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6'-O-beta-D-Glucosylgentiopicroside

Cat No.:V33752 Purity: ≥98%
6'-O-beta-D-Glucosylgentiopicroside is an iridoid extracted from the roots of G. straminea.
6'-O-beta-D-Glucosylgentiopicroside
6'-O-beta-D-Glucosylgentiopicroside Chemical Structure CAS No.: 115713-06-9
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
6'-O-beta-D-Glucosylgentiopicroside is an iridoid extracted from the roots of G. straminea. 6'-O-beta-D-Glucosylgentiopicroside strongly inhibits fMLP-induced superoxide production.
6'-O-beta-D-Glucosylgentiopicroside (CAS#: 115713-06-9) is a natural iridoid glycoside compound found in Gentiana species, particularly in Gentiana scabra and other medicinal plants used in traditional Chinese medicine. It is a derivative of gentiopicroside, one of the major active constituents of Gentiana, with an additional glucose moiety at the 6'-position. The compound has the molecular formula C22H30O14 and a molecular weight of 518.47. It exhibits various biological activities including anti-inflammatory, hepatoprotective, and antioxidant properties.
Biological Activity I Assay Protocols (From Reference)
Targets
The specific molecular targets of 6'-O-beta-D-Glucosylgentiopicroside are not fully characterized. As an iridoid glycoside, it may interact with multiple cellular targets involved in inflammation, oxidative stress, and liver protection. The compound exhibits anti-inflammatory activity, likely through inhibition of inflammatory mediators and signaling pathways such as NF-κB and MAPK. Its hepatoprotective effects may involve antioxidant mechanisms and modulation of liver enzyme activities.
ln Vitro
6'-O-beta-D-Glucosylgentiopicroside is a natural iridoid glycoside found in Gentiana species. It is a derivative of gentiopicroside with an additional glucose moiety at the 6'-position. The compound has a molecular weight of 518.47 and formula C22H30O14. It exhibits anti-inflammatory, hepatoprotective, and antioxidant properties. As an iridoid glycoside, it is a member of a class of natural compounds known for their diverse biological activities. The compound is commonly used in research on liver protection, inflammation, and oxidative stress.
ln Vivo
No specific in vivo activity data are documented for 6'-O-beta-D-Glucosylgentiopicroside. As a natural product with anti-inflammatory and hepatoprotective properties, it has potential for in vivo efficacy in models of liver injury, inflammation, and oxidative stress. The compound's natural origin and use in traditional medicine suggest it may be well-tolerated. Further in vivo studies including pharmacokinetics and efficacy in animal models would be valuable for therapeutic development.
Enzyme Assay
In vitro antioxidant assays are commonly used to evaluate 6'-O-beta-D-Glucosylgentiopicroside. The DPPH radical scavenging assay involves incubating varying concentrations of the compound with DPPH solution (0.1 mM in ethanol) for 30 minutes at room temperature. The decrease in absorbance at 517 nm is measured. ABTS radical scavenging, FRAP, and ORAC assays can also be performed. For anti-inflammatory activity, enzyme assays measuring COX-2 or LOX inhibition may be conducted. For hepatoprotective activity, liver enzyme inhibition assays (e.g., ALT, AST) can be performed using liver homogenates.
Cell Assay
Cell-based assays for 6'-O-beta-D-Glucosylgentiopicroside include evaluation of anti-inflammatory and hepatoprotective effects. For anti-inflammatory activity, macrophages (e.g., RAW 264.7) are treated with the compound prior to LPS stimulation; inflammatory markers such as NO, TNF-α, and IL-6 are measured. For hepatoprotective activity, hepatocytes (e.g., HepG2) are treated with the compound and then exposed to hepatotoxic agents (e.g., CCl4, acetaminophen). Cell viability is measured by MTT or CCK-8 assays. Liver enzyme levels (ALT, AST) in cell culture supernatants may be measured. The compound shows concentration-dependent protective effects.
Animal Protocol
No specific in vivo animal models are documented for 6'-O-beta-D-Glucosylgentiopicroside. For potential in vivo studies, the compound could be administered orally or intraperitoneally to rodents in models of liver injury (e.g., CCl4-induced hepatotoxicity, acetaminophen-induced liver injury) or inflammation. Doses would be selected based on preliminary pharmacokinetic and tolerability assessments. Endpoints may include serum liver enzyme levels (ALT, AST), inflammatory cytokine levels, oxidative stress markers (MDA, SOD, GSH), and liver histology. The compound's natural origin suggests it may be suitable for oral administration.
ADME/Pharmacokinetics
6'-O-beta-D-Glucosylgentiopicroside has a molecular weight of 518.47 and formula C22H30O14. As a glycoside, the compound is relatively hydrophilic and may have limited oral bioavailability. Glycosides are typically metabolized by gut microbiota to release the aglycone, which may be absorbed. The compound should be stored as powder under appropriate conditions. Solubility in aqueous and organic solvents should be determined experimentally. Further PK studies would be necessary for in vivo applications.
Toxicity/Toxicokinetics
No specific toxicity data are documented for 6'-O-beta-D-Glucosylgentiopicroside. As a natural compound found in Gentiana species used in traditional medicine, it is expected to have low toxicity. However, systematic toxicity studies including acute toxicity, subchronic toxicity, genotoxicity, and organ-specific toxicity would be required for therapeutic development. The compound is intended for research use only and is not approved for human therapeutic applications. Standard laboratory safety practices should be followed when handling the compound.
References

Inhibitory effects of secoiridoids from the roots of Gentiana straminea on stimulus-induced superoxide generation, phosphorylation and translocation of cytosolic compounds to plasma membrane in human neutrophils. Phytother Res. 2012 Feb;26(2):168-73.

Additional Infomation
According to reports, 6'-O-β-D-glucosylgentiol has been found in Gentiana macrophylla, Gentiana scabra, and other organisms with available data.
6'-O-beta-D-Glucosylgentiopicroside is a natural iridoid glycoside found in Gentiana species, including Gentiana scabra and other medicinal plants used in traditional Chinese medicine. It is a derivative of gentiopicroside with an additional glucose moiety at the 6'-position. The compound exhibits anti-inflammatory, hepatoprotective, and antioxidant properties. It is commonly used in research on liver protection, inflammation, and oxidative stress. The compound is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H30O14
Molecular Weight
518.4652
Exact Mass
518.163
CAS #
115713-06-9
PubChem CID
10864232
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Boiling Point
860.2±65.0 °C at 760 mmHg
Flash Point
294.4±27.8 °C
Vapour Pressure
0.0±0.6 mmHg at 25°C
Index of Refraction
1.650
LogP
-2.83
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
14
Rotatable Bond Count
7
Heavy Atom Count
36
Complexity
875
Defined Atom Stereocenter Count
12
SMILES
C=C[C@H]1[C@@H](OC=C2C1=CCOC2=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
InChi Key
BERNCPGDRADLCG-KEXDUYRESA-N
InChi Code
InChI=1S/C22H30O14/c1-2-8-9-3-4-31-19(30)10(9)6-32-20(8)36-22-18(29)16(27)14(25)12(35-22)7-33-21-17(28)15(26)13(24)11(5-23)34-21/h2-3,6,8,11-18,20-29H,1,4-5,7H2/t8-,11-,12-,13-,14-,15+,16+,17-,18-,20+,21-,22+/m1/s1
Chemical Name
(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 (~192.88 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.82 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 25.0 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 (4.82 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (4.82 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9288 mL 9.6438 mL 19.2875 mL
5 mM 0.3858 mL 1.9288 mL 3.8575 mL
10 mM 0.1929 mL 0.9644 mL 1.9288 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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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

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.
             (2) Be sure to add the solvent(s) in order.

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