Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H22O18 |
| Molecular Weight | 634.4528 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]1[C@@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C4=C(C=C(O)C(O)=C4O)C(=O)O[C@H]1[C@H](O)[C@@H](OC(=O)C5=CC(O)=C(O)C(O)=C5)O2
InChI
InChIKey=TUSDEZXZIZRFGC-VPIGZIKCSA-N
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/t13-,19-,22-,23+,27+/m0/s1
| Molecular Formula | C27H22O18 |
| Molecular Weight | 634.4528 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1324981 | https://www.ncbi.nlm.nih.gov/pubmed/24679441 | https://www.ncbi.nlm.nih.gov/pubmed/28962079 | https://www.ncbi.nlm.nih.gov/pubmed/28791374
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1324981 | https://www.ncbi.nlm.nih.gov/pubmed/24679441 | https://www.ncbi.nlm.nih.gov/pubmed/28962079 | https://www.ncbi.nlm.nih.gov/pubmed/28791374
Corilagin is a polyphenol, ellagitannin and hydrolyzable tannin that can be isolated from a variety of plants. This compound displays the ability to inhibit squalene epoxidase, a key enzyme in cholesterol synthesis, and NFκB pathway activation and also prevent the release of TNF-α at an IC50 of 76 μM. Additional studies show that Corilagin significantly inhibits type 1 plasminogen activator inhibitor (PAI-1) in rat plasma. Also has been reported to result in an increase in plasma tissue-type plasminogen activator (tPA) which results in the thrombolytic effect of Corilagin. In other studies, Corilagin showed some other pharmaceutical activities, such as antiviral effects in vitro, antinociceptive activity, anti-hyperalgesic activity, and action of anti-tumor in hepatocellular carcinoma and ovarian cancer.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibition of human immunodeficiency viral replication by tannins and related compounds. | 1992 May |
|
| Inhibitory activity of flavonoids and tannins against HIV-1 protease. | 2000 Sep |
|
| Plant tannins inhibit the induction of aberrant crypt foci and colonic tumors by 1,2-dimethylhydrazine in mice. | 2001 |
|
| Gallotannin biosynthesis: beta-glucogallin: hexagalloyl 3-O-galloyltransferase from Rhus typhina leaves. | 2001 Nov |
|
| New TNF-alpha releasing inhibitors, geraniin and corilagin, in leaves of Acer nikoense, Megusurino-ki. | 2001 Oct |
|
| Frontal immunoaffinity chromatography with mass spectrometric detection: a method for finding active compounds from traditional Chinese herbs. | 2003 Aug 15 |
|
| Antihypertensive effects of tannins isolated from traditional Chinese herbs as non-specific inhibitors of angiontensin converting enzyme. | 2003 Aug 8 |
|
| Mechanisms of action of corilagin and tellimagrandin I that remarkably potentiate the activity of beta-lactams against methicillin-resistant Staphylococcus aureus. | 2004 |
|
| Poly(ADP-ribose) glycohydrolase as a target for neuroprotective intervention: assessment of currently available pharmacological tools. | 2004 Aug 16 |
|
| Analysis of polyphenolic antioxidants in star fruit using liquid chromatography and mass spectrometry. | 2004 Jan 2 |
|
| Determination of hydrolyzable tannins in the fruit of Terminalia chebula Retz. by high-performance liquid chromatography and capillary electrophoresis. | 2004 Jun |
|
| Cytoprotective effect of gallotannin in oxidatively stressed HaCaT keratinocytes: the role of poly(ADP-ribose) metabolism. | 2004 Mar |
|
| Dual role for poly(ADP-ribose)polymerase-1 and -2 and poly(ADP-ribose)glycohydrolase as DNA-repair and pro-apoptotic factors in rat germinal cells exposed to nitric oxide donors. | 2004 May 28 |
|
| Tannins and related compounds induce nitric oxide synthase and cytokines gene expressions in Leishmania major-infected macrophage-like RAW 264.7 cells. | 2005 Dec 1 |
|
| Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia. | 2005 Jan |
|
| Chemical identification of the sources of commercial Fructus Chebulae. | 2005 Jul-Aug |
|
| Subcellular compartmentation and differential catalytic properties of the three human nicotinamide mononucleotide adenylyltransferase isoforms. | 2005 Oct 28 |
|
| Enzymology of gallotannin and ellagitannin biosynthesis. | 2005 Sep |
|
| Nitric oxide radical scavenging active components from Phyllanthus emblica L. | 2006 Mar |
|
| Aleppo tannin: structural analysis and salivary amylase inhibition. | 2007 Apr 9 |
|
| Evaluation of free radical scavenging and antityrosinase activities of standardized longan fruit extract. | 2007 Feb |
|
| Differential apoptosis by gallotannin in human colon cancer cells with distinct p53 status. | 2007 Mar |
|
| Mono-galloyl glucose derivatives are potent poly(ADP-ribose) glycohydrolase (PARG) inhibitors and partially reduce PARP-1-dependent cell death. | 2008 Dec |
|
| Penta-O-galloyl-beta-D-glucose induces S- and G(1)-cell cycle arrests in prostate cancer cells targeting DNA replication and cyclin D1. | 2009 May |
|
| Lysis of Microcystis aeruginosa with extracts from Chinese medicinal herbs. | 2009 Sep 23 |
|
| Separation and purification of hydrolyzable tannin from Geranium wilfordii Maxim by reversed-phase and normal-phase high-speed counter-current chromatography. | 2010 Aug |
|
| Neuroprotective effects of naturally occurring polyphenols on quinolinic acid-induced excitotoxicity in human neurons. | 2010 Jan |
|
| Effect of Corilagin on anti-inflammation in HSV-1 encephalitis and HSV-1 infected microglias. | 2010 Jun 10 |
|
| 1,2,3,6-tetra-O-galloyl-beta-D-allopyranose gallotannin isolated, from Euphorbia jolkini, attenuates LPS-induced nitric oxide production in macrophages. | 2010 Sep |
|
| Antimicrobial, antioxidant and cytotoxic activities and phytochemical screening of some yemeni medicinal plants. | 2010 Sep |
|
| Intestinal alpha-glucosidase inhibitory activity and toxicological evaluation of Nymphaea stellata flowers extract. | 2010 Sep 15 |
Sample Use Guides
Mice were treated with 20, 40, 80 mg/kg/day of Corilagin for consecutive four weeks
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:44:44 GMT 2023
by
admin
on
Fri Dec 15 19:44:44 GMT 2023
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| Record UNII |
62LOS9TW6D
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| Record Status |
Validated (UNII)
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| Record Version |
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CORILAGIN
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