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Trillium govanianum , commonly known as Nag Chhatri and Teen Patra, is a popular herbal supplement traditionally used for curing different inflammatory and sexual disorders, infection and wound healing. Steroidal saponins are considered as active components of this species. The present study demonstrated the isolation of nine steroidal saponins, including one new compound named as govanoside B ( 9 ) and eight known, pregna-chacotrioside ( 1 ), pennogenin-triglycoside ( 2 ), borassoside E ( 3 ), pennogenin-tetraglycoside ( 4 ), protodioscin ( 5 ), clintonioside B ( 6 ), pennogenin-diglycoside ( 7 ) and borassoside D ( 8 ). This is the first report on the isolation of 1 , 2 , 4 , 5 , 6 , 7 and 8 from rhizomes of T. govanianum . The extract, fractions and isolated compounds were further evaluated for their DPPH and ABTS radical scavenging activity.

In the ongoing research on potent antitumor agents from the rhizomes of Asparagus cochinchinensis, seven undescribed steroidal saponins asparagusoside A-G (1-7), along with twenty known ones (8-27), were isolated and elucidated via analyzing their 1D, 2D NMR, mass spectroscopic data and chemical methods. All isolated compounds were evaluated for their cytotoxic effects against human large cell lung carcinoma cells (NCI-H460) in vitro. Among them, compounds 7, 9 and 27 showed more significant antitumor activities than the positive control cisplatin (11.56 μM) with IC 50 values of 1.39, 3.04, and 2.25 μM, respectively. Further research about asparagusoside G (7) showed G0/G1 arrest in NCI-H460 cell line cycle and induced cell death by apoptosis in a dose‑dependent way., (Copyright © 2021 Elsevier Inc. All rights reserved.)

Tomatoes are widely consumed, however, studies on tomato seeds are limited. In this study, we isolated 11 compounds including saponins and flavonol glycosides from tomato seeds and evaluated their effects on epidermal hydration. Among the isolated compounds, tomato seed saponins (10 µM) significantly increased the mRNA expression of proteins related to epidermal hydration, including filaggrin, involucrin, and enzymes for ceramide synthesis, by 1.32- to 1.91-fold compared with the control in HaCaT cells. Tomato seed saponins (10 µM) also decreased transepidermal water loss by 7 to 13 g/m 2 ·h in the reconstructed human epidermal keratinization (RHEK) models. Quantitative analysis of the ceramide content in the stratum corneum (SC) revealed that lycoperoside H (1-10 µM) is a promising candidate to stimulate ceramide synthesis via the upregulation of ceramide synthase-3, glucosylceramide synthase, and β-glucocerebrosidase, which led to an increase in the total SC ceramides (approximately 1.5-fold) in concert with ceramide (NP) (approximately 2-fold) in the RHEK models. Evaluation of the anti-inflammatory and anti-allergic effects of lycoperoside H demonstrated that lycoperoside H is suggested to act as a partial agonist of the glucocorticoid receptor and exhibits anti-inflammatory effects (10 mg/kg in animal test). These findings indicate that lycoperoside H can improve epidermal dehydration and suppress inflammation by increasing SC ceramide and steroidal anti-inflammatory activity.

A systematic phytochemical study on the components in the seeds of Allium tuberosum was performed, leading to the isolation of 27 steroidal glycosides (SGs 1 - 27 ). The structures of SGs were identified mainly by nuclear magnetic resonance and mass spectrometries as well as the necessary chemical evidence. In the SGs, 1 - 10 and 22 - 26 are new steroidal saponin analogues. An in vitro bioassay indicates that 1 , 2 , 7 , 8 , 10 , 13 - 15 , 20 , 23 , and 26 display promotional roles in testosterone production of rat Leydig cells with the EC 50 values of 1.0 to 4.5 μM, respectively.

Phytochemical analysis of the fruits of Raphia vinifera led to the isolation of four new steroidal saponins (1-4), along with six known secondary metabolites (6-10). The structures of the isolated compounds were determined based on the analyses of NMR and mass spectrometric data, and chemical degradation reactions. Among the compounds tested, 1 and 4 showed the most promising cytotoxic activity against the drug-sensitive CCRF-CEM leukemia cell lines, with IC 50 values of 3.55 µM and 7.14 µM, respectively., (Copyright © 2020 Elsevier Inc. All rights reserved.)

A phytochemical study on the rhizomes of Trillium tschonoskii led to the isolation of fourteen new steroidal saponins, trillitschosides S1-S14 (1-14), along with ten known analogues (15-24). Their structures were established mainly by spectroscopic analyses as well as necessary chemical evidence. All isolated compounds were screened for the cytotoxicity against HepG2 cells, and the results demonstrated that only the known compounds 21-24 exhibited the remarkable cytotoxic activity against HepG2 cells which is much better than the positive control of 5-FU., (Copyright © 2020 Elsevier Inc. All rights reserved.)

Two novel steroidal saponins, timosaponin V and W (1 and 2), together with seven known steroidal saponins (3-9), were isolated from the rhizomes of Anemarrhena asphodeloides Bunge. Their structures were elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, 1 H- 1 H COSY, and NOESY), and MS analyses. The cytotoxic activities of the isolates were evaluated. Compound 1 showed a significant cytotoxic activity against MCF-7 and HepG2 cell lines with IC 50 values of 2.16 ± 0.19 μM and 2.01 ± 0.19 μM, respectively., (Copyright © 2019 Elsevier Inc. All rights reserved.)

Timosaponin AIII, a major steroidal saponin found in Anemarrhena asphodeloides Bge., which has been widely used as anti-pyretic, anti-diabetic, anti-inflammatory, anti-platelet aggregator and anti-depressant agents in traditional Chinese medicine. Recent pharmacological study showed that timosaponin AIII had potent cytotoxicity, which was potential to be developed as an anticancer agent, however the molecular mechanism underlying the anticancer activity has not been fully elucidated. This review aims to give a systematic summary of the study of timosaponin AIII to reveal its anti-tumor activities by investigating invasion and migration, apoptosis, autophagy and reversing multi-drug resistance. Furthermore, we also make an overview of the mechanisms identified till now. These meaningful findings may provide novel insights on exploiting timosaponin AIII as a new anti-tumor agent., (Copyright © 2018 Elsevier Inc. All rights reserved.)

Datura metel L. (Solanaceae) is an annual herb that has been widely used in the traditional medicine for the treatment of coughs, bronchial asthma, and rheumatism. Chemical investigation of an acidic methanol extract of the whole plants of D. metel resulted in the isolation of five new steroidal saponins (1-3, 5, and 6), named metelosides A-E, and four known compounds (4, 7-9). Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra. The structures of metelosides A and B were found to be unusual among the reported spirostane-type steroidal saponins due to the presence of the acetamide groups in the molecules. Compounds 2, 4, 5, and 6 were shown to be cytotoxic against three cancer cell lines, including HepG2, MCF-7, and SK-Mel-2 cells. Furthermore, compounds 3, 4, and 7 exhibited modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated BV cells., (Copyright © 2017 Elsevier Inc. All rights reserved.)

Two new steroidal saponins, named timosaponin P (1) and timosaponin Q (2), were isolated from the rhizome parts of Anemarrhena asphodeloides Bunge using various chromatographic methods. Their structures and absolute configurations were elucidated by a combination of spectroscopic and spectrometric data, including 1D, 2D NMR, HR-ESI-MS and ECD calculations, and this is the first time the absolute configuration of C-23 of steroidal saponin was confirmed by ECD calculations., (Copyright © 2017 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.)

Objective Taccaoside, a steroidal saponin, has been shown to be cytotoxic, although the mechanism of cytotoxicity remains unclear. This study examined the effect of taccaoside on the human hepatocellular carcinoma (HCC) cell lines SMMC-7721 and Bel-7404. Methods The antiproliferative effect of taccaoside were measured using the 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide assay. Cells were stained with Hoechst 33258 to observe morphology. Cell cycle and apoptosis were analysed by flow cytometry. Caspase activation was detected using specific assays, and PARP, Bax and Bcl-2 expression were analysed using western blotting. Results Taccaoside showed antiproliferative effect on HCC cell lines growth in a concentration- and time-dependent manner. Taccaoside arrested cell cycle in the G2/M phase and induced caspase-dependent apoptosis. Western blotting indicated that taccaoside upregulated Bax expression and downregulated Bcl-2 expression. PARP cleavage was observed following taccaoside treatment. Conclusions This study showed that taccaoside may inhibit HCC cell proliferation by inducing apoptosis.

In this study seven strains of the genus Arthrobacter were screened by biotransformation to discover glycosylating patterns on steroid saponins. A strain of Arthrobacter nitroguajacolicus (CPCC 203516) was found to have the ability of fructosylation. Crude enzyme of the strain was extracted for the further study of conversion characteristics and patterns. Sucrose was used as a non-activated sugar donor, and fifteen steroidal saponins were involved. Nine furostan saponins of the substrates were converted, and ten products were isolated and identified. Based on the HR-ESI-MS, 1D, and 2D NMR spectral data, one fructosyl was added to furostan saponins at C6-OH of 26-O-β-D-glucopyranosyl by A. nitroguajacolicus for all nine products. One product was distinguished by an additional fructosyl at the position of C6-OH on the first added fructosyl. Spirostan saponins of the substrates could not be converted. Steroidal saponins embracing a fructosyl are quite rare according to other reports based on similar studies. This study successfully converted furostan saponins into new compounds., (Copyright © 2014 Elsevier Ltd. All rights reserved.)

Phytochemical study on dragon's blood of Dracaena cambodiana led to a new steroidal saponin, cambodianoside G(1), and six known ones (2-7). The structure of the new compound was elucidated on the basis of detailed spectroscopic analysis. Evaluation of antibacterial activities showed that compound 7 exhibited antibacterial activity against Staphylococcus aureus.

Two new steroidal saponins, timosaponin X (1) and timosaponin Y (2), and one new pregnane glycoside, timopregnane B (3), were isolated from the rhizomes of Anemarrhena asphodeloides, as well as three known compounds 25S-timosaponin BII (4), protodesgalactotigonin (5), and timosaponin BII-a (6) isolated from this plant for the first time. By the detailed analysis of 1D, 2D NMR, MS spectra, and chemical evidences, the structures of new compounds were elucidated as 26-O-β-d-glucopyranosyl-(25S)-5β-22-methoxy-furost-3β,26-diol 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranoside (1), 5β-pseudo-spirost-3β,15α,23α-triol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (2), (5β,17α)-Δ((16)(17))-20-one-pregn-2β,3β-diol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (3).

Background: Paullinia pinnata L. (Sapindaceae) is an African woody vine, which is widely used in traditional medicine for the treatment of human malaria, erectile dysfunction and bacterial infections. A phytochemical investigation of its methanol leaf and stem extracts led to the isolation of seven compounds which were evaluated for their antimicrobial properties. Methods: The extracts were fractionated and compounds were isolated by chromatographic methods. Their structures were elucidated from their spectroscopic data in conjunction with those reported in literature. The antimicrobial activities of the crude extracts, fractions and compounds were evaluated against bacteria, yeasts and dermatophytes using the broth micro-dilution technique. Results: Seven compounds: 2-O-methyl-L-chiro-inositol (1), β-sitosterol (2), friedelin (3), 3β-(β-D-Glucopyranosyloxy) stigmast-5-ene (4), (3β)-3-O-(2'-Acetamido-2'-deoxy-β-D-glucopyranosyl) oleanolic acid (5), (3β,16α-hydroxy)-3-O-(2'-Acetamido-2'-deoxy-β-D-glucopyranosyl) echinocystic acid (6) and (3β)-3-O-[β-D-glucopyranosyl-(1"-3')-2'-acetamido-2'-deoxy-β-D-galactopyranosyl]oleanolic acid (7) were isolated. Compounds 5 and 7 showed the best antibacterial and anti-yeast activities respectively (MIC value range of 0.78-6.25 and 1.56-6.25 µg/ml), while 6 exhibited the best anti-dermatophytic activity (MIC value range of 6.25-25 µg/ml). Conclusion: The results of the present findings could be considered interesting, taking into account the global disease burden of these susceptible microorganisms, in conjunction with the search for alternative and complementary medicines. [ABSTRACT FROM AUTHOR]

Abstract: The naturally derived trisaccharide steroidal saponin 1 and structurally modified derivatives 2 and 3 bearing the same sarsasapogenin aglycon were synthesized concisely via a direct transglycosylation strategy. The antitumor activities of the synthetic trisaccharide saponins 1–3 and their corresponding α-isomers 1a–3a were preliminarily evaluated against human gastric adenocarcinoma cell (MKN-45) and human epithelial cervical cancer cell (HeLa) by CCK-8 assay. [Copyright &y& Elsevier]

Abstract: Two new furostanol saponins, 3-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl]-26-O-β-d-glucopyranosyl-25(R)-furosta-5,22(23)-dien-3β,20α,26-triol (1), 3-O-[β-d-glucopyranosyl-(1→3)-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl]-26-O-β-d-glucopyranosyl-20(R)-methoxyl-25(R)-furosta-5,22(23)-dien-3β,26-diol (2) were isolated from the Dioscorea panthaica along with five known steroidal saponins (3–7). The structures of the new saponins were determined by detailed analysis of spectral data (including 2D NMR spectroscopy). The inhibitory activities of the saponins against α-glucosidase were investigated, gracillin (4) and 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl]-26-O-β-d-glucopyranosyl-25(R)-furosta-5,20(22)-dien-3β,26-diol (5) were found to exhibit potent activities with IC50 values of 0.11±0.04mM and 0.09±0.01mM. [Copyright &y& Elsevier]

Abstract: A rare 16β-H steroidal alkaloid saponin (1), an avenacoside-type saponin (2), two steroidal saponins (4, 5), one revised-structure steroidal saponin (3) and six known compounds (6–11) were isolated from aerial parts of Solanum surattense Burm. f. Their structures were established on the basis of physical data, as well as by using spectroscopic (HRESIMS, 1D and 2D NMR), and chemical analysis methods. Compounds 1 and 11 showed cytotoxicity against A549 cell line with IC50 values of 20.3 and 15.7μM, respectively. [Copyright &y& Elsevier]

Abstract: Steroidal saponins are the major bioactive constituents of Dioscorea zingiberensis C. H. Wright (D. zingiberensis). In this work, ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS/MS) was applied to the separation and characterization of steroidal saponins in crude extracts from D. zingiberensis. The results showed that fragment ions from glycosidic and cross-ring cleavages gave a wealth of structural information related to aglycone skeletons, sugar types and the sequence of sugar units. According to the summarized fragmentation patterns, identification of steroidal saponins from D. zingiberensis could be fulfilled, even when reference standards were unavailable. As a result, a total of thirty-one saponins with five aglycone skeletons, including fourteen new trace saponins, were identified or tentatively elucidated in crude extracts from D. zingiberensis based on their retention times, the mass spectrometric fragmentation patterns, and MS and MS/MS data. [Copyright &y& Elsevier]

Rhizoma Paridis saponins are bioactive steroidal saponins derived from Paris polyphylla. Optimization of the ionization process was performed with electrospray ionization tandem mass spectrometry in both positive and negative-ion modes. Negative-ion ESI was adopted for generation of the precursor deprotonated molecules to achieve the best ionization sensitivity for the analytes. Positive ionization was used to choose the most abundant fragment ion. Furthermore, according to the characteristic fragmentation behavior of known steroidal saponins isolated from this plant (polyphyllin D, formosanin C, gracillin, Paris H, Paris VII, and dioscin), 23 constituents were structurally characterized on the basis of their retention time and ESI analyses, including four pairs of naturally occurring isomers. Five of these 23 constituents were new compounds. The analytical method of LC–MS n in positive and negative-ion modes has been developed for the direct structural elucidation of steroid saponins of this kind in plant extracts. [ABSTRACT FROM AUTHOR]

Abstract: Two new steroidal saponins with a new aglycone moiety, aspafiliosides E (1) and F (2), were isolated from the roots of Asparagus filicinus Buch.–Ham. Their structures were fully elucidated on the basis of detailed spectroscopic study and chemical analysis. [Copyright &y& Elsevier]

Two new pregnane saponins, solanigroside A (1) and solanigroside B (2), along with two known compounds (3 and 4), were isolated from 60% ethanolic extract of the dried herb of Solanum nigrum L. The structures of 1 and 2 were elucidated as 5α-pregn-16-en-3β-ol-20-one 3-O-β-d-xylopyranosyl-(1 → 3)-O-[α-l-arabinopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-O-β-d-galactopyranoside (1) and 5α-pregn-16-en-3β-ol-20-one 3-O-β-d-glucopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-galactopyranoside (2), respectively, on the basis of extensive spectroscopic analysis as well as comparison with reported spectroscopic data of related compounds. This paper deals with the isolation and structural characterisation of pregnane glycosides from S. nigrum L. [ABSTRACT FROM AUTHOR]

Abstract: Applicability of 13C and 1H NMR chemical shifts for the assignment of the 25R/25S configuration of the 27-methyl group in the case of furostane-type steroidal saponins has been investigated. A comparative study of 13C NMR data suggest that chemical shift values for C-20, C-21, C-22, C-23, C-24, C-25, C-26 and C-27 resonances were not much influenced by R/S configuration of the 27-Me group, thus reflecting limited application of 13C NMR chemical shifts for such stereochemical determinations. In contrast, 1H NMR chemical shifts (δ a, δ b) for geminal protons of glycosyloxy methylene (H2-26) exhibit pronounced dependence and the difference (Δ ab = δ a − δ b) among their chemical shifts [Δ ab =<0.48 for 25R; Δ ab =>0.57 for 25S] seems to be of general applicability for ascertaining 25R/25S orientation of the 27-methyl group of furostane-type steroidal saponins. [Copyright &y& Elsevier]