U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H13N3O
Molecular Weight 287.316
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUTECARPINE

SMILES

c1ccc2c(c1)c3CCn4c(-c3[nH]2)nc5ccccc5c4=O

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
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/21423291

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Determination of evodiamine and rutaecarpine in Evodia rutaecarpa (Juss.) Benth after compatibility with Coptis chinensis Franch].
2001 Dec
Induction of cytochrome P450-dependent monooxygenase in mouse liver and kidney by rutaecarpine, an alkaloid of the herbal drug Evodia rutaecarpa.
2001 Nov 30
Modulation of drug-metabolizing enzymes by extracts of a herbal medicine Evodia rutaecarpa in C57BL/6J mice.
2002 Aug 2
The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes.
2002 Mar
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
Characterization of in vitro metabolites of rutaecarpine in rat liver microsomes using liquid chromatography/tandem mass spectrometry.
2004
[Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth].
2004 Aug
Characterization of the Phase II metabolites of rutaecarpine in rat by liquid chromatography-electrospray ionization-tandem mass spectrometry.
2005 Dec
Alteration of the pharmacokinetics of theophylline by rutaecarpine, an alkaloid of the medicinal herb Evodia rutaecarpa, in rats.
2005 Feb
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
Determination of evodiamine and rutecarpine in human serum by liquid chromatography-tandem mass spectrometry.
2006 Jul
The effects of rutaecarpine on the pharmacokinetics of acetaminophen in rats.
2007 Dec
One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine.
2008 Apr
Rutaecarpine induces chloride secretion across rat isolated distal colon.
2008 Apr
Progress in the studies on rutaecarpine.
2008 Feb 6
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
A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine.
2009 Aug 7
Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1).
2009 Mar 15
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
Effects of evodiamine and rutaecarpine on the secretion of corticosterone by zona fasciculata-reticularis cells in male rats.
2009 Oct 1
Synthesis and biological properties of benzo-annulated rutaecarpines.
2010
Optimization of extraction of evodiamine and rutaecarpine from fruit of Evodia rutaecarpa using modified supercritical CO(2).
2010 Dec 10
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

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.
Route of Administration: Oral
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
RUTAECARPINE
Common Name English
RUTECARPINE [MI]
Common Name English
NSC-258317
Code English
Classification Tree Code System Code
DSLD 1394 (Number of products:104)
Created by admin on Sat Jun 26 16:37:54 UTC 2021 , Edited by admin on Sat Jun 26 16:37:54 UTC 2021
Code System Code Type Description
MESH
C028632
Created by admin on Sat Jun 26 16:37:54 UTC 2021 , Edited by admin on Sat Jun 26 16:37:54 UTC 2021
PRIMARY
PUBCHEM
65752
Created by admin on Sat Jun 26 16:37:54 UTC 2021 , Edited by admin on Sat Jun 26 16:37:54 UTC 2021
PRIMARY
EPA CompTox
84-26-4
Created by admin on Sat Jun 26 16:37:54 UTC 2021 , Edited by admin on Sat Jun 26 16:37:54 UTC 2021
PRIMARY
CAS
84-26-4
Created by admin on Sat Jun 26 16:37:54 UTC 2021 , Edited by admin on Sat Jun 26 16:37:54 UTC 2021
PRIMARY
MERCK INDEX
M9702
Created by admin on Sat Jun 26 16:37:54 UTC 2021 , Edited by admin on Sat Jun 26 16:37:54 UTC 2021
PRIMARY Merck Index
FDA UNII
8XZV289PRY
Created by admin on Sat Jun 26 16:37:54 UTC 2021 , Edited by admin on Sat Jun 26 16:37:54 UTC 2021
PRIMARY