(25R)-2α-hydroxy-5α-spirostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside | 1499187-77-7

• 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: (25R)-2α-hydroxy-5α-spirostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,15R,16R,18S)-15-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1499187-77-7
• 化学式: C₅₁H₈₄O₂₄
• 分子量: 1081.21
• InChiKey: OJXYLGQQFXELNY-BFOPJGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.94
• 重原子数：
  75.0
• 可旋转键数：
  12.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  375.52
• 氢给体数：
  14.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  (25R)-2α-hydroxy-5α-spirostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside 在 alpha-L-rhamnosidase 、 potassium acetate 、 溶剂黄146 作用下， 以 aq. buffer 为溶剂， 反应 49.0h， 以2.7 mg的产率得到支脱皂苷元
  参考文献：
  名称：

  Steroidal glycosides from the bulbs of Bessera elegans and their cytotoxic activities

  摘要：

  Examination of the bulbs of Bessera elegans (Liliaceae) led to isolation of nine new and five known steroidal glycosides. The structures of the nine compounds were determined based on the results of spectroscopic analysis, including two-dimensional NMR, and hydrolysis followed by chromatographic and spectroscopic analysis. The isolated compounds and derivatives were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human diploid fibroblasts. One compound, the pseudo-furostanol glycoside, induced apoptosis in HL-60 and A549 cells in a time-dependent manner and cell-cycle arrest at the G0/G1 phase in A549 cells. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.09.023
• 作为产物：
  描述：

  (25R)-26-[(β-D-glucopyranosyl)oxy]-2α,22α-dihydroxy-5α-furostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside 在 β-D-glucosidase 、 sodium acetate 、 溶剂黄146 作用下， 以 aq. buffer 为溶剂， 反应 27.0h， 以2 mg的产率得到(25R)-2α-hydroxy-5α-spirostan-3β-yl O-β-D-galactopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside
  参考文献：
  名称：

  Steroidal glycosides from the bulbs of Bessera elegans and their cytotoxic activities

  摘要：

  Examination of the bulbs of Bessera elegans (Liliaceae) led to isolation of nine new and five known steroidal glycosides. The structures of the nine compounds were determined based on the results of spectroscopic analysis, including two-dimensional NMR, and hydrolysis followed by chromatographic and spectroscopic analysis. The isolated compounds and derivatives were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human diploid fibroblasts. One compound, the pseudo-furostanol glycoside, induced apoptosis in HL-60 and A549 cells in a time-dependent manner and cell-cycle arrest at the G0/G1 phase in A549 cells. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.09.023