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PubMed2004

[Effects of arsenic trioxide, ginseng saponin and beta-elemene on telomere-telomerase system in K562 cell line].

The aim was to explore the modulating and inhibiting effects of arsenic trioxide, ginseng saponin and beta-elemene on telomere length and telomerase activity in K562 cell line, and to study their anti-tumor mechanism and seek new method of therapy for acute leukemia. Human erythroleukemia cell line K562 was co-cultured with arsenic trioxide, ginseng saponin, beta-elemene separately, cells were collected after 24, 48 and 72 hours for further detecting. Telomere length and telomerase activity were detected by the methods of Southern-blot and PCR-ELISA respectively. The effects of these drugs on telomere length and telomerase activity were observed at different concentrations and length of time. The results showed that (1) telomerase activity of K562 cells decreased after co-cultured with arsenic trioxide, ginseng saponin and beta-elemene. The inhibiting effects depended on drug concentrations and length of time. When co-cultured at proper concentration and period of time, telomerase activity could be inhibited; (2) viability of K562 cells decreased after co-cultured with arsenic trioxide, ginseng saponin and beta-elemene, the inhibiting effect depends on drug concentrations and length of time; (3) after co-cultured with arsenic trioxide, ginseng saponin, and beta-elemene for 72 hours, telomere length of K562 cell line prolonged a little. It is concluded that (1) arsenic trioxide, ginseng saponin and beta-elemene can inhibit telomerase activity in K562 cell line, the suppression of telomerase activity may be one of the mechanisms of anti-tumor effect; (2) arsenic trioxide, ginseng saponin and beta-elemene can inhibit the growth of K562 cell line, the inhibiting effect depends on concentration and time; (3) when telomerase activity was suppressed, the telomere length prolonged a little, indicating that in K562 cell line may exist another mechanism to regulate telomere length, except telomerase activation.

Arsenic Trioxide↗
PubMed1995

Effect of saponin from Quillaja saponaria (molina) on antibody, tumour necrosis factor and interferon-gamma production.

Saponin has been described to contain adjuvant activity in vaccination protocols, in protection against disease, and on humoral immune response. In this paper we describe the effect of a pure saponin from Quillaja saponaria (molina) on the immune response elicited in mice by two antigens, BSA and Crotalus durissus terrificus (South American rattlesnake) venom. Antibody production as measured by ELISA shows that saponin was able to increase antibody synthesis to both antigens. Moreover, mice immunized with verom plus saponin were completely protected against the lethal effects of the venom. The effect of saponin was also evaluated for cytokine production. Tumour necrosis factor activity about 2.9 times higher than in control mice was detectable in sera from animals immunized with saponin. Interferon-gamma was produced only when BSA and saponin were injected together into the mice.

Adjuvants, Immunologic↗
PubMed2001

Separation of naturally occurring triterpenoidal saponins by capillary zone electrophoresis.

A high-performance capillary electrophoresis (HPCE) was successfully applied to the separation and quantitation of naturally occurring oleanene triterpenoidal saponins. The HPCE adapted to the separation of two pairs of disteriomeric saponins (1-2) or (3-4), obtained from Trifolium alexandrinum seeds, was based on capillary zone electrophoresis (CZE) in borate buffer with UV detection at 195 nm. An usual technique for isolation and group separation of saponins was developed as an appropriate purification step prior to determination of individual saponins by CZE. The separation parameters such as borate concentration, pH and applied voltage were varied in order to find the best compromise that complied with demands for high separation, short duration and sufficiently high detector response. The optimum running conditions were found to be 60 mM borate buffer, pH 10 and 12 kV. Under the alkaline borate electrolyte, no resolution was achieved for the saponins (1 and 3) or (2 and 4) in a single mixture, except when 20 mM beta-cyclodextrin was added to the running electrolyte. With the combined techniques of group separation, purification and CZE, a rapid and efficient method for the determination of naturally occurring diasteriomeric saponins is now available.

Buffers↗
PubMedDate not supplied

Analysis of bisdesmosidic saponins in Saponaria vaccaria L. by HPLC-PAD-MS: identification of new quillaic acid and gypsogenin 3-O-trisaccharides.

A high-performance liquid chromatographic method using photodiode array and single quadrupole electrospray mass detection for analysis and profiling of bisdesmosidic saponins in Saponaria vaccaria seed was developed. Profiles of seed extract from three different plant sources were obtained and found to contain the same saponins, albeit in different proportions. Several known saponins were identified by selected ion extraction of quasi-molecular ions from the total ion chromatogram and confirmed by their mass spectra. Application of high cone voltages afforded mass spectra containing key diagnostic fragments and relatively strong singly charged quasi-molecular ions. In addition to previously identified saponins, several new quillaic acid and gypsogenin bisdesmosides could be detected via mass spectral analysis. Five of these were tentatively identified as pentose homologues of known saponins, having an added xylosyl residue linked to the 3-O-glucuronyl group (1 --> 3). The stereochemistry and identity of the xylosyl linkage in the new saponins was determined by chemical means. Previously reported vaccaric or segetalic acid-type bisdesmosides could not be detected in any of the extracts.

Carbohydrate Conformation↗
PubMed2004

Evaluation of bioactive saponins and triterpenoidal aglycons for their binding properties on human endothelin ETA and angiotensin AT1 receptors.

Different types of triterpenes including saponins and aglycons were evaluated for their ability to inhibit [3H] BQ-123 and [3H] angiotensin II binding to the human endothelin 1 ETA and angiotensin II AT1 receptors, respectively. Selectivity for only one of the two receptors was exhibited by asiatic acid and its saponins (ETA) and oleanolic acid (AT1). To a lesser extent betulinic acid, beta-amyrin and friedelin also showed selectivity for the ETA receptor. To address the question whether the effect of saponins on cell membranes might interfere with the normal binding of specific radioligands to their receptors, the activity of saponins with different haemolytic properties were compared. Highly haemolytic saponins such as alpha-hederin and beta-escine showed partial (60%) inhibition of radioligand-binding to the ETA receptor and complete inhibition (100%) to the AT1 receptor. Moreover, the haemolytically inactive kryptoescine, at the same concentration, caused complete inhibiton of radioligand-binding to both receptors, indicating that inhibition of receptor binding was not related to the membrane-interacting properties of saponins.

Animals↗
PubMed2006

Antidermatophyte activity of medicago extracts and contained saponins and their structure-activity relationships.

Saponin-rich extracts of Medicago sativa L. have been shown to display antifungal activity against a range of common fungibut only a few individual saponins have been tested against dermatophytes. Total saponins were separately obtained from roots and aerial parts of Medicago sativa, M. murex, M. arabica and M. hybrida. Nineteen saponins and three parent triterpenoids, were tested against three dermatophytic fungi Microsporum gypseum, Trichophyton interdigitale and T. tonsurans using mircowell plate serial dilution assay to determine the Minimum Inhibitory Concentration (MIC). Miconazole was used as a positive control. T. tonsurans appeared to be the most sensitive of the dermatophytes to the active compounds. Aglycones showed less antifungal effect than the glycosides, which displayed a range of activities. Monodesmosidic glycosides of medicagenic acid were the most active compounds, especially the 3-O-beta-D-glucopyranoside, which displayed MIC less than 0.09mm against all three fungi, although those of hederagenin and zanhic acid also showed weak activity (MIC 3.3mm against two fungal species). Bidesmosidic saponins had weaker activity than monodesmosidic ones. This corresponds to activity of these and similar compounds against other fungal species but this is the first comprehensive report of activity of Medicago saponins against dermatophytes.

Antifungal Agents↗
PubMed2004

Multiple-stage tandem mass spectrometry for differentiation of isomeric saponins.

Four isomers of steroidal saponins were differentiated using multiple-stage tandem mass spectrometry combined with electrospray ionization (ESI-MS(n)). With the addition of lithium salt, the [M+Li](+) ions of saponins were observed in the ESI spectra. MS(n) spectra of these [M+Li](+) ions provided detailed structural information and allowed differentiation of the four isomeric saponins. The cross-ring cleavage ions from the saccharide chains of the saponins could be used as diagnostic ions for information concerning the linkage of the sugar moieties of the saponins. The masses of the X, A, Y and C type fragment ions formed from [M+Li](+) ions of the isomeric saponins provided information defining the methyl group locations.

Binding Sites↗
PubMed1996

Studies on bioactive saponins from Chinese medicinal plants.

In our recent studies on bioactive saponins, two Chinese medicinal plants: Mussaenda pubescens Ait.f (Rubiaceae) and Clematis chinensis Osbeck (Ranunculaceae), were investigated. Of the two medicinal plants, M. pubescens is a Chinese folk medicine which has been used as a diuretic, antiphlogistic, diaphoretic and antipyretic agent, and has also been used to detoxify mushroom poisons and to terminate early pregnancy. Clematis chinensis is a Chinese traditional medicine which has been used as an analgesic, diuretic, antitumor, antiinflammatory and insecticidal agent for ages. As a result of our studies, eighteen saponins were identified from M. pubescens, among which seventeen were new compounds, while eleven saponins were isolated from C. chinensis, three of which were new compounds. In the course of our structural studies, mass fragment analysis in FAB-mass spectra and 1H- and 13C-NMR spectra were used to determine the structures of the sapogenin and oligosaccharide moieties. In those more complicated and minor saponins, various 2D-NMR experiments were carried out on 400-, 500- or 600-MHz NMR instruments, which permitted the identification of new sapogenins in glycoside form. In addition, it was also possible to assign all the proton and carbon signals of the sugar units on the basis of 1H-1H DQF COSY, TOCSY and HMQC spectra, which further permitted the establishment of linkage sites and sequences among the sugar units and aglycones by means of NOESY, ROESY and HMBC spectra. When the proton signals of sugar units are overlapped seriously in 1H-NMR spectra, peracetylation is a very helpful technique which can spread proton signals in wider range, thus simplifying their assignment by means of 2D-NMR spectra. When some of the sugar proton signals of a peracetylate are also overlapped coincidentally, alternation of deuterated solvents for measuring NMR spectra can circumvent the difficulties. Pharmacological tests indicated that mussaendoside O, the most abundant saponin from M. pubescens, can inhibit significantly the secretions of the lachrymal and salivary glands induced by galanthamine, and can also inhibit the contraction of the isolated longitudinal muscle strip from guinea pig ileum evoked by an M-Ach receptor agonist (carbachol, 10(-6) M) at concentrations of 10(-4) and 10(-5) M. From these results, the saponin should be an antagonist of the M-Ach receptor, and was presumed to be responsible for its antitoxicity activity toward some mushroom poisons of medicinal plant origin. In addition, mussaendoside O also showed immunopromotive and hemolytic activities.

Animals↗
PubMed1980

Specific perforation of muscle cell membranes with preserved SR functions by saponin treatment.

The effects of saponin on Xenopus and frog skeletal muscle fibres were examined. The twitch of Xenopus single fibres was first potentiated slightly and then irreversibly abolished by 5-10 microgram/ml of saponin. Treatment with saponin at 5-10 microgram/ml or higher concentrations for 30 min resulted in perforation of the muscle cell membrane, indicated by the following evidence. (i) Fibres became responsive to contractile activating solutions with a pCa-tension relationship similar to that of mechanically skinned fibres. (ii) Removal and re-introduction of MgATP became effective in bringing fibres into rigor and the relaxed state, respectively. (iii) After the saponin treatment large contractions due to Ca release from the SR could be elicited by substitution of Cl for methanesulphonate in the medium. (iv) The treatment decreased the optical path length across the fibre, indicating loss of soluble proteins. (v) The lattice spacing of myofilaments was wider after the treatment as in mechanically skinned fibres. Contractile response of mechanically skinned fibres and their SR responses such as Ca uptake, Ca-induced Ca release and Cl-induced Ca release were not affected by treatment with 50 microgram/ml saponin for 30 min, while 150 microgram/ml or higher concentrations severely impaired by the SR functions. It is possible, therefore, to make chemically skinned skeletal muscle fibres in which the functions of the SR are preserved by applying 10-50 microgram/ml saponin.

Animals↗
PubMed1999

In vitro anticomplementary activity of hederagenin saponins isolated from roots of Dipsacus asper.

Anticomplementary activity of hederagenin and related saponins isolated from Dipsacus asper was investigated in vitro. HN saponin F (3) was most potent with IC50 value of 3.7x10(-5) M followed by 3-O-beta-D-glucopyranosyl-(1->3)-alpha-L-rhamnopyranosyl-(1->2)-beta-L-+ ++arabi nopyranosyl hederagenin 28-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyrano side (8), 3-O-beta-L-arabinopyranosyl hederagenin 28-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside (5), dipsacus saponin A (4), and hederagenin (1) on the classical pathway (CP) of complement system, while the saponins 3-5 did not show the inhibition of hemolysis and rather increase the hemolysis on the alternative pathway (AP). However, all of C-3 monodesmosides [prosapogenin CP (2), dipsacus saponin B (6), and dipsacus saponin C (7)] evoked hemolysis directly on the erythrocytes.

Animals↗
PubMed1984

Interaction of saponin and digitonin with black lipid membranes and lipid monolayers.

The effects of the plant glycosides saponin as well as digitonin on the electrical conductance of black lipid membranes and the effect of these agents on the surface pressure of lipid monofilms was investigated. Both saponin and digitonin induced channel-like fluctuations in planar bilayers made either of diphytanoylphosphatidylcholine ( DPhPC ) or of DPhPC and cholesterol 2: 1 (w/w). In cholesterol-free bilayers the amount needed to induce an increase in conductance was 0.3-1 mg/ml for saponin and about 0.2 mg/ml for digitonin. In contrast, in cholesterol-containing bilayers the concentration needed to induce pores was about 10 micrograms/ml for both saponin and digitonin. In cholesterol-containing membranes the fluctuating pores induced by saponin were about 3-times more permeable to K+ than to Cl- and the macroscopic current showed an ohmic behaviour. Surface pressure experiments demonstrate that both glycosides could penetrate into lipid monofilms of pure DPhPC spread at the air/water interface with an initial surface pressure of 30 mN/m. The increase in surface pressure was considerably enhanced in cholesterol-containing films. It is assumed that the channel-like fluctuations induced by saponin as well as digitonin, in both cholesterol-free and cholesterol-rich bilayers are due to the formation of micellar structures within the lipid lattice. Probably the penetration of the glycosides into the lipid bilayer is considerably enhanced by the presence of cholesterol.

Animals↗
PubMed1986

Stimulation of mixed-function oxidation by NADPH in perfused mouse livers. Studies with saponin-permeabilized tissue.

In perfused livers from fed and fasted beta-naphthoflavone-treated C57BL/6J mice, maximal rates of p-nitroanisole O-demethylation were 30-40 mu moles/g/hr and 15-20 mu moles/g/hr respectively. The detergent saponin, at concentrations ranging from 0.001 to 0.005%, was infused between 2 and 30 min to establish optimal conditions to permeabilize plasma membranes. Permeabilization was assessed by release of lactate dehydrogenase and stimulation of p-nitroanisole O-demethylation by citrate. Saponin (0.005% for 5 min) alone had little effect on the rates of p-nitroanisole O-demethylation or conjugation of p-nitrophenol by perfused livers. Further, dicarboxylates or NADPH had no effect on rates of monooxygenation by perfused mouse liver in the absence of saponin. In saponin-treated livers from fasted mice, however, rates of monooxygenation were increased rapidly by infusion of dicarboxylates (10 mM malate, citrate, or isocitrate) or an NADPH-generating system (60 and 110% respectively), over a 6-8 min period. During this time period, cellular energetics were not comprised as reflected by normal rates of glucuronidation of p-nitrophenol. Thus, non-permeable metabolites can enter saponin-permeabilized cells in the perfused liver. Rates of monooxygenation were increased 40-60% in livers from fed mice by citrate, NADPH (200 microM) or an NADPH-generating system. In contrast, saponin decreased mixed-function oxidation assayed in isolated microsomes incubated with an NADPH-generating system. Taken together, these data support the hypothesis that maximal rates of monooxygenation in intact hepatocytes from fed as well as fasted mice is limited by the availability of NADPH.

Animals↗
PubMed1993

Spermicidal activity of an antifungal saponin obtained from the tropical herb Mollugo pentaphylla.

The ethyl acetate fraction of Mollugo pentaphylla, a tropical herb, contains an antifungal saponin (mollugogenol-A). We report here the spermicidal effects of this saponin. Washed sperm (> 100 x 10(6) with > 50% motility) from normal volunteers were incubated with varying concentrations (0-300 micrograms/ml) of mollugogenol-A at 30 degrees C. Sperm motility, velocity and viability were assessed at 0, 30, 60 minutes both manually and by using computer assisted semen analysis (CASA). Samples collected at 0 and 60 minutes were evaluated for membrane lipid peroxidation, superoxide dismutase (SOD) activity and transmission electron microscopy. A dose- and time-dependent effect of this saponin on sperm motion and viability was observed. The maximal spermicidal effect (4-5 fold decrease in motility and viability) was observed with 300 micrograms/ml dose of saponin. A three-fold increase in sperm membrane lipid peroxidation with corresponding inhibition of SOD activity were observed after 60 minutes incubation with this spermicidal agent. Transmission electron microscopy of saponin-treated samples revealed significant damage to the sperm membrane in both head and tail regions, and the acrosomal membranes were notably swollen and disrupted. These results indicate that this natural saponin has a potential spermicidal effect besides its known antifungal activity. The likely mechanism of its action involves sperm membrane damage by increased lipid peroxidation.

Acrosome↗
PubMed1993

Genetic and chemical polymorphisms of saponins in soybean seed.

The variation in saponin composition in soybean seeds is explained by different combinations of five genes controlling the utilization of soyasapogenol glycosides as substrates. The function of these genes is variety-specific and organ-specific. Phenotypes of over 1000 soybeans were classified into eight saponin types, and the frequency of phenotypes was different between the cultivated [Glycine max (L.) Merr.] and the wild soybean (G. soja Sieb. & Zucc.). The AaBc saponin type predominated in G. soja (58.4% of test collections), but was only found in 0.3% of G. max. Four unidentified arabinoside saponins were detected in the seeds of the AaBc type soybeans. The mode of inheritance of saponin types is explained by a combination of co-dominant, dominant and recessive acting genes. The combined chemical and genetic data show that the directed manipulation of soybean saponin composition is a possibility for the future.

Arabinose↗
PubMed1995

Molluscicidal saponins from Catunaregam nilotica.

Two new saponins were isolated from the fruits of Catunaregam nilotica Stapf, syn. Lachnosiphonium nilotica; Randia nilotica; Xeromphis nilotica. Their structures were determined mainly by spectroscopic methods as 3- O-[O-alpha-L-rhamnopyranosyl-(1-->3)-O-[O-beta-D-glucopyranosyl-(1 -->3)]- beta-D-glucopyranosyl]oleanolic acid and 28-O-beta-D- glucopyranosyl-3-O-[O-alpha-L-rhamnopyranosyl-(1-->3)-O[O-beta-D- glucopyranosyl]-beta-D-glycopyranosyl]oleanolate. The monodesmosidic saponin is a potent molluscicide against the schistosomiasis transmitting snail Biomphalaria glabrata with a LC50 value of 3 ppm. In addition two known saponins, 3-O-[2', 3'-di-O-(beta-D-glucopyranosyl)-beta-D- glucopyranosyl]oleanolic acid and 3-O-[O-beta-D-glucopyranosyl(1-->3)- beta-D-glucopyranosyl]oleanolic acid, were identified and their molluscicidal activity determined, the LC50 values being 26 and 3 ppm, respectively. Initial molluscicidal screening of the crude water and ethanol extracts revealed 100% snail mortality at concentrations of 100 and 50 ppm, respectively. The haemolytic activity of the molluscicidal saponins was determined as well and the HC50 values towards bovine erythrocytes found to be 3 ppm for the new saponin, and 16 and 2 ppm, respectively, for the two known saponins.

Animals↗
PubMed1990

Ca2(+)-dependent synthesis of prostaglandin I2 and mobilization of arachidonic acid from phospholipids in cultured endothelial cells permeabilized with saponin.

The feasibility of using saponin as a permeabilization agent to study the effect of free Ca2+ concentration ([Ca2+]f) on prostaglandin I2 (PGI2) synthesis and mobilization of arachidonic acid from membrane phospholipids was investigated in cultured bovine pulmonary artery endothelial cells (BPAEC). Treatment of BPAEC with 20 micrograms/ml saponin caused selective permeabilization of the plasma membrane as determined by measurements of the release of lactate dehydrogenase and beta-hexosaminidase. In cells prelabeled with [3H]arachidonic acid for 22 h, permeabilization with 20 micrograms/ml saponin induced PGI2 synthesis and release of [3H]arachidonic acid from membrane phospholipids. These effects were dependent upon [Ca2+]f in the range 72 nM to 5 microM. Release of [3H]arachidonic acid from phospholipid classes was determined in suspensions of BPAEC prelabeled with [3H]arachidonic acid and permeabilized with 20 micrograms/ml saponin. At [Ca2+]f optimal for PGI2 synthesis, 16.2% of the total incorporated [3H]arachidonic acid was released from phosphatidylinositol (3.4%), phosphatidylethanolamine (3.5%) and phosphatidylcholine (9.3%). The time course and dependence upon [Ca2+]f of [3H]arachidonic acid release from phospholipids correlated with PGI2 synthesis. The amount of PGI2 synthesized in permeabilized BPAEC was similar to that in cell cultures treated with the calcium ionophore A23187. In comparison, however, PGI2 synthesis induced by A23187 was associated with less release of [3H]arachidonic acid from membrane phospholipids, e.g., 2.3% versus 16.2%. The greater loss of [3H]arachidonic acid from phospholipids in saponin-permeabilized BPAEC was most likely due to the loss of cell integrity and/or nonspecific effects of the detergent on phospholipases. Despite these limitations, the Ca2+ dependence observed for PGI2 synthesis and [3H]arachidonic acid mobilization suggest that saponin-permeabilization may provide a useful system for studies of the intracellular events triggered by the rise in intracellular Ca2+ which culminate in PGI2 synthesis.

6-Ketoprostaglandin F1 alpha↗
PubMed1984

Effects of reticuloendothelial blockade on acute saponin poisoning in mice.

The effect of carbon particles on acute saponin poisoning in mice was studied. Pretreatment of mice with 5-10 mg of carbon particles resulted in protection from saponin intoxication even when given at a lethal dose. The protective effect of carbon particles decreased with increasing time interval between carbon-pretreatment and saponin administration although carbon particles remained in the tissues. Neither simultaneous (as a mixture with saponin) nor post-treatment of carbon particles brought about protection. Histological observations revealed that parenchymal and endothelial cells of the liver and spleen were protected from damage by saponin with the carbon-pretreatment. The results suggest that the reticuloendothelial-system (RES) blockade by carbon particles resulted in the reinforcement of RES, and consequently protected the animals from saponin poisoning, although the mechanism is not yet known.

Animals↗
PubMed2006

Acylation with diangeloyl groups at C21-22 positions in triterpenoid saponins is essential for cytotoxicity towards tumor cells.

Saponins are natural surfactants, found in many plants. Certain saponins are bioactive compounds with anticancer, antivirus and hemolytic activities. The mechanism is unknown. A saponin with antitumor activity was identified in Xanthoceras sorbifolia Bunge (Sapindaceae) and purified. This saponin is a triterpenoid saponin with a trisaccharide chain attached at C3 of the aglycone and two angeloyl groups acylated at C21 and C22. It inhibits the growth of tumor cells with IC50=2 microg/ml in OVCAR3 cells. To study the structure-activity relationship, the diangeloyl group or the carbohydrates of Xanifolia-Y were removed and tested for activity. It was found that removal of both angeloyl groups in C21 and C22 positions completely abolished its activity (IC50>120 microg/ml). However, when carbohydrates were remove, its activity was reduced but was not abolished (IC50=10 microg/ml). These results suggest that a presence of diangeloyl group in the triterpene structure play an essential role for activity. By comparison, compounds with a similar structure as Xanifolia-Y but have only one angeloyl group at C22: Xanifolia-X (IC50=6 microg/ml) or at C21: beta-escin (IC50=10 microg/ml), have less activity. Results suggest that diangeloyl group in both C21 and C22 positions are important contributing activity. Similar results were observed in hemolytic activity. It is concluded that acylation with angeloyl group at C21 and C22 positions of triterpenoid saponin is essential for its activity.

Acylation↗