3β-hydroxyergosta-8,24(28)-dien-7-one | 1175710-04-9

• 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: 3β-hydroxyergosta-8,24(28)-dien-7-one
• 英文别名: 3beta-Hydroxyergosta-8,24(28)-dien-7-one；(3S,5R,10S,13R,14R,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,5,6,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• CAS: 1175710-04-9
• 化学式: C₂₈H₄₄O₂
• 分子量: 412.656
• InChiKey: XNNFSCUGVQFHNA-KLARHEOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-hydroxyergosta-8,24(28)-dien-7-one 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 10.0h， 生成 [(3S,5R,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-7-oxo-1,2,3,4,5,6,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  7-Nor-ergosterolide, a Pentalactone-Containing Norsteroid and Related Steroids from the Marine-Derived Endophytic Aspergillus ochraceus EN-31

  摘要：

  7-Nor-ergosterolide (1), a rare 7-norsteroid with an unusual pentalactone B-ring system, and two new steroid derivatives, 3 beta,11 alpha-dihydroxyergosta-8,24(28)-dien-7-one (2) and 3 beta-hydroxyergosta-8,24(28)-dien-7-one (3), were characterized from the culture extract of Aspergillus ochraceus EN-31, an endophytic fungus isolated from the marine brown alga Sargassum kjellmanianum. In addition, nine known related steroids were isolated and identified. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The absolute configuration of the new steroids (1-3) was determined by application of the modified Mosher's method. Compound 1, which represents the first example of a 7-nor-ergosteroid possessing a pentalactone B-ring system in a naturally occurring steroid, displayed cytotoxicity against NCl-H460, SMMC-7721, and SW1990 cell lines with IC50 values of 5.0, 7.0, and 28.0 mu g/mL, respectively. Compound 2 also displayed cytotoxicity against the SMMC-7721 cell line with an IC50 value of 28.0 mu g/mL.

  DOI：

  10.1021/np100386q

文献信息

• 7-Nor-ergosterolide, a Pentalactone-Containing Norsteroid and Related Steroids from the Marine-Derived Endophytic <i>Aspergillus ochraceus</i> EN-31
  作者：Chuan-Ming Cui、Xiao-Ming Li、Li Meng、Chun-Shun Li、Cai-Guo Huang、Bin-Gui Wang

  DOI：10.1021/np100386q

  日期：2010.11.29

  7-Nor-ergosterolide (1), a rare 7-norsteroid with an unusual pentalactone B-ring system, and two new steroid derivatives, 3 beta,11 alpha-dihydroxyergosta-8,24(28)-dien-7-one (2) and 3 beta-hydroxyergosta-8,24(28)-dien-7-one (3), were characterized from the culture extract of Aspergillus ochraceus EN-31, an endophytic fungus isolated from the marine brown alga Sargassum kjellmanianum. In addition, nine known related steroids were isolated and identified. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The absolute configuration of the new steroids (1-3) was determined by application of the modified Mosher's method. Compound 1, which represents the first example of a 7-nor-ergosteroid possessing a pentalactone B-ring system in a naturally occurring steroid, displayed cytotoxicity against NCl-H460, SMMC-7721, and SW1990 cell lines with IC50 values of 5.0, 7.0, and 28.0 mu g/mL, respectively. Compound 2 also displayed cytotoxicity against the SMMC-7721 cell line with an IC50 value of 28.0 mu g/mL.