(20R,22R)-1α-acetoxy-14α,20-dihydroxywitha-5,24-dienolide-3β-(O-β-D-glucopyranoside) | 227179-07-9

• 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: (20R,22R)-1α-acetoxy-14α,20-dihydroxywitha-5,24-dienolide-3β-(O-β-D-glucopyranoside)
• 英文别名: [(1S,3R,8R,9S,10R,13R,14R,17S)-17-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-1-yl] acetate
• CAS: 227179-07-9
• 化学式: C₃₆H₅₄O₁₂
• 分子量: 678.818
• InChiKey: ACXRDVCAKSUCPM-SOTUBAIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (20R,22R)-1α-acetoxy-14α,20-dihydroxywitha-5,24-dienolide-3β-(O-β-D-glucopyranoside) 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以12.7 mg的产率得到(R)-6-[(R)-1-Hydroxy-1-((1S,3R,8R,9S,10R,13R,14R,17S)-1,3,14-trihydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-3,4-dimethyl-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  New Withanolide Glycosides from Physalis peruviana L.

  摘要：

  Four new withanolide glycosides (1-4) have been isolated from Physalis peruviana. Their structures were established as (20R, 22R)-1α-acetoxy-14α, 20-dihydroxywitha-5, 24-dienolide-3β-(O-β-D-glucopyranoside) (1), (20S, 22R)-1α-acetoxy-27-hydroxywitha-5, 24-dienolide-3β-(O-β-D-glucopyranoside) (2), (20R, 22R)-20, 27-dihydroxy-1-oxowitha-5, 24-dienolide-3β-(O-β-D-glucopyranoside) (3), and (20R, 22R)-14α, 20, 27-trihydroxy-1-oxowitha-5, 24-dienolide-3β-(O-β-D-glucopyranoside) (4) on the basis of spectroscopic data including two dimensional NMR techniques and through chemical transformations.

  DOI：

  10.1248/cpb.47.477

文献信息

• New Withanolide Glycosides from Physalis peruviana L.
  作者：Saeed AHMAD、Rehana YASMIN、Abdul MALIK

  DOI：10.1248/cpb.47.477

  日期：——

  Four new withanolide glycosides (1-4) have been isolated from Physalis peruviana. Their structures were established as (20R, 22R)-1α-acetoxy-14α, 20-dihydroxywitha-5, 24-dienolide-3β-(O-β-D-glucopyranoside) (1), (20S, 22R)-1α-acetoxy-27-hydroxywitha-5, 24-dienolide-3β-(O-β-D-glucopyranoside) (2), (20R, 22R)-20, 27-dihydroxy-1-oxowitha-5, 24-dienolide-3β-(O-β-D-glucopyranoside) (3), and (20R, 22R)-14α, 20, 27-trihydroxy-1-oxowitha-5, 24-dienolide-3β-(O-β-D-glucopyranoside) (4) on the basis of spectroscopic data including two dimensional NMR techniques and through chemical transformations.