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PubMed1998

Two new sulfated saponins from the roots of Gypsophila bermejoi.

Two new sulfated saponins (1 and 2) were isolated from a butanol-soluble extract of the roots of Gypsophila bermejoi and were identified by a combination of chemical degradation and spectral methods as the 3beta-sulfate ester of gypsogenin 28-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-beta -D-glucopyranoside (1), and the 23-sulfate ester of hederagenin 28-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-beta -D-glucopyranoside (2), respectively. Plants of the genus Gypsophila (Caryophyllaceae) are important industrially because of the capacity of their saponin constituents to behave like natural detergents.1 Saponins from this genus are based on oleanolic acid (3-hydroxyolean-12-en-28-oic acid), with gypsogenin being the main pentacyclic triterpenoidal aglycon found. In general, this aglycon is substituted at the C-3 hydroxyl and/or C-28 carboxylic acid groups by saccharide units.2

Carbohydrate Sequence↗
PubMed1999

Antifungal jujubogenin saponins from Colubrina retusa.

Antifungal assay-guided isolation of the 95% ethanol extract of the stems of Colubrina retusa yielded jujubogenin 3-O-alpha-L-arabinofuranosyl(1-->2)-[beta-D-glucopyranosyl (1-->3)]-alpha-L-arabinopyranoside (1), which showed modest growth-inhibitory effects against Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus (MICs, 50 microg/mL). In addition, two new minor saponins, jujubogenin 3-O-alpha-L-arabinofuranosyl(1-->2)-[2-O-(trans, cis)p-coumaroyl-beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopy ranosi de (2), and jujubogenin 3-O-(5-O-malonyl)-alpha-L-arabinofuranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranoside (3), were obtained. Saponin 2 was marginally active against only C. neoformans, with a MIC of 50 microg/mL, while 3 was inactive. NMR spectroscopy was used extensively for the structure determination of these compounds. The previously reported ambiguity of the NMR assignments of jujubogenin saponins for carbons -26 to -29 was clarified by a comprehensive analysis of the NMR spectra of 1.

Antifungal Agents↗
PubMed1999

Biologically active triterpene saponins from callus tissue of Polygala amarella.

A new bioactive saponin (1), together with a known saponin (polygalasaponin XXVIII) has been isolated from the callus tissue culture of Polygala amarella. Based on spectroscopic data, especially direct and long-range heteronuclear 2D NMR analysis and on chemical transformations, the structure of 1 was elucidated as 3-O-beta-D-glucopyranosyl presenegenin-28-O-beta-D-galactopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-fucopyranoside. Both saponins showed significant immunological properties based on the enhancement of granulocyte phagocytosis in vitro.

Adjuvants, Immunologic↗
PubMed2000

Antiproliferative triterpene saponins from Trevesia palmata.

During the course of a study of plants of the family Araliaceae, antiproliferative activity was demonstrated by the crude saponin fraction of Trevesia palmata. After chromatographic purification, six new bisdesmosidic saponins (1-6), along with two known triterpenoid saponins, (7 and 8), were isolated. The structures of 1-6 were determined by (1)H-(1)H correlation spectroscopy (COSY-DQF, 1D TOCSY, 2D HOHAHA, 1D ROESY) and (1)H-(13)C (HSQC, HMBC) spectroscopy. The antiproliferative activity of compounds 1-8 and of their prosapogenins (2a-7a) prepared by alkaline hydrolysis, was evaluated using three continuous culture cell lines.

Animals↗
PubMed1997

Metabolism of saponins from Narthecium ossifragum--a plant implicated in the aetiology of alveld, a hepatogenous photosensitization of sheep.

One sheep was dosed over 4 consecutive days with 2.1 kg of leaves and flower stems of Narthecium ossifragum before it was killed. Sarsasapogenin and smilagenin glycosides, in the ratio 9:1, were the dominant saponins present in the dosed plant material. GC-MS analyses of the free and conjugated sapogenin content of samples recovered from the sheep identified three distinct regions of metabolic activity. In the first metabolic region, in the rumen and omasum, the ingested plant saponins were hydrolysed to the parent sapogenins, before being oxidized at C-3 and reduced to give the epi analogues of the ingested sapogenins. The second metabolic region consisted of the duodenum, jejunum, the liver and associated ducts. Sapogenins appear to be absorbed in the jejunum and may be transported via the portal vein to the liver, where 3 alpha-OH-5 beta-H sapogenins (epismilagenin and episarsasapogenin), but not 3 beta-OH-5 alpha-H sapogenins (smilagenin and sarsasapogenin), are conjugated and excreted into the bile as episarsasapogenin and epismilagenin conjugates in the ratio 4:1. In the third metabolic region, in the caecum and the colon, the epi-sapogenin conjugates were hydrolysed to free epi-sapogenins. The absence of free and/or conjugated sapogenins in urine, collected 24 h after dosing commenced, indicates that saponins and their metabolites are not likely to be implicated in the kidney disease occurring in ruminants ingesting N. ossifragum.

Animals↗
PubMed2005

Effect of ginseng saponins on enhanced dopaminergic transmission and locomotor hyperactivity induced by nicotine.

Several studies have shown that behavioral hyperactivity induced by psychomotor stimulants is prevented by ginseng saponins. In an attempt to investigate whether the effect of ginseng saponins is through their inhibitory action on the enhanced dopaminergic transmission by psychomotor stimulants, we examined the effects of ginseng total saponin (GTS) presynaptically on nicotine-induced dopamine (DA) release in the striatum of freely moving rats using in vivo microdialysis technique and postsynaptically on the in vitro and in vivo binding of [3H]raclopride to DA D2 receptors. Also, we examined the effects of GTS on nicotine-induced locomotor hyperactivity and on nicotine-induced Fos protein expression in the nucleus accumbens and striatum. Systemic pretreatment with GTS (100 and 400 mg/kg, intraperitoneally (i.p.)) resulted in a dose-dependent inhibition of locomotor hyperactivity induced by nicotine. GTS decreased nicotine-induced DA release in the striatum in a dose-dependent manner. However, GTS had no effects on resting levels of locomotor activity and extracellular DA in the striatum. GTS inhibited the in vitro binding of [3H]raclopride to rat striatal membranes with an IC50 of 5.14+/-1.09 microM. High doses of GTS (400 and 800 mg/kg, i.p.) resulted in decreases in the in vivo binding of [3H]raclopride in the striatum. GTS decreased nicotine-induced Fos protein expression in the nucleus accumbens and striatum, reflecting the inhibition by GTS of nicotine-induced enhancement of dopaminergic transmission. The results of the present study suggest that GTS acts not only on dopaminergic neurons directly or indirectly to prevent nicotine-induced DA release but also postsynaptically by binding to DA D2 receptors. This may explain the blocking effect of GTS on behavioral activation induced by nicotine and conceivably by other psychostimulants. Our data raise the possibility that GTS, by attenuating nicotine-induced enhancement of dopaminergic transmission, may prove to be a useful therapeutic agent for nicotine addiction and warrant further investigation on its effect on nicotine's rewarding property.

Animals↗
PubMed1987

Differential permeabilization of membranes by saponin treatment of isolated rat hepatocytes. Release of secretory proteins.

Monolayer cultures of rat hepatocytes were treated with increasing concentrations of saponin (prepared from Gypsophila plants) for 30 min at 6 degrees C. Differential permeabilization of the intracellular membranes could be demonstrated: at 0.040 mg of saponin/ml the plasma membrane was permeabilized, as assessed by the release of 50% of the total cellular amount of lactate dehydrogenase, and at 0.20 mg/ml the endoplasmic reticulum was permeabilized, as measured by the release of 50% of pulse-35S-labelled albumin. The Golgi complex was permeabilized at an intermediate saponin concentration, as indicated by the release of homogeneously 35S-labelled albumin; about half the intracellular albumin is located in this organelle. At 1.0 up to 5.0 mg of saponin/ml 90-95% of the radioactively labelled albumin was released. Even at 5.0 mg/ml less than 10% of the membrane of the endoplasmic reticulum was solubilized, as judged by the degree of release of a membrane-bound enzyme specific for this organelle. These results demonstrate the usefulness of saponin as a tool for investigating the interior of different intracellular compartments.

Albumins↗
PubMed1999

Quillaja saponin formulations that stimulate proinflammatory cytokines elicit a potent acquired cell-mediated immunity.

We examined the ability of various Quillaja saponins in iscom-matrix formulations to induce proinflammatory cytokines, such as interleukin (IL)-1alpha and IL-6, and to stimulate acquired immune responses to influenza virus envelope proteins. The A-fraction of Quillaja saponins (QH-A) was shown to stimulate antigen-presenting cells (APC) to produce proinflammatory cytokines, and elicited a high primary antigen-specific antibody response and potent cell-mediated responses, as measured by T-cell proliferation, production of cytokines and cytotoxic T-lymphocyte (CTL) activity. The C-fraction of Quillaja saponins (QH-C) was shown to have a low capacity to stimulate proinflammatory cytokines and elicited low primary antibody and T-cell responses. However, the QH-C iscom-matrix mediated a potent booster effect, resulting in a high secondary antibody response. The ability of APC to discriminate and to respond to QH-A formulations more efficiently than to QH-C with release of proinflammatory cytokines, which precedes a potent acquired immune response, identifies an important mechanism through which some adjuvants may exert their immunoenhancing activities.

Animals↗
PubMed2000

Three new saponins from Tribulus terrestris.

Three new steroidal saponins 1-3, together with five known steroidal saponins, L-mannitol and an inorganic salt were isolated from Tribulus terrestris L. (Zygophyllaceae). The structures of the new steroidal saponins were elucidated as hecogenin 3-O-beta-xylopyranosyl(1-->3)-beta-glucopyranosyl(1-->4)-beta-galactopyr anoside (1), hecogenin 3-O-beta-glucopyranosyl(1-->2)-beta-glucopyranosyl(1-->4)- beta-galactopyranoside (2) and 3-O-[beta-xylopyranosyl(1-->2)-[beta-xylopyranosyl(1-->3)]-beta- glucopyranosyl(1-->4)-[alpha-rhamnopyranosyl(1-->2)]-beta-galactopyranos yl]- 26-O-beta-glucopyranosyl-22-methoxy-(3 beta,5 alpha,25R)-furostan-3,26-diol (3). Structure elucidation was accomplished by 1D and 2D NMR spectra (13C-1H COSY, HMQC, HMBC, 1H-1H COSY, TOCSY, and NOESY), mass spectrometry (FABMS, ESIMS) and chemical methods.

Carbohydrate Sequence↗
PubMed2001

Dammarane triterpene saponin from Bacopa monniera as the superoxide inhibitor in polymorphonuclear cells.

The hydroalcoholic extract of the whole plant of Bacopa monniera Wettst. (Scrophulariaceae), exhibited an inhibitory effect on superoxide released from polymorphonuclear (PMN) cells in the nitroblue tetrazolium (NBT) assay. The major saponin bacoside A(3) was found to be responsible for this effect in the herb. This compound showed 85, 91.66, 91.66, and 83 % inhibitions of NBT reduction at the concentrations of 200, 100, 50, and 25 microg/ml, respectively, with an IC(50) value of 10.22 microg/ml. These inhibitory effects were compared with those of the standard positive controls, quercetin and ascorbic acid with IC(50) of 111 and 14.16 microg/ml, respectively. Another major saponin bacopasaponin C was found to be much less potent as compared to bacoside A(3) whereas the remaining two mixtures of saponins were found to be inactive.

Carbohydrate Sequence↗
PubMed2002

Cycloartane and oleanane saponins from egyptian astragalus spp. as modulators of lymphocyte proliferation.

From the roots of Astragalus kahiricus DC., three known saponins, namely, astraversianin VI, astraversianin X, astragaloside VIII, and a new saponin were isolated and identified by spectral data. The structure of the latter was elucidated by spectral means and assigned as cycloastragenol 3- O-[ beta- D-(2',3'-diacetyl, 4'- trans-2-butenoyl)-xylopyranosyl], 6- O- beta- D-xylopyranoside (kahiricoside I). From the aerial parts of A. hamosus L., the known compounds azukisaponin V and peregrinoside I were isolated. As judged by in vitro tests, the saponins isolated from Astragalus spp. endemic to Egypt were not cytotoxic against a variety of human cancer cells. However, dose-related modulation of lymphocyte proliferation was observed, and structure-activity relationships are described.

Adjuvants, Immunologic↗
PubMed1998

Preventive effects of saponins from the Pueraria lobata root on in vitro immunological liver injury of rat primary hepatocyte cultures.

Preventive effects of nine saponins obtained from Puerariae Radix (the roots of Pueraria lobata) on in vitro immunological liver injury in primary cultured rat hepatocytes were studied. Although all tested saponins showed hepatoprotective action, the levels of activity of individual saponins differed. Structure-activity relationships for the sapogenol moiety suggested that the hydroxy group at C-29 would reduce the hepatoprotective activity while the hydroxy group at C-21 could enhance the hepatoprotective activity. Furthermore, structure-activity relationships for the sugar moiety suggested that the oxygen-bearing group at C-5" would enhance the hepatoprotective activity, though the configuration of the hydroxy group at C-3" could be less important for hepatoprotective activity.

Animals↗
PubMed1996

Main ginseng saponin metabolites formed by intestinal bacteria.

Ginseng saponin metabolites produced by human intestinal bacteria and the urinary and blood compounds after oral administration of Ginseng extract and its saponins in human and specific pathogen-free rats were examined in order to elucidate their metabolites absorbed from the intestines. The main metabolites of ginsenosides Rb1, Rb2, Rc, Re, and Rg1 after anaerobic incubation with fecal flora were identified as 20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol (I) 20-O-[alpha-L-arabinopyranosyl (1-->6)-beta-D-glucopyranosyl]-20(S)-protopanaxadiol (II), 20-O-[alpha-L- arabinofuranosyl(1-->6)-beta-D-glucopyranosyl]-20(S)-protopanaxadiol+ ++ (III), and 20(S)-protopanaxatriol (IV), though the metabolic rate and mode were affected by fermentation media. Furthermore, metabolites I-IV and 20(S)-protopanaxadiol (XII) were detected in blood (0.3-5.1 micrograms/ml) and in urine (2.2-96 micrograms/ day) after the oral administration of Ginseng extract (150 mg/ kg/day) to human and of total saponin (1 g/kg/day) to rats.

Animals↗
PubMed1994

Interactions of ginseng extract, ginseng separated fractions, and some triterpenoid saponins with glucose transporters in sheep erythrocytes.

The effects of Panax ginseng extract, ginseng saponins, and some other triterpenoid saponins on glucose uptake were examined by using sheep erythrocytes. Initial rates of glucose transport were determined by measurements of 2-deoxy-D-glucose (2-DG) uptake. From kinetic analysis apparent Km and Vmax values of facilitated glucose transport in sheep erythrocytes were calculated as 2.3 +/- 0.08 mM and 1.4 +/- 0.05 nmol/min/10(9) cells. The results showed that ginseng extract stimulated glucose uptake in sheep erythrocytes dose-dependently. Ginseng saponins, in general, also stimulated glucose transport. The maximum effect was observed at 1 microM of ginsenoside Rb1 showing an increase of 24 +/- 5% above basal activity. However, ginsenoside Rg3, chikusetsusaponin Ia, and glycyrrhetic acid induced significant inhibitory effects on glucose transport in sheep erythrocytes.

Animals↗
PubMed1990

New biologically active triterpene-saponins from Randia dumetorum.

Two new triterpene-saponins, 3-O-[O-beta-D-glucopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----3)-( beta- D-glucuronopyranosyl)]oleanolic acid (1), 3-O-[O-beta-D-glucopyranosyl-(1----6)-O-beta-D-glucopyranosyl- (1----3)-(beta-D-glucuronopyranosyl)]oleanolic acid (2) together with five known saponins (3-7) were isolated from the methanolic extract of the fruits of Randia dumetorum (Retz) Lam. (Rubiaceae). Their structures were established on the basis of chemical and spectral data. The compounds 1, 3, 4, 5 were found to enhance significantly the proliferation of human lymphocytes in vitro. The crude saponin fraction showed haemolytic, molluscicidal, and immunostimulating activities.

Animals↗
PubMed2001

Avicins, a family of triterpenoid saponins from Acacia victoriae (Bentham), inhibit activation of nuclear factor-kappaB by inhibiting both its nuclear localization and ability to bind DNA.

Triterpenoid saponins, which are present in leguminous plants and some marine animals, possess a broad range of biological actions. We have earlier reported the extraction of avicins, a family of triterpenoid saponins obtained from the Australian desert tree Acacia victoriae (Leguminosae: Mimosoideae) that inhibit tumor cell growth and induce apoptosis, in part, by perturbing mitochondrial function. These saponins have also been found to prevent chemical-induced carcinogenesis in mice. This study examines the effect of a triterpene mixture (F094) and a single molecular species (avicin G) isolated from the mixture on tumor necrosis factor (TNF)-induced activation of nuclear transcription factor-kappaB (NF-kappaB) in Jurkat cells (human T cell leukemia). Both F094 and avicin G were found to be potent inhibitors of TNF-induced NF-kappaB. Treatment of Jurkat cells with avicin G resulted in a much slower accumulation of the p65 subunit of NF-kappaB into the nucleus whereas the degradation of IkappaBalpha was unaffected. Avicin G also impaired the binding of NF-kappaB to DNA in in vitro binding assays. Treatment of cells with DTT totally reversed the avicin G-induced inhibition of NF-kappaB activity, suggesting that sulfhydryl groups critical for NF-kappaB activation were being affected. Avicin G treatment resulted in decreased expression of NF-kappaB-regulated proteins such as inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX-2). Thus, the avicins may prove important for reducing both oxidative and nitrosative cellular stress and thereby suppressing the development of malignancies and related diseases.

Acacia↗
PubMed1984

myo-Inositol 1,4,5-trisphosphate stimulates protein phosphorylation in saponin-permeabilized human platelets.

In an attempt to establish a system with physiological substrates and phospholipid surfaces to investigate Ca2+- and 1,2-diacylglycerol-dependent protein kinase C activation, saponized platelets were used. Saponin, through interaction with plasma membrane cholesterol, makes cells permeable without major disruption of organelles. Washed platelets, prelabeled with 32P, were treated with 1-50 micrograms of saponin per ml. Permeabilization was evident at a concentration of 10 micrograms of saponin per ml, as indicated by the action of extracellular Ca2+ on the phosphorylation of the 20,000- and 40,000-Da proteins. These proteins are, respectively, the substrates for myosin light chain kinase and protein kinase C. Activation of these enzymes occurred when the estimated free [Ca2+] was changed from approximately equal to 80 nM to 300 nM. The effect of Ca2+ on kinase C-induced phosphorylation was potentiated by 1,2-didecanoylglycerol (1 microM). myo-Inositol 1,4,5-trisphosphate (5-20 microM) increased phosphorylation of the 20,000- and 40,000-Da proteins. This action was time and concentration dependent. The effect of myo-inositol 1,4,5-trisphosphate on the activation of kinase C was additive with 1,2-didecanoylglycerol. The action of myo-inositol 1,4,5-trisphosphate could be due to mobilization of Ca2+ from platelet organelles and/or to a direct effect on protein kinases.

Blood Platelets↗
PubMed1981

The effect of dietary protein source and saponins on serum lipids and the excretion of bile acids and neutral sterols in rabbits.

1. Four groups of six rabbits were given purified diets in which the dietary variables were protein source (isolated soya-bean protein or cow's-milk protein) with or without saponin supplementation (10 g/kg). 2. Rabbits given soya-based diets showed significantly lower serum concentrations of triglyceride and cholesterol (P less than 0.01). The latter changes were confined to the cholesterol fractions of beta-lipoproteins. 3. These changes in serum cholesterol were associated with a significantly increased excretion of acid and neutral sterols in animals given soya-bean protein. 4. There was no evidence to suggest that the effect of dietary protein source on serum lipids and the excretion of total and individual sterols was influenced by saponin supplementation. 5. These results do not support the hypothesis that the hypocholesterolaemia associated with plant proteins is due to the presence of saponins.

Animals↗