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At least 19 recordsLinked to original sources
PubMed1995

Effect of soybean saponins and gypsophila saponin on morphology of colon carcinoma cells in culture.

The effect of saponins on colonic epithelial carcinoma cell (HCT-15) morphology was studied. Cells in culture were incubated with different concentrations of soybean saponins (SS) or gypsophila saponin (GS) for 24 hr. Scanning electron microscopy revealed a very rough and granular cell surface in cells treated with the lowest concentration of GS (40 ppm). Minor morphological changes were observed in the cell surface of soybean saponin-treated cells at a concentration of 1200 ppm. Examination by transmission electron microscopy indicated a dose-dependent effect of saponins on intracellular morphology of colonic epithelial carcinoma cells. Cells treated with 600 ppm or more of soybean saponins developed numerous cytoplasmic vesicles, had decreased density of cytoplasmic material and demonstrated deformations in plasma and nuclear membranes. Gypsophila saponin at a concentration of 40 ppm produced few changes in intracellular and membrane structure, whereas 80 ppm saponin induced the formation of vesicles. However, at both concentrations, changes in the density of cytoplasmic material was less extensive than in soybean saponin-treated cells. The highest concentration of gypsophila saponin used (160 ppm) completely destroyed the plasma membrane. These results indicate that soybean saponins and gypsophila saponin interact with cell membranes and induce significant dose-dependent cell morphological changes; however, they appear to act through different mechanisms.

Adenocarcinoma↗
PubMed2005

The impact of saponins or saponin-containing plant materials on ruminant production--a review.

Saponins are steroid or triterpene glycoside compounds found in a variety of plants. Some saponin-containing plants, mainly legumes, have been used as animal feed, but others are toxic. Several studies on the effect of saponins on ruminant production have also been reported. Some in vitro and in vivo experiments that demonstrate the beneficial effects of saponin such as defaunation of the rumen and manipulation of the end products of fermentation are described. Defaunation is the selective removal of protozoa from the rumen microbial ecosystem by a cell membrane cholesterol-saponin interaction, which causes cell rupture. Because protozoa in the rumen cause protein turnover by predating on bacteria, defaunation increases the nitrogen utilization of the ruminant and may lead to an increase in growth, milk, or wool production. The growth-promoting effect was evident in the high roughage diet suggesting that the application of saponins or saponin-containing plant materials may be beneficial for the subsistence farmers in developing countries. Saponins are deglycosylated by rumen microbes. Some sapogenins have been detected in the digestive tract of ruminants; however, the direct action of these compounds on the host animal is still unclear. No information on the effects of saponin on ruminant reproduction is available. There is an urgent need for a systematic evaluation of the most active structural components of the saponins, and their interaction with the microbial community, the host animal, and the diet. Along with these studies, the direct effects of saponins or their microbial degradation products on the host must be examined in order to get the full understanding of the metabolism and beneficial effects of saponins on animals.

Animals↗
PubMed1999

Korean red ginseng saponins with low ratios of protopanaxadiol and protopanaxatriol saponin improve scopolamine-induced learning disability and spatial working memory in mice.

The effects of two ginseng saponins having a different ratio of protopanaxadiol (PD) and protopanaxatriol saponins (PT) on the learning impairment induced by scopolamine, and learning and memory in mice were investigated in a passive avoidance task and a Morris water maze task. The ratio of PD and PT was 1.24 and 1.46, respectively. Before training, the ginseng saponins were administered intraperitoneally at doses of 50 and 100 mg/kg. The two saponins improved the scopolamine-induced learning impairment at different dosages in mice, 50 and 100 mg/kg, respectively. However, the two saponins did not show a favorable effect on learning and memory in normal mice. Korean red ginseng saponin with a low PD/PT ratio had an improving effect on spatial working memory, but the saponin with a high PD/PT ratio did not. This finding suggests that the PD/PT ratio of the ginseng saponins may be an important factor in the pharmacological role of red ginseng as a medicinal herb.

Animals↗
PubMed1997

Haemolytic activities of plant saponins and adjuvants. Effect of Periandra mediterranea saponin on the humoral response to the FML antigen of Leishmania donovani.

An 87.7% (P < 0.01) and 84% (P < 0.001) of protection against visceral leishmaniasis was achieved in CB hamsters and Balb/c mice, respectively, with saponin combined to the fucose-mannose ligand of Leishmania donovani (FML). However, an undesirable haemolytic effect was described for several saponins. Aiming to improve the formulation with FML/saponin, we comparatively analysed the haemolytic potential of recently characterized plant saponins and currently used adjuvants. The haemolytic activity of steroidic saponins from Agave sisalana; Smilax officinalis as well as commercial saponin (Riedel De Haën's), was higher than that of triterpenoid ones (Bredemeyera floribunda; Periandra mediterranea) and the Freund's complete adjuvant. The concentration resulting in 50% haemolysis was 500 micrograms ml-1 for aluminum hydroxide. The low haemolytic effect of P. mediterranea saponin was abolished by removal of its glycidic moiety and its sapogenin fraction as well as the Freund's Incomplete Adjuvant were non-haemolytic within this range. Furthermore, the adjuvant effect of three doses of P. mediterranea saponin injected with the FML antigen of L. donovani, was assayed in mice, either by the intraperitoneal (i.p.) or the subcutaneous (s.c.) route. The anti-FML IgG antibody levels increased and detectable levels were observed up to 3 months in the s.c. group. The response was expanded in both groups after an injection with a fourth vaccine dose. The IgG response showed increased levels of IgG2a only in the i.p. group, while IgG2b and IgG1 but not IgG3 antibodies were higher than controls in both groups. In conclusion, the results suggest that the recently described triterpenoid fractions of P. mediterranea can be safely used as adjuvant with low or non-haemolytic effect.

Adjuvants, Immunologic↗
PubMed2006

The saponin-mediated enhanced uptake of targeted saporin-based drugs is strongly dependent on the saponin structure.

Saponins are a group of plant glycosides consisting of a steroid or triterpenoid aglycone to which one or more sugar chains are attached. They exhibit cell membrane-permeabilizing properties and, thus, have been investigated for their therapeutic potential. Recently, at a non-permeabilizing concentration saponinum album from Gypsophila paniculata L. has been described to enhance the cytotoxicity of a chimeric toxin in a cell culture model. To elucidate whether this enhancing effect is also mediated by other saponins, we analyzed the ability of seven different saponins to enhance the cytotoxicity of a targeted chimeric toxin. The chimeric toxin is composed of saporin, a plant ribosome-inactivating toxin, a cleavable adapter, and human epidermal growth factor (EGF). Cytotoxicity on EGF receptor (EGFR)-bearing cells was analyzed both alone and after combined application of saponin and chimeric toxin. Only two of the tested saponins, quillajasaponin and saponinum album, enhanced cytotoxicity by more than 1,000-fold, whereas the enhancement factors of the other saponins were only approximately 10-fold. In contrast to saponinum album, quillajasaponin enhanced the cytotoxicity both on control cells lacking EGFR and on target cells, indicating that, in this case, the enhancement is not target cell receptor specific. This is also the case for some of the saponins with low enhancement factors. Saponinum album resulted in a more than 13,600-fold receptor-specific enhancement, decreasing the 50% inhibitory concentration (IC(50)) from 2.4 nM to 0.18 pM, which renders it the best option to promote saporin-3-based drug uptake while retaining specificity for the EGFR.

Animals↗
PubMed2002

[Isolation and identification of steroidal saponins in total saponin from Dioscorea nipponica Makino].

AIM: To investigate the water-soluble steroidal saponins in total saponin from Dioscorea nipponica Makino and look for new active compounds. METHODS: The compounds were isolated with silica gel, PTLC and HPLC, and their structures were elucidated by acid hydrolysis, physical and chemical data and spectral analysis (IR, NMR, MS, HMQC, HMBC) as well as chemical correlations. RESULTS: The two steroidal saponins (water-insoluble saponin and water-soluble saponin) were isolated from the total saponin of Dioscorea nipponica Makino. The structures were elucidated as diosgenin 3-O-[alpha-L-rhamnopy ranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]]-beta-D-glucopyranoside (I), diosgenin 3-O-[alpha-L-rhamnopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside (II). CONCLUSION: Compound II is a new steroidal saponin and firstly isolated from Dioscorea nipponica Makino. It was named as dioscin Dc.

Dioscorea↗
PubMed1976

Studies about the adjuvant activity of saponin fractions in foot and mouth disease vaccine. III. Comparison of the irritant, adjuvant and hemolytic activities of six commercial saponins and their hemolytic fractions obtained by chromatography on sephadex G 100.

12 experimental vaccines were prepared to compare the irritant and adjuvant activity in cattle of 6 commercial saponin preparations and their hemolytic fractions. It is still not known if a single substance is responsible for the irritant, adjuvant and hemolytic activities of the saponin preparations. The quantities of saponin added were standardised on the base of a constant hemolytic activity rather than on a weight of powder per dose of vaccine base. A FMD vaccine was used to reveal the adjuvant activity. It was concluded that the irritation is related to the hemolytic activity and not to the weight of powder. Irritation is slightly reduced when a toxic effect appears. The adjuvant activity was higher for untreated saponin preparations with high hemolytic activity used at low dose and for one of the chromatographic saponin fractions. The adjuvant activity is reduced when toxic effect appear. Toxicity of less hemolytic saponins used at high dose is removed by chromatography. Highly hemolytic saponins used at low dose become toxic after chromatographic treatment.

Adjuvants, Immunologic↗
PubMed1993

Effects of seed saponins of Thea sinensis L. (Ryokucha saponin) on alcohol absorption and metabolism.

We evaluated the effects of the seed saponins of Thea sinensis L. on alcohol absorption and metabolism in rats and mice. An ethanolic extract from the seeds of T. sinensis was orally administered to the rats 1 hr before or 0.5 hr after administration of ethanol (2 g/kg), and the blood ethanol assayed 0.5, 1, 2, 3, and 4 hr after ethanol administration. The ethanol level decreased after both pre- and post-administration of the extract. The extract was further purified to obtain a saponin fraction which was orally administered to mice 1 hr before ethanol administration. Blood, liver, and stomach were obtained 0, 1, 3, and 6 hr after ethanol administration, and the ethanol, acetaldehyde, acetate, and acetone concentrations in each specimen were measured by head space gas chromatography. The saponin fraction decreased the ethanol levels in the blood and liver but increased that in the stomach five-fold over the control level, suggesting inhibition of alcohol absorption. The ethanol disappearance time from the blood was shortened, suggesting the promotion of alcohol disappearance. The acetate and acetone levels were unaffected. However, the acetaldehyde level decreased in the blood, liver, and stomach. The decreases in the ethanol and acetaldehyde levels in the liver suggested the protective effects of the seed saponins on the liver. The saponins did not directly inhibit hepatic alcohol dehydrogenase activity. The seed saponins of T. sinensis seem to suppress alcohol absorption by slowing gastric emptying and by inhibiting absorption across the cell membranes of the digestive tract.

Acetaldehyde↗
PubMed1997

Isolation and structure elucidation of a highly haemolytic saponin from the Merck saponin extract using high-field gradient-enhanced NMR techniques.

Saponins SAPO50 and SAPO30, of which SAPO50 is highly haemolytic, have been isolated from the commercial Merck Saponin. Their structures have been determined exclusively by high-field gradient-enhanced NMR methods. The 1H and 13C NMR spectra of these saponins in pyridine-deuterium oxide have been assigned by homonuclear and heteronuclear correlation experiments. Anomeric configurations were obtained by combined use of 1JCH, 3JH-1.H-2, and 1D-NOESY data. Sugar residues were identified by use of 3JHH values obtained from their subspectra recorded using an optimized 1D-zeta-TOCSY sequence. Linkage assignments were made using the ge-HMBC and 1D-NOESY spectra. This study shows that SAPO50 represents a hitherto undescribed saponin with the following structure: 3-O-beta-D-xylopyranosyl-(1-->3)-[beta-D-galactopyranosyl- (1-->2)]-beta-D-glucuronopyranosyl gypsogenin 28-O-(6-deoxy-beta-D-glucopyranosyl)-(1-->4)-[beta-D-xylopyranosyl-(1--> 3)- beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D- fucopyranoside. SAPO30, however, corresponds to a saponin previously described [D. Frechet, B. Christ, B. Monegier du Sorbier, H. Fischer, and M. Vuilhorgne, Phytochemistry, 30 (1991) 927-931].

Carbohydrate Conformation↗
PubMed2003

Structures of new dammarane-type Triterpene Saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal Ginseng Saponins.

The saponin fraction from the flower buds of Panax notoginseng exhibited protective effect on liver injury induced by d-galactosamine and lipopolysaccharide. From the saponin fraction with hepatoprotective effect, five new dammarane-type triterpene saponins, notoginsenosides-O (1), -P (2), -Q (3), -S (4), and -T (5), were isolated together with nine known protopanaxadiol oligoglycosides. The structures of the new saponins were elucidated on the basis of chemical and physicochemical evidence. The principal dammarane-type triterpene saponins from the roots and flower buds of Panax notoginseng were found to show potent hepatoprotective effects.

Animals↗
PubMed2005

Bioactive saponins and glycosides. XXIII. Triterpene saponins with gastroprotective effect from the seeds of Camellia sinensis--theasaponins E3, E4, E5, E6, and E7.

The saponin fraction from the seeds of the tea plant [Camellia sinensis (L.) O. KUNTZE (Theaceae)] was found to exhibit potent protective effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. Five new triterpene saponins, theasaponins E3 (1), E4 (2), E5 (3), E6 (4), and E7 (5), were isolated together with 11 known saponins from the saponin fraction. The chemical structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated saponins, theasaponins E1 (6), E2 (7), and E5 (3) and assamsaponin C (10) showed an inhibitory effect on ethanol-induced gastric mucosal lesions at a dose of 5.0 mg/kg, p.o. and their activities were stronger than that of omeplazole. With regard to the structure-activity relationships of theasaponins, the following structural requirements for a protective effect on ethanol-induced gastric lesions were suggested; 1) the 21- and/or 22-acyl groups are essential for the activity, 2) acetylation of the 16-hydroxyl group reduce the activity.

Animals↗
PubMed2001

[Saponins and hemolytic activity. Saponins and glycosides from five species of Sapindaceae].

The haemolytic activity of saponins has been a known phenomenon for many years. In this work, structure-activity relationships were established from various triterpene saponins distinguishing hemolytic activity between mono- and bidesmosidic saponins. Saponins structure in Sapindaceae serve as a chimiotaxonomic criteria for dividing the species into two sub-families. In order to verify this criteria, five species were studied: Smelophyllum capense and Dimocarpus fumatus from the sub-family Sapindoideae, Filicium decipiens, Hippobromus pauciflorus, and Harpullia cupanioides from the sub-family Dodonaeoideae. Structure of eleven new saponins were elucidated from four species by the study of homo- and heteronuclear advanced NMR experiments and MS. Other metabolites were also isolated from Dimocarpus fumatus, including isoprenypchromenes and three new glycosides of long chain fatty alcohols.

Carbohydrate Sequence↗
PubMed2005

Isolation of a new saponin and cytotoxic effect of saponins from the root of Platycodon grandiflorum on human tumor cell lines.

A novel triterpenoid saponin, deapioplatycoside E (1) was isolated from the root extract of Platycodon grandiflorum, together with the seven known saponins 2 - 8, i. e., platycoside E (2), deapioplatycodin D3 (3), platycodin D3 (4), polygalacin D2 (5), platycodin D2 (6), deapioplatycodin D (7) and platycodin D (8). The structure of the new saponin 1 was determined on the basis of spectral analysis and chemical evidence. The crude saponin fraction (ED50: ca. 10 - 15 microg/mL) and compounds 6 - 8 (ED50: ca. 4 - 18 microg/mL) exhibited significant inhibition on the proliferation of five kinds of cultured human tumor cell lines, i. e., A549 (non-small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCT-15 (colon), in vitro.

Antineoplastic Agents, Phytogenic↗
PubMed1996

Application of MS-MS for the rapid, comparative analysis of saponin mixtures as exemplified by the deacylated and partially deacylated triterpenoid saponins of Bellis annua.

While most species of the Bellis genus are characterized by saponins in concentrations of ca.4% dry weight, Bellis annua only contains ca.0.3% saponins. Hence positive-ion electrospray ionization mass spectrometry, including MS-MS analysis, has been used extensively for the rapid identification of the saponins of B. annua obtained after mild alkaline hydrolysis. The saponin composition is similar to that of other Bellis species and, in addition, glycosides of the rare bellisonic acid, which has recently been found in B. bernardii, have been identified.

Carbohydrate Conformation↗
PubMed1995

Effect of soybean saponins and gypsophilla saponin on growth and viability of colon carcinoma cells in culture.

The effects of soybean saponins (SS) and gypsophilla saponin (GS) on the growth and viability of colon tumor (HCT-15) cells in culture were investigated. Cells were incubated in various concentrations of saponins for 1 hour (short term) or 48 hours (long term). Cell growth and viability were monitored at 24 and 48 hours. SS and GS inhibited cell growth and reduced cell viability in a dose-dependent manner in long-term treatment. The viability of cells was also reduced by short-term treatment with GS. The saponins differed in their effects on cell surface morphology: GS induced a rough and granular cell surface, whereas SS-treated cells displayed only minor morphological alterations. Changes in membrane permeability were assessed by measuring leakage of the cytoplasmic enzyme lactate dehydrogenase from cells. GS showed a concentration-dependent increase in lactate dehydrogenase leakage, whereas SS did not exhibit this effect. These results suggest that SS and GS have a significant growth-inhibitory effect on colon tumor cells in culture. However, it would appear that they are acting through different mechanisms.

Cell Division↗
PubMed1993

Saponin and sapogenol. XLVII. On the constituents of the roots of Glycyrrhiza uralensis Fischer from northeastern China. (1). Licorice-saponins A3, B2, and C2.

From the air-dried root of Glycyrrhiza uralensis, collected in the northeastern part of China, ten new oleanane-type triterpene oligoglycosides were isolated together with glycyrrhizin (1) and several known flavonoids. Among the newly isolated triterpene oligoglycosides, the chemical structures of licorice-saponin A3 (2), licorice-saponin B2 (3), and licorice-saponin C2 (4) have been determined, on the basis of chemical and physicochemical evidence, to be expressed as 30-O-beta-D-glucopyranosylglycyrrhizin, 11-deoxo-glycyrrhizin, and 3-O-[beta-D-glucuronpyranosyl(1-->2)-beta-D-glucuronpyranosyl++ +]oleana- 11,13(18)-dien-30-oic acid, respectively. During the course of these studies, facile conversions from glycyrrhizin (1) to licorice-saponins A3 (2), B2 (3), and C2 (4) have been accomplished.

Carbohydrate Sequence↗
PubMed1996

Photosensitivity in South Africa. IX. Structure elucidation of a beta-glucosidase-treated saponin from Tribulus terrestris, and the identification of saponin chemotypes of South African T. terrestris.

Saponin C, a beta-glucosidase-treated saponin isolated from ethanol-water extracts of a South African collection of Tribulus terrestris, was shown by one- and two-dimensional NMR spectroscopy to be ruscogenin 1-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-6)-acetylglucopyranoside++ +. GC-MS analysis of the hydrolysed ethanol-water (4:1) extracts of T.terrestris specimens from two of four sites, revealed high levels of ruscogenin and potentially lithogenic diosgenin saponins. Specimens from two other sites contained non-lithogenic saponins derived predominantly from tigogenin, neotigogenin, gitogenin and neo-gitogenin.

Animals↗