jaborosalactone 5

• 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: jaborosalactone 5
• 英文别名: (5R,5aR,6aS,6bR,12aS,12bS,12cS)-5a-hydroxy-3-(hydroxymethyl)-3',4',6b,12c-tetramethylspiro[1,2,6,6a,10,12,12a,12b-octahydrobenzo[j]aceanthrylene-5,5'-furan]-2',4,7-trione
• 化学式: C₂₈H₃₂O₆
• 分子量: 464.558
• InChiKey: WEGSTRJZXDTPCG-JQOZULIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  jaborosalactone 5 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 56.0h， 以3%的产率得到(22R,23S)-21,12β,22a-trihydroxy-1,22-dioxo-12,23-cycloergostan-2,5,17,24-tetraen-26,23-olide
  参考文献：
  名称：

  Antiproliferative and quinone reductase-inducing activities of withanolides derivatives

  摘要：

  Two new and five known withanolides (jaborosalactones 2, 3, 4, 5, and 24) were isolated from the leaves of Jaborosa runcinata Lam. We also obtained some derivatives from jaborosalactone 5, which resulted to be the major isolated metabolite. The natural compounds as well as derivatives were evaluated for their antiproliferative activity and the induction of quinone reductase 1 (QR1; NQ01) activity. Structure activity relationships revealed valuable information on the pharmacophore of withanolide-type compounds. Three compounds of this series showed significantly higher antiproliferative activity than jaborosalactone 5. The effect of these compounds on the cell cycle was determined. Furthermore, the ability of major compounds to induce QR1 was evaluated. It was found that all the active test compounds are monofunctional inducers that interact with Keap1. The most promising derivatives prepared from jaborosalactone 5 include (23R)-4 beta,12 beta,21-trihydroxy-1,22-dioxo-12,23-cycloergostan-2,5,17,24-tetraen-26,23-olide (18) and (23R)-21-acetoxy-12 beta-hydroxy-1,22-dioxo-12,23-cycloergostan-2,5,17,24-tetraen-26,23-lactame (20). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.045

文献信息

• Antiproliferative and quinone reductase-inducing activities of withanolides derivatives
  作者：Manuela E. García、Viviana E. Nicotra、Juan C. Oberti、Carla Ríos-Luci、Leticia G. León、Laura Marler、Guannan Li、John M. Pezzuto、Richard B. van Breemen、José M. Padrón、Idaira Hueso-Falcón、Ana Estévez-Braun

  DOI：10.1016/j.ejmech.2014.05.045

  日期：2014.7

  Two new and five known withanolides (jaborosalactones 2, 3, 4, 5, and 24) were isolated from the leaves of Jaborosa runcinata Lam. We also obtained some derivatives from jaborosalactone 5, which resulted to be the major isolated metabolite. The natural compounds as well as derivatives were evaluated for their antiproliferative activity and the induction of quinone reductase 1 (QR1; NQ01) activity. Structure activity relationships revealed valuable information on the pharmacophore of withanolide-type compounds. Three compounds of this series showed significantly higher antiproliferative activity than jaborosalactone 5. The effect of these compounds on the cell cycle was determined. Furthermore, the ability of major compounds to induce QR1 was evaluated. It was found that all the active test compounds are monofunctional inducers that interact with Keap1. The most promising derivatives prepared from jaborosalactone 5 include (23R)-4 beta,12 beta,21-trihydroxy-1,22-dioxo-12,23-cycloergostan-2,5,17,24-tetraen-26,23-olide (18) and (23R)-21-acetoxy-12 beta-hydroxy-1,22-dioxo-12,23-cycloergostan-2,5,17,24-tetraen-26,23-lactame (20). (C) 2014 Elsevier Masson SAS. All rights reserved.