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.

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.

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）.

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.

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.