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 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-hexalr...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.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
Two new isospirostanol sapogenins named(25R)-5/%spirostane-(1αα3a)-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 sapo...Two new isospirostanol sapogenins named(25R)-5/%spirostane-(1αα3a)-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.展开更多
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
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, ...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.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
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
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 nutra...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.展开更多
Saponins can be potential candidates for the development of safe biopesticides,due to their widely acknowledged insecticidal,fungicidal and nematicidal activity,but information on their effects on soil biological prop...Saponins can be potential candidates for the development of safe biopesticides,due to their widely acknowledged insecticidal,fungicidal and nematicidal activity,but information on their effects on soil biological properties is still limited.This study aimed to investigate the short-term fate of saponins from Medicago sativa in soil and their dose-effect relationship with microbial biomass and selected enzyme activities in soils with different origin,physical and chemical properties.Microbial degradation of total saponins ranged from 46%to 91%,according to soil characteristics,within 28 days from their incorporation into the soil.Both saponin glycosidic chains and triterpenic aglycones were also microbially degraded,though by dynamics changing among the different soils.In all soils,M.sativa saponins significantly reduced microbial biomass at rates of 10 and 20 mg saponin mixture per g of soil.Microbial enzymatic activities were less affected as indicating an adaptive response of soil microbial communities to the presence of saponins.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 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
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.
文摘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.
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supported by grants from the National Natural Science Foundation of China(No. 81001694)
文摘Two new isospirostanol sapogenins named(25R)-5/%spirostane-(1αα3a)-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.
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.
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.
文摘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.
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.
基金supported by the ROP ERDF 2014-2020 Lombardy-Innovation and Competitiveness.
文摘Saponins can be potential candidates for the development of safe biopesticides,due to their widely acknowledged insecticidal,fungicidal and nematicidal activity,but information on their effects on soil biological properties is still limited.This study aimed to investigate the short-term fate of saponins from Medicago sativa in soil and their dose-effect relationship with microbial biomass and selected enzyme activities in soils with different origin,physical and chemical properties.Microbial degradation of total saponins ranged from 46%to 91%,according to soil characteristics,within 28 days from their incorporation into the soil.Both saponin glycosidic chains and triterpenic aglycones were also microbially degraded,though by dynamics changing among the different soils.In all soils,M.sativa saponins significantly reduced microbial biomass at rates of 10 and 20 mg saponin mixture per g of soil.Microbial enzymatic activities were less affected as indicating an adaptive response of soil microbial communities to the presence of saponins.
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.
