yingweiwo

Astringin

Cat No.:V31023 Purity: ≥98%
Astringin (trans-Astringin) is a natural glycoside found in spruce (Picea sitchensis) and Norway spruce (Picea abies), grape (Vitis vinifera) cell cultures and wine.
Astringin
Astringin Chemical Structure CAS No.: 29884-49-9
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
100mg
Other Sizes
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text

 

  • Business Relationship with 5000+ Clients Globally
  • Major Universities, Research Institutions, Biotech & Pharma
  • Citations by Top Journals: Nature, Cell, Science, etc.
Top Publications Citing lnvivochem Products
Product Description
Astringin (trans-Astringin) is a natural glycoside found in spruce (Picea sitchensis) and Norway spruce (Picea abies), grape (Vitis vinifera) cell cultures and wine. Astringin has potent antioxidant capacity and cancer chemopreventive activity.
Astringin (CAS 29884-49-9), also known as trans-Astringin or 3,4,3',5'-Tetrahydroxystilbene 3'-glucoside, is a phenolic stilbene glucoside structurally related to resveratrol. It is commonly found in plants such as Picea, grapevines (V. vinifera), oak bark, witch hazel, and tea leaves. Astringin has a molecular weight of 406.38 g/mol and a molecular formula of C20H22O9. It is known for its strong antioxidant and anti-inflammatory properties, helping to protect cells from oxidative stress and modulate inflammatory pathways. Astringin also exhibits cardioprotective, neuroprotective, and anticancer potential by influencing cellular signaling and apoptosis. Additionally, it functions as a ferroptosis inhibitor.
Biological Activity I Assay Protocols (From Reference)
Targets
Astringin primarily targets inflammatory pathways and oxidative stress. It inhibits the PI3K/AKT/NF-kappaB pathway, thereby reducing oxidative stress and inflammatory responses. It also modulates the TLR4/MyD88, HMGB1/RAGE, and NF-kappaB pathways to counteract chromium-induced nephrotoxicity. As a ferroptosis inhibitor, Astringin may target pathways involved in iron-dependent cell death. Its antioxidant activity is attributed to its ability to scavenge free radicals, such as DPPH. The compound's anti-inflammatory effects are mediated through the modulation of pro-inflammatory cytokine production and signaling pathways.
ln Vitro
In vitro, Astringin exhibits potent antioxidant capacity, as demonstrated by its ability to scavenge DPPH and ABTS free radicals. It has potent antioxidant and cancer-chemopreventive activity. Astringin inhibits the PI3K/AKT/NF-kappaB pathway, thereby reducing oxidative stress and inflammatory responses. It also functions as a ferroptosis inhibitor. The compound has been shown to have anti-inflammatory effects by modulating inflammatory pathways and reducing the production of pro-inflammatory mediators. Its cardioprotective, neuroprotective, and anticancer activities have been observed in various cell-based assays.
ln Vivo
In vivo, Astringin has demonstrated cardioprotective activity in ischemic and ischemic-reperfused rat hearts. The beneficial effects of Astringin in ischemic hearts may be correlated with its antioxidant activity and upregulation of nitric oxide (NO) production. It also exhibits anti-inflammatory effects by modulating inflammatory pathways. Astringin has been studied for its potential to protect against chromium-induced nephrotoxicity by modulating the TLR4/MyD88, HMGB1/RAGE, and NF-kappaB pathways. Its oral activity suggests that it may be suitable for oral administration in preclinical studies. Further in vivo studies are needed to fully characterize its efficacy and safety profile.
Enzyme Assay
Cell-free assays for Astringin typically involve assessing its antioxidant activity. A common protocol for DPPH radical scavenging assay involves preparing a DPPH solution in methanol and incubating it with various concentrations of Astringin at room temperature for 30 minutes. The absorbance is measured at 517 nm, and the percentage of radical scavenging activity is calculated. For ABTS radical cation decolorization assay, ABTS is oxidized with potassium persulfate to generate the ABTS radical cation, which is then incubated with the compound. The decrease in absorbance at 734 nm is measured. The IC50 value is determined by plotting the percentage of scavenging against the compound concentration.
Cell Assay
For in vitro cellular experiments, cells (e.g., macrophages, cancer cell lines, or neuronal cells) are cultured in appropriate media and treated with Astringin at various concentrations (typically 1-100 uM). For anti-inflammatory studies, macrophages are stimulated with LPS in the presence or absence of the compound, and the production of pro-inflammatory cytokines (e.g., TNF-alpha, IL-6) is measured by ELISA. For antioxidant studies, cells are exposed to oxidative stress (e.g., H2O2) in the presence or absence of the compound, and oxidative stress markers (e.g., ROS, MDA) are measured. For ferroptosis studies, cells are treated with ferroptosis inducers and Astringin, and cell viability and lipid peroxidation are assessed.
Animal Protocol
In vivo animal experiments with Astringin have been performed in rat models of cardiac ischemia-reperfusion injury. A typical protocol involves inducing ischemia in the rat heart by ligation of the coronary artery, followed by reperfusion. Astringin is administered intravenously or orally before or after ischemia, and cardiac function is assessed by measuring infarct size, hemodynamic parameters, and biochemical markers of oxidative stress. For nephroprotection studies, animals are treated with chromium to induce nephrotoxicity, and Astringin is administered orally. Kidney function is assessed by measuring serum creatinine and blood urea nitrogen, and renal tissue is collected for histopathological examination.
ADME/Pharmacokinetics
Pharmacokinetic data for Astringin are limited. As a glucosylated stilbene with a molecular weight of 406.38 g/mol, it is expected to have moderate oral bioavailability. The compound is soluble in DMSO. Its absorption, distribution, metabolism, and excretion properties would need to be characterized in preclinical studies. The compound is stable as a powder and should be stored under recommended conditions. Further pharmacokinetic studies are needed to determine its bioavailability, half-life, and tissue distribution.
Toxicity/Toxicokinetics
The toxicity profile of Astringin has not been extensively characterized. As a natural product with antioxidant and anti-inflammatory activities, it is expected to have a favorable safety profile at pharmacological doses. However, high doses may cause gastrointestinal discomfort or other mild adverse effects. The compound has been reported to have low toxicity in cell-based assays. The compound should be handled with standard laboratory precautions and is intended for research use only. Further toxicological studies are needed to establish its full safety profile.
References

[1]. Highly regioselective hydroxylation of polydatin, a resveratrol glucoside, for one-step synthesis of astringin, a piceatannol glucoside, by P450 BM3. Enzyme Microb Technol. 2017 Feb;97:34-42.

Additional Infomation
Trans-astine is a stilbene compound, a derivative of paclitaxel with a β-D-glucose substituted at the 3-position. It possesses metabolic, antioxidant, and antitumor activities. It is a polyphenol, stilbene compound, β-D-glucoside, and monosaccharide derivative. Its function is related to that of paclitaxel. Astine has been reported in Abies nephrolepis, Picea abies, and other organisms with relevant data. Astine is a metabolite found or produced in Saccharomyces cerevisiae.
Astringin (trans-Astringin) is a phenolic stilbene glucoside structurally related to resveratrol, found in plants such as Picea and grapevines. It has a molecular weight of 406.38 g/mol and a molecular formula of C20H22O9. Astringin exhibits strong antioxidant, anti-inflammatory, and anticancer properties. It inhibits the PI3K/AKT/NF-kappaB pathway and modulates TLR4/MyD88, HMGB1/RAGE, and NF-kappaB pathways. It also functions as a ferroptosis inhibitor. Astringin has cardioprotective activity in ischemic rat hearts and is available as a research compound for studying oxidative stress, inflammation, and cancer. It is not approved for clinical use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H22O9
Molecular Weight
406.3833
Exact Mass
406.126
CAS #
29884-49-9
PubChem CID
5281712
Appearance
White to yellow solid powder
Density
1.593±0.06 g/cm3(Predicted)
Boiling Point
756.1±60.0 °C(Predicted)
Melting Point
218-220 °C
Vapour Pressure
5.06E-24mmHg at 25°C
LogP
0.152
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
5
Heavy Atom Count
29
Complexity
544
Defined Atom Stereocenter Count
5
SMILES
C1=CC(=C(C=C1/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
InChi Key
PERPNFLGJXUDDW-CUYWLFDKSA-N
InChi Code
InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
Chemical Name
(2S,3R,4S,5S,6R)-2-[3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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

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 : ~125 mg/mL (~307.59 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.25 mg/mL (3.08 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 12.5 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: ≥ 1.25 mg/mL (3.08 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 12.5 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 2.4608 mL 12.3038 mL 24.6075 mL
5 mM 0.4922 mL 2.4608 mL 4.9215 mL
10 mM 0.2461 mL 1.2304 mL 2.4608 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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.)
+
+
+

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.

Contact Us