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PubMed1980

The comparative selectivity of adjuvants for humoral and cell-mediated immunity. I. Effect on the antibody response to bovine serum albumin and sheep red blood cells of Freund's incomplete and complete adjuvants, alhydrogel, Corynebacterium parvum, Bordetella pertussis, muramyl dipeptide and saponin.

A comparison was made of seven recognized adjuvants, Freund's incomplete and complete, alhydrogel, Corynebacterium parvum, Bordetella pertussis, muramyl dipeptide and saponin, administered with BSA or SRBC by the S.C. route of immunization. Strong selectivity as well as differences in potency were revealed in relation to these two antigens. Only FIA, FCA, alhydrogel and MDP promoted the primary response to 50 microgram of BSA, and FIA was significantly superior to FCA. Immunological memory to a low dose (0.5 microgram) of BSA, which did not evoke a primary response with any adjuvant, was potentiated by alhydrogel and by MDP and, relatively poorly, by FIA. Radioimmunoelectrophoresis showed that potentiation of the response with MDP was confined to IgG1, whereas alhydrogel, FIA and FCA stimulated both IgG1 and IgG2. Saponin was outstandingly the best adjuvant for both primary and secondary haemagglutinin responses to SRBC. Of the others, alhydrogel for the primary, and alhydrogel and B. pertussis for the secondary were active to a lesser degree. The results show that the relative potency of adjuvants differs markedly according to the antigen used, and suggest that saponin may be a particularly effective adjuvant for antigens in cell membranes.

Acetylmuramyl-Alanyl-Isoglutamine↗
PubMed1980

Immunogenicity studies of foot and mouth disease vaccines at different concentrations of antigen and saponin.

Frenkel-type monovalent O1 and C vaccines were tested for immunogenicity under field conditions, in a large cattle farm. Both vaccines were applied in four dilutions, to furnish different concentrations of antigen, and each dilution was tested with 4 and 8 mg/dose levels of saponin, and without adjuvant. In adult multivaccinated already one eight of the standard bovine dose of both preparations developed a satisfactory booster effect, and presence or absence of the adjuvant played little role. In the growing (5-7 months old) primary vaccinated immune response to vaccination depended on the applied dose of antigen; the higher the latter, the firmer immunity was developed. The immunogenicity-enhancing effect of saponin, too, was more pronounced in the young than in the adult vaccinated. The result of the immunization was significantly improved by the use of 8 mg saponin per dose, compared to that found with 4 mg or no adjuvant in the vaccine. The best vaccination results were obtained on combination on the highest antigen conentrations with 8 mg saponin/dose. The type O1 antigen proved to be about half as strong, as the type C one, having elicited the same degree of immunity as C in a roughly double dose.

Animals↗
PubMed1983

45Ca distribution and transport in saponin skinned vascular smooth muscle.

45Ca distribution and transport were studied in chemically skinned strips of caudal artery from Kyoto Wistar rats. Sarcolemmal membranes were made hyperpermeable by exposure for 60 min to solutions containing 0.1 mg/ml of saponin. Skinned helical strips responded with graded contractions to changes in ethylene glycol bis-(beta-aminoethyl ether)-N,N'-tetraacetic acid buffered free Ca solutions (10(-7) to 10(-5) M) and were sensitive to the Mg-ATP concentration. Tissues loaded in the presence of 10(-7) M Ca contracted in response to 10 mM caffeine. These experiments indicate the strips are skinned and possess a functional regulatory and contractile system and an intact Ca sequestering system. 45Ca distributes in three compartments in skinned caudal artery strips. The Ca contents of two components are linear functions of the Ca-ethylene glycol bis-(beta-aminoethyl ether)-N,N'-tetraacetic acid concentration and desaturate at rapid rates. They correspond to the extracellular and cytoplasmic spaces. A significantly smaller component releases Ca at comparatively slower rates. 45Ca uptake by the slow component consists of an ATP-dependent and an ATP-independent fraction. The 45Ca content of the ATP-dependent fraction is a function of the free Ca concentration and is independent of the Ca-ethylene glycol bis-(beta-aminoethyl ether)-N,N'-tetraacetic acid concentration. Its content was enhanced by oxalate and was abolished by Triton X-100 skinning solutions. The ATP-independent component was not affected by Triton X-100 skinning and may represent Ca binding to cytoplasmic molecules and structures. The sequestered Ca was released with caffeine or Ca but not by epinephrine. The observations indicate that the sarcoplasmic reticulum and mitochondria of vascular smooth muscle strips skinned with saponin retain their functional integrity after saponin skinning.

Animals↗
PubMed1994

[Ginseng saponin treatment for intrauterine growth retardation].

Twenty eight patients with intrauterine growth retardation (IUGR) in 31-34 gestational weeks were clinically treated with Chang Bai Shan ginseng saponin tablets, while 26 pregnant women with IUGR were nutritionally treated as controls. The results indicated that in the experiment and control groups, the height of fundus and fetal diparietal diameter (BPD) gradually approached to those of the normal pregnancy group. The urinary estrogens/creatinine (E/C) ratio and serum human placental lactogen (hPL) were close to those of the normal pregnancy group (P > 0.05) after 35 gestational weeks. The weight of neonates treated nutritionally and with ginseng saponin approached to that of the normal pregnancy group. There was no significant difference as compared with the normal pregnancy group (P > 0.05). Glucose and albumen levels in blood of neonates were not significantly different between experiment and control groups, but they were higher than those in IUGR group (P < 0.05). The present results suggest that in treating IUGR, ginseng saponin may show the same effect as in the nutritional treatment.

Adult↗
PubMed1993

Pharmacologic consequences of cholesterol absorption inhibition: alteration in cholesterol metabolism and reduction in plasma cholesterol concentration induced by the synthetic saponin beta-tigogenin cellobioside (CP-88818; tiqueside).

Natural and synthetic saponins inhibit cholesterol absorption and reduce plasma cholesterol levels in experimental animals and are therefore of potential pharmacologic utility in the treatment of hypercholesterolemia. To determine the effects of this class of compounds on cholesterol absorption and metabolism, we evaluated the effects of the synthetic saponin, beta-tigogenin cellobioside (tiqueside; CP-88818), on male golden Syrian hamsters. When administered as either a single oral bolus or as a dietary supplement for up to 2 weeks, tiqueside inhibited cholesterol absorption in a dose-dependent manner in both the presence and absence of dietary cholesterol. Administration of tiqueside to chow-fed hamsters as a 0.2% dietary supplement (150 mg/kg per day) for 4 days resulted in a 68% decrease in intestinal cholesterol absorption with no change in either bile absorption or cholesterol 7 alpha-hydroxylase activity, suggesting that tiqueside inhibits cholesterol absorption without interfering with enterohepatic bile acid recirculation. Under these conditions, hepatic cholesterol levels were also reduced in a dose-dependent manner. Hepatic cholesterol reduction was highly correlated with cholesterol absorption inhibition, and induced compensatory increases in both hepatic HMG-CoA reductase activity and hepatic low density lipoprotein (LDL) receptor levels. Compensatory increases in intestinal HMG-CoA reductase activity were also noted after tiqueside administration, and are consistent with a luminal mechanism for tiqueside action. As a consequence of these changes to cholesterol metabolism, tiqueside administration induced plasma cholesterol reductions that were highly correlated with both hepatic cholesterol reduction and cholesterol absorption inhibition. Tiqueside also produced comparable plasma cholesterol lowering in a variety of other species fed either cholesterol-free diets (hamster, rat, mouse, dog) or cholesterol-containing diets (hamster, rat, rabbit, mouse, cynomolgus monkey, rhesus monkey, SEA quail) indicating the ubiquity of tiqueside action. For all species evaluated except the dog, the reduction in plasma cholesterol was due primarily to a reduction in circulating non-HDL cholesterol levels with little or no change in HDL cholesterol levels. Taken together, these results indicate that inhibition of cholesterol absorption by tiqueside produces profound effects on cholesterol metabolism without affecting bile acid metabolism, and that these changes lead to reductions primarily in plasma non-HDL cholesterol concentrations. The synthetic saponin, tiqueside, may thus represent a prototypical form of therapy for the treatment of hypercholesterolemia.

Amino Acid Sequence↗
PubMed1996

Cytotoxicity of triterpenoid saponins. Part 1: Activities against tumor cells in vitro and hemolytical index.

Genuine saponins from Solidago virgaurea L., Heteropappus altaicus (Willd.) Novopokr., H. biennis (Ldb.) Tamamsch., and Helianthus annuus L. (Asteraceae) as well as related carbohydrate modified glycosides of polygalacic acid and echinocystic acid were investigated in view of their structure related cytotoxicity in the YAC-1- and in the P-815-tumor cell model. The cytotoxic activities are influenced by both, the O-glycosylation pattern at carbon atom 3 and 28 of the sapogenin. The IC50-values of bisdesmosides of polygalacic acid are lower than those of the corresponding prosapogenins. The acylglycosidic carbohydrate sequence 1-fucose-2 <-- 1-rhamnose-4 <-- 1-xylose-3 <-- 1-rhamnose of these bisdesmosides showed the highest cytotoxic effect. One etherglycosidic linked glucose unit at C-3 of the aglycone is essential, a difference in activity to the disaccharide laminaribiose at the same position cannot be observed. In the case of echinocystic acid glycosides the acylglycosidic carbohydrate sequence 1-arabinose-2 <-- 1-rhamnose-4 <-- 1-glucose seems to influence the rate of the cytotoxic effects. By comparing the concentration of the saponins with the complete hemolysis time it is possible to determine the hemolytical index in a very short time. Cytotoxicity against tumor cells correlated with the basic structure of the saponins are in accordance with the hemolytical effect. Sugar moieties play an important role for the hemolytical index.

Antineoplastic Agents, Phytogenic↗
PubMed1996

Saponins as vaccine adjuvants.

Naturally occurring triterpene glycosides (saponins) from Quillaja saponaria have considerable adjuvant activity. Adjuvant functions include stimulation of high levels of antibody to T-dependent and T-independent antigens, induction of mouse IgG1, IgG2b, and IgG2a isotypes, and induction of cytotoxic T lymphocyte responses. This article reviews responses due to specific saponins of saponin preparations, effect of formulation, structure/function studies, and use in different preclinical and clinical vaccine applications.

Adjuvants, Immunologic↗
PubMed1998

QS-21 and QS-7: purified saponin adjuvants.

QS-21 and QS-7 are two adjuvant-active saponins that can be obtained in high purity from Quillaja saponaria Molina extracts. QS-21 is a highly characterized compound and is known to be a potent adjuvant for antibody and CD8+ CTL response to subunit antigens. Less is known about the activity and structure of the hydrophilic saponin QS-7. Hence, we have carried out a detailed structural and immunological characterization. As with QS-21, QS-7 was shown to be a 3,28-O-bisglycoside quillaic acid, with some differences being a higher degree of glycosylation and a considerably shorter fatty acyl unit in QS-7. These differences were correlated to a lower lytic activity against sheep red blood cells. Different doses of QS-7 were evaluated for stimulation of immune response to the antigen ovalbumin, given three times by subcutaneous route to C57BL/6 mice. QS-7 doses of 40 micrograms or higher were shown to induce a strong CD8+ CTL response reproducibly against E. G7-OVA targets (similar to that induced by a 5-10 micrograms dose of QS-21). QS-7 (at doses above 5 micrograms) was also shown to stimulate CTL against peptide 18 of HIV-1IIIB gp120 after three immunizations of Balb/c mice with recombinant gp120 and different doses of QS-7. These data suggest that a hydrophilic saponin with low lytic activity can stimulate MHC Class I CTL responses although a higher minimum dose may be required for some antigens.

Adjuvants, Immunologic↗
PubMed2006

High-performance liquid chromatographic assay for the active saponins from Panax notoginseng in rat tissues.

A reversed-phase liquid chromatographic method was used to determine the ginsenosides Rg1, Rb1 and Rd of Panax notoginseng in rat tissues (kidney, liver, heart, spleen and lung) after the administration of total saponins of P. notoginseng. The tissue samples were treated with solid-phase extraction prior to HPLC. The calibration curves for the three saponins were linear in the given concentration ranges. The intra-day and inter-day assay coefficients in tissues were between 76 and 120% respectively. The recoveries of all the tissues were higher than 70%. This method was applied to evaluate the distribution of the three major saponins of P. notoginseng in rat tissues.

Animals↗
PubMed2005

Characteristic fragmentation behavior of some glucuronide-type triterpenoid saponins using electrospray ionization tandem mass spectrometry.

The fragmentation behavior of some glucuronide-type triterpenoid saponins from Symplocos chinensis, and their analogues escin Ia and Ib, were investigated by positive ion electrospray ionization tandem mass spectrometry using a quadrupole linear ion trap mass spectrometer. The fragmentation patterns of these saponins significantly changed in accordance with structural variations in the glucuronyl residue of the oligosaccharide chain. It was found that the carboxyl group and hydroxyl group at the C-3' position of the glucuronyl residue were the key sites for determining the fragmentation behavior of these compounds. When the carboxyl group was esterified, only the C(2alpha) ion, and no B(2alpha) ion, and cationized aglycone were observed. When the hydroxyl group at C-3' was acylated, the inherent cross-ring cleavage was hindered. However, glycosidic cleavages always occurred, regardless of the crucial structural variations. The results of the present studies can benefit the determination of trace triterpenoid saponins of this type in crude plant extracts, and also provide background information to aid the structural investigations of similar glycoconjugates.

Escin↗
PubMed2006

Adjuvant effects of protopanaxadiol and protopanaxatriol saponins from ginseng roots on the immune responses to ovalbumin in mice.

Protopanaxadiol saponins (Rg3, Rd, Rc, Rb1 and Rb2) and protopanaxatriol saponins (Rg1, Re and Rg2) isolated from the root of Panax ginseng C.A. Meyer were evaluated for their adjuvant effects on the immune responses to ovalbumin (OVA) in mice. BALB/c mice were subcutaneously injected twice at a 3-week interval with 10 microg of ovalbumin or 10 microg of OVA plus 50 microg of ginsenosides Rg3, Rd, Rc, Rb1, Rb2, Rg1, Re or Rg2 or Quil A (n=5). Blood samples were collected for measuring specific total-IgG, IgG1 and IgG2a, and splenocytes were harvested for determining lymphocyte proliferation as well as IFN-gamma and IL-5 production 2 weeks after the boosting. The results indicated that OVA-specific antibody responses were significantly higher in mice immunized with OVA co-administered with Rg1, Re, Rg2, Rg3 and Rb1 but not with Rd, Rc and Rb2 when compared with the control (immunized with OVA only). Significantly enhanced splenocyte proliferative responses to Con A, LPS and OVA as well as the production of both IL-5 and IFN-gamma stimulated by OVA were also detected in mice immunized with OVA co-administered with Rg1 but not with Rb1, Re and Rg3. Of the ginsenosides studied, Rg1, Re, Rg2, Rg3 and Rb1 have more potent adjuvant properties than the others, indicating that they are the major constituents contributing to the adjuvant activities of total ginseng saponins. Varieties of ginsenosides in adjuvant activity might be attributed to the varieties of molecular conformations determined by the side sugar chains attaching to their dammarane skeleton.

Adjuvants, Immunologic↗
PubMed1994

Steroidal saponins from the bulbs of Lilium speciosum x L. nobilissimum 'Star Gazer' and their antitumour-promoter activity.

The fresh bulbs of the oriental hybrid lily, Lilium speciosum x L. nobilissimum 'Star Gazer' yielded a new steroidal saponin, (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-O-[6-O-acetyl-beta-D-glucopyranos yl- (1-->4)]-beta-D-glucopyranoside], along with four known steroidal saponins, (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-O-]beta-D-glucopyranosyl-(1-->4)] - beta-D-glucopyranoside], (25R)-27-O-[(S)-3-hydroxy-3-methylglutaryl]- spirost-5-ene-3 beta, 27-diol 3-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D- glucopy-ranoside] and (25R)-27-O-[(S)-3-hydroxy-3-methylglutaryl]- spirost-5-eene-3 beta, 27-diol 3-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-O- O-[beta-D-glucoyranosyl-(1-->4)]-beta-D-glucoyranoside]. The structure of The structure of the new saponin was determined by means of spectroscopic analysis and hydrolysis. The methyl ester of 5 showed potent inhibitory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated 32P incorporation into phospholipids of HeLa cells.

Antineoplastic Agents, Phytogenic↗
PubMed2002

Glycosyl trifluoroacetimidates. 2. Synthesis of dioscin and xiebai saponin I.

Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin I (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.

Journal Article↗
PubMed1997

Effects of MCI-154 on calcium sensitivity of contractile system and calcium release from sarcoplasmic reticulum in saponin-skinned rat myocardium.

AIM: To explore the possible mechanisms underlying the positive inotropic effect of MCI-154. METHODS: Skinned fibers with disrupted or preserved sarcoplasmic reticulum (SR) were prepared by saponin 500 or 50 mg.L-1. The tension-pCa relationship and pCa50 of saponin (500 mg.L-1)-skinned fibers were taken as the indices of Ca2+ sensitivity of contractile proteins. The amplitude of caffeine-induced contracture was an index of Ca2+ release from SR in saponin (50 mg.L-1)-skinned fibers. RESULTS: 1) MCI-154 (0.1 mmol.L-1) showed a Ca2+ sensitizing effect on contractile proteins. The pCa50 was increased to 5.84 (5.54-6.14) compared with control value 5.54 (5.30-5.79) (P < 0.01, n = 8). Hill coefficient n was decreased by 0.29 (P < 0.01, n = 8); 2) No contracture was produced by MCI-154 in preparations with preserved SR. Caffeine-induced contracture before and after MCI-154 treatment were not changed (P > 0.05, n = 4). CONCLUSION: MCI-154 directly enhances the Ca2+ sensitivity of contractile protein but has little effect on Ca2+ release from SR in rat skinned cardiac fibers.

Animals↗
PubMed2001

[Screening of steroidal saponins from the bulbs of Lilium brownii var. colchesteri by combination of high performance liquid chromatography-electrospray ionization mass spectrometry and electron impact mass spectrometry].

With the combination of high performance liquid chromatography-electrospray ionization mass spectrometry (HPLC/ESI-MS) and electron impact mass spectrometry (EI-MS), two steroidal saponins, one compound containing three glycosyls and tigogenin and the other one containing three glycosyls and diosgenin, from the bulbs of Lilium brownii var. calchesteri in China have been screened. In the method, on-line HPLC/ESI-MS allows us to obtain rapidly useful information about the molecular weight and the glycosyl chain of glycoside without the necessity of isolating individual compounds, but little information about steroidal sapogenins. Just with 1 mg to 2 mg of pure sample, off-line EI-MS allows us to acquire useful information about a steroidal sapogenin of saponins, but it is difficult to obtain the molecular ion peak. The combination of HPLC/ESI-MS and EI-MS is well suitable for rapidly screening steroidal saponins from plants.

Chromatography, High Pressure Liquid↗
PubMed2004

[Two new triterpenoid saponins from Lysimachia capillipes Hemsl].

AIM: To study the triterpenoid saponins in the whole plants of Lysimachia capillipes Hemsl.. METHODS: Column chromatography (including AB-8 macroporous resin, silica gel and ODS) was used to separate triterpenoid saponins whose structures were elucidated by ESI-MS, NMR (1D and 2D) and hydrolysis methods. RESULTS: Two new triterpenoid saponins were isolated and established as 3beta, 22alpha-dihydroxy-16alpha-angeloyloxy-28-->13-lactone-oleanane-3-O-[beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinpyranosyl]-22-O-(6-acetyl)-beta-D-glucopyranoside (I), 3beta, 13beta, 22alpha-trihydroxy-16alpha-acetyloxyoleanane-28-oic acid Na-3-O-[beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinpyranosyl]-22-O-beta-D-glucopyranoside (II). CONCLUSION: Compounds I and II are new compounds and named as capilliposide I and capilliposide J.

Flavonoids↗
PubMed1991

[Separation and quantitative determination of three saponins in licorice root by high performance liquid chromatography].

A new analytical method for the separation and simultaneous determination of three saponins in Licorice root by high performance liquid chromatography has been developed. The saponins, glycyrrhizic acid (S-I), uralsaponin B (S-II) and uralsaponin A (S-III) were separated and determined by use of the solvent system CH3CN-3% HOAc (H2O) (47:53) at 248 nm, and with gradient increasing flow rate, the operation can be completed in 20 min. This method is sensitive and acuate with good reproducibility. The contents of three saponins in Chinese Licorice roots derived from four Glycyrrhiza species were determined.

Anti-Infective Agents↗
PubMed1991

On the structure of immune-stimulating saponin-lipid complexes (iscoms).

Immune-stimulating complexes (iscoms) are stable complexes of cholesterol, phospholipid and Quil A, a triterpene saponin mixture in the size range from 40 to 100 nm. They can be used as antigen carriers in subunit vaccines. In this paper it is demonstrated that iscoms are rigid, negatively charged vesicles in which small water soluble molecules like carboxyfluorescein cannot be retained. The negative zeta-potential prevents iscoms from aggregation. The chemical composition of iscoms in one dispersion varied considerably. A typical example of the composition of iscoms is cholesterol/phospholipid/Quil A = 1.0:1.2:6.2 by weight for the iscom matrix, that is iscoms without antigen, and 1.0:1.3:5.1 for antigen-containing iscoms. A hypothetical model for the structure of the iscom matrix and related structures is presented, based on analytical chemical, physico-chemical and electronmicroscopic data. In this model iscoms are considered to be multi-micellar structures, shaped and stabilized by hydrophobic interactions, electrostatic repulsion, steric factors and possibly hydrogen bonds. The individual micelles are relatively flat, ring-shaped structures, the center offering space for one of the two bulky sugar chains of the saponins.

Adjuvants, Immunologic↗