SenkirkineCAS# 2318-18-5 |
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Quality Control & MSDS
3D structure
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| Cas No. | 2318-18-5 | SDF | Download SDF |
| PubChem ID | 5281752 | Appearance | White powder |
| Formula | C19H27NO6 | M.Wt | 365.42 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Synonyms | Renardine | ||
| Solubility | Soluble in chloroform and methan | ||
| Chemical Name | (1R,4Z,6R,7R,11Z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione | ||
| SMILES | CC=C1CC(C(C(=O)OCC2=CCN(CCC(C2=O)OC1=O)C)(C)O)C | ||
| Standard InChIKey | HPDHKHMHQGCNPE-QLJRNOHWSA-N | ||
| Standard InChI | InChI=1S/C19H27NO6/c1-5-13-10-12(2)19(3,24)18(23)25-11-14-6-8-20(4)9-7-15(16(14)21)26-17(13)22/h5-6,12,15,24H,7-11H2,1-4H3/b13-5-,14-6-/t12-,15-,19-/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. Brood pattern analysis with Senkirkine shows maximum sensitivity in the late spermatid stage of spermatogenesis. |
Senkirkine Dilution Calculator
Senkirkine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7366 mL | 13.6829 mL | 27.3658 mL | 54.7315 mL | 68.4144 mL |
| 5 mM | 0.5473 mL | 2.7366 mL | 5.4732 mL | 10.9463 mL | 13.6829 mL |
| 10 mM | 0.2737 mL | 1.3683 mL | 2.7366 mL | 5.4732 mL | 6.8414 mL |
| 50 mM | 0.0547 mL | 0.2737 mL | 0.5473 mL | 1.0946 mL | 1.3683 mL |
| 100 mM | 0.0274 mL | 0.1368 mL | 0.2737 mL | 0.5473 mL | 0.6841 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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Structure-activity relationship in the passage of different pyrrolizidine alkaloids through the gastrointestinal barrier: ABCB1 excretes heliotrine and echimidine.[Pubmed:24375927]
Mol Nutr Food Res. 2014 May;58(5):995-1004.
SCOPE: 1,2-Unsaturated pyrrolizidine alkaloids (PA) are found in plants such as Asteraceae and Boraginaceae families. Acute PA poisoning via contaminated food or feed causes severe damage to liver depending on species-specific oral bioavailability. For assessing PA bioavailability, their passage across the intestinal barrier was investigated using Caco-2 cells. METHODS: Differentiated Caco-2 cells were exposed in transport chambers to the PA heliotrine (Hn), echimidine (Em), senecionine (Sc), and Senkirkine (Sk). Cell supernatants were analyzed by LC-MS/MS. RESULTS: PA pass Caco-2 monolayer from the apical into basolateral compartment depending on their chemical structure. Compared to the cyclic diesters Sc and Sk with a passage rate of 47% +/- 4 and 40% +/- 3, respectively, the transferred amount of the monoester Hn (32% +/- 3) and open-chained diester Em (13% +/- 2) was substantially lower. This suggested an active transport of Hn and Em. Using Madin-Darby canine kidney II/P-glycoprotein (ABCB1)-overexpressing cells, the active excretion of Hn and Em by ABCB1 from the gastrointestinal epithelium into the gut lumen was shown. CONCLUSION: PA cross the intestinal barrier structure-dependently. The passage of the noncyclic PA Hn and Em is reduced by an ABCB1-driven efflux into the gastrointestinal lumen resulting in a decreased oral bioavailability.
Mutagenic activity of the pyrrolizidine alkaloids seneciphylline and senkirkine in Drosophila and their transfer into rat milk.[Pubmed:6423472]
Food Chem Toxicol. 1984 Mar;22(3):223-5.
Seneciphylline and Senkirkine, two pyrrolizidine alkaloids that occur in animal feeds and medicinal herbs, respectively, have been tested for their ability to produce sex-linked recessive lethals in males of Drosophila melanogaster using the Basc test (3-day feeding method). Seneciphylline was found to be mutagenic at concentrations of 10(-5), 10(-4) and 10(-3)M, which produced 3.8% sex-linked recessive lethals (983 chromosomes tested). 9.0% (708) and 15.3% (327), respectively. Senkirkine (10(-5)M) produced 4.4% sex-linked recessive lethals (2541 chromosomes tested) against 0.17% (9081) in controls. Brood pattern analysis with Senkirkine showed maximum sensitivity in the late spermatid stage of spermatogenesis, which agrees with evidence that pyrrolizidine alkaloids act as indirect mutagens. Flies fed with milk from lactating rats given an oral dose of 25 mg seneciphylline/kg showed 1.2% sex-linked recessive lethals (1477 chromosomes tested), against 0.3% (1533) in controls.
