A benzoquinone with diverse biological activities
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Embelin

Item No. 11838

Technical Information
Formal Name
2,5-dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione
CAS Number
550-24-3
Synonyms
  • NSC 91874
Molecular Formula
C17H26O4
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 5 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 3 mg/ml
λmax
289 nm
SMILES
O=C(C(O)=C1)C(CCCCCCCCCCC)=C(O)C1=O
InChi Code
InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
InChi Key
IRSFLDGTOHBADP-UHFFFAOYSA-N
Origin
Plant/Embelia ribes
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Embelin is a benzoquinone that has been found in E. ribes and has diverse biological activities.1 It inhibits viral replication of the influenza A subtype H1N1 and the influenza B subtype Victoria-like in MDCK cells (IC50s = 0.3 and 0.2 µM, respectively).2 It is also an inhibitor of X-linked inhibitor of apoptosis (XIAP; IC50 = 4.1 µM in a fluorescence polarization assay).3 Embelin (20-50 µM) induces apoptosis and increases caspase-9 levels in PC3 prostate cancer cells. It completely inhibits TNF-α-induced NF-κB and IκB kinase (IKK) activation and inhibits TNF-α-induced IκBα phosphorylation in KBM5 human myeloid cells when used at a concentration of 50 µM.1 It is active against the Gram-positive bacteria B. subtilis, S. aureus, and M. luteus (MICs = 20, 20, and 25 µg/ml, respectively) and the Gram-negative bacteria P. aeruginosa, K. pneumoniae, and E. coli (MICs = 25, 25, and 45 µg/ml, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ahn, K.S., Sethi, G., and Aggarwal, B.B. Embelin, an inhibitor of X chromosome-linked inhibitor-of-apoptosis protein, blocks nuclear factor-κB (NF-κB) signaling pathway leading to suppression of NF-κB-regulated antiapoptotic and metastatic gene products. Mol. Pharmacol. 71(1), 209-219 (2007).

    2. Hossan, M.S., Fatima, A., Rahmatullah, M., et alAntiviral activity of Embelia ribes Burm. f. against influenza virus in vitro. Arch. Virol. 163(8), 2121-2131 (2018).

    3. Nikolovska-Coleska, Z., Xu, L., Hu, Z., et alDiscovery 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. Med. Chem. 47(10), 2430-2440 (2004).

    4. Radhakrishnan, N., Gnanamani, A., and Mandal, A.B. A potential antibacterial agent embelin, a natural benzoquinone extracted from Embelia ribes. Biol. Med. 3(2), 1-7 (2011).