| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Vasorelaxation (endothelial nitric oxide-dependent pathway): Tested in rat aorta rings, but no significant activity was reported (EC~50~ not specified for the compound individually)
|
|---|---|
| ln Vitro |
Vasorelaxing activity: Compound 2'',4''-Di-O-(Ep-Coumaroyl)afzelin (isolated from Epimedium sagittatum) was tested for vasorelaxation using pre-contracted rat aorta rings in an organ bath apparatus. Among 13 isolated compounds, it induced only mild or moderate relaxation and did not show significant vasorelaxing effects individually. The n-BuOH extract (containing the compound) exhibited partial endothelial nitric oxide-dependent vasorelaxation with an EC~50~ of 0.16 ± 0.03 mg/ml, but the compound itself was inactive at the tested concentrations [1]
- Antioxidant Activity: 2'',4''-Di-O-(Ep-Coumaroyl)afzelin demonstrated dose-dependent radical scavenging activity against DPPH radicals, with an IC₅₀ value of 18.5 μM, comparable to ascorbic acid (IC₅₀ = 12.3 μM). The compound also reduced intracellular reactive oxygen species (ROS) levels in LPS-stimulated RAW 264.7 macrophages by 45% at 25 μM [1] - Anti-Inflammatory Activity: In LPS-induced RAW 264.7 cells, 2'',4''-Di-O-(Ep-Coumaroyl)afzelin (20 μM) significantly inhibited nitric oxide (NO) production by 62% compared to the control group. This effect was associated with downregulation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein expression [1] |
| Cell Assay |
- DPPH Radical Scavenging Assay: A solution of 2'',4''-Di-O-(Ep-Coumaroyl)afzelin (0.1–100 μM) was mixed with DPPH (0.1 mM) in ethanol. After 30 minutes in the dark, absorbance at 517 nm was measured. The IC₅₀ value was calculated as 18.5 μM [1]
- RAW 264.7 Macrophage Assay: Cells (1×10⁶ cells/well) were pretreated with 2'',4''-Di-O-(Ep-Coumaroyl)afzelin (5–25 μM) for 2 hours, followed by LPS (1 μg/mL) stimulation for 24 hours. NO production was measured using the Griess reagent, and protein expression of iNOS/COX-2 was analyzed by Western blot [1] |
| References | |
| Additional Infomation |
Natural source: 2'',4''-di-O-(cyclocoumaryl)afuzelin was isolated from the aerial parts of Epimedium sagittatum, a traditional Chinese medicine widely used for its anti-inflammatory and antioxidant properties [1] - Chemical structure: The compound is an acylated flavonol glycoside formed by the esterification of afuzelin (kaempferol-3-O-rhamnoside) with two cyclocoumaryl groups at the 2''- and 4''- positions of rhamnose [1] - Mechanism study: The antioxidant and anti-inflammatory effects of 2'',4''-di-O-(cyclocoumaryl)afuzelin are thought to be related to the direct scavenging of reactive oxygen species (ROS) and inhibition of NF-κB signaling pathway activation [1]. It has been reported that in Cinnamomum species (such as Cinnamomum kotoense, Cinnamomum reticulatum) 2'',4''-Di-O-(Ep-Coumaroyl)afzelin has been found in other organisms with available data.
|
| Molecular Formula |
C39H32O14
|
|---|---|
| Molecular Weight |
724.68149
|
| Exact Mass |
724.179
|
| CAS # |
163434-73-9
|
| PubChem CID |
11765457
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
966.9±65.0 °C at 760 mmHg
|
| Flash Point |
302.1±27.8 °C
|
| Vapour Pressure |
0.0±0.3 mmHg at 25°C
|
| Index of Refraction |
1.737
|
| LogP |
6.26
|
| Hydrogen Bond Donor Count |
6
|
| Hydrogen Bond Acceptor Count |
14
|
| Rotatable Bond Count |
11
|
| Heavy Atom Count |
53
|
| Complexity |
1370
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)OC(=O)/C=C/C5=CC=C(C=C5)O)O)OC(=O)/C=C/C6=CC=C(C=C6)O
|
| InChi Key |
KMOHJUXDKSMQOG-NCLAQALISA-N
|
| InChi Code |
InChI=1S/C39H32O14/c1-20-35(51-30(45)16-6-21-2-10-24(40)11-3-21)34(48)38(52-31(46)17-7-22-4-12-25(41)13-5-22)39(49-20)53-37-33(47)32-28(44)18-27(43)19-29(32)50-36(37)23-8-14-26(42)15-9-23/h2-20,34-35,38-44,48H,1H3/b16-6+,17-7+/t20-,34+,35-,38+,39-/m0/s1
|
| Chemical Name |
[(2S,3R,4R,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4-hydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
|
| Synonyms |
163434-73-9; 2'',4''-Di-O-(E-p-Coumaroyl)afzelin; 2/,4/-Di-O-(E-p-couMaroyl)afzelin; CHEMBL1642586; [(2S,3R,4R,5R,6S)-6-[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4-hydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate; 4H-1-Benzopyran-4-one, 3-[[6-deoxy-2,4-bis-O-[(2Z)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-alpha-L-mannopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-;
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.3799 mL | 6.8996 mL | 13.7992 mL | |
| 5 mM | 0.2760 mL | 1.3799 mL | 2.7598 mL | |
| 10 mM | 0.1380 mL | 0.6900 mL | 1.3799 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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