OBJECTIVE The total steroid saponins(TSSN)isolated from Dioscorea zingiberensis C.H.Wright(D.zingiberensis)has shown a variety of beneficial bioactivities.However,there are no reports about the neuroprotective effects...OBJECTIVE The total steroid saponins(TSSN)isolated from Dioscorea zingiberensis C.H.Wright(D.zingiberensis)has shown a variety of beneficial bioactivities.However,there are no reports about the neuroprotective effects of the TSSN until now.Therefore,we explored the neuroprotective effects of TSSN on rats against transient focal cerebral ischemia-reperfusion(I/R)and the underlying mechanisms.METHODS The healthy adult Sprague-Dawley rats were randomly assigned into six groups.After pre-treatment with the TSSN intragastrically for six days,the rats were subjected to the ischemia injury by the surgery of middle cerebral artery occlusion(MCAO)for 90 min.Some indexes were evaluated and detected.RESULTS As compared to the I/R group,TSSN group of rats,especially given the 30 mg·kg^-1 of TSSN,not only marked reduction in the neurological deficit scores,cerebral infarct volume,and brain edema,but also an increase in neuron survival(Nissl bodies)in the hippocampal cornuammons 1(CA1)and cortex hemisphere of the ipsilateral ischemia.At the same time,the inflammatory cytokines in serum induced by MCAO were significantly alleviated by the TSSN pre-administration.What′s more,the increase of caspase-3 was evidently reduced in the CA1 and cortex of the hemisphere injured brain.Finally,the down-regulating anti-apoptotic Bcl-2 and up-regulating pro-apoptotic Bax proteins were obviously suppressed.CONCLUSION TSSN plays a potential neuroprotective role against a severe injury induced by transient focal cerebral ischemic reperfusion in a rat experimental model,and this role may be mediated by its antiinflammatory and anti-apoptotic actions.展开更多
Steroid saponins are secondary metabolites with multiple medicinal values that are found in large quantities in natural medicines,especially Vernonia amygdalina,a famous nature medicine for the treatment of tonsilliti...Steroid saponins are secondary metabolites with multiple medicinal values that are found in large quantities in natural medicines,especially Vernonia amygdalina,a famous nature medicine for the treatment of tonsillitis,diabetes,pneumonia.The current study was designed to combine molecular networking(MN)with diagnostic ions for rapid identification ofΔ^(7,9(11))stigmastane-type saponins which were theα-glucosidase inhibitory active substances in V.amygdalina.First,theα-glucosidase inhibitory activities of fiveΔ^(7,9(11))stigmastane-type steroid saponins that were previously isolated were screened,which indicated that theΔ^(7,9(11))stigmastane-type steroid saponin was one of the active constituents responsible for ameliorating diabetes.Furthermore,a strategy was proposed to identify stigmastane-type steroid saponins and verify the plausibility of derived fragmentation pathways by applying MN,MolNetEnhancer and unsupervised substructure annotation(MS2LDA).Based on this strategy,other sevenΔ^(7,9(11))stigmastane-type steroid saponins were identified from this plant.Our research provide scientific evidence for the antidiabetic potential of the steroid saponin-rich extract of V.amygdalina leaf.展开更多
The Smilax species,widely distributed in tropical region of the world and the warm areas of East Asia and North America,are extensively used as folk medicine to treat inflammatory disorders.Chemical investigation on S...The Smilax species,widely distributed in tropical region of the world and the warm areas of East Asia and North America,are extensively used as folk medicine to treat inflammatory disorders.Chemical investigation on Smilax species showed they are rich sources of steroidal saponins with diversified structure types,including spirostane,isospirostane,furostane,pregnane,and cholestane.This review mainly summarizes the steroidal saponins(1–104)reported from the genus Smilax between 1967 and 2016,and their biological activities.The relationship between structures of steroidal saponins and related biological activities were briefly discussed.展开更多
Two new steroidal saponins, diuranthosides D and E, were isolated from the whole plant of Diuranthera inarticulata Wang et K. Y. Lang. By means of spectral and chemical analysis, the structure of the new compounds wer...Two new steroidal saponins, diuranthosides D and E, were isolated from the whole plant of Diuranthera inarticulata Wang et K. Y. Lang. By means of spectral and chemical analysis, the structure of the new compounds were established as neotigogenin-3-O-(-D-glucopyranosyl (1?3)-(-D-xylopyranosyl-(1?3)-[(-D-glucopyranosyl(1?2)]-(-D-glucopyranosyl(1?4)-(-D-galactopyranoside (1) and neotigogenin-3-O-(-D-glucopyranosyl(1?3)-(-D-glucopyranosyl (1?3)-(-D-xylopyranosyl(1?3)-[(-D-glucopyranosyl(1?2)]-(-D-glucopyranosyl(1?4)-(-D-galactopyranoside (2) respectively.展开更多
Two new minor steroidal saponins, (25R) spirostan-3β-ol-6-one-3-O-[α-L- arabinopyranosyl(1-4)]-β-D-glucopyranosidc (1) and (25S) spirost-5-en -3β, 17α, 27-triol-3-O- [α-L-arabinopyranosyl(1-6)]-β-D-glucopyranos...Two new minor steroidal saponins, (25R) spirostan-3β-ol-6-one-3-O-[α-L- arabinopyranosyl(1-4)]-β-D-glucopyranosidc (1) and (25S) spirost-5-en -3β, 17α, 27-triol-3-O- [α-L-arabinopyranosyl(1-6)]-β-D-glucopyranosidc (2) were isolated from the roots of Smilax lebrunii. Their structures were established on thc basis of chemical and spectral methods.展开更多
Objective:Tribulus terrestris L.(T.terrestris)is a highly valuable traditional Chinese medicine used to treat stroke,inflammation,pulmonary fibrosis,liver cancer,and urolithiasis.To identify the basic substance respon...Objective:Tribulus terrestris L.(T.terrestris)is a highly valuable traditional Chinese medicine used to treat stroke,inflammation,pulmonary fibrosis,liver cancer,and urolithiasis.To identify the basic substance responsible for the anti-inflammatory effect of TST(total saponins of Tribulus),its chemical composition was systematically studied,and its effect of inhibiting nitric oxide generation and the expression of related inflammatory factors were determined.Methods:To separate chemical constituents from T.terrestris by column chromatography.Spectroscopic methods,including 1D and 2D nuclear magnetic resonance spectroscopy(NMR)and mass spectrometry(MS)techniques,were used to elucidate the isolated compounds.The anti-inflammatory activities of TST and several compounds were evaluated in vitro.Results:Fifteen steroidal saponins,including 9 furostanol steroidal saponins(1,2,3,4,5,6,7,8,and 15)and 6 isospirostanol steroidal saponins(9,10,11,12,13,and 14),were isolated from T.terrestris.TST significantly decreased the expression of tumor necrosis factor-a(TNF-a)and interleukin-6(IL-6)in RAW 264.7 cells stimulated by lipopolysaccharides.Compounds 13 and 15 evidently reduced TNF-a expression.Compounds 6,10,12,13,and 15 markedly reduced IL-6 expression.Conclusions:Compounds 1 was a novel furostanol steroidal saponin,named 26-O-b-D-glucopyranosyl-(25R)-5afurostan-12-carbonyl-20(22)-en-3b,26-diol-3-O-{b-D-xylopyranosyl-(1→2)-[b-D-xylopyranosyl-(1→3)]-b-D-glucopyranosyl-(1→4)-[a-L-rhamnopyranosyl-(1→2)]-b-D-galactopyranoside}.Compounds 2 was isolated from the family Zygophyllaceae for the first time,and 5 and 6 were isolated from the Tribulus genus.TST and compounds 6,10,12,13,and 15 exerts antiinflammatory activity.展开更多
Two new C27 steroidal glycosides, named taccaoside A (1) and B (2), were isolated from the traditional Chinese herb Tacca plantaginea. The spectroscopic and chemical evidences revealed their structures to be 26-O--D-...Two new C27 steroidal glycosides, named taccaoside A (1) and B (2), were isolated from the traditional Chinese herb Tacca plantaginea. The spectroscopic and chemical evidences revealed their structures to be 26-O--D-glucopyranosyl-(25R)-3?26-dihydroxy furost-5,20-diene -3-O-[?L-rhamnopyranosyl(12)]-[?L-rhamnopyranosyl(13)]--D-glucopyranoside (1) and 26-O--D-glucopyranosyl-(25R)-3?26-dihydroxy furost-5,20-diene-3-O-[?L-rhamnopyranosyl- (12)]-[?D-glucopyranosyl(13)--L-rhamnopyranosyl(13)]--D-glucopyranoside (2), res- pectively.展开更多
Phytochemical investigation on the roots of Asparagus cochinchinensis led to the isolation of one new furostanol saponin,named 26-O-β-d-glucopyranosyl-22α-hydroxyl-(25R)-Δ5(6)-furost-3β,26-diol-3-O-α-l-rhamnopyra...Phytochemical investigation on the roots of Asparagus cochinchinensis led to the isolation of one new furostanol saponin,named 26-O-β-d-glucopyranosyl-22α-hydroxyl-(25R)-Δ5(6)-furost-3β,26-diol-3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranoside(1),along with three known congeners(2‒4).The structure of new saponin was elucidated via comprehensive inspection of its HRMS and NMR spectral data as well as chemical technology,whereas those of known ones were identified by comparison of their NMR and MS spectral data with those reported in literatures.All isolated saponins were evaluated for their cytotoxic effects on two human liver(MHCC97H)and lung adenocarcinoma(H1299)cancer cells in vitro.Among them,both 1 and 2 showed significant cytotoxicity against above mentioned cell lines.Further studies revealed that these two saponins could significantly inhibit their proliferation of MHCC97H and H1299 cells.展开更多
A new limonoid,17-(5-methoxy-2-oxofuran-3-yl)-28-deoxonimbolide(1),and a new C21 steroidal saponin,2a,4a-dihydroxy-pregn-5-en-16-one-3a-O-D-glucopyranoside(2),together with 11 known compounds were isolated from the me...A new limonoid,17-(5-methoxy-2-oxofuran-3-yl)-28-deoxonimbolide(1),and a new C21 steroidal saponin,2a,4a-dihydroxy-pregn-5-en-16-one-3a-O-D-glucopyranoside(2),together with 11 known compounds were isolated from the methanol extract of the leaves of Azadirachta indica.The structures were elucidated by means of spectroscopic analysis and putative biosynthetic origins.All the compounds were evaluated for their antibacterial activities against six bacterial strains.展开更多
Five new saponins,including three steroid saponins,paristenoids A-C(1-3),and two triterpenoid saponins,paristenoids D-E(4-5),along with four known ones(6-9)were isolated from the rhizomes of Paris polyphylla var.steno...Five new saponins,including three steroid saponins,paristenoids A-C(1-3),and two triterpenoid saponins,paristenoids D-E(4-5),along with four known ones(6-9)were isolated from the rhizomes of Paris polyphylla var.stenophylla.The structures of the isolated compounds were identified nainly by detailed spectroscopic analysis,including extensive 1D and 2D NMR,MS,as well as chemical methods.Compound 3 is a new cyclocholestanol-type steroidal saponin with a rare 6/6/6/5/5 fused-rings cholestanol skeleton,and this skeleton has been first found from the genus Paris.The cytotoxicities of the isolated compounds against three human three glioma cell lines(U87MG,U251MG and SHG44)were evaluated,and compound 7 displayed certain inhibitory effect with ICso values of 15.22±1.73,18.87±1.81 and 17.64±1.69μmol^(-1),respectively.展开更多
Sugar-sugar glycosyltransferases play important roles in constructing complex and bioactive saponins.Here,we characterized a series of UDP-glycosyltransferases responsible for biosynthesizing the branched sugar chain ...Sugar-sugar glycosyltransferases play important roles in constructing complex and bioactive saponins.Here,we characterized a series of UDP-glycosyltransferases responsible for biosynthesizing the branched sugar chain of bioactive steroidal saponins from a widely known medicinal plant Paris polyphylla var.yunnanensis.Among them,a 2'-O-rhamnosyltransferase and three 6'-O-glucosyltrasferases catalyzed a cascade of glycosylation to produce steroidal diglycosides and triglycosides,respectively.These UDP-glycosyltransferases showed astonishing substrate promiscuity,resulting in the generation of a panel of 24 terpenoid glycosides including 15 previously undescribed compounds.A mutant library containing 44 variants was constructed based on the identification of critical residues by molecular docking simulations and protein model alignments,and a mutant UGT91AH1^(Y187A)with increased catalytic efficiency was obtained.The steroidal saponins exhibited remarkable antifungal activity against four widespread strains of human pathogenic fungi attributed to ergosterol-dependent damage of fungal cell membranes,and 2'-O-rhamnosylation appeared to correlate with strong antifungal effects.The findings elucidated the biosynthetic machinery for their production of steroidal saponins and revealed their potential as new antifungal agents.展开更多
AIM: To develop and validate a high performance liquid chromatography(HPLC) coupled with diode array and evaporative light scattering detectors(DAD-ELSD) method for the quantitative determination and fingerprint analy...AIM: To develop and validate a high performance liquid chromatography(HPLC) coupled with diode array and evaporative light scattering detectors(DAD-ELSD) method for the quantitative determination and fingerprint analysis of ten active constituents in three chemical classes(namely, xanthone glycosides, steroidal saponins, and alkaloids) in Zhimu-Huangbai herb pair(ZB). METHOD: Chromatographic separation was performed on a Diamonsil C18 column(4.6 mm × 250 mm, 5 μm, Dikma) by gradient elution using acetic acid in acetonitrile solution at a flow rate of 1.0 mL·min–1 at 260 nm. The drift tube temperature of ELSD was set to 60 ℃ and nebulizer gas pressure was 4.0 Bar. Method validation was performed to assure its linearity, limits of detection and quantification, precision, repeatability, stability, and accuracy. RESULTS: The HPLC-DAD-ELSD method allowed the quantification of ten compounds(phellodendrine, jatrorrhizine, palmatine, berberine, neomangiferin, mangiferin, timosaponin E-I, timosaponin B-II, timosaponin B, and timosaponin A-III), and was successfully applied to fingerprint analysis for ten batches of ZB samples. CONCLUSION: This was the first time to apply the combination of DAD and ELSD for the simultaneous determination of ten active ingredients in ZB. The results showed that the combination of quantitative analysis for marker ingredients and chemical fingerprint for the TCM herb pair provides a potentially powerful, widely introduced, and internationally accepted strategy for assessment of complex TCM formulas.展开更多
The steroidal saponins are one of the saponin types that exist in an unbound state and have various pharmacological activities,such as anticancer,anti-inflammatory,antiviral,antibacterial and nerves-calming properties...The steroidal saponins are one of the saponin types that exist in an unbound state and have various pharmacological activities,such as anticancer,anti-inflammatory,antiviral,antibacterial and nerves-calming properties.Cancer is a growing health problem worldwide.Significant progress has been made to understand the antitumor effects of steroidal saponins in recent years.According to reported findings,steroidal saponins exert various antitumor activities,such as inhibiting proliferation,inducing apoptosis and autophagy,and regulating the tumor microenvironment,through multiple related signaling pathways.This article focuses on the advances in domestic and foreign studies on the antitumor activity and mechanism of actions of steroidal saponins in the last five years to provide a scientific basis and research ideas for further development and clinical application of steroidal saponins.展开更多
AIM: To investigate the chemical constituents of Dioscorea zingiberensis C. H. Wright. METHODS: The compounds were isolated by various chromatographic techniques, and the structures of the new steroidal saponins were ...AIM: To investigate the chemical constituents of Dioscorea zingiberensis C. H. Wright. METHODS: The compounds were isolated by various chromatographic techniques, and the structures of the new steroidal saponins were elucidated by extensive 1D- and 2D-NMR, MS, and IR spectral analysis. RESULTS: The 70% EtOH extract of the rhizomes of Dioscorea zingiberensis afforded two new steroidal saponins, zingiberenosides A(1) and B(2), along with eight known analogues, 3β, 26-dihydroxy-25(R)-furosta-△5, 20(22)-diene-3-O-α-Lrhamnopyranosyl-(1→2)-O-β-D-glucopyranoside(3), methyl parvifloside(4), deltoside(5), methyl deltoside(6), zingiberensis new saponin(7), deltonin(8), progenin III(9) and diosgenin-diglucoside(10). CONCLUSION: Two new steroidal saponins were isolated from Dioscorea zingiberensis and their structures determined.展开更多
A high-performance liquid chromatography coupled with an evaporative light scattering detector(HPLC-ELSD)has been developed to evaluate the quality of Asparagus filicinus through a simultaneous determination of six st...A high-performance liquid chromatography coupled with an evaporative light scattering detector(HPLC-ELSD)has been developed to evaluate the quality of Asparagus filicinus through a simultaneous determination of six steroidal saponins and one ecdysone,including aspafiliosides A,B,C,E,G,filiasparoside A and 20-hydroxyecdysone.With a C_(18) analytical column,the seven analytes were separated efficiently using acetonitrile-water as the mobile phase in a gradient program.The method limits of detection ranged 0.1250.225μg,and the method limits of quantitation ranged 0.408-0.720μg,respectively.The intra-and inter-day precisions of the method were evaluated and were all less than 3%.All the recoveries for the spiked analytes ranged 95.16%-100.61%.The proposed method was succesfully applied to quantify the seven components in thirteen samples from different localities in China.展开更多
Two new steroidal saponms(2, 3) and two known compounds(1, 4) were isolated from 75% ethanol extract ofAllii macrostemonis bulbus by various spectral methods. The two new steroidal saponins were respectively eluci...Two new steroidal saponms(2, 3) and two known compounds(1, 4) were isolated from 75% ethanol extract ofAllii macrostemonis bulbus by various spectral methods. The two new steroidal saponins were respectively elucidated as (25S)-26-O-β-D-glucopyranosyl-5α-furostanol-2α,3β,22,26-tetrol-3-O-β-D-glucopyranosyl(1→2)-[β-D- glucopyranosyl(1→3)]-β-D-glucopyranosyl(1→4 )-β-D-galactopyranoside(2 ) and 26-O-β-D-glucopyranosyl-5α- furostanol-25( 27)-ene-3β,22,26-tetrol-3-O-β-D-glucopyranosyl( 1→2 )-[β-D-glucopyranosyl( 1→3 )] -β-D-glucopyranosyl- (1→4)-β-D-galactopyranoside(3). Compound 4 was obtained from this medical plant for the first time. The activity experiments of proliferation inhibition on tumor cells were performed by cell counting kit-8(CCK-8) method for compound 2(25S-configuration) and its isomer(compound 1, 25R-configttration). The results show that compounds 1 and 2 have weak inhibition on lung cancer A549 cells, melanoma A375 cells and breast cancer MCF-7 cells as well as certain inhibitory effect on liver cancer HepG2 cells, and the inhibitory effect of compound 1 is stronger than that of compound 2.展开更多
Over the past 30 years,the genus Solanum has received considerable attention in chemical and biological studies.Solanum is the largest genus in the family Solanaceae,comprising of about 2000 species distributed in the...Over the past 30 years,the genus Solanum has received considerable attention in chemical and biological studies.Solanum is the largest genus in the family Solanaceae,comprising of about 2000 species distributed in the subtropical and tropical regions of Africa,Australia,and parts of Asia,e.g.,China,India and Japan.Many of them are economically signifcant species.Previous phytochemical investigations on Solanum species led to the identifcation of steroidal saponins,steroidal alkaloids,terpenes,favonoids,lignans,sterols,phenolic comopunds,coumarins,amongst other compounds.Many species belonging to this genus present huge range of pharmacological activities such as cytotoxicity to diferent tumors as breast cancer(4T1 and EMT),colorectal cancer(HCT116,HT29,and SW480),and prostate cancer(DU145)cell lines.The biological activities have been attributed to a number of steroidal saponins,steroidal alkaloids and phenols.This review features 65 phytochemically studied species of Solanum between 1990 and 2018,fetched from SciFinder,Pubmed,ScienceDirect,Wikipedia and Baidu,using“Solanum”and the species’names as search terms(“all felds”).展开更多
Two new steroidal saponins,named timosaponin P(1) and timosaponin Q(2),were isolated from the rhizome parts of Anemarrhena asphodeloides Bunge using various chromatographic methods.Their structures and absolute config...Two new steroidal saponins,named timosaponin P(1) and timosaponin Q(2),were isolated from the rhizome parts of Anemarrhena asphodeloides Bunge using various chromatographic methods.Their structures and absolute configurations were elucidated by a combination of spectroscopic and spectrometric data,including 1D,2D NMR,HR-ESI-MS and ECD calculations,and this is the first time the absolute configuration of C-23 of steroidal saponin was confirmed by ECD calculations.展开更多
Rhizoma Paridis(RP,M®),a traditional Chinese medicine,is the rhizoma of Paris polyphylla var.yunnanensis(PPY)or P.polyphylla var.chinensis which are widely used as important raw materials for several Chinese pate...Rhizoma Paridis(RP,M®),a traditional Chinese medicine,is the rhizoma of Paris polyphylla var.yunnanensis(PPY)or P.polyphylla var.chinensis which are widely used as important raw materials for several Chinese patent drugs.However,the wild resources of these herbs have become less and less due to their slow-growing characteristics and previously excessive excavation.This review covers untiring investigations on alternative resources of RP by our research group over the past decades,including non-medicinal parts of PPY as well as other plants of Liliaceae and Liliflorae families.The arial parts of PPY and the whole plants of Trillium kamtschaticum might be alternative resources for RP based on the fact that they shared the same or similar saponins and bioactivities.展开更多
基金National Natural Science Foundation of China(81603267)Fundamental Research Funds for the Central UniversitiesShaanxi Key Laboratory of "Qiyao"Resources and Anti-tumor Activities
文摘OBJECTIVE The total steroid saponins(TSSN)isolated from Dioscorea zingiberensis C.H.Wright(D.zingiberensis)has shown a variety of beneficial bioactivities.However,there are no reports about the neuroprotective effects of the TSSN until now.Therefore,we explored the neuroprotective effects of TSSN on rats against transient focal cerebral ischemia-reperfusion(I/R)and the underlying mechanisms.METHODS The healthy adult Sprague-Dawley rats were randomly assigned into six groups.After pre-treatment with the TSSN intragastrically for six days,the rats were subjected to the ischemia injury by the surgery of middle cerebral artery occlusion(MCAO)for 90 min.Some indexes were evaluated and detected.RESULTS As compared to the I/R group,TSSN group of rats,especially given the 30 mg·kg^-1 of TSSN,not only marked reduction in the neurological deficit scores,cerebral infarct volume,and brain edema,but also an increase in neuron survival(Nissl bodies)in the hippocampal cornuammons 1(CA1)and cortex hemisphere of the ipsilateral ischemia.At the same time,the inflammatory cytokines in serum induced by MCAO were significantly alleviated by the TSSN pre-administration.What′s more,the increase of caspase-3 was evidently reduced in the CA1 and cortex of the hemisphere injured brain.Finally,the down-regulating anti-apoptotic Bcl-2 and up-regulating pro-apoptotic Bax proteins were obviously suppressed.CONCLUSION TSSN plays a potential neuroprotective role against a severe injury induced by transient focal cerebral ischemic reperfusion in a rat experimental model,and this role may be mediated by its antiinflammatory and anti-apoptotic actions.
基金supported by the National Natural Science Foundation of China(No.81573550)。
文摘Steroid saponins are secondary metabolites with multiple medicinal values that are found in large quantities in natural medicines,especially Vernonia amygdalina,a famous nature medicine for the treatment of tonsillitis,diabetes,pneumonia.The current study was designed to combine molecular networking(MN)with diagnostic ions for rapid identification ofΔ^(7,9(11))stigmastane-type saponins which were theα-glucosidase inhibitory active substances in V.amygdalina.First,theα-glucosidase inhibitory activities of fiveΔ^(7,9(11))stigmastane-type steroid saponins that were previously isolated were screened,which indicated that theΔ^(7,9(11))stigmastane-type steroid saponin was one of the active constituents responsible for ameliorating diabetes.Furthermore,a strategy was proposed to identify stigmastane-type steroid saponins and verify the plausibility of derived fragmentation pathways by applying MN,MolNetEnhancer and unsupervised substructure annotation(MS2LDA).Based on this strategy,other sevenΔ^(7,9(11))stigmastane-type steroid saponins were identified from this plant.Our research provide scientific evidence for the antidiabetic potential of the steroid saponin-rich extract of V.amygdalina leaf.
基金the State Key Laboratory of Phytochemistry and Plant Resources in West China,Kunming Institute of Botany,Chinese Academy of Sciences(No.P2015-KF07)Science and Technology Program of Guangzhou,China(No.201607010147)Guangdong Medical Science Foundation(No.A2015225).
文摘The Smilax species,widely distributed in tropical region of the world and the warm areas of East Asia and North America,are extensively used as folk medicine to treat inflammatory disorders.Chemical investigation on Smilax species showed they are rich sources of steroidal saponins with diversified structure types,including spirostane,isospirostane,furostane,pregnane,and cholestane.This review mainly summarizes the steroidal saponins(1–104)reported from the genus Smilax between 1967 and 2016,and their biological activities.The relationship between structures of steroidal saponins and related biological activities were briefly discussed.
基金the Special Project of Biological Science and Technology of the Chinese Academy of Sciences (STZ-97-3-08).
文摘Two new steroidal saponins, diuranthosides D and E, were isolated from the whole plant of Diuranthera inarticulata Wang et K. Y. Lang. By means of spectral and chemical analysis, the structure of the new compounds were established as neotigogenin-3-O-(-D-glucopyranosyl (1?3)-(-D-xylopyranosyl-(1?3)-[(-D-glucopyranosyl(1?2)]-(-D-glucopyranosyl(1?4)-(-D-galactopyranoside (1) and neotigogenin-3-O-(-D-glucopyranosyl(1?3)-(-D-glucopyranosyl (1?3)-(-D-xylopyranosyl(1?3)-[(-D-glucopyranosyl(1?2)]-(-D-glucopyranosyl(1?4)-(-D-galactopyranoside (2) respectively.
基金Project supported by the Nahonal Natural Sciencc Foundahon and the grant for doctoral program from State Education Commission of China
文摘Two new minor steroidal saponins, (25R) spirostan-3β-ol-6-one-3-O-[α-L- arabinopyranosyl(1-4)]-β-D-glucopyranosidc (1) and (25S) spirost-5-en -3β, 17α, 27-triol-3-O- [α-L-arabinopyranosyl(1-6)]-β-D-glucopyranosidc (2) were isolated from the roots of Smilax lebrunii. Their structures were established on thc basis of chemical and spectral methods.
基金the Tianjin Research Program of Application Foundation and Advanced Technology(Grant No.19JCYBJC28500)National Science and Technology Major Projects for New Drug Development of China(Grant No.2011ZX09201-201-33)National Natural Science Foundation of China(Grant No.81973792).
文摘Objective:Tribulus terrestris L.(T.terrestris)is a highly valuable traditional Chinese medicine used to treat stroke,inflammation,pulmonary fibrosis,liver cancer,and urolithiasis.To identify the basic substance responsible for the anti-inflammatory effect of TST(total saponins of Tribulus),its chemical composition was systematically studied,and its effect of inhibiting nitric oxide generation and the expression of related inflammatory factors were determined.Methods:To separate chemical constituents from T.terrestris by column chromatography.Spectroscopic methods,including 1D and 2D nuclear magnetic resonance spectroscopy(NMR)and mass spectrometry(MS)techniques,were used to elucidate the isolated compounds.The anti-inflammatory activities of TST and several compounds were evaluated in vitro.Results:Fifteen steroidal saponins,including 9 furostanol steroidal saponins(1,2,3,4,5,6,7,8,and 15)and 6 isospirostanol steroidal saponins(9,10,11,12,13,and 14),were isolated from T.terrestris.TST significantly decreased the expression of tumor necrosis factor-a(TNF-a)and interleukin-6(IL-6)in RAW 264.7 cells stimulated by lipopolysaccharides.Compounds 13 and 15 evidently reduced TNF-a expression.Compounds 6,10,12,13,and 15 markedly reduced IL-6 expression.Conclusions:Compounds 1 was a novel furostanol steroidal saponin,named 26-O-b-D-glucopyranosyl-(25R)-5afurostan-12-carbonyl-20(22)-en-3b,26-diol-3-O-{b-D-xylopyranosyl-(1→2)-[b-D-xylopyranosyl-(1→3)]-b-D-glucopyranosyl-(1→4)-[a-L-rhamnopyranosyl-(1→2)]-b-D-galactopyranoside}.Compounds 2 was isolated from the family Zygophyllaceae for the first time,and 5 and 6 were isolated from the Tribulus genus.TST and compounds 6,10,12,13,and 15 exerts antiinflammatory activity.
文摘Two new C27 steroidal glycosides, named taccaoside A (1) and B (2), were isolated from the traditional Chinese herb Tacca plantaginea. The spectroscopic and chemical evidences revealed their structures to be 26-O--D-glucopyranosyl-(25R)-3?26-dihydroxy furost-5,20-diene -3-O-[?L-rhamnopyranosyl(12)]-[?L-rhamnopyranosyl(13)]--D-glucopyranoside (1) and 26-O--D-glucopyranosyl-(25R)-3?26-dihydroxy furost-5,20-diene-3-O-[?L-rhamnopyranosyl- (12)]-[?D-glucopyranosyl(13)--L-rhamnopyranosyl(13)]--D-glucopyranoside (2), res- pectively.
基金the National Natural Science Foundation of China(Grant Nos.31770388 and U1802281)the Second Tibetan Plateau Scientific Expedition and Research(STEP)program(Grant No.2019QZKK0502).
文摘Phytochemical investigation on the roots of Asparagus cochinchinensis led to the isolation of one new furostanol saponin,named 26-O-β-d-glucopyranosyl-22α-hydroxyl-(25R)-Δ5(6)-furost-3β,26-diol-3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranoside(1),along with three known congeners(2‒4).The structure of new saponin was elucidated via comprehensive inspection of its HRMS and NMR spectral data as well as chemical technology,whereas those of known ones were identified by comparison of their NMR and MS spectral data with those reported in literatures.All isolated saponins were evaluated for their cytotoxic effects on two human liver(MHCC97H)and lung adenocarcinoma(H1299)cancer cells in vitro.Among them,both 1 and 2 showed significant cytotoxicity against above mentioned cell lines.Further studies revealed that these two saponins could significantly inhibit their proliferation of MHCC97H and H1299 cells.
基金the Natural Science Foundation of China(81225024)the National Science and Technology Support Program of China(2013BAI11B02)。
文摘A new limonoid,17-(5-methoxy-2-oxofuran-3-yl)-28-deoxonimbolide(1),and a new C21 steroidal saponin,2a,4a-dihydroxy-pregn-5-en-16-one-3a-O-D-glucopyranoside(2),together with 11 known compounds were isolated from the methanol extract of the leaves of Azadirachta indica.The structures were elucidated by means of spectroscopic analysis and putative biosynthetic origins.All the compounds were evaluated for their antibacterial activities against six bacterial strains.
基金supported by the National Natural Science Foundation of China(Nos.81973192 and 81902185)the Key Research and Development Projects of Shaanxi Province(Nos.2021ZDLSF04-07,2021SF-175 and 2022SF-314)+1 种基金the Natural Science Basic Research Program of Shaanxi Province(No.2022JQ-780)the Key Scientific Research Project of Shaanxi Administration of Traditional Chinese Medicine(No.2021-02-ZZ-003).
文摘Five new saponins,including three steroid saponins,paristenoids A-C(1-3),and two triterpenoid saponins,paristenoids D-E(4-5),along with four known ones(6-9)were isolated from the rhizomes of Paris polyphylla var.stenophylla.The structures of the isolated compounds were identified nainly by detailed spectroscopic analysis,including extensive 1D and 2D NMR,MS,as well as chemical methods.Compound 3 is a new cyclocholestanol-type steroidal saponin with a rare 6/6/6/5/5 fused-rings cholestanol skeleton,and this skeleton has been first found from the genus Paris.The cytotoxicities of the isolated compounds against three human three glioma cell lines(U87MG,U251MG and SHG44)were evaluated,and compound 7 displayed certain inhibitory effect with ICso values of 15.22±1.73,18.87±1.81 and 17.64±1.69μmol^(-1),respectively.
基金supported financially by the National Natural Science Foundation of China (Nos.82222072 and U1902214)Yunnan Key Research and Development Program (No.2019ZF011-2,China)the Research Project of Sichuan Province (2022JDJQ0055,China)。
文摘Sugar-sugar glycosyltransferases play important roles in constructing complex and bioactive saponins.Here,we characterized a series of UDP-glycosyltransferases responsible for biosynthesizing the branched sugar chain of bioactive steroidal saponins from a widely known medicinal plant Paris polyphylla var.yunnanensis.Among them,a 2'-O-rhamnosyltransferase and three 6'-O-glucosyltrasferases catalyzed a cascade of glycosylation to produce steroidal diglycosides and triglycosides,respectively.These UDP-glycosyltransferases showed astonishing substrate promiscuity,resulting in the generation of a panel of 24 terpenoid glycosides including 15 previously undescribed compounds.A mutant library containing 44 variants was constructed based on the identification of critical residues by molecular docking simulations and protein model alignments,and a mutant UGT91AH1^(Y187A)with increased catalytic efficiency was obtained.The steroidal saponins exhibited remarkable antifungal activity against four widespread strains of human pathogenic fungi attributed to ergosterol-dependent damage of fungal cell membranes,and 2'-O-rhamnosylation appeared to correlate with strong antifungal effects.The findings elucidated the biosynthetic machinery for their production of steroidal saponins and revealed their potential as new antifungal agents.
基金supported by the Natural Science Foundation of Shanghai City,China(No.10411969800)the National Nature Science Foundation of China(Nos.81202866 and 81302856)
文摘AIM: To develop and validate a high performance liquid chromatography(HPLC) coupled with diode array and evaporative light scattering detectors(DAD-ELSD) method for the quantitative determination and fingerprint analysis of ten active constituents in three chemical classes(namely, xanthone glycosides, steroidal saponins, and alkaloids) in Zhimu-Huangbai herb pair(ZB). METHOD: Chromatographic separation was performed on a Diamonsil C18 column(4.6 mm × 250 mm, 5 μm, Dikma) by gradient elution using acetic acid in acetonitrile solution at a flow rate of 1.0 mL·min–1 at 260 nm. The drift tube temperature of ELSD was set to 60 ℃ and nebulizer gas pressure was 4.0 Bar. Method validation was performed to assure its linearity, limits of detection and quantification, precision, repeatability, stability, and accuracy. RESULTS: The HPLC-DAD-ELSD method allowed the quantification of ten compounds(phellodendrine, jatrorrhizine, palmatine, berberine, neomangiferin, mangiferin, timosaponin E-I, timosaponin B-II, timosaponin B, and timosaponin A-III), and was successfully applied to fingerprint analysis for ten batches of ZB samples. CONCLUSION: This was the first time to apply the combination of DAD and ELSD for the simultaneous determination of ten active ingredients in ZB. The results showed that the combination of quantitative analysis for marker ingredients and chemical fingerprint for the TCM herb pair provides a potentially powerful, widely introduced, and internationally accepted strategy for assessment of complex TCM formulas.
基金supported by the National Natural Science Foundation of China(No.81503295)2011 Program for Excellent Scientific and Technological Innovation Team of Jiangsu Higher Education+1 种基金Funded by the Priority Academic Program Development of Jiangsu Higher Education InstitutionsJiangsu Province 2011 Plan for Collaborative Innovation
文摘The steroidal saponins are one of the saponin types that exist in an unbound state and have various pharmacological activities,such as anticancer,anti-inflammatory,antiviral,antibacterial and nerves-calming properties.Cancer is a growing health problem worldwide.Significant progress has been made to understand the antitumor effects of steroidal saponins in recent years.According to reported findings,steroidal saponins exert various antitumor activities,such as inhibiting proliferation,inducing apoptosis and autophagy,and regulating the tumor microenvironment,through multiple related signaling pathways.This article focuses on the advances in domestic and foreign studies on the antitumor activity and mechanism of actions of steroidal saponins in the last five years to provide a scientific basis and research ideas for further development and clinical application of steroidal saponins.
基金supported by the Science and Technology Achievement Transformation Project of Jiangsu Province(No.BA2010144)the scientific and technological major special project for "Significant Creation of New Drugs"(No.2012ZX09101231)
文摘AIM: To investigate the chemical constituents of Dioscorea zingiberensis C. H. Wright. METHODS: The compounds were isolated by various chromatographic techniques, and the structures of the new steroidal saponins were elucidated by extensive 1D- and 2D-NMR, MS, and IR spectral analysis. RESULTS: The 70% EtOH extract of the rhizomes of Dioscorea zingiberensis afforded two new steroidal saponins, zingiberenosides A(1) and B(2), along with eight known analogues, 3β, 26-dihydroxy-25(R)-furosta-△5, 20(22)-diene-3-O-α-Lrhamnopyranosyl-(1→2)-O-β-D-glucopyranoside(3), methyl parvifloside(4), deltoside(5), methyl deltoside(6), zingiberensis new saponin(7), deltonin(8), progenin III(9) and diosgenin-diglucoside(10). CONCLUSION: Two new steroidal saponins were isolated from Dioscorea zingiberensis and their structures determined.
基金This investigation was supported by the grants from the Science and Technology Commission of Shanghai Municipality(04DZ19806)the Natural Science Foundation of China(30925042)the State Key Program from the Ministry of Science and Technology,China(2009ZX09502-013).
文摘A high-performance liquid chromatography coupled with an evaporative light scattering detector(HPLC-ELSD)has been developed to evaluate the quality of Asparagus filicinus through a simultaneous determination of six steroidal saponins and one ecdysone,including aspafiliosides A,B,C,E,G,filiasparoside A and 20-hydroxyecdysone.With a C_(18) analytical column,the seven analytes were separated efficiently using acetonitrile-water as the mobile phase in a gradient program.The method limits of detection ranged 0.1250.225μg,and the method limits of quantitation ranged 0.408-0.720μg,respectively.The intra-and inter-day precisions of the method were evaluated and were all less than 3%.All the recoveries for the spiked analytes ranged 95.16%-100.61%.The proposed method was succesfully applied to quantify the seven components in thirteen samples from different localities in China.
基金Supported by the National Natural Science Foundation of China(No.31201295).
文摘Two new steroidal saponms(2, 3) and two known compounds(1, 4) were isolated from 75% ethanol extract ofAllii macrostemonis bulbus by various spectral methods. The two new steroidal saponins were respectively elucidated as (25S)-26-O-β-D-glucopyranosyl-5α-furostanol-2α,3β,22,26-tetrol-3-O-β-D-glucopyranosyl(1→2)-[β-D- glucopyranosyl(1→3)]-β-D-glucopyranosyl(1→4 )-β-D-galactopyranoside(2 ) and 26-O-β-D-glucopyranosyl-5α- furostanol-25( 27)-ene-3β,22,26-tetrol-3-O-β-D-glucopyranosyl( 1→2 )-[β-D-glucopyranosyl( 1→3 )] -β-D-glucopyranosyl- (1→4)-β-D-galactopyranoside(3). Compound 4 was obtained from this medical plant for the first time. The activity experiments of proliferation inhibition on tumor cells were performed by cell counting kit-8(CCK-8) method for compound 2(25S-configuration) and its isomer(compound 1, 25R-configttration). The results show that compounds 1 and 2 have weak inhibition on lung cancer A549 cells, melanoma A375 cells and breast cancer MCF-7 cells as well as certain inhibitory effect on liver cancer HepG2 cells, and the inhibitory effect of compound 1 is stronger than that of compound 2.
文摘Over the past 30 years,the genus Solanum has received considerable attention in chemical and biological studies.Solanum is the largest genus in the family Solanaceae,comprising of about 2000 species distributed in the subtropical and tropical regions of Africa,Australia,and parts of Asia,e.g.,China,India and Japan.Many of them are economically signifcant species.Previous phytochemical investigations on Solanum species led to the identifcation of steroidal saponins,steroidal alkaloids,terpenes,favonoids,lignans,sterols,phenolic comopunds,coumarins,amongst other compounds.Many species belonging to this genus present huge range of pharmacological activities such as cytotoxicity to diferent tumors as breast cancer(4T1 and EMT),colorectal cancer(HCT116,HT29,and SW480),and prostate cancer(DU145)cell lines.The biological activities have been attributed to a number of steroidal saponins,steroidal alkaloids and phenols.This review features 65 phytochemically studied species of Solanum between 1990 and 2018,fetched from SciFinder,Pubmed,ScienceDirect,Wikipedia and Baidu,using“Solanum”and the species’names as search terms(“all felds”).
基金supported by the National Natural Science Foundation of China(No.81573560)the National Training Programs of Innovation and Entrepreneurship for Undergraduates(No.G12123)
文摘Two new steroidal saponins,named timosaponin P(1) and timosaponin Q(2),were isolated from the rhizome parts of Anemarrhena asphodeloides Bunge using various chromatographic methods.Their structures and absolute configurations were elucidated by a combination of spectroscopic and spectrometric data,including 1D,2D NMR,HR-ESI-MS and ECD calculations,and this is the first time the absolute configuration of C-23 of steroidal saponin was confirmed by ECD calculations.
基金supported by the National Natural Science Foundation of China(Nos.31570363,31770391,and 31600283)the Natural Science Foundation of Yunnan Province(2015FA031 and 2017FB128)+2 种基金the Science and Technology Research Program(Grant No.KIB2016001)of Kunming Institute of Botany,CAS,Guiding Program of Interdisciplinary Studies from Kunming Institute of Botany,CAS(Grant No.KIB2017004)the Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China(P2017-ZZ04)Kunming Institute of Botany,Chinese Academy of Sciences.
文摘Rhizoma Paridis(RP,M®),a traditional Chinese medicine,is the rhizoma of Paris polyphylla var.yunnanensis(PPY)or P.polyphylla var.chinensis which are widely used as important raw materials for several Chinese patent drugs.However,the wild resources of these herbs have become less and less due to their slow-growing characteristics and previously excessive excavation.This review covers untiring investigations on alternative resources of RP by our research group over the past decades,including non-medicinal parts of PPY as well as other plants of Liliaceae and Liliflorae families.The arial parts of PPY and the whole plants of Trillium kamtschaticum might be alternative resources for RP based on the fact that they shared the same or similar saponins and bioactivities.