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To optimize the utilization of the sea star Patiria (=Asterina) pectinifera, which has demonstrated potential pharmaceutical properties in Chinese folk medicine, ten glycosides of polyhydroxy steroids, pectiniferosides A–J (1–10), were isolated and characterized. These compounds possess 3β, 6α, 8, 15α (or β), 16β-pentahydroxycholestane aglycones with sulfated and (or) methylated monosaccharides. The chemical structures of 1–10 were determined using NMR spectroscopy and HR-ESI-MS. The discovery of saponins with multiple substitution patterns in sea stars exemplified the molecular diversity of secondary metabolites in marine echinoderms. These compounds exhibited no embryotoxicity or teratogenicity at a concentration of 100 μM in a bioassay with marine medaka (Oryzias melastigma) embryos, implying that these compounds may not be ecologically toxic to marine fish embryos. In addition, none of the compounds exhibited significant cytotoxicity against five human cancer cell lines at 40 μM or anti-inflammatory activities at 50 μM, suggesting their potential for further structural optimization to enhance bioactivity. The research on the constituents of P. pectinifera provides a potential foundation for drug development and marine ecotoxicology. [ABSTRACT FROM AUTHOR]

To optimize the utilization of the sea star Patiria (=Asterina) pectinifera, which has demonstrated potential pharmaceutical properties in Chinese folk medicine, ten glycosides of polyhydroxy steroids, pectiniferosides A–J (1–10), were isolated and characterized. These compounds possess 3β, 6α, 8, 15α (or β), 16β-pentahydroxycholestane aglycones with sulfated and (or) methylated monosaccharides. The chemical structures of 1–10 were determined using NMR spectroscopy and HR-ESI-MS. The discovery of saponins with multiple substitution patterns in sea stars exemplified the molecular diversity of secondary metabolites in marine echinoderms. These compounds exhibited no embryotoxicity or teratogenicity at a concentration of 100 μM in a bioassay with marine medaka (Oryzias melastigma) embryos, implying that these compounds may not be ecologically toxic to marine fish embryos. In addition, none of the compounds exhibited significant cytotoxicity against five human cancer cell lines at 40 μM or anti-inflammatory activities at 50 μM, suggesting their potential for further structural optimization to enhance bioactivity. The research on the constituents of P. pectinifera provides a potential foundation for drug development and marine ecotoxicology.

Two novel steroidal saponins, trilliumosides K (1) and L (2), were isolated from the rhizomes of Trillium govanianum led by bioactivity-guided phytochemical investigation along with seven known compounds: govanoside D (3), protodioscin (4), borassoside E (5), 20-hydroxyecdysone (6), 5,20-hydroxyecdysone (7), govanic acid (8), and diosgenin (9). The structure of novel compounds 1-2 was established using analysis of spectroscopic data including 1D and 2D nuclear magnetic resonance (NMR) and high resolution mass spectrometry (HR-ESI-MS) data. All isolated compounds were evaluated for in vitro cytotoxic activity against a panel of human cancer cell lines. Compound 1 showed significant cytotoxic activity against the A-549 (Lung) and SW-620 (Colon) cancer cell lines with IC50 values of 1.83 and 1.85 μΜ, respectively whereas the IC50 value of Compound 2 against the A-549 cell line was found to be 1.79 μΜ. Among the previously known compounds 3, 5, and 9, the cytotoxic IC50 values were found to be in the range of 5-10 μΜ. Comprehensive anti-cancer investigation revealed that Compound 2 inhibited in vitro migration and colony-forming capability in the A-549 cell line. Additionally, the mechanistic analysis of Compound 2 on the A-549 cell line indicated distinctive alterations in nuclear morphology, increased reactive oxygen species (ROS) production, and decreased levels of mitochondrial membrane potential (MMP). By upregulating the pro-apoptotic protein BAX and downregulating the anti-apoptotic protein BCL-2, the aforementioned actions eventually cause apoptosis, a crucial hallmark in cancer research, which activates Caspase-3. To the best of our knowledge, this study reports the first mechanistic anticancer evaluation of the compounds isolated from the rhizomes of T. govanianum with remarkable cytotoxic activity in the desired micromolar range. [ABSTRACT FROM AUTHOR]

The roots of the plant Cynanchum otophyllum C. K. Schneid (Apocynaceae), known as Qingyangshen in Chinese, are used for a long time as a traditional medicine by different ethnic communities in the Yunnan province (China). The multiple properties and applications of this herbal medicine have been analyzed. C. otophyllum is a perennial herbal liana, nonedible, and generally wild harvested. A cultivation method has been proposed to increase the fruit set level. Qingyangshen is used essentially to treat epilepsy, rheumatism, or other inflammatory diseases. The plant can be found also in diverse polyherbal preparations used in cosmetic or as food supplement (detox products), and in phyto-preparations claimed to reduce hair loss. The plant is a rich reservoir of C-21 steroidal glycosides. Many bioactive compounds have been isolated from this plant and some of them have been pharmacologically characterized, such as otophyllosides, cynotophyllosides, cynanotins, cynotogenins, cynanchins, all briefly evocated here. The plant presents also interesting features in other domains. In particular, leave extracts of C. otophyllum C. K. Schneid contain proteases which are exploited for the local preparation of a cheese-like milk cake. Qingyangshen herbal preparation can be useful to treat epilepsy and inflammation. It has applications beyond medicine in the cosmetic and food industry.

Objective: Response surface methodology was used to optimize the extraction process of steroidal glycosides from Cynanchum auriculatum Royle ex Wight by complex enzymatic method, and its effects on alcohol dehydrogenase activity and human hepatoma cell HepG2 were analyzed. Methods: Four experimental factors; enzymolysis duration, temperature, compound enzyme dose and pH were used as responses to a single-factor experiment of the Response Surface Methodology on the steroidal glycoside yields, using perennial C. auriculatum as the target material. The alcohol-induced hepatocyte damage model of HepG2 was used to investigate the contents of ALT, LDH, and GSH and changes in cell shape. Results: The results show that the optimum extraction conditions of steroidal glycoside enzyme were obtained at an enzymolysis duration of 100 min, a temperature of 46 ℃, enzyme dose of 1.30% and pH of 5.0. Consequently, the actual extraction rate of （2.80±0.04）% was achieved using the optimized process conditions, which was close to the expected value. Compared with the model group, it significantly suppresses the growth of ALT and LDH while increasing the amount of intracellular GSH, and the cell damage was restored. Conclusion: The compound enzyme method can effectively extract the steroidal glycosides of Cynanchum auriculatum Royle ex Wight; steroidal glycosides of C. auriculatum have hepatoprotective effect.

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Two non-sulfated steroidal glycosides, cistoindosides A-B were isolated from organic extract of the marine 'old woman octopus' Cistopus indicus (family Octopodidae). Their structures were characterized as 3β-acteoxy-23β-hydroxy-cholesta-9-ene-β-D-xylopyranoside (cistoindoside A) and 22,23-epoxy-3β-hydroxy-cholesta-5-ene-β-D-4'-O-acetoxy-xylopyranoside (cistoindoside B). Cistoindoside B, glycosylated with β-D-4'-O-acetoxy-xylopyranoside in conjunction with epoxy moieties displayed superior anti-inflammatory properties as acknowledged by its promising 5-lipoxygenase attenuation potential (IC50 2.11 µM) than the 5-lipoxygenase inhibitor drug zileuton (IC50 3.76 µM). The anti-inflammatory properties were corroborated by the promising antioxidant activities (IC50 ∼ 1.0–1.5 mM) of these steroid glycosides. Sizeably greater electronic properties, balanced hydrophobic-lipophilic properties (log POW ∼ 4.0) and comparatively lower steric factors were directly proportional to their bioactivities. Molecular simulation studies in the active sites of 5-lipoxygenase displaying lesser binding energies and inhibition constant (Ki) of cistoindoside B could be correlated with anti-inflammatory properties. Cistoindosides could be projected for their utilization as potential bioactive leads in functional food and pharmaceutical applications. [ABSTRACT FROM AUTHOR]

Two new furostanol saponins, named parisverticillatosides A and B (1 and 2), together with eleven known steroidal glycosides (3–13), were isolated from the roots of Paris verticillata M.Bieb. The structures of the new compounds were established based on extensive spectroscopic analysis and chemical evidence. Interestingly, Compounds 1 and 2 were identified as a pair of epimers that only differ in the configuration of C-23. The discovery of new Compounds 1 and 2 extended the diversity and complexity of the saponin family in the genus Paris. The cytotoxicity of all saponins against human glioblastoma U87 and U251 cell lines was evaluated. The results showed that the new furostanol saponins 1 and 2 were inactive, while the spirostanol saponins 4 and 5 exhibited notable cytotoxicity against two cell lines with IC 50 values of 1.44–3.98 μM. [Display omitted] • Two new saponins along with 11 known ones were isolated from Paris verticillata M.Bieb. • The new compounds were identified as a pair of epimers. • Compounds 4 and 5 exhibited significant cytotoxicity against U87 and U251 cells with IC 50 values of 1.44 to 3.98 μM. [ABSTRACT FROM AUTHOR]

Polygonatum species have been used as traditional medicines and functional foods in Asia and Europe since ancient times. In this study, a fast and simple method based on liquid chromatography coupled with electrospray ionization mass spectrometry (LC-ESI-MS) was developed to systematically analyze and identify the steroidal glycosides in four major Polygonatum species distributed in Japan, including P. odoratum, P. falcatum, P. macranthum, and P. sibiricum. As a result, 31 steroidal glycosides were tentatively identified, including 18 known and 13 previously unreported glycosides. Their structures were identified by the interpretation of chromatographic behavior and ESI-MS fragmentation patterns. The identification of 31 steroidal glycosides was indicative of a common biogenetic pathway in Polygonatum species. Our study disclosed the chemical profiling of steroidal glycosides in the plants of Polygonatum species, which will benefit better phytochemotaxonomical and phytochemical understanding and quality control for their medicinal usage. [ABSTRACT FROM AUTHOR]

Callus and suspension cell cultures of rare foxglove species, Digitalis ciliata and D. grandiflora, were induced from cotyledons and hypocotyls of in vitro seedlings, and their growth and phytochemical profiles were investigated. In both species, callus induction was more efficient from leaf explants (60–80%) than from hypocotyl explants (15–35%). Callus cultures of both species grew well with growth indices ranged from 5 to 10 depending on the genotype. Suspension culture growth profiles also differed between the two species with a 10–11-days lag-phase observed for D. grandiflora and a bi-phasic growth curve without lag-phase recorded for D. ciliata. The main growth characteristics of the D. grandiflora suspension cell culture (maximum biomass accumulation ~ 14 g/L, growth index ~ 10, economic coefficient ~ 0.42, biomass productivity ~ 0.53 g/(L × day)) were 1.5–3 times higher than those for D. ciliata. Ten compounds were identified in cell biomass using UPLC-ESI-Q-TOF-MS: phenylethanoids digiciliside A, digiciliside B, maxoside, purpureaside E, their methyl derivatives and isomers, and two furostanol glycosides with aglycone tigogenin. Phenylethanoid glycosides were major compounds and comprised 0.8–1.1% of dry weight. During the two-years cultivation, suspension cultures retained the ability to accumulate most of the identified compounds evidencing for stability of species-specific secondary metabolism in cultured foxglove cells during this period. Key message: Phenylethanoid glycosides (1.1% DW) and steroidal furostanol glycosides were identified in callus and suspension cell cultures of rare medicinal species Digitalis ciliata and D. grandiflora developed for the first time. [ABSTRACT FROM AUTHOR]

Rhizogenic, callus, and suspension cultures in vitro were obtained for Digitalis lanata and their growth, cytophysiological and biochemical characteristics were investigated. The obtained cultures were characterized by good growth characteristics (growth indexes I in the range of 5–13). Suspension cell culture had a specific growth rate μ within 0.2–0.3 days–1 and it was characterized by a two-phase growth curve (growth retardation during the exponential phase). In the obtained cultures, a study of the qualitative and quantitative composition of secondary metabolites by UPLC-ESI-MS and HPLC-ESI-MS showed the absence of cardiac glycosides. At the same time, phenylethanoids and steroidal glycosides of the furostanol type were found in all studied cultures. The total content of phenylethanoids in callus and suspension cultures was approximately 0.5% of the dry biomass. Based on the results of mass spectrometry, ten phenylethanoid structures, including digiciliside A, digiciliside B, maxoside, purpureaside E, and their methyl derivatives and isomers, and also seven furostanol glycosides with aglycones tigogenin and gitogenin were identified. It has been shown that the composition of secondary metabolites depends on the degree of cell differentiation: furostanol glycosides were prevalent in a rhizogenic culture consisting mainly of differentiated cells, while the diversity of phenylethanoids significantly increases in callus and suspension cell cultures consisting of dedifferentiated cells. The results of the study confirm the hypothesis put forward in our previous works about the specificity of secondary metabolism and its high intensity in plant cell cultures. [ABSTRACT FROM AUTHOR]

Abstract Two new C21 steroidal glycosides, paniculatumosides H and I, together with four known ones were isolated from the roots of Cynanchum paniculatum (Bge.) Kitag. Their structures were identified by spectroscopic methods including extensive 1D and 2D NMR techniques. All compounds were subjected to detect the anti-tobacco mosaic virus (TMV) activities and their cytotoxities against three human tumor cell lines (SMMC-7721, MDA-MB-231 and A549). The results showed that compounds 1 and 5 exhibited potent protective activities against TMV, while 2, 4 and 6 had moderate effects on the SMMC-7721 cancer cells viability. Graphical Abstract

As our ongoing chemical investigation, two new pregnane steroidal glycosides, cynataihosides G (1), with a new aglycone, and H (2) were isolated from the 95% ethanol extract of Cynanchum taihangense. Their structures were elucidated on the basis of 1 D and 2 D NMR spectral data, HR-ESI-MS analysis and qualitative chemical methods. The compounds were subjected to detect the cytotoxicity against three human tumor cell lines (HL-60, THP-1 and PC-3). The compounds displayed no significant cytotoxicity. Supplemental data for this article can be accessed at . Supplemental data for this article can be accessed at . [ABSTRACT FROM AUTHOR]

Two new pregnane glycosides, 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside} (1) and 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}(2), have been isolated along with two known spirostanol saponins from the underground parts of Hosta ventricosa. Their structures were elucidated on the basis of chemical and spectral evidence. The anti-inflammatory activities of these steroidal glycosides were evaluated using a xylene-induced ear edema model. Our results indicated that the compounds exhibited promising anti-inflammatory activities. [ABSTRACT FROM AUTHOR]

Extracts from the rhizomes of Paris species have been used in Asia to help treat inflammation, infection, analgesia, detoxification, dysentery, etc. Analysis of the chemical components from the rhizomes of Paris vietnamensis showed that they contained polyphenols, flavons, flavonols, flavonoids, tannins and steroidal and triterpenoid saponins. In this study, P. vietnamensis was identified from the sample collected from Sapa, Laocai province, Vietnam and three steroidal glycosides from rhizomes of this species were evaluated for anticancer and antimicrobial activity in vitro. The samples were identified as belonging to P. vietnamensis species through a combination of morphological characteristics and DNA barcodes based on the nucleotide sequence of the ITS and matK. All three steroidal glycosides exhibited strong cytotoxic activity against SK-LU-1, HeLa and MKN7 cell lines with IC50 values ranging from 1.07 to 4.37 µmol L−1, and exhibited high antimicrobial activity against strains of Serratia marcescens, Escherichia coli, Lactobacillus plantarum and Bacillus subtilis. This study provides information on the antibacterial and inhibitory activities of steroidal glycosides derived from the rhizomes of P. vietnamensis collected from Sapa, Laocai province, Vietnam on cancer cell lines. Thus, P. vietnamensis could be used as an alternative to other species of the Paris genus for anticancer and antimicrobial treatment.

Plants link interactions between aboveground and belowground organisms. Herbivore-induced changes in plant chemistry are hypothesized to impact entire food webs by changing the strength of trophic cascades. Yet, few studies have explored how belowground herbivores affect the behaviors of generalist predators, nor how such changes may act through diverse changes to the plant metabolome. Using a factorial experiment, we tested whether herbivory by root-knot nematodes (Meloidogyne incognita) affected the aboveground interaction among milkweed plants (Asclepias fascicularis or Asclepias speciosa), oleander aphids (Aphis nerii), and aphid-tending ants (Linepithema humile). We quantified the behaviors of aphid-tending ants, and we measured the effects of herbivore treatments on aphid densities and on phytochemistry. Unexpectedly, ants tended aphids primarily on the leaves of uninfected plants, whereas ants tended aphids primarily at the base of the stem of nematode-infected plants. In nematode-infected plants, aphids excreted more sugar per capita in their ant-attracting honeydew. Additionally, although plant chemistry was species-specific, nematode infection generally decreased the richness of plant secondary metabolites while acting as a protein sink in the roots. Path analysis indicated that the ants' behavioral change was driven in part by indirect effects of nematodes acting through changes in plant chemistry. We conclude that belowground herbivores can affect the behaviors of aboveground generalist ant predators by multiple paths, including changes in phytochemistry, which may affect the attractiveness of aphid honeydew rewards. [ABSTRACT FROM AUTHOR]

Three sesquiterpene glycosides, i.e., nerolidol derivatives, and steroidal glycosides of the 3-furostanol and 1-spirostanol series, one of which was new and characterized as (25R)-26-O-β-D-Glcp-5α-furostan-3β,22α,26-triol 3-O-β-D-Xylp-(1→3)-[O-β-D-Glcp-(1→3)-O-β-D-Glcp-(1→2)]-O-β-D-Glcp-(1→4)-O-β- D-Galp, were isolated from flowers of Yucca elephantipes Regel cultivated in Georgia. The structures of the glycosides were elucidated using one- and two-dimensional NMR (1H, 13C, HSQC, HMBC, COSY) and mass spectrometry (ESI-MS). [ABSTRACT FROM AUTHOR]

Effect of synthetic analogs of auxins—2.4-dichlorophenoxyacetic (2.4-D) and α-naphthylacetic (α-NAA) acids—on growth characteristics and accumulation of steroidal glycosides was investigated in suspension cell culture of Tribulus terrestris L. It was found that the substitution of α-NAA for 2.4-D in the nutrient medium brought about a rise in the content of steroidal glycosides in the cultured cells (up to six times) and broadened their structural diversity (nine identified oligofurostanosides when growing culture on the medium with α-NAA vs. five compounds on the medium with 2.4-D). Positive influence of α-NAA exerted on biosynthetic characteristics of T. terrestris suspension cell culture was accompanied by changes in cell morphology (cytodifferentiation), the extent of their aggregation, and gradual decrease (during 3–4 cycles of growing) in culture viability up to its extinction. Simultaneous presence of both synthetic analogs of auxins (α-NAA and 2.4-D) in the growing medium also caused a rise in the content of steroidal glycosides in the cells of T. terrestris, although it was less pronounced (up to three times); however, the culture showed a relatively steady growth and great viability in this case. It was concluded that these two auxin analogs differently influenced the growth of plants' cells in vitro and biosynthesis of substances of specialized metabolism, 2.4-D promoted cell proliferation, whereas α-NAA induced cytodifferentiation and activated the production of secondary compounds. This conclusion is corroborated by the data concerning plant cell cultures of other species of medicinal plants accumulating secondary metabolites from other groups. For instance, in the experiments with suspension cell culture of Panax ginseng C.A. Mey., substitution in the growth medium of α-NAA for 2.4-D brought about a rise in the content and diversity of triterpene glycosides (ginsenosides) associated with an elevated cell aggregation and deterioration of culture's viability. Comparison of production of steroidal glycosides in plant cell cultures of T. terrestris and Dioscorea deltoidea Wall. that is grown for more than 40 years has shown that both cultures accumulated only furostanol (rather than spirostanol) glycosides that promoted cell proliferation. In suspension cell culture of Dioscorea, a high level of oligofurostanosides (up to 12% of dry biomass) was accumulated when growing culture on the medium with 2.4-D. Thus, investigation into the production of furostanol glycosides in plant cultured cells points to a multifactor system of regulation of secondary metabolism in vitro. Different synthetic auxin analogs may exert alternative influences on growth and biosynthetic processes. At the same time, prolonged culturing leads to an autoselection of cells with the properties promoting proliferation, specifically, with a high content of furostanol glycosides. [ABSTRACT FROM AUTHOR]

The protected cultivation technology, through which the various inbred generations with the combination of economic valuable traits and different level of sterility can be produced, is used in order to accelerate the breeding program. However, there is a negative effect of inbreeding depression and self-incompatibility can often occur and cause the loss of valuable breeding forms. The aim of the work was to study the influence of steroidal glycosides capsicoside (SGC) on exhibition of CMS, and morphobiological parameters of 13 inbred generations that were produced from fertile plant and partly sterile plants with level of sterility 10% and 50%. The seeds were soaked for 24 hours in water solution of SGC with concentration 10-3%, and in water control. Then the seeds were dried up and sown in the greenhouse. The stecklings and roots obtained were vernalized at 3-5Co. Mother plants were grown under 18 hour photoperiod in greenhouse with supplementary lighting. Inbreeding seeds were obtained in individual cloth isolators. It was shown that for all generations the treatment with SGC improved the seed germination (4-8% more), increased the root index and its length (12-24% more), decreased betanin content (22-48% less) in comparison with control. The action of SGC on the other morphological and biochemical traits such as height of leaf rosette, leaf number, plant and root weight, head size, number of generative buds, and nitrate content was defined by the level of sterility of mother plant. The most expressed effect for all traits mentioned was seen in inbreeding generations of sterile plants with high level of sterility. After action effect of seed treatment with SGC on development of seed plants from inbreeding generations, not depending on sterility level of mother plants, showed the positive influence on plant habitus of seed mother plants, decreasing the plant height, but increasing stem number and functional parameters of microgametophyte in fertile plants. This caused the improved seed formation 1.6-2.2 times higher during inbreeding process and increased the portion of plants with high productivity. The SGC had no effect on exhibition of CMS trait. Thus, the SGC is worth using in valuable highly inbreeding forms inclined to self-sterility, in order to enlarge the genetic variation and output of divers generations. However, it should be taken into consideration that the complicated effect on the plant traits can be noticed in inbreeding generation of red beet and may have an effect on the result of selection process at the root stage.

Pericarps of Digitalis ciliata Trautv. yielded 12 steroidal compounds, three of which were new, i.e., two furostanol and one spirostanol glycosides. [ABSTRACT FROM AUTHOR]

Steroidal saponins are a group of glycosides widely distributed among monocotyledonous families. They exert a wide spectrum of biological effects including cytotoxic and antitumor properties which are the most studied. This review is an update of our previous paper—Saponins as cytotoxic agents (Podolak et al. in Phytochem Rev 9:425–474, 2010) and covers studies that were since published (2010–2018). In this paper we refer to steroidal saponins presenting results of cytotoxicity studies, mechanisms of action and structure–activity relationships. [ABSTRACT FROM AUTHOR]

• Four new furostanol saponins were isolated from Aspidistra elatior Blume. • The structures were determined by chemical evidence and spectroscopic analyses. • 1 and 2 were a pair of diastereoisomeric furostanol saponins with highly oxidized structural feature. • 3 and 4 showed moderate anti-inflammatory activities. Four new furostanol saponins, named aspidsaponins E-H (1–4) were isolated from the rhizomes of Aspidistra elatior Blume. Their structures were determined based on chemical methods and spectral data. Compounds 1 and 2 were a pair of diastereoisomeric furostanol saponins and possessed the highly oxidized structural feature of 1β, 2β, 3β, 4β, 5β, 26-hexanol-steroids, and compounds 3 - 4 were steroidal glycosides with a tetra-saccharide chain at C3. The isolated compounds (1–4) were tested in vitro for inhibitory activities against LPS-induced nitric oxide production in RAW264.7 macrophages. Among them, compounds 3 and 4 showed excellent anti-inflammatory activities with IC 50 values 82.1 and 65.9 μM, respectively. [ABSTRACT FROM AUTHOR]

Extracts from the rhizomes of Paris species have been used in Asia to help treat inflammation, infection, analgesia, detoxification, dysentery, etc. Analysis of the chemical components from the rhizomes of Paris vietnamensis showed that they contained polyphenols, flavons, flavonols, flavonoids, tannins and steroidal and triterpenoid saponins. In this study, P. vietnamensis was identified from the sample collected from Sapa, Laocai province, Vietnam and three steroidal glycosides from rhizomes of this species were evaluated for anticancer and antimicrobial activity in vitro. The samples were identified as belonging to P. vietnamensis species through a combination of morphological characteristics and DNA barcodes based on the nucleotide sequence of the ITS and matK. All three steroidal glycosides exhibited strong cytotoxic activity against SK-LU-1, HeLa and MKN7 cell lines with IC50 values ranging from 1.07 to 4.37 µmol L−1, and exhibited high antimicrobial activity against strains of Serratia marcescens, Escherichia coli, Lactobacillus plantarum and Bacillus subtilis. This study provides information on the antibacterial and inhibitory activities of steroidal glycosides derived from the rhizomes of P. vietnamensis collected from Sapa, Laocai province, Vietnam on cancer cell lines. Thus, P. vietnamensis could be used as an alternative to other species of the Paris genus for anticancer and antimicrobial treatment. [ABSTRACT FROM AUTHOR]

Screening assays showed that total glycoside-rich fraction (TG) of rhizomes of Polygonatum sibiricum unveiled remarkable anti-proliferative activities against three cancer cell lines (A549, HepG2, and Caco2). Activity-guided isolation of TG afforded seven undescribed steroidal glycosides (polygonosides 1 – 7), along with 24 known glycosides. Their structures were established by 1D and 2D NMR spectroscopic analyses, high-resolution mass spectrometry, and chemical evidence. The isolated steroidal glycosides were tested for their antiproliferative activities against A549, HepG2, and Caco2 cells. Compounds 8 , 10 , 11 , and 16 possessed stronger anticancer activities against A549 cells than the positive control Bay (25.8 μM), with IC 50 values ranging from 5.8 to 24.2 μM. Compound 10 reduced the expression of Blc-2 and pro-caspase3 and increased the production of Bax as determined by western blotting. Molecular docking experiment suggested that 10 bound stably to the BH3-binding groove of the Bcl-2 protein by hydrogen bond interactions. These compounds could be candidates for anticancer agents with cytotoxic activity. Image 1 • Undescribed and 24 known glycosides were identified from Polygonatum sibiricum. • Glycosides were suggested to be effective material basis for the cytotoxic effects. • The cytotoxic action mechanism of compound 10 was investigated. [ABSTRACT FROM AUTHOR]

Two new C21 steroidal glycosides, paniculatumosides H and I, together with four known ones were isolated from the roots of Cynanchum paniculatum (Bge.) Kitag. Their structures were identified by spectroscopic methods including extensive 1D and 2D NMR techniques. All compounds were subjected to detect the anti-tobacco mosaic virus (TMV) activities and their cytotoxities against three human tumor cell lines (SMMC-7721, MDA-MB-231 and A549). The results showed that compounds 1 and 5 exhibited potent protective activities against TMV, while 2, 4 and 6 had moderate effects on the SMMC-7721 cancer cells viability. [ABSTRACT FROM AUTHOR]

Four new steroidal glycosides (1–4), including two steroidal saponins named lililancifoloside B and C (1 – 2), one pregnane glycoside named lililancifoloside D (3), and one C22-steroidal lactone glycoside named lililancifoloside E (4), together with five known ones (5–9), were isolated from the bulbs of Lilium lancifolium Thunb. By using spectroscopic analysis, including 1D, 2D NMR, and HR-ESI-MS, the structures of 1–4 were elucidated. All isolates were tested for their cytotoxic potential against the MCF-7, MDA-MB-231, HepG2, and A549 cell lines. Compound 6 distinguished out among them, IC 50 values of 3.31, 5.23, 1.78, and 1.49 μM against the four cell lines, respectively. Other compounds such as compound 3 , 5 , and 9 have also shown specific cytotoxic activity. Next, studies showed that compound 6 might cause HepG2 cells to undergo a cell cycle arrest during the G2/M phase and apoptosis. [Display omitted] • Four new steroidal glycosides were isolated from the bulbs of Lilium lancifolium Thunb.. • The cytotoxicity of all isolates against MCF-7, MDA-MB-231, HepG2, and A549 cell lines were investigated. • Compound 6 displayed significant cytotoxic activitity against all tested cell lines. • Studies revealed that compound 6 could induce cell cycle arrest at G2/M phase and apoptosis in HepG2 cells. [ABSTRACT FROM AUTHOR]

Dioscorea deltoidea is a medicinal plant valued for its high content of steroidal glycosides (SG)—bioactive compounds with cardioprotective and immunomodulation actions, also used to treat reproductive system disorders. To overcome the limitations of natural resources of this species, a suspension cell culture of D. deltoidea was developed as a renewable and ecologically sustainable source of raw biomass and SG. Cell culture demonstrated stable and intensive growth in the laboratory (20 L) and industrial (630 L) bioreactors operated under a semi-continuous regime (specific growth rate 0.11–1.12 day−1, growth index 3.5–3.7). Maximum dry weight accumulation (8.5–8.8 g/L) and SG content (47–57 mg/g DW) were recorded during the stationary phase. Bioreactor-produced cell biomass contained inorganic macro (K, Ca, Mg, Na) and micro (Zn, Mn, Fe, B, Al, Cu, Cr, Se, Co, Ni) elements in concentrations within the safe range of dietary recommendations. Acute toxicity test showed no or insignificant changes in organ weight, hematological panel and blood biochemistry of laboratory animals fed with 2000 and 5000 mg/kg dry biomass. The results suggest that cell culture of D. deltoidea grown in bioreactors has great potential to be used as functional foods and a component of specialized dietary supplements in complex therapy of reproductive system disorders and mineral deficiency.

Dioscorea villosa, commonly known as “Wild Yam” and native to North America, is well documented for its pharmacological properties due to the presence of steroidal glycosides. However, the hepatoprotective potential of these compounds has not been studied so far. The present investigation was aimed to study the hepatoprotective effect of the steroidal glycosides from D. villosa against H2O2, a known hepatotoxin, in human liver cell line (HepG2). Cytotoxicity assessment was carried out in cells exposed to various concentrations (10–50 μM) of compounds for 24 h using MTT assay and morphological changes. All tested compounds were known and among them, spirostans (zingiberensis saponin I, dioscin, deltonin and progenin III) were found to be cytotoxic whereas, furostans (huangjiangsu A, pseudoprotodioscin, methyl protobioside, protodioscin, and protodeltonin) were non-cytotoxic. Further, HepG2 cells were pretreated with biologically safe concentrations (10, 30, and 50 μM) of non-cytotoxic compounds and then cytotoxic (0.25 mM) concentration of H2O2. After 24 h, cell viability was assessed by MTT and NRU assays, while morphological changes were observed under the microscope. The results showed that treatment of HepG2 cells with compounds prior to H2O2 exposure effectively increased cell viability in a concentration-dependent manner. Furthermore, huangjiangsu A, pseudoprotodioscin, methyl protobioside, protodioscin, and protodeltonin at 50 μM increased GSH level and decreased intracellular ROS generation against H2O2-induced damages. The results from this study revealed that compounds isolated from D. villosa have hepatoprotective potential against H2O2-induced cytotoxicity and ROS generation and could be promising as potential therapeutic agents for liver diseases.

Examination of the bulbs of Lilium pumilum (Liliaceae) led to the isolation of four novel steroidal glycosides (1–4) with a 2,3,4-trisubstituted β-d-glucopyranosyl unit. In 1 and 3, the α-L-arabinopyranosyl moiety is linked to C-3 of the inner trisubstituted β-D-glucopyranosyl group and is present as an usual 4C1 conformation. In contrast, in 2 and 4, the α-L-arabinopyranosyl moiety, which is attached to C-4 of the inner trisubstituted β-D-glucopyranosyl group, is present as a 1C4 conformation. The structures of the new steroidal glycosides were determined based on the results of spectroscopic analyses, including two-dimensional (2D) NMR data and hydrolysis.

Biological activity of steroidal glycosides from the bulbs of Allium cyrillii Ten. have been investigated. It is shown that they have not possess bactericidal properties, but have high fungicidal and growth-regulatory activity.

Abstract Bioassay-guided isolation of the 80% methanol extract of the aerial parts of Chrysophthalmum montanum (DC.) Boiss. (Asteraceae) led to the isolation of four known guaianolide-type sesquiterpene lactones, 6 α -acetoxy-4 α -hydroxy-1 β H-guaia-9.11(13)-dien-12.8 α -olide (1) , 6 α -acetoxy-4 α -hydroxy-9 β.10 β -epoxy-1 β H-guaia-11(13)-en-12.8 α -olide (2) , 4 α ,6 α -dihydroxy-1 β ,5 α ,7 α H-guaia-9(10),11(13)-dien-12,8 α -olide (3) , and (4 α ,5 α ,8 β ,10 β)-4,10-dihydroxy-1,11(13)-guaidien-12,8-olide (4), along a steroidal glycoside mixture (5a and 5b). The structures of the compounds were identified on the basis of spectroscopic data. Among them, 2, 4 and a steroidal glycoside mixture were obtained from C. montanum for the first time. All isolates were also first time assayed for in vitro cytotoxicities against four human cancer cell lines, i.e. breast (MCF-7, MDA-MB 231), colon (HT-29), and lung (PC3). Among the isolates, 1 – 3 showed significant inhibitory effect on the proliferation of cancer cells with viability ranging from 6.86 to 26.51%, while steroidal glycoside mixture showed no cytotoxicity, except against HT-29 (viability 61.99%). Compound 4 exhibited strong and selective cell growth inhibition against HT-29 with viability 20.99% and was identified as a promising compound with high selectivity between cancer cells and normal human lung cells (BEAS-2B), especially against HT-29 (IC 50 = 12.2 μg/mL) compared to that of cisplatin. These results suggested that 4 is worthy of further study to determine its cytotoxicity mechanisms. Graphical abstract Image 1 [ABSTRACT FROM AUTHOR]

Solanum dulcamara (Bittersweet nightshade) shows significant intraspecific variation in glycoalkaloid (GA) composition and concentration. We previously showed that constitutive differences in overall GA levels are correlated with feeding preference of the grey field slug (GFS; Deroceras reticulatum). One particularly preferred accession, ZD11, contained low GA levels, but high levels of previously unknown structurally related uronic acid conjugated compounds (UACs). Here we test whether different slug species as well as insect herbivores show similar feeding preferences among six S. dulcamara accessions with different GA chemotypes. In addition, we investigate whether slug feeding can lead to induced changes in the chemical composition and affect later arriving herbivores. A leaf disc assay using greenhouse-grown plants showed that three slug species similarly preferred accessions with low GA levels. Untargeted metabolomic analyses showed that previous slug feeding consistently increased the levels of N-caffeoyl-putrescine and a structurally related metabolite, but not the levels of GAs and UACs. Slug-induced responses only affected slug preference in one accession. A common garden experiment using the same six accessions revealed that ZD11 received the highest natural gastropod feeding damage, but suffered the lowest damage by specialist flea beetles. The latter preferred to feed on accessions with high GA levels. Our study indicates that different selection pressures imposed by generalist gastropods and specialist insects may explain part of the observed chemical diversity in S. dulcamara. [ABSTRACT FROM AUTHOR]

The phytochemical investigation of the whole plant of Polygonatum multiflorum resulted in the isolation of two new steroidal glycosides, polmultoside A (4) and polmultoside B (5), along with three known glycosides protobioside (1), protodeltonin (2) and huangjiangsu A (3). The structures of the isolated compounds have been elucidated by extensive 1D (1H, 13C) and 2D (COSY, HSQC, HMBC) NMR spectral data analysis, as well as high-resolution mass determinations. [ABSTRACT FROM AUTHOR]

Dioscorea villosa, commonly known as “Wild Yam” and native to North America, is well documented for its pharmacological properties due to the presence of steroidal glycosides. However, the hepatoprotective potential of these compounds has not been studied so far. The present investigation was aimed to study the hepatoprotective effect of the steroidal glycosides from D. villosa against H2O2, a known hepatotoxin, in human liver cell line (HepG2). Cytotoxicity assessment was carried out in cells exposed to various concentrations (10–50 μM) of compounds for 24 h using MTT assay and morphological changes. All tested compounds were known and among them, spirostans (zingiberensis saponin I, dioscin, deltonin and progenin III) were found to be cytotoxic whereas, furostans (huangjiangsu A, pseudoprotodioscin, methyl protobioside, protodioscin, and protodeltonin) were non-cytotoxic. Further, HepG2 cells were pretreated with biologically safe concentrations (10, 30, and 50 μM) of non-cytotoxic compounds and then cytotoxic (0.25 mM) concentration of H2O2. After 24 h, cell viability was assessed by MTT and NRU assays, while morphological changes were observed under the microscope. The results showed that treatment of HepG2 cells with compounds prior to H2O2 exposure effectively increased cell viability in a concentration-dependent manner. Furthermore, huangjiangsu A, pseudoprotodioscin, methyl protobioside, protodioscin, and protodeltonin at 50 μM increased GSH level and decreased intracellular ROS generation against H2O2-induced damages. The results from this study revealed that compounds isolated from D. villosa have hepatoprotective potential against H2O2-induced cytotoxicity and ROS generation and could be promising as potential therapeutic agents for liver diseases. [ABSTRACT FROM AUTHOR]

Four new furostanol saponins, named aspidsaponins A–D ( 2–5 ), together with one known steroidal saponin ( 1 ) were isolated from the rhizomes of Aspidistra elatior Blume. Their structures were determined on the basis of chemical methods and spectral data. Compounds 1 and 2 , 4 and 5 were two pairs of diastereoisomeric furostanol saponins, and 3-5 were rarely steroidal glycosides of the C4-linked sugar and possessed highly oxidized structural feature. The isolated compounds ( 1–5 ) were tested in vitro for their cytotoxic activities against four cancer cell lines A549, Caski, HepG2 and MCF-7. Among them, compounds 1 and 2 showed notable cytotoxic activities against the four cancer cell lines with IC 50 values ranging from 3.8–13.8 μM. [ABSTRACT FROM AUTHOR]

Solanum nigrum L., is traditionally used for the management of the various liver disorders. Investigating the effect of polarity based fractionation of S. nigrum for its hepatoprotective effect on Hep G2 cells in vitro to provide base of its activity by quantifying in steroidal glycosides responsible for hepatoprotective potential. A new UPLC-ESI-MS/MS method following a high performance thin layer chromatography (HPTLC) has been developed and validated for quantification of steroidal glycosides and aglycone (solasonine, solamargine, and solasodine, respectively). The in vitro antioxidant potential, total phenolics, and flavonoid content were also determined in different fractions. The newly developed UPLC-ESI-MS/MS and HPTLC methods were linear (r2 ≥ 0.99), precise, accurate, and showing recovery more than 97%. The n-butanol enriched fraction of S. nigrum berries was found to be the most potent hepatoprotective fraction against all other fractions as it showed significantly (p < 0.01) better in vitro anti-oxidant potential than other fractions. Quantification by both methods revealed that, content of steroidal glycosides and aglycones are more than 20% in n-butanol fraction as compared to other fractions. The screened steroidal glycoside n-butanol enriched fraction underwent bioefficacy studies against D-galactosamine and H2O2 induced toxicity in HepG2 cell line showing significant (p < 0.05) liver protection. However, developed method can be used for the quality control analysis with respect to targeted metabolites and it can be explored for the pharmacokinetic and pharmacodynamic analysis in future.

Steroidal glycosides are important sources of innovative drugs. The increased diversification of steroidal glycosides will expand the probability of discovering active molecules. It is an efficient approach to diversify steroidal glycosides by using steroidal glycosyltransferases. OcUGT1, a uridine diphosphate-d-glucose (UDP-Glc)-dependent glycosyltransferase from Ornithogalum caudatum, is a multifunctional enzyme, and its glycodiversification potential towards steroids has never been fully explored. Herein, the glycodiversification capability of OcUGT1 towards 25 steroids through glucosylation and transglucosylation reactions were explored. Firstly, each of 25 compounds was glucosylated with UDP-Glc. Under the action of OcUGT1, five steroids (testosterone, deoxycorticosterone, hydrocortisone, estradiol, and 4-androstenediol) were glucosylated to form corresponding mono-glucosides and biosides. Next, OcUGT1-mediated transglucosylation activity of these compounds with another sugar donor ortho-nitrophenyl-β-d-glucopyranoside (oNPGlc) was investigated. Results revealed that the same five steroids could be glucosylated to generate mono-glucosides and biosides by OcUGT1 through transglucosylation reactions. These data indicated that OcUGT1-assisted glycodiversification of steroids could be achieved through glucosylation and transglucosylation reactions. These results provide a way to diversify steroidal glycosides, which lays the foundation for the increase of the probability of obtaining active lead compounds.

In this paper, the ultrasound assisted extraction method for isolation of steroidal glycosides from D . deltoidea plant cell suspension culture with a subsequent HPLC-MS determination was developed. After the organic solvent was selected via a two-factor experiment the optimization via Latin Square 4 × 4 experimental design was carried out for the following parameters: extraction time, organic solvent concentration in extraction solution and the ratio of solvent to sample. It was also shown that the ultrasound assisted extraction method is not suitable for isolation of steroidal glycosides from the D . deltoidea plant material. The results were double-checked using the multiple successive extraction method and refluxing extraction. Optimal conditions for the extraction of steroidal glycosides by the ultrasound assisted extraction method were: extraction time, 60 min; acetonitrile (water) concentration in extraction solution, 50%; the ratio of solvent to sample, 400 mL/g. Also, the developed method was tested on D . deltoidea cell suspension cultures of different terms and conditions of cultivation. The completeness of the extraction was confirmed using the multiple successive extraction method. [ABSTRACT FROM AUTHOR]

Two new C21 steroidal glycosides, cynataihosides E (1) and F (2), together with a known one, sublanceoside H2 (3), were isolated from Cynanchum taihangense. The aglycone of cynataihoside F (2) was also a new compound. Their structures were elucidated on the basis of NMR spectroscopic data, HR-ESI-MS analysis, and chemical evidence. Their cytotoxic activities against three human tumor cell lines (HL-60, THP1, and Caco2) were reported. [ABSTRACT FROM AUTHOR]

The bulbs of Lilium brownii Brown var. viridulum Baker (lily) are commonly known as “Bai-he” for both functional food and medicine in China. In this study, the combination of bio-assay guided fractionation and chemical analysis revealed that steroidal glycoside rich L. brownii fraction (SGL) exhibited potential anti-hyperglycaemic activity. Further investigations demonstrated that SGL could increase glucose consumption in HepG2 cells and 3T3-L1 adipocytes by 1.61- and 2.13-fold, respectively, and enhance 3T3-L1 preadipocyte differentiation. Total 29 steroidal glycosides in SGL were positively or tentatively identified using liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (LC-Q-TOF-MS/MS), which afforded us a comprehensive understanding of the bioactive fraction. These results suggested that steroidal glycosides in L. brownii possessed desirable potential in glucose metabolism and insulin sensitivity. This is the first report on the determination of anti-hyperglycaemic activity in steroidal glycoside rich fraction of lily bulbs and characterization of the chemical profiles by LC-Q-TOF-MS/MS.

Callus and suspension plant cell cultures of Tribulus terrestris L., a valuable medicinal plant producing steroidal glycosides, were obtained. The seeds from an American population of T. terrestris were used as explants. Regulation of the production and growth of cell cultures, as well as the biosynthetic characteristics of the cell lines, were studied. The combination of phytohormones of 2,4-D (2.0 mg/L) and BAP (1.0 mg/L) was found to be optimal for callus induction and cultivation. Suspension cell culture obtained in liquid medium of the same composition showed such high growth characteristics during prolonged cultivation (more than 2 years) as a maximum accumulation of dry biomass of 13 g/L, specific growth rate at exponential phase of 0.24 day-1, and economical coefficient of 0.39. A semicontinuous mode of cultivation was used to grow the plant cell suspension in a lab-scale bioreactor. Screening of the steroidal glycosides in the obtained cell cultures was carried out. Steroidal glycosides were not found in the callus cultures. However, as was demonstrated by TLC and UPLC ESI MS methods, the suspension culture contained furostanol glycosides, and their amount increased during the cultivation process. These results support the hypothesis of the autoselection of cultivated cells containing compounds promoting their proliferation in vitro. [ABSTRACT FROM AUTHOR]

Nine steroidal compounds, three of which were new (two furostanol and one spirostanol glycosides), were isolated from pericarp of Digitalis ferruginea L. fruit. [ABSTRACT FROM AUTHOR]

Three new bidesmosidic cholestane-type steroidal glycosides, 16 -O-β - d -glucopyranosyl-cholest-5-en-3 β ,16 β -diol-22-one-3 -O-α - l -rhamnopyranosyl-(1 → 2) -O- [( β - d -glucopyranosyl(1 → 4)] -O-β - d -glucopyranoside ( 1 ), 16 -O-β - d -glucopyranosylcholest-5-en-3 β ,16 β -diol-22-one-3 -O-α - l -rhamnopyranosyl-(1 → 2) -O-β - d -glucopyranoside ( 2 ), and 16 -O-β - d -glucopyranosylcholestan-3 β ,16 β -diol-6,22-dione-3 -O-α - l -rhamnopyranosyl-(1 → 2) -O-β - d -glucopyranoside ( 3 ) were isolated from a methanolic extract of Panicum turgidum . In addition four known compounds, pennogenin 3 β - O - α - l -rhamnopyranosyl-(1 → 2)- O -[ α - l -rhamnopyranosyl-(1 → 4)- O - α - l -rhamnopyranosyl-(1 → 4)]- O - β - d -glucopyranoside ( 4 ), yamogenin 3 β - O - α - l -rhamnopyranosyl-(1 → 2)- O -[ α - l -rhamnopyranosyl-(1 → 4)] -O-β - d -glucopyranoside ( 5 ), yamogenin 3 β - O - α - l -rhamnopyranosyl-(1 → 2) -O- [ α - l -rhamnopyranosyl-(1 → 4)- O - α - l -rhamnopyranosyl-(1 → 4)]- O - β - d -glucopyranoside ( 6 ), and pennogenin 3 β - O - α - l -rhamnopyranosyl-(1 → 2) -O- [ α - l -rhamnopyranosyl-(1 → 4)] -O-β - d -glucopyranoside ( 7 ) were also isolated and characterized . Their structures were established using extensive spectroscopic methods including 1D and 2D NMR and HRESIMS. The isolated compounds were screened for cytotoxicity towards a panel of mammalian cell lines and 4 – 7 were found to be cytotoxic. [ABSTRACT FROM AUTHOR]

Solanum nigrum L., is traditionally used for the management of the various liver disorders. Investigating the effect of polarity based fractionation of S. nigrum for its hepatoprotective effect on Hep G2 cells in vitro to provide base of its activity by quantifying in steroidal glycosides responsible for hepatoprotective potential. A new UPLC-ESI-MS/MS method following a high performance thin layer chromatography (HPTLC) has been developed and validated for quantification of steroidal glycosides and aglycone (solasonine, solamargine, and solasodine, respectively). The in vitro antioxidant potential, total phenolics, and flavonoid content were also determined in different fractions. The newly developed UPLC-ESI-MS/MS and HPTLC methods were linear (r² ≥ 0.99), precise, accurate, and showing recovery more than 97%. The n-butanol enriched fraction of S. nigrum berries was found to be the most potent hepatoprotective fraction against all other fractions as it showed significantly (p < 0.01) better in vitro anti-oxidant potential than other fractions. Quantification by both methods revealed that, content of steroidal glycosides and aglycones are more than 20% in n-butanol fraction as compared to other fractions. The screened steroidal glycoside n-butanol enriched fraction underwent bioefficacy studies against D-galactosamine and H2O2 induced toxicity in HepG2 cell line showing significant (p < 0.05) liver protection. However, developed method can be used for the quality control analysis with respect to targeted metabolites and it can be explored for the pharmacokinetic and pharmacodynamic analysis in future. [ABSTRACT FROM AUTHOR]

Background: Dregea sinensis Hemsl. plant of the genus Dregea volubilis (Asclepiadaceae), plays a vital role in anticancer, antidepression, and immunoregulation. Steroidal glycosides are the main constituents of this herb, which were significant biological active ingredients. Objective: The objective of this study is to recognize the mechanism of anticancer, antidepression, and immunoregulation of D. sinensis Hemsl. Materials and Methods: Seventy-two steroidal glycosides of D. sinensis Hemsl. were evaluated on the docking behavior of tumor-associated proteins (PI3K, Akt, mTOR), depression-related proteins (MAO-A, MAO-B) and immune-related proteins (tumor necrosis factor-a [TNF-α], tumor necrosis factor receptor 2 [TNFR2], interleukin-2Rα [IL-2Rα]) using Discovery Studio version 3.1 (Accelrys, San Diego, USA). Results: The molecular docking analysis revealed that mostly steroidal glycosides of D. sinensis Hemsl. exhibited powerful interaction with the depression-related protein (MAO-A) and the immune-related proteins (TNFR2, IL-2Rα). Some ligands exhibited high binding energy for the tumor-associated proteins (PI3K, Akt, mTOR) and the immune-related protein (TNF-α), but MAO-B showed none interaction with the ligands. Conclusion: This study has paved better understanding of steroidal glycosides from D. sinensis Hemsl. as potential constituents to the prevention of associated cancer, depression and disorders of immunoregulation. Abbreviations used: PI3K: Phosphatidyl inositol 3-kinase; Akt: Protein kinase B; mTOR: Mammalian target of rapamycin; MAO-A: Monoamine oxidase A; MAO-B: Monoamine oxidase B; TNF-α: Tumor necrosis factor a; TNFR2: Tumor necrosis factor receptor 2; IL-2Ra: The alpha subunit (CD25) of the interleukin-2 receptor; DS: Discovery Studio; PDB: Protein Database Bank; 3D: three-dimensional. [ABSTRACT FROM AUTHOR]

Four new C 21 steroidal glycosides, cynataihosides A ( 1 ), B ( 2 ), C ( 5 ) and D ( 6 ), together with two known compounds, cynanoside J ( 3 ) and glaucoside H ( 4 ), were isolated from the 95% ethanol extract of Cynanchum taihangense . The aglycone of cynataihoside A ( 1 ) was also a new compound, and that of cynataihoside B ( 2 ) was unusual. Their structures were elucidated on the basis of 1D- and 2D- NMR spectroscopic data, HR-ESI–MS analysis and qualitative chemical methods. The compounds were subjected to detect the cytotoxicity against three human tumor cell lines (HL-60, THP1 and Caco2). Compound 2 selectively showed potent cytotoxic activity on Caco2 cells with IC 50 value of 1.23 μM, being more effective than the positive control (5-fluorouracil, IC 50 = 6.76 μM). Compound 5 was more sensitive to THP1 cell line than HL-60 and Caco2 cell lines with IC 50 values of 7.85 μM. Moreover, the structure-activity relationship of the C 21 steroidal glycosides on the cell lines was analyzed. [ABSTRACT FROM AUTHOR]

Five new compounds, i.e., four furostanol glycosides and one triterpene saponin, were isolated from roots of Digitalis ciliata. The structures of the obtained compounds were established using 1D and 2D NMR (H, C, HSQC, HMBC, COSY) and mass spectroscopy (ESI-MS). [ABSTRACT FROM AUTHOR]