| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Natural alkaloid from Sceletium tortuosum
|
|---|---|
| ln Vitro |
Continuing our systematic investigation on the Iberian Narcissus plants, we haveanalyzed Narcissus pallidulus Graells (Amaryllidaceae). Even though there have beensome efforts aimed to regard this species in a separate genus, at present it is included inthe section Ganymedes, a primitive group in the Narcissus L. genus (2). No phytochem-ical analysis has been reported on this plant. In the present communication we reportthe isolation and structure elucidation of mesembrenone [1], an alkaloid belonging tothe mesembrine group. Although both amaryllidaceous and mesembrine-type al-kaloids have common biogenetic precursors, further studies have demonstrated that thebiosyntheses of these two classes of alkaloids are fundamentally different (3). The pres-ence of mesembrenone in N. pallidulus is of chemotaxonomic interest because mesem-brines seem to be restricted to Aizoaceae-Mesembryanthemoideae (Dicotyledones) (4).Only twice before has the occurrence of mesembrane-type alkaloids in this plant family,namely amisine from Hymenocallis arenicola (5) and mesembrenol from Crinum oligan-thum (6), been reported. Some doubts were cast on this finding because of its unexpect-edness (7). However, our present communication gives support to the sporadic pres-ence in the Amaryllidaceae of such alkaloids as those found in some Sceletium (Aizoaceae)species [1].
|
| References | |
| Additional Infomation |
Mesembrenone is a member of pyrrolidines.
Mesembrenone has been reported in Bergeranthus scapiger, Lampranthus blandus, and other organisms with data available. Alkaloid isolation.—The fresh plants (2.35 kg) were exhaustively extracted with EtOH at roomtemperature. The EtOH extract was filtered, concentrated under reduced pressure, and then acidified withHO Ac up to a 5% solution. The filtered acidic solution was washed with Et20 to remove neutral materialand extracted with CHC13. The alkaloids detected in the CHC13 phase were present in so little amount thatthey could not be chemically characterized. The aqueous acidic solution was alkalinized with Na2C03 topH 8-9 and the alkaloids extracted with CHC13. The CHC13 phase was then washed with a Na2C03 solu-tion, and the solvent was removed to give an alkaloid residue (2485 mg). The crude alkaloid extract wasthen chromatographed on a Si gel column (170 g). Elution with an increasing polarity solution of EtOAc-EtOH (10:2) afforded an amorphous alkaloid, which was further purified by means of preparative tic. Aftersolubilization with EtOH, this residue was treated with picric acid and was crystallized in MeOH/Me2CO,yielding 73.7 mg of crystals [1]. |
| Molecular Formula |
C17H21NO3
|
|---|---|
| Molecular Weight |
287.354
|
| Exact Mass |
287.152
|
| Elemental Analysis |
C, 71.06; H, 7.37; N, 4.87; O, 16.70
|
| CAS # |
468-54-2
|
| PubChem CID |
216272
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
383.9±42.0 °C at 760 mmHg
|
| Flash Point |
186.0±27.9 °C
|
| Vapour Pressure |
0.0±0.9 mmHg at 25°C
|
| Index of Refraction |
1.563
|
| Source |
Bergeranthus scapiger, Lampranthus blandus
|
| LogP |
1.37
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
21
|
| Complexity |
436
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
CN1CC[C@@]2(C=CC(=O)C[C@@H]21)C3=CC(=C(C=C3)OC)OC
|
| InChi Key |
HDNHBCSWFYFPAN-IRXDYDNUSA-N
|
| InChi Code |
InChI=1S/C17H21NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-7,10,16H,8-9,11H2,1-3H3/t16-,17-/m0/s1
|
| Chemical Name |
(3aR,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,7,7a-tetrahydroindol-6-one
|
| Synonyms |
Mesembrenone; 468-54-2; (+)-Mesembrenone; Mesembrenone, (+)-; (3aR,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,7,7a-tetrahydroindol-6-one; HT8JNS8E79; CHEMBL4781238;
|
| 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)
|
| 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
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 | 3.4801 mL | 17.4004 mL | 34.8008 mL | |
| 5 mM | 0.6960 mL | 3.4801 mL | 6.9602 mL | |
| 10 mM | 0.3480 mL | 1.7400 mL | 3.4801 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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