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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
The cardioprotection of rutaecarpine is mediated by endogenous calcitonin related-gene peptide through activation of vanilloid receptors in guinea-pig hearts.
2002 Aug
The depressor and vasodilator effects of rutaecarpine are mediated by calcitonin gene-related peptide.
2003 Feb
Physicochemical characterization of rutaecarpine-loaded microemulsion system.
2005 Aug
Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract.
2005 Feb
Effects of Evodia rutaecarpa and rutaecarpine on the pharmacokinetics of caffeine in rats.
2005 Jul
Characterization of human liver cytochrome P450 enzymes involved in the metabolism of rutaecarpine.
2006 Apr 11
In vitro and in vivo antiallergic effect of the fructus of Evodia rutaecarpa and its constituents.
2007 Jan
Radical reactions with 3H-quinazolin-4-ones: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin.
2007 Jan 7
One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine.
2008 Apr
Rutaecarpine inhibits hypoxia/reoxygenation-induced apoptosis in rat hippocampal neurons.
2008 Dec
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
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
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
A new quinolone and other constituents from the fruits of Tetradium ruticarpum: effects on neutrophil pro-inflammatory responses.
2010 Jul
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