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Fortschritte Der Chemie Organischer... 1997
Review
Topics: Disaccharides; Glycosides; Magnetic Resonance Spectroscopy; Mass Spectrometry; Monosaccharides; Pregnanes; Spectrophotometry; Trisaccharides
PubMed: 9250024
DOI: 10.1007/978-3-7091-6529-4_3 -
Phytochemistry Feb 2022Seven undescribed pregnane glycosides named amurensides A-G and two known aglycones were isolated from the whole herb of Adonis amurensis Regel & Radde. Their structures...
Seven undescribed pregnane glycosides named amurensides A-G and two known aglycones were isolated from the whole herb of Adonis amurensis Regel & Radde. Their structures were established based on 1D and 2D NMR spectroscopic analyses, high-resolution mass spectrometry, and acid hydrolysis. The cytotoxicity of all compounds against three tumor cell lines (HepG2, Caco-2, and A549) were evaluated. Among them, amurensides A-C and E showed moderate inhibitory effects on the growth of HepG2 cells, with IC values ranging from 15.6 to 48.7 μM (sorafenib, 7.5 ± 1.9 μM). Amurensides A、D and F displayed inhibitory effects on the growth of A549 cells with IC values of 18.8 ± 1.2, 12.4 ± 0.6, and 30.4 ± 0.1 μM (cis-platinum, 6.1 ± 0.1 μM), respectively.
Topics: Adonis; Caco-2 Cells; Glycosides; Humans; Pregnanes
PubMed: 34875526
DOI: 10.1016/j.phytochem.2021.113046 -
Molecules (Basel, Switzerland) Aug 2022For our interest in the potential biologically active and structurally unique steroidal glycosides, continued phytochemical investigation of was carried out; twelve new...
For our interest in the potential biologically active and structurally unique steroidal glycosides, continued phytochemical investigation of was carried out; twelve new seco-pregnane glycosides, cynataihosides I-L (-), M-T (-), and two known glycosides, glaucoside A () and atratcynoside F (), were isolated from the 95% ethanol extract of . Two new aglycones were found among compounds , , , and . The structures of the glycosides were elucidated based on 1D and 2D NMR spectroscopic data, HR-ESI-MS analysis, and chemical evidence. The cytotoxicity of compounds against three human tumor cell lines (HL60, THP-1, and PC-3) were evaluated by MTT assay. Compound displayed significant cytotoxicity against THP-1 and PC-3 cell line with IC values of 5.08 and 22.75 μm, respectively. Compounds and exhibited moderate and selective cytotoxicity on HL60 and THP-1 with IC values of 17.78 and 16.02 μm, respectively.
Topics: Cynanchum; Glycosides; Humans; Molecular Structure; Plant Roots; Pregnanes
PubMed: 36080268
DOI: 10.3390/molecules27175500 -
Journal of Natural Products Mar 2023subsp. , more commonly known as caustic vine, is a leafless succulent that grows in the northern arid zone of Australia. Toxicity toward livestock has been reported for...
subsp. , more commonly known as caustic vine, is a leafless succulent that grows in the northern arid zone of Australia. Toxicity toward livestock has been reported for this species, along with use in traditional medicine and its potential anticancer activity. Disclosed herein are novel -pregnane aglycones cynavimigenin A () and cynaviminoside A (), together with new pregnane glycosides cynaviminoside B () and cynavimigenin B (). Cynavimigenin B () contains an unprecedented 7-oxobicyclo[2.2.1]heptane moiety in the -pregnane series, likely arising from a pinacol-type rearrangement. Interestingly, these isolates displayed only limited cytotoxicity in cancer and normal human cell lines, in addition to low activity against acetylcholinesterase and bioassays, suggesting that - are not associated with the reported toxicity of this plant species.
Topics: Humans; Cynanchum; Caustics; Acetylcholinesterase; Australia; Glycosides; Pregnanes; Plant Roots
PubMed: 36795946
DOI: 10.1021/acs.jnatprod.2c01037 -
Molecules (Basel, Switzerland) Sep 2022Lindl. is an important genus of the Apocynaceae family, not only as ornamental plants but also for its medicinal uses. In Brazil, species are indicated to treat asthma...
Lindl. is an important genus of the Apocynaceae family, not only as ornamental plants but also for its medicinal uses. In Brazil, species are indicated to treat asthma and skin infections, their anti-inflammatory potential and wound healing properties are also reported in the literature. Concerning their chemical composition, this group of plants is a conspicuous producer of pregnane glycosides. is an endemic species from the Brazilian semiarid region not studied by any phytochemical methods. In view of the medicinal potential of species, this study aimed to isolate new pregnane glycosides from . To achieve this main goal, modern chromatography techniques were employed. Five new pregnane glycosides, dardanols A-E, were isolated from the roots of by HPLC. Their structures were determined using extensive 1D and 2D-NMR and mass spectrometry (MS and HRESIMS) data. The cytotoxicity and the anti-inflammatory potential of these compounds were evaluated. The first was evaluated by measuring proinflammatory cytokines and nitric oxide production by stimulated macrophages. Dardanols were able to inhibit the production of nitric oxide and reduce IL-1β and TNF-α. The current work demonstrates the chemodiversity of Brazilian semiarid species and contributes to amplifying knowledge about the biological potential of the genus.
Topics: Anti-Inflammatory Agents; Apocynaceae; Glycosides; Nitric Oxide; Plant Extracts; Plants; Pregnanes; Tumor Necrosis Factor-alpha
PubMed: 36144723
DOI: 10.3390/molecules27185992 -
Journal of Natural Products Jun 2019Three new C pregnane steroids, chonemorphols A-C (1, 3, and 4), 11 new C steroidal glycosides, chonemorphosides A-K (2 and 5-14), and 11 known compounds (15-25) were...
Three new C pregnane steroids, chonemorphols A-C (1, 3, and 4), 11 new C steroidal glycosides, chonemorphosides A-K (2 and 5-14), and 11 known compounds (15-25) were obtained from the vines and leaves of Chonemorpha megacalyx Pierre. Their structures were established using extensive spectroscopic data. The X-ray crystallographic data of 1 and 3 permitted definition of their absolute configurations. Notably, 1 and 2 possessed an uncommon 6/5/6/5/5-fused steroidal ring system. Compound 7 displayed significant cytotoxicity against several cancer cell lines with IC values of 2.0-3.6 μM.
Topics: Apocynaceae; Cell Line, Tumor; Glycosides; Humans; Molecular Structure; Plant Leaves; Pregnanes
PubMed: 31148449
DOI: 10.1021/acs.jnatprod.9b00013 -
Natural Product Research Jan 2020Development of a novel agent for control of schistosomiasis is a mandate. anti-schistosomal activity of the aerial parts of were examined. Chromatographic...
Development of a novel agent for control of schistosomiasis is a mandate. anti-schistosomal activity of the aerial parts of were examined. Chromatographic investigations of the ethanol extract (EE) were afforded three compounds. Pregnane glycoside (CI) 12--hydroxy-benzoyl-20-acetyl-boucerin-3--D-glucopyranosyl-(1→4)--D-cymaropyranosyl-(1→4)-D-cymaropyranoside, in addition to two flavonoids (CII) luteolin-4'---D-neohesperidoside and (CIII)quercetin-3-rutinoside were recognized spectral analysis. The schistosomicidal effects were evaluated using scanning electron microscope (SEM). bioassays on the viability (mobility, morphological changes and mortality) of adults, cercariae, miracidia and eggs at different concentrations 2.5, 5, 12.5, 25 and 50 μg/ml of EE and 2.6, 5.2, 13, 26 and 52 μM of CI in incubation times 1,2,4,6,12hrs were carried out. EE and CI evidenced anti-schistosomal activity with a dose and incubation time-dependent fashion. The effect of EE and CI was evident by the topography damage showed by SEM. EE proved moderate cytotoxicity with IC of 8.48 µg/ml.
Topics: Animals; Apocynaceae; Flavonoids; Glycosides; Plant Extracts; Pregnanes; Schistosoma mansoni; Schistosomicides
PubMed: 30404547
DOI: 10.1080/14786419.2018.1528584 -
Hippocampus Jul 2022The ability of endogenous neurosteroids (NSs) with pregnane skeleton modified at positions C-3 and C-5 to modulate the functional activity of inhibitory glycine...
The ability of endogenous neurosteroids (NSs) with pregnane skeleton modified at positions C-3 and C-5 to modulate the functional activity of inhibitory glycine receptors (GlyR) and ionotropic ɣ-aminobutyric acid receptors (GABA R) was estimated. The glycine and GABA-induced chloride current (I and I ) were measured in isolated pyramidal neurons of the rat hippocampus and in isolated rat cerebellar Purkinje cells, respectively. Our experiments demonstrated that pregnane NSs affected I and I in a different manner. At low concentrations (up to 5 μM), tested pregnane NSs increased or did not change the peak amplitude of the I , but reduced the I by decreasing the peak amplitude and/or accelerating desensitization. Namely, allopregnanolone (ALLO), epipregnanolone (EPI), pregnanolone (PA), pregnanolone sulfate (PAS) and 5β-dihydroprogesterone (5β-DHP) enhanced the I in Purkinje cells. Dose-response curves plotted in the concentration range from 1 nM to 100 μM were smooth for EPI and 5β-DHP, but bell-shaped for ALLO, PA and PAS. The peak amplitude of the I was reduced by PA, PAS, and 5α- and 5β-DHP. In contrast, ALLO, ISO and EPI did not modulate it. Dose-response curves for the inhibition of the I peak amplitude were smooth for all active compounds. All NSs accelerated desensitization of the I . The dose-response relationship for this effect was smooth for ALLO, PA, PAS and 5β-DHP, but it was U-shaped for EPI, 5α-DHP and ISO. These results, together with our previous results on NSs with androstane skeleton, offer comprehensive overview for understanding the mechanisms of effects of NSs on I and I .
Topics: 5-alpha-Dihydroprogesterone; Animals; Chlorides; Glycine; Neurons; Neurosteroids; Pregnanes; Pregnanolone; Rats; Rats, Wistar; Receptors, GABA-A; gamma-Aminobutyric Acid
PubMed: 35703084
DOI: 10.1002/hipo.23449 -
Journal of Asian Natural Products... Dec 2023Two new pregnane glycosides ( and ), together with four known ones (- ), were isolated from the roots of Royle ex Wight (Asclepiadaceae). On the basis of detailed...
Two new pregnane glycosides ( and ), together with four known ones (- ), were isolated from the roots of Royle ex Wight (Asclepiadaceae). On the basis of detailed spectroscopic analysis and chemical method, the structures of new compounds were characterized to be metaplexigenin 3---D-cymaropyranosyl- (1→4)--L-diginopyranosyl-(1→4)--D-cymaropyranoside (), metaplexigenin 3---L-diginopyranosyl-(1→4)--D-cymaropyranoside (). All the isolated compounds (-) were tested for their inhibitory activity against the growth of human colon cancer cell lines HCT-116. Compounds and showed significant cytoxicities with IC values of 43.58 µM and 52.21 µM.
Topics: Humans; Cynanchum; Plant Roots; Pregnanes; Glycosides; Molecular Structure
PubMed: 37178131
DOI: 10.1080/10286020.2023.2211550 -
Phytochemistry Sep 2023Eighteen previously unreported pregnane glycosides, namely marsdenosides S1-S18, along with 15 known analogues, have been isolated from the stems of Marsdenia...
Eighteen previously unreported pregnane glycosides, namely marsdenosides S1-S18, along with 15 known analogues, have been isolated from the stems of Marsdenia tenacissima. The structures of the undescribed compounds were elucidated by spectroscopic means, and their absolute configurations were established on the basis of time-dependent density functional theory (TD-DFT) based electronic circular dichroism (ECD) calculation, X-ray crystallography and acid hydrolysis. All the isolates were evaluated for their chemo-reversal ability against P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) in MCF-7/ADR cell line, and nine ones displayed moderate MDR reversal activity with reversal folds in the range of 2.45-9.01. The most active 12-O-acetyl-20-O-benzoyl-(14,17,18-orthoacetate)-dihydrosarcostin-3-O-β-d-thevetopyranosyl-(1 → 4)-O-β-d-oleandropyranosyl-(1 → 4)-O-β-d-cymaropyranoside increased the sensitivity of MCF-7/ADR cell to adriamycin comparably to the reference drug verapamil (RF = 8.93).
Topics: Marsdenia; Molecular Structure; Glycosides; Pregnanes; Drug Resistance, Multiple
PubMed: 37414237
DOI: 10.1016/j.phytochem.2023.113787