Procyanidin C1CAS# 37064-30-5 |
Quality Control & MSDS
3D structure
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| Cas No. | 37064-30-5 | SDF | Download SDF |
| PubChem ID | 169853 | Appearance | Beige-brown powder |
| Formula | C45H38O18 | M.Wt | 866.77 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | Cinnamtannin A1; (-)-Epicatechin (4β-8)-(-)-epicatechin (4β-8)-(-)-epicatechin; Proanthocyanidin C1 | ||
| Solubility | Soluble in methan | ||
| Chemical Name | (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol | ||
| SMILES | C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=C(C(=CC(=C34)O)O)C5C(C(OC6=CC(=CC(=C56)O)O)C7=CC(=C(C=C7)O)O)O)C8=CC(=C(C=C8)O)O)O)O)O)C9=CC(=C(C=C9)O)O)O | ||
| Standard InChIKey | MOJZMWJRUKIQGL-XILRTYJMSA-N | ||
| Standard InChI | InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1 | ||
| 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. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Procyanidin C1 has anti-inflammatory effects, can inhibit IKKb activity in vitro and reduce the LPS-induced production of ROS, thus, it exerts the anti-inflammatory effects by inhibiting ERK1/2 and IKKb activity. Procyanidin C1 could be useful as a lead compound to develop inhibitors of cancer metastasis and other diseases related to epithelial-to-mesenchymal transition (EMT). Procyanidin C1 may represent a novel and potentially therapeutically relevant compound for the treatment of cardiovascular diseases, it -induced vasorelaxation is associated with the activation of the calcium-dependent NO/cGMP pathway, involving potassium channel activation. |
| Targets | NO | TGF-β/Smad | ROS | Syk | IL Receptor |
| In vitro | Procyanidin C1 from apple extracts inhibits Fc epsilon RI-mediated mast cell activation.[Pubmed: 18594151]Int Arch Allergy Immunol. 2008;147(3):213-21.Polyphenol-enriched fractions, which are extracted from unripe apples (Rosaceae, Malus spp.), consisting of procyanidins (polymers of catechins) are known to have an anti-allergenic effect on patients with various allergic diseases. Although it has been reported that apple extracts inhibit histamine release from mast cells, the molecular mechanisms for this anti-allergenic effect are not well understood. To elucidate the molecular mechanisms by which apple extracts induce their anti-allergenic effects, the effects of purified apple extract components on high-affinity receptors for IgE (Fc epsilon RI)-mediated mast cell activation were investigated. Immunosuppressive Effects of A-Type Procyanidin Oligomers from Cinnamomum tamala.[Pubmed: 25530780]Evid Based Complement Alternat Med. 2014;2014:365258.Cinnamon barks extracts have been reported to regulate immune function; however, the component(s) in cinnamon barks responsible for this effect is/are not yet clear. The aim of this study is to find out the possible component(s) that can be used as therapeutic agents for immune-related diseases from cinnamon bark. |
| Kinase Assay | Procyanidin C1 from Cinnamomi Cortex inhibits TGF-β-induced epithelial-to-mesenchymal transition in the A549 lung cancer cell line.[Pubmed: 24141365]Procyanidin C1 causes vasorelaxation through activation of the endothelial NO/cGMP pathway in thoracic aortic rings.[Pubmed: 24971771 ]J Med Food. 2014 Jul;17(7):742-8.The aim of this study was to clarify the efficacy of Procyanidin C1 (Pro C1) for modulating vascular tone. Int J Oncol. 2013 Dec;43(6):1901-6.Cancer metastasis is one of the most critical events in cancer patients, and the median overall survival of stage IIIb or IV patients with metastatic lung cancer in the TNM classification is only 8 or 5 months, respectively. We previously demonstrated that Juzentaihoto, a Japanese traditional medicine, can inhibit cancer metastasis through the activation of macrophages and T cells in mouse cancer metastatic models; however, the mechanism(s) through which Juzentaihoto directly affects tumor cells during the metastasis process and which herbal components from Juzentaihoto inhibit the metastatic potential have not been elucidated. |
Procyanidin C1 Dilution Calculator
Procyanidin C1 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.1537 mL | 5.7685 mL | 11.5371 mL | 23.0742 mL | 28.8427 mL |
| 5 mM | 0.2307 mL | 1.1537 mL | 2.3074 mL | 4.6148 mL | 5.7685 mL |
| 10 mM | 0.1154 mL | 0.5769 mL | 1.1537 mL | 2.3074 mL | 2.8843 mL |
| 50 mM | 0.0231 mL | 0.1154 mL | 0.2307 mL | 0.4615 mL | 0.5769 mL |
| 100 mM | 0.0115 mL | 0.0577 mL | 0.1154 mL | 0.2307 mL | 0.2884 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. | |||||
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Procyanidin C1 causes vasorelaxation through activation of the endothelial NO/cGMP pathway in thoracic aortic rings.[Pubmed:24971771]
J Med Food. 2014 Jul;17(7):742-8.
The aim of this study was to clarify the efficacy of Procyanidin C1 (Pro C1) for modulating vascular tone. Pro C1 induced a potent vasorelaxant effect on phenylephrine-constricted endothelium-intact thoracic aortic rings, but had no effect on denuded thoracic aortic rings. Moreover, Pro C1 caused a significant increase in nitric oxide (NO) production in endothelial cells. Pro C1-induced vasorelaxation and Pro C1-induced NO production were significantly decreased in the presence of a nonspecific potassium channel blocker (tetraethylammonium chloride [TEA]), an endothelial NO synthase inhibitor (N(G)-monomethyl-L-arginine [L-NMMA]), and a store-operated calcium entry inhibitor (2-aminoethyl diphenylborinate [2-APB]). Pro C1-induced vasorelaxation was also completely abolished by an inhibitor of soluble guanyl cyclase, which suggests that the Pro C1 effects observed involved cyclic guanosine monophosphate (cGMP) production. Interestingly, Pro C1 significantly enhanced basal cGMP levels. Taken together, these results indicate that Pro C1-induced vasorelaxation is associated with the activation of the calcium-dependent NO/cGMP pathway, involving potassium channel activation. Thus, Pro C1 may represent a novel and potentially therapeutically relevant compound for the treatment of cardiovascular diseases.
Procyanidin C1 from Cinnamomi Cortex inhibits TGF-beta-induced epithelial-to-mesenchymal transition in the A549 lung cancer cell line.[Pubmed:24141365]
Int J Oncol. 2013 Dec;43(6):1901-6.
Cancer metastasis is one of the most critical events in cancer patients, and the median overall survival of stage IIIb or IV patients with metastatic lung cancer in the TNM classification is only 8 or 5 months, respectively. We previously demonstrated that Juzentaihoto, a Japanese traditional medicine, can inhibit cancer metastasis through the activation of macrophages and T cells in mouse cancer metastatic models; however, the mechanism(s) through which Juzentaihoto directly affects tumor cells during the metastasis process and which herbal components from Juzentaihoto inhibit the metastatic potential have not been elucidated. In this study, we focused on the epithelial-to-mesenchymal transition (EMT), which plays an important role in the formation of cancer metastasis. We newly determined that only the Cinnamomi Cortex (CC) extract, one of 10 herbal components of Juzentaihoto, inhibits TGF-beta-induced EMT. Moreover, the contents of catechin trimer in CC extracts were significantly correlated with the efficacy of inhibiting TGF-beta-induced EMT. Finally, the structure of the catechin trimer from CC extract was chemically identified as Procyanidin C1 and the compound showed inhibitory activity against TGF-beta-induced EMT. This illustrates that Procyanidin C1 is the main active compound in the CC extract responsible for EMT inhibition and that Procyanidin C1 could be useful as a lead compound to develop inhibitors of cancer metastasis and other diseases related to EMT.
Immunosuppressive Effects of A-Type Procyanidin Oligomers from Cinnamomum tamala.[Pubmed:25530780]
Evid Based Complement Alternat Med. 2014;2014:365258.
Cinnamon barks extracts have been reported to regulate immune function; however, the component(s) in cinnamon barks responsible for this effect is/are not yet clear. The aim of this study is to find out the possible component(s) that can be used as therapeutic agents for immune-related diseases from cinnamon bark. In this study, the immunosuppressive effects of fraction (named CT-F) and five procyanidin oligomers compounds, cinnamtannin B1, cinnamtannin D1 (CTD-1), parameritannin A1, procyanidin B2, and Procyanidin C1, from Cinnamomum tamala or Cinnamomum cassia bark were examined on splenocytes proliferation model induced by ConA or LPS. Then, the effects of activated compound CTD-1 on cytokine production and 2,4-dinitrofluorobenzene (DNFB) induced delayed-type hypersensitivity (DTH) response were detected to evaluate the immunosuppressive activity of CTD-1. It was found that CT-F and CTD-1 significantly inhibited the splenocyte proliferation induced by ConA or LPS. CTD-1 dose-dependently reduced the level of IFN-gamma and IL-2 and intensively suppressed DNFB-induced DTH responses. These findings suggest that the immunosuppressive activities of cinnamon bark are in part due to procyanidin oligomers. CTD-1 may be a potential therapeutic agent for immune-related diseases.
Procyanidin C1 from apple extracts inhibits Fc epsilon RI-mediated mast cell activation.[Pubmed:18594151]
Int Arch Allergy Immunol. 2008;147(3):213-21.
BACKGROUND: Polyphenol-enriched fractions, which are extracted from unripe apples (Rosaceae, Malus spp.), consisting of procyanidins (polymers of catechins) are known to have an anti-allergenic effect on patients with various allergic diseases. Although it has been reported that apple extracts inhibit histamine release from mast cells, the molecular mechanisms for this anti-allergenic effect are not well understood. To elucidate the molecular mechanisms by which apple extracts induce their anti-allergenic effects, the effects of purified apple extract components on high-affinity receptors for IgE (Fc epsilon RI)-mediated mast cell activation were investigated. METHODS: The anti-allergic effect of oral administration of apple procyanidin extracts on passive cutaneous anaphylactic responses of BALB/c mice was assessed. We evaluated the effects of Procyanidin C1 (PC1) [epicatechin-(4beta-->8)-epicatechin-(4beta-->8)-epicatechin], a component of the procyanidin fraction, on mouse bone-marrow-derived mast cell degranulation, cytokine production, protein tyrosine phosphorylation and on the generation of intracellular reactive oxygen species (ROS) of cells stimulated by Fc epsilon RI cross-linking in vitro. RESULTS: In an in vivo study, oral administration of the procyanidin fraction suppressed the mast-cell-dependent allergic reaction. In in vitro studies, PC1 dose-dependently decreased Fc epsilon RI-mediated degranulation and cytokine production of mast cells. Furthermore, PC1 inhibited tyrosine phosphorylation of Syk and linker for activation of T cells, and the ROS generation in stimulated mast cells. CONCLUSIONS: PC1 suppresses Fc epsilon RI-mediated mast cell activation by inhibiting intracellular signaling pathways. These observations provide evidence for the anti-allergenic effects of the procyanidin-enriched apple extract.
