TRYPTANTHRIN Property

Melting point:

258 °C(Solv: ethanol (64-17-5))

Boiling point:

469.3±28.0 °C(Predicted)

Density 

1.45±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: soluble2mg/mL (warmed)

pka

-3.06±0.20(Predicted)

form 

powder

color 

faint yellow to dark yellow

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

InChIKey

VQQVWGVXDIPORV-UHFFFAOYSA-N

Safety

WGK Germany 

3

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

TRYPTANTHRIN Chemical Properties,Usage,Production

Description

The matured fruit of Couroupita guianensis yields two highly unsaturated alkaloids. Couroupitine A is obtained in the form of yellow needles when crystallized from MeOH-CHCI3. It gives an ultraivolet spectrum with absorption maxima at 225 and 251 nm and an inflexion at 315 nm in EtOH.

Uses

Tryptanthrin is natural alkaloid, and a potent inhibitor of cyclooxygenase COX-2 and 5-lipoxygenase acting as an anti-inflammatory agent.

Definition

ChEBI: Tryptanthrine is an organonitrogen heterocyclic compound, an organic heterotetracyclic compound and an alkaloid antibiotic.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Tryptanthrin is a plant alkaloid with anti-inflammatory and anti cancer activities. Tryptanthrin blocks leukotriene production in neutrophils and in whole blood assays, and in an in vivo rat pleurisy model. The compound also inhibits P-glycoprotein, and sensitizes resistant cancer cell lines to killing by cytotoxic agents.

in vitro

in human hepatocyte-derived hepg2 cells, tryptanthrin inhibited the reactive oxygen species formation, mitochondrial dysfunction, and cell death triggered by tert-butyl hydroperoxide (tbhp). furthermore, tryptanthrin reversed the reduction of glutathione (gsh) induced by tbhp. specifically, nuclear translocation, transactivation of nuclear factor erythroid 2-related factor 2 (nrf2), and phosphorylation of extracellular signal-regulated kinase (erk) were evoked by the treatment of tryptanthrin. additionally, the expression of the heme oxygenase 1 and glutamate was upregulated by tryptanthrin [1].

in vivo

balb/c (h-2d) mice, intraperitoneally (i.p.) inoculated with leukemia wehi-3b jcs cells, were injected i.p with tryptanthrin at doses of 0.04 mg/kg, 0.08 mg/kg and 0.16 mg/kg body weight for 5 consecutive days. tryptanthrin inhibited the growth of wehi-3b jcs cells in balb/c mice, and at the dosages of 0.08 mg/kg and 0.16 mg/kg, significant inhibition was seen. moreover, tryptanthrin, in a dose-dependent fashion, triggered cell cycle arrest of the wehi-3b jcs cells at g0/g1 phase [2].

References

Sen, Mahato, Dutta, Tetrahedron Lett., 609 (1974)