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Procyanidin B3

Procyanidin B3

Catalog No. BCN6316
Size Price Stock
5mg $418 In stock
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Chemical structure

Procyanidin B3

Biological Activity of Procyanidin B3

1. Procyanidin B3 (B3) is a procyanidin dimer that is widely studied due to its high abundance in the human diet and antioxidant activity.
2. Procyanidin B3 (B3) has stronger anti-inflammatory activity than that of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agents.
3. Procyanidin B3 (B3) prevented the progression of osteoarthritis (OA) and heterotopic cartilage formation, by inhibiting H2O2-induced apoptosis in primary chondrocytes, suppressing H2O2- or IL-1ß−induced nitric oxide synthase (iNOS) production, and preventing IL-1ß−induced suppression of chondrocyte differentiation marker gene expression in primary chondrocytes.

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Chemical Properties of Procyanidin B3

Cas No. 23567-23-9 SDF Download SDF
Chemical Name (2R,3S,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl]chroman-3,5,7-triol
SMILES O[C@H]1Cc2c(O)cc(O)c([C@H]3[C@H](O)[C@H](Oc4cc(O)cc(O)c34)c5ccc(O)c(O)c5)c2O[C@@H]1c6ccc(O)c(O)c6
Standard InChI InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1
Type of Compound Flavonoids Appearance Powder
Formula C30H26O12 M.Wt 578.52
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of Procyanidin B3

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7285 mL 8.6427 mL 17.2855 mL 34.571 mL 43.2137 mL
5 mM 0.3457 mL 1.7285 mL 3.4571 mL 6.9142 mL 8.6427 mL
10 mM 0.1729 mL 0.8643 mL 1.7285 mL 3.4571 mL 4.3214 mL
50 mM 0.0346 mL 0.1729 mL 0.3457 mL 0.6914 mL 0.8643 mL
100 mM 0.0173 mL 0.0864 mL 0.1729 mL 0.3457 mL 0.4321 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Preparation of Procyanidin B3

This product is isolated and purified from the fruits of Vitis vinifera L.

References on Procyanidin B3

Influence of carbohydrates on the interaction of procyanidin B3 with trypsin.[Pubmed: 21950419]

Using STD-NMR, it was possible to identify the binding of Procyanidin B3 to trypsin. The tested carbohydrates prevented the association of Procyanidin B3 and trypsin by a competition mechanism in which the ionic character of carbohydrates and their ability to encapsulate procyanidins seem crucial leading to a reduction in STD signal and light scattering and to a recovery of the proteins intrinsic fluorescence.

Procyanidin B3 prevents articular cartilage degeneration and heterotopic cartilage formation in a mouse surgical osteoarthritis model.[Pubmed: 22629448]

Procyanidin B3 (B3) is a procyanidin dimer that is widely studied due to its high abundance in the human diet and antioxidant activity. Here, we evaluated the role of Procyanidin B3 isolated from grape seeds in the maintenance of chondrocytes in vitro and in vivo. We observed that Procyanidin B3 inhibited H(2)O(2)-induced apoptosis in primary chondrocytes, suppressed H(2)O(2)- or IL-1ß-induced nitric oxide synthase (iNOS) production, and prevented IL-1ß-induced suppression of chondrocyte differentiation marker gene expression in primary chondrocytes. Moreover, Procyanidin B3 treatment enhanced the early differentiation of ATDC5 cells. To examine whether Procyanidin B3 prevents cartilage destruction in vivo, OA was surgically induced in C57BL/6J mice followed by oral administration of Procyanidin B3 or vehicle control. Daily oral Procyanidin B3 administration protected articular cartilage from OA and prevented chondrocyte apoptosis in surgically-induced OA joints. Furthermore, Procyanidin B3 administration prevented heterotopic cartilage formation near the surgical region. iNOS protein expression was enhanced in the synovial tissues and the pseudocapsule around the surgical region in OA mice fed a control diet, but was reduced in mice that received Procyanidin B3. Together, these data indicated that in the OA model, Procyanidin B3 prevented OA progression and heterotopic cartilage formation, at least in a part through the suppression of iNOS. These results support the potential therapeutic benefits of Procyanidin B3 for treatment of human OA and heterotopic ossification.

Osteoarthritis: Procyanidin B3 prevents OA in vivo.[Pubmed: 22744145]

Procyanidin B3 prevents articular cartilage degeneration and heterotopic cartilage formation in a mouse surgical osteoarthritis model.

Procyanidin B3, an inhibitor of histone acetyltransferase, enhances the action of antagonist for prostate cancer cells via inhibition of p300-dependent acetylation of androgen receptor.[Pubmed: 20955177]

Increasing evidence suggests that AR (androgen receptor) acetylation is critical for prostate cancer cell growth. In the present study, we identified Pro-B3 (Procyanidin B3) as a specific HAT (histone acetyltransferase) inhibitor. Procyanidin B3 selectively inhibited the activity of HATs, but not other epigenetic enzymes. Procyanidin B3 substantially inhibited the p300-mediated AR acetylation, both in vitro and in vivo. Procyanidin B3 inhibited both p300-dependent and agonist-induced AR transcription. We demonstrate that the p300-mediated AR acetylation is critical for the hormone responsiveness of AR. Interestingly, B3 treatment efficiently enhanced the antagonist activity of flutamide through suppression of p300 HAT activity, demonstrating that relative p300 activity is critical for the antagonist action. Finally, Procyanidin B3 treatment inhibited acetylation-dependent prostate cell proliferation and expression of cell-cycle control genes, subsequently increasing cell death, indicating the functional importance of AR acetylation for prostate cancer cell growth.


Procyanidin B3 ,23567-23-9,Nature Products, supplier, inhibitor,Antagonist,Blocker,Modulator,Agonist, activators, activates, potent, BioCrick

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