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 a...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.展开更多
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 ...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.展开更多
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 compre...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）.展开更多
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...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.展开更多
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 carcin...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.展开更多
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-sitoste...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.展开更多
基金Project supported by the National Natural Science Foundation of China(No.29372077).
文摘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.
基金support from the Natural Science Foundation of China(Nos.29070070,29372077).
文摘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.
基金supported by the National Natural Science Foundation of China(No30873154)National Specific Project of New Drugs Innovation(No2009ZX09103-328)Scientific Foundation of Shanghai China(No 08DZ1971600)
文摘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）.
文摘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.
基金the National Natural Science Foundation of China(No.31860076)Outstanding Young Talent Project of Zunyi Medical University(No.17zy-002)+3 种基金Technology Support Program of Zunyi(No.ZSKH-HZ-ZI-2020-88)Science and Technology Project of Zunyi[ZSKH-HZ(2020)No.60/55]Special Project of Zunyi Medical University for Academic New Talents[No.QKHPT(2018)5772-067/062]Guizhou Provincial Chinese Medicine Administration Project(No.QZYY-2019-064)。
文摘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.
文摘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.
