Physicochemical Properties
| Molecular Formula | C25H26O6 |
| Molecular Weight | 422.47 |
| Exact Mass | 422.172 |
| CAS # | 129280-34-8 |
| PubChem CID | 21591148 |
| Appearance | White to off-white solid powder |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 668.1±55.0 °C at 760 mmHg |
| Melting Point | 191 - 193 °C |
| Flash Point | 229.0±25.0 °C |
| Vapour Pressure | 0.0±2.1 mmHg at 25°C |
| Index of Refraction | 1.650 |
| LogP | 6.94 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 31 |
| Complexity | 745 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | QNLGNISMYMFVHP-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C25H26O6/c1-13(2)5-7-15-9-16(10-20(27)23(15)28)18-12-31-21-11-19(26)17(8-6-14(3)4)24(29)22(21)25(18)30/h5-6,9-12,26-29H,7-8H2,1-4H3 |
| Chemical Name | 3-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one |
| 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) |
Biological Activity
| Targets | Apoptosis, Autophagy[2] |
| ln Vitro | Isoangustone A (10 and 20 μM; 48 and 72 h) promotes cell cycle arrest in the G1 phase and decreases the proliferation of SK-MEL-28 cells [1]. Via the Akt/GSK3β and MKK4/MKK7/JNKs signaling pathways, isoangustone A (10 and 20 μM; 48 h) promotes the reduction in the amount of G1 phase-related proteins [1]. Through ATP competition, isoangustone A directly binds to and inhibits the kinase activities of PI3-K, MKK4, and MKK7 [1]. By triggering AMPK signaling, isoangustone A (20 μM; 0.5–4 h) stimulates autophagy in colorectal cancer cells [2]. [2] Isoangustone A (1–20 μM; 0-100 min) decreases the respiration of mitochondria. In SW480 cells, isoangustone A (15 μM; 6 h) causes apoptosis [2]. In human renal mesangial cells, isoangustone A (1–20 μM; 3 days) reduces fibrosis and inflammation [3]. |
| ln Vivo | The tumor development, volume, and weight of mice SK-MEL-28 xenografts are greatly reduced by isoangustone A (2 or 10 mg/kg; ip; daily for 35 days) [1]. |
| Cell Assay |
Cell Proliferation Assay[1] Cell Types: SK-MEL-28 Tested Concentrations: 10 and 20 μM Incubation Duration: 48 and 72 h Experimental Results: Inhibited proliferation in a dose- and time-dependent manner. Cell Cycle Analysis[1] Cell Types: SK-MEL-28 Tested Concentrations: 10 and 20 μM Incubation Duration: 48 h Experimental Results: Caused cell cycle arrest at G1 phase. Western Blot Analysis[1] Cell Types: SK-MEL-28 Tested Concentrations: 10 and 20 μM Incubation Duration: 48 h Experimental Results: Inhibited the expression of cyclin D1 and cyclin E. Suppressed phosphorylation of Rb in a dose-dependent manner. Inhibited the phosphorylation of Akt (Ser473, Thr308) and GSK3β (Ser9). Suppressed the phosphorylation of JNK1/2, but had no effect on ERK1/2 or p38. Cell Autophagy Assay[2] Cell Types: SW480 cells Tested Concentrations: 20 μM Incubation Duration: 0.5, 2 and 4 h Experimental Results: Deformed mitochondria, nondegradable cellular debris were all observable together with autophagic vacuoles in cells after 4 h. Apoptosis Analysis[2] Cell Types: SW480 cells Tested Concentrations: 15 μM Incubation Duration: |
| Animal Protocol |
Animal/Disease Models: Male Balb/c nu/nu (nude) mice, SK-MEL-28 xenograft model[1] Doses: 2 or 10 mg/kg Route of Administration: intraperitoneal (ip)injection, daily for 35 days Experimental Results: Dramatically suppressed tumor weight compared to the control group. Markedly inhibited the expression of proliferating cell nuclear antigen (PCNA). diminished phosphorylation levels of Akt. |
| References |
[1]. Isoangustone A, a novel licorice compound, inhibits cell proliferation by targeting PI3K, MKK4, and MKK7 in human melanoma. Cancer Prev Res (Phila). 2013 Dec;6(12):1293-303. [2]. Isoangustone A induces autophagic cell death in colorectal cancer cells by activating AMPK signaling. Fitoterapia. 2021 Jul;152:104935. [3]. Isoangustone A suppresses mesangial fibrosis and inflammation in human renal mesangial cells. Exp Biol Med (Maywood). 2011 Apr 1;236(4):435-44. |
| Additional Infomation |
Isoangustone A is a member of isoflavanones. Isoangustone A has been reported in Glycyrrhiza uralensis, Glycyrrhiza glabra, and Glycyrrhiza inflata with data available. |
Solubility Data
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3670 mL | 11.8352 mL | 23.6703 mL | |
| 5 mM | 0.4734 mL | 2.3670 mL | 4.7341 mL | |
| 10 mM | 0.2367 mL | 1.1835 mL | 2.3670 mL |