[Microbiologic transformation of sterols and sapogenins].
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17-Ketosteroids↗
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Results for “SAPOGENINS”
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Steroidal sapogenins from Trigonella occulta.
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Plants, Medicinal↗
[The alkaloid and steroid sapogenin content of Solanum globiferum].
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Alkaloids↗
[Alkaloid and steroid-sapogenin content in Solanum umbellatum].
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Saponins↗
Metabolism of saponins from Narthecium ossifragum--a plant implicated in the aetiology of alveld, a hepatogenous photosensitization of sheep.
One sheep was dosed over 4 consecutive days with 2.1 kg of leaves and flower stems of Narthecium ossifragum before it was killed. Sarsasapogenin and smilagenin glycosides, in the ratio 9:1, were the dominant saponins present in the dosed plant material. GC-MS analyses of the free and conjugated sapogenin content of samples recovered from the sheep identified three distinct regions of metabolic activity. In the first metabolic region, in the rumen and omasum, the ingested plant saponins were hydrolysed to the parent sapogenins, before being oxidized at C-3 and reduced to give the epi analogues of the ingested sapogenins. The second metabolic region consisted of the duodenum, jejunum, the liver and associated ducts. Sapogenins appear to be absorbed in the jejunum and may be transported via the portal vein to the liver, where 3 alpha-OH-5 beta-H sapogenins (epismilagenin and episarsasapogenin), but not 3 beta-OH-5 alpha-H sapogenins (smilagenin and sarsasapogenin), are conjugated and excreted into the bile as episarsasapogenin and epismilagenin conjugates in the ratio 4:1. In the third metabolic region, in the caecum and the colon, the epi-sapogenin conjugates were hydrolysed to free epi-sapogenins. The absence of free and/or conjugated sapogenins in urine, collected 24 h after dosing commenced, indicates that saponins and their metabolites are not likely to be implicated in the kidney disease occurring in ruminants ingesting N. ossifragum.
Animals↗
Investigation of spectrophotometrically determined substances in Yucca extract by GC/MS, TLC and on-column injection GC.
Spectrophotometrically determined substances in Yucca extract, listed as "Yucca foam extract" in the "List of Existing Food Additives in Japan", were investigated by GC/MS, TLC and GC. A TLC method using an anisaldehyde color developing reagent similar to that employed in spectrophotometry was established for selective detection of sapogenins in Yucca extract. Several steroidal sapogenins were found by GC/MS in the fractions corresponding to spots on the TLC plate, and these were assumed to have contributed to the color development in spectrophotometry. Sarsasapogenin and smilagenin were the dominant sapogenins. An on-column injection GC method to determine these sapogenins in Yucca extract was also developed. The sum of these two sapogenins in Yucca extract was 0.9%. The total amount of sapogenin estimated by GC was approximately 2%, which was similar to that measured by spectrophotometry.
Chromatography, Gas↗
Effect of sarsasapogenin and its derivatives on the stimulus coupled responses of human neutrophils.
METHODS: The effects of three sapogenins (sarsasapogenin, tigogenin and hecogenin) on the stimulus-induced superoxide generation and protein tyrosyl phosphorylation in human neutrophils were investigated. RESULTS: When the cells were preincubated with sapogenin, three sapogenins dose-dependently suppressed the superoxide generations induced by N-formyl-methionyl-leucyl-phenylalanine (fMLP) and phorbol 12-myristate 13-acetate (PMA), respectively. In both cases, their effects were in the order: sarsasapogenin>tigogenin>hecogenin. While sarsasapogenin suppressed the superoxide generation induced by arachidonic acid (AA) as well, the superoxide generation was scarcely suppressed by tigogenin and significantly enhanced by hecogenin. In parallel to their effects on the superoxide generation, the three sapogenins dose-dependently suppressed the fMLP-induced and PMA-induced tyrosyl phosphorylations of 45 kDa protein in neutrophils, respectively. CONCLUSIONS: Of the sapogenins tested, sarsasapogenin may have the most clinical use as it suppresses superoxide generation.
Arachidonic Acid↗
Glucuronidation of amines and hydroxylated xenobiotics and endobiotics catalyzed by expressed human UGT1.4 protein.
Glucuronide conjugation of tertiary amine xenobiotics represents a unique and important metabolic pathway for these compounds in humans. In this study, we show that human UDP-glucuronosyltransferase 1.4 protein, stably expressed in human embryonic kidney 293 cells, catalyzes the N-glucuronidation of primary, secondary, and tertiary amine substrates. In addition, the substrate specificity of the expressed enzyme toward many hydroxylated and carboxylic acid-containing compounds was examined. Of the hydroxylated compounds tested, only sapogenins gave glucuronidation rates comparable with those observed for amine substrates. The apparent KM and Vmax values for sapogenins were such that the efficiency of glucuronidation (Vmax/KM) for these compounds was higher than that determined for amine substrates. Human UDP-glucuronosyltranferase 1.4 also catalyzes the glucuronidation of monoterpenoid alcohols and simple phenolic compounds. The enzyme kinetic values determined for these substrates suggested that this enzyme may have relatively limited significance for the conjugation of these classes of compounds. Of the endobiotics tested, androstanediol and progestins were glucuronidated at high rates by expressed human UDP-glucuronosyltransferase 1.4 protein. The glucuronidation efficiency for 5alpha-pregnane-3beta,20alpha-diol was comparable with that determined for the sapogenins. Because UDP-glucuronosyltransferases are integral membrane proteins, the effects of different detergents on the catalytic activity of the expressed enzyme were determined. The results show that detergents (such as Lubrol PX, Emulgen 911, and Triton X-100) are inhibitory for the quaternary ammonium-linked glucuronidation of chlorpromazine and imipramine catalyzed by expressed human UDP-glucuronosyltransferase 1.4. In contrast, CHAPS and nonanoyl-N-methylglucamide are less inhibitory toward the glucuronidation of these compounds. The results suggest that human UDP-glucuronosyltransferase 1.4 may be an important enzyme for the detoxication of environmentally derived amines and sapogenins and for the conjugation of progestins.
Antipsychotic Agents↗
Ovine metabolism of saponins: evaluation of a method for estimating the ovine uptake of steroidal saponins from Narthecium ossifragum.
A sheep was dosed three times per day over six consecutive days with 70 g Narthecium ossifragum, and once on the seventh day with 70 g N. ossifragum. Additionally, it was dosed once on days 1-7 with 20 mg of [20,23,23-2H3]sarsasapogenin. After 7 days, the sheep was killed and GC-MS analysis of the free and conjugated sapogenin content in bile, urine, rumen, duodenum, jejunum, colon and rectum samples collected from the sheep, faecal samples collected on days 4-7, and dosed plant material was performed. The N. ossifragum contained mainly sarsasapogenin and smilagenin. Only neglible levels of deuterium-labelled sarsasapogenins were detected in the samples from the animal. Ingested saponins were quickly hydrolysed in the rumen to free sapogenins and, in part, epimerized at C-3 to afford episapogenins. The absorption of free sapogenins appeared to occur in the jejunum. The concentration of sapogenins in faeces reached a plateau 108 h after dosing started.
Animals↗
Ruminal metabolism in sheep of saponins from Yucca schidigera.
Fifty-five mg per kg live weight of crystallized Yucca schidigera saponins, corresponding to 26 mg/kg live weight of sapogenins, was given daily intraruminally to two lambs for 11 consecutive days. Neither of the lambs showed any sign of toxicity throughout the experimental period. One lamb was killed 5 h after the last dose and GC-MS analysis of the free and conjugated sapogenin content samples of liver, and of the contents of the rumen, omasum, abomasum, duodenum, jejunum, ileum, colon and rectum, of faecal samples collected before dosing started, and of parts of the administered Yucca saponin were performed. The Yucca material contained mainly sarsasapogenin and smilagenin saponins. Ingested saponins were quickly hydrolysed in the rumen to free sapogenins and, in part, epimerized at C-3 to afford episapogenins. The absorption of free sapogenins appeared to occur in the jejunum. The metabolism of Yucca saponins was identical to that of Narthecium ossifragum saponins, and it is suggested that Yucca saponins could replace N. ossifragum saponins for toxicity studies on the latter plant.
Animals↗
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↗
Structure of a new echinocystic acid bisdesmoside isolated from Codonopsis lanceolata roots and the cytotoxic activity of prosapogenins.
We isolated a new saponin named codonoposide (1) from the roots of Codonopsis lanceolata (Campanulaceae) and characterized it as 3-O-[beta-D-xylopyranosyl(1-3)-beta-D-glucuronopyranosyl]-3beta,16alpha-dihydroxyolean-28-oic acid 28-O-[beta-D-xylopyranosyl (1-3)-alpha-L-rhamnopyranosyl (1-2)-alpha-L-arabinopyranosyl] ester by chemical, physicochemical, and 2DNMR techniques. Complete hydrolysis of 1 produced a sapogenin (1a), and the partial hydrolysis and further isolation afforded two prosapogenins (1b, 1c). The structures of 1a, 1b, and 1c were found to be 3beta,16alpha-dihydroxyolean-28-oic acid (echinocystic acid, 1a), 3-O-beta-D-glucuronopyranoside of 1a, and 3-O-beta-D-xylopyranosyl (1-3)-beta-D-glucuronopyranoside of 1a, respectively, on the basis of spectroscopic data. On MTT assay, 1a showed marginal cytotoxic activity whereas 1b exhibited more cytotoxicity than 1a. However, the bisdesmosylsaponin 1 exhibited no cytotoxicity (IC(50)>0.3 mM against tested cell lines). This result indicated that glycoside linkage of glucuronic acid at C-3 enhances the cytotoxicity of sapogenin (1a), and additive glycosylation of xylose to 1b strongly enhances the cytotoxicity of 3-O-monosaccharides (1b). Therefore, true forms of codonoposide for the cytotoxicity must be sapogenins or prosapogenins.
Carbohydrate Conformation↗
Analysis of ginsenosides by chromatography and mass spectrometry: release of 20 S-protopanaxadiol and 20 S-protopanaxatriol for quantitation.
To facilitate studies on the possible presence of ginseng products in serum, tissues, and excretions, a procedure to optimize the analysis of the ginseng specific products, i.e., ginsenosides, had to be worked out. With the present method the two sapogenins, 20S-protopanaxadiol and 20S-protopanaxatriol, can be produced from ginsenosides Rb1, Rc, Rd, Re, and Rg1 in 80% yield by using an improved alkaline cleavage procedure. In contrast to previously described acid hydrolysis procedures for ginsenosides, our alkaline conditions caused no epimerization, no hydroxylation, and no cyclization of the side chain. Furthermore, no unchanged ginsenosides were recovered. The products of alkaline and acidic cleavage were separated, identified, and characterized by GC, GC-MS, and HPLC. In contrast to alkaline cleavage, treatment with acid afforded a number of side products. The C-20S-epimers of the ginseng sapogenins could be distinguished from C-20R epimers by difference in mass spectra and retention time after trimethylsilylation.
Chromatography, Gas↗
Hemolysis caused by polyoxyethylene-derived surfactants. Evidence for peroxide participation.
The hemolytic properties of nonionic surfactants of the series CH3(CH2)15-17-O-(CH2CH2O)nCH2CH2OH were investigated and compared to those of saponins, sapogenins and H2O2. Antioxidants and anaerobic conditions were shown to inhibit the hemolysis, while glycyrrhizin was found to enhance it. Similar effects were obtained for H2O2 hemolysis, but not for saponin and sapogenin hemolysis. It is proposed that peroxides and free radicals are mainly responsible for the polyoxyethylene derived surfactants induced hemolysis.
Animals↗
Antiprotozoal compounds from Asparagus africanus.
Two antiprotozoal compounds have been isolated from the roots of Asparagus africanus Lam. (Liliaceae), a new sapogenin, 2 beta, 12 alpha-dihydroxy-(25R)-spirosta-4,7-dien-3-one (1), which was named muzanzagenin, and the lignan (+)-nyasol (2), (Z)-(+)-4,4'-(3-ethenyl-1-propene-1,3-diyl)-bisphenol. The structure of the sapogenin was elucidated by MS and by 1D and 2D NMR methods and established by a single crystal X-ray analysis. (+)-Nyasol potently inhibits the growth of Leishmania major promastigotes, the IC50 being 12 microM, and moderately inhibits Plasmodium falciparum schizonts with the IC50 49 microM. These concentrations only moderately affect the proliferation of human lymphocytes. Muzanzagenin showed a moderate in vitro activity in all three tests, the IC50 against leishmania promastigotes was 70 microM, and against four different malaria schizont strains the IC50 values were 16, 163, 23, and 16 microM, respectively.
Animals↗
Phytochemical analysis and anti-allergic study of Agave intermixta Trel. and Cissus sicyoides L.
Agave intermixta Trel. (Maguey) and Cissus sicyoides L. (Bejuco caro) are Caribbean plant species from the Dominican Republic used locally in traditional popular medicine that have shown an antiinflammatory effect in experimental animal models. A phytochemical analysis on these species allowed us the isolation and identification of the steroidal sapogenins hecogenin and diosgenin from Maguey and the hydroxystilbene resveratrol from Bejuco caro. The effects of these plant extracts and their isolated constituents on compound-48/80-induced histamine release from peritoneal mast cells were investigated. Significant inhibition was produced by 0.5 mg mL(-1) of a methanolic extract of Bejuco (41.1%) and by its constituent resveratrol (82.4%) at a dose of 250 microM. However, none of the steroidal sapogenins from A. intermixta showed a significant inhibitory effect on histamine release from mast cells. From these results, it can be deduced that the in-vitro anti-allergic activity towards the release of histamine from mast cells shown by the methanolic extract of C. sicyoides may be mediated by its constituent resveratrol and might contribute to the antiinflammatory activity shown by this species.
Agave↗
Low temperature crystal structure of natural diosgenone.
The molecular structure of diosgenone, a natural steroidal sapogenin, closely related to diosgenin and isolated from Solanum nudum, was solved by single crystal X-ray diffractometry at 120 K and refined by full-matrix least-squares to an agreement factor, R1 = 0.054. It crystallizes in the monoclinic space group P2(1), with a = 15.1870(4) A, b = 7.2710(2) A, c = 21.2840(6) A, beta = 99.251(1) degrees, and four molecules in the unit cell (Z = 4). The results constitute the first structural report on a steroidal sapogenin from the diosgenin group.
Crystallography, X-Ray↗
[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↗