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～...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.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
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,...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.展开更多
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-tiglogycamelliag...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.展开更多
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.Th...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.展开更多
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 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
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
文摘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.
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.
文摘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.
基金Acknowledgments The authors would like to thank the National Natural Science Foundation of China （grant No. 30471506, 30570322, 39670654, 30671818） and the Science and Technology Foundation of Forest （No. 2006BAD03AI 5） for providing funds to the research.
基金supported by the National Nature Science Foundation of China(No.21302052)the“Program for New Century Excellent Talents in University”awarded to ZHANG Jian(No.NECT-11-0739)+1 种基金the Postgraduate Research&Practice Innovation Program of Jiangsu Province(No.SJKY19_0658)Jiangsu Funding Program for Excellent Postdoctoral Talent,and“Jiangsu Funding Program for Excellent Postdoctoral Talent”awarded to SHEN Pingping.
文摘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.
基金financially supported by E&T Modern Center for Natural Products of Liaoning Province of China (No.2008402021)
文摘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.
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.
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.
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）.
