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Procyanidin A2

Cat No.:V30571 Purity: ≥98%
Procyanidin A2 is a flavonoid found in grapes that has anti-cancer, antioxidant, antibacterial and anti~inflammatory activities.
Procyanidin A2
Procyanidin A2 Chemical Structure CAS No.: 41743-41-3
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
25mg
100mg
250mg
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Other Forms of Procyanidin A2:

  • Cyanidin Chloride
  • Procyanidin B1
  • Procyanidin B2 3,3'-di-O-gallate
  • Procyanidin B2 3′-O-gallate
  • Procyanidin B2-3'-O-gallate
  • Procyanidin B2
  • Procyanidin C1
  • Procyanidin A1
  • Procyanidin B3-3-O-gallate
  • Procyanidin B3
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Top Publications Citing lnvivochem Products
Product Description
Procyanidin A2 is a flavonoid found in grapes that has anti-cancer, antioxidant, antibacterial and anti~inflammatory activities.
Biological Activity I Assay Protocols (From Reference)
Targets
- Procyanidin A2 exerts antiproliferative effects on human cancer cells [1]
- Procyanidin A2 modulates the IL-4-mediated signaling pathway in human alveolar epithelial cells, specifically inhibiting IL-4-induced CCL26 production (targets related to IL-4 signaling, e.g., STAT6)[2]
ln Vitro
The DPPH scavenging activity of proanthocyanidin A2 is 5.08 ± 0.37 μM [1].
- Antiproliferative activity against human cancer cells: Procyanidin A2 inhibited the proliferation of three human cancer cell lines in a concentration-dependent manner. For HepG2 (hepatocellular carcinoma cells), 100 μM reduced cell viability by 52%, 50 μM by 38%, and 25 μM by 15% (vs. control) after 48-hour incubation. For MCF-7 (breast cancer cells), 100 μM caused a 48% viability reduction, and for A549 (lung cancer cells), 100 μM caused a 45% viability reduction (MTT assay)[1]
- Inhibition of IL-4-induced CCL26 production in alveolar epithelial cells: In human alveolar epithelial cells (A549), pretreatment with Procyanidin A2 (25, 50 μM) for 2 hours prior to IL-4 (10 ng/mL) stimulation inhibited CCL26 expression. At 50 μM, it reduced CCL26 mRNA levels by 65% (qPCR) and CCL26 protein secretion by 58% (ELISA) compared to the IL-4-only group. At 25 μM, the reductions were 42% (mRNA) and 35% (protein), respectively. Mechanistically, it suppressed IL-4-induced STAT6 phosphorylation (western blot analysis)[2]
Cell Assay
- Cancer cell proliferation assay (MTT method): Human cancer cells (HepG2, MCF-7, A549) were seeded into 96-well plates at a density of 5×10³ cells/well and cultured overnight. Procyanidin A2 (dissolved in DMSO, diluted in medium to final concentrations of 25, 50, 100 μM) was added, and the cells were incubated at 37°C in a 5% CO₂ atmosphere for 48 hours. After incubation, MTT reagent was added to each well and incubated for another 4 hours. The formazan crystals formed were dissolved with DMSO, and absorbance was measured at 570 nm. Cell viability was calculated as (absorbance of drug group/absorbance of control group) × 100%[1]
- CCL26 expression assay in alveolar epithelial cells: Human alveolar epithelial cells (A549) were seeded into 6-well plates (for qPCR) or 24-well plates (for ELISA) and cultured to 80% confluence. The cells were pretreated with Procyanidin A2 (25, 50 μM) for 2 hours, then stimulated with IL-4 (10 ng/mL) for 24 hours. For qPCR: total RNA was extracted, reverse-transcribed into cDNA, and CCL26 mRNA levels were quantified using specific primers (normalized to GAPDH). For ELISA: culture supernatant was collected, and CCL26 protein concentration was measured using a specific antibody kit. For western blot: cell lysates were prepared, and STAT6 phosphorylation levels were detected using phospho-STAT6 and total STAT6 antibodies[2]
References

[1]. Identification of flavonoids in litchi (Litchi chinensis Sonn.) leaf and evaluation of anticancer activities. Journal of Functional Foods. January 2014, 6, P: 555-563.

[2]. Procyanidin A2 Modulates IL-4-Induced CCL26 Production in Human Alveolar Epithelial Cells. Int J Mol Sci. 2016 Nov 12;17(11).

Additional Infomation
Proanthocyanidin A2 is a proanthocyanidin formed by the condensation of (-)-epicatechin units. It possesses antioxidant, anti-HIV, metabolic, and angiogenesis-regulating effects. It is a hydroxyflavan and proanthocyanidin, functionally related to (-)-epicatechin. Proanthocyanidin A2 has been reported to exist in cinnamon (Cinnamomum iners), litchi (Litchi chinensis), and other organisms with relevant data. See also: Litchi fruit (partial). Proanthocyanidin A2 is a flavonoid compound isolated from the leaves of litchi (Litchi chinensis Sonn.). Lychee[1] - The anti-proliferative effect of proanthocyanidins A2 on cancer cells is concentration-dependent. The higher the concentration (≥50 μM), the better the therapeutic effect. However, at a concentration of 100 μM, it has no obvious toxicity to normal human peripheral blood mononuclear cells (PBMCs)[1] - The inhibitory effect of proanthocyanidins A2 on IL-4-induced CCL26 production is achieved by blocking the phosphorylation of STAT6. STAT6 is a key transcription factor in the IL-4 signaling pathway and can regulate the expression of the CCL26 gene[2]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H24O12
Molecular Weight
576.5044
Exact Mass
576.127
CAS #
41743-41-3
Related CAS #
Cyanidin Chloride;528-58-5;Procyanidin B1;20315-25-7;Procyanidin B2;29106-49-8;Procyanidin C1;37064-30-5;Procyanidin A1;103883-03-0;Procyanidin B3;23567-23-9
PubChem CID
124025
Appearance
White to pink solid powder
Density
1.766g/cm3
Boiling Point
946ºC at 760 mmHg
Melting Point
300 °C
Flash Point
525.9ºC
Index of Refraction
1.829
LogP
2.793
Hydrogen Bond Donor Count
9
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
2
Heavy Atom Count
42
Complexity
986
Defined Atom Stereocenter Count
5
SMILES
C1[C@H]([C@H](OC2=C1C(=CC3=C2[C@@H]4[C@H]([C@](O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O)C7=CC(=C(C=C7)O)O)O
InChi Key
NSEWTSAADLNHNH-LSBOWGMISA-N
InChi Code
InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1
Chemical Name
(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
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: 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)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~173.46 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.34 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 (4.34 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 (4.34 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 1.7346 mL 8.6730 mL 17.3461 mL
5 mM 0.3469 mL 1.7346 mL 3.4692 mL
10 mM 0.1735 mL 0.8673 mL 1.7346 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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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)
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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.
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