Britannin is a naturally occurring sesquiterpene lactone found in Inula caspica and Asteraceae family of plants with antiproliferative activity on the MCF-7 and MDA-MB-468 human breast cancer cells. Britannin inhibits growth of MCF-7 and MDA-MB-468 breast cancer cells through the activation of the mitochondrial apoptotic pathway and may potentially serve as an agent for breast cancer therapy.
Physicochemical Properties
| Molecular Formula | C19H26O7 |
| Molecular Weight | 366.40554 |
| Exact Mass | 366.168 |
| CAS # | 33627-28-0 |
| PubChem CID | 14466541 |
| Appearance | White to off-white solid powder |
| Density | 1.25±0.1 g/cm3 |
| Melting Point | 189-191 ºC |
| LogP | 1.374 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 26 |
| Complexity | 656 |
| Defined Atom Stereocenter Count | 8 |
| SMILES | C[C@@H]1C[C@H]2[C@H]([C@@H]([C@]3([C@H]1[C@H](C[C@@H]3O)OC(=O)C)C)OC(=O)C)C(=C)C(=O)O2 |
| InChi Key | JXEGMONJOSAULB-IZZBGLMFSA-N |
| InChi Code | InChI=1S/C19H26O7/c1-8-6-12-15(9(2)18(23)26-12)17(25-11(4)21)19(5)14(22)7-13(16(8)19)24-10(3)20/h8,12-17,22H,2,6-7H2,1,3-5H3/t8-,12+,13+,14+,15-,16-,17+,19-/m1/s1 |
| Chemical Name | [(3aS,5R,5aS,6S,8S,8aS,9S,9aR)-9-acetyloxy-8-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] acetate |
| 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) |
Biological Activity
| References |
[1].The suppressive effects of Britannin (Bri) on human liver cancer through inducing apoptosis and autophagy via AMPK activation regulated by ROS. Biochem Biophys Res Commun. 2018 Mar 11;497(3):916-923. [2].Britanin suppresses LPS-induced nitric oxide, PGE2 and cytokine production via NF-\u03baB and MAPK inactivation in RAW 264.7 cells. Int Immunopharmacol. 2013 Feb;15(2):296-302. [3].Anti-proliferative activity and apoptotic potential of britannin, a sesquiterpene lactone from Inula aucheriana. Nat Prod Commun. 2012 Aug;7(8):979-80 |
Solubility Data
| Solubility (In Vitro) | DMSO : ~250 mg/mL (~682.30 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.68 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.68 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.08 mg/mL (5.68 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7292 mL | 13.6459 mL | 27.2918 mL | |
| 5 mM | 0.5458 mL | 2.7292 mL | 5.4584 mL | |
| 10 mM | 0.2729 mL | 1.3646 mL | 2.7292 mL |