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| Targets |
α-Viniferin targets multiple proteins and pathways. It is a specific, reversible, and non-competitive inhibitor of acetylcholinesterase (AChE). It also inhibits prostaglandin H2 synthase (cyclooxygenase) with an inhibitory potency that is approximately 3- to 4-fold stronger than that of resveratrol. In addition, α-viniferin inhibits protein kinase C and down-regulates STAT-1-inducible inflammatory genes by inhibiting ERK-mediated STAT-1 activation in IFN-γ-stimulated macrophages. This multi-targeted mechanism of action makes it a valuable tool for studying inflammation, cancer, and neurodegenerative diseases.
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| ln Vitro |
In vitro, α-viniferin exhibits potent anti-inflammatory activity by inhibiting the production of nitric oxide (NO), IP-10, and MIG in IFN-γ-stimulated macrophages. It demonstrates significant anticancer activity against various cancer cell lines. As an acetylcholinesterase inhibitor, it shows specific and reversible inhibition of AChE activity. Its inhibitory activity against prostaglandin H2 synthase is about 3- to 4-fold stronger than that of resveratrol. α-Viniferin also exhibits antibacterial effects against Gram-positive bacteria such as Staphylococcus aureus. Its anti-diabetic and anti-tuberculosis activities have also been reported.
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| ln Vivo |
In vivo, α-viniferin has demonstrated efficacy in animal models of inflammation and arthritis. Its ability to inhibit acetylcholinesterase suggests potential benefits in Alzheimer's disease models. The compound's anti-tumor activity has been observed in preclinical models. As a potent anti-inflammatory agent, it reduces inflammatory responses by modulating ERK-mediated STAT-1 activation. However, detailed in vivo efficacy data and comprehensive pharmacokinetic profiles are limited in publicly available sources, as the compound is primarily used as a research tool for studying polyphenol biology.
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| Enzyme Assay |
The in vitro enzyme inhibition assay for α-Viniferin typically uses purified enzymes such as acetylcholinesterase or prostaglandin H2 synthase. For AChE inhibition, the assay is performed in 96-well plates using Ellman's method with acetylthiocholine as a substrate. The compound is incubated with the enzyme at varying concentrations (typically 0.1 to 100 µM) for 10-30 minutes, and the reaction is initiated by adding the substrate. The absorbance is measured at 412 nm, and IC50 values are calculated from dose-response curves. For prostaglandin H2 synthase inhibition, the compound is incubated with the enzyme and arachidonic acid, and prostaglandin production is measured by ELISA. Positive controls and negative controls are included in each assay run.
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| Cell Assay |
For in vitro cellular assays, macrophages (e.g., RAW 264.7) or cancer cell lines are treated with α-Viniferin at concentrations ranging from 0.1 to 100 µM for 1-24 hours. For anti-inflammatory studies, cells are stimulated with IFN-γ or LPS, and the production of inflammatory mediators such as NO, IP-10, and MIG is measured by Griess assay or ELISA. STAT-1 activation and ERK phosphorylation are assessed by Western blotting. For anticancer studies, cell viability is assessed using MTT or CellTiter-Glo assays, and apoptosis is quantified by Annexin V/PI staining. All experiments include appropriate controls and are performed in triplicate.
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| Animal Protocol |
For in vivo efficacy studies, rodent models of inflammation (e.g., carrageenan-induced paw edema) or arthritis are used. α-Viniferin is administered orally or intraperitoneally at doses ranging from 1 to 50 mg/kg, typically once or twice daily. Inflammatory markers are measured in blood and tissue homogenates by ELISA. For neuroprotective studies, models of Alzheimer's disease (e.g., scopolamine-induced memory impairment) may be used, and cognitive function is assessed by behavioral tests. At study endpoint, tissues are harvested for histological analysis and biochemical assays. All animal procedures are conducted in accordance with institutional guidelines.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for α-Viniferin are limited in publicly accessible literature. As a polyphenolic compound with a molecular weight of 678.7 g/mol, it is expected to have poor oral bioavailability due to extensive first-pass metabolism and poor aqueous solubility. Following oral administration, the compound is likely metabolized by phase II conjugation (glucuronidation, sulfation) in the liver and intestine. The compound is eliminated primarily via biliary and renal excretion. Due to its natural product origin and use as a research tool, comprehensive PK studies have not been well-documented. Further studies are needed to characterize its absorption, distribution, metabolism, and excretion.
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| Toxicity/Toxicokinetics |
Preclinical toxicology studies of α-Viniferin are limited. As a natural polyphenol, it is generally considered to have a favorable safety profile. In acute toxicity studies, the compound is tolerated at moderate doses with no significant adverse effects. No significant organ toxicity or hematological abnormalities are reported at pharmacological doses. The compound shows no evidence of genotoxicity in standard in vitro assays. The safety profile supports its use as a research reagent, though comprehensive toxicology studies would be required for clinical development. The compound is for research use only and is not approved for human use.
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| References | |
| Additional Infomation |
(+)-α-glucanthin is a nine-membered macrocyclic compound with a cyclic skeleton containing three 6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran groups. It was isolated from Caragana chamlague Lamarck and exhibits significant inhibitory activity against acetylcholinesterase (EC 3.1.1.7). It possesses anti-inflammatory properties, inhibits acetylcholinesterase activity, and functions as a plant metabolite. It is a polyphenolic compound, belonging to the macrocyclic class of compounds, and is also a member of the 1-benzofuran group. Its function is related to resveratrol. (+)-α-glucanthin has been reported in Caragana sinica, Caragana korshinskii, and other organisms with available data.
α-Viniferin is a naturally occurring resveratrol trimer with a wide range of pharmacological activities, including anti-inflammatory, antioxidant, anti-arthritic, anti-tumor, anti-Alzheimer's, anti-tuberculosis, and anti-diabetic effects. It inhibits acetylcholinesterase, prostaglandin H2 synthase, and protein kinase C, and down-regulates STAT-1-inducible inflammatory genes. It is not approved for human use and has not entered clinical trials. It is available as a high-purity research reagent (≥98%) for laboratory use only. Its multi-targeted activity makes it a valuable tool for studying inflammation, cancer, neurodegenerative diseases, and polyphenol biology. |
| Molecular Formula |
C42H30O9
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|---|---|
| Molecular Weight |
678.6822
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| Exact Mass |
678.188
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| CAS # |
62218-13-7
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| PubChem CID |
196402
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| Appearance |
White to yellow solid powder
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| Density |
1.5±0.1 g/cm3
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| Index of Refraction |
1.768
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| LogP |
5.38
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
51
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| Complexity |
1080
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| Defined Atom Stereocenter Count |
6
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| SMILES |
C1=CC(=CC=C1[C@H]2[C@@H]3C4=C5[C@@H]([C@H](OC5=CC(=C4)O)C6=CC=C(C=C6)O)C7=C8[C@H]([C@@H](OC8=CC(=C7)O)C9=CC=C(C=C9)O)C1=C3C(=CC(=C1)O)O2)O
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| InChi Key |
KUTVNHOAKHJJFL-ZSIJVUTGSA-N
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| InChi Code |
InChI=1S/C42H30O9/c43-22-7-1-19(2-8-22)40-37-28-13-25(46)17-32-35(28)39(42(50-32)21-5-11-24(45)12-6-21)30-15-27(48)18-33-36(30)38(29-14-26(47)16-31(49-40)34(29)37)41(51-33)20-3-9-23(44)10-4-20/h1-18,37-48H/t37-,38-,39+,40+,41+,42-/m1/s1
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| Chemical Name |
(2R,3R,10R,11R,18S,19S)-3,11,19-tris(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.12,5.110,13.021,25.09,27.017,26]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaene-7,15,23-triol
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 1.4734 mL | 7.3672 mL | 14.7345 mL | |
| 5 mM | 0.2947 mL | 1.4734 mL | 2.9469 mL | |
| 10 mM | 0.1473 mL | 0.7367 mL | 1.4734 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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