[6]-Gingerol

[6]-Gingerol is an active compound isolated from Ginger (Zingiber officinale Rosc), exhibits a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation.

Product information

CAS Number: 23513-14-6

Molecular Weight: 294.39

Formula: C17H26O4

Synonym:

(S)-(+)-[6]Gingerol

6-Gingerol

Chemical Name: (5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

Smiles: CCCCC[C@H](O)CC(=O)CCC1C=C(OC)C(O)=CC=1

InChiKey: NLDDIKRKFXEWBK-AWEZNQCLSA-N

InChi: InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3/t14-/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : ≥ 50 mg/mL (169.84 mM)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

[6]-gingerol inhibits colon cancer cell proliferation and induced apoptosis, while the normal colon cells are unaffected. [6]-gingerol down-regulates phorbol myristate acetate induced phosphorylation of ERK1/2 and JNK MAP kinases and activation of AP-1 transcription factor, but has only little effects on phosphorylation of p38 MAP kinase and activation of NF-kappa B. [6]-gingerol treatment is shown to restore impaired intestinal barrier function and to suppress proinflammatory responses in DSS-treated Caco-2 monolayers. AMPK is activated on [6]-gingerol treatment. Treatment with [6]-gingerol results in a significant decrease in the viability of osteosarcoma cells in a dose-dependent fashion. In parallel, the number of cells arrested at the sub-G1 cell cycle phase is significantly increased. [6]-gingerol induces activation of caspase cascades and regulates cellular levels of Bcl2 and Bax.

In Vivo:

In animal studies, [6]-gingerol significantly ameliorates DSS-induced colitis by restoration of body weight loss, reduction in intestinal bleeding, and prevention of colon length shortening. In addition, [6]-gingerol suppresses DSS-elevated production of proinflammatory cytokines (IL-1β, TNFα, and IL-12).

References:

1. Radhakrishnan EK, et al. [6]-Gingerol induces caspase-dependent apoptosis and prevents PMA-induced proliferation in colon cancer cells by inhibiting MAPK/AP-1 signaling. PLoS One. 2014 Aug 26;9(8):e104401.
2. Chang KW, et al. 6-Gingerol modulates proinflammatory responses in dextran sodium sulfate (DSS)-treated Caco-2 cells and experimental colitis in mice through adenosine monophosphate-activated protein kinase (AMPK) activation. Food Funct. 2015 Oct;6(10):3334-41.
3. Fan J, et al. 6-Gingerol inhibits osteosarcoma cell proliferation through apoptosis and AMPK activation. Tumour Biol. 2015 Feb;36(2):1135-41.

Products are for research use only. Not for human use.