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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
Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus.
1992 Jan
Antifungal activity of anthraquinone derivatives from Rheum emodi.
2000 Sep
Cytotoxic and DNA damage-inducing activities of low molecular weight phenols from rhubarb.
2001 Jul-Aug
In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus.
2001 Mar
Inhibitory effects of Cassia tora L. on benzo[a]pyrene-mediated DNA damage toward HepG2 cells.
2001 May
[Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth. var. officinalis (Dode) Huang].
2001 Oct
[Studies on the chemical constituents in root of Rheum rhizastachyum].
2002 Apr
Four new compounds from the seeds of Cassia fistula.
2002 Aug
Emodin induces apoptosis in human promyeloleukemic HL-60 cells accompanied by activation of caspase 3 cascade but independent of reactive oxygen species production.
2002 Dec 15
[Study on the quantitative change of anthraquinonoids of Rhei in the preparation of dachengqi].
2002 Jan
[Determination of six effective components in Rheum by cyclodextrin modified micellar electrokinetic chromatography].
2002 Oct
Antimycobacterial anthraquinone-chromanone compound and diketopiperazine alkaloid from the fungus Chaetomium globosum KMITL-N0802.
2002 Sep
Cytotoxicity of natural hydroxyanthraquinones: role of oxidative stress.
2002 Sep-Oct
Simultaneous determination of hydroxyanthraquinones in rhubarb and experimental animal bodies by high-performance liquid chromatography.
2003 Aug
Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi.
2003 Aug
Cynodontin: a fungal metabolite with antifungal properties.
2003 Aug 13
Analysis of the anthraquinones aloe-emodin and aloin by gas chromatography/mass spectrometry.
2004 Dec 20
[Simultaneous determination of 4 anthraquinones in Kuhuang injection by RP-HPLC].
2004 Nov
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
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
Antimycobacterial agents from selected Mexican medicinal plants.
2005 Sep
[Comparative studies on purgative potency among three spieces of certified rhubarb].
2006 Dec
[Simultaneous determination of three kinds of components in sanhuang tablets by high-performance liquid chromatography].
2006 Mar
[Isolation of the chemical constituents from Shuanghuanglian injection and their structural identification].
2006 Oct
Isolation and synthesis of analgesic and anti-inflammatory compounds from Ochna squarrosa L.
2006 Oct 15
Identification of natural compounds with anti-hepatitis B virus activity from Rheum palmatum L. ethanol extract.
2007
[Comparative study on in vitro drug-release between Tuizhang ophthalmic gel and Tuizhang oculentum].
2007 Apr
Comparison of plants used for skin and stomach problems in Trinidad and Tobago with Asian ethnomedicine.
2007 Jan 5
Monodictyquinone A: a new antimicrobial anthraquinone from a sea urchin-derived fungus Monodictys sp.
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
Antiprotozoal activity of Senna racemosa.
2007 Jun 13
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
[Study on correlation of soil nutrients and content of active constituents in root of Rumex gmelini].
2007 Oct
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
Determination of pharmacologically active compounds in root extracts of Cassia alata L. by use of high performance liquid chromatography.
2008 Jan 15
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 Thu Jul 06 00:38:10 UTC 2023
Edited
by admin
on Thu Jul 06 00:38:10 UTC 2023
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 Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6024832
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
FDA UNII
N1ST8V8RR2
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
MESH
C027113
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
CHEBI
3687
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
SMS_ID
100000126027
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
CAS
481-74-3
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-572-2
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
PUBCHEM
10208
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
NSC
37132
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
WIKIPEDIA
Chrysophanic acid
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
EVMPD
SUB33000
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
NSC
646567
Created by admin on Thu Jul 06 00:38:10 UTC 2023 , Edited by admin on Thu Jul 06 00:38:10 UTC 2023
PRIMARY
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