 7-O-[6"-O-acetylglucosyl(1"-->2")]rhamnosyl(1"'-->6")glucoside, has been isolated from the leaves of Calamintha glandulosa together with the known compound acacetin 7-O-rhamnosyl(1"'-->6")glucoside. The occurrence of these flavonoids in the closely related genera Satureja, Micromeria, Acinos and Clinopodium indicates that their distribution may be of taxonomic significance. PMID:11684193

Marin, P D; Grayer, R J; Veitch, N C; Kite, G C; Harborne, J B



Acacetin glycosides as taxonomic markers in Calamintha and Micromeria  

Microsoft Academic Search

A new acetylated flavone glycoside, acacetin 7-O-[6??-O-acetylglucosyl(1???2?)]rhamnosyl(1??6?)glucoside, has been isolated from the leaves of Calamintha glandulosa together with the known compound acacetin 7-O-rhamnosyl(1??6?)glucoside. The occurrence of these flavonoids in the closely related genera Satureja, Micromeria, Acinos and Clinopodium indicates that their distribution may be of taxonomic significance.

Petar D. Marin; Renée J. Grayer; Nigel C. Veitch; Geoffrey C. Kite; Jeffrey B. Harborne



Quinovic acid glycosides from roots of Macfadyena unguis-cati.  


Two glycosides, isolated in good yields from roots of Macfadyena unguis-cati (L.) A. G entry (syn. Doxantha unguis-cati (L.) Miers), gave on hydrolysis the same aglycone (quinovic acid). The sugar moieties have been identified as fucose and glucose respectively. This is the first time that saponins have been found in Bignoniaceae and their occurrence may account of the use of the plant in folk medicine. PMID:17402003

Ferrari, F; Kiyan de Cornelio, I; Delle Monache, F; Marini Bettolo, G B



New antifungal flavone glycoside from Butea monosperma O. Kuntze.  


A new bioactive flavone glycoside was isolated from the methanol soluble fraction of the flowers of Butea monosperma O. Kuntze, which was identified as 5,7-dihydroxy-3,6,4'-trimethoxyflavone-7-O-alpha-L-xylopyranosyl-(1-->3)-O-alpha-L-arabinopyranosyl-(1-->4)-O-beta-D-galactopyranoside (1) by several colour reactions, chemical degradations and spectral analysis. The compound 1 shows antimicrobial activity against various fungal species. PMID:17847718

Yadava, R N; Tiwari, Lata



Flavonol glycosides with ?-D-aldohexoses from Rhododendron irroratum  

Microsoft Academic Search

Two new flavonol glycosides which contain rare ?-D-galactose or ?-D-glucose were obtained from the flowers of Rhododendron irroratum Franch., namely myricetin 3-O-?-D-galactoside-3?-O-?-D-glucoside (1) and myricetin 3-O-?-D-galactoside-3?-O-?-D-galactoside (2). Their structures were determined by UV, IR, HR–ESI–MS, ESI–MS, 1D- and 2D-NMR techniques.

Ming Hua Yang; Jian Guang Luo; Xue Feng Huang; Ling Yi Kong



Two aurone glycosides from heartwood of Pterocarpus santalinus.  


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

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



Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina  

Microsoft Academic Search

Eight iridoid glycosides and four phenolic compounds were isolated from the EtOAc soluble fraction of Veronica peregrina MeOH extract as the radical scavengers for antioxidant activity. The compounds were identified as protocatechuic acid (1), luteolin (2), veronicoside (3), minecoside (4), specioside (5), amphicoside (6), catalposide (7), 6-O-cis-p-coumaroyl catalpol (8), p-hydroxy benzoic acid methyl ester (9), verproside (10), verminoside (11), and

Jong Hwan Kwak; Hyun Jung Kim; Kwang Ho Lee; Se Chan Kang; Ok Pyo Zee



Steroidal glycosides from the aerial part of Asclepias incarnata.  


The aerial part of Asclepias incarnata afforded 34 pregnane glycosides. These were confirmed to have lineolon, isolineolon, ikemagenin, 12-O-nicotinoyllineolon, deacylmetaplexigenin, metaplexigenin, rostratamine, 12-O-acetyllineolon, 15beta-hydroxylineolon and 15beta-hydroxyisolineolon moieties as their aglycones, and 2.6-dideoxyhexopyranose, glucopyranose and allopyranose as the corresponding sugar constituents. Their structures were determined using both spectroscopic and chemical methods. PMID:10731028

Warashina, T; Noro, T



Glycosidically bound volatiles and flavor precursors in Laurus nobilis L.  


Glycosidically bound volatile compounds in different parts (leaves and buds) of Laurus nobilis L. were investigated. After isolation of extracts obtained by Amberlite XAD-2 adsorption and methanol elution, glycosides were analyzed after enzymatic hydrolysis by GC-MS or directly after trifluoroacetyl (TFA) derivatization by GC-MS in EI and NCI mode. In the leaves most of the glycosidically bound volatiles occur as beta-D-glucopyranosides. Among the disaccharides, primeverosides are predominant; smaller amounts of alpha-L-arabinofuranosyl-beta-D-glucopyranosides, rutinosides, and vicianocides could also be identified. Major aglycons comprised benzyl alcohol, some linalool-diols, 2-hydroxy-1,8-cineole and its derivatives such as 2,3-dehydro-1,8-cineole, sobrerols, and menthadien-8-ols. Among the identified nor-carotenoids, 3-oxo-alpha-ionol, the corresponding 7,8-dihydro derivative, and vomifoliol are predominant in leaves. 3-Hydroxy-beta-damascone and 3-hydroxy-7,8-didehydro-beta-ionol, precursors of the sensorially active damascenone, were identified only in the buds. PMID:15769161

Kilic, Ayben; Kollmannsberger, Hubert; Nitz, Siegfried



Minor diterpene glycosides from the leaves of Stevia rebaudiana.  


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-?-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-?-d-glucopyranosyl-?-d-glucopyranosyl ester and compound 2, 12-?-[(2-O-?-d-glucopyranosyl-?-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid ?-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-?-hydroxy-ent-kaur-16-en-19-oic acid existing as a glycoside in S. rebaudiana. The structures of the isolated metabolites 1 and 2 were determined based on comprehensive 1D- and 2D-NMR (COSY, HSQC, and HMBC) studies. A high-quality crystal of compound 3 has formed, which allowed the acquisition of X-ray diffraction data that confirmed its structure. The structural similarities between the new metabolites and the commercially available stevioside sweeteners suggest the newly isolated metabolites should be examined for their organoleptic properties. Accordingly rebaudiosides E, M, N, O, and KA have been isolated in greater than gram quantities. PMID:24758242

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



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


Excess crude protein (CP) in dairy cow diets is excreted mostly as urea nitrogen (N), which increases ammonia (NH) emissions from dairy farms and heightens human health and environmental concerns. Feeding less CP and more tannin to dairy cows may enhance feed N use and milk production, abate NH emissions, and conserve the fertilizer N value of manure. Lab-scale ventilated chambers were used to evaluate the impacts of CP and tannin feeding on slurry chemistry, NH emissions, and soil inorganic N levels after slurry application to a sandy loam soil and a silt loam soil. Slurry from lactating Holstein dairy cows (Bos taurus) fed two levels of dietary CP (low CP [LCP], 155 g kg; high CP [HCP], 168 g kg) each fed at four levels of dietary tannin extract, a mixture from red quebracho (Schinopsis lorentzii) and chestnut (Castanea sativa) trees (0 tannin [0T]; low tannin [LT], 4.5 g kg; medium tannin [MT], 9.0 g kg; and high tannin [HT], 18.0 g kg) were applied to soil-containing lab-scale chambers, and NH emissions were measured 1, 3, 6, 12, 24, 36, and 48 h after slurry application. Emissions from the HCP slurry were 1.53 to 2.57 times greater ( < 0.05) than from the LCP slurry. At trial's end (48 h), concentrations of inorganic N in soils were greater ( < 0.05) in HCP slurry-amended soils than in LCP slurry-amended soils. Emissions from HT slurry were 28 to 49% lower ( < 0.05) than emissions from 0T slurry, yet these differences did not affect soil inorganic N levels. Emissions from the sandy loam soil were 1.07 to 1.15 times greater ( < 0.05) than from silt loam soil, a result that decreased soil inorganic N in the sandy loam compared with the silt loam soil. Larger-scale and longer-term field trails are needed to ascertain the effectiveness of feeding tannin extracts to dairy cows in abating NH loss from land-applied slurry and the impact of tannin-containing slurry on soil N cycles. PMID:22031559

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



Taxifolin Glycoside Blocks Human ether-a-go-go Related Gene K+ Channels  

PubMed Central

Taxifolin glycoside is a new drug candidate for the treatment of atopic dermatitis (AD). Many drugs cause side effects such as long QT syndrome by blocking the human ether-a-go-go related gene (hERG) K+ channels. To determine whether taxifolin glycoside would block hERG K+ channels, we recorded hERG K+ currents using a whole-cell patch clamp technique. We found that taxifolin glycoside directly blocked hERG K+ current in a concentration-dependent manner (EC50=9.6±0.7 µM). The activation curve of hERG K+ channels was negatively shifted by taxifolin glycoside. In addition, taxifolin glycoside accelerated the activation time constant and reduced the onset of the inactivation time constant. These results suggest that taxifolin glycoside blocks hERG K+ channels that function by facilitating activation and inactivation process. PMID:23440017

Yun, Jihyun; Bae, Hyemi; Choi, Sun Eun; Kim, Jung-Ha; Choi, Young Wook; Lim, Inja; Lee, Chung Soo; Lee, Min Won; Ko, Jae-Hong; Seo, Seong Jun



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


Elicitin-mediated acquisition of plant sterols is required for growth and sporulation of Phytophthora spp. This study examined the interactions between elicitins, sterols, and tannins. Ground leaf tissue, sterols, and tannin-enriched extracts were obtained from three different plant species (California bay laurel, California black oak, and Oregon white oak) in order to evaluate the effect of differing sterol/tannin contents on Phytophthora ramorum growth. For all three species, high levels of foliage inhibited P. ramorum growth and sporulation, with a steeper concentration dependence for the two oak samples. Phytophthora ramorum growth and sporulation were inhibited by either phytosterols or tannin-enriched extracts. High levels of sterols diminished elicitin gene expression in P. ramorum; whereas the tannin-enriched extract decreased the amount of 'functional' or ELISA-detectable elicitin, but not gene expression. Across all treatment combinations, P. ramorum growth and sporulation correlated strongly with the amount of ELISA-detectable elicitin (R (2)?= 0.791 and 0.961, respectively). PMID:23689874

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



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


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. PMID:24694706

Schnabel, Thomas; Musso, Maurizio; Tondi, Gianluca



Do salivary proline-rich proteins counteract dietary hydrolyzable tannin in laboratory rats?  


We hypothesized that dietary hydrolyzable tannins would not act as digestibility reducing substances but would be excreted in the feces if the tannin were ingested by rats producing salivary proline-rich proteins (PRPs). To test that hypothesis we used two groups of Sprague-Dawley rats: tannin-naïve rats that were secreting basal levels of salivary PRPs and tannin-habituated rats that were secreting elevated levels of PRPs. The animals were fed for 10-18 d on diets containing 3% (w/w) purified hydrolyzable tannin [pentagalloyl glucose (PGG)] that was periodically spiked with chemically synthesized, radiolabeled 1,2,3,4,6-penta-O-galloyl-[U-14C]-D-glucopyranose (1 microCi per gram diet). The PGG-habituated rats excreted three times more of the consumed 14C in their feces than did the PGG-naive rats (11.4% for PGG-habituated rats vs. 3.5% for PGG-naïve rats, P < 0.05). The addition of 3% PGG to the diet of the PGG-naïve rats had no significant effect on apparent dry matter or nitrogen digestibility (P > 0.05). However, dry matter digestibility and nitrogen digestibility were significantly decreased by PGG in the diets of the PGG-habituated rats (7 and 25%, P < 0.001, respectively). Production of PRPs increased the amount of PGG excreted intact in the feces but at the cost of diminishing apparent dry matter and nitrogen digestibility. PMID:15586668

Skopec, Michele M; Hagerman, Ann E; Karasov, William H



Flocculation of Microcystis aeruginosa using modified larch tannin.  


To flocculate the cyanobacterium Microcystis aeruginosa from water, larch tannin, a natural polymer, was modified by Mannich reaction to obtain a flocculant, named A-TN, which was then quaternized to yield another flocculant, named Q-TN. A-TN and Q-TN were characterized by Fourier transform infrared spectra (FTIR) and zeta potential analysis. The effects of the flocculation parameters, e.g., dosage, pH, cell density, culture time, and extracellular organic materials, were studied. The results showed that Q-TN was effective under a wider range of pH values than A-TN and could work under a pH of 9.0, whereas A-TN could work only under a pH of 7.0. For algal samples with densities from 1 × 10(8) to 5 × 10(9) cells/L, the optimum dosages of Q-TN to achieve more than 90% removal efficiency ranged from 0.5 to 20 mg/L, and the optimum dosages had a good linear relationship with cell density. Furthermore, the required dosage of Q-TN clearly increased along with the algae culture time, most of which was consumed by the extracellular organic materials (EOM) excreted from the cells. The spectra of the three-dimensional excitation-emission matrix showed that 100% of simple aromatic proteins and 78.8% of protein-like substances in the EOM could be removed by Q-TN. However, Q-TN was less effective in humic/fulvic-like substance flocculation. Q-TN functioned to settle the algae cells and a large amount of their metabolites effectively. PMID:23647228

Wang, Li; Liang, Wenyan; Yu, Jian; Liang, Zhixia; Ruan, Lingling; Zhang, Yuanchun



A comparison of flavonoid glycosides by electrospray tandem mass spectrometry  

NASA Astrophysics Data System (ADS)

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.

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



Cardenolide and oxypregnane glycosides from the root of Asclepias incarnata L.  


Twenty-nine new oxypregnane glycosides were obtained along with two known cardenolides, frugoside and gofruside, and three known 12-O-acylated pregnane glycosides from the roots of Asclepias incarnata L. (Asclepiadaceae). By detailed studies of the 1H- and 13C-NMR spectra, the structures were determined to be tri- to penta glycosides of isolineolon, 12-O-acetyllineolon, ikemagenin, 12-O-benzoylisolineolon, and two new 12-O-acylated pregnanes. PMID:10783071

Warashina, T; Noro, T



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

Microsoft Academic Search

This review article presents 209 alkaloid glycosides isolated and identified from plants, microorganisms, and marine invertebrates\\u000a that demonstrate different biological activities. They are of great interest, especially for the medicinal and\\/or pharmaceutical\\u000a industries. These biologically active glycosides have good potential for future chemical preparation of compounds useful as\\u000a antioxidants, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been subdivided

Valery M. Dembitsky



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

SciTech Connect

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 gained from Brachypodium will inform translational research studies, with applications for the improvement of cereal crops and bioenergy grasses.

Tyler, Ludmila [United States Department of Agriculture (USDA), Western Regional Research Center (WRRC), Albany; Bragg, Jennifer [United States Department of Agriculture (USDA), Western Regional Research Center (WRRC), Albany; Wu, Jiajie [United States Department of Agriculture (USDA), Western Regional Research Center (WRRC), Albany; Yang, Xiaohan [ORNL; Tuskan, Gerald A [ORNL; Vogel, John [United States Department of Agriculture (USDA), Western Regional Research Center (WRRC), Albany



Novel phenolic glycoside dimer and trimer from the whole herb of Pyrola rotundifolia.  


From the water-soluble constituents of the whole herb of Pyrola rotundifolia (Pyrolaceae), one novel phenolic glycoside dimer, pyrolaside A (1), and one novel phenolic glycoside trimer, pyrolaside B (2), together with two known phenolic glycosides homoarbutin (3) and isohomoarbutin (4), were isolated. The structures were elucidated by spectroscopic analysis and confirmed with chemical degradation. In vitro tests for antimicrobial activity showed pyrolaside B (2) to possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Micrococcus luteus. PMID:16079548

Chang, Jun; Inui, Taichi



Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effects  

Microsoft Academic Search

Purification of polar fractions from cacao liquor extracts gave 17 phenolics including four new compounds. The new compounds were characterized as a C-glycosidic flavan, an O-glycoside of a dimeric and two O-glycosides of trimeric A-linked proanthocyanidins, on the basis of spectroscopic data. Isolated polyphenols showed inhibitory effects on nicotinamide adenine dinucleotide phosphate-dependent lipid peroxidation in microsomes and on the autoxidation

Tsutomu Hatano; Haruka Miyatake; Midori Natsume; Naomi Osakabe; Toshio Takizawa; Hideyuki Ito; Takashi Yoshida



[Malignant cardiac tumors].  


Cardiac neoplasms are a rare occurrence in clinical practice. The various frequencies of primary and secondary malignant tumors vary from report to report, approximately 1% in most autopsy series and 4% in cancer patient's autopsies. Cardiac malignancies account for less 1% of cardiac surgery and about for 0.1% of cardiac echographic studies. The presence of metastatic tumor to the heart usually indicates widespread metastases. Lung carcinomas are the most commonly encountered tumor followed by breast and pancreas cancer and melanoma. Apart from primary pericardial mesothelioma, primary cardiac tumors are high-grade sarcomas with a high metastatic potency that often becomes evident early after surgery. Symptoms are non specific, occur late in the disease and affect few patients; especially secondary neoplasms of the heart take their course so fast that they cannot become symptomatic. The signs of cardiac neoplasms are divided into systemic symptoms (fever, arthralgias and myalgias), cardiac symptoms (congestive heart failure, arrhythmia, chest pain) and uncommon embolisms. Diagnosis is actually made easier with cardiac echography. Cardiac RMI is helpful to estimate vessels and pericardium involvement. Due to its poor prognosis, treatment of cardiac metastases is restricted to best supportive care. For primary cardiac neoplasms, surgery must be carefully discussed because operative intervention is often followed by rapid widespread metastases that adjuvant chemotherapy cannot avoid in most cases. PMID:15899620

Debourdeau, Philippe; Gligorov, Joseph; Teixeira, Luis; Aletti, Marc; Zammit, Christine



Cardiac gated ventilation  

SciTech Connect

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

Hanson, C.W. III [Hospital of the Univ. of Pennsylvania, Philadelphia, PA (United States). Dept. Anesthesia; Hoffman, E.A. [Univ. of Iowa College of Medicine, Iowa City, IA (United States). Div. of Physiologic Imaging



Cardiac gated ventilation  

NASA Astrophysics Data System (ADS)

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

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



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

PubMed Central

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

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



Turbidimetric and photometric determination of total tannins in tea using a micro-flow-batch analyzer.  


Both turbidimetric and photometric determinations of total tannins in samples of green and black tea, using a micro-flow-batch analyzer (?FBA) were studied. The miniaturized system was formed using photocurable urethane-acrylate resin and ultraviolet lithography technique. The turbidimetric method was based on the precipitation reaction of Cu (II) with tannins in acetate medium at a pH of 4.5. The photometric method was based on the complexation reaction of tannins with ferrous tartrate. The turbidimetric ?FBA was able to test 200 samples per hour. The photometric ?FBA allowed 300 analyses per hour, generating 136?L of residue per analysis. The paired t test, at a 95% confidence level, showed no statistically significant differences between results obtained by both methods and the reference method. The urethane-acrylate ?FBA maintained satisfactory physical and chemical properties, and represents an improvement over conventional flow-batch analyzer. PMID:22265564

Lima, Marcelo B; Andrade, Stéfani I E; Harding, David P; Pistonesi, Marcelo F; Band, Beatriz S F; Araújo, Mário C U



Direct anthelmintic effects of condensed tannins towards different gastrointestinal nematodes of sheep: in vitro and in vivo studies  

Microsoft Academic Search

In vitro and in vivo studies were conducted to determine possible direct anthelmintic effects of condensed tannins towards different ovine gastrointestinal nematodes. A larval development\\/viability assay was used to investigate the effect of a condensed tannin extract (Quebracho) towards larvae of Haemonchuscontortus, Teladorsagiacircumcincta and Trichostrongylusvitrinus. The development to infective larvae and their viability was assessed in all three species and

S Athanasiadou; I Kyriazakis; F Jackson; R. L Coop



Effect of drying method and length of storage on tannin and total phenol concentrations in Pigeon pea seeds  

Microsoft Academic Search

Total phenols and condensed tannins in Pigeon pea seeds were determined by flow injection spectrophotometry. Folin-Denis and vanillin assays were used for total phenol and condensed tannin, respectively. Three Pigeon pea accessions were cultivated in a greenhouse. After harvesting, one access was separated into two aliquots. One aliquot was freeze-dried (?196 °C), and the other was dried in a forced

Edilene C. Ferreira; Ana Rita A. Nogueira; Gilberto B. Souza; Luiz A. R. Batista



Mangrove tannins in aquatic ecosystems: Their fate and possible influence on dissolved organic carbon and nitrogen cycling  

Microsoft Academic Search

We describe the fate of mangrove leaf tannins in aquatic ecosystems and their possible influence on dissolved organic nitrogen (DON) cycling. Tannins were extracted and purified from senescent yellow leaves of the red mangrove (Rhizophora mangle) and used for a series of model experiments to investigate their physical and chemical reactivity in natural environments. Physical processes investigated included aggregation, adsorption

Nagamitsu Maie; Oliva Pisani



Effect of variety and harvesting management on the concentration of tannins and alkaloids in tagasaste ( Chamaecytisus palmensis)  

Microsoft Academic Search

The first part of this study evaluated contents of hydrolysable tannins (HT) and condensed tannins (CT) of 65 accessions of tagasaste. In the second part, the effects of harvesting stage and growing season on the contents of HT, CT and alkaloids in different plant parts of the widely grown tagasaste variety ‘MOA’ was studied in a randomized complete block design.

Getnet Assefa; K. Sonder; M. Winkc; C. Kijora; N. Steinmueller; K. J. Peters



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

PubMed Central

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 ascariosis. PMID:24810761

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



Nano-porous solid-state photovoltaic cell sensitized with tannin  

NASA Astrophysics Data System (ADS)

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

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



New hydrolyzable tannins, shephagenins A and B, from Shepherdia argentea as HIV-1 reverse transcriptase inhibitors.  


Two new hydrolyzable tannins, shephagenins A and B, were isolated along with hippophaenin A and strictinin from the leaf extract of Shepherdia argentea, which showed a remarkable inhibitory activity against human immunodeficiency virus (HIV)-1 reverse transcriptase. Their structures, having a gluconic acid core, have been elucidated on the basis of spectroscopic and chemical methods. The inhibitory effect of the leaf extract on HIV-1 reverse transcriptase was found to be due to tannins, and their activities were stronger than that of (-)-epigallocatechin gallate as a positive control. PMID:8795264

Yoshida, T; Ito, H; Hatano, T; Kurata, M; Nakanishi, T; Inada, A; Murata, H; Inatomi, Y; Matsuura, N; Ono, K; Nakane, H; Noda, M; Lang, F A; Murata, J



Toxicity of tannins towards the free-living nematode Caenorhabditis elegans and the brine shrimp Artemia salina.  


Toxicities of gallo- and condensed tannins towards the free-living nematode Caenorhabditis elegans is dependent on the tannins' molecular sizes. In the present paper we investigate the toxicity of ellagitannins to C elegans and the toxicity of ellagi-, gallo-, and condensed tannins to the brine shrimpArtemia salina. Ellagitannins 1 and 2 were isolated from Euphorbia supina and identified as tellimagrandin I and rugosin A methyl ester, respectively. An ellagitannin preparation from Cornus officinalis was chromatographically fractionated into ellagitannins A through H, having different molecular weights and specific rotations. Three of the ten ellagitannins, 2, G, and H produced significant toxicity towards C. elegans, showing the presence of an activity-structure relationship, as opposed to the results from tests of gallo- and condensed tannins. Ellagi-, gallo-, and condensed tannins also produced toxicity in A. salina. PMID:12182536

Yamasaki, Toru; Sato, Masashi; Mori, Tomoaki; Mohamed, Ahmed S A; Fujii, Kyoko; Tsukioka, Junko



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


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, Caninae, and Synstylae. PMID:25220498

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



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

PubMed Central

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-based antivirals. PMID:24498245

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



Pentasaccharide glycosides from the tubers of sweet potato (Ipomoea batatas).  


Sweet potato ( Ipomoea batatas) has been used as food and herb in many countries. In this research on the active constituents of sweet potato, nine compounds were isolated and identified, including seven new resin glycosides, batatosides A-G (1- 7), along with two known compounds, batatinoside I ( 8) and simonin IV ( 9). The structures of 1- 9 have been established by a combination of spectroscopic and chemical methods. The major characteristics of the new compounds are the presence of three different substituents. The absolute configuration of aglycones was established as S by Mosher's method. Batatoside E ( 5) showed weak cytotoxic activity against Hep-2 cells. PMID:18341282

Yin, Yongqin; Li, Yi; Kong, Lingyi



Pentasaccharide resin glycosides from Ipomoea cairica and their cytotoxic activities.  


Six partially acylated pentasaccharide resin glycosides, cairicosides A-F, were isolated from the aerial parts of Ipomoea cairica. These compounds were characterized as a group of macrolactones of simonic acid A, partially acylated with different organic acids. The lactonization site of 11S-hydroxyhexadecanoic acid (jalapinolic acid) was bound to the second saccharide moiety at C-3 in cairicosides A-E, while at C-2 in cairicoside F. Structures were established by spectroscopic and chemical methods. Compounds cairicosides A-E exhibited moderate cytotoxicity against a small panel of human tumor cell lines with IC50 values in the range of 4.28-14.31?M. PMID:23954073

Yu, Bangwei; Luo, Jianguang; Wang, Junsong; Zhang, Dongming; Yu, Shishan; Kong, Lingyi



Three new dammarane glycosides from heat processed ginseng  

Microsoft Academic Search

Three new dammarane glycosides were isolated from the processed ginseng (SG; Sun Ginseng). Their structure were determined\\u000a to be 3?,12?-dihydroxydammar-20(21),24-diene-3-O-?-D-glucopyranosyl(1 ? 2)-?-D-glucopyranoside; 3?,12?-dihydroxydammar-20(21),24-diene-3-O-?-D-\\u000a glucopyranoside and 3?,6?,12?-trihydroxydammar-20(21),24-diene-6-O-?-D-glucopyr-anoside based on spectroscopic evidences.\\u000a The compounds were named as ginsenoside Rk1 Rk2, and Rk3 respectively.

II Ho Park; Na Young Kim; Sang Beom Han; Jong Moon Kim; Sung Won Kwon; Hyun Jung Kim; Man Ki Park; Jeong Hill Park



Melitidin: a flavanone glycoside from Citrus grandis 'Tomentosa'.  


Citrus grandis 'Tomentosa' is a traditional Chinese medicine, used as an antitussive. In this research, melitidin, a flavanone glycoside, was isolated from this species for the first time by using chromatographic methods. The structure was confirmed through comprehensive analyses of its ultraviolet, infrared, 1H and 13C NMR, HMBC and HMQC spectroscopic and high-resolution mass spectrometric data. Meliditin showed a good antitussive effect on cough induced by citric acid in Guinea pig, suggesting that it was a contributor to the antitussive effect of C. grandis 'Tomentosa'. PMID:23738451

Zou, Wei; Wang, Yonggang; Liu, Haibin; Luo, Yulong; Chen, Si; Su, Weiwei



Inhibition of amyloid ? aggregation by acteoside, a phenylethanoid glycoside.  


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

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



A dammarane glycoside derived from ginsenoside Rb3.  


A dammarane glycoside, designated compound Mx (C-Mx), was isolated from the hydrolysate of 20(S)-protopanaxadiol type ginsenosides containing G-Rb(3) from Panax notoginseng leaves with crude snailase. Its chemical structure was elucidated to be 20-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranosyl-20(S)-protopanaxadiol on the basis of spectral analysis. Its cytotoxicity against breast cancer cell line MCF-7 and effects on the sensitivity to doxocubicin of doxocubicin-resistant MCF-7 cells were also investigated. The new compound showed moderate cytotoxicity and partial reversal of doxocubicin resistance. PMID:15684516

He, Kejiang; Liu, Yong; Yang, Yi; Li, Peng; Yang, Ling



Glycosides from whole plants of Glechoma hederacea L.  


From dried whole plants of Glechoma hederacea L. (Labiatae), seven known glycosides were isolated and identified: (6R,7E,9R)-megastigma-4,7-dien-3-one 9-O-beta-D-glucopyranoside (1), apigenin 7-O-neohesperidoside (2), chrysoeriol 7-O-neohesperidoside (3), (+)-pinoresinol 4,4'-bis-O-beta-D-glucopyranoside (4), (+)-syringaresinol 4,4'-bis-O-beta-D-glucopyranoside (5), (+)-lariciresinol 4,4'-bis-O-beta-D-glucopyranoside (6), and (7R,8R)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan 4-O-beta-D-glucopyranoside (7). PMID:18553179

Kikuchi, Masao; Goto, Junichi; Noguchi, Saori; Kakuda, Rie; Yaoita, Yasunori



Glycosides from whole plants of Glechoma hederacea L  

Microsoft Academic Search

From dried whole plants of Glechoma hederacea L. (Labiatae), seven known glycosides were isolated and identified: (6R,7E,9R)-megastigma-4,7-dien-3-one 9-O-?-d-glucopyranoside (1), apigenin 7-O-neohesperidoside (2), chrysoeriol 7-O-neohesperidoside (3), (+)-pinoresinol 4,4?-bis-O-?-d-glucopyranoside (4), (+)-syringaresinol 4,4?-bis-O-?-d-glucopyranoside (5), (+)-lariciresinol 4,4?-bis-O-?-d-glucopyranoside (6), and (7R,8R)-threo-7,9,9?-trihydroxy-3,3?-dimethoxy-8-O-4?-neolignan 4-O-?-d-glucopyranoside (7).

Masao Kikuchi; Junichi Goto; Saori Noguchi; Rie Kakuda; Yasunori Yaoita



Two new phenolic glycosides from the rhizome of Gastrodia elata  

Microsoft Academic Search

Two new phenolic glycosides, named parishins F–G (1–2), together with known parishin E, were isolated from the rhizome of Gastrodia elata. The new structures were established as 1,3-di-[4-O-(?-d-glucopyranosyl) benzyl]-2-{4-O-[?-d-glucopyranosyl-(1 ? 6)-?-d-glucopyranosyl] benzyl} citrate (1) and 2-[4-O-(?-d-glucopyranosyl)benzyl] citrate (2), by means of MS, 1D, and 2D NMR spectral analyses, as well as chemical methods.

Li Wang; Hong-Bin Xiao; Li Yang; Zheng-Tao Wang



Two new flavonoid glycosides from Artemisia frigida Willd  

Microsoft Academic Search

An investigation of the n-BuOH-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new flavonoid glycosides, named friginoside A and friginoside B. Their structures were characterized as 5,7-dihydroxy-3?,4?,5?-trimethoxy flavone 7-O-?-d-glucuronide (1) and 5,7-dihydroxy-3?,4?,5?-trimethoxyflavone 7-O-?-d-glucuronyl-(1 ? 2)O-?-d-glucuronide (2) on the basis of 1D and 2D NMR spectral analysis.

Qing-Hu Wang; Wu-Li-Ji Ao; Xiu-Lan Wang; Xiao-Hua Bao; Jin-Hui Wang



Two new flavonoid glycosides from Artemisia frigida Willd.  


An investigation of the n-BuOH-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new flavonoid glycosides, named friginoside A and friginoside B. Their structures were characterized as 5,7-dihydroxy-3',4',5'-trimethoxy flavone 7-O-?-d-glucuronide (1) and 5,7-dihydroxy-3',4',5'-trimethoxyflavone 7-O-?-d-glucuronyl-(1 ? 2)O-?-d-glucuronide (2) on the basis of 1D and 2D NMR spectral analysis. PMID:21061216

Wang, Qing-Hu; Ao, Wu-Li-Ji; Wang, Xiu-Lan; Bao, Xiao-Hua; Wang, Jin-Hui



7-O-Methylated anthocyanidin glycosides from Catharanthus roseus.  


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. PMID:18164044

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



A new steroidal glycoside from the seeds of Hyoscyamus niger.  


A new steroidal glycoside hyoscyamoside G (1), together with two known analogues hyoscyamoside E (2) and hyoscyamoside F1 (3), was isolated from the seeds of Hyoscyamus niger. The structure of 1 was established as (22R,24Z)-1?,3?,7?,22,26-pentakishydroxylergost-22-O-?-d-gulcopyranosyl-5,24-diene-26-O-?-d-glucopyranoside, by means of chemical and spectroscopic methods including HRESI-MS, 1D and 2D NMR. In vitro, compound 2 showed cytotoxicity against human lung cancer cell H460 with IC50 value of 66 ?g/mL. PMID:23745717

Zhang, Wenna; Zhang, Wei; Luo, Jianguang; Kong, Lingyi



Two new glycosides from the fruits of Morinda citrifolia L.  


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

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



A new flavonol glycoside from the aerial part of Rudbeckia laciniata.  


The phytochemical investigation of Rudbeckia laciniata L. obtained a new flavonol glycoside (1), together with four flavonol glycosides (2-5) and eight quinic acid derivatives (6-13). The structure was elucidation by means of spectroscopic methods and chemical evidence. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using the sulforhodamine B bioassay. PMID:24062080

Lee, Seung Young; Shin, Young June; Choi, Sang Un; Lee, Kang Ro



Antioxidant and cholinesterases inhibitory activities of Verbascum xanthophoeniceum Griseb. and its phenylethanoid glycosides  

Microsoft Academic Search

The members of Verbascum L. (Scrophulariaceae) are known to be rich in phenylethnoid glycosides, and among them Verbascum xanthophoeniceum is an endemic plant species for the Balkan region, Northwestern, and Southern Turkey. A scheme was developed for the isolation of the main active constituents that accumulate in plant aerial parts. The antioxidant activities of total methanol extracts, collected phenylethanoid glycosides

Milen Georgiev; Kalina Alipieva; Ilkay Orhan; Radoslav Abrashev; Petko Denev; Maria Angelova



Glycosides of 19-formylthevetiogenin and 5 alpha-thevetiogenin from Thevetia neriifolia.  


C-nor-D-homo-homologues of cannogenin and uzarigenin glycosides were isolated along with known cardenolide glycosides from the frozen fresh leaves of Thevetia neriifolia. A bisdesmosidic tetraoside of 3 beta,14,21-trihydroxy-5 beta,14 beta-pregnan-20-one was also obtained from the polar fraction and the structure established. PMID:7765761

Abe, F; Yamauchi, T; Yahara, S; Nohara, T



Selective sequestration of iridoid glycosides from their host plants in Longitarsus flea beetles  

Microsoft Academic Search

We investigated in eight species of the flea beetles genus Longitarsus (Coleoptera, Chrysomelidae) whether the beetles take up iridoid glycosides from their host plants of the Lamiaceae, Plantaginaceae, and Scrophulariaceae. Five of the beetle species, L. australis, L. lewisii, L. melanocephalus, L. nigrofasciatus, and L. tabidus, could be shown to sequester iridoid glycosides in concentrations between 0.40 and 1.55% of

Gunther Willinger; Susanne Dobler



Biochemical detoxication: mechanism of differential tiger swallowtail tolerance to phenolic glycosides  

Microsoft Academic Search

Phenolic glycosides, commonly occurring allelochemicals in the plant family Salicaceae, are differentially toxic to subspecies of the eastern tiger swallowtail and responsible for striking differences in the abilities of Papilio glaucus canadensis and P.g. glaucus to utilize the Salicaceae as food plants. This research was designed to test the hypothesis that particularly high esterase activity confers resistance to phenolic glycosides

R. L. Lindroth



The Cyanogenic Glycoside Amygdalin Does Not Deter Consumption of Ripe Fruit by Cedar Waxwings  

Microsoft Academic Search

Cyanogenic glycosides are common secondary compounds in ripe fruits that are dispersed by birds. These substances are toxic to some mammals. We examined the repellent effect of amygdalin, a cyanogenic glycoside, on Cedar Waxwings (Bombycilla cedrorum). Amygdalin did not reduce food ingestion in Cedar Waxwings, even at relatively high concentrations. In addition, these birds did not exhibit preference for amygdalin-free

H. M Struempf; J. E Schondube; Carlos Martinez del Rio



Merremins A-G, Resin Glycosides from Merremia hederacea with Multidrug Resistance Reversal Activity.  


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 ?M. Compound 5 and murucoidin V, with 20-membered rings, were more active than compound 1, with an 18-membered ring. PMID:25310730

Wang, Wen-Qiong; Song, Wei-Bin; Lan, Xiao-Jing; Huang, Min; Xuan, Li-Jiang



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


Meeting the rising consumer demand for natural food ingredients, steviol glycosides, the sweet principle of Stevia rebaudiana Bertoni (Bertoni), have recently been approved as food additives in the European Union. As regulatory constraints require sensitive methods to analyze the sweet-tasting steviol glycosides in foods and beverages, a HILIC-MS/MS method was developed enabling the accurate and reliable quantitation of the major steviol glycosides stevioside, rebaudiosides A-F, steviolbioside, rubusoside, and dulcoside A by using the corresponding deuterated 16,17-dihydrosteviol glycosides as suitable internal standards. This quantitation not only enables the analysis of the individual steviol glycosides in foods and beverages but also can support the optimization of breeding and postharvest downstream processing of Stevia plants to produce preferentially sweet and least bitter tasting Stevia extracts. PMID:24206531

Well, Caroline; Frank, Oliver; Hofmann, Thomas



Growth of sheep fed tannin-rich Albizia gummifera with or without polyethylene glycol.  


Twenty-four intact male Bonga lambs were studied in a 100-day experiment to evaluate the effect of feeding tannin rich leaves of Albizia gummifera (AG) on nutrient utilization, growth performance, and carcass composition. The dietary treatments consisted of hay alone (T1, control), AG at 30 % of control diet + T1 (T2), and T2 + polyethylene glycol 6000 (PEG) (T3, 40 mg PEG, 1 kg AG/head on a dry mass (DM) basis. The lambs were individually fed at 50 g DM/kg live weight. In the last 10 days of the experiment, all animals from each treatment were harnessed with feces collection bags. At the end of the experiment, lambs were slaughtered after overnight fasting for measurements of carcass characteristics. Crude protein, neutral detergent fiber, and condensed tannin contents of AG were 300, 586, and 108 g/kg DM, respectively. Lambs fed AG with PEG had higher (P?tannins on livestock performance. Leaves of AG enhance digestibility and performance in tropical hay-fed sheep, and the addition of PEG further improves this effect, likely due to the binding of tannins. PMID:24832590

Yisehak, Kechero; Biruk, Kebede; Abegaze, Beyene; Janssens, Geert P J



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


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

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



Influence of thorns and tannins on white-tailed deer browsing after mowing  

Microsoft Academic Search

We used caged and uncaged plants to compare shoot growth, biomass, spinescence, nutrient, and tannin content of blackbrush acacia (Acacia rigidula Benth.), honey mesquite (Prosopis glandulosa Torr.), and spiny hackberry (Celtis pallida Torr.) 6 and 12 weeks after mowing, and estimated white-tailed deer (Odocoileus virginianus Raf.) use of sprouts of each species stripped of spines and unstripped. Blackbrush acacia grew

Jason R. Schindler; Timothy E. Fulbright; T. D. A. Forbes



linkage between a phenolic acid and the carbohydrate of hydrolysable tannins.  

E-print Network

at an internal peptide derived from Endo-Lys C hydrolysis and HPLC purifi- cation. From the amino acid sequence. Purified enzyme has been obtained and 13 amino acids were se- quenced at the N terminus and 10 amino acidslinkage between a phenolic acid and the carbohydrate of hydrolysable tannins. TAH has

Paris-Sud XI, Université de


Field studies of the relationship between herbivore damage and tannin concentration in bracken ( Pteridium aquilinum Kuhn)  

Microsoft Academic Search

The acceptance of secondary plant metabolites as herbivore deterrents rests primarily on their deleterious effects on herbivores. Efforts to demonstrate differential fitness in natural plant populations with varying concentrations of tannin have failed, since coevolved plant predators may physiologically or behaviorally circumvent the defense, which results in apparently equal amounts of damage to defended and undefended individuals. In this study,

Alice S. Tempel



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

PubMed Central

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

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



Inuence of balsam poplar tannin fractions on carbon and nitrogen dynamics in Alaskan taiga oodplain soils  

E-print Network

In¯uence of balsam poplar tannin fractions on carbon and nitrogen dynamics in Alaskan taiga. In the Alaskan taiga, changes in nutrient cycling caused by balsam poplar (Populus balsamifera) secondary poplar; Taiga 1. Introduction Disturbance and succession dominate the landscape structure of the Alaskan

Fierer, Noah


Influence of Myriophyllum spicatum Derived Tannins on Gut Microbiota of Its Herbivore Acentria ephemerella  

Microsoft Academic Search

The submerged living larvae of Acentria ephemerella were fed in the laboratory with either M. spicatum or Potamogeton perfoliatus, two of their host plants. Larvae exhibited a reduced growth when fed M. spicatum, a freshwater angiosperm that contains high concentrations of tannins, secondary metabolites known for their herbivore-deterrent and antimicrobial properties. In this study, we investigated the influence of food-derived

Oliver Walenciak; Walter Zwisler; Elisabeth M. Gross



The effect of a condensed tannin-containing forage on methane emission by goats1  

Microsoft Academic Search

The objective of this study was to com- pare methane emission by goats consuming the con- densed tannin-containing forage sericea lespedeza (Les- pedeza cuneata) or a mixture of crabgrass (Digitaria ischaemum) and Kentucky 31 tall fescue (Festuca arun- dinacea). Two groups of 12 Angora does (initial average BW = 41.5 ± 2.7 kg) that previously grazed a pasture of sericea

R. Puchala; B. R. Min; A. L. Goetsch; T. Sahlu



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


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

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



Condensed Tannin Concentrations of Three Lotus Species Grown in Different Environments  

Microsoft Academic Search

A B S T R A C T Condensed tannins (CT) present in Lotus spp., depending on their concentration in the plant, can prevent bloating and improve protein absorption in ruminants. With the objective to know the variability of this characteristic, the CT concentration (% dry matter basis) was determined by the butanol-HCl procedure in 13 cultivars of Lotus corniculatus

Hernán Acuña; Alex Concha; Marcos Figueroa



Feeding and digesting fiber and tannins by an herbivorous rodent, Octodon degus (Rodentia: Caviomorpha)  

Microsoft Academic Search

Differences in feeding rates and digestive efficiency of alternative experimental diets differing in cellulose or fiber and a secondary metabolite (the hydrolyzable tannin, tannic acid [TA]) were assessed with the herbivorous burrowing caviomorph rodent Octodon degus (degu). Degus live in open scrub subjected to summer droughts. The in vitro activity of the digestive enzyme sucrase was not significantly different between

Francisco Bozinovic; F. Fernando Novoa; Pablo Sabat



Variability of total flavonoid, polyphenol and tannin contents in some Lythrum salicaria populations.  


Lythrum salicaria L. can vary in some morphological and phytochemical features according to its habitat. The present study investigates and compares the total flavonoid, polyphenol and tannin composition of twelve populations of L. salicaria collected from different ecological habitats in south-west Hungary. We studied the plant heights and soil moistures of the habitats analyzing the potential correlation between the morphological and environmental factors and chemical compositions. Total flavonoid, polyphenol and tannin contents were determined according to the valid spectroscopic methods of the European Pharmacopoeia. Total flavonoid content was higher in the populations collected during the main blooming period in August than at the beginning of flowering in July. Higher values for total polyphenol and tannin were detected in flowering branch tips in August than in July, and higher ones in leaves and shoots in July than in August. The highest flavonoid content was measured in the leaves, followed by the flowering branches and shoots as opposed to the total polyphenol and tannin contents, which were higher in the flowering branch tips than in the other organs. PMID:22164772

Bencsik, Tímea; Horváth, Györgyi; Papp, Nóra



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

Microsoft Academic Search

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

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



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


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 3?-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 3?-caffeate (IC(50) = 0.85 ± 0.1 ?M) and to a lesser extent for the flacourtosides A and E (1 and 5, respectively), and scolochinenoside D (IC(50) values ~10 ?M). PMID:22439591

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



Phenylethanoid glycosides from the stems of Callicarpa peii (hemostatic drug).  


Two new trisaccharide intermediates of phenylethanoid glycosides, peiioside A(1)/A(2) (1a/1b) and peiioside B (2), were isolated from the n-BuOH fraction of MeOH extract of the stems of Callicarpa peii H.T. Chang, together with five biogenetic relevant known compounds 3-7. The structures of compounds 1 and 2 were elucidated by extensive spectroscopic methods (especially 2D-NMR techniques) and acid-catalyzed hydrolysis as O-?-l-rhamnopyranosyl-(1??3')-O-[?-d-apiofuranosyl-(1??6')] -4'-O-[(E)-caffeoyl]-d-glucopyranoside] (1a/1b), 3,4-dihydroxy-?-phenylethoxy-O-[?-d-apiofuranosyl-(1??6')-?-l-rhamnopyranosyl-(1??3')-O-?-d-glucopyranoside] (2), respectively. On the basis of the isolated compounds, a presumable biogenetic pathway of the biologically interesting phenylethanoid glycosides about forsythoside B (3) and acteoside (4) isolated from this species was proposed. Isolation of five related intermediates (1-2, 5-7) provided further support for the biogenetic path. This is the first report about phytochemical research on C. peii and the biogenetic hypothesis of forsythoside B and acteoside. PMID:23262269

Wu, Ai-Zhi; Zhai, Ya-Jing; Zhao, Zhong-Xiang; Zhang, Cui-Xian; Lin, Chao-Zhan; Zhu, Chen-Chen



Separation of phenylpropanoid glycosides from a Chinese herb by HSCCC.  


An effective high-speed counter-current chromatography method was established for the preparative isolation and purification of two phenylpropanoid glycosides from the Tibetan medicinal plant Pedicularis longiflora Rudolph. var. tubiformis (Klotz). Tsoong. With a two-phase solvent system composed of chloroform-n-butanol-methanol-water (4:3:4:5, v/v), 40 mg of an extract of Pedicularis longiflora Rudolph. var. tubiformis (Klotz). Tsoong was separated to yield 20 mg of verbascoside and 18 mg of isoacteoside, with purity values of 97 and 98%, respectively. The chemical structures of these two components were identified by proton and carbon nuclear magnetic resonance. In addition, the antioxidant activity of the two phenylpropanoid glycosides was evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH)-high-performance liquid chromatography, and the results showed that the two components exhibited strong antioxidant DPPH radical scavenging activity, with IC50 values of 15.6 and 18.9 µg/mL, respectively. PMID:23680899

Chen, Chen; Zhao, Xiao-Hui; Yue, Hui-Lan; Li, Yu-Lin; Chen, Tao



Angling for Uniqueness in Enzymatic Preparation of Glycosides  

PubMed Central

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

Trincone, Antonio



Potent antiviral flavone glycosides from Ficus benjamina leaves.  


Crude ethanol extracts from Ficus benjamina leaves strongly inhibit Herpes Simplex Virus 1 and 2 (HSV-1/2) as well as Varicella Zoster Virus (VZV) cell infection in vitro. Bioassay-guided fractionation of the crude extract demonstrated that the most efficient inhibition of HSV-1 and HSV-2 was obtained with the flavonoid fraction. The present study was aimed to further isolate, purify and identify substances with potent antiviral activity from the flavonoid fraction of F. benjamina extracts. Flavonoids were collected from the leaf ethanol extracts through repeated purification procedure and HPLC analysis. The antiviral activity of each substance was then evaluated in cell culture. Three known flavone glycosides, (1) quercetin 3-O-rutinoside, (2) kaempferol 3-O-rutinoside and (3) kaempferol 3-O-robinobioside, showing highest antiviral efficiency were selected and their structure was determined by spectroscopic analyses including NMR and mass spectrometry (MS). These three flavones were highly effective against HSV-1 reaching a selectivity index (SI) of 266, 100 and 666 for compound 1, 2 and 3, respectively, while the SI of their aglycons, quercetin and kaempferol amounted only in 7.1 and 3.2, respectively. Kaempferol 3-O-robinobioside showed similar SI to that of acyclovir (ACV), the standard anti-HSV drug. Although highly effective against HSV-1 and HSV-2, these flavone glycosides did not show any significant activity against VZV. PMID:22155188

Yarmolinsky, Ludmila; Huleihel, Mahmoud; Zaccai, Michele; Ben-Shabat, Shimon



Binding affinity of hydrolyzable tannins to parotid saliva and to proline-rich proteins derived from it.  


Proline-rich proteins (PRP) in human parotid saliva have a high affinity for dietary polyphenolic compounds (tannins), forming stable complexes that may modulate the biological and nutritional properties of the tannin. The formation of such complexes may also have an important role in the modulation or promotion of the sensation of oral astringency perceived when tannin-rich foods and beverages are consumed. The major classes of PRP (acidic, basic, and glycosylated) have been isolated from human saliva, and the relative binding affinities of a series of hydrolyzable tannins, which are found in a number of plant-derived foods and beverages, to these PRP classes have been determined using a competition assay. All of the classes of PRP have a high capacity for hydrolyzable tannins. Within the narrow range of binding affinities exhibited, structure/binding relationships with the levels of tannin galloylation, hexahydroxydiphenoyl esterification, and degree of polymerization were identified. No individual class of human salivary PRP appears to have an exclusive affinity for a particular type of hydrolyzable tannin. PMID:10725160

Bacon, J R; Rhodes, M J



The gastroprotective effects of Eugenia dysenterica (Myrtaceae) leaf extract: the possible role of condensed tannins.  


We applied a taxonomic approach to select the Eugenia dysenterica (Myrtaceae) leaf extract, known in Brazil as "cagaita," and evaluated its gastroprotective effect. The ability of the extract or carbenoxolone to protect the gastric mucosa from ethanol/HCl-induced lesions was evaluated in mice. The contributions of nitric oxide (NO), endogenous sulfhydryl (SH) groups and alterations in HCl production to the extract's gastroprotective effect were investigated. We also determined the antioxidant activity of the extract and the possible contribution of tannins to the cytoprotective effect. The extract and carbenoxolone protected the gastric mucosa from ethanol/HCl-induced ulcers, and the former also decreased HCl production. The blockage of SH groups but not the inhibition of NO synthesis abolished the gastroprotective action of the extract. Tannins are present in the extract, which was analyzed by matrix assisted laser desorption/ionization (MALDI); the tannins identified by fragmentation pattern (MS/MS) were condensed type-B, coupled up to eleven flavan-3-ol units and were predominantly procyanidin and prodelphinidin units. Partial removal of tannins from the extract abolished the cytoprotective actions of the extract. The extract exhibits free-radical-scavenging activity in vitro, and the extract/FeCl3 sequence stained gastric surface epithelial cells dark-gray. Therefore, E. dysenterica leaf extract has gastroprotective effects that appear to be linked to the inhibition of HCl production, the antioxidant activity and the endogenous SH-containing compounds. These pleiotropic actions appear to be dependent on the condensed tannins contained in the extract, which bind to mucins in the gastric mucosa forming a protective coating against damaging agents. Our study highlights the biopharmaceutical potential of E. dysenterica. PMID:24789995

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



Sudden cardiac death  

Microsoft Academic Search

The rate of cardiac deaths that are sudden is approximately 50%, and decreases with age. The causes of sudden cardiac death are diverse, and are a function of age. In children and adolescents, coronary anomalies, hypertrophic cardiomyopathy and myocarditis are frequent substrates for lethal arrhythmias; in adults, coronary atherosclerosis and acquired forms of cardiomyopathy are the most common findings at

Renu Virmani; Allen P Burke; Andrew Farb



Hybrid Pediatric Cardiac Surgery  

Microsoft Academic Search

Minimally invasive strategies can be expanded by combining standard surgical and interventional techniques. We performed a longitudinal prospective study of all pediatric patients who have undergone hybrid cardiac surgery at the University of Chicago Children's Hospital. Hybrid cardiac surgery was defined as combined catheter-based and surgical interventions in either one setting or in a planned sequential fashion within 24 hours.

E. A. Bacha; Z. M. Hijazi; Q. L. Cao; R. Abdulla; J. P. Starr; J. Quinones; P. Koenig; B. Agarwala



Functional cardiac tissue engineering  

PubMed Central

Heart attack remains the leading cause of death in both men and women worldwide. Stem cell-based therapies, including the use of engineered cardiac tissues, have the potential to treat the massive cell loss and pathological remodeling resulting from heart attack. Specifically, embryonic and induced pluripotent stem cells are a promising source for generation of therapeutically relevant numbers of functional cardiomyocytes and engineering of cardiac tissues in vitro. This review will describe methodologies for successful differentiation of pluripotent stem cells towards the cardiovascular cell lineages as they pertain to the field of cardiac tissue engineering. The emphasis will be placed on comparing the functional maturation in engineered cardiac tissues and developing heart and on methods to quantify cardiac electrical and mechanical function at different spatial scales. PMID:22397609

Liau, Brian; Zhang, Donghui; Bursac, Nenad



Preliminary Phytochemical Screening and Antibacterial Studies on the Ethanolic Leaf Extract of Nyctanthes arbortristis Linn  

Microsoft Academic Search

Nyctanthes arbortristis Linn. is extensively used in Indian traditional and folklore medicines to cure various human ailments. The preliminary phytochemical screening of the leaves revealed the presence of alkaloids, tannins, flavonoids, cardiac glycosides and sugars. In vitro antibacterial studies on the ethanolic leaf extracts were carried out on ten medically important bacterial strains, including Salmonella typimurium, Pseudomonas aeruginosa, Klebsiella pneumonia,

M. Sathiya; P. Parimala; K. Muthuchelian



Phytochemical Investigation and Antibacterial Screening of Ethanolic Leaf Extract of Sapindus emarginatus Vahl  

Microsoft Academic Search

Sapindus emarginatus Vahl. is extensively used in Indian traditional and folklore medicines to cure various human ailments. The preliminary phytochemical screening of the leaves revealed the presence of saponins, terpenoids, tannins, acids, flavonoids, cardiac glycosides and sugars. In vitro antibacterial studies on the ethanolic leaf extracts were carried out on ten medically important bacterial strains, including Salmonella typimurium, Pseudomonas aeruginosa,

M. Sathiya; K. Muthuchelian



Determination of infochemicals and the phytochemical screening of the foliage and stem-bark of Senna siamea (lam.) in Yola, Adamawa State  

Microsoft Academic Search

Alkaloids, anthraquinonnes, cardiac glycosides, flavonoids, phlobatannin, polyphenols, saponins, steroids, tannins and terpenoids were ten groups of infochemicals studied in the foliage and stem-bark of Senna siamea (Lam.), a plantation species grown in Yola. The experimental design was the Randomized Complete Block Design (RCBD) with four replications. Results obtained from the experiments indicated that all the ten groups of infochemicals were

Ayuba Daniel Kwada; I. O. Tell


Crotalaria pallida extracts as a putative HIV-protease inhibitors  

Microsoft Academic Search

In the present investigation, we screened the two solvent (methanol and ethanol) extracts of Crotalaria pallida different parts (leaf, flower and stem) for phytochemical analysis and screening for HIV protease inhibitors. The two solvent extracts have yielded the presence of major active compounds viz., flavonoids, terpenoids, cardiac glycosides, anthraquinones, coumarins, steroids, tannins, saponins. For HIV protease inhibitor activity, we used

Govindappa M; Anil Kumar NV



Monitoring of aglycons of yew glycosides (3,5-dimethoxyphenol, myrtenol and 1-octen-3-ol) as first indicator of yew presence.  


The toxicity of yew (Taxus spp) is well known from ancient times and is mainly due to taxins acting as inhibitors of calcium and sodium transport across the cell membrane of cardiac myocytes. The confirmation of yew taxins in body fluids can be carried out by liquid chromatography-tandem mass spectrometry (LC-MS/MS). However, before selecting this precise but expensive technique, an orientation test should be done to ascertain yew presence as toxic agent in the organism. As the 3,5-dimethoxyphenol (3,5-DMP), myrtenol and 1-octen-3-ol appear as glycosidically bound volatile compounds and are very yew specific, the detection of 3,5-DMP and the measurement of 1-octen-3-ol / myrtenol concentration ratio constitute reliable indicators of yew presence in forensic cases. The detection of these compounds is easily performed by gas chromatography-mass spectrometry (GC-MS) (SIM) after an enzymatic hydrolysis (?-glucosidase) allowing the release of volatile compounds from yew glycosides. PMID:22371422

Varlet, V; Augsburger, M



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

PubMed Central

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

Guleria, Praveen; Yadav, Sudesh Kumar



Cardiac involvement in leptospirosis.  


Leptospirosis is a neglected global disease with significant morbidity and mortality. Cardiac complications such as chest pain, arrhythmias, pulmonary oedema and refractory shock have been reported in patients with severe disease. However, the frequency and extent of cardiac involvement in leptospirosis, are under-reported and poorly understood. Multiple factors may contribute to clinical manifestations that suggest cardiac involvement, causing diagnostic confusion. A variety of electrocardiographic changes occur in leptospirosis, with atrial fibrillation, atrioventricular conduction blocks and non-specific ventricular repolarization abnormalities being the most common. Electrolyte abnormalities are likely to contribute to electrocardiographic changes; direct effects on Na(+)-K(+)-Cl(-) transporters in the renal tubules have been postulated. Echocardiographic evidence of myocardial dysfunction has not been adequately demonstrated. The diagnostic value of cardiac biomarkers is unknown. Histopathological changes in the myocardium have been clearly shown, with myocardial inflammation and vasculitis present in postmortem studies. Nonetheless, the pathophysiology of cardiac involvement in leptospirosis is poorly understood. Cardiac involvement, demonstrated electrocardiographically or clinically, tends to predict poor outcome. No specific therapies are available to prevent or treat cardiac involvement in leptospirosis; current management is based on correction of deranged homeostasis and supportive therapy. Evidence suggests that direct myocardial damage occurs in patients with severe leptospirosis, and further studies are recommended to elucidate its pathophysiology, clinical features and contribution to overall prognosis, and to identify appropriate diagnostic investigations and specific therapies. PMID:22818758

Navinan, Mitrakrishnan Rayno; Rajapakse, Senaka



Modeling inherited cardiac disorders.  


Advances in the understanding and treatment of cardiac disorders have been thwarted by the inability to study beating human cardiac cells in vitro. Induced pluripotent stem cells (iPSCs) bypass this hurdle by enabling the creation of patient-specific iPSC-derived cardiomyocytes (iPSC-CMs). These cells provide a unique platform to study cardiac diseases in vitro, especially hereditary cardiac conditions. To date, iPSC-CMs have been used to successfully model arrhythmic disorders, showing excellent recapitulation of cardiac channel function and electrophysiologic features of long QT syndrome types 1, 2, 3, and 8, and catecholaminergic polymorphic ventricular tachycardia (CPVT). Similarly, iPSC-CM models of dilated cardiomyopathy (DCM) and hypertrophic cardiomyopathy (HCM) have shown robust correlation of predicted morphologic, contractile, and electrical phenotypes. In addition, iPSC-CMs have shown some features of the respective phenotypes for arrhythmogenic right ventricular dysplasia/cardiomyopathy (ARVD/C), LEOPARD syndrome, Pompe's disease, and Friedriech's ataxia. In this review, we examine the progress of utilizing iPSC-CMs as a model for cardiac conditions and analyze the potential for the platform in furthering the biology and treatment of cardiac disorders.?? PMID:24632794

Sallam, Karim; Kodo, Kazuki; Wu, Joseph C



Flavonoid Glycosides from the Seeds of Litchi chinensis.  


Seven flavonoid glycosides, including one new (1) and five previously uncharacterized (3-7), were obtained from the seeds of lychee ( Litchi chinensis Sonn. cv. Heiye) by means of repetitive column chromatography and high-performance liquid chromatography (HPLC) preparation. They were identified as litchioside D (1), (-)-pinocembrin 7-O-neohesperidoside (2), (-)-pinocembrin 7-O-rutinoside (3), taxifolin 4'-O-?-d-glucopyranoside (4), kaempferol 7-O-neohesperidoside (5), tamarixetin 3-O-rutinoside (6), and phlorizin (7) on the basis of spectroscopic analysis and comparison of their data to the values reported in the literatures. Among them, compounds 1, 4, and 5 showed in vitro antitumor activity against A549, LAC, Hep-G2, and HeLa cell lines in the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay. PMID:21287989

Xu, Xinya; Xie, Haihui; Hao, Jing; Jiang, Yueming; Wei, Xiaoyi



New spirostanol glycosides from Solanum nigrum and S. jasminoides.  


A new characteristic steroidal glycoside possessing a hydroxyl group at C-23, inunigroside A (1), was isolated from the withered berries of Solanum nigrum L. On the basis of spectroscopic analysis, the structure of 1 was characterized as (5?,22S,23S,25R)-3?,23-dihydroxyspirostane 3-O-?-lycotetraoside. Next, a major steroidal sapogenol, (22R, 25S)-3?,15?-dihydroxy-spirost-5-ene (3), was obtained from the acid hydrolysate of the methanolic extract of the aerial parts of Solanum jasminoides L. A new bisdesmoside, 3-O-?-D-glucopyranosyl-(1?4)-?-D-glucopyranosyl-(1?4)-?-D-glucopyranosyl (22R,25S)-3?,15?-dihydroxyspirost-5-ene 15-O-?-L-rhamnopyranoside (4), named jasminoside A, was isolated from the methanolic extract of S. jasminoides. PMID:22388971

Ohno, Mizuho; Murakami, Kotaro; El-Aasr, Mona; Zhou, Jian-Rong; Yokomizo, Kazumi; Ono, Masateru; Nohara, Toshihiro



Flavonoid glycosides and pharmacological activity of Amphilophium paniculatum  

PubMed Central

Background: Nothing is reported on Amphilophium paniculatum (L.) Kunth. This study aimed at investigation of chemical constituents of the leaves of Amphilophium paniculatum, grown in Egypt, in addition to pharmacological evaluation. Materials and Methods: Isolation of a new compound, along with 5 known flavonoids. Pharmacological activities were carried out on different extracts of A. paniculatum leaves. Results: Identification of a new flavone glycoside, acacetin 8-C-?-D- glucopyranosy l-(1?2)-?-L-rhamnopyranoside (1) in addition to 5 known flavonoids. The 70% ethanol crud extract and its successive chloroform, ethyl acetate, and 100% ethanol extracts showed significant anti-inflammatoryactivity,analgesic effect, antipyretic activity, antioxidant activity, and anti-hyperglycemic activity. Determination of the median lethal dose (LD50) revealed that the different extracts were safe. PMID:23598920

Nassar, Mahmoud I.; Aboutabl, El-Sayed A.; Eskander, Dina M.; Grace, Mary H.; EL-Khrisy, Ezzel-Din A.; Sleem, Amany A.



Enzymatic hydrolysis of steryl glycosides for their analysis in foods.  


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

Münger, Linda H; Nyström, Laura



Sesquiterpene lactone glycosides from Lapsana communis L. subsp. communis  

Microsoft Academic Search

From the latex of Lapsana communis L. subps. communis, five guaianolide glycosides were identified: crepiside E, tectoroside and three new ones: 3-O-P-d-glucopyranosyl-8-O-P-acetyl-1aH,5aH,6PH,7aH-guai-4 (15),10 (14),11 (13)-triene-6,12-olide, 3-O-P-d-glucopyranosyl-8-O-P-acetyl-1aH,5aH,6PH,7aH-guai-3 (4),10 (14), 11 (13)-triene-15-methyl-6,12-olide, and 3-O-P-glucopyranosyl-8-O-P- (4-hydroxyphenyl)-lactyl-1aH,5aH,6PH,7aH-guai-3 (4),10 (14),11 (13)-triene-15-methyl-6,12-olide. Their structures were established by spectroscopic methods.

Didier Fontanel; Christophe Galtier; Jean-Claude Debouzy; Alain Gueiffier; Claude Viel



Sesquiterpene lactone glycosides from Lapsana communis L. subsp. communis.  


From the latex of Lapsana communis L. subps. communis, five guaianolide glycosides were identified: crepiside E, tectoroside and three new ones: 3-O-beta-D-glucopyranosyl-8-O-beta-acetyl-1 alpha H,5 alpha H,6 beta H,7 alpha H-guai-4(15),10(14),11(13)-triene-6,12-olide, 3-O-beta-D-glucopyranosyl-8-O-beta-acetyl-1 alpha H,5 alpha H,6 beta H,7 alpha H-guai-3(4),10(14), 11(13)-triene-15-methyl-6,12-olide, and 3-O-beta-glucopyranosyl-8-O-beta-(4-hydroxyphenyl)-lactyl-1 alpha H,5 alpha H,6 beta H,7 alpha H-guai-3(4),10(14),11(13)-triene-15-methyl-6,12-olide. Their structures were established by spectroscopic methods. PMID:10444857

Fontanel, D; Galtier, C; Debouzy, J C; Gueiffier, A; Viel, C



Tigliane-type diterpenoid glycosides from Euphorbia fischeriana.  


Investigation of whole plants of Euphorbia fischeriana afforded three new tigliane-diterpenoid glycosides, fischerosides A-C (1-3), together with 11 known diterpenoids. Fischerosides A-C (1-3) are the first tigliane-type diterpenoid glucosides. Their structures were determined by a combination of 1D and 2D NMR, MS, and acid hydrolysis. Inhibitory activity against HIV-1 was assessed for compounds 1-5. The new compound 3 showed an EC?? value of 0.02 ?M and a therapeutic index (TI) of 17.50, while prostratin (4) and 12-deoxyphorbol-13,20-diacetate (5) showed significantly greater anti-HIV-1 activity. PMID:21534540

Pan, Li-Li; Fang, Ping-Lei; Zhang, Xing-Jie; Ni, Wei; Li, Lei; Yang, Liu-Meng; Chen, Chang-Xiang; Zheng, Yong-Tang; Li, Chang-Tian; Hao, Xiao-Jiang; Liu, Hai-Yang



Acylated flavonol glycosides from leaves of Stenochlaena palustris.  


From the leaves of Stenochlaena palustris five new O-acylated flavonol glycosides, stenopalustrosides A-E (1-5), have been isolated along with five known compounds, kaempferol 3-O-(3' '-O-E-p-coumaroyl)-(6' '-O-E-feruloyl)-beta-D-glucopyranoside (6), kaempferol 3-O-(3' ',6' '-di-O-E-p-coumaroyl)-beta-D-glucopyranoside (7), kaempferol 3-O-(3' '-O-E-p-coumaroyl)-beta-D-glucopyranoside (8), kaempferol 3-O-(6' '-O-E-p-coumaroyl)-beta-D-glucopyranoside (9); and kaempferol 3-O-beta-D-glucopyranoside (10). The structures of the isolates were elucidated by spectroscopic methods, mainly 1D and 2D NMR. Compounds 1-4 showed significant antibacterial activities against Gram-positive strains. The structural difference between the isolated antibacterial and nonantibacterial compounds is discussed. PMID:9917285

Liu, H; Orjala, J; Sticher, O; Rali, T



Additional minor diterpene glycosides from Stevia rebaudiana Bertoni.  


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-{?-D-glucopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)-?-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {?-D-xylopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)]-O-?-D-glucupyranosyl-ester} (1), and 13-{?-D-6-deoxy-glucopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)-?-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {?-D-glucopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)-?-D-gluco-pyranosyl-ester} (2), on the basis of extensive 1D (1H- and 13C-) 2D NMR (COSY, HSQC and HMBC) and MS spectroscopic data as well as chemical studies. PMID:24184820

Prakash, Indra; Chaturvedula, Venkata Sai Prakash



Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla.  


The organic soluble extract from the leaves of the native North American prairie plant Ipomoea leptophylla (big root morning glory) showed in vitro activity against M. tuberculosis. Bioassay-guided fractionation of this extract resulted in the identification of two new resin glycosides (6, 7). Base-catalyzed hydrolysis of these glycosides gave operculinic acid (1) as the glycosidic acid component as well as trans-cinnamic acid, propanoic acid, and lauric acid. The complete structure elucidation was accomplished through derivatization, 1D and 2D NMR spectroscopy (TOCSY, ROESY, HSQC, HMBC), and MS/MS experiments on 6 and 7 as well as the permethylated derivative 8. PMID:14640518

Barnes, Curtis C; Smalley, Mary K; Manfredi, Kirk P; Kindscher, Kelly; Loring, Hillary; Sheeley, Douglas M



One-pot chemo-, regio-, and stereoselective double-differential glycosidation mediated by lanthanide triflates.  


Nuanced activation of n-pentenyl, thioglycoside, and trichloroacetimidate donors by lanthanide salts coupled with donor/acceptor matching can simplify oligosaccharide assembly. Thus, a one-pot, double-differential glycosidation process can be designed, in which an n-pentenyl acceptor-diol is chemo- and regioselectively glycosidated by using an n-pentenyl ortho ester under the agency of Yb(OTf)(3)/NIS followed by in situ addition of a 2-O-acylated trichloroacetimidate or ethyl thioglycoside to effect stereoselective glycosidation at the remaining OH. PMID:15524445

Jayaprakash, K N; Fraser-Reid, Bert



Absorption, metabolism and elimination of strophanthus glycosides in man.  


In 33 healthy male volunteers, given a single oral and intravenous dose of cymarin (k-strophanthin-alpha), k-strophanthoside (k-strophanthin-gamma) and ouabain (g-strophanthin), enteral absorption and renal excretion of these glycosides and their metabolites were investigated by radioimmunoassay and HPLC. Cymarin was absorbed at 47% of the given dose. After intravenous injection 46% and after oral administration 21% of the given dose, i.e. the total amount as detected by radioimmunoassay which consisted of the unchanged glycoside and its metabolites, were excreted by the kidneys mainly as conjugated metabolites. The half-life of elimination, calculated from the total excreted amount was 13 h (i.v.) and 23 h (p.o.), respectively. k-Strophanthoside was absorbed at 16% of the given dose. After i.v.-injection 73% of the given dose was excreted by the kidneys with a half-life of elimination of 99 h. From this total amount about 70% was excreted as the unchanged drug, the remaining 30% as various metabolites. After oral administration 11% of the given dose were excreted with a half-life of elimination of 22 h. 80% of this amount consisted mainly of conjugated k-strophanthoside and conjugated metabolites as k-strophanthin-beta, cymarin, k-strophanthidin, cymarol and k-strophanthidol. Only 6% was excreted as the unchanged drug. Ouabain was absorbed after oral administration to a minimum of 1.4%. Given intravenously a total renal excretion of 33% of the given dose with a half-life of elimination of 23 h was measured. Of this 80% was unchanged ouabain.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:3821940

Strobach, H; Wirth, K E; Rojsathaporn, K



Tissue and cellular localization of tannins in Tunisian dates (Phoenix dactylifera L.) by light and transmission electron microscopy.  


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 ?m from the sclereid cells of the testa. PMID:24987926

Hammouda, Hédi; Alvarado, Camille; Bouchet, Brigitte; Kalthoum-Chérif, Jamila; Trabelsi-Ayadi, Malika; Guyot, Sylvain



Phosphorus and Other Nutrient Disappearance from Plants Containing Condensed Tannins Using In Situ and Mobile Nylon Bag Techniques  

E-print Network

are esters of phenolic acid and a polyol, usually glucose. Phenolic acid within the molecule can be either gallic acid in gallotannins or other phenolic acid derived from the oxidation of galloyl residues in ellagitannins. Condensed tannins... are esters of phenolic acid and a polyol, usually glucose. Phenolic acid within the molecule can be either gallic acid in gallotannins or other phenolic acid derived from the oxidation of galloyl residues in ellagitannins. Condensed tannins...

Pagan Riestra, Suzika



Effects of NaOH treatment on condensed tannin contents and gas production kinetics of tree leaves  

Microsoft Academic Search

Effects of NaOH treatment on the crude protein (CP), condensed tannin (CT) and in vitro gas production kinetics of leaves of Arbutus andrachne, Glycyrrhiza glabra L. and wheat straw were determined. Wheat straw, which is tannin-free, was used as the standard. The NaOH treatment was completed by pulverization of samples with 0, 20, 40, 60 and 80g\\/L of NaOH solution

O. Canbolat; C. O. Ozkan; A. Kamalak



Cardiac thin filament regulation  

PubMed Central

Myocardial contraction is initiated upon the release of calcium into the cytosol from the sarcoplasmic reticulum following membrane depolarization. The fundamental physiological role of the heart is to pump an amount blood that is determined by the prevailing requirements of the body. The physiological control systems employed to accomplish this task include regulation of heart rate, the amount of calcium release, and the response of the cardiac myofilaments to activator calcium ions. Thin filament activation and relaxation dynamics has emerged as a pivotal regulatory system tuning myofilament function to the beat-to-beat regulation of cardiac output. Maladaptation of thin filament dynamics, in addition to dysfunctional calcium cycling, is now recognized as an important cellular mechanism causing reduced cardiac pump function in a variety of cardiac diseases. Here, we review current knowledge regarding protein–protein interactions involved in the dynamics of thin filament activation and relaxation and the regulation of these processes by protein kinase-mediated phosphorylation. PMID:18421471

Kobayashi, Tomoyoshi; Jin, Lei; de Tombe, Pieter P.



Cardiac ablation procedures  


... 4(6):816-61. Miller JM, Zipes DP. Therapy for cardiac arrhythmias. In: Libby P, Bonow RO, Mann DL, Zipes DP, eds. Braunwald's Heart Disease: A Textbook of Cardiovascular Medicine . 8th ed. Philadelphia, ...


Cardiac muscle cells  

NSDL National Science Digital Library

Cardiac muscles are found only in the heart. They work together to bring deoxygenated blood in and push oxygenated blood out into the body. Essentially, they keep your heart pumping and your body alive.

Nathanael Reveal (None;)



Integrative Cardiac Health Project.  

National Technical Information Service (NTIS)

The Integrative Cardiac Health Project (ICHP) aims to lead the way in Cardiovascular Disease (CVD) Prevention by conducting novel research utilizing a Systems Biology / personalized medicine design to discover and develop practical, effective and preempti...

A. H. Nixon, M. N. Vernalis



Integrative Cardiac Health Project.  

National Technical Information Service (NTIS)

The Integrative Cardiac Health Project (ICHP) aims to lead the way in Cardiovascular Disease (CVD) Prevention by conducting novel research utilizing a Systems Biology / personalized medicine design to discover and develop practical, effective and preempti...

A. H. NIxon, M. N. Vernalis



Integrative Cardiac Health Project.  

National Technical Information Service (NTIS)

The Integrative Cardiac Health Project (ICHP) aims to lead the way in Cardiovascular Disease (CVD) Prevention by conducting novel research utilizing a Systems Biology / personalized medicine design to discover and develop practical, effective and preempti...

A. H. Nixon, M. N. Vernalis



Functional cardiac MR imaging  

NASA Astrophysics Data System (ADS)

Undersampled projection reconstruction acquisitions are investigated for use in functional cardiac MR imaging. 256×256 resolution is obtainable using only 64 projections, with acceptable artifact level. Reduced FOV techniques decrease artifact. Variable angular sampling using projection reconstruction is investigated.

Peters, Dana C.; Epstein, Frederick H.; McVeigh, Elliot R.



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


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. PMID:15896367

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



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


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. PMID:23790904

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



Antioxidant and free radical scavenging effects of the tannins of Terminalia catappa L.  


Reactive oxygen species (ROS) react with biological molecules and destroy the structure of cells and eventually cause free radical-induced disease such as inflammation and cancer. Previous studies showed that an aqueus extract of Terminalia catappa L. exhibited superoxide radical scavenger activity and modification of mitomycin C-induced clasto-genicity. In order to investigate the multiple antioxidant effect of the tannin components of T. catappa L., their ability to prevent lipid peroxidation, superoxide formation and their free radical scavenging activity were evaluated. The results indicated that all of these components showed potent antioxidant activity. Punicalagin and punicalin were the most abundant components and had the strongest anti-oxidative effects of this group of tannins. PMID:11299741

Lin, C C; Hsu, Y F; Lin, T C



Cardiac arrest during pregnancy.  


Cardiac arrest is a rare event during pregnancy. The pregnant population represents a unique subset of cardiac arrest victims. Not only are there unique causes of circulatory collapse during the pregnant state, but the physiological modifications to the maternal physiology during pregnancy require specific modifications to the standard management of the arrest. Lastly, the pregnant victim presents herself with the challenges of a second patient who needs to be considered in the decision-making process. PMID:25314090

Montufar-Rueda, Carlos; Gei, Alfredo



Protein-precipitating capacity of crude condensed tannins of canola and rapeseed hulls  

Microsoft Academic Search

The protein-precipitating potentials (PPP) of soluble condensed tannins (SCT) were determined in hulls from several samples\\u000a of canola and rapeseed varieties. The PPP were expressed as slopes of lines (titration curves) reflecting the amount of SCT-protein\\u000a precipitated vs. the amount of SCT added to the reaction mixture. The slopes (S\\u000a \\u000a p\\u000a ) of titration curves obtained using the protein-precipitation assay

M. Naczk; R. Amarowicz; R. Zadernowski; F. Shahidi



In vitro quality assessment of tannin-containing tropical shrub legumes: protein and fibre digestion  

Microsoft Academic Search

In vitro techniques were evaluated to determine the nutritive value of a selection of tanniniferous tree and shrub legumes (Calliandracalothyrsus, LeucaenaleucocephalaL. diversifolia and L. pallida) compared with lucerne (Medicago sativa). Polyethylene glycol (PEG) was also added to some in vitro fermentations (10mg PEG\\/50mg plant substrate) to assess the effects of tannins on digestion of dry matter (DM), neutral detergent fibre

C. S. McSweeney; B. Palmer; R. Bunch; D. O. Krause



Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry.  


Extractable tannins were analysed by liquid chromatography-electrospray ionisation mass spectrometry in two oak species, North American white oak (Quercus alba) and European red oak (Quercus robur). They mainly included various glucose gallic and ellagic acid esters. The structures were partially determined, and they included grandinin/roburin E, castalagin/vescalagin, gallic acid, valoneic acid bilactone, monogalloyl glucose, digalloyl glucose, trigalloyl glucose, ellagic acid rhamnose, quercitrin and ellagic acid. PMID:10999626

Mämmelä, P; Savolainen, H; Lindroos, L; Kangas, J; Vartiainen, T



Feeny revisited: condensed tannins as anti-herbivore defences in leaf-chewing herbivore communities of  

E-print Network

tested for Quercus velutina and Q. alba in the Missouri Ozarks: abundance and richness of leaf of Quercus R E B E C C A E . F O R K N E R 1 , R O B E R T J . M A R Q U I S 1 and J O H N T . L I L L 2 1 specialists, were negatively correlated with condensed tannins in the canopy of Q. alba. One additional

Lill, John T.


Feeding behavior of graminivorous grasshoppers in response to host-plant extracts, alkaloids, and tannins  

Microsoft Academic Search

Secondary metabolites exhibit the potential to direct food selection by grass-feeding (graminivorous) grasshoppers. We examined the effects of plant extracts and representative secondary metabolites on the feeding behavior of two such grasshoppers,Ageneotettix deorum (Scudder) andPhoetaliotes nebrascensis (Scudder). Three alkaloids and two tannins were bioassayed for their activity as feeding deterrent allelochemicals, as were extracts from the foliage of the graminoids

Simon Mole; Anthony Joern



Curing Kinetics Of Tannin-Phenol-Formal- dehyde Adhesives As Determined By DSC  

Microsoft Academic Search

Differential scanning calorimetry (DSC) was used to compare the thermal curing of two adhesives suitable for using in the\\u000a manufacture of exterior-grade plywood boards: a commercial phenol-formaldehyde (PF) resin, and a tannin-phenol-formaldehyde\\u000a (TPF) resin developed in our laboratory. The experimental curves were well simulated by means of the Model Free Kinetics isoconversional\\u000a method incorporated in the Mettler-Toledo STARe software package.

G. Vázquez; J. González-Álvarez; F. López-Suevos; S. Freire; G. Antorrena



Recent Development of Vegetal Tannins in Corrosion Protection of Iron and Steel  

Microsoft Academic Search

Inhibitors are employed predominantly for corrosion control in closed systems, as a cost-efficiently alternative to the use of high corrosion-resistant materials. Due to the environmental requirements that are currently imposed on the development of cleaner inhibitors, vegetal tannins, a class of natural, non-toxic, biodegradable organic compounds that can be obtained at reduced cost has been proposed. This review relates recent

Afidah A. Rahim; Jain Kassim



Effect of condensed tannins on egg hatching and larval development of Trichostrongylus colubriformis in vitro.  


The effects of condensed tannins extracted from seven forages on the viability of the eggs and first stage (L1) larvae of the sheep nematode Trichostrongylus colubriformis were evaluated in in vitro assays. The extracts of condensed tannins were obtained from Lotus pedunculatus (LP), Lotus corniculatus (LC), sulla (Hedysarum coronarium), sainfoin (Onobrychus viciifolia), Dorycnium pentaphylum (DP), Dorycnium rectum (DR) and dock (Rumex obtusifolius). Extracts containing 200 to 500 microg/ml reduced the proportion of eggs that hatched. The larval development assay was used to evaluate the effect of the extracts on the development of either eggs or L1 larvae to L3 infective larvae. Development was allowed to proceed for seven days by which time the larvae in control incubations had reached the infective L3 stage. Extracts containing 200 microg/ml from LP, DP, DR or dock prevented egg development, and only 11, 8 and 2 per cent of the eggs developed to L3 larvae with extracts from LC, sulla and sainfoin, respectively. When the concentration was 400 microg/ml no eggs developed to L3 larvae. The addition of the extracts after hatching also inhibited the development of L1 to L3 larvae; 200 microg/ml extracted from LP, LC, sulla, sainfoin, DP, DR and dock resulted in only 14, 18, 17, 15, 14, 16 and 4 per cent of L1 larvae developing to the L3 stage compared with 85 per cent for controls, and 400 microg/ml further reduced the development of L1 larvae. Statistical analyses showed that when the extracts were added before hatching they were significantly (P<0.001) more effective at inhibiting the larval development than when they were added after hatching. The condensed tannins from dock had the greatest inhibitory effect on egg development followed by the tannins from DR, sainfoin, DP, LP, sulla and LC. PMID:11837588

Molan, A L; Waghorn, G C; McNabb, W C



A new phenolic glycoside and a new trans-clerodane diterpene from Conyza blinii.  


A new phenolic glycoside, 4-propionyl-2,6-dimethoxyphenyl beta-D-glucopyranoside (1) and a new trans-clerodane diterpene named 19-deacetylconyzalactone (2), were isolated from the aerial parts of Conyza blinii. PMID:11491399

Su, Y F; Guo, D A; Cui, Y J; Liu, J S; Zheng, J H



Ultra-sonication-assisted solvent extraction of quercetin glycosides from 'Idared' apple peels.  


Quercetin and quercetin glycosides are physiologically active flavonol molecules that have been attributed numerous health benefits. Recovery of such molecules from plant matrices depends on a variety of factors including polarity of the extraction solvent. Among the solvents of a wide range of dielectric constants, methanol recovered the most quercetin and its glycosides from dehydrated 'Idared' apple peels. When ultra-sonication was employed to facilitate the extraction, exposure of 15 min of ultrasound wavelengths of dehydrated apple peel powder in 80% to 100% (v/v) methanol in 1:50 (w:v) solid to solvent ratio provided the optimum extraction conditions for quercetin and its glycosides. Acidification of extraction solvent with 0.1% (v/v) or higher concentrations of HCl led to hydrolysis of naturally occurring quercetin glycosides into the aglycone as an extraction artifact. PMID:22117169

Vasantha Rupasinghe, H P; Kathirvel, Priya; Huber, Gwendolyn M



Fast atom bombardment and tandem mass spectrometry for structure determination of steroid and flavonoid glycosides.  


The combination of fast atom bombardment (FAB) and tandem mass spectrometry (MS-MS) was tested for its applicability to generate useful structural information for steroid and flavonoid glycosides. The following compounds were investigated: quercetin, myricitrin, apigetrin, fraxin, rutin, neohesperidin, hesperidin, naringin, apiin, cymarin, digoxin, digitoxin, xanthorhamnin, and frangulin. Upon FAB, the sample molecules are desorbed as (M + H)+, (M - H)-, or as (M + Na)+ or (M + K)+. Collisional activation of (M + H)+ or (M - H)- ions in the MS-MS experiment leads to sequential losses of glycoside moieties in a manner which permits the sequence of glycosides to be established. Some glycosides occur as mixtures of homologs. Proper interpretation of the MS-MS or collisional activation decomposition spectra often allows the homology to be located. In addition to the simple and highly selective fragmentations observed in this combined experiment, FAB and MS-MS also remove interference caused by the ubiquitous matrix ions which are desorbed by FAB. PMID:3728980

Crow, F W; Tomer, K B; Looker, J H; Gross, M L



High-throughput cloning, expression and purification of glycoside hydrolases using Ligation-Independent Cloning (LIC).  


Recent advances in DNA sequencing techniques have led to an explosion in the amount of available genome sequencing data and this provided an inexhaustible source of uncharacterized glycoside hydrolases (GH) to be studied both structurally and enzymatically. Ligation-Independent Cloning (LIC), an interesting alternative to traditional, restriction enzyme-based cloning, and commercial recombinatorial cloning, was adopted and optimized successfully for a high throughput cloning, expression and purification pipeline. Using this platform, 130 genes encoding mainly uncharacterized glycoside hydrolases from 13 different organisms were cloned and submitted to a semi-automated protein expression and solubility screening in Escherichia coli, resulting in 73 soluble targets. The high throughput approach proved to be a powerful tool for production of recombinant glycoside hydrolases for further structural and biochemical characterization and confirmed that thioredoxin fusion tag (TRX) is a better choice to increase solubility of recombinant glycoside hydrolases expressed in E. coli, when compared to His-tag alone. PMID:24680731

Camilo, Cesar M; Polikarpov, Igor



Solubility Enhancement of Steviol Glycosides and Characterization of Their Inclusion Complexes with Gamma-Cyclodextrin  

PubMed Central

Steviol glycosidesrebaudioside (reb) A, C and D have low aqueous solubilities. To improve their aqueous solubilities, inclusion complex of steviol glycosides, reb A, C and D and gamma cyclodextrin were prepared by freeze drying method and further characterized by means of differential scanning calorimetry, Fourier transform infrared spectroscopy and Raman spectroscopy. The effect of gamma cyclodextrin on chemical shifts of the steviol glycosides was also studied in proton NMR experiments as well as in solid state 13C CP/MAS NMR experiments. These results indicated that the steviol glycosides were clearly in inclusion complex formation with the gamma cyclodextrin which also results in solubility enhancement of these steviol glycosides. Phase solubility studies showed that amounts of soluble reb A, C and D increased with increasing amounts of gamma cyclodextrin indicating formation of 1:1 stoichiometric and higher order inclusion complexes. PMID:22174615

Upreti, Mani; Strassburger, Ken; Chen, You L.; Wu, Shaoxiong; Prakash, Indra



Tannin Degradation by a Novel Tannase Enzyme Present in Some Lactobacillus plantarum Strains  

PubMed Central

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

Jiménez, Natalia; Esteban-Torres, María; Mancheño, José Miguel; de las Rivas, Blanca



Tannins and terpenoids as major precursors of Suwannee River fulvic acid  

USGS Publications Warehouse

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.

Leenheer, Jerry A.; Rostad, Colleen E.



Influence of Myriophyllum spicatum-derived tannins on gut microbiota of its herbivore Acentria ephemerella.  


The submerged living larvae of Acentria ephemerella were fed in the laboratory with either M. spicatum or Potamogeton perfoliatus, two of their host plants. Larvae exhibited a reduced growth when fed M. spicatum, a freshwater angiosperm that contains high concentrations of tannins, secondary metabolites known for their herbivore-deterrent and antimicrobial properties. In this study, we investigated the influence of food-derived tannins on gut microbiota. Bacterial densities in the guts did not differ between the food regimes, ranging from 2.8 to 13.3 x 10(6) cells per gut. Gut bacteria were characterized with cultivation techniques and subsequent identification of the strains by molecular methods. We isolated 17 bacterial strains belonging to all subdivisions, i.e., we identified alpha-, beta-, and gamma-proteobacteria, Cytophyaga/Flavobacteria (CF) and several Gram-positive bacteria. All except one Gram-positive strain were found in the guts of larvae fed with P. perfoliatus. Gram-positive bacteria and bacteria of the CF cluster were more sensitive to polyphenol-containing extracts of M. spicatum in an agar diffusion assay than strains of the alpha- or gamma-proteobacteria subdivision. Our results suggest an influence of food-derived tannins on gut microbiota in A. ephemerella. PMID:12474899

Walenciak, Oliver; Zwisler, Walter; Gros, Elisabeth M



Feeding behavior of graminivorous grasshoppers in response to host-plant extracts, alkaloids, and tannins.  


Secondary metabolites exhibit the potential to direct food selection by grass-feeding (graminivorous) grasshoppers. We examined the effects of plant extracts and representative secondary metabolites on the feeding behavior of two such grasshoppers,Ageneotettix deorum (Scudder) andPhoetaliotes nebrascensis (Scudder). Three alkaloids and two tannins were bioassayed for their activity as feeding deterrent allelochemicals, as were extracts from the foliage of the graminoids commonly eaten by these grasshoppers:Agropyron smithii Rydb.,Andropogon hallii Hack.,Andropogon scoparius Michx.,Bouteloua gracilis (H. B. K) Lag. ex Griffiths,Carex heliophila Mack. andStipa comata Trin. & Rupr. Alkaloids strongly deterred feeding but tannins only exhibited a weak effect, even when present at four times the concentration of total phenolics typical for these graminoids. Host-plant extracts also exhibited weak effects, such that we found no evidence for either strong deterrence or phagostimulation. Our results for alkaloids and host-plant extracts are consistent with the view that grass-feeding grasshoppers may be restricted to graminoids because of: (1) the presence of deterrents in nonhosts and (2) the absence of deterrents in hosts. However, our data for tannins show that these are unlikely to be effective barriers to herbivory by these grasshoppers. PMID:24241979

Mole, S; Joern, A



Glycosidation of thioglycosides in the presence of bromine: mechanism, reactivity, and stereoselectivity.  


Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that ?-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, ?-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into ?-bromide that is totally unreactive under the established reaction conditions. PMID:22136383

Kaeothip, Sophon; Yasomanee, Jagodige P; Demchenko, Alexei V



A new flavonoid glycoside from the rhizomes and roots of Smilax scobinicaulis.  


A new flavonoid glycoside, hesperetin-7-O-[?-D-glucopyranosyl-(1 ? 3)]-?-D-glucopyranosyl (1), was isolated from the n-BuOH extract of Smilax scobinicaulis, together with four known flavonoid glycosides, clematine (2), ononin (3), daidzin (4) and puerarin (5). All of the five compounds were reported from this material for the first time. Their structures were determined on the basis of spectroscopic and spectrometric methods. PMID:24483603

Xu, Jing; Feng, Shixiu; Wang, Qi; Zhang, Min; Zhang, Cunli



Acetophenones and new pregnane glycosides from the roots of Vincetoxicum hirundinaria  

Microsoft Academic Search

The roots of Vincetoxicum hirundinaria yielded the known pregnane glycosides cynatratoside E and cynatratoside C and three new pregane glycosides: hirundicoside B, hirundicoside C and hirundicoside D. Their structures have been elucidated by spectral data. Other isolated constituents: 2-hydroxyacetophenone, paenol, apocynine, 4-hydroxyacetophenone, 2,4-dihydroxyacetophenone, hancolupenone, sitosterol and syringic acid. 2-Hydroxyacetophenone was also identified as the major constituent of the essential oil

M Lavault; P Richomme; J Bruneton



Determination of Iridoid Glycosides from Four Turkish Lamium Species by HPLC-ESI\\/MS  

Microsoft Academic Search

An HPLC-ESI\\/MS method that enables fast detection and identification of iridoid glycosides is described. Eleven iridoid glycosides known to occur in the genus Lamium -lamalbide, sesamoside, 6- ?-OH ipolamiide, shanzhiside methyl ester, dehydropenstemoside, barlerin (= 8-O-acetylshanzhiside methyl ester), 6-O-syringyl-8-O-acetylshanzhiside methyl ester, lamerioside, lamiide, eriobioside, and ipolamiide, were identified by means of their retention time and ESI\\/MS data. This method was

Turk J Chem; Erhan PALASKA


High throughput chemiluminescence platform for evaluating antioxidative activity of total flavonoid glycosides from plant extracts  

Microsoft Academic Search

A high throughput chemiluminescence (CL) platform for rapidly evaluating antioxidant activity of total flavonoid glycosides from plant extracts was developed originally based on their inhibition effects on the CL reaction of 1,1-dipheny-2-picrylhydrazyl (DPPH)–luminol or H2O2–luminol system. With the method, total flavonoid glycosides extracts were screened through detecting the inhibited CL intensity, which was reversely correlative to antioxidant activity of the

Hong Yao; Bin Wu; Yiyu Cheng; Haibin Qu



Steroidal glycosides from the aerial part of Asclepias incarnata L. II.  


Thirty new steroidal glycosides were obtained from the aerial part of Asclepias incarnata L. (Asclepiadaceae). These glycosides were confirmed to have lineolon, isolineolon, 12-O-acetyllineolon, 12-O-(Z)-cinnamoyllineolon, metaplexigenin, 15 beta-hydroxylineolon, 15 beta-hydroxyisolineolon, 16 alpha-hydroxyisolineolon, 12-O-tigloyl-16 alpha-hydroxyisolineolon as the aglycone and 2,6-dideoxyhexopyranose as the sugar sequence by spectroscopic methods and chemical evidence. PMID:10705484

Warashina, T; Noro, T



Fate of iridoid glycosides in different life stages of the Buckeye, Junonia coenia (Lepidoptera: Nymphalidae)  

Microsoft Academic Search

The buckeye butterfly,Junonia coenia (Lepidoptera: Nymphalidae), specializes on plants that contain iridoid glycosides. To determine the fate of these compounds in larvae, pupae, and adults of this species, we reared larvae on artificial diets with and without iridoid glycosides, and on leaves of a host plant,Plantago lanceolata (Plantaginaceae). Quantification by gas chromatography showed that newly molted third-, fourth-, and fifth-instar

M. Deane Bowers; Sharon K. Collinge



Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L  

Microsoft Academic Search

Shoot, root, and callus cultures of Scrophularia nodosa L. (Scrophulariaceae) were established and cultivated in vitro. Iridoid glycosides, such as harpagoside, aucubin, and catalpol\\u000a were identified by LC-ESI-MS and their contents determined by HPLC. For comparison intact plants of S. nodosa were analysed. In shoot cultures slightly lower amounts of detectable iridoid glycosides (4.36% dry weight) were determined\\u000a than in

Katja Sesterhenn; Melanie Distl; Michael Wink



Iridoid glycosides isolated from Scrophularia dentata Royle ex Benth. and their anti-inflammatory activity.  


Scrodentosides A-E (1-5), five new acylated iridoid glycosides, together with 19 known ones, were isolated from the whole plant of Scrophularia dentata Royle ex Benth. The structures of these isolated glycosides were elucidated by spectroscopic methods. Bioassay showed that compounds 7 and 11 had significant inhibitory effect against NF-?B activation with IC50 value of 43.7?M and 1.02?M respectively. PMID:25016952

Zhang, Liuqiang; Zhu, Tiantian; Qian, Fei; Xu, Jinwen; Dorje, Gaawe; Zhao, Zhili; Guo, Fujiang; Li, Yiming



A genomics investigation of partitioning into and among flavonoid-derived condensed tannins for carbon sequestration in Populus  

SciTech Connect

The project set out to use comparative (genotype and treatment) and transgenic approaches to investigate the determinants of condensed tannin (CT) accrual and chemical variability in Populus. CT type and amount are thought to effect the decomposition of plant detritus in the soil, and thereby the sequestering of carbon in the soil. The stated objectives were: 1. Genome-wide transcriptome profiling (microarrays) to analyze structural gene, transcription factor and metabolite control of CT partitioning; 2. Transcriptomic (microarray) and chemical analysis of ontogenetic effects on CT and PG partitioning; and 3. Transgenic manipulation of flavonoid biosynthetic pathway genes to modify the control of CT composition. Objective 1: A number of approaches for perturbing CT content and chemistry were tested in Objective 1, and those included nitrogen deficit, leaf wounding, drought, and salicylic acid spraying. Drought had little effect on CTs in the genotypes we used. Plants exhibited unpredictability in their response to salicylic acid spraying, leading us to abandon its use. Reduced plant nitrogen status and leaf wounding caused reproducible and magnitudinally striking increases in leaf CT content. Microarray submissions to NCBI from those experiments are the following: GSE ID 14515: Comparative transcriptomics analysis of Populus leaves under nitrogen limitation: clone 1979. Public on Jan 04, 2010; Contributor(s) Harding SA, Tsai C GSE ID 14893: Comparative transcriptomics analysis of Populus leaves under nitrogen limitation: clone 3200. Public on Feb 19, 2009; Contributor(s) Harding SA, Tsai C GSE ID 16783 Wound-induced gene expression changes in Populus: 1 week; clone RM5. Status Public on Dec 01, 2009; Contributor(s) Harding SA, Tsai C GSE ID 16785 Wound-induced gene expression changes in Populus: 90 hours; clone RM5 Status Public on Dec 01, 2009; Contributor(s) Harding SA, Tsai C Although CT amount changed in response to treatments, CT composition was essentially conserved. Overall phenylpropanoid composition exhibited changes due to large effects on phenolic glycosides containing a salicin moiety. There were no effects on lignin content. Efforts to publish this work continue, and depend on additional data which we are still collecting. This ongoing work is expected to strengthen our most provocative metabolic profiling data which suggests as yet unreported links controlling the balance between the two major leaf phenylpropanoid sinks, the CTs and the salicin-PGs. Objective 2: Ontogenic effects on leaf CT accrual and phenylpropanoid complexity (Objective 2) have been reported in the past and we contributed two manuscripts on how phenylpropanoid sinks in roots and stems could have an increasing effect on leaf CT as plants grow larger and plant proportions of stem, root and leaf change. Tsai C.-J., El Kayal W., Harding S.A. (2006) Populus, the new model system for investigating phenylpropanoid complexity. International Journal of Applied Science and Engineering 4: 221-233. We presented evidence that flavonoid precursors of CT rapidly decline in roots under conditions that favor CT accrual in leaves. Harding SA, Jarvie MM, Lindroth RL, Tsai C-J (2009) A comparative analysis of phenylpropanoid metabolism, N utilization and carbon partitioning in fast- and slow-growing Populus hybrid clones. Journal of Experimental Botany. 60:3443-3452. We presented evidence that nitrogen delivery to leaves as a fraction of nitrogen taken up by the roots is lower in high leaf CT genotypes. We presented a hypothesis from our data that N was sequestered in proportion to lignin content in stem tissues. Low leaf N content and high leaf CT in genotypes with high stem lignin was posited to be a systemic outcome of N demand in lignifiying stem tissues. Thereby, stem lignin and leaf CT accrual might be systemically linked, placing control of leaf phenylpropanoids under systemic rather than solely organ specific determinants. Analyses of total structural and non-structural carbohydrates contributed to the model presented. Harding SA, Xue L, Du L, Nyamd

Harding, Scott, A; Tsai, Chung-jui; Lindroth, Richard, L



UDP-dependent glycosyltransferases involved in the biosynthesis of steviol glycosides.  


A short-term experiment was designed to measure the transcript levels of downstream genes contributing to the biosynthesis of steviol glycosides. Stevia rebaudiana plants were subjected to long- and short-day conditions for different time intervals. Samples from both lower and upper leaves were collected. Using quantitative real-time polymerase chain reaction, the transcript levels of three UDP-dependent glycosyltransferases, UGT85C2, UGT74G1 and UGT76G1, were studied. The results were compared with the steviol glycoside contents measured in the leaves, which were quantified by reversed phase HPLC. In the same daylength condition, steviol glycoside concentration and the transcript levels of the three UGT genes were higher in upper leaves than in lower leaves. Steviol glycosides accumulated more in plants under short-day conditions. Under these conditions, a highly significant correlation was found between UGT85C2 transcription and total steviol glycoside accumulation in the upper leaves. This suggests that the glycosylation of steviol to form steviolmonoside is the rate-limiting step in the glycosylation pathway of steviol glycosides. In these upper leaves, a relatively high accumulation of rebaudioside A compared to stevioside was also observed, however, without correlation with the transcription of UGT76G1. PMID:21477883

Mohamed, Amal A A; Ceunen, Stijn; Geuns, Jan M C; Van den Ende, Wim; De Ley, Marc



Influence of steviol glycosides on the stability of vitamin C and anthocyanins.  


A high level of sweetness and health-promoting properties make steviol glycosides an interesting alternative to sugars or artificial sweeteners. The radical oxygen species scavenging activity of these compounds may influence the stability of labile particles present in food. Model buffer solutions containing steviol glycosides, a selected food antioxidant (vitamin C or anthocyanins), and preservative were analyzed during storage. The addition of steviol glycosides at concentrations of 50, 125, and 200 mg/L increased the stability of both ascorbic and dehydroascorbic acid (degradation rates decreased up to 3.4- and 4.5-fold, respectively); the effect was intensified by higher sweetener concentrations and higher acidity of the solutions. Glycosides used alone did not affect the stability of anthocyanins; however, they enhanced the protective effect of sugars; half-life times increased by ca. 33% in the presence of sucrose (100 g/L) and by ca. 52% when both sucrose (100 g/L) and glycosides (total 200 mg/L) were used. Steviol glycosides concentrations remained stable during experiments. PMID:25376304

Wo?niak, Lukasz; Marsza?ek, Krystian; Sk?pska, Sylwia



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

NASA Astrophysics Data System (ADS)

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.

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



Antitrypanosomal isothiocyanate and thiocarbamate glycosides from Moringa peregrina.  


O-Methyl (1), O-ethyl (2), and O-butyl (3) 4-[(?-L-rhamnosyloxy) benzyl] thiocarbamate (E), along with 4-(?-L-rhamnosyloxy) benzyl isothiocyanate (4) have been isolated from the aerial parts of Moringa peregrina. The compounds were tested for in vitro activity against Trypanosoma brucei rhodesiense and cytotoxicity in rat skeletal myoblasts (L6 cells). The most potent compound was 4 with an IC50 of 0.10 µM against T.b. rhodesiense and a selectivity index of 73, while the thiocarbamate glycosides 1, 2, and 3 showed only moderate activity. Intraperitoneal administration of 50 mg/kg body weight/day of 4 in the T.b. rhodesiense STIB 900 acute mouse model revealed significant in vivo toxicity. Administration of 10 mg/kg body weight/day resulted in a 95% reduction of parasitemia on day 7 postinfection, but did not cure the animals. Because of its high in vitro activity and its ability to irreversibly inhibit trypanothione reductase, an attractive parasite-specific target enzyme, 4-[(?-L-rhamnosyloxy) benzyl] isothiocyanate (4), can be considered as a lead structure for the development and characterization of novel antitrypanosomal drugs. PMID:24310210

Ayyari, Mahdi; Salehi, Peyman; Ebrahimi, Samad Nejad; Zimmermann, Stefanie; Portmann, Lena; Krauth-Siegel, R Luise; Kaiser, Marcel; Brun, Reto; Rezadoost, Hassan; Rezazadeh, Shamsali; Hamburger, Matthias



[Triterpene glycosides from the aerial parts of Pulsatilla chinensis].  


To study the chemical constituents of the aerial parts of Pulsatilla chinensis (Bge.) Regel, various chromatography methods were used. Seven triterpene glycosides were isolated from the n-BuOH extract. Their structures were identified as bayogenin 28-O-alpha-L-rhamnopyranosyl (1 --> 4 ) -beta-D-glucopyranosyl (1 --> 6) -beta-D-glucopyranosyl ester (1), 3-O-alpha-L-arabinopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl (1 --> 4) -beta-D-glucopyranosyl (1 --> 6) -beta-D-glucopyranosyl ester (2), 3-O-alpha-L-rhamnopyranosyl (1 -->-2 ) -alpha-L-arabinopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl (1 --> 4 ) -beta-D-glucopyranosyl (1 --> 6 ) -beta-D-glucopyranosyl ester (3), 3-O-alpha-L-rhamnopyranosyl (1 --> 2 ) -[beta-D-glucopyranosyl (1 --> 4)] -alpha-L-arabinopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl (1 --> 4) -beta-D-glucopyranosyl (1 --> 6) -beta-D-glucopyranosyl ester (4), 3-O-alpha-L-rhamnopyranosyl (1 --> 2) -alpha-L-arabinopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl (1 --> 4) -beta-D-glucopyranosyl (1 --> 6 ) -beta-D-glucopyranosyl ester (5), hederagenin 28-O-alpha-L-rhamnopyranosyl (1 --> 4) -beta-D-glucopyranosyl (1 --> 6) -beta-D-glucopyranosyl ester (6) and pulsatilla saponin (7). Among them, compound 1 is a new compound. Compounds 2 -6 were isolated from this plant for the first time. PMID:17944236

Shi, Bao-Jun; Li, Qian; Zhang, Xiao-Qi; Wang, Ying; Ye, Wen-Cai; Yao, Xin-Sheng



Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina.  


Eight iridoid glycosides and four phenolic compounds were isolated from the EtOAc soluble fraction of Veronica peregrina MeOH extract as the radical scavengers for antioxidant activity. The compounds were identified as protocatechuic acid (1), luteolin (2), veronicoside (3), minecoside (4), specioside (5), amphicoside (6), catalposide (7), 6-O-cis-p-coumaroyl catalpol (8), p-hydroxy benzoic acid methyl ester (9), verproside (10), verminoside (11), and chrysoeriol 7-glucuronide (12) by spectroscopic analysis. All compounds except for 1 and 2 were isolated for the first time from this plant. The antioxidant activity was evaluated by the ORAC(Oxygen Radical Absorbance Capacity) assay, which measures scavenging activity against peroxy radicals induced by 2,2'-azobis (2-methoxypropion-amidine) dihydrochloride, and the ORAC value is expressed as relative trolox equivalent. Compounds 2, 4, 5, 6, 8, and 12 exhibited potent antioxidant activity, and compounds 1, 11 had similar activity with trolox, whereas the other compounds showed weaker activity than trolox. PMID:19280150

Kwak, Jong Hwan; Kim, Hyun Jung; Lee, Kwang Ho; Kang, Se Chan; Zee, Ok Pyo



Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria.  


Four chalcone glycosides (1-4), including three new natural products, and three flavanones (5-7) were isolated from the methanol extract of stem bark of Maclura tinctoria. The new compounds have been characterized as 4'-O-beta-D-(2' '-p-coumaroyl)glucopyranosyl-4,2',3'-trihydroxychalcone (1), 4'-O-beta-D-(2' '-p-coumaroyl-6' '-acetyl)glucopyranosyl-4,2',3'-trihydroxychalcone (2), and 3'-(3-methyl-2-butenyl)-4'-O-beta-D-glucopyranosyl-4,2'-dihydroxychalcone (3); the known derivatives were elucidated as 4'-O-beta-D-(2' '-acetyl-6' '-cinnamoyl)glucopyranosyl-4,2',3'-trihydroxychalcone (4), eriodictyol 7-O-beta-D-glucopyranoside (5), naringenin (6), and naringenin 4'-O-beta-D-glucopyranoside (7). Their structures were determined by 1D and 2D NMR and ESIMS. The antioxidant activity of all the isolated compounds was determined by measuring free-radical-scavenging effects using two different assays, namely, the Trolox Equivalent Antioxidant Capacity (TEAC) assay and the coupled oxidation of beta-carotene and linoleic acid (autoxidation assay). The results showed that compound 3 was the most active in both antioxidant assays. PMID:12932124

Cioffi, Giuseppina; Morales Escobar, Luis; Braca, Alessandra; De Tommasi, Nunziatina



Polyketide Glycosides from Bionectria ochroleuca Inhibit Candida albicans Biofilm Formation.  


One of the challenges presented by Candida infections is that many of the isolates encountered in the clinic produce biofilms, which can decrease these pathogens' susceptibilities to standard-of-care antibiotic therapies. Inhibitors of fungal biofilm formation offer a potential solution to counteracting some of the problems associated with Candida infections. A screening campaign utilizing samples from our fungal extract library revealed that a Bionectria ochroleuca isolate cultured on Cheerios breakfast cereal produced metabolites that blocked the in vitro formation of Candida albicans biofilms. A scale-up culture of the fungus was undertaken using mycobags (also known as mushroom bags or spawn bags), which afforded four known [TMC-151s C-F (1-4)] and three new [bionectriols B-D (5-7)] polyketide glycosides. All seven metabolites exhibited potent biofilm inhibition against C. albicans SC5314, as well as exerted synergistic antifungal activities in combination with amphotericin B. In this report, we describe the structure determination of the new metabolites, as well as compare the secondary metabolome profiles of fungi grown in flasks and mycobags. These studies demonstrate that mycobags offer a useful alternative to flask-based cultures for the preparative production of fungal secondary metabolites. PMID:25302529

Wang, Bin; You, Jianlan; King, Jarrod B; Cai, Shengxin; Park, Elizabeth; Powell, Douglas R; Cichewicz, Robert H



Glycosidic moiety changes the spectroscopic properties of dl-?-tocopherol in DMSO\\/water solution and in organic solvents  

Microsoft Academic Search

In this study we estimated how conjugation with a sugar moiety influences the spectral properties of tocopherol and relate the spectroscopic properties of glycosides to solvent properties such as viscosity and polarity.Spectroscopic properties (absorption, fluorescence, fluorescence anisotropy and fluorescence lifetime) of three dl-?-tocopheryl glycosides (dl-?-tocopheryl orthoacetate derivative and glycosides of dl-?-tocopherol model compounds: 2,2,5,7,8-pentamethyl-6-chromanol and Trolox) were studied in DMSO\\/water

G. Neunert; P. Polewski; P. Walejko; M. Markiewicz; S. Witkowski; K. Polewski



Pediatric sudden cardiac arrest.  


Pediatric sudden cardiac arrest (SCA), which can cause sudden cardiac death if not treated within minutes, has a profound effect on everyone: children, parents, family members, communities, and health care providers. Preventing the tragedy of pediatric SCA, defined as the abrupt and unexpected loss of heart function, remains a concern to all. The goal of this statement is to increase the knowledge of pediatricians (including primary care providers and specialists) of the incidence of pediatric SCA, the spectrum of causes of pediatric SCA, disease-specific presentations, the role of patient and family screening, the rapidly evolving role of genetic testing, and finally, important aspects of secondary SCA prevention. This statement is not intended to address sudden infant death syndrome or sudden unexplained death syndrome, nor will specific treatment of individual cardiac conditions be discussed. This statement has been endorsed by the American College of Cardiology, the American Heart Association, and the Heart Rhythm Society. PMID:22451713



FeCl3-promoted and ultrasound-assisted synthesis of resveratrol O-derived glycoside analogs.  


Phenol derived O-glycosides were synthesized using a direct and convenient O-glycosidation, starting from acetylated sugars in the presence of FeCl3, an inexpensive, mild and benign Lewis acid catalyst. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions leading to the corresponding ?-O-glycosides as the major anomer. Post-synthetic transformations of iodophenol intermediates led to new resveratrol O-glycoside analogs in good overall yields. PMID:24961448

Marzag, Hamid; Robert, Guillaume; Dufies, Maeva; Bougrin, Khalid; Auberger, Patrick; Benhida, Rachid



Dynamic Control of Cardiac Alternans  

NASA Astrophysics Data System (ADS)

A dynamic control technique was used to suppress a cardiac arrhythmia called an alternans rhythm in a piece of dissected rabbit heart. Our control algorithm adapted to drifting system parameters, making it well suited for the control of physiological rhythms. Control of cardiac alternans rhythms may have important clinical implications since they often precede serious cardiac arrhythmias and are a harbinger of sudden cardiac death.

Hall, Kevin; Christini, David J.; Tremblay, Maurice; Collins, James J.; Glass, Leon; Billette, Jacques



Penetrating Cardiac Injury: A Review  

PubMed Central

Cardiac injury presents a great challenge to the emergency resident because these injuries require urgent intervention to prevent death. Sometimes serious cardiac injury may manifest only subtle or occult symptoms or signs. As there is an epidemic of cardiac injuries in Kashmir valley due to problems of law and order, we herein present a review on management of such injuries. PMID:24829887

Lateef Wani, Mohd; Ahangar, Ab Gani; Wani, Shadab Nabi; Irshad, Ifat; Ul-Hassan, Nayeem



Cardiac Response and Personality Organization  

ERIC Educational Resources Information Center

This study examines the level and variability of cardiac response during complex problem-solving and interposed rest periods and their differing relationships to estimates of personality integration on the Rorschach. Findings suggest cardiac variability may be a more differentiated measure than level of cardiac response. (Author)

Blatt, Sidney J.; Feirstein, Alan



Removing tannins from medicinal plant extracts using an alkaline ethanol precipitation process: a case study of danshen injection.  


The alkaline ethanol precipitation process is investigated as an example of a technique for the removal of tannins extracted from Salviae miltiorrhizae Radix et Rhizoma for the manufacture of Danshen injection. More than 90% of the tannins can be removed. However, the recoveries of danshensu, rosmarinic acid, and salvianolic acid B were less than 60%. Total tannin removal increased as the refrigeration temperature decreased or the amount of NaOH solution added increased. Phenolic compound recoveries increased as refrigeration temperature increased or the amount of NaOH solution added decreased. When operated at a low refrigeration temperature, a relative high separation selectivity can be realized. Phenolic compound losses and tannin removal were mainly caused by precipitation. The formation of phenol salts, whose solubility is small in the mixture of ethanol and water used, is probably the reason for the precipitation. A model considering dissociation equilibrium and dissolution equilibrium was established. Satisfactory correlation results were obtained for phenolic compound recoveries and total tannin removal. Two important parameters in the model, which are the water content and pH value of alkaline supernatant, are suggested to be monitored and controlled to obtain high batch-to-batch consistency. PMID:25405288

Gong, Xingchu; Li, Yao; Qu, Haibin



Assessment of Anti-nutritive Activity of Tannins in Tea By-products Based on In vitro Rumen Fermentation.  


Nutritive values of green and black tea by-products and anti-nutritive activity of their tannins were evaluated in an in vitro rumen fermentation using various molecular weights of polyethylene glycols (PEG), polyvinyl pyrrolidone (PVP) and polyvinyl polypyrrolidone as tannin-binding agents. Significant improvement in gas production by addition of PEG4000, 6000 and 20000 and PVP was observed only from black tea by-product, but not from green tea by-product. All tannin binding agents increased NH3-N concentration from both green and black tea by-products in the fermentation medium, and the PEG6000 and 20000 showed relatively higher improvement in the NH3-N concentration. The PEG6000 and 20000 also improved in vitro organic matter digestibility and metabolizable energy contents of both tea by-products. It was concluded that high molecular PEG would be suitable to assess the suppressive activity of tannins in tea by-products by in vitro fermentation. Higher responses to gas production and NH3-N concentration from black tea by-product than green tea by-product due to PEG indicate that tannins in black tea by-product could suppress rumen fermentation more strongly than that in green tea by-product. PMID:25358316

Kondo, Makoto; Hirano, Yoshiaki; Ikai, Noriyuki; Kita, Kazumi; Jayanegara, Anuraga; Yokota, Hiro-Omi



Assessment of Anti-nutritive Activity of Tannins in Tea By-products Based on In vitro Rumen Fermentation  

PubMed Central

Nutritive values of green and black tea by-products and anti-nutritive activity of their tannins were evaluated in an in vitro rumen fermentation using various molecular weights of polyethylene glycols (PEG), polyvinyl pyrrolidone (PVP) and polyvinyl polypyrrolidone as tannin-binding agents. Significant improvement in gas production by addition of PEG4000, 6000 and 20000 and PVP was observed only from black tea by-product, but not from green tea by-product. All tannin binding agents increased NH3-N concentration from both green and black tea by-products in the fermentation medium, and the PEG6000 and 20000 showed relatively higher improvement in the NH3-N concentration. The PEG6000 and 20000 also improved in vitro organic matter digestibility and metabolizable energy contents of both tea by-products. It was concluded that high molecular PEG would be suitable to assess the suppressive activity of tannins in tea by-products by in vitro fermentation. Higher responses to gas production and NH3-N concentration from black tea by-product than green tea by-product due to PEG indicate that tannins in black tea by-product could suppress rumen fermentation more strongly than that in green tea by-product. PMID:25358316

Kondo, Makoto; Hirano, Yoshiaki; Ikai, Noriyuki; Kita, Kazumi; Jayanegara, Anuraga; Yokota, Hiro-omi



Domestication and defence: Foliar tannins and C/N ratios in cassava and a close wild relative  

NASA Astrophysics Data System (ADS)

Plant domestication is accompanied by shifts in resource allocation, as a result of farmer selection for genotypes that give high yields in agricultural habitats. Relaxed natural selection for chemical and physical defences in these habitats could facilitate resource allocation to yield. We compared the concentrations of tannins, and C/N ratios, which are often correlated with investment in cell-wall compounds, in leaves of landraces of domesticated cassava ( Manihot esculenta) and a close wild relative in French Guiana. Foliar concentrations of tannins were about 1.9 times higher in the wild relative than in domesticated cassava. Histochemical analyses showed that tannins were present in nearly all palisade and spongy parenchyma cells of the wild taxon, but in only some cells of these tissues in M. esculenta. C/N ratios were also 1.9 times higher in leaves of the wild relative than in those of domesticated cassava. Tannins accounted for only a small proportion of total carbon, and the higher C/N ratio in wild than in domesticated cassava may reflect higher investment in carbon-containing compounds additional to tannins, such as cell-wall compounds. The divergence in these traits between cassava and this close wild relative mirrors a broad pattern observed in wild plant species across habitats varying in resource availability. One explanation for our results is that domestication in cassava may have favoured a shift from a resource conservation strategy to a resource acquisition strategy.

Mondolot, Laurence; Marlas, Amandine; Barbeau, Damien; Gargadennec, Annick; Pujol, Benoît; McKey, Doyle



Advanced Cardiac Life Support.  

ERIC Educational Resources Information Center

This document contains materials for an advanced college course in cardiac life support developed for the State of Iowa. The course syllabus lists the course title, hours, number, description, prerequisites, learning activities, instructional units, required text, six references, evaluation criteria, course objectives by units, course…

Kirkwood Community Coll., Cedar Rapids, IA.


Cardiac and Pulmonary Injury  

Microsoft Academic Search

Cardiac and pulmonary injuries present major chal- lenges in diagnosis and treatment. Distinct differences between penetrating and blunt trauma of these or- gans exist. Outcomes for severe injuries are still grave. Organized trauma systems can provide optimal care by minimizing prehospital time, allowing easy access to imaging modalities, and offering state-of-the-art treatment strategies. A multidisciplinary approach, including surgeons, intensivists, and

George C. Velmahos; Muhammad U. Butt



The cardiac malpositions.  


Dextrocardia was known in the 17th century and was 1 of the first congenital malformations of the heart to be recognized. Fifty years elapsed before Matthew Baillie published his account of complete transposition in a human of the thoracic and abdominal viscera to the opposite side from what is natural. In 1858, Thomas Peacock stated that "the heart may be congenitally misplaced in various ways, occupying either an unusual position within the thorax, or being situated external to that cavity." In 1915, Maude Abbott described ectopia cordis, and Richard Paltauf's remarkable illustrations distinguished the various types of dextrocardia. In 1928, the first useful classification of the cardiac malpositions was proposed, and in 1966, Elliott et al's radiologic classification set the stage for clinical recognition. The first section of this review deals with the 3 basic cardiac malpositions in the presence of bilateral asymmetry. The second section deals with cardiac malpositions in the presence of bilateral left-sidedness or right-sidedness. Previous publications on cardiac malpositions are replete with an arcane vocabulary that confounds rather than clarifies. Even if the terms themselves are understood, inherent complexity weighs against clarity. This review was designed as a guided tour of an unfamiliar subject. PMID:21861958

Perloff, Joseph K



Nonexercise cardiac stress testing  

SciTech Connect

Many patients who require evaluation for coronary artery disease are unable to undergo exercise stress testing because of physiologic or psychological limitations. Drs Vacek and Baldwin describe three alternative methods for assessment of cardiac function in these patients, all of which have high levels of diagnostic sensitivity and specificity. 23 references.

Vacek, J.L.; Baldwin, T. (Univ. of Kansas Medical Center, Kansas City (USA))



Cardiac disease in pregnancy.  


Cardiac disease complicates approximately 1% to 3% of pregnancies and is responsible for 10% to 15% of maternal mortality. The number of women of childbearing age with congenital disease is increasing as advances in diagnosis and treatment improve survival rates and overall health, allowing successful pregnancy. Pregnant women with severe cardiac disease or women who experience a cardiac event during pregnancy will require admission and stabilization in an adult critical care unit. This group of patients can prove challenging for the obstetrical staff and the critical care staff because they require blending of the knowledge and skills of 2 highly specialized areas of healthcare. The key component to a comprehensive and organized approach to management that ensures the best possible outcome for the woman is a multidisciplinary team that devises a plan on the basis of the most current information, communicates with each other and the patient effectively, and assumes responsibility for implementation of the plan. The purpose of this article is to review management of the woman with cardiac disease throughout pregnancy. PMID:16456361

Arafeh, Julie M R; Baird, Suzanne McMurtry



Rapid identification of polyphenol C-glycosides from Swertia franchetiana by HPLC-ESI-MS-MS.  


High-performance liquid chromatography coupled to positive ion electrospray ionization tandem mass spectrometry (MS) and diode array detection was employed to identify the polyphenol C-glycosides in the extract of Swertia franchetiana, a traditional Chinese/Tibetan herb. The neutral loss scan of the extract of S. franchetiana using the characteristic losses of 120 and 150 u provided a detailed profile of the polyphenol C-glycosides in the complex mixture. On-line UV spectroscopy along with MS-MS and MS-MS-MS mass spectra analysis produced with and without in-source collision induced dissociation was contributed to discriminate and identify the polyphenol C-glycosides. Three xanthone C-glycosides (i.e., mangiferin, isomangiferin, and 1,6,7-trihydroxyl-2-C-glucosexanthone) and three flavone C-glycosides (i.e., isoorientin, isovitexin, and swertisin) were tentatively identified. Isomangiferin and 1,6,7-trihydroxyl-2-C-glucosexanthone were for the first time found in this plant. PMID:19298704

Sun, Yanguo; Zhang, Xi; Xue, Xingya; Zhang, Yan; Xiao, Hongbin; Liang, Xinmiao



Phenolic Glycosides with antiproteasomal activity from Centaurea urvillei DC. subsp. urvillei.  


A new flavanone glycoside, naringenin-7-O-?-D-glucuronopyranoside, and a new flavonol glycoside, 6-hydroxykaempferol-7-O-?-D-glucuronopyranoside were isolated together with 12 known compounds, 5 flavone glycoside; hispidulin-7-O-?-D-glucuronopyranoside, apigenin-7-O-?-D-methylglucuronopyranoside, hispidulin-7-O-?-D-methylglucuronopyranoside, hispidulin-7-O-?-D-glucopyranoside, apigenin-7-O-?-D-glucopyranoside, a flavonol; kaempferol, two flavone; apigenin, and luteolin, a flavanone glycoside; eriodictyol-7-O-?-D-glucuronopyranoside, and three phenol glycoside; arbutin, salidroside, and 3,5-dihydroxyphenethyl alcohol-3-O-?-D-glucopyranoside from Centaurea urvillei subsp. urvillei. The structure elucidation of the new compounds was achieved by a combination of one- ((1)H and (13)C) and two-dimensional NMR techniques (G-COSY, G-HMQC, and G-HMBC) and LC-ESI-MS. The isolated compounds were tested for their antiproteasomal activity. The results indicated that kaempferol, a well known and widely distributed flavonoid in the plant kingdom, was the most active antiproteasomal agent, followed by apigenin, eriodictyol-7-O-?-D-glucuronopyranoside, 3,5-dihydroxyphenethyl alcohol-3-O-?-D-glucopyranoside, and salidroside, respectively. PMID:20937505

Gülcemal, Derya; Alanku?-Çal??kan, Ozgen; Karaalp, Canan; Ors, Ahmet Uygar; Ballar, Petek; Bedir, Erdal



Isolation of some glycosides as aroma precursors in young leaves of Japanese pepper (Xanthoxylum piperitum DC.).  


To clarify the formation mechanism for the major alcoholic aroma compounds in young leaves of Japanese pepper, the glycosides were isolated as aroma precursors. The presence of glycosides of the main alcoholic aroma constituents was indirectly determined by enzymatic hydrolysis and trifluoroacetylation (TFA) of the glycoside-containing fraction. After Amberlite XAD-2 column chromatography, ODS flash chromatography, and high-performance liquid chromatography (HPLC), two new compounds, namely, (3S,6S)-cis-linalool-3,7-oxide beta-D-glucopyranoside and 2-methylpropanyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside, were isolated. In addition, (3S,6R)-cis-linalool-3,6-oxide beta-D-glucopyranoside, which absolute configuration was the first determined, and six known glycosides, citronellyl beta-D-glucopyranoside, linalyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside, (Z)-3-hexenyl beta-D-glucopyranoside, benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside, dendranthemoside A, and 3,6-dihydroxy-5,6-dihydro-beta-ionol 9-beta-D-glucopyranoside, were isolated. All of these glycosides were isolated for the first time from the leaves of Japanese pepper. Their structures were established on the basis of spectral data and chemical evidence. The ratios of stereoisomers of the aglycon moieties of citronellyl beta-D-glucopyranoside and linalyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside were investigated by a chiral GC analysis and compared with those of free citronellol and linalool in the aroma concentrate. PMID:11743780

Jiang, L; Kojima, H; Yamada, K; Kobayashi, A; Kubota, K



Biomechanics of Early Cardiac Development  

PubMed Central

Biomechanics affect early cardiac development, from looping to the development of chambers and valves. Hemodynamic forces are essential for proper cardiac development, and their disruption leads to congenital heart defects. A wealth of information already exists on early cardiac adaptations to hemodynamic loading, and new technologies, including high resolution imaging modalities and computational modeling, are enabling a more thorough understanding of relationships between hemodynamics and cardiac development. Imaging and modeling approaches, used in combination with biological data on cell behavior and adaptation, are paving the road for new discoveries on links between biomechanics and biology and their effect on cardiac development and fetal programming. PMID:22760547

Goenezen, Sevan; Rennie, Monique Y.



Ethical Issues in Cardiac Surgery  

PubMed Central

While ethical behavior has always been part of cardiac surgical practice, ethical deliberation has only recently become an important component of cardiac surgical practice. Issues such as informed consent, conflict of interest, and professional self-regulation, among many others, have increasingly attracted the attention of cardiac surgeons. This review covers several broad topics of interest to cardiac surgeons and cardiologists, and treats several other topics more briefly. There is much uncertainty about what the future holds for cardiac surgical practice, research, and culture, and we discuss the background of ethical issues to serve as a platform for envisioning what is to come. PMID:22642634

Kavarana, Minoo N.; Sade, Robert M.



Bioprospecting metagenomics of decaying wood: mining for new glycoside hydrolases  

SciTech Connect

To efficiently deconstruct recalcitrant plant biomass to fermentable sugars in industrial processes, biocatalysts of higher performance and lower cost are required. The genetic diversity found in the metagenomes of natural microbial biomass decay communities may harbor such enzymes. Our goal was to discover and characterize new glycoside hydrolases (GHases) from microbial biomass decay communities, especially those from unknown or never previously cultivated microorganisms. From the metagenome sequences of an anaerobic microbial community actively decaying poplar biomass, we identified approximately 4,000 GHase homologs. Based on homology to GHase families/activities of interest and the quality of the sequences, candidates were selected for full-length cloning and subsequent expression. As an alternative strategy, a metagenome expression library was constructed and screened for GHase activities. These combined efforts resulted in the cloning of four novel GHases that could be successfully expressed in Escherichia coli. Further characterization showed that two enzymes showed significant activity on p-nitrophenyl-{alpha}-L-arabinofuranoside, one enzyme had significant activity against p-nitrophenyl-{beta}-D-glucopyranoside, and one enzyme showed significant activity against p-nitrophenyl-{beta}-D-xylopyranoside. Enzymes were also tested in the presence of ionic liquids. Metagenomics provides a good resource for mining novel biomass degrading enzymes and for screening of cellulolytic enzyme activities. The four GHases that were cloned may have potential application for deconstruction of biomass pretreated with ionic liquids, as they remain active in the presence of up to 20% ionic liquid (except for 1-ethyl-3-methylimidazolium diethyl phosphate). Alternatively, ionic liquids might be used to immobilize or stabilize these enzymes for minimal solvent processing of biomass.

Li L. L.; van der Lelie D.; Taghavi, S.; McCorkle, S. M.; Zhang, Y.-B.; Blewitt, M. G.; Brunecky, R.; Adney, W. S.; Himmel, M. E.; Brumm, P.; Drinkwater, C.; Mead, D. A.; Tringe, S. G.



Characterization of Five ?-Glycoside Hydrolases from Cellulomonas fimi ATCC 484.  


The Gram-positive bacterium Cellulomonas fimi produces a large array of carbohydrate-active enzymes. Analysis of the collection of carbohydrate-active enzymes from the recent genome sequence of C. fimi ATCC 484 shows a large number of uncharacterized genes for glycoside hydrolase (GH) enzymes potentially involved in biomass utilization. To investigate the enzymatic activity of potential ?-glucosidases in C. fimi, genes encoding several GH3 enzymes and one GH1 enzyme were cloned and recombinant proteins were expressed in Escherichia coli. Biochemical analysis of these proteins revealed that the enzymes exhibited different substrate specificities for para-nitrophenol-linked substrates (pNP), disaccharides, and oligosaccharides. Celf_2726 encoded a bifunctional enzyme with ?-d-xylopyranosidase and ?-l-arabinofuranosidase activities, based on pNP-linked substrates (CfXyl3A). Celf_0140 encoded a ?-d-glucosidase with activity on ?-1,3- and ?-1,6-linked glucosyl disaccharides as well as pNP-?-Glc (CfBgl3A). Celf_0468 encoded a ?-d-glucosidase with hydrolysis of pNP-?-Glc and hydrolysis/transglycosylation activities only on ?-1,6-linked glucosyl disaccharide (CfBgl3B). Celf_3372 encoded a GH3 family member with broad aryl-?-d-glycosidase substrate specificity. Celf_2783 encoded the GH1 family member (CfBgl1), which was found to hydrolyze pNP-?-Glc/Fuc/Gal, as well as cellotetraose and cellopentaose. CfBgl1 also had good activity on ?-1,2- and ?-1,3-linked disaccharides but had only very weak activity on ?-1,4/6-linked glucose. PMID:25225266

Gao, Juan; Wakarchuk, Warren



Antioxidant constituents and a new triterpenoid glycoside from Flos Lonicerae.  


As a component of our continuing investigations into herb-derived antioxidant agents, we have evaluated the antioxidant effects of Flos Lonicerae (Lonicera japonica flowers), via 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, total reactive oxygen species (ROS), hydroxyl radical (*OH), and peroxynitrite (ONOO-) assays. Among the methanolic extract and the dichloromethane, ethyl acetate, n-butanol, and water fractions, the EtOAc fraction of Flos Lonicerae exhibited marked scavenging/inhibitory activities, as follows: IC50 values of 4.37, 27.58 +/- 0.71, 0.47 +/- 0.05, and 12.13 +/- 0.79 microg/mL in the DPPH, total ROS, ONOO-, and *OH assays, respectively. Via a bioactivity-guided fractionation approach, a new triterpenoid glycoside, oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-xylopyranosyl(1-->6)]-beta-D-glucopyranosyl ester (12), along with eleven known compounds, including chrysoeriol (1), luteolin (2), 5-hydroxymethyl-2-furfural (3), caffeic acid (4), protocatechuic acid (5), chrysoeriol 7-O-beta-D-glucopyranoside (6), isorhamnetin 3-O-beta-D-glucopyranoside (7), kaempferol 3-O-beta-D-glucopyranoside (8), quercetin 3-O-beta-D-glucopyranoside (9), hederagenin 3-O-alpha-L-arabinopyranoside (10), and luteolin 7-O-beta-D-glucopyranoside (11), were isolated from the EtOAc fraction. The structures of isolated compounds 1-12 were elucidated via spectroscopic analyses. Compound 12 was isolated from a natural source for the first time. Compounds 2, 4, 5, 7, 9, and 11 evidenced marked scavenging activities, with IC50 values of 2.08-11.76 microM for DPPH radicals, and 1.47-6.98 microM for ONOO-. PMID:17328234

Choi, Chun-Whan; Jung, Hyun Ah; Kang, Sam Sik; Choi, Jae Sue



Bioprospecting metagenomics of decaying wood: mining for new glycoside hydrolases  

PubMed Central

Background To efficiently deconstruct recalcitrant plant biomass to fermentable sugars in industrial processes, biocatalysts of higher performance and lower cost are required. The genetic diversity found in the metagenomes of natural microbial biomass decay communities may harbor such enzymes. Our goal was to discover and characterize new glycoside hydrolases (GHases) from microbial biomass decay communities, especially those from unknown or never previously cultivated microorganisms. Results From the metagenome sequences of an anaerobic microbial community actively decaying poplar biomass, we identified approximately 4,000 GHase homologs. Based on homology to GHase families/activities of interest and the quality of the sequences, candidates were selected for full-length cloning and subsequent expression. As an alternative strategy, a metagenome expression library was constructed and screened for GHase activities. These combined efforts resulted in the cloning of four novel GHases that could be successfully expressed in Escherichia coli. Further characterization showed that two enzymes showed significant activity on p-nitrophenyl-?-L-arabinofuranoside, one enzyme had significant activity against p-nitrophenyl-?-D-glucopyranoside, and one enzyme showed significant activity against p-nitrophenyl-?-D-xylopyranoside. Enzymes were also tested in the presence of ionic liquids. Conclusions Metagenomics provides a good resource for mining novel biomass degrading enzymes and for screening of cellulolytic enzyme activities. The four GHases that were cloned may have potential application for deconstruction of biomass pretreated with ionic liquids, as they remain active in the presence of up to 20% ionic liquid (except for 1-ethyl-3-methylimidazolium diethyl phosphate). Alternatively, ionic liquids might be used to immobilize or stabilize these enzymes for minimal solvent processing of biomass. PMID:21816041



Biodegradable lightweight construction boards based on tannin\\/hexamine bonded hemp shaves  

Microsoft Academic Search

3  , with a dry I.B. strength of up to 0.34?MPa, a formaldehyde release well within the emission class E1 and certificate as\\u000a normal flammable and not burning dripped off (DIN 4102-B2) were fabricated by mixing hemp shaves with a borate-modified mimosa\\u000a tannin-hexamine binder and press the masses as fast as 6?s\\/mm thickness at 70°C to one-layer boards. Different drying processes

M. Theis; B. Grohe



Combining ability for condensed tannin concentration among five cotton (Gossypium hirsutum L.) genotypes  

E-print Network

was analyzed using the HCl-butanol method. Sampling was done at first bloom and at two weeks after first bloom. Combining ability was determined using Griffing's Method 2 Model I lysi . Nao t lacy ot d l'oth w plac d terminals of parents and growth rates... at first bloom, College Station, TX, 1988. . . . . . 30 13 14 Estimates of general combining ability (gca) effects for tannin concentration of the true leaf on the 6th main stem node from the terminal of five cotton genotypes at first bloom, College...

Altamarino, Teresita Protacio



Removal of metal ions by modified Pinus radiata bark and tannins from water solutions  

Microsoft Academic Search

Pinus radiata bark and tannins, chemically modified with an acidified formaldehyde solution were used for removing metal ions from aqueous solutions and copper mine acidic residual waters. The adsorption ability to different metal ions [V(V), Re(VII), Mo(VI), Ge(IV), As(V), Cd(II), Hg(II), Al(III), Pb(II), Fe(II), Fe(III), Cu(II)] and the factors affecting their removal from solutions were investigated. Effect of pH on

Graciela Palma; Juanita Freer; Jaime Baeza



Tannin analysis of chestnut bark samples (Castanea sativa Mill.) by HPLC-DAD-MS.  


In the present investigation, an HPLC-DAD/ESI-MS method for the complete analysis of tannins and other phenolic compounds of different commercial chestnut bark samples was developed. A total of seven compounds (vescalin, castalin, gallic acid, vescalagin, 1-O-galloyl castalagin, castalagin and ellagic acid) were separated and quantified, being 1-O-galloyl castalagin tentatively identified and found for the first time in chestnut bark samples. Thus, this method provided information regarding the composition and quality of chestnut bark samples, which is required since these samples are commercialised due to their biochemical properties as ingredients of food supplements. PMID:24679783

Comandini, Patrizia; Lerma-García, María Jesús; Simó-Alfonso, Ernesto Francisco; Toschi, Tullia Gallina



Effects of gamma radiation on total phenolics, trypsin and tannin inhibitors in soybean grains  

NASA Astrophysics Data System (ADS)

The objective was determining possible radiation-induced alterations (with doses of 2, 4 and 8 kGy) in raw or cooked grains from five soybean cultivars through the analysis of some antinutrient. Total phenolic ranged from 2.46 to 10.83 mg/g, the trypsin inhibited from 18.19 to 71.64 UTI/g and tannins from 0.01 to 0.39 mg/g. All the antinutrient studied underwent reduction with increases in the doses and cooking process was effective too.

de Toledo, T. C. F.; Canniatti-Brazaca, S. G.; Arthur, V.; Piedade, S. M. S.