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PubMed1998

Multiple-stage tandem mass spectrometry for structural characterization of saponins.

Nanoelectrospray ion trap multiple-stage tandem mass spectrometry was applied to characterize saponins present in HPLC fractions from Quil A, a commercially available bark extract. An analytical strategy was developed based on recognition of carbohydrate sequence ions as well as glycosidic ring-cross ions formed by gamma-hydrogen rearrangements and successive retro-Diels-Alder fragmentations. These ions could be used for the determination of several glycosidic linkages, ring sizes, and positions of acyl groups. The presence of an acyl group on a monosaccharide residue facilitated the determination of the substitution pattern, due to the induction of ring-cross fragmentation. Deuteriomethylation resulted in a more extended set of ring-cross ions, thus allowing determination of additional glycosidic linkages. An analysis typically consumed 200 ng of sample and a total of 1-4 h for measurement and interpretation. The applied method is attractive as a pre-NMR analysis, especially because it resulted rapidly in an overall idea of the structure even when starting from scratch. The multiple-stage tandem approach enabled structural determination of saponins to a more detailed level than achievable with current single-stage tandem mass spectrometry.

Carbohydrate Sequence↗
PubMedDate not supplied

NMR and LC-MSn characterisation of two minor saponins from Ilex paraguariensis.

Two minor saponins obtained from the methanolic extract of the leaves of Ilex paraguariensis have been characterised by 13C-NMR, 1H-NMR, API-MS and chemical hydrolysis as oleanolic acid-3-O-(beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)-(28-->1)- beta-D-glucopyranosyl ester (guaiacin B) and oleanolic acid-3-O-(beta-D-glucopyranosyl-(1-->3)-(alpha-L-rhamnopyranosyl- (1-->2))-alpha-L-arabinopyranosyl)-(28-->1)-beta-D-glucopyranosyl ester (nudicaucin C). Both are isomeric forms of the known matesaponins 1 (MSP 1) and 2 (MSP 2) and differ only by the nature of the aglycone: they have oleanolic acid instead of ursolic acid, as found in the matesaponins. These minor saponins have not been fully separated from their major isomers MSP 1 and 2 and were characterised by in-mixture NMR analysis, LC-MS and LC-MSn experiments.

Base Sequence↗
PubMed1987

Ultrastructural demonstration of exocytosis in intact and saponin-permeabilized cultured bovine chromaffin cells.

Exocytosis is the release of intracellular vesicular contents directly to the cell exterior after fusion of the vesicular and plasma membranes. It is generally accepted as the process by which transmitters and hormones are released from neurons and neurosecretory cells. There is overwhelming biochemical evidence that exocytosis is the mechanism by which catecholamines are released from adrenal chromaffin cells. With the exception of the hamster, however, there is little ultrastructural evidence to support such a mechanism. We have used a modified in vitro tannic-acid method to visualize exocytosis by transmission electron microscopy in intact and saponin-permeabilized bovine chromaffin cells. When cells are exposed to tannic-acid-containing medium, the content of vesicles involved in exocytosis is coagulated in situ as the vesicle opens to the exterior. Numerous exocytotic profiles were observed. The exposed vesicle contents appeared more granular than those of vesicles in the cell interior. Tannic acid also made the plasma membrane more distinct. Small holes were apparent in the plasma membrane of saponin-treated cells, with little disruption of underlying cytoplasmic structure. Furthermore, when these cells were stimulated with calcium, exocytosis was evident only at regions of intact plasma membrane, not at the holes. Parallel measurements of secretion showed no secretion in the presence of tannic acid. Pretreatment with tannic acid prevented subsequent secretion by intact cells and markedly reduced that of permeabilized cells, indicating a probable change in the nature of the plasma membrane.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed2005

Immunological-adjuvant saponins from the roots of Panax notoginseng.

The total saponin extract from the dried roots of Panax notoginseng (Burk.) F. H. Chen possesses immunological-adjuvant activities. Guided by in vivo immunological tests, further study on this fraction afforded three active dammarane-type saponins. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods, including 1D- and 2D-NMR. The novel compound (20S)-protopanaxatriol 20-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1), and the two known compounds ginsenoside Rh4 (2) and notoginsenoside K (3) exhibited immunological-adjuvant activities on the humoral immune responses of ICR mice against ovalbumin (OVA).

Animals↗
PubMed1985

Intracellular Ca2+ sequestration in cultured mouse fibroblasts: ATP-dependent Ca2+ uptake by saponin-permeabilized Swiss 3T3 cells.

Intracellular Ca2+ sequestration was studied by determining 45Ca2+ uptake by saponin-permeabilized Swiss 3T3 mouse fibroblasts. Uptake was enhanced by addition of ATP and was dependent on the concentrations of ATP and saponin. ADP and UTP also enhanced uptake, but less than did ATP. Mitochondrial Ca2+ uptake was distinguished from nonmitochondrial uptake by the use of antimycin A plus oligomycin at various Ca2+ concentrations. Major sites for sequestration at 10(-5) M Ca2+ are probably mitochondrial and those at 10(-7) M Ca2+ nonmitochondrial, because these drugs inhibited ATP-dependent Ca2+ uptake at 10(-5) M but not at 10(-7) M. A23187 completely inhibited uptake, regardless of the Ca2+ concentration. Effects of various agents on sequestration were tested; ruthenium red, 2,4-dinitrophenol, monovalent cation ionophores, and melittin markedly decreased ATP-dependent Ca2+ uptake at 10(-5) M Ca2+. The calmodulin antagonists trifluoperazine (TFP) and W-7 inhibited Ca2+ uptake at both 10(-5) and 10(-7) M Ca2+, TFP more so than W-7, especially at 10(-5) M. These results suggest that intracellular Ca2+ in Swiss 3T3 cells is regulated by mitochondrial and nonmitochondrial Ca2+ stores in an ATP-dependent way and that in a physiological resting state the nonmitochondrial Ca2+ store, probably the endoplasmic reticulum, is the major site for the sequestration.

2,4-Dinitrophenol↗
PubMed2001

Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection.

This paper describes the first analytical method suitable for the determination of steroidal saponins in Tribulus terrestris. A separation by high performance liquid chromatography (HPLC) was achieved by using a reversed-phase (RP-18) column, evaporative light scattering (ELS) detection, and a water/acetonitrile gradient as the mobile phase. The marker compound, protodioscin, was detected at a concentration as low as 10.0 microg/mL. Several different samples of plant material were successfully analyzed, and depending on origin and plant part used for extraction, significant differences in the composition of the saponins were observed. The analysis of market products showed considerable variations of 0.17 to 6.49% in the protodioscin content.

Chromatography, High Pressure Liquid↗
PubMed1979

Cytotoxic saponins from the Chinese herbal drug Yunnan Bai Yao.

Two cytotoxic saponins were isolated from the acetone extracts of the herbal preparation "Yunnan Bai Yao" by column chromatography. They were identified as a 3-([alpha-L-rhamnopyranosyl()Rha leads to 2Glu)]-[alpha-L-arabinofuranosyl(1Ara leads to 4Glu)]-beta-D-glucopyranosyl)-25(R)-spirost-5-en-3beta-ol (I) and 3-([alpha-L-rhamnopyranosyl(1Rha leads to 4Rha)-alpha-L-rhamnopyranosyl(1Rha leads to 4Glu)]-[alpha-L-rhamnopyranosyl(1Rha leads to 2Glu)]-beta-D-glucopyranosyl)-25(R)-spirost-5-en-3 beta-ol (VI). Both saponins exhibited significant cytotoxicity in the standard P-388, L-1210, and 9KB tissue culture screens.

Animals↗
PubMed1995

DS-1, a modified Quillaja saponin, enhances ocular and nasal absorption of insulin.

The purpose of this study was to test DS-1, a modified Quillaja saponin, for its efficacy as an absorption enhancer. Anesthetized rats receiving eyedrops or nosedrops formulated with regular pork insulin in saline showed no hypoglycemic response, indicating no systemic absorption of insulin. However, rats receiving eyedrops or nosedrops formulated with insulin plus 0.025-0.10% DS-1 showed rapid absorption of insulin and a concomitant decrease in serum D-glucose levels. No response was observed following sublingual or buccal delivery of insulin. In conclusion, the modified saponin DS-1 was efficacious at enhancing nasal or ocular insulin delivery at extremely low concentrations. The mechanism of DS-1 action is not yet known.

Absorption↗
PubMed2005

Characterization of two minor saponins from Cordia piauhiensis by 1H and 13C NMR spectroscopy.

A careful NMR analysis with full assignment of the 1H and 13C spectral data for two minor saponins isolated from stems of Cordia piauhiensis is reported. These saponins were isolated by high-performance liquid chromatography and characterized as 3beta-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]pomolic acid 28-O-[beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl] ester (1) and 3beta-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]oleanolic acid 28-O-[beta-D-xylopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl] ester (2). Their structures were established using a combination of 1D and 2D (1H, 1H-COSY, TOCSY, NOESY, gs-HMQC and gs-HMBC) NMR techniques, electrospray ionization mass spectrometry and chemical evidence.

Carbohydrate Sequence↗
PubMed2005

Complete 1H and 13C NMR assignments of six saponins from Sapindus trifoliatus.

Complete 1H and 13C spectral assignments are reported for six saponins from the pericarp of Sapindus trifoliatus (Hindi name: Reetha) collected from Madhya Pradesh and Maharashtra, India, using only 1D and 2D NMR methods. The structures of the compounds were elucidated as hederagenin 3-O-(3-O-acetyl-beta-D-xylopyranosyl)-(1-3)-alpha-L-rhamnopyranosyl-(1-2)-alpha-L-ara-binopyranoside, hederagenin 3-O-(4-O-acetyl-beta-D-xylop-yranosyl)-(1-3)-alpha-L-rhamnopyranosyl-(1-2)-alpha-L-arabinop-yranoside, hederagenin 3-O-(3,4-O-diacetyl-beta-D-xylopy-ranosyl)-(1-3)-alpha-L-rhamnopyranosyl-(1-2)-alpha-L-arabinopy-ranoside, hederagenin 3-O-(3,4-O-diacetyl-alpha-L-arabinop-yranosyl)-(1-3)-alpha-L-rhamnopyranosyl-(1-2)-alpha-L-arabinop-yranoside, hederagenin 3-O-(beta-D-xylopyranosyl)-(1-3)-alpha-L-rhamnopyranosyl-(1-2)-alpha-L-arabinopyranoside and he-deragenin 3-O-(alpha-L-arabinopyranosyl)-(1-3)-alpha-L-rhamno-pyranosyl-(1-2)-alpha-L-arabinopyranoside. It is concluded that saponins of this complexity approach the limit of structural complexity, which can be solved by NMR alone, precisely and quickly.

Carbon Isotopes↗
PubMedDate not supplied

Analysis and quantitative determination of group B saponins in processed soybean products.

Pure analytical standards for the major saponins present in processed soy products, the group B saponins (soyasaponins I, II, III and IV), were isolated in mg quantities by a combination of processing, precipitation/re-solubilisation, TLC and preparative HPLC. These standards were determined to be pure by LC-ESI/MS analysis and NMR. The standards were used to perfect a facile analytical HPLC method using spectrometric detection to determine the percent composition of the group B soyasaponins in various products from processing of soybean.

Chromatography, High Pressure Liquid↗
PubMed2003

A new bioactive steroidal saponin from Sansevieria cylindrica.

A new steroidal saponin was isolated from the leaves of Sansevieria cylindrica. Its structure was established as (3beta,12beta,15alpha,25S)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl 12-O- (6-deoxy-alpha-L-mannopyranosyl)-15-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside. The structural identification was performed using detailed analyses of (1)H and (13)C NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR, HMBC and HMQC) and chemical conversions. The steroidal saponin showed no haemolytic effects in the in vitro assays and demonstrated inhibition of the capillary permeability activity.

Acetic Acid↗
PubMed2003

Biological activities of synthetic saponins and cardiac glycosides.

Comparisons of the biological activities of diosgenyl (DIO) beta-D-xylopyranosyl- (1 --> 2)-alpha-D-glucopyranoside (2DXalpha) and beta-D-glucopyranosyl- (1 --> 3)-beta-D-glucopyranoside (3GLbeta) or methyl glycyrrhetinate (GAM) 2DXalpha and 3GLbeta with those of the other DIO- or GAM- glycosides confirmed our assumption that both haemolytic and antifungal activities of DIO-glycosides (steroid saponins) generally parallel each other, while almost all haemolytic GAM-glycosides (triterpenoid saponins) have no antifungal activity. By comparisons of digitoxigenyl (DIG) 2DXalpha, beta-D-xylopyranosyl- (1 --> 2)-beta-D-glucopyranoside (2DXbeta) and 3GLbeta with the other DIG-glycosides, the previous supposition on DIG-diglycosides (cardiac diglycosides) has been developed into the assumption that those having a (1 --> 4), (1 --> 3) or (1 --> 2)beta sugar linkage show stronger anti-ATPase and antiviral activities than those with a (1 --> 6) or (1 --> 2)alpha linkage.

Adenosine Triphosphatases↗
PubMed2003

The cytotoxicity of methyl protoneogracillin (NSC-698793) and gracillin (NSC-698787), two steroidal saponins from the rhizomes of Dioscorea collettii var. hypoglauca, against human cancer cells in vitro.

In our continuous studies of anticancer activity of steroidal saponins from the rhizomes of Dioscorea collettii var. hypoglauca (Dioscoreaceae), methyl protoneogracillin (NSC-698793) and gracillin (NSC-698787) were tested for cytotoxicity against human cancer cell lines from leukemia and eight solid tumor diseases. As a result, methyl protoneogracillin was cytotoxic against all the test cell lines with GI(50) < 100 micro M, especially selectively against two leukemia lines (CCRF-CEM and RPMT-8226), one colon cancer line (KM12), two central nervous system (CNS) cancer lines (SF-539 and U251), one melanoma line (M14), one renal cancer line (786-0), one prostate cancer line (DU-145), and one breast cancer line (MDA-MB-435), with GI(50) < or = 2.0 micro M. Leukemia, CNS cancer, and prostate cancer were the most sensitive subpanels, while ovarian cancer was the least sensitive subpanels. The preliminary toxicity studies showed that the maximum tolerant dose was 600 mg/kg for methyl protoneogracillin to mice. Gracillin was cytotoxic against most cell lines with GI(50), TGI and LC(50) at micromolar levels, but no activity against EKVX (non-small cell lung cancer), HT29 (colon cancer), OVCAR-5 (ovarian cancer), and SN12C (renal cancer). Based on structure-activity relationship, C-25 R/S con fi guration was critical for leukemia selectivity between methyl protoneogracillin and methyl protogracillin. F-ring was critical to selectivity between furostanol (methyl protoneogracillin and methyl protogracillin) and spirostanol (gracillin) saponins in this study. By an analysis of COMPARE software, no compounds in the NCI's database had similar mean graphs to those of methyl protoneogracillin and gracillin, respectively, indicating potential novel mechanism(s) of action involved. Put all in together, methyl protoneogracillin has been selected as a potential anticancer candidate for hollow fi ber assay to nude mice, but gracillin will not be pursued due to lack of selectivity against human cancer diseases.

Animals↗
PubMed2006

Antimicrobial activity of saponins from Medicago sp.: structure-activity relationship.

The antimicrobial activity of saponins from Medicago sativa, M. arborea and M. arabica against a selection of medically important yeasts, Gram-positive and -negative bacteria was investigated. Structure-activity growth inhibitory effects of related prosapogenins and sapogenins are also described. Increasing antibiotic activity was observed going from the saponin extracts to the sapogenin samples, suggesting that the sugar moiety is not important for the antimicrobial efficacy. Activity was especially high against Gram-positive bacteria (Bacillus cereus, B. subtilis, Staphylococcus aureus and Enterococcus faecalis) with M. arabica being the species showing a broader spectrum of action. Discrete antifungal activity was also observed, mainly against Saccharomyces cerevisiae. The observed antimicrobial properties of M. sativa and M. arborea were related to the content of medicagenic acid, while hederagenin seems to contribute to the bioactivity of M. arabica total sapogenins.

Anti-Bacterial Agents↗
PubMed2006

Reduction of fat storage in mice fed a high-fat diet long term by treatment with saponins prepared from Kochia scoparia fruit.

The fresh fruit (Japanese name, Tonburi) of Kochia scoparia has been used as a food garnish in Japanese-style dishes from ancient times, and may prevent metabolic syndromes such as hyperlipidemia, hypertension, obesity and atherosclerosis. This study was performed to clarify whether an ethanol extract of K. scoparia fruit prevented obesity induced in mice by a high-fat diet for 9 weeks. The ethanol extract of K. scoparia fruit prevented the increases in body weight and parametrial adipose tissue weight induced by the high-fat diet. Furthermore, consumption of a high-fat diet containing 1% or 3% K. scoparia extract significantly increased the fecal content and the fecal triacylglycerol level at day 3 compared with those in the high-fat diet group. The ethanol extract (250 mg/kg) and total saponins (100 mg/kg) of K. scoparia inhibited the elevation of the plasma triacylglyccerol level 2 or 3 h after the oral administration of the lipid emulsion. Total saponins, momordin Ic, 2'-O-beta-d-glucopyranosyl momordin Ic and 2'-O-beta-d-glucopyranosyl momordin IIc isolated from K. scoparia fruit inhibited the pancreatic lipase activity (in vitro). These findings suggest that the anti-obesity actions of K. scoparia extract in mice fed a high-fat diet may be partly mediated through delaying the intestinal absorption of dietary fat by inhibiting pancreatic lipase activity.

Animals↗
PubMed2001

Antiinflammatory and antioxidant property of saponins of tea [Camellia sinensis (L) O. Kuntze] root extract.

Two groups of saponins, TS-1 and TS-2, isolated from tea root extract (TRE) were tested for antiinflammatory and in vitro antioxidant activity. Both TS-1 and TS-2 inhibited carrageenan-induced paw oedema in rats. The antioxidant activity of these compounds was evaluated using the xanthine-xanthine oxidase system. The study indicated that the previously observed antitumour activity of TRE might be mediated through scavenging of free radicals by saponins and their antiinflammatory activity.

Animals↗
PubMed1994

Measurement of fluorescence changes of NAD(P)H and of fluorescent flavoproteins in saponin-skinned human skeletal muscle fibers.

Saponin-skinned human muscle fibers from M. vastus lateralis were immobilized in a quartz capillary to detect the fluorescence changes of NAD(P)H and of fluorescent flavoproteins. To get sufficient intense fluorescence signals from a small amount of muscle tissue the NAD(P)H fluorescence was excited by means of an HeCd laser at 325 nm and the flavoprotein fluorescence by an argon-ion laser at 454 nm or by the second wavelength of a HeCd laser at 442 nm. Using this experimental setup the fluorescence spectra of NAD(P)H, of alpha-lipoamide dehydrogenase and of electron-transfer flavoprotein were detected in saponin-skinned human muscle fibers. These fibers behaved identically to isolated mitochondria: (i) The addition of substrates caused an increase in reduction of mitochondrial NAD+, (ii) the addition of ADP caused its reoxidation, and (iii) the addition of respiratory chain inhibitors led to an almost complete reduction of NAD+. It was observed that the redox state of the NAD(P) system and of the alpha-lipoamide dehydrogenase reached after addition of 1 mM ADP correlates with the rate of active state respiration with NAD-dependent substrates. Therefore, this fluorimetric method is suitable to compare the mitochondrial oxidation capacities of NAD-dependent substrates in less then 5 mg wet weight muscle tissue. Moreover, the maximal changes in fluorescence of NAD(P)H and flavoproteins correlate with the amount of mitochondrial marker enzymes per milligram muscle tissue. Using this method a myopathy caused by a diminished content of mitochondria per milligram muscle tissue was observed.

Adenosine Diphosphate↗