New Flavone C-Glycosides from Scleranthus perennis and Their Anti-Collagenase Activity.
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ABSTRACT:
SUBMITTER: Jakimiuk K
PROVIDER: S-EPMC8468783 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:Inflammation is related to many diseases. Lindera akoensis Hayata was often used in folktherapy in Taiwan for inflammation. In this study, three new flavonol acyl glycosides, namelykaempferol-3-O--D-4",6"-di-(E)-p-coumaroylglucoside (1), 3"-(E)-p-coumaroylafzelin (2) and 40-Omethyl-2",4"-di-(E)-p-coumaroylquercitrin (3), and three components, 3-dodecyl-4-hydroxy-5-methyldihydrofuran-2-one (4), 2-acetoxyclovan-9-ol (5), (1,4,6)-trihydroxyeudesmane(6) that were isolated from the natural product for the first time were obtained along with 25 knowncompounds from L. akoensis. Their structures were determined by comprehensive spectroscopicanalyses (1D and 2D NMR, EI-, ESI- and HRESI-MS). The ability of 1 to decrease the LPS-stimulatedproduction of nitrite in RAW264.7 cell was evaluated, showing an IC50 value of 36.3 ± 3.2 μM.This result supports the value of L. akoensis as a traditional medicine resource.
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Project description:The antitumor activity of natural flavonoids has been exhaustively reported. Previously it has been demonstrated that prenylation of flavonoids allows the discovery of new compounds with improved antitumor activity through the activation of caspase-7 activity. The synthesis of twenty-five flavonoids (4?28) with one or more alkyl side chains was carried out. The synthetic approach was based on the reaction with alkyl halide in alkaline medium by microwave (MW) irradiation. The in vitro cell growth inhibitory activity of synthesized compounds was investigated in three human tumor cell lines. Among the tested compounds, derivatives 6, 7, 9, 11, 13, 15, 17, and 18 revealed potent growth inhibitory activity (GI50 < 10 ?M), being the growth inhibitory effect of compound 13 related with a pronounced caspase-7 activation on MCF-7 breast cancer cells and yeasts expressing human caspase-7. A quantitative structure-activity relationship (QSAR) model predicted that hydrophilicity, pattern of ring substitution/shape, and presence of partial negative charged atoms were the descriptors implied in the growth inhibitory effect of synthesized compounds. Docking studies on procaspase-7 allowed predicting the binding of compound 13 to the allosteric site of procaspase-7.
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Project description:Microctis Folium (MF), the dried leaves of Microcos paniculata, is widely used as a medical and food dual-purpose herb in South-east Asia and China. However, the quality control of MF is not well studied. A simple and reliable quality control method was urgently needed for its growing usage. Herein, at first, its main active components were identified by UPLC-ESI-qTOF-MS, and a representative MF flavone glycosides profile consisting of ten compounds was illustrated, which is the most detailed one up to now. Successively, using vitexin as the reference substance, a novel QAMS method with HPLC for quantification of the ten identified flavone glycosides was developed and methodologically validated. Furthermore, making use of the abovementioned QAMS method, quantitative profiling of 21 batches of prepared MF slices collected from different hospital pharmacies were performed. As a result, the total contents of ten flavone glucosides and the content of specific compound showed obvious variations. Using the ten compounds' contents dataset, the 21 batches of samples were divided into two distinct clusters by HCA. In sum, our results indicated that it was of great importance to take quality control of prepared MF slices and we presented a robust and simple method for their quantitative determination, which should be beneficial for the quality control of MF and its derived products.
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Project description:A new sesquilignan glycoside 1, together with seven known phenolic glycosides 2-8 were isolated from the aerial parts of Capsella bursa-pastoris. The chemical structure of the new compound 1 was elucidated by extensive nuclear magnetic resonance (NMR) data (¹H- and 13C-NMR, ¹H-¹H correlation spectroscopy (¹H-¹H COSY), heteronuclear single-quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC), and nuclear overhauser effect spectroscopy (NOESY)) and HR-FABMS analysis. The anti-inflammatory effects of 1-8 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 4 and 7 exhibited moderate inhibitory effects on nitric oxide production in LPS-activated BV-2 cells, with IC50 values of 17.80 and 27.91 µM, respectively.
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Project description:Interest in the antioxidant activity of bamboo leaves is growing. To discover new sources of natural antioxidants, a TLC bioautography method combined with a new image processing method was developed to evaluate the antioxidant activity of leaf extracts from 15 different species of bamboo. The results showed that the methanolic extract of Bambusa. textilis McClure possessed the highest antioxidant activity among the selected bamboo species. To rapidly identify the antioxidant compounds, the crude extract of B. textilis McClure was analysed by HPLC-UV, and HPLC-micro-fractionation of the extract was carried out. Based on TLC bioautography-guided fractionation, three antioxidant fractions were isolated from B. textilis McClure by preparative chromatography. These three antioxidant compounds were identified as isoorientin 4''-O ?-D-xylopyranoside, isoorientin 2''-O-?-L-rhamnoside and isoorientin according to their UV, MS, and NMR data. The proposed TLC screening method could therefore be an easy way to evaluate the antioxidant activity of bamboo leaves, and the results achieved should prove very helpful for promoting their utilization, as B. textilis McClure can be considered a promising plant source of natural antioxidants.
| S-EPMC6268801 | biostudies-other
Project description:BackgroundOwing to their roles in tissue remodelling in health and disease, several studies have reported investigations on plant extracts as inhibitors of proteinases and as anti-oxidants.MethodsThe anti-ageing and anti-oxidant properties of 23 plant extracts (from 21 plant species) were assessed as anti-elastase and anti-collagenase activities and in selected anti-oxidant assays along with phenolic content.ResultsAnti-elastase activities were observed for nine of the extracts with inhibitory activity in the following order: white tea (approximately 89%), cleavers (approximately 58%), burdock root (approximately 51%), bladderwrack (approximately 50%), anise and angelica (approximately 32%). Anti-collagenase activities were exhibited by sixteen plants of which the highest activity was seen in white tea (approximately 87%), green tea (approximately 47%), rose tincture (approximately 41%), and lavender (approximately 31%). Nine plant extracts had activities against both elastase (E) and collagenase (C) and were ranked in the order of white tea (E:89%, C:87%) > bladderwrack (E:50%, C:25%) > cleavers (E:58%, C:7%) > rose tincture (E:22%, C:41%) > green tea (E:10%: C:47%) > rose aqueous (E: 24%, C:26%) > angelica (E:32%, C:17%) > anise (E:32%, C:6%) > pomegranate (E:15%, C:11%).Total phenolic content varied between 0.05 and 0.26 mg gallic acid equivalents (GAE)/mL with the exception of white tea (0.77 mg GAE/mL). For anti-oxidant assessment, the Trolox equivalent anti-oxidant capacity (TEAC) assay revealed activity for all extracts. White tea had the highest activity equivalent to approximately 21 microM Trolox for a 6.25 microg aliquot. In addition, seven extracts exhibited activities = 10 microM Trolox with witch hazel (6.25 microg = 13 microM Trolox) and rose aqueous (6.25 microg = 10 microM Trolox) showing very high activities at low concentrations. A high activity for white tea was also found in the superoxide dismutase (SOD) assay in which it exhibited ~88% inhibition of reduction of nitroblue tetrazolium. High activities were also observed for green tea (86.41%), rose tincture (82.77%), witch hazel (82.05%) and rose aqueous (73.86%).ConclusionFrom a panel of twenty three plant extracts, some one dozen exhibit high or satisfactory anti-collagenase or anti-elastase activities, with nine having inhibitory activity against both enzymes. These included white tea which was found to have very high phenolic content, along with high TEAC and SOD activities.
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Project description:Cymbidium kanran, an orchid exclusively distributed in Northeast Asia, has been highly valued as a decorative plant and traditional herbal medicine. Here, C. kanran extracts were prepared in 70% aqueous methanol using ultrasound-assisted extraction (UAE) and subjected to liquid chromatography-photodiode array detection and ultra-high performance liquid chromatography-quadrupole-time-of-flight-mass spectrometry analysis, which were used for quantitative and qualitative analysis, respectively. It was found that the extracts were rich in flavone C-glycosides including vicenin-2, vicenin-3, schaftoside, vitexin, and isovitexin. Ten deep eutectic solvents (DESs) were synthesized by combining choline chloride (hydrogen bond acceptor) with various polyols and diols (hydrogen bond donors) and were tested as a medium for the efficient production of extracts enriched with potentially bioactive flavone C-glycosides from C. kanran. A DES named ChCl:DPG, composed of choline chloride and dipropylene glycol at a 1:4 molar ratio, exhibited the best extraction yields. Then, the effects of extraction conditions on the extraction efficiency were investigated by response surface methodology. Lower water content in the extraction solvent and longer extraction time during UAE were desirable for higher extraction yields. Under the statistically optimized conditions, in which 100 mg of C. kanran powder were extracted in 0.53 mL of a mixture of ChCl:DPG and water (74:26, w/w) for 86 min, a total of 3.441 mg g-1 flavone C-glycosides including 1.933 mg g-1 vicenin-2 was obtained. This total yield was 196%, 131%, and 71% more than those obtained using 100% methanol, water, and 70% methanol, respectively.
| S-EPMC6150217 | biostudies-literature
Project description:BackgroundFlavone C-glycosides are difficult to be deglycosylated using traditional chemical methods due to their solid carbon-carbon bond between sugar moieties and aglycones; however, some bacteria may easily cleave this bond because they generate various specific enzymes.ResultsA bacterial strain, named W12-1, capable of deglycosylating orientin, vitexin, and isovitexin to their aglycones, was isolated from human intestinal bacteria in this study and identified as Enterococcus faecalis based on morphological examination, physiological and biochemical identification, and 16S rDNA sequencing. The strain was shown to preferentially deglycosylate the flavone C-glycosides on condition that the culture medium was short of carbon nutrition sources such as glucose and starch, and its deglycosylation efficiency was negatively correlated with the content of the latter two substances.ConclusionThis study provided a new bacterial resource for the cleavage of C-glycosidic bond of flavone C-glycosides and reported the carbon nutrition sources reduction induced deglycosylation for the first time.
| S-EPMC6537369 | biostudies-literature