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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
Rutaecarpine, a quinazolinocarboline alkaloid, inhibits prostaglandin production in RAW264.7 macrophages.
2001 Aug
Modulation of drug-metabolizing enzymes by extracts of a herbal medicine Evodia rutaecarpa in C57BL/6J mice.
2002 Aug 2
Effect of structural modification on the inhibitory selectivity of rutaecarpine derivatives on human CYP1A1, CYP1A2, and CYP1B1.
2003 Aug 4
The depressor and vasodilator effects of rutaecarpine are mediated by calcitonin gene-related peptide.
2003 Feb
Evodiamine, a constituent of Evodiae Fructus, induces anti-proliferating effects in tumor cells.
2003 Jan
Involvement of capsaicin-sensitive sensory nerves in cardioprotection of rutaecarpine in rats.
2003 Jun 15
Stimulation of calcitonin gene-related peptide synthesis and release: mechanisms for a novel antihypertensive drug, rutaecarpine.
2004 Sep
Inhibition of UVA irradiation-modulated signaling pathways by rutaecarpine, a quinazolinocarboline alkaloid, in human keratinocytes.
2004 Sep 13
Physicochemical characterization of rutaecarpine-loaded microemulsion system.
2005 Aug
Characterization of the Phase II metabolites of rutaecarpine in rat by liquid chromatography-electrospray ionization-tandem mass spectrometry.
2005 Dec
Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract.
2005 Feb
Involvement of CGRP in the inhibitory effect of rutaecarpine on vasoconstriction induced by anaphylaxis in guinea pig.
2005 Feb 15
The protective effects of rutaecarpine on gastric mucosa injury in rats.
2005 May
Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine.
2006 Apr
Development and validation of HPLC methods for the analysis of phenethylamine and indoloquinazoline alkaloids in Evodia species.
2006 Mar
Oxidative metabolism of the alkaloid rutaecarpine by human cytochrome P450.
2006 May
Chemical and biological comparisons on Evodia with two related species of different locations and conditions.
2006 Nov 24
The effects of rutaecarpine on the pharmacokinetics of acetaminophen in rats.
2007 Dec
In vitro and in vivo antiallergic effect of the fructus of Evodia rutaecarpa and its constituents.
2007 Jan
Short communication: in vivo evaluation of microemulsion system for oral and parenteral delivery of rutaecarpine to rats.
2007 May
Rutaecarpine induces chloride secretion across rat isolated distal colon.
2008 Apr
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
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
Up-regulation of CYP1A1 by rutaecarpine is dependent on aryl hydrocarbon receptor and calcium.
2009 Dec 21
Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1).
2009 Mar 15
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
Synthesis and biological properties of benzo-annulated rutaecarpines.
2010
Synthesis and evaluation of novel rutaecarpine derivatives and related alkaloids derivatives as selective acetylcholinesterase inhibitors.
2010 Apr
Regulation of dioxin receptor function by different beta-carboline alkaloids.
2010 Aug
Anti-proliferative effects of evodiamine on human thyroid cancer cell line ARO.
2010 Aug 15
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
Investigation on fragmentation pathways of rutaecarpine and its two derivatives using electrospray ionization ion-trap time-of-flight tandem mass spectrometry.
2010 Sep
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