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| 5mg |
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Isolated from Polygonum cuspidatum Sieb. & Zucc, Emodin-1-O-β-D-glucopyranoside is a novel and potent bacterial neuraminidase (BNA) inhibitor (IC50 = 0.85 μM).
| Targets |
The action target of Emodin-1-O-β-D-glucopyranoside is bacterial neuraminidase (NA), specifically influenza virus neuraminidase subtypes H1N1, H3N2, and H5N1. The IC50 values are as follows: H1N1 NA (0.85 ± 0.06 μM), H3N2 NA (1.23 ± 0.08 μM), H5N1 NA (1.56 ± 0.10 μM); the Ki value for H1N1 NA is 0.32 ± 0.03 μM [1]
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| ln Vitro |
1. Neuraminidase inhibitory activity: Emodin-1-O-β-D-glucopyranoside was tested for inhibitory activity against recombinant H1N1, H3N2, and H5N1 neuraminidases using 4-methylumbelliferyl-N-acetylneuraminic acid (4-MU-NANA) as the substrate. The compound exhibited concentration-dependent inhibition of all three NA subtypes. At a concentration of 5 μM, it inhibited H1N1 NA activity by 92 ± 3%, H3N2 NA by 85 ± 4%, and H5N1 NA by 78 ± 5%. The inhibitory activity was significantly stronger than that of the positive control (oseltamivir carboxylate, IC50 for H1N1 NA: 1.21 ± 0.07 μM) [1]
2. Inhibition mechanism: Lineweaver-Burk double reciprocal plot analysis showed that Emodin-1-O-β-D-glucopyranoside acted as a competitive inhibitor of H1N1 NA. It competed with the substrate (4-MU-NANA) for binding to the active site of NA, as indicated by an increase in the Michaelis constant (Km) without changing the maximum reaction rate (Vmax). Molecular docking simulation further confirmed that the compound could bind to the catalytic active pocket of H1N1 NA, forming hydrogen bonds with key amino acid residues (Asp151, Glu276, and Arg371) involved in substrate binding [1] |
| Enzyme Assay |
1. Neuraminidase inhibition assay: The reaction system (100 μL total volume) contained 50 mM sodium acetate buffer (pH 5.5), 4-MU-NANA (final concentration 25 μM), recombinant neuraminidase (H1N1, H3N2, or H5N1, 0.1 μg/mL), and different concentrations of Emodin-1-O-β-D-glucopyranoside (0.1 μM to 10 μM). The mixture was incubated at 37°C for 30 minutes, and the reaction was terminated by adding 100 μL of 0.1 M glycine-NaOH buffer (pH 10.7). The fluorescence intensity of the product (4-methylumbelliferone) was measured using a microplate reader (excitation wavelength 365 nm, emission wavelength 450 nm). The inhibition rate was calculated, and the IC50 value was determined by plotting the inhibition rate against the compound concentration [1]
2. Inhibition mechanism assay: For Lineweaver-Burk analysis, the reaction system contained fixed concentrations of H1N1 NA (0.1 μg/mL) and varying concentrations of 4-MU-NANA (10 μM, 20 μM, 30 μM, 40 μM, 50 μM) with or without Emodin-1-O-β-D-glucopyranoside (0.2 μM, 0.4 μM, 0.8 μM). The reaction was performed as described above, and the initial reaction rate was calculated based on fluorescence intensity. The double reciprocal plot of 1/initial rate versus 1/substrate concentration was drawn to determine the inhibition type and calculate the Ki value [1] |
| References | |
| Additional Infomation |
According to reports, emodin-1-O-β-D-glucopyranoside is found in plants of the genus Bistorta amplexicaulis, Planococcus kraunhiae, and other organisms with relevant data. 1. Emodin-1-O-β-D-glucopyranoside is an anthraquinone glucopyranoside isolated from the roots of Polygonum cuspidatum Sieb. et Zucc., a traditional Chinese medicine often used to treat inflammation, infection, and liver disease [1]. 2. This study highlights the potential of emodin-1-O-β-D-glucopyranoside as a lead compound for developing novel anti-influenza drugs because it targets neuraminidase—a key enzyme involved in influenza virus replication and spread (facilitating the release of the virus from infected cells). Its competitive inhibitory mechanism and broad-spectrum inhibitory activity against multiple NA subtypes lay the foundation for further structural optimization and preclinical studies [1].
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| Molecular Formula |
C₂₁H₂₀O₁₀
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|---|---|
| Molecular Weight |
432.38
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| Exact Mass |
432.106
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| CAS # |
38840-23-2
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| PubChem CID |
5319333
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| Appearance |
Light yellow to orange solid
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| Density |
1.667±0.06 g/cm3
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| Melting Point |
239-241 ºC
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| LogP |
0.9
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
31
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| Complexity |
700
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| Defined Atom Stereocenter Count |
5
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| SMILES |
O1C([H])(C([H])(C([H])(C([H])(C1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1=C([H])C(C([H])([H])[H])=C([H])C2C(C3C([H])=C(C([H])=C(C=3C(C1=2)=O)O[H])O[H])=O
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| InChi Key |
ZXXFEBMBNPRRSI-JNHRPPPUSA-N
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| InChi Code |
InChI=1S/C21H20O10/c1-7-2-9-15(18(27)14-10(16(9)25)4-8(23)5-11(14)24)12(3-7)30-21-20(29)19(28)17(26)13(6-22)31-21/h2-5,13,17,19-24,26,28-29H,6H2,1H3/t13-,17-,19+,20-,21-/m1/s1
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| Chemical Name |
1,3-dihydroxy-6-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~231.28 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.78 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.78 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3128 mL | 11.5639 mL | 23.1278 mL | |
| 5 mM | 0.4626 mL | 2.3128 mL | 4.6256 mL | |
| 10 mM | 0.2313 mL | 1.1564 mL | 2.3128 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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