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| | TRYPTANTHRIN Basic information |
| Product Name: | TRYPTANTHRIN | | Synonyms: | TRYPTANTHRIN;tryptanthrine;6,12-Dihydroindolo[2,1-b]quinazoline-6,12-dione;Trypanthrine;NSC 349447;CouroupitineAIndolo(2,1-b)quinazoline-6,12-dioneTryptanthrine;TRYPTANTHRIN-D4;INDOLO[2,1-B]QUINAZOLINE-6,12-DIONE | | CAS: | 13220-57-0 | | MF: | C15H8N2O2 | | MW: | 248.24 | | EINECS: | | | Product Categories: | Indoles and derivatives | | Mol File: | 13220-57-0.mol |  |
| | 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 |
| 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) |
| | TRYPTANTHRIN Preparation Products And Raw materials |
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