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At least 37 records · Page 2Linked to original sources

PubMed2005

Hypoglycemic effects of steroidal sapogenins isolated from Jamaican bitter yam, Dioscorea polygonoides.

In this study, three steroidal sapogenins (Delta3 diosgenin, diosgenin, and pennogenin) and the phytosterols, stigmasterol and beta-sitosterol were isolated from Jamaican bitter yam, Dioscorea polygonoides. Their effects on fasting blood glucose and intestinal amylase and ATPases in streptozotocin-induced diabetic rats were studied. The diabetic rats (fed supplemented and unsupplemented diets) lost weight significantly compared to the normal group. There was a significant increase in the activity of alpha-amylase in the proximal region of the small intestinal mucosa of diabetic rats fed sapogenin extract or commercial diosgenin. However, this did not result in increased fasting blood glucose. Instead, supplementation of the diet with bitter yam sapogenin extract significantly decreased fasting blood glucose compared to the diabetic group. Supplementation of the diet with bitter yam sapogenin extract or commercial diosgenin significantly reduced Na+-K+-ATPase activity in all three regions compared to the diabetic control group. Commercial diosgenin supplementation resulted in a significant increase in Ca2+ ATPase activity in proximal region compared to the diabetic control and bitter yam sapogenin extract groups. The effect of bitter yam sapogenin extract or commercial diosgenin on intestinal Na+-K+-ATPase activity could account for their hypoglycemic properties. However, there was adverse effect on the body weight.

Adenosine Triphosphatases↗

PubMed2004

Summer variation in the concentration of steroidal sapogenins in and the degree of fungal infection on Narthecium ossifragum plants from Møre og Romsdal County, Norway.

Thirty-nine leaf samples of Narthecium ossifragum collected from eight sites in Møre og Romsdal County, Norway, during June-September 1997 and 41 leaf samples collected at five sites in the same county during June-August 1998 were analysed for the concentrations of steroidal sapogenins using GC-MS. The 1998 samples were also examined for fungal elements (conidia and hyphae) after incubation in a moist chamber for 10-14 days. The highest 1997 and 1998 leaf sapogenin concentrations (4881 and 7115 mg/kg dry matter, respectively) were 13-14 times greater than the lowest sapogenin concentrations found (344 and 531 mg/kg dry matter, respectively). The results did not reveal systematic differences in sapogenin concentrations between the two seasons, or between samples harvested early or late in the same seasons, or between sapogenin concentrations in plants harvested at different sites. Cladosporium magnusianum was the predominant fungus found in the samples. The degree of fungal infection on the samples was in generally low, but the number of C. magnusianum colonies in the moist chamber preparations and fungal elements (conidia and hyphae) in leaf washings and on leaves tended to increase with time. Factor analysis and multiple regression analysis performed on the chemical and fungal results suggest that sporulation may have occurred in the fungi in response to increase in sapogenin concentrations.

Cladosporium↗

PubMed2005

Antinociceptive and anti-inflammatory effects of the saponin and sapogenins obtained from the stem of Akebia quinata.

The stem of Akebia quinata Decasisne (Lardizabalaceae) has been used to treat urinary tract inflammatory disease. It has been reported that saponins in medicinal plants may act as bioactive components after biodegradation to sapogenins in the gastrointestinal tract. To find the active components, we obtained the methanol (MeOH) extract from A. quinata stems and fractionated this extract into CHCl(3), butanol (BuOH), and H(2)O fractions. A saponin-containing BuOH fraction was refluxed in an acidic solution to yield the hydrolyzed fraction. Silica gel column chromatography separated kalopanaxsaponin A (1) from the BuOH fraction, and oleanolic acid (2) and hederagenin (3) were obtained from the hydrolyzed fraction. The antinociceptive effect was tested by hot plate-writhing and tail-flicks methods using mice, and the anti-inflammatory effect was assayed using carrageenan-induced rat edema against the following samples: the MeOH extract of A. quinata stems, its fractions, the isolated saponin, kalopanaxsaponin A, and the sapogenins hederagenin and oleanolic acid. The MeOH extract exhibited antinociceptive/anti-inflammatory effects by oral administration of 100 and 250 mg/kg doses, indicating that the MeOH extract has an antinociceptive/anti-inflammatory activity. The BuOH fraction (crude saponin) also significantly exhibited those bioactivities. Treatments with 10 and 30 mg/kg perorally of these two sapogenins produced significant antinociceptive/ anti-inflammatory effects in the rat, suggesting that the sapogenins may act as resultant active compounds. Compounds 2 and 3 inhibited dye leakage into the peritoneal cavity induced by acetic acid, and the latter was more active than the former. The anti-inflammtory effects were further supported by the reduction of carrageenan-induced lipid peroxidation and hydroxy radical content in serum. These results suggest that the antinociceptive/anti-inflammatory properties of the stem of A. quinata can be attributed to the sapogenins oleanolic acid and hederagenin.

Administration, Oral↗

PubMed2006

Intestinal disaccharidases and some renal enzymes in streptozotocin-induced diabetic rats fed sapogenin extract from bitter yam (Dioscorea polygonoides).

In this study, the effects of bitter yam sapogenin extract or commercial diosgenin on intestinal disaccharidases and some renal enzymes in diabetic rats were investigated. Diabetic male Wistar rats were fed diets supplemented with 1% sapogenin extract or commercial diosgenin for 3 weeks. Plasma glucose, intestinal disaccharidases and the activities of transaminases, acid phosphatase, glucose-6-phosphatase, ATP citrate lyase, glucose-6-phosphate dehydrogenase and pyruvate kinase were assessed for the level of metabolic changes in the kidney of diabetic rats. Sapogenin extract or commercial diosgenin supplementation resulted in a significant decrease in lactase and maltase activities in all three regions of the intestine compared to the diabetic control group. However, the test diets significantly reduced intestinal sucrase activity in the proximal and mid regions. Test diets supplementation resulted in a significant decrease in the activities of the transaminases compared to the normal and diabetic control groups. The activity of glucose-6-phosphatase was significantly increased while the activities of ATP citrate lyase, pyruvate kinase and glucose-6-phosphate dehydrogenase were significantly reduced in the kidney of the diabetic control rats compared to the normal group. Test diets supplementation did not significantly alter glucose-6-phosphatase, ATP citrate lyase and pyruvate kinase activities compared to the diabetic control. However, there was a significant increase in glucose-6-phosphate dehydrogenase activity toward the normal group. In conclusion, the consumption of bitter yam sapogenin extract or commercial diosgenin demonstrated hypoglycemic properties, which are beneficial in diabetes by reducing intestinal disaccharidases activities; however, bitter yam sapogenin extract may adversely affect the integrity of kidney membrane.

Animals↗

PubMed1990

[Triterpenoid sapogenins in the genus Grindelia].

A saponin fraction has been isolated from the ethanolic extract of Grindeliae herba. The saponin fraction showed strong haemolytic activity. The saponins were detected after separation on TLC by their color reactions and Rf values as well as by their haemolytic activity on blood agar. After hydrolysis, the chemical reactions and Rf values of the sapogenins were described. The main sapogenin was isolated by preparative chromatography and its structure was elucidated by mass, 1H-NMR, 13C-NMR, IR, and UV spectra. The compound is a new natural triterpenoid sapogenin lactone and is named grindeliasapogenin D. Spectral evidence is presented to establish its structure as 2 beta,3 beta,16 alpha,23-tetrahydroxyoleanan-28,13 beta-olide. Two further sapogenins present in small amounts were identified chromatographically as oleanolic acid and bayogenin using authentic reference substances. The aerial parts of Grindelia robusta Nutt, and G. lanceolata Nutt. (Asteraceae) (as well as two commercial extracts) were also investigated with respect to their saponin fraction. The 3 sapogenins mentioned above were detected in all samples. The antibiotic potency of the crude drug is not associated with the saponin fraction but is at least partially due to the resin fraction.

Anti-Infective Agents↗

PubMedDate not supplied

American ginseng. II. Analysis of ginsenosides and their sapogenins in biological fluids.

A gas-liquid chromatography (tlc) method was developed to assay individual ginsenosides and sapogenins in rabbit plasma and urine samples. A flavonoid, panasenoside, and a sterol, stigmasterol, were used as internal standards for ginsenosides and their sapogenins, respectively. Linear relationships of peak height ratio to weight ratio were obtained for ginsenosides (A1, 20-350 microgram; A2, 20-400 microgram; B2, 20-300 microgram; C, 20-500 microgram), and sapogenins (panaxadiol or panaxatriol, 10-200 microgram) in 0.1 ml of the silylation mixture. The glc assay method developed was sensitive to 0.2 microgram of ginsenosides and 0.1 microgram of sapogenins.

Animals↗

PubMedDate not supplied

13C cross-polarization MAS NMR study of some steroidal sapogenins.

Cross-polarization (CP) magic angle spinning (MAS) solid-state 13C NMR spectra of five steroidal sapogenins: tigogenin ((25R)-5alpha-spirostan-3beta-ol), hecogenin (3beta-hydroxy-(25R)-5alpha-spirostan-12-one), diosgenin ((delta5-(25R)-5alpha-spirosten-3beta-ol), sarsasapogenin ((25S)-55beta-spirostan-3beta-ol), and smilagenin ((25R)-5beta-spirostan-3beta-ol) were recorded. The solid-state chemical shifts are almost the same as for solution, which indicate that confirmations of sapogenins are similar in both phases. The doubling of some resonances in the spectra of solid diosgenin shows that there are two molecules in the crystallographic asymmetric unit. The cross-polarization time constants T(CP) and relaxation times in the rotating frame T(1rho)H were obtained from the variable-contact cross-polarization experiments for tigogenin and diosgenin. The values of T(CH) for methyl carbons indicate fast rotation of methyl groups and are close (0.30-0.35 ms), suggesting that the interaction with their intramolecular neighbors is similar. The values of T(1rho)H for carbons of tigogenin are longer than of diosgenin. Very efficient cross-polarization dynamics results in short time required for obtaining a spectrum of sapogenin of remarkably good quality.

Carbon Isotopes↗

PubMed1980

[Effect of vitamin E and protein quality on the hemolytic effect of Trigonella sapogenins in rats].

The influence of vitamin E (9, 90, 450 mg dl-alpha-tocopherol acetate/100 g diet), protein quality and temperature (70 degrees C for 10 min) on the sapogenin-induced hemolysis was studied in rats fed with diets containing different amounts of fenugreek-seed seedflour. Significant increased hemolysis rates were found in rats on diets with the following protein components: 1/3 Trigonella + 2/3 Cornflour (69.7 +/- 11.6% hemolysis), 100% Trigonella (21.0 +/- 8.6% hemolysis), 1/3 Trigonella + 2/3 Casein (14.1 +/- 10.7% hemolysis). The diets of these groups of animals contained raw Trigonella seeds and 9 mg vitamin E/100 g diet, which covers the requirements of rats on this vitamin. With this tocopherol supplement the applied heat treatment had no influence on the sapogenin effects on the erythrocytes. In the groups with the 10th fold and 50th fold of the vitamin E supplementation no significant hemolysis rate was observed. From these results we conclude that when fenugreek seeds are to be used in animal nutrition, a qualitative good protein supply as well as a sufficient intake of vitamin E should be considered in order to compensate the hemolytic effect of Trigonella sapogenins.

Animals↗

PubMed1978

A quantitative gas-liquid chromatographic method for the estimation of hecogenin and tigogenin in the leaves, juice and sapogenin concentrates of Agave sisalana.

A gas-liquid chromatographic method has been devised for the routine estimation of the hecogenin [3beta-hydroxy-(25R)-5beta-spirostan-12-one] and tigogenin [ (25R)-5beta-spirostan-3beta-ol] contents of Agave sisalana leaf and juice samples and of the crude sapogenin concentrates known as "coffee grounds". Because of partial degradation of the sapogenins in the GLC system it was found necessary to acetylate the compounds prior to their estimation. In East African samples the tigogenin proportion of the total sapogenin content is usually about 10%. At this level, the 95% inverse tolerance limits on predicted tigogenin weights are approximately +/- 7%.

Chromatography, Gas↗

PubMed1999

Acyl-CoA: cholesterol acyltransferase inhibitory activity of ginseng sapogenins, produced from the ginseng saponins.

Ginseng sapogenins were produced from ginseng saponins, isolated from Korean ginseng roots. Ginseng saponins very mildly inhibited acyl-CoA:cholesterol acyltransferase (ACAT) in vitro, however, the sapogenins showed strong inhibitory activity on microsomal ACAT. Therefore, the sapogenins will be one of key ingredients of ginseng affected a lowering of the serum total cholesterol level.

Animals↗

PubMed2005

Changes in some liver enzymes in streptozotocin-induced diabetic rats fed sapogenin extract from bitter yam (Dioscorea polygonoides) or commercial diosgenin.

The effects of steroidal sapogenin extract from bitter yam or commercial diosgenin on liver enzyme changes were investigated Diabetic male Wistar rats were fed diets supplemented with 1% steroidal sapogenin extract or commercial diosgenin for three weeks. Plasma glucose levels and the activities of hepatic glucose-6-phosphatase, pyruvate kinase and glucose-6-phosphate dehydrogenase were assessed Liver total cholesterol, HDL-cholesterol and total phospholipid were also measured. Plasma glucose decreased significantly (p < 0.05) in diabetic rats fed the three test diets compared to the diabetic control. The three test diets significantly decreased glucose-6-phosphatase activity compared to the diabetic control The activities of ATP-citrate lyase, pyruvate kinase and glucose-6-phosphate dehydrogenase were significantly reduced in the liver of diabetic rats compared to normal control. Supplementation of the diet with bitter yam steroidal sapogenin extract or commercial diosgenin did not significantly alter ATP citrate lyase and pyruvate kinase activities but significantly increased glucose-6-phosphate dehydrogenase activity in the liver compared to diabetic rats. This study shows that the feeding of the two test diets to diabetic rats results in alterations in the metabolism of glucose with subsequent reduction in plasma glucose concentration.

Animals↗

PubMed1992

Anti-inflammatory effect of natural steroid sapogenins on oral aphthous ulcers.

The search in plants for sapogenins has been stimulated by the need for readily accessible sources of sapogenins which can be converted in the laboratory to animal sterols of therapeutic importance. The present study represents a clinical trial for the investigation of the antiinflammatory effect of natural steroidal sapogenins on oral aphthous ulcers.

Adolescent↗

PubMed1995

Anti-elastase and anti-hyaluronidase activities of saponins and sapogenins from Hedera helix, Aesculus hippocastanum, and Ruscus aculeatus: factors contributing to their efficacy in the treatment of venous insufficiency.

Triterpene and steroid saponins and sapogenins of medicinal plants (Aesculus hippocastanum L., Hedera helix L., Ruscus aculeatus L.) are claimed to be effective for the treatment/prevention of venous insufficiency. In this work we evaluated the inhibitory effects of these plant constituents on the activity of elastase and hyaluronidase, the enzyme systems involved in the turnover of the main components of the perivascular amorphous substance. The results evidence that for Hedera helix L., the sapogenins only non-competitively inhibit hyaluronidase activity in a dose-dependent fashion, showing comparable IC50 values (hederagenin IC50 = 280.4 microM; oleanolic acid IC50 = 300.2 microM); both the saponins hederacoside C and alpha-hederin are very weak inhibitors. The same behaviour is observed for serine protease porcine pancreatic elastase: the glycosides are devoid of inhibitory action, while genins are potent competitive inhibitors (oleanolic acid IC50 = 5.1 microM; hederagenin IC50 = 40.6 microM). Constituents from Aesculus hippocastanum L. show inhibitory effects only on hyaluronidase, and this activity is mainly linked to the saponin escin (IC50 = 149.9 microM), less to its genin escinol (IC50 = 1.65 mM). By contrast, ruscogenins from Ruscus aculeatus L., ineffective on hyaluronidase activity, exhibit remarkable anti-elastase activity (IC50 = 119.9 microM; competitive inhibition). The mechanism of elastase inhibition by triterpene and steroid aglycones, with a nitroanilide derivative as substrate, is discussed.

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↗

PubMed2004

Supercritical fluid extraction of sapogenins from tubers of Smilax china.

Supercritical CO(2) fluid extraction (SFE-CO(2)) was used to extract the sapogenins after acid hydrolysis from Smilax china tubers. The influence of extraction variables, such as modifier, pressure, temperature and extraction time, were studied. SFE-CO(2) was found to produce higher yield than conventional solvent extraction. The highest yield (0.454%) of sapogenins, mostly containing diosgenin, was obtained using 35 MPa pressure, 65 degrees C and 95% EtOH as a modifier for 180 min, higher than that obtained with conventional extraction methods (0.385%).

Chromatography, Supercritical Fluid↗

PubMed1985

Analysis of soybean sapogenins by high-performance liquid chromatography.

A method for the analysis of soybean sapogenins is described. The method is based on the extraction of soybean saponins from a defatted sample. The triterpene glycosides are then hydrolysed with subsequent analysis of the liberated sapogenins by high-performance liquid chromatography using gradient elution and mass detection. By use of a sapogenin/carbohydrate ratio, an estimate of the total saponin content can be made.

Chromatography, High Pressure Liquid↗

PubMed1998

Stimulatory effects of starfish sapogenins (Asterias amurensis and Lethasterias nanimensis chelifera) on molluscan heart (Spisula sachalinensis).

Sapogenins from the starfish Asterias amurensis and Lethasterias nanimensis chelifera, 5 alpha-pregn-9(11)-ene-3 beta,6 alpha-diol-20-one, 5 alpha-cholest-9(11)-ene-3 beta,6 alpha-diol-23-one, 5 alpha-cholesta-9(11),24(25)-diene-3 beta,6 alpha-diol-23-one, (20E)-5 alpha-cholesta-9(11),20(22)-diene-3 beta,6 alpha-diol-23-one and 24 zeta-methyl-5 alpha-cholesta-9(11),20(22)-diene-3 beta,6 alpha-diol-23-one, stimulated the contractile force of the heart of the mollusk Spisula sachalinensis at concentration of 5 x 10(-5) M. Ouabain, a specific inhibitor of Na+,K(+)-ATPase, at concentration of 5 x 10(-5) M had no effect on this physiological model. Starfish sapogenins of the cholestane series moderately inhibited rat brain cortex Na+,K(+)-ATPase and decreased Ca2+ influx into Ehrlich carcinoma cells. In contrast, pregnane asterogenin asterone did not inhibit Na+,K(+)-ATPase and increased the influx of Ca2+ into cells. These effects were not the result of cell membrane damage, because none of the compounds tested have hemolytic activity.

Animals↗

PubMed2006

The sapogenin atroviolacegenin and its diglycoside atroviolaceoside from Allium atroviolaceum.

A phytochemical analysis of broadleaf wild leek, Allium atroviolaceum, has led to the isolation of a new sapogenin, named atroviolacegenin (1, Chart 1), and its diglycoside derivative, named atroviolaceoside (2), both possessing a hydroxyl group at C-27, a rare feature among sapogenins and saponins. On the basis of chemical and spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry, the structures of the new compounds were elucidated as (25R)-5alpha-spirostan-2alpha,3beta,6beta,27-tetrol (1) and (25R)-5alpha-spirostan-2alpha,3beta,6beta,27-tetrol 3-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranoside (2). These compounds are accompanied by three known spirostanol and furostanol saponins. In addition, 4,4'-dihydroxy-3-methoxychalcone, p-coumaroyl-N-tyrosine, and p-feruloyl-N-tyrosine have been found in the flowers and bulbs. Atroviolacegenin and atroviolaceoside were assayed to evaluate their antispasmodic activity in the guinea-pig isolated ileum and the data compared to those previously found for tropeosides (3a/3b and 4a/4b) from Tropea red onion bulbs. The absence of activity for both atroviolacegenin and atroviolaceoside highlighted the key role of the furostanol-type aglycone moiety for antispasmodic activity.

Allium↗