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1.
Boldoa purpurascens is used in Latin America and the Caribbean as a potent diurectic. Phytochemical analysis has shown the presence of flavonoids and other active compounds. In the present work, three flavonol glycosides were isolated from the leaves of the plant. Their structures have been determined by mass spectrometry and by 1D and 2D NMR analysis as 6-methoxykaempferol-3-O-[α-l-rhamnopyranosyl-(1”’ → 2”)]-β-d-xylopyranoside (1); 3,4′,5-trihydroxy-6,7-methylenedioxyflavone-3-O-[α-l-rhamnopyranosyl-(1”’ → 2”)]-β-d-glucopyranoside (2); and 3,4′,5′,5-tetrahydroxy-6,7-methylenedioxyflavone-3-O-[α-l-rhamnopyranosyl-(1”’ → 2”)]-β-d-xylopyranoside (3). Compounds 1 and 3 are reported for the first time from nature. The NF-κB luciferase assay showed that these compounds have a partial inhibitory effect on NF-κB activation, compound 2 being the most potent one. In the carrageenan induced paw oedema assay in rats, the flavonoid fraction showed acute anti-inflammatory activity, with the highest percentage of inhibition (75.8%) at a dose of 40 mg/kg. 相似文献
2.
Stefano Dall’Acqua Ignazio Castagliuolo Federica Ditadi Gabbriella Innocenti 《Carbohydrate research》2010,345(5):709-714
A new triterpene glycoside, repandoside (1) was isolated together with six known saponins (2-7) from the methanol extract of Cyclamen repandum tubers. The isolated saponins were characterized by high resolution mass spectrometry and both 1D and 2D NMR experiments. The in vitro effect of saponins on LPS-induced IL-8 and TNF-α mRNA level (by quantitative RT-PCR) and protein release (by ELISA) was evaluated in human THP-1 macrophages. We found that compounds 1 (repandoside), 2 (deglucocyclamin) and 4 (anagalloside B) at 100 μM inhibited the LPS-induced IL-8 and TNF-α expressions. 相似文献
3.
Phytochemical investigation of the rhizomes of Smilax trinervula led to isolation and structure elucidation of eight lignan glycosides, including five new lignans, namely, (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4′-O-β-d-glucopyranoside (1), (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4-O-β-d- glucopyranoside (2) (7S, 8R)-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-4′, 7-epoxy-8, 5′-neolignan 9′-O-β-d-glucopyranoside (3), (7R, 8R)-4, 9, 9′-trihydroxy-3, 5-dimethoxy-7.O.4′, 8.O.3′- neolignan 9′-O-β-d-glucopyranoside (4), and (7S, 8R)-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-8, 4′-oxy-neolignan 4-O-β-d-glucopyranoside (5), along with three known compounds (6-8). Their structures were established mainly on the basis of 1D and 2D NMR spectral data, ESI–MS and comparison with the literature. Compounds 1-8 were tested in vitro for their cytotoxic activity against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Compounds 3 and 5 exhibited cytotoxic activity against Lovo cells, with IC50 value of 10.4 μM and 8.5 μM, respectively. 相似文献
4.
A novel iridoid glycoside trimer named forsydoitriside A (1) and five new iridoid glycosides (2–6) were isolated from the fruits of Forsythia suspensa together with two known compounds (7, 8). These new structures were elucidated by comprehensive spectroscopic data and the comparison of experimental and calculated electronic circular dichroism spectra. Compounds 1–8 were all assayed on acetaminophen-induced HepG2 cell damage. The results exhibited that compounds 2, 3, 5 and 6 possessed strong hepatoprotective activities against the damage in HepG2 cell. 相似文献
5.
Five triterpene glycosides have been isolated from the leaves of Acanthopanax giraldii Harms (Araliaceae), which are elucidated as: hederagenin-3-O-α-L-rhamnopyranosyl (1→2) -α-L-arabinopyranoside ( Ⅰ ), hederagenin-28-α-L-rhamnopyranosyl- (1→4) -β -D-glu- copyranosyl-(1→6)-β -D-glucopyranosylester ( Ⅱ ), 3-O-α-L-arabinopyranosyl-hederagenin- 28-β -D-glucopyranosyl- ( 1→6 ) -β -D-glucopyranosylester ( Ⅲ ), 3-O-α-L-arabinopyranosyl- hederagenin-28-α-L-rhamnopyranosyl- ( 1→4 ) -β -D-glucopyranosyl- ( 1→6 ) -β -D-glucopyra-nosylester ( Ⅳ ) and 3-O-α-L-rhamnopyranosyl- (1→2) -α-L-arabinopyranosyl-hederagenin-28-α-L-rhamnopyranosyl-( 1→4 )-β -D-glucopyranosyl-( 1→6 )-β -D-glucopyranosylester ( Ⅴ ). All of them are reported in this genus for the first time. Perhaps the findings are valuable for chemotaxonomy of Acanthopanax genus. 相似文献
6.
Fu Li Hong-Mei Pan Xin Liu Bin Chen Ya-Xiong Tang Xing-Jun Xi Ming-Kui Wang 《Phytochemistry letters》2013,6(4):640-644
Five new phenanthrene glycosides, denneanosides A–E (1–5), and one new 9,10-dihydrophenanthrene glycoside, denneanoside F (6) were isolated from the stem of Dendrobium denneanum. The chemical structures of the new compounds were established on the basis of extensive spectroscopic data. The isolated compounds were evaluated for their in vitro cytotoxic activity against SNU387 hepatocellular carcinoma cell line. Compounds 1–3 showed moderate cytotoxic activities while compounds 4–6 showed weak activities. 相似文献
7.
Three new dimeric monoterpene glycosides, paeonidanins F–H (1–3) were isolated from the roots of Paeonia lactiflora. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1–3 showed inhibitory effects against nitric oxide (NO) and pro-inflammatory cytokine TNF-α release in LPS-induced RAW 246.7 macrophages. 相似文献
8.
Arafa I. Hamed Milena Masullo Mohamed G. Sheded Usama A. Mahalel Moatz M. Tawfik Angela Perrone Sonia Piacente 《Phytochemistry letters》2011,4(3):353-356
Continuing our investigations on medicinal plants of the Egyptian desert, two new triterpene glycoside derivatives, along with three known compounds have been isolated from the roots of Salsola imbricata, a shrub widely growing in Egypt. Their structures have been established as 3-O-β-d-xylopyranosyl-(1 → 2)-O-β-d-glucuronopyranosyl-akebonic acid 28-O-β-d-glucopyranoside and 3-O-β-d-xylopyranosyl-(1 → 2)-O-β-d-glucuronopyranosyl-29-hydroxyoleanolic acid 28-O-β-d-glucopyranoside on the basis of spectroscopic methods including 1D- (1H, 13C) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments as well as mass spectrometry analysis. 相似文献
9.
Investigation of whole seeds of Lupinus angustifolius L. (Leguminosae) yielded the two triterpenoid saponins with branched monosaccharide chain 3 beta,21 beta,22 beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranoside (3) and 3 beta,21 beta,22 beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-O-alpha-L-rhamnopyranoside (4) along with the known compounds soyasaponin I (1) and 3 beta,21 beta,22 beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-O-alpha-L-rhamnopyranoside (2). The structures of the compounds were elucidated using hydrolysis, FAB-MS and extensive NMR experiments. Compounds 2-4 showed moderate antifungal activity against Candida albicans with MIC values of 25, 25 and 30 microg/ml, respectively. Only soyasaponin I was found weakly hemolytic (HC(50) >500 microg/ml). 相似文献
10.
Three new pregnane glycosides, 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-(20R)-pregn-5-ene-3β,20-diol (1), 3-O-α-L-arabinopyranosyl-(20R)-pregn-5-ene-3β,20-diol-20-O-β-D-glucopyranoside (2), 3-O-α-L-arabinopyranosyl-(20R)-pregn-5-ene-3β,20-diol-20-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (3) were isolated along with four known compounds, 4-7, from the leaves and stems of Brucea javanica. Their structures were determined by detailed analyses of 1D- and 2D-NMR spectroscopic data. All of the compounds isolated from Brucea javanica were tested for the antifeedant activities against the larva of Pieris rapae. Compounds 1, 3, and 5 showed significant antifeedant activities after 72 h incubation. 相似文献
11.
Two new flavanone glycosides, named scugalerosides A and B (1-2), were isolated from the whole plant of Scutellaria galericulata. Their chemical structures including absolute configurations were established on the basis of detailed physical data analyses. In vitro, two new compounds showed anti-inflammatory activities, with the inhibition rates of release of β-glucuronidase from polymorphonuclear leukocytes of rats being 43.7% and 45.1% at concentrations of 10 μM. 相似文献
12.
Four new phenylpropanoid glycosides, clausenaglycosides A–D (1–4), along with fourteen known compounds (5–18) were isolated from the leaves and twigs of Clausena dunniana var. robusta. The structures of the isolated compounds were determined by a combination of 1D and 2D NMR, MS, and CD spectroscopic data. The NF-κB inhibitory activity was evaluated in HeLa cells. Compound 17 displayed a moderate inhibition against NF-κB activation. 相似文献
13.
Le Ba Vinh Yunjeong Lee Yoo Kyong Han Jong Seong Kang Jung Up Park Young Ran Kim Seo Young Yang Young Ho Kim 《Bioorganic & medicinal chemistry letters》2017,27(23):5149-5153
Panax ginseng has been the subject of extensive research on potential medicinal materials. The goal of this study was search the chemical constituents and biological activities of processed Panax ginseng, Korean red ginseng. Our efforts led to the isolation eleven compounds (1–11) including two new compounds 1 and 2 from Korean red ginseng using various chromatographic techniques. Chemical structures of isolated compounds were demonstrated by spectroscopic methods (1D-, 2D-NMR, and HR-ESI-MS). The anti-inflammatory effects of the compounds were investigated by inhibiting IL-6 and TNF-α secretion in LPS-activated RAW264.7 cells. Additionally, the effects of the compounds on the expression of COX-2 and iNOS were examined by Western blotting. Compound 1 significantly reduced the level of proinflammatory cytokines IL-6 and TNF-α secretion in LPS-activated RAW264.7 cells and the expression of COX-2 and iNOS inflammatory enzymes in the cells. These results suggested that compound 1, a new ginsenoside might useful in treatment of inflammation. 相似文献
14.
《Bioorganic & medicinal chemistry letters》2014,24(24):5688-5691
Two new cycloartenol triterpene saponins, 3β,16α-dihydroxy-12-acetoxy-16,22-cyclo-23-ketone-24R,25-epoxy-cycloartane-3-O-β-d-galactopyranoside (1), 3β,16α-dihydroxy-12-acetoxy-16,22-cyclo-23-ketone-24R,25-epoxy-cycloartane-7-ene-3-O-β-d-xylopyranoside (2), were isolated from the ethyl acetate soluble fraction of the roots of Cimicifuga simplex Wormsk. Their structures were established by detailed spectroscopic analysis, including extensive 2D NMR data. Their anti-proinflammatory activities were also carried out by LPS-stimulated IL-6, IL-23 and TNF-α genes expression in RAW cells in vitro using Q-PCR method. 相似文献
15.
Calabria LM Piacente S Kapusta I Dharmawardhane SF Segarra FM Pessiki PJ Mabry TJ 《Phytochemistry》2008,69(4):961-972
Nine triterpene saponins (1-9) were isolated from leaves and stems of Silphium radula Nutt. (Asteraceae). Their structures were determined by extensive 1D ((13)C, (1)H, DEPT, TOCSY) and 2D NMR (NOESY, HSQC, HMBC) and ESI-MS studies. The compounds were identified as 3beta,6beta,16beta-trihydroxyolean-12-en-23-al-3-O-beta-glucopyranosyl-16-O-beta-glucopyranoside (1), urs-12-ene-3beta,6beta,16beta-triol-3-O-beta-galactopyranosyl-(1-->2)-beta-glucopyranoside (2), 3beta,6beta,16beta-trihydroxyolean-12-en-23-oic acid-3-O-beta-glucopyranosyl-16-O-beta-glucopyranoside (3), urs-12-ene-3beta,6beta,16beta,21beta-tetraol-3-O-beta-glucopyranoside (4), olean-12-ene-3beta,6beta,16beta,21beta-tetraol-3-O-beta-glucopyranoside (5), olean-12-ene-3beta,6beta,16beta,21beta,23-pentaol-3-O-beta-glucopyranosyl-16-O-beta-glucopyranoside (6), olean-12-ene-3beta,6beta,16beta-triol-3-O-beta-glucopyranosyl-16-O-alpha-arabinopyranosyl-(1-->2)-beta-glucopyranoside (7), olean-12-ene-3beta,6beta,16beta,23-tetraol-3-O-beta-glucopyranosyl-16-O-alpha-arabinopyranosyl-(1-->2)-beta-glucopyranoside (8), 3beta,6beta,16beta,21beta-tetrahydroxyolean-12-en-23-al-3-O-beta-glucopyranoside (9). The presence of a 6beta-hydroxyl function was not common in the oleanene or ursene class and the aglycones of these compounds were not found previously in the literature. Moreover, the cytotoxic activities of the isolated compounds were tested against human breast cancer cell line MDA-MB-231. Results showed that compound 2 decreased cell proliferation in a statistically significant manner at 25 microg/ml. 相似文献
16.
Two new triterpene glycosides, argusides B and C (1 and 2, resp.), have been isolated from the sea cucumber Bohadschia argus Jaeger collected in the South China Sea. Their structures have been established by spectral analysis (2D-NMR and ESI-MS) and chemical evidence. Compounds 1 and 2 both possess a holostane-type triterpene aglycone with a C(9)==C(11) bond and a OH group at C(12), but differ in their substituents at C(17) and the hexasaccharide moiety. The two glycosides exhibited significant cytotoxicities against four human tumor cell lines (A549, HCT-116, HepG2, and MCF-7). In comparison with the positive control V-16 (etoposide), 1 and 2 showed higher cytotoxicities to A549 and HCT-116 cell lines. 相似文献
17.
Two new triterpene glycosides, argusides D and E (1 and 2, resp.), have been isolated from the sea cucumber Bohadschia argus Jaeger collected in the South China Sea. Their structures have been established by spectral analysis (ESI-MS, and 1D- and 2D-NMR) and chemical evidence. Compounds 1 and 2 both possess an holostane-type triterpene aglycone with a C(9)=C(11) bond, an OH group at C(12), and tetrasaccharide moieties, but differ in the side chains. The two glycosides exhibited significant cytotoxicities against four human tumor cell lines, A549, HCT-116, HepG2, and MCF-7. 相似文献
18.
Kovalchuk SN Kozhemyako VB Atopkina LN Silchenko AS Avilov SA Kalinin VI Rasskazov VA Aminin DL 《The Journal of steroid biochemistry and molecular biology》2006,101(4-5):226-231
Estrogenic potency of six triterpene glycosides, Holothurin A, Holotoxin A1, Frondoside A, Cucumarioside A2-2 and Cauloside C, that are natural products and semi-synthesized Ginsenoside-Rh2, were examined with yeast two-hybrid system, including expressed genes of human estrogen receptor, hER, the co-activator TIF2 and lacZ as a reporter gene. Only Ginsenoside-Rh2 exhibited significant moderate estrogenic activity in the concentration range of 10−7 to 10−6 M. Its effect was approximately 30% of the activity of 17β-estradiol applied at half-effective concentration. This indicates Ginsenosides-Rh2 is a weak phytoestrogen. The sea cucumber triterpene glycosides, Holothurin A, Holotoxin A1, Cucumarioside A2-2 and Frondoside A, and plant glycoside Cauloside C had no appreciable estrogenic activity. Data obtained by yeast two-hybrid assay reflect structure–activity relationship between tested compounds and 17β-estradiol. Only Ginsenoside-Rh2 has some similarity in chemical structure with 17β-estradiol that might explain affinity of this glycoside to the hER receptor. 相似文献
19.
20.
Abdel-Sattar E Harraz FM Al-ansari SM El-Mekkawy S Ichino C Kiyohara H Ishiyama A Otoguro K Omura S Yamada H 《Phytochemistry》2008,69(11):2180-2186
Five pregnane glycosides were isolated from Caralluma tuberculata (1-5), in addition to a known one (russelioside E, 6). The structures of the isolated compounds were elucidated by the analysis of NMR data and FAB-MS experiments. All the isolated compounds were tested for their antimalarial and antitrypanosomal activities as well as their cytotoxicity against human diploid embryonic cell line (MRC5). 相似文献