| Identification | Back Directory | [Name]
Brevilin A | [CAS]
16503-32-5 | [Synonyms]
Brevilin A
6-O-Angeloylplenolin
2-Butenoic acid,2-methyl-,(3S,3aR,4S,4aR,7aR,8R,9aR)-2,3,3a,4,4a,5,7a,8,9,9a-decahydro-3,4a,8-trimethyl-2,5-dioxoazuleno[6,5-b]furan-4-ylester, (2Z)- | [Molecular Formula]
C20H26O5 | [MDL Number]
MFCD04034623 | [MOL File]
16503-32-5.mol | [Molecular Weight]
346.42 |
| Chemical Properties | Back Directory | [Boiling point ]
494.0±45.0 °C(Predicted) | [density ]
1.17±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO:100.0(Max Conc. mg/mL);288.67(Max Conc. mM) | [form ]
A solid | [color ]
White to off-white | [InChI]
1S/C20H26O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-14(16)9-11(3)13-7-8-15(21)20(13,17)5/h6-8,11-14,16-17H,9H2,1-5H3/b10-6-/t11-,12+,13+,14-,16-,17+,20+/m1/s1 | [InChIKey]
KUPPZVXLWANEJJ-UXPPPGSFSA-N | [SMILES]
C(O[C@H]1[C@]2([H])[C@H](C)C(=O)O[C@]2([H])C[C@@H](C)[C@@]2([H])[C@@]1(C)C(=O)C=C2)(=O)/C(/C)=C\C |
| Hazard Information | Back Directory | [Uses]
Brevilin A can be used using a selective extraction method to obtain natural substances, and can also be applied to prepare derivatives to use for anti-cancer activity. | [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 | [Enzyme inhibitor]
This naturally occurring sesquiterpenoid (FW = 346.40 g/mol; CAS 16503- 32-5) from the volatile oils of the plant Centipeda minima inhibits (IC50 = 10 μg/mL) STAT3 phosphorylation in the Jak/STAT signal transduction pathway of A549R cells. Brevilin A showed high specificity on Janus Kinase activity and following STAT3 signaling without directly affecting some other signals, including p65, AKT and GSK-3β phosphorylation, as well as Src kinase activity. Brevilin A is also an antibiotic with activity against Giardia (IC50 = 16 μM) and Entamoeba histolitica (IC50 = 4–9 μM). | [in vivo]
Brevilin A (oral gavage; 10 and 20 mg/kg; once daily; 16 d) inhibits CNE-2 xenograft tumor growth, and inhibits PI3K/AKT and STAT3 signaling in vivo[2]. | Animal Model: | Male BALB/c nude mice injected with CNE-2 cells[2] | | Dosage: | 10 and 20 mg/kg | | Administration: | Oral gavage; 10 and 20 mg/kg; once daily; 16 days | | Result: | Decreased average tumor volumes and weights treated with 20 mg/kg by 36.3% and 46.0%, respectively, compared to vehicle control.
Inhibited the protein expression of p-AKT and p-STAT3 at both low and high doses. |
| [IC 50]
STAT3: 10.6 μM (IC50) |
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