TRYPTANTHRIN Chemical Properties

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 Information

WGK Germany 

3

HS Code 

29339900

TRYPTANTHRIN Usage And Synthesis

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)

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