Edgeworoside C

In Silico Identification of Potential Natural Product Inhibitors of Human Proteases Key to SARS-CoV-2 Infection.[Pubmed:32842606]

Molecules. 2020 Aug 22;25(17):3822.

Presently, there are no approved drugs or vaccines to treat COVID-19, which has spread to over 200 countries and at the time of writing was responsible for over 650,000 deaths worldwide. Recent studies have shown that two human proteases, TMPRSS2 and cathepsin L, play a key role in host cell entry of SARS-CoV-2. Importantly, inhibitors of these proteases were shown to block SARS-CoV-2 infection. Here, we perform virtual screening of 14,011 phytochemicals produced by Indian medicinal plants to identify natural product inhibitors of TMPRSS2 and cathepsin L. AutoDock Vina was used to perform molecular docking of phytochemicals against TMPRSS2 and cathepsin L. Potential phytochemical inhibitors were filtered by comparing their docked binding energies with those of known inhibitors of TMPRSS2 and cathepsin L. Further, the ligand binding site residues and non-covalent interactions between protein and ligand were used as an additional filter to identify phytochemical inhibitors that either bind to or form interactions with residues important for the specificity of the target proteases. This led to the identification of 96 inhibitors of TMPRSS2 and 9 inhibitors of cathepsin L among phytochemicals of Indian medicinal plants. Further, we have performed molecular dynamics (MD) simulations to analyze the stability of the protein-ligand complexes for the three top inhibitors of TMPRSS2 namely, qingdainone, Edgeworoside C and adlumidine, and of cathepsin L namely, ararobinol, (+)-oxoturkiyenine and 3alpha,17alpha-cinchophylline. Interestingly, several herbal sources of identified phytochemical inhibitors have antiviral or anti-inflammatory use in traditional medicine. Further in vitro and in vivo testing is needed before clinical trials of the promising phytochemical inhibitors identified here.

Coumarins from Edgeworthia chrysantha.[Pubmed:24531219]

Molecules. 2014 Feb 13;19(2):2042-8.

A new coumarin, edgeworic acid (1), was isolated from the flower buds of Edgeworthia chrysantha, together with the five known coumarins umbelliferone (2), 5,7-dimethoxycoumarin (3), daphnoretin (4), Edgeworoside C (5), and edgeworoside A (6). Their structures were established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift-correlated NMR pulse sequences (1H-1H COSY, HSQC and HMBC), in combination with acetylation reactions.

Separation and determination of the effective components in the alabastrum of Edgeworthia chrysantha Lindl. by micellar electrokinetic capillary chromatography.[Pubmed:16269220]

J Pharm Biomed Anal. 2006 Mar 18;40(5):1137-42.

A rapid and efficient micellar electrokinetic capillary chromatography (MEKC) method was developed to analyze Edgeworoside C (1), kaempferol-3-O-beta-D-glucoside (2) and rutin (3) in the alabastrum of Edgeworthia chrysantha Lindl. for the first time. The factors that affect the separation were studied, such as the concentrations of the buffer, SDS, and organic modifier, the apparent pH, the applied voltage and temperature. The analytes were well separated within 15 min with an electrolyte containing 25 mM Na(2)B(4)O(7), 30 mM NaH(2)PO(4), 60mM SDS and 15% acetonitrile (pH(*) 9.1) at 25 kV and 15 degrees C. The correlation coefficients between the peak areas of analytes and the corresponding concentrations were 0.9976-0.9981 under the optimum conditions. The relative standard deviations (R.S.D.) of the migration time and peak area were in the range 0.6-1.7 and 1.9-5.3%, respectively. The contents of analytes in E. chrysantha Lindl. collected from the different places were successfully determined with the recoveries ranging from 95.9 to 104.3%. And, the results demonstrated that there was significant difference between the two real samples.

Preparative isolation and purification of syringin and edgeworoside C from Edgeworthia chrysantha Lindl by high-speed counter-current chromatography.[Pubmed:15330108]

J Chromatogr A. 2004 Jul 23;1043(2):329-32.

The bioactive compound syringin along with Edgeworoside C were separated from the n-butanol extract of the stems and barks of Edgeworthia chrysantha Lindl (E. papyrifera) by high-speed counter-current chromatography (HSCCC) while it was difficult to purify each compound by silica gel column chromatography. Syringin was isolated from this plant for the first time. The two-phase solvent system used was composed of ethyl acetate-ethanol-water at an optimized volume ratio of 15:1:15 (v/v/v). Preparative HSCCC yielded, from 110mg of the partially purified extract, 28mg of syringin and 45 mg Edgeworoside C each at over 96% purity by high-performance liquid chromatography analysis. Their structures were identified by electron impact ionization MS, 1H NMR and 13C NMR.