京尼平
| 中文名称 | 京尼平 |
|---|---|
| 中文同义词 | (1S,2R,6S)-2-羟基-9-(羟甲基)-3-氧代二环丙[4.3.0]壬-4,8-二烯-5-甲酸甲酯;京尼平;格尼泊素;京尼平(格尼泊素、尼泊素、栀子苷元);GENIPIN 京尼平;格尼泊素,GENIPIN;京尼平(栀子苷元,格尼泊素);京尼平, ≥98% (HPLC), POWDER |
| 英文名称 | Genipin |
| 英文同义词 | Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate;cyclopenta(c)pyran-4-carboxylicacid,1,4a-alpha,5,7a-alpha-tetrahydro-1-hydrox;GENIPIN;1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester;Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate;(1R)-1,4aα,5,7aα-Tetrahydro-1-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester;(1R)-1,4aα,5,7aα-Tetrahydro-1α-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester;Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona- |
| CAS号 | 6902-77-8 |
| 分子式 | C11H14O5 |
| 分子量 | 226.23 |
| EINECS号 | 636-196-5 |
| 植物来源 | 栀子 |
| 相关类别 | 科研试剂;对照品;小分子抑制剂;中药对照品;标准品;植物提取物;细胞生物学;小分子抑制剂，天然产物;细胞信号和神经生物学;植物化学药;植物成分单体;特色原料;分析对照品;标准品-中药标准品;原料;有机原料;标准品 -中药标准品;环烯醚萜;标准品，对照品;天然高含量单体;化工原料;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;科研原料;医药原料;生物化工 |
| Mol文件 | 6902-77-8.mol |
| 结构式 |  |
京尼平 性质
| 熔点 | 118.0 to 123.0 °C |
|---|---|
| 沸点 | 287.83°C (rough estimate) |
| 密度 | 1.1230 (rough estimate) |
| 折射率 | 1.4720 (estimate) |
| 储存条件 | Inert atmosphere,Room Temperature |
| 溶解度 | 二甲基亚砜：≥25mg/mL |
| 形态 | 粉末 |
| 酸度系数(pKa) | 12.06±0.60(Predicted) |
| 颜色 | 白色到近乎白色 |
| 最大波长(λmax) | 240nm(MeOH)(lit.) |
| InChI | InChI=1S/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1 |
| InChIKey | AZKVWQKMDGGDSV-BCMRRPTOSA-N |
| SMILES | [C@@H]1(O)OC=C(C(OC)=O)[C@@]2([H])CC=C(CO)[C@@]12[H] |
| CAS 数据库 | 6902-77-8(CAS DataBase Reference) |
京尼平的制备方法一般采用从栀子中提取京尼平苷，再用β－葡萄糖苷酶水解，然后用乙醚萃取、真空浓缩、重结晶而制得，也可以采用微生物转化法制备。
Genipin ((+)-Genipin) 是衍生自 Gardenia jasminoides Ellis 果实的天然交联剂。Genipin 抑制细胞中的 UCP2 (解偶联蛋白 2)。Genipin 具有多种生物活性，包括蛋白质调节，抗肿瘤，抗炎症，免疫抑制，抗血栓形成和对海马神经元的保护。Genipin 也可用于 2 型糖尿病研究。
Genipin increases mitochondrial membrane potential, increased ATP levels, closed KATP channels, and stimulated insulin secretion in pancreatic islet cells. Genipin causes suppression of insulin signal transduction through hyperactivation of c-Jun N-terminal kinase (JNK) and subsequent serine phosphorylation of insulin receptor substrate-1 (IRS-1), thus impairing insulin-stimulated glucose uptake in 3T3-L1 adipocytes.
Genipin activates IRS-1, PI3-K, and downstream signaling pathway and increases concentrations of calcium, resulting in glucose transporter 4 (GLUT4) translocation and glucose uptake increase in C2C12 myotubes.
Cytochrome c content increases significantly in the cytosol of Genipin-treated FaO cells. Activation of caspase-3 and caspase-7 is ultimately responsible for Genipin-induced apoptotic process in hepatoma cells. ROS level notably increases in Hep3B cells treated with 200 μM Genipin.
安全信息
| 危险品标志 | Xn |
|---|---|
| 危险类别码 | 22 |
| 安全说明 | 3/14-36/37/39 |
| 危险品运输编号 | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS号 | GY5828000 |
| 危险等级 | 6.1 |
| 包装类别 | III |
| 海关编码 | 29329990 |
| 更新日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
|---|---|---|---|---|---|
| 2024/01/25 | HY-17389 | Genipin | 25 mg | 544元 | |
| 2024/01/25 | HY-17389 | 京尼平 Genipin | 6902-77-8 | 10mM * 1mLin DMSO | 598元 |