A natural sesquiterpene with diverse effects
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Zerumbone

Item No. 15400

Technical Information
Formal Name
(2E,6E)-2,6,9,9-tetramethyl-2,6,10E-cycloundecatrien-1-one
CAS Number
471-05-6
Molecular Formula
C15H22O
Formula Weight
Purity
≥95%
Solid white crystals or powder
DMSO: solubleEthanol: soluble
SMILES
CC1(C)C/C=C(C)/CC/C=C(C)\C(/C=C/1)=O
InChi Code
InChI=1S/C15H22O/c1-12-6-5-7-13(2)14(16)9-11-15(3,4)10-8-12/h7-9,11H,5-6,10H2,1-4H3/b11-9+,12-8+,13-7-
InChi Key
GIHNTRQPEMKFKO-WHILTJODSA-N
Origin
Plant/Curcuma zerumbet
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Zerumbone is a natural monocyclic sesquiterpene first isolated from rhizomes of the wild ginger Z. zerumbet.1 It potently inhibits the activation of Epstein-Barr virus by phorbol esters (IC50 = 140 nM).1,2 Zerumbone inhibits Sonic hedgehog signaling and induces apoptosis in cancer cell lines.3,4,5 It has also been shown to have anti-oxidant and anti-inflammatory activities, contributing to immunomodulatory and hepatoprotective effects.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Murakami, A., Takahashi, M., Jiwajinda, S., et alIdentification of zerumbone in Zingiber zerumbet smith as a potent inhibitor of 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus activation. Biosci. Biotechnol. Biochem. 63(10), 1811-1812 (1999).

    2. Murakami, A., Takahashi, D., Kinoshita, T., et alZerumbone, a southeast asian ginger sesquiterpene, markedly suppresses free radical generation, proinflammatory protein production, and cancer cell proliferation accompanied by apoptosis: The α,β-unsaturated carbonyl group is a prerequisite. Carcinogenesis 23(5), 795-802 (2002).

    3. Stanton, B.Z., and Peng, L.F. Small-molecule modulators of the Sonic Hedgehog signaling pathway. Mol. Biosyst. 6(1), 44-54 (2010).

    4. Sun, Y., Sheng, Q., Cheng, Y., et alZerumbone induces apoptosis in human renal cell carcinoma via Gli-1/Bcl-2 pathway. Pharmazie 68(2), 141-145 (2013).

    5. Sehrawat, A., Arlotti, J.A., Murakami, A., et alZerumbone causes Bax- and Bak-mediated apoptosis in human breast cancer cells and inhibits orthotopic xenograft growth in vivo. Breast Cancer Res. Treat. 136(2), 429-441 (2012).

    6. Rahman, H.S., Rasedee, A., How, C.W., et alZerumbone-loaded nanostructured lipid carriers: Preparation, characterization, and antileukemic effect. Int. J. Nanomedicine 8, 2769-2781 (2013).