16α,23α-epoxy-2β,3β,7β,20β,26-pentahydroxy-10α,23α-cucurbit-5,24-(E)-dien-11-one 2-O-β-D-glucopyranoside | 1135141-75-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 16α,23α-epoxy-2β,3β,7β,20β,26-pentahydroxy-10α,23α-cucurbit-5,24-(E)-dien-11-one 2-O-β-D-glucopyranoside
• 英文别名: (1S,2S,4R,6S,8S,9R,10R,13S,14R,16S,17R,21S)-8,17,21-trihydroxy-6-[(E)-3-hydroxy-2-methylprop-1-enyl]-2,8,10,13,18,18-hexamethyl-16-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicos-19-en-12-one
• CAS: 1135141-75-1
• 化学式: C₃₆H₅₆O₁₂
• 分子量: 680.833
• InChiKey: AFXPJFXBBQEMAB-VPBSPBINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  48
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  16α,23α-epoxy-2β,3β,7β,20β,26-pentahydroxy-10α,23α-cucurbit-5,24-(E)-dien-11-one 2-O-β-D-glucopyranoside 在 β-glucosidase 作用下， 生成 可得然胶 、 16α,23α-epoxy-2β,3β,7β,20β,26-pentahydroxy-10α,23α-cucurbit-5,24-(E)-dien-11-one
  参考文献：
  名称：

  Cucurbitane-Type Triterpenoids from the Stems of Cucumis melo

  摘要：

  Phytochemical investigation of the stems of Cucumis melo led to the isolation and identification of 21 cucurbitane-type triterpenoids, including nine new compounds (1-9) and 12 known compounds. Their structures were determined on the basis of spectroscopic analyses, chemical methods, and comparison with spectroscopic data in the literature. Two known compounds, cucurbitacin B (10) and cucurbitacin A (11), showed significant cytotoxic activity against the proliferation of A549/ATCC and BEL7402 cells in vitro. Of the new compounds, only compound 7 was weakly cytotoxic. The inhibitory effects of all compounds on the Jak-Stat3 signaling pathway were evaluated, but only cucurbitacin B (10) showed significant inhibitory activity of phosphotyrosine STAT3.

  DOI：

  10.1021/np800692t