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Vitexin 4"-O-glucoside

Alias: Vitexin 4" O glucoside; Vitexin 4"-O-glucoside; Vitexin 4" O-glucoside
Cat No.:V18127 Purity: ≥98%
Vitexin 4'-O-glucoside is a novel and potent inhibitor of HIV-1 Protease.
Vitexin 4"-O-glucoside
Vitexin 4"-O-glucoside Chemical Structure CAS No.: 178468-00-3
Product category: Plants
This product is for research use only, not for human use. We do not sell to patients.
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25mg
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Product Description
Vitexin 4'-O-glucoside is a novel and potent inhibitor of HIV-1 Protease. It's a flavonoid fraction from the leaves of Crataegus pinnatifida.
Vitexin 4"-O-glucoside is a flavonoid glycoside found in various plants, particularly in species of the genus Vitex and other medicinal plants. It is a derivative of vitexin, a C-glycosyl flavonoid, with an additional glucose moiety at the 4" position. Vitexin 4"-O-glucoside has been studied for its antioxidant, anti-inflammatory, and neuroprotective activities.
Biological Activity I Assay Protocols (From Reference)
Targets
Vitexin 4"-O-glucoside targets multiple pathways including antioxidant defense systems, inflammatory pathways, and neuroprotective signaling. It exerts antioxidant effects by scavenging free radicals and upregulating antioxidant enzyme activity. Its anti-inflammatory activity is mediated through inhibition of pro-inflammatory cytokine production and modulation of NF-κB signaling. The compound also shows neuroprotective effects by reducing oxidative stress and inflammation in neuronal cells.
ln Vitro
In vitro, vitexin 4"-O-glucoside demonstrates antioxidant activity by scavenging free radicals and reducing oxidative stress in cell-based assays. It shows anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines such as TNF-α, IL-1β, and IL-6. The compound exhibits neuroprotective effects by protecting neuronal cells from oxidative stress-induced damage. Specific EC₅₀/IC₅₀ values for these activities are documented in the literature. It is soluble in DMSO and other organic solvents.
ln Vivo
In vivo, vitexin 4"-O-glucoside has been studied in animal models of oxidative stress, inflammation, and neurodegenerative disorders. It shows antioxidant and anti-inflammatory effects in various disease models. The compound's neuroprotective activity has been demonstrated in models of cerebral ischemia, Alzheimer's disease, and Parkinson's disease. Further studies are needed to fully characterize its therapeutic potential and safety profile.
Enzyme Assay
Antioxidant activity is assessed using cell-free assays such as DPPH radical scavenging, ABTS radical scavenging, and ferric reducing antioxidant power (FRAP) assays. Vitexin 4"-O-glucoside is tested at various concentrations, and IC₅₀ values are calculated. Enzyme inhibition assays may be performed to assess inhibition of enzymes such as xanthine oxidase or lipoxygenase. Anti-inflammatory activity is assessed by measuring inhibition of inflammatory mediator production in activated immune cells.
Cell Assay
In vitro cellular assays use various cell lines including neuronal cells (e.g., SH-SY5Y, PC12), immune cells (macrophages, microglia), and other cell types. Cells are treated with vitexin 4"-O-glucoside at various concentrations. Antioxidant activity is assessed by measuring ROS levels using fluorescent probes. Anti-inflammatory activity is measured by cytokine production (ELISA) and NF-κB activation. Neuroprotective effects are assessed by measuring cell viability (MTT assay) and apoptosis markers in cells exposed to oxidative stress or neurotoxic agents.
Animal Protocol
In vivo efficacy is evaluated in animal models of oxidative stress, inflammation, and neurodegenerative disorders. Vitexin 4"-O-glucoside is administered orally or intraperitoneally. Endpoints include oxidative stress markers (MDA, SOD, GSH), inflammatory markers (cytokine levels, COX-2, iNOS), behavioral assessments (in models of neurodegenerative diseases), and histopathological analysis of tissues. Pharmacokinetic studies are conducted to determine plasma concentrations and tissue distribution.
ADME/Pharmacokinetics
Vitexin 4"-O-glucoside is a flavonoid glycoside. Specific chemical properties including molecular weight, molecular formula, and CAS number are documented in the literature. The compound is typically stored at -20°C and protected from light. It is soluble in DMSO and other organic solvents. Specific pharmacokinetic parameters are documented in the literature from preclinical studies. As a glycoside, it may undergo deglycosylation in the gastrointestinal tract or liver before absorption.
Toxicity/Toxicokinetics
Specific toxicity data for vitexin 4"-O-glucoside are documented in preclinical studies. The compound is generally well-tolerated at therapeutic doses based on its natural occurrence in foods and medicinal plants. No significant toxicity has been reported at doses used in research studies. Standard laboratory safety precautions should be followed when handling this compound. It is intended for research use only and not for human therapeutic applications.
References

[1]. An Efficient Method for the Preparative Isolation and Purification of Flavonoids From Leaves of Crataegus Pinnatifida by HSCCC and Pre-HPLC. Molecules. 2017 May 9;22(5):767.

Additional Infomation
Vitexin glucoside belongs to the flavonoid class of compounds and is a C-glycoside compound.
Vitexin 4"-O-glucoside is a flavonoid glycoside with antioxidant, anti-inflammatory, and neuroprotective activities. It is found in various medicinal plants and has been studied for its potential in the treatment of oxidative stress-related diseases, inflammatory conditions, and neurodegenerative disorders. The compound's antioxidant and anti-inflammatory properties make it a promising candidate for further research in the fields of neuroprotection and natural product pharmacology. It is commercially available as a research compound and reference standard.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C33H40O19
Molecular Weight
740.66
Exact Mass
594.158
Elemental Analysis
C, 53.51; H, 5.44; O, 41.04
CAS #
178468-00-3
PubChem CID
56776173
Appearance
Light yellow to yellow solid powder
LogP
-1.9
Hydrogen Bond Donor Count
10
Hydrogen Bond Acceptor Count
15
Rotatable Bond Count
6
Heavy Atom Count
42
Complexity
971
Defined Atom Stereocenter Count
10
SMILES
O([C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@@H]1[C@@H](CO)O[C@@H](C2C(=CC(=C3C(C=C(C4C=CC(=CC=4)O)OC=23)=O)O)O)[C@@H]([C@H]1O)O
InChi Key
NDSUKTASTPEKBX-LXXMDOISSA-N
InChi Code
InChI=1S/C27H30O15/c28-7-15-19(34)20(35)23(38)27(41-15)42-24-16(8-29)40-26(22(37)21(24)36)18-12(32)5-11(31)17-13(33)6-14(39-25(17)18)9-1-3-10(30)4-2-9/h1-6,15-16,19-24,26-32,34-38H,7-8H2/t15-,16-,19-,20+,21-,22-,23-,24-,26+,27+/m1/s1
Chemical Name
8-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms
Vitexin 4" O glucoside; Vitexin 4"-O-glucoside; Vitexin 4" O-glucoside
HS Tariff Code
2934.99.03.00
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 (~168.20 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.21 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 (4.21 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 (4.21 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 1.3501 mL 6.7507 mL 13.5015 mL
5 mM 0.2700 mL 1.3501 mL 2.7003 mL
10 mM 0.1350 mL 0.6751 mL 1.3501 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 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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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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