methyl (1R,2S,4R,5S,6S,11S,15R,18R,20S,23S)-20-hydroxy-5,8,8,15,19,19,23-heptamethyl-3-oxahexacyclo[13.8.0.02,4.05,14.06,11.018,23]tricos-13-ene-11-carboxylate | 1028332-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: methyl (1R,2S,4R,5S,6S,11S,15R,18R,20S,23S)-20-hydroxy-5,8,8,15,19,19,23-heptamethyl-3-oxahexacyclo[13.8.0.02,4.05,14.06,11.018,23]tricos-13-ene-11-carboxylate
• CAS: 1028332-93-5
• 化学式: C₃₁H₄₈O₄
• 分子量: 484.72
• InChiKey: BRRJNWSSDUUZGC-MSTDTBLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 (1R,2S,4R,5S,6S,11S,15R,18R,20S,23S)-20-hydroxy-5,8,8,15,19,19,23-heptamethyl-3-oxahexacyclo[13.8.0.02,4.05,14.06,11.018,23]tricos-13-ene-11-carboxylic acid 以 甲醇 、 乙醚 为溶剂， 反应 12.0h， 以1.9 mg的产率得到methyl (1R,2S,4R,5S,6S,11S,15R,18R,20S,23S)-20-hydroxy-5,8,8,15,19,19,23-heptamethyl-3-oxahexacyclo[13.8.0.02,4.05,14.06,11.018,23]tricos-13-ene-11-carboxylate
  参考文献：
  名称：

  Oleanane and Taraxerane Glycosides from the Roots of Gomphrena macrocephala

  摘要：

  Phytochemical screening of the roots of Gomphrena macrocephala, with particular attention to its triterpene glycoside constituents, has resulted in the isolation of two new oleanane glycosides (1 and 2) and a new taraxerane glycoside (3). The structures of 1-3 were determined as 11 alpha, 12 alpha-epoxy-3 beta-[(O-beta-D-glucuronopyranosyl)oxy]olean-28,13-olide (1), 11 alpha, 12 alpha-epoxy-3 beta-[(O-beta-D-galactopyranosyl-(1 -> 3)-O-[beta-D-glucopyranosyl-(1 -> 2)]-beta-D-glucuronopyranosyl)oxy] olean-28,13-olide (2), and 11 alpha, 12 alpha-epoxy-3 beta-[(O-beta-D-glucuronopyranosyl)oxy] taraxer-14-en-28-oic acid beta-D-glucopyranosyl ester (3), respectively, on the basis of their spectroscopic data and the results of hydrolysis. The aglycones (1a and 3a) of 1-3 with an epoxy group showed cytotoxic activity against HSC-2 human oral squamous carcinoma cells.

  DOI：

  10.1021/np068014r