Two new triterpenoids, 3 β, 15α, 21 β, 23-tetrahydroxy-12-oleanen-28-oic acid (1), 3β , 6 α , 21β, 23-tetrahydroxy-12-oleanen-28-oic acid (2), together with seven known compounds, viz., paeonol (3), 3, 4-dihydro...Two new triterpenoids, 3 β, 15α, 21 β, 23-tetrahydroxy-12-oleanen-28-oic acid (1), 3β , 6 α , 21β, 23-tetrahydroxy-12-oleanen-28-oic acid (2), together with seven known compounds, viz., paeonol (3), 3, 4-dihydroxybenzoic acid (4), scosoletin (5), anthraquinones chrysophanol (6), 4H-1-benzopyran-4-one, 5, 7-dihydroxy-2-methyl (7),β-sitosterol (8) and stigmasterol glucoside (9) were isolated by the chromatography of the silica gel, RP-18 and Sephadex-LH 20 from the EtOAc extract of Neonauclea sessilifolia (Roxb.) Merr. ( Rubiaceae ). Their structures were elucidated based on spectral analysis including 1D-, 2D-NMR (HMQC, HMBC), IR and EIMS. Among them, compound 6 was shown to possess inhibitory activity on the growth of Mycobacterium tuberculosis (Zopf) Lehmann et Neumann with a minimum inhibitory amount of 25μg, compounds 2 and 4 also showed weak inhibitory activities on the growteof M. tuberculosis.展开更多
An organic layer prepared from the seed of Aceriphyllum rossii was studied to identify the active compounds for protein tyrosine phosphatase 1B（PTP1B） inhibition.Bioassay guided fractionation resulted in the isolati...An organic layer prepared from the seed of Aceriphyllum rossii was studied to identify the active compounds for protein tyrosine phosphatase 1B（PTP1B） inhibition.Bioassay guided fractionation resulted in the isolation of PTP1B inhibitory activity of triterpenes（1-4）.These four compounds were identified as aceriphyllic acid C（1）,aceriphyllic acid D（2）,aceriphyllic acid E（3） and aceriphyllic acid F（4）.The isolated 1-4 compounds inhibited PTP1B with IC50 values ranged from（2.1±1.5） μmol/L to（11.2±2.5） μmol/L.Kinetic analysis of PTP1B inhibition by aceriphyllic acid C（1） and aceriphyllic acid D（2） suggested that oleanane-type triterpenes inhibited PTP1B activity in a mixed-type manner.展开更多
Seven oleanene triterpenes were isolated from the roots of Potentilla discolor Bge and their structures were identified as 3-oxoolean-12-en-27-oic acid（1）, gypsogenic acid（2）, 3α-hydroxyolean-12-en-27-oic acid（3...Seven oleanene triterpenes were isolated from the roots of Potentilla discolor Bge and their structures were identified as 3-oxoolean-12-en-27-oic acid（1）, gypsogenic acid（2）, 3α-hydroxyolean-12-en-27-oic acid（3）, 3β-hydroxyolean-12-en-27-oic acid（4）, aceriphyllic acid A（5）, aceriphyllic acid A methyl ester（6）, and oleanolic acid（7）. Compounds 1–7 inhibited protein tyrosine phosphatase 1B（PTP1B） activity, with IC50 values ranging from（7.5±0.5） to（22.7±0.5） μmol/L. Among the isolates, compounds 1, 2, 3 and 7 from the Potentilla discolor Bge were found to exhibit selective PTP1 B inhibitory activity.展开更多
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
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
Protein tyrosine phosphatase 1 B(PTP1 B) has led to an intense interest in developing its inhibitors as anti-diabetes, anti-obesity and anti-cancer agents. The fruits of Rubus chingii(Chinese raspberry) were used as a...Protein tyrosine phosphatase 1 B(PTP1 B) has led to an intense interest in developing its inhibitors as anti-diabetes, anti-obesity and anti-cancer agents. The fruits of Rubus chingii(Chinese raspberry) were used as a kind of dietary traditional Chinese medicine. The methanolic extract of R. chingii fruits exhibited significant PTP1 B inhibitory activity. Further bioactivity-guided fractionation resulted in the isolation of three PTP1 B inhibitory ursane-type triterpenes: ursolic acid(1), 2-oxopomolic acid(2), and 2α, 19α-dihydroxy-3-oxo-urs-12-en-28-oic acid(3). Kinetics analyses revealed that 1 was a non-competitive PTP1 B inhibitor, and 2 and 3 were mixed type PTP1 B inhibitors. Compounds 1-3 and structurally related triterpenes(4-8) were further analyzed the structure-activity relationship, and were evaluated the inhibitory selectivity against four homologous protein tyrosine phosphatases(TCPTP, VHR, SHP-1 and SHP-2). Molecular docking simulations were also carried out, and the result indicated that 1, 3-acetoxyurs-12-ene-28-oic acid(5), and pomolic acid-3β-acetate(6) bound at the allosteric site including α3, α6, and α7 helix of PTP1 B.展开更多
Two new pentacyclic triterpene acids, 1a, 3b-dihydroxyl-olean-12-en-28-oic acid and 1a, 2a, 3b-trihydroxyl-olean-12-en-28-oic acid, were isolated from the arial parts of Sabia parviflora.
A new triterpene saponin with 28-nor-urs-12（13）,18（17）-dien-3β-ol as aglycone,named ilexsaponin C（1） was isolated from the roots of Ilex pubescens,together with three known saponins 2,3 and 4.The structure of 1...A new triterpene saponin with 28-nor-urs-12（13）,18（17）-dien-3β-ol as aglycone,named ilexsaponin C（1） was isolated from the roots of Ilex pubescens,together with three known saponins 2,3 and 4.The structure of 1 was elucidated on the basis of spectral analysis including 1D and 2D NMR and HR-ESI-MS.Saponins 1 and 4 exhibited significant XOD inhibitory activity in the test.展开更多
Four new triterpene saponins, mandshunosides F–I(1–4), together with five known compounds(5–9), were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of sp...Four new triterpene saponins, mandshunosides F–I(1–4), together with five known compounds(5–9), were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidences and hydrolysis products. Bisdesmosidic saponin(3–9) showed modest suppression of NO production with the inhibition ratios in the range of 51.3%– 64.6% at 50 μmol·L^(-1), whereas monodesmosidic saponins with a free carboxyl group at C-28(1 and 2) showed potent inhibitory activities with IC_(50) values being 12.7 and 8.3 μmol·L^(-1), respectively.展开更多
AIM: To study the chemical constituents and bioactivity of the stem bark of Mitragyna diversifolia. METHOD: Compounds were isolated by various chromatographic methods. Their structures were elucidated on the basis of ...AIM: To study the chemical constituents and bioactivity of the stem bark of Mitragyna diversifolia. METHOD: Compounds were isolated by various chromatographic methods. Their structures were elucidated on the basis of spectroscopic techniques(IR, UV, MS, and NMR), and they were evaluated for their cytotoxic activities by the MTT method. RESULTS: Eight triterpenes were isolated and identified as 3α, 6β, 19α-trihydroxy-urs-12-en-28-oic acid(1), 3β, 6β, 19α- trihydroxy-urs-12-en-28-oic acid(2), 3-oxo-6β-19α-dihydroxy-urs-12-en-28-oic acid(3), 3β, 6β, 19α-trihydroxy-urs-12-en-24, 28-dioic acid 24-methyl ester(4), 3β, 6β, 19α, 24-tetrahydroxy-urs-12-en-28-oic acid(5), rotundic acid(6), 23-nor-24-exomethylene- 3β, 6β, 19α-trihydroxy-urs-12-en-28-oic acid(7), and pololic acid(8), respectively. All of the isolates were tested against two human tumor cell lines, MCF-7(breast) and HT-29(colon). CONCLUSION: Compound 1 was a new triterpene. Compounds 5-7 exhibited potent inhibitory effects on the growth of MCF-7 and HT-29 cells, and the others showed no cytotoxicity.展开更多
A new triterpene 1, 1 beta, 2 alpha, 3 beta -trihydroxylup-20 (29) -ene was isolated from Cephalomappa sinensis. The structure was elucidated mainly on the basis of 1D and 2D NMR spectral means.
Four new oleanane triterpene saponins were isolated and purified from the whole plant of Clinopodium urticifolium. They were 3B 16B, 23, 28-tetrahydroxyoleana-9 (11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-...Four new oleanane triterpene saponins were isolated and purified from the whole plant of Clinopodium urticifolium. They were 3B 16B, 23, 28-tetrahydroxyoleana-9 (11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 1; 3B, 16B, 21B, 23, 28-pentahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 2; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]-B-D-fucopyranoside 3; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-gluco-pyranosyl-(1-4)-B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]- B-D-fucopyranoside 4. Their structures were elucidated on the basis of interpretation of NMR and MS data and from chemical evidence.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
One new dammarane-type triterpene saponin,named(20S)-3β,20,21-trihydroxydammar-24-ene 3-O-[α-L-rhamnopyranosyl- (1→2)][β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(1),was isolated from the aerial parts of Gynoste...One new dammarane-type triterpene saponin,named(20S)-3β,20,21-trihydroxydammar-24-ene 3-O-[α-L-rhamnopyranosyl- (1→2)][β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(1),was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino.Its structural elucidation was accomplished mainly on the basis of the interrelation of spectroscopic methods, such as IR,HR-TOF-MS,NMR.展开更多
A new derivative of triterpene named Erigeronol 1 was isolated from the EtOH extract of the aerial part of Conyza canadensis together with 15 known compounds for the first time from this plant.The structure of Erigero...A new derivative of triterpene named Erigeronol 1 was isolated from the EtOH extract of the aerial part of Conyza canadensis together with 15 known compounds for the first time from this plant.The structure of Erigeronol 1 was elucidated as 3-O-（hydroxyacetyl） -23,28-dihydroxy-β-amyrin by hydrolysis and spectroscopic analysis.Erigeronol 1 showed potent cytotoxic activity with IC_（50） value of 7.77±0.47μg/mL against melanoma B16 determined by the 3-（4,5-dimethylthiazo-2-yl）-2,5-diphenyltetrazolium bromide（MTT） method.展开更多
Alismatis Rhizoma(AR)is widely used in Chinese medicine,and its major bioactive components,triterpenes,reportedly possess various pharmacological activities.Therefore,it is very important to study the metabolism of tr...Alismatis Rhizoma(AR)is widely used in Chinese medicine,and its major bioactive components,triterpenes,reportedly possess various pharmacological activities.Therefore,it is very important to study the metabolism of triterpenes in vivo.However,the metabolism of AR triterpene extract has not been comprehensively elucidated due to its complex chemical components and metabolic pathways.In this study,an ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry method,which was based on the characteristic ions from an established database of known triterpenes,was used to analyze the major metabolites in rats following the oral administration of Alismatis Rhizoma extracts(ARE).As a result,a total of 233 constituents,with 85 prototype compounds and 148 metabolites,were identified for the first time.Hydrogenation,oxidation,sulfate and glucuronidation conjugation were the major metabolic pathways for triterpenes in AR.In addition,the mutual in vivo transformation of known ARE triterpenes was discovered and confirmed for the first time.Those results provide comprehensive insights into the metabolism of AR in vivo,which will be useful for future studies on its pharmacodynamics and pharmacokinetics.Moreover,this established strategy may be useful in metabolic studies of similar compounds.展开更多
One new Iriterpene saponin was isolated from Panaxjaponicus C. A. Meyer var major （Burk.） C. Y. Wu et K. M. Feng, and established as oleanolic acid 3-O-[β-D-glucopyranosyl-（1 →2）-β-D-glucuronopyranosyl-6＇-O-n-...One new Iriterpene saponin was isolated from Panaxjaponicus C. A. Meyer var major （Burk.） C. Y. Wu et K. M. Feng, and established as oleanolic acid 3-O-[β-D-glucopyranosyl-（1 →2）-β-D-glucuronopyranosyl-6＇-O-n-butyl ester] which showed mod- erate antitumor activities against the A2780 cells and OVCAR-3 cells. Its structure was established by means of spectral data, particularly NMR, including HSQC and HMBC techniques.展开更多
Objective:To evaluate the photoprotective,antioxidant,antiglycation,and antiacne activities of crude extract(CESs)and triterpene saponin fraction(TSSs)of Sapindus saponaria.Methods:HPLC-MS purification was performed o...Objective:To evaluate the photoprotective,antioxidant,antiglycation,and antiacne activities of crude extract(CESs)and triterpene saponin fraction(TSSs)of Sapindus saponaria.Methods:HPLC-MS purification was performed on a Symmetry TM C18 column.The saponins were identified by a UV detector.Antioxidant activity was evaluated by DPPH and O_(2)^(−)radicals scavenging,and FRAP and TBARS assays.Glycation activity was assessed by relative electrophoretic mobility and inhibition of advanced glycation end products(AGEs)formation.Additionally,antiacne activity was determined by inhibition of Cutibacterium acnes,and photoprotective effect was evaluated by Mansur’s method.Results:Most of the triterpene saponins detected in the fraction by HPLC-MS analysis were hederagenin as the aglycon.CESs and TSSs presented varying antioxidant activity in DPPH(CESs:75.69%and TSSs:83.65%),FRAP(CESs:425.39μM TE/g DW and TSSs:649.36μM TE/g DW),TBARS(CESs:42.96%and TSSs:52.16%)and O_(2)^(−)radicals scavenging(CESs:61.33%and TSSs:86.69%)tests.CESs and TSSs also exhibited antiglycation activity comparable to bovine serum albumin treated with aminoguanidine.In addition,CESs and TSSs showed inhibition of AGE formation(34.48%and 61.85%,respectively).Antiacne activity against Cutibacterium acnes was observed with a minimum inhibitory concentration equal to minimum bactericidal concentration(CESs:36.11µg/mL and TSSs:18.34µg/mL).In photoprotective assays,CESs and TSSs showed maximum absorbance of 1.42 to 0.20 and 2.80 to 1.30,respectively,in the wavelength range of 260 to 400 nm.Furthermore,CESs and TSSs showed sun protection factors of 8.89 and 14.89,respectively.Conclusions:Sapindus saponaria fruit extracts show strong antioxidant potential and antiglycation activity against bovine serum albumin glycation and AGE formation.Besides,they presented antibacterial activity against Cutibacterium acnes and photoprotective effect against UV-A and UV-B.展开更多
Two new cycloartane triterpenes were separated from the leaves of Quercus valiabilis Blume. The structures were identified as 4α,14α-dimethyl-9β,19-cycloergost-3α-yl-24-one and 4α,14α-dimethyl-9β,19-cycloergost...Two new cycloartane triterpenes were separated from the leaves of Quercus valiabilis Blume. The structures were identified as 4α,14α-dimethyl-9β,19-cycloergost-3α-yl-24-one and 4α,14α-dimethyl-9β,19-cycloergost-24(24′)-en-3α-yl-acetate.展开更多
Four new protopanaxatriol-type triterpenes(1-2)and glucosides(3-4),were isolated from the rot roots of Panax notoginseng(Burk.)Chen,along with four known ones(5-8).Their structures were elucidated on the basis of exte...Four new protopanaxatriol-type triterpenes(1-2)and glucosides(3-4),were isolated from the rot roots of Panax notoginseng(Burk.)Chen,along with four known ones(5-8).Their structures were elucidated on the basis of extensive spectroscopic analysis(HRESIMS,NMR,UV,IR,and OR)and acidic hydrolysis.The possible transformation pathway of these compounds were also speculated from ginsenoside Rg_(1).Compound 1,with a uniqueα,β-unsaturated ketene in its side chain,showed significant inhibitory effects against NO production on Murine macrophage cells(IC_(50)=4.12±0.20μM)and comparable cytotoxicities against five human cancer cell lines(myeloid leukemia HL-60,lung cancer A-549 cells,hepatocellular carcinoma SMMC7721,breast cancer MCF-7,and colon cancer SW480)to positive control,cisplatin(DDP).展开更多
文摘Two new triterpenoids, 3 β, 15α, 21 β, 23-tetrahydroxy-12-oleanen-28-oic acid (1), 3β , 6 α , 21β, 23-tetrahydroxy-12-oleanen-28-oic acid (2), together with seven known compounds, viz., paeonol (3), 3, 4-dihydroxybenzoic acid (4), scosoletin (5), anthraquinones chrysophanol (6), 4H-1-benzopyran-4-one, 5, 7-dihydroxy-2-methyl (7),β-sitosterol (8) and stigmasterol glucoside (9) were isolated by the chromatography of the silica gel, RP-18 and Sephadex-LH 20 from the EtOAc extract of Neonauclea sessilifolia (Roxb.) Merr. ( Rubiaceae ). Their structures were elucidated based on spectral analysis including 1D-, 2D-NMR (HMQC, HMBC), IR and EIMS. Among them, compound 6 was shown to possess inhibitory activity on the growth of Mycobacterium tuberculosis (Zopf) Lehmann et Neumann with a minimum inhibitory amount of 25μg, compounds 2 and 4 also showed weak inhibitory activities on the growteof M. tuberculosis.
基金The Scientific Research Foundation for the Returned Overseas Chinese Scholars(Grant No.20091590)State Education Ministry and Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules(Yanbian University),Ministry of Education,China(Grant No.201003)
文摘An organic layer prepared from the seed of Aceriphyllum rossii was studied to identify the active compounds for protein tyrosine phosphatase 1B（PTP1B） inhibition.Bioassay guided fractionation resulted in the isolation of PTP1B inhibitory activity of triterpenes（1-4）.These four compounds were identified as aceriphyllic acid C（1）,aceriphyllic acid D（2）,aceriphyllic acid E（3） and aceriphyllic acid F（4）.The isolated 1-4 compounds inhibited PTP1B with IC50 values ranged from（2.1±1.5） μmol/L to（11.2±2.5） μmol/L.Kinetic analysis of PTP1B inhibition by aceriphyllic acid C（1） and aceriphyllic acid D（2） suggested that oleanane-type triterpenes inhibited PTP1B activity in a mixed-type manner.
基金Science and Technology Development Program of Jilin Province(Grant No.20150101225JC)
文摘Seven oleanene triterpenes were isolated from the roots of Potentilla discolor Bge and their structures were identified as 3-oxoolean-12-en-27-oic acid（1）, gypsogenic acid（2）, 3α-hydroxyolean-12-en-27-oic acid（3）, 3β-hydroxyolean-12-en-27-oic acid（4）, aceriphyllic acid A（5）, aceriphyllic acid A methyl ester（6）, and oleanolic acid（7）. Compounds 1–7 inhibited protein tyrosine phosphatase 1B（PTP1B） activity, with IC50 values ranging from（7.5±0.5） to（22.7±0.5） μmol/L. Among the isolates, compounds 1, 2, 3 and 7 from the Potentilla discolor Bge were found to exhibit selective PTP1 B inhibitory activity.
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.
基金supported by the National Natural Science Foundation of China(No.81628012)
文摘Protein tyrosine phosphatase 1 B(PTP1 B) has led to an intense interest in developing its inhibitors as anti-diabetes, anti-obesity and anti-cancer agents. The fruits of Rubus chingii(Chinese raspberry) were used as a kind of dietary traditional Chinese medicine. The methanolic extract of R. chingii fruits exhibited significant PTP1 B inhibitory activity. Further bioactivity-guided fractionation resulted in the isolation of three PTP1 B inhibitory ursane-type triterpenes: ursolic acid(1), 2-oxopomolic acid(2), and 2α, 19α-dihydroxy-3-oxo-urs-12-en-28-oic acid(3). Kinetics analyses revealed that 1 was a non-competitive PTP1 B inhibitor, and 2 and 3 were mixed type PTP1 B inhibitors. Compounds 1-3 and structurally related triterpenes(4-8) were further analyzed the structure-activity relationship, and were evaluated the inhibitory selectivity against four homologous protein tyrosine phosphatases(TCPTP, VHR, SHP-1 and SHP-2). Molecular docking simulations were also carried out, and the result indicated that 1, 3-acetoxyurs-12-ene-28-oic acid(5), and pomolic acid-3β-acetate(6) bound at the allosteric site including α3, α6, and α7 helix of PTP1 B.
文摘Two new pentacyclic triterpene acids, 1a, 3b-dihydroxyl-olean-12-en-28-oic acid and 1a, 2a, 3b-trihydroxyl-olean-12-en-28-oic acid, were isolated from the arial parts of Sabia parviflora.
基金financially supported by the Postgraduate Innovation Project of Jiangsu Province,China(No. CX09B_284Z)
文摘A new triterpene saponin with 28-nor-urs-12（13）,18（17）-dien-3β-ol as aglycone,named ilexsaponin C（1） was isolated from the roots of Ilex pubescens,together with three known saponins 2,3 and 4.The structure of 1 was elucidated on the basis of spectral analysis including 1D and 2D NMR and HR-ESI-MS.Saponins 1 and 4 exhibited significant XOD inhibitory activity in the test.
基金supported by the National Natural Science Foundation of China(No.81503234)
文摘Four new triterpene saponins, mandshunosides F–I(1–4), together with five known compounds(5–9), were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidences and hydrolysis products. Bisdesmosidic saponin(3–9) showed modest suppression of NO production with the inhibition ratios in the range of 51.3%– 64.6% at 50 μmol·L^(-1), whereas monodesmosidic saponins with a free carboxyl group at C-28(1 and 2) showed potent inhibitory activities with IC_(50) values being 12.7 and 8.3 μmol·L^(-1), respectively.
基金supported by the National Science Foundation of China(No.21272275)the Program for Changjiang Scholars and Innovative Research Team in University(No.PCSIRT-IRT1193)
文摘AIM: To study the chemical constituents and bioactivity of the stem bark of Mitragyna diversifolia. METHOD: Compounds were isolated by various chromatographic methods. Their structures were elucidated on the basis of spectroscopic techniques(IR, UV, MS, and NMR), and they were evaluated for their cytotoxic activities by the MTT method. RESULTS: Eight triterpenes were isolated and identified as 3α, 6β, 19α-trihydroxy-urs-12-en-28-oic acid(1), 3β, 6β, 19α- trihydroxy-urs-12-en-28-oic acid(2), 3-oxo-6β-19α-dihydroxy-urs-12-en-28-oic acid(3), 3β, 6β, 19α-trihydroxy-urs-12-en-24, 28-dioic acid 24-methyl ester(4), 3β, 6β, 19α, 24-tetrahydroxy-urs-12-en-28-oic acid(5), rotundic acid(6), 23-nor-24-exomethylene- 3β, 6β, 19α-trihydroxy-urs-12-en-28-oic acid(7), and pololic acid(8), respectively. All of the isolates were tested against two human tumor cell lines, MCF-7(breast) and HT-29(colon). CONCLUSION: Compound 1 was a new triterpene. Compounds 5-7 exhibited potent inhibitory effects on the growth of MCF-7 and HT-29 cells, and the others showed no cytotoxicity.
文摘A new triterpene 1, 1 beta, 2 alpha, 3 beta -trihydroxylup-20 (29) -ene was isolated from Cephalomappa sinensis. The structure was elucidated mainly on the basis of 1D and 2D NMR spectral means.
基金the National Laboratory of Applied Organic Chemistry,Lanzhou University for NMR,HRESIMSto the National Natural Science Foundation of China for financial support(No.29772010).
文摘Four new oleanane triterpene saponins were isolated and purified from the whole plant of Clinopodium urticifolium. They were 3B 16B, 23, 28-tetrahydroxyoleana-9 (11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 1; 3B, 16B, 21B, 23, 28-pentahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 2; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]-B-D-fucopyranoside 3; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-gluco-pyranosyl-(1-4)-B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]- B-D-fucopyranoside 4. Their structures were elucidated on the basis of interpretation of NMR and MS data and from chemical evidence.
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.
基金supported by E&T modern center for Natural products of Liaoning Province of China (No.2006-19-10)
文摘One new dammarane-type triterpene saponin,named(20S)-3β,20,21-trihydroxydammar-24-ene 3-O-[α-L-rhamnopyranosyl- (1→2)][β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(1),was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino.Its structural elucidation was accomplished mainly on the basis of the interrelation of spectroscopic methods, such as IR,HR-TOF-MS,NMR.
文摘A new derivative of triterpene named Erigeronol 1 was isolated from the EtOH extract of the aerial part of Conyza canadensis together with 15 known compounds for the first time from this plant.The structure of Erigeronol 1 was elucidated as 3-O-（hydroxyacetyl） -23,28-dihydroxy-β-amyrin by hydrolysis and spectroscopic analysis.Erigeronol 1 showed potent cytotoxic activity with IC_（50） value of 7.77±0.47μg/mL against melanoma B16 determined by the 3-（4,5-dimethylthiazo-2-yl）-2,5-diphenyltetrazolium bromide（MTT） method.
基金financially supported by the National Natural Science Foundation of China(Grant No.81803717 and U1603104).
文摘Alismatis Rhizoma(AR)is widely used in Chinese medicine,and its major bioactive components,triterpenes,reportedly possess various pharmacological activities.Therefore,it is very important to study the metabolism of triterpenes in vivo.However,the metabolism of AR triterpene extract has not been comprehensively elucidated due to its complex chemical components and metabolic pathways.In this study,an ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry method,which was based on the characteristic ions from an established database of known triterpenes,was used to analyze the major metabolites in rats following the oral administration of Alismatis Rhizoma extracts(ARE).As a result,a total of 233 constituents,with 85 prototype compounds and 148 metabolites,were identified for the first time.Hydrogenation,oxidation,sulfate and glucuronidation conjugation were the major metabolic pathways for triterpenes in AR.In addition,the mutual in vivo transformation of known ARE triterpenes was discovered and confirmed for the first time.Those results provide comprehensive insights into the metabolism of AR in vivo,which will be useful for future studies on its pharmacodynamics and pharmacokinetics.Moreover,this established strategy may be useful in metabolic studies of similar compounds.
基金financially supported by Chinese Academy of Nutritional Sciences,Shanghai Institutes for Biological Sciences
文摘One new Iriterpene saponin was isolated from Panaxjaponicus C. A. Meyer var major （Burk.） C. Y. Wu et K. M. Feng, and established as oleanolic acid 3-O-[β-D-glucopyranosyl-（1 →2）-β-D-glucuronopyranosyl-6＇-O-n-butyl ester] which showed mod- erate antitumor activities against the A2780 cells and OVCAR-3 cells. Its structure was established by means of spectral data, particularly NMR, including HSQC and HMBC techniques.
基金supported by the São Paulo Research Foundation Grant-FAPESP No.2013/10039-1.
文摘Objective:To evaluate the photoprotective,antioxidant,antiglycation,and antiacne activities of crude extract(CESs)and triterpene saponin fraction(TSSs)of Sapindus saponaria.Methods:HPLC-MS purification was performed on a Symmetry TM C18 column.The saponins were identified by a UV detector.Antioxidant activity was evaluated by DPPH and O_(2)^(−)radicals scavenging,and FRAP and TBARS assays.Glycation activity was assessed by relative electrophoretic mobility and inhibition of advanced glycation end products(AGEs)formation.Additionally,antiacne activity was determined by inhibition of Cutibacterium acnes,and photoprotective effect was evaluated by Mansur’s method.Results:Most of the triterpene saponins detected in the fraction by HPLC-MS analysis were hederagenin as the aglycon.CESs and TSSs presented varying antioxidant activity in DPPH(CESs:75.69%and TSSs:83.65%),FRAP(CESs:425.39μM TE/g DW and TSSs:649.36μM TE/g DW),TBARS(CESs:42.96%and TSSs:52.16%)and O_(2)^(−)radicals scavenging(CESs:61.33%and TSSs:86.69%)tests.CESs and TSSs also exhibited antiglycation activity comparable to bovine serum albumin treated with aminoguanidine.In addition,CESs and TSSs showed inhibition of AGE formation(34.48%and 61.85%,respectively).Antiacne activity against Cutibacterium acnes was observed with a minimum inhibitory concentration equal to minimum bactericidal concentration(CESs:36.11µg/mL and TSSs:18.34µg/mL).In photoprotective assays,CESs and TSSs showed maximum absorbance of 1.42 to 0.20 and 2.80 to 1.30,respectively,in the wavelength range of 260 to 400 nm.Furthermore,CESs and TSSs showed sun protection factors of 8.89 and 14.89,respectively.Conclusions:Sapindus saponaria fruit extracts show strong antioxidant potential and antiglycation activity against bovine serum albumin glycation and AGE formation.Besides,they presented antibacterial activity against Cutibacterium acnes and photoprotective effect against UV-A and UV-B.
文摘Two new cycloartane triterpenes were separated from the leaves of Quercus valiabilis Blume. The structures were identified as 4α,14α-dimethyl-9β,19-cycloergost-3α-yl-24-one and 4α,14α-dimethyl-9β,19-cycloergost-24(24′)-en-3α-yl-acetate.
基金This work was supported by the Major Science and Technique Programs in Yunnan Province(2016ZF001-001)the Science and Technology Planning Project of Yunnan Province(2013FC008)Yung-Chi Cheng academician workstation of Yunnan provincial academy of science and technology(2015IC017).
文摘Four new protopanaxatriol-type triterpenes(1-2)and glucosides(3-4),were isolated from the rot roots of Panax notoginseng(Burk.)Chen,along with four known ones(5-8).Their structures were elucidated on the basis of extensive spectroscopic analysis(HRESIMS,NMR,UV,IR,and OR)and acidic hydrolysis.The possible transformation pathway of these compounds were also speculated from ginsenoside Rg_(1).Compound 1,with a uniqueα,β-unsaturated ketene in its side chain,showed significant inhibitory effects against NO production on Murine macrophage cells(IC_(50)=4.12±0.20μM)and comparable cytotoxicities against five human cancer cell lines(myeloid leukemia HL-60,lung cancer A-549 cells,hepatocellular carcinoma SMMC7721,breast cancer MCF-7,and colon cancer SW480)to positive control,cisplatin(DDP).
