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PubMed1988

Comparison of the chromatographic properties of sterols, select additional steroids and triterpenoids: gravity-flow column liquid chromatography, thin-layer chromatography, gas-liquid chromatography and high-performance liquid chromatography.

The chromatographic properties of approximately 100 sterols, select steroids of plant origin (sapogenins and steroidal alkaloids) and triterpenoids has been evaluated in this laboratory by monitoring their elution characteristics in adsorption (gravity column and thin-layer methods with and without the addition of silver nitrates), gas and reversed-phase high-performance liquid chromatography. The utility of each methodology to act in one or another chromatographic mode-separation, radio-chemical purification, quantitation and structural elucidation, is discussed. The importance of the tilt of the -OH group at C-3 as well as the polarity, size, an shape of the rest of the molecule as it effects the hydrogen-bonding ability of the -OH group is demonstrated through changes in chromatographic behavior that result from the step-wise introduction of double bonds, methyl, bromo, oxygen, nitrogen and cyclopropyl groups into 5 alpha-cholestanol. An independent aid in the structure identification and quantitation of the compounds was use of a multiple-wavelength diode array detector in which different wavelengths of the UV spectrum (200-400 nm) were simultaneously monitored following passage of the sample through a reversed-phase C18 column.

Chromatography, Gas↗

PubMed1994

Cardioactive steroid saponins and other constituents from the aerial parts of Tribulus cistoides.

From the petrol extract of the aerial parts of Tribulus cistoides three steroid sapogenins and two N-acyltyramines were isolated, whereas the methanolic extract gave nine steroid saponins, among them the cardioactive cistocardin, saponin-3, saponin-4 and saponin-7. Furthermore, a furostanol diglycoside was isolated besides 5'-(hydroxysulphonyloxy) jasmonic acid, D-(+)-pinitol and sucrose. The structures were established by spectroscopic investigations of the isolated compounds and their hydrolysis products. 5'-(Hydroxysulphonyloxy) jasmonic acid has been prepared by partial synthesis.

Animals↗

PubMed1998

Enzymatic hydrolysis of the cytotoxic triterpenoid glycoside virgaureasaponin 1.

The cytotoxic compound, virgaureasaponin 1, was converted using several optimized enzymecatalysed hydrolyses to the 28-O-beta-D-xylopyranosyl (1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (2), and the 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L- rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (3) and 28-O-beta-D-xylyopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2) - beta-D-fucopyranoside (4) both lacking the glucose moiety at C-3 of the aglycone. The terminal rhamnose of the acylglycosidic bonded tetrasaccharide was cleaved by naringinase to give compound 2. The new acylglycosides 3 and 4 were obtained with the help of a relatively crude beta-glucuronidase preparation, but the cleavage of the sapogenin bonded glucose was impossible using several beta-glucosidase preparations directly. These derivatives were used for the investigation of the relationship between the saponin carbohydrate structure and their cytotoxic activity.

Animals↗

PubMed2000

Triterpenoid glycosides and a triterpene from Ilex brevicuspis.

Two saponins and a sapogenin were isolated from the leaves of Ilex brevicuspis. Their structures were established by means of spectroscopic methods as brevicuspisaponin 1 (3-O-alpha-L-arabinopyranosyl-20(S)-19 alpha,24-dihydroxyursolic acid), brevicuspisaponin 2 (3-O-alpha-L-arabinopyranosyl-20(S)-19 alpha,23,24-trihydroxyursolic acid) and 23-methylester of 20(S)-3 beta,19 alpha,24-trihydroxyurs-12-en-23,28-dioic acid.

Glycosides↗

PubMed2000

Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides.

Naturally occurring saponins 3 and 4 have a normal type F ring and alpha-arranged CH(3)-21 group. Treatments of pseudosaponin peracetates 18 and 19 derived from 3 and 4, respectively, with alcoholic KOH, followed by acidification with acetic acid, gave spirostanols 20 and 22 having iso type F rings as major products. Structural analyses of sapogenins and saponins derived from pseudo derivatives 11, 12, 18 and 19 were performed by comparisons of their 1H-NMR spectral data and the X-ray analytical data of 3-O-p-bromobenzoyl sarsasapogenin 7, 3-O-acetyl diosgenin 13 and saponin 20. The mechanisms of ring-closure reaction of the side chain at C-22 of pseudosapogenins and pseudosaponins were deduced using stereomodels of the spirostanols derived from 11 under various reaction conditions. Inhibitory activities of saponin diglycosides 3, 4, 20, 21 and 25 on human platelet agglutinations induced by ADP and ristocetin were compared.

Adenosine Diphosphate↗

PubMed1997

Haemolytic activities of plant saponins and adjuvants. Effect of Periandra mediterranea saponin on the humoral response to the FML antigen of Leishmania donovani.

An 87.7% (P < 0.01) and 84% (P < 0.001) of protection against visceral leishmaniasis was achieved in CB hamsters and Balb/c mice, respectively, with saponin combined to the fucose-mannose ligand of Leishmania donovani (FML). However, an undesirable haemolytic effect was described for several saponins. Aiming to improve the formulation with FML/saponin, we comparatively analysed the haemolytic potential of recently characterized plant saponins and currently used adjuvants. The haemolytic activity of steroidic saponins from Agave sisalana; Smilax officinalis as well as commercial saponin (Riedel De Haën's), was higher than that of triterpenoid ones (Bredemeyera floribunda; Periandra mediterranea) and the Freund's complete adjuvant. The concentration resulting in 50% haemolysis was 500 micrograms ml-1 for aluminum hydroxide. The low haemolytic effect of P. mediterranea saponin was abolished by removal of its glycidic moiety and its sapogenin fraction as well as the Freund's Incomplete Adjuvant were non-haemolytic within this range. Furthermore, the adjuvant effect of three doses of P. mediterranea saponin injected with the FML antigen of L. donovani, was assayed in mice, either by the intraperitoneal (i.p.) or the subcutaneous (s.c.) route. The anti-FML IgG antibody levels increased and detectable levels were observed up to 3 months in the s.c. group. The response was expanded in both groups after an injection with a fourth vaccine dose. The IgG response showed increased levels of IgG2a only in the i.p. group, while IgG2b and IgG1 but not IgG3 antibodies were higher than controls in both groups. In conclusion, the results suggest that the recently described triterpenoid fractions of P. mediterranea can be safely used as adjuvant with low or non-haemolytic effect.

Adjuvants, Immunologic↗

PubMed2000

Cytotoxic saponins from bulbs of Allium porrum L.

An extensive phytochemical analysis of the saponin content has been undertaken on leek, Allium porrum L., sown and collected at different seasons. As a result of this investigation, eight saponins (1-8) have been isolated, four of them (5-8) being novel compounds. Compounds 5 and 6, possessing the same tetrasaccharide moiety of compounds 1 and 3, display very unusual spirostane aglycones, 12-ketoporrigenin and 2,12-diketoporrigenin (named porrigenin C), respectively, recently isolated for the first time as free sapogenin in the same plant. Compounds 7 and 8 are rare cholestane bidesmosides possessing a di- and trisaccharide residues linked to a polyhydroxycholesterol aglycone, respectively. The structures of the isolated compounds have been determined by nondegradative spectroscopic analysis, mainly based on NMR. All the eight saponins isolated from leek were tested for their cytotoxic activity against two different cell lines in vitro, and compounds 1, 2, and 6 resulted particularly active.

Allium↗

PubMed2002

Variation in diosgenin levels among 10 accessions of fenugreek seeds produced in western Canada.

A collection of 10 accessions of fenugreek (Trigonella foenum-graecum L.), an annual legume, was grown during two summers at three plot locations in western Canada to assess whether genetic (accession) and environmental factors (site and year of production) influenced levels of diosgenin, a steroidal sapogenin. The 60 harvested seed samples, each analyzed by single determinations on three subsamples of defatted and dried seed material, were hydrolyzed by a microscale procedure in water containing 2-propanol (70%) and sulfuric acid (1 M). The extracts were analyzed by capillary gas chromatography with 6-methyldiosgenin as internal standard. Diosgenin levels from mature seeds ranged from 0.28 to 0.92% (28-92 microg/10 mg). Analysis of variance on combined diosgenin levels from the three sites and two years revealed that accession, accession x year, and site x year effects were significant for diosgenin content, whereas site, year, and site x accession effects were not. Four accessions, CN 19062, CN 19067, CN 19070, and CN 19071, were identified with high levels of diosgenin on the basis of the 2-year data set. In these accessions, mean levels of diosgenin plus yamogenin from seven site years were estimated at 0.70, 0.98, 0.84, and 0.87%, respectively.

2-Propanol↗

PubMed2005

The impact of saponins or saponin-containing plant materials on ruminant production--a review.

Saponins are steroid or triterpene glycoside compounds found in a variety of plants. Some saponin-containing plants, mainly legumes, have been used as animal feed, but others are toxic. Several studies on the effect of saponins on ruminant production have also been reported. Some in vitro and in vivo experiments that demonstrate the beneficial effects of saponin such as defaunation of the rumen and manipulation of the end products of fermentation are described. Defaunation is the selective removal of protozoa from the rumen microbial ecosystem by a cell membrane cholesterol-saponin interaction, which causes cell rupture. Because protozoa in the rumen cause protein turnover by predating on bacteria, defaunation increases the nitrogen utilization of the ruminant and may lead to an increase in growth, milk, or wool production. The growth-promoting effect was evident in the high roughage diet suggesting that the application of saponins or saponin-containing plant materials may be beneficial for the subsistence farmers in developing countries. Saponins are deglycosylated by rumen microbes. Some sapogenins have been detected in the digestive tract of ruminants; however, the direct action of these compounds on the host animal is still unclear. No information on the effects of saponin on ruminant reproduction is available. There is an urgent need for a systematic evaluation of the most active structural components of the saponins, and their interaction with the microbial community, the host animal, and the diet. Along with these studies, the direct effects of saponins or their microbial degradation products on the host must be examined in order to get the full understanding of the metabolism and beneficial effects of saponins on animals.

Animals↗

PubMed2005

Triterpenoid glycosides from leaves of Medicago arborea L.

Eighteen triterpene saponins (1-18) from Medicago arborea leaves have been isolated and their structures elucidated by spectroscopic, spectrometric (1D and 2D NMR, FAB-MS, ESI-MS/MS), and chemical methods. They have been identified as glycosides of medicagenic, zanhic, and 2beta-hydroxyoleanolic acids, soyasapogenol B, bayogenin, and 2beta,3beta-dihydroxyolean-12-en-23-al-28-oic acid. Twelve of them, identified as 3-O-beta-D-glucopyranosyl-28-O-[alpha-L-arabinopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside] zanhic acid (3), 3-O-beta-D-glucopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside] zanhic acid (4), 3-O-[alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->2)-beta-D-glucopyranosyl]-2beta-hydroxyoleanolic acid (5), 3-O-beta-D-glucuronopyranosyl-28-O-[alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]medicagenic acid (6), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]bayogenin (9), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]-2beta,3beta-dihydroxyolean-12-en-23-al-28-oic acid (10), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]zanhic acid (12), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-[alpha-L-arabinopyranoside(1-->3)]-alpha-L-rhamnopyrano-syl(1-->2)-alpha-L-arabinopyranoside]zanhic acid (13), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyrano-syl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]zanhic acid (14), 3-O-[alpha-L-arabinopyranosyl-(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl]-28-O-[beta-D-xylopyranosyl(1-->4)-[beta-D-apiofurano-syl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]zanhic acid (16), 3-O-[beta-D-glucopyrano-syl(1-->2)-beta-D-glucopyranosyl]-28-O-[beta-D-xylopyranosyl(1-->4)-[alpha-L-arabinopyranosyl(1-->3)]-alpha-L-rhamno-pyranosyl (1-->2)-alpha-L-arabinopyranoside]zanhic acid (17), and 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyrano-side]medicagenic acid (18), are reported as new natural compounds. The presence of the aldehydic group on the sapogenin moiety of saponin 10 is discussed in the framework of a possible elucidation of the biosynthesis of these metabolites.

Carbohydrates↗

PubMed1998

Alfalfa Saponins and Their Implication in Animal Nutrition.

Alfalfa (Medicago sativa L.) is of immense importance as livestock fodder for both developed and lesser developed countries as it contains a high amount of protein, and yield of dry matter is also very high. The main antinutritional components present in this plant are saponins, and their unfavorable effects on animal performance have restricted the optimum use of this high-protein plant as an animal feed. The occurrence, chemistry, analysis, and consequences of intake of alfalfa saponins are reviewed. The information synthesized may lead to planning of more detailed studies on isolation and characterization of saponins and sapogenins to gain a better understanding of the biological activities of the aglycon and carbohydrate moieties of saponins.

Journal Article↗

PubMed1999

Studies on the constituents of Gliricidia sepium (Leguminosae) leaves and roots: isolation and structure elucidation of new triterpenoid saponins and aromatic compounds.

Our research program on the Central American fooder plant Gliricidia sepium led to the discovery of two new triterpene saponins (1 and 2) and known aromatic compounds. The new compounds possess 3beta,21beta, 24-trihydroxy-22-oxoolean-12-ene as an aglycon. The oligosaccharide moiety linked to C-3 of the aglycon contained two pyranoses (glucuronic acid and xylose); in addition the glucose residue of both 1 and 2 is also linked to C-21. Structure elucidation of these new compounds through the extensive use of 1D and 2D NMR techniques have provided detailed information about the sapogenin and the saccharide chains, inclusive of sugar sequence and the position of glycosylation.

Central America↗

PubMed2002

An assisted solvolysis of 23-spirostanyl bromides and tosylates. A new rearrangement of spirostanes to the bisfuran systems.

Steroidal sapogenins bearing a good leaving group at C23 undergo a completely stereospecific rearrangement under a variety of conditions via a mechanism involving neighboring-group participation by the acetal oxygen atom in the departure of the nucleofuge from C23. The reactions of equatorial (23S)-23-bromo- or (23S)-23-tosyloxyspirostanes with either the alpha (25R) or beta (25S) oriented 25-methyl group lead to the bisfuran products with inversion of configuration at C23. The reactions of the starting compounds with axial substituents (23R) at C23 require drastic conditions and result in the formation of the corresponding olefin accompanied by the rearranged product (in the case of the 25S isomer only).

Combinatorial Chemistry Techniques↗

PubMed2001

Triterpene saponins from Vietnamese ginseng (Panax vietnamensis) and their hepatocytoprotective activity.

The methanol extract of Vietnamese ginseng (Panax vietnamensis) was found to possess hepatocytoprotective effects on D-galactosamine (D-GalN)/tumor necrosis factor-alpha (TNF-alpha)-induced cell death in primary cultured mouse hepatocytes. Further chemical investigation of the extract afforded two new dammarane-type triterpene saponins, ginsenoside Rh(5) (1) and vina-ginsenoside R(25) (2), as well as eight known dammarane-type triterpene saponins, majonoside R(2) (3), pseudo-ginsenoside RT(4) (4), vina-ginsenosides R(1) (5), R(2) (6), and R(10) (7), ginsenosides Rg(1) (8), Rh(1) (9), and Rh(4) (10), and a known sapogenin protopanaxatriol oxide II (11). Their structures were elucidated on the basis of spectral analysis. In addition, by the using LC-electrospray ionization (ESI)-MS method, five known saponins, ginsenosides Rb(1), Rb(2), Rc, Rd, and Re (12--16), were also identified in the extract. Among the compounds isolated, majonoside R(2) (3), the main saponin in Vietnamese ginseng, showed strong protective activity against D-GalN/TNF-alpha-induced cell death in primary cultured mouse hepatocytes. This demonstrates that the hepatocytoprotective effect of Vietnamese ginseng is due to dammarane-type triterpene saponins that have an ocotillol-type side chain, a characteristic constituent of Vietnamese ginseng.

Animals↗

PubMed2004

Comparative study on triterpene saponins of Ginseng drugs.

A comparative study on the triterpene saponins of 47 samples of Ginseng drugs derived from 12 Panax taxa was conducted using a reverse-phase high-performance liquid chromatography (HPLC)method. Eleven ginsenosides, which represent 4 types of typical sapogenins, were chosen as standards for quantitative determination in order to characterize the chemical constituent pattern of each Ginseng drug and investigate the relationship between genetic varieties and chemical constituent pattern. The results showed that the ginsenoside compositions in Ginseng drugs of different origins were of considerable variability. Total saponin contents varied by 10-fold from the highest drug to the lowest one. Chikusetsu-ninjin derived from P. japonicus (Japan) was found to have the highest content (192.80 - 296.18 mg/g) and Ginseng from P. ginseng to be the lowest (5.78 - 15.63 mg/g). Two main groups (I and II) suggested by phytochemical data were clearly observed; group I mainly containing dammarane saponins consisted of P. ginseng, P. quinquefolius, P. notoginseng, P. vietnamensis and P. vietnamensis var. fuscidiscus; and group II containing a large amount of oleanolic acid saponins was com-posed of P.japonicus (apan), P. zingiberensis, P.japonicus (China),P. japonicus var. angustifolius, P. japonicus var. major, P. japonicus var. bipinnatifidus and P. stipuleanatus. The ratios of the subtotal of dammarane saponins to that of oleanolic acid saponins (D/0) were found to be > 1.9 and < 0.25 for groups I and II, respectively. The drug samples derived from the same botanical origin revealed similar constituent patterns, in other words, each Panaxtaxon showed its own characteristic chromatographic profile,which appeared in the specific shape of an 11-direction radar graph constructed on the basis of the result of quantitative analysis. Similarities of chemical constitution were seen among the closely phylogenetically-related taxa, including P. ginseng and P.quinquefolius, P. vietnamensis and P. vietnamensis var.fuscidiscus,P. japonicus (China) and its varieties were demonstrated, except P. japonicus (Japan) and P. zingiberensis.

Chromatography, High Pressure Liquid↗

PubMed2005

Structure-activity relationships for saponins from Allium hirtifolium and Allium elburzense and their antispasmodic activity.

A phytochemical study of Allium hirtifolium Boiss flowers has led to the isolation of high amounts of six new furostanol and spirostanol saponins, named hirtifoliosides A1/A2 (1a/ 1b), B (2), C1/C2 ( 3a/ 3b), and D(4) along with three known spirostanol saponins, alliogenin 3- O-beta-D-glucopyranoside, gitogenin 3- O-beta-D-glucopyranosyl-(1-->4)- O-beta-D-glucopyranoside, and agapanthagenin 3- O-beta-D-glucopyranoside. High concentrations of the following known flavonol glycosides have been isolated from both flowers and bulbs: kaempferol 3- O-beta-D-rhamnopyranosyl-(1-->2)-glucopyranoside, kaempferol 3- O-beta-D-glucopyranosyl-(1-->4)-glucopyranoside, kaempferol 3-O-glucopyranoside, kaempferol 7-O-glucopyranoside. The isolated saponins along with the four saponins elburzensosides A1/A2 and C1/C2 and the sapogenin agapanthagenin, previously described from A. elburzense, have been subjected to biological assays for evaluating possible antispasmodic activity in the guinea-pig isolated ileum. The obtained results served as a basis for the establishment of structure-activity relationships within this class of antispasmodic agents. They highlight the positive effects of a hydroxyl group at position 5 and of a glucose unit at position 26 and demonstrate the detrimental effects of both a hydroxyl group at position 6 and of a glucose unit at position 3. Among the tested compounds, elburzensosides C1/C2 and agapanthagenin showed the highest activity in reducing induced contractions as measured by the reduction of histamine release by about 50 %. The observed effect therefore contributes to the explanation of the traditional use of onion and garlic in the treatment of disturbances of the gastrointestinal tract.

Allium↗

PubMed1991

Glyyunnansapogenins G and H: Two New Pentacyclic Triterpenoids of the 18alphaH-Oleana-9(11),12-diene Type from Glycyrrhiza yunnanensis Roots.

Two new pentacyclic triterpenoid sapogenins of the 18alpha H-oleana-9(11),12-diene type named glyyunnansapogenins G and H were isolated from the roots of GLYCYRRHIZA YUNNANENSIS Cheng f. et L. K. Tai. Their structures were elucidated as 18alpha H-oleana-9(11),12-diene-3beta,21alpha,29-triol and 18alpha H-3beta,21alpha-dihydroxyoleana-9(11),12-dien-29-oic acid, respectively, by spectroscopic methods. This is the first report of the occurrence of the 18alpha H series of oleana-9(11),12-diene compounds in nature.

Journal Article↗

PubMed2004

Antimicrobial properties of plant secondary metabolites.

Increasing awareness of hazards associated with the use of antibiotic and chemical feed additives has accelerated investigations into plants and their extracts as feed additives. The present review mainly discusses two classes of plant secondary compounds in this context, i.e. essential oils and saponins. The broader potential of plants and their extracts is illustrated by the progress of an EC Framework 5 project, 'Rumen-up'. Dietary inclusion of a commercial blend of essential oils causes markedly decreased NH3 production from amino acids in rumen fluid taken from sheep and cattle. This effect is mediated partly by the effects on hyper-NH3-producing bacteria and the protein- and starch-fermenting rumen bacterium, Ruminobacter amylophilus. Saponin-containing plants and their extracts suppress the bacteriolytic activity of rumen ciliate protozoa and thereby enhance total microbial protein flow from the rumen. The effects of some saponins are transient, because saponins are hydrolysed by bacteria to their corresponding sapogenin aglycones, which are much less toxic to protozoa. Saponins also have selective antibacterial effects that may prove useful in, for example, controlling starch digestion. The 'Rumen-up' project began with a targetted collection of European plants and their extracts, which partners have tested for their effects on rumen proteolysis, protozoa, methanogenesis and lactate production. A success rate of about 5% in terms of positive hits illustrates that plant secondary compounds, of which essential oils and saponins comprise a small proportion, have great potential as 'natural' manipulators of rumen fermentation to benefit the farmer and the environment in the future.

Ammonia↗