Description
Embelin (550-24-3) inhibitsthe lysine acetyl transferase PCAFin vitro and in vivo(in vitroIC50=7.2 mM). Inhibits H3K9 acetylation in mouse liver tissue while leaving levels of H3K14, H4K8, H4K12 unchanged.1 Also inhibits X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 μM, competing with Smac peptide). Binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Induces apoptosis and alters gene expression profiles in breast cancer cells.3Possesses anti-inflammatory and analgesic activityin vivo.4Cell-permeable.
Chemical Properties
Orange Solid
Uses
Embelin is a natural benzoquinone found in plants of the Myrsinaceae family. Embelin has a wide range of biological activity as it inhibits the growth of bacteria, fungi, protozoa and parasites. Embelin also displays contraceptive and pro-apoptotic properties.
Definition
ChEBI: A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, an
ineoplastic and inhibitory activity towards hepatitis C protease.
Biological Activity
Cell-permeable, non-peptide inhibitor of X-linked inhibitor of apoptosis (XIAP) (IC 50 = 4.1 μ M in competition binding assay with Smac peptide); binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Inhibits cell growth, induces apoptosis and activates caspase-9 in prostate cancer cells (IC 50 4-6 μ M), but has a weaker effect on normal prostate cells (IC 50 = 19-20 μ M). Overcomes the protective effect of XIAP on apoptosis in XIAP-transfected Jurkat cells. Anti-tumor, analgesic and anti-inflammatory in vivo .
References
[1] RAHUL MODAK. Probing p300/CBP Associated Factor (PCAF)-Dependent Pathways with a Small Molecule Inhibitor[J]. ACS Chemical Biology, 2013, 8 6: 1311-1323. DOI:
10.1021/cb4000597[2] ZANETA NIKOLOVSKA-COLESKA. Discovery of Embelin as a Cell-Permeable, Small-Molecular Weight Inhibitor of XIAP through Structure-Based Computational Screening of a Traditional Herbal Medicine Three-Dimensional Structure Database[J]. Journal of Medicinal Chemistry, 2004, 47 10: 2430-2440. DOI:
10.1021/jm030420+[3] PRIYANK SHAH. Embelin inhibits proliferation, induces apoptosis and alters gene expression profiles in breast cancer cells[J]. Pharmacological Reports, 2016, 68 3: Pages 638-644. DOI:
10.1016/j.pharep.2016.01.004[4] M CHITRA. Antitumor, anti-inflammatory and analgesic property of embelin, a plant product.[J]. Chemotherapy, 1994, 40 2: 109-113. DOI:
10.1159/000239181
