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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
Structure of CHRYSOPHANIC ACID

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

HIDE SMILES / InChI

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

TargetsConditions
PubMed

PubMed

TitleDatePubMed
Antifungal activity of anthraquinone derivatives from Rheum emodi.
2000 Sep
Determination of pKa values of anthraquinone compounds by capillary electrophoresis.
2001 Feb
[Studies on the anthraquinones of Cassia siamea].
2001 Jul
Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity.
2001 Jul 23
Cytotoxic and DNA damage-inducing activities of low molecular weight phenols from rhubarb.
2001 Jul-Aug
[Study on the quantitative change of anthraquinonoids of Rhei in the preparation of dachengqi].
2002 Jan
Antimycobacterial anthraquinone-chromanone compound and diketopiperazine alkaloid from the fungus Chaetomium globosum KMITL-N0802.
2002 Sep
Capillary electrophoresis for simultaneous determination of emodin, chrysophanol, and their 8-beta-D-glucosides.
2003 Apr
Transcriptional suppression of the HIV promoter by natural compounds.
2003 Mar
[Phenolic compounds isolated from rhizoma of Aster tataricus].
2003 Oct
[Simultaneous determination of 4 anthraquinones in Kuhuang injection by RP-HPLC].
2004 Nov
Studies on chemical constituents of Rheum glabricaule.
2005 Aug
PTP1B inhibitors from Ardisia japonica.
2005 Feb
[Influence of processing rhubarb on it's anthraquinone contents].
2005 Jun
Antimycobacterial agents from selected Mexican medicinal plants.
2005 Sep
[Study on the selection of crude drugs of rhubarb dispensing granule].
2006 Apr
PTP1B inhibitors from Saussrurea lappa.
2006 Apr-May
Different polyketide folding modes converge to an identical molecular architecture.
2006 Aug
[Comparative study on in vitro drug-release between Tuizhang ophthalmic gel and Tuizhang oculentum].
2007 Apr
Large-scale separation of hydroxyanthraquinones from Rheum palmatum L. by pH-zone-refining counter-current chromatography.
2007 Dec 28
Simultaneous analysis of eight bioactive compounds in Danning tablet by HPLC-ESI-MS and HPLC-UV.
2007 Feb 19
Simultaneous determination of eight active components in Chinese medicine 'YIQING' capsule using high-performance liquid chromatography.
2007 Jan 4
Synergistic interaction of physcion and chrysophanol on plant powdery mildew.
2007 May
Patents

Sample Use Guides

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
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
by admin
on Fri Dec 16 21:57:50 UTC 2022
Edited
by admin
on Fri Dec 16 21:57:50 UTC 2022
Record UNII
N1ST8V8RR2
Record Status Validated (UNII)
Record Version
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Name Type Language
CHRYSOPHANIC ACID
MI   WHO-DD  
Common Name English
CHRYSOPHANIC ACID [MI]
Common Name English
4,5-DIHYDROXY-2-METHYLANTHRAQUINONE
Systematic Name English
3-METHYLCHRYSAZIN
Common Name English
CHRYSOPHANOL
Common Name English
1,8-DIHYDROXY-3-METHYL-9,10-ANTHRACENEDIONE
Systematic Name English
NSC-37132
Code English
C.I. NATURAL YELLOW 23
Code English
NSC-646567
Code English
2-METHYL-4,5-DIHYDROXYANTHRAQUINONE
Systematic Name English
C.I. 75400
Code English
Chrysophanic acid [WHO-DD]
Common Name English
1,8-DIHYDROXY-3-METHYLANTHRAQUINONE
Systematic Name English
3-METHYL-1,8-DIHYDROXYANTHRAQUINONE
Systematic Name English
Code System Code Type Description
MERCK INDEX
M3532
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY Merck Index
EPA CompTox
DTXSID6024832
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
FDA UNII
N1ST8V8RR2
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
MESH
C027113
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
CHEBI
3687
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
CAS
481-74-3
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
ECHA (EC/EINECS)
207-572-2
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
PUBCHEM
10208
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
NSC
37132
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
WIKIPEDIA
Chrysophanic acid
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
EVMPD
SUB33000
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
NSC
646567
Created by admin on Fri Dec 16 21:57:50 UTC 2022 , Edited by admin on Fri Dec 16 21:57:50 UTC 2022
PRIMARY
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