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Results for “SAPOGENINS”

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PubMed1993

An attempt to reproduce crystal-associated cholangitis in lambs in experimental dosing of sarsasapogenin or diosgenin alone and in combination with sporidesmin.

No liver damage occurred in a group of 21 lambs dosed intraruminally with up to 9 g of sarsasapogenin or diosgenin daily for 10 consecutive days. In contrast, seven out of 15 lambs dosed with 0.1 mg of sporidesmin/kg liveweight in combination with sarsasapogenin and three out of six lambs dosed with sporidesmin in combination with diosgenin developed liver lesions. These were typical of those induced by sporidesmin. One lamb dosed with sporidesmin in combination with 9 g of diosgenin developed a crystal-associated cholangitis typical of Panicurn intoxication and alveld. No sapogenins were detected in urine by gas chromatography-mass spectrometry. The results suggest that orally administered sarsasapogenin and diosgenin are either not hepatotoxic per se or are too poorly absorbed to elicit a toxic response. The results provide only weak evidence that sporidesmin may be involved in the aetiology of Panicurn intoxication.

Journal Article↗

PubMed1976

Field studies on the African fruit bat Epomophorus wahlbergi (Sundevall), with special reference to male calling.

Social interactions, site attachment and group cohesion were studied in a free-living colony of Epomophorus fruit bats. Daily activites in an undisturbed colony were recorded. Special attention was paid to the peculiar calling behavior of courting male during the night. Structure and repetition rate of their sounds were analyzed in the laboratory. A special mode of acoustic interaction was found and related to the observed spacing out of calling males. By following feeding animals in the field and by analysis of their faeces we found that besides fruits they eat special leaves which afford steroidal sapogenins.

Animals↗

PubMed2005

UDP-glucuronosyltransferase 1A4 polymorphisms in a Japanese population and kinetics of clozapine glucuronidation.

The UDP-glucuronosyltransferase (UGT) family plays a major role in the excretion of endobiotics and xenobiotics and their metabolites. Human UGT1A4 catalyzes the glucuronidation of primary, secondary, and tertiary amines, sapogenins, androgens, and progestins. We directly sequenced polymerase chain reaction-amplified fragments of the UGT1A4 gene from 100 healthy adult Japanese volunteers and calculated their mutation frequency. We identified four single nucleotide polymorphisms (SNPs): three in exon 1 (142T > G: L48V, 448T > C: L150L, 804G > A: P268P), and one in intron 1 (867 + 43C > T). We found three types of alleles with distinct SNP combinations that coded for different amino acid sequences: L48V-L150L-P268P-867 + 43C > T (frequency, 0.155), L48V (0.01), and P268P (0.01) (wild-type frequency was 0.825). The L48V mutant gave twice the efficiency (V(max)/K(m)) for the antipsychotic drug clozapine as the wild-type. Efficiencies of L48V for trans-androsterone, imipramine, and cyproheptadine were increased, but the efficiency for tigogenin was reduced. L48V therefore increased or decreased the glucuronidation activity, depending upon the substrates. This study shows the importance of identifying patients with the L48V polymorphism when calculating dosage, and when considering the potential adverse effects of drugs that are substrates of UGT1A4.

Alleles↗

PubMed2006

Antifungal activity of C-27 steroidal saponins.

As part of our search for new antifungal agents from natural resources, 22 C-27 steroidal saponins and 6 steroidal sapogenins isolated from several monocotyledonous plants were tested for their antifungal activity against the opportunistic pathogens Candida albicans, Candida glabrata, Candida krusei, Cryptococcus neoformans, and Aspergillus fumigatus. The results showed that the antifungal activity of the steroidal saponins was associated with their aglycone moieties and the number and structure of monosaccharide units in their sugar chains. Within the 10 active saponins, four tigogenin saponins (compounds 1 to 4) with a sugar moiety of four or five monosaccharide units exhibited significant activity against C. neoformans and A. fumigatus, comparable to the positive control amphotericin B. The antifungal potency of these compounds was not associated with cytotoxicity to mammalian cells. This suggests that the C-27 steroidal saponins may be considered potential antifungal leads for further preclinical study.

Animals↗

PubMed1997

Dietary diosgenin attenuates subacute intestinal inflammation associated with indomethacin in rats.

We investigated the effects of dietary diosgenin (Dio), a plant-derived sapogenin, on indomethacin (Indo)-induced intestinal inflammation and alterations in bile secretion in rats. In anesthetized rats, bile secretion, intestinal inflammation, and blood chemistry were assessed 3 days after two subcutaneous injections of Indo given 24 h apart. Dio (> 80 mg.kg-1.day-1) pretreatment significantly inhibited weight and food intake decreases and intestinal inflammation. This protective effect was confirmed by examination of gross and histological findings and intestinal myeloperoxidase activity. Dio significantly increased biliary cholesterol (Chol) output and prevented the decreases in bile flow, bile acid output, and biliary alpha-muricholic acid and the increases in biliary hyodeoxycholic acid, deoxycholic acid, and hydrophobicity index of bile. Significantly more biliary Chol and phospholipids were present in macromolecules separate from bile acids and Indo in Dio-treated rats. Dio significantly increased the elimination constant of Indo and reduced plasma Indo levels at 3 and 12 h but did not influence biliary secretion of Indo for 3.5 h after injection. Although Dio dose-dependently attenuated subacute intestinal inflammation and normalized bile secretion in this model, it may also compromise the anti-inflammatory action of indo.

Acute Disease↗

PubMed2001

In vitro effect of fenugreek extracts on intestinal sodium-dependent glucose uptake and hepatic glycogen phosphorylase A.

Fenugreek (Trigonella foenum-graecum L. seed) is a food with traditional medicinal use in diabetes. Beneficial effects have been demonstrated in diabetic animals and both insulin-dependent and non-insulin-dependent diabetic subjects. Effects of a lipid extract A, crude ethanolic extract B, further sub-fractions of B (saponin-free C, saponin D and sapogenin E) and a gum fibre fraction F on intestinal sodium-dependent glucose uptake were investigated in vitro using rabbit intestinal brush border membrane vesicles. All fractions except A inhibited glucose-uptake at 0.33 and/or 3.3 mg/mL (p < 0.001). Greatest inhibition was observed with fractions D and E. Diosgenin and trigonelline (compounds reported in fenugreek) also inhibited glucose-uptake (IC50 values approximately 3 mg/ml, equivalent to 8 mM and 19 mM respectively) but did not account for the activity of the crude extracts. Fenugreek extracts had no effect on basal levels of glycogen phosphorylase a (HGPa) activity in rat hepatocyte suspensions. However fractions C and E caused a marginal but statistically significant inhibition (18.9 and 15.1% respectively, p < 0.05) of glucagon induction of this enzyme suggesting a glucagon-antagonist effect. Diosgenin (1.65 mg/ml; 4 mM) inhibited glucagon-induced HGPa activity by 20% (p < 0.05), and was more effective than trigonelline (non significant inhibition of 9.4% at 1.65 mg/ml, 10 mM).

Animals↗

PubMed2001

Experimentally induced cholangiohepatopathy by dosing sheep with fractionated extracts from Brachiaria decumbens.

Cholangiohepatopathy was induced in 5 lambs by oral administration of extracts from signal grass (Brachiaria decumbens) in Brazil. Grossly there were pale foci multifocally distributed throughout the hepatic parenchyma in 4 lambs. The microscopic changes, which were similar to those produced by other steroidal sapogenins-containing plants such as Tribulus terrestris and Panicum spp., included multifocal cholangitis, bile duct proliferation, and the presence of crystals in the biliary system.

Administration, Oral↗

PubMed2004

The mitotic-arresting and apoptosis-inducing effects of diosgenyl saponins on human leukemia cell lines.

Diosgenyl saponins are the most abundant steroid saponins, and exert a large variety of biological functions. In a previous report, we showed that dioscin was able to induce cytotoxicity and apoptosis in human myeloblast leukemia HL-60 cells. This study further investigated the action mechanisms underlying this effect. The activation of caspase-9 and -3, but not caspase-8, together with the down-regulation of anti-apoptotic Bcl-2 protein, demonstrated that the apoptotic signaling triggered by dioscin was mediated through the intrinsic mitochondria-dependent pathway. We also investigated its anti-proliferative effect on human chronic myelogenous leukemia K562 cells. Flow cytometry analysis showed that dioscin treatment induced the accumulation of cells in the G(2)/M phase. Cytomorphology with DAPI and Wright-Giemsa staining demonstrated the enlargement of cell volume and multinucleation in the treated cells. Subsequent apoptosis was delineated with phosphatidylserine externalization and DNA hypodiploidy. Trillin was one of the hydrolysates of dioscin. We demonstrated that it could induce multinucleation in HL-60, K562 and human promyelocytic leukemia NB(4) cells, suggesting its extensive mitotic-arresting effects. As the diosgenyl sapogenin, diosgenin was also shown to be able to induce multinucleation and apoptosis in K562 cells in a similar manner to dioscin. These findings suggest that diosgenyl saponins have the properties to induce mitotic arrest and apoptosis, suggesting that they may be a new kind of antimitotic agent.

Antineoplastic Agents, Phytogenic↗

PubMed1990

Saponins from leaves of Acanthopanax hypoleucus Makino.

From the leaves of Acanthopanax hypoleucus Makino (Araliaceae), five triterpenoidal saponins, having oleanolic acid and hederagenin as sapogenins, were isolated. On the basis of chemical and spectral data, the structures of two new saponins, named hypoleucosides A (1), and B (5) were elucidated as follows: 1; 3-O-beta-D-glucopyranosyl 11 alpha-methoxy-oleanolic acid 28-O-beta-D-glucopyranosyl ester, 5; 3-O-beta-D-glucopyranosyl-(1----2)-alpha-L-arabinopyranosyl-(1---- 4)-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl-(1----6)-beta-D-glucopyranosyl ester.

Animals↗

PubMed1992

Isolation and structure elucidation of gymnemic acids, antisweet principles of Gymnema sylvestre.

The structure of gymnemagenin (3 beta,16 beta,21 beta,22 alpha,23,28-hexahydroxy-olean-12-ene), the sapogenin of the antisweet principles of Gymnema sylvestre, was established by X-ray analysis of the 3 beta,23;21 beta,22 alpha-di-O-isopropylidene derivative. On the basis of this result, the structure of deacylgymnemic acid was elucidated as the 3-O-beta-glucuronide from the carbon-13 nuclear magnetic resonance spectra. Five antisweet principles, gymnemic acid-III, -IV, -V, -VIII, and -IX, were isolated in pure states from the hot water extract of leaves of Gymnema sylvestre. Of these, three (GA-III, -IV, and -V) were known, while two (GA-VIII and -IX) were new compounds. The structures of GA-VIII and -IX were elucidated as 3'-O-beta-D-arabino-2-hexulopyranosyl gymnemic acid-III and -IV, respectively.

Carbon Isotopes↗

PubMed1994

Triterpenoid saponins from Ardisia crenata and their inhibitory activity on cAMP phosphodiesterase.

Two novel triterpenoid saponins, ardisicrenoside C (1) [3 beta-O-(alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)- [beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)-16 alpha, 28-dihydroxy-olean-12-en-30-oic acid 30-O-beta-D-glucopyranosyl ester] and ardisicrenoside D (2) [3 beta-O-(beta-D-xylopyranosyl-(1-->2)- beta-D-glucopyranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L- arabinopyranosyl)-16 alpha, 28-dihydroxy-olean-12-en-30-oic acid 30-O-beta-D-glucopyranosyl ester] were isolated from the roots of Ardisia crenata. Structure assignments are based on spectroscopic data including 2D-NMR (correlation spectroscopy (COSY), homonuclear Hartmann-Hahn spectroscopy (HOHAHA), heteronuclear correlated spectroscopy (HETCOR), heteronuclear multiple bond correlation (HMBC) and rotating frame NOE spectroscopy (ROESY)) experiments and some chemical reactions. In addition, the isolated saponins along with their prosapogenins and sapogenins have been evaluated for their inhibitory activity on cAMP phosphodiesterase as a primary screening test for new medicinal compounds.

3',5'-Cyclic-AMP Phosphodiesterases↗

PubMed1999

Steroidal saponins from the bulbs of Allium karataviense.

Chemical examination of the bulbs of Allium karataviense led to the isolation of five new spirostanol saponins (7-11) and a new furostanol saponin (12), together with a known steroidal sapogenin (1) and five known saponins (2-6). The structures of the new saponins were determined by detailed analysis of their spectral data, including two-dimensional NMR spectroscopy. The steroidal saponins produced by A. karataviense, except for 5 and 6, were found to be based upon (25R)-5 alpha-spirostane-2 alpha,3 beta,5,6 beta-tetrol (alliogenin) and contain a beta-D-glucopyranosyl moiety with the formation of an O-glycoside linkage to C-2 of the polyhydroxylated steroidal skeleton as the common structural feature. The isolated compounds were evaluated for cytostatic activity against human promyelocytic leukemia HL-60 cells.

Allium↗

PubMed2000

Bioactive saponins and glycosides. XVII. Inhibitory effect on gastric emptying and accelerating effect on gastrointestinal transit of tea saponins: structures of assamsaponins F, G, H, I, and J from the seeds and leaves of the tea plant.

Following the investigation of assamsaponins A, B, C, D, and E, four new saponins termed assamsaponins F, G, H, and I were isolated from the seeds of the tea plant (Camellia sinensis L. var. assamica PIERRE), while assamsaponin J was isolated from its leaves. The structures of assamsaponins F-J were elucidated on the basis of chemical and physicochemical evidence and found to be 16,22-O-diacetyl-21-O-angeloyltheasapogenol E 3-O-[beta-D-galactopyranosyl (1-->2)][beta-D-glucopyranosyl(1 -->2)- alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, 21-O-angeloyl-22-O-acetyltheasapogenol E 3-O-[beta-D-galactopyranosyl(1--> 2)][beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]- beta-D-glucopyranosiduronic acid, 21-O-angeloyl-28-O-acetyltheasapogenol E 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-glucopyranosyl(1--> 2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, 21-O-tigloyl-28-O-acetyltheasapogenol E 3-O-[beta-D-galactopyranosyl(1--> 2)][beta-D-glucopyranosyl(1--> 2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, and 16,21-O-diacetyl-22-O-cinnamoyltheasapogenol B 3-O-[beta-D-galactopyranosyl(l-->2)][beta-D-rhamnopyranosy(1-->2)- alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, respectively. The saponin mixture from the seeds of the tea plant was found to exhibit an inhibitory effect on gastric emptying and an accelerating effect on gastrointestinal transit in mice. Theasaponin E1 the principle saponin of the tea plant, showed potent activity, while theasaponin E2 showed none, so that the position of the acyl groups in the sapogenin moiety is important from a pharmacological point of view.

Animals↗

PubMedDate not supplied

Suggested pharmacophagy of the African bushhopper Phymateus leprosus (Fabricius) (Pyrgomorphidae, Orthoptera).

The bushhopper Phymateus leprosus (Fabricius) in the field shows a special appetite for the milkweed Asclepias fruticosa. Asclepiadaceae, like Apocynaceae and Scrophulariaceae, contain cardiac glycosides. Raw and purified extracts of these plants phagostimulate larval and adult P. leprosus. We also screened natural and half-synthetic compounds found in those plant extracts. While saponins and sapogenins did not stimulate the animals, many cardiac glycosides and aglycones, offered on filter paper, proved to be phagostimulants.

Animals↗

PubMed1975

Chemico-pharmacological studies on saponins of Panax ginseng C. A. Meyer. I. Chemical part.

For the purpose of clarification of pharmacological actions of ginseng saponins we tried the isolation of ginseng saponins on a larger scale and succeeded in the isolation of eight saponins in a pure state and in sufficient amounts for the pharmacological assay. These eight saponins agreed all completely with the authentic samples of Shibata-Shoji and co-workers in molecular formula of saponins and sapogenins, sugars and TLC. The physical properties of saponins were shown. As other components of ginseng, there were isolated small amounts of panaxadiol, panaxatriol, daucosterol from the first running of column chromatography and mannitol, sucrose and glucose from the ethanol insoluble aqueous extract.

Chromatography, Thin Layer↗

PubMed2003

Ovine metabolism of diosgenin coated on cellulose in relation to hepatogenous photosensitization of ruminants.

Diosgenin (2.25 g) was coated onto cellulose and dosed daily to a lamb for 12 d by intraruminal intubation. Upon completion of dosing, samples of gut contents and internal organs were subjected to chemical analysis and histological examination. No clinical signs, changes in serum chemistry, or microscopic organ changes were observed. GC-MS analyses showed that in the rumen diosgenin was metabolised to free and, to a lesser extent, conjugated derivatives of tigogenin, smilagenin and epismilagenin. Reduction of diosgenin to smilagenin and tigogenin, and epimerization of smilagenin to epismilagenin, appeared to continue in the duodenum, ileum and jejunum. Deconjugation and the epimerization of smilagenin to epismilagenin appeared to continue in the cecum and colon. Epismilagenin was the dominant conjugated sapogenin constituent identified in a bile sample.

Administration, Oral↗

PubMed1976

Antibiotic action of beta-ursolic acid.

The antimicrobial action of beta-ursolic acid (triterpenoid sapogenin from the ursan group) has been studied. At the concentration of 300 mug/ml, this substance inhibited growth of all strains of staphylococci investigated. MIC for Gram-positive bacteria ranged between 50 and 500 mug/ml, and 100 to 800 mug/ml for Gram-negative bacteria and yeasts. Acquired resistance to beta-ursolic acid was transient.

Anti-Bacterial Agents↗

PubMed2005

Diosgenin, a plant steroid, induces apoptosis in COX-2 deficient K562 cells with activation of the p38 MAP kinase signalling and inhibition of NF-kappaB binding.

Diosgenin is a steroidal sapogenin with antitumor properties. We previously showed that diosgenin induced apoptosis in human erythroleukemia (HEL) cells. In order to elucidate the mechanism of its apoptotic activity, we investigated the effect of diosgenin on nuclear factor-kappaB (NF-kappaB) binding and on three groups of human mitogen-activated protein kinases (MAPKs) in relation to diosgenin-induced apoptosis in different erythroleukemia cell lines (K562 and HEL). Our results showed that diosgenin decreased DNA binding of NF-kappaB in K562 and HEL cells after 48-h diosgenin treatment. This inhibition of NF-kappaB binding was correlated with strong apoptosis in both erythroleukemia cell lines. Diosgenin-induced apoptosis was associated with cyclo-oxygenase-2 (COX-2) up-regulation in HEL cells but not in K562 cells which are COX-2 deficient. Furthermore, diosgenin inhibited extracellular signal-regulated kinase (ERK) activation only in HEL cells. However, diosgenin activated p38 MAPK in both cell lines and activated c-jun NH2-terminal kinases (JNKs) only in HEL cells. Pre-treatment with a selective p38 inhibitor inhibited diosgenin-induced DNA fragmentation in K562 cells. For the first time, our results suggest that inhibition of NF-kappaB nuclear binding and p38 MAPK activation are involved in the diosgenin-mediated signal cascades in K562 cells for inducing/regulating DNA fragmentation.

Apoptosis↗