RUTECARPINE

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 Search

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
Sources: http://www.itmonline.org/articles/evodia/evodia.htm
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 189 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10669112	Inhibitor 7728
PI3K-Akt signaling pathway 23 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26972495	Modulator 780
AMPK signaling pathway 4 Target ID: map04152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26972495	Modulator 780

Conditions

Condition	Modality	Highest Phase	Product
Cardiovascular diseases 70 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20336017	Preventing	Approved 8043	Unknown Approved Use Unknown
Heart failure 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21423291	Preventing	Approved 8043	Unknown Approved Use Unknown
Hyperlipidemia 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26972495	Preventing	Approved 8043	Unknown Approved Use Unknown
Cancer 569 Sources: http://www.biolreprod.org/content/83/Suppl_1/134	Preventing	Approved 8043	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Rutaecarpine-induced block of delayed rectifier K+ current in NG108-15 neuronal cells.	2001 Dec	11684147
The cardioprotection of rutaecarpine is mediated by endogenous calcitonin related-gene peptide through activation of vanilloid receptors in guinea-pig hearts.	2002 Aug	12221592
The depressor and vasodilator effects of rutaecarpine are mediated by calcitonin gene-related peptide.	2003 Feb	12624816
Characterization of in vitro metabolites of rutaecarpine in rat liver microsomes using liquid chromatography/tandem mass spectrometry.	2004	15150830
Protective effects of rutaecarpine in cardiac anaphylactic injury is mediated by CGRP.	2004 Dec	15643546
Characterization of the Phase II metabolites of rutaecarpine in rat by liquid chromatography-electrospray ionization-tandem mass spectrometry.	2005 Dec	16418066
Involvement of CGRP in the inhibitory effect of rutaecarpine on vasoconstriction induced by anaphylaxis in guinea pig.	2005 Feb 15	15582719
Novel inhibitors of acetyl- and butyrylcholinesterase derived from the alkaloids dehydroevodiamine and rutaecarpine.	2005 Mar	15725500
The protective effects of rutaecarpine on gastric mucosa injury in rats.	2005 May	15931578
Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine.	2006 Apr	16423507
Immunosuppressive effects of rutaecarpine in female BALB/c mice.	2006 Jul 1	16412592
Calcitonin gene-related Peptide-mediated depressor effect and inhibiting vascular hypertrophy of rutaecarpine in renovascular hypertensive rats.	2007 Dec	18091582
In vitro and in vivo antiallergic effect of the fructus of Evodia rutaecarpa and its constituents.	2007 Jan	17202687
Radical reactions with 3H-quinazolin-4-ones: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin.	2007 Jan 7	17164913
[Methodological studies on equivalent relationship between granule for clinical prescription and clinical decoction of fructus evodiae].	2007 Jun	17802873
Short communication: in vivo evaluation of microemulsion system for oral and parenteral delivery of rutaecarpine to rats.	2007 May	17520444
One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine.	2008 Apr	18379119
Rutaecarpine induces chloride secretion across rat isolated distal colon.	2008 Apr	18187619
Solid dispersion of rutaecarpine improved its antihypertensive effect in spontaneously hypertensive rats.	2008 Dec	19016276
Molecular authentication and quality control using a high performance liquid chromatography technique of Fructus Evodiae.	2008 Feb	18239294
Calcitonin gene-related peptide-mediated antihypertensive and anti-platelet effects by rutaecarpine in spontaneously hypertensive rats.	2008 Oct	18625276
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	18729042
A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine.	2009 Aug 7	19527008
Up-regulation of CYP1A1 by rutaecarpine is dependent on aryl hydrocarbon receptor and calcium.	2009 Dec 21	19853001
[Determination of evodiamine and rutaecarpine of compound Wuzhuyu cataplasm in plasma by SPE-HPLC: application to its pharmacokinetics].	2009 Nov	20209967
[Assay of evodin, evodiamine and rutaecarpine in Fructus Evodiae by QAMS].	2009 Nov	20209915
Effects of evodiamine and rutaecarpine on the secretion of corticosterone by zona fasciculata-reticularis cells in male rats.	2009 Oct 1	19639602
Synthesis and biological properties of benzo-annulated rutaecarpines.	2010	20930379
Synthesis and evaluation of novel rutaecarpine derivatives and related alkaloids derivatives as selective acetylcholinesterase inhibitors.	2010 Apr	20079560
Regulation of dioxin receptor function by different beta-carboline alkaloids.	2010 Aug	20449727
Anti-proliferative effects of evodiamine on human thyroid cancer cell line ARO.	2010 Aug 15	20503248
Optimization of extraction of evodiamine and rutaecarpine from fruit of Evodia rutaecarpa using modified supercritical CO(2).	2010 Dec 10	21067761
A new quinolone and other constituents from the fruits of Tetradium ruticarpum: effects on neutrophil pro-inflammatory responses.	2010 Jul	20658672
Pharmacological effects of rutaecarpine as a cardiovascular protective agent.	2010 Mar 15	20336017
Accelerated senescence of endothelial progenitor cells in hypertension is related to the reduction of calcitonin gene-related peptide.	2010 May	20375903
Reversal of isoprenaline-induced cardiac remodeling by rutaecarpine via stimulation of calcitonin gene-related peptide production.	2010 Oct	20962894
Investigation on fragmentation pathways of rutaecarpine and its two derivatives using electrospray ionization ion-trap time-of-flight tandem mass spectrometry.	2010 Sep	20814986
Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages.	2013 Mar 7	23337743
A HAMP promoter bioassay system for identifying chemical compounds that modulate hepcidin expression.	2015 May	25633564

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

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)