A polyphenol flavonoid dimer with diverse biological activities
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Isomer(s)
25200Procyanidin A2
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Procyanidin A1

Item No. 38893

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3S,8S,14R,15R)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-8,14-methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol
CAS Number
103883-03-0
Synonyms
  • Epicatechin-(4β→8,2β→O→7)-catechin
  • Proanthocyanidin A1
  • Procyanidol A1
Molecular Formula
C30H24O12
Formula Weight
576.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
OC1=C(C[C@H](O)[C@@H](C2=CC(O)=C(O)C=C2)O3)C3=C([C@@]([C@H]4O)([H])C(C(O)=CC(O)=C5)=C5O[C@@]4(C6=CC(O)=C(O)C=C6)O7)C7=C1
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
InChi Key
NSEWTSAADLNHNH-TXZJYACMSA-N
Origin
Plant/Grape seeds
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Procyanidin A1 is a polyphenol flavonoid dimer of (–)-epicatechin (Item No. 11807) and (+)-catechin (Item No. 70940) that has been found in R. spiciferum and has diverse biological activities.1,2,3,4 It binds to placenta growth factor (PlGF) and VEGF (Kds = 394 and 476 nM, respectively) and increases the activity of JAK2 (EC50 = 660 nM).1,2 Procyanidin A1 scavenges superoxide radicals (IC50 = 14.7 µM) and inhibits the cytopathic effects of HIV-1 in MT-4 cells (IC50 = 14 µg/ml).3 It increases the proliferation of isolated mouse splenocytes and peritoneal macrophages when used at concentrations ranging from 25 to 100 µM and DAMI megakaryoblasts (EC50 = 8.58 µM).2,4 Procyanidin A1 (50 mg/kg) prevents decreases in the number of platelets in peripheral blood and megakaryocytes in the bone marrow in a mouse model of thrombocytopenia induced by the DNA cross-linking agent carboplatin (Item No. 13112).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pesca, M.S., Dal Piaz, F., Sanogo, R., et al. Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities. J. Nat. Prod. 76(1), 29-35 (2013).

    2. Wang, R., Hu, X., Wang, J., et al. Proanthocyanidin A1 promotes the production of platelets to ameliorate chemotherapy-induced thrombocytopenia through activating JAK2/STAT3 pathway. Phytomedicine 95:153880, (2022).

    3. De Bruyne, T., Pieters, L., Witvrouw, M., et al. Biological evaluation of proanthocyanidin dimers and related polyphenols. J. Nat. Prod. 62(7), 954-958 (1999).

    4. Liu, Y.Z., Cao, Y.G., Ye, J.Q., et al. Immunomodulatory effects of proanthocyanidin A-1 derived in vitro from Rhododendron spiciferum. Fitoterapia 81(2), 108-114 (2010).