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| 5mg |
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| 10mg |
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| 25mg |
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| Targets |
Procyanidin A1 targets signaling pathways downstream of protein kinase C (PKC) activation and Ca²⁺ influx from internal stores in RBL-2H3 cells. [1]
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| ln Vitro |
Procyanidin A1 inhibited antigen-stimulated β-hexosaminidase release from RBL-2H3 cells in a dose-dependent manner, with an IC50 value of 20.3 μM. The average β-hexosaminidase release in the absence of the compound was 33.2% of total cellular enzyme activity. Procyanidin A1 also inhibited degranulation induced by phorbol-12-myristate-13-acetate (PMA, a PKC activator) and 2,5-di(tert-butyl)-1,4-hydroquinone (DTBHQ, a Ca²⁺-ATPase inhibitor that releases Ca²⁺ from intracellular stores), with an IC50 of 29.7 μM. There was no significant difference in inhibitory activity between procyanidin A1 and its stereoisomer procyanidin A2. (+)-Catechin (the monomeric unit) showed no inhibitory activity against β-hexosaminidase release. These results indicate that procyanidin A1 inhibits degranulation downstream of PKC activation or Ca²⁺ influx from internal stores. [1]
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| ln Vivo |
Ovalbumin-immunized mice's serum levels of IgE and IgG1 are inhibited by proanthocyanidin A1 [2].
Oral administration of procyanidin A1 (1 to 10 mg/kg/d for 21 consecutive days) to mice immunized intraperitoneally with ovalbumin (OVA) significantly decreased serum OVA-specific IgE and total IgG1 levels compared to control mice. The compound also suppressed the OVA-induced increases in spleen weight and peripheral white blood cell count. Procyanidin A1 (1–10 mg/kg/d) reduced serum interleukin-4 (IL-4) levels and reversed the OVA-induced decrease in interferon-gamma (IFN-γ) levels back to normal. The effects of procyanidin A1 on immunoglobulin suppression and cytokine regulation were similar to or slightly lower than those of the crude peanut skin extract (PSE). [2] |
| Cell Assay |
RBL-2H3 cells were maintained in DMEM containing 10% fetal bovine serum, kanamycin, and NaHCO₃ at 37°C in a 5% CO₂ incubator. Degranulation was monitored by measuring released β-hexosaminidase activity. Cells were diluted to 2×10⁵ cells/mL in DMEM with 10% FBS, and anti-DNP-IgE was added at a final concentration of 50 ng/mL. A 1-mL aliquot of cell suspension was dispensed into a 24-well plate and incubated at 37°C for 16 h. After washing twice with DMEM containing 2% FBS to remove free IgE, various concentrations of procyanidin A1 were added. After 15 min of incubation, 100 μL of 100 μg/mL DNP-BSA was added and the mixture was incubated at 37°C for 1 h. For PMA/DTBHQ-induced degranulation, cells were stimulated with 50 μL of 100 μM DTBHQ and 50 μL of 100 μg/mL PMA without sensitization with anti-DNP-IgE. Supernatant (50 μL) was mixed with 200 μL of 3.8 mM p-nitrophenyl-2-acetoamide-β-D-glucopyranoside in 0.05 M citrate buffer (pH 4.5) and incubated at 37°C for 1 h. Then 500 μL of 0.2 M glycine buffer (pH 10.0) was added, and absorbance at 405 nm was measured. Total β-hexosaminidase activity was determined by adding 500 μL of 0.2% Triton X-100 to lyse cells. The percentage of β-hexosaminidase release was calculated as (free activity / total activity) × 100. [1]
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| Animal Protocol |
Female 8-10-week-old BALB/c mice weighing 20–21 g were used. Mice were immunized intraperitoneally with 20 mg/mouse ovalbumin (OVA) with alum adjuvant. Ten days after the first immunization, mice received a booster with the same dose of OVA. Procyanidin A1 was dissolved in water and administered orally once daily for 21 consecutive days at doses of 1, 5, or 10 mg/kg/d. Control mice received vehicle (distilled water) on the same regimen. Mice were sacrificed by overdose of ether 7 days after the second immunization. Peripheral blood (20 μL/mouse) was collected on day 21 by retro-orbital venous plexus sampling using an EDTA-coated capillary tube, and white blood cell counts were measured using an automatic hemocytometer. Blood samples were also collected by intraventricular exsanguination at 21 days after the first sensitization; serum was separated by centrifugation after clotting and stored at -80°C for measurement of immunoglobulins and cytokines. Spleen weight was measured at day 21. [2]
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| Toxicity/Toxicokinetics |
Oral administration of procyanidin A1 at doses up to 10 mg/kg/d for 21 consecutive days showed no toxicity in mice, as evidenced by no changes in body weight, liver weight, or plasma alanine aminotransferase (ALT) levels (20.4 ± 1.8 U/mL for 10 mg/kg/d procyanidin A1 vs. 18.3 ± 1.1 U/mL for vehicle only; not significant). No other toxicity data (e.g., LD50, hepatotoxicity, protein binding) are reported. [2]
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| References |
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| Additional Infomation |
Proanthocyanidin A1 is a flavonoid oligomer. It has been reported to exist in Pavetta owariensis, Hypericum perforatum, and other organisms with relevant data. See also: Proanthocyanidin A1 (note moved to).
Procyanidin A1 is an A-type procyanidin dimer found in peanut skin. It was purified from an aqueous extract of peanut skin (PSE) by boiling water extraction, which yielded approximately 7.55 mg of procyanidin A1 per 1 g of dry peanut skin, about six times higher than extraction with 80% methanol. The compound was identified by ESI-MS (m/z 599 [M+Na]⁺; molecular formula C₂₄H₃₀O₁₂), ¹H NMR, ¹³C NMR, and optical rotation ([α]¹⁹D = +45.8°). The upper unit of the dimer is epicatechin, and the lower unit is catechin, with double linkages (C2→O→C7 and C4→C8). Procyanidin A1 inhibits degranulation in RBL-2H3 cells by acting downstream of PKC activation or Ca²⁺ influx. In vivo, it suppresses IgE and IgG1 production and modulates Th1/Th2 cytokine balance (reducing IL-4 and restoring IFN-γ), suggesting potential as a therapeutic food component against allergic diseases. [1][2] |
| Molecular Formula |
C30H24O12
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|---|---|
| Molecular Weight |
576.5044
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| Exact Mass |
576.127
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| CAS # |
103883-03-0
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| Related CAS # |
Cyanidin Chloride;528-58-5;Procyanidin B1;20315-25-7;Procyanidin B2;29106-49-8;Procyanidin C1;37064-30-5;Procyanidin A2;41743-41-3;Procyanidin B3;23567-23-9
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| PubChem CID |
9872976
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| Appearance |
White to off-white solid powder
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| Melting Point |
300 °C
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| LogP |
2.793
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| Hydrogen Bond Donor Count |
9
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
42
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| Complexity |
986
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| Defined Atom Stereocenter Count |
5
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| 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
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| InChi Key |
NSEWTSAADLNHNH-TXZJYACMSA-N
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| 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-/m0/s1
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| Chemical Name |
(1R,5R,6S,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
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~173.46 mM)
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|---|---|
| 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. View More
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. |
| 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.
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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