| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
iNOS
luteolin 5-O-glucoside suppresses the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase‑2 (COX‑2) in LPS‑stimulated RAW 264.7 macrophages. [1] |
|---|---|
| ln Vitro |
At non-toxic quantities and in a dose-dependent way, luteolin 5-O-glucoside suppresses the formation of ROS and NO generated by t-BHP and LPS in RAW 264.7 cells. Additionally, Luteolin 5-O-glucoside can prevent COX-2 and iNOS from being expressed in LPS-stimulated macrophages [1].
- luteolin 5-O-glucoside (up to 200 μM) did not significantly affect cell viability in RAW 264.7 cells as measured by MTT assay. [1] - It inhibited LPS‑induced NO production in a dose‑dependent manner with an IC₅₀ value of 64.36 μM (concentration range not explicitly specified but tested up to 200 μM). [1] - It inhibited t‑BHP‑induced intracellular ROS generation in a dose‑dependent manner with an IC₅₀ value of 2.17 μM (tested concentrations: 2.5–30 μM). [1] - Western blot analysis showed that luteolin 5-O-glucoside (25, 50, 100, 200 μM) suppressed LPS‑mediated increase of iNOS and COX‑2 protein expression in a dose‑dependent manner in RAW 264.7 cells. [1] |
| Cell Assay |
- Cell culture: RAW 264.7 murine macrophages were cultured in Dulbecco’s Modified Eagle’s Medium supplemented with 10% fetal bovine serum, 100 U/mL penicillin, and 100 μg/mL streptomycin at 37 °C in a humidified atmosphere containing 5% CO₂. [1]
- Cell viability (MTT assay): Cells were seeded in 96‑well plates and treated with various concentrations of luteolin 5-O-glucoside for 24 h. Then 100 μL of MTT solution (0.5 mg/mL in phosphate‑buffered saline) was added to each well and incubated for another 2 h. The resulting color was measured at 540 nm using a microplate spectrophotometer. [1] - NO production inhibition: RAW 264.7 cells (1.0 × 10⁵ cells/well in a 24‑well plate) were pretreated with luteolin 5-O-glucoside for 2 h, then stimulated with LPS (1.0 μg/mL) for 18 h. Nitrite concentration in the culture supernatant was measured by adding Griess reagent (100 μL) to 100 μL of supernatant, and absorbance was read at 540 nm. An iNOS inhibitor, AMT, was used as positive control. [1] - Intracellular ROS generation inhibition: RAW 264.7 cells (2.0 × 10⁴ cells/well) were seeded in a black 96‑well plate. After 24 h, cells were treated with luteolin 5-O-glucoside for 2 h, then exposed to t‑BHP (200 μM) to induce ROS. Cells were then incubated with DCFH‑DA (20 μM) for 30 min. Fluorescence intensity was measured at excitation 485 nm and emission 530 nm using a fluorescence microplate reader. [1] - Western blot for iNOS and COX‑2: RAW 264.7 cells were cultured in 100 mm dishes with or without LPS (1.0 μg/mL) and with/without luteolin 5-O-glucoside for 18 h. Cells were washed with ice‑cold PBS and lysed on ice for 30 min. Cell extracts were obtained by centrifugation at 14,000 × g for 20 min at 4 °C. Cytosolic proteins were separated by SDS–PAGE and transferred to PVDF membranes. Membranes were blocked with 5% non‑fat dry milk in TBST buffer for 1 h at room temperature, then incubated with primary antibodies against iNOS, COX‑2, or β‑actin (diluted 1:1000) overnight at 4 °C. After washing, membranes were incubated with HRP‑conjugated secondary antibody (diluted 1:2000) for 1 h at room temperature. Antibody labeling was visualized using chemiluminescent substrate and exposed to X‑ray film. [1] |
| Toxicity/Toxicokinetics |
- In cytotoxicity assays using RAW 264.7 cells, luteolin 5-O-glucoside did not significantly affect cell viability at concentrations up to 200 μM, as assessed by the MTT method. [1]
- Unlike its aglycone luteolin, which exhibited significant cytotoxicity at concentrations higher than 10 μM (p < 0.05), the glucosylated form showed lower cytotoxicity. [1] |
| References | |
| Additional Infomation |
Luteolin 5-glucoside has reportedly been found in Daphne odora, Equisetum hyemale, and other organisms with available data.
- luteolin 5-O-glucoside was isolated as the major compound from the ethyl acetate fraction of Cirsium maackii whole plants, with a yield of 8.23 g from 2.0 kg dried plant material. Quantitative HPLC analysis revealed that the compound constituted 56.07% of the methanolic extract of whole plants (based on relative peak area). [1] - The structure of luteolin 5-O-glucoside is characterized as luteolin 5‑O‑β‑glucopyranoside, with a glucosyl group attached at the C‑5 position. This glycosylation reduces cytotoxicity compared to luteolin while retaining anti‑inflammatory activity through suppression of iNOS and COX‑2 expression. [1] - The anti‑inflammatory mechanism of luteolin 5-O-glucoside is attributed to its ability to inhibit ROS generation, which in turn down‑regulates iNOS and COX‑2 protein expression in LPS‑stimulated macrophages. [1] - The study suggests that flavonoid glycosides such as luteolin 5-O-glucoside may be preferred over aglycones for oral administration as anti‑inflammatory agents, because glycosides are less cytotoxic and are naturally present in high yield in plant extracts. [1] |
| Molecular Formula |
C21H20O11
|
|---|---|
| Molecular Weight |
448.3769
|
| Exact Mass |
448.1
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| CAS # |
20344-46-1
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| PubChem CID |
5317471
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| Appearance |
Light yellow to yellow solid
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
864.2±65.0 °C at 760 mmHg
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| Melting Point |
260-263℃
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| Flash Point |
305.8±27.8 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
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| Index of Refraction |
1.740
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| LogP |
0.13
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| Hydrogen Bond Donor Count |
7
|
| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
4
|
| Heavy Atom Count |
32
|
| Complexity |
714
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1=C([H])C(=C([H])C2=C1C(C([H])=C(C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])O2)=O)O[H]
|
| InChi Key |
KBGKQZVCLWKUDQ-QNDFHXLGSA-N
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| InChi Code |
InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)31-15-5-9(23)4-14-17(15)12(26)6-13(30-14)8-1-2-10(24)11(25)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
|
| Chemical Name |
2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
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 | 2.2303 mL | 11.1513 mL | 22.3025 mL | |
| 5 mM | 0.4461 mL | 2.2303 mL | 4.4605 mL | |
| 10 mM | 0.2230 mL | 1.1151 mL | 2.2303 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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