京尼平
| 中文名稱 | 京尼平 |
|---|---|
| 中文同義詞 | (1S,2R,6S)-2-羥基-9-(羥甲基)-3-氧代二環(huán)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、梔子苷元);GENIPIN 京尼平;格尼泊素,GENIPIN;京尼平(梔子苷元,格尼泊素);京尼平, ≥98% (HPLC), POWDER |
| 英文名稱 | Genipin |
| 英文同義詞 | 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號(hào) | 6902-77-8 |
| 分子式 | C11H14O5 |
| 分子量 | 226.23 |
| EINECS號(hào) | 636-196-5 |
| 植物來(lái)源 | 梔子 |
| 相關(guān)類別 | 科研試劑;對(duì)照品;小分子抑制劑;中藥對(duì)照品;標(biāo)準(zhǔn)品;植物提取物;細(xì)胞生物學(xué);小分子抑制劑，天然產(chǎn)物;細(xì)胞信號(hào)和神經(jīng)生物學(xué);植物化學(xué)藥;植物成分單體;分析對(duì)照品;標(biāo)準(zhǔn)品-中藥標(biāo)準(zhǔn)品;原料;有機(jī)原料;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;特色原料;標(biāo)準(zhǔn)品 -中藥標(biāo)準(zhǔn)品;環(huán)烯醚萜;標(biāo)準(zhǔn)品，對(duì)照品;天然高含量單體;化工原料;科研原料;醫(yī)藥原料;生物化工 |
| Mol文件 | 6902-77-8.mol |
| 結(jié)構(gòu)式 |  |
京尼平 性質(zhì)
| 熔點(diǎn) | 118.0 to 123.0 °C |
|---|---|
| 沸點(diǎn) | 287.83°C (rough estimate) |
| 密度 | 1.1230 (rough estimate) |
| 折射率 | 1.4720 (estimate) |
| 儲(chǔ)存條件 | Inert atmosphere,Room Temperature |
| 溶解度 | 二甲基亞砜：≥25mg/mL |
| 形態(tài) | 粉末 |
| 酸度系數(shù)(pKa) | 12.06±0.60(Predicted) |
| 顏色 | 白色到近乎白色 |
| 最大波長(zhǎng)(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 數(shù)據(jù)庫(kù) | 6902-77-8(CAS DataBase Reference) |
京尼平的制備方法一般采用從梔子中提取京尼平苷，再用β－葡萄糖苷酶水解，然后用乙醚萃取、真空濃縮、重結(jié)晶而制得，也可以采用微生物轉(zhuǎn)化法制備。
Genipin ((+)-Genipin) 是衍生自 Gardenia jasminoides Ellis 果實(shí)的天然交聯(lián)劑。Genipin 抑制細(xì)胞中的 UCP2 (解偶聯(lián)蛋白 2)。Genipin 具有多種生物活性，包括蛋白質(zhì)調(diào)節(jié)，抗腫瘤，抗炎癥，免疫抑制，抗血栓形成和對(duì)海馬神經(jīng)元的保護(hù)。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
| 危險(xiǎn)品標(biāo)志 | Xn |
|---|---|
| 危險(xiǎn)類別碼 | 22 |
| 安全說(shuō)明 | 3/14-36/37/39 |
| 危險(xiǎn)品運(yùn)輸編號(hào) | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS號(hào) | GY5828000 |
| 危險(xiǎn)等級(jí) | 6.1 |
| 包裝類別 | III |
| 海關(guān)編碼 | 29329990 |