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| 5mg |
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Kaempferol-3-O-glucorhamnoside (astragalin) is a naturally occuring and bioactive flavonoid found in plant Thesium chinense Turcz, that inhibits inflammatory responses via MAPK and NF-κB pathways in vitro and in vivo.
| Targets |
The action targets of Kaempferol-3-O-glucorhamnoside are the MAPK signaling pathway (including p38 MAPK, ERK1/2, and JNK) and the NF-κB signaling pathway. [1]
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| ln Vitro |
1. In LPS-stimulated RAW264.7 murine macrophages: Kaempferol-3-O-glucorhamnoside (20 μM, 40 μM) was preincubated with cells for 1 hour before LPS (1 μg/mL) treatment, and after 24 hours of co-incubation, it significantly reduced nitric oxide (NO) production (detected by Griess reagent) and decreased the secretion levels of pro-inflammatory cytokines TNF-α, IL-1β, and IL-6 (measured by ELISA) in a concentration-dependent manner [1]
2. In LPS-stimulated HaCaT human keratinocytes: Kaempferol-3-O-glucorhamnoside (20 μM, 40 μM) was preadministered for 1 hour, followed by LPS (1 μg/mL) stimulation for 6 hours; real-time quantitative PCR (qPCR) results showed that it downregulated the mRNA expression levels of TNF-α, IL-1β, and IL-6 compared with the LPS-only group [1] 3. Mechanism detection in vitro: Western blot analysis revealed that Kaempferol-3-O-glucorhamnoside (20 μM, 40 μM) inhibited the phosphorylation of p38 MAPK, ERK1/2, and JNK in the MAPK pathway, and suppressed the phosphorylation and nuclear translocation of NF-κB p65 subunit as well as the degradation of IκBα in the NF-κB pathway in both LPS-stimulated RAW264.7 cells and HaCaT cells [1] |
| ln Vivo |
1. TPA-induced mouse ear edema model: Male ICR mice (6–8 weeks old) were used; Kaempferol-3-O-glucorhamnoside (10 mg/kg, 20 mg/kg) was administered via intraperitoneal injection 30 minutes before topical application of TPA (2 μg/ear) to the right ear. After 24 hours, the drug significantly reduced ear thickness (measured by a digital caliper) and ear disc weight (punched into 8-mm diameter discs), and decreased myeloperoxidase (MPO) activity (an indicator of neutrophil infiltration) in ear tissue homogenates [1]
2. LPS-induced mouse peritonitis model: Male ICR mice (6–8 weeks old) received intraperitoneal injection of Kaempferol-3-O-glucorhamnoside (20 mg/kg) 30 minutes prior to intraperitoneal injection of LPS (10 mg/kg). After 6 hours, the drug reduced the total number of inflammatory cells in peritoneal exudates (counted by a hemocytometer) and lowered the concentrations of TNF-α, IL-1β, and IL-6 in peritoneal fluid (detected by ELISA) [1] 3. Mechanism detection in vivo: Western blot analysis of liver tissue from LPS-induced mice showed that Kaempferol-3-O-glucorhamnoside (20 mg/kg) inhibited the phosphorylation of p38 MAPK, ERK1/2, JNK, and NF-κB p65 in hepatic tissue compared with the LPS control group [1] |
| Cell Assay |
1. RAW264.7 cell culture and treatment: Cells were maintained in DMEM medium supplemented with 10% fetal bovine serum and 1% penicillin-streptomycin at 37°C in a 5% CO₂ incubator. For experiments, cells were seeded in 96-well plates (for NO and cytokine detection) or 6-well plates (for Western blot) at appropriate densities. After 24 hours of adherence, cells were pretreated with Kaempferol-3-O-glucorhamnoside (20 μM, 40 μM) for 1 hour, then stimulated with LPS (1 μg/mL) for 24 hours (for supernatant collection) or 1 hour (for protein extraction). After treatment, supernatants were collected for NO (Griess reagent) and cytokine (ELISA) detection; cells were lysed to extract total proteins (or nuclear proteins for NF-κB p65) for Western blot [1]
2. HaCaT cell culture and qPCR detection: Cells were cultured in DMEM/F12 medium containing 10% fetal bovine serum and 1% penicillin-streptomycin under 37°C and 5% CO₂. Cells were seeded in 6-well plates and pretreated with Kaempferol-3-O-glucorhamnoside (20 μM, 40 μM) for 1 hour, followed by LPS (1 μg/mL) stimulation for 6 hours. Total RNA was extracted from cells using an RNA extraction kit, reverse-transcribed into cDNA with a reverse transcription kit, and qPCR was performed using specific primers for TNF-α, IL-1β, IL-6, and GAPDH (internal reference) to detect mRNA expression levels [1] 3. Cell viability assay (MTT): RAW264.7 and HaCaT cells were seeded in 96-well plates, treated with Kaempferol-3-O-glucorhamnoside (20 μM, 40 μM) for 25 hours (1 hour pretreatment + 24 hours LPS stimulation), then MTT solution was added and incubated for 4 hours. The supernatant was removed, DMSO was added to dissolve formazan crystals, and absorbance at 570 nm was measured to evaluate cell viability; no significant cytotoxicity was observed in the drug-treated groups [1] |
| Animal Protocol |
1. TPA-induced ear edema experiment: Male ICR mice (n=6 per group) were acclimated for 1 week before the experiment. Kaempferol-3-O-glucorhamnoside was dissolved in dimethyl sulfoxide (DMSO) and then diluted with normal saline to a final DMSO concentration ≤ 0.1% (to avoid solvent toxicity). The drug was administered via intraperitoneal injection at doses of 10 mg/kg and 20 mg/kg; the control group received equal volume of solvent. Thirty minutes after drug administration, 2 μg of TPA (dissolved in acetone) was topically applied to the right ear of each mouse, and the left ear was treated with acetone as a normal control. After 24 hours, mice were sacrificed by cervical dislocation; ear thickness was measured three times at the same site with a digital caliper, and the average value was calculated. Ear discs (8 mm in diameter) were punched from both ears and weighed; the right ear disc weight minus the left ear disc weight was used to evaluate edema degree. Ear tissue was homogenized in physiological saline, centrifuged to collect supernatant, and MPO activity was detected using an MPO assay kit [1]
2. LPS-induced peritonitis experiment: Male ICR mice (n=6 per group) were acclimated for 1 week. Kaempferol-3-O-glucorhamnoside (20 mg/kg) was prepared as the same solvent system as above and administered via intraperitoneal injection; the control group received solvent. Thirty minutes later, mice were injected intraperitoneally with 10 mg/kg LPS (dissolved in normal saline). After 6 hours, mice were sacrificed by cervical dislocation; 5 mL of cold normal saline was injected into the abdominal cavity, and the abdomen was gently massaged for 1 minute. Peritoneal exudate was collected, and the total number of inflammatory cells was counted using a hemocytometer. The remaining exudate was centrifuged, and the supernatant was used to detect TNF-α, IL-1β, and IL-6 concentrations via ELISA. Livers were excised, rinsed with cold normal saline, and stored at -80°C for subsequent Western blot analysis [1] |
| Toxicity/Toxicokinetics |
1. In vitro toxicity: MTT assay showed that kaempferol-3-O-glucorlaminoid at concentrations of 20 μM and 40 μM had no significant effect on the viability of RAW264.7 macrophages and HaCaT keratinocytes compared with the blank control group (no statistically significant difference in absorbance at 570 nm) [1] 2. In vivo toxicity: In in vivo experiments (TPA ear edema and LPS peritonitis models), mice treated with kaempferol-3-O-glucorlaminoid (10 mg/kg, 20 mg/kg) did not show abnormal behavior (such as reduced activity, loss of appetite) or obvious organ damage (liver, spleen, and kidneys observed after sacrifice) [1]
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| References | |
| Additional Infomation |
Kaempferol-3-neohesperidin belongs to the flavonoid class and is a glycoside. Kaempferol-3-neohesperidin has been reported to exist in persimmon (Diospyros cathayensis), soybean (Glycine max), and other organisms with relevant data. Kaempferol-3-O-glucorlaminoid is a natural flavonoid glycoside derived from plants. Studies have confirmed that its anti-inflammatory effect is achieved by inhibiting the overactivation of the MAPK and NF-κB signaling pathways—these two pathways are key pathways for regulating the transcription and secretion of pro-inflammatory cytokines. This study provides preclinical experimental evidence for the potential application of kaempferol-3-O-glucorlaminoid in the treatment of inflammatory diseases such as dermatitis and peritonitis [1].
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| Molecular Formula |
C27H30O15
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| Molecular Weight |
594.5181
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| Exact Mass |
594.158
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| CAS # |
40437-72-7
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| Related CAS # |
40437-72-7
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| PubChem CID |
5318761
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| Appearance |
Light yellow to yellow solid
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| Density |
1.8±0.1 g/cm3
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| Boiling Point |
945.5±65.0 °C at 760 mmHg
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| Melting Point |
182-185 ºC
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| Flash Point |
314.1±27.8 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
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| Index of Refraction |
1.744
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| LogP |
2.66
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| Hydrogen Bond Donor Count |
9
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| Hydrogen Bond Acceptor Count |
15
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
42
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| Complexity |
985
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| Defined Atom Stereocenter Count |
10
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| SMILES |
O(C1([H])C([H])(C([H])(C([H])(C([H])(C([H])([H])[H])O1)O[H])O[H])O[H])C1([H])C([H])(OC2C(C3=C(C([H])=C(C([H])=C3OC=2C2C([H])=C([H])C(=C([H])C=2[H])O[H])O[H])O[H])=O)OC([H])(C([H])([H])O[H])C([H])(C1([H])O[H])O[H]
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| InChi Key |
OHOBPOYHROOXEI-OVNVQJKQSA-N
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| InChi Code |
InChI=1S/C27H30O15/c1-9-17(32)20(35)22(37)26(38-9)42-25-21(36)18(33)15(8-28)40-27(25)41-24-19(34)16-13(31)6-12(30)7-14(16)39-23(24)10-2-4-11(29)5-3-10/h2-7,9,15,17-18,20-22,25-33,35-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22-,25-,26+,27+/m1/s1
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| Chemical Name |
3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
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| Synonyms |
Kaempferol-3-O-glucorhamnoside
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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) |
H2O: ~100 mg/mL (~168.2 mM)
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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 | 1.6820 mL | 8.4101 mL | 16.8203 mL | |
| 5 mM | 0.3364 mL | 1.6820 mL | 3.3641 mL | |
| 10 mM | 0.1682 mL | 0.8410 mL | 1.6820 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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