ginsenoside Rg5 | 74964-14-0

• 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
• 英文名称: ginsenoside Rg5
• 英文别名: Ginsenoside Rg31；(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-(6-methylhepta-2,5-dien-2-yl)-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 74964-14-0
• 化学式: C₄₂H₇₀O₁₂
• 分子量: 767.011
• InChiKey: NJUXRKMKOFXMRX-MHOSXIPRSA-N

物化性质

• 沸点：
  855.6±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  54
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	20(R)-ginsenoside Rg3	38243-03-7	C42H72O13	785.026
  ——	ginsenoside Rg3	126252-51-5	C42H72O13	785.026
  人参皂甙	Ginsenoside Rb1	41753-43-9	C54H92O23	1109.31

反应信息

• 作为产物：
  描述：

  20(R)-ginsenoside Rg3 在 吡啶 、 4-二甲氨基吡啶 、 乙酸酐 、 三乙基硅烷 、 三氟化硼乙醚 、 potassium hydroxide 作用下， 以 二氯甲烷 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 20.0h， 生成 ginsenoside Rg5
  参考文献：
  名称：

  CN108420793

  摘要：

  公开号：

文献信息

• The Preparation of Ginsenoside Rg5, Its Antitumor Activity against Breast Cancer Cells and Its Targeting of PI3K
  作者：Yannan Liu、Daidi Fan

  DOI：10.3390/nu12010246

  日期：——

  Ginsenosides have been reported to possess various pharmacological effects, including anticancer effects. Nevertheless, there are few reports about the antitumor activity and mechanisms of ginsenoside Rg5 against breast cancer cells. In the present study, the major ginsenoside Rb1 was transformed into the rare ginsenoside Rg5 through enzymatic bioconversion and successive acid-assisted high temperature and pressure processing. Ginsenosides Rb1, Rg3, and Rg5 were investigated for their antitumor effects against five human cancer cell lines via the MTT assay. Among them, Rg5 exhibited the greatest cytotoxicity against breast cancer. Moreover, Rg5 remarkably suppressed breast cancer cell proliferation through mitochondria-mediated apoptosis and autophagic cell death. LC3B-GFP/Lysotracker and mRFP-EGFP-LC3B were utilized to show that Rg5 induced autophagosome-lysosome fusion. Western blot assays further illustrated that Rg5 decreased the phosphorylation levels of PI3K, Akt, mTOR, and Bad and suppressed the PI3K/Akt signaling pathway in breast cancer. Moreover, Rg5-induced apoptosis and autophagy could be dramatically strengthened by the PI3K/Akt inhibitor LY294002. Finally, a molecular docking study demonstrated that Rg5 could bind to the active pocket of PI3K. Collectively, our results revealed that Rg5 could be a potential therapeutic agent for breast cancer treatment.

  人参皂苷已被报道具有多种药理学效应，包括抗癌效应。然而，关于人参皂苷Rg5对乳腺癌细胞的抗肿瘤活性和机制的报道很少。在本研究中，通过酶促生物转化和连续的酸辅助高温高压处理，将主要的人参皂苷Rb1转化为罕见的人参皂苷Rg5。通过MTT实验，研究了人参皂苷Rb1、Rg3和Rg5对五种人类癌细胞系的抗肿瘤效应。其中，Rg5对乳腺癌表现出最强的细胞毒性。此外，Rg5通过线粒体介导的凋亡和自噬细胞死亡显著抑制了乳腺癌细胞的增殖。使用LC3B-GFP/Lysotracker和mRFP-EGFP-LC3B表明，Rg5诱导自噬体-溶酶体融合。Western blot实验证明，Rg5降低了PI3K、Akt、mTOR和Bad的磷酸化水平，并抑制了PI3K/Akt信号通路在乳腺癌中的作用。此外，Rg5诱导的凋亡和自噬可被PI3K/Akt抑制剂LY294002显著增强。最后，分子对接研究表明，Rg5可以结合到PI3K的活性口袋。总之，我们的结果揭示了Rg5可能成为乳腺癌治疗的潜在治疗药物。
• The chemical and hydroxyl radical scavenging activity changes of ginsenoside-Rb1 by heat processing
  作者：Yong Jae Lee、Hyun Young Kim、Ki Sung Kang、Jin Gyun Lee、Takako Yokozawa、Jeong Hill Park

  DOI：10.1016/j.bmcl.2008.07.056

  日期：2008.8

  The chemical and hydroxyl radical (.OH) scavenging activity changes of ginsenoside Rb-1 (Rb-1) by heat processing were investigated in this study. Rb-1 was changed into 20(S)-Rg(3), 20(R)-Rg3, Rk(1), and Rg(5) by heat processing through glucosyl elimination and epimerization of carbon-20 by SN1 reaction. The glucosyl moiety, separated from Rb-1, made Maillard reaction product (MRPs) with glycine. The generations of 20(S)-Rg(3) and MRPs were related to the increased OH scavenging activity of Rb-1 by heat processing. (c) 2008 Elsevier Ltd. All rights reserved.
• CN108420793
  申请人：——

  公开号：——

  公开（公告）日：——