3-O-{β-D-xylopyranosyl-(1->3)-α-L-arabinopyranosyl-(1->2)-[α-L-rhamnopyranosyl-(1->4)]-β-D-glucopyranosyl}-(25S)-spirost-5-ene-3β,17α-diol | 1254121-22-6

• 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: 3-O-{β-D-xylopyranosyl-(1->3)-α-L-arabinopyranosyl-(1->2)-[α-L-rhamnopyranosyl-(1->4)]-β-D-glucopyranosyl}-(25S)-spirost-5-ene-3β,17α-diol
• 英文别名: lirigramoside A；(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-5-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6R,7S,8S,9S,12S,13R,16S)-8-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-6-methyloxane-3,4,5-triol
• CAS: 1254121-22-6
• 化学式: C₄₉H₇₈O₂₁
• 分子量: 1003.15
• InChiKey: YBJITCGEQWUYPH-XYHLCLBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  70
• 可旋转键数：
  9
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  315
• 氢给体数：
  11
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  3-O-{β-D-xylopyranosyl-(1->3)-α-L-arabinopyranosyl-(1->2)-[α-L-rhamnopyranosyl-(1->4)]-β-D-glucopyranosyl}-(25S)-spirost-5-ene-3β,17α-diol 、 L-半胱氨酸甲酯盐酸盐 在 盐酸 、 水 、 吡啶 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 、
  参考文献：
  名称：

  Novel steroidal saponins from Liriope graminifolia (Linn.) Baker with anti-tumor activities

  摘要：

  Phytochemical investigation of the underground parts of Liriope graminifolia (Linn.) Baker resulted in the isolation of two new steroidal saponins lirigramosides A (1) and B (2) along with four known compounds. The structures were determined by extensive spectral analysis, including two-dimensional (2D) NMR spectroscopy and chemical methods, to be 3-O-{beta-D-xylopyranosyl-(1 -> 3)-alpha-L-arabinopyranosyl-( 1 -> 2)-[alpha-L-rhamnopyranosyl-(1 -> 4)]-beta-D-glucopyranosyl-(25S)-spirost-5-ene-3 beta, 17 alpha-diol (1), 1-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-(25R)-ruscogenin (2), 1-O-beta-D-xylopyranosyl-3-O-alpha-L-rhamnopyranosyl-(25S)-ruscogenin (3), 3-O-alpha-L-rhamnopyranosyl-1-O-sulfo-(25S)-ruscogenin (4), methylophiopogonanone B (5), and 5,7-dihydroxy-3-(4-methoxybenzyl)-6-methyl-chroman-4-one, (ophiopogonanone B, 6), respectively. Compound 1 has a new (25S)-spirost-5-ene-3 beta, 17 alpha-diol ((25S)-pennogenin) aglycone moiety. The isolated compounds were evaluated for their cytotoxic activities against Hela and SMMC-7721 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.015