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| Targets |
Malvidin-3-glucoside chloride targets the NF-κB pathway, reducing IκB-α degradation and p65 nuclear translocation. The compound inhibits TNF-α-induced inflammation in HUVECs and up-regulates endothelial nitric oxide synthase (eNOS) to increase NO production. Its antioxidant activity involves scavenging free radicals and protecting against oxidative stress. The compound's anti-inflammatory effects are primarily mediated through inhibition of the NF-κB signaling pathway.
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| ln Vitro |
Malvidin-3-glucoside chloride inhibits TNF-α-induced inflammation in HUVECs. The compound protects endothelial cells by up-regulating eNOS and inhibiting peroxynitrite-induced NF-κB activation. It exhibits antioxidant activity and is not oxidized in the presence of grape polyphenol oxidase. The compound has neuroprotective effects. These in vitro findings support its potential applications in cardiovascular disease research, inflammation research, and neuroprotection.
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| ln Vivo |
Malvidin-3-glucoside chloride is orally active and has been studied for its cardioprotective and anti-inflammatory effects in vivo. The compound contributes to the health benefits of polyphenol-rich diets. Its ability to inhibit NF-κB and up-regulate eNOS suggests potential for in vivo evaluation in models of cardiovascular disease and inflammation. However, comprehensive in vivo pharmacological studies specifically targeting Malvidin-3-glucoside chloride are limited. The compound is intended for research use only.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Malvidin-3-glucoside chloride typically involve testing its effects on the NF-κB pathway. Cells are treated with varying concentrations of the compound and NF-κB activation is assessed by measuring IκB-α degradation and p65 nuclear translocation. Antioxidant activity is assessed using cell-free systems such as DPPH radical scavenging assays. eNOS activity is measured by monitoring NO production. The compound's purity and identity are confirmed using analytical chemistry methods such as high-performance liquid chromatography and mass spectrometry.
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| Cell Assay |
In vitro cell-based assays for Malvidin-3-glucoside chloride involve culturing HUVECs to evaluate its anti-inflammatory effects. Cells are treated with varying concentrations of the compound and stimulated with TNF-α; inflammatory markers are measured by ELISA. NF-κB activation is assessed by measuring IκB-α degradation and p65 nuclear translocation. eNOS expression and NO production are measured. Cell viability is assessed using standard assays. All experiments are performed with appropriate controls.
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| Animal Protocol |
In vivo animal experiments for Malvidin-3-glucoside chloride would be conducted to evaluate its cardioprotective and anti-inflammatory activities. Animals would be administered the compound orally and cardiovascular parameters assessed. For anti-inflammatory studies, animals with induced inflammation would be treated and inflammatory markers measured. Parameters assessed would include blood pressure, endothelial function, inflammatory markers, and tissue histopathology. Control groups receiving vehicle alone would be included for comparison.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Malvidin-3-glucoside chloride reflect its nature as an anthocyanin glycoside. It has a molecular weight of 528.89 and the molecular formula C23H25ClO12. The compound is orally active. As a glycoside, it may be metabolized by intestinal bacteria to the aglycone. Its bioavailability and color stability have been studied in food science and nutrition research. Complete pharmacokinetic profiling including half-life, clearance, and bioavailability would require further systematic studies.
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| Toxicity/Toxicokinetics |
The toxicity profile of Malvidin-3-glucoside chloride has been evaluated in the context of its use as a food pigment and research chemical. As a naturally occurring anthocyanin found in many fruits and vegetables, it is generally recognized as safe at dietary levels. The compound has a purity suitable for research use. Proper handling procedures including use of personal protective equipment are recommended when working with pure compound. The compound is not approved for human therapeutic use and is intended for research purposes only.
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| References | |
| Additional Infomation |
See also: Malvaceae 3-O-β-D-glucoside (note moved to).
Malvidin-3-glucoside chloride (CAS# 7228-78-6) is also known as Oenin chloride, Malvidin-3-O-glucoside chloride, and NSC 70532. It has the molecular formula C23H25ClO12 and a molecular weight of 528.89. The compound is an orally active NF-κB inhibitor that protects endothelial cells by up-regulating eNOS and inhibiting peroxynitrite-induced NF-κB activation. It exhibits antioxidant, anti-inflammatory, cardioprotective, and neuroprotective properties. |
| Molecular Formula |
C23H25CLO12
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| Molecular Weight |
528.89
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| Exact Mass |
528.103
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| CAS # |
7228-78-6
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| PubChem CID |
11249520
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| Appearance |
Brown to dark brown Solid
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| Boiling Point |
180-190ºC at 0.25 MM HG
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| Melting Point |
70-71ºC
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
36
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| Complexity |
669
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| Defined Atom Stereocenter Count |
5
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| SMILES |
[Cl-].O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1=C([H])C2=C(C([H])=C(C([H])=C2[O+]=C1C1C([H])=C(C(=C(C=1[H])OC([H])([H])[H])O[H])OC([H])([H])[H])O[H])O[H]
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| InChi Key |
YDIKCZBMBPOGFT-DIONPBRTSA-N
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| InChi Code |
InChI=1S/C23H24O12.ClH/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23;/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27);1H/t17-,19-,20+,21-,23-;/m1./s1
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| Chemical Name |
(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
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| Synonyms |
Oenin chloride; Malvidin-3-O-glucoside chloride; Malvidin-3-glucoside chloride
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8908 mL | 9.4538 mL | 18.9075 mL | |
| 5 mM | 0.3782 mL | 1.8908 mL | 3.7815 mL | |
| 10 mM | 0.1891 mL | 0.9454 mL | 1.8908 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.
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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