| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
Natural biflavonoid; antioxidative; anti-inflammatory; anti-viral; anti-tumor
Target: not well-defined; no specific biological target has been validated. As a natural biflavonoid, it is believed to modulate multiple signaling pathways, potentially including those involved in antioxidant, anti-inflammatory, and anticancer effects. Detailed target information is lacking in the available literature. |
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| ln Vitro |
Bioassay-directed fractionation of an ethanolic extract of Selaginella moellendorffii has led to the isolation of a known biflavone, ginkgetin (1). A dose-dependent inhibition was observed with 1 on the growth of OVCAR-3 (human ovarian adenocarcinoma) cells with 50% inhibition occurring at 1.8 micrograms/mL. Nonbioactive fractions yielded four additional known biflavones, amentoflavone 7,4',7",4"'-tetramethyl ether, kayaflavone, podocarpusflavone A, and amentoflavone[1].
In vitro, amentoflavone (parent compound) has been shown to inhibit the PI3K/Akt/mTOR signaling pathway, induce apoptosis in pancreatic cancer cells, inhibit cell migration, and cause cell cycle arrest at the S phase. For the tetramethyl derivative, no specific in vitro activity data have been reported, but it is expected to have enhanced solubility, stability, and potentially altered bioactivity compared to the parent compound. |
| ln Vivo |
No in vivo efficacy data have been reported specifically for Amentoflavone 7,4',7'',4'''-tetramethyl ether in animal models. For the parent compound amentoflavone, in vivo studies have demonstrated anti-cancer activity in xenograft models. The tetramethyl derivative may have improved pharmacokinetic properties due to increased lipophilicity and metabolic stability.
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| Enzyme Assay |
No cell-free assays have been reported for this compound. For the parent compound amentoflavone, cell-free assays include PI3K kinase activity assays (recombinant PI3K enzyme incubated with varying concentrations of amentoflavone, ATP, and PIP2 substrate, with product PIP3 quantified by ELISA). The tetramethyl derivative may be used in similar assays to determine its inhibitory potency, but no published data exist.
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| Cell Assay |
Biological Assays. OVCAR-3 cells were obtained from the American Type Culture Collection (ATCC: HTB-161). HEK, HeLa, and HepG2 cells were kindly provided by the Cell Bank, Veterans General Hospital, Taipei, Taiwan. Cells were grown in RPMI 1640 medium supplemented with glutamine and 10% fetal calf serum. To perform the growth inhibition assays, cells were seeded into 12-well tissue culture plates at a density of 0.2−1 × 105 cells in 1 mL medium per well. Prior to each assay, the seeded cells were preincubated overnight at 37 °C in a humidified incubator containing 5% CO2. Each experiment was carried out in triplicate. At time zero, the spent medium was replaced with 1 mL of fresh medium containing 0.5−10 μg of test compound dissolved in DMSO. Cells were harvested for viability counting subsequent to incubation at timed intervals. The medium was removed, and the wells were rinsed with 1 mL of phosphate-buffered saline. The cells were harvested with trypsin-EDTA, suspended in culture media, and microscopically counted after the trypan blue exclusion staining. Cytotoxicity of the compounds at various concentrations was calculated as the net growth inhibition (%) of the cells relative to that of controls containing an equivalent amount of DMSO only[1].
No cell-based assays have been reported for this tetramethyl derivative. For the parent compound amentoflavone, pancreatic cancer cell lines (BxPC3, Panc-1) are seeded in 96-well plates and treated with amentoflavone (0-100 uM, 24-72 h). Cell viability is measured by MTT or CCK-8 assay. Apoptosis is assessed by Annexin V/PI flow cytometry. Cell cycle is analyzed by propidium iodide staining. PI3K/Akt/mTOR pathway activity is assessed by Western blot for phospho-Akt, phospho-mTOR, and downstream effectors. The tetramethyl derivative remains to be evaluated in similar assays. |
| Animal Protocol |
No animal studies have been conducted with this tetramethyl derivative. For the parent compound amentoflavone, xenograft mouse models bearing pancreatic cancer cells (BxPC3) are used. The compound is administered intraperitoneally at doses of 10-50 mg/kg daily for 2-4 weeks, with tumor volume measured by calipers. Tumor tissues are harvested for Western blot analysis of PI3K/Akt/mTOR pathway and immunohistochemistry for Ki67. The tetramethyl derivative has not been tested in vivo.
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| ADME/Pharmacokinetics |
PK properties have not been reported for this tetramethyl derivative. As a biflavone (MW 594.56, LogP ~4.5), expected PK in rodents after oral administration: low oral bioavailability due to extensive phase II metabolism and poor aqueous solubility. Tmax 1-3 h, plasma half-life 4-8 h. The compound is likely metabolized by glucuronidation and sulfation. The tetramethyl modification may improve metabolic stability compared to the parent compound.
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| Toxicity/Toxicokinetics |
No toxicity data have been reported for this compound. As a natural biflavonoid derivative, it is likely to have low acute toxicity. The parent compound amentoflavone is generally considered safe at moderate doses. However, no formal toxicological studies have been performed. The compound is for research use only and not for human consumption.
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| References | |
| Additional Infomation |
It has been reported that 4H-1-benzopyran-4-one, 5-hydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-7-methoxy-2-(4-methoxyphenyl)-,(+)- exists in Japanese cedar, Selaginella tamariscina, and other organisms for which data are available.
Amentoflavone 7,4',7'',4'''-tetramethyl ether is a research compound, not an approved drug. It is used as an analytical reference standard in natural product chemistry and for structure-activity relationship studies of biflavonoids. The parent compound amentoflavone has been studied for its anticancer, anti-inflammatory, antioxidant, and neuroprotective activities. The tetramethyl derivative may serve as a lead compound for developing more stable and bioavailable biflavonoid-based therapeutics. It is of interest for research on oxidative stress and inflammation. |
| Molecular Formula |
C34H26O10
|
|---|---|
| Molecular Weight |
594.58032
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| Exact Mass |
594.152
|
| CAS # |
3778-25-4
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| PubChem CID |
5490003
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| Appearance |
Off-white to yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
813.5±65.0 °C at 760 mmHg
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| Melting Point |
292-294℃
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| Flash Point |
264.5±27.8 °C
|
| Vapour Pressure |
0.0±3.0 mmHg at 25°C
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| Index of Refraction |
1.657
|
| Source |
Cryptomeria japonica, Selaginella moellendorffii
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| LogP |
5.8
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
44
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| Complexity |
1110
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)OC)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)OC)O)OC
|
| InChi Key |
VXQYICLHHMETFH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C34H26O10/c1-39-19-8-5-17(6-9-19)27-15-24(37)33-25(38)16-29(42-4)31(34(33)44-27)21-11-18(7-10-26(21)41-3)28-14-23(36)32-22(35)12-20(40-2)13-30(32)43-28/h5-16,35,38H,1-4H3
|
| Chemical Name |
5-hydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
|
| Synonyms |
7''-O-Methylsciadopitysin; 3778-25-4; 22783-08-0; W 13; Amentoflavone 7,4',7'',4'''-tetramethyl ether; 4H-1-Benzopyran-4-one, 5-hydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-7-methoxy-2-(4-methoxyphenyl)-, (+)-; 5-hydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-7-methoxy-2-(4-methoxyphenyl)chromen-4-one; 5-hydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl)-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-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) |
DMSO : ~1 mg/mL (~1.68 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 | 1.6819 mL | 8.4093 mL | 16.8186 mL | |
| 5 mM | 0.3364 mL | 1.6819 mL | 3.3637 mL | |
| 10 mM | 0.1682 mL | 0.8409 mL | 1.6819 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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