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1.
Three new spirostane-type glycosides (1–3) were isolated from the whole plant of Allium flavum. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25R)-2α-hydroxyspirost-5-en-3β-yl O-β-d-xylopyranosyl-(1 → 3)-[β-d-galactopyranosyl-(1→2)]-β-d-galactopyranosyl-(1→4)-β-d-galactopyranoside (1), (20S,25R)-2α-hydroxyspirost-5-en-3β-yl O-β-d-xylopyranosyl-(1 → 3)-[β-d-glucopyranosyl-(1→2)]-β-d-galactopyranosyl-(1→4)-β-d-galactopyranoside (2), and (20S,25R)-spirost-5-en-3β-yl O-α-l-rhamnopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1→2)]-β-d-glucopyranoside (3). The three saponins were evaluated for cytotoxicity against a human cancer cell line (colorectal SW480).  相似文献   

2.
Four new oleanane type triterpenoid saponins (1–4) and three known saponins (5–7) were isolated from the whole plant of Clematis lasiandra Maxim. The structures of the four new compounds were elucidated as 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl hederagenin (1), 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl oleanolic acid 28-O-β-d-glucopyranosyl ester (2), 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl hederagenin (3) and 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-α-l-arabinopyranosyl hederagenin (4) on the basis of extensive spectroscopic analysis and chemical evidence. Compounds 1–7 were evaluated for their cytotoxicity against human tumor cell lines HL-60, Hep-G2 and SGC-7901, and all of the evaluated saponins showed significant cytotoxicity to those three tumor cell lines with IC50 in the range from 1.40 to 19.50 μmol/L except for compounds 2 and 6.  相似文献   

3.
Four new triterpenoids, sweriyunnangenin A (1), sweriyunnanosides A (2), B (3) and C (4), along with nineteen known compounds (5–23) were isolated from Swertia yunnanensis. Based on extensive spectroscopic analyses (1D- and 2D-NMR, HRESIMS, UV, IR, [α]D), the structures of sweriyunnangenin A (1), sweriyunnanosides A (2), B (3) and C (4) were elucidated as taraxer-14-ene-3α,6β-diol, oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 2)-O-β-d-glucopyranoside, 2α,3β-di-hydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl (1 → 6)-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranoside and hederagenin 28-O-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranoside, respectively. Twenty-two compounds were evaluated for their anti-HBV activities on the HepG 2.2.15 cell line in vitro, of which nine compounds showed potent anti-HBV activities. Compounds 1, 5–6, 14–16 and 19 showed activities against the secretion of HBsAg (IC50 values from 0.10 to 1.76 mM) and HBeAg (IC50 values from 0.04 to 1.41 mM), and compounds 11 and 13–16 exhibited significant inhibition on HBV DNA replication (IC50 values from 0.01 to 0.09 mM).  相似文献   

4.
Two new trisaccharide intermediates of phenylethanoid glycosides, peiioside A1/A2 (1a/1b) and peiioside B (2), were isolated from the n-BuOH fraction of MeOH extract of the stems of Callicarpa peii H.T. Chang, together with five biogenetic relevant known compounds 3–7. The structures of compounds 1 and 2 were elucidated by extensive spectroscopic methods (especially 2D-NMR techniques) and acid-catalyzed hydrolysis as O-α-l-rhamnopyranosyl-(1″ → 3′)-O-[β-d-apiofuranosyl-(1‴ → 6′)] -4′-O-[(E)-caffeoyl]-d-glucopyranoside] (1a/1b), 3,4-dihydroxy-β-phenylethoxy-O-[β-d-apiofuranosyl-(1‴ → 6′)-α-l-rhamnopyranosyl-(1″ → 3′)-O-β-d-glucopyranoside] (2), respectively. On the basis of the isolated compounds, a presumable biogenetic pathway of the biologically interesting phenylethanoid glycosides about forsythoside B (3) and acteoside (4) isolated from this species was proposed. Isolation of five related intermediates (1–2, 5–7) provided further support for the biogenetic path. This is the first report about phytochemical research on C. peii and the biogenetic hypothesis of forsythoside B and acteoside.  相似文献   

5.
Five new ursane-type triterpenoidal saponins (1–5), together with five known ones (6–10), were isolated from the EtOH extract of the roots of Ilex cornuta. The structures of saponins 1–5 were elucidated as 19α-hydroxyurs-12-en-28-oic acid 3β-O-β-D-glucuronopyranoside (1), 19α-hydroxyurs-12-en-28-oic acid 3β-O-β-D-glucuronopyranoside-6-O-ethyl ester (2), 19α-hydroxyurs-12-en-28-oic acid 3β-O-α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyranoside (3), 3β-O-[α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyranosyl]-19α-hydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (4) and 3β-O-[α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyranoside-6-O-methyl ester]-19α-hydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (5), on the basis of spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR) and chemical reactions. Protective effects of compounds 1–10 against H2O2-induced H9c2 cardiomyocyte injury were tested. Compounds 1–5, 7, and 10 showed cell-protective effects. Among them compound 5 exhibited the highest activity. No significant DPPH radical scavenging activity was observed for compounds 1–10.  相似文献   

6.
Five new triterpenoid saponins, named as sibiricasaponins A–E (1–5), were isolated and identified from the aerial parts of Polygala sibirica L., together with nine known triterpenoid saponins (6–14). The chemical structures of the five new triterpenoid saponins (1–5) were elucidated as 3β,19α-dihydroxyurso-12-ene-23,28-dioic acid 3-O-β-d-glucuronopyranoside (1), pomolic acid 3-O-(3-O-sulfo)-α-l-arabinopyranoside (2), pomolic acid 3-O-(4-O-sulfo)-β-d-xylopyranoside (3), pomolic acid 3-O-(2-O-acetyl-3-O-sulfo)-α-l-arabinopyranoside (4), and 3-O-β-d-glucopyranosyl medicagenic acid 28-O-β-d-galactopyranosyl (1 → 4)-β-d-xylopyranosyl (1 → 4)-α-l-rhamnopyranosyl (1 → 2)-(4-O-acetyl)-[β-d-apiofuranosyl (1 → 3)]-β-d-fucopyranosyl ester (5), respectively, on the basis of spectroscopic data and physicochemical evidences. These isolated compounds (1–14) were evaluated for their anti-ischemic effects on oxygen/glucose deprivation (OGD) model in vitro, and only compound 7 showed a weak anti-ischemia effect, with EC50 value of 46.7 μM.  相似文献   

7.
Two new flavonoids, quercetin-3-O-β-d-xylopyranosyl-(1 → 2)-α-d-ribopyranoside (1) and kaempferol-3-O-β-d-xylopyranosyl-(1 → 2)-α-d-ribopyranoside (2), and one new phenolic derivative, gallicin-p-O-(6′-O-caffeoyl)-β-d-glucoside (3), together with twelve known compounds were isolated from the leaves of Rosa sericea (Rosaceae family). The structures of the new compounds were established by means of spectroscopic analysis including one- and two-dimensional NMR spectroscopy. Some of the isolated compounds were tested for the cytotoxicity of a breast cancer cell (MCF-7) line. The results showed that rubanthrone A (4) has moderate cytotoxicity against the MCF-7 cell line.  相似文献   

8.
Three new polyacetylenes, 8-(Z)-decene-4, 6-diyne-1, 3, 10-triol (1), 1, 3S, 8S-trihydroxydec-9-en-4, 6-yne (2), 3S, 8S-dihydroxydec-9-en-4, 6-yne 1-O-β -D-glucopyranoside (3), and one new glucosyl caffeoate, 1-O-ethyl-6-O-caffeoyl-β -D-glucopyranose (4), together with 34 known compounds were isolated from Artemisia capillaris. The structures of the new compounds were determined by extensive spectroscopic analyses including 1D and 2D NMR, HRESIMS, [α]D and CD experiments. Among them, 19 compounds showed activity inhibiting HBsAg secretion; 20 compounds showed activity inhibiting HBeAg secretion; and 25 compounds possessed inhibitory activity against HBV DNA replication according to our anti-HBV assay on HepG 2.2.15 cell line in vitro. The most active compound 12 could inhibit not only the secretions of HBsAg and HBeAg, but also HBV DNA replication with IC50 values of 15.02 μM (SI = 111.3), 9.00 μM (SI = 185.9) and 12.01 μM (SI = 139.2).  相似文献   

9.
A new (2α,3β)-23-sulphonyl-2,3-dihydroxyurs-12-en-28-oic acid O-α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1) together with eighteen known compounds were isolated from Centella erecta (L.f.) Fern. Their structures were elucidated mainly by NMR and HRESIMS, as well as on comparison with the reported data.  相似文献   

10.
Four steroidal saponins were isolated from the anti-anoxic fraction of the 60% EtOH extract of Selaginella uncinata, including two new compounds, (3β, 7β, 12β, 25R)-spirost-5-ene-3, 7, 12-triol-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 4)]-O-β-d-glucopyranoside (1), (2α, 3β, 12β, 25R)-spirost-5-ene-2, 3, 12-triol-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 4)]-O-β-d-glucopyranoside (2) and two known compounds, (3β, 12β, 25R)-spirost-5-ene-3,12-diol-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 4)]-O-β-d-glucopyranoside, (3), (1α, 3β, 25R)-spirost-5-ene-2-diol-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-rhamnopyranosyl(1 → 4)]-O-β-d-glucopyranoside (4). The four compounds showed potent protective effect against anoxia in the anoxic PC12 cells assay, among which compounds 1 and 2 were the most active. To our knowledge, this is the first study to report the steroidal saponins in the plant S. uncinata and demonstrate their protective effect against anoxia in PC12 cell assay.  相似文献   

11.
Two new saponins of 20, 26-epoxy derivatives of pseudojujubogenin, hoduloside XI (1) and hoduloside XII (2) were isolated from the seeds of Hovenia trichocarpa. The structures of the new compounds were established by extensive NMR experiments and chemical methods. Hoduloside XI was confirmed to be 3-O-{β-d-glucopyranosyl(1 → 3)-[β-d-xylopyranosyl(1 → 2)]-α-l-arabinopyranosyl}-20, 26-epoxypseudojujubogenin. Hoduloside XII was identified as 3-O-{β-d-xylopyranose(1 → 2)glucopyranosyl(1 → 3)[rhamnopyranose(1 → 2)]β-d-glucopyranosyl}-20, 26-epoxypseudojujubogenin. The in vitro cytotoxic activity of compounds 1 and 2 was assayed. They displayed inhibitive activities against human cancer cell lines HL60 and K562.  相似文献   

12.
Two new furostanol glycosides, named tribufurosides I (1) J (2), were isolated from the fruits of Tribulus terrestris L. by a combination of chemical and spectroscopic methods. Its structures were established as 26-O-β-d-glucopyranosyl-(25S)-5α-furost-12-one-2α,3β,22α,26-tetraol-3-O-β-d-glucopyranosyl (1 → 2)-β-d-glucopyranosyl (1 → 4)-β-d-galactopyranoside (1) and 26-O-β-d-glucopyranosyl-(25R)-5α-furost-20(22)-en-12-one-2α,3β,26-triol-3-O-β-d-glucopyranosyl (1 → 4)-β-d-galactopyranoside (2).  相似文献   

13.
The occurrence of the two new cis-fused A/B rings furostanol saponins (25S)-26-O-β-d-glucopyranosyl-5β-furostan-1β,3β,22α,26-tetraol-1-O-β-d-glucopyranoside and (25S)-26-O-β-d-glucopyranosyl-5β-furostan-1β,2β,3β,5β,22α,26-hexaol and the known compounds (25S)-26-O-β-d-glucopyranosyl-5β-furostan-3β,22α,26-triol-3-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranoside and (25S)-26-O-β-d-glucopyranosyl-5β-furostan-3β,22α,26-triol-3-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranoside, trans-resveratrol, (+) catechin and (−) epicatechin in the rhizomes of Smilax aspera is reported. All saponins have been isolated as their 22-OMe derivatives, which were further subjected to extensive spectroscopic analysis. The isolated furostanol saponins were evaluated for cytotoxic activity against human normal amniotic and human lung carcinoma cell lines using neutral red and MTT assays. In vitro experiments showed significant cytotoxicity in a dose dependent manner with IC50 values in the range of 32.98-94.53 µM.  相似文献   

14.
The stem bark of Euonymus japonicus Thunb. led to the isolation of three new glycosylsphingolipids (1–3), 1-O-[-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl]-(2S,3R,9E)-2-N-[(2R)-hydroxystearoyl]-octadecasphinga-9-ene (euojaposphingoside A, 1), 1-O-[β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl]-(2S,3R,4R,11E)-2-N-[(2R)-hydroxydocasanoyl]-octadecasphinga-11-ene (euojaposphingoside B, 2), 1-O-[β-D-glucopyranosyl]-2′-O-[β-D-glucopyranosyl]-(2S,3R,4R,11E)-2-N-[(2R)-hydroxytetracosanoyl]-octadecasphinga-11-ene (euojaposphingoside C, 3) along with three known glycosylsphingolipids (4–6), 1-O-[β-D-glucopyranosyl]-(2S,3R,9E)-3-hydroxymethyl-2-N-[(2R)-hydroxynonacosanoyl)-tridecasphinga-9-ene (4), 1-O-[β-D-glucopyranosyl]-(2S,3R,9E,12E)-2-N-[(2R)-hydroxytetracosanoyl] octadecasphinga-9,12–diene (5), 1-O-[β-D-glucopyranosyl]-(2S,3R,5R,9E)-2-N-[tridecanoyl] nonacosasphinga-9-ene (6), lupeol (7), stigmasterol (8), sitosterol (β and α) (9,10) and β-carotene (11). The structure of all the compounds was achieved by spectroscopic and chemical data analysis. The antiplasmodial, antileismanial and cytotoxic activity of all compounds was tested.  相似文献   

15.
Two new sesquiterpene lactones, 1β-sulfate-5α, 6βH-eudesma-3-en-12, 6α-olide (1) and 1β-(p-hydroxyphenyl acetyl)-15-O-β-d-glucopyranosyl-5α, 6βH-eudesma-3-en-12, 6α-olide (2) were isolated from Sonchus arvensis L. (Asteraceae), together with eight known compounds. Their structures were elucidated through spectroscopic and chemical methods. They were evaluated for antibacterial activity. Among them, compounds 1 and 7 exhibited antibacterial activity against oral pathogen Streptococcus mutans ATCC 25175 with MIC values of 15.6 and 62.5 µg/ml, respectively.  相似文献   

16.
Fourteen pregnane-type steroidal alkaloids were isolated from the ethanolic extracts of whole Sarcococca hookeriana var. digyna plants. Their structures were elucidated on the basis of spectral data. Three of them were identified as new steroidal alkaloids: (S)-20-(N,N-dimethylamino)-16α,17α-epoxy-3β-methoxy-pregn-5-ene (1), (20S)-20-(N,N-dimethylamino)-3β-tigloylamino-5α-pregn-11β-ol (2), and (20S)-2α,4β-bis(acetoxy)-20-(N,N-dimethylamino)-3β-tigloylamino-5α-pregnane (3). Some of the isolated compounds showed estrogen biosynthesis-promoting effects in human ovarian granulosa-like KGN cells. The EC50 values for the most effective compounds, vagnine B (6) and funtumafrine C (12), were 71 μM and 67 μM, respectively.  相似文献   

17.
Sour jujube is a common fruit and traditional medicine in China. Bioactivity-guided fractionation of sour jujube was used to determine the chemical identity of potent antiproliferative and antioxidant constituents. Four novel ursane-type triterpenoids, together with 8 known were isolated and identified. The new triterpenoids were elucidated to be 2α,3β,13β,23-tetrahydroxy-urs-11-en-28-oic acid (3), 2α,3β-dihydroxy-urs-20(30)-en-28-oic acid (9), 2α,3β,28-trihydroxy-urs-20(30)-ene (10), and 3β,12β,13β-trihydroxy-ursan-28-oic acid (11). Among the triterpenoids isolated, 2α,3β,19α-trihydroxy-urs-12-en-28-oic acid (7), 9 and 10 showed high potent inhibitory activity toward the proliferation of HepG2 cells, which the IC50 values were lower than 5 μM. Compounds 9 and 10 also exhibited pronounced activity against MCF-7 cells, with IC50 value of 0.8 ± 0.03 and 1.5 ± 0.1 μM, respectively. Compound 10 showed high antioxidant activity with an EC50 of 0.8 ± 0.02 μM, which was 18.9 times higher than ascorbic acid in antioxidant capacity.  相似文献   

18.
Three new oleanane bidesmosidic triterpenoid saponins, named leiyemudanosides A–C (1–3) were isolated from the roots of Caulophyllum robustum Maxim. Their structures were established by chemical and detailed spectroscopic analysis as 3-O-α-l-arabinopyranosyl-caulophyllogenin-28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1), 3-O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl-caulophyllogenin-28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (2), and 3-O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl-echinocystic acid-28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (3), respectively.  相似文献   

19.
Six flavonol glycosides, compounds 1-3 from A. burnatii Gáyer and 4-6 from A. variegatum L., were obtained from their methanol extracts of aerial parts. The identified structures were quercetin 3-O-β-d-glucopyranoside-7-O-(6-E-p-coumaroyl)-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (1), quercetin 3-O-β-d-glucopyranoside-7-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (2), quercetin 3-O-β-d-glucopyranoside-7-O-(6-E-caffeoyl)-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (3), kaempferol 3-O-β-d-galactopyranoside-7-O-α-l-arabinopyranoside (4), quercetin 3-O-β-d-glucopyranoside (5), and kaempferol 3-O-β-d-glucopyranoside (6). Compounds 1, 2 and 4 were isolated for the first time. The antioxidant potential of the methanol extracts and pure compounds was tested with different assays.  相似文献   

20.
Two new cucurbitane triterpenoids, 7β-hydroxycucurbitacin F-25-O-acetate (1) and 2β,3β,20(S),26,27-pentahydroxy-16α,23(S)-epoxycucurbita-5,24-dien-11-one (2) along with eleven known cucurbitane triterpenoids (3–13, resp.) were isolated from the rhizomes of Hemsleya amabilis Diels. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated cucurbitane triterpenoids were evaluated against the HeLa human cancer cell lines. Hemslecin A (5), the main ingredient of H. amabilis, exhibited the significant cytotoxicity with IC50 value of 0.389 μM.  相似文献   

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