6α-O-[β-D-xylopyranosyl-(1->3)-β-D-quinovopyranosyl]-(25S)-5α-spirostan-3β,23β-diol | 713144-09-3

• 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: 6α-O-[β-D-xylopyranosyl-(1->3)-β-D-quinovopyranosyl]-(25S)-5α-spirostan-3β,23β-diol
• 英文别名: 6-O-β-D-xylopyranosyl-(1''→3')-β-D-quinovopyranosyl-(23R,25S)-3β,6α,23-trihydroxy-5α-spirostane；(2S,3R,4S,5R)-2-[(2R,3R,4S,5R,6R)-2-[(1R,2S,3'R,4S,5'S,6S,7S,8R,9S,12S,13R,16S,18S,19S)-3',16-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl]oxyoxane-3,4,5-triol
• CAS: 713144-09-3
• 化学式: C₃₈H₆₂O₁₃
• 分子量: 726.902
• InChiKey: FOCICMJCJFCWOL-XFQGNVHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  51
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  197
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 6α-O-[β-D-xylopyranosyl-(1->3)-β-D-quinovopyranosyl]-(25S)-5α-spirostan-3β,23β-diol 在 吡啶 作用下， 反应 3.0h， 以15 mg的产率得到[(1R,2S,3'R,4S,5'S,6S,7S,8R,9S,12S,13R,16S,18S,19S)-3'-acetyloxy-19-[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-triacetyloxyoxan-2-yl]oxyoxan-2-yl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl] acetate
  参考文献：
  名称：

  Antimycotic Spirostanol Saponins from Solanum hispidum Leaves and Their Structure−Activity Relationships

  摘要：

  A new spirostanol saponin, together with three known saponins, were isolated from the leaves of Solanum hispidum. The structure of the new saponin was elucidated as 6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta -ol (1) on the basis of spectroscopic analysis (H-1 NMR, C-13 NMR, H-1-H-1 COSY, HMQC, HMBC, and HRFABMS). All of the isolated compounds showed antimycotic activity. The most active compound was 6alpha-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-quinovopyranosyl]-(25S)-5alpha-spirostan-3beta-ol (2) (MIC = 25 mug/mL against both Trichophyton mentagrophytes and T. rubrum). The structure-activity relationships of the isolated compounds and those isolated from S. chrysotrichum are discussed.

  DOI：

  10.1021/np0305019

文献信息

• Antimycotic Spirostanol Saponins from <i>Solanum </i><i>hispidum</i> Leaves and Their Structure−Activity Relationships
  作者：Manases González、Alejandro Zamilpa、Silvia Marquina、Víctor Navarro、Laura Alvarez

  DOI：10.1021/np0305019

  日期：2004.6.1

  A new spirostanol saponin, together with three known saponins, were isolated from the leaves of Solanum hispidum. The structure of the new saponin was elucidated as 6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta -ol (1) on the basis of spectroscopic analysis (H-1 NMR, C-13 NMR, H-1-H-1 COSY, HMQC, HMBC, and HRFABMS). All of the isolated compounds showed antimycotic activity. The most active compound was 6alpha-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-quinovopyranosyl]-(25S)-5alpha-spirostan-3beta-ol (2) (MIC = 25 mug/mL against both Trichophyton mentagrophytes and T. rubrum). The structure-activity relationships of the isolated compounds and those isolated from S. chrysotrichum are discussed.