Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “SAPONINS”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 253 records · Page 14Linked to original sources
PubMed2005

Structure and biological activity of protopanaxatriol-type saponins from the roots of Panax notoginseng.

The further purification of the total saponins from the roots of Panax notoginseng by using ordinary and reversed-phase silica-gel, as well as Sephadex LH-20 chromatography afford seven adjuvant active protopanaxatriol-type saponins (PTS), ginsenosides-Rh1 (Rh1),-Rh4 (Rh4),-Rg1 (Rg1),-Re (Re), notoginsenosides-R1 (R1),-R2 (R2),-U (U). These saponins were evaluated for their haemolytic activities and adjuvant potentials on the cellular and humoral immune responses of ICR mice against ovalbumin (OVA). The effect of the substitution pattern of these PTS on their biological activities was investigated and structure-activity relationships were established. Among seven PTS, the haemolytic activity of Rh1 was higher than that of other six compounds (p<0.001) The HD50 values of Rh4 and U were significantly bigger than those of R2, Rg1 and Re (p<0.05 or p<0.01). Seven PTS could significantly increase the concanavalin A (Con A)-, lipopolysaccharide (LPS)- and OVA-induced splenocyte proliferation in the OVA-immunized mice (p<0.01 or p<0.001). The OVA-specific IgG, IgG1, IgG2a and IgG2b antibody levels in serum were also significantly enhanced by seven PTS compared with OVA control group (p<0.01 or p<0.001). The structure-activity relationship studies suggested that the number, the length and the position of sugar side chains, and the type of glucosyl group in the structure of PTS could not only affect their haemolytic activities and adjuvant potentials, but have significant effects on the nature of the immune responses. The information about this structure/function relationship might be useful for developing semisynthetic tetracyclic triterpenoid saponin derivatives with immunological adjuvant activity, as well as a reference to the distribution of the functional groups composing the saponin molecule.

Animals↗
PubMed2006

Tandem mass spectrometric analysis of a complex triterpene saponin mixture of Chenopodium quinoa.

A nano-HPLC electrospray ionization multi-stage tandem mass spectrometry (nLC-ESI-MS/MS) approach was applied to a complex crude triterpene saponin extract of Chenopodium quinoa seed coats. In ESI-MS/MS spectra of triterpene saponins, characteristic fragmentation reactions are observed and allow the determination of aglycones, saccharide sequences, compositions, and branching. Fragmentation of aglycones provided further structural information. The chemical complexity of the mixture was resolved by a complete profiling. Eighty-seven triterpene saponins comprising 19 reported and 68 novel components were identified and studied by MS. In addition to four reported, five novel triterpene aglycones were detected and characterized according to their fragmentation reactions in ESI-MS/MS and electron ionization mass spectrometry (EI-MS). As a novelty fragmentation pathways were proposed and analyzed based upon quantum chemical calculations using a hybrid Hartree-Fock density functional method. Accuracy of the assignment procedure was proven by isolation and structure determination of a novel compound. As the relative distribution and composition of saponins varies between different cultivars and soils, the presented strategy allows a rapid and complete analysis of Chenopodium quinoa saponin distribution and composition, and is particularly suitable for quality control and screening of extracts designated for pharmaceutical, agricultural, and industrial applications.

Chenopodium quinoa↗
PubMed2005

A rapid HPLC-ESI-MS/MS for qualitative and quantitative analysis of saponins in "XUESETONG" injection.

'XUESETONG' injection, one of the most widely used proprietary medicines in traditional Chinese medicine, consists of total saponins made from Panax notoginseng, which is a highly valued and important Chinese medicinal herb. It is used to treat cardiovascular diseases. In order to control the quality of XUESETONG injection, a rapid HPLC-ESI-MS/MS method was developed for qualitative and quantitative determination of the saponins. The analyses were performed on SB-C18 column using gradient elution in 25 min. Full scan and time programmed selected reaction monitoring (SRM) were used for qualitative and quantitative analysis of saponins, respectively. Twenty-seven saponins were identified and nine of them including notoginsenoside R1, ginsenoside Rb1, Rb2, Rb3, Rc, Rd, Re, Rf and Rg1 were quantified. Ten XUESETONG injections were analyzed and compared. The results showed that there is a great variation among different samples. In conclusion, the developed method is rapid, accurate and sensitive for qualitative and quantitative analysis of saponins in XUESETONG injection. Moreover, it also can be used for the quality control of P. notoginseng raw material and its preparations.

Chromatography, High Pressure Liquid↗
PubMed2006

Glucuronide triterpene saponins from Bersama engleriana.

Five 3-O-glucuronide triterpene saponins (1-5) were isolated from the stem bark of Bersama engleriana Gurke along with two known saponins, polyscias saponin C and aralia saponin 15, and one major C-glycoside xanthone, mangiferin. The structures of the saponins were established mainly by means of spectroscopic methods (one- and two-dimensional NMR spectroscopy as well as FAB-, HRESI-mass spectrometry) as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-betulinic acid (1), 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl]-oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-xylopyranosyl-(1-->6)-beta-d-glucopyranosyl]-oleanolic acid (3), 3-O-[beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl]-oleanolic acid (4), and 3-O-[beta-d-glucopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-d-xylopyranosyl-(1-->6)-beta-D-glucopyranosyl]-oleanolic acid (5).

Carbohydrate Conformation↗
PubMed2006

Saponins, classification and occurrence in the plant kingdom.

Saponins are a structurally diverse class of compounds occurring in many plant species, which are characterized by a skeleton derived of the 30-carbon precursor oxidosqualene to which glycosyl residues are attached. Traditionally, they are subdivided into triterpenoid and steroid glycosides, or into triterpenoid, spirostanol, and furostanol saponins. In this study, the structures of saponins are reviewed and classified based on their carbon skeletons, the formation of which follows the main pathways for the biosynthesis of triterpenes and steroids. In this way, 11 main classes of saponins were distinguished: dammaranes, tirucallanes, lupanes, hopanes, oleananes, taraxasteranes, ursanes, cycloartanes, lanostanes, cucurbitanes, and steroids. The dammaranes, lupanes, hopanes, oleananes, ursanes, and steroids are further divided into 16 subclasses, because their carbon skeletons are subjected to fragmentation, homologation, and degradation reactions. With this systematic classification, the relationship between the type of skeleton and the plant origin was investigated. Up to five main classes of skeletons could exist within one plant order, but the distribution of skeletons in the plant kingdom did not seem to be order- or subclass-specific. The oleanane skeleton was the most common skeleton and is present in most orders of the plant kingdom. For oleanane type saponins, the kind of substituents (e.g. -OH, =O, monosaccharide residues, etc.) and their position of attachment to the skeleton were reviewed. Carbohydrate chains of 18 monosaccharide residues can be attached to the oleanane skeleton, most commonly at the C3 and/or C17 atom. The kind and positions of the substituents did not seem to be plant order-specific.

Molecular Structure↗
PubMed2006

Acylated and deacylated saponins of Quillaja saponaria mixture as adjuvants for the FML-vaccine against visceral leishmaniasis.

The adjuvant of the FML-vaccine against murine and canine visceral leishmaniasis, the Riedel de Haen saponin mixture, was fractionated by ion exchange chromatography on DEAE-cellulose to afford one TLC homogeneous Quillaja saponaria Molina QS21 saponin fraction (18.0%), a mixture of two deacylsaponins (19.4%), sucrose (39.9%), sucrose and glucose (19.7%), rutin (0.8%) and quercetin (2.2%), that were identified by comparison of 1H and 13C NMR spectroscopy. The QS21 shows the typical aldehyde group in C-23 (65% equatorial) and a normonoterpene moiety acylated in C-28. The deacylsaponins show the aldehyde group but do not have the normonoterpene moiety. Balb/c mice were vaccinated with 150 microg of FML antigen of Leishmania donovani and 100 microg of each obtained fraction and further challenged by infection with 10(8) amastigotes of Leishmania chagasi. The safety analysis and the effect on humoral and cellular immune responses and in clinical signs showed that the QS21 saponin and the deacylsaponins are the most active adjuvant compounds of the Riedel the Haen saponin mixture. Both induced the highest and non-significantly different increases in DTH, CD4+ T lymphocytes in spleen, IFN-gamma in vitro, body weight gain and the most pronounced reduction of parasite burden in liver (95% for QS21 and 86% for deacylsaponins; p>0.05). While the QS21 showed mild toxicity, significant adjuvant effect on the anti-FML humoral response before and after infection, and decrease in liver relative weight, the deacylsaponins showed no toxicity, less haemolysis and antibody and DTH responses increased mainly after infection, still inducing a stronger Leishmania-specific in vitro splenocyte proliferation. Our results confirm in the Riedel de Haen saponin extract the presence of deacylsaponins normonoterpene-deprivated which are non-toxic and capable of inducing a specific and strong immunoprotective response in vaccination against murine visceral leishmaniasis.

Acylation↗
PubMed1979

Effects of soy protein and saponins on serum, tissue and feces steroids in rat.

Four groups of rats were fed, for 45 days, one of the following semipurified diets containing sucrose 55% (w/w) and (a) casein 25%, (b) casein 24%, saponins (from Saponaria officinalis) 1%, (c) isolated soy protein 25%, (d) soy protein 24%, saponins 1%. The soy protein diet, compared to the casein one, produced an increase in the fecal excretion of neutral sterols on the 29th and 42nd days, without any modification in the liver, aorta and serum cholesterol concentrations. The effect of soy protein cannot be attributed to its saponin content but other substances associated to soy protein may interfere. With the casein diet, added saponins increased the fecal excretion of neutral sterols and bile acids and decreased liver and aorta cholesterol levels. Serum cholesterol was found unchanged. The effects of saponins were suppressed or greatly reduced with the soy protein diet. These results could be explained by binding of the sterols in insoluble forms.

Animals↗
PubMed1988

High-performance liquid chromatographic determination of molluscicidal saponins from Phytolacca dodecandra (Phytolaccaceae).

A high-performance liquid chromatographic method is described for the determination of oleanane saponins in Phytolacca dodecandra (Phytolaccaceae), a plant with potent molluscicidal properties. The molluscicidal monodesmosidic saponins of the berries were determined at 254 nm as their 4-bromophenacyl derivatives, whereas the non-derivatized bidesmosidic saponins, lacking a free carboxyl group, were determined at 206 nm. A comparison of different extraction procedures showed that with cold water predominantly monodesmosidic saponins were obtained, whereas hot water gave mainly bidesmosidic (non-molluscicidal) saponins.

Chromatography, High Pressure Liquid↗
PubMed1993

Saponins from leaves of Acanthopanax sieboldianus.

Two new triterpenoid saponins named sieboldianoside A and B were isolated from the leaves of Acanthopanax sieboldianus together with five known triterpenoid saponins, kalopanax-saponins A and B, saponin A, CP3, sapindoside B, and a known flavonol glycoside, kaempferol 3-O-rutinoside. On the basis of chemical and spectral evidence, the structures of the new saponins (sieboldianoside A and B) were concluded to be alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)- beta-D-glucopyranosyl esters of hederagenin and oleanolic acid 3-O-beta-D- xylopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopy ranosides, respectively.

Carbohydrate Sequence↗
PubMed2003

Saponins in cereals.

Saponins are a diverse family of secondary metabolites that are produced by many plant species, particularly dicots. These molecules commonly have potent antifungal activity and their natural role in plants is likely to be in protection against attack by pathogenic microbes. They also have a variety of commercial applications including use as drugs and medicines. The enzymes, genes and biochemical pathways involved in the synthesis of these complex molecules are largely uncharacterized for any plant species. Cereals and grasses appear to be generally deficient in saponins with the exception of oats, which produce both steroidal and triterpenoid saponins. The isolation of genes for saponin biosynthesis from oats is now providing tools for the analysis of the evolution and regulation of saponin biosynthesis in monocots. These genes may also have potential for the development of improved disease resistance in cultivated cereals.

Biological Evolution↗
PubMed1997

Triterpenoid saponins from Mimusops elengi.

A novel minor triterpenoid saponin mimusin (3-O-[beta-D-glucopyranosyl- (1-->6)-beta-D-glucopyranosyl]-2 beta,3 beta,6 beta,23-tetrahydroxyolean- 12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L- rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside was isolated from the seeds of Mimusops elengi, in addition to two known triterpenoid saponins, Mi-saponin A and 16 alpha-hydroxy Mi-saponin A. The structure of the minor saponin was established by comparing its 13C NMR and LS-MS linked-scan, ESI-MS data with FAB-MS of the mimusopsin isolated earlier from the same source.

Carbohydrate Conformation↗
PubMed1998

Adjuvant action of Chenopodium quinoa saponins on the induction of antibody responses to intragastric and intranasal administered antigens in mice.

Saponins extracted from the seed of Chenopodium quinoa (quinoa) were studied for their ability to act as mucosal adjuvants upon their intragastric or intranasal administration together with model antigens in mice. Quinoa saponins, co-administered intragastrically or intranasally with cholera toxin or ovalbumin, potentiated specific IgG and IgA antibody responses to the antigens in serum, intestinal and lung secretions. The potentiating effect of the saponins appeared, to some extent, mediated by increased permeability of the mucosa, allowing increased uptake of the antigen. The intragastric administration of 99mTc-radio-labeled human serum albumin together with quinoa saponins revealed an increased presence of the radiolabeled protein in blood, liver, spleen and lungs of mice. This study indicates the potential of quinoa saponins as adjuvants for mucosally administered vaccines.

Adjuvants, Immunologic↗
PubMed1999

Duration of immunity, efficacy and safety in sheep of a recombinant Taenia ovis vaccine formulated with saponin or selected adjuvants.

The efficacy and safety of a recombinant Taenia ovis protein was tested in sheep using 13 different adjuvant formulations, including oil adjuvants, aluminium salts, saponin, Iscoms and DEAE-dextran. The oil adjuvants, saponin and DEAE-dextran gave the highest antibody responses and greatest degree of protection against challenge infection with T. ovis eggs. Duration of immunity studies with a saponin based vaccine showed that highly significant protection (>90% reduction of cyst numbers) was achieved when sheep were challenge infected one month after immunisation. Significant protection (79%) was still present when sheep were challenged 6 months after immunisation. The optimum dose for this batch of saponin was 10 mg, which stimulated a peak antibody titre of 38,400, 4 weeks after immunisation and did not cause injection site reactions. Dialysed saponin was shown to retain its adjuvant properties and allowed an increase in dose to 30 mg without site reaction, resulting in a peak antibody titre of 51,200.

Adjuvants, Immunologic↗
PubMed2003

Fractionation, structural studies, and immunological characterization of the semi-synthetic Quillaja saponins derivative GPI-0100.

Unfractionated GPI-0100 (UFGPI-0100) containing semi-synthetic derivatives of deacylated Quillaja saponins (DS saponins) modified at the glucuronic acid residue was resolved by reverse phase low-pressure liquid chromatography (RP-LPLC) into two fractions, RP18-1 and RP18-2, with different compositions and adjuvanticity. The fraction RP18-1 contained DS saponin adducts of N-dicyclohexylurea, and stimulated Th2 immunity with production of IgG1, while the RP18-2 fraction contained the dodecylamide derivatives of DS saponins and stimulated Th1 immunity with production of IgG2a, IFN-gamma, IL-2, and CTL. The strong immune stimulatory properties of RP18-2, relative to RP18-1, and the formation of RP18-1/RP18-2 mixed micelles may account for the effective stimulation of Th1 immunity by UFGPI-0100. UFGPI-0100 was free of acylated quillaja saponin components, including the more stable QS-7.

Adjuvants, Immunologic↗
PubMed1999

Lipoprotein lipase activation by red ginseng saponins in hyperlipidemia model animals.

The effect of ginseng saponins isolated from red ginseng (a steamed and dried root of Panax ginseng) has been studied in a cyclophosphamide (CPM)-induced hyperlipidemia model in fasted rabbits. In this model, chylomicrons and very low density lipoprotein (VLDL) accumulation was known to occur as a result of reduction in lipoprotein lipase (LPL) activity in the heart and heparin-releasable heart LPL. Oral administration of ginseng saponins at a dose of 0.01 g/kg for 4 weeks was found to reverse the increase in serum triglycerides (TG) and concomitant increase in cholesterol produced by CPM treatment, especially in chylomicrons and VLDL. In addition, ginseng saponins treatment led to a recovery in postheparin plasma LPL activity and heparin-releasable heart LPL activity, which were markedly reduced by CPM treatment. In rats given 15% glycerol/15% fructose solution, postheparin plasma LPL activity declined to two third of normal rats, whereas ginseng saponins reversed it to normal levels. In the present study we first demonstrated that ginseng saponins sustained LPL activity at a normal level or protected LPL activity from being decreased by several factors, resulting in the decrease of serum TG and cholesterol.

Administration, Oral↗
PubMedDate not supplied

Scale-up of centrifugal impeller bioreactor for hyperproduction of ginseng saponin and polysaccharide by high-density cultivation of panax notoginseng cells.

Scale-up of a novel centrifugal impeller bioreactor (CIB) was demonstrated for production of valuable plant-specific secondary metabolites by high-density cell cultures. Initial kLa was identified to be a key factor affecting cell growth and production of ginseng saponin and polysaccharide by high-density cultivation of Panax notoginseng cells in a 3-L CIB. A high level of ginseng saponin and polysaccharide production was obtained at an initial kLa value of 30.2 h(-1). A maximum dry cell weight (DW) and production titer of ginseng saponin and polysaccharide reached 22.0 +/- 0.3, 1.5 +/- 0.1, and 2.7 +/- 0.2 g/L on day 15 with their corresponding productivity of 1140 +/- 42, 81 +/- 8, and 150 +/- 17 mg/(L.d), respectively. Based on initial kLa level, the CIB high-cell-density cultivation process was successfully scaled up from 3 L to 30 L. A maximum DW and production titer of ginseng saponin and polysaccharide in a 30-L CIB reached 25.5 +/- 0.5, 1.7 +/- 0.1, and 2.9 +/- 0.1 g/L (on day 15) at an initial kLa value of 28.7 h(-1), respectively, and their corresponding productivity was 1340 +/- 56, 91 +/- 9, and 164 +/- 15 mg/(L.d). Furthermore, by adopting a fed-batch cultivation strategy, a maximum DW and concentrations of total saponin and polysaccharide in the 30-L CIB were enhanced to 30.3 +/- 1.0, 2.1 +/- 0.1, and 3.5 +/- 0.2 g/L with their corresponding productivity of 1467 +/- 87, 102 +/- 13, and 179 +/- 18 mg/(L.d), respectively. The work suggests that the CIB may have great potential in large-scale high-density plant cell cultures for efficient production of useful secondary metabolites.

Bioreactors↗
PubMed2001

Cholesterol solubilization in aqueous micellar solutions of quillaja saponin, bile salts, or nonionic surfactants.

Quillaja saponin in aqueous solution enhanced cholesterol solubility by as much as a factor of 10(3) at room temperature. Increased temperature and [NaCl] increased cholesterol solubility, whereas solubility was greatest at an aqueous pH of 4.6 at 298 K. Although various saponin sources were observed to differ in their abilities to solubilize cholesterol, trends in their solubilization properties with changing aqueous phase parameters were consistent. Surfactant molecules containing fused-ring structures as their hydrophobic portion, such as sodium cholate, sodium deoxycholate, and quillaja saponin, solubilized cholesterol significantly better than the linear hydrocarbon chain surfactants Tween 20 and Triton X-100. Mixtures of surfactants studied were found to exhibit synergistic effects: they formed micelles at lower concentrations than did those formed by the individual surfactants themselves, and they had a better ability to solubilize cholesterol. The knowledge obtained from these studies improves our understanding of cholesterol association with saponin and other types of surfactants and enhances the potential for using saponins for the solubilization and extraction of hydrophobic solutes in various pharmacological and industrial applications.

Bile Acids and Salts↗
PubMed2002

Determination of saponins in legumes by direct densitometry.

Research has shown that dietary saponins may have health benefits. A simple, rapid method for the determination of saponins in legumes, using densitometry, is described. Saponin preparations, after pretreatment to remove nonsaponin components, are spotted in rows on a thin-layer chromatography plate, along with soyasaponin standards. The plate, without solvent development, is directly treated with sulfuric acid and heated. Violet spots develop which have a density proportional to the amount of saponin present. The standard curve has a correlation coefficient of 0.99 and is linear over the range of 1.25 to 10 microg of soyasaponins applied. The method has a coefficient of variation of less than 3% and compares favorably with quantitative thin-layer chromatography. Using this method the saponin contents of defatted soy flour (0.58%), dried navy beans (0.32%), and dried kidney beans (0.29%) were determined, and these results were found to be consistent with previous reports in the literature.

Chromatography, Thin Layer↗