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 |
|---|---|---|
| Emodin Attenuates Cigarette Smoke Induced Lung Injury in a Mouse Model via Suppression of Reactive Oxygen Species Production. | 2015-11 |
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| Involvement of PPARγ in emodin-induced HK-2 cell apoptosis. | 2015-02 |
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| Emodin inhibits human sperm functions by reducing sperm [Ca(2+)]i and tyrosine phosphorylation. | 2015-01 |
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| In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats. | 2014-08-05 |
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| Antitubercular and antibacterial activity of quinonoid natural products against multi-drug resistant clinical isolates. | 2014-07 |
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| Inhibitory effects of herbal constituents on P-glycoprotein in vitro and in vivo: herb-drug interactions mediated via P-gp. | 2014-03-01 |
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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. | 2014-01-20 |
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| Emodin inhibits growth and induces apoptosis in an orthotopic hepatocellular carcinoma model by blocking activation of STAT3. | 2013-10 |
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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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| Bioactive anthraquinones from endophytic fungus Aspergillus versicolor isolated from red sea algae. | 2012-10 |
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| A new herb-drug interaction of Polygonum cuspidatum, a resveratrol-rich nutraceutical, with carbamazepine in rats. | 2012-09-15 |
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| Emodin induces embryonic toxicity in mouse blastocysts through apoptosis. | 2012-09-04 |
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| Effects of an anthraquinone derivative from Rheum officinale Baill, emodin, on airway responses in a murine model of asthma. | 2012-07 |
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| Inhibition of cytochrome p450 enzymes by quinones and anthraquinones. | 2012-02-20 |
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| Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. | 2011-12-15 |
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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. | 2011-05 |
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| The anthraquinone derivative emodin attenuates methamphetamine-induced hyperlocomotion and startle response in rats. | 2010-12 |
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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. | 2010-12 |
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| Emodin suppresses lipopolysaccharide-induced pro-inflammatory responses and NF-κB activation by disrupting lipid rafts in CD14-negative endothelial cells. | 2010-12 |
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| Dose-dependent hepatoprotective effect of emodin against acetaminophen-induced acute damage in rats. | 2010-11 |
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| Inhibition of ATP-induced macrophage death by emodin via antagonizing P2X7 receptor. | 2010-08-25 |
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| Apoptosis induced by emodin is associated with alterations of intracellular acidification and reactive oxygen species in EC-109 cells. | 2010-08 |
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| Emodin enhances sensitivity of gallbladder cancer cells to platinum drugs via glutathion depletion and MRP1 downregulation. | 2010-04-15 |
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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. | 2010-04 |
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| Anti-tumor activity of emodin against human chronic myelocytic leukemia K562 cell lines in vitro and in vivo. | 2010-02-10 |
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| A CE-based assay for human protein kinase CK2 activity measurement and inhibitor screening. | 2010-01 |
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| Emodin induces a reactive oxygen species-dependent and ATM-p53-Bax mediated cytotoxicity in lung cancer cells. | 2009-11-25 |
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| In vitro anti-fibrotic activities of herbal compounds and herbs. | 2009-10 |
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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. | 2009-10 |
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| Chinese medicines as a resource for liver fibrosis treatment. | 2009-08-20 |
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| Quinalizarin as a potent, selective and cell-permeable inhibitor of protein kinase CK2. | 2009-07-15 |
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| Eurycomanone induce apoptosis in HepG2 cells via up-regulation of p53. | 2009-06-10 |
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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. | 2009-05-12 |
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| Emodin reverses CCl induced hepatic cytochrome P450 (CYP) enzymatic and ultrastructural changes: The in vivo evidence. | 2009-03 |
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| Is senna laxative use associated to cathartic colon, genotoxicity, or carcinogenicity? | 2009 |
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| Influence of food polyphenols on aryl hydrocarbon receptor-signaling pathway estimated by in vitro bioassay. | 2008-12 |
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| Participation of cathepsin B in emodin-induced apoptosis in HK-2 Cells. | 2008-10-01 |
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| Exploration of Emodin to treat alpha-naphthylisothiocyanate-induced cholestatic hepatitis via anti-inflammatory pathway. | 2008-08-20 |
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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. | 2008-03-14 |
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| Topical anti-inflammatory activity of Polygonum cuspidatum extract in the TPA model of mouse ear inflammation. | 2008-02-08 |
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| The anthraquinone derivative Emodin ameliorates neurobehavioral deficits of a rodent model for schizophrenia. | 2008 |
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| Molecular mechanism of emodin action: transition from laxative ingredient to an antitumor agent. | 2007-09 |
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| Emodin induces apoptosis through caspase 3-dependent pathway in HK-2 cells. | 2007-03-07 |
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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. | 2007-02-15 |
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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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| Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules. | 1996-09-03 |
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| Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase. | 1995-11-15 |
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| Cloning and expression of a rat liver phenobarbital-inducible UDP-glucuronosyltransferase (2B12) with specificity for monoterpenoid alcohols. | 1995-10-01 |
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| Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. | 1994-09-01 |
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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C1967
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ACTIVE MOIETY
METABOLITE (PARENT)
