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Rhein-8-glucoside

Cat No.:V34243 Purity: ≥98%
Rhein 8-Glucoside (Rhein 8-O-β-D-Glucopyranoside) is an anthraquinone glycoside found in rhubarb.
Rhein-8-glucoside
Rhein-8-glucoside Chemical Structure CAS No.: 34298-86-7
Product category: Plants
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
Other Sizes
Official Supplier of:
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Product Description
Rhein 8-Glucoside (Rhein 8-O-β-D-Glucopyranoside) is an anthraquinone glycoside found in rhubarb. Has a purgative effect.
Rhein 8-O-β-D-glucopyranoside (RG) is an anthraquinone glycoside isolated from the water extract of rhubarb (Rheum palmatum). It is a constituent of the Kampo medicine daikonzoto (DKT), which is clinically used for constipation. RG is known to be transformed by intestinal bacteria into rhein, an aglycone anthraquinone. The study investigates the influence of RG on the metabolism and purgative action of sennoside A, the main laxative constituent of rhubarb. [1]
Biological Activity I Assay Protocols (From Reference)
ln Vitro
The effect of Rhein 8-O-β-D-glucopyranoside (RG) on the metabolic activity of sennoside A (SA) was assessed using mouse fecal suspension under anaerobic conditions. SA (0.2 mM) was incubated with various concentrations of RG, and the remaining SA was quantified by HPLC. The metabolic ratio of SA (percentage of SA remaining compared to control) was significantly accelerated by increasing the level of RG, indicating that RG promotes the metabolism of SA by intestinal bacteria. [1]
In separate experiments, rhein (the aglycone of RG), emodin, and aloe-emodin also significantly accelerated SA metabolism in a dose-dependent manner, similar in potency to RG. This suggests that the anthraquinone moiety is responsible for the acceleration. [1]
ln Vivo
The purgative action of Rhein 8-O-β-D-glucopyranoside (RG) alone and in combination with sennoside A (SA) was evaluated in mice by observing fecal consistency over 10 hours and calculating a feces score (0=normal, 1=soft, 2=unformed). When administered alone, RG showed purgative activity only at higher doses: at 33.4 and 66.8 mg/kg, the feces score was approximately 1.0; at doses of 16.8 mg/kg or less, no purgative activity was observed. [1]
When co-administered with SA (15 mg/kg), RG significantly stimulated the purgative activity of SA in a dose-dependent manner at doses of 2.1, 4.2, 8.4, and 16.8 mg/kg. Compared to SA alone, the feces score was markedly increased, demonstrating a synergistic purgative activity-promoting effect of RG on SA. [1]
Animal Protocol
Male ddY mice (30–40 g) were housed under a 12 h light-dark cycle at 21–24°C for at least one week with free access to food and water prior to experiments. Only mice that excreted normal feces during a 1 h observation period before administration were used. [1]
For purgative action evaluation, Rhein 8-O-β-D-glucopyranoside (RG) was prepared in 0.5% sodium hydrogen carbonate. Sennoside A (SA) was prepared in 0.01 M potassium phosphate buffer (pH 7.4). SA was administered orally at 15 mg/kg alone or in combination with RG at doses of 2.1, 4.2, 8.4, and 16.8 mg/kg. The mixture was given as a single oral dose. After administration, fecal condition was observed at 1 h intervals for 10 h. The worst fecal consistency each hour was graded (0: normal, 1: soft, 2: unformed), and the feces score was calculated as the mean total consistency level per hour per mouse. [1]
ADME/Pharmacokinetics
Rhein 8-O-β-D-glucopyranoside (RG) is an anthraquinone glycoside that is transformed by intestinal bacteria into rhein, which is an aglycone anthraquinone abundant in rhubarb. [1]
References

[1]. The influence of rhein 8-O-β-D-glucopyranoside on the purgative action of sennoside A from rhubarb in mice. Biol Pharm Bull. 2012;35(12):2204-8.

Additional Infomation
According to reports, rhubarb and senna leaves contain emodin-8-glucoside, and relevant data is available for reference.
Rhein 8-O-β-D-glucopyranoside (RG) is a constituent of rhubarb that contributes to the purgative action of sennoside A (SA) by accelerating the metabolism of SA via intestinal bacteria. The acceleration of SA metabolism is caused by constituents possessing an anthraquinone skeleton, including RG, rhein, emodin, and aloe-emodin. The interaction between SA and other anthraquinones in rhubarb enhances the purgative activity of SA. This study highlights a useful interaction in Kampo medicine where multiple constituents work synergistically. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H18O11
Molecular Weight
446.3610
Exact Mass
446.085
CAS #
34298-86-7
PubChem CID
5320961
Appearance
Light yellow to yellow solid
LogP
0.4
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
4
Heavy Atom Count
32
Complexity
756
Defined Atom Stereocenter Count
5
SMILES
O1C([H])(C([H])(C([H])(C([H])(C1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1=C([H])C([H])=C([H])C2C(C3C([H])=C(C(=O)O[H])C([H])=C(C=3C(C1=2)=O)O[H])=O
InChi Key
WYKUTTFFZMQCGO-HTRBZNBPSA-N
InChi Code
InChI=1S/C21H18O11/c22-6-12-16(25)18(27)19(28)21(32-12)31-11-3-1-2-8-14(11)17(26)13-9(15(8)24)4-7(20(29)30)5-10(13)23/h1-5,12,16,18-19,21-23,25,27-28H,6H2,(H,29,30)/t12-,16-,18+,19-,21-/m1/s1
Chemical Name
4-hydroxy-9,10-dioxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-2-carboxylic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~224.03 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 4.55 mg/mL (10.19 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 45.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2403 mL 11.2017 mL 22.4034 mL
5 mM 0.4481 mL 2.2403 mL 4.4807 mL
10 mM 0.2240 mL 1.1202 mL 2.2403 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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