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Details

Stereochemistry ACHIRAL
Molecular Formula C18H13N3O
Molecular Weight 287.3153
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUTECARPINE

SMILES

O=C1N2CCC3=C(NC4=C3C=CC=C4)C2=NC5=C1C=CC=C5

InChI

InChIKey=ACVGWSKVRYFWRP-UHFFFAOYSA-N
InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2

HIDE SMILES / InChI

Description

Rutaecarpine is an indolopyridoquinazolinone alkaloid isolated from Evodia rutaecarpa and related herbs, first isolated by Asahina and Kashiwaki. Among the active components of evodia are quinolone and indoloquinazoline alkaloids, such as evodiamine and rutaecarpine. A significant portion of the analgesic effects of evodia is attributed to these alkaloids. Rutaecarpine has also been shown to have anti-inflammatory action that is related to inhibition of COX-2, as well as other mechanisms. Evodia rutaecarpa ('Wu-Chu-Yu') remains the most popular and multi-purpose herb traditionally used in China for treatment of headache, abdominal pain, postpartum hemorrhage, dysentery and amenorrhea. Rutaecarpine is one of the main active component isolated from 'Wu-Chu-Yu'. Rutaecarpine has been shown to have cardiovascular biological effects such as inotropic and chronotropic, vasorelaxant, anti-platelet aggregation and anti-inflammatory effects. Furthermore, rutaecarpine has the potential for use as an anti-atherosclerosis agent with a novel mechanism. Rutaecarpine prevents hypoxia-reoxygenation-induced myocardial cell apoptosis via inhibition of NADPH oxidases. Also was shown, that rutaecarpine could be effective in preventing the growth of a variety of cancer cells, including downregulating the estrogen receptor of breast cancer.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
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.
2001 Apr
[Determination of evodiamine and rutaecarpine in Evodia rutaecarpa (Juss.) Benth after compatibility with Coptis chinensis Franch].
2001 Dec
Rutaecarpine-induced block of delayed rectifier K+ current in NG108-15 neuronal cells.
2001 Dec
The cardioprotection of rutaecarpine is mediated by endogenous calcitonin related-gene peptide through activation of vanilloid receptors in guinea-pig hearts.
2002 Aug
Modulation of drug-metabolizing enzymes by extracts of a herbal medicine Evodia rutaecarpa in C57BL/6J mice.
2002 Aug 2
Induction of cytochrome P450s by rutaecarpine and metabolism of rutaecarpine by cytochrome P450s.
2004 Aug
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.
2005 Apr 29
Novel inhibitors of acetyl- and butyrylcholinesterase derived from the alkaloids dehydroevodiamine and rutaecarpine.
2005 Mar
The protective effects of rutaecarpine on gastric mucosa injury in rats.
2005 May
Characterization of human liver cytochrome P450 enzymes involved in the metabolism of rutaecarpine.
2006 Apr 11
Determination of evodiamine and rutecarpine in human serum by liquid chromatography-tandem mass spectrometry.
2006 Jul
Immunosuppressive effects of rutaecarpine in female BALB/c mice.
2006 Jul 1
One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine.
2008 Apr
Solid dispersion of rutaecarpine improved its antihypertensive effect in spontaneously hypertensive rats.
2008 Dec
Rutaecarpine inhibits hypoxia/reoxygenation-induced apoptosis in rat hippocampal neurons.
2008 Dec
Quality evaluation of Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography with photodiode-array detection.
2008 Dec 1
Molecular authentication and quality control using a high performance liquid chromatography technique of Fructus Evodiae.
2008 Feb
Reduction of asymmetric dimethylarginine in the protective effects of rutaecarpine on gastric mucosal injury.
2008 Oct
Calcitonin gene-related peptide-mediated antihypertensive and anti-platelet effects by rutaecarpine in spontaneously hypertensive rats.
2008 Oct
Induction of NAD(P)H: quinone reductase by rutaecarpine isolated from the fruits of Evodia rutaecarpa in the murine hepatic Hepa-1c1c7 cell line.
2008 Sep
A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine.
2009 Aug 7
The permeability and the efflux of alkaloids of the Evodiae fructus in the Caco-2 model.
2009 Jan
Involvement of prolylcarboxypeptidase in the effect of rutaecarpine on the regression of mesenteric artery hypertrophy in renovascular hypertensive rats.
2009 Mar
Evodiamine and rutaecarpine inhibit migration by LIGHT via suppression of NADPH oxidase activation.
2009 May 1
Isolation of secondary metabolites from Hortia oreadica (Rutaceae) leaves through high-speed counter-current chromatography.
2009 May 8
[Assay of evodin, evodiamine and rutaecarpine in Fructus Evodiae by QAMS].
2009 Nov
Synthesis and evaluation of novel rutaecarpine derivatives and related alkaloids derivatives as selective acetylcholinesterase inhibitors.
2010 Apr
Optimization of extraction of evodiamine and rutaecarpine from fruit of Evodia rutaecarpa using modified supercritical CO(2).
2010 Dec 10
A new quinolone and other constituents from the fruits of Tetradium ruticarpum: effects on neutrophil pro-inflammatory responses.
2010 Jul
Reversal of isoprenaline-induced cardiac remodeling by rutaecarpine via stimulation of calcitonin gene-related peptide production.
2010 Oct
Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages.
2013 Mar 7
A HAMP promoter bioassay system for identifying chemical compounds that modulate hepcidin expression.
2015 May

Sample Use Guides

In Vivo Use Guide
The appropriate dose of evodia depends on several factors such as the user's age, health, and several other conditions. At this time there is not enough scientific information to determine an appropriate range of doses for evodia. Keep in mind that natural products are not always necessarily safe and dosages can be important. Be sure to follow relevant directions on product labels and consult your pharmacist or physician or other healthcare professional before using. Evodia is a tree that is native to China and Korea. Evodia fruit, which has a strong bitter taste, is commonly used in Traditional Chinese Medicine. The fruit and root bark are also used as medicine in other herbal practice. Among the active components of evodia are quinolone and indoloquinazoline alkaloids, such as evodiamine and rutaecarpine.
Route of Administration: Oral
In Vitro Use Guide
Rutaecarpine was reported to inhibited monocyte migration, which indicates its potential for anti-atherosclerosis activity. There were evaluzted the effect of rutaecarpine on endothelial dysfunction, and focused on the regulation of connexin expression in endothelial cells by rutaecarpine. Endothelia damage was induced by exposing HUVEC-12 to Ox-LDL (100 mg/L) for 24h, which decreased the expression of protective proteins Cx37 and Cx40, but induced atherogenic Cx43 expression, in both mRNA and protein levels, concomitant with the impaired propidium iodide diffusion through the gap junctions. Pretreatment with rutaecarpine effectively recovered the expression of Cx37 and Cx40, but inhibited Cx43 expression, thereby improving gap junction communication and significantly prevented the endothelial dysfunction
Name Type Language
RUTECARPINE
MI  
Common Name English
8,13-DIHYDROINDOLO(2',3':3,4)PYRIDO(2,1-B)QUINAZOLIN-5(7H)-ONE
Systematic Name English
RUTECARPINE [MI]
Common Name English
NSC-258317
Code English
Code System Code Type Description
MESH
C028632
Created by admin on Tue Oct 22 14:38:17 UTC 2019 , Edited by admin on Tue Oct 22 14:38:17 UTC 2019
PRIMARY
PUBCHEM
65752
Created by admin on Tue Oct 22 14:38:17 UTC 2019 , Edited by admin on Tue Oct 22 14:38:17 UTC 2019
PRIMARY
EPA CompTox
84-26-4
Created by admin on Tue Oct 22 14:38:17 UTC 2019 , Edited by admin on Tue Oct 22 14:38:17 UTC 2019
PRIMARY
CAS
84-26-4
Created by admin on Tue Oct 22 14:38:17 UTC 2019 , Edited by admin on Tue Oct 22 14:38:17 UTC 2019
PRIMARY
MERCK INDEX
M9702
Created by admin on Tue Oct 22 14:38:17 UTC 2019 , Edited by admin on Tue Oct 22 14:38:17 UTC 2019
PRIMARY Merck Index