Ginsenoside CK

ChemicalBook > CAS DataBase List > 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 COMPOUND K(P);Compound K-Ginsenoside CK;Lappaconitine hydrochloride;Ginsenoside Compound K >=96% (HPLC)
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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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 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

Shanghai Standard Technology Co., Ltd.

Product: Ginsenoside CK 39262-14-1
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2020-01-02

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

39262-14-1

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract