518-17-2 | Evodiamine

Packsize	Purity	Availability	Price	Discounted Price
50mg	≥98%	in stock	$48.00	$34.00
100mg	≥98%	in stock	$84.00	$59.00
250mg	≥98%	in stock	$156.00	$109.00
1g	≥98%	in stock	$546.00	$382.00

Description

• Catalog Number: AI51606
• Chemical Name: Evodiamine
• CAS Number: 518-17-2
• Molecular Formula: C19H17N3O
• Molecular Weight: 303.3578
• MDL Number: MFCD06407824
• SMILES: O=C1c2ccccc2N(C2N1CCc1c2[nH]c2c1cccc2)C

Computed Properties

• Complexity: 495
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Heavy Atom Count: 23
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• XLogP3: 3.1

Literature

• Evodiamine, a plant alkaloid, induces calcium/JNK-mediated autophagy and calcium/mitochondria-mediated apoptosis in human glioblastoma cells.

  Chemico-biological interactions 20130905

• Berberine and evodiamine influence serotonin transporter (5-HTT) expression via the 5-HTT-linked polymorphic region.

  The pharmacogenomics journal 20121001

• New tricks for an old natural product: discovery of highly potent evodiamine derivatives as novel antitumor agents by systemic structure-activity relationship analysis and biological evaluations.

  Journal of medicinal chemistry 20120913

• Transdermal behaviors comparisons among Evodia rutaecarpa extracts with different purity of evodiamine and rutaecarpine and the effect of topical formulation in vivo.

  Fitoterapia 20120701

• Evodiamine, a dual catalytic inhibitor of type I and II topoisomerases, exhibits enhanced inhibition against camptothecin resistant cells.

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20120515

• Cytotoxic effect of evodiamine in SGC-7901 human gastric adenocarcinoma cells via simultaneous induction of apoptosis and autophagy.

  Oncology reports 20120501

• Pharmacokinetic comparisons of rutaecarpine and evodiamine after oral administration of Wu-Chu-Yu extracts with different purities to rats.

  Journal of ethnopharmacology 20120131

• Six alkaloids inhibit secretion of IL-1α, TXB(2), ET-1 and E-selectin in LPS-induced endothelial cells.

  Immunological investigations 20120101

• Enhanced antitumor efficacy of gemcitabine by evodiamine on pancreatic cancer via regulating PI3K/Akt pathway.

  International journal of biological sciences 20120101

• Simultaneous determination and pharmacokinetic analysis of seven alkaloids and two flavonoids from rat plasma by HPLC-DAD after oral administration of Wuzhuyu decoction.

  Journal of Asian natural products research 20120101

• In vitro cellular uptake of evodiamine and rutaecarpine using a microemulsion.

  International journal of nanomedicine 20120101

• A drug screening method based on the autophagy pathway and studies of the mechanism of evodiamine against influenza A virus.

  PloS one 20120101

• Binding mode pediction of evodiamine within vanilloid receptor TRPV1.

  International journal of molecular sciences 20120101

• Induction of apoptosis by evodiamine involves both activation of mitotic arrest and mitotic slippage.

  Oncology reports 20111201

• Simultaneous determination of evodiamine and rutecarpine in rabbit plasma by LC-ESI-MS and its application to pharmacokinetics.

  Die Pharmazie 20111201

• [Studies on pharmacokinetics of evodiamine and rutaecarpine in rats plasma after oral administration extracts of euodiae fructus].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20111201

• Molecular mechanisms of activation of endothelial nitric oxide synthase mediated by transient receptor potential vanilloid type 1.

  Cardiovascular research 20110801

• Evodiamine inhibits 12-O-tetradecanoylphorbol-13-acetate-induced activator protein 1 transactivation and cell transformation in human hepatocytes.

  Phytotherapy research : PTR 20110701

• Acid sphingomyelinase contributes to evodiamine-induced apoptosis in human gastric cancer SGC-7901 cells.

  DNA and cell biology 20110601

• Inhibitory effects of Zuo-Jin-Wan and its alkaloidal ingredients on activator protein 1, nuclear factor-κB, and cellular transformation in HepG2 cells.

  Fitoterapia 20110601

• [Determination of evodiamine and rutacarpine in zhuyu hewei zhitong capsules by HPLC].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110401

• Evodiamine improves congnitive abilities in SAMP8 and APP(swe)/PS1(ΔE9) transgenic mouse models of Alzheimer's disease.

  Acta pharmacologica Sinica 20110301

• [Optimization of a HPLC determination method for Evodia rutaecarpa].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110201

• New strategies in the discovery of novel non-camptothecin topoisomerase I inhibitors.

  Current medicinal chemistry 20110101

• Enhanced transdermal delivery of evodiamine and rutaecarpine using microemulsion.

  International journal of nanomedicine 20110101

• [Synthesis, physicochemical and pharmacological properties of pentacyclic alkaloid-analogues].

  Acta pharmaceutica Hungarica 20110101

• Optimization of extraction of evodiamine and rutaecarpine from fruit of Evodia rutaecarpa using modified supercritical CO(2).

  Journal of chromatography. A 20101210

• Selection of evodiamine as a novel topoisomerase I inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents.

  Journal of medicinal chemistry 20101111

• Evodiamine as a novel antagonist of aryl hydrocarbon receptor.

  Biochemical and biophysical research communications 20101105

• Evodiamine induces caspase-dependent apoptosis and S phase arrest in human colon lovo cells.

  Anti-cancer drugs 20100901

• Anti-proliferative effects of evodiamine on human thyroid cancer cell line ARO.

  Journal of cellular biochemistry 20100815

• Protein tyrosine kinase pathway-derived ROS/NO productions contribute to G2/M cell cycle arrest in evodiamine-treated human cervix carcinoma HeLa cells.

  Free radical research 20100701

• A new quinolone and other constituents from the fruits of Tetradium ruticarpum: effects on neutrophil pro-inflammatory responses.

  Chemistry & biodiversity 20100701

• Inhibitory effect and transcriptional impact of berberine and evodiamine on human white preadipocyte differentiation.

  Fitoterapia 20100601

• Evodiamine-induced human melanoma A375-S2 cell death was mediated by PI3K/Akt/caspase and Fas-L/NF-kappaB signaling pathways and augmented by ubiquitin-proteasome inhibition.

  Toxicology in vitro : an international journal published in association with BIBRA 20100401

• Inhibitory effect of evodiamine alone and in combination with rosiglitazone on in vitro adipocyte differentiation and in vivo obesity related to diabetes.

  International journal of obesity (2005) 20100201

• Immobilizing topoisomerase I on a surface plasmon resonance biosensor chip to screen for inhibitors.

  Journal of biomedical science 20100101

• Evodiamine inhibits adipogenesis via the EGFR-PKCalpha-ERK signaling pathway.

  FEBS letters 20091119

• [Assay of evodin, evodiamine and rutaecarpine in Fructus Evodiae by QAMS].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20091101

• [Determination of evodiamine and rutaecarpine of compound Wuzhuyu cataplasm in plasma by SPE-HPLC: application to its pharmacokinetics].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20091101

• Effects of evodiamine and rutaecarpine on the secretion of corticosterone by zona fasciculata-reticularis cells in male rats.

  Journal of cellular biochemistry 20091001

• Evodiamine represses hypoxia-induced inflammatory proteins expression and hypoxia-inducible factor 1alpha accumulation in RAW264.7.

  Shock (Augusta, Ga.) 20090901

• Antiproliferation and apoptosis induced by evodiamine in human colorectal carcinoma cells (COLO-205).

  Chemistry & biodiversity 20090601

• Evodiamine: a novel anti-cancer alkaloid from Evodia rutaecarpa.

  Molecules (Basel, Switzerland) 20090518

• Evodiamine and rutaecarpine inhibit migration by LIGHT via suppression of NADPH oxidase activation.

  Journal of cellular biochemistry 20090501

• [Study on vitro release and transdermal behaviors of Yulian cataplasm].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090401

• Evodiamine stabilizes topoisomerase I-DNA cleavable complex to inhibit topoisomerase I activity.

  Molecules (Basel, Switzerland) 20090327

• Intragastric administration of evodiamine suppresses NPY and AgRP gene expression in the hypothalamus and decreases food intake in rats.

  Brain research 20090109

• The permeability and the efflux of alkaloids of the Evodiae fructus in the Caco-2 model.

  Phytotherapy research : PTR 20090101

• Enhancement of apoptosis of human hepatocellular carcinoma SMMC-7721 cells through synergy of berberine and evodiamine.

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20081201

• Immunoregulatory effect of evodiamine in mice of various germlines.

  Zhongguo shi yan xue ye xue za zhi 20080801

• Reactive oxygen species and nitric oxide regulate mitochondria-dependent apoptosis and autophagy in evodiamine-treated human cervix carcinoma HeLa cells.

  Free radical research 20080501

• Evodiamine improves diet-induced obesity in a uncoupling protein-1-independent manner: involvement of antiadipogenic mechanism and extracellularly regulated kinase/mitogen-activated protein kinase signaling.

  Endocrinology 20080101

• Nitric oxide activated by p38 and NF-kappaB facilitates apoptosis and cell cycle arrest under oxidative stress in evodiamine-treated human melanoma A375-S2 cells.

  Free radical research 20080101

• Critical roles of reactive oxygen species in mitochondrial permeability transition in mediating evodiamine-induced human melanoma A375-S2 cell apoptosis.

  Free radical research 20071001

• [Methodological studies on equivalent relationship between granule for clinical prescription and clinical decoction of fructus evodiae].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20070601

• Anti-proliferative effects of evodiamine on human prostate cancer cell lines DU145 and PC3.

  Journal of cellular biochemistry 20070501

• Anti-inflammatory effects and mechanisms of the ethanol extract of Evodia rutaecarpa and its bioactive components on neutrophils and microglial cells.

  European journal of pharmacology 20070126

• In vitro and in vivo antiallergic effect of the fructus of Evodia rutaecarpa and its constituents.

  Biological & pharmaceutical bulletin 20070101

• Chemical and biological comparisons on Evodia with two related species of different locations and conditions.

  Journal of ethnopharmacology 20061124

• Caspase-dependent and caspase-independent apoptosis induced by evodiamine in human leukemic U937 cells.

  Molecular cancer therapeutics 20060901

• Determination of evodiamine and rutecarpine in human serum by liquid chromatography-tandem mass spectrometry.

  Analytical and bioanalytical chemistry 20060701

• Evodiamine inhibits in vitro angiogenesis: Implication for antitumorgenicity.

  Life sciences 20060404

• Anti-inflammatory principles from the fruits of Evodia rutaecarpa and their cellular action mechanisms.

  Archives of pharmacal research 20060401

• Development and validation of HPLC methods for the analysis of phenethylamine and indoloquinazoline alkaloids in Evodia species.

  Journal of separation science 20060301

• [Effect of protein kinase C on human melanoma A375-S2 cell death induced by evodiamine].

  Yao xue xue bao = Acta pharmaceutica Sinica 20051101

• Evodiamine induced human melanoma A375-S2 cell death partially through interleukin 1 mediated pathway.

  Biological & pharmaceutical bulletin 20050601

• Antitumor mechanism of evodiamine, a constituent from Chinese herb Evodiae fructus, in human multiple-drug resistant breast cancer NCI/ADR-RES cells in vitro and in vivo.

  Carcinogenesis 20050501

• Evodiamine abolishes constitutive and inducible NF-kappaB activation by inhibiting IkappaBalpha kinase activation, thereby suppressing NF-kappaB-regulated antiapoptotic and metastatic gene expression, up-regulating apoptosis, and inhibiting invasion.

  The Journal of biological chemistry 20050429

• Roles of SIRT1 and phosphoinositide 3-OH kinase/protein kinase C pathways in evodiamine-induced human melanoma A375-S2 cell death.

  Journal of pharmacological sciences 20050401

• Induction of mitotic arrest and apoptosis in human prostate cancer pc-3 cells by evodiamine.

  The Journal of urology 20050101

• Protective effects of evodiamine on myocardial ischemia-reperfusion injury in rats.

  Planta medica 20041201

• Evodiamine functions as an agonist for the vanilloid receptor TRPV1.

  Organic & biomolecular chemistry 20040821

• [Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth].

  Yao xue xue bao = Acta pharmaceutica Sinica 20040801

• Inhibitory effects of evodiamine on the growth of human prostate cancer cell line LNCaP.

  International journal of cancer 20040710

• Induction of mitotic arrest and apoptosis by evodiamine in human leukemic T-lymphocytes.

  Life sciences 20040521

• Inhibition by evodiamine of hepatocyte growth factor-induced invasion and migration of tumor cells.

  Biological & pharmaceutical bulletin 20040401

• Atypical apoptosis in L929 cells induced by evodiamine isolated from Evodia rutaecarpa.

  Journal of Asian natural products research 20040301

• Evodiamine induces tumor cell death through different pathways: apoptosis and necrosis.

  Acta pharmacologica Sinica 20040101

• Intracellular regulation of evodiamine-induced A375-S2 cell death.

  Biological & pharmaceutical bulletin 20031101

• [Evodiamine induces A375-S2 cell death through two different pathways].

  Yao xue xue bao = Acta pharmaceutica Sinica 20030901

• The nociceptive and anti-nociceptive effects of evodiamine from fruits of Evodia rutaecarpa in mice.

  Planta medica 20030501

• [Advances in pharmacological study of Evodia rutaecarpa and its effective constituents].

  Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20030401

• Protective effects of calcitonin gene-related peptide-mediated evodiamine on guinea-pig cardiac anaphylaxis.

  Naunyn-Schmiedeberg's archives of pharmacology 20030301

• Evodiamine, a constituent of Evodiae Fructus, induces anti-proliferating effects in tumor cells.

  Cancer science 20030101

• Effects of evodiamine on gastrointestinal motility in male rats.

  European journal of pharmacology 20021220

• Anti-invasive and metastatic activities of evodiamine.

  Biological & pharmaceutical bulletin 20021101

• [Studies on evodiamine induced HeLa cell apoptosis].

  Yao xue xue bao = Acta pharmaceutica Sinica 20020901

• Modulation of drug-metabolizing enzymes by extracts of a herbal medicine Evodia rutaecarpa in C57BL/6J mice.

  Life sciences 20020802

• Pharmacological profile of evodiamine in isolated rabbit corpus cavernosum.

  European journal of pharmacology 20020620

• The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes.

  Drug metabolism and disposition: the biological fate of chemicals 20020301

• [Determination of evodiamine and rutaecarpine in Evodia rutaecarpa (Juss.) Benth after compatibility with Coptis chinensis Franch].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20011201

• Capsaicin-like anti-obese activities of evodiamine from fruits of Evodia rutaecarpa, a vanilloid receptor agonist.

  Planta medica 20011001

• Inhibitory effects of evodiamine on in vitro invasion and experimental lung metastasis of murine colon cancer cells.

  Biological & pharmaceutical bulletin 20010801

• Inhibitory effect of evodiamine on aldosterone release by Zona glomerulosa cells in male rats.

  The Chinese journal of physiology 20010630

• The positive inotropic and chronotropic effects of evodiamine and rutaecarpine, indoloquinazoline alkaloids isolated from the fruits of Evodia rutaecarpa, on the guinea-pig isolated right atria: possible involvement of vanilloid receptors.

  Planta medica 20010401