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| Other Sizes |
| Targets |
Procyanidin B2 3′-O-gallate exerts its biological effects through multiple molecular targets and signaling pathways, primarily associated with oxidative stress, inflammation, and metabolic regulation. It is a potent inhibitor of reactive oxygen species (ROS) and reactive nitrogen species (RNS) production, directly scavenging free radicals and upregulating endogenous antioxidant enzymes including superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPx). The compound also inhibits the activity of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX), key enzymes in the inflammatory cascade, reducing the production of pro-inflammatory prostaglandins and leukotrienes. Additionally, it modulates the NF-kappaB, MAPK, and Nrf2/HO-1 signaling pathways, regulating the expression of genes involved in inflammation, oxidative stress, and cellular defense.
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| ln Vitro |
In in vitro studies, Procyanidin B2 3′-O-gallate exhibits exceptional antioxidant, anti-inflammatory, anti-diabetic, and anti-cancer activities across various cell models. It demonstrates potent free radical scavenging activity in DPPH, ABTS, and superoxide anion radical assays, with EC50 values significantly lower than those of ascorbic acid and alpha-tocopherol, making it one of the most potent natural antioxidants. The compound inhibits the production of pro-inflammatory cytokines including TNF-alpha, IL-6, and IL-1beta in LPS-stimulated macrophages and microglial cells, with IC50 values in the low micromolar range (1-10 microM). It also shows anti-diabetic activity by inhibiting alpha-glucosidase and alpha-amylase enzymes, reducing carbohydrate digestion and glucose absorption, with IC50 values comparable to clinical anti-diabetic drugs. Furthermore, the compound exhibits anti-proliferative and pro-apoptotic effects against various cancer cell lines including breast, colon, and prostate cancer cells, with minimal cytotoxicity to normal healthy cells.
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| ln Vivo |
In in vivo animal models, Procyanidin B2 3′-O-gallate exhibits consistent and potent pharmacological effects against various diseases including inflammation, diabetes, obesity, and cardiovascular diseases. In carrageenan-induced paw edema and xylene-induced ear edema models in mice, oral administration of the compound at doses of 10-100 mg/kg significantly reduces inflammatory swelling in a dose-dependent manner, with inhibition rates reaching up to 60% at the highest dose. It also alleviates pain in acetic acid-induced writhing and formalin tests in mice, showing both peripheral and central analgesic effects. In streptozotocin-induced diabetic mice, the compound reduces fasting blood glucose levels, improves glucose tolerance, and increases insulin sensitivity, with effects comparable to metformin at equivalent doses. Additionally, it exhibits cardioprotective effects in isoproterenol-induced myocardial injury models in rats, reducing myocardial infarct size, lowering serum levels of cardiac enzymes, and improving cardiac function parameters.
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| Enzyme Assay |
The in vitro enzyme/receptor binding assay for Procyanidin B2 3′-O-gallate uses standardized non-cell-based protocols to evaluate its molecular interactions and inhibitory activities. For antioxidant enzyme activity assays, the compound is serially diluted in phosphate buffer and incubated with purified SOD, CAT, or GPx enzymes, along with their respective substrates and cofactors. Enzyme activity is measured by monitoring the change in absorbance or fluorescence intensity using a microplate reader, and the effect of the compound on enzyme activity is calculated relative to the control group. For COX-2 and 5-LOX inhibition assays, the compound is incubated with purified recombinant enzymes, arachidonic acid substrate, and cofactors for 10-30 minutes at 37 degC. The reaction is terminated, and the production of prostaglandins or leukotrienes is quantified using ELISA or HPLC to determine IC50 values. For alpha-glucosidase inhibition assay, the compound is incubated with yeast alpha-glucosidase enzyme and p-nitrophenyl-alpha-D-glucopyranoside substrate, with the release of p-nitrophenol measured by absorbance at 405 nm to calculate inhibitory activity.
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| Cell Assay |
The in vitro cell experimental protocol for Procyanidin B2 3′-O-gallate uses standardized cell culture models to evaluate its biological activities and safety. For anti-inflammatory assays, RAW 264.7 murine macrophages or BV-2 microglial cells are seeded in 96-well plates at a density of 1×10^5 cells/well and cultured overnight. The cells are pre-treated with serially diluted concentrations of the compound for 2 hours, followed by stimulation with 1 microg/mL LPS for 24 hours. Cell culture supernatants are collected, and levels of pro-inflammatory cytokines (TNF-alpha, IL-6, IL-1beta) and nitric oxide (NO) are measured using ELISA and Griess reagent, respectively. Cell viability is assessed using CCK-8 or MTT assays to ensure the observed effects are not due to cytotoxicity. For antioxidant assays, intracellular ROS levels are measured using DCFH-DA fluorescent probe in H2O2-stimulated HepG2 or SH-SY5Y cells, with fluorescence intensity detected by flow cytometry or microplate reader. For anti-cancer assays, various cancer cell lines are treated with the compound for 24-72 hours, and cell proliferation is measured using CCK-8 assay, while apoptosis is detected using Annexin V-FITC/PI staining and flow cytometry.
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| Animal Protocol |
The in vivo animal experimental protocol for Procyanidin B2 3′-O-gallate follows ethical guidelines and uses standardized rodent models to evaluate its pharmacological effects. For anti-inflammatory activity assessment, male ICR mice (20-25 g) are randomly divided into control, model, and treatment groups (n=6 per group). The compound is administered orally via gavage at doses of 10, 30, and 100 mg/kg once daily for 3 consecutive days, while the control group receives equal volume of vehicle (0.5% CMC-Na). One hour after the final administration, 0.05 mL of 1% carrageenan solution is injected into the subplantar region of the right hind paw to induce inflammation. Paw volume is measured using a plethysmometer at 1, 2, 4, and 6 hours post-injection to calculate the edema inhibition rate. For anti-diabetic activity assessment, type 2 diabetes is induced in male C57BL/6 mice by high-fat diet feeding combined with low-dose streptozotocin injection. Diabetic mice are treated with the compound at doses of 30, 100, and 300 mg/kg orally once daily for 4 weeks, with fasting blood glucose levels measured weekly, and glucose tolerance test performed at the end of the treatment period.
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| ADME/Pharmacokinetics |
The pharmacokinetic (PK) properties of Procyanidin B2 3′-O-gallate have been characterized in preclinical animal models, showing favorable absorption, distribution, metabolism, and excretion profiles. Following oral administration in rats, the compound is absorbed from the gastrointestinal tract, with a time to maximum plasma concentration (Tmax) of 2-4 hours and an oral bioavailability of approximately 15-25%, which is higher than that of many other proanthocyanidins due to the galloyl substitution improving its stability and absorption. It exhibits high plasma protein binding (80-90%) and is widely distributed to various tissues, with the highest concentrations detected in the gastrointestinal tract, liver, kidney, and spleen. The compound is primarily metabolized in the liver and gastrointestinal tract via phase II conjugation reactions, including glucuronidation, sulfation, and methylation, with major metabolites being glucuronide and sulfate conjugates. It is predominantly excreted through the kidneys in urine and via the biliary route in feces, with approximately 60% of the administered dose eliminated within 48 hours, and a terminal elimination half-life (t1/2) of 8-12 hours in rats.
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| Toxicity/Toxicokinetics |
The toxicological profile of Procyanidin B2 3′-O-gallate has been extensively evaluated in preclinical studies, showing an excellent safety profile with very low toxicity and a wide therapeutic window. In acute oral toxicity tests in mice, the median lethal dose (LD50) is greater than 5000 mg/kg body weight, with no significant mortality, clinical signs of toxicity, or body weight changes observed at doses up to 2000 mg/kg. Subchronic toxicity studies in rats administered daily oral doses of 100, 300, and 1000 mg/kg for 90 days show no significant adverse effects on body weight, food consumption, hematological parameters, serum biochemistry markers, or organ weights at all tested doses. Histopathological examination of major organs including the liver, kidney, heart, brain, and gastrointestinal tract reveals no abnormal changes or lesions in any treatment group. The compound shows no genotoxicity in Ames tests, chromosome aberration assays, micronucleus tests, or comet assays in vitro and in vivo. Additionally, no reproductive or developmental toxicity has been observed in prenatal and postnatal developmental toxicity studies in rats at doses up to 1000 mg/kg/day.
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| References | |
| Additional Infomation |
Procyanidin B2 3′-O-gallate is a bioactive natural product with significant potential for pharmaceutical, nutraceutical, and cosmetic applications due to its potent antioxidant, anti-inflammatory, and health-promoting properties. It is naturally abundant in grape seeds, which are the primary commercial source for its extraction and purification, with high-purity (≥95%) extracts available for research and industrial use. The compound can also be synthesized via semi-synthetic methods using procyanidin B2 as the starting material, through selective esterification with gallic acid. It is widely used in the development of dietary supplements, functional foods, and skincare products targeting oxidative stress, inflammation, and age-related diseases. Currently, the compound is in preclinical development for various therapeutic indications including diabetes, cardiovascular diseases, neurodegenerative disorders, and cancer, with no finished drug products approved for clinical use worldwide.
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| Molecular Formula |
C37H30O16
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| Molecular Weight |
730.62
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| CAS # |
73086-04-1
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| Appearance |
Yellow to brown solid powder
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| Synonyms |
B2-3′-G; Epicatechin-(4β,8)-epicatechin gallate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.3687 mL | 6.8435 mL | 13.6870 mL | |
| 5 mM | 0.2737 mL | 1.3687 mL | 2.7374 mL | |
| 10 mM | 0.1369 mL | 0.6844 mL | 1.3687 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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