| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
|
||
| 25mg |
|
||
| 100mg | |||
| Other Sizes |
Demethyleneberberine is a potent and naturally occuring mitochondria-targeted antioxidant. Demethyleneberberine alleviates mice colitis and inhibits the inflammatory responses by inhibiting NF-κB pathway and regulating the balance of Th cells. Demethyleneberberine could serve as a AMPK activator for treating non-alcoholic fatty liver disease (NAFLD).
| Targets |
Demethyleneberberine targets AMP-activated protein kinase (AMPK) [3]
Demethyleneberberine targets nuclear factor kappa B (NF-κB) signaling pathway [2] Demethyleneberberine acts as a mitochondria-targeted antioxidant [1] |
|---|---|
| ln Vitro |
#### From Literature [1]
- In ethanol-treated HepG2 cells, Demethyleneberberine (10, 20, 40 μM) dose-dependently reduced intracellular reactive oxygen species (ROS) production and mitochondrial superoxide levels [1] - It improved mitochondrial membrane potential (ΔΨm) and increased ATP production, alleviating ethanol-induced mitochondrial dysfunction [1] - Downregulated the expression of lipogenic genes (SREBP-1c, FASN) and upregulated fatty acid oxidation-related gene (PPARα) in HepG2 cells [1] #### From Literature [2] - In LPS-induced RAW264.7 macrophages, Demethyleneberberine (5, 10, 20 μM) inhibited the production of pro-inflammatory cytokines (TNF-α, IL-6, IL-1β) and nitric oxide (NO) [2] - It suppressed NF-κB activation by inhibiting IκBα phosphorylation and p65 nuclear translocation [2] - In TNF-α-treated Caco-2 intestinal epithelial cells, the compound enhanced tight junction protein (ZO-1, occludin) expression, improving intestinal barrier integrity [2] #### From Literature [3] - In palmitic acid (PA)-treated HepG2 cells, Demethyleneberberine (10, 20, 40 μM) reduced lipid accumulation (Oil Red O staining) and intracellular triglyceride (TG) content [3] - It activated AMPK phosphorylation (p-AMPK) and upregulated downstream energy metabolism-related genes (PGC-1α, CPT1A) [3] - Decreased PA-induced ROS generation and malondialdehyde (MDA) levels, while increasing superoxide dismutase (SOD) and glutathione (GSH) activities [3] |
| ln Vivo |
#### From Literature [1] (Alcoholic Liver Disease Model)
- In C57BL/6 mice fed an ethanol-containing Lieber-DeCarli diet for 4 weeks, oral administration of Demethyleneberberine (25, 50 mg/kg/day) dose-dependently reduced hepatic steatosis (H&E staining) and TG content [1] - Improved mitochondrial function in liver tissue, as evidenced by increased mitochondrial DNA copy number and complex I/III/IV activities [1] - Reduced hepatic oxidative stress (decreased MDA, increased SOD/GSH-Px activities) and inhibited hepatocyte apoptosis (TUNEL staining) [1] #### From Literature [2] (Inflammatory Bowel Disease Model) - In DSS-induced colitis mice, oral administration of Demethyleneberberine (25, 50 mg/kg/day) for 7 days alleviated weight loss, colon shortening, and histological damage (H&E staining) [2] - Reduced colonic pro-inflammatory cytokine (TNF-α, IL-6, IL-1β) levels and NF-κB p65 nuclear translocation [2] - Restored T-helper cell homeostasis by increasing Treg cell percentage and decreasing Th1/Th17 cell percentages in mesenteric lymph nodes [2] #### From Literature [3] (Non-Alcoholic Fatty Liver Disease Model) - In ob/ob mice or high-fat diet (HFD)-fed C57BL/6 mice, oral administration of Demethyleneberberine (25, 50 mg/kg/day) for 8 weeks reduced hepatic steatosis and liver weight [3] - Activated hepatic AMPK phosphorylation and upregulated fatty acid oxidation-related proteins (CPT1A, PGC-1α) [3] - Decreased hepatic oxidative stress and inflammation (reduced TNF-α, IL-6 mRNA expression) [3] |
| Enzyme Assay |
#### From Literature [1] (Mitochondrial Function Assays)
- Mitochondrial membrane potential (ΔΨm) assay: HepG2 cells were loaded with a ΔΨm-sensitive fluorescent dye, treated with Demethyleneberberine (10, 20, 40 μM) and ethanol, and fluorescence intensity was measured by flow cytometry [1] - ATP assay: Ethanol-treated HepG2 cells were lysed, and ATP content was quantified using a luciferase-based assay kit; results were normalized to protein concentration [1] - Oxidative stress assays: Cells/tissues were homogenized, and SOD, GSH-Px activities, and MDA levels were measured using colorimetric assay kits [1] #### From Literature [3] (AMPK Activity Assay) - HepG2 cells were treated with Demethyleneberberine (10, 20, 40 μM) and palmitic acid, then lysed [3] - AMPK activity was determined by measuring the phosphorylation of its substrate (ACC) via Western blot, with p-ACC/ACC ratio reflecting AMPK activation [3] |
| Cell Assay |
- HepG2 cells were cultured in DMEM medium with 10% fetal bovine serum, treated with Demethyleneberberine (10, 20, 40 μM) for 2 hours, then exposed to ethanol (100 mM) for 24 hours [1]
- ROS detection: Cells were loaded with DCFH-DA fluorescent probe, incubated for 30 minutes, and fluorescence intensity was measured by flow cytometry [1] - Lipid accumulation assay: Cells were stained with Oil Red O, eluted with isopropanol, and absorbance was measured at 510 nm [1] - Western blot: Cells were lysed, proteins separated by SDS-PAGE, and blotted with antibodies against SREBP-1c, FASN, PPARα, and β-actin [1] #### From Literature [2] - RAW264.7 cells were treated with Demethyleneberberine (5, 10, 20 μM) for 1 hour, then stimulated with LPS (1 μg/mL) for 24 hours [2] - Cytokine detection: Culture supernatants were collected, and TNF-α, IL-6, IL-1β levels were measured by ELISA [2] - NF-κB translocation assay: Cells were fixed, permeabilized, stained with p65 antibody and DAPI, and observed under confocal microscopy [2] - Caco-2 cells were treated with Demethyleneberberine (5, 10, 20 μM) and TNF-α (10 ng/mL) for 24 hours; tight junction proteins were detected by Western blot [2] #### From Literature [3] - HepG2 cells were treated with Demethyleneberberine (10, 20, 40 μM) and palmitic acid (200 μM) for 24 hours [3] - Triglyceride assay: Cells were lysed, and TG content was measured by colorimetric assay [3] - Western blot: Blotted with antibodies against p-AMPK, AMPK, PGC-1α, CPT1A, and β-actin [3] |
| Animal Protocol |
#### From Literature [1] (Alcoholic Liver Disease)
- Male C57BL/6 mice (6–8 weeks old) were randomly divided into control, ethanol model, and Demethyleneberberine (25, 50 mg/kg/day) groups (n=8 per group) [1] - Mice were fed a Lieber-DeCarli ethanol diet (5% ethanol) for 4 weeks; the compound was dissolved in 0.5% carboxymethylcellulose sodium and administered by oral gavage once daily [1] - At the end of treatment, mice were sacrificed; liver tissues were collected for H&E staining, TG assay, mitochondrial function analysis, and Western blot [1] - Serum was collected to detect ALT, AST levels [1] #### From Literature [2] (Inflammatory Bowel Disease) - Male C57BL/6 mice (6–8 weeks old) were randomly divided into control, DSS model, and Demethyleneberberine (25, 50 mg/kg/day) groups (n=8 per group) [2] - Colitis was induced by adding 3% DSS to drinking water for 7 days; the compound was administered by oral gavage once daily during DSS exposure [2] - Body weight and colon length were measured; colon tissues were collected for H&E staining, cytokine assay, and Western blot [2] - Mesenteric lymph nodes were isolated for flow cytometry analysis of T-cell subsets [2] #### From Literature [3] (Non-Alcoholic Fatty Liver Disease) - Male ob/ob mice or HFD-fed C57BL/6 mice (6–8 weeks old) were randomly divided into control, model, and Demethyleneberberine (25, 50 mg/kg/day) groups (n=8 per group) [3] - The compound was dissolved in 0.5% carboxymethylcellulose sodium and administered by oral gavage once daily for 8 weeks [3] - Mice were sacrificed; liver tissues were collected for H&E staining, TG assay, and Western blot [3] - Serum was collected to detect glucose, insulin, and lipid profiles [3] |
| Toxicity/Toxicokinetics |
In all animal models, oral administration of methylene berberine (25–50 mg/kg/day) for 4–8 weeks did not cause significant changes in body weight, liver function (ALT, AST), or kidney function (BUN, Cr) [1][2][3]. No obvious clinical toxicities (somnolence, loss of appetite, organ damage) were observed in the treatment group mice [1][2][3].
|
| References |
|
| Additional Infomation |
Demethylberberine belongs to the isoquinoline class of compounds. It has been reported that demethylberberine is found in Thalictrum javanicum, and related data have been reported. Demethylberberine is a natural isoquinoline alkaloid isolated from plants of the Berberidaceae family [1][2][3]. Its core mechanisms include mitochondrial-targeted antioxidant activity, AMPK activation, and NF-κB signaling pathway inhibition [1][2][3]. It has therapeutic potential for metabolic and inflammatory diseases, including alcoholic liver disease, non-alcoholic fatty liver disease, and inflammatory bowel disease [1][2][3]. This compound exerts tissue protective effects by regulating lipid metabolism, reducing oxidative stress, inhibiting inflammation, and maintaining cell barrier function [1][2][3].
|
| Molecular Formula |
C19H18NO4
|
|---|---|
| Molecular Weight |
324.3505
|
| Exact Mass |
323.116
|
| CAS # |
25459-91-0
|
| Related CAS # |
Demethyleneberberine chloride;16705-03-6
|
| PubChem CID |
363209
|
| Appearance |
Light yellow to yellow solid powder
|
| LogP |
1.649
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
24
|
| Complexity |
447
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
HVTCKKMWZDDWOY-UHFFFAOYSA-O
|
| InChi Code |
InChI=1S/C19H17NO4/c1-23-18-4-3-11-7-15-13-9-17(22)16(21)8-12(13)5-6-20(15)10-14(11)19(18)24-2/h3-4,7-10,22H,5-6H2,1-2H3/p+1
|
| Chemical Name |
9,10-dimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2,3-diol
|
| 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 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)
|
| Solubility (In Vitro) |
DMSO : ~10 mg/mL (~30.83 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.71 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0831 mL | 15.4154 mL | 30.8309 mL | |
| 5 mM | 0.6166 mL | 3.0831 mL | 6.1662 mL | |
| 10 mM | 0.3083 mL | 1.5415 mL | 3.0831 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
