Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H8O5 |
| Molecular Weight | 256.2103 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC(O)=C(O)C2=C1C(=O)C3=C(C=CC=C3)C2=O
InChI
InChIKey=BBNQQADTFFCFGB-UHFFFAOYSA-N
InChI=1S/C14H8O5/c15-8-5-9(16)14(19)11-10(8)12(17)6-3-1-2-4-7(6)13(11)18/h1-5,15-16,19H
| Molecular Formula | C14H8O5 |
| Molecular Weight | 256.2103 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Purpurin (1,2,4-trihydroxy-9,10-anthraquinone), a natural red anthraquinone pigment in madder root (Rubia tinctorum L.), possesses antifungal activity against Candida species. Purpurin is also a specific inhibitor of adipocyte-derived leucine aminopeptidase (A-LAP) and can be developed as a new anti-angiogenic agent.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| A dose response analysis of purpurin derivatives used as photosensitizers for the photodynamic treatment of transplantable FANFT induced urothelial tumors. | 1987 Jun |
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| Antiretroviral activities of anthraquinones and their inhibitory effects on reverse transcriptase. | 1991 Mar-Apr |
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| Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase. | 1995 Nov 15 |
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| Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules. | 1996 Sep 3 |
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| Linkage and redox isomerism in ruthenium complexes of catecholate, semi-quinone, and o-acylphenolate ligands derived from tri- and tetrahydroxy-9,10-anthracenediones. | 2001 Aug 13 |
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| Photodynamic therapy in oncology. | 2001 Jun |
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| Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5. | 2001 Sep |
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| Preventive effects of anthraquinone food pigments on the DNA damage induced by carcinogens in Drosophila. | 2001 Sep 1 |
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| Structure of acid-stable carmine. | 2002 Feb |
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| Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. | 2002 Oct 31 |
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| Photophysical and photochemical properties of 1,2,4-trihydroxy-9,10-anthraquinone adsorbed on inorganic oxides. | 2003 Jun |
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| Protection against Trp-P-2 DNA adduct formation in C57bl6 mice by purpurin is accompanied by induction of cytochrome P450. | 2003 May 21 |
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| The specificity of cross-reactivity: promiscuous antibody binding involves specific hydrogen bonds rather than nonspecific hydrophobic stickiness. | 2003 Oct |
|
| Isolation of colour components from native dye-bearing plants in northeastern India. | 2005 Feb |
|
| A multivariate study of the performance of an ultrasound-assisted madder dyes extraction and characterization by liquid chromatography-photodiode array detection. | 2009 Jan |
|
| Horseradish peroxidase-catalyzed oxidation of chlorophyll a with hydrogen peroxide: characterization of the products and mechanism of the reaction. | 2010 May |
|
| Novel antifungal activity of purpurin against Candida species in vitro. | 2010 Nov |
Patents
Sample Use Guides
The antifungal activity of purpurin (1,2,4-trihydroxy-9,10-anthraquinone) was evaluated by a broth microdilution assay against a total of 24 Candida isolates representing six species. The minimum inhibitory concentration (MIC) range of purpurin was 1.28-5.12 μg/ml. Mechanistic studies using the rhodamine 6G extrusion assay indicated that purpurin inhibited the energy-dependent efflux pumps of the Candida isolates in a dose-dependent manner. Furthermore, purpurin demonstrated a dose-dependent depolarization of mitochondrial membrane potential.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:14:09 GMT 2023
by
admin
on
Sat Dec 16 02:14:09 GMT 2023
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| Record UNII |
L1GT81LS6N
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| Record Status |
Validated (UNII)
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| Record Version |
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1,2,4-TRIHYDROXYANTHRAQUINONE
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m9326
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DTXSID4021214
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