Ginsenoside Rh4

CAS# 174721-08-5

Ginsenoside Rh4

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Quality Control of Ginsenoside Rh4

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Chemical structure

Ginsenoside Rh4

3D structure

Chemical Properties of Ginsenoside Rh4

Cas No. 174721-08-5 SDF Download SDF
PubChem ID 21599928 Appearance Powder
Formula C36H60O8 M.Wt 620.9
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in methan
Chemical Name (2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2E)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES CC(=CCC=C(C)C1CCC2(C1C(CC3C2(CC(C4C3(CCC(C4(C)C)O)C)OC5C(C(C(C(O5)CO)O)O)O)C)O)C)C
Standard InChIKey OZTXYFOXQFKYRP-TXRYYSRHSA-N
Standard InChI InChI=1S/C36H60O8/c1-19(2)10-9-11-20(3)21-12-15-35(7)27(21)22(38)16-25-34(6)14-13-26(39)33(4,5)31(34)23(17-36(25,35)8)43-32-30(42)29(41)28(40)24(18-37)44-32/h10-11,21-32,37-42H,9,12-18H2,1-8H3/b20-11+/t21-,22-,23+,24-,25-,26+,27+,28-,29+,30-,31+,32-,34-,35-,36-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Ginsenoside Rh4

The roots of Panax ginseng C. A. Mey.

Biological Activity of Ginsenoside Rh4

DescriptionGinsenoside Rh4 is a rare saponin obtained from Panax notoginseng. Ginsenoside Rh4 activates Bax, caspase 3, caspase 8, and caspase 9. Ginsenoside Rh4 also induces autophagy. Ginsenoside Rh4 could be safely used as adjuvant with low or non-haemolytic effect; it has cytotoxic activity and its aglycone against cancer cell lines.
TargetsCaspase | Autophagy | Bcl-2/Bax
In vivo

Immunological adjuvant effect of ginsenoside Rh4 from the roots of Panax notoginseng on specific antibody and cellular response to ovalbumin in mice.[Pubmed: 17311234]

Chem Biodivers. 2007 Feb;4(2):232-40.


METHODS AND RESULTS:
Ginsenoside Rh4 (1), a saponin isolated from the roots of Panax notoginseng (Burk.) F. H. Chen, was evaluated for its haemolytic activity and adjuvant potential on specific antibody and cellular response to ovalbumin (OVA) in mice. Compound 1 showed a slight haemolytic effect, its concentration inducing 50% of the maximum haemolysis (HD(50) value) being 407+/-12 microg/ml using a 0.5% suspension of red blood cells. Ginsenoside Rh4 significantly increased the concanavalin A (Con A)-, lipopolysaccharide (LPS)-, and OVA-induced splenocyte proliferation in OVA-immunized mice especially at a dose of 25 microg (P<0.05, P<0.01, or P<0.001). The OVA-specific serum IgG, IgG1, and IgG2b antibody levels were also significantly enhanced by 1 at a dose of 25 microg compared to the OVA control group (P<0.05 or P<0.01). Moreover, the enhancing effect of Ginsenoside Rh4 on the OVA-specific IgG2b antibody responses to OVA in mice was more significant than that of Alum (Al(OH)(3) gel; P<0.01).
CONCLUSIONS:
These results suggest that Ginsenoside Rh4 could be safely used as adjuvant with low or non-haemolytic effect.

Protocol of Ginsenoside Rh4

Structure Identification
Planta Med. 1996 Feb;62(1):86-7.

Ginsenoside Rh4, a genuine dammarane glycoside from Korean red ginseng.[Pubmed: 8720394]


METHODS AND RESULTS:
A genuine glycoside, named Ginsenoside Rh4, was isolated from Korean red ginseng (Panax ginseng C. A. Meyer) through repeated column chromatography, and its chemical structure was established to be 6-O-beta-D-glucopyranosyldammar-20(22),24-diene-3 beta,6 alpha,12 beta-triol by spectral and chemical methods. The stereochemistry of a double bond at C-20(22) of Ginsenoside Rh4 was characterized as (E) from a NOESY experiment in the 1H-NMR of the aglycone.
CONCLUSIONS:
Cytotoxic activities of Ginsenoside Rh4 and its aglycone against cancer cell lines were evaluated by use of the SRB method.

Ginsenoside Rh4 Dilution Calculator

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Ginsenoside Rh4 Molarity Calculator

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Preparing Stock Solutions of Ginsenoside Rh4

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6106 mL 8.0528 mL 16.1057 mL 32.2113 mL 40.2641 mL
5 mM 0.3221 mL 1.6106 mL 3.2211 mL 6.4423 mL 8.0528 mL
10 mM 0.1611 mL 0.8053 mL 1.6106 mL 3.2211 mL 4.0264 mL
50 mM 0.0322 mL 0.1611 mL 0.3221 mL 0.6442 mL 0.8053 mL
100 mM 0.0161 mL 0.0805 mL 0.1611 mL 0.3221 mL 0.4026 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Ginsenoside Rh4

Ginsenoside Rh4 is a rare saponin obtained from Panax notoginseng. Ginsenoside Rh4 activates Bax, caspase 3, caspase 8, and caspase 9. Ginsenoside Rh4 also induces autophagy.

In Vitro:Ginsenoside Rh4 causes cytochrome C release and activates the death receptor Fas, the pro-apoptotic protein Bax, and caspase 3, caspase 8, and caspase 9. Ginsenoside Rh4 induces caspase-dependent apoptosis via both the intrinsic and extrinsic pathways in Caco-2 and HCT-116 cells. The CCK-8 assay reveals that Ginsenoside Rh4 can significantly inhibit the growth of colorectal carcinoma cells, such as Caco-2 and HCT-116 cells, to varying degrees. Ginsenoside Rh4 dramatically reduces cell viability in a concentration- and time-dependent manner. In particular, treatment with 120 and 180 μM Ginsenoside Rh4 results in marked Caco-2 cell death of 44.51±1.23% and 75.74±2.91%, respectively, after incubation for 48 h. Similar results are observed in HCT-116 cells treated with concentrations of 120 μM (33.62±1.98%) and 180 μM Ginsenoside Rh4 (59.88±2.31%). In contrast, concentrations of Rh4 from 120 to 300 μM cause no obvious toxic effects on the normal human colon epithelial cell line CCD-18Co, and a slight difference in the effect is observed between 24 and 48 h of treatment. In the colony formation assay, the number of colonies is found to be significantly decreased in Caco-2 and HCT-116 cells, whereas the number of colonies is almost unchanged in CCD-18Co cells[1].

In Vivo:To assess whether Ginsenoside Rh4 can inhibit the growth of colorectal cancer, a colorectal cancer xenograft model is established by inoculating nude mice with Caco-2 cells. Mice treated with 20 and 40 mg/kg Ginsenoside Rh4 and 40 mg/kg CAMPTO exhibit smaller tumors than the control after 30 days of treatment, showing inhibition rates of 29.91%, 66.30% and 77.82%, respectively. However, there is a significant difference in body weight between the Ginsenoside Rh4-treated group and the CAMPTO-treated group. The body weights of the 20 and 40 mg/kg Ginsenoside Rh4-treated groups (15.95±0.35 g and 18.35±0.44 g) are markedly higher, whereas the body weight of the CAMPTO-treated group is lower (10.85±0.28 g) than that of the solvent control group (14.19±0.25 g)[1].

References:
[1]. Wu Q, et al. Ginsenoside Rh4 induces apoptosis and autophagic cell death through activation of the ROS/JNK/p53 pathway in colorectal cancer cells. Biochem Pharmacol. 2018 Feb;148:64-74.

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References on Ginsenoside Rh4

Ginsenoside Rh4, a genuine dammarane glycoside from Korean red ginseng.[Pubmed:8720394]

Planta Med. 1996 Feb;62(1):86-7.

A genuine glycoside, named Ginsenoside Rh4, was isolated from Korean red ginseng (Panax ginseng C. A. Meyer) through repeated column chromatography, and its chemical structure was established to be 6-O-beta-D-glucopyranosyldammar-20(22),24-diene-3 beta,6 alpha,12 beta-triol by spectral and chemical methods. The stereochemistry of a double bond at C-20(22) of Ginsenoside Rh4 was characterized as (E) from a NOESY experiment in the 1H-NMR of the aglycone. Cytotoxic activities of Ginsenoside Rh4 and its aglycone against cancer cell lines were evaluated by use of the SRB method.

Description

Ginsenoside Rh4 is a rare saponin obtained from Panax notoginseng. Ginsenoside Rh4 activates Bax, caspase 3, caspase 8, and caspase 9. Ginsenoside Rh4 also induces autophagy.

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