Corilagin, a ellagitannin/gallotannin, is a natural product extracted from Caesalpinia coriaria (Jacq.) Willd. It can also be found in Alchornea glandulosa and in the leaves of Punica granatum. It is a weak carbonic anhydrase inhibitor. Corilagin inhibits activity of reverse transcriptase of RNA tumor viruses. Corilagin inhibits the growth of Staphylococcus aureus with a MIC of 25 μg/mL. Corilagin shows good anti-tumor activity on hepatocellular carcinoma and ovarian cancer. Corilagin shows a low level of toxicity toward normal cells and tissues.
Physicochemical Properties
| Molecular Formula | C27H22O18 |
| Molecular Weight | 634.4528 |
| Exact Mass | 634.08 |
| Elemental Analysis | C, 51.11; H, 3.50; O, 45.39 |
| CAS # | 23094-69-1 |
| PubChem CID | 73568 |
| Appearance | White to off-white solid powder |
| Density | 2.1±0.1 g/cm3 |
| Boiling Point | 1280.8±65.0 °C at 760 mmHg |
| Melting Point | >200ºC dec |
| Flash Point | 418.8±27.8 °C |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.881 |
| LogP | 2.34 |
| Hydrogen Bond Donor Count | 11 |
| Hydrogen Bond Acceptor Count | 18 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 45 |
| Complexity | 1090 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | C1[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)O)OC(=O)C4=CC(=C(C(=C4C5=C(C(=C(C=C5C(=O)O1)O)O)O)O)O)O)O |
| InChi Key | TUSDEZXZIZRFGC-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(39)45-27-22(38)23-19(35)13(43-27)5-42-25(40)7-3-11(30)17(33)20(36)14(7)15-8(26(41)44-23)4-12(31)18(34)21(15)37/h1-4,13,19,22-23,27-38H,5H2 |
| Chemical Name | 14,15,16,24,25,26,53,55-octahydroxy-3,8-dioxo-53,54,55,56-tetrahydro-52H-4,7-dioxa-5(4,2)-pyrana-1,2(1,2)-dibenzenacyclooctaphane-56-yl 3,4,5-trihydroxybenzoate |
| 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
| ln Vitro |
SGC7901 and BGC823 cell growth is inhibited by corilagin (0-50 μM, 24 h), causing the cells to round[2]. Corilagin (0-30 μM, 24 h) induces apoptosis in BGC823 and SGC7901 cells[2]. In SGC7901 and BGC823 cells, corilagin (0-30 μM, 24 h) increased cleaved PARP and decreased the protein levels of procaspase-8, -9, and -3[2]. In SGC7901 and BGC823 cells, corilagin (0-30 μM, 24 h) induces autophagy (enhancement of acidic vesicles, increased level of LC3II)[2]. In SGC7901 and BGC823 cells, corilagin (0-30 μM, 24 h) induces ROS generation[2]. Hey and SKOv3ip cells undergo apoptosis and G2 cell cycle arrest when exposed to corilagin (40 μM) for 24 or 48 hours[3]. Hey, SKOv3ip, and HO8910PM cell secretion of TGF-β1 is inhibited by corilagin (0-80 μM, 1-3 days)[3]. |
| ln Vivo |
In Hep3B hepatocellular carcinoma, corilagin (15 mg/kg, i.p., for 7 days) exhibits anti-tumor activity[4]. Mice exposed to APAP are protected against hepatotoxicity by corilagin (0–20 mg/kg, i.p.)[5]. |
| Cell Assay |
Cell Line: SGC7901 and BGC823 cell Concentration: 0, 10, 20, 30, 40 and 50 µM Incubation Time: 24 h Result: exhibited a concentration-dependent inhibition of cell proliferation. |
| Animal Protocol | Animal Model: Hep3B mouse model for hepatocellular carcinoma[4]. Dosage: 15 mg/kg Administration: Intraperitoneal injection (i.p.) Result: Inhibited tumor growth without toxic effects. |
| References |
[1]. Corilagin, a promising medicinal herbal agent. Biomed Pharmacother. 2018 Mar;99:43-50. [2]. Corilagin induces apoptosis, autophagy and ROS generation in gastric cancer cells in vitro. Int J Mol Med. 2019 Feb;43(2):967-979. [3]. A potential anti-tumor herbal medicine, Corilagin, inhibits ovarian cancer cell growth through blocking the TGF-β signaling pathways. BMC Complement Altern Med. 2013 Feb 15;13:33. [4]. In vivo anti-tumour activity of corilagin on Hep3B hepatocellular carcinoma. Phytomedicine. 2010 Dec 15;18(1):11-5. [5]. Corilagin reduces acetaminophen-induced hepatotoxicity through MAPK and NF-κB signaling pathway in a mouse model. Am J Transl Res. 2020 Sep 15;12(9):5597-5607. |
| Additional Infomation |
Corilagin is an ellagitannin with a hexahydroxydiphenoyl group bridging over the 3-O and 6-O of the glucose core. It has a role as an antihypertensive agent, an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, a non-steroidal anti-inflammatory drug and an antioxidant. It is an ellagitannin and a gallate ester. Corilagin has been reported in Euphorbia prostrata, Phyllanthus tenellus, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~157.62 mM) H2O : ~5 mg/mL (~7.88 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.28 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 (3.28 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 (3.28 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. Solubility in Formulation 4: 5.88 mg/mL (9.27 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5762 mL | 7.8808 mL | 15.7617 mL | |
| 5 mM | 0.3152 mL | 1.5762 mL | 3.1523 mL | |
| 10 mM | 0.1576 mL | 0.7881 mL | 1.5762 mL |