Rutaecarpine

Names

[ CAS No. ]:
84-26-4

[ Name ]:
Rutaecarpine

[Synonym ]:
ruteacarpine
Rutecarpine
MFCD00210551
Indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one, 8,13-dihydro-
RUTECARPINE 95+
8,13-Dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one

Biological Activity

[Description]:

Rutaecarpine, an alkaloid of Evodia rutaecarpa, is an inhibitor of COX-2 with an IC50 value of 0.28 μM.

[Related Catalog]:

Natural Products >> Alkaloid

Research Areas >> Inflammation/Immunology

[Target]

COX-2:0.28 μM (IC50, in BMMC)

COX-1:8.7 μM (IC50, in BMMC)

[In Vitro]

Rutaecarpine has shown a variety of intriguing biological properties such as anti-thrombotic, anticancer, anti-inflammatory and analgesic, anti-obesity and thermoregulatory, vasorelaxing activity, as well as effects on the cardiovascular and endocrine systems[2]. Rutaecarpine inhibits COX-2 and COX-1 dependent phases of PGD2 generation in BMMC in a concentration-dependent manner with an IC50 of 0.28 μM and 8.7 μM, respectively. It inhibits COX-2-dependent conversion of exogenous arachidonic acid to PGE2 in a dose-dependent manner by the COX-2-transfected HEK293 cells[1].

[In Vivo]

Rutaecarpine showed in vivo anti-inflammatory activity on rat l-carrageenan induced paw edema by intraperitoneal administration[1]. Rutaecarpine significantly decreases the number of antibody-forming cells and causes weight decrease in spleen in a dose-dependent manner. In addition, rutaecarpine administered mice exhibit reduced splenic cellularity, decreased numbers of total T cells, CD4+ cells, CD8+ cells, and B cells in spleen. IL-2, interferon and IL-10 mRNA expressions are suppressed significantly by rutaecarpine treatment. The number of CD4+IL-2+ cells is reduced significantly following administration of mice with rutaecarpine[3].

[Cell Assay]

Rutaecarpine is dissolved in DMSO and diluted with appropriate medium before use. COX-1 and COX-2 cDNA-transfected HEK293 cells are prepared. For measuring inhibitory activity on COX-1 and COX-2 by rutaecarpine, cells in 1 mL of culture medium are seeded into each well of 24-well. After culture for 4 days, the supernatants are removed and 250 mL of fresh medium is added to the cells with or without rutaecarpine. After preincubation for 5 h at 37°C, the cells are further incubated at 37°C for 30 min with 50 mM arachidonic acid. All reactions are stopped by centrifugation at 120 g at 4°C for 5 min. Concentrations of PGE2 in the supernatant are measured[1].

[Animal admin]

Rats: Rutaecarpine is dissolved in 0.1% carboxymethyl cellulose and diluted with appropriate medium before use. Male Splague-Dawley (SD) rats (180-220 g) are used in the study. Rutaecarpine administered intraperitoneally and, 1 h later, l-carrageenan solution is injected to right hind paw of rats. Paw volumes are measured using plethysmometer 5 h after l-carrageenan injection[1]. Mice: For the antibody response to SRBCs, rutaecarpine is administered at a single dose of 10 mg/kg, 20 mg/kg, 40 mg/kg or 80 mg/kg in 10 mL of 1% povidone solution intravenously. Control animals are given 1% povidone solution at 10 mL/kg. Specific pathogen-free female BALB/c mice are used in the study[3].

[References]

[1]. Moon TC, et al. A new class of COX-2 inhibitor, rutaecarpine from Evodia rutaecarpa. Inflamm Res. 1999 Dec;48(12):621-5.

[2]. Lee SH, et al. Progress in the studies on rutaecarpine. Molecules. 2008 Feb 6;13(2):272-300.

[3]. Jeon TW, et al. Immunosuppressive effects of rutaecarpine in female BALB/c mice.Toxicol Lett. 2006 Jul 1;164(2):155-66.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
550.1±60.0 °C at 760 mmHg

[ Melting Point ]:
259.5 - 260ºC

[ Molecular Formula ]:
C₁₈H₁₃N₃O

[ Molecular Weight ]:
287.315

[ Flash Point ]:
286.5±32.9 °C

[ Exact Mass ]:
287.105865

[ PSA ]:
50.68000

[ LogP ]:
2.03

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.792

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: 18 mg/mL clear yellow solution, soluble

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Pharmacological effects of rutaecarpine as a cardiovascular protective agent.

Molecules 15(3) , 1873-81, (2010)

Many studies indicate that traditional Chinese herbs are beneficial in the prevention and treatment of cardiovascular diseases. Evodia rutaecarpa ('Wu-Chu-Yu') remains the most popular and multi-purpo...

Transdermal behaviors comparisons among Evodia rutaecarpa extracts with different purity of evodiamine and rutaecarpine and the effect of topical formulation in vivo.

Fitoterapia 83(5) , 954-60, (2012)

Evodiamine (EVO) and rutaecapine (RUT), the major active components from Evodia rutaecarpa extract (EE), are recognized as a depended analgesic agent. This study was designed to investigate the effect...

Effects of rutaecarpine on the metabolism and urinary excretion of caffeine in rats.

Arch. Pharm. Res. 34(1) , 119-25, (2011)

Although rutaecarpine, an alkaloid originally isolated from the unripe fruit of Evodia rutaecarpa, has been reported to reduce the systemic exposure of caffeine, the mechanism of this phenomenon is un...