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Isorhamnetin 3-O-galactoside

Cat No.:V29678 Purity: ≥98%
Isorhamnetin 3-O-galactoside (Cacticin), a flavonoid glycoside extracted from Artemisia capillaris Thunberg, improves CCl4-induced liver injury by enhancing the antioxidant defense system and reducing inflammatory signaling pathways.
Isorhamnetin 3-O-galactoside
Isorhamnetin 3-O-galactoside Chemical Structure CAS No.: 6743-92-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
100mg
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Product Description
Isorhamnetin 3-O-galactoside (Cacticin), a flavonoid glycoside extracted from Artemisia capillaris Thunberg, improves CCl4-induced liver injury by enhancing the antioxidant defense system and reducing inflammatory signaling pathways. Isorhamnetin 3-O-galactoside (Cacticin) has antithrombotic and anti~inflammatory effects.
Isorhamnetin 3-O-galactoside (CAS 6743-92-6), also known as Cacticin, is a flavonoid glycoside isolated from Artemisia capillaris Thunberg and other plants such as Ginkgo biloba, Hippophae rhamnoides (sea buckthorn), and Brassica species. With a molecular formula of C₂₂H₂₂O₁₂ and a molecular weight of 478.40 g/mol, this compound ameliorates CCl₄-induced hepatic damage by enhancing the anti-oxidative defense system and reducing inflammatory signaling pathways. Isorhamnetin 3-O-galactoside has antithrombotic and anti-inflammatory activities. It inhibits thrombin and factor Xa function, reduces the rate of thrombin-catalyzed fibrin polymerization, inhibits TNF-α-induced PAI-1 secretion, reduces the PAI-1/t-PA ratio, and decreases FXa generation and FVa/FXa-mediated thrombin generation.
Biological Activity I Assay Protocols (From Reference)
Targets
Isorhamnetin 3-O-galactoside targets multiple pathways involved in thrombosis, inflammation, and oxidative stress. It inhibits thrombin and factor Xa function, key enzymes in the coagulation cascade. The compound reduces the rate of thrombin-catalyzed fibrin polymerization and inhibits TNF-α-induced PAI-1 secretion. It reduces the PAI-1/t-PA ratio and decreases FXa generation and FVa/FXa-mediated thrombin generation. Its anti-inflammatory activity is mediated through the reduction of inflammatory signaling pathways. Its antioxidant activity is mediated through the enhancement of the anti-oxidative defense system.
ln Vitro
In vitro studies have demonstrated that isorhamnetin 3-O-galactoside has antithrombotic and anti-inflammatory activities. It inhibits thrombin and factor Xa function and reduces the rate of thrombin-catalyzed fibrin polymerization. The compound inhibits TNF-α-induced PAI-1 secretion, reduces the PAI-1/t-PA ratio, and decreases FXa generation and FVa/FXa-mediated thrombin generation. It ameliorates CCl₄-induced hepatic damage by enhancing the anti-oxidative defense system and reducing inflammatory signaling pathways. However, detailed in vitro potency data, such as IC₅₀ values for specific activities, are not extensively documented in the available literature.
ln Vivo
In vivo, isorhamnetin 3-O-galactoside has been shown to ameliorate CCl₄-induced hepatic damage. Its antithrombotic and anti-inflammatory activities suggest potential therapeutic applications in thrombotic and inflammatory diseases. However, comprehensive in vivo efficacy and safety studies are needed to fully evaluate its therapeutic potential.
Enzyme Assay
In vitro non-cell enzyme assays for isorhamnetin 3-O-galactoside typically involve measuring its antithrombotic activity by assessing the inhibition of thrombin and factor Xa activity using chromogenic substrates. The compound is incubated with the enzyme and substrate, and the production of chromophore is measured spectrophotometrically. Its antioxidant activity can be measured using DPPH, ABTS, or FRAP assays. Its anti-inflammatory activity can be assessed by measuring the inhibition of inflammatory mediators in cell-free systems.
Cell Assay
In vitro cell-based assays for isorhamnetin 3-O-galactoside use various cell lines to study its biological activities. For antithrombotic studies, endothelial cells or platelets are used, and parameters such as thrombin generation, fibrin polymerization, and PAI-1 secretion are assessed. For anti-inflammatory studies, macrophages or other immune cells stimulated with LPS are used, and the production of inflammatory cytokines is measured by ELISA. For hepatoprotective studies, hepatocytes treated with CCl₄ are used, and parameters such as cell viability, oxidative stress markers, and inflammatory markers are assessed.
Animal Protocol
In vivo animal studies for isorhamnetin 3-O-galactoside would likely employ models of thrombosis, inflammation, and liver injury. For antithrombotic studies, models of venous or arterial thrombosis are used. For anti-inflammatory studies, standard models such as carrageenan-induced paw edema are used. For hepatoprotective studies, models of CCl₄-induced liver injury are used, and parameters such as liver function markers, oxidative stress markers, and histopathology of liver tissues are assessed. Pharmacokinetic studies in these models provide information about the compound's absorption, distribution, metabolism, and excretion.
ADME/Pharmacokinetics
Isorhamnetin 3-O-galactoside has a molecular weight of 478.40 g/mol and a molecular formula of C₂₂H₂₂O₁₂. It is a flavonoid glycoside also known as Cacticin. The compound has a purity of ≥95%. It should be stored long-term in a cool, dry place. Detailed pharmacokinetic parameters such as absorption, distribution, metabolism, and excretion have not been extensively characterized. As a flavonoid glycoside, the compound is expected to have moderate oral bioavailability.
Toxicity/Toxicokinetics
The toxicity profile of isorhamnetin 3-O-galactoside has not been comprehensively evaluated in published studies. As a natural flavonoid from various plants, it is generally considered to have low toxicity. The compound is classified as a research reagent and is not intended for human therapeutic use without further safety evaluation. Standard laboratory safety precautions should be followed when handling the compound.
References

[1]. Isorhamnetin-3-O-galactoside Protects against CCl4-Induced Hepatic Injury in Mice. Biomol Ther (Seoul). 2012 Jul;20(4):406-12.

[2]. Anti-inflammatory activities of isorhamnetin-3-O-galactoside against HMGB1-induced inflammatory responses in both HUVECs and CLP-induced septic mice. J Cell Biochem. 2013 Feb;114(2):336-45.

[3]. Antithrombotic and profibrinolytic activities of isorhamnetin-3-O-galactoside and hyperoside. Food Chem Toxicol. 2013 Mar;53:197-204.

Additional Infomation
Isorhamnetin-3-O-β-D-glucopyranoside is a glycosyloxyflavonoid formed by the substitution of isorhamnetin at the 3-position with a β-D-glucose residue. It is a metabolite. It is a monosaccharide derivative belonging to the glycosyloxyflavonoid, monomethoxyflavonoid, trihydroxyflavonoid, and β-D-glucopyranoside categories. Functionally, it is associated with both isorhamnetin and β-D-glucose. Isorhamnetin-3-O-glucopyranoside has been reported in Anoectochilus formosanus, Halocnemum strobilaceum, and other organisms with relevant data. Isorhamnetin-3-O-glucopyranoside is a metabolite found or produced in Saccharomyces cerevisiae. See also: Ginkgo (partial).
Isorhamnetin 3-O-galactoside is a flavonoid glycoside isolated from Artemisia capillaris Thunberg and other plants. It is also known as Cacticin. The compound ameliorates CCl₄-induced hepatic damage by enhancing the anti-oxidative defense system and reducing inflammatory signaling pathways. It has antithrombotic and anti-inflammatory activities. Isorhamnetin 3-O-galactoside inhibits thrombin and factor Xa function, reduces the rate of thrombin-catalyzed fibrin polymerization, inhibits TNF-α-induced PAI-1 secretion, reduces the PAI-1/t-PA ratio, and decreases FXa generation and FVa/FXa-mediated thrombin generation. Not approved for clinical use; intended for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H22O12
Molecular Weight
478.4029
Exact Mass
478.111
CAS #
6743-92-6
PubChem CID
5318645
Appearance
Light yellow to yellow solid powder
Density
1.75±0.1 g/cm3
Boiling Point
834.4±65.0 °C at 760 mmHg
Melting Point
267-269 ºC
Flash Point
291.3±27.8 °C
Vapour Pressure
0.0±3.2 mmHg at 25°C
Index of Refraction
1.750
LogP
1.71
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
5
Heavy Atom Count
34
Complexity
773
Defined Atom Stereocenter Count
5
SMILES
COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
InChi Key
CQLRUIIRRZYHHS-LFXZADKFSA-N
InChi Code
InChI=1S/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14-,16-,18+,19-,22+/m1/s1
Chemical Name
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-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: 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 (~209.03 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.0903 mL 10.4515 mL 20.9030 mL
5 mM 0.4181 mL 2.0903 mL 4.1806 mL
10 mM 0.2090 mL 1.0452 mL 2.0903 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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