(25R)-2α-hydroxyspirost-5-en-3β-yl O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside | 70880-60-3

• 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: (25R)-2α-hydroxyspirost-5-en-3β-yl O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside
• 英文别名: karatavioside A；(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,15R,16R)-15-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 70880-60-3
• 化学式: C₅₀H₈₀O₂₃
• 分子量: 1049.17
• InChiKey: XVPVVWNZAJAPLF-MMPILWSFSA-N

物化性质

• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  73
• 可旋转键数：
  11
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  355
• 氢给体数：
  13
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  (25R)-26-[(O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl)oxy]-2α-hydroxy-22α-methoxyfurost-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside 在 β-D-glucosidase 作用下， 以 aq. acetate buffer 为溶剂， 反应 48.0h， 以1.7 mg的产率得到(25R)-2α-hydroxyspirost-5-en-3β-yl O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside
  参考文献：
  名称：

  Karataviosides G–K, five new bisdesmosidic steroidal glycosides from the bulbs of Allium karataviense

  摘要：

  We have analyzed the steroidal glycosides in Allium karataviense bulbs, and isolated five new bisdesmosidic steroidal glycosides: karataviosides G-K (1-5). The structures were elucidated by extensive spectroscopic analysis, including 2D NMR and enzymatic and hydrolytic cleavage. Karatavioside G (1) is an entirely novel furostanol glycoside, which has an O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl unit at C-26 of the aglycone. Although a variety of cholestanol glycosides have been isolated, mainly from Liliaceae and Agavaceae, karataviosides J and K (4 and 5) are also notable because they are the most polar cholestanol bisdesmosides discovered, in which a lycotetraose is attached to C-3 of the aglycone, and a glucose or O-glucosyl-(1→3)-glucose is attached at C-16. The isolated glycosides were also evaluated for their cytotoxic activities against cultured tumor cell lines.

  DOI：

  10.1016/j.steroids.2014.09.010

文献信息

• Karataviosides G–K, five new bisdesmosidic steroidal glycosides from the bulbs of Allium karataviense
  作者：Minpei Kuroda、Kazutomo Ori、Hiroshi Takayama、Hiroshi Sakagami、Yoshihiro Mimaki

  DOI：10.1016/j.steroids.2014.09.010

  日期：2015.1

  We have analyzed the steroidal glycosides in Allium karataviense bulbs, and isolated five new bisdesmosidic steroidal glycosides: karataviosides G-K (1-5). The structures were elucidated by extensive spectroscopic analysis, including 2D NMR and enzymatic and hydrolytic cleavage. Karatavioside G (1) is an entirely novel furostanol glycoside, which has an O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl unit at C-26 of the aglycone. Although a variety of cholestanol glycosides have been isolated, mainly from Liliaceae and Agavaceae, karataviosides J and K (4 and 5) are also notable because they are the most polar cholestanol bisdesmosides discovered, in which a lycotetraose is attached to C-3 of the aglycone, and a glucose or O-glucosyl-(1→3)-glucose is attached at C-16. The isolated glycosides were also evaluated for their cytotoxic activities against cultured tumor cell lines.