(20S,23S)-3β,20-dihydroxyldammarane-24-ene-21-oic acid-21, 23-lactone | 1189533-03-6

• 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: (20S,23S)-3β,20-dihydroxyldammarane-24-ene-21-oic acid-21, 23-lactone
• 英文别名: (3S,5S)-3-hydroxy-3-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-(2-methylprop-1-enyl)oxolan-2-one
• CAS: 1189533-03-6
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: UVWSKJGMKBMOEV-OVFYZRPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (20S,23S)-3β,20-dihydroxyldammarane-24-ene-21-oic acid-21, 23-lactone 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以70.9%的产率得到(20S,23S)-3-oxo-20,23-dihydroxydammar-24-en-21-oic acid 21,23-lactone
  参考文献：
  名称：

  绞股蓝的Dammaranes及其衍生物的合成作为蛋白酪氨酸磷酸酶1B的抑制剂

  摘要：

  蛋白酪氨酸磷酸酶1B（PTP1B）是胰岛素通路负调控的关键因素，也是治疗糖尿病和肥胖症的有希望的靶标。在此，将由天然三萜皂苷1b制得的皂甙元2b在3位上进行修饰，以通过酯化，氧化和还原胺化反应建立达玛烷衍生物库，并作为PTP1B抑制剂进行评价。3- ø -对位-Carboxylphenyl取代的衍生物5b中被发现在体外抑制活性的最佳蛋白质酪氨酸磷酸酶1B（IC 50  = 0.27μM），其中3- ö -元-carboxylphenyl取代5A 在PTP1B和T细胞蛋白酪氨酸磷酸酶之间表现出最佳的选择性（接近五倍）。

  DOI：

  10.1016/j.bmc.2010.04.073
• 作为产物：
  描述：

  (20S,23S)-3β,20-dihydroxydammar-24-en-21-oic acid-21,23-lactone-3-O-[β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 D-吡喃木糖 、 D-葡萄糖 、 (20S,23S)-3β,20-dihydroxyldammarane-24-ene-21-oic acid-21, 23-lactone 、 (3S,5R)-3-hydroxy-3-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-(2-methylprop-1-enyl)oxolan-2-one
  参考文献：
  名称：

  Dammarane Glycosides from the Root of Machilus yaoshansis

  摘要：

  Nine new dammarane triterpene glycosides (1-3 and 8-13) and 12 known analogues have been isolated from an ethanol extract of the roots of Machilus yaoshansis. Compounds 1-7 have an uncommon 20,23-dihydroxydammar-24-en-21-oic acid-21,23-lactone moiety that was previously reported in compounds isolated from Gynostemma pentaphyllum. The configurations of the lactone moieties in 1-3 were determined by comparison of the experimental ECD spectra of 1-3 and the hydrolysates, 1a and 1b, with the corresponding calculated ECD spectra. On the basis of NMR and ECD data analysis of 1-7, the previously reported C-20 and C-23 configurations of 4-7 and related derivatives from Gynostemma pentaphyllum were revised. In addition, the application of NMR data and Cotton effects to the determination of the relative and absolute configurations of the gamma-lactone moiety in 3 beta,20,23-trihydroxydammar-24-en-21-oic acid-21,23-lactone derivatives is discussed.

  DOI：

  10.1021/np300310a

文献信息

• Dammarane Glycosides from the Root of <i>Machilus yaoshansis</i>
  作者：Maoluo Gan、Mingtao Liu、Lishe Gan、Sheng Lin、Bo Liu、Yanling Zhang、Jiachen Zi、Weixia Song、Jiangong Shi

  DOI：10.1021/np300310a

  日期：2012.7.27

  Nine new dammarane triterpene glycosides (1-3 and 8-13) and 12 known analogues have been isolated from an ethanol extract of the roots of Machilus yaoshansis. Compounds 1-7 have an uncommon 20,23-dihydroxydammar-24-en-21-oic acid-21,23-lactone moiety that was previously reported in compounds isolated from Gynostemma pentaphyllum. The configurations of the lactone moieties in 1-3 were determined by comparison of the experimental ECD spectra of 1-3 and the hydrolysates, 1a and 1b, with the corresponding calculated ECD spectra. On the basis of NMR and ECD data analysis of 1-7, the previously reported C-20 and C-23 configurations of 4-7 and related derivatives from Gynostemma pentaphyllum were revised. In addition, the application of NMR data and Cotton effects to the determination of the relative and absolute configurations of the gamma-lactone moiety in 3 beta,20,23-trihydroxydammar-24-en-21-oic acid-21,23-lactone derivatives is discussed.
• Dammaranes from Gynostemma pentaphyllum and synthesis of their derivatives as inhibitors of protein tyrosine phosphatase 1B
  作者：Ji-Qing Xu、Qiang Shen、Jia Li、Li-Hong Hu

  DOI：10.1016/j.bmc.2010.04.073

  日期：2010.6.1

  (PTP1B) is a key factor in the negative regulation of insulin pathway and a promising target for treatment of diabetes and obesity. Herein, the sapogenin 2b, prepared from the natural triterpene saponin 1b, was modified at 3-position to establish the dammarane derivatives library via esterification, oxidation and reductive amination reaction and evaluated as PTP1B inhibitors. 3-O-para-Carboxylphenyl

  蛋白酪氨酸磷酸酶1B（PTP1B）是胰岛素通路负调控的关键因素，也是治疗糖尿病和肥胖症的有希望的靶标。在此，将由天然三萜皂苷1b制得的皂甙元2b在3位上进行修饰，以通过酯化，氧化和还原胺化反应建立达玛烷衍生物库，并作为PTP1B抑制剂进行评价。3- ø -对位-Carboxylphenyl取代的衍生物5b中被发现在体外抑制活性的最佳蛋白质酪氨酸磷酸酶1B（IC 50  = 0.27μM），其中3- ö -元-carboxylphenyl取代5A 在PTP1B和T细胞蛋白酪氨酸磷酸酶之间表现出最佳的选择性（接近五倍）。