A new spirostanol sulfonate, spirost-5,25（27）-dien-1β,3β-diol 1-sulfonate（1）, was isolated from the rhizomes of Helleborus thibetanus（Ranunculaceae）, and the structure was identified on the basis of a detailed...A new spirostanol sulfonate, spirost-5,25（27）-dien-1β,3β-diol 1-sulfonate（1）, was isolated from the rhizomes of Helleborus thibetanus（Ranunculaceae）, and the structure was identified on the basis of a detailed spectroscopic analyses, including 2D NMR spectrometry, IR and HRESI-MS.展开更多
A new spirostanol saponin presenting strong activity of inducing morphological deformation of Pyricularia oryzae mycelia was isolated from Dioscorea futshauensis R. Kunth by bioactivity-guided fractionation. The struc...A new spirostanol saponin presenting strong activity of inducing morphological deformation of Pyricularia oryzae mycelia was isolated from Dioscorea futshauensis R. Kunth by bioactivity-guided fractionation. The structure was established as (25S)-spirost-5-en-3 beta, 27-diol-3-O- [alpha -L-rhamnopyranosyl (1 -->2)-beta -D glucopyranosyl (1 -->3)]-beta -D-glucopyranoside on the basis of chemical evidences and spectral analysis, especially by 2D-NMR techniques.展开更多
A new spirostanol steroidal saponin, named maireioside A （1）, together with three known steroidal saponins, hypoglaucin G （2）, parisaponin I （3）, and diosgenin-3-O-α-L-rhamnopyranosyl （1→4）-[α-L-rhamnopyran...A new spirostanol steroidal saponin, named maireioside A （1）, together with three known steroidal saponins, hypoglaucin G （2）, parisaponin I （3）, and diosgenin-3-O-α-L-rhamnopyranosyl （1→4）-[α-L-rhamnopyranosyl （1→2）]-β-D-glucopyranoside （4）, were isolated from the rhizomes of Paris mairei. The structure elucidation was accomplished by 1D and 2D NMR methods, HR-ESI-MS, and hydrolysis. C 2009 Qiang Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.展开更多
Phytochemical investigation of the rhizomes of Paris polyphylla var.stenophylla led to the isolation of two new highly oxygenated spirostanol saponins,named paristenosides A(1)and B(2),together with seven known compou...Phytochemical investigation of the rhizomes of Paris polyphylla var.stenophylla led to the isolation of two new highly oxygenated spirostanol saponins,named paristenosides A(1)and B(2),together with seven known compounds.Their structures were established mainly on the base of NMR spectroscopic techniques and mass spectrometry,as well as chemical methods.In addition,the cytotoxicity of the two new saponins was tested.Graphical Abstract Two new highly oxygenated spirostanol saponins,paristenosides A(1)and B(2),were isolated from the rhizomes of Paris polyphylla var.stenophylla.Their structures were established mainly based on NMR spectroscopic techniques and mass spectrometry,as well as chemical methods.展开更多
Using thioglycosides as donors, trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N-iodosuccinimide(NIS) as promoter, a modified procedure for the glycosylation of spirostanol was developed. A series of saponins w...Using thioglycosides as donors, trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N-iodosuccinimide(NIS) as promoter, a modified procedure for the glycosylation of spirostanol was developed. A series of saponins were synthesized in mild condition with excellent yields.展开更多
Gross saponins of Tribulus terrestris（GSTT） have exact effect on cardiovascular and cerebrovascular diseases.But as a mixture,the specific efficient component of GSTT is still unknown.Nine monomers of spirostanol sa...Gross saponins of Tribulus terrestris（GSTT） have exact effect on cardiovascular and cerebrovascular diseases.But as a mixture,the specific efficient component of GSTT is still unknown.Nine monomers of spirostanol saponins were isolated and idendified as JA―JI（named transitorily） by means of NMR spectrometry.After bio-activity screening on them,we defined that monomers tigogenin 3-O-β-D-xylopyranosyl（1→2）-[β-D-xylopyranosyl（1→3）]-β-D-glucopyranosyl（1→4）-[α-L-rhamnopyranosyl（1→2）]-β-D-galactopyranoside（compound JB） and hecogenin3-O-β-D-glucopyranosyl（1→4）-β-D-galactopyranoside（compound JG） have cytoprotective bio-activity.Compound JB display effective dose in 10-8 and 10-9 mol/L,and JG in 10-6―10-9 mol/L.Survival rate,lactate dehydrogenase（LDH） and apoptosis also show that JB（at dose 10-8,10-9 and 10-10 mol/L） can protect myocardial injury caused by hypoxia/reoxygenation（H/R）.While morphology change also shows JG has cytoprotective bio-activity.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
A facile glycosylation for the synthesis of spirostanol glycosides was reported. Using cadmium carbonate as a catalyst in CH3CN, a series of saponins was synthesized efficiently in a satisfactory yield.
Two minor steroidal saponins were isolated from the roots of Smilax menispermoidea.One of them is new and its structure was established as(25S) spirost-5-en-3β,17α,27-triol-3-O-[α-L-rhamnopyranosyl(1-4)]-β-D-gluco...Two minor steroidal saponins were isolated from the roots of Smilax menispermoidea.One of them is new and its structure was established as(25S) spirost-5-en-3β,17α,27-triol-3-O-[α-L-rhamnopyranosyl(1-4)]-β-D-gluco- pyranoside using spectroscopic and chemical methods.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
目的:研究南川木波罗枝条的化学成分。方法:采用硅胶、Diaion HP20大孔吸附树脂、MCI gel CHP 20P树脂凝胶、Sephadex LH-20凝胶、ODS等柱色谱分离手段,对南川木波罗枝条的95%乙醇提取物进行化学成分的分离纯化,根据化合物的理化性质及...目的:研究南川木波罗枝条的化学成分。方法:采用硅胶、Diaion HP20大孔吸附树脂、MCI gel CHP 20P树脂凝胶、Sephadex LH-20凝胶、ODS等柱色谱分离手段,对南川木波罗枝条的95%乙醇提取物进行化学成分的分离纯化,根据化合物的理化性质及光谱数据鉴定其结构。结果:分离了10个化合物,分别鉴定为diosgenin(1),prosapogenin of dioscin(2),progeninⅡ(3),薯蓣皂苷元-3-O-α-L-吡喃鼠李糖基(1→4)-α-L-吡喃鼠李糖基(1→3)-β-D-吡喃葡萄糖苷(4),7-oxositosterol acilglicosilado(5),咖啡酸乙酯(6),邻苯二甲酸二丁酯(7),松脂素(8),(7S,8S,8'R)-5,5'-二甲氧基落叶松树脂醇(9),棕榈酸(10)。结论:除化合物6,10外,其他化合物均为首次从桑科植物中分离得到。化合物4为首次以天然产物的形式从自然界获得。展开更多
基金Supported by the Program for New Century Excellent Talents in University, China(No.NCET-09-0589) China Postdoc-toral Science Foundation(No. 20090450775)
文摘A new spirostanol sulfonate, spirost-5,25（27）-dien-1β,3β-diol 1-sulfonate（1）, was isolated from the rhizomes of Helleborus thibetanus（Ranunculaceae）, and the structure was identified on the basis of a detailed spectroscopic analyses, including 2D NMR spectrometry, IR and HRESI-MS.
文摘A new spirostanol saponin presenting strong activity of inducing morphological deformation of Pyricularia oryzae mycelia was isolated from Dioscorea futshauensis R. Kunth by bioactivity-guided fractionation. The structure was established as (25S)-spirost-5-en-3 beta, 27-diol-3-O- [alpha -L-rhamnopyranosyl (1 -->2)-beta -D glucopyranosyl (1 -->3)]-beta -D-glucopyranoside on the basis of chemical evidences and spectral analysis, especially by 2D-NMR techniques.
文摘A new spirostanol steroidal saponin, named maireioside A （1）, together with three known steroidal saponins, hypoglaucin G （2）, parisaponin I （3）, and diosgenin-3-O-α-L-rhamnopyranosyl （1→4）-[α-L-rhamnopyranosyl （1→2）]-β-D-glucopyranoside （4）, were isolated from the rhizomes of Paris mairei. The structure elucidation was accomplished by 1D and 2D NMR methods, HR-ESI-MS, and hydrolysis. C 2009 Qiang Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
基金This work is funded by the National Natural Science Funding of China(Grand No.31570363)the Key Research Program of the Chinese Academy of Sciences(Grand No.KSZDEW-Z-004-03-4)the Natural Science Foundation of Yunnan Province(Grand No.2015FA031).
文摘Phytochemical investigation of the rhizomes of Paris polyphylla var.stenophylla led to the isolation of two new highly oxygenated spirostanol saponins,named paristenosides A(1)and B(2),together with seven known compounds.Their structures were established mainly on the base of NMR spectroscopic techniques and mass spectrometry,as well as chemical methods.In addition,the cytotoxicity of the two new saponins was tested.Graphical Abstract Two new highly oxygenated spirostanol saponins,paristenosides A(1)and B(2),were isolated from the rhizomes of Paris polyphylla var.stenophylla.Their structures were established mainly based on NMR spectroscopic techniques and mass spectrometry,as well as chemical methods.
基金Financial support of this research from the National Natural Science Foundaion of China(20372085)is gratefully acknowledged by the authors.
文摘Using thioglycosides as donors, trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N-iodosuccinimide(NIS) as promoter, a modified procedure for the glycosylation of spirostanol was developed. A series of saponins were synthesized in mild condition with excellent yields.
基金Supported by the National Natural Science Foundation of China(Nos.30472020 and 30672654)
文摘Gross saponins of Tribulus terrestris（GSTT） have exact effect on cardiovascular and cerebrovascular diseases.But as a mixture,the specific efficient component of GSTT is still unknown.Nine monomers of spirostanol saponins were isolated and idendified as JA―JI（named transitorily） by means of NMR spectrometry.After bio-activity screening on them,we defined that monomers tigogenin 3-O-β-D-xylopyranosyl（1→2）-[β-D-xylopyranosyl（1→3）]-β-D-glucopyranosyl（1→4）-[α-L-rhamnopyranosyl（1→2）]-β-D-galactopyranoside（compound JB） and hecogenin3-O-β-D-glucopyranosyl（1→4）-β-D-galactopyranoside（compound JG） have cytoprotective bio-activity.Compound JB display effective dose in 10-8 and 10-9 mol/L,and JG in 10-6―10-9 mol/L.Survival rate,lactate dehydrogenase（LDH） and apoptosis also show that JB（at dose 10-8,10-9 and 10-10 mol/L） can protect myocardial injury caused by hypoxia/reoxygenation（H/R）.While morphology change also shows JG has cytoprotective bio-activity.
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.
文摘A facile glycosylation for the synthesis of spirostanol glycosides was reported. Using cadmium carbonate as a catalyst in CH3CN, a series of saponins was synthesized efficiently in a satisfactory yield.
基金Project supported by the National Natural Scicnce Foundation of Chinathe grant for doctoral program from State Education Commission of China
文摘Two minor steroidal saponins were isolated from the roots of Smilax menispermoidea.One of them is new and its structure was established as(25S) spirost-5-en-3β,17α,27-triol-3-O-[α-L-rhamnopyranosyl(1-4)]-β-D-gluco- pyranoside using spectroscopic and chemical methods.
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.
文摘目的:研究南川木波罗枝条的化学成分。方法:采用硅胶、Diaion HP20大孔吸附树脂、MCI gel CHP 20P树脂凝胶、Sephadex LH-20凝胶、ODS等柱色谱分离手段,对南川木波罗枝条的95%乙醇提取物进行化学成分的分离纯化,根据化合物的理化性质及光谱数据鉴定其结构。结果:分离了10个化合物,分别鉴定为diosgenin(1),prosapogenin of dioscin(2),progeninⅡ(3),薯蓣皂苷元-3-O-α-L-吡喃鼠李糖基(1→4)-α-L-吡喃鼠李糖基(1→3)-β-D-吡喃葡萄糖苷(4),7-oxositosterol acilglicosilado(5),咖啡酸乙酯(6),邻苯二甲酸二丁酯(7),松脂素(8),(7S,8S,8'R)-5,5'-二甲氧基落叶松树脂醇(9),棕榈酸(10)。结论:除化合物6,10外,其他化合物均为首次从桑科植物中分离得到。化合物4为首次以天然产物的形式从自然界获得。
