水飞蓟宾
| 中文名称 | 水飞蓟宾 |
|---|---|
| 中文同义词 | (2R,3R)-3,5,7-三羟基-2-[(2R,3R)-3-(4-羟基-3-甲氧基苯基)-2-羟甲基-2,3-二氢苯并[1,4]二英-6-基]苯并二氢吡喃-4-酮;水飞蓟宾(A + B混合物);(2R,3R)-3,5,7-三羟基-2-(3-(4-羟基-3-甲氧基苯基)-2-(羟甲基)-2,3-二氢苯并[B][1,4]二噁烷-6-基)苯并二氢吡喃-4-酮;化合物 SILYBIN |
| 英文名称 | Silybin |
| 英文同义词 | Silybin A,B (Mixture);Silybin (Mixture of Diastereomers);4H-1-Benzopyran-4-one, 2-[2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-;(2R,3R)-3,5,7-Trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one |
| CAS号 | 802918-57-6 |
| 分子式 | C25H22O10 |
| 分子量 | 482.44 |
| EINECS号 | 806-403-5 |
| 相关类别 | 科研原料;对照品;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals |
| Mol文件 | 802918-57-6.mol |
| 结构式 |  |
水飞蓟宾 性质
| 熔点 | 152-153°C |
|---|---|
| 沸点 | 793.0±60.0 °C(Predicted) |
| 密度 | 1.527±0.06 g/cm3(Predicted) |
| 储存条件 | Refrigerator |
| 溶解度 | 丙酮（少量，超声处理，加热），DMSO（少量溶解），甲醇（少量，加热） |
| 酸度系数(pKa) | 7.39±0.60(Predicted) |
| 形态 | 固体 |
| 颜色 | 淡黄色至米色 |
| InChIKey | SEBFKMXJBCUCAI-DBMPWETRSA-N |
| SMILES | [C@H]1(C2=CC=C3OC(CO)C(C4=CC=C(O)C(OC)=C4)OC3=C2)OC2=CC(O)=CC(O)=C2C(=O)[C@@H]1O |
水飞蓟宾属于黄酮木脂素类化合物，从水飞蓟Silybum marianum (L.)Gaertn.的种子中提取分离得到。水飞蓟宾由2种非对映异构体水飞蓟宾A（2R,3R,10R,11R）和水飞蓟宾B（2R,3R,10S,11S）等比例混合组成，具有多种生物活性，尤为突出的是保护肝脏和清除自由基的作用。类白色结晶性粉末，无臭，味微苦涩。有引湿性，不溶于水，溶于丙酮，略溶于甲醇、乙醇，难溶于氯仿，易溶于稀碱溶液。其葡甲胺易溶于水。本品系从菊科水飞蓟属植物水飞蓟果实中提取分离的一种黄酮类化合物。口服吸收良好,达峰时间约1.5h，口服后48h排出量约为20%，其中80%以代谢物形式由胆汁排出，其余大部分以原形从尿中排出。水飞蓟宾能够稳定肝细胞膜，保护肝细胞的酶系统，清除肝细胞内的活性氧自由基，从而提高肝脏的解毒能力，避免肝细胞长期接触毒物。 经实验结果表明，对四氯化碳、毒蕈碱等肝脏毒物引起的各种类型肝损伤具有不同程度的保护和治疗作用，并对四氯化碳引起的丙氨酸氨基转移酶的升高有一定的阻止作用。水飞蓟宾是一种来自于天然植物的类黄酮物质，水飞蓟宾被证明可以抑制细胞增殖和诱导细胞凋亡，同时具有抗血管生成的特性。肿瘤细胞凋亡的诱导是由内质网应激介导的。水飞蓟宾起着STAT3靶向抑制剂的作用以及抑制免疫检查点PD-L1和EMT的调节作用，是一种有前途的NSCLC佐剂。也有文献证明通过下调肌动蛋白细胞骨架和PI3K / Akt分子通路抑制癌细胞。多项研究表明，水飞蓟宾通过与肿瘤抑制基因p53相互作用发挥其保护作用。Silybin 是一种从草蓟 (Silybum marianum) 种子中分离出来的黄素寡糖。Silybin 诱导凋亡 (apoptosis)，并具有保肝，抗氧化，抗炎，抗癌活性。
Silybin (0-200 mM; for 72 hours) has growth inhibition in a time- and dose-dependent manner.
Silybin (68 μM; for 72 hours) induces apoptosis and increases the cells in G1-phase of ~22%.
Silybin (68 μM; for 72 hours) induces AKT activity inhibition.
Cell Viability Assay
| Cell Line: | HepG2 cell growth |
| Concentration: | 0-200 mM |
| Incubation Time: | For 72 hours |
| Result: | Had growth inhibition in a time- and dose-dependent manner with an IC 50 of 68 μM. |
Apoptosis Analysis
| Cell Line: | HepG2 cell growth |
| Concentration: | 68 μM |
| Incubation Time: | For 72 hours |
| Result: | Induced apoptosis in a higher number of cells (60%) when compared to untreated cells. |
Cell Cycle Analysis
| Cell Line: | HepG2 cell growth |
| Concentration: | 68 μM |
| Incubation Time: | For 72 hours |
| Result: | Increased the cells in G1-phase of ~22% and decreased of 47% the cells in S-phase. |
Western Blot Analysis
| Cell Line: | HepG2 cell growth |
| Concentration: | 68 μM |
| Incubation Time: | For 72 hours |
| Result: | Induced AKT activity inhibition. |
Silybin (50, 100 mg/kg/day; given intragastrically for the last 4 weeks) significantly lowers both serum and hepatic lipid accumulation.
| Animal Model: | Male C57BL/6J mice (6-8 weeks old) with nonalcoholic fatty liver disease (NAFLD) |
| Dosage: | 50, 100 mg/kg |
| Administration: | Given intragastrically; daily; for the last 4 weeks |
| Result: | Significantly lowered both serum and hepatic lipid accumulation. |
用途
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