6-Gingerol

Names

[ Name ]:
6-Gingerol

[Synonym ]:
3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-(+)-
(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
3-Decanone (5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)
(+)-Gingerol
(S)-[6]Gingerol
(S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone
3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-
3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-
(+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone
(S)-(+)-[6]Gingerol
(+)-[6]-Gingerol
6-Gingerol
(S)-(6)-Gingerol
(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxy-phenyl)decan-3-one
Gingerol
UNII-925QK2Z900
(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone
(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
MFCD00210507
[6]-Gingerol

Biological Activity

[Description]:

[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.

[Related Catalog]:

Signaling Pathways >> Epigenetics >> AMPK

Signaling Pathways >> PI3K/Akt/mTOR >> AMPK

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Natural Products >> Flavonoids

[Target]

AMPK

Apoptosis

[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[1]. [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[2]. 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[3].

[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)[2].

[Cell Assay]

[6]-gingerol stock (20 mg/mL) is prepared in ethanol and the working concentrations are prepared by diluting this stock in dimethyl sufoxide (DMSO). For MTT assay, 5×103 cells/well of human colon cancer cells and 104 cells/well of mouse IECs are seeded in 96-well plates. Cells are treated with [6]-gingerol for 48 h,72 h or 96 h before performing MTT assay and for 16 h before Annexin-V staining[1].

[Animal admin]

Mice: Mice with DSS-induced colitis are given different oral dosages of [6]-gingerol daily for 14 days. Body weight and colon inflammation are evaluated, and level of proinflammatory cytokines in colon tissues is measured[2].

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
453.0±35.0 °C at 760 mmHg

[ Melting Point ]:
30 - 32ºC

[ Molecular Formula ]:
C₁₇H₂₆O₄

[ Molecular Weight ]:
294.386

[ Flash Point ]:
159.0±19.4 °C

[ Exact Mass ]:
294.183105

[ PSA ]:
66.76000

[ LogP ]:
2.48

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.523

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HE0757000

CHEMICAL NAME :: 3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-(+)-

CAS REGISTRY NUMBER :: 23513-14-6

LAST UPDATED :: 199412

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C17-H26-O4

MOLECULAR WEIGHT :: 294.43

WISWESSER LINE NOTATION :: QY5&1V2R DQ CO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 58100 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 200 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 122,87,1983

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H315-H319-H335

[ Precautionary Statements ]:
P261-P301 + P310-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
UN 2811 6.1 / PGIII

[ RTECS ]:
HE0757000

[ HS Code ]:
2914509090

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

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Related Compounds

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