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Purity: ≥98%
| Targets |
Natural furoquinoline alkaloid
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| ln Vitro |
Skimmianine is a furoquinoline alkaloid present mainly in the Rutaceae family. It has been reported to have analgesic, antispastic, sedative, anti-inflammatory, and other pharmacologic activities. Despite its critical pharmacological function, its metabolite profiling is still unclear[1].
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| ln Vivo |
In this study, the in vivo metabolite profiling of skimmianine in rats was investigated using ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS). The metabolites were predicted using MetabolitePilotTM software. These predicted metabolites were further analyzed by MS² spectra, and compared with the detailed fragmentation pathway of the skimmianine standard and literature data. A total of 16 metabolites were identified for the first time in rat plasma, urine, and feces samples after oral administration of skimmianine. Skimmianine underwent extensive Phase I and Phase II metabolism in rats. The Phase I biotransformations of skimmianine consist of epoxidation of olefin on its furan ring (M1) followed by the hydrolysis of the epoxide ring (M4), hydroxylation (M2, M3), O-demethylation (M5-M7), didemethylation (M14-M16). The Phase II biotransformations include glucuronide conjugation (M8-M10) and sulfate conjugation (M11-M13). The epoxidation of 2,3-olefinic bond followed by the hydrolysis of the epoxide ring and O-demethylation were the major metabolic pathways of skimmianine. The results provide key information for understanding the biotransformation processes of skimmianine and the related furoquinoline alkaloids[1].
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| Cell Assay |
Two milliliters of plasma sample were loaded onto a pretreated solid-phase extraction (SPE) column. The column was washed with 6 mL of water, followed by elution using 6 mL of methanol. The methanol eluate was evaporated to dryness at 35 °C. The residue was reconstituted in 300 μL of acetonitrile and water (50:50, v/v) and centrifuged at 15,493× g for 15 min. The supernatant was used for LC-MS analysis.
Two milliliters of urine sample were prepared using the same method as the plasma samples with a minor change. Rather than 300 μL of acetonitrile and water (50:50, v/v), the residue was dissolved in 600 μL of acetonitrile and water (50:50, v/v) and centrifuged at 15,493× g for 15 min. The supernatant was collected for LC-MS analysis.
The feces sample was extracted with 15 times the amount of methanol–water (70:30, v/v). The extract was centrifuged at 15,493× g for 15 min. The supernatant was collected.[1]
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| Animal Protocol |
Male Sprague–Dawley rats (250 ± 20 g) used in this study were provided by the Experimental Animal Center of Guangzhou University of Chinese Medicine. The laboratory animal license number is SCXK 2013-0020. These animals were maintained in an air-conditioned animal facility at 23 ± 2 °C, with a humidity of 55% ± 5% and a 12 h light/dark cycle for 5 days before use. The rats had free access to water and a standard diet. Animal welfare and experimental procedures were strictly in accordance with the guidelines of the Committee on the Care and Use of Laboratory Animals in China and the related ethical regulations of Guangzhou University of Chinese Medicine.
The rats were randomly divided into 3 groups, with A for the blank control group, B for plasma collection group, and C for the urine and feces collection group, 6 rats per group. Before administration, the rats were fasted for 12 h but were allowed water access ad libitum. Skimmianine suspension in a 0.5% carboxymethyl cellulose sodium aqueous solution was orally administered to Groups B and C at a dose of 20 mg·kg−1 body weight, while a 0.5% carboxymethyl cellulose sodium aqueous solution was orally administered to Group A. The rats of Group B were anesthetized at 0.5 h, 1 h, 2 h, 3 h, 4 h, and 6 h after doses, respectively. The blood samples were collected from aorta abdominalis in heparinized tubes. All blood samples were then centrifuged at 1274× g for 15 min at 4 °C and mixed together to produce the pooled plasma. Blank plasma samples collected from Group A were prepared following the same procedures. For the collection of urine and feces samples after dose, the rats of Group C were put into metabolic cages individually. The samples were collected at 24 h post-intake, respectively, while control urine and feces samples were collected before drug administration. All samples were stored at −80 °C. The frozen urine and feces samples were thawed at room temperature before use. |
| References | |
| Additional Infomation |
Skimmianine is an organonitrogen heterocyclic compound, an organic heterotricyclic compound, an oxacycle and an alkaloid antibiotic.
Skimmianine is a natural product found in Ruta macrophylla, Teclea simplicifolia, and other organisms with data available. |
| Molecular Formula |
C14H13NO4
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|---|---|
| Molecular Weight |
259.2573
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| Exact Mass |
259.084
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| Elemental Analysis |
C, 64.86; H, 5.05; N, 5.40; O, 24.68
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| CAS # |
83-95-4
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| PubChem CID |
6760
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| Appearance |
Typically exists as white to off-white solids at room temperature
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
401.6±40.0 °C at 760 mmHg
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| Melting Point |
178°
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| Flash Point |
196.7±27.3 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.621
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| LogP |
2.86
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
19
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| Complexity |
314
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| Defined Atom Stereocenter Count |
0
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| SMILES |
N1C2C(=CC=C(C=2OC)OC)C(OC)=C2C=1OC=C2
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| InChi Key |
SLSIBLKBHNKZTB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H13NO4/c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2/h4-7H,1-3H3
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| Chemical Name |
COC1=C2N=C(OC=C3)C3=C(OC)C2=CC=C1OC
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| Synonyms |
Skimmianine; 83-95-4; Skimmianin; 4,7,8-Trimethoxyfuro[2,3-b]quinoline; Chloroxylonine; Skimmiamine; .beta.-Fagarine; Furo[2,3-b]quinoline, 4,7,8-trimethoxy-;
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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) |
DMSO : ~33.33 mg/mL (~128.56 mM)
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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 | 3.8571 mL | 19.2857 mL | 38.5713 mL | |
| 5 mM | 0.7714 mL | 3.8571 mL | 7.7143 mL | |
| 10 mM | 0.3857 mL | 1.9286 mL | 3.8571 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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