Santonin
(Synonyms: 山道年; Alpha-Santonin) 目录号 : GC38666
A sesquiterpenoid lactone
Cas No.:481-06-1
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
Santonin is a sesquiterpenoid lactone that has been found in Artemisia.1 It has been used as a building block in the synthesis of terpenoids. Santonin is an anthelmintic that induces paralysis of A. lumbricoides.2
1.Banerjee, A.K., Vera, W.J., and Gonzalez, N.C.Synthesis of terpenoid compounds from α-santoninTetrahedron49(122)4761-4788(1993) 2.Hermoso, R., and Monteoliva, M.Survival study of parasitic helminths. III. Effects of antihelminthic and other drugs on survival of Ascaris lumbricoidesRev. Iber. Parasitol.31(4)567-585(1970)
| Cas No. | 481-06-1 | SDF | |
| 别名 | 山道年; Alpha-Santonin | ||
| Canonical SMILES | O=C1[C@@H](C)[C@@](CC[C@@]2(C)C=CC(C(C)=C23)=O)([H])[C@]3([H])O1 | ||
| 分子式 | C15H18O3 | 分子量 | 246.3 |
| 溶解度 | DMSO: 62.5 mg/mL (253.76 mM) | 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 | 4.0601 mL | 20.3004 mL | 40.6009 mL |
| 5 mM | 0.812 mL | 4.0601 mL | 8.1202 mL |
| 10 mM | 0.406 mL | 2.03 mL | 4.0601 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。
Naturally Occurring Sesquiterpene Lactone-Santonin, Exerts Anticancer Effects in Multi-Drug Resistant Breast Cancer Cells by Inducing Mitochondrial Mediated Apoptosis, Caspase Activation, Cell Cycle Arrest, and by Targeting Ras/Raf/MEK/ERK Signaling Pathway
Med Sci Monit 2019 May 18;25:3676-3682.PMID:31101800DOI:10.12659/MSM.915246.
BACKGROUND Sesquiterpene lactones have gained tremendous attention owing to their potent anticancer properties. The main focus of this study was to evaluate the anticancer effects of a naturally occurring sesquiterpene lactone, Santonin, against human breast cancer SK-BR-3 cells. MATERIAL AND METHODS Cell counting kit 8 assay was used for the determination of cell viability. Apoptosis was detected by DAPI (4',6-diamidino-2-phenylindole) and annexin V/propidium iodide (IP) staining. Flow cytometry was used for cell cycle analysis and western blotting was used for the estimation of protein expression. RESULTS Results showed that Santonin exerts significant anti-proliferative effects on the SK-BR-3 breast cancer cells in a concentration dependent manner. Santonin showed an IC₅₀ of 16 µM against SK-BR-3 cells. DAPI staining showed that Santonin caused DNA fragmentation in the SK-BR-3 cells, which is indicative of apoptosis. Annexin V/PI staining showed that apoptotic cell percentage increased up to 34.32% at 32 µM concentration of Santonin. Santonin also caused an increase in the expression of Bax, caspase-3, and caspase-9, and a decrease in the expression of Bcl-2. Santonin also caused the arrest of the SK-BR-3 cells at the G2/M phase of the cell cycle and suppressed the expression of cyclin A and B1. Finally, Santonin could also block the Raf/MEK/ERK pathway in breast cancer cells. CONCLUSIONS The findings of this study suggest the potential for the naturally occurring sesquiterpene lactone Santonin in breast cancer treatment and also suggest that it could be developed as a promising anticancer agent.
Transformation of Santonin to a Naproxen Analogue with Anti-Inflammatory Activity
J Nat Prod 2019 Jun 28;82(6):1710-1713.PMID:31125226DOI:10.1021/acs.jnatprod.8b00318.
Santonin, a natural product, was aromatized with molecular iodine as the catalyst. The new compound was characterized as ( S)-methyl-2-(7-hydroxy-5,8-dimethylnaphthalen-2-yl) propanoate (2) based on 2D NMR spectroscopic data. Structurally, compound 2 was highly similar to the anti-inflammatory drug naproxen. The new naproxen analogue had significant potency against cyclooxygenase 1 and 2 (IC50 = 31.0 and 66.1 μM, respectively).
Pharmacological Evaluation of Artemisia cina Crude CO2 Subcritical Extract after the Removal of Santonin by Means of High Speed Countercurrent Chromatography
Molecules 2020 Jun 12;25(12):2728.PMID:32545512DOI:10.3390/molecules25122728.
Artemisia species are highly important due to their economic significance as medicines, fodder and food. Artemisia cina is an endemic species to Kazakhstan. In folk medicine, water extract of A. cina was used in the treatment of bronchial asthma while the alcohol extract has larvicidal and antituberculosis activity. The most common and most extensively studied compound from this species is the terpenoid Santonin. The toxicity of this compound occurs at the doses of 60 mg for children and 200 mg for adults causing among other issues xanthopsia, leading to blindness. Having this in mind, the main idea of this work was to remove Santonin from the crude extract and to check if the santonin-free extract would still be of any pharmacological importance. A CO2 subcritical extract was chromatographed using high-speed countercurrent chromatography (HSCCC) for the removal of Santonin. The santonin-free CO2 subcritical extract (SFCO2E) as well as the isolated compound pectolinarigenin, a flavonoid, were assessed for their pharmacological actions. From the results obtained we can safely suggest that HSCCC is an efficient methodology to completely remove Santonin from the CO2 subcritical extract. It was also possible to observe promising antinociceptive and anti-inflammatory activities for both SFCO2E and pectolinarigenin at concentrations that can justify the production of a phytomedicine with this endemic plant from Kazakhstan.
Antipyretic activity of alpha- and beta-santonin
J Ethnopharmacol 1988 Jul-Aug;23(2-3):285-90.PMID:3193791DOI:10.1016/0378-8741(88)90007-4.
The antipyretic activity of two sesquiterpene lactones, beta-santonin and arsubin, isolated from the lipid fraction of Artemisia coerulescens subsp. gallica was determined in rats along with the activity of alpha-santonin. In its alpha- and beta-forms, Santonin caused a decrease in the body temperature of rats made febrile by the subcutaneous injection of beer yeast. This decrease, more pronounced in the case of beta-santonin, was dose-dependent and antagonized by pretreatment with haloperidol, an agent that also opposes the antipyretic activity of dopamine. These findings seem to show that the alpha- and beta-forms of Santonin act on rectal temperature in a way similar to dopamine.
Photoinduced Rearrangement of Dienones and Santonin Rerouted by Amines
Angew Chem Int Ed Engl 2018 Jan 22;57(4):904-908.PMID:29266649DOI:10.1002/anie.201710463.
The photoinduced rearrangement pathways of simple 2,5-dienones and the natural product Santonin were found to be effectively rerouted by amines, giving rise to unprecedented products. Either cis olefins or cyclobutenes were obtained from 4,4-disubstituted 2,5-dienone upon irradiation (365 nm) in the presence of various amines depending on the solvent. Previously undescribed [4.4.0] and [5.3.0] fused-ring-containing products were obtained when Santonin was irradiated (365 nm) in the presence of methylamine. The amines present in these reactions were incorporated into the products by means of amide-group formation.