(25R)-2α,3β-dihydroxy-5α-spirostane 3-O-α-L-rhamnopyranosyl-(1→2)-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: (25R)-2α,3β-dihydroxy-5α-spirostane 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside
• 英文别名: gitogenin 3b-O-[2-O-(α-L-rhamnopyanosyl)-β-D-galactopyranoside]；gitogenin 3-O-α-L-rhamnopyranosyl-(1-2)-β-D-galactopyranoside；tuberoside A；gitogenin 3-O-[O-α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranoside]；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(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-6-methyloxane-3,4,5-triol
• 化学式: C₃₉H₆₄O₁₃
• 分子量: 740.929
• InChiKey: KHIZMXXBPIYCQP-CLBBDDOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  52
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  197
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (25R)-2α,3β-dihydroxy-5α-spirostane 3-O-α-L-rhamnopyranosyl-(1→2)-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45 mg的产率得到支脱皂苷元
  参考文献：
  名称：

  玉簪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：

  从玉簪的地下部分分离出三种新的螺甾醇皂苷和两种新的呋甾醇皂苷。它们的结构被确定为 (25R)-5 alpha-spirostane-2 alpha, 3 beta-diol (gitogenin) 3-O-{O-alpha-L -rhamnopyranosyl-(1-->2)-beta-D-吡喃半乳糖苷}，gitogenin 3-O-{O-alpha-L-rhamnopyranosyl-(1-->2) -O-[β-D-吡喃葡萄糖基-(1-->4)]-β-D-吡喃半乳糖苷-， (25R)-5 alpha-spirostan-3 beta-ol (tigogenin) 3-O-{O-alpha-L-rhamnopyranosyl-(1-->2) -O-[beta-D-glupyranosyl-(1-- >4)]-β-D-吡喃半乳糖苷-, 26-O-β-D-吡喃葡萄糖基-22-O-甲基-(25R)-5

  DOI：

  10.1016/0031-9422(96)00030-1
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 12.0h， 以50.2 mg的产率得到(25R)-2α,3β-dihydroxy-5α-spirostane 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the Cytotoxic Gitogenin 3β-O-[2-O-(α-l-Rhamnopyranosyl)-β-d-galactopyranoside] and its Congeners

  摘要：

  (25R)-5a-螺甾-2a,3b-二醇 (gitogenin) 3β-O-[2-O-(α-l-鼠李吡喃糖基)-β-d-半乳吡喃糖苷] (1)，一种从长茎黄精（百合科）地下部分分离得到的细胞毒性螺甾皂苷，被简明地合成出来。在此过程中，其类似物2-4也被制备出来。所有四个化合物在抑制癌细胞生长方面与薯蓣皂苷具有相当的效力。

  DOI：

  10.1055/s-2006-926316

文献信息

• Synthesis of the Cytotoxic Gitogenin 3β-<i>O</i>-[2-<i>O</i>-(α-l-Rhamnopyranosyl)-β-d-galactopyranoside] and its Congeners
  作者：Yingxia Li、Biao Yu、Yichun Zhang、Tiantian Guo、Huashi Guan、Yan Hao

  DOI：10.1055/s-2006-926316

  日期：——

  (25R)-5a-Spirostan-2a,3b-diol (gitogenin) 3β-O-[2-O-(α-l-rhamnopyranosyl)-β-d-galactopyranoside] (1), a cytotoxic spirostan saponin isolated from the underground parts of Hosta longipes (Liliaceae), was concisely synthesized. In this context, its congeners 2-4 were also prepared. All four compounds showed comparable potency to dioscin in inhibition against the growth of tumor cells.

  (25R)-5a-螺甾-2a,3b-二醇 (gitogenin) 3β-O-[2-O-(α-l-鼠李吡喃糖基)-β-d-半乳吡喃糖苷] (1)，一种从长茎黄精（百合科）地下部分分离得到的细胞毒性螺甾皂苷，被简明地合成出来。在此过程中，其类似物2-4也被制备出来。所有四个化合物在抑制癌细胞生长方面与薯蓣皂苷具有相当的效力。
• Steroidal saponins from Hosta longipes and their inhibitory activity on tumour promoter-induced phospholipid metabolism of HeLa Cells
  作者：Yoshihiro Mimaki、Toshihiro Kanmoto、Minpei Kuroda、Yutaka Sashida、Yoshiko Satomi、Atsuko Nishino、Hoyoku Nishino

  DOI：10.1016/0031-9422(96)00030-1

  日期：1996.7

  3-O-O-alpha-L -rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl -(1-->4)]-beta-D-galactopyranoside}, respectively. The isolated saponins and their derivatives were examined for inhibitory activity on 12-O-tetradecanoylphorbor-13-acetate-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to find new antitumour-promoter compounds.

  从玉簪的地下部分分离出三种新的螺甾醇皂苷和两种新的呋甾醇皂苷。它们的结构被确定为 (25R)-5 alpha-spirostane-2 alpha, 3 beta-diol (gitogenin) 3-O-O-alpha-L -rhamnopyranosyl-(1-->2)-beta-D-吡喃半乳糖苷}，gitogenin 3-O-O-alpha-L-rhamnopyranosyl-(1-->2) -O-[β-D-吡喃葡萄糖基-(1-->4)]-β-D-吡喃半乳糖苷-， (25R)-5 alpha-spirostan-3 beta-ol (tigogenin) 3-O-O-alpha-L-rhamnopyranosyl-(1-->2) -O-[beta-D-glupyranosyl-(1-- >4)]-β-D-吡喃半乳糖苷-, 26-O-β-D-吡喃葡萄糖基-22-O-甲基-(25R)-5