Silybin B
(Synonyms: 水飞蓟宾B) 目录号 : GC37639
Silybin B 是从 Silybum marianum 中分离出的一种黄酮木脂素，具有抗肿瘤活性。Silybin B 是水飞蓟素最有效的抗纤维原性和抗低聚物成分，是一种有前景的抗阿尔茨海默病药物候选。
Cas No.:142797-34-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Silybin B, a flavonolignan separated from Silybum marianum, has anti-tumor activity. Silybin B is the most potent antifibrillogenic and anti-oligomeric component of silymarin and proposes it as a promising anti Alzheimer's disease drug candidate[1][2].
[1]. An-Shen Lin, et al. Cancer Preventive Agents. 7. Antitumor-Promoting Effects of Seven Active Flavonolignans from Milk Thistle (Silybum marianum.) on Epstein-Barr Virus Activation, Pharmaceutical Biology, 45:10, 735-738. [2]. Sciacca MFM, et al. Inhibition of Aβ Amyloid Growth and Toxicity by Silybins: The Crucial Role of Stereochemistry. ACS Chem Neurosci. 2017 Aug 16;8(8):1767-1778.
| Cas No. | 142797-34-0 | SDF | |
| 别名 | 水飞蓟宾B | ||
| Canonical SMILES | O=C1[C@H](O)[C@@H](C2=CC=C(O[C@@H](CO)[C@H](C3=CC=C(O)C(OC)=C3)O4)C4=C2)OC5=CC(O)=CC(O)=C15 | ||
| 分子式 | C25H22O10 | 分子量 | 482.44 |
| 溶解度 | DMSO : 250 mg/mL (518.20 mM; Need ultrasonic) | 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 | 2.0728 mL | 10.364 mL | 20.728 mL |
| 5 mM | 0.4146 mL | 2.0728 mL | 4.1456 mL |
| 10 mM | 0.2073 mL | 1.0364 mL | 2.0728 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。
Silybin B exerts protective effect on cisplatin-induced neurotoxicity by alleviating DNA damage and apoptosis
J Ethnopharmacol 2022 Apr 24;288:114938.PMID:34999144DOI:10.1016/j.jep.2021.114938.
Ethnopharmacological relevance: Silybum marianum is a traditional Chinese medicine that has been used for treating liver disease. Silybin consisting of silybin A and Silybin B, is a member of Silybum marianum, and exerts a therapeutic effect on many diseases. However, the protective effect of silybin on cisplatin-induced neurotoxicity and the stereoisomer contributing to the effect remain unknown. Aim of the study: The present study aimed to study the effect of silybin on cisplatin-induced neuronal injury, compare the difference of protective effect between silybin A and Silybin B, and the potential mechanism. Materials and methods: High performance liquid chromatography (HPLC) was used to separate silybin A and Silybin B. X-ray crystallographic analysis in combination with experimental and calculated ECD were performed to identify the structure of silybin A and Silybin B. The toxicity of the silybin or cisplatin against murine hippocampal neuronal HT22 cells was determined through MTT assay. The cell cycle and cell apoptosis were measured by PI staining and Annexin V-FITC/PI staining, respectively, and then subjected to flow cytometry. Western blot analysis was conducted to quantify the expression of proteins related to apoptosis and DNA damage. Immunofluorescence was used to evaluate the expression of DNA damage marker. In vivo experiment, the behavioral analysis was determined through pole test, swimming test and Morris water maze test. The index of superoxide dismutase (SOD), reduced glutathione (GSH), total antioxidant capacity (T-AOC) and lipid peroxidation (LPO) were examined to evaluate the antioxidant capacity in mice brain. Nissl staining and Tunel assay were used to detect the neuronal viability and apoptosis in hippocampus. Results: We successfully separated and identified silybin A and Silybin B. We found both silybin A and Silybin B alleviated cisplatin-induced apoptosis and cell cycle arrest in HT22 cells, and Silybin B was more effective. We chose Silybin B for further mechanism investigation, and found Silybin B alleviated DNA damage by enhancing phosphorylation of ATR and decreasing expression of γ-H2AX. In the in vivo experiment, we observed that Silybin B markedly improved the behavioral abnormalities in cisplatin-treated mice, reduced LPO level while increased SOD, GSH and T-AOC in mice brain tissue. Nissl staining and Tunel assay showed that Silybin B alleviated cisplatin-induced hippocampal damage. Conclusions: These results suggest that Silybin B might serve as a promising drug candidate in mitigating cisplatin-induced neural injury in the brain and thereby improving the chemotherapeutic outcomes.
Chemistry of silybin
Nat Prod Rep 2014 Sep;31(9):1138-57.PMID:24977260DOI:10.1039/c3np70122k.
Silybin, a secondary metabolite isolated from the seeds of the blessed milk thistle (Silybum marianum) was discovered as the first member of a new family of natural compounds called flavonolignans in 1959. Over the years it has received the research attention of many organic chemists. This research has resulted in a number of semisynthetic derivatives prepared in an effort to modulate and better target the biological activities of silybin or to improve its physical properties, such as its solubility. A fundamental breakthrough in silybin chemistry was the determination of the absolute configurations of silybin A and Silybin B, and the development of methods for their separation. This review covers articles dealing with silybin chemistry and also summarizes all the derivatives prepared.
Relative Bioavailability of Silybin A and Silybin B From 2 Multiconstituent Dietary Supplement Formulations Containing Milk Thistle Extract: A Single-dose Study
Clin Ther 2018 Jan;40(1):103-113.e1.PMID:29273470DOI:10.1016/j.clinthera.2017.11.013.
Purpose: The purpose of this study was to compare the bioavailability between 2 milk thistle-containing dietary supplements, Product B and IsaGenesis, in healthy volunteers. Methods: Bioavailability between Product B, originally formulated as a powdered capsule, and IsaGenesis, reformulated as a soft gel, were compared by measuring silybin A and Silybin B as surrogate pharmacokinetic markers for differences in absorption and bioavailability. For this randomized, open-label, crossover pharmacokinetic study, 12 healthy volunteers consumed a single-dose serving of each supplement separated by at least a 7-day washout period. Serial blood samples were obtained at 0, 0.5, 1, 1.5, 2, 3, 4, 6, and 8 hours and analyzed via LC-MS/MS. Findings: Rapid absorption and elimination of silybin A and Silybin B have been observed after oral administration of both Product B and IsaGenesis. However, the absorption rate and extent, as indicated by mean the Cmax and mean plasma AUC, were significantly higher for the IsaGenesis soft gel formulation. The dose-corrected mean Cmax was 365% and 450% greater for silybin A and B, respectively, relative to powdered Product B. The time to Tmax was reached, on average, at least 1 hour earlier with IsaGenesis relative to Product B for both silybin A and Silybin B. Implications: The IsaGenesis soft gel formulation provided substantially greater absorption and bioavailability of silybin A and Silybin B relative to the powdered Product B supplement. ClinicalTrials.gov Identifier: NCT02529605.
Silybin B and Cianidanol Inhibit Mpro and Spike Protein of SARS-CoV-2: Evidence from in silico Molecular Docking Studies
Curr Pharm Des 2021;27(32):3476-3489.PMID:33302853DOI:10.2174/1381612826666201210122726.
Background: The main proteases (Mpro) and Spike Proteins (SP) of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2) play a major role in viral infection development by producing several non-structural proteins (nsPs) and penetrating the host cells, respectively. In this study, the potential of in silico molecular docking-based drug repositioning approach was exploited for identifying the inhibitors of Mpro and SP of SARS-CoV-2. Methods: A total of 196 compounds, including various US-FDA-approved drugs, vitamins, and their analogs, were docked with Mpro (PDB IDs: 6YB7 and 6Y84), and the top six ligands were further tested for ADME properties, followed by docking with SP (PDB IDs: 6LXT and 6W41). Results: Out of 196 compounds, binding energy (DE) of Silybin B (6YB7: DE: -11.20 kcal/mol; 6Y84: DE: - 10.18 kcal/mol; 6LXT: DE: -10.47 kcal/mol; 6W41: DE: -10.96 kcal/mol) and Cianidanol (6YB7: DE: -8.85 kcal/mol; 6LXT: DE: -9.36 kcal/mol; 6Y84: DE: -10.02 kcal/mol; 6W41: DE: -9.52 kcal/mol) demonstrated better binding and ADME properties compared with the currently endeavored drugs like Hydroxychloroquine and Lopinavir. Additionally, Elliptinone, Diospyirin, SCHEMBL94263, and Fiboflavin have shown encouraging results. Fiboflavin, an immunity booster, was found to inhibit both the Mpro and spike protein of SARSCoV- 2. It was observed that amino acid residues MET6, ALA7, PHE8, PRO9, ASP295, GLY302, VAL303, and THR304 play significant roles in protein-ligand interactions through hydrogen bonds and Vander Waals forces. Conclusion: Silybin B and Cianidanol showed excellent binding and ADME properties compared with the currently endeavored drugs and can be exploited as therapeutic options against SARS-CoV-2 infection after experimental validation and clinical trials.
A comparison of the diastereoisomers, silybin A and Silybin B, on the induction of apoptosis in K562 cells
Nat Prod Commun 2011 Nov;6(11):1653-6.PMID:22224281doi
Two diastereoisomers of silybin, silybin A and Silybin B, were separated from silymarin by HPLC in our previous study. The present study assessed the effects of the diastereoisomers on cell apoptosis, and compared these with their mixture, silybin, in human chronic myeloid leukemia K562 cells. Both isomers showed stronger effects on cell growth inhibition and apoptosis induction than silybin. Compared with Silybin B, silybin A showed higher effects on the production of intracellular reactive oxygen species and Ca2+. These results suggest that silybin A and Silybin B have similar potency on apoptosis induction with different oxidative effects. Antagonistic effects may exist between silybin A and Silybin B, partially through ROS production and Ca2+ increase.