Procyanidin C1
(Synonyms: 原花青素 C1; PCC1) 目录号 : GC44689
A polyphenol flavonoid with HIV-related and antioxidant activities
Cas No.:37064-30-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| Cell experiment [1]: | |
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Cell lines |
RAW 264.7 macrophage cells and Bone marrow derived macrophages(BMDMs) |
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Preparation Method |
RAW 264.7 macrophage cells (1×105 cells/well) and BMDMs (0.5×106 cells/well) were cultured in 48-well and 12-well plates with DMEM containing 10% FBS, and then incubated at 37℃ under 5% CO2 in an incubator until they reached 95% confluence. Procyanidin C1 (at concentrations of 31.25 and 62.5μg/ml) was added to each well and incubated at 37℃ for 24h. |
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Reaction Conditions |
31.25μg/ml and 62.5μg/ml |
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Applications |
Procyanidin C1 significantly (P |
| Animal experiment [2]: | |
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Animal models |
Male ICR mice weighing 35–40g |
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Preparation Method |
Male ICR mice were treated with a single oral dose of flavan3-ols（FL）, epicatechin（EC）, procyanidin B2（B2), procyanidin C1(C1), cinnamtannin A2(A2), or pentamer fraction(P5). The animals were sacrificed and blood and brown adipose tissue (BAT) sampled. The plasma catecholamine (CA) levels and BAT uncoupling protein (UCP)-1 mRNA expression were determined. |
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Applications |
A single dose of 10mg/kg FL significantly increased plasma CA and UCP-1 mRNA levels. B2, procyanidin C1, and A2, but not EC and P5 (all at 1mg/kg), significantly increased plasma adrenaline levels. Plasma noradrenaline was significantly elevated by B2 and A2, but not by EC, procyanidin C1, or P5. UCP-1 mRNA levels were significantly increased by procyanidin C1 and P5. In the dose response study of A2, 10-3mg/kg A2 increased UCP-1 mRNA levels significantly, but not 10-2 and 10-1mg/kg A2. In addition, combination treatment with 10-1mg/kg A2 and yohimbine, an α2 adrenalin blocker, remarkably increased UCP-1 mRNA levels. |
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References: [1]. Sung NY, Yang MS, et al. The procyanidin trimer C1 induces macrophage activation via NF-κB and MAPK pathways, leading to Th1 polarization in murine splenocytes. Eur J Pharmacol. 2013;714(1-3):218-228. [2]. Nakagawa Y, Ishimura K, et al. Comparison of the sympathetic stimulatory abilities of B-type procyanidins based on induction of uncoupling protein-1 in brown adipose tissue (BAT) and increased plasma catecholamine (CA) in mice. PLoS One. 2018;13(7):e0201203. Published 2018 Jul 30. |
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Procyanidin C1 is a polyphenolic compound, it is found in a variety of vegetables and fruits and has a wide range of biological activities, including antioxidant and anti-inflammatory anticancer roles[1,2]
Procyanidin C is a catechin trimer purified from Cinnamomi Cortex and it showed inhibitory activity against TGF-β-induced EMT[3]. Treatment with procyanidin C1 in BMDMs resulted in a significant decrease in prostaglandin E2 and cyclooxygenase-2 levels, as well as the expression of cell surface molecules (CD80, CD86, and MHC class II), which was induced by LPS[1]. procyanidin C1 induced cell cycle arrest at S-phase and activated check point kinases, Chk1 and 2 in both MCF-7 and MDA-MB- 231 cells. At 48 h treatment procyanidin C1 induced DNA damage. In addition, procyanidin C1 decreased the Bcl2 levels and increased the BAX levels in both MCF-7 and MDA-MB- 231cells, which indicate that the procyanidin C1 inhibits breast cancer cell growth by inhibiting proliferation and by inducing apoptosis[2]
Procyanidin C1, a polyphenolic component of grape seed extract, increases the healthspan and lifespan of mice through its action on senescent cells[4]. In vivo, zebrafish larvae (AB strain) 3 days post-fertilization were incubated with NAC or procyanidins (C, EC, ECG, B1, B2, B3, B4, B1-G, B2-G, C1) in 300 μM H2 O2 for 4 days. Different grape seed procyanidins increased the survival of PC12 cells challenged with H2 O2 , improved the movement behavior disorder of zebrafish caused by H2 O2 , inhibited the increase of ROS and MDA and the decrease of GSH-Px, CAT, and SOD activities, and up-regulated the Nrf2/ARE pathway. The neuroprotective effects of the procyanidin trimer C1 treatment group were greater than the other treatment groups[5]
References:
[1].Byun EB, Sung NY, et al. The procyanidin trimer C1 inhibits LPS-induced MAPK and NF-κB signaling through TLR4 in macrophages. Int Immunopharmacol. 2013;15(2):450-456.
[2].Koteswari LL, Kumari S, et al. A comparative anticancer study on procyanidin C1 against receptor positive and receptor negative breast cancer. Nat Prod Res. 2020;34(22):3267-3274.
[3].Kin R, Kato S, et al. Procyanidin C1 from Cinnamomi Cortex inhibits TGF-β-induced epithelial-to-mesenchymal transition in the A549 lung cancer cell line. Int J Oncol. 2013;43(6):1901-1906.
[4].Xu Q, Fu Q, Li Z, et al. The flavonoid procyanidin C1 has senotherapeutic activity and increases lifespan in mice. Nat Metab. 2021;3(12):1706-1726.
[5].Nakano N, Nishiyama C, Tokura T, et al. Procyanidin C1 from apple extracts inhibits Fc epsilon RI-mediated mast cell activation. Int Arch Allergy Immunol. 2008;147(3):213-221.
原花青素C1是一种多酚类化合物，存在于多种蔬菜和水果中，具有广泛的生物活性，包括抗氧化和抗炎抗癌作用[1,2] /p>\n
原花青素 C 是一种从肉桂皮层纯化的儿茶素三聚体，它对 TGF-β 诱导的 EMT 显示出抑制活性[3]。在 BMDM 中用原花青素 C1 处理导致前列腺素 E2 和环氧合酶 2 水平显着降低，以及由 LPS 诱导的细胞表面分子（CD80、CD86 和 MHC II 类）的表达 [1]。原花青素 C1 在 MCF-7 和 MDA-MB-231 细胞中诱导 S 期细胞周期停滞并激活检查点激酶 Chk1 和 2。在 48 小时处理原花青素 C1 诱导 DNA 损伤。此外，原花青素 C1 降低了 Bcl2 水平，增加了 MCF-7 和 MDA-MB-231 细胞中的 BAX 水平，这表明原花青素 C1 通过抑制增殖和诱导细胞凋亡来抑制乳腺癌细胞生长[2]
原花青素 C1 是葡萄籽提取物的一种多酚成分，可通过其对衰老细胞的作用延长小鼠的健康寿命和寿命[4]。在体内，将受精后 3 天的斑马鱼幼虫（AB 株）与 NAC 或原花青素（C、EC、ECG、B1、B2、B3、B4、B1-G、B2-G、C1）在 300 μM H< sub>2 O2 4 天。不同葡萄籽原花青素提高H2 O2 PC12细胞存活率，改善H2 O引起的斑马鱼运动行为障碍2 ，抑制ROS和MDA的增加以及GSH-Px、CAT和SOD活性的降低，并上调Nrf2/ARE通路。原花青素三聚体C1治疗组的神经保护作用优于其他治疗组[5]
| Cas No. | 37064-30-5 | SDF | |
| 别名 | 原花青素 C1; PCC1 | ||
| Canonical SMILES | OC1=CC=C([C@H]2OC(C([C@H]3C4=C(O)C=C(O)C=C4O[C@H](C5=CC(O)=C(O)C=C5)[C@@H]3O)=C(O)C=C6O)=C6[C@H](C7=C(O)C=C(O)C8=C7O[C@H](C9=CC=C(O)C(O)=C9)[C@H](O)C8)[C@H]2O)C=C1O | ||
| 分子式 | C45H38O18 | 分子量 | 866.8 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 10 mg/ml | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.1537 mL | 5.7683 mL | 11.5367 mL |
| 5 mM | 0.2307 mL | 1.1537 mL | 2.3073 mL |
| 10 mM | 0.1154 mL | 0.5768 mL | 1.1537 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
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1. 首先保证母液是澄清的；
2.
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The flavonoid Procyanidin C1 has senotherapeutic activity and increases lifespan in mice
Nat Metab 2021 Dec;3(12):1706-1726.PMID:34873338DOI:10.1038/s42255-021-00491-8.
Ageing-associated functional decline of organs and increased risk for age-related chronic pathologies is driven in part by the accumulation of senescent cells, which develop the senescence-associated secretory phenotype (SASP). Here we show that Procyanidin C1 (PCC1), a polyphenolic component of grape seed extract (GSE), increases the healthspan and lifespan of mice through its action on senescent cells. By screening a library of natural products, we find that GSE, and PCC1 as one of its active components, have specific effects on senescent cells. At low concentrations, PCC1 appears to inhibit SASP formation, whereas it selectively kills senescent cells at higher concentrations, possibly by promoting production of reactive oxygen species and mitochondrial dysfunction. In rodent models, PCC1 depletes senescent cells in a treatment-damaged tumour microenvironment and enhances therapeutic efficacy when co-administered with chemotherapy. Intermittent administration of PCC1 to either irradiated, senescent cell-implanted or naturally aged old mice alleviates physical dysfunction and prolongs survival. We identify PCC1 as a natural senotherapeutic agent with in vivo activity and high potential for further development as a clinical intervention to delay, alleviate or prevent age-related pathologies.
Procyanidin C1 from Viola odorata L. inhibits Na+,K+-ATPase
Sci Rep 2022 Apr 29;12(1):7011.PMID:35487935DOI:10.1038/s41598-022-11086-y.
Members of the Viola genus play important roles in traditional Asian herbal medicine. This study investigates the ability of Viola odorata L. extracts to inhibit Na+,K+-ATPase, an essential animal enzyme responsible for membrane potential maintenance. The root extract of V. odorata strongly inhibited Na+,K+-ATPase, while leaf and seeds extracts were basically inactive. A UHPLC-QTOF-MS/MS metabolomic approach was used to identify the chemical principle of the root extract's activity, resulting in the detection of 35,292 features. Candidate active compounds were selected by correlating feature area with inhibitory activity in 14 isolated fractions. This yielded a set of 15 candidate compounds, of which 14 were preliminarily identified as procyanidins. Commercially available procyanidins (B1, B2, B3 and C1) were therefore purchased and their ability to inhibit Na+,K+-ATPase was investigated. Dimeric procyanidins B1, B2 and B3 were found to be inactive, but the trimeric Procyanidin C1 strongly inhibited Na+,K+-ATPase with an IC50 of 4.5 µM. This newly discovered inhibitor was docked into crystal structures mimicking the Na3E1∼P·ADP and K2E2·Pi states to identify potential interaction sites within Na+,K+-ATPase. Possible binding mechanisms and the principle responsible for the observed root extract activity are discussed.
Procyanidin C1 Location, Interaction, and Aggregation in Two Complex Biomembranes
Membranes (Basel) 2022 Jul 5;12(7):692.PMID:35877895DOI:10.3390/membranes12070692.
Procyanidins are known for their many benefits to human health and show a plethora of biological effects. One of the most important procyanidin is the procyanidin trimer C1 (PC1). Due to its relatively high lipid-water partition coefficient, the properties of PC1 could be attributed to its capability to interact with the biomembrane, to modulate its structure and dynamics, and to interact with lipids and proteins, however, its biological mechanism is not known. We have used all-atom molecular dynamics in order to determine the position of PC1 in complex membranes and the presence of its specific interactions with membrane lipids, having simulated a membrane mimicking the plasma membrane and another mimicking the mitochondrial membrane. PC1 has a tendency to be located at the membrane interphase, with part of the molecule exposed to the water solvent and part of it reaching the first carbons of the hydrocarbon chains. It has no preferred orientation, and it completely excludes the CHOL molecule. Remarkably, PC1 has a tendency to spontaneously aggregate, forming high-order oligomers. These data suggest that its bioactive properties could be attributed to its membranotropic effects, which therefore supports the development of these molecules as therapeutic molecules, which would open new opportunities for future medical advances.
How Procyanidin C1 sticks to collagen: The role of proline rings
Biophys Chem 2021 Sep;276:106627.PMID:34089979DOI:10.1016/j.bpc.2021.106627.
Molecular interactions between proteins and polyphenols are responsible for many natural phenomena like colloidal turbidity, astringency, denaturation of enzymes and leather tanning. Although these phenomena are well known, there are open questions about the specific interactions involved in the complexation process. In this work, Molecular Dynamic (MD) simulations and the topology of the electron density analysis were used to study the interactions between the flavonoid Procyanidin C1 and a collagen fragment solvated in water. Root mean square deviation; root mean square fluctuation and hydrogen bonds occupancy were examined after 50 ns. The interactions were also analyzed by means of the quantum theory of atoms in molecules. Our results show that the main interactions are hydrogen bonds between -OH groups of the polyphenol and CO groups of the peptide bond. Stacking interactions between proline rings and phenol rings, that is CH⋯π hydrogen bonds, also stabilize the dynamic structure of the complex.
The Procyanidin C1-Dependent Inhibition of the Hydrolysis of Potato Starch and Corn Starch Induced by Pancreatin
Molecules 2021 Oct 11;26(20):6121.PMID:34684702DOI:10.3390/molecules26206121.
Procyanidins are contained in various foods, and their effects on starch hydrolysis have been reported. In Japan, black soybeans, which contain a trimeric procyanidin, Procyanidin C1 (proC1), are cooked with rice and used to prepare dumplings. In this study, the effects of proC1 on the pancreatin-induced formation of reducing sugars and starch hydrolysis were studied using potato starch and corn starch. ProC1 inhibited both reactions; the inhibition was greater in potato starch than corn starch when added to heated potato starch and corn starch. When heated with proC1, its inhibitory effects decreased, especially in potato starch, suggesting the important role of proC1 itself for the inhibition of potato starch hydrolysis. ProC1 also inhibited the hydrolysis when added to heated, longer amylose (average molecular weight: 31,200), and the inhibition decreased when heated with the amylose. On the other hand, proC1 could not inhibit the hydrolysis when added to heated, shorter amylose (average molecular weight: 4500), but could when heated with the amylose, suggesting the important role of the degradation products of proC1 for the inhibition. We discuss the mechanism of the proC1-dependent inhibition of amylose hydrolysis, taking the molecular weight into account.