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
SMILES
CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C1
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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. | 1994 Sep-Oct |
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| Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase. | 1995 Nov 15 |
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| Cloning and expression of a rat liver phenobarbital-inducible UDP-glucuronosyltransferase (2B12) with specificity for monoterpenoid alcohols. | 1995 Oct 1 |
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| Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules. | 1996 Sep 3 |
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| The effect of emodin-assisted early enteral nutrition on severe acute pancreatitis and secondary hepatic injury. | 2007 |
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| Inhibition of human cytochrome p450 1b1 further clarifies its role in the activation of dibenzo[a,l]pyrene in cells in culture. | 2007 |
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| 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 |
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| Emodin induces apoptosis through caspase 3-dependent pathway in HK-2 cells. | 2007 Mar 7 |
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| Molecular mechanism of emodin action: transition from laxative ingredient to an antitumor agent. | 2007 Sep |
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| The anthraquinone derivative Emodin ameliorates neurobehavioral deficits of a rodent model for schizophrenia. | 2008 |
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| Exploration of Emodin to treat alpha-naphthylisothiocyanate-induced cholestatic hepatitis via anti-inflammatory pathway. | 2008 Aug 20 |
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| Influence of food polyphenols on aryl hydrocarbon receptor-signaling pathway estimated by in vitro bioassay. | 2008 Dec |
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| Topical anti-inflammatory activity of Polygonum cuspidatum extract in the TPA model of mouse ear inflammation. | 2008 Feb 8 |
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| 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 |
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| Participation of cathepsin B in emodin-induced apoptosis in HK-2 Cells. | 2008 Oct 1 |
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| Is senna laxative use associated to cathartic colon, genotoxicity, or carcinogenicity? | 2009 |
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| Chinese medicines as a resource for liver fibrosis treatment. | 2009 Aug 20 |
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| Quinalizarin as a potent, selective and cell-permeable inhibitor of protein kinase CK2. | 2009 Jul 15 |
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| Eurycomanone induce apoptosis in HepG2 cells via up-regulation of p53. | 2009 Jun 10 |
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| Emodin reverses CCl induced hepatic cytochrome P450 (CYP) enzymatic and ultrastructural changes: The in vivo evidence. | 2009 Mar |
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| Emodin targets the beta-hydroxyacyl-acyl carrier protein dehydratase from Helicobacter pylori: enzymatic inhibition assay with crystal structural and thermodynamic characterization. | 2009 May 12 |
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| Emodin induces a reactive oxygen species-dependent and ATM-p53-Bax mediated cytotoxicity in lung cancer cells. | 2009 Nov 25 |
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| In vitro anti-fibrotic activities of herbal compounds and herbs. | 2009 Oct |
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| 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 |
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| 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 |
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| Emodin enhances sensitivity of gallbladder cancer cells to platinum drugs via glutathion depletion and MRP1 downregulation. | 2010 Apr 15 |
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| Apoptosis induced by emodin is associated with alterations of intracellular acidification and reactive oxygen species in EC-109 cells. | 2010 Aug |
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| Inhibition of ATP-induced macrophage death by emodin via antagonizing P2X7 receptor. | 2010 Aug 25 |
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| The anthraquinone derivative emodin attenuates methamphetamine-induced hyperlocomotion and startle response in rats. | 2010 Dec |
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| Emodin triggers DNA double-strand breaks by stabilizing topoisomerase II-DNA cleavage complexes and by inhibiting ATP hydrolysis of topoisomerase II. | 2010 Dec |
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| Emodin suppresses lipopolysaccharide-induced pro-inflammatory responses and NF-κB activation by disrupting lipid rafts in CD14-negative endothelial cells. | 2010 Dec |
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| Anti-tumor activity of emodin against human chronic myelocytic leukemia K562 cell lines in vitro and in vivo. | 2010 Feb 10 |
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| A CE-based assay for human protein kinase CK2 activity measurement and inhibitor screening. | 2010 Jan |
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| Dose-dependent hepatoprotective effect of emodin against acetaminophen-induced acute damage in rats. | 2010 Nov |
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| Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. | 2011 Dec 15 |
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| 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 |
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| Inhibition of cytochrome p450 enzymes by quinones and anthraquinones. | 2012 Feb 20 |
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| Effects of an anthraquinone derivative from Rheum officinale Baill, emodin, on airway responses in a murine model of asthma. | 2012 Jul |
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| Bioactive anthraquinones from endophytic fungus Aspergillus versicolor isolated from red sea algae. | 2012 Oct |
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| A new herb-drug interaction of Polygonum cuspidatum, a resveratrol-rich nutraceutical, with carbamazepine in rats. | 2012 Sep 15 |
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| Emodin induces embryonic toxicity in mouse blastocysts through apoptosis. | 2012 Sep 4 |
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| 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 |
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| Emodin inhibits growth and induces apoptosis in an orthotopic hepatocellular carcinoma model by blocking activation of STAT3. | 2013 Oct |
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| In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats. | 2014 Aug 5 |
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| Inhibition of Epstein-Barr virus lytic cycle by an ethyl acetate subfraction separated from Polygonum cuspidatum root and its major component, emodin. | 2014 Jan 20 |
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| Antitubercular and antibacterial activity of quinonoid natural products against multi-drug resistant clinical isolates. | 2014 Jul |
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| Inhibitory effects of herbal constituents on P-glycoprotein in vitro and in vivo: herb-drug interactions mediated via P-gp. | 2014 Mar 1 |
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| Involvement of PPARγ in emodin-induced HK-2 cell apoptosis. | 2015 Feb |
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| Emodin inhibits human sperm functions by reducing sperm [Ca(2+)]i and tyrosine phosphorylation. | 2015 Jan |
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| Emodin Attenuates Cigarette Smoke Induced Lung Injury in a Mouse Model via Suppression of Reactive Oxygen Species Production. | 2015 Nov |
Patents
Sample Use Guides
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
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
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NCI_THESAURUS |
C1967
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ACTIVE MOIETY
METABOLITE (PARENT)
