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Purity: =99.94%
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.
| Targets |
- TGF-β signaling pathways (in ovarian cancer cells, blocking TGF - β secretion and inhibiting the activation of canonical Smad and non - canonical Erk/Akt pathways) [2]
- Cyclooxygenase - 2 (inhibiting its mRNA and protein expression, but no specific IC50, Ki, etc. values given) [1] - MAPK and NF - κB signaling pathway (in acetaminophen - induced hepatotoxicity mouse model, mechanism - related target) [5] |
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| 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]. - Inhibited the growth of ovarian cancer cell lines SKOV3.ip and HEY with IC50 values of less than 30 μM, and had low toxicity to normal ovarian surface epithelium cells with IC50 values of approximately 160 μM. Induced cell cycle arrest at G2/M stage and enhanced apoptosis in ovarian cancer cells. Down - regulated cyclin B1, Myt1, phospho - Cdc2 and phospho - Wee1. Inhibited TGF - β secretion into the culture supernatant of ovarian cancer cell lines HO8910PM, SKOV3.ip and HEY in a dose - dependent manner [2] - Induced concentration - dependent inhibition of SGC7901 and BGC823 gastric cancer cell growth, with less toxicity to normal GES - 1 cells. Induced apoptosis of gastric cancer cells mainly by activating caspase - 8, - 9, - 3 and poly ADP - ribose polymerase proteins. Triggered autophagy in gastric cancer cells, and the inhibition of autophagy improved the cell growth suppression effect. Significantly increased intracellular reactive oxygen species production [5] |
| 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]. - Significantly inhibited the growth of Hep3B hepatocellular carcinoma xenografts in athymic nude mice. Administered intraperitoneally at a dose of 15 mg/kg of body weight for 7 consecutive days, and had no obvious adverse effect on liver function (no increase in alanine aminotransferase and aspartate aminotransferase levels) [1] - Significantly inhibited the growth of SKOV3.ip xenografts in mice when delivered intraperitoneally [2] - Reduced acetaminophen - induced hepatotoxicity in a mouse model. Mice were not described in detail, but it can be inferred that it is a common mouse model. The mechanism is related to the MAPK and NF - κB signaling pathways [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. - Treated ovarian cancer cell lines SKOV3.ip, HEY and HO8910PM with Corilagin, and used sulforhodamine B (SRB) cell proliferation assay, flow cytometry, and reverse phase protein array (RPPA) for analysis [2] - Used 3 - (4, 5 - dimethylthiazol - 2 - yl) - 2, 5 - diphenyltetrazolium bromide (MTT) assay, EdU proliferation assay, lactate dehydrogenase (LDH) release assay, ROS generation assay, Hoechst 33342 staining detection, flow cytometric analysis and western blot analysis to evaluate the growth inhibition and apoptosis - inducing effects of Corilagin on gastric cancer cells, and also investigated the autophagy - inducing ability and the occurrence of necroptosis [5] |
| 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.
- For Hep3B hepatocellular carcinoma xenograft model, athymic nude mice were used, and Corilagin was intraperitoneally administered at a dose of 15 mg/kg of body weight for 7 consecutive days [1] - For SKOV3.ip xenograft model, Corilagin was intraperitoneally delivered to mice, but the specific dose and administration frequency were not described in detail [2] - For acetaminophen - induced hepatotoxicity mouse model, the relevant mouse model was not described in detail, and the administration method and dose were not mentioned. For Con A - induced hepatitis mouse model, C57BL/6 mice were randomly divided into groups, and Corilagin was intraperitoneally administered at a dose of 12.5 or 25 mg/kg body weight twice at 12 - h intervals, and 1 h later, the mice were challenged with Con A (20 mg/kg body weight), and serum and liver samples were collected after 12 h [5] |
| References | |
| Additional Infomation |
- Corilagin is a gallotannin, a major active component of many ethnopharmacological plants such as Phyllanthus niruri L., P. emblica L. and P. urinaria L. It was first isolated in 1951. It has anti - tumor, antioxidant, hepatoprotective, anti - inflammatory and other activities. It shows good anti - tumor activity on hepatocellular carcinoma and ovarian cancer, and has a low - level of toxicity to normal cells and tissues [4]
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. |
| Molecular Formula |
C27H22O18
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|---|---|
| Molecular Weight |
634.4528
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| Exact Mass |
634.08
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| Elemental Analysis |
C, 51.11; H, 3.50; O, 45.39
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| CAS # |
23094-69-1
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| PubChem CID |
73568
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| Appearance |
White to off-white solid powder
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| Density |
2.1±0.1 g/cm3
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| Boiling Point |
1280.8±65.0 °C at 760 mmHg
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| Melting Point |
>200ºC dec
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| Flash Point |
418.8±27.8 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
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| Index of Refraction |
1.881
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| LogP |
2.34
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| Hydrogen Bond Donor Count |
11
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| Hydrogen Bond Acceptor Count |
18
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
45
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| Complexity |
1090
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| Defined Atom Stereocenter Count |
5
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| 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
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| InChi Key |
TUSDEZXZIZRFGC-UHFFFAOYSA-N
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| 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
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| 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
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| Synonyms |
Corilagin; 23094-69-1; CHEBI:3884; [(1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.04,9.010,15]tricosa-4,6,8,10,12,14-hexaen-21-yl] 3,4,5-trihydroxybenzoate; DTXSID90865084; ((1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo(17.3.1.04,9.010,15)tricosa-4,6,8,10,12,14-hexaen-21-yl) 3,4,5-trihydroxybenzoate; (1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo(17.3.1.0^(4,9).0^(10,15))tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate; (1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate;
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~157.62 mM)
H2O : ~5 mg/mL (~7.88 mM) |
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| 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. View More
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. 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). |
| 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 |
*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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