StephanineCAS# 517-63-5 |
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| Cas No. | 517-63-5 | SDF | Download SDF |
| PubChem ID | 160501 | Appearance | Cryst. |
| Formula | C19H19NO3 | M.Wt | 309.4 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | CN1CCC2=CC3=C(C4=C2C1CC5=C4C=CC=C5OC)OCO3 | ||
| Standard InChIKey | UEAPAHNNFSZHMW-CQSZACIVSA-N | ||
| Standard InChI | InChI=1S/C19H19NO3/c1-20-7-6-11-8-16-19(23-10-22-16)18-12-4-3-5-15(21-2)13(12)9-14(20)17(11)18/h3-5,8,14H,6-7,9-10H2,1-2H3/t14-/m1/s1 | ||
| 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 | 1. l-Stephanine is a potent and highly selective alpha 1 adrenoceptor blocker, inhibits anococcygeus muscle contraction induced by phenylephrine with pA2 values of 6.76. 2. Stephanine and crebanine have high inhibitory activity against gram-positive animal pathogenic bacteria, with MIC values of 0.078-0.312g/l, but low inhibitory activity against gram-negative animal pathogenic bacteria, they also inhibit hyphal growth of the plant pathogens Cercospora kaki. 3. Stephanine, pseudopalmatine , tetrahydropalmatine , and xylopinine show significant antiplasmodial activities with IC(50) ranged from 1.2 uM to 52.3 uM. |
| Targets | Adrenergic Receptor | Antifection |
Stephanine Dilution Calculator
Stephanine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.2321 mL | 16.1603 mL | 32.3206 mL | 64.6412 mL | 80.8016 mL |
| 5 mM | 0.6464 mL | 3.2321 mL | 6.4641 mL | 12.9282 mL | 16.1603 mL |
| 10 mM | 0.3232 mL | 1.616 mL | 3.2321 mL | 6.4641 mL | 8.0802 mL |
| 50 mM | 0.0646 mL | 0.3232 mL | 0.6464 mL | 1.2928 mL | 1.616 mL |
| 100 mM | 0.0323 mL | 0.1616 mL | 0.3232 mL | 0.6464 mL | 0.808 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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[Blocking actions of l-stephanine, xylopine and 7 other tetrahydroisoquinoline alkaloids on alpha adrenoceptors].[Pubmed:2576175]
Zhongguo Yao Li Xue Bao. 1989 Jul;10(4):302-6.
The blocking action and selectivity of 9 tetrahydroisoquinoline alkaloids on alpha adrenoceptors have been investigated in isolated tissues. DehydroStephanine and berbamine suppressed the inhibition of clonidine for the electrically stimulated twitch response of rat vas deferens, with pA2 values of 5.36 and 5.49, respectively. l-Crebanine, l-tetrahydrocoptisine, berberine, l-stepholidine and l-tetrahydropalmatine had obvious blocking effects on alpha 1 and alpha 2 adrenoceptors. l-Stephanine and xylopine could competitively inhibit anococcygeus muscle contraction induced by phenylephrine with pA2 values of 6.76 and 6.68, respectively. These 2 alkaloids showed no effect on the inhibition of clonidine for contractile response of rat vas deferens to field stimulation, and their selectivity ratios to block alpha 1 and alpha 2 adrenoceptors were 57.5 and 47.9, respectively. These results indicate that l-Stephanine and xylopine are 2 potent and highly selective alpha 1 adrenoceptor blockers.
New antiplasmodial alkaloids from Stephania rotunda.[Pubmed:23127648]
J Ethnopharmacol. 2013 Jan 9;145(1):381-5.
ETHNOPHARMACOLOGICAL RELEVANCE: Stephania rotunda Lour. (Menispermaceae) is a creeper growing in many countries of Asia and commonly found in the mountainous areas of Cambodia. As a folk medicine, it has been mainly used for the treatment of fever and malaria. The pharmacological activity is mostly due to alkaloids. Thus the aim of this study is to isolate new bioactive alkaloids from Stephania rotunda and to evaluate their in vitro antiplasmodial activity. MATERIALS AND METHODS: Alkaloids were isolated and identified from dichloromethane and aqueous extracts using a combination of flash chromatography, high performance liquid chromatography, mass spectrometry and nuclear magnetic resonance. The purified compounds were tested for in vitro antiplasmodial activity on chloroquine-resistant W2 strain of Plasmodium falciparum. RESULTS: A new aporphine alkaloid named vireakine (2) along with two known alkaloids Stephanine (1) and pseudopalmatine (8), described for the first time in Stephania rotunda, and together five known alkaloids tetrahydropalmatine (3), xylopinine (4), roemerine (5), cepharanthine (6) and palmatine (7) were isolated and identified. The structure of the new alkaloid was established on the basis of 1D and 2D NMR experiments and mass spectrometry. The compounds were evaluated for their in vitro antiplasmodial and cytotoxic activities. All tested compounds showed significant antiplasmodial activities with IC(50) ranged from 1.2 muM to 52.3 muM with a good selectivity index for pseudopalmatine with IC(50) of 2.8 muM against W2 strain of Plasmodium falciparum and IC(50)>25 muM on K562S cells. CONCLUSIONS: This study provides evidence to support the use of Stephania rotunda for the treatment of malaria and/or fever by the healers. Alkaloids of the tuber exhibited antiplasmodial activity and particularly cepharanthine and pseudopalmatine.
