Ginsenoside Rc

Names

[ Name ]:
Ginsenoside Rc

[Synonym ]:
EINECS 234-253-5
Ginsenoside Rc
(3β,12β)-20-{[6-O-(α-L-Arabinofuranosyl)-β-D-glucopyranosyl]oxy}-12-hydroxydammar-24-en-3-yl 2-O-β-D-glucopyranosyl-β-D-glucopyranoside
β-D-Glucopyranoside, (3β,12β)-20-[(6-O-α-L-arabinofuranosyl-β-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-β-D-glucopyranosyl-
20-((6-O-α-L-Arabinofuranosyl-β-D-glucopyranosyl)oxy)-12β-hydroxydammar-24-en-3β-yl 2-O-β-D-glucopyranosyl-β-D-glucopyranoside
MFCD00133368
Ginsenoside-Rc from Panax ginseng (Korean ginseng) root

Biological Activity

[Description]:

Ginsenoside Rc, one of major Ginsenosides from Panax ginseng, enhances GABA receptorA (GABAA)-mediated ion channel currents (IGABA). Ginsenoside Rc inhibits the expression of TNF-α and IL-1β.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Signaling Pathways >> Immunology/Inflammation >> Interleukin Related

Signaling Pathways >> Apoptosis >> TNF Receptor

Natural Products >> Terpenoids and Glycosides

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

[Target]

GABA Receptor

TNF-α

IL-1β

[In Vitro]

Ginsenoside Rc, one of major Ginsenosides from Panax ginseng, enhances γ-aminobutyric acid (GABA) receptorA (GABAA)-mediated ion channel currents. Ginsenoside Rc enhances GABA-mediated ion currents in oocytes expressing the GABAA receptor[1]. Ginsenoside Rc significantly inhibits the expression of macrophage-derived cytokines, such as TNF-α and IL-1β. Ginsenoside Rc also markedly suppresses the activation of TANK-binding kinase 1/IκB kinase ε/interferon regulatory factor-3 and p38/ATF-2 signaling in activated RAW264.7 macrophages, human synovial cells, and HEK293 cells. Ginsenoside Rc exerts its anti-inflammatory actions by suppressing TANK-binding kinase 1/IκB kinase ε/interferon regulatory factor-3 and p38/ATF-2 signaling. Ginsenoside Rc suppresses the nuclear translocation of phospho-ATF-2 and phospho-FRA-1, whereas the translocation of p65 at its peak time points (30 and 60 min) is not decreased by Ginsenoside Rc treatment. Ginsenoside Rc regulates the expression of the proinflammatory cytokine TNF-α, which is produced by macrophages, by suppressing AP-1 activation[2].

[Kinase Assay]

To evaluate the effects of Ginsenoside Rc on kinase activity, immunoprecipitated TBK1, IKKε, and p38 are incubated in reaction buffer in the presence or absence of Ginsenoside Rc. The reactions are initiated by the addition of Mg-ATP. After a 30 min incubation at 30°C, the reactions are stopped by the addition of sample buffer and the samples are boiled. Kinase activity is assessed by immunoblotting with antibodies against the phospho-forms of IKKε, IRF-3, and ATF-2[2].

[References]

[1]. Lee BH, et al. Effects of Ginsenoside Metabolites on GABAA Receptor-Mediated Ion Currents. J Ginseng Res. 2012 Jan;36(1):55-60.

[2]. Yu T, et al. Ginsenoside Rc from Panax ginseng exerts anti-inflammatory activity by targeting TANK-bindingkinase 1/interferon regulatory factor-3 and p38/ATF-2. J Ginseng Res. 2017 Apr;41(2):127-133.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
1128.3±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₅₃H₉₀O₂₂

[ Molecular Weight ]:
1079.269

[ Flash Point ]:
636.2±34.3 °C

[ Exact Mass ]:
1078.592407

[ PSA ]:
357.06000

[ LogP ]:
5.10

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.622

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LY9536300

CHEMICAL NAME :: Ginsenoside RC

CAS REGISTRY NUMBER :: 11021-14-0

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C53-H90-O22

MOLECULAR WEIGHT :: 1079.43

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 410 mg/kg

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

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 50 mg/kg

REFERENCE :: CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 24,2400,1976

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

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

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LY9536300

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

[A quantitative method using one marker for simultaneous assay of ginsenosides in Panax ginseng and P. notoginseng].

Yao Xue Xue Bao 43(12) , 1211-6, (2008)

Current quality control patterns are limited to industrial application, for most of the natural chemical reference substances are expensive and unavailable. Herein, a method, quantitative analysis of ...

Microbial transformation of ginsenosides Rb1, Rb3 and Rc by Fusarium sacchari.

J. Appl. Microbiol. 109(3) , 792-8, (2010)

This study examined the transformation pathways of ginsenosides G-Rb(1) , G-Rb(3) , and G-Rc by the fungus Fusarium sacchari.Ginsenosides G-Rb(1) , G-Rb(3) and G-Rc were isolated from leaves of Radix ...

[Chemical constituents of flower-buds of Panax ginseng--isolation and identification of ginsenoside-Rb3 and ginsenoside-Rc].

Zhong Yao Tong Bao 9(4) , 172-3, (1984)