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=CC2=C(C(O)=C1O)C(=O)C(O)=CC=C2
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 |
|---|---|---|
| Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations. | 1995 Apr |
|
| Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay. | 2001 Feb |
|
| Design, synthesis, and biological evaluation of a series of simple and novel potential antimalarial compounds. | 2001 Jul 23 |
|
| Flow-injection chemiluminescent determination of vanadium(IV) and total vanadium by means of catalysis on the periodate oxidation of purpurogallin. | 2002 Dec 6 |
|
| Coordination of aluminium with purpurogallin and theaflavin digallate. | 2003 Sep 1 |
|
| Discovery, characterization, and structure-activity relationships studies of proapoptotic polyphenols targeting B-cell lymphocyte/leukemia-2 proteins. | 2003 Sep 25 |
|
| Metabolism of pyrogallol to purpurogallin by human erythrocytic hemoglobin. | 2004 Aug |
|
| [Separation and identification of two benzotropolones from teapigment]. | 2004 Jun |
|
| Benzotropolone inhibitors of estradiol methylation: kinetics and in silico modeling studies. | 2005 Apr 1 |
|
| Protection by tropolones against H2O2-induced DNA damage and apoptosis in cultured Jurkat cells. | 2005 Feb |
|
| Potent inhibitory effects of black tea theaflavins on off-odor formation from citral. | 2006 Apr 19 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
| Peroxidase activity can dictate the in vitro lignin dehydrogenative polymer structure. | 2007 Feb |
|
| Cytotoxicity of chloroquine in isolated rat hepatocytes. | 2007 Jul-Aug |
|
| A cellular model to monitor proteasome dysfunction by alpha-synuclein. | 2009 Aug 25 |
|
| Biocatalysis in water-in-ionic liquid microemulsions: a case study with horseradish peroxidase. | 2009 Jan 20 |
|
| Deficiency in chromosome congression by the inhibition of Plk1 polo box domain-dependent recognition. | 2009 Jan 23 |
|
| Parallel metatranscriptome analyses of host and symbiont gene expression in the gut of the termite Reticulitermes flavipes. | 2009 Oct 15 |
|
| Phytic Acid Exposure Alters AflatoxinB1-induced Reproductive and Oxidative Toxicity in Albino Rats (Rattus norvegicus). | 2009 Sep |
|
| 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 Apr 15 |
|
| Computational analysis of phosphopeptide binding to the polo-box domain of the mitotic kinase PLK1 using molecular dynamics simulation. | 2010 Aug 12 |
|
| Natural products in regression and slowing of progression of atherosclerosis. | 2010 Dec |
|
| Explaining the atypical reaction profiles of heme enzymes with a novel mechanistic hypothesis and kinetic treatment. | 2010 May 17 |
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
by
admin
on
Edited
Fri Dec 15 17:53:02 GMT 2023
by
admin
on
Fri Dec 15 17:53:02 GMT 2023
|
| Record UNII |
L3Z7U4N28P
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
8647
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY | |||
|
Purpurogallin
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY | |||
|
35676
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY | |||
|
569-77-7
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY | |||
|
5281571
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY | |||
|
646653
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY | |||
|
m9327
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY | Merck Index | ||
|
L3Z7U4N28P
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY | |||
|
DTXSID40205436
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY | |||
|
209-324-9
Created by
admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
|
PRIMARY |