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PubMed1994

Cytotoxic saponins from New Zealand Myrsine species.

The observed biological activity in two New Zealand Myrsine species has been shown to be due to the presence of triterpene saponins. From Myrsine australis a series of eight oleanane-type saponins was obtained, with compounds 1-4 and 7 and 8 being novel. Also isolated were ardisiacrispin A [5] and ardisiacrispin B [6]. The structures of the new compounds were determined by chemical and spectroscopic techniques. Extracts of Myrsine salicina yielded only one saponin, 5. Saponins 1-8 were shown to be combinations of four oleanane triterpenes bonded to beta-D-xylp(1-->2)-beta-D-glcp(1-->4)-[beta-D-glcp(1-->2)]-alpha-L -arap (compounds 1, 3, 5, 7) and this same tetrasaccharide with alpha-L-rhap replacing the beta-D-xylp unit (compounds 2, 4, 6, 8).

Animals↗
PubMed1998

Evaluation of biological activities of triterpenoid saponins from Maesa lanceolata.

From a bioassay-guided fractionation procedure using Herpes simplex virus type 1 as the target model, a virucidal saponin mixture (maesasaponin mixture B) was isolated from the MeOH extract of leaves of Maesa lanceolata. The maesasaponin mixture B consisted of six homologous oleanane-type triterpenoid saponins 1-6, identified by 1H, 13C, and 2D NMR spectroscopy and mass spectrometry. The maesasaponin mixture B (1-6) showed several biological activities expected for saponins. It exhibited a moderate virucidal activity against enveloped viruses. The maesasaponin mixture B (1-6) was tested for further properties. The saponin mixture was found to be highly hemolytic and molluscicidal: it hemolyzed 50% of human erythrocytes (1% suspension) at a concentration estimated at 1.6 microg/mL and exerted against Biomphalaria glabrata snails a severe toxic effect with LD95 and LD50 values of 4.1 and 2.3 ppm, respectively. In addition, the maesasaponin mixture B (1-6) showed moderate fungistatic and antimutagenic properties. The evaluation of these diverse activities is described.

Animals↗
PubMed1999

Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells.

Two new triterpene saponins (8 and 9) and seven previously reported triterpene saponins (1-7) based upon oleanolic acid or hederagenin, along with two known lignans, (+)-pinoresinol (10) and beta-peltatin (11), were isolated from a saponin fraction prepared from the MeOH extract of the roots of Pulsatilla chinensis. The structures of the new saponins were determined by spectroscopic analysis, including 2D NMR spectroscopic techniques, and the results of hydrolytic cleavage. The isolated compounds and some derivatives were evaluated for their cytotoxic activity against HL-60 human leukemia cells.

Antineoplastic Agents, Phytogenic↗
PubMed1987

Effect of guanosine triphosphate on the release and uptake of Ca2+ in saponin-permeabilized macrophages and the skeletal-muscle sarcoplasmic reticulum.

The effects of GTP, with or without polyethylene glycol (PEG), on the release and uptake of Ca2+ were examined by using saponin-treated macrophages and sarcoplasmic reticulum isolated from skeletal muscles. The application of GTP in concentrations in the range 0.1-10 microM induced a gradual, small but sustained release of Ca2+ from the saponin-treated macrophages. The addition of PEG to GTP markedly enhanced the GTP-mediated Ca2+ release. GTP at the same concentration ranges used for Ca2+ release decreased the amount of Ca2+ uptake, at a steady state, but stimulated the rate of Ca2+ accumulation in the presence of oxalate, the Ca2+-precipitating anion. The addition of PEG abolished the GTP-evoked stimulation of Ca2+ accumulation in the presence of oxalate. The stimulating effect on the rate of Ca2+ accumulation by GTP and its elimination by PEG were not due to changes in the permeability of oxalate by either GTP or PEG, or both. The Ca2+-releasing effect of GTP without PEG was enhanced by eliminating the uptake activity by decreasing the content of ATP. These results indicate that GTP has an inherent activity to release Ca2+ from non-mitochondrial intracellular stores of saponin-treated macrophages, and PEG enhances the GTP-mediated Ca2+ release, partly owing to its eliminating effect on GTP-stimulated Ca2+ uptake activity. These effects of GTP observed with saponin-permeabilized macrophages were not apparent in the isolated skeletal-muscle sarcoplasmic reticulum.

Animals↗
PubMed1994

Saponin-induced release of cell-surface-anchored Thy-1 by serum glycosylphosphatidylinositol-specific phospholipase D.

A glycosylphosphatidylinositol-specific phospholipase D (GPI-PLD) was purified from human serum and used for studies on the release of GPI-anchored Thy-1 glycoprotein from mouse T lymphoma cells Y191. Previous studies have shown that whereas GPI-PLD is highly active against detergent-solubilized GPI-anchored proteins, it is normally unable to release GPI-containing proteins anchored in a lipid bilayer. Confirming these findings, the addition of GPI-PLD to intact Y191 cells did not result in cleavage of Thy-1. However, pretreatment of cells with saponin, a cholesterol-sequestering agent, rendered Thy-1 susceptible to hydrolysis. Very little solubilization of GPI-containing Thy-1 occurred under these conditions. From experiments with reconstituted liposomes it was inferred that the effect of saponin on cells was to aid in the presentation of Thy-1 to GPI-PLD. Furthermore, it was concluded that cholesterol-saponin complexes formed in the membrane were not alone responsible for the effect. Rather, additional molecules in the plasma membrane are possibly involved in the presentation of Thy-1 on saponin-treated cells. This finding may have implications for a physiological role of circulating GPI-PLD in the regulation of GPI-anchored proteins on cells.

Animals↗
PubMed1997

An improved method for thick film preparation using saponin as a lysing agent.

Thick film examination for malaria is often hampered by the presence of cellular debris obscuring parasites. This is a major problem for diagnostic laboratories that do not have a high exposure to material identification. Films that are relatively free of cellular debris, allowing easier identification of parasites are an obvious advantage. Saponin has been used by researchers to liberate malarial parasites for harvesting from infected erythrocytes. It has also been used for thick film preparations for diagnosis, but has not gained widespread acceptance, possibly due to the persistence of cellular debris inherent in the technique. In the present study the saponin method for thick film examination has been modified by the inclusion of a centrifugation step to remove cellular debris. Thick films were run in parallel with films made using the standard Fields stain technique and the original saponin. Results indicate that the modified saponin technique provides superior preparations free of cellular debris.

Animals↗
PubMed2000

Effect of steroidal saponin from Yucca schidigera extract on ruminal microbes.

The effects of steroidal saponins (SAP) isolated from Yucca schidigera extract on ruminal bacteria and fungi were investigated in pure culture studies. Prevotella bryantii, Ruminobacter amylophilus, Selenomonas ruminantium and Streptococcus bovis were cultured through ten 24-h transfers in ruminal fluid medium containing 0 or 25 microg SAP ml-1 (measured as smilagenin equivalents). The four strains, each non-exposed or pre-exposed to SAP, were then inoculated into medium containing 0 or 250 microgram smilagenin equivalents ml-1 and 24-h growth curves were determined. The cellulolytic ruminal bacteria Ruminococcus flavefaciens, Fibrobacter succinogenes and Rc. albus were cultured for 72 h on Whatman no. 1 filter paper in medium containing 0, 9, 90 or 180 microgram SAP ml-1 for the determination of filter paper digestion and endoglucanase activity. The ruminal bacteria differed in their responses to SAP. Steroidal saponins in the medium reduced the growth of Strep. bovis (P < 0.01 at 2, 3, 4, 5, 6 and 8 h), P. bryantii (P < 0.05 at 4, 5, 6, 8, 10 and 24 h) and Rb. amylophilus (P < 0.05 at 14 and 24 h), but the growth of S. ruminantium was enhanced (P < 0.05) at 10, 14 and 24 h. The growth curves of all four non-cellulolytic species were similar (P > 0.05) between pre-exposed and non-exposed cultures and the concentrations of total SAP and soluble (deglycosylated) SAP in the liquid fraction were unchanged (P > 0.05) over time. Steroidal saponins inhibited the digestion of filter paper by all three cellulolytic bacteria, but F. succinogenes was less (P < 0.05) sensitive to SAP and more (P < 0. 05) effective at deglycosylating SAP than were Rc. flavefaciens or Rc. albus. Transmission electron microscopy revealed that SAP altered the cell walls of the SAP-inhibited non-cellulolytic bacteria. The ruminal fungi, Neocallimastix frontalis and Piromyces rhizinflata, were cultured on filter paper in medium containing 0, 0. 45, 2.25 or 4.5 microgram SAP ml-1. Filter paper digestion by both fungi was completely inhibited by 2.25 microgram SAP ml-1. Steroidal saponins from Y. schidigera inhibit cellulolytic ruminal bacteria and fungi, but their effects on amylolytic bacteria are species dependent and similar to the effects of ionophores. As such, SAP may be useful in nutritional applications targeting starch-digesting ruminal micro-organisms.

Amyloid↗
PubMed2000

Antileishmanial activity of three saponins isolated from ivy, alpha-hederin, beta-hederin and hederacolchiside A1, as compared to their action on mammalian cells cultured in vitro.

The in vitro antileishmanial activity of three saponins isolated from ivy, alpha-hederin, beta-hederin and hederacolchiside A1, was investigated on Leishmania infantum. The assessment of possible targets (membrane integrity, membrane potential, DNA synthesis and protein content) was performed in both Leishmania promastigotes and human monocytes (THP1 cells). Results observed in Leishmania showed that the saponins exhibited a strong antiproliferative activity on all stages of development of the parasite by altering membrane integrity and potential: hederacolchiside A1 appeared to be the most active compound against both promastigotes and amastigotes. Results observed in THP1 cells demonstrated that the saponins exerted also a potent antiproliferative activity against human monocytes, by producing a significant DNA synthesis inhibition. The ratio between antileishmanial activity on amastigotes and toxicity to human cells suggested that the saponins could be considered as possible antileishmanial drugs.

Animals↗
PubMed2000

A new steroidal saponin from the leaves of Agave americana.

A new bisdesmosidic spirostanol saponin, along with three known saponins, were isolated from Agave americana (Agavaceae). The structure of the new saponin was elucidated as (25R)-3 beta,6 alpha-dihydroxy-5 alpha-spirostan-12-one 3,6-di-O-beta-D-glucopyranoside. Among the isolated saponins, hecogenin tetraglycoside showed cytotoxic activity against HL-60 human promyelocytic leukemia cells with an IC50 value of 4.3 micrograms/mL.

Antineoplastic Agents, Phytogenic↗
PubMed2001

Investigations of the mechanism of membrane activity of selected triterpenoid saponins.

The experiments with different triterpenoid saponins showed a significant difference in the microphysiometric activity between acylated and non-acylated compounds. Only acylated saponins in low concentrations were able to activate the metabolism of endothelial cells after short-time incubation in a transient manner lasting approximately 2 hours. The strongest effect was produced by virgaureasaponin b, an incubation with 4 microg/ml over 6 min induced a stimulation of the metabolic activity of 190% maximum after 30 min. This treatment did not induce non-reversible toxic effects, and could be repeated in the same way after a recovery period. The saponins without acylation in the glycosidic part did not induce metabolic stimulation, even in concentrations higher than observed for the acylated compounds. The current interpretation of the results is connected with the suggestion that especially acylated saponins are able to integrate into the cellular membrane transiently. This integration might induce pore-like structures which change the membrane permeability associated with alterations in the ionic homeostasis between intracellular and extracellular compartments.

Animals↗
PubMed2005

Saponins from Chinese Buckeye Seed reduce cerebral edema: metaanalysis of randomized controlled trials.

To evaluate the effects of saponins from Chinese Buckeye Seed in the treatment of cerebral edema in patients with stroke or cerebral trauma, a metaanalysis of randomized controlled trials was conducted. Randomized trials that compare the effects of treatment with saponins from Chinese Buckeye Seed to placebo treatment, to lack of treatment, to non-specific treatment, or to mannitol treatment for cerebral edema were identified with electronic and manual searches. No blinding and language limitations were applied. The methodological quality of trials was assessed with the Jadad scale plus allocation concealment. The metaanalysis was performed where data were available. Forty-one randomized controlled trials involving 4066 patients were identified. The methodological quality of the trials was generally low. The combined results showed that intravenous administration of saponins from Chinese Buckeye Seed increased the total effective rate, reduced the mortality and the incidence of renal function impairment in comparison to control treatment. No serious adverse event was reported. Based on the metaanalysis, saponins from Chinese Buckeye Seed can reduce cerebral edema in patients with stroke or cerebral trauma. However, the evidence is not sufficient due to the generally low methodological quality of the studies. Further trials are needed with sufficiently numerous group size and rigorous design.

Aesculus↗
PubMed2005

Structure-activity-relationship of saponins to enhance toxic effects of agrostin.

Saponins with an aldehyde function bound at C-4 from different plant origins increase the cytotoxicity of the lectin agrostin by enhancing its penetration through the cell membrane. Experiments with different pure saponins in combination with agrostin showed that also the glycosidic part of acidic bisdesmosidic saponins especially the oligosaccharidic ester chain at C-28 plays an important role in the potentiation of agrostin's cytotoxicity as result of an interaction between saponins and lectins at the cell membrane.

Antineoplastic Agents↗
PubMed2005

Structure-activity relationships for saponins from Allium hirtifolium and Allium elburzense and their antispasmodic activity.

A phytochemical study of Allium hirtifolium Boiss flowers has led to the isolation of high amounts of six new furostanol and spirostanol saponins, named hirtifoliosides A1/A2 (1a/ 1b), B (2), C1/C2 ( 3a/ 3b), and D(4) along with three known spirostanol saponins, alliogenin 3- O-beta-D-glucopyranoside, gitogenin 3- O-beta-D-glucopyranosyl-(1-->4)- O-beta-D-glucopyranoside, and agapanthagenin 3- O-beta-D-glucopyranoside. High concentrations of the following known flavonol glycosides have been isolated from both flowers and bulbs: kaempferol 3- O-beta-D-rhamnopyranosyl-(1-->2)-glucopyranoside, kaempferol 3- O-beta-D-glucopyranosyl-(1-->4)-glucopyranoside, kaempferol 3-O-glucopyranoside, kaempferol 7-O-glucopyranoside. The isolated saponins along with the four saponins elburzensosides A1/A2 and C1/C2 and the sapogenin agapanthagenin, previously described from A. elburzense, have been subjected to biological assays for evaluating possible antispasmodic activity in the guinea-pig isolated ileum. The obtained results served as a basis for the establishment of structure-activity relationships within this class of antispasmodic agents. They highlight the positive effects of a hydroxyl group at position 5 and of a glucose unit at position 26 and demonstrate the detrimental effects of both a hydroxyl group at position 6 and of a glucose unit at position 3. Among the tested compounds, elburzensosides C1/C2 and agapanthagenin showed the highest activity in reducing induced contractions as measured by the reduction of histamine release by about 50 %. The observed effect therefore contributes to the explanation of the traditional use of onion and garlic in the treatment of disturbances of the gastrointestinal tract.

Allium↗
PubMed2006

Detection of saponins in extracts from the rhizomes of Paris species and prepared Chinese medicines by high performance liquid chromatography-electrospray ionization mass spectrometry.

A highly sensitive and specific method, based on high performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS), was developed for simultaneous detection of eleven steroidal saponins and one phytoecdysone in extracts from the rhizomes of thirteen PARIS species and four prepared Chinese medicines (PCMs). The HPLC experiments were performed by means of a reversed-phase C18 column (4.6 mm x 150 mm, 5 microm) and mobile phase system consisting of 0.1 % aqueous formic acid and acetonitrile under gradient elution conditions. The most intensive electrospray ionization signals were found in the negative ion spectra due to HCOO- adducts. The limits of detection (LODs) for the saponins were lower than 40 ng/mL in selected ion monitoring (SIM) mode. The identification of the saponins in the extracts of PARIS species and PCMs was confirmed using their retention times and mass spectral comparisons to standard compounds. The validated method was successfully applied for simultaneous detection of twelve standard compounds in the analytes so that it provided a new means for quality evaluation of Rhizoma Paridis and Chinese multiherb remedies that contain Rhizoma Paridis. The results showed that most species of PARIS contain steroidal saponins, which provided evidence for expanding the botanical origin of Rhizoma Paridis.

Chromatography, High Pressure Liquid↗
PubMed1990

Inhibitory effects of saponins from Tetrapleura tetraptera on the LH released by cultured rat pituitary cells.

Ethanolic extracts from stem bark of Tetrapleura tetraptera exerted an inhibitory effect on the luteinizing hormone (LH) released by cultured rat pituitary cells. These extracts contained triterpenic saponins, tannins, and flavonoids as estimated through phytochemical screening. Saponins were extracted. They apparently inhibited the luteinizing hormone-releasing hormone (LHRH)-induced LH release, the inhibition level being dose-dependent. Yet, the intracellular LH content remained constant whatever the saponin concentration, which demonstrated a lack of effect on the true release process. Accordingly, an interaction between saponins and LH released into the medium was demonstrated, which led to a decrease in the amount of immunoassayable hormone. This decrease was both time- and dose-dependent. It occurred even in the presence of serum in the medium, which suggests that the inactivation process may occur in vivo. Taken together, these results could explain the anti-gonadotrope properties of T. tetraptera extracts that are used as natural contraceptives in Ivory Coast pharmacopoeia.

Animals↗
PubMed1992

Time course and inhibition of saponin-induced hemolysis.

Hemolytic activities of 3 steroid saponins reached plateaus within 5 min, whereas those of 4 triterpenoid saponins did not within 60 min. Erythrocytes pretreated with a low concentration of tigogenin were resistant to hemolysis of some of these saponins, but those pretreated with hecogenin or tomatidine were as sensitive as non-treated erythrocytes. Therefore, the ketone group of hecogenin or the amino group of tomatidine would weaken the interactions between the erythrocytes and these sapogenins. Furthermore, incubations of these saponins with a small amount of cholesterol diminished the hemolytic activities.

Animals↗
PubMed1979

Effects of saponins on bile acids and plasma lipids in the rat.

1. The effects of feeding isolated saponins on plasma lipid concentrations and on concentrations of biliary and faecal bile acids and neutral sterols were studied in the rat. 2. The animals were given one of four diets, i.e. a standard low-cholesterol synthetic diet, the diet + 10 g saponins/kg, the diet + 10 g cholesterol/kg, the diet + 10 g cholesterol + 10 g saponins/kg. 3. Saponins partially reversed the hypercholesterolaemia caused by the high-cholesterol diet and increased both the rate of bile acid secretion and the faecal excretion of bile acids and neutral sterols. The proportionate contribution of the primary bile acids (particularly chenodeoxycholic) to faecal excretion was also increased by saponins. 4. The results are discussed in relation to the hypothesis that saponins act by inducing the adsorption of bile acids by dietary fibre.

Animals↗
PubMed2002

Rumen fermentation and nitrogen balance of lambs fed diets containing plant extracts rich in tannins and saponins, and associated emissions of nitrogen and methane.

Tannins were added to experimental diets at levels of 1 and 2 g/kg DM (hydrolysable tannins; Castanea sativa wood extract) and saponins at 2 and 30 mg/kg DM (sarsaponin; Yucca schidigera extract). These levels were far below thresholds expected to be adverse in ruminants. Effects were measured in lambs by comparison with unsupplemented control diets calculated to be either deficient (10%) or adequate in protein. The diets consisted of hay, concentrate (1:1) and extra wheat starch with increasing body weight. Ruminal pH, VFA concentration, protozoa count and apparent digestibilities of organic matter and fibre did not differ among treatments. The low tannin dose significantly decreased bacteria count compared to the high saponin dose. Saponin supplementation and the high tannin dose showed some potential to reduce ruminal ammonia concentration. This was associated with weak trends towards lower urine N excretion (only tannins) and ammonia emission from manure. Methane release was increased by the low tannin dose compared to the unsupplemented control. Diet effects on heat production were not systematic. In conclusion, the extracts rich in tannins or saponins gave only slight indications for either increased body nitrogen retention or reduced nitrogen emission. However, effects might have been larger with more pronounced dietary protein deficit.

Animal Feed↗