Saponins from Furcraea selloa var. marginata

Four steroidal saponins were isolated from the leaves of Furcraea selloa var. marginata. These included one furostanol saponin, furcreafurostatin (1), and three known spirostanol saponins, furcreastatin (3), yuccaloeside C (4) and cantalasaponin-1 (5). The 22-O-methyl ether (2) of furcreafurostatin (1) was also characterized. The structures were determined by using a combination of spectroscopic techniques.     

Protective effect of saponins from Argania spinosa against free radical-induced oxidative haemolysis

Saponins from Argania spinosa at a non-haemolytic concentration diminish by 53.2% erythrocyte haemolysis induced by free radicals. 2 mM aspirin and acetaminophen diminish by 75% and 68% , respectively, erythrocyte haemolysis induced by free radicals, while 0.3 muM vitamin E shows no significant antioxidant activity. Interestingly, a combination of 1 mg/l of A. spinosa saponins and vitamin E at 0.3 muM resulted in a 68% level of protection against free radical-induced erythrocyte haemolysis, which may suggest that A. spinosa saponins enhance the antioxidant effect of vitamin E. In contrast, no synergic effect was observed for acetaminophen (2 mM) when in combination with vitamin E (0.3 muM). These results demonstrate the antioxidant properties of saponins from A. spinosa and their ability to potentate the antioxidant effect of vitamin E.     

A novel hepatoprotective saponin from Celosia cristata L.

A new saponin, cristatain (1), together with four other saponins, celosin A (2), celosin B (3), celosin C (4) and celosin D (5) were isolated from the seeds of Celosia cristata L. (Amaranthaceae). Their structures were established by chemical and spectroscopic analyses. For the first time, the saponins were found in C. cristata L. In addition, compound 1 exhibited significant hepatoprotective effect on carbon tetrachloride (CCl₄)- and N,N-dimethylformamide (DMF)–induced hepatotoxicity in mice, which were evidenced by significant decreases in the values of asparate aminotransferase (AST), alanine aminotransferase (ALT) and alkaline phosphatase (ALP) of serum and histopathological examinations compared to controls.     

Anti-thrombotic activity and chemical characterization of steroidal saponins from Dioscorea zingiberensis C.H. Wright

Steroidal saponins have long attracted scientific attention, due to their structural diversity and significant biological activities. Total steroidal saponins (TSS) extracted from the rhizomes of Dioscorea zingiberensis C.H. Wright (DZW) constitute an effective treatment for cardiovascular disease. However, the active constituents contained in DZW rhizomes and their pharmacological properties are not fully understood. The aim of this work is to determine and quantify the active constituents in DZW rhizomes using fingerprint technique, and evaluate its anti-thrombotic activity using inferior vena cava ligation thrombosis rat model and pulmonary thrombosis mice model after being gavaged with TSS for 1 or 2 weeks. In the study, a chemical fingerprint method was firstly established and validated to quantify and standardize TSS from DZW rhizomes including parvifloside, protodeltonin, protodioscin, protogracillin, zingiberensis saponin, deltonin, dioscin and trillin. TSS extracted from DZW rhizomes were showed to have the inhibitions on platelet aggregation (PAG) and thrombosis, and prolong activated partial thromboplastin time (APTT), thrombin time (TT), and prothrombin time (PT) in a dose-dependent manner in rats. TSS also prolonged the bleeding time and clotting time in a dose-dependent manner in mice. The results indicate that TSS could inhibit thrombosis by both improving the anticoagulation activity and inhibiting PAG action, suggesting that TSS from DZW rhizomes have the potential to reduce the risk of cardiovascular diseases by anti-thrombotic action.     

Antiproliferative activity of Saponaria vaccaria constituents and related compounds

Total methanolic extracts of Saponaria vaccaria seed derived from several varieties, as well as various purified components obtained through successive chromatographic separations of total extracts were evaluated for their growth inhibitory activity in WiDr (colon), MDA-MB-231 (breast), NCI-417 (lung) and PC-3 (prostate) human cancer cells as well as the non-tumorigenic fibroblast BJ (CRL-2522) cell line using MTT colorimetric assay. Purified bisdesmosidic saponins segetoside H and I were further examined using microscopy and apoptosis assays. Bisdesmosidic saponins exhibited dose-dependent growth inhibitory and selective apoptosis-inducing activity. Growth inhibitory effects were particularly strong in a breast (MDA-MB-231) and a prostate (PC-3) cancer cell line. Total extracts exhibited a different preference being most active against a colon cancer cell line (WiDr). In a comparison of varieties, all of the total seed extracts exhibited similar dose-dependent activities, but with some variation in potency. Monodesmosidic saponins vaccarosides A and B, phenolic vaccarin, and cyclopeptide segetalin A, co-occurring seed substituents, did not exhibit activity. The non-tumorigenic fibroblast cell line BJ (CRL 2522) was growth inhibited but did not undergo apoptosis when treated with bisdesmosidic saponins at low micromolar concentrations. Saponin-rich extracts from Kochia scoparia seed and Chenopodium quinoa were also evaluated alongside Saponaria saponins but did not exhibit activity. Closely related Quillaja saponins exhibited activity but were less potent.     

Structure elucidation of two triterpenoid saponins from rhizome of Anemone raddeana Regel

Two new 27-hydroxy-oleanolic acid type triterpenoid saponins, raddeanoside 20 (1) and raddeanoside 21(2) were isolated from the rhizome of Anemone raddeana Regel. The structures of the two compounds were elucidated as 27-hydroxy-oleanolic acid 3-O-α-l-rhamnopyranosyl(1→2) [β-d-glucopyranosyl (1→4)]-α-l-arabinopyranoside (1) and 3-O-α-l-rhamnopyranosyl (1→2)-α-l-arabinopyranosyl-27-hydroxy-oleanolic acid 28-O-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl (1→6)-β-d-glucopyranoside (2) on the basis of chemical and spectral evidence.     

Chemical characteristics of saponins from Paris fargesii var. brevipetala and cytotoxic activity of its main ingredient, paris saponin H

More attention was paid to the anti-tumor activity of Rhizoma Paridis (RP) recently, of which the wild resource was decreased significantly. This study was aimed to elucidate the chemical characteristics of Paris fargesii var. brevipetala (PFB) that may be administrated as alternate resource of legal RP. A HPLC-ELSD method was established to characterize the steroid saponins in rhizomes of PFB and two legal Paris species [Paris polyphylla var. chinensis (PPC) and P. polyphylla var. yunnanensis (PPY)] in Chinese Pharmacopoeia (CP). Ten saponins (paris saponins I, II, V, VI, VII, H, gracillin and other three paris saponins) were involved as standards. The results indicated that PFB contained pennogenyl saponins as the main components with small amounts of diosgenin saponins. The total contents of the detected saponins in PFB ranged from 9.12mg/g to 85.33mg/g. Nine of the twelve PFB samples own a total content of paris saponins I, II, VI, and VII more than 6.0mg/g (meeting the standard of CP 2010 edition). Principal Component Analysis (PCA) and Partial Least Squares-Discriminate Analysis (PLS-DA) both confirmed the fact that saponin profiles of PFB, PPC and PPY were different from each other. In addition, paris saponin H (Ps H), the predominant saponin of PFB (>50%), was tested in vitro to evaluate its cytotoxic activities on HepG2, A549, RPE and L929 cells with a positive control of Cisplatin. Ps H showed a remarkable cytotoxic activity on A549 cells with an IC(50) value of 1.53±0.08μg/mL.     

Chemical study and medical application of saponins as anti-cancer agents

Saponins are a group of naturally occurring plant glycosides, characterized by their strong foam-forming properties in aqueous solution. The presence of saponins has been reported in more than 100 families of plants out of which at least 150 kinds of natural saponins have been found to possess significant anti-cancer properties. There are more than 11 distinguished classes of saponins including dammaranes, tirucallanes, lupanes, hopanes, oleananes, taraxasteranes, ursanes, cycloartanes, lanostanes, cucurbitanes and steroids. Due to the great variability of their structures, saponins always display anti-tumorigenic effects through varieties of antitumor pathways. In addition, there are a large amount of saponins that still either remain to be trapped or studied in details by the medicinal chemists. This article reviews many such structures and their related chemistry along with the recent advances in understanding mechanism of action and structure–function relationships of saponins at the molecular and cellular levels. These aglycones have been described and their classification and distribution have been listed in the review. Some special saponins with strong antitumor effects have also been exhibited. Ginsenosides, belonging to dammaranes, have been found beneficial targeted on inhibition of tumor angiogenesis by suppressing its inducer in the endothelial cells of blood vessels, and then on prevention of adhering, invasion, and metastasis of tumor cells. Dioscin, one of the steroidal saponins, and its aglycone diosgenin also have been extensively studied on its antitumor effect by cell cycle arrest and apoptosis. Other important molecules discussed include oleanane saponins such as avicins, platycodons, saikosaponins, and soysaponins along with tubeimosides.     

New pregnane saponins from Ecdysanthera rosea and their cytotoxicity

Two new pregnane saponins elucidated as ecdysantheroside A (1) and ecdysantheroside B (2) and six known compounds (3-8) based on spectral data (MS, IR, 1D and 2D NMR) were isolated from the stem bark of Ecdysanthera rosea. The cytotoxicity against six cell lines of these compounds was tested by MTT assay. The results revealed that compounds 5 and 7 showed cytotoxicity against all the cell lines. Compound 2 showed cytotoxicity against cells A549, MDA435, HepG2, and HUVEC, while compound 4 showed cytotoxicity against cells A549, CEM, and HUVEC. Compound 6 had cytotoxicity against the others except cell HepG2.     

Triterpenoid saponins from Clematis tangutica and their cardioprotective activities

Phytochemical investigation of the whole plants of Clematis tangutica led to the isolation of three new triterpenoid saponins (1–3), together with four known saponins (4–7). Their structures were determined by extensive spectral analysis and chemical evidences. Compounds 1–7 were evaluated for their cardioprotective activities in cardiomyocytes anoxia/reoxygenation (A/R) model. The results showed that those saponins exhibited cardioprotective effects by decreasing the levels of creatine kinase-MB (CK-MB) and lactate dehydrogenase (LDH).     

Saponins from Glycine max Merrill (soybean)

Saponins are a diverse group of plant secondary metabolites with a wide array of activities, as well as a significant role in nutrition and health. Saponins occur as multi-component mixtures of compounds with very similar polarities. Soysaponins are a special group of saponins. These represent the main source of saponins in Glycine max (soybeans, Fabaceae). In a study of the chemical profiling of plants, to investigate the possible misidentification and authentication of dietary supplements, the hydro-alcoholic extract of G. max was investigated. Three new saponins, designated as soysaponins M1 (1), M2 (2) and M3 (3) along with seven known soysaponins (4–10) were isolated by normal and reverse phase liquid chromatography. All compounds were characterized by spectroscopic techniques including 2D NMR spectroscopy.     

“青引”燕麦中皂甙提取工艺研究

研究利用索氏浸提法提取燕麦中皂甙工艺条件。以乙醇-正丁醇为溶剂,以皂甙RC为标准品,采用分光光度法定量分析燕麦提取液中总皂甙含量,采用正交试验对料液比、乙醇浓度、浸提温度对提取率的影响。结果表明,正交试验最佳提取条件为料液比：1∶7;乙醇浓度：70%;浸提温度：70℃,提取率为1.716%;主次顺序依次为：料液比〉浸提温度〉乙醇浓度。该方法操作方便,简单易行,具有推广应用价值。     

Selective modulation of P-glycoprotein activity by steroidal saponines from Paris polyphylla

Bio-guided fractionation of the roots of Paris polyphylla (Trilliaceae), based on inhibition of P-glycoprotein-mediated daunorubicin efflux in K562/R7 cell line, led to isolation and identification of the three saponins 3-O-Rha(1-->2)[Ara(1-->4)]Glc-pennogenine, gracillin and polyphyllin D, and the two ecdysteroids 20-hydroxyecdysone and pinnatasterone. These compounds were tested for multidrug reversion on P-glycoprotein (ABCB1) with both drug-selected and transfected cell lines, and also on Breast Cancer Resistance Protein (BCRP/ABCG2). By contrast to a weak efficiency on BCRP, the three saponins displayed significant effects as inhibitors of P-glycoprotein-mediated drug efflux.     

Larvicidal activity of Solanum villosum Mill (Solanaceae: Solanales) leaves to Anopheles subpictus Grassi (Diptera: Culicidae) with effect on non-target Chironomus circumdatus Kieffer (Diptera: Chironomidae)

Chloroform-methanol extract of mature leaves from Solanum villosum Mill (Solanaceae: Solanales) was investigated to establish its biocontrol potentiality under laboratory condition against larval forms of Anopheles subpictus Grassi (Diptera: Culicidae), the vector of human malaria. All the graded concentrations (30, 50, 100 and 200 ppm) showed significant (P < 0.05) larval mortality and results of regression equations revealed that the mortality rates were positively correlated with the concentrations of the extract (R ² close to 1). LC₅₀ values for all instars were between 24.20 and 33.73 ppm after 24 h and between 23.47 and 30.63 ppm after 48 h of exposure period. Significant changes in the larval mortality (F < 0.05) was also recorded between instars during single “ANOVA” analysis. This extract also demonstrated no toxicity to larvae of Chironomus circumdatus Kieffer (Diptera: Chironomidae) which were found to be present as most common non-target dipteran insect in the habitats of A. subpictus. Qualitative and chromatographic analysis of the solvent extract revealed the presence of carbohydrates, saponins, terpenoids, volatile oil, steroids, phenols and flavonoids as major bioactive phytochemicals.     

Optimization of the selective preparation of 20(R)-ginsenoside Rg3 catalyzed by d,l-tartaric acid using response surface methodology

The optimization of the selective preparation of 20(R)-ginsenoside Rg3 converting protopanaxadiol type saponins (PPD saponins) by the commercially available d, l-tartaric acid was carried out using response surface methodology (RSM) based on a three-factor and six-level central composite design. The optimal 20(R)-ginsenoside Rg3 de% was predicted to be 94.52% in the combination of the factors (d, l-tartaric acid concentration 1.19 mol/L, temperature 107.9 °C and time 2.79 h) through the canonical analysis with maximum responses. Under the optimum reaction conditions, the actual 20(R)-ginsenoside Rg3 de% was 96.49%. 20(R)-ginsenoside Rg3 (1) and 20(S)-ginsenoside Rg3 (2) were separated and identified by ¹H-NMR and ¹³C-NMR. Therefore, the RSM was effective to optimize the preparation of 20(R)-ginsenoside Rg3 by converting PPD saponins using d, l-tartaric acid.     

Steroidal saponins from Fritillaria pallidiflora Schrenk

Five new steroidal saponins, Pallidifloside D (1), Pallidifloside E (2), Pallidifloside G (5), Pallidifloside H (6) and Pallidifloside I (7), together with seven other steroidal saponins (3, 4, 8-12) were isolated from the dry bulbs of Fritillaria pallidiflora Schrenk. Their structures were established by spectroscopic techniques (IR, MS, 1D and 2D NMR) and chemical means. The isolated steroidal saponins were evaluated for cyotoxic activity against human C6 brain gliomas and Hela cervix cancer cell lines using MTT assays. Compounds 1, 10, 11, 12 showed cytotoxicity against C6 and Hela cell lines with IC(50) values in the range of 5.1-75.8μM.     

Lipidated steroid saponins from Dioscorea villosa (wild yam)

Two groups of lipidated steroid saponins including seven new compounds (2, 3, 5, and 7–10) were isolated from the widely used botanical, wild yam (Dioscorea villosa), employing a fractionation protocol of metabolomic mining. This methodology recently led to the isolation of 14 diarylheptanoids from the same plant. Together with these lipidated steroid saponins, they establish additional new markers for D. villosa. The lipidation of steroids with analog long-chain fatty acids containing different degrees of unsaturation generates an entire series of compounds which are difficult to purify and analyze. The structures of the two series of lipidated steroid saponins (series A and B) were established by a combination of 1D and 2D NMR as well as GC–MS after chemical modification. Series A was determined to be a mixture of lipidated spirostanol glycosides (1–5), while series B (6–10) was proved to be a mixture of five lipidated clionasterol glucosides. The latter group represents the first derivatives of clionasterol to be found in D. villosa. The discovery of this specific structural type of aliphatic esters of steroid saponins expands the characterization of the secondary metabolome of D. villosa. It may also inspire biological studies which take into account the lipophilic character and significantly altered physiochemical characteristics of these otherwise relatively polar phytoconstituents.     

Two new cytotoxic triterpenoid saponins from the roots of Clematis argentilucida

Bioassay-guided fractionation of the n-BuOH extract of the roots of Clematis argentilucida led to the isolation of two new triterpenoid saponins along with a known one, cussonside B (3). By extensive spectral analysis and chemical evidences, the structures of the two new saponins were determined to be 3β-O-[β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] hederagenin-11,13-dien-28-oic acid (1) and 3β-O-{β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl} oleanolic acid (2), respectively. Saponin 1 is the first example of triterpenoid saponins with two double bonds located at C-11 and C-13 in the aglycone from the genus Clematis. The two new saponins exhibited significant cytotoxicity against human leukemia HL-60 cell lines, human hepatocellular carcinoma Hep-G2 cell lines and human glioblastoma U251MG cell lines with a range of IC(50) values from 2.74 to 25.40μM, while 3 showed inactivity against all of the three cancer cell lines.     

Triterpene saponins from Tabellae Clinopodii

Three new triterpene saponins, named Clinoposaponin A, Clinoposaponin B, and Clinoposaponin C along with three known triterpene saponins were isolated from the Tabellae Clinopodii. The structures of these compounds were elucidated by means of various spectroscopic analyses. All of the isolated compounds were tested against Hela, HCT-8, AGS, and MCF-7 human cancer cell lines and showed moderate cytotoxic activities with IC₅₀ values between 4.1 and 19.7 μM.     

Three triterpenoid saponins from the roots of Polygala japonica Houtt

Three new triterpenoid saponins polygalasaponins LI-LIII (1-3) with two acylation groups in oligosaccharide chain, together with three known saponins were isolated from the roots of Polygala japonica Houtt. (4-6). The neuroprotective effects of these compounds on neuron-like PC12 cells were evaluated in vitro. Compounds 5 and 6 show neuroprotective effects in Aβ(25-35) model at the concentration of 10μM.