theonellasterol | 76758-19-5

• 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: theonellasterol
• 英文别名: (3S,5R,9R,10R,13R,17R)-17-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-4-methylidene-1,2,3,5,6,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
• CAS: 76758-19-5
• 化学式: C₃₀H₅₀O
• 分子量: 426.726
• InChiKey: CVZFQTIJNREPCP-HFLKTIQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  theonellasterol 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以84%的产率得到(24S)-24-ethyl-3β-hydroxyl-5α-cholest-4-one
  参考文献：
  名称：

  Preliminary Structure-Activity Relationship on Theonellasterol, a New Chemotype of FXR Antagonist, from the Marine Sponge Theonella swinhoei

  摘要：

  Using theonellasterol as a novel FXR antagonist hit, we prepared a series of semi-synthetic derivatives in order to gain insight into the structural requirements for exhibiting antagonistic activity. These derivatives are characterized by modification at the exocyclic carbon-carbon double bond at C-4 and at the hydroxyl group at C-3 and were prepared from theonellasterol using simple reactions. Pharmacological investigation showed that the introduction of a hydroxyl group at C-4 as well as the oxidation at C-3 with or without concomitant modification at the exomethylene functionality preserve the ability of theonellasterol to inhibit FXR transactivation caused by CDCA. Docking analysis showed that the placement of these molecules in the FXR-LBD is well stabilized when on ring A functional groups, able to form hydrogen bonds and π interactions, are present.

  DOI：

  10.3390/md10112448
• 作为产物：
  描述：

  theonellasterone 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 苯 为溶剂， 反应 0.33h， 以72 mg的产率得到theonellasterol
  参考文献：
  名称：

  Marine Natural Products. XXX. Two New 3-Keto-4-methylene Steroids, Theonellasterone and Conicasterone, and a Diels-Alder Type Dimeric Steroid Bistheonellasterone, from the Okinawan Marine Sponge Theonella swinhoei.

  摘要：

  从冲绳海洋海绵Theonella swinhoei中分离出两种新的3-酮-4-亚甲基类固醇，即theonellasterone（3）和conicasterone（4），以及一种Diels-Alder型二聚类固醇，即bistheonellasterone（5），以及两种已知的4-亚甲基固醇，即theonellasterol（1）和conicasterol（2）。这些类固醇的结构已经根据化学和物理化学证据得到阐明。Bistheonellasterone（5）被认为是通过theonellasterone（3）及其Δ4-异构体的Diels-Alder环加成生物合成的。非常有趣的是，在光学显微镜下，theonellasterone（3）和conicasterone（4）被看作是沉积在新鲜海洋海绵组织中的晶体。

  DOI：

  10.1248/cpb.40.1773

文献信息

• 4-Methylenesterols from a Sponge Theonella swinhoei
  作者：Jheng-Kun Guo、Ching-Ying Chiang、Mei-Chin Lu、Wen-Been Chang、Jui-Hsin Su

  DOI：10.3390/md10071536

  日期：——

  Three new 4-methylenesterols, theonellasterol K (1), acetyltheonellasterol (2) and acetyldehydroconicasterol (3), along with two known sterols, theonellasterol (4) and theonellasterone (5), were isolated from the sponge Theonella swinhoei. The structures of these compounds were elucidated on the basis of their spectroscopic data and comparison of the NMR data with those of known analogues. Compound

  从海绵 Theonella swinhoei 中分离出三种新的 4-亚甲基甾醇，theonellasterol K (1)、乙酰基theonellasterol (2) 和 acetyldehydroconicasterol (3)，以及两种已知的甾醇，theonellasterol (4) 和 theonellasterone (5)。这些化合物的结构基于它们的光谱数据和核磁共振数据与已知类似物的比较来阐明。化合物 1 对 HCT-116、K562 和 Molt 4 癌细胞系表现出显着的细胞毒活性。