annoglaucin | 164991-79-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: annoglaucin
• 英文别名: (5S)-5-Methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,2a(2)R,5R,5a(2)R)-octahydro-5a(2)-[(1S)-1-hydroxyundecyl][2,2a(2)-bifuran]-5-yl]tridecyl]-2(5H)-furanone；(2S)-2-methyl-4-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2H-furan-5-one
• CAS: 164991-79-1
• 化学式: C₃₇H₆₆O₈
• 分子量: 638.926
• InChiKey: QFFLFGFTHVFFDL-GIPZGXSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  45
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  annoglaucin 在 二乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以5 mg的产率得到(R)-5-{(6R,11R)-6,11-Dihydroxy-11-[(2R,5R,2'R,5'R)-5'-((S)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-undecyl}-3-(2-oxo-propyl)-dihydro-furan-2-one
  参考文献：
  名称：

  Purpuracenin: a new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Annona purpurea1Part 36 in the series `Chemical Studies on Mexican Plants Used in Traditional Medicine'. For part 35 see (Chávez & Mata, 1998).12Taken in part from the Ph.D. thesis of Daniel Chávez.2

  摘要：

  Purpuracenin, a novel cytotoxic acetogenin and annoglaucin, a known compound, were isolated from the seeds of Annona purpurea. Their structures were elucidated by a combination of chemical and spectral methods including MS and NMR spectral measurements. The absolute configurations of both compounds are presented. The new compound and annoglaucin exhibited potent cytotoxic activity in vitro against six human solid tumor cell lines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00553-6

文献信息

• EXTRACTS, FRACTIONS AND COMPOSITIONS COMPRISING ACETOGENINS AND THEIR APPLICATIONS
  申请人：GOKARAJU Ganga Raju

  公开号：US20120201884A1

  公开（公告）日：2012-08-09

  The current disclosure discloses acetogenin(s), extract(s)/fraction(s) standardized to acetogenin(s) comprising terminal α,β-unsaturated-γ-methyl-γ-lactone moiety derived from Annona squamosa or their compositions for prevention, treatment, inhibition or controlling inflammation and immune related diseases or disorders mediated through cytokines/chemokines or other biomarkers. The disclosure further discloses said Annona squamosa derived acetogenin(s), extract(s)/fraction(s) or their compositions for prevention, treatment, inhibition or controlling metabolic diseases/disorders.
• Purpuracenin: a new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Annona purpurea1Part 36 in the series `Chemical Studies on Mexican Plants Used in Traditional Medicine'. For part 35 see (Chávez & Mata, 1998).12Taken in part from the Ph.D. thesis of Daniel Chávez.2
  作者：Daniel Chávez、Rachel Mata

  DOI：10.1016/s0031-9422(98)00553-6

  日期：1999.3

  Purpuracenin, a novel cytotoxic acetogenin and annoglaucin, a known compound, were isolated from the seeds of Annona purpurea. Their structures were elucidated by a combination of chemical and spectral methods including MS and NMR spectral measurements. The absolute configurations of both compounds are presented. The new compound and annoglaucin exhibited potent cytotoxic activity in vitro against six human solid tumor cell lines. (C) 1999 Elsevier Science Ltd. All rights reserved.