engeletin and astilbin

This study aimed to isolate, prepare and identify the main flavonoids from a standardized

Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Benzothiazoles; Biphenyl Compounds; Catechin; Chromatography, High Pressure Liquid; Flavonoids; Flavonols; Glycosides; Lipopolysaccharides; Magnetic Resonance Spectroscopy; Mice; Picrates; RAW 264.7 Cells; Smilax; Sulfonic Acids

Rhizoma smilacis glabrae (RSG, tufuling) has been widely used in traditional Chinese medicine for deoxidation, dampness relief, and easing joint movement. The chemical composition of RSG has been systematically confirmed, and some of its compounds have been revealed to possess antioxidant, anti-inflammatory, immunomodulatory, hypouricemic, and hepatoprotective effects.. We aimed to clarify whether a RSG extract attenuates hyperuricemia, paw edema, and renal injury in mice with potassium oxonate (PO)- and monosodium urate (MSU)-induced chronic hyperuricemia and gout.. RSG water extract was obtained and analyzed by HPLC-DAD-MS/MS. To establish a murine model with chronic hyperuricemia and gout, PO was orally administered daily from day 0 to day 24, whereas MSU was injected into the tibiotarsal joint on day 21. The mice in the drug intervention groups were treated once daily with doses of allopurinol or RSG extract from day 21 to day 24. The diameter of the ankle joints was measured with calipers. Serum TNF-α and IL-1β concentrations, hepatic XOD activity, and uric acid, creatinine, and blood urea nitrogen (BUN) levels were also determined. The right kidney and articular cavities were fixed, cut into sections, and stained with hematoxylin and eosin.. Nine compounds in the RSG water extract were unambiguously identified as 5-O-caffeoylshikimic acid, neoastilbin, astilbin, taxifolin, neoisoastilbin, isoastilbin, engeletin, isoengeletin, and trans-resveratrol. The RSGE treatment dose-dependently reduced PO- and MSU-induced paw edema, serum TNF-α, IL-1β, IL-6, IL-12, uric acid, and BUN, while significantly elevated serum IL-10, urinary uric acid and creatinine levels as compared with the respective values in the hyperuricemic and gouty mice group (vehicle group). Moreover, the hepatic XOD activity was dose-dependently reduced by the RSGE treatment. In addition, RSGE treatment not only ameliorated the infiltration of inflammatory cells, tubular dilation and vacuole formation in renal tubular, but also improved the synovial hyperplasia, reduced inflammatory cells infiltration into the synovium, and diminished the erosive damage in the cartilage.. The murine model with chronic hyperuricemia and gout be built in present study is consistent with the clinical symptoms of patients with long-standing hyperuricemia and acute gouty arthritis. RSG water extract has potent efficacy in ameliorating murine hyperuricemia and gout induced by PO and MSU.

Topics: Animals; Antioxidants; Arthritis, Gouty; Disease Models, Animal; Drugs, Chinese Herbal; Edema; Flavonols; Glycosides; Gout; Hyperuricemia; Interleukin-1beta; Kidney; Liver; Male; Mice, Inbred BALB C; Oxonic Acid; Phytotherapy; Plant Extracts; Rhizome; Smilax; Tandem Mass Spectrometry; Uric Acid

Four pairs of diastereomers were successfully isolated and separated from the water extract of Engelhardia roxburghiana by high performance counter-current chromatography (HPCCC) using a two-step procedure. The diastereomers were initially separated by a two-phase solvent system composed of n-hexane-n-butanol-0.1% trifluoroacetic acid (1:2:3, v/v/v) and followed by the same solvent system using hydroxypropyl-β-cyclodextrin (HP-β-CD) as an additive. The chromatographic conditions, elution mode, and concentrations of the additive were refined. The two-step HPCCC isolation yielded 43.7mg (2S, 3S)-astilbin, 27.6mg (2R, 3R)-astilbin, 5.9mg (2S, 3R)-astilbin, 4.8mg (2R, 3S)-astilbin, 6.9mg (2S, 3S)-engelitin, 3.1mg (2R, 3R)-engelitin, 8.2mg (2S, 3R)-engelitin, and 6.0mg (2R, 3S)-engelitin from 384mg crude extract in four runs with purities of 99.3%, 96.2%, 99.8%, 99.9%, 97.0%, 96.5%, 96.1%, and 96.8%, respectively. The present study revealed that HP-β-CD can be used as an additive in HPCCC to effectively improve the resolution of the diastereomers. The established HPCCC method may serve as an approach to obtain high purity diastereomers on a large scale.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; beta-Cyclodextrins; Chromatography, High Pressure Liquid; Circular Dichroism; Countercurrent Distribution; Flavonols; Glycosides; Juglandaceae; Plant Extracts; Stereoisomerism

The rhizomes of Smilax glabra (SG) has long been used in Traditional Chinese and Thai herbal medicine to treat a variety of infectious diseases and immunological disorders.. To investigate the in vitro anti-allergic activities of crude extracts andpure isolated flavonoid compounds from SG by determination of inhibitory effect on antigen-induced release of β-hexosaminidasefrom RBL-2H3 cells.. The in vitro inhibitory effects ofcrude aqueous and organic extracts on β-hexosaminidase release in RBL-2H3 cells were evaluated as an in vitro indication ofpossible anti-allergic activity. Bioassay-guided fractionation of extracts was used to isolate flavonoid compounds from the ethanolic extracts.. The 95% and 50% ethanolic extracts of SG showed remarkably high anti-allergic activity, with IC50 values of 5.74 ± 2.44 and 23.54 ± 4.75 µg/ml, much higher activity than that for Ketotifen (IC50 58.90 µM). The water extract had negligible activity (IC50 > 100 µg/ml). The two isolated flavonols, Engeletin and Astilbin, showed weak anti-allergic activity, IC50 values 97.46 ± 2.04 and >100 µg/ml, respectively.. The 95% and 50% ethanolic extracts of SG showed strong anti-allergic activity, but two flavonol constituents did not show any significant anti-allergic activity. These findings suggest that a combination of effects of various phytochemicals in crude extracts used in traditional medicine, are responsible for the purported anti-allergic activity of SG herbal preparations. The plethora of constituents in crude extracts, as yet unidentified, are likely to be acting synergistically to account for the strong observed anti-allergic in vitro activity.

Topics: Animals; Anti-Allergic Agents; beta-N-Acetylhexosaminidases; Cells, Cultured; Flavonoids; Flavonols; Glycosides; Medicine, Traditional; Plant Extracts; Plants, Medicinal; Rats; Rhizome; Smilax

This study aimed to simultaneously determine the contents of astilbin and engeletin in dong medicine "sunl gaems" of Guizhou origin by quantitative analysis of multi-components by single marker (QAMS), with astilbin as the internal standard substance. On UPLC and HPLC chromatograms, different models of instruments were used to investigate relative correction factors (RCF), in order to discuss the interoperability of RCFs established in different chromatographic systems. The engeletin content was calculated based on the established RCFs and compared by the one point external standard method and the external standard working curve method, in order to verify the accuracy of QAMS. According to the result, in different chromatograms, the ratios between RCF and retention time of engeletin and astilbin had a good reproducibility, with RSD between 2.0% and 1.8%, both were less than 3%. The relative differences among results of QAMS, the external standard working curve method of dong medicine "sunl gaems" ranged between 1.6% and 3.9%, with RSD between 2.02%-0.80% in line with relevant requirements and Pearson correlation coefficient at 0.9998 (P <0.01). The findings showed that QAMS was an accurate, reliable and highly reproducible method to determine the contents of astilbin and engeletin in dong medicine "sunl gaems" of Guizhou origin and so could be used to control the inherent quality of the herb.

Topics: Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flavonols; Glycosides

Rhizoma Smilacis Glabrae (RSG) is a commonly used herbal material in functional food and Traditional Chinese Medicine. A HPLC chromatographic fingerprint was developed for its quality control and species differentiation. Nine peaks were found in the chromatogram of RSG and all these peaks were identified by diode array detection and electrospray ionization-MS/MS: 5-O-caffeoylshikimic acid, taxifolin, engeletin, isoengeletin, trans-resveratrol, astilbin and its three stereoisomers. Six of these constituents were consistently found in 18 batches of samples. The standard fingerprint of RSG was generated by mean simulation of all tested samples. Using the standard fingerprint, RSG could be easily differentiated from Rhizoma Smilacis Chinae and Rhizoma Heterosmilacis, the two species that can be confused with RSG.

Topics: Chromatography, High Pressure Liquid; Flavonols; Glycosides; Quercetin; Resveratrol; Rhizome; Shikimic Acid; Stilbenes; Tandem Mass Spectrometry

Rhizoma Smilacis Glabrae (RSG) and Rhizoma Smilacis Chinae (RSC) are two herbal materials that belong to the same genera and are both listed in the Chinese Pharmacopoeia. Chemical constituents in the two species were compared by HPLC-DAD-MS/MS. Many common constituents were found in both species, including shikimic acid, 5-O-caffeoylshikimic acid, trans-resveratrol, taxifolin, astilbin and its three stereoisomers, engeletin and isoengeletin. However, syringic acid was found only in RSG, while chlorogenic acid was found only in RSC.

Topics: Chromatography, High Pressure Liquid; Flavonols; Glycosides; Quercetin; Shikimic Acid; Tandem Mass Spectrometry

Engeletin, a flavonoid compound, was isolated from the leaves of Engelhardia roxburghiana for the first time, along with astilbin, another flavonoid. The chemical structures of engeletin and astilbin were confirmed by (1)H and (13)C nuclear magnetic resonance (NMR) and mass spectrometry (MS) spectra, and their anti-inflammatory activities were studied in lipopolysaccharide (LPS)-stimulated mouse J774A.1 macrophage cells. LPS induced the inflammatory state in macrophage cells and increased mRNA expressions of pro-inflammatory cytokines. Engeletin and astilbin exhibited remarkable inhibitory effects on interleukin (IL)-1β and IL-6 mRNA expression. Significant inhibition of LPS-mediated mRNA expressions were also seen in LPS binding toll-like receptor (TLR)-4, pro-inflammatory cytokine tumor necrosis factor (TNF)-α, IL-10, chemoattractant monocyte chemotactic protein (MCP)-1, and cyclooxygenase (COX)-2 genes. The reduced expression of these cytokines may alleviate immune response and reduce inflammatory activation, indicating that engeletin and astilbin may serve as potential anti-inflammatory agents.

Topics: Animals; Anti-Inflammatory Agents; Flavonols; Gene Expression Regulation; Glycosides; Interleukin-1beta; Juglandaceae; Macrophages; Mice; Plant Extracts; Plant Leaves; Toll-Like Receptor 4

Two dihydroflavonol glycosides, engeletin and astilbin, were isolated from an EtOAc extract of the leaves of Stelechocarpus cauliflorus R.E. Fr. (Annonaceae). The inhibitory activity of engeletin against a recombinant human aldose reductase (IC50 value=1.16 microM) was twice that of quercetin as a positive control (2.48 microM), and 23 times greater than that of astilbin (26.7 microM). Engeletin inhibited the enzyme uncompetitively. Astilbin was about as potent as the positive control, quercetin, in its inhibition of advanced glycation end-products formation. These flavonoids displayed therapeutic potential in the prevention and treatment of diabetic complications.

Topics: Aldehyde Reductase; Annonaceae; Flavonols; Glycation End Products, Advanced; Glycosides; Molecular Structure; Plant Extracts; Plant Leaves