Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H8O5 |
| Molecular Weight | 220.1782 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(O)C(O)=C2C(=C1)C=CC=C(O)C2=O
InChI
InChIKey=WDGFFVCWBZVLCE-UHFFFAOYSA-N
InChI=1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14)
| Molecular Formula | C11H8O5 |
| Molecular Weight | 220.1782 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26055176 | https://www.ncbi.nlm.nih.gov/pubmed/22449709 |
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26055176 | https://www.ncbi.nlm.nih.gov/pubmed/22449709 |
Purpurogallin (2,3,4,5 tetrahydroxybenzo[7]annulen 6 one) is a benzotropolone containing the natural product, which occurs in the nut gall of Quercus spp. Purpurogallin is synthesized by the chemical oxidation of pyrogallol and has been shown to have biological properties, such as hydroxyl radical scavenging properties and to protect erythrocytes against lysis induced by peroxyl radicals. Purpurogallin can inhibit 2-hydroxy and 4-hydroxyestradiol methylation by catechol-O-methyltransferase, human immunodeficiency virus 1, integrase and prolyl endopeptidases. In addition, purpurogallin has also been known to have anticancer activities through the inhibition of the DNA synthesis of tumor cells (20), tyrosine-specific protein kinases and the interaction between Bcl xL and BH3 peptides. A number of studies have reported the antioxidant and anti-inflammatory effects of purpurogallin (15,23 27); however, the actual molecular mechanisms involving signal transduction cascades underlying the purpurogallin induced anti-inflammatory effects have not yet been elucidated.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Natural products in regression and slowing of progression of atherosclerosis. | 2010-12 |
|
| Computational analysis of phosphopeptide binding to the polo-box domain of the mitotic kinase PLK1 using molecular dynamics simulation. | 2010-08-12 |
|
| Explaining the atypical reaction profiles of heme enzymes with a novel mechanistic hypothesis and kinetic treatment. | 2010-05-17 |
|
| Hybrid inorganic/organic alumina adsorbents-functionalized-purpurogallin for removal and preconcentration of Cr(III), Fe(III), Cu(II), Cd(II) and Pb(II) from underground water. | 2010-04-15 |
|
| Parallel metatranscriptome analyses of host and symbiont gene expression in the gut of the termite Reticulitermes flavipes. | 2009-10-15 |
|
| Phytic Acid Exposure Alters AflatoxinB1-induced Reproductive and Oxidative Toxicity in Albino Rats (Rattus norvegicus). | 2009-09 |
|
| A cellular model to monitor proteasome dysfunction by alpha-synuclein. | 2009-08-25 |
|
| Deficiency in chromosome congression by the inhibition of Plk1 polo box domain-dependent recognition. | 2009-01-23 |
|
| Biocatalysis in water-in-ionic liquid microemulsions: a case study with horseradish peroxidase. | 2009-01-20 |
|
| Cytotoxicity of chloroquine in isolated rat hepatocytes. | 2007-02-01 |
|
| Peroxidase activity can dictate the in vitro lignin dehydrogenative polymer structure. | 2007-02 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Potent inhibitory effects of black tea theaflavins on off-odor formation from citral. | 2006-04-19 |
|
| Benzotropolone inhibitors of estradiol methylation: kinetics and in silico modeling studies. | 2005-04-01 |
|
| Protection by tropolones against H2O2-induced DNA damage and apoptosis in cultured Jurkat cells. | 2005-02 |
|
| Metabolism of pyrogallol to purpurogallin by human erythrocytic hemoglobin. | 2004-08 |
|
| [Separation and identification of two benzotropolones from teapigment]. | 2004-06 |
|
| Discovery, characterization, and structure-activity relationships studies of proapoptotic polyphenols targeting B-cell lymphocyte/leukemia-2 proteins. | 2003-09-25 |
|
| Coordination of aluminium with purpurogallin and theaflavin digallate. | 2003-09-01 |
|
| Flow-injection chemiluminescent determination of vanadium(IV) and total vanadium by means of catalysis on the periodate oxidation of purpurogallin. | 2002-12-06 |
|
| Design, synthesis, and biological evaluation of a series of simple and novel potential antimalarial compounds. | 2001-07-23 |
|
| Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay. | 2001-02 |
|
| Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations. | 1995-04 |
Sample Use Guides
BV2 murine microglial cells were used for activity evaluation. Cell viability was measured based on the formation of blue formazan metabolized from colorless MTT (Sigma Aldrich) by mitochondrial dehydrogenases, which are active only in live cells. In brief, BV2 cells were plated into 24 well plates at a density of 2x105 cells/well for 24 h and then washed. The cells incubated with various concentrations of purpurogallin for 1 h were treated with or without 0.5 μg/ml LPS for 24 h and then incubated in 0.5 mg/ml MTT solution. Three hours later, the supernatant was removed and the forma¬tion of formazan was measured at 540 nm using a microplate reader.
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 18:56:13 GMT 2025
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| Record UNII |
L3Z7U4N28P
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| Record Status |
Validated (UNII)
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