yingweiwo

Proanthocyanidins

Cat No.:V25246 Purity: ≥98%
Proanthocyanidin (Procyanidin) is a class of polyphenolic compounds widely distributed in higher plants, consisting of electrophilic flavanyl units.
Proanthocyanidins
Proanthocyanidins Chemical Structure CAS No.: 20347-71-1
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
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
Proanthocyanidin (Procyanidin) is a class of polyphenolic compounds widely distributed in higher plants, consisting of electrophilic flavanyl units. Proanthocyanidin works as an antioxidant and anticancer agent. Proanthocyanidin also displays anti-inflammatory, cardioprotective, antibacterial and antifungal properties and may be used to study chronic venous insufficiency, capillary fragility, sunburn and retinopathy.
Proanthocyanidins are a class of polyphenolic compounds widely distributed in higher plants. They are condensed tannins with various pharmacological properties. They are used as antioxidants and anticancer agents. They exhibit anti-inflammatory, cardioprotective, antibacterial, and antifungal properties. They are studied for chronic venous insufficiency, capillary fragility, sunburn, and retinopathy.
Biological Activity I Assay Protocols (From Reference)
Targets
Proanthocyanidins have multiple targets and mechanisms of action. They act as potent antioxidants by scavenging free radicals. They exhibit anticancer effects through mechanisms involving inhibition of cell proliferation and induction of apoptosis. They modulate inflammatory signaling pathways and exhibit antimicrobial activity through membrane disruption or enzyme inhibition. Their cardioprotective effects are related to improved blood circulation and reduced LDL oxidation.
ln Vitro
Complex polymer combinations called proanthocyanidins are found in plants. Berries such as cranberries, apples, pears, and red wine, together with tea and chocolate, are the main sources of nutrition[1]. Because proanthocyanidin is found in cranberries (Vaccinium macrocarpon Ait.), it has the most intriguing antibacterial activity. The efficacy of cranberry consumption in avoiding urinary tract infections (UTIs) has been proven by several clinical trials. Escherichia coli is responsible for about 85% of UTIs, despite the fact that numerous other microbes can also cause them. As P-fimbriae are proteinaceous fibers on the bacterial cell wall, they are responsible for attachment to uroepithelial cells, which is why their presence on E. coli has been clearly identified as a virulence factor. According to recent research, cranberry proanthocyanidin may prevent P-fimbriated E. coli from sticking to uroepithelial cells. It seems that proanthocyanidin with at least one A-type linkage is associated with the antiadhesion activity of cranberry juice[1].
In vitro, proanthocyanidins demonstrate antioxidant activity in various assays, such as DPPH radical scavenging. They exhibit anticancer effects by inhibiting the growth of cancer cell lines. They show anti-inflammatory activity by reducing the production of pro-inflammatory cytokines. They also demonstrate antibacterial and antifungal activity against a range of pathogens.
ln Vivo
Investigated are the effects of Proanthocyanidin from cacao liquor on 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine-induced mutagenesis and in vivo carcinogenesis in female Sprague-Dawley rats. When tested in the presence of the S-9 mixture, proanthocyanidin exhibits potent antimutagenic actions in the Ames test. They also considerably suppress breast carcinogenesis, but not rat pancreatic carcinogenesis in the start stage[1].
In vivo, proanthocyanidins are believed to support cardiovascular health by improving blood circulation, reducing blood pressure, and preventing the oxidation of LDL cholesterol. They possess anti-inflammatory effects and support immune function. They have been studied for their potential anti-cancer properties and for the treatment of chronic venous insufficiency, capillary fragility, sunburn, and retinopathy.
Enzyme Assay
In vitro enzyme/receptor binding studies for proanthocyanidins are not typically focused on a single target due to their complex mixture nature. Studies may involve measuring their antioxidant capacity using assays like DPPH, ABTS, or FRAP. Their ability to inhibit enzymes such as cyclooxygenase (COX) or lipoxygenase (LOX) may be assessed for anti-inflammatory activity. Binding to proteins may be studied using surface plasmon resonance.
Cell Assay
In vitro cellular assays for proanthocyanidins involve culturing cancer cell lines (e.g., breast, colon, prostate) in the presence of serial dilutions of the extract. Cell viability is assessed using MTT or CellTiter-Glo assays. Apoptosis is quantified by flow cytometry with Annexin V/PI staining. Anti-inflammatory activity is assessed in macrophages by measuring cytokine production (e.g., TNF-α, IL-6) upon LPS stimulation.
Animal Protocol
In vivo animal studies for proanthocyanidins include models of cardiovascular disease, inflammation, and cancer. For cardiovascular studies, animals are treated with proanthocyanidins and blood pressure, lipid profiles, and markers of oxidative stress are measured. For anti-inflammatory studies, models such as carrageenan-induced paw edema are used. Standard protocols include dose-response assessment and comparison to vehicle or reference treatments.
ADME/Pharmacokinetics
Pharmacokinetic properties of proanthocyanidins are complex due to their polymeric nature and mixture of compounds. They have a molecular weight of 594.52 and a molecular formula of C₃₀H₂₆O₁₃ for the monomeric unit. They are poorly absorbed and are extensively metabolized by gut microbiota. Their bioavailability is low, and they are primarily excreted in feces. Their metabolites may contribute to their biological activity.
Toxicity/Toxicokinetics
Toxicological data for proanthocyanidins indicate that they are generally safe, as they are naturally occurring compounds found in many foods. They are considered to have low toxicity. High doses may cause gastrointestinal upset. They are not considered carcinogenic or mutagenic. Their use as dietary supplements is common, and they have a favorable safety profile.
References

[1]. Proanthocyanidins, anthocyanins and cardiovascular diseases. Food research international 2014 v.59 pp. 41-52.

[2]. Proanthocyanidins in health care: current and new trends. Curr Med Chem. 2004 May;11(10):1345-59.

Additional Infomation
Procyanidin are oligomeric compounds formed from catechin and epicatechin molecules. They depolymerize under oxidative conditions to form anthocyanins. Procyanidin have been reported to exist in wild peas (Lathyrus laxiflorus), purple grapes (Vitis amurensis), and other organisms with relevant data.
Proanthocyanidins are a class of polyphenolic compounds with diverse pharmacological properties. They are also known as condensed tannins. They are used as antioxidants and are studied for their potential in treating various diseases including cancer, cardiovascular disease, and inflammatory conditions. They are available as dietary supplements and are found in many foods such as grapes, berries, and cocoa.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H26O13
Molecular Weight
594.519649982452
Exact Mass
594.137
CAS #
20347-71-1
PubChem CID
107876
Appearance
Light brown to black solid powder
Density
1.9±0.1 g/cm3
Boiling Point
986.4±65.0 °C at 760 mmHg
Flash Point
550.3±34.3 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.876
LogP
1.46
Hydrogen Bond Donor Count
10
Hydrogen Bond Acceptor Count
13
Rotatable Bond Count
4
Heavy Atom Count
43
Complexity
957
Defined Atom Stereocenter Count
0
InChi Key
HGVVOUNEGQIPMS-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H26O13/c31-14-7-19(35)16-11-25(28(41-23(16)9-14)12-1-3-17(33)20(36)5-12)43-30(13-2-4-18(34)21(37)6-13)29(40)27(39)26-22(38)8-15(32)10-24(26)42-30/h1-10,25,27-29,31-40H,11H2
Chemical Name
2-(3,4-dihydroxyphenyl)-2-[[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-3,4-dihydrochromene-3,4,5,7-tetrol
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 : 100 mg/mL
H2O : 5 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (Infinity mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (Infinity 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 1.6820 mL 8.4101 mL 16.8203 mL
5 mM 0.3364 mL 1.6820 mL 3.3641 mL
10 mM 0.1682 mL 0.8410 mL 1.6820 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