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Ginsenoside CK

CAS No.
39262-14-1
Chemical Name:
Ginsenoside CK
Synonyms
IH-901;CoMpoundCK;Ginsenoside K;Ginsenosinde CK;20S-Ginsenoside C;S-Ginsenoside C-K;GINSENOSIDE COMPOUND K(P);Compound K-Ginsenoside CK;Lappaconitine hydrochloride;Ginsenoside Compound K >=96% (HPLC)
CBNumber:
CB92332311
Molecular Formula:
C36H62O8
Molecular Weight:
622.88
MDL Number:
MFCD07772261
MOL File:
39262-14-1.mol
Last updated:2024-03-22 10:44:05

Ginsenoside CK Properties

Melting point 181~183℃
Boiling point 723.1±60.0 °C(Predicted)
Density 1.19
solubility DMF: 10 mg/ml; DMSO: 10 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
pka 12.94±0.70(Predicted)
form powder
color White
Stability Hygroscopic
InChIKey FVIZARNDLVOMSU-SFEJUJENNA-N
LogP 5.500 (est)
FDA UNII G8D4792Q7K

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312+P330-P501
NFPA 704
0
2 0

Ginsenoside CK price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SMB00348 Ginsenoside Compound K ≥96% (HPLC) 39262-14-1 5MG $214 2024-03-01 Buy
Sigma-Aldrich PHL80461 Ginsenoside C-K phyproof? Reference Substance 39262-14-1 10MG $777 2024-03-01 Buy
Sigma-Aldrich SMB00348 Ginsenoside Compound K ≥96% (HPLC) 39262-14-1 25MG $756 2023-06-20 Buy
Cayman Chemical 29926 Ginsenoside CK 39262-14-1 5mg $49 2024-03-01 Buy
Cayman Chemical 29926 Ginsenoside CK 39262-14-1 10mg $82 2024-03-01 Buy
Product number Packaging Price Buy
SMB00348 5MG $214 Buy
PHL80461 10MG $777 Buy
SMB00348 25MG $756 Buy
29926 5mg $49 Buy
29926 10mg $82 Buy

Ginsenoside CK Chemical Properties,Uses,Production

Properties

Ginsenoside CK is a white crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from ginseng rhizome, Gynostemma pentaphyllum.

Pharmacological action

Ginsenoside CK is the main metabolite of protopanaxadiol saponins in human intestinal tract. Studies have shown that the pharmacological activities of ginsenosides are mainly mediated through its metabolic component CK, and CK has a variety of pharmacological activities, such as anti-inflammatory, anti-tumor, anti-allergic, anti-diabetic, hepatoprotective, neuroprotective, and cardiovascular protection.

Anti-cancer properties

Ginsenoside CK (CK) is a promising clinical antitumor drug that effectively inhibits the proliferation of liver and lung cancer and metastasis of human osteosarcoma and liver cancer in vitro and in vivo. CK exerts a greater antitumor effect against hormone-independent breast cancer cells than the other 16 ginsenosides[2]. 

Description

Ginsenoside compound K (C-K) is a metabolite of the protopanaxadiol-type saponins of Panax ginseng C.A. Meyer, has long been used to treat against the development of cancer, inflammation, allergies, and diabetes; C-K acts as a unique HUVEC migration inhibitor by regulating MMP expression, as well as the activity of SPHK1 and its related sphingolipid metabolites. C-K exhibits anti-inflammatory effects by reducing iNOS and COX-2, C-K exhibits an inhibition against the activity of CYP2C9 and CYP2A6 in human liver microsomes with IC50s of 32.0±3.6 μM and 63.6±4.2 μM, respectively. C-K promotes Aβ clearance by enhancing autophagy via the mTOR signaling pathway in primary astrocytes.

Uses

Ginsenoside C-K is reported to exhibit anti-wrinkle effects. Also, it potentiates tumor necrosis factor (TNF)-related apotosis-inducing ligand (TRAIL)-induced apotosis in HCT116 colon cancer.

Definition

ChEBI: Ginsenoside C-K is a ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 20 has been converted to the corresponding beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position. It has a role as a plant metabolite, an antineoplastic agent, a hepatoprotective agent, an anti-allergic agent and an anti-inflammatory agent. It is a beta-D-glucoside, a 12beta-hydroxy steroid, a ginsenoside, a tetracyclic triterpenoid, a 3beta-hydroxy steroid and a 3beta-hydroxy-4,4-dimethylsteroid. It derives from a hydride of a dammarane.

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.

Biochem/physiol Actions

Ginsenoside compound K (GCK, 20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol, C36H62O8, also known as M1, IH-901, Ginsenoside CK), belonging to tetracyclic dammarane-type triterpenoid saponins. Ginsenosides are poorly absorbed from the gut by oral administration. Still, their major intestinal bacterial metabolite GCK is absorbed, indicating that the in vivo action of ginsenosides oral administration is mediated by their intestinal bacterial metabolic component GCK. The various processes used for GCK synthesis include enzymatic use, microbial conversion, heating, mycelial fermentation, and metabolic engineering[1-3].

Mechanism of action

Mechanistically, Ginsenoside CK (CK) was found to inhibit hormone-independent breast cancer growth by decreasing cyclin D1 expression to induce G1 cycle arrest and induce apoptosis in MCF-7 human breast cancer cells by activating adenosine 5′-monophosphate (AMP)-activated protein kinase (AMPK) through the production of reactive oxygen species (ROS). High glutamine-addicted TNBC cells were particularly sensitive to CK treatment. Ginsenoside CK exerted antitumor activity against TNBC by suppressing glutamine consumption and glutamate production via downregulation of glutaminase 1 (GLS1) expression. CK treatment further decreased cellular ATP production, reduced the utilisation of amino acids associated with glutamine metabolism, and induced glutathione (GSH) depletion and reactive oxygen species (ROS) accumulation, consequently triggering apoptosis in TNBC. Furthermore, CK decreased GLS1 expression in SUM159 xenograft mouse mammary tumors and significantly inhibited tumor growth with few side effects[2].

References

[1] Anshul Sharma, Hae-Jeung Lee. “Ginsenoside Compound K: Insights into Recent Studies on Pharmacokinetics and Health-Promoting Activities.” Biomolecules (2020).
[2] Bo Zhang. “Ginsenoside CK induces apoptosis in triple-negative breast cancer cells by targeting glutamine metabolism.” Biochemical pharmacology 1 1 (2022): 115101.
[3] Mengshi Tang . “Ginsenoside compound K- a potential drug for rheumatoid arthritis.” Pharmacological research 166 (2021): Article 105498.

6892-79-1
39262-14-1
Synthesis of Ginsenoside CK from FOLIENETRIOL

Ginsenoside CK Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 203)Suppliers
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Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
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NanJing Spring & Autumn Biological Engineering CO., LTD.
+8613815430202 sale02@cqherb.com CHINA 376 58

View Lastest Price from Ginsenoside CK manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ginsenoside CK pictures 2024-04-24 Ginsenoside CK
39262-14-1
US $0.00 / g 1g 50%-98% HPLC 100kg Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
Ginsenoside CK pictures 2024-04-23 Ginsenoside CK
39262-14-1
US $0.00 / g 1g ≥98% HPLC 1000kg Changsha Staherb Natural Ingredients Co., Ltd.
Ginsenoside CK pictures 2024-04-12 Ginsenoside CK
39262-14-1
US $0.00 / kg 1kg 98% 2000ton Shaanxi Haibo Biotechnology Co., Ltd
  • Ginsenoside CK pictures
  • Ginsenoside CK
    39262-14-1
  • US $0.00 / g
  • 50%-98% HPLC
  • Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
  • Ginsenoside CK pictures
  • Ginsenoside CK
    39262-14-1
  • US $0.00 / g
  • ≥98% HPLC
  • Changsha Staherb Natural Ingredients Co., Ltd.
  • Ginsenoside CK pictures
  • Ginsenoside CK
    39262-14-1
  • US $0.00 / kg
  • 98%
  • Shaanxi Haibo Biotechnology Co., Ltd

Ginsenoside CK Spectrum

(20S)-20-(β-D-Glucopyranosyloxy)dammara-24-ene-3β,12β-diol (20S)-20-O-β-D-Glucopyranosylprotopanaxadiol 20-(β-D-Glucopyranosyloxy)-5α-dammara-24-ene-3β,12β-diol 20-(β-D-Glucopyranosyloxy)dammar-24-ene-3β,12β-diol IH-901 20(S)-Protopanaxadiol 20-O-D-glucopyranoside GINSENOSIDE COMPOUND K(P) b-D-Glucopyranoside, (3b,12b)-3,12-dihydroxydaMMar-24-en-20-yl S-Ginsenoside C-K 20S-Ginsenoside C CoMpoundCK Ginsenoside K Ginsenosinde CK Ginsenosidecompound K, 98%, from Panax ginseng C. A. Mey. (2S,3R,4S,5S,6R)-2-[(2S)-2-[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol (3b,12b)-3,12-Dihydroxydammar-24-en-20-yl b-D-glucopyranoside β-D-Glucopyranoside, (3β,12β)-3,12-dihydroxydammar-24-en-20-yl Ginsenoside Compound K >=96% (HPLC) Compound K-Ginsenoside CK (2S,3R,4S,5S,6R)-2-(((S)-2-((3S,5R,8R,9R,10R,12R,13R,14R,17S)-3,12-Dihydroxy-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylhept-5-en-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (3beta,12beta)-3,12-dihydroxydammar-24-en-20-yl beta-D-glucopyranoside Lappaconitine hydrochloride 39262-14-1 chemical reagent pharmaceutical intermediate phytochemical reference standards from Chinese medicinal herbs (TCM). standardized herbal extract