| Size | Price | |
|---|---|---|
| 1mg | ||
| Other Sizes |
| Targets |
Natural flavonoid
|
|---|---|
| ln Vitro |
7-Prenyloxyaromadendrin (compound 5) exhibits antiproliferative activity in A549, HBL-100, HeLa, SW1573, and T-47D cells, with GI50 values ranging from 16 to 20 μM[2]. 7-Prenyloxyaromadendrin (compound 5) is inactive against B. subtilis and B. cereus; at 50 μg/disk, there is no zone of inhibition[1].
Objective: To isolate secondary metabolites from the aerial parts of Pterocaulon alopecuroides, elucidate their structures and evaluate their antiproliferative activities on selected human cancer cell lines. Materials and Methods: The ethanolic extract of P. alopecuroides afforded five compounds, which were characterized using spectroscopic techniques and by comparison with data from the literature. Antiproliferative activities of all isolates were evaluated. Results: The compounds 7-(2,3-dihydroxy-3-methylbutoxy)-6-methoxycoumarin (1), 5,6-methylenedioxy- 7-(2,3-dihydroxy-3-methylbutoxy) coumarin (2), Dihydrokaempferol (3), 5,7,4´-trihydroxy- 6-(α,α-dimethylallyl)dihydroflavonol (4) and 5,4´-dihydroxy-7-(γ,γ-dimethylallyloxy)dihydroflavonol (5) were isolated. The antiproliferative activity of all compounds was evaluated in a panel of six human solid tumor cell lines showing GI50 values for the most active compounds in the low micromolar range. Conclusion: Compound 2 is reported for first time from P. alopecuroides. Isolated coumarins show no antiproliferative activity, whilst among flavonoids compound 5 showed the best antiproliferative activity [2]. |
| References | |
| Additional Infomation |
7-Prenyloxyaromadendrin has been reported in Pterocaulon virgatum and Moquiniastrum paniculatum with data available.
Three flavonoids, (2 R,3 R)-5,4'-dihydroxy-3'- O-methyl-7-(gamma,gamma-dimethylallyloxy)dihydroflavonol 1, (2 R,3 R)-5,7,4'-trihydroxy-3'- O-methyl-6-(alpha,alpha-dimethylallyl)dihydroflavonol 2, and (2 R,3 R)-5,7,4'-trihydroxy-6-(alpha,alpha-dimethylallyl)dihydroflavonol 3, together with three known flavonoids ( 4 - 6), were isolated from the aerial parts of PTEROCAULON ALOPECUROIDES. The structures of the compounds were determined by mass and by 1 D and 2 D NMR spectroscopy. Screening of the antibacterial activity of all six compounds was conducted by a disc diffusion test against BACILLUS CEREUS, BACILLUS SUBTILIS, SALMONELLA TYPHIMURIUM and PROTEUS MIRABILIS. The minimum inhibitory concentration (MIC) of the active compounds ( 2, 3, 4, 6) was determined by a microdilution assay. These compounds were active only against both Gram+ bacteria with MIC values < or = 200 microg/mL. [1] |
| Molecular Formula |
C20H20O6
|
|---|---|
| Molecular Weight |
356.37
|
| Exact Mass |
356.125
|
| CAS # |
78876-50-3
|
| PubChem CID |
23900109
|
| Appearance |
White to light yellow solid
|
| Density |
1.343±0.06 g/cm3
|
| Boiling Point |
624.3±55.0 °C at 760 mmHg
|
| LogP |
3.7
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
26
|
| Complexity |
520
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
O=C1[C@H](O)[C@@H](C2C=CC(O)=CC=2)OC2C=C(C=C(C1=2)O)OC/C=C(\C)/C
|
| InChi Key |
CITFYDYEWQIEPX-VQTJNVASSA-N
|
| InChi Code |
InChI=1S/C20H20O6/c1-11(2)7-8-25-14-9-15(22)17-16(10-14)26-20(19(24)18(17)23)12-3-5-13(21)6-4-12/h3-7,9-10,19-22,24H,8H2,1-2H3/t19-,20+/m0/s1
|
| Chemical Name |
(2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-(3-methylbut-2-enoxy)-2,3-dihydrochromen-4-one
|
| Synonyms |
7-Prenyloxyaromadendrin; 78876-50-3; (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-(3-methylbut-2-enoxy)-2,3-dihydrochromen-4-one; MEGxp0_001833; 7-Prenyloxyaromadendrin
|
| 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 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)
|
| 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
|
|---|---|
| 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 | 2.8061 mL | 14.0304 mL | 28.0607 mL | |
| 5 mM | 0.5612 mL | 2.8061 mL | 5.6121 mL | |
| 10 mM | 0.2806 mL | 1.4030 mL | 2.8061 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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