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Zerumbone

Zerumbone

Product ID Z1970
Cas No. 471-05-6
Purity ≥99%
Product Unit SizeCostQuantityStock
10 mg $67.80 In stock
50 mg $277.90 In stock
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  • Description
  • Product Info
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  • References
  • Description
  • Product Info
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Description

Zerumbone is a cyclic sesquiterpene compound found in ginger root. Zerumbone exhibits a wide variety of beneficial properties, including anti-hyperlipidemic, anticancer chemotherapeutic, anti-angiogenic, antioxidative, antinociceptive, and anti-inflammatory activities. In an animal model of nonalcoholic fatty liver disease, zerumbone upregulates expression of PPARα and enzymes involved in lipid oxidation and downregulates expression of fatty acid synthase and lipogenic genes, resulting in decreased total cholesterol and triglyceride levels in plasma and improvements in lipid sensitivity. In several cancer cell lines, zerumbone inhibits expression of VEGF and activity of IKKα and NF-κB and activates caspases 3 and 9 and cleavage of poly(ADP)-ribose polymerase (PARP), resulting in apoptosis and decreased cellular proliferation. In both cellular and animal models, this compound displays antioxidative benefit, activating Nrf2 and increasing expression of heme oxygenase 1 (HO-1), resulting in decreased levels of reactive oxygen species (ROS). In vivo, zerumbone exhibits antinociceptive characteristics and is thought to act through L-arginine-NO-cGMP-PKC-K+ channel pathways and TRPV1 channels. Zerumbone also decreases paw edema and granulomatous tissue formation in animal models of inflammation.

Product Info

Cas No.

471-05-6

Purity

≥99%

Formula

C15H22O

Formula Wt.

218.33

Chemical Name

(2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one

IUPAC Name

(2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one

Solubility

DMSO (≥10 mg/mL)

Appearance

White to off white powder

Shipping and Storage

Store Temp

4°C

Ship Temp

Ambient

Downloads

MSDS

Z1970 MSDS PDF

Info Sheet

Z1970 Info Sheet PDF

References

Tsuboi K, Matsuo Y, Shamoto T, et al. Zerumbone inhibits tumor angiogenesis via NF-κB in gastric cancer. Oncol Rep. 2014 Jan;31(1):57-64. PMID: 24220661.

Tzeng TF, Liou SS, Chang CJ, et al. Zerumbone, a Natural Cyclic Sesquiterpene of Zingiber zerumbet Smith, Attenuates Nonalcoholic Fatty Liver Disease in Hamsters Fed on High-Fat Diet. Evid Based Complement Alternat Med. 2013;2013:303061. PMID: 24223615.

Sun Y, Sheng Q, Cheng Y, et al. Zerumbone induces apoptosis in human renal cell carcinoma via Gli-1/Bcl-2 pathway. Pharmazie. 2013 Feb;68(2):141-5. PMID: 23469687.

Weng HY, Hsu MJ, Wang CC, et al. Zerumbone suppresses IKKα, Akt, and FOXO1 activation, resulting in apoptosis of GBM 8401 cells. J Biomed Sci. 2012 Oct 5;19:86. PMID: 23035900.

Shin JW, Ohnishi K, Murakami A, et al. Zerumbone induces heme oxygenase-1 expression in mouse skin and cultured murine epidermal cells through activation of Nrf2. Cancer Prev Res (Phila). 2011 Jun;4(6):860-70. PMID: 21367956.

Perimal EK, Akhtar MN, Mohamad AS, et al. Zerumbone-induced antinociception: involvement of the L-arginine-nitric oxide-cGMP -PKC-K+ ATP channel pathways. Basic Clin Pharmacol Toxicol. 2011 Mar;108(3):155-62. PMID: 20955360.

Sulaiman MR, Perimal EK, Akhtar MN, et al. Anti-inflammatory effect of zerumbone on acute and chronic inflammation models in mice. Fitoterapia. 2010 Oct;81(7):855-8. PMID: 20546845.

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