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.

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）.

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.

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.