25-hydroxydacryhainansterone | 58347-77-6

• 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: 25-hydroxydacryhainansterone
• 英文别名: 25-Hydroxydacrihainansterone；(2S,3R,5R,10S,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 58347-77-6
• 化学式: C₂₇H₄₂O₇
• 分子量: 478.626
• InChiKey: LUFONRHFFBQBJJ-MFLHRAQLSA-N

物化性质

• 熔点：
  151-153 °C
• 沸点：
  728.3±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  138
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  土克甾酮 在 palladium on activated charcoal sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以72%的产率得到25-hydroxydacryhainansterone
  参考文献：
  名称：

  Stereoselective catalytic hydrogenation of Δ7-6-ketosteroids in the presence of sodium nitrite

  摘要：

  Catalytic hydrogenation with Pd-C as a catalyst in the presence of sodium nitrite is a simple, convenient and high yielding stereoselective reduction of olefinic function of Delta(7)-6-ketosteroids to the corresponding dihydro analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00580-x

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
• Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone
  作者：Natalya A. Veskina、Aliya Sh. Ibragimova、Ilgiz V. Galyautdinov、Leonard M. Khalilov、Victor N. Odinokov

  DOI：10.1016/j.mencom.2010.09.019

  日期：2010.9

  9 alpha,14 alpha-epoxy-14-deoxy-20-hydroxyecdysone diacetonideon treatment with NaBH4 undergoes reduction of 6-keto group and cleavage of allylic oxetane ring, the 6-keto reduction is accompanied by beta ->alpha epimerization of the adjacent HC5 centre. Subsequent re-oxidation of the 6-CHOH fragment into ketone with pyridinium chlorochromate and acidic deprotection affords 25-hydroxydachryhainansterone possessing beta-HC5 configuration due to the re-epimerisation at this centre
• 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.