Properties Pharmacological action Anti-cancer properties
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Ginsenoside CK

Properties Pharmacological action Anti-cancer properties
Product Name
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 C-K-RM;GINSENOSIDE COMPOUND K(P);Compound K-Ginsenoside CK;Lappaconitine hydrochloride
CBNumber
CB92332311
Molecular Formula
C36H62O8
Formula Weight
622.88
MOL File
39262-14-1.mol
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Ginsenoside CK Property

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
InChI
InChI=1/C36H62O8/c1-20(2)10-9-14-36(8,44-31-30(42)29(41)28(40)23(19-37)43-31)21-11-16-35(7)27(21)22(38)18-25-33(5)15-13-26(39)32(3,4)24(33)12-17-34(25,35)6/h10,21-31,37-42H,9,11-19H2,1-8H3/t21-,22+,23+,24-,25+,26-,27-,28+,29-,30+,31-,33-,34+,35+,36-/s3
InChIKey
FVIZARNDLVOMSU-SFEJUJENNA-N
SMILES
C[C@@]12CC[C@@]3([H])C([C@@H](O)CC[C@]3(C)[C@@]1([H])C[C@@H](O)[C@]1([H])[C@@]([H])([C@](C)(CCC=C(C)C)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC[C@@]21C)(C)C |&1:1,4,7,11,13,16,18,20,22,31,32,33,35,37,44,r|
LogP
5.500 (est)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SMB00348
Product name
Ginsenoside Compound K
Purity
≥96% (HPLC)
Packaging
5MG
Price
$214
Updated
2024/03/01
Sigma-Aldrich
Product number
PHL80461
Product name
Ginsenoside C-K
Purity
phyproof? Reference Substance
Packaging
10MG
Price
$777
Updated
2024/03/01
Sigma-Aldrich
Product number
SMB00348
Product name
Ginsenoside Compound K
Purity
≥96% (HPLC)
Packaging
25MG
Price
$756
Updated
2023/06/20
Cayman Chemical
Product number
29926
Product name
Ginsenoside CK
Packaging
5mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
29926
Product name
Ginsenoside CK
Packaging
10mg
Price
$82
Updated
2024/03/01
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Ginsenoside CK Chemical Properties,Usage,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.

Ginsenoside CK Preparation Products And Raw materials

Raw materials

Preparation Products

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Ginsenoside CK Suppliers

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View Lastest Price from Ginsenoside CK manufacturers

Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
Product
Ginsenoside CK 39262-14-1
Price
US $0.00/g
Min. Order
1g
Purity
50%-98% HPLC
Supply Ability
100kg
Release date
2024-03-14
Shaanxi Dideu Medichem Co. Ltd
Product
Ginsenoside CK 39262-14-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
1KG
Release date
2024-07-19
Shaanxi Haibo Biotechnology Co., Ltd
Product
Ginsenoside CK 39262-14-1
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
2000ton
Release date
2023-08-21

39262-14-1, Ginsenoside CKRelated Search:

Ginsenoside Rc Ginsenoside Rd Ginsenoside Rb1 GINSENOSIDE RB2 Ginsenoside-Rg5 SECO-ISOLARICIRESINOL DIGLUCOSIDE yemuoside YM(10) PROTOGRACELLIN GINSENOSIDEF1 Ginsenoside Rg1 Ginsenoside Rh1 Ginsenoside Rb3 Ginsenoside Rk3 Ginsenoside Rg2 Ginsenoside Rh2 GinsenosideRo Ginsenoside Re Ginsenoside Rf

  • (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
  • Ginsenoside compound K|||Ginsenoside K
  • Ginsenoside C-K-RM
  • 39262-14-1
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract