CHRYSOPHANIC ACID

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 Search

SMILES

CC1=CC(O)=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=C1

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22848001 | https://www.ncbi.nlm.nih.gov/pubmed/21089180 | https://www.ncbi.nlm.nih.gov/pubmed/29344652 | https://www.ncbi.nlm.nih.gov/pubmed/20877234

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Japanese encephalitis virus 1 Target ID: CHEMBL613729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24395532	Inhibitor 8504
Dual specificity phosphatase Cdc25B 13 Target ID: CHEMBL4804 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17497420	Inhibitor 8504
Protein-tyrosine phosphatase 1B 34 Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27049294	Inhibitor 8504	12.3 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL4102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24763362	Inhibitor 8504	36.12 µM [IC50]
Cyclooxygenase-1 131 Target ID: CHEMBL2949 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24763362	Inhibitor 8504	46.21 µM [IC50]
purinergic receptor activity 1 Target ID: GO:0035586 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26724370	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
Japanese encephalitis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24395532	Primary	Basic research	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21089180 https://www.ncbi.nlm.nih.gov/pubmed/29344652 https://www.ncbi.nlm.nih.gov/pubmed/27171670 https://www.ncbi.nlm.nih.gov/pubmed/20169580	Primary	Basic research	Unknown Approved Use Unknown
Cardiomyopathy 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28738526	Primary	Preclinical	Unknown Approved Use Unknown
Ulcerative colitis 125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20877234	Primary	Preclinical	Unknown Approved Use Unknown
Diabetes mellitus 93 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27049294	Primary	Basic research	Unknown Approved Use Unknown
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26724370	Primary	Preclinical	Unknown Approved Use Unknown

F_unbound

Value	Dose	Co-administered	Analyte	Population
11.7% REVIEW https://pubmed.ncbi.nlm.nih.gov/31373015/			CHRYSOPHANIC ACID plasma	Homo sapiens

PubMed

Title	Date	PubMed
Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus.	1992 Jan	1310583
[Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth. var. officinalis (Dode) Huang].	2001 Oct	12579972
[Studies on the chemical constituents in root of Rheum rhizastachyum].	2002 Apr	12774374
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	12445860
[Studies on the chemical constituents of the stems of Alyxia sinensis (I)].	2002 Feb	12774386
[Study on the quantitative change of anthraquinonoids of Rhei in the preparation of dachengqi].	2002 Jan	12774360
Simultaneous determination of hydroxyanthraquinones in rhubarb and experimental animal bodies by high-performance liquid chromatography.	2003 Aug	12945670
Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi.	2003 Aug	12932135
Cynodontin: a fungal metabolite with antifungal properties.	2003 Aug 13	12903946
Transcriptional suppression of the HIV promoter by natural compounds.	2003 Mar	12719011
Bhimamycin A to approximately E and bhimanone: isolation, structure elucidation and biological activity of novel quinone antibiotics from a terrestrial Streptomycete.	2003 Nov	14763559
[Study on releasing rate of chrysophanol from Ruyi Jinhuang plaster].	2004 Aug	15506283
Microbial glycosylation of four free anthraquinones by Absidia coerulea.	2004 Jan	15000479
Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru.	2004 Mar	15043409
Evaluation of Rhubarb using antioxidative activity as an index of pharmacological usefulness.	2004 Mar	15036474
Antigenotoxic properties of Cassia tea (Cassia tora L.): mechanism of action and the influence of roasting process.	2004 Nov 19	15501482
Chrysophanol glycosides from callus cultures of monocotyledonous Kniphofia spp. (Asphodelaceae).	2004 Oct	15467251
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	15527141
[Studies on the chemical constituents in herb of Mentha haplocalyx].	2005 Jul	16161444
[Influence of processing rhubarb on it's anthraquinone contents].	2005 Jun	16124606
[Study on the optimal harvesting time of Rumex gmelini by analyzing the contents of principal components].	2005 Jun	16110856
High-performance thin layer chromatography method for quantitative determination of four major anthraquinone derivatives in Rheum emodi.	2005 Jun 10	16001557
Simultaneous determination of anthraquinones, their 8-beta-D-glucosides, and sennosides of Rhei Rhizoma by capillary electrophoresis.	2005 May	15863933
[Study on the selection of crude drugs of rhubarb dispensing granule].	2006 Apr	16913494
PTP1B inhibitors from Saussrurea lappa.	2006 Apr-May	16864436
Determination of five anthraquinones in medicinal plants by capillary zone electrophoresis with beta-cyclodextrin addition.	2006 Aug 4	16806252
[Comparative studies on purgative potency among three spieces of certified rhubarb].	2006 Dec	17348197
[Studies on chemical constituents of hairy root of Cassia obtusifolia].	2006 Feb	16573002
[Simultaneous determination of resveratrol, emodin, chrysophanol, physcion, in root of Polygonam cuspidatum and its extract by HPLC].	2006 Feb	16572998
[Simultaneous determination of three kinds of components in sanhuang tablets by high-performance liquid chromatography].	2006 Mar	16759005
[Isolation of the chemical constituents from Shuanghuanglian injection and their structural identification].	2006 Oct	17062354
Isolation and synthesis of analgesic and anti-inflammatory compounds from Ochna squarrosa L.	2006 Oct 15	16824764
Preparative isolation and purification of hydroxyanthraquinones from Rheum tanguticum Maxim. on normal phase silica gel: using a Flash Master Personal system.	2007	17516248
[Comparative study on in vitro drug-release between Tuizhang ophthalmic gel and Tuizhang oculentum].	2007 Apr	17608219
Efficient isolation of anthraquinone-derivatives from Trichoderma harzianum ETS 323.	2007 Apr 10	17067682
Ferulic acid esters from Euphorbia hylonoma.	2007 Jan	17067756
Monodictyquinone A: a new antimicrobial anthraquinone from a sea urchin-derived fungus Monodictys sp.	2007 Jul	17603212
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	17370297
Alvaradoins E-N, antitumor and cytotoxic anthracenone C-glycosides from the leaves of Alvaradoa haitiensis.	2007 Jun	17552563
Antiprotozoal activity of Senna racemosa.	2007 Jun 13	17481835
Chemical constituents from the roots of Homonoia riparia.	2007 Mar	17520829
Simultaneous determination of anthraquinones in rhubarb by high-performance liquid chromatography and capillary electrophoresis.	2007 Mar 23	17289060
Anthraquinones, Cdc25B phosphatase inhibitors, isolated from the roots of Polygonum multiflorum Thunb.	2007 May 20	17497420
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	18379097
Simultaneous determination of eight major bioactive compounds in Dachengqi Tang (DT) by high-performance liquid chromatography.	2008 Apr 29	18445276
Development and validation of a UPLC method for quality control of rhubarb-based medicine: fast simultaneous determination of five anthraquinone derivatives.	2008 Aug 5	18440751
Determination of pharmacologically active compounds in root extracts of Cassia alata L. by use of high performance liquid chromatography.	2008 Jan 15	18371725
Paeciloxanthone, a new cytotoxic xanthone from the marine mangrove fungus Paecilomyces sp. (Tree1-7).	2008 Jan-Feb	18253881
Simultaneous determination of anthraquinones in radix Polygoni multiflori by capillary gas chromatography coupled with flame ionization and mass spectrometric detection.	2008 Jul 18	18262194
Lipoxygenase inhibitory constituents from rhubarb.	2008 May	18481015

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Wed Apr 02 17:55:58 GMT 2025` Edited by `admin` on `Wed Apr 02 17:55:58 GMT 2025`
Record UNII	N1ST8V8RR2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHRYSOPHANOL

Preferred Name

English

CHRYSOPHANIC ACID

Common Name

English

CHRYSOPHANIC ACID [MI]

Common Name

English

4,5-DIHYDROXY-2-METHYLANTHRAQUINONE

Systematic Name

English

3-METHYLCHRYSAZIN

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