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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:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20336017 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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
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
Protective effects of rutaecarpine in cardiac anaphylactic injury is mediated by CGRP.
2004 Dec
Characterization of the Phase II metabolites of rutaecarpine in rat by liquid chromatography-electrospray ionization-tandem mass spectrometry.
2005 Dec
Involvement of CGRP in the inhibitory effect of rutaecarpine on vasoconstriction induced by anaphylaxis in guinea pig.
2005 Feb 15
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
Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine.
2006 Apr
Immunosuppressive effects of rutaecarpine in female BALB/c mice.
2006 Jul 1
Calcitonin gene-related Peptide-mediated depressor effect and inhibiting vascular hypertrophy of rutaecarpine in renovascular hypertensive rats.
2007 Dec
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
[Methodological studies on equivalent relationship between granule for clinical prescription and clinical decoction of fructus evodiae].
2007 Jun
Short communication: in vivo evaluation of microemulsion system for oral and parenteral delivery of rutaecarpine to rats.
2007 May
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
Solid dispersion of rutaecarpine improved its antihypertensive effect in spontaneously hypertensive rats.
2008 Dec
Molecular authentication and quality control using a high performance liquid chromatography technique of Fructus Evodiae.
2008 Feb
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
Up-regulation of CYP1A1 by rutaecarpine is dependent on aryl hydrocarbon receptor and calcium.
2009 Dec 21
[Determination of evodiamine and rutaecarpine of compound Wuzhuyu cataplasm in plasma by SPE-HPLC: application to its pharmacokinetics].
2009 Nov
[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
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
Pharmacological effects of rutaecarpine as a cardiovascular protective agent.
2010 Mar 15
Accelerated senescence of endothelial progenitor cells in hypertension is related to the reduction of calcitonin gene-related peptide.
2010 May
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

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
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