DihydroberberineCAS# 483-15-8 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 483-15-8 | SDF | Download SDF |
| PubChem ID | 10217 | Appearance | Yellow crystals |
| Formula | C20H19NO4 | M.Wt | 337.36 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Synonyms | Dihydroumbellatine | ||
| Solubility | Soluble to 57.46 mg/l in water | ||
| SMILES | COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2)OCO5)OC | ||
| Standard InChIKey | FZAGOOYMTPGPGF-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Dihydroberberine has anti-tumor activity. It also improves in vivo efficacy in terms of counteracting increased adiposity, tissue triglyceride accumulation, and insulin resistance in high-fat-fed rodents, thus is potential therapeutic reagents for type 2 diabetes treatment. |
| Targets | AMPK |
| In vitro | Studies on the synthesis andin vitro anti-tumor activity of dihydroberberine derivatives.[Pubmed: 18982493]Arch Pharm Res. 1997 Oct;20(5):476-9.
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| In vivo | Berberine and its more biologically available derivative, dihydroberberine, inhibit mitochondrial respiratory complex I: a mechanism for the action of berberine to activate AMP-activated protein kinase and improve insulin action.[Pubmed: 18285556]Diabetes. 2008 May;57(5):1414-8.Berberine (BBR) activates AMP-activated protein kinase (AMPK) and improves insulin sensitivity in rodent models of insulin resistance. We investigated the mechanism of activation of AMPK by BBR and explored whether derivatization of BBR could improve its in vivo efficacy.
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| Animal Research | 8,8-Dimethyldihydroberberine with improved bioavailability and oral efficacy on obese and diabetic mouse models.[Pubmed: 20663675]Bioorg Med Chem. 2010 Aug 15;18(16):5915-24.The clinical use of the natural alkaloid berberine (BBR) as an antidiabetic reagent is limited by its poor bioavailability. Our previous work demonstrated that Dihydroberberine (dhBBR) has enhanced bioavailability and in vivo efficacy compared with berberine. |
Dihydroberberine Dilution Calculator
Dihydroberberine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.9642 mL | 14.821 mL | 29.6419 mL | 59.2839 mL | 74.1048 mL |
| 5 mM | 0.5928 mL | 2.9642 mL | 5.9284 mL | 11.8568 mL | 14.821 mL |
| 10 mM | 0.2964 mL | 1.4821 mL | 2.9642 mL | 5.9284 mL | 7.4105 mL |
| 50 mM | 0.0593 mL | 0.2964 mL | 0.5928 mL | 1.1857 mL | 1.4821 mL |
| 100 mM | 0.0296 mL | 0.1482 mL | 0.2964 mL | 0.5928 mL | 0.741 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Studies on the synthesis andin vitro anti-tumor activity of dihydroberberine derivatives.[Pubmed:18982493]
Arch Pharm Res. 1997 Oct;20(5):476-9.
Three types of Dihydroberberine derivatives such as spirobenzylisoquinoline, benzindenoazepine and cyclopropanated quinolizine species were synthesized from Dihydroberberine for the investigation on their anti-tumor activity. Among them, cyclopropanated quinolizine species were more effective than spirobenzylisoquinoline and benzindenoazepine against P-388 and L-1210 leukemia cell.
Berberine and its more biologically available derivative, dihydroberberine, inhibit mitochondrial respiratory complex I: a mechanism for the action of berberine to activate AMP-activated protein kinase and improve insulin action.[Pubmed:18285556]
Diabetes. 2008 May;57(5):1414-8.
OBJECTIVE: Berberine (BBR) activates AMP-activated protein kinase (AMPK) and improves insulin sensitivity in rodent models of insulin resistance. We investigated the mechanism of activation of AMPK by BBR and explored whether derivatization of BBR could improve its in vivo efficacy. RESEARCH DESIGN AND METHODS: AMPK phosphorylation was examined in L6 myotubes and LKB1(-/-) cells, with or without the Ca(2+)/calmodulin-dependent protein kinase kinase (CAMKK) inhibitor STO-609. Oxygen consumption was measured in L6 myotubes and isolated muscle mitochondria. The effect of a BBR derivative, Dihydroberberine (dhBBR), on adiposity and glucose metabolism was examined in rodents fed a high-fat diet. RESULTS; We have made the following novel observations: 1) BBR dose-dependently inhibited respiration in L6 myotubes and muscle mitochondria, through a specific effect on respiratory complex I, similar to that observed with metformin and rosiglitazone; 2) activation of AMPK by BBR did not rely on the activity of either LKB1 or CAMKKbeta, consistent with major regulation at the level of the AMPK phosphatase; and 3) a novel BBR derivative, dhBBR, was identified that displayed improved in vivo efficacy in terms of counteracting increased adiposity, tissue triglyceride accumulation, and insulin resistance in high-fat-fed rodents. This effect is likely due to enhanced oral bioavailability. CONCLUSIONS: Complex I of the respiratory chain represents a major target for compounds that improve whole-body insulin sensitivity through increased AMPK activity. The identification of a novel derivative of BBR with improved in vivo efficacy highlights the potential importance of BBR as a novel therapy for the treatment of type 2 diabetes.
8,8-Dimethyldihydroberberine with improved bioavailability and oral efficacy on obese and diabetic mouse models.[Pubmed:20663675]
Bioorg Med Chem. 2010 Aug 15;18(16):5915-24.
The clinical use of the natural alkaloid berberine (BBR) as an antidiabetic reagent is limited by its poor bioavailability. Our previous work demonstrated that Dihydroberberine (dhBBR) has enhanced bioavailability and in vivo efficacy compared with berberine. Here we synthesized the 8,8-dimethylDihydroberberine (Di-Me) with improved stability, and bioavailability over dhBBR. Similar to BBR and dhBBR, Di-Me inhibited mitochondria respiration, increased AMP:ATP ratio, activated AMPK and stimulated glucose uptake in L6 myotubes. In diet-induced obese (DIO) mice, Di-Me counteracted the increased adiposity, tissue triglyceride accumulation and insulin resistance, and improved glucose tolerance at a dosage of 15mg/kg. Administered to db/db mice with a dosage of 50mg/kg, Di-Me effectively reduced random fed and fasting blood glucose, improved glucose tolerance, alleviated insulin resistance and reduced plasma triglycerides, with better efficacy than dhBBR at the same dosage. Our work highlights the importance of Dihydroberberine analogs as potential therapeutic reagents for type 2 diabetes treatment.
