Ampelopsin C is a novel and potent modulator of AMPK signaling pathway
Physicochemical Properties
| Molecular Formula | C42H32O9 |
| Molecular Weight | 680.69808 |
| Exact Mass | 680.205 |
| Elemental Analysis | C, 74.11; H, 4.74; O, 21.15 |
| CAS # | 130518-20-6 |
| PubChem CID | 182979 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.523g/cm3 |
| Index of Refraction | 1.781 |
| LogP | 7.755 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 51 |
| Complexity | 1180 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | OC1=CC=C(C2OC3=C4C5=C(C(=C3)O)C(C3=CC=C(O)C=C3)C(C3=CC(O)=CC(O)=C3)C5C(C3=C(O)C=C(O)C=C3C24)C2=CC=C(O)C=C2)C=C1 |
| InChi Key | QDEHKEFWCRAFDN-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C42H32O9/c43-23-7-1-19(2-8-23)33-35(22-13-26(46)15-27(47)14-22)40-34(20-3-9-24(44)10-4-20)36-29(16-28(48)17-30(36)49)37-39-32(18-31(50)38(33)41(39)40)51-42(37)21-5-11-25(45)12-6-21/h1-18,33-35,37,40,42-50H |
| Chemical Name | 2-(3,5-dihydroxyphenyl)-3,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.04,18.07,19.011,16]nonadeca-4(18),5,7(19),11(16),12,14-hexaene-5,13,15-triol |
| Synonyms | Viniferol D; ampelopsin C; 130518-20-6; 2-(3,5-dihydroxyphenyl)-3,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.04,18.07,19.011,16]nonadeca-4(18),5,7(19),11(16),12,14-hexaene-5,13,15-triol; (+)-Viniferol D; (+)-Ampelopsin C; DTXSID20926773; CID 71307315; |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| Targets |
Modulates c-Myc/Skp2/Fbw7/HDAC2 pathway; Activates AMPK signaling pathway [1][2] |
| ln Vitro |
Ampelopsin (50–200 μM) dose-dependently inhibited proliferation of human lung adenocarcinoma A549 and H1299 cells (IC50 ≈ 100 μM at 48 h). Induced G0/G1 cell cycle arrest by downregulating cyclin D1/CDK4 and upregulating p21/p27 [1] Triggered mitochondrial apoptosis: Increased Bax/Bcl-2 ratio (2.1-fold), activated caspase-3/-9, induced PARP cleavage, and caused cytochrome c release. Suppressed c-Myc/Skp2/Fbw7/HDAC2 cascade, elevating p21/p27 levels [1] Protected HUVECs from high glucose (30 mM)-induced oxidative stress: Reduced ROS by 68% and increased SOD activity by 2.1-fold. Induced autophagy via AMPK phosphorylation (3.2-fold increase), shown by enhanced LC3-II accumulation and autophagic flux [2] |
| Cell Assay |
Anti-proliferation: Cells treated with 0–200 μM Ampelopsin for 24–72 h. Viability assessed by MTT assay. Cell cycle distribution analyzed via PI staining and flow cytometry [1] Apoptosis: Annexin V-FITC/PI staining for apoptotic rates. Western blot for Bax, Bcl-2, cleaved caspases, PARP, cytochrome c. siRNA knockdown of c-Myc/Skp2/Fbw7 to validate pathway [1] Autophagy: High glucose-treated HUVECs pretreated with 20–80 μM Ampelopsin. Autophagosomes visualized by LC3 immunofluorescence. Autophagic flux monitored using bafilomycin A1. AMPK involvement confirmed by compound C (inhibitor) [2] Oxidative stress: Intracellular ROS measured by DCFH-DA fluorescence. SOD activity assessed by WST-1 assay [2] |
| References |
[1]. Ampelopsin induces apoptosis by regulating multiple c-Myc/S-phase kinase-associated protein 2/F-box and WD repeat-containing protein 7/histone deacetylase 2 pathways in human lung adenocarcinoma cells. Mol Med Rep. 2015 Jan;11(1):105-12. [2]. Ampelopsin protects endothelial cells from hyperglycemia-induced oxidative damage by inducing autophagy via the AMPK signaling pathway. Biofactors. 2015 Nov-Dec;41(6):463-75. |
| Additional Infomation |
Ampelopsin (dihydromyricetin) is a flavonoid from Ampelopsis grossedentata with anticancer and antioxidant properties [1][2] Anticancer mechanism: Suppresses c-Myc/Skp2/Fbw7/HDAC2 axis → stabilizes p21/p27 → induces G1 arrest and mitochondrial apoptosis in lung cancer [1] Cytoprotective mechanism: Activates AMPK → enhances autophagy → clears ROS and protects endothelial cells from hyperglycemia damage [2] Viniferol D has been reported in Vitis vinifera with data available. |
Solubility Data
| 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 |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4691 mL | 7.3454 mL | 14.6908 mL | |
| 5 mM | 0.2938 mL | 1.4691 mL | 2.9382 mL | |
| 10 mM | 0.1469 mL | 0.7345 mL | 1.4691 mL |