| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
(-)-Stylopine (S-Stylopine) is the S-enantiomer of Stylopine [(±)-Stylopine; Tetrahydrocoptisine; (R,S±)-Stylopine; NSC-110382; NSC-404529], which is a naturally occurring isoquinoline alkaloid isolated from C. impatiens with anti-inflammatory and antioxidant activities. Stylopine is a potent AKR1C3 (Aldo-keto reductase 103) inhibitor that significantly inhibits AKR1C3 in intact cells without a considerable cytotoxic effect. It also inhibits LPS-induced NF-κB activation and production of nitric oxide (NO), TNF-α, and IL-6 in isolated mouse peritoneal macrophages when used at concentrations ranging from 0.001 to 1 µg/ml. Tetrahydrocoptisine (10 and 30 mg/kg) inhibits xylene-induced ear edema in mice, and it decreases serum levels of TNF-α in a mouse model of LPS-induced septic shock. It reduces the severity of ethanol-induced gastric ulcers in mice when administered at doses of 10 or 20 mg/kg.
| Targets |
Natural alkaloid; anti-inflammatory; anti-parasitic
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| ln Vitro |
Stylopine is a major component of the leaf of Chelidonium majus L. (Papaveraceae), which has been used for the removal of warts, papillomas and condylomas, as well as the treatment of liver disease, in oriental countries. Stylopine per se had no cytotoxic effect in unstimulated RAW 264.7 cells, but concentration-dependently reduced nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor-alpha (TNF-alpha) and interleukin-1beta (IL-1beta), and the IL-6 production and cyclooxygenase-2 (COX-2) activity caused by the LPS stimulation. The levels of inducible nitric oxide synthase (iNOS) and COX-2 protein expressions were markedly suppressed by stylopine in a concentration dependent manner. These results suggest that stylopine suppress the NO and PGE2 production in macrophages by inhibiting the iNOS and COX-2 expressions. These biological activities of stylopine may contribute to the anti-inflammatory activity of Chelidonium majus.
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| References |
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| Additional Infomation |
(S)-stylopine is a berberine alkaloid isolated from the plants of the family papaveraceae. It has a role as a plant metabolite. It is an organic heterohexacyclic compound, an an (S)-7,8,13,14-tetrahydroprotoberberine and a berberine alkaloid.
(S)-Stylopine has been reported in Corydalis solida, Corydalis racemosa, and other organisms with data available. See also: Chelidonium majus flowering top (part of). |
| Molecular Formula |
C19H17NO4
|
|---|---|
| Molecular Weight |
323.342585325241
|
| Exact Mass |
323.116
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| Elemental Analysis |
C, 70.58; H, 5.30; N, 4.33; O, 19.79
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| CAS # |
84-39-9
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| Related CAS # |
(±)-Stylopine;4312-32-7;(±)-Stylopine hydrochloride;96087-21-7
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| PubChem CID |
440583
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
2.737
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
0
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| Heavy Atom Count |
24
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| Complexity |
502
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| Defined Atom Stereocenter Count |
1
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| SMILES |
[C@@H]12CC3C=CC4OCOC=4C=3CN1CCC1=CC3OCOC=3C=C21
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| InChi Key |
UXYJCYXWJGAKQY-HNNXBMFYSA-N
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| InChi Code |
InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m0/s1
|
| Chemical Name |
(1S)-5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-2,4(8),9,15(23),16(20),21-hexaene
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| Synonyms |
(S)-Stylopine; Stylopine; 84-39-9; l-Tetrahydrocoptisine; CHEBI:18285; (-)-Tetrahydrocoptisine; (12bS)-6,7,12b,13-tetrahydro-2H,4H,10H-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinoline; 2,3:9,10-Bis(methylenedioxy)-13a-alpha-berbine;
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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 | 3.0927 mL | 15.4636 mL | 30.9272 mL | |
| 5 mM | 0.6185 mL | 3.0927 mL | 6.1854 mL | |
| 10 mM | 0.3093 mL | 1.5464 mL | 3.0927 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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