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At least 325 records · Page 18Linked to original sources
PubMed2006

Cytotoxic steroidal saponins from Polygonatum punctatum.

Four new steroidal saponins, polypunctosides A-D (1-4, resp.), were isolated from the rhizomes of Polygonatum punctatum, together with five known steroidal saponins. On the basis of chemical and spectral evidence, the structures of the new saponins were established as (3beta,23S,25R)-23-(alpha-L-arabinopyranosyloxy)spirost-5-en-3-yl 4-O-(6-deoxy-alpha-L-mannopyranosyl)-D-glucopyranoside (1), (3beta,23S,25R)-23-[(2-O-acetyl-alpha-L-arabinopyranosyl)oxy]spirost-5-en-3-yl 4-O-(6-deoxy-alpha-L-mannopyranosyl)-D-glucopyranoside (2), (3beta,23S,25R)-23-[(3-O-acetyl-alpha-L-arabinopyranosyl)oxy]spirost-5-en-3-yl 4-O-(6-deoxy-alpha-L-mannopyranosyl)-D-glucopyranoside (3), and (3beta,23S,25R)-23-[(4-O-acetyl-alpha-L-arabinopyranosyl)oxy]spirost-5-en-3-yl 4-O-(6-deoxy-alpha-L-mannopyranosyl)-D-glucopyranoside (4). The cytotoxic activity of the isolated saponins was evaluated towards HeLa cells.

Cytotoxins↗
PubMedDate not supplied

Determination of saponins and alkaloids in Caulophyllum thalictroides (blue cohosh) by high-performance liquid chromatography and evaporative light scattering detection.

The roots of Caulophyllum thalictroides, traditionally used for the treatment of menstrual difficulties and as an aid in childbirth, contain saponins, which are considered to be responsible for the uterine stimulant effects, together with teratogenic alkaloids. An HPLC method has been developed which permits the determination of the triterpene saponins in the plant and also the separation of four alkaloids. The best results were obtained with a C-12 stationary phase using ammonium acetate buffer (pH 8.0) and acetonitrile as mobile phase. Owing to their low UV absorbance, the saponins were detected by evaporative light scattering, whereas the alkaloids were monitored by UV at 310 nm. The identities of the compounds were confirmed in an LC-MS experiment. Different plant samples and commercial products have been analysed using the described method, and remarkable qualitative and quantitative variations were revealed. Comparing the daily uptake of total saponins, a difference of greater than 100-fold was observed within the various products; the alkaloid content on the other hand was more uniform.

Alkaloids↗
PubMed1995

Glycosyl compositions and structural characteristics of the potential immuno-adjuvant active saponins in the Quillaja saponaria Molina extract quil A.

Fifty saponin components of Quil A, a commercially available extract from the bark of the South American tree Quillaja saponaria Molina, were partially structurally characterised. The molecular weights were determined by fast-atom bombardment mass spectrometry. The glycosyl and elemental composition of all the saponins was determined by applying our recently developed method, monomer mapping, consisting of a computer program and accurate mass measurements. Support for the presumed identity of the aglycone, i.e. quillaic acid, was found in the accurate mass determination, 1H NMR measurement and chemical reactions. The saponin composition of Quil A was shown to consist of pairs. Within the 3-O bound glycosyl moiety of a pair there was a structural difference: a pentose and rhamnose were interchanged. Structural differences between different pairs were located in the 28-O bound glycosyl moiety. A structural element, unknown to date and of which the elemental composition was deduced to be C8H12O5, was found in the 28-O bound glycosyl moiety of several saponins.

Adjuvants, Immunologic↗
PubMed2002

Structural characterization of steroidal saponins by electrospray ionization and fast-atom bombardment tandem mass spectrometry.

The structural characterization of four steroidal saponin compounds involving two and three sugar groups, namely spirostanol saponins and furostanol saponins, were investigated by positive ion fast-atom bombardment (FAB), electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS) techniques. Important structural information was obtained from collision-induced dissociation (CID) and FAB-MS spectra with different liquid matrices. It was found that a characteristic fragmentation involving the loss of 144 Da arising from the cleavage of the E-ring was observed when there was no sugar chain at the C-26 position. When a glucoside group was substituted at the C-26 position, this C-26 sugar moiety was preferentially eliminated. All of these compounds produced a major product ion with a stable skeleton structure at m/z 255. The results of this paper can assist structural analysis of mixtures of steroidal saponins.

Drugs, Chinese Herbal↗
PubMed1996

Triterpene and steroid saponins isolated from two Melilotus species.

Four new triterpene saponins of the oleanan series-melilotosides I, II, III, IV and nonglycosylated soyasapogenol B have been isolated from roots of Melilotus albus Medik. (Leguminosae) and four steroid saponins were isolated from M. tauricus (Bieb.) ser. seeds. The chemical structure of the saponins and of their aglycone was proved based on chemical transformations and spectral data. Melilotoside I has the structure of 3-O-[a-L-arabinopyranosyl] soyasapogenol B, melilotoside II that of 3-O-[beta-D-galactopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl] soyasapogenol B, melilotoside III that of 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-beta-D-galactopyranosyl-(1-->2)-O -alpha-L-arabinopyranosyl] soyasapogenol B, and melilotoside IV that of 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl-(1- ->3)]- O-beta-D-galactopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl soyasapogenol B. The steroid saponins have been identified as 3-O-beta-D-glucopyranoside-diosgenin (V); 3-O-alpha-L-rhamnopyranosyl (1-->2)-[alpha-L-rhamnopyranosyl(1-->3)-O-beta-D-glucopyranoside- diosgenin (VI),26-O-beta-D-glucopyranoside (25R)-furost-5-ene 3beta,22alpha, 26-triol (VII), and 3-O-alpha-L-rhamnopyranosyl(1-->4)-alpha-O-beta-D- glucopyranoside(25R)-furost-5-ene 3beta,22alpha,26-triol-26-O-beta-D- glucopyranoside (VIII).

Fabaceae↗
PubMed1975

The effect of alfalfa saponins on growth and lysis of Physarum polycephalum.

The prelytic events associated with the interaction of saponins with Physarum polycephalum membrane components were studied. It was found that alfalfa saponins form interaction products with membranal sterols, proteins and phospholipids. The interaction of saponins with proteins affect also certain membranal enzymic activities such as NADH oxidase and Malate dehydrogenase. It is suggested that although the interaction of the saponin with sterols is much more specific than with other membranal components, the lysis of plasmodia of P. polycephalum should be attributed to a concerted attack on the various membrane constituents. In continuation of these interactions, the changes of permeability of plasmodia membrane were expressed by increment of inorganic sodium ions and water influx, traced by lysis, while no efflux of ions was observed.

Cell Membrane↗
PubMed1989

Calmodulin loss in vascular smooth muscle following Triton X-100 or saponin skinning.

The calmodulin (CaM) content of intact and chemically skinned strips of rat caudal artery was measured using a 125I-CaM radioimmunoassay. The total CaM measured following homogenization of arterial tissue with EGTA and EGTA/Triton X-100 was 2.58 mumol/kg wet tissue. Based on a smooth muscle volume of 40%, this value corresponds to a cellular CaM concentration of 6.5 microM. Approximately 97% of total CaM was soluble and approximately 3% was EGTA-nonextractable. Permeabilization of the plasmalemma with 0.15 mg/ml saponin or 0.5% Triton X-100 caused significant detergent-dependent loss of CaM. At the end of a 1 h skinning period, tissues exposed to saponin lost 30% of total CaM. By comparison, tissues skinned under the same conditions with Triton X-100 lost 50%. During a subsequent 4 h exposure to relaxing solution, total tissue CaM continued to decline. The exponential loss over the 5 h period was described by a first order model having diffusible and nondiffusible CaM components. The diffusible CaM component of saponin skinned tissue (59%) was significantly less than the diffusible component of those skinned with Triton X-100 (88%); however, the rate coefficients for CaM diffusion (0.78 h-1 and 0.91 h-1, respectively) did not statistically differ. The nondiffusible component of CaM was significantly larger in saponin treated strips (42%) than in Triton X-100 permeabilized tissue (12%). Arterial strips skinned with Triton X-100, which were subsequently exposed to relaxing solution for up to 22 h, lost significantly more CaM than those retained in Triton X-100 skinning solution for a comparable duration.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1989

Functional aspects of calcium transport in sarcoplasmic reticulum vesicles derived from frog skeletal muscle treated with saponin.

To study the physiological aspects of the excitation-contraction cycle, saponin (10-100 micrograms ml-1) was used as a skinning agent on muscle and sarcotubular vesicles derived from fast muscles (sartorius and tibialis anterior) of Rana esculenta. The vesicles showed similar Ca2+-ATPase activity and similar protein profiles carried out by SDS-PAGE. Calcium transport in untreated vesicles and those treated with different concentrations of saponin seemed to have the same quantitative and qualitative parameters if the saponin was used in a range between 10 and 50 micrograms ml-1. Our results confirm that saponin may be considered to be a valid skinning agent for the external membranes of fast skeletal muscles.

Animals↗
PubMed1986

Comparison of vasoconstrictor actions of norepinephrine and potassium chloride before and after damage of endothelium by saponin.

Using isolated and perfused mesenteric arterial preparations of dogs, vasoconstrictor responses to intraluminal norepinephrine and potassium chloride were investigated in the presence and absence of the endothelium. Intraluminal administration of saponin readily removed the endothelium. Saponin (1-3 mg) caused an increase in perfusion pressure, and then approximately 20 min later perfusion pressure became stable at a somewhat higher level than that of the control. A larger dose of saponin (10 mg) caused a tremendous but temporary increase of perfusion pressure. KCl-induced vasoconstriction was significantly enhanced by pretreatment with 0.3, 1, and 3 mg saponin, but norepinephrine-induced constriction was not modified significantly. Moreover, it was demonstrated that diltiazem, a potent Ca antagonist, inhibited the KCl-induced vasoconstriction more readily in the absence than in the presence of the endothelium.

Animals↗
PubMed1991

Implication of steroid saponins and sapogenins in the hypocholesterolemic effect of fenugreek.

The transformation of fenugreek subfractions, rich in steroid saponins, was studied upon their passage through the digestive tract to determine the contribution of saponins and/or diosgenin and other steroid sapogenins to the hypocholesterolemic effect of fenugreek seeds. Feces of alloxan diabetic dogs fed fenugreek subfractions were analyzed, and diosgenin, smilagenin and gitogenin were identified and measured using capillary gas chromatography/mass spectrometry. Our results show that saponins are, in part (about 57%), hydrolyzed into sapogenins in the digestive tract. It appears that saponins may be implicated, alone or together with diosgenin, in the observed hypocholesterolemic effect of fenugreek seeds in diabetic dogs.

Alloxan↗
PubMed1991

Triterpenoidal saponins from the bark of Kalopanax pictum var. typicum.

One new triterpenoidal saponin, saponin F(2) has been isolated from the bark of Kalopanax pictum Nakai var. typicum (Araliaceae), together with one known saponin, kizuta saponin K12 (1). On the basis of chemico-spectral evidences, the structure of 2 has been elucidated to be 3-O-beta-D-xylopyranosyl(1-->3)-alpha- L-rhamnopyranosyl(1-->2)-alpha- L-arabinopyranosyl-23-hydroxyolean-12-en-28-O-alpha-L- rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosy l ester.

Carbohydrate Sequence↗
PubMed2002

UDP-glucuronic acid:soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds.

We detected UDP-glucuronic acid:soyasapogenol glucuronosyltransferase (UGASGT) activity in the microsomal fraction from germinating soybean (Glycine max [L.] Merr.) seed. A microsomal fraction was isolated from germinating soybean seed and treated with various detergents to solubilize the enzyme. UGASGT activity was monitored throughout purification using UDP-[U-(14)C]glucuronic acid and soyasapogenol B as substrates. Purification of UGASGT was achieved by HiTrap Q, Superdex 200, and HiTrap Blue chromatography procedures. This resulted in >205-fold enrichment relative to the starting homogenate. UGASGT was found to require divalent cations for activity. Studies on the substrate specificity of UGASGT demonstrated that the specificity for the sugar residue transferred was very high, as activity was scarcely found when UDP-glucuronic acid was replaced by other UDP sugars: UDP-glucose and UDP-galactose. Soyasapogenols, which are the aglycons of soybean saponin, are usable acceptors, but glycyrrhetinic acid, sophoradiol, beta-amyrin, and flavonoids are not. These findings suggest that this UGASGT was a specific enzyme for UDP-glucuronic acid as a donor and soyasapogenols as acceptors, and that it was related to the biosynthesis of the sugar chain in soybean saponin. This study provides a basis for the molecular characterization of a key enzyme in saponin biosynthesis in soybean. The isolation of the gene may enable its use in the elucidation of the biosynthesis and physiological role of saponins in soybean.

Carbon Radioisotopes↗
PubMed1996

Cholesterol-independent membrane disruption caused by triterpenoid saponins.

The membrane-disrupting activity of 15 triterpenoid saponins, obtained from Chinese plants of the genus Aralia, was investigated using phosphatidylcholine liposomes with and without cholesterol. The permeability of the membrane was examined by monitoring the induced fluorescent dye release from the liposome. On the basis of the obtained results, the structure-activity relationship among glucuronides of oleanolic acid was discussed. This takes into account particularly the variation in the carboxyl function. Namely, the saponins could induce a permeability change on liposomal membrane without cholesterol when they are glycosylated at both C-3 and C-28 of the oleanolic acid. There also exists a great similarity in the time-course curves for dye-release within such saponins, reflecting their similar action with the lipid bilayer membrane. The saponins glycosylated only at C-3 could also exhibit the same activity with somewhat different action profiles when the glucuronic acid is esterified, while those with the free glucuronic acid required cholesterol in the liposomes to induce permeability change thereof.

Cholesterol↗
PubMed1985

ATP depletion in human platelets caused by permeabilization with saponin does not prevent serotonin secretion induced by collagen.

Saponin (5 to 25 micrograms/ml) produced a concentration-dependent decrease in the cellular content of total ATP and [32P]ATP in 32P-labeled human platelets. In platelets whose ATP had been profoundly decreased by saponin, Ca2+ produced phosphomonoesteratic cleavage of the polyphosphoinositides with a concomitant accumulation of phosphatidylinositol. Collagen still induced secretion of serotonin in platelets that had been treated with saponin in the presence or absence of Ca2+. This effect of collagen occurred in the absence of the formation of cyclooxygenase metabolites. In platelet permeabilized with saponin, agonist-induced secretion and aggregation seems to be unrelated to protein phosphorylation, breakdown of the inositol phospholipids by phospholipase C and formation of cyclooxygenase metabolites.

Adenosine Triphosphate↗
PubMed1980

Alfalfa saponins and alfalfa seeds. Dietary effects in cholesterol-fed rabbits.

Since alfalfa meal prevents hypercholesterolemia and atherosclerosis in rabbits and alfalfa saponins prevent the expected rise in cholesterolemia induced by dietary cholesterol in monkeys, the experiments being reported here were performed to determine whether alfalfa saponins affect atherogenesis in rabbits. In addition, the effects of alfalfa seeds were studied. Cholesterol-feb rabbits were randomly assigned to 3 groups: (a) control animals (N = 18); (b) animals maintained on a diet containing 1.0 to 1.2% alfalfa saponins (N = 18); and (c) animals maintained on a diet containing 40% alfalfa seeds (N = 17). Results after a 4-month observation period demonstrated that alfalfa saponins and alfalfa seeds reduce hypercholesterolemia, aortic sudanophilia, and the concentration of cholesterol in aortic intima-plus-media and in the liver, but do not induce changes in the hematocrit.

Animals↗
PubMed1993

Triterpenoid saponins from Anemone hupehensis.

Four triterpenoid saponins were isolated from Anemone hupehensis. On the basis of chemical and spectroscopic evidence, two new saponins, hupehensis saponins D and E, were elucidated as 3-O-beta-D-glucopyranosyl (1-->3)-beta-D-ribopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl oleanolic acid-28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside and 3-O-beta-D-glucopyransoyl (1-->3-beta-D-ribopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl hederagenin-28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside. The two known saponins were identified as huzhangosides B and D.

Carbohydrate Sequence↗
PubMed1992

Triterpenoid saponins from Argania spinosa.

Five new oleanane saponins named arganine A, B, D, E and F and two known saponins: arganine C and mi-saponin A were isolated from the kernel of Argania spinosa. The structures of these saponins were elucidated by using 1H NMR, 1H-1H COSY NMR, 13C NMR, FAB mass spectrometry and chemical evidence.

Carbohydrate Sequence↗
PubMed1992

Triterpenoidal saponins from Madhuca butyracea.

Two new triterpenoidal saponins, butyrosides A and B, were isolated from the seeds of Madhuca butyracea, along with two known saponins, Mi-saponin A and 16 alpha-hydroxy Mi-saponin A. On the basis of chemical and spectroscopic evidence, the structures of butyrosides A and B were established to be 3-O-beta-D-glucopyranosyl protobassic acid 28-O-beta-D-apiofuranosyl(1----3)-beta-D-xylopyranosyl (----4)-alpha-L-rhamnopyranosyl(1----2)-alpha-L-arabinopyranoside and 3-O-beta-D-glucopyranosyl 16 alpha-hydroxy protobassic acid 28-O-beta-D-apiofuranosyl(1----3)-beta-D-xylopyranosyl (1----4)-alpha-L-rhamnopyranosyl(1----2)-alpha-L-arabinopyranoside , respectively.

Carbohydrate Sequence↗