三七叶苷 | 88105-29-7

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 三七叶苷
• 中文别名: 三七总苷；灯盏细辛浸膏粉；三七总皂苷
• 英文名称: notoginsenoside Fe
• 英文别名: ginsenoside Mb；Notoginsenoside Fe；(2R,3R,4S,5S,6R)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-methylhept-5-en-2-yl]-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 88105-29-7
• 化学式: C₄₇H₈₀O₁₇
• 分子量: 917.142
• InChiKey: MYBAONSAUGZRAX-UBQYYSLZSA-N

物化性质

• 沸点：
  994.1±65.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  64
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  278
• 氢给体数：
  11
• 氢受体数：
  17

制备方法与用途

生物活性

三七皂苷Fe（Notoginsenoside Fe）是从珠子参变种中分离出的天然化合物。这种白色结晶粉末可溶于甲醇、乙醇和DMSO等有机溶剂，来源于三七花。

化学性质

三七皂苷Fe是一种白色结晶粉末，能够溶解在甲醇、乙醇及DMSO等有机溶剂中。

用途

该化合物常用于含量测定、鉴定以及药理实验。此外，它还具有治疗心脑血管疾病的药理作用。

反应信息

• 作为产物：
  描述：

  人参皂甙 在 水 作用下， 反应 72.0h， 以67%的产率得到三七叶苷
  参考文献：
  名称：

  Biotransformation of the Principal Ginsenosides of Panax ginseng Into Minor Glycosides Through the Action of Bacterium Paenibacillus sp. BG134

  摘要：

  细菌 Paenibacillus sp. BG134 能够将主要的 20(S)-原人参二醇皂苷 Rc、Rb2、Rd 和 Rb1 生物转化为相应的次要糖苷 C-Mc1、C-O 和 F-2。与其他几种微生物相比，Paenibacillus sp. BG134 的特异性在于它只切割其碳水化合物组分中的末端 C-3 和 C-20 β-D-葡萄糖。

  DOI：

  10.1007/s10600-014-1054-1

文献信息

• Overexpression and characterization of a glycoside hydrolase family 1 enzyme from Cellulosimicrobium cellulans sp. 21 and its application for minor ginsenosides production
  作者：Ye Yuan、Yanbo Hu、Chenxing Hu、Jiayi Leng、Honglei Chen、Xuesong Zhao、Juan Gao、Yifa Zhou

  DOI：10.1016/j.molcatb.2015.06.015

  日期：2015.10

  rare ginsenosides Gypenoside XVII (Gyp XVII), compound O, ginsenoside Mb and ginsenoside F2. Scaled-up production using 1 g of the PPDGM resulted in 292 mg Gyp XVII, 134 mg CO, 184 mg Mb, and 62 mg F2, with chromatographic purities. These results suggest that CcBgl1A would be potentially useful in the preparation of pharmacologically active minor ginsenosides Gyp XVII, CO, Mb and F2.

  从人参皂苷转化菌株Cellulosimicrobium cellulans sp。克隆了一个新的β-葡萄糖苷酶基因（ccbgl1a）。21.该酶在大肠杆菌中过表达，用镍金属亲和层析法对含N端His标签的重组β-葡萄糖苷酶（CcBgl1A）进行了充分的纯化，纯化倍数为1.9倍，比活性为31.5 U / mg。估计重组CcBgl1A的分子量约为46 kDa。CcBgl1A在35°C和pH 5.5下表现出最佳活性。然而，在40℃以上，酶稳定性显着降低。该酶对原人参二醇型人参皂苷混合物（PPDGM）具有很高的生物转化能力，可将人参皂苷Rb1，Rb2，Rc和Rd的外部C-3葡萄糖部分水解为稀少的人参皂苷人参皂甙XVII（Gyp XVII），化合物O，人参皂甙Mb和人参皂甙F2。使用1 g PPDGM进行规模化生产，得到292 mg Gyp XVII，134 mg CO，184 mg Mb和62 mg
• Hydrolysis of the outer <b>β</b>-(1,2)-<b><scp>d</scp></b>-glucose linkage at the C-3 position of ginsenosides by a commercial <b>β</b>-galactosidase and its use in the production of minor ginsenosides
  作者：Yeong-Su Kim、Do-Yeon Kim、Dong Wook Kang、Chang-Su Park

  DOI：10.1080/10242422.2018.1483348

  日期：2019.1.2

  Commercial beta-galactosidase from Aspergillus oryzae (SUMILACT L-TM) was used for the bioconversion of the ginsenosides Rb1, Rb2, Rc, Rd, and Rg3 to gypenoside-XVII, compound-O, compound-MC1, F2, and Rh2, respectively. The optimal conditions were pH 4.5, 50 degrees C, 60 U center dot mL(-1) enzyme, and 8.0 mM substrate. Interestingly, the enzyme hydrolyzed only the outer beta-(1,2)-d-glucose linkage at the C-3 position of ginsenosides. Under optimum conditions, the enzyme completely converted Rb1, Rb2, Rc, Rd, and Rg3 to gypenoside-XVII, compound-O, compound-MC1, F2, and Rh2, respectively, with the highest productivity.
• Ginsenoside Mc1 improves liver steatosis and insulin resistance by attenuating ER stress
  作者：Eun Roh、Hwan-Jin Hwang、Joo Won Kim、So-hyeon Hong、Jung A Kim、You-Bin Lee、Kyung Mook Choi、Sei Hyun Baik、Hye Jin Yoo

  DOI：10.1016/j.jep.2020.112927

  日期：2020.9

  Ethnopharmacological relevance: Ginsenoside, a major pharmacologically active ingredient in ginseng, has been known to exhibit beneficial properties such as antioxidant and anti-inflammatory effects. Ginsenoside compound Mc1 is one of the newly identified de-glycosylated ginsenosides. Endoplasmic reticulum (ER) stress has implicated in the development of non-alcoholic fatty liver disease (NAFLD) through apoptosis and lipid accumulation.Aim of the study: We aimed to examine the protective effects of Mc1 treatment on ER stress-induced cell death and impaired insulin signaling in HepG2 human hepatoblastoma cells and ER stress-induced liver steatosis and insulin resistance in a diet-induced obesity (DIO) mouse model.Materials and methods: HepG2 cells were treated with palmitate and Mc1 to evaluate the effects of Mc1 on ER stress-induced damage. C57BL/6 mice were fed with a high-fat diet (HFD) for 4 weeks and received an intraperitoneal injection of either vehicle or Mc1 (10 mg/kg/day). The control mice were fed with a chow diet and injected with vehicle for the same period. ER stress, cell death, and degree of steatosis were evaluated in the liver tissues of mice. The effect of Mc1 treatment on glucose metabolism was also determined.Results: Mc1 co-treatment reduced the palmitate-induced ER stress and death of HepG2 cells. The palmitate-induced insulin resistance improved after Mc1 co-treatment. Consistent with the in vitro data, chronic Mc1 supplementation reduced ER stress and apoptotic damage in the liver of obese mice. Mc1 treatment ameliorated glucose intolerance and insulin resistance through the suppression of c-Jun N-terminal kinase (JNK) phosphorylation. In addition, Mc1 treatment reduced obesity-induced lipogenesis and prevented fat accumulation in the liver of DIO mice.Conclusions: Mc1 exerted protective effects against ER stress-induced apoptotic damage, insulin resistance and lipogenesis in palmitate-treated hepatocytes and in the liver of DIO mice. Therefore, Mc1 supplementation could be a potential therapeutic strategy to prevent NAFLD in patients with obesity and insulin resistance.
• Biotransformation of Ginsenoside Rc into C-Mc1 by the Bacterium Sphingopyxis sp. BG97
  作者：L. N. Ten、S. M. Chae、S.-A. Yoo

  DOI：10.1007/s10600-014-1019-4

  日期：2014.7