3β-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-(20S,24S)-epoxydammarane-12β,25-diol

• 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: 3β-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-(20S,24S)-epoxydammarane-12β,25-diol
• 英文别名: (20S,24S)-20,24-epoxy-12,25-dihydroxydammaran-3-yl O-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside；gynoside B；(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-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-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₄₂H₇₂O₁₄
• 分子量: 801.025
• InChiKey: VBWLFPXNVMBQCR-HJMNTHRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  56
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  228
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  在 palladium hydroxide, 20 wt% on carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以23 mg的产率得到3β-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-(20S,24S)-epoxydammarane-12β,25-diol
  参考文献：
  名称：

  Synthesis of Ocotillol-Type Ginsenosides

  摘要：

  A total of 14 ocotillol-type ginsenosides were conveniently synthesized employing glycosylation of ocotillol sapogenin derivatives with glucosyl ortho-alkynylbenzoate donors under the promotion of a gold(I) catalyst as the key step. Relying on a rational protecting group strategy and the unexpected regioselectivity of the glycosylation of the 3,25-diol sapogenins (2a/2b, 5a/5b) for the tertiary 25-OH, mono 3-O-glucosyl ocotillol-PPD, 6-O-glucosyl ocotillol-PPT, 25-O-glucosyl ocotillol-PPD/PPT and 3,25-di-O-glucosyl ocotillol-PPD/PPT ginsenosides were prepared in which the configuration at the C-24 is either R or S.

  DOI：

  10.1021/acs.joc.6b01265

文献信息

• Semisynthesis and bioactive evaluation of oxidized products from 20(S)-ginsenoside Rg3, Rh2, protopanaxadiol (PPD) and their 20(R)-epimers as cytotoxic agents
  作者：Jie Yang、Xuwen Li、Ting Sun、Yan Gao、Yanxin Chen、Yongri Jin、Yang Li

  DOI：10.1016/j.steroids.2015.12.005

  日期：2016.2

  eight compounds (3, 8, 9, 10, 15, 16, 19 and 22) with the cyclized side chain were firstly identified. Most of the tested compounds possessed cytotoxicity to a certain degree against the two types of cells which implied these oxidized products could play a certain role on anti-cancer functions of the raw materials in vivo. Meanwhile, the results proved that the configurations at C-20 or C-24 and the number

  已从20（S）-人参皂苷Rg3，Rh2、20（S）-原人参二醇（PPD）和它们的20（R）表观分子系统地合成了一系列氧化产物，并评估了其中大多数产物的抗细胞毒性活性首次通过MTT法检测HeLa细胞和HepG2细胞。根据全面的（1）H NMR，（13）C NMR，二维（2D）NMR和质谱数据，获得了22种产物并进行了阐明，其结果在以前的文献中已有报道。获得全部四种奥古洛尔型皂苷（20S，24R（delta86，delta85）; 20S，24S（delta87，delta88）; 20R，24R（delta86，delta86）; 20R，24S（delta86，delta87），此外，还得到了8种化合物首先鉴定了具有环化侧链的（3、8、9、10、15、16、19和22）。大多数测试化合物对两种类型的细胞都具有一定程度的细胞毒性，这暗示这些氧化产物可能对原料的体内抗癌功能起一定作用。同时，结
• Synthesis of Ocotillol-Type Ginsenosides
  作者：Renzeng Shen、Xin Cao、Stephane Laval、Jiansong Sun、Biao Yu

  DOI：10.1021/acs.joc.6b01265

  日期：2016.11.4

  A total of 14 ocotillol-type ginsenosides were conveniently synthesized employing glycosylation of ocotillol sapogenin derivatives with glucosyl ortho-alkynylbenzoate donors under the promotion of a gold(I) catalyst as the key step. Relying on a rational protecting group strategy and the unexpected regioselectivity of the glycosylation of the 3,25-diol sapogenins (2a/2b, 5a/5b) for the tertiary 25-OH, mono 3-O-glucosyl ocotillol-PPD, 6-O-glucosyl ocotillol-PPT, 25-O-glucosyl ocotillol-PPD/PPT and 3,25-di-O-glucosyl ocotillol-PPD/PPT ginsenosides were prepared in which the configuration at the C-24 is either R or S.