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

Molecular Formula	C15H10O5
Molecular Weight	270.2369
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/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
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
Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues.	2001 Dec 17	11720861
In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus.	2001 Mar	11428243
Effects and mechanisms of emodin on cell death in human lung squamous cell carcinoma.	2001 Sep	11522592
Induction of cytochromes P450 1A1 and 1B1 by emodin in human lung adenocarcinoma cell line CL5.	2001 Sep	11502733
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
Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context.	2003 Dec	14644660
Tumor necrosis factor-alpha and troglitazone regulate plasminogen activator inhibitor type 1 production through extracellular signal-regulated kinase- and nuclear factor-kappaB-dependent pathways in cultured human umbilical vein endothelial cells.	2003 Dec	14534369
Emodin induces apoptosis of human cervical cancer cells through poly(ADP-ribose) polymerase cleavage and activation of caspase-9.	2003 Jul 25	12892828
Transcriptional suppression of the HIV promoter by natural compounds.	2003 Mar	12719011
Neuraminidase inhibitors from Reynoutria elliptica.	2003 May	12785732
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
Emodin enhances arsenic trioxide-induced apoptosis via generation of reactive oxygen species and inhibition of survival signaling.	2004 Jan 1	14729614
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.	2004 Jan 9	14557274
Evaluation of a real-time polymerase chain reaction method for the quantification of CYP1B1 gene expression in MCF-7 human breast carcinoma cells.	2004 Mar-Apr	14990334
Synthesis and biological evaluation of new derivatives of emodin.	2004 Nov 15	15498672
Influence of functional group substitutions on the carcinogenicity of anthraquinone in rats and mice: analysis of long-term bioassays by the National Cancer Institute and the National Toxicology Program.	2005 Mar-Apr	15804751
The effect of emodin-assisted early enteral nutrition on severe acute pancreatitis and secondary hepatic injury.	2007	18288270
Emodin induces apoptosis through caspase 3-dependent pathway in HK-2 cells.	2007 Mar 7	17240509
Exploration of Emodin to treat alpha-naphthylisothiocyanate-induced cholestatic hepatitis via anti-inflammatory pathway.	2008 Aug 20	18590720
Influence of food polyphenols on aryl hydrocarbon receptor-signaling pathway estimated by in vitro bioassay.	2008 Dec	17869316
The catalytic subunit of human protein kinase CK2 structurally deviates from its maize homologue in complex with the nucleotide competitive inhibitor emodin.	2008 Mar 14	18242640
Is senna laxative use associated to cathartic colon, genotoxicity, or carcinogenicity?	2009	20107583
Emodin targets the beta-hydroxyacyl-acyl carrier protein dehydratase from Helicobacter pylori: enzymatic inhibition assay with crystal structural and thermodynamic characterization.	2009 May 12	19433000
Validation of a new yeast-based reporter assay consisting of human estrogen receptors alpha/beta and coactivator SRC-1: application for detection of estrogenic activity in environmental samples.	2009 Oct	19161236
Role of Rad51 down-regulation and extracellular signal-regulated kinases 1 and 2 inactivation in emodin and mitomycin C-induced synergistic cytotoxicity in human non-small-cell lung cancer cells.	2010 Apr	20042515
Apoptosis induced by emodin is associated with alterations of intracellular acidification and reactive oxygen species in EC-109 cells.	2010 Aug	20651850
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011 Dec 15	21872416
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
Inhibition of cytochrome p450 enzymes by quinones and anthraquinones.	2012 Feb 20	22185593
Effects of an anthraquinone derivative from Rheum officinale Baill, emodin, on airway responses in a murine model of asthma.	2012 Jul	22484343
Emodin induces embryonic toxicity in mouse blastocysts through apoptosis.	2012 Sep 4	22609528
Emodin inhibits human sperm functions by reducing sperm [Ca(2+)]i and tyrosine phosphorylation.	2015 Jan	25463531

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:23:01 UTC 2023` Edited by `admin` on `Fri Dec 15 15:23:01 UTC 2023`
Record UNII	KA46RNI6HN
Record Status	`Validated (UNII)`
Record Version

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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