Three new cycloartane triterpene glycosides were isolated from the rhizomes of Actaea asiatica. Their structures were elucidated as 25-ethoxyl-cimigenol-3-O-β-D-xylopyranoside 1, 2'-O-acetyl soulieoside C 2, 2'-O-a...Three new cycloartane triterpene glycosides were isolated from the rhizomes of Actaea asiatica. Their structures were elucidated as 25-ethoxyl-cimigenol-3-O-β-D-xylopyranoside 1, 2'-O-acetyl soulieoside C 2, 2'-O-acetyl cimiracemoside M 3.展开更多
Ten cucurbitane-type triterpene glycosides,including five new compounds named charantosides H(1),J(2),K(3),momor-characoside A(4),goyaglycoside-l(5),and five known compounds(6-10),were isolated from the EtOAc extract ...Ten cucurbitane-type triterpene glycosides,including five new compounds named charantosides H(1),J(2),K(3),momor-characoside A(4),goyaglycoside-l(5),and five known compounds(6-10),were isolated from the EtOAc extract of Momor-dica charantia fruits.The chemical structures of these compounds were identified by 1D and 2D NMR and HRESIMS spectroscopic analyses.Configurations of new compounds were determined by ROESY correlations and comparison of their 13C NMR data with literature reported values.All compounds were evaluated for their inhibition againstα-glucosidase,in which compounds 2,5,7,8,9 showed moderate inhibitory activities with IC50 values ranging from 28.40 to 63.26μM comparing with the positive control(acarbose,IC5087.65±6.51μM).展开更多
Further studies on the sea cucumber Bohadschia marmorata Jaeger led to the isolation of a new holostan-type triterpene glycoside,Marmoroside C(1)together with a known triterpene glycoside(2).On the basis of spectr...Further studies on the sea cucumber Bohadschia marmorata Jaeger led to the isolation of a new holostan-type triterpene glycoside,Marmoroside C(1)together with a known triterpene glycoside(2).On the basis of spectroscopic analyses,including two- dimensional NMR techniques,and chemical reactions,the structure of the new triterpene glycoside was elucidated as 3-O-[3-O- methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodium-sulfato-β-D-xylo- pyranosyl]-25-acetoxy-22-oxo-9(11)-holostene-3β,12α,17α-triol.展开更多
Objective To study the new triterpene glycosides from sea cucumber Holothuria scabra with cytotoxic activity. Methods Triterpene glycosides from H. scabra were separated and purified by chromatography on DA-101, silic...Objective To study the new triterpene glycosides from sea cucumber Holothuria scabra with cytotoxic activity. Methods Triterpene glycosides from H. scabra were separated and purified by chromatography on DA-101, silica gel, and reversed-phase silica gel column, as well as RP-HPLC. Their structures were elucidated on the basis of spectral data and chemical evidence. Results Three triterpene glycosides were identified as scabraside D (1), fuscocineroside C (2), and 24-dehydroechinoside A (3). Their inhibition on P-388, A549, MKN-28, HCT116, and MCF-7 cells were significant. Conclusion Scabraside D (1) is a new triterpene glycoside, and compounds 2 and 3 are isolated from H. scabra for the first time. The glycosides 1-3 show the in vitro cytotoxicity against five human tumor cell lines in comparison to 10-hydroxycamptothecin.展开更多
A new cycloartane triterpene glycoside was isolated from the rhizome of Souliea vaginata. Its structure was established as 12-deacetyloxy-15α-hydroxy-23-epi-26-deoxyactein by spectroscopic and chemical methods.
A new triterpene glycoside, leucospilotaside A, along with a known saponin, isolated from sea cucumber Holothuria leucospilota, and its structure was elucidated as 3β-O-[4-O-sodiumsulfate-β-d-quinovopyranosyl-(1 → ...A new triterpene glycoside, leucospilotaside A, along with a known saponin, isolated from sea cucumber Holothuria leucospilota, and its structure was elucidated as 3β-O-[4-O-sodiumsulfate-β-d-quinovopyranosyl-(1 → 2)-β-d-xylopyranosyl]-holosta-22-ketone-9-en-17α,25α-diol (1) by extensive spectroscopic analysis and chemical methods. Leucospilotaside A (1) has a ketone carbonyl group (22) in the aglycon side chain.展开更多
A new triterpene glycoside, leucospilotaside C, along with two known saponin, was isolated from sea cucumber Holothuria leucospilota collected from the South China Sea, and its structure was elucidated as 3-0-{4′-O-s...A new triterpene glycoside, leucospilotaside C, along with two known saponin, was isolated from sea cucumber Holothuria leucospilota collected from the South China Sea, and its structure was elucidated as 3-0-{4′-O-sodiumsulfate-β′-D-xylopyranosyl}- holosta-22,25-epoxy-9-ene-3β,12α,17α-triol (1) by extensive spectroscopic analysis and chemical methods. The glycosides have the same triterpene aglycone, but differ in the oligosaccharide moieties.展开更多
Abstract: A new sulfated triterpene glycoside named as 17-dehydroxyholothurin A 1 was isolated from the sea cucumber Holothuria impatiens. Its structure was elucidated on the basis of spectroscopic data (2D NMR and...Abstract: A new sulfated triterpene glycoside named as 17-dehydroxyholothurin A 1 was isolated from the sea cucumber Holothuria impatiens. Its structure was elucidated on the basis of spectroscopic data (2D NMR and MS) and chemical evidence. Compound 1 showed cytotoxic activity against cancer cell lines MKN-28, MFC-7, KB, HL-60 and Hep G2 with IC50 values of 1.98, 4.53, 2.01, 4.69 and 2.80 ×10^-6 tool/L, respectively.展开更多
A new triterpene glycoside, 24S-cycloartane-3 beta, 16 beta, 24, 25, 30-pentaol 3-O-(2-O-beta-D-xylosyl)-beta-D-xyloside was isolated from Thalictrum smithii. Its structure was determined by spectroscopic and chemical...A new triterpene glycoside, 24S-cycloartane-3 beta, 16 beta, 24, 25, 30-pentaol 3-O-(2-O-beta-D-xylosyl)-beta-D-xyloside was isolated from Thalictrum smithii. Its structure was determined by spectroscopic and chemical methods.展开更多
A new oleanane-rype triterpene glycoside, Aster saponin G, was isolated from the root of Aster tataricus L.F. (Compositae). and its structure was elucidated on the basis of spectral and chemical methods. Aster saponin...A new oleanane-rype triterpene glycoside, Aster saponin G, was isolated from the root of Aster tataricus L.F. (Compositae). and its structure was elucidated on the basis of spectral and chemical methods. Aster saponin G is 3-0[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]-2β,3β, 16α-trihydroxyolean-12-en-28-oic acid(asterogenic acid) 28-0-[β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl] ester展开更多
A new disulfated triterpene glycoside named intercedenside B was isolated from the sea cucumber Mensamaria intercedens Lampert. The structure was deduced from the spectral data.
A new triterpene glycoside, pomolic acid 3-O-6″-methyl-β-D-glucuronopyranosyl-(1→3)-α-L-arabino- pyranoside, and a new flavonol glycoside, quercetin 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside togeth...A new triterpene glycoside, pomolic acid 3-O-6″-methyl-β-D-glucuronopyranosyl-(1→3)-α-L-arabino- pyranoside, and a new flavonol glycoside, quercetin 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside together with three known triterpene saponins and two flavonol glycosides, were isolated from the leaves of Ilex cornuta. Their structures were established on the basis of spectroscopic analysis.展开更多
Ds-echinoside A (DSEA),a non-sulfated triterpene glycoside,was isolated from the sea cucumber Pearsonothuria graeffei.In vitro and in vivo investigations were conducted on the effects of DSEA on tumor cell adhesion,mi...Ds-echinoside A (DSEA),a non-sulfated triterpene glycoside,was isolated from the sea cucumber Pearsonothuria graeffei.In vitro and in vivo investigations were conducted on the effects of DSEA on tumor cell adhesion,migration,invasion,and angiogenesis.In this study,we found that DSEA inhibited the proliferation of human hepatocellular liver carcinoma cells Hep G2,with a half-maximal inhibitory concentration (IC50) of 2.65 μmol/L,and suppressed Hep G2 cell adhesion,migration,and invasion in a dose-dependent manner.DSEA also reduced tube formation of human endothelial cells ECV-304 on matrigel in vitro and attenuated neovascularization in the chick embryo chorioallantoic membrane (CAM) assay in vivo.Immunocytochemical analysis revealed that DSEA significantly decreased the expression of matrix metalloproteinase-9 (MMP-9),which plays an important role in the degradation of basement membrane in tumor metastasis and angiogenesis.DSEA also increased the protein expression level of tissue inhibitor of metalloproteinase-1 (TIMP-1),an important regulator of MMP-9 activation.From the results of Western blotting,the expressions of nuclear factor-kappa B (NF-κB) and vascular endothelial growth factor (VEGF) were found to be remarkably reduced by DSEA.These findings suggest that DSEA exhibits a significant antimetastatic activity through the specific inhibition of NF-κB-dependent MMP-9 and VEGF expressions.展开更多
Microbial transformation of a triterpene glycoside, quinovic acid 3-O-β-D-quinovopyranoside by Streptomyces griseus ACCT 13273 was achieved with the aim of generating new bio-active derivatives. Preparative-scale bio...Microbial transformation of a triterpene glycoside, quinovic acid 3-O-β-D-quinovopyranoside by Streptomyces griseus ACCT 13273 was achieved with the aim of generating new bio-active derivatives. Preparative-scale biotransformation with standard two-stage fermentation protocol afforded a new oxidized metabolite, as a result of the hydroxylation of the methyl group at C-30, which was difficult to achieve by chemical means. The metabolite was elucidated based on extensive NMR and high-resolution mass spectral analyses.展开更多
文摘Three new cycloartane triterpene glycosides were isolated from the rhizomes of Actaea asiatica. Their structures were elucidated as 25-ethoxyl-cimigenol-3-O-β-D-xylopyranoside 1, 2'-O-acetyl soulieoside C 2, 2'-O-acetyl cimiracemoside M 3.
基金supported by a program of the National Natural Science Foundation of China(Nos.31872675 and 81373288)the cooperation program between Chinese Academy of Sciences and Guangdong Province(2013B09110011).
文摘Ten cucurbitane-type triterpene glycosides,including five new compounds named charantosides H(1),J(2),K(3),momor-characoside A(4),goyaglycoside-l(5),and five known compounds(6-10),were isolated from the EtOAc extract of Momor-dica charantia fruits.The chemical structures of these compounds were identified by 1D and 2D NMR and HRESIMS spectroscopic analyses.Configurations of new compounds were determined by ROESY correlations and comparison of their 13C NMR data with literature reported values.All compounds were evaluated for their inhibition againstα-glucosidase,in which compounds 2,5,7,8,9 showed moderate inhibitory activities with IC50 values ranging from 28.40 to 63.26μM comparing with the positive control(acarbose,IC5087.65±6.51μM).
文摘Further studies on the sea cucumber Bohadschia marmorata Jaeger led to the isolation of a new holostan-type triterpene glycoside,Marmoroside C(1)together with a known triterpene glycoside(2).On the basis of spectroscopic analyses,including two- dimensional NMR techniques,and chemical reactions,the structure of the new triterpene glycoside was elucidated as 3-O-[3-O- methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodium-sulfato-β-D-xylo- pyranosyl]-25-acetoxy-22-oxo-9(11)-holostene-3β,12α,17α-triol.
基金National High-Tech Research and Development Project (863 Project, 2006AA09Z417)National Natural Science Foundation of China (20772155)
文摘Objective To study the new triterpene glycosides from sea cucumber Holothuria scabra with cytotoxic activity. Methods Triterpene glycosides from H. scabra were separated and purified by chromatography on DA-101, silica gel, and reversed-phase silica gel column, as well as RP-HPLC. Their structures were elucidated on the basis of spectral data and chemical evidence. Results Three triterpene glycosides were identified as scabraside D (1), fuscocineroside C (2), and 24-dehydroechinoside A (3). Their inhibition on P-388, A549, MKN-28, HCT116, and MCF-7 cells were significant. Conclusion Scabraside D (1) is a new triterpene glycoside, and compounds 2 and 3 are isolated from H. scabra for the first time. The glycosides 1-3 show the in vitro cytotoxicity against five human tumor cell lines in comparison to 10-hydroxycamptothecin.
文摘A new cycloartane triterpene glycoside was isolated from the rhizome of Souliea vaginata. Its structure was established as 12-deacetyloxy-15α-hydroxy-23-epi-26-deoxyactein by spectroscopic and chemical methods.
文摘A new triterpene glycoside, leucospilotaside A, along with a known saponin, isolated from sea cucumber Holothuria leucospilota, and its structure was elucidated as 3β-O-[4-O-sodiumsulfate-β-d-quinovopyranosyl-(1 → 2)-β-d-xylopyranosyl]-holosta-22-ketone-9-en-17α,25α-diol (1) by extensive spectroscopic analysis and chemical methods. Leucospilotaside A (1) has a ketone carbonyl group (22) in the aglycon side chain.
基金supported by the State Foundation for High-tech Project"863"from the Ministry of Science and Technology,China (No.2001AA624100)grant from National Natural Science Foundation of China (No.20772155).
文摘A new triterpene glycoside, leucospilotaside C, along with two known saponin, was isolated from sea cucumber Holothuria leucospilota collected from the South China Sea, and its structure was elucidated as 3-0-{4′-O-sodiumsulfate-β′-D-xylopyranosyl}- holosta-22,25-epoxy-9-ene-3β,12α,17α-triol (1) by extensive spectroscopic analysis and chemical methods. The glycosides have the same triterpene aglycone, but differ in the oligosaccharide moieties.
文摘Abstract: A new sulfated triterpene glycoside named as 17-dehydroxyholothurin A 1 was isolated from the sea cucumber Holothuria impatiens. Its structure was elucidated on the basis of spectroscopic data (2D NMR and MS) and chemical evidence. Compound 1 showed cytotoxic activity against cancer cell lines MKN-28, MFC-7, KB, HL-60 and Hep G2 with IC50 values of 1.98, 4.53, 2.01, 4.69 and 2.80 ×10^-6 tool/L, respectively.
文摘A new triterpene glycoside, 24S-cycloartane-3 beta, 16 beta, 24, 25, 30-pentaol 3-O-(2-O-beta-D-xylosyl)-beta-D-xyloside was isolated from Thalictrum smithii. Its structure was determined by spectroscopic and chemical methods.
基金Project supported by the Nationl Science Foundation of China
文摘A new oleanane-rype triterpene glycoside, Aster saponin G, was isolated from the root of Aster tataricus L.F. (Compositae). and its structure was elucidated on the basis of spectral and chemical methods. Aster saponin G is 3-0[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]-2β,3β, 16α-trihydroxyolean-12-en-28-oic acid(asterogenic acid) 28-0-[β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl] ester
文摘A new disulfated triterpene glycoside named intercedenside B was isolated from the sea cucumber Mensamaria intercedens Lampert. The structure was deduced from the spectral data.
文摘A new triterpene glycoside, pomolic acid 3-O-6″-methyl-β-D-glucuronopyranosyl-(1→3)-α-L-arabino- pyranoside, and a new flavonol glycoside, quercetin 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside together with three known triterpene saponins and two flavonol glycosides, were isolated from the leaves of Ilex cornuta. Their structures were established on the basis of spectroscopic analysis.
基金Project supported by the National High-Tech R & D Program (863) of China (No. 2007AA091805)and the National Natural Science Foundation of China (Nos. 30972284 and 30871944)
文摘Ds-echinoside A (DSEA),a non-sulfated triterpene glycoside,was isolated from the sea cucumber Pearsonothuria graeffei.In vitro and in vivo investigations were conducted on the effects of DSEA on tumor cell adhesion,migration,invasion,and angiogenesis.In this study,we found that DSEA inhibited the proliferation of human hepatocellular liver carcinoma cells Hep G2,with a half-maximal inhibitory concentration (IC50) of 2.65 μmol/L,and suppressed Hep G2 cell adhesion,migration,and invasion in a dose-dependent manner.DSEA also reduced tube formation of human endothelial cells ECV-304 on matrigel in vitro and attenuated neovascularization in the chick embryo chorioallantoic membrane (CAM) assay in vivo.Immunocytochemical analysis revealed that DSEA significantly decreased the expression of matrix metalloproteinase-9 (MMP-9),which plays an important role in the degradation of basement membrane in tumor metastasis and angiogenesis.DSEA also increased the protein expression level of tissue inhibitor of metalloproteinase-1 (TIMP-1),an important regulator of MMP-9 activation.From the results of Western blotting,the expressions of nuclear factor-kappa B (NF-κB) and vascular endothelial growth factor (VEGF) were found to be remarkably reduced by DSEA.These findings suggest that DSEA exhibits a significant antimetastatic activity through the specific inhibition of NF-κB-dependent MMP-9 and VEGF expressions.
文摘Microbial transformation of a triterpene glycoside, quinovic acid 3-O-β-D-quinovopyranoside by Streptomyces griseus ACCT 13273 was achieved with the aim of generating new bio-active derivatives. Preparative-scale biotransformation with standard two-stage fermentation protocol afforded a new oxidized metabolite, as a result of the hydroxylation of the methyl group at C-30, which was difficult to achieve by chemical means. The metabolite was elucidated based on extensive NMR and high-resolution mass spectral analyses.