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The study was aimed to estimate the effect of plant secondary metabolites present in ruminants diet and phytogenic feed additives on liver microsomal metabolism of albendazole and fenbendazole. The selected phytocompounds comprised of flavonoids (apigenin, quercetin) and saponins (hederagenin, medicagenic acid). The experiments were performed on liver microsomal fraction obtained from routinely slaughtered cows. The intensity of albendazole and fenbendazole metabolism in the presence of flavonoids and saponins was analyzed in equimolar concentration (100 μM). The obtained results revealed that both flavonoids and saponins intensify the metabolism of albendazole and fenbendazole in bovine microsomes. In the case of albendazole, apigenin and quercetin doubled the amount of degraded drug and the amount of produced albendazole sulfoxide. Additionally, both flavonoids increased the amount of produced albendazole sulfone. Saponins, hederagenin, and medicagenic acid intensified the degradation of albendazole (1.8-fold) and the production of albendazole sulfoxide (twofold). Medicagenic acid inhibited the production of albendazole sulfone. In the case of fenbendazole, the degradation of the drug and the production of oxfendazole were increased four and five times in the presence of saponins and flavonoids, respectively. The enhancement of benzimidazoles' metabolism caused by the studied plant metabolites could change pharmacokinetics and the efficacy of benzimidazoles' treatment in cattle.

Bioactive natural products were firstly obtained from biogas slurry. Three new 29 carbon skeletons of the pentacyclic triterpenoid compounds 24-norolean-12-ene-3,22-dione (1), 3β-hydroxy-24-norolean-12-ene-22-one (2), 3α-hydroxy-24-norolean-12-ene-22-one (3), as well as one known compound S-equol (4) were isolated and purified from the MeOH extract of chicken manure biogas slurry. The molecular structures of the four compounds were elucidated based on the extensive spectroscopic data analysis, and the structure of Compound 1 was further confirmed by single-crystal X-ray diffraction. The structures of Compounds 1, 2, and 3 are similar with oleanolicum and hederagenin that has excellent anti-tumor activities. The cytotoxicity against five cancer cell lines (Hela, A549, MCF7, PC3, and B16) of Compounds 1–4 was tested. Similar to Compound 4 (S-equol), Compounds 1–3 (pentacyclic triterpenoids) showed cytotoxicity activity against different tumor cell lines. Compounds 1–3 showed slightly lower cytotoxicity activities than Compound 4. The IC50 of Compound 4 was determined to be 9.7–27.6 μM, while the IC50 values of 1–3 were 17.6–65.3 μM. There are no significant differences in the cytotoxicity capacities between Compounds 1, 2, and 3.

Three new oleanane-type glycosides, 1-3, were isolated from the whole plant of Tremastelma palaestinum (L.) Janchen, along with eight known triterpene glycosides. The structures of the new compounds were established as 3-O-[β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]hederagenin (1), 3-O-[β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]hederagenin 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester (2), and 3-O-[α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]oleanolic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester (3) by using 1D- and 2D-NMR techniques and mass spectrometry. This is the first report on the phytochemical investigation of a species belonging to Tremastelma genus.

The four hederagenin glycosides 1–4 were efficiently synthesized through one-pot sequential glycosylations with glycose 1-(trichloroacetimidate)s as donors, resulting in a significantly simplified synthetic procedure without isolation of glycosylation intermediates. The activity of the synthetic hederagenin glycosides 1–4 against α-glucosidase type IV was evaluated; hederagenin glycoside 4 containing an α-L-rhamnopyranosyl unit showed the best activity with an IC50 value of 47.9 μM.

BACKGROUND: Spotted medic [Medicago arabica (L.) Huds.] is a minor forage species containing saponins which are reported to be biologically active. This study assessed the concentration and composition pattern of spotted medic saponins during the growing season and at senescence. The pattern of saponins was based on identification and quantification of their constituent sapogenins. At senescence, individual saponin concentrations of aerial and subterranean plant organs were also determined. RESULTS: Leaf total saponin content did not vary during the growing season and decreased remarkably at senescence. Seven sapogenins were identified and quantified during the season, bayogenin and hederagenin being the most abundant ones throughout. Total saponin content varied among plant organs at senescence, with the highest concentration in roots. A variable number of saponins from one (in seeds) to 19 (in leaves) were quantified. A clear relationship between leaf concentrations of sapogenins and those of their derivative saponins was revealed by correlation analysis. CONCLUSION: The species displayed a sapogenins/saponins pattern markedly different from those of other perennial or annual Medicago species. Saponins of queretaroic acid and 2β-hydroxy queretaroic acid had no precedent in the Leguminosae. The high concentration of biologically active hederagenin suggested further assessment of possible effects on feeding animals. Copyright © 2010 Society of Chemical Industry

A hydrophilic interaction chromatography (HILIC) and reverse-phase liquid chromatography (RPLC) coupled with electrospray TOF MS method was developed for the analysis and characterization of constituents in the radix of Cyathula officinalis Kuan. Separation parameters of HILIC such as buffer pH, mobile phase strength, and organic modifier were evaluated. Fructose, glucose, and sucrose were identified by HILIC-ESI/TOF MS. Reverse-phase liquid chromatography-ESI/TOF MS were applied for quick and sensitive identification of major saponins in Cyathula officinalis. In-source collision-induced dissociation has been performed to elucidate the fragmentation pathways of oleanane-, hederagenin-, and gypsogmin-type saponins. Twelve saponins were characterized in this plant for the first time, and four of them were presumed to be new compounds. In addition, one phytoecdysteroid (cyasterone) and one coumarin (6,7-dimethoxycoumarin) were detected at the same time. The present method was capable of rapid characterizing and providing structure information of constituents from herbal drugs.

Triterpene saponins are a group of bioactive compounds abundant in the genus Medicago, and have been studied extensively for their biological and pharmacological properties. In this article, we evaluated the effects of the ectopic expression of AsOXA1 cDNA from Aster sedifolius on the production of triterpene saponins in barrel medic (Medicago truncatula Gaertn.). AsOXA1 cDNA encodes beta-amyrin synthase, a key enzyme involved in triterpene saponin biosynthesis. One of the four transgenic lines expressing AsOXA1 accumulated significantly larger amounts of some triterpenic compounds in leaf and root than did control plants. In particular, the leaf exhibited significantly higher levels of bayogenin, medicagenic acid and zanhic acid. The amounts of medicagenic acid and zanhic acid, which represent the core of the M. truncatula leaf saponins, were 1.7 and 2.1 times higher, respectively, than the amounts extracted from the control line. In root, the production of bayogenin, hederagenin, soyasapogenol E and 2beta-hydroxyoleanolic acid was increased significantly. The increase in the total amounts of triterpenic compounds observed in the leaves of transgenic lines correlated with the AsOXA1 expression level. Interestingly, the plants expressing AsOXA1 showed, under different growth conditions, improved nodulation when compared with the control line. Nodulation enhancement was also accompanied by a significant change in the soyasapogenol B content. Our results indicate that the ectopic expression of AsOXA1 in barrel medic leads to a greater accumulation of triterpene saponins and enhanced root nodulation.

AIM: To study the chemical constituents from the leaves of Ilex pernyi. METHODS: The chemical constituents were isolated by various column chromatographic methods and their structures were identified by spectral data together with physicochemical analysis. RESULTS Nine known compounds were isolated and identified as 2α 3β, 23-trihydroxyurs-12-en-28-oic acid β-D-glucopyranosyl ester (1), hederagenin 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranoside (2), hederagenin 3-O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranoside (3), hederagenin 3-O-β-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside (4), 3-O-β-D-glucopyranosyl-23-hydroxyursolic acid (5), chikusetsusaponin Ⅳa (6), 3β-23-dihydroxy-urs-12-en-28-oic acid 3-O-β-D-glucuronopyranoside 6'-O-methyl ester (7), ilexoside XXXVII (8), 3-O-β-D-glucuronopyranosyl-2α, 3β 23-trihydroxyurs-12-en-28-oic acid β-D-glucopyranosyl ester (9). CONCLUSION: The nine compounds were isolated from this plant for the first time.

Two new triterpenoid saponins, hederagenin 3-O-α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranoside named akeboside La (compound 1), oleanolic acid 3-O-α-L-arabinopyranosyl-(1→2)-β-D-glucopyranoside named akeboside Lb (compound 2), along with five known saponins, oleanolic acid 3-O-α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranoside (compound 3), hederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (compound 4), oleanolic acid 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (compound 5),3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-α-Dglucopyranosyl-(1→6)-β-D-glucopyranoside (compound 6), 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (compound 7) were isolated from the n-butanol part of the 80% ethanol extracts of the dried stems of Akebia quinata (Thunb.) Decne.Compound 5 was isolated from plants of genus Akebia for the first time. The structures were elucidated on the basis of physicochemical properties and spectral data.

To investigate saponins from the roots of Pulsatilla cernua (Thunb.) Bercht. et Opiz., two new compounds together with five known triterpenoid saponins were isolated. The structures of the two new triterpenoid saponins, named cernuasides A and B, were elucidated as 3-O-[p-β-D-xylopyranosyl(12)]-[α-L-rhamnopyranosyl(14)]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 1) and 3-O-[α-L-arabinopyranosyl(13)]-[α-L-rhamnopyranosyl (12)]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 2) by 1D, 2D-NMR techniques, ESIMS analysis, as well as chemical methods.

Four new triterpenoid saponins, named scheffarboside A – D (1–4), along with five known saponins were isolated from the stems of Schefflera arboricola. The structures of the four new saponins were determined as 3-O-(O-β-glucuronopyranosyl-(1 3)-O-α-rhamnopyranosyl-(1 2)-α-arabinopyranosyl)oleanolic acid (1), 3-O-(O-α-arabinopyranosyl-(1 4)-O-α-arabinopyranosyl-(1 3)-O-α-rhamnopyranosyl-(1 2)-α-arabinopyranosyl)oleanolic acid (2), 3-O-(O-α-arabinopyranosyl-(1 4)-O-α-arabinopyranosyl-(1 3)-O-α-rhamnopyranosyl-(1 2)-α-arabinopyranosyl)hederagenin (3), 3-O-(O-α-arabinopyranosyl-(1 4)-O-α-arabinopyranosyl-(1 3)-O-α-rhamnopyranosyl-(1 2)-α-arabinopyranosyl)oleanolic acid O-α-rhamnopyranosyl-(1 4)-O-β-glucopyranosyl-(1 6)-β-glucopyranosylester (4), respectively, on the basis of spectroscopic and chemical degradation methods.

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.

Saponin-rich extracts of Medicago sativa L. have been shown to display antifungal activity against a range of common fungibut only a few individual saponins have been tested against dermatophytes. Total saponins were separately obtained from roots and aerial parts of Medicago sativa, M. murex, M. arabica and M. hybrida. Nineteen saponins and three parent triterpenoids, were tested against three dermatophytic fungi Microsporum gypseum, Trichophyton interdigitale and T. tonsurans using mircowell plate serial dilution assay to determine the Minimum Inhibitory Concentration (MIC). Miconazole was used as a positive control. T. tonsurans appeared to be the most sensitive of the dermatophytes to the active compounds. Aglycones showed less antifungal effect than the glycosides, which displayed a range of activities. Monodesmosidic glycosides of medicagenic acid were the most active compounds, especially the 3-O-beta-D-glucopyranoside, which displayed MIC less than 0.09mm against all three fungi, although those of hederagenin and zanhic acid also showed weak activity (MIC 3.3mm against two fungal species). Bidesmosidic saponins had weaker activity than monodesmosidic ones. This corresponds to activity of these and similar compounds against other fungal species but this is the first comprehensive report of activity of Medicago saponins against dermatophytes.

To search for new and bioactive compounds from traditional Chinese medicines, a new glycoside, 3-O-[alpha-L-rhamnopyranosyl-(1 -> 3)-(n-butyl-beta-D-glucopyranosiduronate)]-28-O-beta-D-glucopyranosyl oleanolic acid (1), was isolated from the roots of Cyathula officinalis Kuan, along with 3-O-(methyl-beta-D-glucopyranosiduronate)-28-O-beta-D-glucopyranosyl oleanolic acid (2), 3-O-beta-D-glucopyranosyl oleanolic acid (3), 3-O-beta-D-glucuronopyranosyl oleanolic acid (4), 3-O-[alpha-L-rhamnopyranosyl-(1 -> 3)-(beta-D-glucuronopyranosyl)] oleanolic acid (5), 3-O-(beta-D-glucuronopyranosyl)-28-O-beta-D-glucopyranosyl oleanolic acid (6), 28-O-beta-D-glucuronopyranosyl-(1 -> 4)-beta-D-glucopyranosyl hederagenin (7), 3-O-[alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranosyl oleanolic acid (8), and 3-O-[beta-D-glucopyranosyl-(1 -> 3)-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranosyl oleanolic acid (9). The structures of these compounds were determined based on spectral and chemical evidence. The 50 per cent growth-inhibiting (GI(50)) of compounds 1 and 5 against MDA-MB-231 (a human breast cancer cell line) was 3.44 x 10(-4) and 4.66 x 10(-4) mol/L, respectively.

The biosynthesis of triterpene saponins is poorly characterized in spite of the importance of these glycosylated secondary metabolites for plant defense and animal health. The model legume Medicago truncatula synthesizes more than 30 different saponins based on at least five triterpene aglycones; soyasapogenols B and E, medicagenic acid, hederagenin and bayogenin. We have employed an inducible cell culture system, DNA array-based and in silico transcript profiling, and targeted metabolite profiling, to identify triterpene glycosyltransferases (GTs) from among the more than 300 GTs expressed in M. truncatula. Two uridine diphosphate glucosyltransferases were functionally characterized; UGT73K1 with specificity for hederagenin and soyasapogenols B and E, and UGT71G1 with specificity for medicagenic acid. The latter enzyme also glycosylated certain isoflavones and the flavonol quercetin with higher efficiency than triterpenes; however, integrated transcript and metabolite profiling supported a function for UGT71G1 in terpenoid but not (iso)flavonoid biosynthesis in the elicited cell cultures.

Hederagenin on treatment with concentrated sulphuric acid at −5–0°C underwent a rearrangement leading to the formation of a new triterpenoidal skeleton, 3-isopropylidene-A-nor-5-β-methyl-Δ910-oleanenolactone.

A new monoterpene glycoside, mudanpioside J (3), was isolated from the root cortex of Paeonia suffruticosa. Its structure has been established on the basis of spectral evidence. In addition, six known compounds, campesterol (4), 4-hydroxyacetopenone (5), kaempferol (6), 3-hydroxy-4-methoxybenzoic acid (7), hederagenin (8) and galloylpaeoniflorin (9) were also isolated. A screening test of monoterpene glycosides and aromatic acids derived from P. suffruticosa and P. lactiflora on arachidonic acid, thrombin, collagen and PAF induced rabbit platelet aggregation suggests aromatic acids may play an important role in inhibition of platelet aggregation, inflammation and hemorrhage due to bacterial infection.

The complete 1H and 13C assignment of the pentacyclic triterpenoid hederagenin (3,23-dihydroxy-12-oleanan-28-oic acid) from Nigella sativa was carried out using a two-dimensional approach. The combined use of HMBC and HMQC were applied for the structural assignment and configurational information was obtained from the ROESY spectrum. Copyright © 1999 John Wiley & Sons, Ltd.

A rapid and sensitive liquid chromatography tandem mass spectrometry (LC-MS/MS) was developed and validated for simultaneous quantification of oleanolic acid and hederagenin in rat plasma. After the two analytes were extracted with liquid-liquid extraction, chromatographic separation was performed on a C18 column with acetonitrile and water (85:15, v/v) as mobile phase at a flow rate of 0.4 mL/min. Calibration curves exhibited good linearity (r > 0.995) over the ranges of 0.41-82.0 ng/mL for oleanolic acid and 0.32-64.0 ng/mL for hederagenin, respectively. The lower limit of quantifications (LLOQs) in plasma were 0.41 ng/mL for oleanolic acid and 0.32 ng/mL for hederagenin. The established LLOQs were within the concentration needed for the assay in plasma, which met the requirements to evaluate their pharmacokinetics of oleanolic acid and hederagenin. This developed assay was successfully applied in the pharmacokinetic study of oleanolic acid and hederagenin in rats after oral administration of Rhizoma Clematidis extract.

The chemical characterization of the saponins and sapogenins isolated from roots and aerial parts of two alfalfa cultivars with differing saponin content is reported. A procedure for the extraction and quantification of saponins is described, and the identification of the major components of the saponin mixture has been performed using thin layer chromatography and high performance liquid chromatography. Characterization, using gas chromatography (GC) and GC/mass spectral analysis, of sapogenins released following acid hydrolysis allowed the identification of medicagenic acid, hederagenin, soyasapogenols B, C, D, E and F as the major compounds, together with oleanolic acid. Quantitative analysis of the sapogenins in aerial parts and roots of the two cultivars is reported and discussed.

From the pericarps of Sapindus emarginatus (Sapindaceae), three new acetylated triterpene saponins were isolated together with hederagenin and five known triterpene saponins, as well as one known sweet acyclic sesquiterpene glycoside, mukurozioside IIb. The structures of new compounds were elucidated as hederagenin 3-O-(2-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside, 23-O-acetyl-hederagenin 3-O-(4-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside and oleanolic acid 3-O-(4-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside by chemical and spectroscopic data.

BACKGROUND: Triterpenic saponins from Sapindus mukorossi Gaertn. and Diploknema butyracea JF Gmelin were evaluated for in vitro antifungal activity against four phytopathogenic fungi. The study of the structure–antifungal activity relationships of protobassic acid saponins was widened by including semi-synthetic derivatives. RESULTS:Diploknema butyracea saponins exhibited significant antifungal activity against three fungi (ED50 230–455 µg mL−1), whereas S. mukorossi saponin was effective against two fungi (ED50 181–407 µg mL−1). The n-butanol extract after preparative HPLC separation provided two saponins from D. butyracea saponin mixture: 3-O-[β-D-glucopyarnosyl-β-D-glucopyranosyl]-16-α-hydroxyprotobassic acid-28-O-[arabinopyranosyl-glucopyranosyl-xylopyranosyl]-arabinopyranoside (MI-I), and 3-O-β-D-glucopyranosyl-glucopyranosyl-glucopyranosyl-16-α-hydroxyprotobassic acid-28-O-[arabinopyranosyl-xylopyranosyl-arabinopyranosyl]-apiofuranoside (MI-III). The single saponin extracted from S. mukorossi saponin mixture was identified as 3-O-[O-acetyl-β-D-xylopyranosyl-β-D-arabinopyranosyl-β-D-rhamnopyranosyl] hederagenin-28-O[β-D-glucopyranosyl-β-D-glucopyranosyl-β-D-rhamnopyranosyl] ester (SM-I). Monodesmosides resulting from the partial degradation of hederagenin and hydroxyprotobassic acid bisdesmosides exhibited significant reduction in antifungal effect. Further removal of sugar moiety yielded complete loss in activity. The antifungal activity of the triterpenic saponins was associated with their aglycone moieties, and esterification of the hydroxyl group led to change in antifungal activity. CONCLUSION:Sapindus mukorossi saponin, which is effective against Rhizoctonia bataticola (Taub.) Briton Jones and Sclerotium rolfsii Sacc., can be exploited for the development of a natural fungicide. A sugar moiety is a prerequisite for the antifungal activity of triterpenic saponin. Copyright © 2010 Society of Chemical Industry

The collisional activation spectra of lithiated and bariated cations and deprotonated anions of the triterpenoic acids hederagenin and oleanoic acid and their acetyl derivatives were examined. On collisional activation these precursors undergo similar charge-remote fragmentations including ring cleavage reactions and loss of substituents from the ring furthest from the site of charge. The presence of a double bond in ring C induces charge-remote retro-Diels-Alder reaction in these molecules

Four monodesmosidic triglycosides, bearing up to two acetyl moieties on the terminal sugar, have been isolated from the pericarp of fruits of Sapindus rarak DC (Sapindaceae). The positions of the acetyl groups and interglycosidic linkages have been established by proton nuclear magnetic resonance spectroscopy, including double-quantum filtered phase-sensitive COSY and homonuclear Overhauser enhancement difference measurements. A method for the qualitative analysis of saponins by reversed phase high pressure liquid chromatography (HPLC) has been developed. The total saponin content was determined by HPLC analysis of hederagenin liberated by acidic hydrolysis of the methanolic extract. The molluscicidal activity (LC100/24h) of the saponins ranges from 6.25 to 12.5 ppm.

A gas chromatographic method has been developed for the analysis of saponins in quinoa (Chenopodium quinoa Willd). The method, which involves separation and quantitation of the trimethylsilylated sapogenols, has been applied to the analysis of the UK-grown crop obtained by selection from lowland Chilean ecotypes. Total saponin contents of 1·03 and 1·19% were found for material grown in 1987 and 1988. The major aglycone in the quinoa saponin mixture was identified as phytolaccagenic acid (>40% total), with hederagenin (∼25%) and oleanolic acid (30%) aglycones also being present. The effects of washing and abrasion on total and individual saponin content were investigated; the data obtained suggest differential cellular locations of the individual saponins. The processing of quinoa led to changes in sensory characteristics; removal of saponins was associated with reductions in bitterness and astringency. Microscopic analysis revealed considerable differences in washed and abraded samples, both before and after cooking; in particular the abraded samples showed a greater degree of cellular disruption.

Several individual alfalfa (Medicago sativa L) root saponins were tested for their haemolytic activities using two methods, namely the haemolytic index test and a haemolytic micromethod. It was shown that individual saponins gave different haemolytic activities depending on their structure and also on the haemolytic test used. Generally it was found that saponin monodesmosides were more active than their bisdesmosidic analogues. These differences in haemolytic activities may strongly influence the results of saponin determination with haemolysis-based methods.

GULCIN, Ilhami/0000-0001-5993-1668 WOS: 000235626300008 PubMed: 16444666 The antioxidant activity of a triterpenoid glycoside [3-O-(beta-D-glucopyranosyl)-hederagenin; OGH] isolated from the berries of Hedera colchica, an ivy species endemic in Georgia, was investigated. The antioxidant properties of OGH were evaluated using different antioxidant assays: 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH-) scavenging, total antioxidant activity, reducing power, superoxide anion radical (O-2(-)) scavenging, hydrogen peroxide (H2O2) scavenging and metal chelating activities. The total antioxidant activity was measured according to the ferric thiocyanate method. alpha-Tocopherol and trolox, a water-soluble analogue of tocopherol, were used as reference antioxidant compounds. At a 30 mu g/mL concentration, the inhibitory effects of OGH on the peroxidation of linoleic acid emulsion was found to be 95.3%, whereas a-tocopherol and trolox exhibited 88.8% and 86.2% inhibition of peroxidation in the system, respectively. In addition, OGH had effective DPPH center dot scavenging, superoxide anion radical scavenging, hydrogen peroxide scavenging, total reducing power and metal chelation of ferrous ions activities. These various antioxidant activities were compared with (c)-tocopherol and trolox. Copyright (c) 2006 John Wiley & Sons, Ltd.

From the aerial parts of Cornulaca monacantha, three new triterpenoidal saponins have been isolated and their genuine structures were identified as 3-O-[beta-xylopyranosyl-(1-->3)-beta- glucuronopyranosyl]-30-methylphytolaccagenate (2), 3-O-[beta-xylopyranosyl- (1-->3)-beta-glucuronopyranosyl]-30-methylphytolaccagenate 28-O-beta-gluco-pyranoside (3) and 3-O-[beta-xylopyranosyl-(1-->3)-beta- glucurono-pyranosyl]-30-methylserjanate 28-O-beta glucopyranoside (4) together with nine known saponins of oleanolic acid (5-9), hederagenin (1, 10, 11) and 30-methyl phytolaccagenate (12).

Four triterpenoid saponins (1–4) have been isolated from the berries of Hedera helixL.(Araliaceae) by droplet counter-current and preparative liquid chromatography. The structures have been established by FD./MS. and 13C-NMR. spectroscopy. The isolated compounds were found to possess strong molluscicidal activity against the bilharziasis-transmitting snail Biomphalaria glabrata. Saponin 4, identified as hederagenin 3-O-β-D-glucopyranosyl-(1 2)-β-D-glucopyranoside, is a new natural product.

Anlaslich der Gewinnung von Hederagenin (1) sind die Perikarpien von Sapindus mukorossi Gaertn. auf unbekannte Inhaltsstoffe untersucht worden. Es sind Stigmasterin, Stigmasteryl-β-D-glucopyranosid, β-Amyrin (2), 28-Norolean-12-en-3β, 17β-diol (3) und 3,23-Ethylidenhederagenin (4) gefunden worden, wobei 4 moglicherweise ein Artefakt darstellt. Ferner sind die im Perikarp frei vorliegenden Fettsauren bestimmt worden. On Constituents of the Pericarps of Sapindus mukorossi Gaertn. In occasion of the isolation of hederagenin (1) the pericarps of Sapindus mukorossi Gaertn. were examined with regard to unknown constituents. Stigmasterol, stigmasteryl β-D-glucopyranoside, p-amyrin (2), 2-norolean-l 2-ene-3p, 1 7 p-diol(3) and 3,23-ethylidenehederagenin (4) were isolated; 4 may be an artifact. The free fatty acids in the pericarps were estimated.

Four triterpene saponins have been isolated, separated and purified from the roots of black medick trefoil. These have been identified as soyasaponin 1, hederagenin 3-O-β-D-glucopyranoside, medicagenic acid 3-O-β-D-glucopyranoside and medicagenic acid 3,28-di(O-β-D-glucopyranoside). The biological significance of the presence of these compounds is discussed.

A sapogenin isolated from the acid hydrolysates of roots or tops of alfalfa (Medicago sativa) has properties and constants identical to those of hederagenin. The corresponding saponin was isolated from a mixture of alfalfa saponins by successive chromatography on Al2 O3 and DEAE-Sephadex columns. Upon acid hydrolysis it yields glucose, arabinose and hederagenin, similarly to the saponin isolated from Hedera helix.

Hederagenin on treatment with concentrated sulphuric acid at −5–0°C underwent a rearrangement leading to the formation of a new triterpenoidal skeleton, 3-isopropylidene-A-nor-5-β-methyl-Δ910-oleanenolactone.