(20R,22R)-2β,3β,9α,14α,20,22,25-heptahydroxy-5α-cholest-7-en-6-one

• 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: (20R,22R)-2β,3β,9α,14α,20,22,25-heptahydroxy-5α-cholest-7-en-6-one
• 英文别名: (5α)-9α,20-dihydroxyecdysone；9α,20-dihydroxy-5α-ecdysone；(2S,3R,5S,9S,10S,13R,14S,17S)-2,3,9,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
• 化学式: C₂₇H₄₄O₈
• 分子量: 496.642
• InChiKey: AHHRNGCAWAPZKG-GNWVCWHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  159
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  脱皮甾酮 2,3:20,22-二缩丙酮 在 高氯酸 、 氧气 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (20R,22R)-2β,3β,9α,14α,25-pentahydroxy-20,22-isopropylidenedioxy-5α-cholest-7-en-6-one 、 (20R,22R)-2β,3β,9α,14α,20,22,25-heptahydroxy-5α-cholest-7-en-6-one
  参考文献：
  名称：

  Hydroxylation and epimerization of ecdysteroids in alkaline media: Stereoselective synthesis of 9α-hydroxy-5α-ecdysteroids

  摘要：

  Autoxidation of diacetonides of 20-hydroxyecdysone and ponasterone A under treatment with excess of NaOH in methanol leads to the formation of 9α-hydroxy-5α-ecdysteroids previously not described. Their structures have been determined by detailed NMR analysis. Catalytic hydrogenation (Pd-C, MeOH-MeONa) of hydroxylated ecdysteroids affords the 7,8α-dihydro-9α-hydroxy-5α-ecdysteroids.

  DOI：

  10.1016/j.steroids.2014.06.019

文献信息

• 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.