Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H10O4 |
Molecular Weight | 254.2375 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC2=C(C(O)=C1)C(=O)C3=C(C=CC=C3O)C2=O
InChI
InChIKey=LQGUBLBATBMXHT-UHFFFAOYSA-N
InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
Molecular Formula | C15H10O4 |
Molecular Weight | 254.2375 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Chrysophanic acid (Chrysophanol) is a member of the anthraquinone family abundant in rhubarb, a widely used herb for obesity treatment in Traditional Korean Medicine. Chrysophanol has been shown to induce cell death in different types of cancer cells. Chrysophanol inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. Chrysophanol also effectively suppresses breast cancer cell proliferation and facilitates chemosentivity through modulation of the NF-κB signaling pathway. A treatment of chrysophanol could reduce significantly the
clinical signs and the levels of inflammatory mediators in a colitis model caused by DSS treatment.
The anti-inflammatory activities of chrysophanol could be attributed, at least in part, to
the inhibition of proinflammatory cytokine production (TNF-α and IL-6), COX-2, and iNOS protein
expression. These effects of chrysophanol are caused by the inhibition of LPS-induced NF-κB
activation, IκB-α degradation, and caspase-1 activation. These results provide experimental evidence
showing that chrysophanol might prove useful in the treatment of inflammatory diseases.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL613729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24395532 |
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Target ID: CHEMBL4804 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17497420 |
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Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27049294 |
12.3 µM [IC50] | ||
Target ID: CHEMBL4102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24763362 |
36.12 µM [IC50] | ||
Target ID: CHEMBL2949 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24763362 |
46.21 µM [IC50] | ||
Target ID: GO:0035586 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26724370 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Antifungal activity of anthraquinone derivatives from Rheum emodi. | 2000 Sep |
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Determination of pKa values of anthraquinone compounds by capillary electrophoresis. | 2001 Feb |
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[Studies on the anthraquinones of Cassia siamea]. | 2001 Jul |
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Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity. | 2001 Jul 23 |
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Cytotoxic and DNA damage-inducing activities of low molecular weight phenols from rhubarb. | 2001 Jul-Aug |
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[Study on the quantitative change of anthraquinonoids of Rhei in the preparation of dachengqi]. | 2002 Jan |
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Antimycobacterial anthraquinone-chromanone compound and diketopiperazine alkaloid from the fungus Chaetomium globosum KMITL-N0802. | 2002 Sep |
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Capillary electrophoresis for simultaneous determination of emodin, chrysophanol, and their 8-beta-D-glucosides. | 2003 Apr |
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Transcriptional suppression of the HIV promoter by natural compounds. | 2003 Mar |
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[Phenolic compounds isolated from rhizoma of Aster tataricus]. | 2003 Oct |
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[Simultaneous determination of 4 anthraquinones in Kuhuang injection by RP-HPLC]. | 2004 Nov |
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Studies on chemical constituents of Rheum glabricaule. | 2005 Aug |
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PTP1B inhibitors from Ardisia japonica. | 2005 Feb |
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[Influence of processing rhubarb on it's anthraquinone contents]. | 2005 Jun |
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Antimycobacterial agents from selected Mexican medicinal plants. | 2005 Sep |
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[Study on the selection of crude drugs of rhubarb dispensing granule]. | 2006 Apr |
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PTP1B inhibitors from Saussrurea lappa. | 2006 Apr-May |
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Different polyketide folding modes converge to an identical molecular architecture. | 2006 Aug |
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[Comparative study on in vitro drug-release between Tuizhang ophthalmic gel and Tuizhang oculentum]. | 2007 Apr |
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Large-scale separation of hydroxyanthraquinones from Rheum palmatum L. by pH-zone-refining counter-current chromatography. | 2007 Dec 28 |
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Simultaneous analysis of eight bioactive compounds in Danning tablet by HPLC-ESI-MS and HPLC-UV. | 2007 Feb 19 |
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Simultaneous determination of eight active components in Chinese medicine 'YIQING' capsule using high-performance liquid chromatography. | 2007 Jan 4 |
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Synergistic interaction of physcion and chrysophanol on plant powdery mildew. | 2007 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20877234
Experimental
colitis in mice was induced by a 5% DSS dissolved in the drinking water for 7 days.
Chrysophanol was administered at doses of 5 mg/kg once a day for 7 days prior to 5% DSS
supplement.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21089180
Chrysophanol (80 and 120 uM) significantly blocks cell proliferation when combined with the mTOR inhibitor, Rapamycin. Chrysophanol inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K, and significantly blocks cell proliferation. Chrysophanol dose dependently decreases CCK-8 and the viability of EGFR-overexpressing SNU-C5 cells. Chrysophanol treatment dose-dependently decreases EGF induced phosphorylation of EGFR at Tyr1068. Chrysophanol (80 and 120 uM) reduces the phosphorylation levels of mTOR at Ser2448. Chrysophanol (80 and 120 uM) also decreases the phosphorylation levels of p70S6K at Thr389.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 16 21:57:50 UTC 2022
by
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Record UNII |
N1ST8V8RR2
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Record Status |
Validated (UNII)
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M3532
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DTXSID6024832
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C027113
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37132
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Chrysophanic acid
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646567
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