SeneciphyllineCAS# 480-81-9 |
- Spartioidine
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| Cas No. | 480-81-9 | SDF | Download SDF |
| PubChem ID | 5281750 | Appearance | White powder |
| Formula | C18H23NO5 | M.Wt | 333.4 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Synonyms | Jacodine; α-Longilobine | ||
| Solubility | Soluble in chloroform | ||
| SMILES | CC=C1CC(=C)C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O | ||
| Standard InChIKey | FCEVNJIUIMLVML-QPSVUOIXSA-N | ||
| Standard InChI | InChI=1S/C18H23NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4-/t14-,15-,18-/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. Seneciphylline, one of the hepatotoxic pyrolizidine alkaloids, can induce a marked arterial and arteriolar hypertrophy of the lung of young Wistar rats a month after a single s. c. injection of 50–80 mg/kg. 2. Seneciphylline and senkirkine, two pyrrolizidine alkaloids, have mutagenic activity in Drosophila and their transfer into rat milk. 3. Seneciphylline can significantly increased the activities of epoxide hydrase and glutathione-S-transferase but cause reduction of cytochrome P-450 and related monooxygenase activities. |
| Targets | P450 (e.g. CYP17) |
Seneciphylline Dilution Calculator
Seneciphylline Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.9994 mL | 14.997 mL | 29.994 mL | 59.988 mL | 74.985 mL |
| 5 mM | 0.5999 mL | 2.9994 mL | 5.9988 mL | 11.9976 mL | 14.997 mL |
| 10 mM | 0.2999 mL | 1.4997 mL | 2.9994 mL | 5.9988 mL | 7.4985 mL |
| 50 mM | 0.06 mL | 0.2999 mL | 0.5999 mL | 1.1998 mL | 1.4997 mL |
| 100 mM | 0.03 mL | 0.15 mL | 0.2999 mL | 0.5999 mL | 0.7499 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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Effect of seneciphylline and senecionine on hepatic drug metabolizing enzymes in rats.[Pubmed:6533413]
J Ethnopharmacol. 1984 Dec;12(3):271-8.
The effect of oral administration of the pyrrolizidine alkaloids, Seneciphylline and senecionine, from Senecio vulgaris (Compositae) on activities of hepatic epoxide hydrase, glutathione-S-transferase, aminopyrine-N-demethylase and arylhydrocarbon hydroxylase (AHH) was investigated in microsomes of young male albino rats. Seneciphylline significantly increased the activities of epoxide hydrase and glutathione-S-transferase but caused reduction of cytochrome P-450 and related monooxygenase activities. Senecionine failed to stimulate epoxide hydrase while it diminished the activities of glutathione-S-transferase, aminopyrine demethylase and AHH. Seneciphylline and senecionine could not produce any prominent in vitro effect on the hepatic drug metabolizing enzymes under study, except slight stimulation of epoxide hydrase activity by both the alkaloids and slight reduction of aminopyrine demethylase activity by senecionine.
Effects of the pyrrolizidine alkaloids senecionine, retrorsine and seneciphylline on aminopyrine N-demethylase activity on the rat liver S-10 fraction.[Pubmed:7268806]
Toxicol Lett. 1981 Jun-Jul;8(4-5):217-22.
The effects of individual pyrrolizidine alkaloids on the mixed-function oxidase (MFO) enzyme aminopyrine N-demethylase were determined in rat liver 10 000 X g supernatant. The pyrrolizidine alkaloids, senecionine, Seneciphylline and retrorsine were obtained from Senecio vulgaris. Senecionine and Seneciphylline were found to be linear mixed-type inhibitors while retrorsine was found to be a competitive inhibitor of aminopyrine N-demethylase. The average Ki's +/- S.E. for senecionine, Seneciphylline and retrorsine were 0.18 +/- 0.02, 0.33 +/- 0.06 and 0.92 +/- 0.05 mM, respectively.
Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays.[Pubmed:24981118]
J Chem Ecol. 2014 Jun;40(6):609-16.
Pyrrolizidine alkaloids (PAs) are feeding deterrents and toxic compounds to generalist herbivores. Among the PAs of Jacobaea vulgaris Gaertn, jacobine and erucifoline are the most effective against insect herbivores as indicated by correlative studies. Because little is known about the effect of jacobine and erucifoline as individual PAs, we isolated these compounds from their respective Jacobaea chemotypes. These PAs and other commercially available senecionine-like PAs, including senecionine, Seneciphylline, retrorsine, and senkirkine, were tested as free base and N-oxide forms at a range of 0-70 ppm. Feeding bioassays using live insects are closer to the natural pattern but require relatively large amounts of test compounds. We, therefore, compared the toxicity of PAs using both Spodoptera exigua cell line and larval injection bioassays. Both bioassays led to similar results in the order of PA toxicity, indicating that the cell lines are a valuable tool for a first toxicity screen. Testing individual PAs, jacobine and erucifoline were the most toxic PAs, suggesting their major role in plant defense against generalist herbivores. Senkirkine and Seneciphylline were less toxic than jacobine and erucifoline but more toxic than retrorsine. Senecionine was not toxic at the tested concentrations. For all toxic PAs, the free base form was more toxic than the N-oxide form. Our results demonstrate that structural variation of PAs influences their effectiveness in plant defense.
