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)
