Steroidal Glycosides Research Articles

Total Synthesis of Starfish Cyclic Steroid Glycosides.

Starfishes have evolved with a special type of secondary metabolites, namely starfish saponins, to ward off various predators and parasites; among them, the starfish cyclic steroid glycosides stand out structurally, featuring a unique 16-membered ring formed by bridging the steroidal C3 and C6 with a trisaccharide. The rigid cyclic scaffold and the congested and vulnerable steroid-sugar etherate linkage present an unprecedented synthetic challenge. Here we report a collective total synthesis of the major starfish cyclic steroid glycosides, namely luzonicosides A (1) and D (2) and sepositoside A (3), with an innovative approach, which entails a de novo construction of the ether-linked hexopyranosyl units, use of olefinic pyranoses as sugar precursors, and a decisive ring-closing glycosylation under the mild gold(I)-catalyzed conditions.

Total Synthesis of Starfish Cyclic Steroid Glycosides

AbstractStarfishes have evolved with a special type of secondary metabolites, namely starfish saponins, to ward off various predators and parasites; among them, the starfish cyclic steroid glycosides stand out structurally, featuring a unique 16‐membered ring formed by bridging the steroidal C3 and C6 with a trisaccharide. The rigid cyclic scaffold and the congested and vulnerable steroid‐sugar etherate linkage present an unprecedented synthetic challenge. Here we report a collective total synthesis of the major starfish cyclic steroid glycosides, namely luzonicosides A (1) and D (2) and sepositoside A (3), with an innovative approach, which entails a de novo construction of the ether‐linked hexopyranosyl units, use of olefinic pyranoses as sugar precursors, and a decisive ring‐closing glycosylation under the mild gold(I)‐catalyzed conditions.

Six C21 steroidal glycosides from Cynanchum wallichii Wight roots and their multidrug resistance reversal activities

Six unidentified C21 steroidal glycosides, cynwallosides A−F, as well as twenty-two known compounds, were isolated from the roots of Cynanchum wallichii Wight. The structures of cynwallosides A−F were determined by spectroscopic analysis and acidic hydrolysis. Most of these twenty-eight compounds were found to significantly reverse drug resistance in both the MCF-7/ADR and HepG2/ADM cell lines by suppressing P-gp protein expression. Further investigation revealed that three compounds suppressed P-gp expression by significantly inactivating the JNK and NF-κB pathways.

Solamargine induces autophagy-mediated apoptosis and enhances bortezomib activity in multiple myeloma.

Multiple myeloma (MM) is an incurable plasma cell malignancy with a poor survival rate. Conventional chemotherapeutic agent‐induced adverse events, including toxicity, neuropathy or drug resistance, significantly decrease the patients' quality of life and can even lead to interruption of treatment. Therefore, novel therapeutic drugs and strategies are urgently needed to improve MM therapy and patient outcomes. Here, we show that solamargine (SM), a steroidal alkaloid glycoside isolated from a Chinese herb Solanum nigrum L., exhibits promising anti‐MM activity. In particular, SM suppressed the viability of MM cell lines (ARP‐1 and NCI‐H929) in a concentration‐ and time‐dependent manner, inducing apoptosis in these cells. RNA‐seq analysis showed that treatment with SM led to the upregulation of genes associated with cell death and autophagy in H929 cells. Further, we found that treatment with SM activated autophagy in the MM cells, as incubation with 3‐Methyladenine, an inhibitor of autophagy, significantly alleviated SM‐triggered apoptosis and inhibition of viability in MM cells. Interestingly, we also observed a synergistic effect between SM and bortezomib (BTZ), a common chemotherapeutic agent for MM, in both MM cells and human bone marrow CD138+ primary myeloma cells. We also confirmed the single‐agent efficacy of SM and the synergistic effects between SM and BTZ in an MM xenograft mouse model. Collectively, these findings indicate that SM exerts an anti‐MM effect, at least in part, by activating cell autophagy and reveal that SM alone or in combination with BTZ is a potential therapeutic strategy for treating MM.

Antibacterial, phytochemical and GC-MS analysis of <i>Thevetia peruviana</i> extracts: An approach in drug formulation

<i>Thevetia peruviana</i> is a large flowering shrub in the Apocynaceae family used medicinally. The current study aims to determine the phytochemicals and antimicrobial potential of <i>T. peruviana</i>. GC-MS was used to screen the ethanol and n-hexane extracts. Leaf extracts (ethanol and hexane) revealed alkaloids, phenols, anthraquinones, cardiac glycosides, flavonoids, tannins, steroid glycosides, carbohydrates, proteins, terpenoids, terpenoids and fixed oils and fats. GC-MS analysis of the ethanol and hexane extract revealed 24 bioactive metabolites. <i>T. peruviana</i> leaf extracts inhibited tested pathogens at 50, 100, and 200 mg/ml concentrations. A plethora of secondary metabolites demonstrated promising pharmacological benefits. The bioactive chemicals are utilised to treat bacterial infections, cancer, diabetes, and inflammation. This study demonstrated the antibacterial activity of several plants used in traditional medicine.

Phytochemicals and Antimicrobial Evaluation of Tapinathus bangwensis Leaves

Background: The leaves of Tapinathus bangwensis have been used in the treatment of infectious and non-infectious diseases by the herbalist. This instigated evaluation of extract and fractions of Tapinathus bangwensis leaves for antimicrobial activity against some pathogenic organisms and identifications of the phytoconstituents.
 Methods: The standard phytochemical methods and GC-MS were used to identify the phytoconstituents of extract and fractions. The antimicrobial activity was determined using agar dilution method.
 Results: The phytochemical analysis revealed the presence of saponins, flavonoids, tannins, terpenoids and steroidal glycosides in the extract whereas n-hexane fraction contains terpenoids only, ethyl acetate contains flavonoids, tannins, terpenoids, saponins and n-butanol contains saponins, tannins and cardiac glycosides. The GC-MS analysis identified fatty acids, phthalic acid esters, saturated and unsaturated hydrocarbons in the extract and fraction. Most of the compounds identified possess antimicrobial, anticancer, antioxidant and cytotoxicity effects. However, the antimicrobial activity showed that Escherichia coli alone was susceptible to the extract with mics of 5 mg /ml. Escherichia coli, Salmonella typhi, Streptococcus pneumoniae, Proteus mirabilis, and Candidiaalbicans were susceptible to the n-hexane fraction which showed good activity with MIC range of 2.5-5 mg/ml. Escherichia coli, Staphylococcus aureus and Candida albicans were susceptible to ethyl acetate fraction with MIC range of 2.5-5mg/ml and Escherichia coli and Candida albicans were susceptible to ethyl acetate fraction with MIC range of 2.5-5mg/ml and Escherichia coli and candida albicans were susceptible to butanol fraction. with MIC range of 2.5-5mg/ml. klebsiella pneumoniae was not susceptible to the extract and any of the fractions.
 Conclusion: The findings provide justification for the use of Tapinathus bangwensis leaves as antimicrobial agent. Hence, the phytochemicals if isolated can serve as a template for the development of antimicrobial agent.

New steroidal glycosides from the rhizomes of Smilax nipponica and their anti-inflammatory activities

Herein, five new steroidal glycosides (Smilnipponicoside A-E) with five known congeners were isolated from the ethanol extracts of the rhizomes of Smilax nipponica Miq. Their structures were established by 2D NMR spectroscopic techniques (HMBC, HSQC, 1H,1H-COSY and NOESY), together with mass spectrometry, then comparison with the data in literature. The new compounds were subjected to evaluate anti-inflammatory in vitro. Compounds 1, 2 and 3 were found to have modest anti-inflammatory effects through suppression of TNF-α production in LPS-stimulated RAW 264.7 cells.

Specificity of Growth and Synthesis of Secondary Metabolites in Cultures in vitro Digitalis lanata Ehrh.

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.

Characterization of Three Paris polyphylla Glycosyltransferases from Different UGT Families for Steroid Functionalization

Plant steroid glycosides, such as phytosterol glycosides, steroidal saponins, and steroidal glycoalkaloids, are natural products with great pharmaceutical values. In this study, we characterized three UDP-glycosyltransferases (UGTs) involved in the glycosylation of steroidal sapogenin from Paris polyphylla. Substrate specificity analysis revealed that UGT73CR1 could glycosylate steroidal sapogenins and steroidal alkaloids, with the highest affinity for diosgenin. The residues His27 and Asp129 of UGT73CR1 are conserved in corresponding positions of plant glycosyltransferases, which are crucial for activating the C-3 OH of the receptor substrates. In comparison, UGT80A33 and UGT80A34 exhibited a higher affinity for cholesterol than other steroids. UGT80s have a larger active pocket, which allows them to accommodate the side chain of sterols. In summary, we assessed three P. polyphylla glycosyltransferases from two UGT families for the functionalization of steroidal molecules, which will provide a basis for the future biomanufacturing of diverse bioactive steroid glycosides.

Cytotoxic triterpene and steroidal glycosides from the seeds of Digitalis purpurea and the synergistic cytotoxicity of steroidal glycosides and etoposide in SBC-3 cells

The phytochemical investigations of the seeds of Digitalis purpurea have revealed their richness in cardenolide and pregnane glycosides exhibiting potent cytotoxicity; further chemical examinations of the D. purpurea seeds have achieved the isolation of six triterpene glycosides (1–6), six spirostanol glycosides (7–12), and three furostanol glycosides (13–15), including seven previously unidentified compounds (1–3, 10–12, and 14). Here, the structures of 1–3, 10–12, and 14 were determined via extensive spectroscopic analyses, including two-dimensional (2D) NMR; hydrolysis, followed by chromatographic and spectroscopic analyses; and X-ray crystallographic analysis. The cytotoxic activities of the isolated compounds (1–15) against SBC-3 small cell lung carcinoma and TIG-3 normal human diploid fibroblast cells were evaluated. Triterpene glycoside 3 and spirostanol glycoside 9 exhibited considerable cytotoxicity with IC50 values of 1.0 and 1.7 µM, respectively; they induced apoptotic cell death, which was accompanied by the activation of caspase-3 in SBC-3 cells. Spirostanol glycoside 7 exhibited cytotoxicity toward the SBC-3 cells (IC50 1.3 μM). Additionally, 7 at 0.1 and 1.0 µM synergistically enhanced the cytotoxicity of etoposide against SBC-3 cells; compound 7 induced the release of DAMPs; the release of HMGB1, the secretion of ATP, and the exposure of CALR in the SBC-3 cells. Furthermore, the combination of 7 and etoposide resulted in increasing the extracellular release of DAMPs. These data indicated that 7, as well as its combination with etoposide, might potentially cause immunogenic cell death.

Application of Ultrasound Assisted Extraction on Ripe Banana Peels (Musa balbisiana Colla) and its Potential as an Antioxidant and Antigout Agent

The utilization of stone bananas is still very minimal, especially banana peels which will only end up as waste. Despite the fact that stone bananas are a fruit high in metabolites, they have numerous health benefits.The banana peels (Musa balbisiana Colla) was extracted with ultrasound-assisted extraction to determine the content of secondary metabolites, total fernol, antioxidant capacity using the DPPH and FRAP methods, as well as the potential for antigout activity in the extract. Ultrasound-assisted extraction is a less expensive, simpler, and more reliable alternative to traditional extraction methods. Musa balbisiana Colla banana peel extract contains alkaloids, saponins, tannins, steroid glycosides and phenols as secondary metabolites. The results obtained from determining the total phenol content was 397.50±0.41 GAE/g sample. Then the results of testing for free radical scavenging activity with the DPPH and FRAP methods showed IC50 values of 143.97±0.17mg/L and 151.08± 0.32mg/L, respectively. Meanwhile the antigout activity was obtained 27.95±0.08% which was greater than Alupurinol, so that Musa balbisiana Colla banana peel has the potential as an alternative compound to reduce uric acid levels.

Insight into isolation and elucidation of cytotoxic ergostanoids from the mushroom Sarcosphaera crassa (Santi) Pouzar: An edible mushroom

Sarcosphaera crassa is a mushroom consumed in Europe and Anatolia after being cooked well. The cytotoxic activity of the extracts of unbaked S. crassa against MCF7, HT29, HeLa cancer cell lines and toxicity against PDF fibroblast healthy cell lines were studied using MTT assay. Acetone and methanol extracts of the mushroom exhibited significant cytotoxic activity. Further investigation of cytotoxic extracts afforded two new fatty acid sterols (1–2), a new ergosterol glycoside (4), and seven known compounds, including a fatty acid sterol (3), a steroid glycoside (5), two ergostanoids (6–7) and three sugars (8–10). These compounds were identified as brassicasteryl heptadecanoate (1), brassicasteryl palmitoleate (2), brassicasteryl linoleate (3), brassicasterol β-ᴅ-xylofuranoside (4), brassicasterol β-ᴅ-glucoside (5), brassicasterol (6), ergosterol-endoperoxide (7), mannitol (8), erythritol (9) and turanose (10). Among them, 7 exhibited a moderate cytotoxic activity against HeLa (IC50: 70.1 ± 2.0 µg/mL) and high activity against HT29 (IC50: 38.8 ± 0.9 µg/mL), and MCF7 (IC50: 62.9 ± 1.3 µg/mL) cancer cell lines. Compounds 4, 5, and 6 also exhibited significant cytotoxic activity against HT29 and MCF7. Moreover, all compounds exhibited weak toxicity against PDF healthy cell lines. This study indicates the potential use of Sarcosphaera crassa as a natural source of cytotoxic ergostanoids, which can be considered a dietary supplement for cancer prevention.

Steroidal saponins from Trillium tschonoskii rhizome repress cancer stemness and proliferation of intrahepatic cholangiocarcinoma

A phytochemical study was carried out on the extract of Trillium tschonoskii rhizomes, resulting in the isolation of thirty-six steroidal glycosides (1–36). Their structures were established mainly by spectroscopic analyses as well as necessary chemical evidence, of which 1–25 were identified as new analogues. Herein, all the isolated analogues were screened for the cytotoxicity against intrahepatic cholangiocarcinoma (ICC) cell lines of HuCCT1 and RBE through tumor colony formation and CCK-8 survival analysis, and the results demonstrated that three compounds 9, 12, and 26 significantly repressed tumor colony and sphere formation in both cell lines, respectively. Furthermore, the three analogues possessed a remarkable inhibitory role of organoid formation established from hydrodynamic induced mouse primary intrahepatic cholangiocarcinoma. Moreover, the functional assays of flow cytometry analysis, cancer stemness related gene expression, and western blotting assays all indicated that compound 26 could significantly repress cancer stem markers. Taken together, these results demonstrate that steroidal glycosides derived from T. tschonoskii rhizomes could be potentially implicated in human ICC therapy.

Steroidal alkaloids and their glycosides from the bulbs of Fritillaria unibracteata

Seven undescribed steroidal alkaloids, including two jervine-type steroidal alkaloids, fritiunibras A-B (1–2), and five cevanine-type steroidal alkaloid glycosides, fritiunibras C-G (3–7), along with six known cevanine-type steroidal alkaloids and their glycosides (8–13) were isolated from the bulbs of Fritillaria unibracteata Hsiao et K. C. Hsia. Their structures were determined by interpretation of comprehensive spectroscopic and single-crystal X-ray diffraction analysis. The absolute configurations of sugar moieties were determined by HPLC analysis and compared with standards after hydrolysis and derivatization. Furthermore, their inhibitory effects on NO production and cytotoxic activities were evaluated.

In Vitro Antibacterial Activity, Preliminary Phytochemical Screening Profile, and In Vivo Toxicity of Seven Traditional Medicinal Plants in Ethiopia

The threat of antibiotic-resistance calls for novel antibacterial agents. This study was aimed at screening medicinal plants for their antibacterial properties, phytochemical content and safety. Leaves of Allophylus abyssinicus (Hochst.) Radlk., Dicliptera laxata C.B.Clarke, Ligustrum vulgare L., Solanecio gigas (Vatke) c. Jeffrey and Gymnanthemum myrianthum (Hook.f.) H.Rob.; leaf and stem-bark of Olinia rochetiana A. Juss. and the seed of Cucurbita pepo L. were used. Chloroform and ethanol were used to extract G. myrianthum, D. laxata and O. rochetiana; ethyl acetate and methanol for the rest, and water for all. The extracts were tested against clinical/standard strains of Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi and Staphylococcus aureus by the agar-diffusion method. The minimum inhibitory concentrations (MIC) and minimum bactericidal concentrations (MBC) were determined. Acute toxicity to mice was checked and preliminary phytochemical screening was done. Thirteen extracts, out of 24, were active (inhibition zone >7 mm) at differing levels (9.67±0.33-25.66±0.57 mm) against at least one bacterial strain. The MICs and MBCs were 1.95-15.6 mg/mL and 7.8-125 mg/mL respectively. The aqueous extract of S. gigas, methanol extracts of L. vulgare and A. abyssinicus, and ethanol extract of O. rochetiana leaf were the most active (MIC 1.95mg/ml) against S. aureus. Ethyl acetate extracts of A. abyssinicus, L. vulgare and S. gigas; aqueous of C. pepo, O. rochetiana and G. myrianthum; and all D. laxata had no antibacterial activity. P. aeruginosa was the least susceptible to any extract, although the methanol and aqueous extracts of S. gigas performed better against it. Preliminary phytochemical screening of selected extracts for phenols, flavonoids, tannins, steroids, terpenoids, steroidal glycosides, alkaloids, saponins, resins and glycosides showed positivity at least for four of these phytochemicals with glycoside and terpenoids in nearly all extracts and resin in none. The plants were not toxic to mice at 2000 mg/kg. Further consideration of S. gigas, L. vulgare, A. abyssinicus and O. rochetiana is recommended in light of their promising potential and safety.

Steroidal saponins with cytotoxic activity from the stems and leaves of Paris fargesii

The stems and leaves of P. fargesii are rich in steroidal glycosides, some of which display significant cytotoxic activity.

PHYTOANALYTICAL AND PHYTOCHEMICAL INVESTIGATION OF ESSENTIAL OILS OF LEAVES OF TWO MAJOR COMMERCIAL VARIETIES Citrus aurantium L. AND Citrus sinensis L.

Plants are the fashionable foundation of drugs for the mainstream of the world people. The present study was carried out to investigate the constituents of leaves of two major commercial verities of sweet and bitter orange Citrus aurantium L and Citrus sinensis L. Alkaloids, flavonoids, steroidal glycosides, volatile oils, terpenoids, and sterols were confirmed by preliminary phytochemical studies. The physicochemical parameters like Loss on drying, Extractive values, and Ash values were also evaluated. GC-MS analysis of essential oils of Citrus aurantium L. contains 25 compounds and Citrus sinensis L. showed the presence of 30 bio-active compounds. The major components of Citrus aurantium are 1,3-Cyclohexadiene, trans-3-Caren-2-ol, Eucalyptol, γ-Terpinene, Linalool, 2- Cyclohexen-1-ol, 6-Octenal, Terpinen-4-ol, Benzene, α-Terpinyl acetate, 2,6-Octadien-1-ol, Cyclohexane, Caryophyllene, Tetra methyl bicyclo undeca-2,6-diene, 4-Isopropyl-3,7-dimethyloctahydro-1H-cyclopentane, Naphthalene, Caryophyllene oxide, 1-Naphthalenol, Cardinol, and Phytol. Whereas Citrus sinensis L essential oil shows the presence of Eucalyptol, α- Phellandrene, D-Limonene, 3-Carene, Eucalyptol, β-Ocimene, γ-Terpinene, Linalool, Isoneral, Terpinen-4-ol, 6-Octenal, 3,7-dimethyl, α-Terpineol, Citronellol, 2,6-Octadien-1-ol, Neral, Geraniol, trans-Geranic acid methyl ester, 6-Octen-1-ol, 2,6-Octadien-1-ol, 3,7-dimethyl acetate, 3,7-dimethylacetate, Geranyl acetate, Caryophyllene, Humulene, Caryophyllene oxide, and Phytol as the notable compounds. However, both species show similar compounds in their GC-MS analysis with little difference. This study will help us to know the similarities and differences between the closely related medicinally important species of C.sinensis and C.aurantium on their phytochemical nature.

Characterization of seahorse (Hippocampus comes L.) extracts originating from culture and nature in Pesawaran, Lampung, Indonesia.

Indonesia is an archipelagic country with a mega biodiversity, among others, in the marine area. Seahorses (Hippocampus spp.) are a marine fish known to have biocompounds used in traditional medicine "Jamu," such as Hippocampus comes L. (HCL). The present study aims to analyze and compare the chemical contents of cultured seahorse (CS) and natural seahorse (NS) extracts. The CS and NS were identified morphometrically. After freeze-drying, the seahorses were ground into powder with a grinder. The seahorse powder was extracted with ethanol and a water solvent. The extract contained biocompounds, proximate, amino acids, and steroids with high-performance liquid chromatography. The study found unique characteristics of HCL. The highest yield was obtained in NS using a water solvent (18.6%). The biocompounds in seahorses consist of alkaloids and triterpenoids. The highest proximate of water content (11.03%) and ash content (42.50%) was found in NS. In addition, other compounds were also detected in CS, such as fat (7.48%) and protein (47.67%). Both of HCL's different sources had all essential and nonessential amino acids in which the highest concentration were in NS, i.e., L-arginine (56,537.22 mg/kg), L-lysine (17,794.17), glycine (113,649.80 mg/kg), L-proline (47,056.15), and L-alanine (43,451.81). The analysis of the steroid compound of the extract suggested the presence of steroid glycosides. The highest yield of the seahorse extract with a water solvent is about 18.6% and protein content of 47.67% in CS. The crude extract has alkaloids, triterpenoids, and glycine (113,649.80 mg/kg) in NS with water, suggesting the presence of steroid glycosides.

Brief Review on Shatavari (Asparagus racemosus) and Its Medicinal Uses

Asparagus racemosus is another name for shatavari. It belongs to the family asparagaceae. It is an adaptable plant as well. The adaptation of human body to mental and physical stress is said to be achieved by the help of adaptogenic herbs like these.
 Shatavari is an ayurvedic medicine staple that is made available in the form of analeptic for the wellbeing and vitality of person.
 It is popular among all therapeutic plants due to various active biochemicals present in it such as steroidal glycosides, saponins (Shatavarins I, II, III, and IV), flavonoids, polyphenols, vitamins and alkaloids (racemosol). Shatavari extracts from its different parts like roots, flowers, leaves and stems are effective in treating female organs which are involved in reproduction.
 For centuries, ayurvedic medicine has employed shatavari. However, there haven't been enough human trials to recommend it for any medical problem. It is, however, safe to consume it in modest doses, and doing so will allow you to benefit from its antioxidant and immune-boosting properties.
 Except for being an indigenous medicinal plant which known to be important for its sapogenin content which is the precursor of many active pharmacological steroids, it also has many medicinal uses like antioxytoxic (shatavarin four),spasmodic to uterus, hypertensive as well as hypoglycemic activity, anticoagulant activity, antiviral activity, anticancer and antidysentric activity. In ayurvedic medicine asparagus racemosus is considered as tonic specific to females .Despite of being a herb which is rejuvenating it is used in infertility cases of females, increases libido , enhances ovulation as well as folliculogenesis, also increases lactation.

Steroidal Glycosides from the Aerial Parts of Avena sativa L. and Their Cytotoxic Activity.

Twelve steroidal glycosides (1-12) were isolated from the aerial parts of Avena sativa L. (Poaceae). Among the isolated compounds, 1 was directly isolated from the plant for the first time, and 2-6 were new steroidal glycosides. The structures of 1-6 were determined by analysis of their spectroscopic data, chemical transformations, and chromatographic and spectroscopic analyses of the hydrolyzed products. Compounds 5 and 6 were novel steroidal glycosides with a B-ring contracted skeleton (B-nor steroid). Compounds 1, 9, 11, and 12 were cytotoxic to HL-60 human promyelocytic leukemia cells, MIA PaCa-2 human pancreatic carcinoma cells, and A549 human lung adenocarcinoma cells with IC50 values ranging from 0.79 to 13.5 μM. HL-60 cells treated with 1 exhibited apoptotic characteristics, namely, condensed nuclear chromatin, accumulation of sub-G1 cells, and activation of caspase-3. Additionally, the loss of the mitochondrial membrane potential and the release of cytochrome c into the cytoplasm in 1-treated HL-60 cells suggested that 1 induced apoptosis through a mitochondrial-dependent apoptotic pathway.