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1

Naturally occurring cardiac glycosides.  

PubMed

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

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

1986-05-12

2

Anticancer activity of cardiac glycosides  

PubMed Central

Retrospective clinical data indicate that cardiac glycosides (CGs), notably digoxin, prolong the survival of carcinoma patients treated with conventional chemotherapy. CGs are known to influence the immune response at multiple levels. In addition, recent results suggest that CGs trigger the immunogenic demise of cancer cells, an effect that most likely contributes to their clinical anticancer activity.

Kepp, Oliver; Menger, Laurie; Vacchelli, Erika; Adjemian, Sandy; Martins, Isabelle; Ma, Yuting; Sukkurwala, Abdul Qader; Michaud, Mickael; Galluzzi, Lorenzo; Zitvogel, Laurence; Kroemer, Guido

2012-01-01

3

Antiproliferative Cardiac Glycosides from the Latex of Antiaris toxicaria.  

PubMed

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

2013-09-13

4

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

PubMed

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

2004-01-01

5

Comparative topo-optical investigation of cardiac glycoside localization  

Microsoft Academic Search

Summary The aldehyde-bisulfite-toluidine blue (ABT) reaction is a selective topo-optical test of vicinal-OH and amino-OH groups. The localization of cardiac glycoside was investigated morphologically. After digoxin the sarcolemma membranes, capillaries and sinus node showed strong basophilia and negative birefringence. The topo-optical reaction are useful for the histopathological examination. The new method gives the possibility to the digoxin intoxication with a

P. Sótonyi; E. Somogyi

1983-01-01

6

Ex Vivo Activity of Cardiac Glycosides in Acute Leukaemia  

PubMed Central

Background Despite years of interest in the anti-cancerous effects of cardiac glycosides (CGs), and numerous studies in vitro and in animals, it has not yet been possible to utilize this potential clinically. Reports have demonstrated promising in vitro effects on different targets as well as a possible therapeutic index/selectivity in vitro and in experimental animals. Recently, however, general inhibition of protein synthesis was suggested as the main mechanism of the anti-cancerous effects of CGs. In addition, evidence of species differences of a magnitude sufficient to explain the results of many studies called for reconsideration of earlier results. Principal Findings In this report we identified primary B-precursor and T-ALL cells as being particularly susceptible to the cytotoxic effects of CGs. Digitoxin appeared most potent and IC50 values for several patient samples were at concentrations that may be achieved in the clinic. Significant protein synthesis inhibition at concentrations corresponding to IC50 was demonstrated in colorectal tumour cell lines moderately resistant to the cytotoxic effects of digoxin and digitoxin, but not in highly sensitive leukaemia cell lines. Conclusion It is suggested that further investigation regarding CGs may be focused on diagnoses like T- and B-precursor ALL.

Hallbook, Helene; Felth, Jenny; Eriksson, Anna; Fryknas, Marten; Bohlin, Lars; Larsson, Rolf; Gullbo, Joachim

2011-01-01

7

Cardiac glycosides block cancer growth through HIF-1?- and NF-?B-mediated Plk1.  

PubMed

Cardiac glycosides as inhibitors of the sodium/potassium adenosine triphosphatase (sodium pump) have been reported to block cancer growth by inducing G2/M phase arrest in many cancer cells. However, no detailed studies have been performed to distinguish between these two phases of cardiac glycoside-arrested cells. Furthermore, the underlying mechanisms involved in this cell cycle arrest process are still not known. Here, we report that bufalin and other cardiac glycosides potently induce mitotic arrest by the downregulation of polo-like kinase 1 (Plk1) expression. Live-cell imaging results demonstrate that bufalin-treated cells exhibit a marked delay in entering prophase at an early stage and are then arrested at prometaphase or induced entry into apoptosis. This phenotypic change is attributed to the downregulation of Plk1. We also show that bufalin and the knockdown of sodium pump reduce Plk1, at least in part, through downregulation of the nuclear transcription factors, hypoxia-inducible factor-1? (HIF-1?) and nuclear factor-kappa B (NF-?B). These findings suggest that cardiac glycosides induce mitotic arrest and apoptosis through HIF-1?- and NF-?B-mediated downregulation of Plk1 expression, demonstrating that HIF-1? and NF-?B are critical targets of cardiac glycosides in exerting their anticancer action. PMID:23615397

Xie, Chuan-Ming; Liu, Xiao-Yu; Yu, Sidney; Cheng, Christopher H K

2013-04-24

8

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

Microsoft Academic Search

Cardiac steroids are used to treat various diseases including congestive heart failure and cancer. The aim of this study was to investigate the anti-leukemic activity of UNBS1450, a hemi-synthetic cardenolide belonging to the cardiac steroid glycoside family. Here, we report that, at low nanomolar concentrations, UNBS1450 induces apoptotic cell death. Subsequently, we have investigated the molecular mechanisms leading to apoptosis

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

2011-01-01

9

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

Microsoft Academic Search

Giant nerve fibers of squid Sepioteuthis sepioidea 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, and embedded in Epon, and structural complexes along the axolemma were studied. These complexes consist of a portion of axolemma

GLORIA M. VILLEGAS; JORGE VILLEGAS

1976-01-01

10

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

Microsoft Academic Search

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 LC50 value of cardiac glycosides against GAS was time dependent and the LC50 value at 96h was as low as 3.71mg\\/L, which was comparable with that of metaldehyde at 72h (3.88mg\\/L). These

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

2011-01-01

11

Simultaneous analysis of cardiac glycosides in blood and urine by thermoresponsive LC-MS-MS  

Microsoft Academic Search

A new thermoresponsive polymer separation column was applied to simultaneous analysis of four cardiac glycosides (CGs) being\\u000a widely used for the treatment of arrhythmias and heart failure in human blood and urine. This column is composed of an N-isopropylacrylamide polymer, the surface of which undergoes a reversible alteration from hydrophilic to hydrophobic by changing\\u000a temperature. The chromatographic separation and retention

Sanae Kanno; Kanako Watanabe; Itaru Yamagishi; Seishiro Hirano; Kayoko Minakata; Kunio Gonmori; Osamu Suzuki

2011-01-01

12

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

PubMed

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

2011-06-01

13

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

Microsoft Academic Search

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

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

2006-01-01

14

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

SciTech Connect

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

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

1986-03-05

15

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

PubMed

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

2012-11-02

16

Mediation of cardiac glycoside insensitivity in the monarch butterfly ( Danaus plexippus ): Role of an amino acid substitution in the ouabain binding site of Na + ,K + ATPase  

Microsoft Academic Search

The Monarch butterfly (Danaus plexippus) sequesters cardiac glycosides (CG) for its chemical defense against predators. Larvae and adults of this butterfly are insensitive towards dietary cardiac glycosides, whereas other Lepidoptera are sensitive and intoxicated by ouabain. Ouabain inhibits Na+,K+-ATPase by binding to its ?-subunit. We have amplified and cloned the DNA-sequence encoding the respective ouabain binding site. Instead of the

F. Holzinger; M. Wink

1996-01-01

17

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.

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

2011-01-01

18

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.

1986-03-05

19

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

PubMed

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

2012-11-13

20

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

PubMed Central

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

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

2006-01-01

21

Autophagic cell death of human pancreatic tumor cells mediated by oleandrin, a lipid-soluble cardiac glycoside.  

PubMed

Lipid-soluble cardiac glycosides such as bufalin, oleandrin, and digitoxin have been suggested as potent agents that might be useful as anticancer agents. Past research with oleandrin, a principle cardiac glycoside in Nerium oleander L. (Apocynaceae), has been shown to induce cell death through induction of apoptosis. In PANC-1 cells, a human pancreatic cancer cell line, cell death occurs not through apoptosis but rather through autophagy. Oleandrin at low nanomolar concentrations potently inhibited cell proliferation associated with induction of a profound G(2)/M cell cycle arrest. Inhibition of cell cycle was not accompanied by any significant sub G1 accumulation of cells, suggesting a nonapoptotic mechanism. Oleandrin-treated cells exhibited time- and concentration-dependent staining with acridine orange, a lysosomal stain. Subcellular changes within PANC-1 cells included mitochondrial condensation and translocation to a perinuclear position accompanied by vacuoles. Use of a fluorescent oleandrin analog (BODIPY-oleandrin) revealed co-localization of the drug within cell mitochondria. Damaged mitochondria were found within autophagosome structures. Formation of autophagosomes was confirmed through electron microscopy and detection of green fluorescent protein-labeled light chain 3 association with autophagosome membranes. Also observed was a drug-mediated inhibition of pAkt formation and up-regulation of pERK. Transfection of Akt into PANC-1 cells or inhibition of pERK activation by MAPK inhibitor abrogated oleandrin-mediated inhibition of cell growth, suggesting that the reduction of pAkt and increased pERK are important to oleandrin's ability to inhibit tumor cell proliferation. The data provide insight into the mechanisms and role of a potent, lipid-soluble cardiac glycoside (oleandrin) in control of human pancreatic cancer proliferation. PMID:18048883

Newman, Robert A; Kondo, Yasuko; Yokoyama, Tomohisa; Dixon, Susan; Cartwright, Carrie; Chan, Diana; Johansen, Mary; Yang, Peiying

2007-12-01

22

Effect of cardiac glycosides and sodium ethacrynate on transepithelial sodium transport in in vivo micropuncture experiments and on isolated plasma membrane Na?K ATPase in vitro of the rat  

Microsoft Academic Search

In parallel micropuncture experiments employing peritubular capillary perfusion techniquesin vivo and biochemical techniques on the simultaneously isolated Na-K ATPase from kidney cortexin vitro, the effects of various cardiac glycosides and sodium ethacrynate on transepithelial sodium transport in proximal tubules of the rat were examined. Cardiac glycosides with an inhibitory potency for this ATPase varying over approximately a 100 fold range

A. Z. Györy; U. Brendel; R. Kinne

1972-01-01

23

Quercetin provides greater cardioprotective effect than its glycoside derivative rutin on isoproterenol-induced cardiac fibrosis in the rat.  

PubMed

Quercetin exhibits numerous pharmacological effects, including the capacity for cardioprotection. This study aimed to investigate whether quercetin or its glycoside derivative rutin has any protective action against isoproterenol (ISO) induced cardiac fibrosis, and investigate the structure-activity relationship. Male Wistar rats were injected subcutaneously with ISO (15 mg·(kg body mass)(-1)) to induce experimental cardiac fibrosis. The cardioprotective effect of co-treatment with quercetin (25 or 50 mg·kg(-1)) or rutin (25 or 50 mg·kg(-1)) was investigated in ISO-induced cardiac fibrosis in rats. The administration of quercetin and rutin signifcantly decreased the cardiac weight index and myocardial enzyme activity, increased the activity of superoxide dismutase in the serum, and inhibited the ISO-induced increase in angiotensin?II and aldosterone in the plasma. Furthermore, overexpression of transforming growth factor ?1 (TGF-?1), connective tissue growth factor (CTGF), and excessive deposition of extracellular matrix (ECM) in isoproterenol-treated myocardial tissues were normalized by quercetin and rutin. Our results suggest that both quercetin and rutin exhibited cardioprotective effects in cardiac fibrosis induced by ISO in the rat heart. Moreover, the effects of rutin are weaker than quercetin at the same dose. The mechanism of these effects may be related to antioxidative stress, inhibition of the renin-angiotensin-aldosterone system, decrease in the expression of TGF-?1 and CTGF, and the subsequent reduction in the deposition of the ECM. PMID:24117263

Li, Min; Jiang, Yichuan; Jing, Wuhui; Sun, Bo; Miao, Chunsheng; Ren, Liqun

2013-07-13

24

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

Microsoft Academic Search

Ouabain added to physiological salt solutions bathing the isolated frog retina irreversibly abolishes the electrical response to light (the electroretino- gram 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

ROBERT N. FRANK; TIMOTHY H. GOLDSMITH

1967-01-01

25

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

PubMed

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

2011-09-26

26

A novel high-pressure liquid-liquid extraction process for downstream processing in biotechnology: extraction of cardiac glycosides.  

PubMed

This investigation examines phase equilibrium phenomena that can be used to create two water-like solvents for liquid-liquid extraction in downstream processing in biotechnology: a completely miscible, binary liquid mixture of water and a hydrophilic organic solvent (e. g., an alcohol) reveals a liquid phase split, when it is pressurized with a "near-critical" gas (i.e., a substance which at ambient conditions is a gas, near its critical temperature). This phase split results in two hydrophilic liquid phases. Making use of this phenomenon in process development first requires research on the phase split phenomenon and, second, research on the feasibility of biomolecule extraction and separation. In this study, basic fluid phase equilibrium phenomena are briefly described. Then, experimental results are reported for the partitioning of small amounts of cardiac glycosides (digitoxin and digoxin) on coexisting liquid phases in the high-pressure, three-phase, vapor-liquid-liquid equilibrium of the ternary system of "near critical" CO(2) + water + 1-propanol, at 313 K and 333 K. Finally, a process for extraction and separation of the aforementioned glycosides by means of the high-pressure phase equilibrium phenomenon is discussed. PMID:10898865

Adrian, T; Freitag, J; Maurer, G

2000-09-01

27

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.

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

2013-01-01

28

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

PubMed

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 Ca(2+) 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

Wha Jun, Dong; Hwang, Mihwa; Kim, Hyun Jung; Hwang, Soo Kyung; Kim, Sunshin; Lee, Chang-Hun

2013-10-04

29

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

30

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

PubMed Central

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

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

1977-01-01

31

Ecological tannin assays  

Microsoft Academic Search

Estimations of condensed tannin content are generally based on calibration standard curves from Quebracho condensed tannins. We generated calibration standard curves from eight Sonoran Desert species for comparison with estimates of tannin concentrations derived from the Quebracho standard curve. Estimates of leaf tannin concentrations of each of the eight species using each species standard curve differed significantly with the estimates

C. S. Wisdom; A. Gonzalez-Coloma; P. W. Rundel

1987-01-01

32

Cardiac glycoside overdose  

MedlinePLUS

Lapostolle F, Borron SW. Digitalis. In: Shannon MW, Borron SW, Burns MJ, eds. Haddad and Winchester's Clinical Management of Poisoning and Drug Overdose . 4th ed. Philadelphia, Pa: Saunders Elsevier; 2007:chap ...

33

Studies of Tannin Formaldehyde Adhesives.  

National Technical Information Service (NTIS)

Tannins are organic complex compounds generally used for tanning different kinds of leather in tanneries. Although there are numerous uses of tannins, the present study is mainly concerned with the preparation of adhesives from tannins. Different solvent ...

M. M. Anwer

1985-01-01

34

Cardiac glycosides correct aberrant splicing of IKBKAP-encoded mRNA in familial dysautonomia derived cells by suppressing expression of SRSF3.  

PubMed

The ability to modulate the production of the wild-type transcript in cells bearing the splice-altering familial dysautonomia (FD) causing mutation in the IKBKAP gene prompted a study of the impact of a panel of pharmaceuticals on the splicing of this transcript, which revealed the ability of the cardiac glycoside digoxin to increase the production of the wild-type, exon-20-containing, IKBKAP-encoded transcript and the full-length I?B-kinase-complex-associated protein in FD-derived cells. Characterization of the cis elements and trans factors involved in the digoxin-mediated effect on splicing reveals that this response is dependent on an SRSF3 binding site(s) located in the intron 5' of the alternatively spliced exon and that digoxin mediates its effect by suppressing the level of the SRSF3 protein. Characterization of the digoxin-mediated effect on the RNA splicing process was facilitated by the identification of several RNA splicing events in which digoxin treatment mediates the enhanced inclusion of exonic sequence. Moreover, we demonstrate the ability of digoxin to impact the splicing process in neuronal cells, a cell type profoundly impacted by FD. This study represents the first demonstration that digoxin possesses splice-altering capabilities that are capable of reversing the impact of the FD-causing mutation. These findings support the clinical evaluation of the impact of digoxin on the FD patient population. PMID:23711097

Liu, Bo; Anderson, Sylvia L; Qiu, Jinsong; Rubin, Berish Y

2013-06-18

35

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

SciTech Connect

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

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

1986-05-01

36

Microbial degradation of tannins – A current perspective  

Microsoft Academic Search

Tannins are water-soluble polyphenolic compounds having wide prevalence in plants. Hydrolysable and condensed tannins are the two major classes of tannins. These compounds have a range of effects on various organisms – from toxic effects on animals to growth inhibition of microorganisms. Some microbes are, however, resistant to tannins, and have developed various mechanisms and pathways for tannin degradation in

Tej K. Bhat; Bhupinder Singh; Om P. Sharma

1998-01-01

37

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.

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

1972-01-01

38

ANTIOXIDANT ACTIVITY OF EXTRACTS, CONDENSED TANNIN FRACTIONS, AND PURE FLAVONOIDS FROM PHASEOLUS VULGARIS L. SEED COAT COLOR GENOTYPES  

Technology Transfer Automated Retrieval System (TEKTRAN)

Seed coat color of dry bean (Phaseolus vulgaris L.) is determined by the presence and amounts of flavonol glycosides, anthocyanins and condensed tannins (proanthocyanidins). To date, most work on P. vulgaris focused on the antinutritional effects of the seed coat polyphenolics but nothing had been ...

39

Analysis of condensed tannins: a review  

Microsoft Academic Search

Plant condensed tannins (proanthocyanidins, PAs) have both positive and negative effects on feed digestibility and animal performance, depending both on the quantity and biological activity of the tannins that are present. In this review, the chemistry and analysis of condensed tannins (PAs) are examined. Our first focus is on the complexity of the structures of condensed tannins and our second

P Schofield; D. M Mbugua; A. N Pell

2001-01-01

40

Tannin Adhesives - From Laboratory to Industry.  

National Technical Information Service (NTIS)

The past research program on tannin-based adhesives, the research achievements attained and their translation into industrial application, as well as cost and technical advantages of tannin adhesives in current industrial use are discussed. In particular,...

H. O. Scharfetter A. Pizzi

1981-01-01

41

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

1987-01-01

42

Choosing appropriate methods and standards for assaying tannin  

Microsoft Academic Search

Tannins are chemically diverse polyphenolics that have multiple biological activities. Attempts to establish the ecological significance of tannins have been hindered by the complexities of tannin analysis. A multitude of analytical procedures for tannins has been described, but it is difficult for the nonspecialist to select appropriate methods. We have classified the most common procedures for determining tannin as either

Ann E. Hagerman; Larry G. Butler

1989-01-01

43

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

1990-01-01

44

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.

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

2012-01-01

45

Phenolic characterization of commercial enological tannins  

Microsoft Academic Search

Enological tannins are widely used in winemaking process to improve different characteristics of wines. A wide spectrum of\\u000a enological tannins is now available on the market; however, the tannins’ chemical nature and botanical origin are not always\\u000a clearly defined in the commercial products. The aim of this work was the chemical characterization of ten commercial plant-derived\\u000a tanning agents of enological

Elías Obreque-Slíer; Alvaro Peña-Neira; Remigio López-Solís; Cristián Ramírez-Escudero; Fernando Zamora-Marín

2009-01-01

46

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

47

Pharmacologically active tannins isolated from medicinal plants.  

PubMed

Starting with the isolation of a crystalline tannin (geraniin) of mild property from a popular herb medicine (Geranii herba), various polyphenolic compounds including those belonging to new classes of tannins (oligomeric hydrolyzable tannins, complex tannins, and other metabolites and condensates) have been isolated from various medicinal plants. Noticeable biological and pharmacological activities (inhibition of carcinogenesis, host-mediated antitumor activity, antiviral activity, and inhibition of active oxygen, such as inhibition of lipid peroxidation and lipoxygenase, xanthine oxidase, and monoamine oxidase) have been found for several of these polyphenolic compounds. PMID:1417694

Okuda, T; Yoshida, T; Hatano, T

1992-01-01

48

Steroidal glycosides from Agave utahensis.  

PubMed

Three new spirostanol glycosides (1-3) and a new furostanol glycoside (4), together with two known spirostanol glycosides (5 and 6) were isolated from the whole plants of Agave utahensis (Agavaceae). The structures of the new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage. PMID:17202720

Yokosuka, Akihito; Mimaki, Yoshihiro

2007-01-01

49

Sorption of polyphenolics (tannins) to natural soils  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

50

Accumulation of Uranium by Immobilized Persimmon Tannin  

Microsoft Academic Search

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

Takashi Sakaguchi; Akira Nakajima

1994-01-01

51

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

1998-01-01

52

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.

2008-12-01

53

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

Microsoft Academic Search

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

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

2009-01-01

54

Radial diffusion method for determining tannin in plant extracts  

Microsoft Academic Search

Tannin in plant extracts can be determined by reacting the tannin with a protein and quantitating the precipitated complex. In the new assay described here, a tannin-containing solution is placed in a well in a protein-containing agar slab. As the tannin diffuses into the gel and complexes with protein, a visible ring of precipitation develops. The area of the ring

Ann E. Hagerman

1987-01-01

55

Pregnane glycosides from Sansevieria trifasciata  

Microsoft Academic Search

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

Yoshihiro Mimaki; Toshihiro Inoue; Minpei Kuroda; Yutaka Sashida

1997-01-01

56

Pregnane glycosides from Sansevieria trifasciata.  

PubMed

Phytochemical analysis of the whole plant of Sansevieria trifasciata, one of the most common Agavaceae plants, has resulted in the isolation of four new pregnane glycosides. Their structures have been determined by spectroscopic analysis and acid- and alkaline-catalysed hydrolysis to be 1 beta,3 beta-dihydroxypregna-5,16-dien-20-one glycosides. This is believed to be the first report of the isolation of the pregnane glycosides from a plant of the family Agavaceae. PMID:8983214

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

1997-01-01

57

Hydrolyzable tannin analysis in food.  

PubMed

The discovery of plant polyphenols in food is perhaps one of the biggest breakthroughs in modern food science. Plant polyphenols are known for their role in food quality and safety, since they contribute significantly to taste, flavour, colour, stability etc., while they are increasingly recognised as important factors in long-term health, contributing towards reducing the risk of chronic disease. Almost 200years ago, hydrolyzable tannins (HTs) were the first group of plant polyphenols subjected to analytical chemical research. Despite the lack of commercially available standards, food analysis research offers a wealth of papers dealing with extraction optimisation, identification and quantification of HTs. The object of this review is to summarise analytical chemistry applications and the tools currently used for the analysis of HTs in food. PMID:22953913

Arapitsas, Panagiotis

2012-06-01

58

Immunological functions of steryl glycosides.  

PubMed

Steryl glycosides, sterols glycosylated at the 3?-hydroxy group, have been widely found in plants, algae, and fungi, but are rare in bacteria and animals. Glycosylation of sterols is known to modify properties of the cell membrane and confer resistance against stresses by freezing or heat-shock on cells. Furthermore, accumulating evidence obtained from recent research suggests important biological functions of steryl glycosides, including regulation of host defenses against pathogens, lipid metabolism, and developmental events. This review is focused on the immunological functions of steryl glycosides, such as modulation of host immune functions upon exposure to cholesteryl glycosides produced by pathogenic bacteria. PMID:22936327

Shimamura, Michio

2012-08-31

59

Aroma glycosides from Hovenia dulsis.  

PubMed

From the fresh leaves of Hovenia dulsis var. tomentella, two new aroma glycosides named kenposide A and B have been isolated together with the known glycoside, icariside C1. Their structures were determined on the basis of chemical and spectral evidence. PMID:7764288

Yoshikawa, K; Nagai, M; Wakabayashi, M; Arihara, S

1993-11-01

60

Anticancer and antioxidant tannins from Pimenta dioica leaves.  

PubMed

Two galloylglucosides, 6-hydroxy-eugenol 4-O-(6'-O-galloyl)-beta-D-4C1-glucopyranoside (4) and 3-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol-2-O-(2',6'-di-O-galloyl)-beta-D -4C1-glucopyranoside (7), and two C-glycosidic tannins, vascalaginone (10) and grandininol (14), together with fourteen known metabolites, gallic acid (1), methyl gallate (2), nilocitin (3), 1-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-(alpha/beta)-D-glucopyranose (5), 4,6-(S)-hexahydroxydiphenoyl-(alpha/beta)-D-glucopyranose (6), 3,4,6-valoneoyl-(alpha/beta)-D-glucopyranose (8), pedunculagin (9), casuariin (11), castalagin (12), vascalagin (13), casuarinin (15), grandinin (16), methyl-flavogallonate (17) and ellagic acid (18), were identified from the leaves of Pimenta dioica (Merr.) L. (Myrtaceae) on the basis of their chemical and physicochemical analysis (UV, HRESI-MS, 1D and 2D NMR). It was found that 9 is the most cytotoxic compound against solid tumour cancer cells, the most potent scavenger against the artificial radical DPPH and physiological radicals including ROO*, OH*, and O2-*, and strongly inhibited the NO generation and induced the proliferation of T-lymphocytes and macrophages. On the other hand, 3 was the strongest NO inhibitor and 16 the highest stimulator for the proliferation of T-lymphocytes, while 10 was the most active inducer of macrophage proliferation. PMID:17913067

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

61

A method to determine tannin concentration by the measurement and quantification of protein — tannin interactions  

Microsoft Academic Search

Protein determinations on protein-tannin complexes after protein isolation (gel filtration and trichloroacetic acid [TCA] precipitation) or phenolic extraction (polyvinyl pyrrolidone [PVP] and organic solvent precipitation) were unsuccessuful. Kjeldahl determinations of the amount of unprecipitated protein bovine serum albumin [BSA] showed a sigmoid relationship with increasing concentrations of tannins. A similar relationship was found for the reduced viscosity of BSA and

A. M. Amory; C. L. Schubert

1987-01-01

62

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

PubMed

A combination of high-resolution mass spectrometry and modern HPLC column technology, assisted by diode array detection, was used for accurate characterization of water-soluble polyphenolic compounds in the pistils, stamens, petals, sepals, stems, leaves, roots and seeds of Geranium sylvaticum. The organs contained a large variety of polyphenols, five types of tannins (ellagitannins, proanthocyanidins, gallotannins, galloyl glucoses and galloyl quinic acids) as well as flavonoids and simple phenolic acids. In all, 59 compounds were identified. Geraniin and other ellagitannins dominated in all the green photosynthetic organs. The other organs seem to produce distinctive polyphenol groups: pistils accumulated gallotannins; petals acetylglucose derivatives of galloylglucoses; stamens kaempferol glycosides, and seeds and roots accumulated proanthocyanidins. The intra-plant distribution of the different polyphenol groups may reflect the different functions and importance of various types of tannins as the defensive chemicals against herbivory. PMID:23790750

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

2013-06-19

63

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))

1994-01-01

64

Tannin oxidation: intra- versus intermolecular reactions.  

PubMed

Grape and apple condensed tannin fractions were autoxidized at high concentrations (5 g/L) in aqueous solutions and analyzed by thiolysis (depolymerization followed by HPLC analysis) and small angle X-ray scattering (SAXS). Structural parameters of native (unoxidized) tannin polymers were derived from SAXS according to the wormlike chain model: the length per monomer is 15 A, the length of the statistical segment 17 A, and the cross section of the macromolecule has a radius within the range 3-4.5 A. The rather short length of the statistical segment is an effect of the different location of interflavanol linkages, which cause a loss of orientational correlation between successive monomers. Oxidation created new bonds that were resistant to thiolysis, and, according to thiolysis, some of these new bonds were intramolecular. However, according to SAXS, oxidation at high tannin concentration caused the weight average degree of polymerization to increase, indicating that intermolecular reactions took place as well, creating larger macromolecules. In the case of the smaller grape seed tannins, these intermolecular reactions took place "end to end" leading to the formation of longer linear macromolecules, at least in the earlier stages of oxidation. In the case of the larger apple tannins, the SAXS patterns were characteristic of larger branched macromolecules. Accordingly, the intermolecular reactions were mainly "end to middle". This is in agreement with the higher probabilities of "end to middle" reactions arising from a higher ratio extension unit/terminal unit in the latter case. PMID:20831276

Poncet-Legrand, Céline; Cabane, Bernard; Bautista-Ortín, Ana-Belén; Carrillo, Stéphanie; Fulcrand, Hélène; Pérez, Javier; Vernhet, Aude

2010-09-13

65

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

2013-03-01

66

Bacterial Mechanisms to Overcome Inhibitory Effects of Dietary Tannins  

Microsoft Academic Search

High concentrations of tannins in fodder plants inhibit gastrointestinal bacteria and reduce ruminant performance. Increasing\\u000a the proportion of tannin-resistant bacteria in the rumen protects ruminants from antinutritional effects. The reason for the\\u000a protective effect is unclear, but could be elucidated if the mechanism(s) by which tannins inhibit bacteria and the mechanisms\\u000a of tannin resistance were understood. A review of the

Alexandra H. Smith; Erwin Zoetendal; Roderick I. Mackie

2005-01-01

67

Tannins in nutrient dynamics of forest ecosystems - a review  

Microsoft Academic Search

Tannins make up a significant portion of forest carbon pools and foliage and bark may contain up to 40% tannin. Like many other plant secondary compounds, tannins were believed to function primarily as herbivore deterrents. However, recent evidence casts doubts on their universal effectiveness against herbivory. Alternatively, tannins may play an important role in plant–plant and plant–litter–soil interactions. The convergent

Tamara E. C. Kraus; Randy A. Dahlgren; Robert J. Zasoski

2003-01-01

68

Dry bean tannins: A review of nutritional implications  

Microsoft Academic Search

Tannins are one of several antinutritional factors present in dry beans and are located mainly in the seed coat or testa.\\u000a The tannin content of dry beans ranges from 0.0 to 2.0% depending on the bean species and color of the seed coat. Many high\\u000a tannin bean varieties are of lower nutritional quality than low tannin varieties of beans. Naturally

N. R. Reddy; M. D. Pierson; S. K. Sathe; D. K. Salunkhe

1985-01-01

69

Phenolic acid and condensed tannin concentrations of six cotton genotypes  

Microsoft Academic Search

Phenolic acids and condensed tannins have been implicated in plant resistance to insects and diseases. The objective of this study was to determine phenolic acid and condensed tannin concentrations in six cotton (Gossypium hirsutum L.) genotypes that display varying degrees of spider mite [Tetranychus urticae (Koch)] resistance. Since phenolic acids are precursors for condensed tannins in the shikimate pathway, the

K. E. Lege; J. T. Cothren; C. W. Smith

1995-01-01

70

Extraction of tannin from fresh and preserved leaves  

Microsoft Academic Search

The extractability of tannin from fresh, lyophilized, and dried leaves collected at various times in the growing season was determined using the radial diffusion assay for protein-precipitating phenolics. The amount of tannin extracted depended on the method of leaf preservation and on the maturity of the leaf. Early in the season, more tannin was extracted from lyophilized leaves than from

Ann E. Hagerman

1988-01-01

71

Models of suppressive effect of tannins. Analysis of the suppressive effect of tannins on ruminal degradation by compartmental models  

Microsoft Academic Search

Three compartmental models were developed to evaluate the suppressive effects of tannins on the extent and rate of degradation of tree foliage. The first model was based on the assumption that tannins modify the parameters of the degradation kinetics, the second was based on the assumption that tannins bind material, independent of the basic degradation kinetics, and the third combined

Y. Aharoni; N. Gilboa; N. Silanikove

1998-01-01

72

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.

73

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

PubMed

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

2009-05-27

74

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.

2008-06-01

75

Do all tannins have similar nutritional effects? A comparison of three Brazilian fodder legumes  

Microsoft Academic Search

Three tropical legumes, namely Leucaena leucocephala, Sesbania sesban and Cajanus cajan, were subjected to chemical analysis plus in vitro, in situ and in vivo evaluations. Three different assays were used to determine total tannins: adsorption to polyvinyl pyrrolidine (PVPP-tannins), radial diffusion (RD-tannins) and protein precipitation capacity (BSA-tannins). Total phenols, total tannins and condensed tannins were highest for Sesbania. RD-tannins were

D. M. S. S. Vitti; A. L. Abdalla; I. C. S. Bueno; J. C. Silva Filho; C. Costa; M. S. Bueno; E. F. Nozella; C. Longo; E. Q. Vieira; S. L. S. Cabral Filho; P. B. Godoy; I. Mueller-Harvey

2005-01-01

76

Effect of marine glycosides on adenosinetriphosphatase activity.  

PubMed

Marine glycosides from the sea cucumbers Actinopyga agassizi, Holothuria atra, Bohadschia argus, Cucumaria fraudatrix, Astichopus multifidus and Thelenota ananas inhibit both Na+-K+ ATPase and Mg2+-ATPase of rat brain in vitro. The glycoside-cholesterol complex of these compounds does not influence ATPase activity. Asterosaponins from starfishes Linckia guildingi and Linckia laevigata possess a slight inhibiting effect. The triterpene glycosides from sea cucumbers are more powerful inhibitors than steroidal glycosides from starfishes. PMID:6213068

Gorshkov, B A; Gorshkova, I A; Stonik, V A; Elyakov, G B

1982-01-01

77

Triterpene glycosides from Schefflera octophylla.  

PubMed

In addition to 3-epi-betulinic acid, three triterpene glycosides were isolated from leaves of Schefflera octophylla. The structures of the glycosides have been determined as 28-O-[alpha-L-rhamnopyranosyl(1----4)-O-beta-D-glucopyranosyl(1----6)-be ta-D- glucopyranosides of 3 alpha-hydroxy-lup-20(29)-ene-23,28-dioic acid, 3 alpha,11 alpha- dihydroxy-lup20(29)-ene-23,28-dioic acid and 3-epi-betulinic acid by spectroscopic data and chemical transformations. The last two compounds were found for the first time in the plant kingdom. PMID:1367650

Sung, T V; Steglich, W; Adam, G

1991-01-01

78

[Phenyl glycosides from Curculigo orchioides].  

PubMed

One new phenyl glycoside and two new chlorophenyl glycosides were isolated from rhizomes of Curculigo orchioides (Chinese name: Xian Mao, Hypoxidaceae). Based on HRMS, FABMS, 1H-, 13C-NMR and other spectral data as well as chemical evidence, the structures of curculigoside B, curculigine B and C were elucidated to be 2-beta-D-glucopyranosyloxy-5-hydroxybenzyl-2'-methoxy-6'-hydroxybe nzoate (I),24-dichloro-3-methyl-5-methoxy-phenol-O-beta-D-apiofuranosyl (1-6)-beta-D-glucopyanoside (III) and 2,4,6-trichloro-3-methyl-5-methoxyphenol-O-beta-D-xylopyranosyl (1-6)-beta-D-glucopyranoside (IV), respectively. PMID:1442056

Xu, J P; Xu, R S

1992-01-01

79

Effects and fate of tannins in ruminant animals, adaptation to tannins, and strategies to overcome detrimental effects of feeding tannin-rich feeds  

Microsoft Academic Search

Trees and shrub foliage and agro-industrial by-products are of importance in animal production because they do not compete with human food and can provide significant protein supplements, especially in the dry season. But, these feed resources are generally rich in antinutritional factors, particularly tannins. The amount of tannins that they contain vary widely and largely unpredictably, and their effects on

H. P. S. Makkar

2003-01-01

80

Flavonoid glycosides from viscum alniformosanae  

PubMed

Two new flavonoid glycosides, (2S)-5-hydroxy-7, 3'-dimethoxyflavanone-4'-O-beta-[apiosyl (1 --> 2)]glucoside (1) and rhamnazin-4'-O-beta-[apiosyl (1 --> 2)]glucoside (2) were isolated from Viscum alniformosanae. Structures were elucidated by NMR and mass spectroscopic analysis. PMID:10543905

Chou; Ko; Lin

1999-10-01

81

Catalytic regioselective oxidation of glycosides.  

PubMed

Discrimination among equals: A catalytic method for the selective oxidation of unprotected glycosides, both monosaccharides and disaccharides, has been developed. The resulting ketosaccharides are isolated in moderate to excellent yields. This approach provides a basis for protecting-group-free synthetic transformations of carbohydrates. PMID:23780519

Jäger, Manuel; Hartmann, Marcel; de Vries, Johannes G; Minnaard, Adriaan J

2013-06-18

82

Flavanone glycosides from Alhagi pseudalhagi.  

PubMed

Two new flavanone glycosides, alhagitin and alhagidin, have been isolated from the whole plant of Alhagi pseudalhagi and their structures established respectively as naringenin 5-methyl ether 4'-glucoside and hesperitin 7-galactosyl(1-->2)[rhamnosyl(1-->6)]glucoside by chemical and spectroscopic methods. PMID:10389270

Singh, V P; Yadav, B; Pandey, V B

1999-06-01

83

Kaurane glycosides from Inula britannica  

Microsoft Academic Search

Two new diterpene glycosides have been isolated from Inula britannica and their structures established as 17-O-?-d-glucopyranosyl-16-?-H-ent-kauran-19-oic acid and 17-O-?-d-glucopyranosyl-16-?-H-ent-kauran-19-oicacid-19-O-?-d-glucopyranoside, respectively, from their spectral data, and chemical and enzymatic evidence. In addition, six known compounds were also identified.

Yu Shao; Nai-Shen Bai; Bing-Nan Zhou

1996-01-01

84

Recovery of uranium from seawater by immobilized tannin  

SciTech Connect

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

Sakaguchi, T.; Nakajima, A.

1987-06-01

85

MALDI–TOF mass spectrometry of polyflavonoid tannins  

Microsoft Academic Search

Matrix-Assisted Laser Desorption\\/Ionization Time-of-Flight (MALDI–TOF) appears to be a suitable method for examining polyflavonoid tannin oligomers. It appears capable to determine aspects of the structure and characteristics of polyflavonoid tannins, which are otherwise too difficult to determine by other techniques. It has been possible to determine by MALDI–TOF for the two major industrial polyflavonoid tannins which exist, namely mimosa and

H. Pasch; A. Pizzi; K. Rode

2001-01-01

86

Tannin-binding salivary proteins in three captive rhinoceros species  

Microsoft Academic Search

Tannin-binding salivary proteins (TBSP) are considered to be counter-defences acquired in the course of evolution by animals whose natural forage contains such tannins. As tannins mostly occur in browse material but not in grasses, it is assumed that grazers do not have a need for TBSP. Whereas it has been shown in several non-ungulate species that TBSP can be induced

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

2005-01-01

87

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). 721.10666 Section...bis(fattyalkyl) dimethyl, salts with tannins (generic). (a) Chemical substance...bis(fattyalkyl) dimethyl, salts with tannins (PMN P-12-437) is subject to...

2013-07-01

88

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

Microsoft Academic Search

Received 29 July 2002\\/Accepted 25 February 2003 Tannins are plant-derived polyphenols with antimicrobial effects. The mechanism of tannin toxicity towards Escherichia coli was determined by using an extract from Acacia mearnsii (Black wattle) as a source of condensed tannins (proanthocyanidins). E. coli growth was inhibited by tannins only when tannins were exposed to oxygen. Tannins auto-oxidize, and substantial hydrogen peroxide

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

2003-01-01

89

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

Microsoft Academic Search

The ability of foliar tannins to increase plant resistance to herbivores is potentially determined by the composition of the\\u000a tannins; hydrolyzable tannins are much more active as prooxidants in the guts of caterpillars than are condensed tannins.\\u000a By manipulating the tannin compositions of two contrasting tree species, this work examined: (1) whether increased levels\\u000a of hydrolyzable tannins increase the resistance

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

2009-01-01

90

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

PubMed

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

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

2013-06-01

91

Triterpenoid glycosides from Bacopa monnieri  

Microsoft Academic Search

Two triterpenoid glycosides have been isolated along with 10 known saponins from Bacopa monnieri. Structures of the compounds have been elucidated as 3-O-[?-d-glucopyranosyl-(1?3)-?-d-glucopyranosyl] jujubogenin (1) and 3-O-[?-d-glucopyranosyl-(1?3)-?-d-glucopyranosyl] pseudojujubogenin (2) by high resolution NMR spectral data and chemical correlations. Further, the chemical compositions of bacosides A and B have been delineated.

Chillara Sivaramakrishna; Chirravuri V. Rao; Golakoti Trimurtulu; Mulabagal Vanisree; Gottumukkala V. Subbaraju

2005-01-01

92

Steroidal glycosides from Ruscus ponticus.  

PubMed

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

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

2011-02-26

93

Metabolism of tomato steroidal glycosides in humans.  

PubMed

Pregnane glycosides have been isolated in small amounts, along with the major components furostanol and spirostanol glycosides, from Dioscoreaceae, Taccaceae, and Solanaceae, suggesting that pregnane glycosides might be biosynthesized from furostanol and spirostanol glycosides. Recently, commercial natural foods composed of diosgenin have been used for the treatment of diseases such as osteoporosis and premenstrual syndrome in women. It is anticipated that diosgenin would be metabolized into a type of steroidal hormone, for instance progesterone, however, this metabolism has not been confirmed. Therefore, we have examined the metabolites in the urine of subjects who ingested tomatoes, which contain a considerable amount of the steroidal glycoside esculeoside A. The occurrence of steroidal hormones in the metabolites has been recognized. It has been proven that when a steroidal glycoside is administered, it is partly metabolized into a type of steroidal hormone exhibiting various physiological activities. PMID:16946542

Noguchi, Eishin; Fujiwara, Yukio; Matsushita, Sayaka; Ikeda, Tsuyoshi; Ono, Masateru; Nohara, Toshihiro

2006-09-01

94

Applicability of insoluble tannin to treatment of waste containing americium  

Microsoft Academic Search

The applicability of insoluble tannin adsorbent to the treatment of aqueous waste contaminated with americium has been investigated. Insoluble tannin is considered highly applicable because it consists of only carbon, hydrogen and oxygen and so its volume can be easily reduced by incineration. This report describes measurements of the americium distribution coefficient in low concentration nitric acid. The americium distribution

Tatsuro Matsumura; Shigekazu Usuda

1998-01-01

95

Microbial interactions with tannins: nutritional consequences for ruminants  

Microsoft Academic Search

Polyphenolics are widely distributed in the plant kingdom and are often present in the diet of herbivores. The two major groups of plant polyphenolic compounds other than lignin are condensed and hydrolysable tannins. These compounds can have toxic and\\/or antinutritional effects on the animal. It is well established that tannins complex with dietary proteins can reduce nitrogen supply to the

C. S McSweeney; B Palmer; D. M McNeill; D. O Krause

2001-01-01

96

Douglas-Fir Bark Tannin Decomposition in Two Forest Soils.  

National Technical Information Service (NTIS)

Purified Douglas-fir bark tannin equivalent to the amount in a 2-inch bark mulch was added to two widely different soils in the laboratory. About 22 percent of the tannin decomposed in 180 days. Soil microflora generally increased. Nitrate production was ...

W. B. Bollen K. C. Lu

1969-01-01

97

THE BIOCHEMISTRY OF TANNINS: ROLE IN RUMINANT NUTRITION  

Technology Transfer Automated Retrieval System (TEKTRAN)

Tannins are high molecular weight, water-soluble polyphenols that form reversible complexes with proteins through pH-dependent hydrogen bonding and hydrophobic interactions. Hydrolyzable tannins (HT) contain a carbohydrate core esterified with gallic or hexahydroxydiphenic acids. Binding of HT to ...

98

HPLC retention thermodynamics of grape and wine tannins.  

PubMed

The effect of grape and wine tannin structure on retention thermodynamics under reversed-phase high-performance liquid chromatography conditions on a polystyrene divinylbenzene column was investigated. On the basis of retention response to temperature, an alternative retention factor was developed to approximate the combined temperature response of the complex, unresolvable tannin mixture. This alternative retention factor was based upon relative tannin peak areas separated by an abrupt change in solvent gradient. Using this alternative retention factor, retention thermodynamics were calculated. Van't Hoff relationships of the natural log of the alternative retention factor against temperature followed Kirchoff's relationship. An inverse quadratic equation was fit to the data, and from this the thermodynamic parameters for tannin retention were calculated. All tannin fractions exhibited exothermic, spontaneous interaction, with enthalpy-entropy compensation observed. Normalizing for tannin size, distinct tannin compositional effects on thermodynamic parameters were observed. The results of this study indicate that HPLC can be valuable for measuring the thermodynamics of tannin interaction with a hydrophobic surface and provides a potentially valuable alternative to calorimetry. Furthermore, the information gathered may provide insight into understanding red wine astringency quality. PMID:23565723

Barak, Jennifer A; Kennedy, James A

2013-04-24

99

Vegetable oil thermosets reinforced by tannin-lipid formulations.  

PubMed

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

2012-09-10

100

Tannin-binding salivary proteins in three captive rhinoceros species.  

PubMed

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

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

2005-01-01

101

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

Microsoft Academic Search

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

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

2010-01-01

102

[Effect of the interaction of tannins with coexisting substances. VIII. Inhibitory effect of tannins on discoloration of natural pigments].  

PubMed

The discoloration of shikonin (1) and beta-carotene (2), occurring during storage of their ethanol solutions in the presence of oxygen in an illuminated room, was remarkably suppressed by hydrolyzable tannins, such as geraniin (4) and tannic acid JP (3) in the solution. The inhibitory effect of tannins was enhanced by the coexistence of metallic ion. The irradiation with ultraviolet lamp (254 and 365 nm) gave, at the first stage of the discoloration, two products, one of which was found to be 5,8-dihydroxy-2-(1-hydroxy-3-oxo-4-methyl-4-pentenyl)-1,4-naphthoquinone (7). The presence of hydrolyzable tannins induced higher accumulation of these two products in the solution, showing that the secondary structural transformations of these two products were strongly inhibited by these coexisting tannins. These results suggest that tannins could be efficient inhibitors of discoloration of natural pigments. PMID:7738780

Mori, K; Chou, T; Yoshida, T; Okuda, T

1995-03-01

103

Are tannins a double-edged sword in biology and health?  

Microsoft Academic Search

Vegetable tannins are water-soluble polyphenols that are present in many plant foods. They can be divided into hydrolysable and condensed tannins. Tannins are considered nutritionally undesirable because they precipitate proteins, inhibit digestive enzymes and affect the utilization of vitamins and minerals. Tannin components have also been implicated in the high levels of cheek and oesophageal cancers in certain regions of

King-Thom Chung; Cheng-I Wei; Michael G Johnson

1998-01-01

104

Costs and benefits of defense by tannins in a neotropical tree  

Microsoft Academic Search

The costs and benefits of defense by tannins were investigated for a neotropical tree, Cecropia peltata L. (Moraceae). Seedlings of equal age were grown under uniform conditions in a greenhouse for 18 months. Within a plant, leaf tannin concentrations measured in different years were highly correlated. Tannin concentrations differed substantially among individuals; plants with high tannin content had lower damage

Phyllis D. Coley

1986-01-01

105

Benzyl Benzoate Glycosides from Oligoneuron rigidum.  

PubMed

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

2012-11-01

106

Two phenolic glycosides from Curculigo orchioides Gaertn.  

PubMed

One new glycoside derivative from syringic acid and one new phenol glycoside, curculigoside E (1) and orchioside D (2), were isolated and characterized from the rootstock of Curculigo orchioides collected in the Nawalparasi District (Nepal). The structures of the new isolated compounds were elucidated by means of spectroscopic methods such as 1D, 2D NMR and MS. PMID:19285123

Dall'Acqua, Stefano; Shrestha, Bharat Babu; Comai, Stefano; Innocenti, Gabbriella; Gewali, Mohan Bikram; Jha, Pramod Kumar

2009-03-11

107

Oleanane and ursane glycosides from Schefflera octophylla.  

PubMed

Twelve triterpene glycosides were isolated from the bark of Schefflera octophylla of Vietnamese origin. Three of them were identified as asiaticoside, cauloside D and 3 alpha-hydroxyurs-12-ene-23,28-dioic acid 28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside. The structures of nine new glycosides were elucidated by chemical and spectroscopic evidence. Including the known compounds, the 12 glycosides consisted of six pairs of corresponding ursene and oleanene glycosides and all of them had the same triose moiety at the C-28 position. The names scheffurosides A-F and scheffoleosides B-F were proposed for corresponding pairs of ursene and oleanene glycosides, respectively. PMID:7765658

Maeda, C; Ohtani, K; Kasai, R; Yamasaki, K; Nguyen, M D; Nguyen, T N; Nguyen, K Q

1994-11-01

108

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

PubMed Central

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

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

2003-01-01

109

Electrochemical removal of tannins from aqueous solutions  

SciTech Connect

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

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

2000-02-01

110

Tannins from Canarium album with potent antioxidant activity.  

PubMed

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

2008-05-01

111

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))

1993-01-01

112

Rapid screening of tannase producing microbes by using natural tannin.  

PubMed

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

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

2012-06-01

113

Rapid screening of tannase producing microbes by using natural tannin  

PubMed Central

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

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

2012-01-01

114

Total tannin content in distinct Quercus robur L. galls  

Microsoft Academic Search

The total tannin contents of three different Quercus robur L. galls collected from Estonia, three reference galls, and two plants were estimated. The dry common oak gall-apples tannin content was 47.2%; in brown shiny galls - 4.2%, and in grape galls - 3.4%; in Chinese galls - 89.1%, in Turkey galls - 81.4%, and in pistacia galls - 52.4%; in

Urve Paaver; Vallo Matto; Ain Raal

2010-01-01

115

Structural features and antioxidant activity of tannin from persimmon pulp  

Microsoft Academic Search

Phenolic compounds from persimmon pulp were extracted with methanol acidified with 1% HCl, and then purified on AB-8 macroporous resin. The tannic extracts obtained were fractionated by polysulfone ultrafiltration membrane with molecular weight cutoff of 10,000Da into two fractions: low molecular weight tannin (LMWT) and high molecular weight tannin (HMWT). HPLC–MS analysis showed that gallic acid was one of the

Hai-Feng Gu; Chun-Mei Li; Yu-juan Xu; Wan-feng Hu; Mei-hong Chen; Qiong-hong Wan

2008-01-01

116

Tannins, xenobiotic metabolism and cancer chemoprevention in experimental animals  

Microsoft Academic Search

Summary  Tannins are plant polyphenolic compounds that are contained in large quantities in food and beverages (tea, red wine, nuts,etc.) consumed by humans daily. It has been shown that various tannins exert broad cancer chemoprotective activity in a number\\u000a of animal models. This review summarizes the recent literature regarding both the mechanisms involved, and the specific organ\\u000a cancer models used in

Ch. Nepka; E. Asprodini; D. Kouretas

1999-01-01

117

Thermodynamics aspect of tannin sorption on polymeric adsorbents  

Microsoft Academic Search

Hypercrosslinked polydivinylbenzene and gel type poly(styrene-co-divinylbenzene) post-crosslinked with isocyanuric acid and macroporous crosslinked poly (N-vinyl acetamide) adsorbent were prepared for adsorbing tannin from aqueous. The sorption isotherms were measured and the isosteric enthalpy was quantitatively correlated with the fractional loading for the tannin sorption onto the three polymeric adsorbents. Surface energetic heterogeneity was observed for the three adsorbents and described

Haitao Li; Yinchun Jiao; Mancai Xu; Zuoqing Shi; Binqlin He

2004-01-01

118

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

2005-01-01

119

Anaerobic treatment of natural tannin extracts in UASB reactors.  

PubMed

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

López-Fluza, J; Omil, F; Méndez, R

2003-01-01

120

Phenolic glycosides from Curculigo orchioides Gaertn.  

PubMed

Five new chlorophenolic glucosides, curculigine E (1), curculigine F (2), curculigine G (3), curculigine H (5), curculigine I (6) and one new phenolic glycoside, orcinoside H (4), together with eight known phenolic glycosides (7-14) were isolated from the Curculigo orchioides Gaertn. Their structures were established by spectroscopic techniques (IR, UV, MS, 1D and 2D NMR). The isolated phenolic glycosides were evaluated for antiosteoporotic activity against MC3T3-E1 cell line using MTT assays. Compounds 1, 2, 3, and 5 showed moderate antiosteoporotic activity with the proliferation rate of 10.1-14.1%. PMID:23353659

Wang, Zhen-Hui; Huang, Jian; Ma, Xiao-Ci; Li, Guo-Yu; Ma, Yue-Ping; Li, Ning; Wang, Jin-Hui

2013-01-23

121

A new furostanol glycoside from Tribulus terrestris.  

PubMed

Besides two known glycosides, a new furostanol glycoside was isolated from the Fruits of Tribulus terrestris L. The structure of the new furostanol glycoside was established as 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furostane-20(22)-en-12-one-3beta, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside (1) on the basis of 1D and 2D-NMR techniques, including COSY, HMBC, and HMQC correlations. PMID:20335931

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

2010-01-27

122

Antibiofilm phenylethanoid glycosides from Penstemon centranthifolius.  

PubMed

Bioassay-guided fractionation of the antibacterial ethyl acetate-ethanol (50 : 50) extract obtained from the aerial parts of Penstemon centranthifolius led to the isolation of six phenylethanoid glycosides (1-6) and eleven iridoid glycosides (7-17). Their structures were determined on the basis of spectroscopic analysis and comparison with the literature. Among them, two phenylethanoid glycosides, 4'''-O-acetylverbascoside (1) and verbascoside (2), were found to show significant inhibition of the formation of bacterial biofilms by Escherichia coli UTI89. Compound 1 showed 77% biofilm inhibition at 2.5 microg/mL, and compound 2 showed 60% inhibition at 5 microg/mL. PMID:19827017

Ye, Miao; Zhao, Yun; Norman, Vanessa L; Starks, Courtney M; Rice, Stephanie M; Goering, Matt G; O'Neil-Johnson, Mark; Eldridge, Gary R; Hu, Jin-Feng

2010-05-01

123

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

PubMed

Three new ellagitannin monomers, nilotinins M5-M7 (1-3), a dimer, nilotinin D10 (4), and a trimer, nilotinin T1 (5), together with three known dimers, hirtellin D (7) and tamarixinins B (8) and C (9), and a trimer, hirtellin T2 (6), were isolated from Tamarix nilotica dried leaves. The structures of the tannins were elucidated by intensive spectroscopic methods and chemical conversions into known tannins. The new trimer (5) is a unique macrocyclic type whose monomeric units are linked together by an isodehydrodigalloyl and two dehydrodigalloyl moieties. Additionally, dimeric and trimeric macrocyclic-type tannins isolated from T. nilotica in this study were assessed for possible cytotoxic activity against four human tumor cell lines. Tumor-selective cytotoxicities of the tested compounds were higher than those of synthetic and natural potent cytotoxic compounds, including polyphenols, and comparable with those of 5-fluorouracil and melphalan. PMID:23675651

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

2013-05-15

124

Cell membrane receptors for cardiac glycosides in the heart  

Microsoft Academic Search

Summary Cell membranes contain special binding proteins for hormones and drugs. These binding sites (“receptors”) located on the outside surface are linked to or are part of an enzyme facing the inner side of the membrane and are transducing and probably amplifying the information carried by the pharmacological agent to the cell.

E. Erdmann

1977-01-01

125

Cardiac glycoside analogs in combination with emodin for cancer therapy  

US Patent & Trademark Office Database

A method and medicine for treating leukemia or other cancer includes administering to a patient diagnosed with leukemia or other cancer a treatment regimen that includes periodic doses of a combination of emodin and digoxin.

2013-09-24

126

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

PubMed

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

2012-06-13

127

Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides.  

PubMed

[structure: see text] Leaves of the edible passion fruit plant, Passiflora edulis, contain benzylic beta-D-allopyranosides 1 and 2, representatives of a rare class of natural glycosides with D-allose as the only sugar constituent. The glycoside 1 is the first known cyanogenic glycoside containing a sugar different from D-glucose attached directly to the cyanohydrin center. Asymmetric perturbation of the (1)L(b) transition of the benzene chromophore was shown to be useful for determination of absolute configuration of the cyanohydrin center of aromatic cyanogenic glycosides. PMID:11440577

Christensen, J; Jaroszewski, J W

2001-07-12

128

A new phenolic glycoside from prunella vulgaris.  

PubMed

A new phenolic glycoside was isolated from the spikes of Prunella vulgaris. Its structure was elucidated as gentisic acid 5-O-beta-D-(6'-salicylyl)-glucopyranoside by spectroscopic evidence and chemical analysis. PMID:21800544

Gu, Xiao-jie; Li, You-bin; Mu, Jun; Zhang, Yi

2011-05-01

129

Antioxidant potential of hydroxycinnamic acid glycoside esters.  

PubMed

Hydroxycinnamic acids are natural antioxidants found in fruits, vegetables, and cereals. In this study, the antioxidant activity of various types of hydroxycinnamoyl glycoside esters that mimic the structure of polymeric carbohydrates was studied in different model systems prone to oxidation, namely, liposomes and emulsions. In addition, radical scavenging activity against the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical was tested. It was found that the esterification in the primary hydroxyl group of the glycoside resulted in the improved radical scavenging activity of both sinapoyl and feruloyl glycosides compared to conjugation to the secondary hydroxyl group. Increased activity was also observed, particularly in the case of feruloyl glucosides in inhibiting the oxidation of liposomes emulsions. The results showed that sinapic and ferulic acid glycoside esters were as effective or more efficient antioxidants than their free forms. In conclusion, the strength of their antioxidant effect depends on the nature of conjugation. PMID:18494493

Kylli, Petri; Nousiainen, Paula; Biely, Peter; Sipilä, Jussi; Tenkanen, Maija; Heinonen, Marina

2008-05-22

130

Engineering of cellobiose phosphorylase for glycoside synthesis.  

PubMed

Disaccharide phosphorylases are increasingly applied for glycoside synthesis, since they are very regiospecific and use cheap and easy to obtain donor substrates. A promising enzyme is cellobiose phosphorylase (CP), which was discovered more than 50 years ago. Many other bacterial CP enzymes have since then been characterized, cloned and applied for glycoside synthesis. However, the general application of wild-type CP for glycoside synthesis is hampered by its relatively narrow substrate specificity. Recently we have taken some successful efforts to broaden the substrate specificity of Cellulomonas uda CP by directed evolution and protein engineering. This review will give an overview of the obtained results and address the applicability of the engineered CP enzymes for glycoside synthesis. CP is the first example of an extensively engineered disaccharide phosphorylase, and may provide valuable information for protein engineering of other phosphorylase enzymes. PMID:21803082

de Groeve, Manu R M; Desmet, Tom; Soetaert, Wim

2011-07-20

131

Three new glycosides from Hylocereus undatus.  

PubMed

Three new glycosides, undatusides A-C (1-3), and 11 known compounds (4-14) were isolated from the flowers of Hylocereus undatus. Their structures were elucidated on the basis of spectroscopic data and chemical method. PMID:21751841

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

2011-08-01

132

Two flavonol glycosides from Vancouveria hexandra.  

PubMed

In addition to two known glycosides, ikarisoside F and epimedin A, two new glycosides of a flavonol with a gamma, gamma-dimethylallyl group were isolated from the underground and the aerial parts of Vancouveria hexandra. The structures were determined to be des-O-methylanhydroicaritin 3,7-diglucoside and anhydroicaritin 3-glucosyl (1----3)rhamnoside-7-glucoside by means of spectral analysis. PMID:1367883

Mizuno, M; Kanie, Y; Iinuma, M; Tanaka, T; Lang, F A

1992-01-01

133

Investigations of Mustard Oil Glycosides. IV. Phenyl-Thiourethane-d-Glycoside.  

National Technical Information Service (NTIS)

Particular interest is offered by the decomposition to which phenyl-thio-urethane-d-glycoside is subjected by the influence of water and acids. It assumes here, as it does in respect to its stability, a median position between thiorethane-glycosides synth...

W. Schneider D. Clibben

1968-01-01

134

Genetic Manipulation of Condensed Tannins in Higher Plants1  

PubMed Central

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

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

1998-01-01

135

Cycloartane Glycosides from Sutherlandia frutescens  

PubMed Central

Four new cycloartane glycosides, sutherlandiosides A–D (1–4), were isolated from the South African folk medicine Sutherlandia frutescens and their structures established by spectroscopic methods and X-ray crystallography as 1S,3R,24S,25-tetrahydroxy-7S,10S-epoxy-9,10-seco-9,19-cyclolanost-9(11)-ene 25-O-?-d-glucopyranoside (1), 3R,7S,24S,25-tetrahydroxycycloartan-1-one 25-O-?-d-glucopyranoside (2), 3R,24S,25-trihydroxycycloartane-1,11-dione 25-O-?-d-glucopyranoside (3), and 7S,24S,25-trihydroxycycloart-2-en-1-one 25-O-?-d-glucoyranoside (4). Compound 1 represents the first secocycloartane skeleton possessing a 7,10-oxygen bridge. Compounds 2–4 are also the first examples of naturally occurring cycloartanes with a C-1 ketone functionality. Biosynthetic considerations and chemical evidence suggest that the presence of the C-1 ketone in 2 may facilitate the ring opening of the strained cyclopropane system.

Fu, Xiang; Li, Xing-Cong; Smillie, Troy J.; Carvalho, Paulo; Mabusela, Wilfred; Syce, James; Johnson, Quinton; Folk, William; Avery, Mitchell A.; Khan, Ikhlas A.

2012-01-01

136

WALNUT AND PISTACHIO HYDROLYZABLE TANNINS: COMPARISON OF CHEMICAL STRUCTURES AND AFLATOXIN INHIBITING PROPERTIES  

Technology Transfer Automated Retrieval System (TEKTRAN)

Pistachio and walnut fruit tissues contain hydrolyzable tannins that inhibit the growth and aflatoxin production of Aspergillus flavus. Walnut hydrolyzable tannins, located in the kernel seed coat, are composed of glucose esterified with gallic acid and hexahydroxydiphenic acid, which spontaneously...

137

On the molluscicidal activity of tannin containing plants.  

PubMed

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

1983-06-01

138

Tannins characterisation in new and historic vegetable tanned leathers fibres by spot tests  

Microsoft Academic Search

This paper describes the adaptation and evaluation of three chemical tests for tannins characterisation in vegetable tanned leathers. Tests were performed on fibres of new leathers tanned with different known vegetable tannins and historic leathers. Rhodanine test, nitrous acid test and acid butanol test, developed to identify, respectively, gallotannins, ellagitannins and condensed tannins, are described. Ferric test and vanillin test,

Lina Falcão; Maria Eduarda M. Araújo

2011-01-01

139

Adsorption removal of boron in aqueous solutions by amine-modified tannin gel  

Microsoft Academic Search

A tannin gel (TG) synthesized from condensed tannin molecules has a remarkable ability to adsorb various metal ions in aqueous solutions. In the present study, the adsorption removal of boron in solutions at various pHs and temperatures has been examined using the TG and the amine-modified tannin gel (ATG) prepared with ammonia treatment of the TG. The adsorption amounts of

Shintaro Morisada; Tetsuzen Rin; Takeshi Ogata; Yoen-Ho Kim; Yoshio Nakano

2011-01-01

140

Evaluation of tannin biopolymer as a coagulant aid for coagulation of colloidal particles  

Microsoft Academic Search

Tannin is a biodegradable anionic polymer. Tannin as a coagulant aid can be a potential substitute for synthetic anionic polyelectrolytes in water treatment because it can: (1) avoid the health effects from residual aluminum(III) and synthetic polymers, and (2) produce biodegradable sludge. In the present work, the coagulant characteristics of the tannin obtained from valonia were examined and whether or

Mahmut Özacar; ?. Ayhan ?engil

2003-01-01

141

Reduction of persimmon astringency by complex formation between pectin and tannins  

Microsoft Academic Search

The effects of interactions between soluble pectin and soluble tannins on the astringency of persimmon fruit were studied. The astringency of both fresh juice and a solution of tannins purified from persimmon fruit was significantly reduced by the addition of soluble pectin. The change was probably due to complex formation between the pectin and soluble tannins. In intact fruit, a

Satoshi Taira; Miki Ono; Naoko Matsumoto

1997-01-01

142

Stimulatory effects of tannins and cholic acid on tryptic hydrolysis of proteins: Ecological implications  

Microsoft Academic Search

The biochemical basis for considering tannins as digestion inhibitors has been reexamined. Both stimulatory and inhibitory effects of tannins on tryptic hydrolysis are reported. We show how stimulation may result from tannin-induced structural changes in the substrate protein, effectively denaturing it. The surfactant and bile constituent cholic acid also produced similar stimulatory effects. These results have considerable implications for normal

Simon Mole; Peter G. Waterman

1985-01-01

143

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

Microsoft Academic Search

Summary In alpine ecosystems, tannin-rich-litter decomposi- tion occurs mainly under snow. With global change, variations in snowfall might affect soil temperature and microbial diversity with biogeochemical con- sequences 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

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

2008-01-01

144

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

PubMed

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

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

2012-04-20

145

Condensed Tannin Concentration of Rhizomatous and Nonrhizomatous Birdsfoot Trefoil in Grazed Mixtures and Monocultures  

Microsoft Academic Search

in the lower digestive tract (Barry and Manley, 1986), thereby facilitating ruminal escape protein utilization Condensed tannins in forage legumes can be beneficial or detrimen- (Waghorn et al., 1999). tal to ruminant livestock performance, depending on concentration. The objective of this research was to determine condensed tannin Concentrations of condensed tannins considered to concentration in birdsfoot trefoil (Lotus corniculatus L.)

L. Wen; C. A. Roberts; J. E. Williams; R. L. Kallenbach; P. R. Beuselinck; R. L. McGraw

2003-01-01

146

New steroidal glycosides from rhizomes of Clintonia udensis.  

PubMed

A total of 10 steroidal glycosides, together with three new spirostanol glycosides (6-8), a new furostanol glycoside (9), and a new cholestane glycoside (10), were isolated from the rhizomes of Clintonia udensis (Liliaceae). The structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including 2-D nuclear magnetic resonance (NMR) data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. The isolated glycosides were evaluated for their cytotoxic activity against HL-60 leukemia cells. Spirostanol glycosides 1 and 2, and furostanol glycoside 4 showed cytotoxic activity with IC(50) values of 3.2+/-0.02, 2.2+/-0.12, and 2.2+/-0.06 microg/ml, respectively. Neither the spirostanol and furostanol saponins with a hydroxy group at C-1 (6 and 9) and C-12 (7 and 8) nor cholestane glycosides (5 and 10) exhibited apparent cytotoxic activity at a sample concentration of 10 microg/ml. PMID:18603808

Matsuo, Yukiko; Watanabe, Kazuki; Mimaki, Yoshihiro

2008-07-07

147

Phenylethanoid and iridoid glycosides from Veronica persica.  

PubMed

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

2002-06-01

148

?-Type Glycosidic Bond Formation by Palladium-Catalyzed Decarboxylative Allylation.  

PubMed

Decarboxylative allylation of glycals: A ?-type glycosidic bond has been constructed in high regio- and stereoselectivity by means of a palladium-catalyzed decarboxylative O-glycosylation. Various kinds of glycals with different protecting groups have been examined for this reaction to afford a diverse set of glycosylated products, including phenolic O-glycosides, thiophenolic S-glycoside, aliphatic O-glycosides, and disaccharides with excellent ?-selectivity and reasonable to excellent yields. PMID:24108596

Xiang, Shaohua; Lu, Zhiqiang; He, Jingxi; Le Maihoang, Kim; Zeng, Jing; Liu, Xue-Wei

2013-09-17

149

Tannins and related polyphenols of euphorbiaceous plants. XI. Three new hydrolyzable tannins and a polyphenol glucoside from Euphorbia humifusa.  

PubMed

Three new hydrolyzable tannins, euphormisins M1, M2, and M3, were isolated from Euphorbia humifusa WILLD., and respectively characterized as 1,3,6-tri-O-galloyl-4-O- brevifolincarboxyl-beta-D-glucose (19), an oxidative metabolite (23) of geraniin, and 1,3,6-tri-O-galloyl-alpha-D-glucose (18), by spectroscopic and chemical methods. A new ellagic acid glucoside (16) and fifteen known tannins, including geraniin (8) and four dimers [euphorbins A (13), B (14), excoecarianin (15) and eumaculin A (12)], were also isolated. PMID:7954930

Yoshida, T; Amakura, Y; Liu, Y Z; Okuda, T

1994-09-01

150

Novel efficient routes to indoxyl glycosides for monitoring glycosidase activities.  

PubMed

A new efficient synthesis for broad access to indoxyl glycosides was developed. Indoxylic acid allyl ester linked to a sugar structure served as the key intermediate in this route. Selective ester cleavage and mild decarboxylation led to the corresponding indoxyl glycosides in good yields. This synthesis was applied for preparation of indoxyl glycosides of fucose, sialic acid, and 6'-sialyl lactose. PMID:23829284

Böttcher, Stephan; Hederos, Markus; Champion, Elise; Dékány, Gyula; Thiem, Joachim

2013-07-05

151

Bioactive phenylpropanoid glycosides from Tabebuia avellanedae.  

PubMed

Three novel phenylpropanoid glycosides 2, 5, 6 were isolated from water extract of Tabebuia avellanedae, together with three known phenylpropanoid glycosides 1, 3, 4. All compounds were identified on the basis of spectroscopic analysis and chemical methods and, for known compounds, by comparison with published data. All isolated compounds showed strong antioxidant activity in the DPPH assay, and compound 5 give the highest antioxidant activity among all compounds, with an IC?? of 0.12 µM. All compounds exhibited moderate inhibitory effect on cytochrome CYP3A4 enzyme. PMID:23797703

Suo, Maorong; Ohta, Tomihisa; Takano, Fumihide; Jin, Shouwen

2013-06-24

152

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.

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

2008-01-01

153

Accumulation of hydrolyzable tannins by Aleurites fordii callus culture.  

PubMed

A callus culture of Aleurites fordii Hemsley (Euphorbiaceae) producing five galloylglucoses and an ellagitannin, geraniin, was established. The production of pentagalloylglucose was remarkably enhanced under light irradiation compared with that in the dark. Cell growth and tannin production were also greatly affected by changing the concentrations and composition of nitrogen sources. PMID:12494350

Taniguchi, Shoko; Uechi, Kyoko; Kato, Reiko; Ito, Hideyuki; Hatano, Tsutomu; Yazaki, Kazufumi; Yoshida, Takashi

2002-12-01

154

Manipulation of tannins in oaks by galling cynipids  

Microsoft Academic Search

We measured the protein precipitation capacity of tannins in the tissues of Quercus crispula and Quercus serrata galls induced by a cynipid (Trigonaspis sp.) to examine the nutrition hypothesis on gall induction. The protein precipitation capacity was significantly lower in\\u000a the nutritive tissues of galls, on which the cynipids feed, than in ungalled sound leaves and in the outer gall

Noriyuki Ikai; Naoki Hijii

2007-01-01

155

Dietary circumvention of acorn tannins by blue jays  

Microsoft Academic Search

Blue jays consume large quantities of acorns to fuel energy-demanding caching flights in the fall. Yet blue jays possess no known physiological adaptation to counter the negative effects of a high tannin diet on protein digestion. Dietary experiments were conducted to determine if blue jays could subsist on an acorn-only diet, and if they could not, to determine whether supplements

W. Carter Johnson; Libby Thomas; Curtis S. Adkisson

1993-01-01

156

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

PubMed

• Climate change could increase the frequency with which plants experience abiotic stresses, leading to changes in their metabolic pathways. These stresses may induce the production of compounds that are structurally and biologically different from constitutive compounds. • We studied how warming and altered precipitation affected the composition, structure, and biological reactivity of leaf litter tannins in Acer rubrum at the Boston-Area Climate Experiment, in Massachusetts, USA. • Warmer and drier climatic conditions led to higher concentrations of protective compounds, including flavonoids and cutin. The abundance and structure of leaf tannins also responded consistently to climatic treatments. Drought and warming in combination doubled the concentration of total tannins, which reached 30% of leaf-litter DW. This treatment also produced condensed tannins with lower polymerization and a greater proportion of procyanidin units, which in turn reduced sequestration of tannins by litter fiber. Furthermore, because of the structural flexibility of these tannins, litter from this treatment exhibited five times more enzyme (?-glucosidase) complexation capacity on a per-weight basis. Warmer and wetter conditions decreased the amount of foliar condensed tannins. • Our finding that warming and drought result in the production of highly reactive tannins is novel, and highly relevant to climate change research as these tannins, by immobilizing microbial enzymes, could slow litter decomposition and thus carbon and nutrient cycling in a warmer, drier world. PMID:21371041

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

2011-03-04

157

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

PubMed

By inhibiting soil enzymes, tannins play an important role in soil carbon (C) and nitrogen (N) mineralization. The role of tannin chemistry in this inhibitory process, in conjunction with enzyme classes and isoforms, is less well understood. Here, we compared the inhibition efficiencies of mixed tannins (MTs, mostly limited to angiosperms) and condensed tannins (CTs, produced mostly by gymnosperms) against the potential activity of ?-glucosidase (BG), N-acetyl-glucosaminidase (NAG), and peroxidase in two soils that differed in their vegetation histories. Compared with CTs, MTs exhibited 50% more inhibition of almond (Prunus dulcis) BG activity and greater inhibition of the potential NAG activity in the gymnosperm-acclimatized soils. CTs exhibited lower BG inhibition in the angiosperm-acclimated soils, whereas both types of tannins exhibited higher peroxidase inhibition in the angiosperm soils than in gymnosperm soils. At all of the tested tannin concentrations, irrespective of the tannin type and site history, the potential peroxidase activity was inhibited two-fold more than the hydrolase activity and was positively associated with the redox-buffering efficiency of tannins. Our finding that the inhibitory activities and mechanisms of MTs and CTs are dependent on the vegetative history and enzyme class is novel and furthers our understanding of the role of tannins and soil isoenzymes in decomposition. PMID:23025512

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

2012-10-01

158

Fast-Setting Phenolic and Tannin-Based 'Honeymoon' Adhesive Systems for Exterior Grade Finger-Joints.  

National Technical Information Service (NTIS)

This study describes the development of alternative tannin-based fast-setting adhesives not containing m-aminophenol as well as of phenolic/phenolic, tannin/tannin and tannin/phenolic adhesive systems which can be used for the same purpose.

A. Pizzi D. D. T. Rossouw W. Knueffel M. Singmin

1980-01-01

159

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

PubMed

We examined how tannin structure influences reactivity in tannin assays and carbon and nitrogen mineralization. Condensed tannins from the foliage of ten tree and shrub species and from pecan shells (Carya illinoensis) had different proportions of: (a) epicatechin (cis) and catechin (trans) isomers, (b) procyanidin (PC) and prodelphinidin (PD) monomers, and (c) different chain lengths. The response of each tannin to several widely used tannin assays was determined. Although there was some variation in response to proanthocyanidin (butanol/HCl) and Folin Ciocalteu assays, we did not deduce any predictable relationship between tannin structure and response to either assay. There was little variation in protein precipitation among the different tannins. To assess biological activity, six of the tannins were incubated with forest humus for 22 days. We determined that, while PC-based tannins remained at least partly extractable for the duration of the incubation, tannins with a high proportion of PD subunits rapidly became unextractable from soil. There was a positive correlation between net nitrogen mineralization and cis chemical structure. Carbon mineralization was enhanced initially by the addition of tannins to humus, but after 22 days, a negative correlation between the proportion of cis subunits and respiration was determined. Overall, we were not able to demonstrate consistent effects of structure on either microbial mineralization or reactivity to chemical assays; such relationships remain elusive. PMID:21340461

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

2011-02-22

160

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

NASA Astrophysics Data System (ADS)

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

Wang, Bo; Chen, Jin

2008-11-01

161

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

PubMed

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

Ward, David; Young, Truman P

2002-05-01

162

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

NASA Astrophysics Data System (ADS)

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

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

163

Phenotypic and phylogenetic characterization of ruminal tannin-tolerant bacteria.  

PubMed

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

1998-10-01

164

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.

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

1998-01-01

165

Bacopasaponin DA pseudojujubogenin glycoside from Bacopa monniera  

Microsoft Academic Search

A new dammarane-type pseudojujubogenin glycoside, bacopasaponin D, has been isolated from the reputed Indian medicinal plant Bacopa monniera and defined as 3-O-[?-l-arabinofuranosyl(I?2)?-d-glucopyranosyl]pseudojujubogenin by spectroscopic methods and some chemical transformations. The 13C signals of the saponin were assigned by DEPT, 1H?1H COSY and HSQC techniques.

Saraswati Garai; Shashi B. Mahato; Kazuhiro Ohtani; Kazuo Yamasaki

1996-01-01

166

Chlorination Diversifies Cimicifuga racemosa Triterpene Glycosides  

PubMed Central

Extracts from roots and rhizomes of black cohosh (Cimicifuga racemosa) are widely used as dietary supplements to alleviate menopausal symptoms. State-of-the-art QC measures involve phytochemical fingerprinting of the triterpene glycosides for species identification and chemical standardization by HPLC. In the course of developing materials and methods for standardization procedures, the major C. racemosa triterpene glycoside (1) was isolated ans initially thought to be cimicifugoside (2). Detailed HR-LC-MS and 1/2D NMR analysis of 1 and 2 unambiguously revealed that 1 is its chlorine-containing derivative of 2, namely 25-chlorodeoxycimigenol-3-O-?-D-xyloside. Accordingly, HPLC profiles of black cohosh preparations require revision of the assignments of the chlorinated (1) and non-chlorinated (2) pair. Besides explaining the substantial shift in polarity (?tR[RP-18] ca 20 min), 25-deoxychlorination opens a new pathway of structural diversification in triterpene glycosides chemistry. As chemical conversion of 2 into 1 could be demonstrated, deoxychlorination may be interpreted as artifact formation. Simultaneously, however, it is a potentially significant pathway for the gastric in vivo conversion (“nature's pro drug”) of the relatively polar triterpene glycosides into significantly less polar chlorinated derivatives with altered pharmacological properties.

Chen, Shao-Nong; Lankin, David C.; Nikolic, Dejan; Fabricant, Daniel S.; Lu, Zhi-Zhen; Ramirez, Benjamin; van Breemen, Richard B.; Fong, Harry H. S.; Farnsworth, Norman R.; Pauli, Guido F.

2008-01-01

167

A new withanolide glycoside from physalis peruviana  

PubMed

A new withanolide glycoside, 17beta-hydroxy-14, 20-epoxy-1-oxo-[22R]-3beta-[O-beta-D-glucopyranosyl]-witha-5, 24-dienolide (1), has been isolated from the whole plant of Physalis peruviana. Its identity was determined using a combination of spectroscopic data including 2D NMR techniques and chemical transformations. PMID:10096867

Ahmad; Malik; Afza; Yasmin

1999-03-01

168

Two new triterpenoid glycosides from Curculigo orchioides.  

PubMed

Two new cycloartane triterpenoid glycosides, named curculigosaponin N and curculigosaponin O, were isolated from rhizomes of Curculigo orchioides Gaertn. Their structures were elucidated on the basis of comprehensive spectroscopic analysis including IR, MS, 1D, and 2D NMR (HSQC and HMBC). PMID:22316001

Zuo, Ai-Xue; Shen, Yong; Jiang, Zhi-Yong; Zhang, Xue-Mei; Zhou, Jun; Lü, Jun; Chen, Ji-Jun

2012-02-09

169

Antiproliferative steroidal glycosides from Digitalis ciliata.  

PubMed

Two new compounds, a furostanol glycoside (1) and a pregnane glycoside (4), along with eight known compounds, belonging to the classes of spirostane (2,3), pregnane (5-7) and cardenolide (8-10) glycosides, were isolated from the seeds of Digitalis ciliata. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. For the first time pregnane glycosides of the diginigenin series have been isolated from D. ciliata. The cytotoxic effects of compounds 1-10 on cell viability of several cancer cell lines, namely human breast cancer (MCF-7), human glioblastoma (T98G), human lung adenocarcinoma (A549), human colon carcinoma (HT-29), and human prostate cancer (PC-3) cell lines were evaluated. Compounds 1, 4, 7 and 8 showed antiproliferative effects against MCF-7, HT-29 and A549 cancer cells with IC?? values ranging from 8.3 to 20 ?M. The effects of compounds 1-10 on cell proliferation were evaluated on these three cancer cell lines by cell cycle analysis of DNA content using flow cytometry. Compounds 7, 8 and 10 induced significant changes in G?/M cell cycle phase of all analyzed cells. The obtained results indicate that compounds 7, 8 and 10 are cytostatic compounds effective in reducing cell proliferation by inducing accumulation of the cells in the G?/M phase of the cell cycle. PMID:22245088

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

2012-01-08

170

Chlorination diversifies Cimicifuga racemosa triterpene glycosides.  

PubMed

Extracts from the roots and rhizomes of black cohosh (Cimicifuga racemosa) are widely used as dietary supplements to alleviate menopausal symptoms. State-of-the-art quality control measures involve phytochemical fingerprinting of the triterpene glycosides for species identification and chemical standardization by HPLC. In the course of developing materials and methods for standardization procedures, the major C. racemosa triterpene glycoside (1) was isolated and initially thought to be cimicifugoside (2). Detailed HR-LC-MS and 1D and 2D NMR analysis of 1 and 2 unambiguously revealed that 1 is the chlorine-containing derivative of 2, namely, 25-chlorodeoxycimigenol-3-O-beta-d-xyloside. Accordingly, HPLC profiles of black cohosh preparations require revision of the assignments of the chlorinated (1) and nonchlorinated (2) pair. Besides explaining the substantial shift in polarity (DeltatR[RP-18] ca. 20 min), 25-deoxychlorination opens a new pathway of structural diversification in triterpene glycoside chemistry. As chemical conversion of 2 into 1 could be demonstrated, deoxychlorination may be interpreted as artifact formation. Simultaneously, however, it is a potentially significant pathway for the gastric in vivo conversion ("nature's prodrug") of the relatively polar triterpene glycosides into significantly less polar chlorinated derivatives with altered pharmacological properties. PMID:17555351

Chen, Shao-Nong; Lankin, David C; Nikolic, Dejan; Fabricant, Daniel S; Lu, Zhi-Zhen; Ramirez, Benjamin; van Breemen, Richard B; Fong, Harry H S; Farnsworth, Norman R; Pauli, Guido F

2007-06-08

171

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

SciTech Connect

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

Asquith, T.N.

1985-01-01

172

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.

2012-09-01

173

Phenotypic and Phylogenetic Characterization of Ruminal Tannin-Tolerant Bacteria  

Microsoft Academic Search

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), Hondu- ran and Colombian goats (Capra hircus), white-tail deer (Odocoileus virginianus) from upstate New York, and Rocky

KAREN E. NELSON; MICHAEL L. THONNEY; TINA K. WOOLSTON; STEPHEN H. ZINDER; ALICE N. PELL

1998-01-01

174

Mechanism of hexavalent chromium adsorption by persimmon tannin gel  

Microsoft Academic Search

Mechanism of chromium adsorption by the persimmon tannin (PT) gel was examined. The PT gel can adsorb Cr highly effectively from aqueous solutions containing Cr(VI), while it adsorbed far smaller amounts of Cr from the solution containing Cr(III). The maximum Cr adsorption from the Cr(VI) solution occurred at pH 3. The Cr adsorption from the Cr(VI) solution by the PT

Akira Nakajima; Yoshinari Baba

2004-01-01

175

Rheology of tannin-added phenol formaldehyde adhesives for plywood  

Microsoft Academic Search

2   adhesive consumption in double glue line, which is significantly lower than the aprox. 400?g\\/m2 allowed by commercially available phenol-formaldehyde adhesives. The adhesives prepared with resols containing 36% reactive\\u000a solids, the tannins representing aprox. 20%, has permitted the preparation of eucalyptus plywood boards exceeding the requirements\\u000a of the European norm for exterior grade plywood.

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

2002-01-01

176

A novel glycoside from Acanthus hirsutus (Acanthaceae).  

PubMed

A novel glycoside, hirsutusoide (1), characterized as 2-(o-hydroxyphenyl)-2-hydroxyethenyl-O-beta-glucopyranoside, was isolated from the endemic Acanthus hirsutus Boiss. In addition to compound 1, three known glycosides, luteolin-7-O-beta-D-glucuronide (2), beta-sitosterol-3-O-beta-D-glucopyranoside (3) and (2R)-2-O-beta-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (4), were also isolated. Compound 2 was the first report from this genus. Antimicrobial and antioxidant activity of the extracts and the novel compound were investigated by determining MIC (microg/mL) and IC50 (microg/mL) values, respectively. PMID:20433073

Capanlar, Seval; Böke, Nazli; Ya?a, Ihsan; Kirmizigül, Süheyla

2010-04-01

177

?-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.

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

2013-01-01

178

Antioxidant phenylpropanoid glycosides from Smilax bracteata.  

PubMed

From the ethanolic extract of Smilax bracteata, six phenylpropanoid glycosides, smilasides G-L (1-6), along with four known phenylpropanoid compounds, helonioside A, helonioside B, smilaside E, and (1-p-O-coumaroyl-6-O-feruroyl)-beta-d-fructofuranosyl-alpha-d-glucopyranoside, and fourteen known phenolic compounds were isolated. Their structures were elucidated on the basis of spectroscopic analyses. Moreover, 1-6 exhibited moderate scavenging activities against DPPH radicals. PMID:18329678

Zhang, Lijie; Liao, Chia-Ching; Huang, Hui-Chi; Shen, Ya-Ching; Yang, Li-Ming; Kuo, Yao-Haur

2008-03-10

179

Resin Glycosides from the Morning Glory Family  

Microsoft Academic Search

\\u000a Resin glycosides are part of a very extensive family of secondary metabolites known as glycolipids or lipo-oligosaccharides\\u000a and are constituents of complex resins (glycoresins) (1) unique to the morning glory family, Convolvulaceae (2). These active\\u000a principles are responsible for the drastic purgative action of all the important Convolvulaceous species used in traditional\\u000a medicine throughout the world since ancient times. Several

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

2010-01-01

180

Flavonol and anthraquinone glycosides from Rhamnus formosana.  

PubMed

Two new flavonol triglycosides, and a new anthraquinone glycoside, have been isolated from the roots of Rhamnus formosana. These compounds have been characterized as rhamnazin 3-O-[alpha-L-rhamopyranosyl(1----4)-alpha-L-rhamnopyranosyl(1----6 )]-beta-D-galactopyranoside (rhamnazin 3-isorhamninoside), rhamnocitrin 3-O-isorhamninoside and 1,6,8-trihydroxy-3-methylanthraquinone 1-O-rhamnosyl(1----2)glucoside, respectively. PMID:1367798

Lin, C N; Chung, M I; Gan, K H; Lu, C M

1991-01-01

181

Physiological roles of plant glycoside hydrolases  

Microsoft Academic Search

The functions of plant glycoside hydrolases and transglycosidases have been studied using different biochemical and molecular\\u000a genetic approaches. These enzymes are involved in the metabolism of various carbohydrates containing compounds present in\\u000a the plant tissues. The structural and functional diversity of the carbohydrates implies a vast spectrum of enzymes involved\\u000a in their metabolism. Complete genome sequence of Arabidopsis and rice

Zoran Minic

2008-01-01

182

Bioprospecting metagenomics for new glycoside hydrolases.  

PubMed

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. The aim of this chapter is to describe strategies, based on metagenomic approaches, for the discovery of glycoside hydrolases (GHases) from microbial biomass decay communities, especially those from unknown or never-been-cultivated microorganisms. PMID:22843397

Gilbert, Jack; Li, Luen-Luen; Taghavi, Safiyh; McCorkle, Sean M; Tringe, Susannah; van der Lelie, Daniel

2012-01-01

183

Laccase-mediated oxidation of natural glycosides  

Microsoft Academic Search

Regioselective oxidations of the primary OH's of natural glycosides (thiocolchicoside, colchicoside, amygdalin, asiaticoside, ginsenoside RE) have been performed on a preparative scale by exploiting the laccase–2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) methodology. The influence of water-miscible organic cosolvents on the stability and activity of a laccase from Trametes pubescens has been investigated. The enzyme has been covalently linked to Eupergit C250L and its performances

Lara Baratto; Andrea Candido; Mattia Marzorati; Francesca Sagui; Sergio Riva; Bruno Danieli

2006-01-01

184

Cardiac amyloidosis  

MedlinePLUS

... Primary cardiac amyloidosis - AL type; Secondary cardiac amyloidosis - AA type; Stiff heart syndrome; Senile amyloidosis ... arrhythmias and conduction disturbances (heart block). Secondary amyloidosis (AA type) rarely affects the heart. However, a form ...

185

Perspectives for the industrial enzymatic production of glycosides.  

PubMed

Glycosides are of commercial interest for industry in general and specifically for the pharmaceutical and food industry. Currently chemical preparation of glycosides will not meet EC food regulations, and therefore chemical preparation of glycosides is not applicable in the food industry. Thus, enzyme-catalyzed reactions are a good alternative. However, until now the low yields obtained by enzymatic methods prevent the production of glycosides on a commercial scale. Therefore, high yields should be established by a combination of optimum reaction conditions and continuous removal of the product. Unfortunately, a bioreactor for the commercial scale production of glycosides is not available. The aim of this article is to discuss the literature with respect to enzymatic production of glycosides and the design of an industrially viable bioreactor system. PMID:14524698

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

186

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

Microsoft Academic Search

BACKGROUND: Previous studies suggested that dietary tannin ingestion may induce changes in mouse salivary proteins in addition to the primarily studied proline-rich proteins (PRPs). The aim of the present study was to determine the protein expression changes induced by condensed tannin intake on the fraction of mouse whole salivary proteins that are unable to form insoluble tannin-protein complexes. Two-dimensional polyacrylamide

Elsa Lamy; Gonçalo Graça; Gonçalo da Costa; Catarina Franco; Fernando Capela e Silva; Elvira Sales Baptista; Ana Varela Coelho

2010-01-01

187

Activity of tannins from Stryphnodendron adstringens on Cryptococcus neoformans: effects on growth, capsule size and pigmentation  

Microsoft Academic Search

BACKGROUND: Stryphnodendron adstringens (Mart.) Coville, Leguminosae, also known in Brazil as barbatimão, is rich in tannins and many flavan-3-ols and proanthocyanidins such as prodelphinidins and prorobinetinidins. Previous studies have demonstrated several pharmacological properties of tannins from barbatimão, including anti-candidal activity. METHODS: The antifungal activity of proanthocyanidin polymeric tannins from Stryphnodendron adstringens (subfraction F2.4) was evaluated against three strains of Cryptococcus

Kelly Ishida; Sonia Rozental; João Carlos Palazzo de Mello; Celso Vataru Nakamura

2009-01-01

188

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

Microsoft Academic Search

In order to reduce pollution caused by traditional non-biodegradable plastic films, renewable raw materials from plants and wastes of meat industries have been employed in this work. A hydrolysable chestnut-tree tannin was used for gelatin modification. Films of gelatin and gelatin–tannin were obtained by casting at room conditions. Transition temperatures of both gelatin and gelatin–tannin systems were determined by differential

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

2010-01-01

189

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.

2001-01-01

190

Adsorption mechanism of hexavalent chromium by redox within condensed-tannin gel  

Microsoft Academic Search

We have proposed a new recovery system of hexavalent chromium Cr(VI) that is of great toxicity utilizing condensed-tannin gels derived from a natural polymer with many polyhydroxyphenyl groups. The adsorption mechanism of Cr(VI) to the tannin molecules was clarified. The adsorption mechanism consists of four reaction steps; the esterification of chromate with tannin molecules, the reduction of Cr(VI) to trivalent

Yoshio Nakano; Kenji Takeshita; Toshiro Tsutsumi

2001-01-01

191

Salivary tannin-binding proteins in root vole ( Microtus oeconomus Pallas)  

Microsoft Academic Search

We demonstrated that the root vole (Microtus oeconomus Pallas) produces salivary tannin-binding proteins. The ability of the proteins to bind tannins was demonstrated electrophoretically. It is likely that the proteins are proline-rich, based on their staining characteristics. Production of these proteins was not altered by incorporation of 0.1% of birch tannin or 10% birch bark powder to the diets of

Marja-Riitta Juntheikki; Riitta Julkunen-Tiitto; Ann E. Hagerman

1996-01-01

192

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.

2010-05-01

193

Resin glycosides from the leaves and stems of Ipomoea digitata  

Microsoft Academic Search

Alkaline hydrolysis of the ether-soluble resin glycoside (jalapin) fraction of the leaves and stems of Ipomoea digitata L. (Convolvulaceae) gave six organic acids, isobutyric, (S)-2-methylbutyric, tiglic, n-decanoic, n-dodecanoic, and cinnamic acids, and two glycosidic acids, quamoclinic acid A and operculinic acid A. Further, a new genuine\\u000a resin glycoside, named digitatajalapin I, was isolated from the jalapin fraction, along with three

Masateru Ono; Hitoshi Fukuda; Hiroko Murata; Kazumoto Miyahara

2009-01-01

194

A new flavonoid glycoside from the leaf of Cephalotaxus koreana  

Microsoft Academic Search

A new flavone glycoside, apigenin 5-O-??l-rhamnopyranosyl-(1?3)-?-d-glucopyranoside (1), along with four known flavonol glycosides (2–5), were isolated from the leaf of Cephalotaxus koreana. The new glycoside 1 showed inhibitory activity in superoxide radical scavenging assay with IC50 value of 13.0 ?M, while it showed weak activity in 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging assay. Compounds 2?5 exhibited antioxidant activity in scavenging DPPH and

KiHwan Bae; WenYi Jin; Phuong Thien Thuong; Byung Sun Min; MinKyun Na; Young Mi Lee; Sam Sik Kang

2007-01-01

195

Steroidal glycosides from the aerial parts of Polianthes tuberosa.  

PubMed

A chemical investigation of the aerial parts of Polianthes tuberosa resulted in the isolation of a new bisdesmosidic cholestane glycoside (1) and three new spirostanol saponins (2-4), along with a known cholestane glycoside. The structures of new glycosides were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity on HL-60 human promyelocytic leukemia cells. PMID:11087596

Mimaki, Y; Yokosuka, A; Sashida, Y

2000-11-01

196

Glycosides from the Aerial Parts of Patrinia villosa.  

PubMed

An investigation of the Korean medicinal plant Patrinia villosa (THUNB.) JUSS. (Valerianaceae) led to the isolation of two new flavonoid glycosides, patrivilosides 1 (1) and 2 (2), a new iridoid glycoside, patrinovalerosidate (3), and two new saponins, patrinovilosides A (4) and B (5), along with six known compounds including three flavonoid glycosides and three iridoid glycosides. The structures of the new compounds were elucidated based on analysis of their one dimensional (1D)- and 2D-NMR spectra along with their mass spectrometric data and the results of acid hydrolysis. PMID:23800854

Lee, Joo Young; Kim, Ju Sun; Kim, Yeong Shik; Kang, Sam Sik

2013-06-21

197

Synthesis and Characterization of Glycoside-Based Trisiloxane Surfactant  

Microsoft Academic Search

The synthesis of glycoside-based trisiloxane surfactants of the general formula Me3SiOSiMeR1OSiMe3 (R1 = (CH2)3(OCH2CH2)2OR2, R2 = glycosyl) is described, and the surface activity properties of the surfactant are studied. Diethylene glycol monoallyl\\u000a ether glycoside is synthesized by reacting the diethylene glycol monoallyl ether with glucose. The glycoside-based trisiloxane\\u000a surfactant is prepared by hydrosilylation of the precursor glycoside with hydrogen-containing trisiloxane. The product is\\u000a structurally

Fu Han; Yan-hong Chen; Ya-wen Zhou; Bao-cai Xu

198

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

PubMed

Glycosylation of proteins and lipids is critical to many life processes. Secondary metabolites (or natural products), such as flavonoids, steroids, triterpenes, and antibiotics, are also frequently modified with saccharides. The resulting glycosides include diverse structures and functions, and some of them have pharmacological significance. The saccharide portions of the glycosides often have specific structural characteristics that depend on the aglycones. These molecules also form heterogeneous "glycoform" mixtures where molecules have similar glycosidic linkages but the saccharides vary in the length and type of monosaccharide unit. Thus, it is difficult to purify homogeneous glycosides in appreciable amounts from natural sources. Chemical synthesis provides a feasible access to the homogeneous glycosides and their congeners. Synthesis of a glycoside involves the synthesis of the aglycone, the saccharide, the connection of these two parts, and the overall manipulation of protecting groups. However, most synthetic efforts to date have focused on the aglycones, treating the attachment of saccharides onto the aglycones as a dispensable topic. The synthesis of the aglycone and the synthesis of the saccharide belong to two independent categories of chemistry, and different types of the aglycones and saccharides pose as specific synthetic subjects in their own disciplines. The only reaction that integrates the broad chemistry of glycoside synthesis is the glycosidic bond formation between the saccharide and the aglycone. Focusing on this glycosylation reaction in this Account, we string together our experience with the synthesis of the naturally occurring glycosides. We briefly describe the synthesis of 18 glycosides, including glycolipids, phenolic glycosides, steroid glycosides, and triterpene glycosides. Each molecule represents a prototypical structure of a family of the natural glycosides with interesting biological activities, and we emphasize the general tactics for the synthesis of these diverse structures. We provide a rationale for four tactics for the synthesis of glycosides, based on the stage at which the glycosidic bond is formed between the saccharide and the aglycone. This choice of tactic determines the success or failure of a synthesis, and the flexibility and the overall efficiency of the synthesis as well. Toward the synthesis of heterogeneous glycoform mixtures, we discuss successive and random glycosylation reactions. Finally, we have developed two new glycosylation protocols that address the challenges in the glycosylation of aglycones that are poorly nucleophilic, extremely acid labile, or extremely electrophilic. One of these new protocols takes advantage of glycosyl trifluoroacetimidate donors, and a second protocol uses gold(I)-catalyzed glycosylation with glycosyl ortho-alkynylbenzoate donors. PMID:22493991

Yu, Biao; Sun, Jiansong; Yang, Xiaoyu

2012-04-11

199

Plant and microbial glycoside hydrolases: Volatile release from glycosidic aroma precursors  

Microsoft Academic Search

Following a brief look at the structure and occurrence of glycosidic flavour precursors in plants and fruits, attention is given to mechanisms of enzymatic hydrolysis, the properties of relevant glycosidases, as well as endogenous and exogenous glycosidases affecting flavour release in plants, in fruit juice processing and in winemaking. The constraints for technological applications and future prospects are discussed.

Jean-Emmanuel Sarry; Ziya Günata

2004-01-01

200

Flavonoid glycosides and methylinositol from Ebenus haussknechtii.  

PubMed

Two flavonoid glycosides (compounds 1 and 3) of which one is reported for the first time and a methylinositol (compound 2) were isolated from the aerial parts of Ebenus haussknechtii (Leguminosae). The structures were established as quercetin-7-O-[alpha-L-rhamnopyranosyl(1 --> 6)-beta-D-galactopyranoside] (1), morin-3-O-[4-[5-(4-hydroxyphenyl)pentanoyl]-alpha-L-rhamnopyranosyl(1 --> 6)-beta-D-galactopyranosyl]-7-4'-di-O-methyleter (3), and methylinositol (2) on the basis of chemical and spectroscopic means. The antimicrobial activities of the extracts have also been examined. PMID:17050182

Uyar, Zafer; Böke, Nazli; Türkay, Elçin; Koz, Omer; Ya?a, Ihsan; Kirmizigül, Süheyla

2006-09-01

201

Additional minor diterpene glycosides from Stevia rebaudiana.  

PubMed

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

Chaturvedula, Venkata Sai Prakash; Prakash, Indra

2011-08-01

202

Flavonoid and phenolic glycosides from Salvia officinalis.  

PubMed

Two novel phenolic glycosides cis-p-coumaric acid 4-O-(2'-O-beta-D-apiofuranosyl)-beta-D-glucopyranoside and trans-p-coumaric acid 4-O-(2'-O-beta-D-apiofuranosyl)-beta-D-glucopyranoside were isolated and identified from Salvia officinalis together with 4-hydroxyacetophenone 4-O-(6'-O-beta-D-apiofuranosyl)-beta-D-glucopyranoside, luteolin 7-O-beta-D-glucoside, 7- and 3'-O-beta-D-glucuronide, 6-hydroxyluteolin 7-O-beta-D-glucoside and 7-O-glucuronide, and 6,8-di-C-beta-D-glucosylapigenin (vicenin-2). The luteolin glucuronides and vicenin-2 were identified as new sage constituents. PMID:11142853

Lu, Y; Foo, L Y

2000-10-01

203

ent-Kaurane Glycosides from Tricalysia okelensis  

PubMed Central

Tricalysiosides V and W, two new ent-kaurane glycosides with an acylated disaccharide moiety at the C-3 position, were isolated from the roots of Tricalysia okelensis and their structures established by spectroscopic and chemical methods as ent-kauran-3?,16?,17-triol-19-al 3-O-[5-O-vanilloyl-?-D-apiopyranosyl(1?6)]-?-D-glucopyranoside (1) and ent-kauran-3?,16?,17-triol-19-al 3-O-[5-O-E-sinapoyl-?-D-apiopyranosyl(1?6)]-?-D-glucopyranoside (2).

Xu, Wen-Hui; Jacob, Melissa R.; Agarwal, Ameeta K.; Clark, Alice M.; Liang, Zong-Suo; Li, Xing-Cong

2013-01-01

204

Glycosidic constituents from in vitro Anoectochilus formosanus.  

PubMed

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

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

2000-11-01

205

A new spermatostatic glycoside from the soft coral Sinularia crispa.  

PubMed

The steroid glycoside 1 has been isolated from the Sri Lankan soft coral Sinularia crispa. The structure has been determined by spectroscopic (1H and 13C nmr) techniques. Glycoside 1 showed spermatostatic activity on rat cauda epididymal spermatozoa. PMID:2575139

Tillekeratne, L M; Liyanage, G K; Ratnasooriya, W D; Ksebati, M B; Schmitz, F J

206

Two flavonol glycosides from the underground parts of Vancouveria hexandra.  

PubMed

Two new flavonol glycosides were isolated from the roots and rhizomes of Vancouveria hexandra. The glycosides were determined by chemical and spectral means to be anhydroicaritin 3-galactosyl(1----3) rhamnoside-7-glucoside and anhydroicaritin 3-[6-O-acetyl-galactosyl(1----3)rhamnoside]-7-glucoside. PMID:1366428

Mizuno, M; Iinuma, M; Tanaka, T; Sakakibara, N; Murata, J; Murata, H; Lang, F A

1990-01-01

207

Cycloartane glycosides from the rhizomes of Curculigo orchioides.  

PubMed

Cycloartane glycosides (1-9) were isolated from rhizomes of Curculigo orchioides (Hypoxidaceae), and this structures were determined by spectroscopic analysis and a few chemical transformations. Cytotoxic activity of glycosides (1-9) and their common aglycone (1a) against HL-60 human promyelocytic leukemia cells was also examined. PMID:20965526

Yokosuka, Akihito; Sato, Koji; Mimaki, Yoshihiro

2010-10-19

208

Acylated flavonol glycosides from leaves of Planchonia grandis.  

PubMed

Three acylated flavonol glycosides have been identified from leaves of Planchonia grandis Ridley. They possess kaempferol as aglycone and two triglycosidic chains substituting hydroxyl groups at the 3- and 7-positions. The first glycosidic unit of each chain is esterified by a cis or trans p-coumaric acid. Structural elucidation was achieved by means of UV, NMR and mass spectrometry. PMID:12943780

Crublet, Marie-Laure; Long, Christophe; Sévenet, Thierry; Hadi, Hamid A; Lavaud, Catherine

2003-09-01

209

Acylated flavonol glycosides from leaves of Planchonia grandis  

Microsoft Academic Search

Three acylated flavonol glycosides have been identified from leaves of Planchonia grandis Ridley. They possess kaempferol as aglycone and two triglycosidic chains substituting hydroxyl groups at the 3- and 7-positions. The first glycosidic unit of each chain is esterified by a cis or trans p-coumaric acid. Structural elucidation was achieved by means of UV, NMR and mass spectrometry.

Marie-Laure Crublet; Christophe Long; Thierry Sévenet; Hamid A Hadi; Catherine Lavaud

2003-01-01

210

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

1995-01-01

211

Glycoside hydrolases and glycosyltransferases: families and functional modules  

Microsoft Academic Search

The past year has witnessed the expected increase in the number of solved structures of glycoside hydrolases and glycosyltransferases, and their constitutive modules. These structures show that, while glycoside hydrolases display an extraordinary variety of folds, glycosyltransferases and carbohydrate-binding modules appear to belong to a much smaller number of folding families.

Yves Bourne; Bernard Henrissat

2001-01-01

212

Structural and sequence-based classification of glycoside hydrolases  

Microsoft Academic Search

The diversity of oligo- and polysaccharides provides an abundance of biological roles for these carbohydrates. The enzymes hydrolysing these compounds, the glycoside hydrolases, therefore mediate a wealth of biological functions. Glycoside hydrolases fall into a number of sequence-based families. The recent analysis of these families, coupled with the burgeoning number of 3D structures, provides a detailed insight into the structure,

Bernard Henrissat; Gideon Davies

1997-01-01

213

A method for preparing C-glycosides related to phlorizin  

Microsoft Academic Search

Johnson's Suzuki coupling protocol was employed to prepare C-glycoside analogs of phlorizin (1). In vitro biological evaluation of these C-glycosides indicated the anomeric oxygen is important to the SGLT inhibitory activity of phlorizin (1) and related agents.

J. T Link; Bryan K Sorensen

2000-01-01

214

Caution against Determining Tannins in Soil using the Protein Precipitable Phenolics Assay  

Microsoft Academic Search

The aim of this study was to assess the use of the protein precipitable phenolics assay as a method for estimating tannin in soil samples. This method is more selective than general methods such as Folin assays and is used to differentiate tannin from other phenolics in plant extracts. We evaluated the role of the protein as an agent that

Melanie A. Krook; Ann E. Hagerman

2011-01-01

215

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

Microsoft Academic Search

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

Y.-S. Wong; X. Wang

1991-01-01

216

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

Microsoft Academic Search

Current antifouling coatings are based on toxic compounds that can be harmful to the natural environment. A promising alternative to these compounds is the use of natural products that are non-toxic, but have antifouling properties. Tannins are natural, water-soluble, complex polyphenolic substances, which precipitate proteins and have anticorrosive and antimicrobial properties. In this study, the effect of quebracho tannin as

Miriam Pérez; Mónica García; Guillermo Blustein; Mirta Stupak

2007-01-01

217

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

218

Response of total tannins and phenolics in loblolly pine foliage exposed to ozone and acid rain  

Microsoft Academic Search

Tannin and total phenolic levels in the foliage of loblolly pine (Pinus taeda L.) were examined in order to evaluate the effect of atmospheric pollution on secondary plant metabolism. The trees were exposed to four ozone concentrations and three levels of simulated acid rain. Tannin concentration (quantity per gram) and content (quantity per fascicle) were increased in foliage exposed to

D. N. Jordan; T. H. Green; A. H. Chappelka; B. G. Lockaby; R. S. Meldahl; D. H. Gjerstad

1991-01-01

219

Distribution and concentration of total phenolics, condensed tannins, and nordihydroguaiaretic acid (NDGA) in creosotebush ( Larrea tridentata)  

Microsoft Academic Search

This paper focuses on the presence and distribution of secondary phenolic compounds found within creosotebush [Larrea tridentata (Sess. & Moc. ex DC.) Cov.]. Total phenolics, condensed tannins and nordihydroguaiaretic acid (NDGA) were measured in nine categories of tissue within creosotebush. Total phenolic and condensed tannin concentrations were determined using colorimetric methods while NDGA content was determined with high performance liquid

Paul W. Hyder; E. L. Fredrickson; Rick E. Estell; Mario Tellez; Robert P. Gibbens

2002-01-01

220

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

Microsoft Academic Search

The role that tannins play in tannery wastewater treatment has been evaluated employing a pilot Membrane Bioreactor (MBR) plant and a full scale Conventional Activated Sludge Process (CASP) plant conducted in parallel. The proposed methodology has established the preliminary use of respirometry to examine the biodegradability of a selection of commercial products (synthetic and natural tannins); the subsequent analysis, by

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

2009-01-01

221

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

222

Effect of water deficit on Merlot grape tannins and anthocyanins across four seasons  

Microsoft Academic Search

Tannins and anthocyanins impart important sensory attributes and potential health benefits in wine. The effect of water deficits (WDs) on fruit growth, anthocyanins, and skin tannins was investigated in field grown Vitis vinifera L. ‘Merlot’ berries across four seasons (2004, 2005, 2007, and 2008) by imposing deficits from the onset of ripening until maturity. WD reduced berry weight and increased

Barbara Bucchetti; Mark A. Matthews; Luigi Falginella; Enrico Peterlunger; Simone D. Castellarin

2011-01-01

223

Effect of chloride and condensable tannin in anaerobic degradation of tannery wastewaters  

Microsoft Academic Search

Toxic effect due to chloride and condensable tannin on anaerobic digestion of vegetable tanning wastewater was investigated at different hydraulic retention times viz 24, 48 and 60 hr respectively. The toxicity to anaerobic contact filter was observed at a chloride concentration of 4500 mg\\/l and tannin concentration of 790 mg\\/l respectively under synergistic condition. In the case of constant influent

K. Vijayaraghavan; T. K. Ramanujam

1999-01-01

224

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

225

A critical analysis of techniques for measuring tannins in ecological studies  

Microsoft Academic Search

A series of seventeen plant extracts rich in phenolic materials, including condensed and hydrolysable tannins, have been subjected to a series of chemical analyses in an attempt to gather ecologically significant information about their structure. Procedures investigated were (i) the Folin-Denis and Hagerman and Butler methods for quantifying total phenolics, (ii) the vanillin and proanthocyanidin methods for quantifying condensed tannins,

S. Mole; P. G. Waterman

1987-01-01

226

VARIATION IN MAMMALIAN PHYSIOLOGICAL RESPONSES TO A CONDENSED TANNIN AND ITS ECOLOGICAL IMPLICATIONS  

Microsoft Academic Search

Ansrnacr.-Mule deer (Odocoileus hemionus), domestic sheep (Oois aries), and American black bears (Ursus americanus) were fed quebracho (Schinopsis sp.) tannin to determine the contribution of salivary proteins to nitrogen- and fiber-digestive efficiencies and tannin metabolism. These values were compared to previously published values for laboratory rats (Ratfus rattus) and prairie voles (Microtus ochrogaster). Mule deer, black bears, and laboratory rats

C. T. RossrNS; P. J. AusrrN; T. A. HeNr-rv

227

Condensed tannins deter feeding by browsing ruminants in a South African savanna  

Microsoft Academic Search

The palatability of 14 species of woody plant was assessed for three species of browsing ruminant, namely kudus, impalas and goats. Results show that palatability was most clearly related to leaf contents of condensed tannins. The effect was a threshold one, with all plants containing more than 5% condensed tannins being rejected as food during the wet season period. In

S. M. Cooper; N. Owen-Smith

1985-01-01

228

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

1977-01-01

229

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

USGS Publications Warehouse

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

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

2003-01-01

230

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

USGS Publications Warehouse

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

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

2003-01-01

231

Kinetic analysis of palladium(II) adsorption process on condensed-tannin gel based on redox reaction models  

Microsoft Academic Search

We have developed a novel recovery system of palladium (Pd) from wastes such as spent catalysts or scraps, using tannin gel particles synthesized from condensed-tannin molecules. The Pd(II) ionic species are reduced to metallic Pd(0) on the network of the tannin gel: a two-electron transfer from the tannin gel to Pd(II). The kinetic study of the electron transfer was performed

Yeon-Ho Kim; Takeshi Ogata; Yoshio Nakano

2007-01-01

232

Feeny revisited: condensed tannins as anti-herbivore defences in leaf-chewing herbivore communities of Quercus  

Microsoft Academic Search

Community level oak-tannin-insect patterns have been largely unexplored since Paul Feeny's ground-breaking research. Two hypotheses were tested for Quercus velutina and Q. alba in the Missouri Ozarks: abundance and richness of leaf-chewing herbivores are negatively correlated with foliar condensed tannin concentrations and variation in condensed tannin concentrations explains variation in herbivore community structure. 2. In 2001, foliar condensed tannins in

REBECCA E. F ORKNER; R OBERT J. M ARQUIS

2004-01-01

233

Yeast Effects on Pinot noir Wine Phenolics, Color, and Tannin Composition.  

PubMed

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

2013-10-03

234

Anti-inflammatory actions of tannins isolated from the bark of Anacardium occidentale L.  

PubMed

A mixture of tannins (hydrolysable and non-hydrolysable) obtained from the bark of Anacardium occidentale L., on i.p. injection, demonstrated apparent anti-inflammatory activity in carrageenan- and dextran-induced rat paw oedemas, cotton pellet granuloma test and adjuvant-induced polyarthritis in rats. At higher doses orally administered tannins also had activity in carrageenan paw oedema and adjuvant arthritis experiments. The tannins i.p. also inhibited acetic acid-induced "writhing responses" in mice and were found to antagonise the permeability-increasing effects in rats of certain mediators of inflammation and to inhibit the migration of leucocytes to an inflammatory site. While not appearing to act by the release of adrenal hormones, tannins may produce effects in a non-specific manner by their astringent properties on cell membranes thus affecting cell functions. The above results should be considered while studying the anti-inflammatory actions of plant extracts which contain tannins. PMID:2414605

Mota, M L; Thomas, G; Barbosa Filho, J M

1985-07-01

235

Short-term changes in eating patterns explain the effects of condensed tannins on feed intake in heifers  

Microsoft Academic Search

Ingestion of condensed tannins decreases feed intake in ruminants. Polyethylene glycol (PEG) forms high-affinity complexes with tannins. In two experiments carried out on Holstein heifers, quebracho (Q) from the Aspidosperma quebracho served as source of condensed tannins. The aims of the study were (i) to quantify the effect of Q on feed intake and eating behaviour in cattle fed complete

S. Landau; N. Silanikove; Z. Nitsan; D. Barkai; H. Baram; F. D. Provenza; A. Perevolotsky

2000-01-01

236

Tannin-binding proteins in saliva of deer and their absence in saliva of sheep and cattle  

Microsoft Academic Search

A method has been developed for detecting tannin-binding proteins in the saliva of herbivores. The method is simple and requires only small quantities of crude saliva. The saliva of deer, a browsing ruminant, has been compared to that of domestic sheep and cow, which are grazing ruminants. The browser, which normally ingests dietary tannin, produces tannin-binding proteins, while the grazers

Paul J. Austin; Lisa A. Suchar; Charles T. Robbins; Ann E. Hagerman

1989-01-01

237

In vitro availability of iron and zinc in white and coloured ragi ( Eleusine coracana ): role of tannin and phytate  

Microsoft Academic Search

White and brown ragi (Eleusine coracana) varieties were analysed for tannin, phytate phosphorus, total phosphorus, iron, ionisable iron, zinc and soluble zinc content. White ragi had no detectable tannin while in brown varieties it ranged from 351 to 2392 mg per 100 g. Germination brought about a progressive decrease in tannin and phytate phosphorus and an increase in ionisable ion

P. Udayasekhara Rao; Y. G. Deosthale

1988-01-01

238

Purification of glycoside hydrolases from Bacteroides fragilis.  

PubMed Central

Six glycoside hydrolases in the culture medium of Bacteroides fragilis--alpha-glucosidase, beta-glucosidase, alpha-galactosidase, beta-galactosidase, beta-N-acetylglucosaminidase, and alpha-L-fucosidase-were systematically purified by ammonium sulfate precipitation, gel filtration chromatography, and density gradient isoelectric focusing. The isoelectric focusing resolved the glycosidases into distinct, well-separated fractions and revealed three differently charged forms of beta-N-acetylglucosaminidase and of alpha-L-fucosidase. Furthermore, alpha-glucosidase and beta-N-acetylglucosaminidase were shown to possess dual affinities for the respective galactoside substrates, and beta-galactosidase also hydrolyzed beta-D-fucoside. alpha-Glucosidase was purified to homogeneity, as indicated by a thin-layer isoelectric focusing zymogram technique. The glycosidases, with exception of beta-glucosidase and the acid alpha-L-fucosidase, were each separated from other glycosidic activities to 99%. The molecular weights varied between 58,000 and 125,000. The pH optima ranged from 4.8 to 6.9. Images

Berg, J O; Lindqvist, L; Nord, C E

1980-01-01

239

Saliva of the graminivorous Theropithecus gelada lacks proline-rich proteins and tannin-binding capacity.  

PubMed

Gelada baboons are the sole survivors of the genus Theropithecus and the only known graminivorous primates. They developed special adaptations to their diet such as high-crowned teeth for processing hard and abrasive feed. The fine-tuning of salivary protein composition might be another key mechanism that is used by species for adapting to the environment and competing with rivals for exploiting new ecological niches. In order to test whether gelada (graminivorous) and hamadryas baboons (omnivorous) differ in their salivary protein composition, we compared whole saliva samples of captive Theropithecus gelada and Papio hamadryas using gel electrophoresis and tannin-binding assay. We hypothesized that the amount of proline-rich salivary proteins with tannin-binding capacity is higher in baboons consuming a feed with high dicot/monocot rations. Dicots produce tannins as a chemical defense system, discouraging animals from eating them. In contrast to dicots, monocots do not synthesize tannins. The presence of tannin-binding proteins in saliva should effectively inactivate the dicot tannin-based defense mechanism and increase the dietary breadth and/or the capability to switch between monocots and dicot leaves. The lack of such tannin-binding proteins in saliva would indicate a narrow dietary spectrum more restricted to monocots. We found T. gelada to completely lack proline-rich proteins (PRPs) and tannin-binding capacity similar to a great variety of other grazing mammals. In contrast, P. hamadryas does possess PRPs with tannin-binding activity. The findings support a growing body of evidence suggesting a high-level specialization of T. gelada to grass diets. However, it remains unclear, whether loss of salivary tannin-binding capacity drove the gelada into its narrow feeding niche, or whether this loss is the result of a long process of increased specialization. Thus, from an ecological point of view, T. gelada appears to be more vulnerable to environmental changes than other baboon species owing to its narrow dietary traits. PMID:19431194

Mau, Marcus; Südekum, Karl-Heinz; Johann, Achim; Sliwa, Alexander; Kaiser, Thomas M

2009-08-01

240

Mechanism of hexavalent chromium adsorption by persimmon tannin gel.  

PubMed

Mechanism of chromium adsorption by the persimmon tannin (PT) gel was examined. The PT gel can adsorb Cr highly effectively from aqueous solutions containing Cr(VI), while it adsorbed far smaller amounts of Cr from the solution containing Cr(III). The maximum Cr adsorption from the Cr(VI) solution occurred at pH 3. The Cr adsorption from the Cr(VI) solution by the PT gel was rapid, was faster than VO2+ and Fe3+ adsorptions, and was obeyed the Langmuir adsorption isotherm (Qe= 5.27 mmol g(-1) and K= 16.2 mM). The gel adsorbed Cr from the Cr(VI) solution (pH 1 and 3) showed no ESR signal of Cr(III), while the ESR signal of Cr(III) was observed in the residual solution at pH 1. Hexavalent chromium was, therefore, adsorbed on the PT gel through the esterification of chromate with catechol group. In other words, Cr(VI) should combine with catechol as a hard acid, CrO2(2+) cation. Through the treatment of a Cr(VI) solution with the PT gel, chromium should be recovered as a Cr(IV)-tannin complex at pH 3 or a Cr(III) solution at pH 1 or lower pH region. PMID:15223280

Nakajima, Akira; Baba, Yoshinari

2004-07-01

241

The modulatory effect of Cochlospermum tinctorium a rich aqueous root extract on liver damage induced by carbon tetrachloride in rats  

Microsoft Academic Search

The aqueous root extract of Cochlospermum tinctorium (CTR) was investigated for its phytochemical composition; acute oral toxicity and hepatoprotective effect on carbon tetrachloride (CCl4) induced liver damage in rats. Phytochemical screening indicates the presence of alkaloids, tannins, cardiac glycosides, saponins, flavonoids, triterpenes, cyanogenic glycosides and volatile oils while steroids and anthraquinones were absent. Administration of 5000 mg\\/kg (body weight) of

E. U. Etuk; B. M. Agaie; M. J. Ladan; I. Garba

242

The antimicrobial activities of methanolic extracts of Eucalyptus camaldulensis and Terminalia catappa against some pathogenic microorganisms  

Microsoft Academic Search

Methanolic extracts of leaves of Eucalyptus camaldulensis and Terminalia catappa were studied for in vitro microbial activities by agar dilution method. The phytochemical analysis of the crude extracts of the medicinal plants revealed the presence of saponin, saponin glycosides, steroid, cardiac glycoside, tannins, volatile oils, phenols and balsam (gum). The methanolic extracts of the two plants inhibited the growth of

H. Babayi; I. Kolo; J. I. Okogun; U. J. J. Ijah

2004-01-01

243

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

PubMed

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, Benoît; Solymosi, Katalin; Cheynier, Véronique; Fulcrand, Hélène; Verdeil, Jean-Luc; Conéjéro, Geneviève

2013-09-11

244

Cardiac sarcoidosis.  

PubMed

Cardiac sarcoidosis is a rare entity and may be difficult to diagnose prior to cardiac surgery. We review the imaging and diagnostic studies necessary to make the diagnosis and discuss therapeutic algorithms to manage this disease. doi: 10.1111/jocs.12163 (J Card Surg 2013;28:525-528). PMID:23844704

Zacek, Pavel; Omran, Nedal; Chek, James L; Krbal, Lukas; Vojacek, Jan; Harrer, Jan

2013-07-12

245

[Cardiac radiology].  

PubMed

From the beginning of the era of X-rays, cardiac radiology has become a target of this new technique. Early pioneers, Ciegem, Rieder, Rosenthal, Williams rapidly accumulated extensive experience with fluoroscopy and radiography and publications on cardiac diseases as soon as 1899 and 1901 and 1902. The next step in cardiac diagnosis was achieved by Forsmann in 1929, with the first attempt at cardiac catheterization and angiocardiography. Many clinicians, Moniz, Reboul, Rousthoi contributed to the development of the technique between 1930 and 1940. A further turning point came in 1941 when Cournand demonstrated that cardiac catheterization was a safe method in man. In the technical field major progress came from Scandinavia were rapid filming was born. The management of ischaemic disease, changed dramatically with the demonstration of coronary anatomy, largely due to Sones, Judkins and Amplatz. A further progress was initiated in 1977 by Gruentzig who invented balloon angioplasty. PMID:8550395

Struyven, J

1995-10-01

246

Inhibitory activity of pine needle tannin extracts on some agriculturally resourceful microbes.  

PubMed

Crude extracts of water and solvent extractable tannin fractions from pine needles were found to contain tannin concentrations of 10.15% and 13.15% tannic acid equivalents respectively. Thin Layer Chromatography revealed the presence of four distinct phenolic compounds, amongst which two were tannic acid like compounds. Both the extracts were found to be inhibitory to several microbes of agricultural importance. Amongst the bacterial strains studied, Azotobacter sp (VL-A2) was able to tolerate upto 1000 ppm of crude tannin concentration without any growth inhibition. While growth of Rhizobium (VL-R1) and Bacillus halodurans (MTCC 7181) was inhibited by crude tannin concentrations of 50 and 100 ppm respectively of both water and solvent extracted tannins. Among the fungal genera, Pleurotus djamor was found to tolerate up to 10000 ppm of crude tannins, while Trichoderma virescens (MTCC 6321) and T. reesii could tolerate up to 3000 ppm of both water extractable and acetone extractable crude tannins without any growth inhibition. PMID:23100676

Selvakumar, G; Saha, Supradip; Kundu, S

2007-10-04

247

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

PubMed

The role that tannins play in tannery wastewater treatment has been evaluated employing a pilot Membrane Bioreactor (MBR) plant and a full scale Conventional Activated Sludge Process (CASP) plant conducted in parallel. The proposed methodology has established the preliminary use of respirometry to examine the biodegradability of a selection of commercial products (synthetic and natural tannins); the subsequent analysis, by means of spectrophotometric reading and RP-IPC (Reverse-Phase Ion-Pair) liquid chromatography, estimates the concentrations of natural tannins and naphthalenesulfonic tanning agents in the influent and effluent samples. The results show that a consistent percentage of the Total Organic Carbon (TOC) in the effluent of the biological phase of the plants is attributable to the presence of natural and synthetic (Sulfonated Naphthalene-Formaldehyde Condensates, SNFC) tannins (17% and 14% respectively). The titrimetric tests that were aimed at evaluating the levels of inhibition on the nitrifying biomass samples did not allow a direct inhibiting effect to be associated with the concentration levels of the tannin in the effluent. Nonetheless, the reduced specific growth rates of ammonium and nitrite oxidising bacteria imply that a strong environmental pressure is present, if not necessarily due to the concentration of tannins, due to the wastewater as a whole. The differences that have emerged by comparing the two technologies (CASP and MBR), in regards to the role that tannins play in terms of biodegradability, did not appear to be significant. PMID:18835658

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

2008-08-28

248

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

PubMed

In context with the frequent observations of excessive iron (Fe) storage in captive black rhinoceroses (Diceros bicornis), it has been suggested that both an excessive dietary Fe content and a lack of dietary Fe-chelating substances, such as tannins, is the underlying cause. Therefore, studies on the effects of tannin supplementation to captive diet are warranted. Six captive rhinoceroses were fed their normal zoo diet (N), and a similar diet supplemented with either tannic acid (T, hydrolysable tannin) or quebracho (Q, condensed tannins), and the total antioxidant capacity (TAC) was measured as mmol Trolox equivalents per kg fresh faeces. The TAC values on diets N (1.24 +/- 0.39 mmol/kg fresh faeces) and T (1.34 +/- 0.33 mmol/kg fresh faeces) were similar, but significantly higher on diet Q (2.32 +/- 0.61 mmol/kg fresh faeces). In contrast to expectations, faecal TAC increased with increasing faecal Fe, possibly as a result of the fact that the faecal Fe content was positively correlated to the proportion of concentrate feeds in the diet, which also contain antioxidants, such as vitamin E, in addition to Fe. Increased antioxidant status caused by the use of tannin substances could have a beneficial effect on animal health, but if tannins should be incorporated in designed diets, other tannin sources, such as grape pomace should be tested. PMID:16901277

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

2006-08-01

249

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

PubMed

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

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

2013-07-29

250

Steroidal glycosides from Furcraea foetida and their cytotoxic activity.  

PubMed

Two new spirostanol glycosides (1, 2) and a new furostanol glycoside (3), together with nine known steroidal glycosides (4-12) were isolated from the leaves of Furcraea foetida (Agavaceae). The structures of the new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, HSC-2 human oral squamous carcinoma cells, and HSC-4 human oral squamous carcinoma cells. PMID:19801882

Yokosuka, Akihito; Sano, Tomoe; Hashimoto, Ken; Sakagami, Hiroshi; Mimaki, Yoshihiro

2009-10-01

251

Five new flavonoid glycosides from Nervilia fordii.  

PubMed

Five new flavonoid glycosides, namely nervilifordins F-J (1-5), were isolated from the 60% EtOH extract of the aerial parts of Nervilia fordii, along with three first isolated flavonoids (7, 8, and 13) and five known flavonoids (6, 9-12). The structures of new compounds were elucidated on the basis of 1D and 2D NMR and MS studies. Their anti-inflammatory activities were tested by measuring their inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages. Compounds 2 and 5 showed interesting inhibition effects with their EC50 values of 15.15 ?M and 14.80 ?M, respectively. PMID:23659497

Qiu, Li; Jiao, Yang; Xie, Ji-Zhao; Huang, Gui-Kun; Qiu, Shao-Ling; Miao, Jian-Hua; Yao, Xin-Sheng

2013-05-10

252

Induction of interleukin-1-beta release from human monocytes by cotton bract tannin.  

PubMed

The human T lymphocyte proliferative response to cotton bract tannin was shown to be dependent upon the presence of monocytes. Since monocytes support the T cell mitogenic response by interleukin-1 (IL-1) production, it was anticipated that tannin has IL-1-inducing ability. To examine this possibility, human monocytes were cultured alone or with peripheral blood T lymphocytes, and stimulated with tannin. Control cultures included unstimulated cells, and cells challenged with other IL-1 inducers: concanavalin A (Con A) and lipopolysaccharide from Escherichia coli or Enterobacter agglomerans. IL-1 beta was measured in culture supernatants 24 h after initiation of the culture by the use of an ELISA or an RIA. The results showed that tannin stimulated monocytes to secrete IL-1 beta in a manner similar to Con A, i.e. substantially more cytokine was measured in the supernatants of monocyte-T-lymphocyte co-cultures than in the cultures of monocyte alone. Endotoxin from E. coli was less effective than the endotoxin from E. agglomerans in IL-1 induction. Contaminating endotoxin present in the tannin preparation accounted for the majority of IL-1 beta released from monocytes alone stimulated with tannin, but only 20% of the IL-1 beta released from tannin-stimulated monocyte-T-lymphocyte co-cultures. These results show that tannin itself has IL-1-inducing ability. The dose-response studies show that the extent of IL-1 beta release is dependent on tannin dose and that increased levels of monocyte-produced IL-1 beta precede the increase in T lymphocyte proliferation.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:2210874

Vuk-Pavlovi?, Z; Rohrbach, M S

1990-01-01

253

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

PubMed

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

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

2007-12-01

254

Monomeric and dimeric hydrolysable tannins of Tamarix nilotica.  

PubMed

An ellagitannin monomer, nilotinin M1 (1), and three dimers, nilotinins D1 (2), D2 (3), and D3 (4), were isolated from leaves of Tamarix nilotica (Ehrenb.) Bunge. Structures were elucidated based on analysis of spectroscopic data and chemical correlations with known compounds. In addition, six known tannins, hirtellin A (5) (dimer), remurin A (6), remurin B (7), 1,3-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-beta-D-glucose (8), gemin D (9), and hippomanin A (10) (monomers), were isolated for the first time from this plant species. The reported (13)C NMR assignments of the dehydrodigalloyl moiety and glucose cores of 5 are revised, and the (13)C NMR spectroscopic data for 6 and 7 are also reported for the first time. PMID:19695651

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

2009-08-18

255

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

PubMed

The rational use of hawthorn leafs and flowers from Crataegus spp. for declining cardiac performance is mainly due to flavon-C-glycosides and oligomeric procyanidins (OPC). From OPC-enriched extracts from different batches, a dimeric phenylpropanoid-substituted procyanidin (cinchonain II?b, 1) was isolated and characterized by MS, CD, and NMR. Also the presence of higher oligomeric cinchonains (degree of polymerization 3 to 8) in hawthorn extracts was shown by a specific ultrahigh-pressure liquid chromatography-ESI-qTOF-MS method. Interestingly, strong evidence for the occurrence of oligomeric procyanidin hexosides was found by ultrahigh-pressure liquid chromatography-ESI-qTOF-MS analysis which additionally revealed the presence of peaks indicative of dimeric procyanidin hexosides by their exact mass, which were clearly distinguishable from the cinchonain II type peaks. PMID:23154843

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

2012-11-15

256

The Use of Digitalis Glycosides in the Dog and Cat  

PubMed Central

The author reviews the pharmacological properties of digitalis glycosides and their clinical use in the control of congestive heart failure in the dog and cat. Methods of digitalization, dosage for each drug, toxic effects and drug interactions are described.

Difruscia, R.

1984-01-01

257

Resin glycosides from the aerial parts of Operculina turpethum.  

PubMed

Three glycosidic acids, turpethic acids A-C, and two intact resin glycosides, turpethosides A and B, all having a common pentasaccharide moiety and 12-hydroxy fatty acid aglycones of different chain lengths, were obtained from the aerial parts of Operculina turpethum. Their structures were elucidated by spectroscopic analyses and chemical correlations. The aglycones were characterized as 12-hydroxypentadecanoic acid in two compounds, 12-hydroxyhexadecanoic acid in two other components, and 12-hydroxyheptadecanoic acid in the fifth compound, which were all confirmed by synthesis. The absolute configurations of these aglycones were all established as S by Mosher's method. These compounds represent the first examples of resin glycosides with a monohydroxylated 12-hydroxy fatty acid as an aglycone, and one compound is the first described resin glycoside having a hydroxylated C(17) fatty acid as its aglycone. PMID:22717506

Ding, Wenbing; Jiang, Zi-Hua; Wu, Ping; Xu, Liangxiong; Wei, Xiaoyi

2012-06-18

258

Anti-neutrophilic inflammatory steroidal glycosides from Solanum torvum.  

PubMed

Torvpregnanosides A and B, two pregnane glycosides, and torvoside Q, a 23-keto-spirostanol glycoside, along with twelve known steroidal saponins were isolated from aerial parts of Solanum torvum. Of the latter, four of the 23-hydroxy-spirostanol glycosides, and, a yamogenin glycoside, were in this plant discovered. All structures were identified from spectroscopic data, and all the compounds were tested for in vitro anti-neutrophilic inflammatory activity. Two compounds showed selective inhibition against elastase release and superoxide anion generation, respectively, by human neutrophils with IC50 values of 5.66 and 3.59?M, while two others inhibited both inflammatory mediators with IC50 values of 0.66-3.49?M. Structure-activity relationships are discussed. PMID:23838628

Lee, Chia-Lin; Hwang, Tsong-Long; He, Wan-Jung; Tsai, Yi-Hong; Yen, Chiao-Ting; Yen, Hsin-Fu; Chen, Chao-Jung; Chang, Wei-Yi; Wu, Yang-Chang

2013-07-06

259

Macedonine, a non-glycosidic iridoid from Galium macedonicum  

Microsoft Academic Search

A new non-glycosidic iridoid, macedonine, was isolated from Galium macedonicum. The structure, stereochemistry and conformation were determined by spectral methods and molecular mechanics calculations. Macedonine lacks the 3,4-double bond and the C-1 substituent.

Maya Mitova; Nedjalka Handjieva; Stefan Spassov; Simeon Popov

1996-01-01

260

Cardiac Arrest  

MedlinePLUS

... too slow, or it can stop beating. Sudden cardiac arrest (SCA) occurs when the heart develops an arrhythmia that ... is blocked. There are many possible causes of SCA. They include coronary heart disease, physical stress, and ...

261

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

PubMed Central

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

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

2002-01-01

262

Two new triterpenoidal glycosides from Medicago polymorpha L.  

PubMed

Two new triterpenoid glycosides called medicago-saponins P1 (1) and P2 (2) were isolated together with five known glycosides from the aerial parts of Medicago polymorpha L. (Leguminosae). The structures of 1 and 2 were determined to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl caulophyllogenin 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside and the desglucoside of 1. PMID:8069980

Kinjo, J; Uemura, H; Nakamura, M; Nohara, T

1994-06-01

263

Three New Steroidal Glycosides from the Roots of Cynanchum stauntonii  

PubMed Central

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

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

2013-01-01

264

Steroidal saponins and pregnane glycosides from Smilax microphylla.  

PubMed

Six steroidal saponins and two pregnane glycosides were isolated from the BuOH subfraction of 70% EtOH extract of Smilax microphylla C.H.Wright, among them two were new compounds (1 and 7). Pregnane glycosides were firstly isolated from the genus Smilax (Smilacaceae). Structures of the new compounds were determined on the basis of HR-ESI-MS, 1D and 2D NMR spectroscopic analysis. PMID:23042046

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

2012-10-08

265

Two new glycosides from the florets of Carthamus tinctorius.  

PubMed

Two new glycoside compounds, named saffloquinoside C (1) and (-)-4-hydroxybenzoic acid-4-O-[6'-O-(2?-methylbutyryl)-?-D-glucopyranoside] (2), were isolated from the florets of Carthamus tinctorius. Their structures were elucidated by detailed spectroscopic means including UV, IR, HR-ESI-MS, 1D and 2D NMR, and CD data. Compound 1 was a rare quinochalcone glycoside with six five-membered dioxaspirocycle. PMID:23600648

Jiang, Jian-Shuang; Chen, Zhong; Yang, Ya-Nan; Feng, Zi-Ming; Zhang, Pei-Cheng

2013-04-22

266

Furostanol glycosides from the rhizomes of Helleborus orientalis.  

PubMed

Eight new furostanol glycosides (1-8), together with two known ones (9 and 10), have been isolated from a glycoside-enriched fraction prepared from the rhizomes of Helleborus orientalis (Ranunculaceae). The structures of 1-8 were determined on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HSC-2 cells. PMID:20563660

Mimaki, Yoshihiro; Matsuo, Yukiko; Watanabe, Kazuki; Sakagami, Hiroshi

2010-06-19

267

Characterization and Synergistic Interactions of Fibrobacter succinogenes Glycoside Hydrolases  

Microsoft Academic Search

The objectives of this study were to characterize Fibrobacter succinogenes glycoside hydrolases from different glycoside hydrolase families and to study their synergistic interactions. The gene encoding a major endoglu- canase (endoglucanase 1) of F. succinogenes S85 was identified as cel9B from the genome sequence by reference to internal amino acid sequences of the purified native enzyme. Cel9B and two other

Meng Qi; Hyun-Sik Jun; Cecil W. Forsberg

2007-01-01

268

Antioxidant phenolic glycosides from the bark of Populus ussuriensis Kom.  

PubMed

Study on the EtOAc soluble fraction from the bark of Populus ussuriensis Kom. resulted in the isolation of three phenolic glycosides, including populoside (1), 7-O-?-coumaroylsalirepin (2) and 7-O-caffeoylsalirepin (3), among which 3 is a new compound. The structures of these compounds were elucidated on the basis of spectroscopic evidence. Phenolic glycosides 1-3 exhibited excellent antioxidant activity, evaluated in the ABTS? radical scavenging assay. PMID:19662569

Si, Chuan-Ling; Li, Shu-Ming; Liu, Zhong; Kim, Jin-Kyu; Bae, Young-Soo

2011-07-08

269

Cardiac cameras.  

PubMed

Cardiac imaging with radiotracers plays an important role in patient evaluation, and the development of suitable imaging instruments has been crucial. While initially performed with the rectilinear scanner that slowly transmitted, in a row-by-row fashion, cardiac count distributions onto various printing media, the Anger scintillation camera allowed electronic determination of tracer energies and of the distribution of radioactive counts in 2D space. Increased sophistication of cardiac cameras and development of powerful computers to analyze, display, and quantify data has been essential to making radionuclide cardiac imaging a key component of the cardiac work-up. Newer processing algorithms and solid state cameras, fundamentally different from the Anger camera, show promise to provide higher counting efficiency and resolution, leading to better image quality, more patient comfort and potentially lower radiation exposure. While the focus has been on myocardial perfusion imaging with single-photon emission computed tomography, increased use of positron emission tomography is broadening the field to include molecular imaging of the myocardium and of the coronary vasculature. Further advances may require integrating cardiac nuclear cameras with other imaging devices, ie, hybrid imaging cameras. The goal is to image the heart and its physiological processes as accurately as possible, to prevent and cure disease processes. PMID:21440695

Travin, Mark I

2011-05-01

270

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

PubMed

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

2013-07-23

271

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

1999-01-01

272

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

PubMed

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

2012-07-10

273

Relationship between Red Wine Grades and Phenolics. 1. Tannin and Total Phenolics Concentrations.  

PubMed

Measuring chemical composition is a common approach to support decisions about allocating foods and beverages to grades related to market value. Red wine is a particularly complex beverage, and multiple compositional attributes are needed to account for its sensory properties, including measurement of key phenolic components such as anthocyanins, total phenolics, and tannin, which are related to color and astringency. Color has been shown to relate positively to red wine grade; however, little research has been presented that explores the relationship between astringency-related components such as total phenolic or tannin concentration and wine grade. The aim of this research has been to investigate the relationship between the wine grade allocations of commercial wineries and total phenolic and tannin concentrations, respectively, in Australian Shiraz and Cabernet Sauvignon wines. Total phenolic and tannin concentrations were determined using the methyl cellulose precipitable (MCP) tannin assay and then compared to wine grade allocations made by winemaker panels during the companies' postvintage allocation process. Data were collected from wines produced by one Australian wine company over the 2005, 2006, and 2007 vintages and by a further two companies in 2007 (total wines = 1643). Statistical analysis revealed a positive trend toward higher wine grade allocation and wines that had higher concentrations of both total phenolics and tannin, respectively. This research demonstrates that for these companies, in general, Cabernet Sauvignon and Shiraz wines allocated to higher market value grades have higher total phenolics and higher tannin concentrations and suggests that these compositional parameters should be considered in the development of future multiparameter decision support systems for relevant commercial red wine grading processes. In addition, both tannin and total phenolics would ideally be included because although, in general, a positive relationship exists between the two parameters, this relationship does not hold for all wine styles. PMID:21047137

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

2010-11-01

274

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

2009-01-01

275

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

SciTech Connect

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

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

1987-01-01

276

Nutritional Improvement of Tannin-Containing Sorghums (Sorghum bicolor) by Sodium Bicarbonate  

Microsoft Academic Search

Cereal Chem. 67(6):533-537 Broiler chicks were fed isonitrogenous diets containing either maize or BRY 936 were supplemented with 0.25% NaHCO3 . Levels of 0.5 or (corn) as a cereal constituent or different cultivars of tannin-containing 0.75% NaHCO3 were inferior to the 0.25% level for improving growth sorghum (about 1% tannin measured as catechin equivalent). Compared of chickens for the latter

DRINAH B. C. BANDA-NYIRENDA; PRAN VOHRA

277

Silver nanoparticles stabilized by tannin grafted collagen fiber: synthesis, characterization and antifungal activity  

Microsoft Academic Search

A novel antifungal nano-silver agent (BT-CF-AgNPs) was synthesized by using bayberry tannin (BT) grafted collagen fiber (CF)\\u000a as support, and the antifungal behaviors of the nano-silver were investigated by using Saccharomyces cerevisiae as a typical fungus. Bayberry tannin (BT), a kind of natural polyphenol, was grafted onto the CF surface to improve the loading\\u000a capacity and control the size of

Li He; Hao Wu; Siying Gao; Xuepin Liao; Qiang He; Bi Shi

278

Adsorption mechanism of palladium by redox within condensed-tannin gel  

Microsoft Academic Search

Condensed-tannin gel particles with polyhydroxyphenyl groups were synthesized as the adsorbent for the new recovery system of palladium (Pd), which was simple and generated little secondary waste in comparison with the conventional recovery processes. The properties of condensed-tannin gel particles for the Pd adsorption were examined in PdCl2 aqueous solution and it was found that Pd(II) was adsorbed onto the

Yeon Ho Kim; Yoshio Nakano

2005-01-01

279

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

PubMed

Astringency is thought to result from the interaction between salivary proline-rich proteins (PRP) that belong to the intrinsically unstructured protein group (IUP), and tannins, which are phenolic compounds. IUPs have the ability to bind several and/or different targets. At the same time, tannins have different chemical features reported to contribute to the sensation of astringency. The ability of both electrospray ionization mass spectrometry and tandem mass spectrometry to investigate the noncovalent interaction occurring between a human salivary PRP, IB5, and a model tannin, epigallocatechin 3-O-gallate (EgCG), has been reported. Herein, we extend this method to study the effect of tannin chemical features on their interaction with IB5. We used five model tannins, epigallocatechin (EgC), epicatechin 3-O-gallate (ECG), epigallocatechin 3-O-gallate (EgCG), procyanidin dimer B2 and B2 3'-O-gallate, which cover the main tannin chemical features: presence of a gallate moiety (galloylation), the degree of polymerization, and the degree of B ring hydroxylation. We show the ability of IB5 to bind these tannins. We report differences in stoichiometries and in stability of the IB5•1 tannin complexes. These results demonstrate the main role of hydroxyl groups in these interactions and show the involvement of hydrogen bonds. Finally, these results are in line with sensory analysis, by Vidal et al. (J Sci Food Agric 83:564-573, 2003) pointing out that the chain length and the level of galloylation are the main factors affecting astringency perception. PMID:20665010

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

2010-07-28

280

Inhibitory mechanism of low-carbon steel corrosion by mimosa tannin in sulphuric acid solutions  

Microsoft Academic Search

Mimosa tannin was investigated as inhibitor of low-carbon steel sulphuric acid corrosion in concentrations from 10-5 to 10-1 mol L-1, at the temperature of 298 K in the solutions of pH 1, 2 and 3. The inhibitor effectiveness increases with increase in concentration. The adsorptive behaviour of mimosa tannin in solutions of pH 1 and 2 may be approximated, both

S. Martinez; I. Štern

2001-01-01

281

Inhibitory mechanism of mimosa tannin using molecular modeling and substitutional adsorption isotherms  

Microsoft Academic Search

A semiempirical approach involving quantum chemical calculations was used to rationalize the mimosa tannin inhibitory action. The molecular spatial structure, atomic charges, dipole moment, HOMO–LUMO energy gap and HOMO density of four types of flavanoid units that constitute mimosa tannin, have been theoretically investigated using HyperChem 5.11 computer package. Optimization of the molecular geometry yielded a non-planar structure with the

S Martinez

2003-01-01

282

Nutrient composition and in vitro ruminal fermentation of tropical legume mixtures with contrasting tannin contents  

Microsoft Academic Search

Various combinations of a low-tannin herbaceous legume (Vigna unguiculata) and foliage of tanniniferous shrub legumes (Calliandra calothyrsus, Flemingia macrophylla and Leucaena leucocephala) or a low-tannin shrub legume (Cratylia argentea), all mixed together with a low-quality tropical grass (Brachiaria humidicola), were tested in vitro for differences in the effects on ruminal fermentation. Two experiments with the gas transducer technique were carried

C. D. Stürm; T. T. Tiemann; C. E. Lascano; M. Kreuzer; H. D. Hess

2007-01-01

283

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

PubMed

We studied the defense mechanisms against the negative effects of tannins in acorns by using the Japanese wood mouse (Apodemus speciosus) and acorns of a Japanese deciduous oak Quercus crispula, which contain 9.9% tannins on a dry weight basis. For the experiment, we allocated 26 wood mice into two groups: acclimated (N = 12) and nonacclimated (N = 14). Mice in the nonacclimated group were fed only acorns for 10 d after 4 wk of receiving a tannin-free diet. In contrast, mice in the acclimated group received ca. 3 g acorns daily in addition to the tannin-free diet for the first 4 wk, then they were fed only acorns for 10 d. Body weight, food intake, and digestibility were monitored. In addition, the amount of salivary proline-rich proteins (PRPs) and abundance of tannase-producing bacteria (TPB) in the feces of mice were measured. Of the 14 mice in the nonacclimated group, 8 died, whereas only 1 of the 12 in the acclimated group died. During the first 5 d of feeding acorns only, mice in the nonacclimated group lost, on average, 17.5% of their body mass, while those in the acclimated group lost only 2.5%. Food intake, dry matter digestibility, and nitrogen digestibility were higher in the acclimated group than in the nonacclimated group. The results indicate that wood mice can mitigate the negative effects of tannins by acclimation. Path analysis revealed that increased secretion of PRPs and abundance of Lactobacillus type of TPB might explain the acclimation to tannins. PMID:16770711

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

2006-05-25

284

Cardiac syncope.  

PubMed

Clinicians who diagnose and manage epilepsy frequently encounter diagnoses of a nonneurological nature, particularly when assessing patients with transient loss of consciousness (T-LOC). Among these, and perhaps the most important, is cardiac syncope. As a group, patients with cardiac syncope have the highest likelihood of subsequent sudden death, and yet, unlike sudden unexpected death in epilepsy (SUDEP) for example, it is the norm for these tragic occurrences to be both easily predictable and preventable. In the 12 months following initial presentation with cardiac syncope, sudden death has been found to be 6 times more common than in those with noncardiac syncope (N Engl J Med 309, 1983, 197). In short, for every patient seen with T-LOC, two fundamental aims of the consultation are to assess the likelihood of cardiac syncope as the cause, and to estimate the risk of future sudden death for the individual. This article aims to outline for the noncardiologist how to recognize cardiac syncope, how to tell it apart from more benign cardiovascular forms of syncope as well as from seizures and epilepsy, and what can be done to predict and prevent sudden death in these patients. This is achieved through the assessment triad of a clinical history and examination, risk stratification, and 12-lead electrocardiography (ECG). PMID:23153208

Anderson, Joseph; O'Callaghan, Peter

2012-12-01

285

Resin Glycosides from the Morning Glory Family  

NASA Astrophysics Data System (ADS)

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

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

286

30-normedicagenic acid glycosides from Chenopodium foliosum.  

PubMed

Two new glycosides of 30-normedicagenic acid, namely 3-O-[beta-D-glucuronopyranosyl methyl ester]-2beta,3beta-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28-O-beta-D-glucopyranosyl ester, and 3-O-beta-D-glucopyranosyl-2beta,3beta-dihydroxy-30-noroleane- 12,20(29)-diene-23,28-dioic acid, together with the known 3-O-beta-glucopyranosyl-2beta,3beta-dihydroxy-30-noroleane-12,20(29)-diene-23 ,28-dioic acid 28-O-beta-glucopyranosyl ester, and 3-O-beta-glucuronopyranosyl-2beta,3beta-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28-O-beta-glucopyranosyl ester were isolated from the aerial parts of Chenopodium foliosum Asch. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, UV, IR) and HRMS-ESI. The compounds were tested for cytotoxicity on three leukemic cell lines (BV-173, SKW-3, HL-60). In addition, the saponins showed moderate stimulatory effects on interleukin-2 production in PHA/PMA stimulated Jurkat E6.1 cells. PMID:23285798

Nedialkov, Paraskev T; Kokanova-Nedialkova, Zlatina; Bücherl, Daniel; Momekov, Georgi; Heilmann, Jörg; Nikolov, Stefan

2012-11-01

287

Glycosidic Inhibitors of Melanogenesis from Leaves of Passiflora edulis.  

PubMed

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

2013-10-01

288

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

2007-01-01

289

Study on the Inhibitory Effect of Tannins and Flavonoids against the 1,1Diphenyl2-picrylhydrazyl Radical  

Microsoft Academic Search

Fifty-one tannins and forty-one flavonoids isolated from Oriental medicinal herbs were evaluated for their antioxidant ability with a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-generating system. The results showed that tannins and certain flavonoids are potential free-radical scavengers, and that their activity against the DPPH radical is closely associated with their chemical structure. A comparison of the two classes of compounds showed that tannins

Takako Yokozawa; Cui Ping Chen; Erbo Dong; Takashi Tanaka; Gen-Ichiro Nonaka; Itsuo Nishioka

1998-01-01

290

Effect of tannin on oxidative damage of ocular lens.  

PubMed

The protective effect of geraniin (tannin from Geranium thunbergii) against oxidative damage was examined in the mouse ocular lens. Oxidative damage in the lens was induced by diamide, diazene dicarboxylic acid bis (N,N-dimethylamide); diamide oxidized the sulfhydryl groups in both the membrane and cytoplasm but did not increase lipid peroxide. Geraniin showed protective effects on the changes in the Na+/K+ ratio, GSH level, Na,K-ATPase activity, GSH reductase activity and the sulfhydryl level of the membranous protein in the diamide-treated lens, but such protective effects of geraniin were not observed in the cell-free system of the lens. In addition, geraniin itself was unable to reduce GSSG to GSH and also unable to inhibit the oxidative reaction of the sulfhydryl group to diamide. These results suggest that in the intact lens geraniin would act primarily on the lens cell membrane surface to inhibit an influx of diamide into the inner part of the plasma membrane and the cytoplasm, and consequently that geraniin may protect sulfhydryl groups in the cell membrane and cytoplasm from their oxidation by diamide and keep the redox system of the lens in a normal state. PMID:3184550

Fukaya, Y; Nakazawa, K; Okuda, T; Iwata, S

1988-01-01

291

EBV DNA polymerase inhibition of tannins from Eugenia uniflora.  

PubMed

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

2000-06-30

292

Wirkung von Tannin und Adlerfarn auf die Fertilitaet von Maeusen (Effects of Tannin and Bracken Fern on the Fertility of Mice).  

National Technical Information Service (NTIS)

In a 3-generation test on mice the influence of bracken fern and one of his possibly important constituent parts - tannin - on the fertility was investigated. The substances were given as food additives. A negative influence could not be observed in any c...

A. E. our R. Hruby

1980-01-01

293

Central nervous system depressant action of flavonoid glycosides.  

PubMed

The pharmacological effects on the central nervous system (CNS) of a range of available flavonoid glycosides were explored and compared to those of the glycosides 2S-hesperidin and linarin, recently isolated from valeriana. The glycosides 2S-neohesperidin, 2S-naringin, diosmin, gossipyn and rutin exerted a depressant action on the CNS of mice following i.p. injection, similar to that found with 2S-hesperidin and linarin. We demonstrate in this work that these behavioural actions, as measured in the hole board, thiopental induced sleeping time and locomotor activity tests, are unlikely to involve a direct action on gamma-aminobutyric acid type A (GABA(A)) receptors. The corresponding aglycones were inactive, pointing to the importance of the sugar moieties in the glycosides in their CNS depressant action following systemic administration. The pharmacological properties of the flavonoid glycosides studied here, in addition to our previous results with hesperidin and linarin, opens a promising new avenue of research in the field. PMID:16698011

Fernández, Sebastián P; Wasowski, Cristina; Loscalzo, Leonardo M; Granger, Renee E; Johnston, Graham A R; Paladini, Alejandro C; Marder, Mariel

2006-04-06

294

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

PubMed

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

2011-08-03

295

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

PubMed

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

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

2011-12-01

296

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

NASA Astrophysics Data System (ADS)

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

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

2009-06-01

297

Cardiac emergencies.  

PubMed

The diagnosis and management of pediatric cardiac emergencies can be challenging and complicated. Early presentations are usually the result of ductal-dependent lesions and appear with cyanosis and shock. Later presentations are the result of volume overload or pump failure and present with signs of congestive heart failure. Acquired diseases also present as congestive heart failure or arrhythmias. PMID:23915599

Barata, Isabel Araujo

2013-08-01

298

ISOFLAVONE CONJUGATES AND MINOR GLYCOSIDES EXTRACTED FROM PEANUT HEARTS USING HPLC-MS  

Technology Transfer Automated Retrieval System (TEKTRAN)

High performance liquid chromatography and electrospray mass spectrometry (ESI) was used to characterize isoflavone glycosidic conjugates and minor glycosides extracted from peanut meal. The selected extraction method combined the removal of isoflavones and their conjugates with an alcoholic solvent...

299

New anthraquinone glycosides from the roots of Morinda citrifolia.  

PubMed

Six new anthraquinone glycosides: digiferruginol-1-methylether-11-O-beta-gentiobioside (1); digiferruginol-11-O-beta-primeveroside (2); damnacanthol-11-O-beta-primeveroside (3); 1-methoxy-2-primeverosyloxymethyl-anthraquinone-3-olate (4); 1-hydroxy-2-primeverosyloxymethyl-anthraquinone-3-olate (5); and 1-hydroxy-5,6-dimethoxy-2-methyl-7-primeverosyloxyanthraquinone (6) were isolated from Morinda citrifolia (Rubiaceae) roots together with four known anthraquinone glycosides. The structures of the new compounds were established using spectral methods. For five of the new compounds, the sugar is attached via the hydroxymethyl group of the anthraquinone C-2 carbon. This type of bond is rarely found for anthraquinone glycosides isolated from natural sources. PMID:19233251

Kamiya, Kohei; Hamabe, Wakako; Tokuyama, Shogo; Satake, Toshiko

2009-02-21

300

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

PubMed

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

301

Novel Strategies for Upstream and Downstream Processing of Tannin Acyl Hydrolase  

PubMed Central

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

Rodriguez-Duran, Luis V.; Valdivia-Urdiales, Blanca; Contreras-Esquivel, Juan C.; Rodriguez-Herrera, Raul; Aguilar, Cristobal N.

2011-01-01

302

Novel strategies for upstream and downstream processing of tannin acyl hydrolase.  

PubMed

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

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

2011-09-19

303

Toxicity to endothelial cells mediated by cotton bract tannin. Potential contribution to the pathogenesis of byssinosis.  

PubMed Central

Byssinosis is an occupational disease of textile workers caused by exposure to the bract portion of the cotton plant in the form of mill dust. The authors established an in vitro cytotoxicity assay using 51Cr release to assess time- and dose-dependent toxicity of condensed tannin, a component of bracts, on porcine aortic and pulmonary arterial endothelial cells. Tannin produced dose-dependent toxicity to both types of endothelial cells; aortic endothelial cells were more sensitive than were endothelial cells from the pulmonary artery. Skin fibroblasts were relatively insensitive to tannin. Cytotoxicity was not immediate. Release of 51Cr was preceded by a several-hour period during which the endothelial cells underwent profound morphologic changes (as assessed by light and electron microscopy). Even brief exposure of endothelial cells to tannin produced later toxicity and morphologic changes. Condensed tannin causes time- and dose-dependent injury to endothelial cells in vitro at doses potentially achievable in vivo. Images Figure 10 Figure 11 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Figure 9 Figure 12 Figure 14

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

1986-01-01

304

Adsorption mechanism of palladium by redox within condensed-tannin gel.  

PubMed

Condensed-tannin gel particles with polyhydroxyphenyl groups were synthesized as the adsorbent for the new recovery system of palladium (Pd), which was simple and generated little secondary waste in comparison with the conventional recovery processes. The properties of condensed-tannin gel particles for the Pd adsorption were examined in PdCl2 aqueous solution and it was found that Pd(II) was adsorbed onto the tannin gel particles as a reduced metallic Pd through redox reaction mechanism: chloropalladium(II) species were reduced to Pd(0), while hydroxyl groups of condensed-tannin gel were oxidized during the adsorption. Additionally, it was observed that Pd(II) species containing fewer Cl, such as PdCl2(H2O)2 and PdCl(H2O)3+, were more favorable for the adsorption than PdCl3(H2O)- and PdCl4(2-). By utilizing such characteristics of tannin gel particles, it is expected that they can be applied to recover Pd efficiently and simply with low cost. PMID:15862331

Ho Kim, Yeon; Nakano, Yoshio

2005-04-01

305

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

PubMed

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

2013-05-21

306

Flocculation of Microcystis aeruginosa using modified larch tannin.  

PubMed

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

2013-05-17

307

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

Microsoft Academic Search

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

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

2010-01-01

308

New anthraquinone glycosides from the roots of Morinda citrifolia  

Microsoft Academic Search

Six new anthraquinone glycosides: digiferruginol-1-methylether-11-O-?-gentiobioside (1); digiferruginol-11-O-?-primeveroside (2); damnacanthol-11-O-?-primeveroside (3); 1-methoxy-2-primeverosyloxymethyl-anthraquinone-3-olate (4); 1-hydroxy-2-primeverosyloxymethyl-anthraquinone-3-olate (5); and 1-hydroxy-5,6-dimethoxy-2-methyl-7-primeverosyloxyanthraquinone (6) were isolated from Morinda citrifolia (Rubiaceae) roots together with four known anthraquinone glycosides. The structures of the new compounds were established using spectral methods. For five of the new compounds, the sugar is attached via the hydroxymethyl group of the anthraquinone C-2 carbon.

Kohei Kamiya; Wakako Hamabe; Shogo Tokuyama; Toshiko Satake

2009-01-01

309

Caucasicosides E-M, furostanol glycosides from Helleborus caucasicus.  

PubMed

Nine furostanol glycosides, namely caucasicosides E-M, were isolated from the MeOH extract of the leaves of Helleborus caucasicus, along with 11 known compounds including nine furostanol glycosides, a bufadienolide and an ecdysteroid. Their structures were established by the extensive use of 1D and 2D NMR experiments along with ESIMS(n) analyses. The steroidal composition of leaves of H. caucasicus shows as particular feature the occurrence of steroidal compounds belonging to the 5? series, unusual for Helleborus species, and in particular, caucasicosides F-H are based on a 5?-polyhydroxylated steroidal aglycon never reported before. PMID:21893324

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

2011-09-03

310

Three new steroid glycosides from the starfish Asterina pectinifera.  

PubMed

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

2013-01-23

311

Phenylethanoid and flavone glycosides from Ruellia tuberosa L.  

PubMed

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

2012-03-25

312

Cardiac tamponade.  

PubMed Central

Cardiac tamponade is a cardiological emergency requiring prompt treatment in order to avoid a fatal outcome. It can complicate a number of medical conditions and it is important, therefore, that all practitioners are aware of its presentation, diagnosis and management. These are outlined. We suggest that, with certain specific and important exceptions, percutaneous catheter pericardiocentesis is to be recommended in the management of cardiac tamponade. We include a review of 51 consecutive cases treated at our own institution. Catheter pericardiocentesis was successful in 49 (96%) cases and 36 (80%) patients did not require any further intervention. There were no major and only two minor complications which required no additional treatment. We review previous literature concerning percutaneous pericardiocentesis. Using recommended procedures, pericardiocentesis is successful in 90-100% of cases and major complications are rare. Images Figure 1 Figure 2 Figure 3

Ball, J. B.; Morrison, W. L.

1997-01-01

313

Cardiac optogenetics.  

PubMed

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

Entcheva, Emilia

2013-03-01

314

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.

Weisse, Allen B.

2011-01-01

315

Chemical variation of tannins and triterpenes in Brazilian populations of Maytenus ilicifolia Mart. Ex Reiss.  

PubMed

Maytenus ilicifolia and Maytenus aquifolia species are widely used as a cicatrisation agent, an anti-spasmodic, contraceptive, antiulcerogenic, diuretic and analgesic. Considering the importance of these species in popular medicine, this work is focused on the determination of the chemical content of tannins and the triterpenes friedelan-3-one, friedelan-3-ol and friedelin in 15 native populations of Maytenus ilicifolia distributed in the south and mind-west regions of Brazil. Correlation of the concentration of these compounds with the environmental parameters such as average annual temperature, climate, vegetation, geomorphology, latitude and altitude was determined using Pearson's coefficient. Results showed that average annual temperature and climate have significant effect on tannin content at a 95% confidence level. The highest tannin concentration was found in Ponta Porã population, and for the triterpenes investigated, a significant correlation between their concentrations with the environmental variables studied was not verified. PMID:19675936

Mossi, A J; Mazutti, M; Paroul, N; Corazza, M L; Dariva, C; Cansian, R L; Oliveira, J V

2009-05-01

316

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

PubMed Central

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

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

1995-01-01

317

Gallic acid and hydrolysable tannins are formed in birch leaves from an intermediate compound of the shikimate pathway  

Microsoft Academic Search

Gallic acid is the starting material for hydrolysable tannin synthesis, but the mechanism of its formation in higher plants has not been known. To elucidate the pathway of gallic acid synthesis in the leaves of mountain birch (Betula pubescens ssp. czerepanovii), we studied the effects of glyphosate (N-[phosphonomethyl]-glycine) on the levels of individual hydrolysable tannins. Glyphosate is known to block

Vladimir Ossipov; Juha-Pekka Salminen; Svetlana Ossipova; Erkki Haukioja; Kalevi Pihlaja

2003-01-01

318

Effects of Purified Persimmon Tannin and Tannic Acid on Survival and Reproduction of Bean Bug, Riptortus clavatus  

Microsoft Academic Search

We evaluated the effects of tannic acid and purified persimmon tannin on survival and reproduction of bean bugs, Riptortus clavatus. Feeding behavior of R. clavatus was also examined on sweet (cv. Fuyu) and astringent (cv. Chongdosi) persimmon fruits. Soluble tannin in sweet persimmon fruits decreased from 3% in early June to 0.5% in late September, but it increased from 2

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

2004-01-01

319

Methods and pitfalls of extracting condensed tannins and other phenolics from plants: Insights from investigations on Eucalyptus leaves  

Microsoft Academic Search

Optimal conditions for extraction of tannins and other phenolics from tree foliage and their subsequent storage rarely have been investigated. We investigated methods of drying leaves, optimal solvents, and the effects of light and temperature on the extractability and stability of condensed tannins (proanthocyanidins) and total phenolics from leaves ofEucalyptus trees. Aqueous acetone was a better solvent than aqueous methanol

Steven J. Cork; Andrew K. Krockenberger

1991-01-01

320

Ellagitannins have Greater Oxidative Activities than Condensed Tannins and Galloyl Glucoses at High pH: Potential Impact on Caterpillars  

Microsoft Academic Search

Plants synthesize a diversity of tannin structures but little is known about whether these different types have different oxidative activities in herbivores. Oxidative activities of hydrolyzable and condensed tannins were compared at pH 10 with two methods: EPR spectrometry was used to quantify semiquinone radicals in anoxic conditions and a spectrophotometric assay was used to measure the rate of browning

Raymond V. Barbehenn; Christopher P. Jones; Ann E. Hagerman; Maarit Karonen; Juha-Pekka Salminen

2006-01-01

321

IMPACT OF FORAGE CONDENSED TANNINS ON PROTEIN UTILIZATION AND NITROGEN CYCLING ON DAIRY FARMS: A PROGRESS REPORT  

Technology Transfer Automated Retrieval System (TEKTRAN)

Binding of condensed tannins to protein can moderate proteolysis in forages during ensiling, ruminal digestion, and decay of residues in soil. We are conducting forage quality, feeding, cropping, and manure management studies with tannin-free alfalfa and three birdsfoot trefoil populations containin...

322

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

2008-01-01

323

On the nature of coagulated tannins in astringent-type persimmon fruit after an artificial treatment of astringency removal  

Microsoft Academic Search

There are many reports concerning the astringency removal of persimmon fruit by ethanol or carbon dioxide treatment. However, none are concerned with the chemical characteristics of tannins after astringency removal, so the chemical properties of coagulated tannins after the treatment were investigated. For this purpose, the astringency of ‘Hiratanenashi’ persimmon (Diospyros kaki Thunb.) fruit was removed by enclosing them for

M. Oshida; K. Yonemori; A. Sugiura

1996-01-01

324

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

325

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

2001-01-01

326

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

327

A new stilbene glycoside from the n -butanol fraction of Veratrum dahuricum  

Microsoft Academic Search

A new stilbene glycoside, 5-methylresveratrol-3,4?-O-?-D-diglucopyranoside (1), was isolated from the n-butanol fraction of the rhizomes of Veratrum dahuricum, together with five known stilbenoids: resveratrol-3-O-?-D-glycoside (2), 4?-methylresveratrol-3-O-?-D-glycoside (3), oxyresveratrol-4?-O-?-D-glycoside (4), oxyresveratrol-3-O-?-D-glycoside (5), and oxyresveratrol-3,4?-O-?-D-diglycoside (6), and found for the first time in the investigated plant. The structures of six isolates were identified on the basis of\\u000a 1D and 2D NMR data.

Li-Min Dai; Jian Tang; Hui-Liang Li; Yun-Heng Shen; Cai-Yun Peng; Wei-Dong Zhang

2009-01-01

328

Combined biodegradation and ozonation for removal of tannins and dyes for the reduction of pollution loads  

Microsoft Academic Search

Purpose  Tannins and dyes pose major threat to the environment by generating huge pollution problem. Biodegradation of wattle extract,\\u000a chrome tannin and dye compounds using suitable fungal culture namely Aspergillus niger, Penicillium sp. were carried out. In addition to these, ozone treatment was carried out to get higher degradation rate.\\u000a \\u000a \\u000a \\u000a \\u000a Results  The results were monitored by carrying out chemical oxygen demand (COD),

James Kanagaraj; Asit Baran Mandal

329

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

PubMed

We used ion mobility spectrometry to explore conformational adaptability of intrinsically disordered proteins bound to their targets in complex mixtures. We investigated the interactions between a human salivary proline-rich protein IB5 and a model of wine and tea tannin: epigallocatechin gallate (EgCG). Collisional cross sections of naked IB5 and IB5 complexed with N = 1-15 tannins were recorded. The data demonstrate that IB5 undergoes an unfolded to folded structural transition upon binding with EgCG. PMID:21524106

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

2011-04-27

330

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.

1998-01-01

331

Use of glycoside hydrolase family 8 xylanases in baking  

Microsoft Academic Search

Xylanases have long been used in the baking industry for improving dough stability and flexibility and for increasing bread volume and crumb structure. Only xylanases from glycoside hydrolase families 10 and 11 appear to have been tested in this application and only those from the latter family have as yet found application. Interestingly, enzymes with a putative xylanase activity are

Tony Collins; Anne Hoyoux; Agnès Dutron; Jacques Georis; Bernard Genot; Thierry Dauvrin; Filip Arnaut; Charles Gerday; Georges Feller

2006-01-01

332

Structural revision of two flavanonol glycosides from Smilax glabra.  

PubMed

The structures of two flavanonol glycosides isolated from Smilax glabra, named smitilbin and neosmitilbin, have been revised to isoastilbin and neoastilbin, respectively. The revised structures were determined based on intensive studies of chemical interconversion, NMR spectroscopy, and X-ray crystallographic analysis. The latest NMR data were also summarized. PMID:19199231

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

2009-02-06

333

Cytotoxic phenylpropanoid glycosides from Fagopyrum tataricum (L.) Gaertn  

Microsoft Academic Search

Fagopyrum tataricum (L.) Gaertn (tartary buckwheat) is an ancient dicotyledonous crop belonging to Polygonaceae family. Besides its benefits for human consumption, tartary buckwheat is also an important folk medicine in China for its antioxidant, antitumor, hypotensive, hypoglycemic and hypolipidemic activities. Phytochemical investigation of the ethyl acetate fraction of tartary buckwheat roots led to the isolation of seven new phenylpropanoid glycosides,

Chengjian Zheng; Changling Hu; Xueqin Ma; Cheng Peng; Hong Zhang; Luping Qin

334

A new flavone glycoside from seeds of Daucus carota.  

PubMed

Phytochemical examination of seeds of Daucus carota L. resulted in the isolation of apigenin -4'-O-beta-D-glucoside, kaempferol-3-O-beta-D-glucoside and a new flavone glycoside which was characterised as apigenin-7-O-beta-D-galactopyranosyl-(1-->4)-O-beta-D-mannopyranoside. PMID:17396982

Gupta, K R; Niranjan, G S

1982-12-01

335

Glycosidation of Methanol with Ribose: An Interdisciplinary Undergraduate Laboratory Experiment  

ERIC Educational Resources Information Center

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

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

2010-01-01

336

Physiological functions of solanaceous and tomato steroidal glycosides  

Microsoft Academic Search

Solanaceous plants are widely distributed. They are used as food and in folk medicine. Our studies focused on these plants, starting with Solanum lyratum and S. nigrum, which are used as anti-cancer and anti-herpes agents. Extensive investigations in 45 Solanum plant species revealed that a considerable amount of glycosides such as spirosolane, solanidane, spirostane and furostane is in these plants,

Toshihiro Nohara; Tsuyoshi Ikeda; Yukio Fujiwara; Sayaka Matsushita; Eishin Noguchi; Hitoshi Yoshimitsu; Masateru Ono

2007-01-01

337

Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis  

Microsoft Academic Search

Remarkable advances in glycobiology in recent years have stimulated a resurgence of interest in carbohydrate chemistry. The challenge of producing the complex glycosides and oligosaccharides needed for research in glycobiology has led to the development of enzymatic methods that are now firmly established as part of the synthetic repertoire of the carbohydrate chemist.

David HG Crout; Gabin Vic

1998-01-01

338

New secoiridoid glycosides from the buds of Lonicera macranthoides.  

PubMed

Two new secoiridoid glycosides, named ethyl secologanoside (1) and 6'-O-alpha-L-arabinopyranosyl demethylsecologanol (2), together with three known ones, secologanoside (3), secoxyloganin (4), and loniceroside (5), were isolated from the dried buds of Lonicera macranthoides. The structures of the new compounds were determined on the basis of detailed spectroscopic analyses and acidic hydrolysis. PMID:23413549

Liu, Jiang; Zhang, Jing; Wang, Feng; Chen, Xingfu

2012-12-01

339

Chemically Synthesized Oligosaccharides, 1994. A Searchable Table of Glycosidic Linkages  

Microsoft Academic Search

This review of the literature on oligosaccharide synthesis tabulates over 700 glycosidic linkages that have been chemically synthesized in the “popular literature” in the year 1994. The “popular literature” consists of the following journals, most frequently used for reporting oligosaccharide synthesis: Acta Chem. Scand., Angew. Chem. Intl. Ed. Engl., Aust. J. Chem., Bioorg. Med. Chem., Bioorg. Med. Chem. Lett., Bull.

Frank Barresi; Ole Hindsgaul

1995-01-01

340

New and rare flavonol glycosides from leaves of Syzygium samarangense  

Microsoft Academic Search

Two flavonol glycosides have been isolated and characterised from leaves of Syzygium samarangense. One is the rare mearnsitrin (1) while the second, 2?-C-methyl-5?-O-galloylmyricetin-3-O-a-l-rhamnopyranoside (2), is new. Detailed spectral data are provided for both.

A. G. R Nair; S Krishnan; C Ravikrishna; K. P Madhusudanan

1999-01-01

341

Melanogenesis inhibitory activity of monoterpene glycosides from Gardeniae Fructus.  

PubMed

A new iridoid glycoside, 10-O-(4"-O-methylsuccinoyl)geniposide (7), and two new pyronane glycosides, jasminosides Q and R (13 and 14, resp.), along with nine known iridoid glycosides, 1-6 and 8-10, and two known pyronane glycosides, 11 and 12, were isolated from a MeOH extract of Gardeniae Fructus, the dried ripe fruit of Gardenia jasminoides (Rubiaceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Upon evaluation of compounds 1-14 on the melanogenesis in B16 melanoma cells induced with ?-melanocyte-stimulating hormone (?-MSH), three compounds, i.e., 6-O-p-coumaroylgeniposide (3), 7, and 6'-O-sinapoyljasminoside (12), exhibited inhibitory effects with 21.6-41.0 and 37.5-47.7% reduction of melanin content at 30 and 50 ?M, respectively, with almost no toxicity to the cells (83.7-106.1% of cell viability at 50 ?M). PMID:22899609

Akihisa, Toshihiro; Watanabe, Kensuke; Yamamoto, Ayako; Zhang, Jie; Matsumoto, Masahiro; Fukatsu, Makoto

2012-08-01

342

Absence of cyanogenic glycosides in the tribe Miconieae (Melastomataceae)  

Microsoft Academic Search

In order to compare ant and non-ant defended species of Melastomataceae, production of hydrogen cyanide gas was tested in the field for 51 species of 10 genera of the tribe Miconieae. Using both the picric acid and the Feigl–Anger tests all populations surveyed tested negative for the presence of cyanogenic glycosides. These results confirm that cyanogenesis is rare in the

Fabián A. Michelangeli; Eloy Rodriguez

2005-01-01

343

Antioxidant flavonol glycosides from Elaeocarpus serratus and Filicium decipiens.  

PubMed

Chemical investigation of the leaves of Elaeocarpus serratus yielded myricitrin (1), mearnsetin 3-O-?-D-glucopyranoside (2), mearnsitrin (3), tamarixetin 3-O-?-L-rhamnopyranoside (4) and the fruits of Filicium decipiens yielded three flavonol glycosides, kaempferol 3-O-rutinoside (5), kaempferol 3-O-robinobioside (6) and trifolin (7). Compound 1 showed strong antioxidant activity against DPPH. PMID:21923561

Jayasinghe, Lalith; Amarasinghe, Nilupa R; Arundathie, B G Suranga; Rupasinghe, G Kalinga; Jayatilake, N H Ayona N; Fujimoto, Yoshinori

2011-09-19

344

Glycosidation of Methanol with Ribose: An Interdisciplinary Undergraduate Laboratory Experiment  

ERIC Educational Resources Information Center

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

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

2010-01-01

345

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: http://mycoCLAP.fungalgenomics.ca/

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

2011-01-01

346

Functional genomic analysis of Arabidopsis thaliana glycoside hydrolase family 35  

Microsoft Academic Search

Catalysing the hydrolysis of terminal ?-galactosyl residues from carbohydrates, galactolipids, and glycoproteins, glycoside hydrolase family 35 (?-galactosidases; BGALs) are widely distributed in plants and believed to play many key roles, including modification of cell wall components. Completion of the Arabidopsis thaliana genome sequencing project has, for the first time, allowed an examination of the total number, gene structure, and evolutionary

Young Ock Ahn; Meiying Zheng; David R. Bevan; Asim Esen; Shin-Han Shiu; Jonas Benson; Hsiao-Ping Peng; Joseph T. Miller; Chi-Lien Cheng; Jonathan E. Poulton; Ming-Che Shih

2007-01-01

347

Computational analysis of the phylogeny and thermodynamics of glycoside hydrolases  

Microsoft Academic Search

My research has focused on using computation by means of phylogenetic analysis and molecular mechanics docking studies to further extend knowledge of glycoside hydrolases (GHs). Phylogenetic analysis was used to crystallize the fundamental differences between specific types of cellulases in GH family 6 (GH6). Cellulase enzymes were then examined for functional divergence in order to determine the cause of substrate

John Blakely Mertz

2008-01-01

348

Two new flavonol glycosides from Gymnema sylvestre and Euphorbia ebracteolata  

Microsoft Academic Search

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

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

2004-01-01

349

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

PubMed

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

2012-10-19

350

Differential effects of sugar maple, red oak, and hemlock tannins on carbon and nitrogen cycling in temperate forest soils.  

PubMed

Tannins are abundant secondary chemicals in leaf litter that are hypothesized to slow the rate of soil-N cycling by binding protein into recalcitrant polyphenol-protein complexes (PPCs). We studied the effects of tannins purified from sugar maple, red oak, and eastern hemlock leaf litter on microbial activity and N cycling in soils from northern hardwood-conifer forests of the northeastern US. To create ecologically relevant conditions, we applied tannins to soil at a concentration (up to 2 mg g(-1) soil) typical of mineral soil horizons. Sugar maple tannins increased microbial respiration significantly more than red oak or hemlock tannins. The addition of sugar maple tannins also decreased gross N mineralization by 130% and, depending upon the rate of application, decreased net rates of N mineralization by 50-290%. At low concentrations, the decrease in mineralization appeared to be driven by greater microbial-N immobilization, while at higher concentrations the decrease in mineralization was consistent with the formation of recalcitrant PPCs. Low concentrations of red oak and hemlock tannins stimulated microbial respiration only slightly, and did not significantly affect fluxes of inorganic N in the soil. When applied to soils containing elevated levels of protein, red oak and hemlock tannins decreased N mineralization without affecting rates of microbial respiration, suggesting that PPC formation decreased substrate availability for microbial immobilization. Our results indicate that tannins from all three species form recalcitrant PPCs, but that the degree of PPC formation and its attendant effect on soil-N cycling depends on tannin concentration and the pool size of available protein in the soil. PMID:18210159

Talbot, Jennifer M; Finzi, Adrien C

2008-01-19

351

Inhibition of Steryl Glycoside Biosynthesis by Acyl Coenzyme A and by Digitonin  

PubMed Central

ATP, GTP, CoA, Mg2+, and Mn2+ did not inhibit biosynthesis of steryl glycoside and acylated steryl glycoside when added singly to enzyme preparations from spinach leaves. The combination of ATP (but not GTP), CoA, and Mg2+ or Mn2+ caused marked inhibition, especially of steryl glycoside biosynthesis, when reaction mixture concentrations of the additions were 0.2 millimolar. Inhibition was attributed to acyl-CoA and could be reproduced by palmitoyl-CoA. The inhibition could be partially prevented by bovine serum albumin. The effects of palmitoyl-CoA were distinct at 10 micromolar, and 50% inhibition of biosynthesis was observed at 40 micromolar. Digitonin (0.6 millimolar) stopped steryl glycoside biosynthesis but permitted the conversion of steryl glycoside to acylated steryl glycoside, thus eliminating the possibility that acylated steryl glycoside is formed from sterol + an acyl-glucose donor.

Garcia, Raymond E.; Mudd, J. Brian

1980-01-01

352

Cardiac pacing.  

PubMed

The basic electrophysiology of temporary and permanent cardiac pacing is reviewed, as are the indications, the types of pacing systems, and the methods of implantation. Recent developments in power sources and leads are described. The mercury-zinc battery is now obsolete and is being replaced by lithium, rechargeable, and isotopic power systems. While ventricular pacing continues to be the standard, a brief review of atrial programmed systems is given, including atrial pacing and atrioventricular synchronized and atrioventricular sequential pacing. Conventional pacing is aimed at the control of symptomatic bradycardia. Brief reference is made to experimental pacing systems designed to control ventricular or supraventricular tachyarrhythmias. PMID:453992

Smyth, N P

1979-03-01

353

Gold-catalyzed glycosidations: unusual cleavage of the interglycosidic bond while studying the armed\\/disarmed effect of propargyl glycosides  

Microsoft Academic Search

Armed\\/disarmed effect of propargyl glycosides in the presence of AuBr3 is studied. Observed that oxophilic AuBr3 cleaves interglycosidic bond of an armed disaccharide resulting in the formation of a disaccharide and a 1,6-anhydro sugar. Trisaccharides were obtained after fine tuning the reactivity of the glycosyl donor with different protecting groups.

Abhijeet K. Kayastha; Srinivas Hotha

2010-01-01

354

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

2008-01-01

355

Wood Panel Adhesives from Low Molecular Mass Lignin and Tannin without Synthetic Resins  

Microsoft Academic Search

Mixed interior wood panel tannin adhesive formulations were developed in which lignin was in considerable proportion, 50%, of the wood panel binder, and in which no 'fortification' with synthetic resins, such as isocyanates or phenol-formaldehyde resins as used in the past, was necessary to obtain results satisfying relevant standards. A low molecular mass lignin obtained industrially by formic acid\\/acetic acid

P. Navarrete; H. R. Mansouri; A. Pizzi; S. Tapin-Lingua; B. Benjelloun-Mlayah; H. Pasch; S. Rigolet

2010-01-01

356

Mangrove tannins and their flavanoid monomers as alternative steel corrosion inhibitors in acidic medium  

Microsoft Academic Search

The inhibitive behaviour on steel of flavanoid monomers that constitute mangrove tannins namely catechin, epicatechin, epigallocatechin and epicatechingallate was investigated in an aerated HCl solution via electrochemical methods. The monomers were found to be mainly cathodic inhibitors and the inhibition efficiency was dependent on concentration. To explain the adsorptive behaviour of the molecules on the steel surface, a semiempirical approach

Afidah A. Rahim; E. Rocca; J. Steinmetz; M. J. Kassim; R. Adnan; M. Sani Ibrahim

2007-01-01

357

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

358

5?Reductase inhibitory tannin-related compounds isolated from Shorea laeviforia  

Microsoft Academic Search

Five tannin-related compounds – gallic acid, flavogallonic acid dilactone, valoneic acid dilactone, gallagyldilactone, ellagic acid – were isolated from the heartwood of Shorea laeviforia, and the inhibitory activity of each against rat liver 5 ?-reductase was evaluated. Valoneic acid dilactone and gallagyldilactone exhibited positive inhibitory activity, but gallic acid and ellagic acid did not. Flavogallonic acid dilactone stimulated 5 ?-reductase

Yoshio Hirano; Ryuichiro Kondo; Kokki Sakai

2003-01-01

359

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

360

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

PubMed

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

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

2012-11-17

361

Tannins and catechin gallate mediate the vasorelaxant effect of Arbutus unedo on the rat isolated aorta.  

PubMed

This study examined the vascular effect of Arbutus leaves (aqueous extract) and described the isolation of several fractions responsible for their vasorelaxant activity. The aqueous extract (AE) of leaves was tested on rat aortic rings precontracted with 0.1 microm noradrenaline. At 10(-2) g/L, AE produced an endothelium dependent relaxation of 66% +/- 5%, (n = 8). The leaves of Arbutus were then extracted successively with different solvents and the methanol extract was the most active. When tannins (primarily condensed tannins) were precipitated from the methanol extract, they showed a strong vasorelaxant activity (87% +/- 4%, n = 5), whereas the elimination of tannins in the methanol extract reduced significantly its vasorelaxant activity (42% +/- 8%, n = 8, p < 0.005). The methanol extract was further separated semi-preparatively by reversed-phase HPLC. Four fractions (Fr2, Fr3, Fr4 and Fr6) were the most active and produced 88% +/- 2% (n = 5), 75% +/- 6% (n = 5), 76% +/- 3% (n = 7) and 77% +/- 3% (n = 10) relaxation, respectively. These four fractions mainly correspond to polyphenol compounds. Analysis of Fr6 indicated that this fraction contained catechin gallate. In conclusion, the vasorelaxant activity of Arbutus is likely to be due to polyphenol compounds, primarily condensed tannins and catechin gallate. PMID:15597331

Legssyer, Abdelkhaleq; Ziyyat, Abderrahim; Mekh, Hassane; Bnouham, Mohamed; Herrenknecht, Christine; Roumy, Vincent; Fourneau, Christophe; Laurens, Alain; Hoerter, Jacqueline; Fischmeister, Rodolphe

2004-11-01

362

Use of dye-labeled protein as spectrophotometric assay for protein precipitants such as tannin  

Microsoft Academic Search

Bovine serum albumin has been covalently labeled with Remazol brilliant blue R to provide a substrate for a convenient spectrophotometric assay for protein precipitants. The blue protein is especially useful for measuring protein precipitation by vegetable tannins because its absorption maximum is at a wavelength where plant pigments exhibit minimum absorption. Blue BSA has been used to determine, by competition

Thomas N. Asquith; Larry G. Butler

1985-01-01

363

CONDENSED TANNIN AND POLYPHENOL INTERACTIONS WITH FORAGE PROTEIN AS INFLUENCED BY THE SEVERITY OF MECHANICAL CONDITIONING  

Technology Transfer Automated Retrieval System (TEKTRAN)

The severity of conditioning may alter N fractions in forages, particularly if protein-binding tannins and polyphenols are present. In 2002 and 2003, cuttings of alfalfa, birdsfoot trefoil, and red clover were conventionally conditioned or severely macerated and then conserved as silage and hay. For...

364

Attempts to deactivate tannins in fodder shrubs with physical and chemical treatments  

Microsoft Academic Search

Chopping, water sprinkling, storage under aerobic and anaerobic conditions, urea, wood ash, activated charcoal and polyethylene glycol 4000 (PEG) treatments were evaluated for their efficiency in deactivating tannins in shrub foliage. In a first trial, fresh leaves of Acacia cyanophylla Lindl. (acacia) were stored after chopping or without chopping and spraying or without spraying with water under aerobic or anaerobic

H. Ben Salem; L. Saghrouni; A. Nefzaoui

2005-01-01

365

ANALYSIS OF DETERGENT FIBER FRACTIONS IN HIGH-PECTIN AND HIGH-TANNIN FORAGES  

Technology Transfer Automated Retrieval System (TEKTRAN)

Broadleaf forages often contain substances such as pectin, tannin, and ash that interfere with acid detergent fiber (ADF) measurements. We evaluated the effect of conventional non-sequential (CON) and sequential (SEQ) neutral detergent fiber (NDF) and ADF analysis and correction for acid insoluble ...

366

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

PubMed

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

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

1994-12-01

367

In vitro availability of iron and zinc in white and coloured ragi (Eleusine coracana): role of tannin and phytate.  

PubMed

White and brown ragi (Eleusine coracana) varieties were analysed for tannin, phytate phosphorus, total phosphorus, iron, ionisable iron, zinc and soluble zinc content. White ragi had no detectable tannin while in brown varieties it ranged from 351 to 2392 mg per 100 g. Germination brought about a progressive decrease in tannin and phytate phosphorus and an increase in ionisable iron and soluble zinc content of grain ragi. Both in raw and germinated grain, ionizable iron was significantly higher in white than in brown varieties. While ionisable iron was inversely correlated with the level of tannin and phytate phosphorus, soluble zinc was negatively correlated with phytate phosphorus. After extraction of tannin, ionisable iron of brown ragi rose by 85%. On the other hand, in white varieties, addition of tannin extracted from brown ragi, resulted in a 52-65% decrease in ionisable iron content. These studies indicated that poor iron availability in ragi as judged by its low ionisable iron content was due to the presence of tannin in the grain. PMID:3231591

Udayasekhara Rao, P; Deosthale, Y G

1988-01-01

368

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

PubMed

The purpose of this study was to investigate the effects of tannins on starch digestion in tannin-containing sorghum extracts and wholegrain flours from 12 sorghum varieties. Extracts reduced amylase activity in a tannin concentration-dependent manner when the extract was mixed with the enzyme before substrate (amylopectin) addition, with higher molecular weight tannins showing greater reduction. Conversely, when the extract and substrate were combined before enzyme addition an enhancement in amylase activity was experienced. In uncooked, cooked, and cooked and stored wholegrain sorghum flours, rapidly digestible, slowly digestible, and resistant starches were not correlated with tannin content or molecular weight distribution. Resistant starch increased from 6.5% to 22-26% when tannins were added to starch up to 50% (starch weight). Tannin extracts both reduced and enhanced amylase activity depending on conditions, and, while these trends were clear in extracts, the effects on starch digestion in wholegrain flours was more complex. PMID:23581620

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

2013-04-29

369

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

PubMed Central

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

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

2013-01-01

370

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

PubMed

The impacts of leaf litter from genetically modified hybrid poplar accumulating high levels of condensed tannins (proanthocyanidins) were examined in soil microcosms consisting of moss growing on sieved soil. Moss preferentially proliferated in microcosms with lower tannin content; DGGE (denaturing gradient gel electrophoresis) detected increased fungal diversity in microcosms with low-tannin litter. The proportion of cloned rDNA sequences from Actinobacteria decreased with litter addition while Bacteroidetes, Chloroflexi, Cyanobacteria, and ?-Proteobacteria significantly increased. ?-Proteobacteria were proportionally more numerous at high-tannin levels. Tannins had no significant impact on overall diversity of bacterial communities analyzed with various estimators. There was an increased proportion of N-fixing bacteria corresponding to the addition of litter with low-tannin levels. The addition of litter increased the proportion of Ascomycota/Basidiomycota. Dothideomycetes, Pucciniomycetes, and Tremellomycetes also increased and Agaricomycetes decreased. Agaricomycetes and Sordariomycetes were significantly more abundant in controls, whereas Pucciniomycetes increased in soil with litter from transformed trees (P = 0.051). Richness estimators and diversity indices revealed no significant difference in the composition of fungal communities; PCoA (principal coordinate analyses) partitioned the fungal communities into three groups: (i) those with higher amounts of added tannin from both transformed and untransformed treatments, (ii) those corresponding to soils without litter, and (iii) those corresponding to microcosms with litter added from trees transformed only with a ?-glucuronidase control vector. While the litter from transformed poplars had significant effects on soil microbe communities, the observed impacts reflected known impacts on soil processes associated with tannins, and were similar to changes that would be expected from natural variation in tannin levels. PMID:24133486

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

2013-09-26

371

Cardiac aquaporins.  

PubMed

Aquaporins are a group of proteins with high-selective permeability for water. A subgroup called aquaglyceroporins is also permeable to glycerol, urea and a few other solutes. Aquaporin function has mainly been studied in the brain, kidney, glands and skeletal muscle, while the information about aquaporins in the heart is still scarce. The current review explores the recent advances in this field, bringing aquaporins into focus in the context of myocardial ischemia, reperfusion, and blood osmolarity disturbances. Since the amount of data on aquaporins in the heart is still limited, examples and comparisons from better-studied areas of aquaporin biology have been used. The human heart expresses aquaporin-1, -3, -4 and -7 at the protein level. The potential roles of aquaporins in the heart are discussed, and some general phenomena that the myocardial aquaporins share with aquaporins in other organs are elaborated. Cardiac aquaporin-1 is mostly distributed in the microvasculature. Its main role is transcellular water flux across the endothelial membranes. Aquaporin-4 is expressed in myocytes, both in cardiac and in skeletal muscle. In addition to water flux, its function is connected to the calcium signaling machinery. It may play a role in ischemia-reperfusion injury. Aquaglyceroporins, especially aquaporin-7, may serve as a novel pathway for nutrient delivery into the heart. They also mediate toxicity of various poisons. Aquaporins cannot influence permeability by gating, therefore, their function is regulated by changes of expression-on the levels of transcription, translation (by microRNAs), post-translational modification, membrane trafficking, ubiquitination and subsequent degradation. Studies using mice genetically deficient for aquaporins have shown rather modest changes in the heart. However, they might still prove to be attractive targets for therapy directed to reduce myocardial edema and injury caused by ischemia and reperfusion. PMID:24158693

Rutkovskiy, Arkady; Valen, Guro; Vaage, Jarle

2013-10-25

372

Isolation of a Multispecific Organic Anion and Cardiac Glycoside Transporter from Rat Brain  

Microsoft Academic Search

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

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

1997-01-01

373

Effect of condensed tannins on bovine rumen protist diversity based on 18S rRNA gene sequences.  

PubMed

Molecular diversity of protists from bovine rumen fluid incubated with condensed tannins of Leucaena leucocephala hybrid-Rendang at 20 mg/500 mg dry matter (treatment) or without condensed tannins (control) was investigated using 18S rRNA gene library. Clones from the control library were distributed within nine genera, but clones from the condensed tannin treatment clone library were related to only six genera. Diversity estimators such as abundance-based coverage estimation and Chao1 showed significant differences between the two libraries, although no differences were found based on Shannon-Weaver index and Libshuff. PMID:23205499

Tan, Hui Yin; Sieo, Chin Chin; Abdullah, Norhani; Liang, Juan Boo; Huang, Xiao Dan; Ho, Yin Wan

2012-12-03

374

Dynamics of the glycosidic bond: conformational space of lactose.  

PubMed

The dynamics of the glycosidic bond of lactose was studied by a paramagnetic tagging-based NMR technique, which allowed the collection of an unusually large series of NMR data for a single compound. By the use of distance- and orientation-dependent residual dipolar couplings and pseudocontact shifts, the simultaneous fitting of the probabilities of computed conformations and the orientation of the magnetic susceptibility tensor of a series of lanthanide complexes of lactose show that its glycosidic bond samples syn/syn, anti/syn and syn/anti ?/? regions of the conformational space in water. The analysis indicates a higher reliability of pseudocontact shift data as compared to residual dipolar couplings with the presently available weakly orienting paramagnetic tagging technique. The method presented herein allows for an improved understanding of the dynamic behaviour of oligosaccharides. PMID:21755545

Erdélyi, Máté; d'Auvergne, Edward; Navarro-Vázquez, Armando; Leonov, Andrei; Griesinger, Christian

2011-07-13

375

Isoflavanones and their O-glycosides from Desmodium styracifolium.  

PubMed

Two isoflavanones (5,7-dihydroxy-2',3',4'-trimethoxy-isoflavanone and 5,7-dihydroxy-2'-methoxy-3',4'-methylenedioxy-isoflavanone), four isoflavanone O-glycosides (5,7-dihydroxy-2',3',4'-trimethoxy-isoflavanone 7-O-beta-glucopyranoside, 5,7-dihydroxy-2'-methoxy-3',4'-methylenedioxy-isoflavanone 7-O-beta-glucopyranoside, 5,7-dihydroxy-2',4'-dimethoxy-isoflavanone 7-O-beta-glucopyranoside, and 5,7,4'-trihydroxy-2',3'-dimethoxy-isoflavanone 7-O-beta-glucopyranoside), and a coumaronochromone (3,5,7,4'-tetrahydroxy-coumaronochromone), along with 25 known compounds, were isolated from the aerial parts of Desmodium styracifolium. This is for the first time isoflavanone O-glycosides were isolated from a natural source. PMID:17434190

Zhao, Ming; Duan, Jin-Ao; Che, Chun-Tao

2007-04-16

376

A novel cytotoxic flavonoid glycoside from Physalis angulata.  

PubMed

A new flavonol glycoside, myricetin 3-O-neohesperidoside (1) was isolated from a cytotoxic MeOH extract of the leaves of Physalis angulata. Compound 1 showed remarkable cytotoxicity in vitro against murine leukemia cell line P-388, epidermoid carcinoma of the nasopharynx KB-16 cells, and lung adenocarcinoma A-549 with ED(50) values of 0.048, 0.50 and 0.55 microg ml(-1), respectively. PMID:11543968

Ismail, N; Alam, M

2001-08-01

377

New coumarin glycosides from the leaves of Diospyros crassiflora (Hiern)  

Microsoft Academic Search

Two new 5-methylcoumarin glycosides named diosfeboside A (1) and B (2) and five known compounds namely kaempferol 3-O-?-l-rhamnopyranosyl-(1?2)-?-d-glucopyranoside (3), ursolic acid (4), betulinic acid (5), stigmasterol (6) and stigmasterol 3-O-?-d-glucopyranoside (7) were isolated from the leaves of Diospyros crassiflora (Hiern). Their structures were established through interpretation of 1 and 2D NMR, mass spectra analysis and comparison with reported data. In

Carine Mvot Akak; Céline Mbazoa Djama; Augustin Ephrem Nkengfack; Peng-Fei Tu; Lian-Di Lei

2010-01-01

378

New monocyclic monoterpenoid glycoside from Mentha haplocalyx Briq.  

PubMed Central

Two new monocyclic monoterpenoid glycosides, rel-(1R,2S,3R,4R) p-menthane-1,2,3-triol 3-O-?-D-glucopyranoside (1) and rel- (1S,2R,3S) terpinolene-1,2,3-triol 3-O-?-D-glucopyranoside (2) were isolated from aqueous acetone extract of the aerial parts of Mentha haplocalyx Briq.. Their structures were elucidated through spectral analysis using MS and NMR spectrometers.

2012-01-01

379

A new acylated flavone glycoside from Colebrookea oppositifolia  

Microsoft Academic Search

A new acylated flavone glycoside, echioidinin 2?-O-?-d-(2?-O-acetyl)glucopyranoside (1) along with the three known flavonoids, 5,6,7,8,5?-pentamethoxy-3?,4?-methylenedioxyflavone (2), 5,2?,6?-trihydroxy-7-methoxyflavone (3), and kaempferol 7,4?-dimethyl ether 3-O-?-d-glucopyranoside (4), were isolated from the roots of Colebrookea oppositifolia. The structure of compound 1 was elucidated by extensive spectral and chemical studies.

Ramireddy Venkata Narahari Reddy; Bandi Anil Kumar Reddy; Duvvuru Gunasekar

2009-01-01

380

Ent -kaurane diterpenoids and glycosides: Isolation, properties, and chemical transformations  

Microsoft Academic Search

This review is devoted to ent-kaurane diterpenoids and related glycosides, which represent two naturally occurring groups of compounds with interesting\\u000a structures and properties. Much useful information about the biogenesis and biological activities of these compounds is presented;\\u000a however, the greatest part of the review covers various aspects of the chemical transformations of native ent-kaurane diterpenoids, namely, their reactions via COOH,

E. Kataev; R. N. Khaybullin; R. R. Sharipova; I. Yu. Strobykina

2011-01-01

381

Two acetylated megastigmane glycosides from the leaves of Ilex paraguariensis.  

PubMed

Two acetylated megastigmane glycosides, matenosides A (1) and B (2), have been isolated from the MeOH extract of Ilex paraguariensis leaves, and their structures were elucidated on the basis of spectroscopic analysis. Compounds 1 and 2 exhibited human neutrophil elastase (HNE) inhibitory activity with IC(50) values of 50.4 muM and 11.1 microM, respectively. PMID:20361300

Xu, Guang-Hua; Kim, Young-Hee; Choo, Soo-Jin; Ryoo, In-Ja; Yoo, Jae-Kuk; Ahn, Jong-Seog; Yoo, Ick-Dong

2010-03-30

382

A new phenolic glycoside and cytotoxic constituents from Celosia argentea.  

PubMed

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

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

2010-09-01

383

A new phenolic glycoside and cytotoxic constituents from Celosia argentea  

Microsoft Academic Search

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

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

2010-01-01

384

Ethoxylated glycerol and propylene glycol glycoside palmitates from lactose  

Microsoft Academic Search

Polyoxyethylene polyol glycoside palmitates were prepared by the following successive reactions: transglycosylation of lactose\\u000a by glycerol and propylene glycol to yield crude mixtures of the polyol glucosides and galactosides; alkoxylation with ethylene\\u000a oxide; and tranesterfication by methyl palmitate. Almost all the solid waxy products exhibited low surface and interfacial\\u000a tensions and good emulsion stability; they are expected to be effective

C. L. Mehltretter; C. A. Wilham

1973-01-01

385

Two new flavonol glycosides from Gymnema sylvestre and Euphorbia ebracteolata.  

PubMed

Two new flavonol glycosides, namely kaempferol 3-O-beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-galactopyranoside (1) and quercetin 3-O-6"-(3-hydroxyl-3-methylglutaryl)-beta-D-glucopyranoside (2), have been isolated from the aerial parts of Gymnema sylvestre and Euphorbia ebracteolata, respectively. Their structures were determined on the basis of chemical and spectroscopic methods. PMID:14980834

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

2004-03-15

386

Glycosidically bound flavor compounds of cape gooseberry (Physalis peruviana L.).  

PubMed

The bound volatile fraction of cape gooseberry (Physalis peruviana L.) fruit harvested in Colombia has been examined by HRGC and HRGC-MS after enzymatic hydrolysis using a nonselective pectinase (Rohapect D5L). Forty bound volatiles could be identified, with 21 of them being reported for the first time in cape gooseberry. After preparative isolation of the glycosidic precursors on XAD-2 resin, purification by multilayer coil countercurrent chromatography and HPLC of the peracetylated glycosides were carried out. Structure elucidation by NMR, ESI-MS/MS, and optical rotation enabled the identification of (1S,2S)-1-phenylpropane-1,2-diol 2-O-beta-D-glucopyranoside (1) and p-menth-4(8)-ene-1,2-diol 1-O-alpha-L-arabinopyranosyl-(1-6)-beta-D-glucopyranoside (2). Both glycosides have been identified for the first time in nature. They could be considered as immediate precursors of 1-phenylpropane-1,2-diol and p-menth-4(8)-ene-1,2-diol, typical volatiles found in the fruit of cape gooseberry. PMID:11308344

Mayorga, H; Knapp, H; Winterhalter, P; Duque, C

2001-04-01

387

Development and application of a screening assay for glycoside phosphorylases.  

PubMed

Glycoside phosphorylases (GPs) are interesting enzymes for the glycosylation of chemical molecules. They require only a glycosyl phosphate as sugar donor and an acceptor molecule with a free hydroxyl group. Their narrow substrate specificity, however, limits the application of GPs for general glycoside synthesis. Although an enzyme's substrate specificity can be altered and broadened by protein engineering and directed evolution, this requires a suitable screening assay. Such a screening assay has not yet been described for GPs. Here we report a screening procedure for GPs based on the measurement of released inorganic phosphate in the direction of glycoside synthesis. It appeared necessary to inhibit endogenous phosphatase activity in crude Escherichia coli cell extracts with molybdate, and inorganic phosphate was measured with a modified phosphomolybdate method. The screening system is general and can be used to screen GP enzyme libraries for novel donor and acceptor specificities. It was successfully applied to screen a residue E649 saturation mutagenesis library of Cellulomonas uda cellobiose phosphorylase (CP) for novel acceptor specificity. An E649C enzyme variant was found with novel acceptor specificity toward alkyl beta-glucosides and phenyl beta-glucoside. This is the first report of a CP enzyme variant with modified acceptor specificity. PMID:20188057

De Groeve, M R M; Tran, G H; Van Hoorebeke, A; Stout, J; Desmet, T; Savvides, S N; Soetaert, W

2010-02-24

388

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.

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

2013-01-01

389

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

PubMed Central

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, at the levels of the whole genome and 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. For several glycoside hydrolase familes (GH5, GH13, GH18, GH19, GH28, and GH51), we present a detailed literature review together with an examination of the family structures. This analysis of individual families revealed both similarities and distinctions between monocots and eudicots, as well as between species. Shared evolutionary histories appear to be modified by lineage-specific expansions or deletions. Within GH 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 grass 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.

2010-01-01

390

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

2002-01-01

391

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.

2006-01-01

392

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

PubMed Central

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

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

2011-01-01

393

[Cardiac prosthesis].  

PubMed

It has been demonstrated an intrathoracic artificial heart with membrane pump delivering a pulsed flow and connected with an extracorporeal source of energy can keep a cardiotomized animal alive for several months without biological organic disturbances. The next experimental step would be intrathoracic implantation in man of a similar heart with an energy converter connected to an extracorporeal source giving the patient a 6-8 hour period of autonomy. At rest or during the night the batteries attached to the patient's waist would easily be recharged. Current research concentrates on reduction of artificial heart volume and miniaturization of the energy converter and regulatory electronic circuits. Kinetic pumps, which are small and without valvular prosthesis facilitate miniaturization. They deliver a high-speed continuous flow and have not yet been shown in long-term experiments to be free from biological disturbances. The clinical phase of stage II artificial hearts, due to begin in 1990, will be preceded by attempts at implanting hearts animated by an extracorporeal source of energy, pending cardiac replacement. PMID:6219372

Marion, P

1983-02-26

394

Estimation of aroma glycosides of nutmeg and their changes during radiation processing.  

PubMed

Glycosidically bound volatile compounds of nutmeg were identified as glyco-conjugates of p-cymene-7-ol, eugenol, methoxyeugenol and alpha-terpineol. Using phenyl-beta-glucoside as external standard the contents of these glycosidic precursors were estimated based on the measurement of TLC spot density on a densitometer. p-Cymene-7-ol rutinoside was the major aroma glycoside (3.15 mg/100 g), followed by glucosides of methoxyeugenol (0.61 mg/100 g), eugenol (0.50 mg/100 g) and alpha-terpineol (0.51 mg/100 g). A dose-dependent breakdown of these glycosidic precursors was observed during gamma-radiation processing. Among the four glycosides, alpha-terpineol glucoside was the most sensitive to radiation while p-cymene-7-ol rutinoside was the least sensitive. A reduction in the content of total glycosides by almost 50% was noted at a dose of 5kGy. Partitioning of aroma glycoside into n-butanol from aqueous extracts was found to result in rapid isolation of aroma glycosides, avoiding time consuming pre-purification on Amberlite XAD-2 column. A routine method based on extraction into n-butanol and subsequent quantification of post-irradiation changes in aroma glycosides on a TLC plate using a densitometer is proposed. PMID:16445922

Ananthakumar, Arul; Variyar, Prasad S; Sharma, Arun

2006-01-30

395

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.

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

2012-01-01

396

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

PubMed

Dalbergia odorifera contains high concentrations of flavonoid aglycones and trace flavonoid glycosides. In this study, trace flavonoid glycosides were separated from D. odorifera by titania with matrix solid-phase dispersion (MSPD). Before the MSPD experiment, four standards, including two isoflavone glycosides (genistin and formononetin-8-C-apiosyl (1-6)-glucoside) and their aglycones (genistein and formononetin), were used to compare their retention on a titania column. The effect of acetonitrile concentration and pH on their retention was investigated and a conclusion was drawn that high acetonitrile concentration and pH lead to the greatest difference in the retention of flavonoid as glycosides and aglycones. Besides hydrophilic interaction and ligand-exchange interaction may exist between sugar moiety of flavonoid glycoside and titania, so that flavonoid glycosides have stronger retention than that of aglycones. Based on the chromatographic rule of flavonoid as glycosides and aglycones on the titania column, the MSPD method was optimized to elute high concentration flavonoid aglycones first with 90% acetonitrile and 10% water containing 100 mM ammonium acetate buffer, and then to elute trace flavonoid glycosides with 20% acetonitrile and 80% water containing 1% trifluoroacetate (TFA). Isolated flavonoid glycosides were further analyzed by UPLC-MS/MS, and their fragmentation in MS(2) showed they are C-glycosyl flavonoids. PMID:21491599

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

2011-04-13

397

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

PubMed

The role of litter tannins in controlling soil nitrogen (N) cycling may explain the competitive ability of Kalmia relative to black spruce (Picea mariana), although this has not been demonstrated experimentally. Here, the protein-precipitation capacities of purified tannins and leaf extracts from Kalmia and black spruce were compared. The resistance to degradation of tannin-protein precipitates from both species were compared by monitoring carbon (C) and N dynamics in humus amended with protein, purified tannins or protein-tannin precipitates. The purity of the precipitates was verified using solid-state (13)C nuclear magnetic resonance (NMR) spectra. The ability of mycorrhizal fungi associated with both species to grow on media amended with tannin-protein complexes as the principal N source was also compared. The protein precipitation capacity of Kalmia tannins was superior to those of black spruce. Humus amended with protein increased both mineral and microbial N, whereas humus amended with tannin-protein precipitates increased dissolved organic N. Mycorrhizal fungi associated with Kalmia showed better growth than those associated with black spruce when N was provided as tannin-protein precipitates. These data suggest that Kalmia litter increases the amount of soil N sequestered as tannin-protein complexes, which may improve the competitive ability of Kalmia relative to black spruce by favouring N uptake by mycorrhizas associated with the former. PMID:18811620

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

2008-09-22

398

Interactions between tannins and proteins isolated from broad bean seeds ( Vicia faba Major) yield soluble and non-soluble complexes  

Microsoft Academic Search

The binding of tannin fraction to protein fractions isolated from broad bean seeds was studied by precipitating potential\\u000a and fluorescence quenching methods. The tannin fraction with high proanthocyanidins content was isolated from broad bean coats.\\u000a Storage proteins of broad bean, 11S, 7S, and 2S, were isolated from broad bean cotyledons and purified. Gelatin, BSA, as well\\u000a as broad bean 2S

Magdalena Karama?; Kamila Penkacik; Anna Urbalewicz; Ryszard Amarowicz

399

The effect of plant growth regulators on growth, morphology and condensed tannin accumulation in transformed root cultures of Lotus corniculatus  

Microsoft Academic Search

This study concerns the effects of four different classes of plant growth regulators on root morphology, patterns of growth and condensed tannin accumulation in transgenic root cultures of Lotus corniculatus L. (Bird's-foot trefoil). Growth of transformed roots in 2,4-dichlorophenoxyacetic acid (2,4-D) resulted in decreased tannin levels relative to controls at concentrations of 10-6 M and above, while gibberellic acid (GA3)

Mark P. Robbins; Teresa E. Evans; Phillip Morris

1996-01-01

400

Quaternary Amine Modified Persimmon Tannin Gel: An Efficient Adsorbent for the Recovery of Precious Metals from Hydrochloric Acid Media  

Microsoft Academic Search

Persimmon tannin was chemically modified to prepare a quaternary amine type of adsorption gel, named as quaternary amine modified persimmon tannin (QAPT) gel. The QAPT gel has been used to investigate the adsorption behaviors for Au(III), Pd(II) and Pt(IV) from HCl media. It was found that the gel exhibited good selectivity towards precious metals over a wide concentration range of

Manju Gurung; Birendra Babu Adhikari; Kanjana Khunathai; Hidetaka Kawakita; Keisuke Ohto; Hiroyuki Harada; Katsutoshi Inoue

2011-01-01

401

Bond Formation By Wood Surface Reactions Part Iv Analysis of Furfuryl Alcohol, Tannin and Maleic Acid Bridging Agents  

Microsoft Academic Search

Solid wood panels (Acer saccharum Marsh.) were bonded with various bridging materials following nitric acid activation. These chemical bridging materials included tannin, furfuryl alcohol and mixtures of the two with and without maleic acid. High shear strengths were achieved with a tannin-furfuryl alcohol-maleic acid mixture (T-F-M) with or without the nitric acid activation.The curing reactions of the bridging material were

S. S. Kelley; R. A. Young; R. M. Rammon; R. H. Gillespie

1982-01-01

402

Modulation of Proline-Rich Protein Biosynthesis in Rat Parotid Glands by Sorghums with High Tannin Levels  

Microsoft Academic Search

Feeding of sorghum with a high level of tannin (high-tannin sorghum) to rats caused changes in gene expression in parotid glands similar to isoproterenol treatment. Within 3 days the parotid glands were enlarged about 3-fold and a series of proline-rich proteins were increased about 12-fold. Unlike isoproterenol treatment, no changes were observed in the submandibular glands, and a Mr 220,000

Haile Mehansho; Ann Hagerman; Scott Clements; Larry Butler; John Rogler; Don M. Carlson

1983-01-01

403

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

2007-01-01

404

Synthetic-resin-free wood panel adhesives from mixed low molecular mass lignin and tannin  

Microsoft Academic Search

Mixed interior wood panel tannin adhesive formulations were developed in which lignin is in considerable proportion, 50%,\\u000a of the wood panel binder and in which no “fortification” with synthetic resins, such as isocyanates and phenol-formaldehyde\\u000a resins as used in the past, was necessary to obtain results satisfying relevant standards. A low molecular mass lignin obtained\\u000a industrially by formic acid\\/acetic acid

H. R. Mansouri; P. Navarrete; A. Pizzi; S. Tapin-Lingua; B. Benjelloun-Mlayah; H. Pasch; S. Rigolet

2011-01-01

405

Evidence for the inhibition of the terminal step of ruminal ?-linolenic acid biohydrogenation by condensed tannins  

Microsoft Academic Search

Effects of condensed tannins (CT), either via extract or plant-bound, and saponin extract on ruminal biohy- drogenation of ?-linolenic acid (ALA) were investigated in vitro. Grass-clover hay served as basal diet (con- trol). The control hay was supplemented with extracts contributing either CT from Acacia mearnsii (7.9% of dietary dry matter (DM)) or saponins from Yucca schi- digera (1.1% of

R. Khiaosa-Ard; S. F. Bryner; M. R. L. Scheeder; H.-R. Wettstein; F. Leiber; M. Kreuzer; C. R. Soliva

2009-01-01

406

Effect of Cultivar, Steeping, and Malting on Tannin, Total Polyphenol, and Cyanide Content of Nigerian Sorghum  

Microsoft Academic Search

Cereal Chem. 66(2):87-89 Tannin was estimated in the seeds of 15 Nigerian sorghum cultivars and polyphenol content also decreased by 22,68, and 19% for SRN484, KSV7, found to vary between 0.25% (catechin equivalent) for SSVl 1 and SSV12 and SSV3, respectively, after malting. Cyanide content of the grains varied and 2.92% for SRN484. Total polyphenol content ranged from 0.32% from

BOLANLE A. OSUNTOGUN; STEVE R. A. ADEWUSI; CHARLES C. NWASIKE

407

Association between seed coat polyphenolics (tannins) and disease resistance in common bean.  

PubMed

Common beans (Phaseolus vulgaris L) contain a number of antinutritional factors such as condensed tannins. Reducing tannin concentration might contribute to improving the nutritional quality of common bean. But polyphenolics are involved in resistance to diseases and pests, and reducing tannin concentration may have a negative effect on plant resistance. Furthermore, the effects of tannin on disease resistance in different gene pools or in different seed colors are not defined. To investigate these effects, 790 accessions from a common bean core collection were investigated. Data were subjected to independent sample t-tests, and the calculation of correlation coefficients. The mean coat extracts of black and red bean classes were highest (with 0.129 g/g and 0.124 g/g of seed coat, respectively). Among the gene pools, the coat extract was greater in the Middle American gene pool (0.129 g/g) than in the Andean gene pool (0.108 g/g). Coat extract in the Andean gene pool was positively correlated with susceptibility to Middle American isolates of anthracnose and to common bacterial blight, but negatively correlated with susceptibility to Andean isolates of angular leaf spot and to empoasca. Only empoasca damage showed negative correlation with coat extract in the Middle American gene pool. However within gene pools, the coat extracts of different seed classes varied in correlations with reactions to disease and pest infestations. Significant correlations were particularly associated with the black seed class in both gene pools. The relationships between coat extract and disease reactions are complex. A better understanding will help breeders to select germplasm with improved nutritional quality without adversely affecting disease resistance. PMID:15354788

Islam, F M A; Rengifo, J; Redden, R J; Basford, K E; Beebe, S E

2003-01-01

408

Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry  

Microsoft Academic Search

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

Pirjo Mämmelä; Heikki Savolainen; Lasse Lindroos; Juhani Kangas; Terttu Vartiainen

2000-01-01

409

Tannin, nitrogen, and cell wall composition of green vs. senescent Douglas-fir foliage  

Microsoft Academic Search

Tannin, cell wall, and nitrogen composition of green foliage and needle litter of similar-aged Douglas-fir (Pseudotsuga menziesii Mirb. Franco) from two stands differing in density and crown closure were compared. Trees in the closed-canopy stand had a lower basal area growth rate than those in the open-canopy stand. Stands did not differ in wood basal area\\/ha or forest floor C\\/N

J. D. Horner; R. G. Cates; J. R. Gosz

1987-01-01

410

Wastewater Toxicity of Tannin Versus Chromium-Based Leather Tanneries in Marrakesh, Morocco  

Microsoft Academic Search

The toxicity of leather tanning wastewater from a traditional tannery (TT), which is based on vegetable tannin (VT), was compared\\u000a with wastewater from a tannery combining the use of chromium-based tanning (CT) with VT-based tanning operations. Wastewater\\u000a samples from a TT and a CT plant as well as from five sewer sampling points were collected in Marrakesh, Morocco, and the

E. De Nicola; S. Meriç; C. Della Rocca; M. Gallo; M. Iaccarino; P. Manini; D. Petruzzelli; V. Belgiorno; M. Cheggour; A. Di Gennaro; A. Moukrim; O. Tünay; G. Pagano

2007-01-01

411

Pre-Ozonation of Commercial Textile Tannins: Effects on Biodegradability and Toxicity  

Microsoft Academic Search

The effect of ozonation on the biodegradability and acute toxicity of two frequently used textile dye assisting chemicals, namely natural tannin (NT) having an initial chemical oxygen demand (COD0) of 1195 mg L; initial total organic carbon (TOC0) of 342 mg L; initial 5th-day biochemical oxygen demand (BOD5,0) of 86 mg L; initial ultraviolet absorbance at 280 nm wavelength (UV280,0)

SEBNEM KOYUNLUOGLU; IDIL ARSLAN-ALATON; GULEN EREMEKTAR; FATOS GERMIRLI-BABUNA

2006-01-01

412

Electron spin resonance study on the vanadium adsorption by persimmon tannin gel  

Microsoft Academic Search

The persimmon tannin gel can adsorb vanadium highly effectively from aqueous solutions containing VOCl2 and NH4VO3, respectively. The adsorption of vanadium from the VOCl2 solution had a broad maximum at around pH 5–6, while that from the NH4VO3 solution, a sharp maximum at around pH 3.75 and a broad one at around pH 5–6. The adsorption of vanadium by the

Akira Nakajima

2002-01-01

413

Antibacterial activity of silver nanoparticles stabilized on tannin-grafted collagen fiber  

Microsoft Academic Search

Bayberry tannin (BT), a typical plant polyphenol, was grafted on collagen fiber (CF) in different mass ratios. Subsequently, the BT-grafted CF (BT-CF) was used as carrier and stabilizer to prepare BT-CF stabilized silver nanoparticles (BT-CF-AgNPs). Scanning Electron Microscopy image of BT-CF-AgNPs showed that the BT-CF-AgNPs was in ordered fibrous state. X-ray Diffraction patterns and Transmission Electron Microscopy images offered evidence

Li He; Si-ying Gao; Hao Wu; Xue-pin Liao; Qiang He; Bi Shi

414

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

2002-01-01

415

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

NASA Astrophysics Data System (ADS)

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

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

1999-10-01

416

Application of immobilized tannase from Aspergillus niger for the removal of tannin from myrobalan juice.  

PubMed

Tannase produced optimally on an agroresidue by an Aspergillus niger isolate under submerged fermentation immobilized on sodium alginate beads with 93.6% efficiency was applied for tannin removal from myrobalan/aonla (Phyllanthus emblica) juice. The pH and temperature optima of the immobilized enzyme were found to be 5.4 and 40°C while the corresponding values of the soluble enzyme were 5.8 and 35°C. Maximum tannin removal of 73.6% was obtained at 40°C and 150 rpm in 180 min with 36.6 U/ml of immobilized enzyme while the same amount of the soluble enzyme removed 45.2% of tannin at 37°C and 150 rpm in the same time period. The immobilized beads could be used repeatedly till 7th cycle with 77% efficiency. When preserved at 6°C the beads retained 71.7% of enzyme activity after 60 days. Reduction in vitamin C content, which is responsible for antioxidant property of the fruit, was minimum at only 2% during the treatment. PMID:22815571

Srivastava, Anita; Kar, Rita

2010-03-16

417

Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.  

PubMed

Fifty-seven tannins and related compounds, including gallotannins, ellagitannins, and condensed and complex tannins, were evaluated for their cytotoxicities against human tumor cell lines, including malignant melanoma, lung carcinoma, ileocecal adenocarcinoma, epidermoid carcinoma, malignant melanoma, and medulloblastoma cell lines. Among them, chebulagic acid [1], geraniin [2], sanguiin H-11 [3], 4,5-di-O-galloylquinic acid [12], 1,3,4,5-tetra-O-galloylquinic acid [15], 1(beta)-O-galloylpedunculagin [24], furosin [29], castalagin [38], sanguiin H-2 [34], vescalagin [39], grandinin [40], phyllyraeoidin A [42], (-)-epicatechin 3-O-gallate [50], cinnamtannin B2 [55], and acutissimin A [56] exhibited moderate selective cytotoxicity against PRMI-7951 melanoma cells with ED50 values in the range of 0.1-0.8 microgram/ml. Selective cytotoxicities against the melanoma cells were also observed for strictinin [22], pedunculagin [23], eugeniin [25], elaeocarpusin [28], punicacortein C [37], casuarinin [41], sanguiin H-6 [43], procyanidin B-2 3,3'-di-O-gallate [51], procyanidin C-1 3,3',3"-tri-O-gallate [52], and cinnamtannin B1 [54] with ED50 values of 1-4 micrograms/ml. All of the tannins were found to be inactive (greater than 10 micrograms/ml) against lung carcinoma (A-549), ileocecal adenocarcinoma (HCT-8), epidermoid carcinoma of nasopharnyx (KB), and medulloblastoma (TE-671) tumor cells. PMID:1431932

Kashiwada, Y; Nonaka, G; Nishioka, I; Chang, J J; Lee, K H

1992-08-01

418

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.

2004-01-01

419

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

PubMed

A rational use of water in the leather industry is described by applying the criteria of "clean technologies" by means of membrane processes. A nanofiltration (NF) process was used for recovering tannins and water from exhausted baths and reusing them as tanning agents and washings. Results of experiments performed on laboratory and semi-industrial pilot scale plants, operating and fluid-dynamic conditions and mass balance of the NF process are reported and discussed. Chemical and physical analytical values measured on skins treated with the recovered solutions were very similar to those measured on control skins tanned with standard solutions. According to the obtained results, a process scheme is suggested. It permits both to recover water and to increase the tannin/non tannin (T/NT) ratio in the retentate solution, starting from exhausted tanning baths and by using a NF membrane purification/concentration. The final volume reduction factor of tested exhausted baths was 5.25, the increase of T/NT ratio was from 1.1 to 2.3 and the average permeate flux was 12.5l/m(2)h. Advantages are in terms of: reduction of environmental impact (up to 75% of COD reduction of the global effluent), simplification of cleaning-up processes of wastewaters, decrease of disposal costs, saving of chemicals and water. PMID:12727254

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

2003-05-01

420

Bile acid-binding ability of kaki-tannin from young fruits of persimmon (Diospyros kaki) in vitro and in vivo.  

PubMed

The bile acid-binding ability of a highly polymerized tannin (kaki-tannin) extracted from dried-young fruits of persimmon (Diospyros kaki) was examined. The kaki-tannin was composed mainly of epicatechin, epigallocatechin, epicatechin-3-O-gallate and epigallocatechin-3-O-gallate. Bile acid-binding ability of kaki-tannin was examined against cholic acid, glycocholic acid, taurocholic acid and deoxycholic acid in vitro, and its effect on fecal bile acid excretion in mice was also examined. Although the bile acid-binding ability of kaki-tannin was weaker than that of cholestyramine, kaki-tannin adsorbed all the bile acids tested and significantly promoted fecal bile acid excretion in mice when supplied at 1% (w/w) in the diet. PMID:20922818

Matsumoto, Kenji; Kadowaki, Akio; Ozaki, Natsumi; Takenaka, Makiko; Ono, Hiroshi; Yokoyama, Shin-ichiro; Gato, Nobuki

2010-10-05

421

Steroidal glycosides from the underground parts of Helleborus caucasicus.  

PubMed

Four polyhydroxylated and polyunsaturated furostanol glycosides (1-4), named caucasicosides A (1), B (2), C (3) and D (4), were isolated from the MeOH extract of the underground parts of Helleborus caucasicus, along with four spirostanol derivatives, a furostanol glycoside, a furospirostanol glycoside, 20-hydroxyecdysone and the bufadienolides hellebrigenin and deglucohellebrin. The structures of 1-4 were elucidated as furosta-5,20(22),25(27)-triene-1beta,3beta,11alpha,26-tetrol 26-O-beta-D-glucopyranoside (1), 26-O-beta-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1beta,3beta,11alpha,26-tetrol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (2), 26-O-beta-d-glucopyranosyl-22alpha-methoxyfurosta-5,25(27)-diene-1beta,3beta,11alpha,26-tetrol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (3), 26-O-beta-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1beta,3beta,26-triol 3-O-beta-D-xylopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-4-O-sulfo-alpha-L-arabinopyranoside (4). Structure elucidation was accomplished through the extensive use of 1D- and 2D NMR experiments including 1H-1H (COSY, 1D-TOCSY) and 1H-13C (HSQC, HMBC) spectroscopy along with ESI-MS and HR-ESI-MS. The aglycones of 1-4 have never been reported before. PMID:18226823

Bassarello, Carla; Muzashvili, Tamara; Skhirtladze, Alexandre; Kemertelidze, Ether; Pizza, Cosimo; Piacente, Sonia

2008-01-28

422

Sudden Cardiac Arrest  

MedlinePLUS

... sudden, unexpected loss of heart function, breathing and consciousness. Sudden cardiac arrest usually results from an electrical ... Sudden collapse No pulse No breathing Loss of consciousness Sometimes other signs and symptoms precede sudden cardiac ...

423

Cardiac Arrhythmia Port.  

National Technical Information Service (NTIS)

The overall goal of the Cardiac Arrhythmia PORT was to identify the best strategies to prevent sudden cardiac death among patients with known heart disease. The authors documented substantial increases over time in specialized testing and use of implantab...

M. A. Hlaky

2000-01-01

424

Triterpenoids and their glycosides from the bark of Schefflera octophylla.  

PubMed

A new triterpene and its glycosides were isolated from the bark of Schefflera octophylla together with asiatic acid and asiaticoside. Based on spectroscopic data, especially 2DNMR, and chemical transformations the structures of the new compounds were determined as 3 alpha-hydroxy-urs-12-ene-23,28-dioic acid and 3 alpha-hydroxy-urs-12-ene-23,28-dioic acid 28-O-[alpha-L-rhamnopyranosyl (1----4)-O-beta-D-glucopyranosyl (1----6)]-beta-D-glucopyranoside. For the first time asiaticoside was isolated from a plant other than Centella asiatica. PMID:1367880

Sung, T V; Lavaud, C; Porzel, A; Steglich, W; Adam, G

1992-01-01

425

Gmelinoside I, a new flavonol glycoside from Limonium gmelinii.  

PubMed

Gmelinoside I (1), a new flavonol glycoside, was isolated and chemically characterized as 3,5,7,3',4',5'-hexahydroxy-3-O-alpha-D-galactopyranosylflavone from the aerial part of Limonium gmelinii Kuntze (Plumbaginaceae).. Other compounds were identified as (-)-epigallocatechin-3-O-gallate, myricetin, myricetin-3-O-alpha-L-rhamnopyranoside, myricetin-3-O-beta-D-galactoside-6"-O-gallate and caprolactam. The antibacterial, antifungal and antileishmanial activities of the isolated compounds were evaluated. Myricetin showed moderate antileishmanial activity. PMID:20734940

Kozhamkulova, Zhanar A; Radwan, Mohamed M; Zhusupova, Galiya E; Abilov, Zharilkasin Zh; Rahadilova, Saniya N; Ross, Samir A

2010-07-01

426

Two new glycosides from the fruits of Morinda citrifolia L.  

PubMed

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

2012-10-26

427

Triterpene glycosides from Curculigo orchioides and their cytotoxic activity.  

PubMed

Six new cycloartane glycosides (1-6) were isolated from the rhizomes of Curculigo orchioides. The structures of 1-6 were determined by spectroscopic analyses and the results of hydrolytic cleavage. Compounds 1-6, and their common aglycone (1a), were evaluated for cytotoxic activity against HL-60 human leukemia cells. Compounds 1 and 1a showed cytotoxic activity against HL-60 cells with IC(50) values of 9.0 and 1.8 microM, respectively. The cancer cell growth inhibition of 1a was also examined using a panel of 39 human cancer cell lines in the Japanese Foundation for Cancer Research. PMID:20524638

Yokosuka, Akihito; Sato, Koji; Yamori, Takao; Mimaki, Yoshihiro

2010-06-25

428

Three new phenolic glycosides from Curculigo orchioides G.  

PubMed

Three new phenolic glycosides, curculigosides F-H (1-3), were isolated from rhizomes of Curculigo orchioides Gaertn. Their structures were elucidated based on comprehensive spectroscopic analyses including IR, MS, 1D- and 2D NMR (HSQC, COSY, and HMBC). Curculigosides F-H (1-3) were evaluated for their anti-HBV activity in vitro using the HBV transfected Hep G2.2.15 cell line. Compound 1 exhibited weak activity with an IC(50) value of 2.08 mM on hepatitis B virus (HBV) e antigen (HBeAg) secretion of the HepG2.2.15 cell line. PMID:20550957

Zuo, Ai-Xue; Shen, Yong; Jiang, Zhi-Yong; Zhang, Xue-Mei; Zhou, Jun; Lü, Jun; Chen, Ji-Jun

2010-06-13

429

Four new trace phenolic glycosides from Curculigo orchioides.  

PubMed

Four new trace phenolic glycosides named orcinosides D (1), E (2), F (3), and G (4) were isolated from the rhizomes of Curculigo orchioides Gaertn. Based on comprehensive spectroscopic analyses including IR, FAB-MS, HR-ESI-MS, 1D- and 2D NMR (HSQC, HMBC), their structures were elucidated as orcinol-1-O-beta-D-xylopyranoside (1), orcinol-1-O-beta-D-apiofuranosyl-(1 --> 2)-beta-D-glucopyranoside (2), orcinol-3-O-beta-D-apiofuranosyl-1-O-beta-D-glucopyranoside (3), and 1-O-beta-D-glucopyranosyl-4-ethoxyl-3-hydroxymethylphenol (4). PMID:20390742

Zuo, Ai-Xue; Shen, Yong; Zhang, Xue-Mei; Jiang, Zhi-Yong; Zhou, Jun; Lu, Jun; Chen, Ji-Jun

2010-01-01

430

Acylated flavonol glycosides from the flower of Inula britannica.  

PubMed

Three new acylated flavonol glycosides, patuletin 7-O-(6' '-isobutyryl)glucoside (1), patuletin 7-O-[6' '-(2-methylbutyryl)]glucoside (2), and patuletin 7-O-(6' '-isovaleryl)glucoside (3), were isolated from the n-BuOH extract of Inula britannica flowers by bioassay-guided fractionation, together with other known flavonoids. The structures were elucidated by 1D and 2D NMR, FABMS, and other spectral analyses. The eight flavonoids, including new compounds (1-3), patulitrin (7), nepitrin (8), axillarin (10), patuletin (11), and luteolin (12), showed profound antioxidant activity in DPPH assay and cytochrome-c reduction assay using HL-60 cell culture system. PMID:10650074

Park, E J; Kim, Y; Kim, J

2000-01-01

431

Isoflavonoid glycosides from the flowers of Pueraria lobata.  

PubMed

Pueraria lobata flower is a medicinal herb for treating intoxication, hepatic, and gastrointestinal tract lesions induced by alcohol. This study aims to investigate the isoflavonoid glycosides in P. lobata flowers. Two new isoflavone compounds were isolated from the extract of P. lobata flowers. Their structures were determined to be 5,6,7,4'-tetrahydroxyisoflavone-6,7-di-O-?-D-glucopyranoside and 5,6,7-trihydroxy-4'-methoxyisoflavone-6,7-di-O-?-D-glucopyranoside on the basis of spectroscopic means including HR-ESI-MS, UV, IR, ¹H, and ¹³C NMR. PMID:21462030

Yu, Ying-Lu; Liao, Yi-Ting; Li, Xian; Ye, Yang; Ke, Chang-Qiang; Li, Xi-Qiang; Yang, Xin-Zhou; Yao, Mei-Cun

2011-04-01

432

Characterization of oxidized tannins: comparison of depolymerization methods, asymmetric flow field-flow fractionation and small-angle X-ray scattering  

Microsoft Academic Search

Condensed tannins are a major class of plant polyphenols. They play an important part in the colour and taste of foods and\\u000a beverages. Due to their chemical reactivity, tannins are not stable once extracted from plants. A number of chemical reactions\\u000a can take place, leading to structural changes of the native structures to give so-called derived tannins and pigments. This

Aude Vernhet; Stéphane Dubascoux; Bernard Cabane; Hélène Fulcrand; Eric Dubreucq; Céline Poncet-Legrand

433

Understanding cardiac output  

PubMed Central

Cardiac output is the amount of blood the heart pumps in 1 minute, and it is dependent on the heart rate, contractility, preload, and afterload. Understanding of the applicability and practical relevance of each of these four components is important when interpreting cardiac output values. In the present article, we use a simple analogy comparing cardiac output with the speed of a bicycle to help appreciate better the effects of various disease processes and interventions on cardiac output and its four components.

Vincent, Jean-Louis

2008-01-01

434

Cardiac MRI in Athletes  

Microsoft Academic Search

Cardiac magnetic resonance imaging (CMR) is often used in athletes to image cardiac anatomy and function and is increasingly requested in the context of screening for pathology that can cause sudden cardiac death (SCD). In this thesis, patterns of cardiac adaptation to sports are investigated with CMR.\\u000a\\u000aChapter 2 describes our finding that left-right ratios are preserved across all sports

T. Luijkx

2012-01-01

435

Iodine-hexamethyldisilane (HMDS)-mediated anomerization of peracetylated 1,2-trans-linked alkyl and aryl glycosides  

Microsoft Academic Search

Treatment of peracetylated alkyl and aryl 1,2-trans-glycosides with iodine in the presence of HMDS has been found to result in the anomerization leading to the formation of the respective 1,2-cis-glycosides. In the case of alkyl glycosides with aglycons of short alkyl chain length complete anomerization to the ?-glycosides was observed while with those of longer chain length the process was

Satish Malik; Krupesh J. Shah; K. P. Ravindranathan Kartha

2010-01-01

436

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

Technology Transfer Automated Retrieval System (TEKTRAN)

Glycoside hydrolase genes have been previously cataloged for Oryza sativa (rice), the model dicotyledonous plant Arabidopsis thaliana, and the fast-growing tree Populus trichocarpa (poplar). To improve our understanding of glycoside hydrolases in plants generally and in grasses specifically, we ann...

437

Pediatric cardiac disorders  

Microsoft Academic Search

Although pediatric cardiac disorders are not commonly seen in the Emergency Department, they are important to identify to prevent further morbidity or mortality. Diagnosis may be complicated by the lack of classic complaints such as chest pain or palpitations that are commonly associated with cardiac disorders. In fact, presenting complaints associated with pediatric cardiac disorders, like “fussiness” or “difficulty feeding,”

Ghazala Q Sharieff; Todd W Wylie

2004-01-01

438

Cardiac tumours in children  

Microsoft Academic Search

Cardiac tumours are benign or malignant neoplasms arising primarily in the inner lining, muscle layer, or the surrounding pericardium of the heart. They can be primary or metastatic. Primary cardiac tumours are rare in paediatric practice with a prevalence of 0.0017 to 0.28 in autopsy series. In contrast, the incidence of cardiac tumours during foetal life has been reported to

Orhan Uzun; Dirk G Wilson; Gordon M Vujanic; Jonathan M Parsons; Joseph V De Giovanni

2007-01-01

439

Principles of cardiac anaesthesia  

Microsoft Academic Search

This article describes the anaesthetic management of patients undergoing cardiac surgery. The techniques used are principally those applied to patients with ischaemic heart disease, which represents 56% of all cardiac surgery carried out in the UK. Where appropriate, management strategies for those patients with aortic and mitral valve disease are discussed. Monitoring techniques used for cardiac anaesthesia are detailed along

John W. W. Gothard; James W. Keogh

2009-01-01

440

Induction of uncoupling protein-1 and -3 in brown adipose tissue by kaki-tannin in type 2 diabetic NSY/Hos mice.  

PubMed

Kaki-tannin, a highly polymerized-tannin from the young fruits of persimmon (Diospyros kaki 'Hachiya'), has been shown to have bile acid-binding activity. To verify the effect of kaki-tannin on the metabolism of lipid and glucose in type 2 diabetes, type 2 diabetic NSY/Hos mice were fed an AIN76-modified high fat diet supplemented with 1% (w/w) kaki-tannin for 8weeks. Kaki-tannin induced a 2-fold increase in fecal bile acid excretion and was significantly effective in the prevention of a rise in plasma cholesterol, triglyceride, and insulin levels. Kaki-tannin treatment also prevented fatty liver. To identify the molecular mechanism underlying these effects, gene expression analysis was performed on liver, brown adipose tissue (BAT), and skeletal muscle. The genes related to cholesterol metabolism, including 3-hydroxy-3-methylglutaryl-coenzyme A reductase and sterol regulatory element-binding protein 2, were increased in the liver of the kaki-tannin group. Interestingly, the uncoupling protein-1 (UCP1) gene and the UCP3 gene were significantly increased in the BAT of the kaki-tannin group, which was also confirmed at the protein level. These findings indicated that induction of UCP1 and UCP3 in the BAT by kaki-tannin treatment might influence the energy metabolism, thus contributing beneficial effects to type 2 diabetic NSY/Hos mice. PMID:22079182

Matsumoto, Kenji; Yokoyama, Shin-Ichiro

2011-11-06

441

Alkane1,2-diol-based glycosides and fatty glycosides and wax esters in Roseiflexus castenholzii and hot spring microbial mats  

Microsoft Academic Search

The lipid composition of Roseiflexus castenholzii, a thermophilic filamentous phototrophic bacterium related to uncultivated filamentous phototrophic bacteria that predominate in hot spring microbial mats, is reported. R. castenholzii lipid extracts were dominated by components characterized by alkane-1-ol-2-alkanoate moieties glycosidically bonded to a C6 sugar. Similar fatty glycosides, with an additional fatty acid esterified, were detected by HPLC-MS. R. castenholzii also

Stefan Schouten; Satoshi Hanada; Ellen C. Hopmans; Jaap S. Sinninghe Damsté; David M. Ward

2002-01-01

442

Host plant influences on iridoid glycoside sequestration of generalist and specialist caterpillars.  

PubMed

The effect of diet on sequestration of iridoid glycosides was examined in larvae of three lepidopteran species. Larvae were reared upon Plantago major, or P. lanceolata, or switched from one to the other in the penultimate instar. Junonia coenia is a specialist on iridoid glycoside-producing plants, whereas the arctiids, Spilosoma congrua and Estigmene acrea, are both polyphagous and eat iridoid-producing plants. All species sequestered iridoids. The specialist J. coenia sequestered from three to seven times the amounts sequestered by the two generalist species. Junonia coenia iridoid glycoside content depended on diet, and they sequestered from 5 to 15% dry weight iridoid glycosides. Estigmene acrea iridoid glycoside sequestration was relatively low, around 2% dry weight and did not vary with diet. Spilosoma congrua sequestration varied with diet and ranged from approximately 3 to 6% dry weight. PMID:20809144

Lampert, Evan C; Bowers, M Deane

2010-08-31

443

Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells.  

PubMed

Flavonoid glycosides, isorhamnetin 3-capital O, Cyrillic-beta-d-glucoside, and quercetin 3-O-beta-d-glucoside were isolated from Salicornia herbacea and their inhibitory effects on matrix metalloproteinase-9 and -2 (MMP-9 and -2) were evaluated in human fibrosarcoma cell line (HT1080). In zymography experiments, these flavonoid glycosides led to the reduction of the expression levels and activities of MMP-9 and -2 without any significant difference between these flavonoid glycosides. Protein expression levels of both MMP-9 and MMP-2 were inhibited and TIMP-1 (tissue inhibitor of metalloproteinase-1) protein level was enhanced by these flavonoid glycosides. Moreover, a transfection study carried out with AP-1 reporter construct revealed that the reporter activity was suppressed by treatment with isorhamnetin 3-capital O, Cyrillic-beta-d-glucoside. Therefore, these results suggested that these flavonoid glycosides have a potential as valuable natural chemopreventive agents for cancer. PMID:18715546

Kong, Chang-Suk; Kim, You Ah; Kim, Moon-Moo; Park, Jin-Sook; Kim, Jung-Ae; Kim, Se-Kwon; Lee, Burm-Jong; Nam, Taek Jeong; Seo, Youngwan

2008-07-31

444

Isolation and hydroxylysine glycoside content of some cyanogen bromide-cleaved fragments of collagen from bovine corneal stroma.  

PubMed Central

Six CNBr-cleaved fragments of insoluble collagen from bovine cornea were isolated, characterized and examined for hydroxylysine glycosides. Thus the general distribution of most of the glycoside along the collagen molecule was determined. Collagen from bovine stroma is almost entirely type I. This work forms a basis for the pinpointing of glycoside-attachment sites along the collagen molecules of bovine cornea.

Panjwani, N A; Harding, J J

1978-01-01

445

Antioxidant and antidiabetic properties of condensed tannins in acetonic extract of selected raw and processed indigenous food ingredients from Kenya.  

PubMed

Recently, tannins have received considerable attention as health-promoting component in various plant foods and several studies have reported on its nutraceutical properties. However, no study has established the role of condensed tannins in indigenous foods of Kenya. Therefore, this study was designed to evaluate the antioxidant activity (DPPH and FRAP) and antidiabetic effects (?-amylase and ?-glucosidase inhibition activities) of condensed tannins in some selected raw and traditionally processed indigenous cereals, legumes, oil seeds, and vegetables. The condensed tannin content of the grains and vegetables ranged between 2.55 and 4.35 g/100 g DM and 1.53 and 5.73 g/100 g DM, respectively. The scavenging effect of acetonic extract on DPPH radical ranged from 77% to 90% while the reducing power was found to be 31 to 574 mmol Fe(II)/g DM in all the investigated food ingredients. The condensed tannin extracts of the analyzed samples showed promising antidiabetic effects with potential ?-amylase and ?-glucosidase inhibition activities of 23% to 44% and 58% to 88%, respectively. Condensed tannins extracted from the amaranth grain, finger millet, field bean, sunflower seeds, drumstick, and amaranth leaves exerted significantly higher antioxidant and antidiabetic activities than other food ingredients. Among the traditional processing methods, roasting of grains and cooking of vegetables were found to be more suitable mild treatments for preserving the tannin compound and its functional properties as opposed to soaking + cooking and blanching treatments. The identified elite sources of optimally processed indigenous food ingredients with promising results could be used as health-promoting ingredients through formulation of therapeutic diets. PMID:22417336

Kunyanga, Catherine Nkirote; Imungi, Jasper Kathenya; Okoth, Michael; Momanyi, Clare; Biesalski, Han Konrad; Vadivel, Vellingiri

2011-04-05

446

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

PubMed

Free-ranging browsing herbivores ingest a range of secondary plant compounds, such as tannins, with their natural diet. As many of these substances have been shown to have antibacterial properties, it could be speculated that a lack of such compounds in captive zoo diets could favour the growth of potentially pathogenic intestinal bacteria. The effect of a supplementation of a conventional diet (N, consisting mainly of grass hay and/or lucerne hay and pelleted compound feeds) fed to eight captive black rhinoceroses (Diceros bicornis) from three zoological institutions with either tannic acid (T), a source of hydrolysable tannins, or quebracho (Q), a source of condensed tannins, was investigated. The number of faecal colony forming units (CFU) of Enterobactericeae was determined by colony count of dilution series from fresh faeces applied to MacConkey agar plates. Tannins were added to the diets at approximately 5-15 g/kg dry matter, depending on the varying intake of roughage and compound feeds by the animals. There was no difference in the number of CFU between diets N (95.0 x 10(5) +/- 225.3 x 10(5)/g fresh faeces) and T (164.3 x 10(5) +/- 225.1 x 10(5)/g fresh faeces); in contrast, diet Q led to a significant reduction in CFU (4.3 x 10(5) +/- 6.5 x 10(5)/g fresh faeces) compared with the other diets. These findings suggest that condensed tannins could have the potential to reduce the number of potentially pathogenic intestinal bacteria, and that the deliberate inclusion of tannin sources in the diets of captive wild animals should be further investigated. The fact that tannic acid, shown to have antibacterial effects in various in vitro studies, did not have an effect in this study, emphasizes that the relevance of tannin supplementation for intestinal health must be verified in vivo. PMID:18184377

Clauss, M; Wittenbrink, M M; Castell, J C; Kienzle, E; Dierenfeld, E S; Flach, E J; Macgregor, S K; Hoppe, T; Hummel, J; Streich, W J; Hatt, J-M

2008-02-01

447

Screening for anti-microbial activity and phytochemical constituents of some Nigerian medicinal plants  

Microsoft Academic Search

Anti-microbial activity and phytochemical constituents of methanol extract of Plumeria rubra (flower and leaf) and Eucalyptus globules (leaf) was investigated. Phytochemical screening of the crude extract revealed the presence of tannins, phlobatannins, saponins, flavonoids, steroids, terpenoids, cardiac glycosides and reducing sugar in the plants investigated. Phlobatanins were found to be absent in the methanol extract of Plumeria rubra (flower) and

P. A. Egwaikhide; S. O. Okeniyi; C. E. Gimba

448

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

2008-01-01

449

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

2008-01-01

450

Acylated-oxypregnane glycosides from the roots of Araujia sericifera.  

PubMed

Twenty-three new acylated-oxypregnane glycosides were obtained from the roots of Araujia sericifera. (Asclepiadaceae). These glycosides were confirmed to be tetraglycosides possessing twelve known compounds, 12-O-benzoyllineolon, 12-O-benzoyldeacylmetaplexigenin, ikemagenin, kidjolanin, cynanchogenin, caudatin, rostratamine, penupogenin, 12-O-benzoylisolineolon, 12-O-tigloyldecylmetaplexigenin (incisagenin), 12-O-benzoyl-20-O-acetylsarcostin, 20-O-benzoyl-12-O-(E)-cinnamoyl-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta,20-heptahydroxy-(20S)-pregn-6-ene and ten new acylated-oxypregnanes, 12-O-benzoyl-20S-hydroxyisolineolon, 12-O-tigloyllineolon, 12-O-salicyloyllineolon, 12-O-salicyloyldeacylmetplexigenin, 12-O-benzoyl-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta-hexahydroxypregn-6-en-20-one, 12-O-benzoyl-19-benzoyloxydeacylmetapleligenin, 12-O-benzoyl-19-benzoyloxy-20-O-acetylsarcostin, 12-O-benzoyl-19-salicyloyloxy-20-O-acetylsarcostin, 12-O-benzoyl-5 alpha,6 alpha-epoxydeacylmetaplexigenin, and 12-O-benzoyl-5 alpha,6 alpha-epoxylineolon as their aglycones, using both spectroscopic and chemical methods. PMID:12951444

Warashina, Tsutomu; Noro, Tadakata

2003-09-01

451

Prenylflavonol, acylated flavonol glycosides and related compounds from Epimedium sagittatum.  

PubMed

Chemical examination of the n-BuOH extract from the aerial parts of Epimedium sagittatum led to isolation of three prenylated flavonol glycosides sagittasine A-C, two acylated flavonol glycosides kaempferol-3-O-(2''-E-p-coumaroyl,4''-Z-p-coumaroyl)-alpha-l-rhamnopyranoside and kaempferol-3-O-(3''-Z-p-coumaroyl,4''-E-p-coumaroyl)-alpha-l-rhamnopyranoside, together with known flavonoids, flavonolignans, 2-phenoxychromones, a lignan, and aromatic acid derivatives. Flavonolignans were identified for the first time in this plant. The vasorelaxing properties of the n-BuOH extract of E. sagittatum and 13 isolated compounds were tested using pre-contracted rat aorta rings in an organ bath apparatus. The results indicated that the n-BuOH extract of E. sagittatum produced a partial endothelial nitric oxide-dependent vasorelaxation, with EC(50) of 0.16+/-0.03 mg/ml. However, the 13 compounds tested, generated only a mild or moderate relaxation, and did not possess significant vasorelaxing effect individually. PMID:17618659

Wang, Guei-Jane; Tsai, Tung-Hu; Lin, Lie-Chwen

2007-07-05

452

Allosteric indicator displacement enzyme assay for a cyanogenic glycoside.  

PubMed

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

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

2013-10-07

453

Separation of Phenylpropanoid Glycosides from a Chinese Herb by HSCCC.  

PubMed

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

2013-05-16

454

Aggregation of the salivary proline-rich protein IB5 in the presence of the tannin EgCG.  

PubMed

In the mouth, proline-rich proteins (PRP), which are major components of stimulated saliva, interact with tannins contained in food. We report in vitro interactions of the tannin epigallocatechin gallate (EgCG), with a basic salivary PRP, IB5, studied through electrospray ionization mass spectrometry (ESI-MS), small-angle X-ray scattering (SAXS), and dynamic light scattering (DLS). In dilute protein (IB5) solutions of low ionic strength (1 mM), the proteins repel each other, and the tannins bind to nonaggregated proteins. ESI-MS experiments determine the populations of nonaggregated proteins that have bound various numbers of tannin molecules. These populations match approximately the Poisson distribution for binding to n = 8 sites on the protein. MS/MS experiments confirm that complexes containing n = 1 to 8 EgCG molecules are dissociated with the same energy. Assuming that the 8 sites are equivalent, we calculate a binding isotherm, with a binding free energy ?? = 7.26RT(a) (K(d) = 706 ?M). In protein solutions that are more concentrated (0.21 mM) and at higher ionic strength (50 mM, pH 5.5), the tannins can bridge the proteins together. DLS experiments measure the number of proteins per aggregate. This number rises rapidly when the EgCG concentration exceeds a threshold (0.2 mM EgCG for 0.21 mM of IB5). SAXS experiments indicate that the aggregates have a core-corona structure. The core contains proteins that have bound at least 3 tannins and the corona has proteins with fewer bound tannins. These aggregates coexist with nonaggregated proteins. Increasing the tannin concentration beyond the threshold causes the transfer of proteins to the aggregates and a fast rise of the number of proteins per aggregate. A poisoned growth model explains this fast rise. Very large cationic aggregates, containing up to 10,000 proteins, are formed at tannin concentrations (2 mM) slightly above the aggregation threshold (0.2 mM). PMID:23297743

Canon, Francis; Paté, Franck; Cheynier, Véronique; Sarni-Manchado, Pascale; Giuliani, Alexandre; Pérez, Javier; Durand, Dominique; Li, Joaquim; Cabane, Bernard

2013-01-28

455

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

2008-09-01

456

Tannin-Metal Interactions in Soils: An Incubation-Extraction Approach in Hill-Land Environments  

NASA Astrophysics Data System (ADS)

Tannins, plant polyphenols known to react with proteins, metals and soil organic matter, are commonly found in the vegetation growing in Appalachian hill-lands. Establishing silvopastoral grazing systems in these environments is a means for improving productivity however the fate of tannins in soils and, in particular, the effect on solubility/mobility of metals in soils is poorly understood. Soils from forest and pasture systems were sampled from two depths, treated with tannic acid or related phenolic compounds, and analyzed for metals in solution. The amount of Mn and Ca detected in solution varied among the different phenolic treatments, highest for gallic acid, and was also influenced by depth and land use. As expected, the Ca content in solution was correlated with the electrical conductivity (EC) and the Mn content was correlated with the redox potential in solution. Interestingly, the EC was also correlated with both Mn content and redox potential. The higher Ca content found in solution may result from the low pH of the phenolic compounds. The higher Mn in solution may result from the redox reaction of Mn (IV) oxides with the phenolic compounds, producing soluble Mn2+ and quinones. These quinones are very reactive compounds that can self-polymerize and/or copolymerize with other biomolecules, such as amino-containing compounds and carbohydrates, to form humic-like substances. Successful management of silvopastures, requires an understanding of factors that affect the quality and quantity of plant secondary compounds like tannins entering soil not only to increase forage productivity but also to enhance formation/stabilization of soil organic matter to increase nutrient cycling and reduce the toxicity risk of some metals such as Mn.

Gonzalez, J. M.; Halvorson, J. J.

2007-12-01

457

Effect of irradiation on anti-nutrients (total phenolics, tannins and phytate) in Brazilian beans  

Microsoft Academic Search

The Brazilian bean varieties Phaseolus vulgaris L. var. Carioca and Vigna unguiculata (L.) Walp var. Macaçar were irradiated with doses of 0.5, 1.0, 2.5, 5.0 and 10 kGy and subsequently stored at ambient temperature for 6 months. The anti-nutrients phenolic compounds, tannins and phytate were determined to be 0.48 mg g?1 dry basis, 1.8 mg g?1 dry basis and 13.5 ?mol g?1 dry

Anna Lucia C. H Villavicencio; Jorge Mancini-Filho; Henry Delincée; Ralf Greiner

2000-01-01

458

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.

2007-10-01

459

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

2002-01-01

460

Curingof a phenol–formaldehyde–tannin adhesive in the presence of wood  

Microsoft Academic Search

The\\u000a curing of a phenol–formaldehyde–tannin (PFT) adhesive in the presence\\u000a of pine or eucalyptus wood has been studied using differential scanning calorimetry.\\u000a The influence of the adhesive\\/wood ratio on the activation energy (Ea), the temperature of the\\u000a maximum of the exothermic peak (Tp)\\u000a and the enthalpy of the curing process (?H)\\u000a was analysed. Ea, Tp and ?H\\u000a of the curing

G. Vázquez; J. González-Álvarez; G. Antorrena

2006-01-01

461

The effect of the combination of acids and tannin in diet on the performance and selected biochemical, haematological and antioxidant enzyme parameters in grower pigs  

Microsoft Academic Search

BACKGROUND: The abolition of in-feed antibiotics or chemotherapeutics as growth promoters have stimulated the swine industry to look for alternatives such as organic acids, botanicals, probiotics and tannin. The objective of the present study was to compare the effects of a combination of acids and tannin with diet with organic acids and diet without growth promoters on the growth performance

Marina Štukelj; Zdravko Valen?ak; Mladen Krsnik; Alenka Nemec Svete

2010-01-01

462

Phenotypic and phylogentic characterisation of tannin degrading\\/tolerating bacterial isolates from the rumen of goats fed on pakar (Ficus infectoria) leaves  

Microsoft Academic Search

The tannin degrading\\/tolerating bacteria were isolated from goat rumen fed on tannin rich diet on a medium containing 1% tannic acid. One hundred and twenty five isolates were picked up and screened for their potential to grow on a medium containing tannic acid as one of the ingredients and eight best isolates were selected for further characterisation. The isolates were

B. Singh; L. C. Chaudhary; Neeta Agarwal; D. N. Kamra

2011-01-01

463

Extractability and biological activity of tannins from various tree leaves determined by chemical and biological assays as affected by drying procedure  

Microsoft Academic Search

Leaf samples of Juglans regia (walnut), Rhus typhina (sumach), Aesculus hippocastanum (chestnut) and Salix alba (willow) were either freeze dried or oven dried and the amount of tannins was determined by two chemical assays (Folin Ciocalteau and ferric chloride method). In addition, the biological activity of these tannins was determined by their protein precipitation capacity and by a bioassay based

S. Muetzel; K. Becker

2006-01-01

464

Gut pH, redox conditions and oxygen levels in an aquatic caterpillar: Potential effects on the fate of ingested tannins  

Microsoft Academic Search

Larvae of the freshwater moth Acentria ephemerella (Pyralidae, Lepidoptera) can fully develop on Myriophyllum spicatum, a submerged macrophyte containing 7–10% of its dry mass as tannins. We investigated the physicochemical gut parameters of larvae fed with M. spicatum or Potamogeton perfoliatus, a food plant lacking tannins, and the chemical fate of ingested polyphenols. Microelectrode studies revealed that larval midguts were

Elisabeth M. Gross; Andreas Brune; Oliver Walenciak

2008-01-01

465

Glucose, fructose and sucrose increase the solubility of protein-tannin complexes and at high concentration, glucose and sucrose interfere with bisulphite bleaching of wine pigments.  

PubMed

Wines were modified with increasing sugar concentrations and decreasing tannin concentrations and analysed by a combination of protein precipitation and bisulphite bleaching. Increasing sugar concentration decreased the precipitation of tannin and protein-precipitable polymeric pigments (PPP). The use of a hydrogen bond disruptor (urea) to reduce protein-tannin and protein-pigment complex formation showed that the effect of sugar concentration occurred by increasing the solubility of the tannin-protein complex, not by interfering with protein-tannin complex formation. By increasing the solubility of pigment-protein complexes, non-protein-precipitable polymeric pigments (nPPP) appeared to increase. There was also an increase in total polymeric pigments at each tannin concentration with increasing glucose and sucrose concentration, indicating that sugar concentration might also affect bisulphite bleaching of wine pigments. While a significant effect of sugar concentration on tannin-protein complex solubility was observed, these effects were greatest at sugar concentrations far in excess of normal wine making conditions. Under normal wine making conditions, sugar concentration will have a negligible effect on protein-precipitable tannin, PPP and nPPP concentrations. PMID:23265524

Harbertson, James F; Yuan, Chunlong; Mireles, Maria S; Hanlin, Rachel L; Downey, Mark O

2012-11-12

466

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

PubMed

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

2012-02-28

467

[Application of nuclear magnetic resonance to the determination of the configuration of glycoside bond].  

PubMed

In the structural determination of natural glycosides, nuclear magnetic resonance (NMR) is an important approach in determining the configuration of glycoside bond. The test of coupling constant of the anomeric proton and chemical shift of the anomeric carbon are two common methods, but these methods are not suitable for some sugars. For those sugars, detailed 13C NMR analysis is an alternative choice. This paper summarizes the characteristics of 1H and 13C NMR data of the common monosaccharides published in the literatures, in order to search an approach to determine the configuration of glycoside bond. PMID:21542281

Pei, Yue-hu; Hua, Hui-ming; Li, Zhan-lin; Chen, Gang

2011-02-01

468

Carijoside A, a Bioactive Sterol Glycoside from an Octocoral Carijoa sp. (Clavulariidae)  

PubMed Central

A new bioactive sterol glycoside, 3?-O-(3?,4?-di-O-acetyl-?-d-arabinopyranosyl) -25?-cholestane-3?,5?,6?,26-tetrol-26-acetate) (carijoside A, 1), was isolated from an octocoral identified as Carijoa sp. The structure of glycoside 1 was established by spectroscopic methods and by comparison with spectral data for the other known glycosides. Carijoside A (1) displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils and this compound exhibited moderate cytotoxicity toward DLD-1, P388D1, HL-60, and CCRF-CEM tumor cells.

Liu, Chih-Yang; Hwang, Tsong-Long; Lin, Mei-Ru; Chen, Yung-Husan; Chang, Yu-Chia; Fang, Lee-Shing; Wang, Wei-Hsien; Wu, Yang-Chang; Sung, Ping-Jyun

2010-01-01

469

Carijoside A, a bioactive sterol glycoside from an octocoral Carijoa sp. (Clavulariidae).  

PubMed

A new bioactive sterol glycoside, 3beta-O-(3',4'-di-O-acetyl-beta-D-arabinopyranosyl)-25xi-cholestane-3beta,5alpha,6beta,26-tetrol-26-acetate) (carijoside A, 1), was isolated from an octocoral identified as Carijoa sp. The structure of glycoside 1 was established by spectroscopic methods and by comparison with spectral data for the other known glycosides. Carijoside A (1) displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils and this compound exhibited moderate cytotoxicity toward DLD-1, P388D1, HL-60, and CCRF-CEM tumor cells. PMID:20714421

Liu, Chih-Yang; Hwang, Tsong-Long; Lin, Mei-Ru; Chen, Yung-Husan; Chang, Yu-Chia; Fang, Lee-Shing; Wang, Wei-Hsien; Wu, Yang-Chang; Sung, Ping-Jyun

2010-06-29

470

New cucurbitane triterpenoids and steroidal glycoside from Momordica charantia.  

PubMed

Three new cucurbitane triterpenoids 1-3 and one new steroidal glycoside 4, were isolated together with ten known compounds from Momordica charantia. The structures of new compounds were determined to be 19(R)-n-butanoxy-5 beta,19-epoxycucurbita-6,23-diene-3beta,25-diol 3-O-beta-glucopyranoside (1), 23-O-beta-allopyranosylecucurbita-5,24-dien-7 alpha,3beta,22(R),23(S)-tetraol 3-O-beta-allopyranoside. (2), 23(R),24(S),25-trihydroxycucurbit-5-ene 3-O-{[beta-glucopyranosyl(1-->6)]-O-beta-glucopyranosyl}-25-O-beta-glucopyranoside (3), and 24(R)-stigmastan-3beta,5 alpha,6 beta-triol-25-ene 3-O-beta-glucopyranoside (4), respectively. Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments and chemical reactions. PMID:20032860

Liu, Jie-Qing; Chen, Jian-Chao; Wang, Cui-Fang; Qiu, Ming-Hua

2009-11-25

471

Flavonoid Glycosides from the Seeds of Litchi chinensis.  

PubMed

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

2011-02-02

472

[Steroid furostanol glycosides: a new class of natural adaptogenes (review)].  

PubMed

The present review summarizes experimental data revealed while studying the mechanism of the adaptogenic effect of furostanol glycosides (FG) extracted from Dioscorea deltoidea Wall cell culture under the conditions of biotic stress in tomato plants Lycopersicon esculenium Mill. induced by the gall nematode Meloidogyne incognita Kofoid et White. Comparison of changes in isoprene content (phytosterines, tomatin, and carotenoids) and in the rate of oxidative processes in the leaves and roots of intact and treated plants evidence that FG cause nonspecific defense reactions resulting in the formation of systemic acquired resistance. This formation is presented by the enhancement in photosynthetic apparatus pigment fund, pigments of the violaxanthin cycle in particular, by activation of processes related to POL, and by increase in peroxidase activity-enzyme of antioxidant protection. PMID:19845281

Vasil'eva, I S; Udalova, Zh V; Zinov'eva, S V; Paseshnichenko, V A

473

Acetylated flavonoid glycosides potentiating NGF action from Scoparia dulcis.  

PubMed

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

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

2004-04-01

474

Two new flavonol glycosides as DNA topoisomerase I poisons.  

PubMed

Flavonoids are secondary plant metabolites whose anticancer properties are actually being studied from an epidemiological and pharmacological point of view. They are believed to be implicated in the lower risk of some forms of cancer observed in Asian countries, due to their capacity to control cell proliferation, to act on certain regulatory enzymes as protein kinases or topoisomerases. Based on these precedents