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=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

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 8297
Dual specificity phosphatase Cdc25B 13 Target ID: CHEMBL4804 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17497420	Inhibitor 8297
Protein-tyrosine phosphatase 1B 34 Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27049294	Inhibitor 8297	12.3 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL4102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24763362	Inhibitor 8297	36.12 µM [IC50]
Cyclooxygenase-1 127 Target ID: CHEMBL2949 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24763362	Inhibitor 8297	46.21 µM [IC50]
purinergic receptor activity 1 Target ID: GO:0035586 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26724370	Modulator 828

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 592 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 123 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20877234	Primary	Preclinical	Unknown Approved Use Unknown
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27049294	Primary	Basic research	Unknown Approved Use Unknown
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26724370	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[A new isoflavone from Huoxue Yiqi Tang].	2005 Aug	16201689
[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
Three new isoprenylated flavonoids from the roots of Sophora flavescens.	2005 Jun	15621632
[Study on the selection of crude drugs of rhubarb dispensing granule].	2006 Apr	16913494
PTP1B inhibitors from Saussrurea lappa.	2006 Apr-May	16864436
Different polyketide folding modes converge to an identical molecular architecture.	2006 Aug	16829953
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
[Induction of hairy roots and anthraquinone production in Rheum palmatum].	2006 Sep	17144464
Defensive components in insect eggs: are anthraquinones produced during egg development?	2006 Sep	16835809
Identification of natural compounds with anti-hepatitis B virus activity from Rheum palmatum L. ethanol extract.	2007	17785969
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
Polyketide folding in higher plants: biosynthesis of the phenylanthraquinone knipholone.	2007 Apr 27	17388630
Large-scale separation of hydroxyanthraquinones from Rheum palmatum L. by pH-zone-refining counter-current chromatography.	2007 Dec 28	18022630
Simultaneous analysis of eight bioactive compounds in Danning tablet by HPLC-ESI-MS and HPLC-UV.	2007 Feb 19	17079108
Ferulic acid esters from Euphorbia hylonoma.	2007 Jan	17067756
Rapid separation and determination of structurally related anthraquinones in Rhubarb by pressurized capillary electrochromatography.	2007 Jan 4	16875795
Simultaneous determination of eight active components in Chinese medicine 'YIQING' capsule using high-performance liquid chromatography.	2007 Jan 4	16846714
Comparison of plants used for skin and stomach problems in Trinidad and Tobago with Asian ethnomedicine.	2007 Jan 5	17207273
Cellular absorption of anthraquinones emodin and chrysophanol in human intestinal Caco-2 cells.	2007 Jul	17617731
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
Synergistic interaction of physcion and chrysophanol on plant powdery mildew.	2007 May	17397111
Simultaneous quantification of five anthraquinones in rat plasma by high-performance liquid chromatography with fluorescence detection.	2007 May	17294506
Anthraquinones, Cdc25B phosphatase inhibitors, isolated from the roots of Polygonum multiflorum Thunb.	2007 May 20	17497420
Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase.	2007 Nov	17978503
[Study on correlation of soil nutrients and content of active constituents in root of Rumex gmelini].	2007 Oct	18161286
In situ synthesis of molecularly imprinted polymers on glass microspheres in a column.	2007 Oct	17786412
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
Purification of hydroxyanthraquinones and cinnamic acid from the roots of Rheum officinale Baill.	2008 Feb	18183553
Optimization and validation of a chromatographic method for the simultaneous quantification of six bioactive compounds in Rhizoma et Radix Polygoni Cuspidati.	2008 Jan	18088511
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
Study of interactions of anthraquinones with DNA using ethidium bromide as a fluorescence probe.	2008 Jun	17825605
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 `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

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Name

Type

Language

CHRYSOPHANIC ACID

Common Name

English

CHRYSOPHANIC ACID [MI]

Common Name

English

4,5-DIHYDROXY-2-METHYLANTHRAQUINONE

Systematic Name

English

3-METHYLCHRYSAZIN

Common Name

English

CHRYSOPHANOL

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