Seselin
(Synonyms: 邪蒿素) 目录号 : GC46221
An angular pyranocoumarin with diverse biological activities
Cas No.:523-59-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Seselin is an angular pyranocoumarin that has been found in M. semecarpifolia and has diverse biological activities.1,2,3,4 It is cytotoxic to P388 and HT-29 cells in vitro (EC50s = 8.66 and 9.94 μg/ml).1 Seselin (0.5, 4.5, and 40.5 mg/kg) reduces acetic acid-induced writhing in mice.2 It also reduces paw licking in the first and second phases of the formalin test in mice when administered 30 minutes prior to formalin. Seselin (3, 10, and 30 mg/kg) decreases serum levels of IL-1β, IL-6, and TNF-α in a mouse model of sepsis induced by cecal ligation and puncture and increases survival when administered at a dose of 30 mg/kg.3 It reduces ear edema induced by phorbol 12-myristate 13-acetate in mice (ED45 = 0.25 mg/ear).4
|1. Chou, H.-C., Chen, J.-J., Duh, C.-Y., et al. Cytotoxic and anti-platelet aggregation constituents from the root wood of Melicope semecarpifolia. Planta Med. 71(11), 1078-1081 (2005).|2. Lima, V., Silva, C.B., Mafezoli, J., et al. Antinociceptive activity of the pyranocoumarin seselin in mice. Fitoterapia 77(7-8), 574-578 (2006).|3. Feng, L., Sun, Y., Song, P., et al. Seselin ameliorates inflammation via targeting Jak2 to suppress the proinflammatory phenotype of macrophages. Br. J. Pharmacol. 176(2), 317-333 (2019).|4. GarcÍa-ArgÁez, A.N., RamÍrez Apan, T.O., Parra Delgado, H., et al. Anti-inflammatory activity of coumarins from Decatropis bicolor on TPA ear mice model. Planta Med. 66(3), 279-281 (2000).
| Cas No. | 523-59-1 | SDF | |
| 别名 | 邪蒿素 | ||
| Canonical SMILES | O=C1C=CC(C=CC2=C3C=CC(C)(C)O2)=C3O1 | ||
| 分子式 | C14H12O3 | 分子量 | 228.2 |
| 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 | 4.3821 mL | 21.9106 mL | 43.8212 mL |
| 5 mM | 0.8764 mL | 4.3821 mL | 8.7642 mL |
| 10 mM | 0.4382 mL | 2.1911 mL | 4.3821 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。
Seselin ameliorates inflammation via targeting Jak2 to suppress the proinflammatory phenotype of macrophages
Br J Pharmacol 2019 Jan;176(2):317-333.PMID:30338847DOI:10.1111/bph.14521.
Background and purpose: Sepsis is a serious clinical condition with a high mortality rate. Anti inflammatory agents have been found to be beneficial for the treatment of sepsis. Here, we have evaluated the anti-inflammatory activity of Seselin in models of sepsis and investigated the underlying molecular mechanism(s). Experimental approach: In vivo therapeutic effects of Seselin was evaluated in two models of sepsis, caecal ligation and puncture or injection of LPS, in C57BL/6 mice. In vitro, anti-inflammatory activity of Seselin was assessed with macrophages stimulated with LPS and IFN-γ. Anti inflammatory actions were analysed with immunohistochemical methods, ELISA and Western blotting. Flow cytometry was used to assess markers of macrophage phenotype (pro- or anti-inflammatory). Other methods used included co-immunoprecipitation, cellular thermal shift assay and molecular docking. Key results: In vivo, Seselin clearly ameliorated sepsis induced by caecal ligation and puncture. In lung tissue from septic mice and in cultured macrophages, Seselin down-regulated levels of proinflammatory factors and activity of STAT1 and p65, the master signal pathway molecules for polarization of macrophages into the proinflammatory phenotype. Importantly, adoptive transfer of bone marrow-derived macrophages, pretreated with Seselin, lowered systemic proinflammatory factors in mice challenged with LPS. The underlying mechanism was that Seselin targeted Jak2 to block interaction with IFNγ receptors and downstream STAT1. Conclusions and implications: Seselin exhibited anti-inflammatory activity through its action on Jak2. These results indicated a possible application of Seselin to the treatment of inflammatory disease via blocking the development of the proinflammatory phenotype of macrophages.
Seselin from Plumbago zeylanica inhibits phytohemagglutinin (PHA)-stimulated cell proliferation in human peripheral blood mononuclear cells
J Ethnopharmacol 2008 Sep 2;119(1):67-73.PMID:18577441DOI:10.1016/j.jep.2008.05.032.
Effects of Seselin (C(14)H(12)O(3); MW 228) identified from Plumbago zeylanica on phytohemagglutinin (PHA)-stimulated cell proliferation were studied in human peripheral blood mononuclear cells (PBMC). The data demonstrated that Seselin inhibited PBMC proliferation-activated with PHA with an IC(50) of 53.87+/-0.74 microM. Cell viability test indicated that inhibitory effects of Seselin on PBMC proliferation were not through direct cytotoxicity. The action mechanisms of Seselin may involve the regulation of cell cycle progression, interleukin-2 (IL-2) and interferon-gamma (IFN-gamma) production in PBMC. Since cell cycle analysis indicated that Seselin arrested the cell cycle progression of activated PBMC from the G(1) transition to the S phase. Seselin suppressed IL-2 and IFN-gamma production in a concentration-dependent manner. Furthermore, Seselin significantly decreased the IL-2 and IFN-gamma gene expression in PHA-activated PBMC. Therefore, results elucidated for the first time that Seselin is likely an immunomodulatory agent for PBMC.
Inhibition of multiple SARS-CoV-2 proteins by an antiviral biomolecule, Seselin from Aegle marmelos deciphered using molecular docking analysis
J Biomol Struct Dyn 2022;40(21):11070-11081.PMID:34431451DOI:10.1080/07391102.2021.1955009.
Our earlier experimental and computational report produced evidence on the antiviral nature of the compound Seselin purified from the leaf extracts of Aegle marmelos against Bombyx mori Nuclear Polyhedrosis Virus (BmNPV). In the pandemic situation of COVID-19 caused by the SARS-COV-2 virus, an in silico effort to evaluate the potentiality of the Seselin was made to test its efficacy against multiple targets of SARS-COV-2 such as spike protein S2, COVID-19 main protease and free enzyme of the SARS-CoV-2 (2019-nCoV) main protease. The ligand Seselin showed the best interaction with receptors, spike protein S2, COVID-19 main protease and free enzyme of the SARS-CoV-2 (2019-nCoV) main protease with a binding energy of -6.3 kcal/mol, -6.9 kcal/mol and -6.7 kcal/mol, respectively. Docking analysis with three different receptors identified that all the computationally predicted lowest energy complexes were stabilized by intermolecular hydrogen bonds and stacking interactions. The amino acid residues involved in interactions were ASP1184, GLU1182, ARG1185 and SER943 for spike protein, SER1003, ALA958 and THR961 for COVID-19 main protease, and for SARS-CoV-2 (2019-nCoV) main protease, it was THR111, GLN110 and THR292. The MD simulation and MM/PBSA analysis showed that the compound Seselin could effectively bind with the target receptors. The outcome of pharmacokinetic analysis suggested that the compound had favourable drugability properties. The results suggested that the Seselin had inhibitory potential over multiple SARS-COV-2 targets and hold a high potential to work effectively as a novel drug for COVID-19 if evaluated in experimental setups in the foreseeable future. Communicated by Ramaswamy H. Sarma.
Antinociceptive activity of the pyranocoumarin Seselin in mice
Fitoterapia 2006 Dec;77(7-8):574-8.PMID:17055189DOI:10.1016/j.fitote.2006.09.005.
Seselin an angular pyranocoumarin at dose of 0.5, 4.5 or 40.5 mg/kg inhibited the writhing response induced by acetic acid in a significant and dose-dependent manner, by 19.5%, 26.2% and 41.4%, respectively. Using the same doses, Seselin elicited a significant inhibition of formalin response during the second phase (inflammatory), by 90.3%, 97.8% and 95.3%, respectively. Besides, a significant reduction of licking time was observed during the first phase (neurogenic) at the highest doses of Seselin, by 34.4% and 66.9%, respectively. On the contrary, in the hot plate test no effect was observed after Seselin treatment. In conclusion, Seselin was able to inhibit inflammatory hyperalgesia, suggesting that this natural product possesses both important peripheral anti-inflammatory and antinociceptive properties.
Crystal structure of tetra-hydro-seselin, an angular pyran-ocoumarin
Acta Crystallogr E Crystallogr Commun 2017 Jul 4;73(Pt 8):1117-1120.PMID:28932418DOI:10.1107/S205698901700932X.
In the title compound, tetra-hydro-seselin, C14H16O3, a pyran-ocoumarin [systematic name: 8,8-dimethyl-3,4,9,10-tetra-hydro-2H,8H-pyrano[2,3-f]chromen-2-one] obtained from the hydrogenation of Seselin in the presence of Pd/C in MeOH at room temperature, the dihedral angle between the central benzene ring and the best planes of the outer fused ring systems are 6.20 (7) and 10.02 (8)°. In the crystal, mol-ecules show only very weak inter-molecular C-H⋯O inter-actions.