| Targets |
Natural flavone; anti-inflammatory, anti-tumor, anti-oxidant, neuroprotective, anti-fungal activities
The primary targets of 4′-Hydroxywogonin include inflammatory signaling pathways, oxidative stress pathways, and cancer-related targets. It has been shown to inhibit the production of pro-inflammatory cytokines and reduce the activation of NF-κB and MAPK pathways. The compound also exhibits antioxidant activity by scavenging free radicals and upregulating endogenous antioxidant enzymes. It induces apoptosis in cancer cells through various mechanisms, including modulation of Bcl-2 family proteins and activation of caspases. |
|---|---|
| ln Vitro |
In LPS-stimulated RAW 264.7 macrophages, 4′-Hydroxywogonin (8-Methoxyapigenin; 0.5-15 μM; 0-24 h) suppresses iNOS and COX-2 expression, which prevents NO and PGE2 production[1]. It also displays low cytotoxicity. -Induction of pro-inflammatory cytokines by LPS in RAW 264.7 macrophages and inhibition of LPS-induced activation of NF-κB are both inhibited by hydroxywogonin (0.5-15 μM; 1 and 12 h)[1]. RAW 264.7 macrophages treated with 4′-hydroxywogonin (0.5–15 μM; 1 h) are less susceptible to LPS-induced IκB–α degradation, TAK and IKK activation, and MAPK and AKTin phosphorylation[1]. In LPS-stimulated RAW 264.7 macrophages, 4′-hydroxywogonin (0.5–15 μM; 24 h) minimizes ROS production[1]. When exposed to concentrations and times that vary, 4′-hydroxywogonin (0–10 μg/mL; 24 h) diminishes the survival of SW620 cells and lowers the expression of VEGF-A (vascular endothelial growth factor–A), the main pro-angiogenic cytokine in tumor angiogenesis, both in mRNA and protein[2]. Apoptosis is induced and the expression of C-MYC, BCL-2, and cleaved caspase 3 is reduced by 4′-hydroxywogonin (24 h; SUP-B15 and Jurkat cells)[3].
In vitro, 4′-Hydroxywogonin demonstrates anti-inflammatory activity by reducing the secretion of TNF-α, IL-6, and IL-1β in LPS-stimulated macrophages. It exhibits antioxidant effects by reducing ROS levels and increasing the activity of antioxidant enzymes such as SOD and CAT. In cancer cell lines, it inhibits cell proliferation and induces apoptosis in a dose-dependent manner. The compound has been studied in various cell models, including HepG2, MCF-7, and A549 cells. |
| ln Vivo |
In a mouse model, 4′-hydroxywogonin (10 and 20 mg/kg; ip; male C57BL/6 mice) reduces LPS-induced acute lung damage (ALI)[1].
In vivo activity of 4′-Hydroxywogonin has been reported in animal models of inflammation and cancer. It has shown efficacy in reducing edema in carrageenan-induced paw edema models and inhibiting tumor growth in xenograft models. However, detailed pharmacokinetic and pharmacodynamic data are limited. The compound is primarily studied for its in vitro activities, and further in vivo studies are needed to confirm its therapeutic potential. |
| Enzyme Assay |
In vitro enzyme/receptor binding assays for 4′-Hydroxywogonin typically involve evaluating its antioxidant activity via DPPH, ABTS, and FRAP assays. Anti-inflammatory activity is assessed by measuring cytokine levels in LPS-stimulated macrophages using ELISA. Enzyme inhibition assays may include COX-1, COX-2, and LOX inhibition. The compound is tested at concentrations ranging from 1 to 100 µM.
|
| Cell Assay |
Cell Viability Assay[1]
Cell Types: RAW 264.7 macrophages Tested Concentrations: 0.5, 5 and 15 μM Incubation Duration: 24 hrs (hours) Experimental Results: Had low cytotoxicity in RAW 264.7 macrophages. Western Blot Analysis[1] Cell Types: RAW 264.7 macrophages Tested Concentrations: 0.5, 5 and 15 μM Incubation Duration: 1 hrs (hours) Experimental Results: Attenuated the increase of iNOS and COX-2 mRNA expression induced by LPS in RAW 264.7 cells. Western Blot Analysis[1] Cell Types: RAW 264.7 macrophages Tested Concentrations: 0.5, 5 and 15 μM Incubation Duration: 1 and 12 hrs (hours) Experimental Results: decreased TNF-α, IL-6 and IL-1β mRNA expression in a dose-dependent manner. Inhibited LPS-induced p65 phosphorylation and nuclear translocation. Western Blot Analysis[1] Cell Types: RAW 264.7 macrophages Tested Concentrations: 0.5, 5 and 15 μM Incubation Duration: 1 hrs (hours) Experimental Results: Attenuated LPS induced IκB-α degradation. Attenuated the phosphorylation of ERK1/2 and p38 in a dose-dependent manner. decreased the intensity of the TAK1/TAB1 band. Western Blot Analysis[2] Cell Types: SW620 cells Concen In vitro cellular assays for 4′-Hydroxywogonin involve testing its anti-inflammatory, antioxidant, and anticancer activities. For anti-inflammatory studies, macrophages are treated with LPS and the compound, and cytokine levels are measured. For antioxidant studies, cells are exposed to oxidative stress (e.g., H2O2) in the presence of the compound, and ROS levels are measured. For anticancer studies, cancer cell lines are treated, and cell viability, apoptosis, and cell cycle are assessed. |
| Animal Protocol |
Animal/Disease Models: Male C57BL/6 mice (6-8 weeks old; 20 g) with acute lung injury model[1]
Doses: 10 and 20 mg/kg Route of Administration: intraperitoneal (ip)injection, 12 and 1 h before LPS treatment Experimental Results: Had potential protective effects against inflammation in LPS induced ALI mice. Attenuated the degree of leukocyte infiltration. In vivo animal studies for 4′-Hydroxywogonin include models of inflammation (carrageenan-induced paw edema) and cancer (xenograft tumors). Animals are treated with the compound via oral or intraperitoneal administration at doses typically ranging from 10 to 100 mg/kg. Inflammatory markers and tumor volumes are measured. However, detailed protocols are not consistently reported in the literature. |
| ADME/Pharmacokinetics |
4′-Hydroxywogonin has a molecular formula of C16H12O6 and a molecular weight of 300.26. It appears as a yellow powder with a purity of ≥98%. It is soluble in DMSO and ethanol, but poorly soluble in water. The compound should be stored in a dry, dark place at -20°C. It is stable for up to 1 year under recommended storage conditions. It is intended for research use only and is not for human consumption.
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| Toxicity/Toxicokinetics |
The toxicity profile of 4′-Hydroxywogonin has not been extensively characterized. As a natural flavonoid, it is generally considered to have low toxicity. Standard toxicity studies would include acute oral toxicity, repeated-dose toxicity, and genotoxicity in animal models. The compound is intended for research use only and is not approved for clinical use.
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| References | |
| Additional Infomation |
According to reports, 4'-hydroxybaicalin is found in Scutellaria baicalensis, Scutellaria baicalensis creeping, and other organisms with available data.
4′-Hydroxywogonin (CAS 57096-02-3) is a naturally occurring flavonoid found in Scutellaria species. It has a molecular formula of C16H12O6 and a molecular weight of 300.26. The compound exhibits anti-inflammatory, antioxidant, and anticancer activities. It inhibits pro-inflammatory cytokine production, scavenges free radicals, and induces apoptosis in cancer cells. It is intended for research use only and is not approved for clinical use. |
| Exact Mass |
300.063
|
|---|---|
| CAS # |
57096-02-3
|
| PubChem CID |
5322078
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.5±0.1 g/cm3
|
| Boiling Point |
578.1±50.0 °C at 760 mmHg
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| Flash Point |
220.9±23.6 °C
|
| Vapour Pressure |
0.0±1.7 mmHg at 25°C
|
| Index of Refraction |
1.697
|
| LogP |
1.37
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
22
|
| Complexity |
454
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
OEZZJTAJYYSQKM-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C16H12O6/c1-21-15-12(20)6-10(18)14-11(19)7-13(22-16(14)15)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3
|
| Chemical Name |
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-methoxychromen-4-one
|
| Synonyms |
4'-Hydroxywogonin; 57096-02-3; 5,7,4'-Trihydroxy-8-methoxyflavone; 8-Methoxyapigenin; 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-methoxychromen-4-one; Isoscutellarein 8-methyl ether; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-methoxy-; F 36; Isoscutellarein 8-methyl ether;
|
| 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.) |
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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