zerumbone Chemical Properties

Melting point:

67-69℃

Boiling point:

321.6±42.0 °C(Predicted)

Density 

0.887±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: ≥10mg/mL

form 

powder

color 

white to off-white

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.

LogP

4.168 (est)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

43-50

Safety Statements 

36/37-60-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

zerumbone Usage And Synthesis

Description

Zerumbone (471-05-6) is a natural sesquiterpene ketone isolated from Zingiber sp. Potentiates TRAIL-induced apoptosis via upregulation of death receptor DR4 and DR5 expression. Zerumbone induces apoptosis in T-acute lymphoblastic leukemia cells but has no cytotoxic effect on normal cells. Cell permeable.

Uses

Zerumbone has been used:

• for liquid chromatography with mass spectrometry (LC-MS-MS)
• to investigate its potential application in the prevention
• treatment of esophageal squamous cell carcinomas (ESCC)

Definition

ChEBI: A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillati n from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.

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

Biochem/physiol Actions

Zerumbone is a TRAIL-induced apoptosis potentiator. It potentiates TRAIL-induced apoptosis through the up-regulation of DR4 and DR5 expression and the down-regulation of cFLIP. Zerumbone has very little or no cytotoxic effect on the normal human endothelial cells and dermal fibroblasts. Zerumbone is a sesquiterpene isolated from in Zingiber zerumbet Smith (wild ginger).

Anticancer Research

Zerumbone is isolated from the rhizomes of the wild ginger Zingiber zerumbet. It isfound to suppress the proliferation of breast cancer and colon cancer cells and alsoto prevent initiation and promotion of skin cancer in mice. It also suppresses theNF-κB activation and its sequential suppression of IκBα kinase activity, IκBαphosphorylation, IκBα degradation, p65 phosphorylation, nuclear translocation,and acylation. It downregulates the NF-κB-regulated gene products like FLIP, cyclinD1, TRAF1, COX2, Bfl-1/A1, MMP-9, Bcl-xL, ICAM-1, Bcl-2, c-myc, XIAP,survivin, IAP1, and IAP2, and thus, it potentiates apoptosis (Murakami et al. 2002;Sakinah et al. 2007).

References

1) Leu et al. (2009), A small molecule inhibitor of inducible heat shock protein 70; Mol. Cell, 36 15 2) Abdelwahab et al. (2011), Zerumbone induces apoptosis in T-acute lymphoblastic leukemia cells; Leuk. Res., 35 268

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