(5β,17α)-Δ¹⁶⁽¹⁷⁾-20-one-pregn-2β,3β-diol 3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside

• 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: (5β,17α)-Δ¹⁶⁽¹⁷⁾-20-one-pregn-2β,3β-diol 3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside
• 英文别名: (5β,17)-20-one-pregn-16-ene-2β,3β-diol 3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside；timopregnane B
• 化学式: C₃₃H₅₂O₁₃
• 分子量: 656.768
• InChiKey: GXHVHRYRIPOBCR-WNZYWLLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.87
• 重原子数：
  46.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  215.83
• 氢给体数：
  8.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (5β,17α)-Δ¹⁶⁽¹⁷⁾-20-one-pregn-2β,3β-diol 3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside 在 三氟乙酸 作用下， 反应 5.0h， 生成 葡萄糖 、 口服葡萄糖
  参考文献：
  名称：

  New steroidal glycosides from the rhizome of Anemarrhena asphodeloides

  摘要：

  Two new steroidal saponins, timosaponin X (1) and timosaponin Y (2), and one new pregnane glycoside, timopregnane B (3), were isolated from the rhizomes of Anemarrhena asphodeloides, as well as three known compounds 25S-timosaponin BII (4), protodesgalactotigonin (5), and timosaponin BII-a (6) isolated from this plant for the first time. By the detailed analysis of 1D, 2D NMR, MS spectra, and chemical evidences, the structures of new compounds were elucidated as 26-O-beta-D-glucopyranosyl-(25S)-5 beta-22-methoxy-furost-3 beta, 26-diol 3-O-beta-D-glucopyranosyl( 1 -> 2)-alpha-L-arabinopyranoside (1), 5 beta-pseudo-spirost-3 beta, 15 alpha, 23 alpha-triol 3-O-beta-D-glucopyranosyl-( 1 -> 2)-beta-D-galactopyranoside (2), (5 beta, 17 alpha)-Delta(16(17))-20-one-pregn-2 beta, 3 beta-diol 3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranoside (3).

  DOI：

  10.1080/10286020.2014.942658

文献信息

• New steroidal glycosides from the rhizome of <i>Anemarrhena asphodeloides</i>
  作者：Jian-Chao Yuan、Jie Zhang、Fang-Xu Wang、Xu Pang、Yang Zhao、Cheng-Qi Xiong、Bai-Ping Ma

  DOI：10.1080/10286020.2014.942658

  日期：2014.9.2

  Two new steroidal saponins, timosaponin X (1) and timosaponin Y (2), and one new pregnane glycoside, timopregnane B (3), were isolated from the rhizomes of Anemarrhena asphodeloides, as well as three known compounds 25S-timosaponin BII (4), protodesgalactotigonin (5), and timosaponin BII-a (6) isolated from this plant for the first time. By the detailed analysis of 1D, 2D NMR, MS spectra, and chemical evidences, the structures of new compounds were elucidated as 26-O-beta-D-glucopyranosyl-(25S)-5 beta-22-methoxy-furost-3 beta, 26-diol 3-O-beta-D-glucopyranosyl( 1 -> 2)-alpha-L-arabinopyranoside (1), 5 beta-pseudo-spirost-3 beta, 15 alpha, 23 alpha-triol 3-O-beta-D-glucopyranosyl-( 1 -> 2)-beta-D-galactopyranoside (2), (5 beta, 17 alpha)-Delta(16(17))-20-one-pregn-2 beta, 3 beta-diol 3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranoside (3).