Chrysophanic acid

Description

Chrysophanol is an anthraquinone that has been found in R. palmatum and has diverse biological activities. It induces necrosis in J5 human liver cancer cells when used at concentrations of 25, 50, 75, 100, and 200 μM. Chrysophanol (5, 10, and 50 μM) reduces LPS-induced production of nitric oxide (NO) and prostaglandin E₂ (PGE₂; ) and inhibits LPS-induced DNA oxidation in BV-2 microglia. In vivo, chrysophanol (5 mg/kg) decreases colonic levels of IL-6 and activation of NF-κB and reduces weight loss, diarrhea, and rectal bleeding in a mouse model of colitis induced by dextran sulfate (DSS; ). Chrysophanol (0.1, 1, and 10 mg/kg) increases survival, reduces brain tissue loss, and ameliorates motor balance deficits in a mouse model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO).

Chemical properties

yellow crystalline solid or brown powder

The Uses of Chrysophanic acid

Chrysophanic acid, a natural anthraquinone, is used to study anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells 1. It is also used to study the inhibition of replication of poliovirus types 2 and 3 (Picornaviridae) in vitro 2.

The Uses of Chrysophanic acid

antineoplastic, antibacterial

The Uses of Chrysophanic acid

A topical ointment used in the treatment of dermal conditions such as eczema and herpes.

What are the applications of Application

Chrysophanol is an inducer of intracellular Ca2+ concentration and exhibit antifungal activities

Definition

ChEBI: A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.

Synthesis Reference(s)

Tetrahedron Letters, 20, p. 4911, 1979 DOI: 10.1016/S0040-4039(01)86747-2

General Description

Golden yellow plates or brown powder. Melting point 196°C. Slightly soluble in water. Pale yellow aqueous solutions turn red on addition of alkali. Solutions in concentrated sulfuric acid are red.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Chrysophanic acid is incompatible with strong oxidizing agents.

Fire Hazard

Flash point data for Chrysophanic acid are not available; however, Chrysophanic acid is probably combustible.

Purification Methods

Crystallise chrysophanic acid from EtOH or *benzene and has m 195.6-196.2o, after sublimation it in a vacuum. The yellow mono-acetate has m 188-190o (from MeOH or Me2CO). It forms Ni2+, Co2+ and Cu2+ complexes. [Beilstein 8 H 470, 8 I 725, 8 II 510, 8 III 3808, 8 IV 3277.]