U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
[Phenolic compounds isolated from rhizoma of Aster tataricus].
2003 Oct
[Study on releasing rate of chrysophanol from Ruyi Jinhuang plaster].
2004 Aug
Analysis of the anthraquinones aloe-emodin and aloin by gas chromatography/mass spectrometry.
2004 Dec 20
[Study on the interactions between four components in Ligusticum chuanxiong rhizome and acceptors on cardiac muscle membrane].
2004 Jul
[Study on qualitative and quantitative methods for yinhuang liangxiao granule].
2004 May
[Simultaneous determination of 4 anthraquinones in Kuhuang injection by RP-HPLC].
2004 Nov
Preparative isolation and purification of hydroxyanthraquinones and cinnamic acid from the chinese medicinal herb Rheum officinale Baill. by high-speed counter-current chromatography.
2004 Oct 15
Studies on chemical constituents of Rheum glabricaule.
2005 Aug
[A new isoflavone from Huoxue Yiqi Tang].
2005 Aug
Separation and determination of four active anthraquinones in Chinese herbal preparations by flow injection-capillary electrophoresis.
2005 Aug
Determination and locational variations in the quantity of hydroxyanthraquinones and their glycosides in rhizomes of Rheum emodi using high-performance liquid chromatography.
2005 Dec 2
PTP1B inhibitors from Ardisia japonica.
2005 Feb
[Studies on the chemical constituents in herb of Mentha haplocalyx].
2005 Jul
[Influence of processing rhubarb on it's anthraquinone contents].
2005 Jun
[Study on the optimal harvesting time of Rumex gmelini by analyzing the contents of principal components].
2005 Jun
Three new isoprenylated flavonoids from the roots of Sophora flavescens.
2005 Jun
High-performance thin layer chromatography method for quantitative determination of four major anthraquinone derivatives in Rheum emodi.
2005 Jun 10
Simultaneous determination of anthraquinones, their 8-beta-D-glucosides, and sennosides of Rhei Rhizoma by capillary electrophoresis.
2005 May
Simultaneous determination of anthraquinones in Rhubarb by pressurized liquid extraction and capillary zone electrophoresis.
2005 May
Separation and determination of anthraquinones in Cassia obtusifolia (Leguminosae) by micellar electrokinetic capillary electrophoresis.
2005 Nov
[Screening of antineoplastic components in Radix et Rhizoma Rhei using chromatographic fingerprints].
2005 Sep
Antidiabetic stilbene and anthraquinone derivatives from Rheum undulatum.
2005 Sep
Antimycobacterial agents from selected Mexican medicinal plants.
2005 Sep
Determination of five anthraquinones in medicinal plants by capillary zone electrophoresis with beta-cyclodextrin addition.
2006 Aug 4
[Comparative studies on purgative potency among three spieces of certified rhubarb].
2006 Dec
[Studies on chemical constituents of hairy root of Cassia obtusifolia].
2006 Feb
[Simultaneous determination of resveratrol, emodin, chrysophanol, physcion, in root of Polygonam cuspidatum and its extract by HPLC].
2006 Feb
[Simultaneous determination of three kinds of components in sanhuang tablets by high-performance liquid chromatography].
2006 Mar
Isolation and synthesis of analgesic and anti-inflammatory compounds from Ochna squarrosa L.
2006 Oct 15
Efficient isolation of anthraquinone-derivatives from Trichoderma harzianum ETS 323.
2007 Apr 10
Polyketide folding in higher plants: biosynthesis of the phenylanthraquinone knipholone.
2007 Apr 27
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
Cellular absorption of anthraquinones emodin and chrysophanol in human intestinal Caco-2 cells.
2007 Jul
Simultaneous determination and pharmacokinetic studies of aloe emodin and chrysophanol in rats after oral administration of Da-Cheng-Qi decoction by high-performance liquid chromatography.
2007 Jul
Alvaradoins E-N, antitumor and cytotoxic anthracenone C-glycosides from the leaves of Alvaradoa haitiensis.
2007 Jun
Antiprotozoal activity of Senna racemosa.
2007 Jun 13
Chemical constituents from the roots of Homonoia riparia.
2007 Mar
Synergistic interaction of physcion and chrysophanol on plant powdery mildew.
2007 May
Simultaneous quantification of five anthraquinones in rat plasma by high-performance liquid chromatography with fluorescence detection.
2007 May
Anthraquinones, Cdc25B phosphatase inhibitors, isolated from the roots of Polygonum multiflorum Thunb.
2007 May 20
Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase.
2007 Nov
In situ synthesis of molecularly imprinted polymers on glass microspheres in a column.
2007 Oct
Preparation of 1,8-di-O-alkylaloe-emodins and 15-amino-, 15-thiocyano-, and 15-selenocyanochrysophanol derivatives from aloe-emodin and studying their cytotoxic effects.
2008 Apr
Simultaneous determination of eight major bioactive compounds in Dachengqi Tang (DT) by high-performance liquid chromatography.
2008 Apr 29
Development and validation of a UPLC method for quality control of rhubarb-based medicine: fast simultaneous determination of five anthraquinone derivatives.
2008 Aug 5
Purification of hydroxyanthraquinones and cinnamic acid from the roots of Rheum officinale Baill.
2008 Feb
Determination of pharmacologically active compounds in root extracts of Cassia alata L. by use of high performance liquid chromatography.
2008 Jan 15
Simultaneous determination of anthraquinones in radix Polygoni multiflori by capillary gas chromatography coupled with flame ionization and mass spectrometric detection.
2008 Jul 18
Lipoxygenase inhibitory constituents from rhubarb.
2008 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 Sat Dec 16 19:58:32 GMT 2023
Edited
by admin
on Sat Dec 16 19:58:32 GMT 2023
Record UNII
N1ST8V8RR2
Record Status Validated (UNII)
Record Version
  • Download
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
INCI  
Official 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 Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6024832
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
FDA UNII
N1ST8V8RR2
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
MESH
C027113
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
CHEBI
3687
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
SMS_ID
100000126027
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
CAS
481-74-3
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-572-2
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
PUBCHEM
10208
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
NSC
37132
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
WIKIPEDIA
Chrysophanic acid
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
EVMPD
SUB33000
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
NSC
646567
Created by admin on Sat Dec 16 19:58:32 GMT 2023 , Edited by admin on Sat Dec 16 19:58:32 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY