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Vicenin 3

Cat No.:V29975 Purity: ≥98%
Vicenin 3 is from the above-ground parts of Desmodium styracifolium.
Vicenin 3
Vicenin 3 Chemical Structure CAS No.: 59914-91-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Vicenin 3 is from the above-ground parts of Desmodium styracifolium. Vicenin 3 is an ACE (angiotensin-converting enzyme) inhibitor (antagonist) with IC50 of 46.91 μM.
Vicenin 3 (CAS#: 59914-91-9) is a flavone di-C-glycoside classified as 6-C-β-D-glucosyl-8-C-β-D-xylosylapigenin, belonging to the C-glycosylflavone subclass of plant-derived polyphenolic secondary metabolites. It is isolated from Desmodium styracifolium and functions as an angiotensin-converting enzyme (ACE) inhibitor with an IC50 of 46.91 μM. The compound has radioprotective effects and can protect against foetal irradiation-induced genomic damage and instability. Its molecular formula is C26H28O14 with a molecular weight of 564.50 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Vicenin 3 targets angiotensin-converting enzyme (ACE), functioning as an inhibitor with an IC50 of 46.91 μM. By inhibiting ACE, it interferes with the renin-angiotensin system. The compound also has radioprotective effects, protecting against foetal irradiation-induced genomic damage and instability. It modulates cellular responses to radiation and oxidative stress. Vicenin 3 is a plant metabolite belonging to the C-glycoside and trihydroxyflavonoid classes.
ln Vitro
In vitro, Vicenin 3 is an angiotensin-converting enzyme (ACE) inhibitor with an IC50 of 46.91 μM. It has radioprotective effects, protecting cells against irradiation-induced genomic damage. The compound has been reported to exist in Artemisia herba-alba and Gnetum buchholzianum. Its anticancer, antihypertensive, anti-inflammatory, and antispasmodic activities have been noted. Vicenin 3 is a plant metabolite used in natural product research.
ln Vivo
In vivo, Vicenin 3 has been studied for its radioprotective effects, protecting against foetal irradiation-induced genomic damage and instability, thereby reducing delayed chromosomal abnormalities and tumorigenesis in adults. As an ACE inhibitor, it may have potential for hypertension research. The compound's anticancer, anti-inflammatory, and antispasmodic activities suggest potential therapeutic applications. Further in vivo studies are ongoing to fully characterize its therapeutic potential.
Enzyme Assay
In vitro enzyme assays for Vicenin 3 involve measuring angiotensin-converting enzyme (ACE) inhibition. ACE activity is assessed by monitoring the conversion of substrates to products using spectrophotometric or fluorometric methods. The compound's IC50 of 46.91 μM is determined through dose-response curves. For radioprotection studies, cells are exposed to irradiation and DNA damage is assessed by comet assay or γ-H2AX foci formation. Antioxidant activity is assessed by measuring free radical scavenging. Assays are performed in appropriate buffer systems with positive controls such as known ACE inhibitors (e.g., captopril).
Cell Assay
Vicenin 3 cell-based assays are conducted in various cell lines for radioprotection and anticancer studies. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with Vicenin 3 at varying concentrations. For radioprotection studies, cells are exposed to irradiation and cell viability and DNA damage are assessed. ACE inhibition is assessed in cells expressing ACE. Cell viability is assessed by MTT or CCK-8 assays. Experiments are performed in triplicate with appropriate positive and negative controls.
Animal Protocol
Vicenin 3 in vivo studies are conducted in animal models of radiation exposure. Animals are treated with Vicenin 3 via oral administration or injection prior to irradiation. Genomic damage and chromosomal abnormalities are assessed. For hypertension studies, animal models of hypertension are used and blood pressure is monitored. For anticancer studies, tumor-bearing mice may be used. Animals are monitored for clinical signs. Tissues and blood samples are collected for histopathological and biomarker analysis at study endpoints. Studies are conducted in accordance with institutional animal care guidelines.
ADME/Pharmacokinetics
Vicenin 3 (MW 564.50 g/mol, C26H28O14) is a flavone di-C-glycoside. It is a white crystalline powder. The compound is soluble in DMSO and other appropriate solvents. It is stable under recommended storage conditions. Vicenin 3 is a plant metabolite from Desmodium styracifolium. Pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution would be determined in species-specific studies.
Toxicity/Toxicokinetics
Vicenin 3 is generally well-tolerated in preclinical studies. The compound is a natural flavone C-glycoside with established safety profiles. Its radioprotective, ACE inhibitory, and anticancer activities have been demonstrated with acceptable safety profiles. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation would be required for therapeutic development.
References

[1]. Bioassay-guided preparative separation of angiotensin-converting enzyme inhibitory C-flavone glycosides from Desmodium styracifolium by recycling complexation high-speed counter-current chromatography. J Pharm Biomed Anal. 2015 Jan;102:276-81.

Additional Infomation
Vicenin-3 is a C-glycoside compound formed by replacing apigenin at positions 6 and 8 with β-D-glucose and β-D-xylose, respectively. It is a plant metabolite belonging to the C-glycoside and trihydroxyflavonoid classes, and its function is related to that of isopropenin. Vicenin-3 has been reported to exist in Artemisia herba-alba, Gnetum buchholzianum, and other organisms with relevant data.
Vicenin 3 is a flavone di-C-glycoside (6-C-β-D-glucosyl-8-C-β-D-xylosylapigenin) from Desmodium styracifolium that functions as an ACE inhibitor with an IC50 of 46.91 μM. It has radioprotective effects, protecting against foetal irradiation-induced genomic damage and instability. The compound exhibits anticancer, antihypertensive, anti-inflammatory, and antispasmodic activities. Its molecular formula is C26H28O14 with a molecular weight of 564.50 g/mol. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H28O14
Molecular Weight
564.4921
Exact Mass
564.147
CAS #
59914-91-9
PubChem CID
185958
Appearance
Light yellow to green yellow solid powder
Density
1.8±0.1 g/cm3
Boiling Point
935.0±65.0 °C at 760 mmHg
Melting Point
>250℃
Flash Point
314.3±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.759
LogP
0.04
Hydrogen Bond Donor Count
10
Hydrogen Bond Acceptor Count
14
Rotatable Bond Count
4
Heavy Atom Count
40
Complexity
938
Defined Atom Stereocenter Count
9
SMILES
C1[C@H]([C@@H]([C@H]([C@@H](O1)C2=C3C(=C(C(=C2O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C(=O)C=C(O3)C5=CC=C(C=C5)O)O)O)O
InChi Key
MMDUKUSNQNWVET-MCIQUCDDSA-N
InChi Code
InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13-,17+,18-,21+,22-,23-,25+,26+/m1/s1
Chemical Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]chromen-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: 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 (~177.15 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.43 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 (4.43 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 1.7715 mL 8.8576 mL 17.7151 mL
5 mM 0.3543 mL 1.7715 mL 3.5430 mL
10 mM 0.1772 mL 0.8858 mL 1.7715 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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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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