Seneciphylline
(Synonyms: 千里光菲灵碱) 目录号 : GC44882
An alkaloid with diverse biological activities
Cas No.:480-81-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Seneciphylline is an alkaloid that has been found F. japonicum and has diverse biological activites. It induces autophagy and decreases viability of Huh7.5 cells in a concentration-dependent manner. Seneciphylline is also cytotoxic to HepG2 cells (IC20 = 0.66 mM). Dietary administration of seneciphylline induces sex-linked recessive lethality in male Drosophila. Seneciphylline (80 mg/kg) increases the activity of epoxide hydrase and glutathione-S-transferase and decreases activity of cytochrome P450 and aminopyrine demethylase in rat liver.
| Cas No. | 480-81-9 | SDF | |
| 别名 | 千里光菲灵碱 | ||
| Canonical SMILES | O=C(/C(CC([C@@]1(C)O)=C)=C\C)O[C@]2([H])CCN3[C@]2([H])C(COC1=O)=CC3 | ||
| 分子式 | C18H23NO5 | 分子量 | 333.4 |
| 溶解度 | DMF: 5 mg/ml,DMSO: 2 mg/ml,Ethanol: 1 mg/ml,PBS (pH 7.2): 0.1 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.9994 mL | 14.997 mL | 29.994 mL |
| 5 mM | 0.5999 mL | 2.9994 mL | 5.9988 mL |
| 10 mM | 0.2999 mL | 1.4997 mL | 2.9994 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Seneciphylline, a main pyrrolizidine alkaloid in Gynura japonica, induces hepatotoxicity in mice and primary hepatocytes via activating mitochondria-mediated apoptosis
J Appl Toxicol 2020 Nov;40(11):1534-1544.PMID:32618019DOI:10.1002/jat.4004.
Herbal drug-induced liver injury has been reported worldwide and gained global attention. Thousands of hepatic sinusoidal obstruction syndrome (HSOS) cases have been reported after consumption of herbal medicines and preparations containing pyrrolizidine alkaloids (PAs), which are natural phytotoxins globally distributed. And herbal medicines, such as Gynura japonica, are the current leading cause of PA-induced HSOS. The present study aimed to reveal the mechanism underlying the hepatotoxicity of Seneciphylline (Seph), a main PA in G. japonica. Results showed that Seph induced severe liver injury through apoptosis in mice (70 mg/kg Seph, orally) and primary mouse and human hepatocytes (5-50 μM Seph). Further research uncovered that Seph induced apoptosis by disrupting mitochondrial homeostasis, inducing mitochondrial depolarization, mitochondrial membrane potential (MMP) loss, and cytochrome c (Cyt c) release and activating c-Jun N-terminal kinase (JNK). The Seph-induced apoptosis in hepatocytes could be alleviated by Mdivi-1 (50 μM, a dynamin-related protein 1 inhibitor), as well as SP600125 (25 μM, a specific JNK inhibitor) and ZVAD-fmk (50 μM, a general caspase inhibitor). Moreover, the Seph-induced MMP loss in hepatocytes was also rescued by Mdivi-1. In conclusion, Seph induced liver toxicity via activating mitochondrial-mediated apoptosis in mice and primary hepatocytes. Our results provide further information on Seph detoxification and herbal medicines containing Seph such as G. japonica.
LC-MS/MS method for determination of Seneciphylline and its metabolite, Seneciphylline N-oxide in rat plasma, and its application to a rat pharmacokinetic study
Biomed Chromatogr 2021 Sep;35(9):e5145.PMID:33886121DOI:10.1002/bmc.5145.
A rapid and sensitive ultra-performance liquid chromatography-tandem electrospray ionization mass spectrometry (UPLC-ESI/MS) method was established and validated for simultaneous determination of Seneciphylline and its main metabolite in rat plasma. The plasma sample was prepared by simple methanol-mediated precipitation. Chromatographic separation was achieved within 3 min by gradient elution using acetonitrile and water containing 0.1% formic acid as mobile phase on a Waters ACQUITY BEH C18 column (100 × 2.1 mm, i.d. 1.7 μm). Quantitation was conducted in a positive multiple reaction monitoring mode. The linearity of the method was over the range of 1-1,000 ng/mL, with the lower limit of quantification of 1 ng/mL. The intra- and inter-day precision and accuracy, extraction recovery, and matrix effect of analytes were within the acceptable limit. The analytes were stable during the process of sample collection, preparation, and analysis. The validated method was further applied to a pharmacokinetic study of Seneciphylline in rats after oral and intravenous administration. The results revealed that Seneciphylline was quickly absorbed into plasma (Tmax , 0.23-0.32 h) and reached the maximum concentration of 0.82-1.75 μg/mL after oral administration. Both Seneciphylline and Seneciphylline N-oxide were eliminated from plasma quickly. The low system exposure (oral bioavailability, 5.43-10.31%) was related to the extensive metabolism in the liver and microflora.
Mutagenic activity of the pyrrolizidine alkaloids Seneciphylline and senkirkine in Drosophila and their transfer into rat milk
Food Chem Toxicol 1984 Mar;22(3):223-5.PMID:6423472DOI:10.1016/0278-6915(84)90131-5.
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.
Effect of Seneciphylline and senecionine on hepatic drug metabolizing enzymes in rats
J Ethnopharmacol 1984 Dec;12(3):271-8.PMID:6533413DOI:10.1016/0378-8741(84)90056-4.
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
Toxicol Lett 1981 Jun-Jul;8(4-5):217-22.PMID:7268806DOI:10.1016/0378-4274(81)90104-1.
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.