(25R)-3β-[{O-β-D-xylopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl}oxy]-5α-spirostan-12-one

• 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)-3β-[{O-β-D-xylopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl}oxy]-5α-spirostan-12-one
• 英文别名: hecogenin 3-O-{β-D-xylopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside}；(3β,5α,25R)-12-oxospirostan-3-yl O-β-D-xylopyranosyl-(1-3)-β-D-glucopyranosyl-(1-2)-[β-D-xylopyranosyl-(1-3)]-β-D-glucopyranosyl-(1-4)-β-D-galactopyranoside；hecogenin 3-O-β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside；hecogenin-3-O-β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside；(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-16-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-one
• 化学式: C₅₅H₈₈O₂₇
• 分子量: 1181.29
• InChiKey: VRHRSSKYXDMEDI-LBUHHRECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  82
• 可旋转键数：
  13
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  411
• 氢给体数：
  14
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  (25R)-3β-[{O-β-D-xylopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl}oxy]-5α-spirostan-12-one 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以3.4 mg的产率得到海柯吉宁
  参考文献：
  名称：

  来自Pol菜地上部分的类固醇糖苷。

  摘要：

  化学分析了aerial菜（Polianthes tuberosa）的地上部分，结果分离出了一种新的双去胆固醇胆甾烷糖苷（1）和三种新的螺固醇皂苷（2-4），以及一种已知的胆甾烷苷。通过光谱分析确定新糖苷的结构，包括2D NMR光谱数据和水解裂解的结果。评价分离的化合物对HL-60人早幼粒细胞白血病细胞的细胞毒性活性。

  DOI：

  10.1021/np000230r
• 作为产物：
  描述：

  26-O-β-D-glucopyranosyl-(25R)-5α-furost-3β,22α,26-triol-12-one 3-O-β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside 在 β-glucosidase 作用下， 以 acetate buffer 为溶剂， 反应 16.0h， 以18 mg的产率得到(25R)-3β-[{O-β-D-xylopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl}oxy]-5α-spirostan-12-one
  参考文献：
  名称：

  Spirostanol and Furostanol Glycosides from the Fresh Tubers of Polianthes tuberosa

  摘要：

  Six new steroid glycosides-two spirostanols, polianthosides B and C (1, 2), and four furostanols, polianthosides D-G (3-6)-were isolated from the fresh tubers of Polianthes tuberosa, together with seven known spirostanols (7-13) and a known furostanol (14) saponins. Their structures were elucidated on the basis of spectroscopic analysis and the results of acidic and enzymatic hydrolysis. The cytotoxic activities of 1-14 against HeLa cells are reported.

  DOI：

  10.1021/np034028a