EMODIN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O5
Molecular Weight	270.2369
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=C(O)C=C3O)C2=O

InChI

InChIKey=RHMXXJGYXNZAPX-UHFFFAOYSA-N

InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28831863 | https://www.ncbi.nlm.nih.gov/pubmed/29417945 | https://www.ncbi.nlm.nih.gov/pubmed/29355754

Emodin is a naturally occurring anthraquinone present in the roots of numerous plants and lichens and an active ingredient of various Chinese herbs. Emodin possesses various biological properties and serves as an anti-bacterial and anti-inflammatory agent. Emodin was studied as a potential anti-cancer agent: e.g., it was shown, that compound inhibits the invasion and migration of colon cancer cells in vitro and in vivo by blocking EMT, which is related with the inhibition of Wnt/β-catenin signaling pathway. Besides, emodin effectively ameliorates asthmatic airway inflammation and alternatively activated macrophages (AAMs) polarization, and thus can be a potential agent for the treatment of asthma. It is known that the Inhibition of AAMs is an alternative therapeutic strategy for treating asthma. Some experiments have revealed that emodin can be a beneficial dietary supplement in prolonging lifespan.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Wnt/β-catenin signaling pathway 1 Target ID: Wnt/β-catenin signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/29301594	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
lung cancer 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29355754	Primary	Basic research	Unknown Approved Use Unknown
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29301594	Primary	Preclinical	Unknown Approved Use Unknown
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29417945	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus.	1992 Jan	1310583
Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates.	1994 Sep-Oct	7835232
Cloning and expression of a rat liver phenobarbital-inducible UDP-glucuronosyltransferase (2B12) with specificity for monoterpenoid alcohols.	1995 Oct 1	7574722
Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules.	1996 Sep 3	8790401
Emodin ameliorates glucose-induced morphologic abnormalities and synthesis of transforming growth factor beta1 and fibronectin by human peritoneal mesothelial cells.	2001	11887862
In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus.	2001 Mar	11428243
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
Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.	2003 Dec	14646185
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.	2004 Apr	15120460
Herb medicine Inchin-ko-to (TJ-135) regulates PDGF-BB-dependent signaling pathways of hepatic stellate cells in primary culture and attenuates development of liver fibrosis induced by thioacetamide administration in rats.	2004 Aug	15288473
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.	2004 Jan 9	14557274
Signal pathways involved in emodin-induced contraction of smooth muscle cells from rat colon.	2004 May 15	15133857
Synthesis and biological evaluation of new derivatives of emodin.	2004 Nov 15	15498672
Effect of chemopreventive agents on glutathione S-transferase P1-1 gene expression mechanisms via activating protein 1 and nuclear factor kappaB inhibition.	2004 Sep 15	15313406
Antimycobacterial agents from selected Mexican medicinal plants.	2005 Sep	16105233
Inhibition of human cytochrome p450 1b1 further clarifies its role in the activation of dibenzo[a,l]pyrene in cells in culture.	2007	17623886
Emodin and DHA potently increase arsenic trioxide interferon-alpha-induced cell death of HTLV-I-transformed cells by generation of reactive oxygen species and inhibition of Akt and AP-1.	2007 Feb 15	17077332
Exploration of Emodin to treat alpha-naphthylisothiocyanate-induced cholestatic hepatitis via anti-inflammatory pathway.	2008 Aug 20	18590720
Is senna laxative use associated to cathartic colon, genotoxicity, or carcinogenicity?	2009	20107583
Inhibition of ATP-induced macrophage death by emodin via antagonizing P2X7 receptor.	2010 Aug 25	20452342
A CE-based assay for human protein kinase CK2 activity measurement and inhibitor screening.	2010 Jan	20162588
Dose-dependent hepatoprotective effect of emodin against acetaminophen-induced acute damage in rats.	2010 Nov	19800773
Emodin and [6]-gingerol lessen hypoxia-induced embryotoxicities in cultured mouse whole embryos via upregulation of hypoxia-inducible factor 1α and intracellular superoxide dismutases.	2011 May	21382473
Bioactive anthraquinones from endophytic fungus Aspergillus versicolor isolated from red sea algae.	2012 Oct	23139125
Long-term treatment with san'o-shashin-to, a kampo medicine, markedly ameliorates cardiac ischemia-reperfusion injury in ovariectomized rats via the redox-dependent mechanism.	2013	23615023

Patents

Sample Use Guides

In Vivo Use Guide

murine asthma model: intraperitoneal injection of emodin (20 mg·kg-1·d-1, ip) 1 h prior to DRA (dust mite, ragweed and aspergillus) challenge on days 12-14 significantly decreased pulmonary eosinophil and lymphocyte infiltration, mucus secretion and serum IgE production, as well as IL-4 and IL-5 production in bronchoalveolar lavage fluid.

Route of Administration: Intraperitoneal

In Vitro Use Guide

The potential for emodin to inhibit pancreatic cancer cell proliferation was examined using 4 human pancreatic adenocarcinoma cell lines: Mia Paca-2, BxPC-3, Panc-1, and L3.6pl. Forty-eight-hour treatment with 50 muM emodin inhibited proliferation in Mia Paca-2 cells by 42%, BxPc-3 by 38%, L3.6pl by 56%, and Panc-1 by 18% (all P < .01). In three-fourths of the cell lines, emodin treatment resulted in an increase (from 4.7% to 22%) in the cell population number in apoptosis when measured by flow cytometric analysis

Name

Type

Language

EMODIN

Official Name

English

FRANGULA EMODIN

Common Name

English

RHEUM EMODIN

Common Name

English

EMODIN [INCI]

Common Name

English

EMODOL

Common Name

English

SCHUTTGELB

Common Name

English

NSC-408120

Code

English

NSC-622947

Code

English

EMODIN [MI]

Common Name

English

FRANGULIC ACID

Common Name

English

EMODIN [HSDB]

Common Name

English

1,3,8-TRIHYDROXY-6-METHYL-9,10-ANTHRACENEDIONE

Systematic Name

English

EMODIN [USP-RS]

Common Name

English

ARCHIN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1967