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1.
Two new glycosides, 2-methyl-l-erythritol-4-O-(6-O-trans-sinapoyl)-β-d-glucopyranoside (1) and 2-methyl-l-erythritol-1-O-(6-O-trans-sinapoyl)-β-d-glucopyranoside (2), along with two known triterpenoids (3–4), four quinic acid derivatives (5–8) and one flavonoid (9) were isolated from the fruit of Gardenia jasminoides. Their structures were elucidated through MS and 2D NMR experiments (HMQC and HMBC). Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. Though 2-methyl-d-erythritol and its glycosides have been reported in a few references, this is the first report about 2-methyl-l-erythritol glycosides. Based on this finding, we propose that 2-methyl-l-erythritol might be a new intermediate in the non-mevalonate biosynthesis of terpenoids.  相似文献   

2.
One alkyl glycoside, saussurostelloside A (1), two phenolic glycosides, saussurostellosides B1 (2) and B2 (3), and 27 known compounds, including eleven flavonoids, seven phenolics, six lignans, one neolignan, one phenethyl glucoside and one fatty acid, were isolated from an ethanol extract of Saussurea stella (Asteraceae). Their structures were elucidated by NMR, MS, UV, and IR spectroscopic analysis. Of the known compounds, (+)-medioresinol-di-O-β-d-glucoside (7), picraquassioside C (10), and diosmetin-3′-O-β-d-glucoside (27) were isolated from the Asteraceae family for the first time, while (+)-pinoresinol-di-O-β-d-glucoside (6), di-O-methylcrenatin (11), protocatechuic acid (14), 1,5-di-O-caffeoylquinic acid (17), formononetin (28), and phenethyl glucoside (29) were isolated from the Saussurea genus for the first time. The anti-inflammatory activities of three new compounds (1–3), five lignans ((−)-arctiin (4), (+)-pinoresinol-4-O-β-d-glucoside (5), (+)-pinoresinol-di-O-β-d-glucoside (6), (+)-medioresinol-di-O-β-d-glucoside (7) and (+)-syringaresinol-4-O-β-d-glucoside (8)), one neolignan (picraquassioside C (10)), and one phenolic glycoside (di-O-methylcrenatin (11)) were evaluated by testing their inhibition of the release of β-glucuronidase from PAF-stimulated neutrophils. Only compound 5 showed moderate inhibition of the release of β-glucuronidase, with an inhibition ratio of 39.1%.  相似文献   

3.
Four new xanthones, 3,5,6,8-tetrahydroxyxanthone-1-C-β-d-glucoside (1), 7-hydroxy-3,4,8-trimethoxyxanthone-1-O-(β-d-glucoside) (2), 6-hydroxy-3,5-dimethoxyxanthone-1-O-(β-d-glucoside) (3), 3,4,7,8-tetramethoxyxanthone-1-O-(β-d-glucoside) (4), together with twenty-one known xanthones (5–25) were isolated from the ethanol aqueous extract of Swertia mussotii. Their structures were elucidated via spectroscopic analyses. Oxygen radical absorbance capacity of all the isolated xanthones was systematically evaluated by ORACFL assay. Results disclose that all the tested xanthones display moderate to excellent antioxidant activity, where 1 is the most active compound and 13 is the least one. A preliminary structure–activity relationship is also discussed.  相似文献   

4.
Six new 14-noreudesmane sesquiterpenoids, nicotabacosides A–F (1–6), along with five known sesquiterpenoids (7–11), were isolated from the leaves of Nicotiana tabacum. The structures of compounds 1–6 were elucidated as isorishitin 3-O-β-d-glucopyranoside (1), rishitin 3-O-β-d-glucopyranoside (2), rishitin 2-O-β-d-glucopyranoside (3), 1, 6-dehydro-rishitin 3-O-β-d-glucopyranoside (4), 2-hydroxyl-ligudentatol 3-O-β-d-glucopyranoside (5) and oxyglutinosone 3-O-β-d-glucopyranoside (6) based on extensive spectroscopic analyses (HRESIMS, UV, IR, 1D and 2D NMR). Their absolute configurations were determined by X-ray single-crystal diffraction and comparison of their electronic circular dichroism (ECD) spectra.  相似文献   

5.
Two new 5-O-glucosylflavones, 5-O-β-d-glucopyranosyl cirsimaritin (1) and 5, 4′-O-β-d-diglucopyranosyl cirsimaritin (2), four known flavonoids, cirsimarin (3), cirsimaritin (4), salvigenin (5), 4′, 5-dihydroxy-7-methoxyflavone (6), and a norisoprenoid, vomifoliol (7), have been isolated from the aerial parts of Microtea debilis. All isolates were tested for cytotoxicity in human cancer cell lines (Hep G2, COLO 205, and HL-60) and anti-inflammatory activities in LPS-treated RAW264.7 macrophages. Compound 6 was found to be a potent inhibitor to nitrite production in macrophages. Compounds 2, 4, 6, and 7 showed moderate anti-proliferative activity against COLO-205 cells with IC50 values of 7.1, 13.1, 6.1, and 6.8 μM, respectively.  相似文献   

6.
Four new sesquiterpene lactones (1), (2), (3), and (4), along with three known sesquiterene, namely, 6,7,10-trihydoxyisodaucane (5), 4β,10β-dihydroxyaromadendrane (6), and sescrassidiol (7) were isolated from the stem bark of Illicium burmanicum. The structures of the new compounds were determined using 1D and 2D NMR, and HRESIMS. The anti-inflammatory activities of these compounds were evaluated by measuring the enzymatic activity of luciferase in NF-κB reporters in a (Luc)-HEK 293 cell line treated with lipopolysaccharide (LPS).  相似文献   

7.
Five new saikosaponins, saikosaponin w (1), 21β-hydroxysaikosaponin b2 (2), 6″-O-acetylsaikosaponin e (3), 6″-O-acetylsaikosaponin b1 (4), and 6″-O-acetylsaikosaponin b3 (5), along with twenty-two known ones (6–27), have been isolated from the roots of Bupleurum chinense. Their structures were elucidated on the basis of detailed spectroscopic analysis, including mainly 1D and 2D NMR and HRESI-MS, qualitative chemical methods, and comparison with the literatures. Osteoclast-inhibiting activity of some of the isolated compounds was evaluated in vitro, with five ones have shown significant activity by inhibitory rates ranging from 48.3% to 56.1% at the concentration of 10 μM and with significant differences among groups observed.  相似文献   

8.
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   

9.
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   

10.
Three rare indole-2-S-glycosides, indole-3-acetonitrile-2-S-β-D-glucopyranoside (1), indole-3-acetonitrile-4-methoxy-2-S-β-D-glucopyranoside (2) and N-methoxy-indole-3-acetonitrile-2-S-β-D-glucopyranoside (3), together with 11 known indole alkaloids were isolated from the roots of Isatis indigotica Fort. (Cruciferae). The structures of 1–3 were elucidated on the basis of mass spectrometry and extensive 1D and 2D NMR spectroscopy. All of the isolated compounds were tested for inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages. A plausible biosynthesis pathway of 1–3 is also proposed.  相似文献   

11.
Two new glycosidated coumaramides clerodendiod A (1) and B (2), together with seven known glycosidic compounds were isolated from the branches of Clerodendron cyrtophyllum Turcz. Clerodendiod A and B were elucidated as β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-[6-O-(E)-p-methoxycinnamoyl]-β-D-glucopyranosyl-(1 → 2)-[4-O-((E)-2-(4-acetamidobutylcarbamoyl)vinyl)-phenyl]-α-L-rhamnopyranoside (1) and 6-O-(E)-p-coumaroyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-[6-O-(E)-p-methoxycinnamoyl]-β-D-glucopyranosyl-(1 → 2)-[4-O-((E)-2-(4-acetamidobutylcarbamoyl)vinyl)-phenyl]-α-L-rhamnopyranoside (2) on the basis of chemical and spectral evidence. The isolated new compound 2 was assayed for the inhibition of the NF-κB pathway and showed potent activity in inhibiting NF-κB which its IC50 values was found to be 24.9 nM.  相似文献   

12.
A new compound, named quinquefoloside-Lc (1), together with nine known compounds, was isolated from leaves of Panax quinquefolium, and its structure was elucidated as 3β,12β,20S-trihydroxy-25-methoxydammar-23-ene 3-O-β-d-glucopyranosyl (1 → 2) β-d-glucopyranosyl-20-O-β-d-xylopyanosyl (1 → 6) β-d-glucopyranoside (1), on the basis of MS, 1D-and 2D-NMR experiments as well as by chemical degradation. The cytotoxicity of these compounds against human breast cancer MCF-7 cell line was also tested by MTT method.  相似文献   

13.
Two new sesquiterpenes, together with 32 known compounds(3–34), were isolated from Artemisia sieversiana Ehrhart ex willd. and the compounds 3–21 were isolated from this plant for the first time. The new compounds were elucidated as 2α,9α-dihydroxymuurol-3(4)-en-12-oic acid (1) and 13α-methyl-(5αH,6αH,7αH,8αH)-austricin 8-O-β-D-glucopyranoside (2), respectively. The structural identification of these compounds was mainly achieved by spectroscopic methods including 1D and 2D NMR techniques, and the structure of compound 1 was confirmed by a single crystal X-ray diffraction experiment. Compounds 1–2 were evaluated for cytotoxic activity in vitro against MCF-7, NCI-H460 and Hep-G2 cell lines, respectively.  相似文献   

14.
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   

15.
Six new anthraquinone glycosides: digiferruginol-1-methylether-11-O-β-gentiobioside (1); digiferruginol-11-O-β-primeveroside (2); damnacanthol-11-O-β-primeveroside (3); 1-methoxy-2-primeverosyloxymethyl-anthraquinone-3-olate (4); 1-hydroxy-2-primeverosyloxymethyl-anthraquinone-3-olate (5); and 1-hydroxy-5,6-dimethoxy-2-methyl-7-primeverosyloxyanthraquinone (6) were isolated from Morinda citrifolia (Rubiaceae) roots together with four known anthraquinone glycosides. The structures of the new compounds were established using spectral methods. For five of the new compounds, the sugar is attached via the hydroxymethyl group of the anthraquinone C-2 carbon. This type of bond is rarely found for anthraquinone glycosides isolated from natural sources.  相似文献   

16.
Three sulfated phenolic compounds, juglanin B (11R)-O-sulfate (1), myricetin 3´-O-sulfate (2), and ampelopsin 3´-O-sulfate (3), were isolated from the leaves of Myrica rubra. Compound 1 was a new sulfated lignan, 2 was a new sulfated flavone, and 3 was a known sulfated flavone. The structures of the new compounds (1 and 2) were determined by acid hydrolysis and spectroscopic methods, including IR, FAB-MS, 1D and 2D NMR. The inhibitory activities of compounds 1–3 and their hydrolysates (1a–3a) against LPS-induced cytokine (TNF-α, IL-1β, and IL-6) production in macrophage RAW 264.7 cells were evaluated. The 2 new compounds (1 and 2) and their aglycones (1a and 2a) significantly reduced LPS-induced expression of iNOS and COX-2 proteins.  相似文献   

17.
One new flavanone (S)-5,7,3′,5′-tetrahydroxy-flavanone-7-O-(6″-galloyl)-β-D-glucopyranose (1), together with one known flavanone and four known dihydrochalcones were isolated from the ethyl acetate partitions from an alcoholic extract of the whole plant of Balanophora involucrata Hook. f. All of the compounds were characterized by spectroscopic methods. Their in vitro BACE inhibitory effects were evaluated. Compounds 1, 2, 4, and 5 were found to be a little more active than the positive control, although all of which are below 50% inhibition at 10 μM.  相似文献   

18.
Angiogenesis, the growth of new blood vessels from the pre-existing vasculature is of physiological and pathological importance. Substantial data over the last decade has implicated uncontrolled angiogenesis with various pathological states. Vascular endothelial growth factors (VEGFs) play a critical role in its regulation, and have become one of the most interesting anti-angiogenesis targets. We have investigated the anti-angiogenic potential of plant extracts in a preliminary ELISA screening. The n-BuOH extract obtained from the leaves of Monnina obtusifolia (Polygalaceae) demonstrated an inhibition of VEGF-A or Placental Growth Factor interaction with Flt-1 (VEGF receptor 1), with an inhibition over 50% in particular for VEGF-A/Flt-1 interaction at a concentration of 500 μg/mL. Successively fractionation of the bioactive n-BuOH extracts of M. obtusifolia aerial parts led to the isolation of six new compounds, 1-O-(4-hydroxy-2-methylene-butanoic acid)-6-O-β-d-(4-hydroxy-2-methylene-butanoyl)-glucopyranose (1), 1-O-(isopentenyl)-6-O-β-d-(4-hydroxy-2-methylene-butanoyl)-glucopyranose (2), 1-O-(4-hydroxy-2-methylene-butanoic acid)-6-O-β-d-(isovaleroyl)-glucopyranose (3), 1-O-(3-methylbut-3enyl)-6-O-β-d-(isovaleroyl)-glucopyranose (4), two new sucrose esters, 3,4-O-β-d-di-feruloyl-fructofuranosyl-6-O-α-d-(p-coumaroyl)-glucopyranoside (5), and 3,4-O-β-d-di-feruloyl-fructofuranosyl-6-O-α-d-(caffeoyl)-glucopyranoside (6), together with known flavonoids. Their structures were established on the basis of detailed spectral analysis. Since none of the isolated compounds showed a relevant inhibition of VEGFs, the biological activity observed for the butanolic extract might be due to the presence of a combination of compounds acting synergistically.  相似文献   

19.
Two new 5-methylcoumarin glycosides named diosfeboside A (1) and B (2) and five known compounds namely kaempferol 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (3), ursolic acid (4), betulinic acid (5), stigmasterol (6) and stigmasterol 3-O-β-d-glucopyranoside (7) were isolated from the leaves of Diospyros crassiflora (Hiern). Their structures were established through interpretation of 1 and 2D NMR, mass spectra analysis and comparison with reported data. In vitro cytotoxic activity of the new compounds against human carcinoma cell lines (HL-60, Bel-7402, BGC-823, and KB) was evaluated and no cytotoxicity was observed for each of them.  相似文献   

20.
A new lanostane triterpenoid, 2-hydroxy-24-methylenelanostan-1,8-dien-3-one named klainedoxalanostenone (1) with one new steroid, 6-O-acyl-β-d-glucosyl-β-sitosterol named klainedoxasterol (2) together with ten known compounds including six triterpenoids (3–8), two steroids (9, 10) and two tanins (11, 12) were isolated from the stem bark of Klainedoxa gabonensis. To the best of our knowledge, this is the first report of lanostane-type triterpenoids from this genus. Their structures were determined by extensive analysis of spectroscopic data (1D and 2D NMR, MS) and by comparison with literature data. The xanthine oxidase inhibitory activity of nine compounds (1–6, 8, 10 and 11) were evaluated. Compound 5 showed a good xanthine oxidase inhibitory activity; the other tested compounds were moderately active.  相似文献   

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