(20S)-dammarane-24(25)-ene-3β,20,21-tetrol | 17939-12-7

• 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)-dammarane-24(25)-ene-3β,20,21-tetrol
• 英文别名: Dryobalanol；(2S)-2-[(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]-6-methylhept-5-ene-1,2-diol
• CAS: 17939-12-7
• 化学式: C₃₀H₅₂O₃
• 分子量: 460.741
• InChiKey: ARYNZYKWUXIZOG-AYHBXSNGSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  566.9±35.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3β,20S)-19-oxo-3,20,21-trihydroxydammar-24-ene 3-O-β-D-xylopyranosyl-(1-3)-α-L-arabinopyranoside 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 、 L-(+)-arabinose 、 (20S)-dammarane-24(25)-ene-3β,20,21-tetrol
  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.