| Identification | Back Directory | [Name]
TRYPTANTHRIN | [CAS]
13220-57-0 | [Synonyms]
NSC 349447
Trypanthrine
TRYPTANTHRIN
tryptanthrine
Couroupitine A
INDOLO[2,1-B]QUINAZOLINE-6,12-DIONE
6,12-Dihydroindolo[2,1-b]quinazoline-6,12-dione
CouroupitineAIndolo(2,1-b)quinazoline-6,12-dioneTryptanthrine | [Molecular Formula]
C15H8N2O2 | [MDL Number]
MFCD00012073 | [MOL File]
13220-57-0.mol | [Molecular Weight]
248.24 |
| Chemical Properties | Back Directory | [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) | [form ]
powder | [pka]
-3.06±0.20(Predicted) | [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. | [Major Application]
food and beverages | [InChI]
1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H | [InChIKey]
VQQVWGVXDIPORV-UHFFFAOYSA-N | [SMILES]
N21c3c(cccc3)C(=O)C2=Nc4c(cccc4)C1=O |
| Safety Data | Back Directory | [WGK Germany ]
3 | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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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Sigma-Aldrich
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021-61415566 800-8193336 |
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https://www.sigmaaldrich.cn |
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