To enrich the bioactive cycloartane triterpenoid glycoside named actein and find out more cytotoxic cycloartane triterpenes,a phytochemical study of Cimicifuga foetida was conducted.113 g(0.17%)actein was purified by ...To enrich the bioactive cycloartane triterpenoid glycoside named actein and find out more cytotoxic cycloartane triterpenes,a phytochemical study of Cimicifuga foetida was conducted.113 g(0.17%)actein was purified by recrystallization while eight cycloartane-type triterpenes(1-8)were isolated from the mother liquid.The chemical structures of new compounds(1-4)were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses.Moreover,new compounds showed moderate and broad-spectrum cytotoxicity against 5 human cancer cell lines with IC_(50) values ranging from 4.02 to 15.80μM.展开更多
Six new triterpenoid saponins,aesculusosides A-F(1-6),together with 19 known ones,were isolated from the seeds of Aesculus chinensis.The new structures were elucidated through extensive spectroscopic analyses and by c...Six new triterpenoid saponins,aesculusosides A-F(1-6),together with 19 known ones,were isolated from the seeds of Aesculus chinensis.The new structures were elucidated through extensive spectroscopic analyses and by comparison with previously reported data.Some of the isolates were evaluated for their cytotoxic activities against MCF-7 cell line by an MTT assay,and compounds 15,16,19,and 23-25 exhibited inhibitory activities against MCF-7 with IC50 values ranging from 7.1 to 31.3μM.展开更多
Bioassay-guided fractionation of EtOH extracts obtained from the roots and wood of the Madagascan plant Leptaulus citroides Baill.(Cardiopteridaceae)led to the isolation of ethyl esters of three new triterpenoid sapon...Bioassay-guided fractionation of EtOH extracts obtained from the roots and wood of the Madagascan plant Leptaulus citroides Baill.(Cardiopteridaceae)led to the isolation of ethyl esters of three new triterpenoid saponins(1–3)and the known sesquiterpenoid cinnamosmolide(4).The structures of 1–3 were elucidated by extensive 1D and 2D NMR experiments and mass spectrometry.Compounds 1,2,and 4 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line with IC50 values of 2.8,10.2 and 2.0 lM,respectively.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
In recent years, biosynthesis of triterpenoid saponins in medicinal plants has been widely studied because of their active ingredients with diverse pharmacological activities. Various oxidosqualene cyclases, cytochrom...In recent years, biosynthesis of triterpenoid saponins in medicinal plants has been widely studied because of their active ingredients with diverse pharmacological activities. Various oxidosqualene cyclases, cytochrome P450 monooxygenases, uridine diphosphate glucuronosyltransferases, and transcription factors related to triterpenoid saponins biosynthesis have been explored and identified. In the biosynthesis of triterpenoid saponins, the progress of gene mining by omics-based sequencing, gene screening, gene function verification, catalyzing mechanism of key enzymes and gene regulation are summarized and discussed. By the progress of the biosynthesis pathway of triterpenoid saponins, the large-scale production of some triterpenoid saponins and aglycones has been achieved through plant tissue culture, transgenic plants and engineered yeast cells. However, the complex biosynthetic pathway and structural diversity limit the biosynthesis of triterpenoid saponins in different system. Special focus can further be placed on the systematic botany information of medicinal plants obtained from omics large dataset, and triterpenoid saponins produced by synthetic biology strategies, gene mutations and gene editing technology.展开更多
Two new triterpenoid saponins,ardisicrenoside R and S(1 and 2),and one new phenylpropanoid glycoside,ardicrephenin(3),along with five known compounds(4-8),were isolated from roots of Ardisia crenata.Their structures w...Two new triterpenoid saponins,ardisicrenoside R and S(1 and 2),and one new phenylpropanoid glycoside,ardicrephenin(3),along with five known compounds(4-8),were isolated from roots of Ardisia crenata.Their structures were elucidated on the basis of NMR spectroscopic data and chemical methods.Compounds 2-7 were evaluated for their cytotoxic activities against A549,MCF-7,HepG2 and MDA-MB-231 cell lines by MTT assay.Ardicrenin(6)showed significant cytotoxicity,with IC50 values of 1.17±0.01,1.19±0.06,3.52±0.23,and 16.61±1.02μmol·L^(-1),respectively.展开更多
The present study was designed to investigate the chemical constituents of the roots of Cyathula officinalis. Compounds were isolated by silica gel, Sephadex LH-20, ODS column chromatography, and preparative HPLC. The...The present study was designed to investigate the chemical constituents of the roots of Cyathula officinalis. Compounds were isolated by silica gel, Sephadex LH-20, ODS column chromatography, and preparative HPLC. Their structures were determined on the basis of 1D and 2D NMR techniques, mass spectrometry, and chemical methods. One new oleanane-type triterpenoid saponin, 28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl-(1→3)-β-D-glucopyranosyl] hederagenin(1), was isolated from the roots of Cyathula officinalis. The anti-inflammatory activities of the isolates were evaluated for their inhibitory effects against LPS-induced nitric oxide(NO) production in RAW 264.7 macrophages cells. Compounds 2, 4, and 6 exhibited moderate anti-inflammatory activities.展开更多
The constituents of Cimicifuga plants have been extensively investigated, and the principal metabolites are 9,19-cyclolanostane triterpenoid glycosides, which are distributed widely in Cimicifuga plants, but not in ot...The constituents of Cimicifuga plants have been extensively investigated, and the principal metabolites are 9,19-cyclolanostane triterpenoid glycosides, which are distributed widely in Cimicifuga plants, but not in other members of the Ranunculaceae family, and are considered to be characteristics of the Cimicifuga genus. This type of triterpenoid glycoside possesses several important biological activities. More than 120 cycloartane triterpene glycosides have been isolated from Cimicifuga simplex Wormsk. The aim of this review article is to summarize all the major findings based on the available scientific literatures on C. simplex, with a focus on the identified 9,19-cyclolanostane triterpenoid glycosides. Biological studies of cycloartane triterpene glycosides from Cimicifuga spp. are also discussed.展开更多
Seven new triterpenoid saponins,including five ursane-type saponins,ilexchinenosides R–V(1–5),and two oleananetype saponins,ilexchinenosides W–X(6–7),with four known triterpenoid saponins(8–11)were isolated from ...Seven new triterpenoid saponins,including five ursane-type saponins,ilexchinenosides R–V(1–5),and two oleananetype saponins,ilexchinenosides W–X(6–7),with four known triterpenoid saponins(8–11)were isolated from the leaves of Ilex chinensis.Their structures were elucidated by comprehensive spectroscopic 1 D and 2 D NMR and HR-ESI-MS data.Their sugar moieties were determined by HPLC analysis compared with standards after hydrolysis and derivatization.Compounds 1,2,4,9 and 10 exhibited potential hepatoprotective activity against N-acetyl-p-aminophenol(APAP)-induced Hep G2 cell injury in vitro.展开更多
Objective To study the chemical constituents from the roots of Gypsophila pacifica.Methods The chemical constituents were isolated by various column chromatographic methods and their structures were identified by spec...Objective To study the chemical constituents from the roots of Gypsophila pacifica.Methods The chemical constituents were isolated by various column chromatographic methods and their structures were identified by spectral data together with physicochemical analysis.Results Five compounds were isolated and identified as 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(1),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(2),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(3),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(4),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-α-L-arabino-pyranosyl-(1→4)-α-L-arabinopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(5).Conclusion The five compounds are isolated from this plant for the first time.展开更多
Objective:To study the active ingredients in the root bark of Aralia echinocaulis.Methods:Three triterpenoid saponins were separated from the 70%ethanol extracts and purified by column chromatography and their structu...Objective:To study the active ingredients in the root bark of Aralia echinocaulis.Methods:Three triterpenoid saponins were separated from the 70%ethanol extracts and purified by column chromatography and their structures were determined by spectroscopic analysis.Compound 1 and 3 were evaluated for antioxidant activity by the in vitro DPPH free radical scavenging ability and the protective effect of OH-induced DNA oxidative damage.Results:Compound 1 was a new type of triterpenoid saponin,named as echinocaulisaglycone 3-O-β-Dglucopyranoside(echinocaulisaponin A),and it had good antioxidant activity.Compound 2 was similar to compound 1,named as 1-hydroxyl-echinocaulisaglycone 3-O-β-D-glucopyranoside(echinocaulisaponin B).Compound 3 was also a new type of triterpenoid saponin,named as echinocaulisaglyconeⅡ3-O-a-L-arabinopyranosyl-(1’’→4’)-β-D-glucopyranosiduronic acid(echinocaulisaponin C),and its antioxidant activity was weaker than compound 1.Conclusion:In this study,three new compounds were discovered and two of them were carried out in vitro anti-oxidation studies,laying the foundation for further research on the treatment of related diseases(cardiovascular disease,arthritis,age-related macular degeneration,etc.)through anti-oxidation or quenching free radical function.展开更多
A new triterpenoid saponin was isolated by bioactivity-guided isolation from 揋ualou-xiebai-baijiu-tang?consisting of Fructus trichosanthisi and Bulbus allii macrostemi. Its structure was determined as 3-O-b-D-galacto...A new triterpenoid saponin was isolated by bioactivity-guided isolation from 揋ualou-xiebai-baijiu-tang?consisting of Fructus trichosanthisi and Bulbus allii macrostemi. Its structure was determined as 3-O-b-D-galactopyranosylhederagenin 28-O-b-D-xylopyranosyl (16)- b-D-galactopyranosyl ester by means of chemical evidences and spectral analysis.展开更多
The fruits of Avicennia marina are widely used for both medicine and food in Guangxi of China.As a part of our continuous effort to search for bioactive molecules from the plant,the fruits of A.marina were investigate...The fruits of Avicennia marina are widely used for both medicine and food in Guangxi of China.As a part of our continuous effort to search for bioactive molecules from the plant,the fruits of A.marina were investigated,which has led to one new triterpenoid saponin(1)and 29 known compounds been isolated and their structures were established by using spectroscopic methods and comparing with literature data.The new triterpenoid saponin showed cytotoxicity against GSC3#and GSC-18# with the IC50 values were 12.21 and 5.53 μg/mL respectively,and most of the known compounds had significant antioxidant capacity with the IC_(50) values ranging from 0.36 to 13.07 μg/mL.展开更多
Objective:To investigate the relationship between triterpenoid saponin content and antioxidant,antimicrobial,and α-glucosidase inhibitory activities of 70%ethanolic,butanolic,aqueous,supernate and precipitate extract...Objective:To investigate the relationship between triterpenoid saponin content and antioxidant,antimicrobial,and α-glucosidase inhibitory activities of 70%ethanolic,butanolic,aqueous,supernate and precipitate extracts of Juglans regia leaves.Methods:Triterpenoid saponins of different Juglans regia leaf extracts were measured by the vanillin method.Antioxidant activity was evaluated against DPPH and ABTS free radicals.We also assessed α-glucosidase inhibitory and antimicrobial activities of the leaf extracts.Pearson’s correlation coefficient was evaluated to determine the correlation between the saponin content and biological activities.Results:The butanolic extract was most effective against DPPH with an IC50of 6.63μg/mL,while the aqueous extract showed the highest scavenging activity against ABTS free radical with an IC50of 42.27μg/mL.Pearson’s correlation analysis indicated a strong negative correlation (r=-0.956) between DPPH radical scavenging activity (IC50) and the saponin content in the samples examined.In addition,the aqueous extract showed the best α-glucosidase inhibitory activity compared with other extracts.All the extracts had fair antibacterial activity against Bacillus subtilis,Escherichia coli,and Klebsiella pneumoniae except for the aqueous extract.Conclusions:Juglans regia extracts show potent antioxidant,antimicrobial,and α-glucosidase inhibitory activities.There is a correlation between saponin levels in Juglans regia leaf extracts and the studied activities.However,additional research is required to establish these relationships by identifying the specific saponin molecules responsible for these activities and elucidating their mechanisms of action.展开更多
Assays based on high-performance liquid chromatography(HPLC)and liquid chromatography tandem mass spectrometry(LC–MSn)have been developed and validated for the determination and metabolite identification of the bides...Assays based on high-performance liquid chromatography(HPLC)and liquid chromatography tandem mass spectrometry(LC–MSn)have been developed and validated for the determination and metabolite identification of the bidesmosidic triterpenoid saponin,BTS-1(3-O-β-D-galactopyranosyl-(1-2)-[β-D-xylopyranosyl-(1-3)]-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1-3)-βD-xylopyranosyl-(1-4)-α-L-rhamnopyranosyl-(1-2)-β-D-fucopyranoside),in rat plasma.The assay was successfully applied to a pharmacokinetic study in rats given a single oral dose of BTS-1(400 mg/kg).The results indicated that the compound was rapidly absorbed(Tmax=1.2870.29 h,Cmax=37.475.6 mg/mL)and slowly eliminated(t1/2=13.276.6 h).In addition,secondary glycosides and aglycones of BTS-1 were detected and identified.Since these metabolites are known to be activeα-glucosidase inhibitors,they probably play an important role in mediating the pharmacological effects of the saponin.展开更多
Traditional Chinese medicine(TCM)has been paid much attentions due to the prevention and treatment of steroid hormone disorders.Ginseng,the root of Panax ginseng C.A.Meyer(Araliaceae),is one of the most valuable herbs...Traditional Chinese medicine(TCM)has been paid much attentions due to the prevention and treatment of steroid hormone disorders.Ginseng,the root of Panax ginseng C.A.Meyer(Araliaceae),is one of the most valuable herbs in complementary and alternative medicines around the world.A series of dammarane triterpenoid saponins,also known as phytosteroids,were reported as the primary ingredients of Ginseng,and indicated broad spectral pharmacological actions,including anti-cancer,anti-inflammation and anti-fatigue.The skeletons of the dammarane triterpenoid aglycone are structurally similar to the steroid hormones.Both in vitro and in vivo studies showed that Ginseng and its active ingredients have beneficial hormone-like role in hormonal disorders.This review thus summarizes the structural similarities between hormones and dammarane ginsenosides and integrates the analogous effect of Ginseng and ginsenosides on prevention and treatment of hormonal disorders published in recent twenty years(1998–2018).The review may provide convenience for anticipate structure-function relationship between saponins structure and hormone-like effect.展开更多
AIM: To study the chemical constituents of stems of Gymnema sylvestre(Retz.) Schult. METHODS: Chromatographic techniques using silica gel, C18 reversed phase silica gel, and prep-HPLC were used. The structures were el...AIM: To study the chemical constituents of stems of Gymnema sylvestre(Retz.) Schult. METHODS: Chromatographic techniques using silica gel, C18 reversed phase silica gel, and prep-HPLC were used. The structures were elucidated on the basis of MS and spectroscopic analysis(1D and 2D NMR), as well as chemical methods. RESULTS: Seven compounds were isolated and their structures were elucidated as conduritol A(1), stigmasterol(2), lupeol(3), stigmasterol-3-O-β-D-glucoside(4), the sodium salt of 22α-hydroxy-longispinogenin-3-O-β-D-glucopyranosyl-(1→3)-β-D-glucurono-pyranosyl-28-O-α-L-rhamnopyranoside(5), oleanolic acid-3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside(6), and the sodium salt of 22α-hydroxy-longispinogenin 3-O-β-D-glucuronopyranosyl-28-O-α-L-rhamnopyranoside(7). The inhibition activities of compounds 1, 5-7 on non-enzymatic glycation of protein in vitro were evaluated. CONCLUSION: Compound 7 is a new triterpenoid saponin. It was shown that compounds 1, 5-7 have weak inhibition activities for non-enzymatic glycation of protein in vitro.展开更多
Background:AG8,a triterpenoid saponin isolated from Ardisia gigantifolia Stapf.,our previous studies found that AG8 inhibited the proliferation of triple negative breast cancers(TNBCs)by including ROS generation and t...Background:AG8,a triterpenoid saponin isolated from Ardisia gigantifolia Stapf.,our previous studies found that AG8 inhibited the proliferation of triple negative breast cancers(TNBCs)by including ROS generation and triggering mitochondrial apoptotic pathways.Cancer stem cells(CSCs)capable of maintain relatively low levels of ROS,are vulnerable to the interference of redox state.Compounds capable of generating ROS can affect the finely balanced redox state of CSCs and have potency to selectively kill them.Objective:We selected BT-549 which is most sensitive to AG8 to further study the effects of AG8 on hypoxia-induced proliferation,metastasis and CSCs.Methods:The hypoxia condition was simulated by CoCl2 and cell viability assay of BT-549 cells was performed us-ing MTT.Stemness phenotype were identified using breast CSCs marker(CD24^(−)/low/CD44^(+))and mammosphere formation assay.Cell motility was determined via the wound healing assay and transwell migration.Protein levels of HIF1-α,Oct-4,SOX-2,c-MYC were tested by western blotting.Results:In this study,AG8 showed significant cytotoxic effects on BT-549 triple negative breast cancer cells,but the effects were impaired by HIF1 activation.AG8 inhibited the hypoxia-induced migration and invasion of BT-549 cells.Further studies revealed that hypoxia-induced increases of CD44^(+)CD24^(−)/low and mammosphere population were significantly inhibited by AG8 dose-dependently.Moreover,AG8 decreased the Oct-4 and SOX-2 protein expression without affecting HIF1-αand c-MYC.AG8 significantly inhibited BT-549 xenograft tumors growth in BALB/c nude mice comparing with that of the control group.Conclusion:In summary,AG8 inhibited hypoxia-induced cell migration and invasion through stemness regula-tions,indicating novel mechanisms for the antitumor effects of AG8 against triple negative breast cancer.展开更多
基金This research work was financial supported by Programs of National Natural Science Foundation of China(Nos.81803396 and U1132604)Autonomous Deployment Project(KIB2017010)of Kunming Institute of Botany,CAS,as well as The Major Program of CAS(No.KSZD-EW-Z-004-01).
文摘To enrich the bioactive cycloartane triterpenoid glycoside named actein and find out more cytotoxic cycloartane triterpenes,a phytochemical study of Cimicifuga foetida was conducted.113 g(0.17%)actein was purified by recrystallization while eight cycloartane-type triterpenes(1-8)were isolated from the mother liquid.The chemical structures of new compounds(1-4)were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses.Moreover,new compounds showed moderate and broad-spectrum cytotoxicity against 5 human cancer cell lines with IC_(50) values ranging from 4.02 to 15.80μM.
基金support from the independent topics supported by operational expenses for basic research of China Academy of Chinese Medical Sciences(ZXKT15032).
文摘Six new triterpenoid saponins,aesculusosides A-F(1-6),together with 19 known ones,were isolated from the seeds of Aesculus chinensis.The new structures were elucidated through extensive spectroscopic analyses and by comparison with previously reported data.Some of the isolates were evaluated for their cytotoxic activities against MCF-7 cell line by an MTT assay,and compounds 15,16,19,and 23-25 exhibited inhibitory activities against MCF-7 with IC50 values ranging from 7.1 to 31.3μM.
基金This project was supported by the Fogarty International Center,the National Cancer Institute,the National Institute of Allergy and Infectious Diseases,the National Institute of Mental Health,the National Institute on Drug Abuse,the National Heart Lung and Blood Institute,the National Center for Complementary and Alternative Medicine,the Office of Dietary Supplements,the National Institute of General Medical Sciences,the Biological Sciences Directorate of the National Science Foundation,and the Office of Biological and Environmental Research of the U.S.Department of Energy under Cooperative Agreement U01 TW00313 with the International Cooperative Biodiversity GroupsThis project was also supported by the National Research Initiative of the Cooperative State Research,Education and Extension Service,USDA,Grant#2008-35621-04732These supports are gratefully acknowledged.Work at Virginia Tech was supported by the National Science Foundation under Grant CHE-0722638 for the purchase of the Agilent 6220 mass spectrometer.
文摘Bioassay-guided fractionation of EtOH extracts obtained from the roots and wood of the Madagascan plant Leptaulus citroides Baill.(Cardiopteridaceae)led to the isolation of ethyl esters of three new triterpenoid saponins(1–3)and the known sesquiterpenoid cinnamosmolide(4).The structures of 1–3 were elucidated by extensive 1D and 2D NMR experiments and mass spectrometry.Compounds 1,2,and 4 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line with IC50 values of 2.8,10.2 and 2.0 lM,respectively.
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the Central Significant Increase or Decrease Program of China(No.2060302-1604-05)NSFC(No.81703639)。
文摘In recent years, biosynthesis of triterpenoid saponins in medicinal plants has been widely studied because of their active ingredients with diverse pharmacological activities. Various oxidosqualene cyclases, cytochrome P450 monooxygenases, uridine diphosphate glucuronosyltransferases, and transcription factors related to triterpenoid saponins biosynthesis have been explored and identified. In the biosynthesis of triterpenoid saponins, the progress of gene mining by omics-based sequencing, gene screening, gene function verification, catalyzing mechanism of key enzymes and gene regulation are summarized and discussed. By the progress of the biosynthesis pathway of triterpenoid saponins, the large-scale production of some triterpenoid saponins and aglycones has been achieved through plant tissue culture, transgenic plants and engineered yeast cells. However, the complex biosynthetic pathway and structural diversity limit the biosynthesis of triterpenoid saponins in different system. Special focus can further be placed on the systematic botany information of medicinal plants obtained from omics large dataset, and triterpenoid saponins produced by synthetic biology strategies, gene mutations and gene editing technology.
文摘Two new triterpenoid saponins,ardisicrenoside R and S(1 and 2),and one new phenylpropanoid glycoside,ardicrephenin(3),along with five known compounds(4-8),were isolated from roots of Ardisia crenata.Their structures were elucidated on the basis of NMR spectroscopic data and chemical methods.Compounds 2-7 were evaluated for their cytotoxic activities against A549,MCF-7,HepG2 and MDA-MB-231 cell lines by MTT assay.Ardicrenin(6)showed significant cytotoxicity,with IC50 values of 1.17±0.01,1.19±0.06,3.52±0.23,and 16.61±1.02μmol·L^(-1),respectively.
基金supported by the National New Drug Innovation Major Project of China(No.2012ZX09304005002)the Fundamental Research Funds for the Central Universities(No.JKFP2013003)National Undergraduate Training Program for Innovation and Entrepreneurship(No.G13031)
文摘The present study was designed to investigate the chemical constituents of the roots of Cyathula officinalis. Compounds were isolated by silica gel, Sephadex LH-20, ODS column chromatography, and preparative HPLC. Their structures were determined on the basis of 1D and 2D NMR techniques, mass spectrometry, and chemical methods. One new oleanane-type triterpenoid saponin, 28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl-(1→3)-β-D-glucopyranosyl] hederagenin(1), was isolated from the roots of Cyathula officinalis. The anti-inflammatory activities of the isolates were evaluated for their inhibitory effects against LPS-induced nitric oxide(NO) production in RAW 264.7 macrophages cells. Compounds 2, 4, and 6 exhibited moderate anti-inflammatory activities.
基金supported by the Fund of Education Department of Heilongjiang Province(No.201207)
文摘The constituents of Cimicifuga plants have been extensively investigated, and the principal metabolites are 9,19-cyclolanostane triterpenoid glycosides, which are distributed widely in Cimicifuga plants, but not in other members of the Ranunculaceae family, and are considered to be characteristics of the Cimicifuga genus. This type of triterpenoid glycoside possesses several important biological activities. More than 120 cycloartane triterpene glycosides have been isolated from Cimicifuga simplex Wormsk. The aim of this review article is to summarize all the major findings based on the available scientific literatures on C. simplex, with a focus on the identified 9,19-cyclolanostane triterpenoid glycosides. Biological studies of cycloartane triterpene glycosides from Cimicifuga spp. are also discussed.
基金CAMS Innovation Fund for Medicial Sciences(CIFMS-2019-I2M-1-005)。
文摘Seven new triterpenoid saponins,including five ursane-type saponins,ilexchinenosides R–V(1–5),and two oleananetype saponins,ilexchinenosides W–X(6–7),with four known triterpenoid saponins(8–11)were isolated from the leaves of Ilex chinensis.Their structures were elucidated by comprehensive spectroscopic 1 D and 2 D NMR and HR-ESI-MS data.Their sugar moieties were determined by HPLC analysis compared with standards after hydrolysis and derivatization.Compounds 1,2,4,9 and 10 exhibited potential hepatoprotective activity against N-acetyl-p-aminophenol(APAP)-induced Hep G2 cell injury in vitro.
基金supported by the National Natural Science Foundation of China for Outstanding Young Scientists (No 30525032)
文摘Objective To study the chemical constituents from the roots of Gypsophila pacifica.Methods The chemical constituents were isolated by various column chromatographic methods and their structures were identified by spectral data together with physicochemical analysis.Results Five compounds were isolated and identified as 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(1),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(2),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(3),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(4),3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-α-L-arabino-pyranosyl-(1→4)-α-L-arabinopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside(5).Conclusion The five compounds are isolated from this plant for the first time.
基金National Natural Science Foundation of China(No.81673769)for funding the experiment。
文摘Objective:To study the active ingredients in the root bark of Aralia echinocaulis.Methods:Three triterpenoid saponins were separated from the 70%ethanol extracts and purified by column chromatography and their structures were determined by spectroscopic analysis.Compound 1 and 3 were evaluated for antioxidant activity by the in vitro DPPH free radical scavenging ability and the protective effect of OH-induced DNA oxidative damage.Results:Compound 1 was a new type of triterpenoid saponin,named as echinocaulisaglycone 3-O-β-Dglucopyranoside(echinocaulisaponin A),and it had good antioxidant activity.Compound 2 was similar to compound 1,named as 1-hydroxyl-echinocaulisaglycone 3-O-β-D-glucopyranoside(echinocaulisaponin B).Compound 3 was also a new type of triterpenoid saponin,named as echinocaulisaglyconeⅡ3-O-a-L-arabinopyranosyl-(1’’→4’)-β-D-glucopyranosiduronic acid(echinocaulisaponin C),and its antioxidant activity was weaker than compound 1.Conclusion:In this study,three new compounds were discovered and two of them were carried out in vitro anti-oxidation studies,laying the foundation for further research on the treatment of related diseases(cardiovascular disease,arthritis,age-related macular degeneration,etc.)through anti-oxidation or quenching free radical function.
文摘A new triterpenoid saponin was isolated by bioactivity-guided isolation from 揋ualou-xiebai-baijiu-tang?consisting of Fructus trichosanthisi and Bulbus allii macrostemi. Its structure was determined as 3-O-b-D-galactopyranosylhederagenin 28-O-b-D-xylopyranosyl (16)- b-D-galactopyranosyl ester by means of chemical evidences and spectral analysis.
基金The authors are grateful to the Natural Science Foundation of China(31770388,81225024)the "Ten Thousand Plan",a National High-level Talents Special Support Plan for partial financial support.
文摘The fruits of Avicennia marina are widely used for both medicine and food in Guangxi of China.As a part of our continuous effort to search for bioactive molecules from the plant,the fruits of A.marina were investigated,which has led to one new triterpenoid saponin(1)and 29 known compounds been isolated and their structures were established by using spectroscopic methods and comparing with literature data.The new triterpenoid saponin showed cytotoxicity against GSC3#and GSC-18# with the IC50 values were 12.21 and 5.53 μg/mL respectively,and most of the known compounds had significant antioxidant capacity with the IC_(50) values ranging from 0.36 to 13.07 μg/mL.
基金supported by the Deanship of Scientific Research at Umm Al-Qura University(Grant code:22UQU4331128DSR77).
文摘Objective:To investigate the relationship between triterpenoid saponin content and antioxidant,antimicrobial,and α-glucosidase inhibitory activities of 70%ethanolic,butanolic,aqueous,supernate and precipitate extracts of Juglans regia leaves.Methods:Triterpenoid saponins of different Juglans regia leaf extracts were measured by the vanillin method.Antioxidant activity was evaluated against DPPH and ABTS free radicals.We also assessed α-glucosidase inhibitory and antimicrobial activities of the leaf extracts.Pearson’s correlation coefficient was evaluated to determine the correlation between the saponin content and biological activities.Results:The butanolic extract was most effective against DPPH with an IC50of 6.63μg/mL,while the aqueous extract showed the highest scavenging activity against ABTS free radical with an IC50of 42.27μg/mL.Pearson’s correlation analysis indicated a strong negative correlation (r=-0.956) between DPPH radical scavenging activity (IC50) and the saponin content in the samples examined.In addition,the aqueous extract showed the best α-glucosidase inhibitory activity compared with other extracts.All the extracts had fair antibacterial activity against Bacillus subtilis,Escherichia coli,and Klebsiella pneumoniae except for the aqueous extract.Conclusions:Juglans regia extracts show potent antioxidant,antimicrobial,and α-glucosidase inhibitory activities.There is a correlation between saponin levels in Juglans regia leaf extracts and the studied activities.However,additional research is required to establish these relationships by identifying the specific saponin molecules responsible for these activities and elucidating their mechanisms of action.
基金supported by the National Natural Science Foundation of China(No.81073009)a Project Fund from The Priority Academic Program Development of Jiangsu Higher Education Institutions.
文摘Assays based on high-performance liquid chromatography(HPLC)and liquid chromatography tandem mass spectrometry(LC–MSn)have been developed and validated for the determination and metabolite identification of the bidesmosidic triterpenoid saponin,BTS-1(3-O-β-D-galactopyranosyl-(1-2)-[β-D-xylopyranosyl-(1-3)]-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1-3)-βD-xylopyranosyl-(1-4)-α-L-rhamnopyranosyl-(1-2)-β-D-fucopyranoside),in rat plasma.The assay was successfully applied to a pharmacokinetic study in rats given a single oral dose of BTS-1(400 mg/kg).The results indicated that the compound was rapidly absorbed(Tmax=1.2870.29 h,Cmax=37.475.6 mg/mL)and slowly eliminated(t1/2=13.276.6 h).In addition,secondary glycosides and aglycones of BTS-1 were detected and identified.Since these metabolites are known to be activeα-glucosidase inhibitors,they probably play an important role in mediating the pharmacological effects of the saponin.
基金supported by the National Natural Science Foundation of China(Nos.81530096,81920108033,81573581)the Shanghai Sailing Program(No.19YF 1448800)。
文摘Traditional Chinese medicine(TCM)has been paid much attentions due to the prevention and treatment of steroid hormone disorders.Ginseng,the root of Panax ginseng C.A.Meyer(Araliaceae),is one of the most valuable herbs in complementary and alternative medicines around the world.A series of dammarane triterpenoid saponins,also known as phytosteroids,were reported as the primary ingredients of Ginseng,and indicated broad spectral pharmacological actions,including anti-cancer,anti-inflammation and anti-fatigue.The skeletons of the dammarane triterpenoid aglycone are structurally similar to the steroid hormones.Both in vitro and in vivo studies showed that Ginseng and its active ingredients have beneficial hormone-like role in hormonal disorders.This review thus summarizes the structural similarities between hormones and dammarane ginsenosides and integrates the analogous effect of Ginseng and ginsenosides on prevention and treatment of hormonal disorders published in recent twenty years(1998–2018).The review may provide convenience for anticipate structure-function relationship between saponins structure and hormone-like effect.
基金supported by Program for the Development of Scientific and Technological Plan of Jilin Province(No.20100122)
文摘AIM: To study the chemical constituents of stems of Gymnema sylvestre(Retz.) Schult. METHODS: Chromatographic techniques using silica gel, C18 reversed phase silica gel, and prep-HPLC were used. The structures were elucidated on the basis of MS and spectroscopic analysis(1D and 2D NMR), as well as chemical methods. RESULTS: Seven compounds were isolated and their structures were elucidated as conduritol A(1), stigmasterol(2), lupeol(3), stigmasterol-3-O-β-D-glucoside(4), the sodium salt of 22α-hydroxy-longispinogenin-3-O-β-D-glucopyranosyl-(1→3)-β-D-glucurono-pyranosyl-28-O-α-L-rhamnopyranoside(5), oleanolic acid-3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside(6), and the sodium salt of 22α-hydroxy-longispinogenin 3-O-β-D-glucuronopyranosyl-28-O-α-L-rhamnopyranoside(7). The inhibition activities of compounds 1, 5-7 on non-enzymatic glycation of protein in vitro were evaluated. CONCLUSION: Compound 7 is a new triterpenoid saponin. It was shown that compounds 1, 5-7 have weak inhibition activities for non-enzymatic glycation of protein in vitro.
文摘Background:AG8,a triterpenoid saponin isolated from Ardisia gigantifolia Stapf.,our previous studies found that AG8 inhibited the proliferation of triple negative breast cancers(TNBCs)by including ROS generation and triggering mitochondrial apoptotic pathways.Cancer stem cells(CSCs)capable of maintain relatively low levels of ROS,are vulnerable to the interference of redox state.Compounds capable of generating ROS can affect the finely balanced redox state of CSCs and have potency to selectively kill them.Objective:We selected BT-549 which is most sensitive to AG8 to further study the effects of AG8 on hypoxia-induced proliferation,metastasis and CSCs.Methods:The hypoxia condition was simulated by CoCl2 and cell viability assay of BT-549 cells was performed us-ing MTT.Stemness phenotype were identified using breast CSCs marker(CD24^(−)/low/CD44^(+))and mammosphere formation assay.Cell motility was determined via the wound healing assay and transwell migration.Protein levels of HIF1-α,Oct-4,SOX-2,c-MYC were tested by western blotting.Results:In this study,AG8 showed significant cytotoxic effects on BT-549 triple negative breast cancer cells,but the effects were impaired by HIF1 activation.AG8 inhibited the hypoxia-induced migration and invasion of BT-549 cells.Further studies revealed that hypoxia-induced increases of CD44^(+)CD24^(−)/low and mammosphere population were significantly inhibited by AG8 dose-dependently.Moreover,AG8 decreased the Oct-4 and SOX-2 protein expression without affecting HIF1-αand c-MYC.AG8 significantly inhibited BT-549 xenograft tumors growth in BALB/c nude mice comparing with that of the control group.Conclusion:In summary,AG8 inhibited hypoxia-induced cell migration and invasion through stemness regula-tions,indicating novel mechanisms for the antitumor effects of AG8 against triple negative breast cancer.
