ent-6α,7α,16β,17-tetrahydroxykauran-19-oic acid-16-O-β-D-glucopyranoside | 1152595-68-0

• 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: ent-6α,7α,16β,17-tetrahydroxykauran-19-oic acid-16-O-β-D-glucopyranoside
• 英文别名: ent-6β,7β,16α,17-tetrahydroxykauran-19-oic acid 16-O-β-D-glucopyranoside；pharboside F；(1R,2R,3S,4S,5R,9S,10S,13R,14R)-2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyl-14-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 1152595-68-0
• 化学式: C₂₆H₄₂O₁₁
• 分子量: 530.613
• InChiKey: QUCGBWQRLWOVBR-WSNGDQLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  197
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ent-6α,7α,16β,17-tetrahydroxykauran-19-oic acid-16-O-β-D-glucopyranoside 在 hesperidinase from Aspergillus niger 、 水 作用下， 反应 72.0h， 以1 mg的产率得到6β,7β,16α,17-tetrahydroxy-ent-kauran-19-oic acid
  参考文献：
  名称：

  Diterpene Glycosides from the Seeds of Pharbitis nil

  摘要：

  Six new ent-kaurane diterpene glycosides, pharbosides A-F (1-6), and a new ent-gibbane diterpene glycoside, pharboside G (7), together with three known ent-kaurane diterpenoids, 7 beta, 16 beta, 17-trihydroxy-ent-kauran-6 alpha, 19-olide (8), 6 beta, 7 beta, 16 alpha, 17-tetrahydroxy-ent-kauranoic acid (9), and 6 beta, 7 beta, 16 beta, 17-tetrahydroxy-ent-kauranoic acid (10), were isolated from an ethanolic extract of the seeds of Pharbitis nil. The structures of the new compounds were determined by spectroscopic methods including 1D and 2D NMR analysis. The absolute configurations of the compounds were clarified by CD spectroscopic studies. Full NMR data assignments of the three known compounds (8-10) are reported. The isolated compounds were evaluated for their cytotoxic activities against four human cancer cell lines.

  DOI：

  10.1021/np900101t

文献信息

• Diterpene Glycosides from the Seeds of <i>Pharbitis nil</i>
  作者：Ki Hyun Kim、Sang Un Choi、Kang Ro Lee

  DOI：10.1021/np900101t

  日期：2009.6.26

  Six new ent-kaurane diterpene glycosides, pharbosides A-F (1-6), and a new ent-gibbane diterpene glycoside, pharboside G (7), together with three known ent-kaurane diterpenoids, 7 beta, 16 beta, 17-trihydroxy-ent-kauran-6 alpha, 19-olide (8), 6 beta, 7 beta, 16 alpha, 17-tetrahydroxy-ent-kauranoic acid (9), and 6 beta, 7 beta, 16 beta, 17-tetrahydroxy-ent-kauranoic acid (10), were isolated from an ethanolic extract of the seeds of Pharbitis nil. The structures of the new compounds were determined by spectroscopic methods including 1D and 2D NMR analysis. The absolute configurations of the compounds were clarified by CD spectroscopic studies. Full NMR data assignments of the three known compounds (8-10) are reported. The isolated compounds were evaluated for their cytotoxic activities against four human cancer cell lines.