calonysterone | 51787-31-6

• 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: calonysterone
• 英文别名: (2S,3R,10R,13R,17S)-2,3,6-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-one
• CAS: 51787-31-6
• 化学式: C₂₇H₄₀O₇
• 分子量: 476.61
• InChiKey: XAKKXZNYERXAIY-HTYOSDJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  138
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  calonysterone 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 甲醇 为溶剂， 反应 60.0h， 以51.8%的产率得到
  参考文献：
  名称：

  Side-chain cleaved phytoecdysteroid metabolites as activators of protein kinase B

  摘要：

  Phytoecdysteroids exert their non-hormonal anabolic and adaptogenic effects in mammals, including humans, through a partially revealed mechanism of action involving the activation of protein kinase B (Akt). We have recently found that poststerone, a side-chain cleaved in vivo metabolite of 20-hydroxyecdysone, exerts potent anabolic activity in rats.Here we report the semi-synthetic preparation of a series of side-chain cleaved ecdysteroids and their activity on the Akt phosphorylation in murine skeletal muscle cells. Twelve C-21 ecdysteroids including 8 new compounds were obtained through the oxidative side-chain cleavage of various phytoecdysteroids, or through the base-catalyzed autoxidation of poststerone. The complete H-1 and C-13 NMR spectroscopic assignments of the new compounds are presented. Among the tested compounds, 9 could activate Akt stronger than poststerone revealing that side-chain cleaved derivatives of phytoecdysteroids other than 20-hydroxyecdysone are valuable bioactive metabolites. Thus, our results suggest that the expectable in vivo formation of such compounds should contribute to the bioactivity of herbal preparations containing ecdysteroid mixtures.

  DOI：

  10.1016/j.bioorg.2018.10.049
• 作为产物：
  描述：

  蜕皮激素 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 calonysterone
  参考文献：
  名称：

  Oxidized Metabolites of 20-Hydroxyecdysone and Their Activity on Skeletal Muscle Cells: Preparation of a Pair of Desmotropes with Opposite Bioactivities

  摘要：

  Increasing the activation of protein kinase B (Akt) has been suggested as a key signaling step in the nonhormonal anabolic activity of the phytoecdysteroid 20-hydroxyecdysone (20E) in mammals. Base-catalyzed autoxidation of this compound was shown previously to yield interesting B-ring-modified analogues. Herein is reported a thorough study on this reaction, resulting in the preparation and complete NMR spectroscopic assignments of calonysterone (5) and its previously overlooked desmotropic pair (7), along with two new sensitive metabolites of 20E. The two isomers showed considerable stability in solution. Time dependency of the reaction for yield optimization is also presented; by means of analytical HPLC, the two desmotropes can reach a maximum combined yield of >90%. The activity of these compounds on Akt phosphorylation was tested in murine skeletal muscle cells. Compounds 2 and 5 showed more potent activity than 20E in increasing Akt activation, while compound 7 exerted an opposite effect. As such, the present study provides the first direct evidence for a pair of desmotropes exerting significantly different bioactivities.

  DOI：

  10.1021/acs.jnatprod.5b00249

文献信息

• Base-catalyzed autoxidation of 20-hydroxyecdysone: Synthesis of calonysterone and 920-dihydroxyecdysone
  作者：Apichart Suksamrarn、Penpan Ganpinyo、Chatriwat Sommechai

  DOI：10.1016/s0040-4039(00)73380-6

  日期：1994.6

  Base-catalyzed autoxidation of 20-hydroxyecdysone (2) gave an unusually modified ecdysteroid calonysterone (1) and 9,20-dihydroxyecdysone (4).

  碱催化20-羟基蜕皮激素的自氧化（2）得到了异常修饰的蜕皮甾体钙酮固酮（1）和9,20-二羟基蜕皮激素（4）。
• Side-chain cleaved phytoecdysteroid metabolites as activators of protein kinase B
  作者：Halima Meriem Issaadi、József Csábi、Tusty-Jiuan Hsieh、Tamás Gáti、Gábor Tóth、Attila Hunyadi

  DOI：10.1016/j.bioorg.2018.10.049

  日期：2019.2

  Phytoecdysteroids exert their non-hormonal anabolic and adaptogenic effects in mammals, including humans, through a partially revealed mechanism of action involving the activation of protein kinase B (Akt). We have recently found that poststerone, a side-chain cleaved in vivo metabolite of 20-hydroxyecdysone, exerts potent anabolic activity in rats.Here we report the semi-synthetic preparation of a series of side-chain cleaved ecdysteroids and their activity on the Akt phosphorylation in murine skeletal muscle cells. Twelve C-21 ecdysteroids including 8 new compounds were obtained through the oxidative side-chain cleavage of various phytoecdysteroids, or through the base-catalyzed autoxidation of poststerone. The complete H-1 and C-13 NMR spectroscopic assignments of the new compounds are presented. Among the tested compounds, 9 could activate Akt stronger than poststerone revealing that side-chain cleaved derivatives of phytoecdysteroids other than 20-hydroxyecdysone are valuable bioactive metabolites. Thus, our results suggest that the expectable in vivo formation of such compounds should contribute to the bioactivity of herbal preparations containing ecdysteroid mixtures.
• Oxidized Metabolites of 20-Hydroxyecdysone and Their Activity on Skeletal Muscle Cells: Preparation of a Pair of Desmotropes with Opposite Bioactivities
  作者：József Csábi、Tusty-Jiuan Hsieh、Feria Hasanpour、Ana Martins、Zoltán Kele、Tamás Gáti、András Simon、Gábor Tóth、Attila Hunyadi

  DOI：10.1021/acs.jnatprod.5b00249

  日期：2015.10.23

  Increasing the activation of protein kinase B (Akt) has been suggested as a key signaling step in the nonhormonal anabolic activity of the phytoecdysteroid 20-hydroxyecdysone (20E) in mammals. Base-catalyzed autoxidation of this compound was shown previously to yield interesting B-ring-modified analogues. Herein is reported a thorough study on this reaction, resulting in the preparation and complete NMR spectroscopic assignments of calonysterone (5) and its previously overlooked desmotropic pair (7), along with two new sensitive metabolites of 20E. The two isomers showed considerable stability in solution. Time dependency of the reaction for yield optimization is also presented; by means of analytical HPLC, the two desmotropes can reach a maximum combined yield of >90%. The activity of these compounds on Akt phosphorylation was tested in murine skeletal muscle cells. Compounds 2 and 5 showed more potent activity than 20E in increasing Akt activation, while compound 7 exerted an opposite effect. As such, the present study provides the first direct evidence for a pair of desmotropes exerting significantly different bioactivities.