(3β,20S,23R)-3,20,23-trihydroxydammar-24-en-21-oic acid-21,23-lactone 3-O-[α-L-rhamnopyranosyl-(1→2)]-[β-D-xylopyranosyl-(1→3)]-β-D-6-O-acetylglucopyranoside

• 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,20S,23R)-3,20,23-trihydroxydammar-24-en-21-oic acid-21,23-lactone 3-O-[α-L-rhamnopyranosyl-(1→2)]-[β-D-xylopyranosyl-(1→3)]-β-D-6-O-acetylglucopyranoside
• 英文别名: (3β,20S,23R)-3,20,23-trihydroxydammar-24-en-21-oic acid-21,23-lactone 3-O-[α-L-rhamnopyranosyl-(1-2)]-[β-D-xylopyranosyl-(1-3)]-β-D-6-O-acetylglucopyranoside；[(2R,3R,4S,5R,6R)-3-hydroxy-6-[[(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(3S,5R)-3-hydroxy-5-(2-methylprop-1-enyl)-2-oxooxolan-3-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]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• 化学式: C₄₉H₇₈O₁₈
• 分子量: 955.148
• InChiKey: AXBJYHWXSQPRFA-MWBNBBALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  67
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  270
• 氢给体数：
  8
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (3β,20S,23R)-3,20,23-trihydroxydammar-24-en-21-oic acid-21,23-lactone 3-O-[α-L-rhamnopyranosyl-(1→2)]-[β-D-xylopyranosyl-(1→3)]-β-D-6-O-acetylglucopyranoside 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 、 L-rhamnopyranose 、 (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.