gitogenin 3-O-{O-β-D-glucopyranosyl-(1->2)-O-[O-β-D-apiofuranosyl-(1->4)-β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside}

• 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: gitogenin 3-O-{O-β-D-glucopyranosyl-(1->2)-O-[O-β-D-apiofuranosyl-(1->4)-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-4-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₅₆H₉₂O₂₈
• 分子量: 1213.33
• InChiKey: COBZLHMDIHCUIO-DDBDLJBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  84
• 可旋转键数：
  15
• 环数：
  11.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  434
• 氢给体数：
  16
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  gitogenin 3-O-{O-β-D-glucopyranosyl-(1->2)-O-[O-β-D-apiofuranosyl-(1->4)-β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside} 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以11.4 mg的产率得到gitogenin 3-O-2)-O-<β-D-glucopyranosyl-(1<*>3)>-O-β-D-glucopyranosyl-(1<*>4)-β-D-galactopyranoside>
  参考文献：
  名称：

  吊兰地下部分甾体皂苷及其对肿瘤启动子诱导的hela细胞磷脂代谢的抑制作用

  摘要：

  从新鲜的 Chlorophytum comosum 地下部分中分离出三种新的包含 β-D-apiofuranose 的螺甾醇五糖苷以及四种已知的皂苷。新化合物的结构由光谱数据确定，包括二维核磁共振和部分酸催化水解为 (25R)-5 alpha-spirostane-2 alpha,3 beta-diol 3-O-[O-beta- D-吡喃葡萄糖基-(1-->2)-O-[O-β-D-吡呋喃糖基-(1-->4)-β-D-吡喃葡萄糖基-(1-->3)]-O-β- D-吡喃葡萄糖基-(1-->4)-β-D-吡喃半乳糖苷], (25R)-3 beta-hydroxy-5 alpha-spirostan-12-one (hecogenin) 3-O-[O-beta-D-吡喃葡萄糖基-(1-->2)-O-[O-β-D-吡呋喃糖基-(1- ->4)-β-D-吡喃木糖基-(1-->3)]-O-β-D-吡喃葡

  DOI：

  10.1016/0031-9422(95)00789-x

文献信息

• Steroidal saponins from the underground parts of Chlorophytum comosum and their inhibitory activity on tumour promoter-induced phospholipids metabolism of hela cells
  作者：Yoshihiro Mimaki、Toshihiro Kanmoto、Yutaka Sashida、Atsuko Nishino、Yoshiko Satomi、Hoyoku Nishino

  DOI：10.1016/0031-9422(95)00789-x

  日期：1996.3

  apiofuranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)]-O-beta-D-gluc opyranosyl- (1-->4)-beta-D-galactopyranoside], respectively. The isolated saponins were examined for inhibitory activity using 12-O-tetradecanoylphorbor-13-acetate-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to identify new antitumour-promoter compounds.

  从新鲜的 Chlorophytum comosum 地下部分中分离出三种新的包含 β-D-apiofuranose 的螺甾醇五糖苷以及四种已知的皂苷。新化合物的结构由光谱数据确定，包括二维核磁共振和部分酸催化水解为 (25R)-5 alpha-spirostane-2 alpha,3 beta-diol 3-O-[O-beta- D-吡喃葡萄糖基-(1-->2)-O-[O-β-D-吡呋喃糖基-(1-->4)-β-D-吡喃葡萄糖基-(1-->3)]-O-β- D-吡喃葡萄糖基-(1-->4)-β-D-吡喃半乳糖苷], (25R)-3 beta-hydroxy-5 alpha-spirostan-12-one (hecogenin) 3-O-[O-beta-D-吡喃葡萄糖基-(1-->2)-O-[O-β-D-吡呋喃糖基-(1- ->4)-β-D-吡喃木糖基-(1-->3)]-O-β-D-吡喃葡