(2R,3R,4S,5S,6R)-2-[[(6R,8R,10R,12S,14S)-3,12-dihydroxy-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol | 63223-86-9

• 物质功能分类: 生物化工 - 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
• 英文名称: (2R,3R,4S,5S,6R)-2-[[(6R,8R,10R,12S,14S)-3,12-dihydroxy-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 英文别名: Ginsenoside Rh1
• CAS: 63223-86-9；80952-71-2
• 化学式: C₃₆H₆₂O₉
• 分子量: 638.883
• InChiKey: RAQNTCRNSXYLAH-TVDYJPNFSA-N

物化性质

• 沸点：
  755.1±60.0 °C(Predicted)
• 密度：
  1.23
• 溶解度：
  DMSO：100 mg/mL（156.53 mM；需要超声波）
• LogP：
  3.740 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  45.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  160.07
• 氢给体数：
  7.0
• 氢受体数：
  9.0

安全信息

• WGK Germany：
  3

制备方法与用途

理化性质

人参皂苷Rh1来源为五加科植物人参Panax ginseng C. A. Mey.的干燥根,是一种白色粉末状物质，溶解性:易溶于水、甲醇、乙醇，不溶于乙/醚、苯。

生物活性

20(S)-Ginsenoside Rh1 (Prosapogenin A2, Sanchinoside B2, Sanchinoside Rh1)是从红参中提取的主要生物活性化合物之一，在世界范围内，红参已越来越多地用于增强认知和身体健康。它具有抗发炎、抗氧化、免疫调节作用和对神经系统有积极作用的有效特性。20(S)-Ginsenoside Rh1 可抑制 PPAR-γ、TNF-α、IL-6 和 IL-1β 的表达。

靶点

PPAR-γ

TNF-α

IL-6

IL-1β

Human Endogenous Metabolite

体外研究

The effect of Ginsenoside Rh1 is examined on adipogenesis in 3T3-L1 cells. Ginsenoside Rh1 potently inhibits the adipogenesis, as assessed by Oil-red O staining and lipid contents in 3T3-L1 adipocytes. Ginsenoside Rh1, at concentrations of 50 μM and 100 μM, inhibit the adipogenesis by 50% and 63%, respectively.The expression levels of adipocytespecific genes such as PPAR-γ, C/EBP-α, FAS, aFABP and some genes are examined during early phase of differentiation such as Pref-1, C/EBP-δ and Glucocorticoid receptor (GR). After the treatment with Ginsenoside Rh1 in 3T3-L1 cells, mRNA is extracted on 18 h and 24 h for Pref-1, C/EBP-δ and GR and day 8 for PPAR-γ, C/EBP-α, FAS, aFABP. Then, the expression profiles of adipocyte-specific genes are investigated by RT-PCR. PPAR-γ, C/EBP-α, FAS, and aFABP expressions are significantly increased in DMI-stimulated differentiated adipocyte compared to those of non-stimulated adipocyte cells. However, treatment with DMI in the presence of Ginsenoside Rh1 significantly suppresses the expression levels of PPAR-γ, C/EBP-α, FAS, and aFABP in a dose- dependent manner, whereas the expression levels of Pref-1, C/EBP-δ and GR are not affected.

体内研究

When high-fat diet (HFD) fed mice for 8 weeks, body and epididymal fat weight gains are significantly increased compared to those of low-fat diet (LFD)-fed mice. However, when Ginsenoside Rh1 is treated in HFD-fed mice, body and epididymal fat weight gains are significantly decrease compared with those of the HFD-fed mice. TG, glucose, insulin, total cholesterol, and HDL levels in the blood are significantly increased in HFD-fed mice group compared to LFD-fed mice group. Treatment with Ginsenoside Rh1 in HFD-fed mice significantly lowers TG level alone.

化学性质 

白色粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于人参。

用途 

用于含量测定/鉴定/药理实验等。
药理药效:具有滋补强壮，抗肿瘤作用。

用途 

(20S)-人参皂苷Rh1是人参中的主要成分之一，具有抗炎作用。

反应信息

• 作为产物：
  描述：

  ginsenoside Rg1 在 盐酸 作用下， 反应 0.25h， 以62.7 mg的产率得到(2R,3R,4S,5S,6R)-2-[[(6R,8R,10R,12S,14S)-3,12-dihydroxy-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Studies on the absorption, distribution, excretion and metabolism of ginseng saponins. IV. Decomposition of ginsenoside-Rg1 and -Rb1 in the digestive tract of rats.

  摘要：

  研究了口服后人参皂苷-Rg1和人参皂苷-Rb1在大鼠胃和大肠中的分解情况。在胃中，部分人参皂苷-Rg1被分解，在反相薄层色谱（TLC）上观察到六种分解产物。这六种化合物与人参皂苷-Rg1在弱酸性条件下（0.1N HCl，37°C）水解得到的化合物相同。另一方面，大鼠口服Rb1后，在胃样品的TLC上观察到未鉴定的人参皂苷-Rb1分解产物。该产物不同于Rb1在弱酸性条件下水解形成的分解产物。在大肠中，Rg1分别被四环素敏感细菌和四环素耐药细菌分解为人参皂苷-Rh1和人参皂苷-F1。人参皂苷-Rb1被肠酶和四环素耐药菌分别分解为人参皂苷-Rd和两种未鉴定的产物。

  DOI：

  10.1248/cpb.31.3691