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
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 |
|---|---|---|
| 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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| Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5. | 2001 Sep |
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| Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. | 2002 Oct 31 |
|
| 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.
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201-359-8
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1,2,4-TRIHYDROXYANTHRAQUINONE
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m9326
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DTXSID4021214
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SUBSTANCE RECORD
