Physicochemical Properties
| Molecular Formula | C21H22O11 |
| Molecular Weight | 450.39278 |
| Exact Mass | 450.116 |
| CAS # | 535-96-6 |
| PubChem CID | 6441269 |
| Appearance | Yellow to orange solid powder |
| Density | 1.7±0.1 g/cm3 |
| Boiling Point | 835.4±65.0 °C at 760 mmHg |
| Melting Point | 197-202ºC |
| Flash Point | 293.5±27.8 °C |
| Vapour Pressure | 0.0±3.2 mmHg at 25°C |
| Index of Refraction | 1.751 |
| LogP | -0.18 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 32 |
| Complexity | 658 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | C1=CC(=C(C=C1/C=C/C(=O)C2=C(C(=C(C=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O)O |
| InChi Key | XGEYXJDOVMEJNG-HTFDPZBKSA-N |
| InChi Code | InChI=1S/C21H22O11/c22-8-15-18(28)19(29)20(30)21(32-15)31-14-6-3-10(16(26)17(14)27)11(23)4-1-9-2-5-12(24)13(25)7-9/h1-7,15,18-22,24-30H,8H2/b4-1+/t15-,18-,19+,20-,21-/m1/s1 |
| Chemical Name | (E)-3-(3,4-dihydroxyphenyl)-1-[2,3-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-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 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
| ln Vitro | With IC50 values of 100 and >200 µM, respectively, marein (0-1000 µM; 24 h) suppresses TNFα-induced NF-κB activation as well as HDAC activity [1]. In HepG2 cells, marein (1.25–40 μM; 24 hours) increases the absorption of glucose [2]. Marein (5–10 μM; 24 hours) elevates the amount of liver glycogen, decreases the expression of G6Pase and PEPCK in HepG2 cells, and facilitates the transfer of GLUT1 from intercellular vesicles to the plasma membrane [2]. Marein (5–10 μM; 24 hours) increases the absorption of 2-NBDG and is inhibited by STO-609 and Compound C, an AMPK inhibitor [2]. In PC12 cells, marein (0–40 μM; 24 hours) alters the cytotoxicity of MG [3]. |
| Cell Assay |
Western Blot Analysis [2] Cell Types: HepG2 cell line Tested Concentrations: 5 and 10 μM Incubation Duration: 24 hrs (hours) Experimental Results: The translocation of GLUT1 to the plasma membrane was increased and the phosphorylation levels of AS160 and GSK-3β were diminished in HepG2 cells. Western Blot Analysis[2] Cell Types: HepG2 Cell Line Tested Concentrations: 10 μM Incubation Duration: 0-10 hrs (hours) Experimental Results: Time- and dose-dependent induction of AMPK and Akt phosphorylation in HepG2 cells. Cell viability assay [3] Cell Types: PC12 Cell Line Tested Concentrations: 0-40 μM Incubation Duration: 24 hrs (hours) Experimental Results: Prevents MG-induced loss of PC12 cell viability. Apoptosis analysis[3] Cell Types: PC12 Cell Line Tested Concentrations: 5-10 μM Incubation Duration: 30 minutes Experimental Results: Protection of PC12 cells from MG-induced apoptosis. Western Blot Analysis[3] Cell Types: PC12 Cell Line Tested Concentrations: 5-10 μM Incubation Duration: 30 minutes Experimental Results: Increased Phospho-AMPKα (Thr172) in PC12 cells. |
| References |
[1]. Natural chalcones as dual inhibitors of HDACs and NF-κB. Oncol Rep. 2012 Sep;28(3):797-805. [2]. Protective effects of marein on high glucose-induced glucose metabolic disorder in HepG2 cells. Phytomedicine. 2016 Aug 15;23(9):891-900. [3]. Marein protects against methylglyoxal-induced apoptosis by activating the AMPK pathway in PC12 cells. Free Radic Res. 2016;50(11):1173-1187. |
| Additional Infomation |
Marein is a member of flavonoids and a glycoside. Marein has been reported in Abies pindrow, Viguiera dentata, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~25 mg/mL (~55.51 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.55 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 25.0 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: ≥ 2.5 mg/mL (5.55 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 3: 2.5 mg/mL (5.55 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 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 | 2.2203 mL | 11.1015 mL | 22.2030 mL | |
| 5 mM | 0.4441 mL | 2.2203 mL | 4.4406 mL | |
| 10 mM | 0.2220 mL | 1.1101 mL | 2.2203 mL |