Procyanidin A2
(Synonyms: 原花青素 A2) 目录号 : GC44688
A flavanol dimer with diverse biological properties
Cas No.:41743-41-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Procyanidin A2 is a natural flavanol dimer of (-)-epicatechin that is found in the horse chestnut (A. hippocastanum), mountain cranberry (V. vitis-idaea), and other fruits with antioxidant, anti-inflammatory, antibacterial, antiproliferative, and antidiabetic properties. It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals (IC50 = 5.08 μM) and inhibits STAT3 activation induced by platelet derived growth factor (PDGF) in primary rat vascular smooth muscle cells (VSMCs) when used at a concentration of 30 μg/ml. Procyanidin A2 inhibits growth of S. aureus and E. coli (MICs = 62.5 and 62.5 μg/ml, respectively) and proliferation of human HepG2 liver hepatocellular carcinoma and HeLa cervical cancer cells (EC50s = 62.19 and 66.07 μg/ml, respectively). It also increases insulin secretion from primary mouse pancreatic islets when used at a concentration of 10 μM in vitro and inhibits bisphenol A-induced glucose increases in fasted mice when administered at a dose of 10 μmol/kg per day.
| Cas No. | 41743-41-3 | SDF | |
| 别名 | 原花青素 A2 | ||
| Canonical SMILES | OC1=C(C[C@@H](O)[C@@H](C2=CC(O)=C(O)C=C2)O3)C3=C([C@@]([C@@]4([H])O)([H])C(C(O)=CC(O)=C5)=C5O[C@@]4(C6=CC(O)=C(O)C=C6)O7)C7=C1 | ||
| 分子式 | C30H24O12 | 分子量 | 576.5 |
| 溶解度 | DMSO : 100 mg/mL (173.46 mM; Need ultrasonic) | 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 | 1.7346 mL | 8.673 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 |
| 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，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Procyanidin A2 Modulates IL-4-Induced CCL26 Production in Human Alveolar Epithelial Cells
Int J Mol Sci 2016 Nov 12;17(11):1888.PMID:27845745DOI:10.3390/ijms17111888.
Allergic asthma is an inflammatory lung disease that is partly sustained by the chemokine eotaxin-3 (CCL26), which extends eosinophil migration into tissues long after allergen exposure. Modulation of CCL26 could represent a means to mitigate airway inflammation. Here we evaluated Procyanidin A2 as a means of modulating CCL26 production and investigated interactions with the known inflammation modulator, Interferon γ (IFNγ). We used the human lung epithelial cell line A549 and optimized the conditions for inducing CCL26. Cells were exposed to a range of Procyanidin A2 or IFNγ concentrations for varied lengths of time prior to an inflammatory insult of interleukin-4 (IL-4) for 24 h. An enzyme-linked immunosorbent assay was used to measure CCL26 production. Exposing cells to 5 μM Procyanidin A2 (prior to IL-4) reduced CCL26 production by 35% compared with control. Greatest inhibition by Procyanidin A2 was seen with a 2 h exposure prior to IL-4, whereas IFNγ inhibition was greatest at 24 h. Concomitant incubation of Procyanidin A2 and IFNγ did not extend the inhibitory efficacy of Procyanidin A2. These data provide evidence that Procyanidin A2 can modulate IL-4-induced CCL26 production by A549 lung epithelial cells and that it does so in a manner that is different from IFNγ.
Procyanidin A2 and Its Degradation Products in Raw, Fermented, and Roasted Cocoa
J Agric Food Chem 2017 Mar 1;65(8):1715-1723.PMID:28207258DOI:10.1021/acs.jafc.6b05262.
Cocoa is known as an important source of flavan-3-ols, but their fate "from the bean to the bar" is not yet clear. Here, Procyanidin A2 found in native cocoa beans (9-13 mg/kg) appeared partially epimerized into A2E1 through fermentation, whereas a second epimer (A2E2) emerged after roasting. At m/z 575, dehydrodiepicatechin A was revealed to be the major HPLC peak before fermentation, whereas F1, a marker of well-conducted fermentations, becomes the most intense after roasting. RP-HPLC-ESI(-)-HRMS/MS analysis performed on a Procyanidin A2 model medium after 12 h at 90 °C revealed many more degradation products than those identified in fermented cocoa, including the last epimer of A2, A2 open structure intermediates (m/z 577), and oxidized A-type dimers (m/z 573).
Procyanidin A2, a polyphenolic compound, exerts anti-inflammatory and anti-oxidative activity in lipopolysaccharide-stimulated RAW264.7 cells
PLoS One 2020 Aug 5;15(8):e0237017.PMID:32756588DOI:10.1371/journal.pone.0237017.
Procyandin A2 (PCA2) is a polyphenolic compound which is isolated from grape seeds. It has been reported that PCA2 exhibits antioxidative and anti-inflammatory effects, but its molecular mechanism is still poorly understood. This study tests the hypothesis that PCA2 suppresses lipopolysaccharide (LPS)-induced inflammation and oxidative stress through targeting the nuclear factor-κB (NF-κB), mitogen-activated protein kinase (MAPK), and NF-E2-related factor 2 (Nrf2) pathways in RAW264.7 cells. PCA2 (20, 40, 80 μM) exhibited no significant cytotoxicity in RAW264.7 cells and showed an inhibitory effect on an LPS-induced nitrite level. Pro-inflammatory cytokines like tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), prostaglandin E2 (PGE2), nitric oxide (NO), and reactive oxygen species (ROS) were suppressed by PCA2 with a concentration range of 0-80 μM. The mRNA levels of TNF-α and IL-6 were inhibited by PCA2 (80 μM). The hallmark-protein expression of the NF-κB (p-IKKα/β, p-IκBα, and p-p65) and MAPK (p-p38, p-JNK, and p-ERK) pathways were decreased by PCA2 in LPS-stimulated RAW264.7 cells. In addition, immunofluorescence results indicated that PCA2 (80 μM) promoted the translocation of NF-κB/p65 from the cytoplasm into the nucleus. PCA2 upregulated the expressions of Nrf2 and HO-1 and downregulated the expression of Keap-1. Simultaneously, PCA2 (80 μM) reversed LPS-induced Nrf2 translocation from the nucleus into the cytoplasm. Collectively, PCA2 protect cells against the damage from inflammation and oxidative injury, which suggest a potential therapeutic strategy for inflammatory and oxidative stress through targeting NF-κB, MAPK, and Nrf2 pathways in RAW264.7 cells.
Procyanidin A2, an anti-diabetic condensed tannin extracted from Wendlandia glabrata, reduces elevated G-6-Pase and mRNA levels in diabetic mice and increases glucose uptake in CC1 hepatocytes and C1C12 myoblast cells
RSC Adv 2019 Jun 3;9(30):17211-17219.PMID:35519885DOI:10.1039/c9ra02397f.
To reduce the global burden of diabetes in an affordable way great attention has been paid to the search for functional foods and herbal remedies. One of the most popularly used functional foods in the North Eastern region of India is tender shoots of Wendlandia glabrata DC. In the current study identification of active anti-diabetic constituent of the tender shoots of W. glabrata was guided through α-glucosidase inhibition and Procyanidin A2 was identified with IC50 0.27 ± 0.01 μg mL-1 making it potential source for postprandial management of DM type 2. The study has also demonstrated Procyanidin A2 as a potent anti-diabetic agent that exhibits significant glucose-6-phosphatase inhibitory activities and downregulated mRNA level in diabetic mice as well as increases glucose uptake in hepatocytes and myoblast cells. This study revealed that easily available tender shoots of W. glabrata could be used to make specific dietary recommendations for consumption for affordable management of diabetes.
Gut Microbiota Composition Affects Procyanidin A2-Attenuated Atherosclerosis in ApoE-/- Mice by Modulating the Bioavailability of Its Microbial Metabolites
J Agric Food Chem 2021 Jun 30;69(25):6989-6999.PMID:34142543DOI:10.1021/acs.jafc.1c00430.
Procyanidin A2 (PCA2) has been shown to improve lipid metabolism. However, it remains to know whether it can play a role in preventing atherosclerosis (AS) through gut microbiota. This study examined the effect of PCA2 on high fat diet (HFD)-induced AS in ApoE-/- mice with an intact and antibiotic-depleted microbiota. PCA2 administration for 12 weeks attenuated HFD-induced AS in ApoE-/- mice, evidenced by obviously alleviating the histological abnormalities of the aorta, lipid accumulation, oxidative stress, and inflammation, which were accompanied by downregulating the expression of vascular cell adhesion molecule-1 and intracellular adhesion molecule-1 and upregulating peroxisome proliferator-activated receptor gamma, cholesterol 7 alpha-hydroxylase, and ATP-binding cassette transporter A1. Moreover, PCA2 treatment reshaped the gut microbiota imbalance caused by HFD, especially reducing the ratio of Firmicutes/Bacteroidetes and increasing the abundance of Verrucomicrobia. However, antibiotic intervention almost offset the alleviation of AS by PCA2 and prevented the biotransformation of PCA2 by gut microbiota, thus resulting in a 2327.21-6.27-fold decrease in its microbial metabolites of plasma. There was a marked correlation among the microbiota composition, the bioavailability of PCA2-derived microbial metabolites, and AS indicators. The findings indicate that the gut microbiota robustly influences the bioavailability of microbial metabolites that may partially drive the AS resilience property of PCA2.