Polyhydroxylated Steroidal Sapogenins from Tupistra wattii

Two novel polyhydroxylated steroidal sapogenins, wattigenin B ((25R)-spirost-1beta, 2beta, 3beta, 4beta, 5beta, 6beta, 7alpha-heptol, 1) and wattigenin C ((25S)-spirost-1beta, 2beta, 3beta, 4beta, 5beta, 7alpha-hexalrydroxyl-6-one, 2), together with two known sapogenins, kitigenin (3) and convallagenin B (4), were isolated froth the fresh rhizomes of Tupistra wattii Hook. f. The structures of the compounds were determined on the basis of spectroscopic analysis. The four sapogenins were evaluated for the cytotoxicities on the cancer cell line K562 and A2780a in vitro. Compounds 1 - 4 were obtained from the plant for the first time.

Two New Spirostanol Steroidal Sapogenins from Fermented Leaves of Agave americana

Two new spirostanol sapogenins named agavegenin A and B were isolated from the fermented leaves of Agave americana L. Their structures were elucidated as (23S, 25R)-5a- spirostan-3b, 6a, 11a, 23-tetraol (1) and (23S, 25S)-5a-spirostan-3b, 23, 27-triol (2) by spectral methods.

Variability in the Content of 25α- and 25β-Steroidal Sapogenins among Thirty Morphologically Different Sudanese Seed Accessions of Fenugreek

Seeds of Fenugreek （Trigonellafoenum-graecum L.）, an international spice commodity, are much consumed in Sudan as a food, for flavoring and as a folk-remedy for several ailments, together with local beliefs in nutraceutical benefits. The authors have noted an immense variability in colour and other morphological characters of Fenugreek seeds offered in local Sudanese markets and wondered whether this variability is extended to their chemical composition. Steroidal sapogenins are important chemical constituents of Fenugreek seeds in view of their potential as precursors for the commercial synthesis of steroid drugs and their continually revealed beneficial biological activities. In this study, thirty Sudanese Fenugreek seed accessions collected from different geographical regions in Sudan were analyzed for their 25α-, 25β- and total sapogenin content using a simple and specific infra-red spectroscopic method. The seed accessions exhibited much morphological variability particularly in outer seed coat color and size. Preparative TLC followed by gravimetric analysis showed that steroidal sapogenins, mostly diosgenin and yamogenin, represented more than 70% of the steroids of Fenugreek seeds. Infra-red spectroscopic analysis showed that total 25α-sapogenins （calculated as diosgenin） varied from 0.65% to 1.68%. Total 25β-sapogenin （calculated as yamogenin） varied from 0.38% to 2.03%. The content of total sapogenins （α ＋ β epimeric forms） varied between 1.24% and 3.0% of the oven-dry weight of seeds. β-sapogenins （mostly yamogenin） were dominant over α-sapogenins （diosgenin） in most Sudanese Fenugreek seed accessions.

Two new isospirostanol sapogenins from Reineckia carnea

Two new isospirostanol sapogenins named （25R）-5/%spirostane-（1αα 3a）-diol （1） and （25R）-5/%spirostane-（1α, 2α, 3α, 4α）- tetrol （2） were isolated from the whole herb ofReineckia carnea （Andr.） Kunth. The structures of the sapogenins were elucidated by chemical and spectral methods. methods

Two new dammarane-type sapogenins from Gynostemma pentaphyllum

Two new sapogenins,named（20S,24R）-3β,20,21β,25-tetrahydroxy-21,24-cyclodammarane（1）and 3β-hydroxyetio-17β-dammaranic acid（2）,were isolated from the alkaline hydrolysate of Gynostemma pentaphyllum saponins.Their structures were elucidated by spectroscopic methods.

Mercaptolysis of the E/F Rings of Steroidal Sapogenins:A Concise Synthesis of Δ^(20(22))-Furostene-26-thioethers

Lewis acid catalyzed mercaptolysis of steroidal sapogenins was reinvestigated. Besides obtaining the reported 26-thioacetals 5 under milder conditions, a new type of compounds Δ20(22)-furostene-26-thioethers 6 were also synthesized through the mercaptolysis of steroidal sapogenins, which can be used to the synthesis of the steroidal molecule with side chains.

BF3•Et2O Promoted Sulfuration of Steroidal Sapogenins

A reaction between steroidal sapogenins and hydrogen sulfide promoted by BF3•Et2O is described.The thio-diosgenin and thiotigogenin comprising a sulfur atom on the F ring can be easily afforded in one step under this mild reaction condition.Furthermore,a hypothetical mechanism is also shown.

New steroidal sapogenins from the acid hydrolysis product of the whole glycoside mixture of Welsh onion seeds

Two new steroidal sapogenins（1,2） along with five known steroidal sapogenins were isolated from the acid hydrolysis product of the whole glycoside mixture of Welsh onion（Allium fistulosum L.） seeds.Based on comprehensive spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry,their structures were elucidated as（25R）-19-norspirosta-l,3,5（10）-triene-4 -methyl-2-ol（1）,（25R）-spirost-l,4-diene-3-one-2,6-diol（2）,（25R）-spirost-l,4-diene-3-one-2-ol（3）,（25R）-spirost-4-ene-3-one-2-ol （4）,yuccagenin（5）,gitogenin（6） and tigogenin（7）.

Characteristics and mechanism of enzyme secretion and increase in [ Ca^(2+)]_i in Saikosaponin.(I)stimulated rat pancreatic acinar cells

AIM: This investigation was to reveal the characteristics and mechanism of enzyme secretion and increase in [Ca2+]i stimulated by saikosaponin(I) (SA(I)) in rat pancreatic acini. METHODS:Pancreatic acini were prepared from male Wistar rats. Isolated acinar cells were suspended in Eagle's MEM solution. After adding drugs, the incubation was performed at 37 degrees for a set period of time. Amylase of supernatant was assayed using starch-iodide reaction. Isolated acinar single cell was incubated with Fura-2/AM at 37 degrees, then cells were washed and resuspended in fresh solution and attached to the chamber. Cytoplasm [Ca2+]i of a single cell was expressed by fluorescence ratio F340/F380 recorded in a Nikon PI Ca2+ measurement system. RESULTS: Rate course of amylase secretion stimulated by SA(I) in rat pancreatic acini appeared in bell-like shape. The peak amplitude increased depended on SA(I) concentration. The maximum rate responded to 1 x 10(-5)mol/L SA(I) was 13.1-fold of basal and the rate decreased to basal level at 30 min. CCK-8 receptor antagonist Bt(2)-cGMP markedly inhibited amylase secretion stimulated by SA(I) and the dose-effect relationship was similar to that by CCK-8. [Ca2+]i in a single acinar cell rose to the peak at 5 min after adding 5 x 10(-6)mol/L SA(I) and was 5.1-fold of basal level. In addition, there was a secondary increase after the initial peak. GDP could inhibit both the rate of amylase secretion and rising of [Ca2+]i stimulated by SA(I) in a single pancreatic acinar cell. CONCLUSION: SA(I) is highly efficient in promoting the secretion of enzymes synthesized in rat pancreatic acini and raising intracellular [Ca2+]i. Signaling transduction pathway of SA(I) involves activating special membrane receptor and increase in cytoplasm [Ca2+]i sequentially.

NEW CYCLOARTANE SAPOGENIN AND ITS SAPONINS FROM CURCULIGO ORCHIOIDES

From rhizomes of Curculigo orchioideg(Xian Mao)six new cyclo- artane glycosides named curculigosaponin A～F were isolated.The new triterpenoidal sapogenin named curculigenin A,whlch is common to curculigo- saponin A～F,was formulated as 3β,11α,16β-trihydroxycycloartane-24-one by HR-MS and 2D-NMR technical analysis.On the basis of chemical evidence and spectral data,the structures of these saponins were elucidated.

LEWIS ACID MEDIATED RING F OPENING-ACETYLATION OF STEROIDAL SAPOGENIN

Treatment of steroidal sapogenin diosgenin 1 with Lewis acid ethereal trifluoroborane in acetic anhydride at room temperature afforded a new type of pseudosapugenin 23, 26-diacetyl-△22(23)- pseudo-sapogenin 3 and its C-20 isomer 4 in 54% and 19% yield respectively.The possible mechanism was also suggested.

Reaction of Oncomelania Hupensis to the Allelopathic Triterpene Sapogenin from Nerium Indicum

This paper has analyzed allelopathic effects ofNerium indicum on Oncomelania hupensis through triterpene sapogenins, a potential molluscicide. The snails were treated under six various concentrations （0, 20, 40, 60, 80, 100 mg/L） of triterpene sapogenins and five periods （1, 2, 3, 4, 5 days）. The mortality of snails was positively correlated with the concentration of triterpene sapogenins and exposure time. The results ofprobit analysis showed that the LD50 （Lethal Dose, 50%） oftriterpenoid saponins from N. indicum by immersion for 2, 3, 4, 5 days were 78.31, 30.26, 20.50, 14.19 mg/L, respectively. And the corresponding 95% confidence intervals were 63.60-108.19, 9.49-44.42, 2.86-30.90, 0.23-22.79 mg/L, respectively. The observations of both scanning electron microscope and transmission electron microscope proved that 40 mg/L triterpene sapogenins could cause apparent damage to the structure of soft tissue, liver and intestine of O. hupensis. The esterase （EST） isozyme electrophoresis in liver of O. hupensis treated by 40 mg/L of the concentrations lixivium of the triterpene sapogenins from N. indicum was analyzed for 24, 48, 72, 96, 120 h, respectively. The activity of enzyme was higher than control water group after been treated up to 24-48 h, and then lowered and disappeared after 72 h. It was implicated that the extracted triterpene sapogenin from N. indicum were promising for controlling the snail, which were also providing the foundation for constructing plant community of oleander to control O. hupensis.

Isolation and microbial transformation of tea sapogenin from seed pomace of Camellia oleifera with anti-inflammatory effects

In the current study,tea saponin,identified as the primary bioactive constituent in seed pomace of Camellia oleifera Abel.,was meticulously extracted and hydrolyzed to yield five known sapogenins:16-O-tiglogycamelliagnin B(a),camelliagnin A(b),16-O-angeloybarringtogenol C(c),theasapogenol E(d),theasapogenol F(e).Subsequent biotransformation of compound a facilitated the isolation of six novel metabolites(a1−a6).The anti-inflammatory potential of these compounds was assessed using pathogenassociated molecular patterns(PAMPs)and damage-associated molecular patterns molecules(DAMPs)-mediated cellular inflammation models.Notably,compounds b and a2 demonstrated significant inhibitory effects on both lipopolysaccharide(LPS)and high-mobility group box 1(HMGB1)-induced inflammation,surpassing the efficacy of the standard anti-inflammatory agent,carbenoxolone.Conversely,compounds d,a3,and a6 selectivity targeted endogenous HMGB1-induced inflammation,showcasing a pronounced specificity.These results underscore the therapeutic promise of C.oleifera seed pomace-derived compounds as potent agents for the management of inflammatory diseases triggered by infections and tissue damage.

Anticancer Activity of Diosgenin and Its Molecular Mechanism

Diosgenin, a steroidal sapogenin, obtained from Trigonella foenum-graecum, Dioscorea, and Rhizoma polgonati, has shown high potential and interest in the treatment of various cancers, such as oral squamous cell carcinoma, laryngeal cancer, esophageal cancer, liver cancer, gastric cancer, lung cancer, cervical cancer, prostate cancer, glioma, and leukemia. This article aims to provide an overview of the in vivo, in vitro,and clinical studies reporting the diosgenin’s anticancer effects. Preclinical studies have shown promising effects of diosgenin on inhibiting tumor cell proliferation and growth, promoting apoptosis, inducing differentiation and autophagy, inhibiting tumor cell metastasis and invasion, blocking cell cycle, regulating immunity and improving gut microbiome. Clinical investigations have revealed clinical dosage and safety property of diosgenin. Furthermore, in order to improve the biological activity and bioavailability of diosgenin, this review focuses on the development of diosgenin nano drug carriers, combined drugs and the diosgenin derivatives. However, further designed trials are needed to unravel the diosgenin’s deficiencies in clinical application.

Advances in the pharmacological activities and mechanisms of diosgenin

Diosgenin, a well-known steroid sapogenin derived from plants, has been used as a starting material for production of steroidal hormones. The present review will summarize published literature concerning pharmacological potential of diosgenin, and the underlying mechanisms of actions. Diosgenin has shown a vast range of pharmacological activities in preclinical studies. It exhibits anticancer, cardiovascular protective, anti-diabetes, neuroprotective, immunomodulatory, estrogenic, and skin protective effects, mainly by inducing apoptosis, suppressing malignant transformation, decreasing oxidative stress, preventing inflammatory events, promoting cellular differentiation/proliferation, and regulating T-cell immune response, etc. It interferes with cell death pathways and their regulators to induce apoptosis. Diosgenin antagonizes tumor metastasis by modulating epithelial-mesenchymal transition and actin cytoskeleton to change cellular motility, suppressing degradation of matrix barrier, and inhibiting angiogenesis. Additionally, diosgenin improves antioxidant status and inhibits lipid peroxidation. Its anti-inflammatory activity is through inhibiting production of pro-inflammatory cytokines, enzymes and adhesion molecules. Furthermore, diosgenin drives cellular growth/differentiation through the estrogen receptor(ER) cascade and transcriptional factor PPARγ. In summary, these mechanistic studies provide a basis for further development of this compound for pharmacotherapy of various diseases.

Structure and Activity of a New Sapogenin from Chlorophytum laxum R. Br.

A new steroidal sapogotin named 25-R-spirosta-3,5-dien-12β-ol（1） was isolated from the dried roots of Chlorophytum laxum R. Br. along with five known compounds, namely, diosgenin（2）, stigmasterol（3）, β-sitosterols（4）, estigmasterol-3-O-β-D-glicopyranoside（5） and 3-O-β-authemisol（6）. The structure of compound 1 was elucidated by the analysis of IR, HRESI-MS, 1D and 2D NMR spectral data. Compounds 2--5 were isolated from Chlorophytum laxum R. Br. In addition, all the compounds were evaluated for cytotoxicity on the human nasopharyngeal carcinoma cancer cell line 5-8F. Among them, the newly identified 25-R-spirosta-3,5-dien-12β-ol（1） and diosgenin（2） exhibited high cytotoxicity on 5-8F cells, with IC50 values of 24.8 and 41.9 μmol/L, respectively.