Seneciphylline N-Oxide
(Synonyms: 千里光非灵N-氧化物) 目录号 : GC39042
Seneciphylline N-Oxide 是Senecionine N-oxide 的脱氢产物。Seneciphylline N-Oxide 是从 Senecio erucifolius (Asteraceae) 根部培养物提取得到的天然产物。
Cas No.:38710-26-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Seneciphylline N-Oxide is a dehydrogenation product of Senecionine N-oxide. Seneciphylline N-Oxide is a natural compound isolated from root cultures of Senecio erucifolius (Asteraceae)[1].
[1]. HEINER SANDER, et al. Site of synthesis, metabolism and transloeation of senecionine N-oxide in cultured roots of Senecio erucifolius. Plant Cell, Tissue and Organ Culture volume 18, pages19-31(1989).
| Cas No. | 38710-26-8 | SDF | |
| 别名 | 千里光非灵N-氧化物 | ||
| Canonical SMILES | O=C(O[C@]1([H])CC[N+]2([O-])[C@]1([H])C(COC([C@](C)(O)C(C/3)=C)=O)=CC2)C3=C/C | ||
| 分子式 | C18H23NO6 | 分子量 | 349.38 |
| 溶解度 | Soluble in DMSO | 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 | 2.8622 mL | 14.3111 mL | 28.6221 mL |
| 5 mM | 0.5724 mL | 2.8622 mL | 5.7244 mL |
| 10 mM | 0.2862 mL | 1.4311 mL | 2.8622 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。
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.
Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang)
Rapid Commun Mass Spectrom 2008;22(4):591-602.PMID:18220326DOI:10.1002/rcm.3398.
Senecio scandens Buch.-Ham is a plant source for a commonly used traditional Chinese medicinal (TCM) herb Qianliguang. A TCM herbal proprietary product containing Qianliguang as the major herb for the treatment of sinusitis has been used in China for several decades, and has also been exported to other regions and countries worldwide. In the present study, the aqueous extract of S. scandens collected in the Shanxi Province of China was determined, for the first time, to contain hepatotoxic and tumorigenic pyrrolizidine alkaloids (PAs) by using high-performance liquid chromatography/mass spectrometric (HPLC/MS) analysis in various scanning modes. A total of nine toxic and two non-toxic PAs were detected in the aqueous extract of S. scandens, of which six PAs, namely neoplatyphylline, senecionine, senecionine N-oxide, seneciphylline, Seneciphylline N-Oxide and senkirkine, were unequivocally characterized, while other PAs were tentatively assigned as jacobine, jacozine N-oxide (or erucifoline N-oxide), 7-tigloylplatynecine, usaramine and an isomer of yamataimine. The estimated total content of toxic PAs in S. scandens was 10.82 microg/g herb, which was significantly higher than that (> or =1 microg/g herb) recommended by Belgium and Germany not to be used clinically. Among the PAs definitively identified, senecionine, seneciphylline, and senkirkine are known tumorigens capable of inducing liver tumors in experimental animals, while Seneciphylline N-Oxide and senecionine N-oxide are probably tumorigenic due to their potential conversion into seneciphylline and senecionine via metabolic reduction in the body. Thus, the current finding of the presence of toxic/tumorigenic PAs in S. scandens challenges the safety of using this TCM herb and its proprietary products.
Pyrrolizidine alkaloid variation in Senecio vulgaris populations from native and invasive ranges
PeerJ 2017 Aug 14;5:e3686.PMID:28828276DOI:10.7717/peerj.3686.
Biological invasion is regarded as one of the greatest environmental problems facilitated by globalization. Some hypotheses about the invasive mechanisms of alien invasive plants consider the plant-herbivore interaction and the role of plant defense in this interaction. For example, the "Shift Defense Hypothesis" (SDH) argues that introduced plants evolve higher levels of qualitative defense chemicals and decreased levels of quantitative defense, as they are released of the selective pressures from specialist herbivores but still face attack from generalists. Common groundsel (Senecio vulgaris), originating from Europe, is a cosmopolitan invasive plant in temperate regions. As in other Senecio species, S. vulgaris contains pyrrolizidine alkaloids (PAs) as characteristic qualitative defense compounds. In this study, S. vulgaris plants originating from native and invasive ranges (Europe and China, respectively) were grown under identical conditions and harvested upon flowering. PA composition and concentration in shoot and root samples were determined using Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS). We investigated the differences between native and invasive S. vulgaris populations with regard to quantitative and qualitative variation of PAs. We identified 20 PAs, among which senecionine, senecionine N-oxide, integerrimine N-oxide and Seneciphylline N-Oxide were dominant in the roots. In the shoots, in addition to the 4 PAs dominant in roots, retrorsine N-oxide, spartioidine N-oxide and 2 non-identified PAs were also prevalent. The roots possessed a lower PA diversity but a higher total PA concentration than the shoots. Most individual PAs as well as the total PA concentration were strongly positively correlated between the roots and shoots. Both native and invasive S. vulgaris populations shared the pattern described above. However, there was a slight trend indicating lower PA diversity and lower total PA concentration in invasive S. vulgaris populations than native populations, which is not consistent with the prediction of SDH.
[Simultaneous determination of six pyrrolizidine alkaloids in different parts of Emilia sonchifolia by UPLC-MS/MS]
Zhongguo Zhong Yao Za Zhi 2021 Sep;46(17):4456-4461.PMID:34581050DOI:10.19540/j.cnki.cjcmm.20210623.202.
This study aims to develop a UPLC-MS/MS method for simultaneous determination of six pyrrolizidine alkaloids(PAs)--intermedine N-oxide(ImNO), lycopsamine N-oxide(LyNO), seneciphylline(Sp), Seneciphylline N-Oxide(SpNO), senecionine N-oxide(SnNO), and senkirkine(Sk) in different parts of Emilia sonchifolia. UPLC conditions are as follows: ACQUITY UPLC HSS T3 column(2.1 mm×100 mm, 1.8 μm), mobile phase consisting of 0.05% formic acid and 2.5 mmol·L~(-1) ammonium formate in water(A)-0.05% formic acid and 2.5 mmol·L~(-1) ammonium formate in acetonitrile(B) for gradient elution. MS conditions are as below: electrospray ionization(ESI) in the positive ion mode, multiple reaction monitoring(MRM), and the content of the six PAs was calculated with the external standard method. The results suggested the differences in the six PAs among different parts of E. sonchifolia. Sk was detected in all the four parts, with similar content. SnNO also existed in all the four parts, but the content in roots was significantly higher than that in other parts. Sp and SpNO were found in both roots and flowers, with the content higher in the former than in the later. ImNO and LyNO were only found in leaves, and the content was low. Among the six components detected, ImNO, LyNO, and SpNO were found and determined for the first time, which enriched the toxic components and laid a scientific basis for the quality and safety evaluation of E. sonchifolia.
Generation and characterization of monoclonal antibodies against the pyrrolizidine alkaloid retrorsine
Planta Med 1998 Apr;64(3):259-63.PMID:9581524DOI:10.1055/s-2006-957421.
Monoclonal antibodies against retrorsine were established using a retrorsine-hemisuccinate::bovine-thyroglobuline conjugate as antigen for immunization. In competitive enzyme-linked immunoassays the specificity of the obtained antibodies was tested with 20 different pyrrolizidine alkaloids. Among these the alkaloids acetylgynuramine, gynuramine, integerrimine, neoplatyphylline, platyphylline, rosmarinine, senecionine, and seneciphylline were able to bind the antibody. There was no cross-reactivity with the alkaloids senkirkine, angeloyl-heliotridine, heliotridine, axillarine, anacrotine, monocrotaline, madurensine, otosenine, retronecine, tussilagine, triangularine, and jacoline as well as with Seneciphylline N-Oxide. From this antigen spectrum it can be concluded that besides the necic structure itself the dominant and discriminative epitope consists of the exocyclic ethylidene group of the various diesters.