stachysterone B

• 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: stachysterone B
• 英文别名: (2S,3R,5R,9R,10R,13R,17S)-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-6-one
• 化学式: C₂₇H₄₂O₆
• 分子量: 462.627
• InChiKey: ZYXLMHXQZHELAP-SVJUWISJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  蜕皮激素 在 吡啶 、 phosphomolybdic acid 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 7.36h， 生成 stachysterone B
  参考文献：
  名称：

  摘要：

  Trifluoroacetylation of the 25(OH) -group with subsequent dehydration of the 14(OH)-group takes place in the reaction of 20-hydroxyecdysone 20,22-acetonide and 2,3:20,22-diacetonide with trifluoroacetic anhydride in the presence of pyridine. Dehydration of the 14(OH)-group gives rise to stachisterone B derivatives, which are hydrolyzed to give the phytoecdysteroid stachisterone B.

  DOI：

  10.1023/a:1022433423370

文献信息

• Diversity-oriented synthesis through gamma radiolysis: Preparation of unusual ecdysteroid derivatives activating Akt and AMPK in skeletal muscle cells
  作者：Halima Meriem Issaadi、Zoltán Béni、Tünde Tóth、Miklós Dékány、Tusty-Jiuan Hsieh、György Tibor Balogh、Attila Hunyadi

  DOI：10.1016/j.bioorg.2021.104951

  日期：2021.7

  beneficial, non-hormonal bioactivities in mammals including humans. Gamma irradiations of aqueous solutions of 20E were conducted either in N2- or N2O-saturated solutions. Centrifugal partition chromatography was used to fractionate crude resulting irradiated materials using a biphasic solvent system composed of tert-butyl alcohol - ethyl acetate - water (0.45:0.9:1, v/v/v) in ascending mode. Subsequently

  伽马射线辐射是诱导生物活性化合物化学转化的一种独特方式。在本研究中，我们采用这种方法以多样性为导向合成 20-羟基蜕皮激素 (20E) 的类似物，这是一种丰富的蜕皮甾体，在包括人类在内的哺乳动物中具有一系列有益的非激素生物活性。20E水溶液的伽马辐射在N 2 -或N 2 O-饱和溶液中进行。离心分配色谱法用于使用由叔丁醇组成的双相溶剂系统来分级粗得到的辐照材料。- 丁醇 - 乙酸乙酯 - 水（0.45:0.9:1，v/v/v）在上升模式。随后，产物通过RP-HPLC纯化。分离出 14 种蜕皮甾体，包括 5 种新化合物，并通过一维和二维 NMR 和 HRMS 阐明了它们的结构。化合物2 - 4，7，9，12和15是为它们增加C2C12的AKT-和AMPK磷酸化的能力进行测试鼠骨骼肌管体外。这些化合物对 Akt 的活性与其母体化合物相似。Stachysterone B ( 7 ) 和一种新的环重排化合物
• Rapid, laser-induced conversion of 20-hydroxyecdysone – A follow-up study on the products obtained
  作者：Wan-Chun Lai、Balázs Dankó、József Csábi、Zoltán Kele、Fang-Rong Chang、Mihail L. Pascu、Tamás Gáti、András Simon、Leonard Amaral、Gábor Tóth、Attila Hunyadi

  DOI：10.1016/j.steroids.2014.07.016

  日期：2014.11

  We have recently reported the set-up of an experimental system for the laser-induced photochemical modification of bioactive substances, where two ecdysteroids, 20-hydroxyecdysone (20E) and its diacetonide derivative served as probes. As a direct continuation of our previous work, three new compounds together with five other ecdysteroid derivatives, have been identified from the novel, laser-induced photo-transformation reaction of 20E. The structures and NMR signal assignment were established by comprehensive one- and two-dimensional NMR spectroscopy supported by mass spectroscopy. Possible ways for the formation of each species is also discussed. Similar to their parental compound, the products obtained are potentially bioactive and worthy for further investigations; due to the low yields, however, a different approach for their higher scale production is suggested.
• ——
  作者：V. N. Odinokov、I. V. Galyautdinov、D. V. Nedopekin、L. M. Khalilov

  DOI：10.1023/a:1022433423370

  日期：——

  Trifluoroacetylation of the 25(OH) -group with subsequent dehydration of the 14(OH)-group takes place in the reaction of 20-hydroxyecdysone 20,22-acetonide and 2,3:20,22-diacetonide with trifluoroacetic anhydride in the presence of pyridine. Dehydration of the 14(OH)-group gives rise to stachisterone B derivatives, which are hydrolyzed to give the phytoecdysteroid stachisterone B.