(25S)-1β,4β,5β-trihydroxy-spirostane-3β-yl O-α-L-arabinopyranoside

• 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: (25S)-1β,4β,5β-trihydroxy-spirostane-3β-yl O-α-L-arabinopyranoside
• 英文别名: tupistroside A；(1S,2S,4S,5'S,6R,7S,8R,9S,12S,13S,14R,16S,17S,18R)-5',7,9,13-tetramethyl-16-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-14,17,18-triol
• 化学式: C₃₂H₅₂O₁₀
• 分子量: 596.759
• InChiKey: OVEQGGRXSXVKSO-ZULLFIFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  42
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (25S)-1β,4β,5β-trihydroxy-spirostane-3β-yl O-α-L-arabinopyranoside 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以10 mg的产率得到铃兰皂苷元B
  参考文献：
  名称：

  Polyhydroxylated steroidal constituents from the fresh rhizomes of

  摘要：

  Six new polyhydroxylated steroidal saponins, tupistrosides A-F (1-6), together with nine known steroids, were isolated from the fresh rhizomes of Tupistra yunnanensis. Their structures were elucidated to be (25S)-1 beta,4 beta,5 beta-trihydroxy-spirostane-3 beta-yl-O-alpha-L-arabinopyranoside (1), 1 beta,24 beta-dihydroxy-spirost-5,25(27)-dien-3 alpha-yl-O-beta-D-glucopyranoside (2), (22S,25S)- 1 alpha,2 beta,3 alpha,5 alpha-tetrahydroxy-furo-spirostane-26-yl-O-beta-D-glucopyranoside (3), 1 beta,3 alpha,22 xi-trihydroxy-furost-5,25(27)-dien-26-yl O-beta-D-glucopyranoside (4), 26-O-beta-D-glucopyranosyl-1 beta,22-dihydroxy-furost-5-en-3 alpha-yl O-beta-D-glucopyranoside (5) and 22-methoxy-1 beta,2 beta,3 beta,4 beta,5 beta,7 alpha-hexahydroxy-furost-25(27)-en-6-one-26-yl O-beta-D-glucopyranoside (6), respectively, by means of spectroscopic analysis and the results of acid hydrolysis. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.04.003

文献信息

• Polyhydroxylated steroidal constituents from the fresh rhizomes of
  作者：Q YANG、Y ZHANG、H LI、C YANG

  DOI：10.1016/j.steroids.2005.04.003

  日期：2005.9

  Six new polyhydroxylated steroidal saponins, tupistrosides A-F (1-6), together with nine known steroids, were isolated from the fresh rhizomes of Tupistra yunnanensis. Their structures were elucidated to be (25S)-1 beta,4 beta,5 beta-trihydroxy-spirostane-3 beta-yl-O-alpha-L-arabinopyranoside (1), 1 beta,24 beta-dihydroxy-spirost-5,25(27)-dien-3 alpha-yl-O-beta-D-glucopyranoside (2), (22S,25S)- 1 alpha,2 beta,3 alpha,5 alpha-tetrahydroxy-furo-spirostane-26-yl-O-beta-D-glucopyranoside (3), 1 beta,3 alpha,22 xi-trihydroxy-furost-5,25(27)-dien-26-yl O-beta-D-glucopyranoside (4), 26-O-beta-D-glucopyranosyl-1 beta,22-dihydroxy-furost-5-en-3 alpha-yl O-beta-D-glucopyranoside (5) and 22-methoxy-1 beta,2 beta,3 beta,4 beta,5 beta,7 alpha-hexahydroxy-furost-25(27)-en-6-one-26-yl O-beta-D-glucopyranoside (6), respectively, by means of spectroscopic analysis and the results of acid hydrolysis. (c) 2005 Elsevier Inc. All rights reserved.