26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β,20α,26-triol 3-O-β-D-xylopyranosyl(1->4)-[α-L-rhamnopyranosyl(1->2)]-β-D-glucopyranoside | 1383540-06-4

• 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: 26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β,20α,26-triol 3-O-β-D-xylopyranosyl(1->4)-[α-L-rhamnopyranosyl(1->2)]-β-D-glucopyranoside
• 英文别名: pallidifloside I；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-16-yl]oxy]-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 1383540-06-4
• 化学式: C₅₀H₈₂O₂₂
• 分子量: 1035.19
• InChiKey: SVCOZYRNFNGOCW-ZHRNGQKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  72
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  346
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β,20α,26-triol 3-O-β-D-xylopyranosyl(1->4)-[α-L-rhamnopyranosyl(1->2)]-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 8.0h， 生成
  参考文献：
  名称：

  Steroidal saponins from Fritillaria pallidiflora Schrenk

  摘要：

  Five new steroidal saponins, Pallidifloside D (1), Pallidifloside E (2), Pallidifloside G (5), Pallidifloside H (6) and Pallidifloside I (7), together with seven other steroidal saponins (3,4,8-12) were isolated from the dry bulbs of Fritillaria pallidiflora Schrenk. Their structures were established by spectroscopic techniques (IR, MS, 1D and 2D NMR) and chemical means. The isolated steroidal saponins were evaluated for cyotoxic activity against human C6 brain gliomas and Hela cervix cancer cell lines using MTT assays. Compounds 1, 10, 11, 12 showed cytotoxicity against C6 and Bela cell lines with IC50 values in the range of 5.1-75.8 mu M. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2012.03.008
• 作为产物：
  描述：

  (25R)-26-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-16β-acetoxy-22-oxo-cholest-5-en-3β-yl-O-[2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-4-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-6-O-benzoyl-β-D-glucopyranoside] 在 lithium hydroxide monohydrate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 以62%的产率得到26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β,20α,26-triol 3-O-β-D-xylopyranosyl(1->4)-[α-L-rhamnopyranosyl(1->2)]-β-D-glucopyranoside
  参考文献：
  名称：

  呋喃甾醇糖苷的合成：一种有效的α-葡萄糖苷酶抑制剂的发现†

  摘要：

  已经开发了一种方便的合成糠醛甾醇糖苷的方法，该方法具有高效掺入26- O- β- D-吡喃葡萄糖基单元和易于形成半缩酮环E的特点。七种糠醛甾醇皂苷的总合成包括fun素B使用容易获得的16β-乙酰氧基-22-氧代-26-羟基胆甾醇衍生物作为有效的构建基块可有效地获得，，，，，、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、还评估了合成皂苷的α-葡萄糖苷酶抑制活性，这表明fun药苷B是开发α-葡萄糖苷酶抑制剂的高度潜在的先导。

  DOI：

  10.1039/c6ob01766e

文献信息

• Steroidal saponins from Fritillaria pallidiflora Schrenk
  作者：Shuo Shen、Guoyu Li、Jian Huang、Chaojun Chen、Bu Ren、Ga Lu、Yong Tan、Jiaxu Zhang、Xian Li、Jinhui Wang

  DOI：10.1016/j.fitote.2012.03.008

  日期：2012.6

  Five new steroidal saponins, Pallidifloside D (1), Pallidifloside E (2), Pallidifloside G (5), Pallidifloside H (6) and Pallidifloside I (7), together with seven other steroidal saponins (3,4,8-12) were isolated from the dry bulbs of Fritillaria pallidiflora Schrenk. Their structures were established by spectroscopic techniques (IR, MS, 1D and 2D NMR) and chemical means. The isolated steroidal saponins were evaluated for cyotoxic activity against human C6 brain gliomas and Hela cervix cancer cell lines using MTT assays. Compounds 1, 10, 11, 12 showed cytotoxicity against C6 and Bela cell lines with IC50 values in the range of 5.1-75.8 mu M. (C) 2012 Elsevier B.V. All rights reserved.
• Synthesis of furostanol glycosides: discovery of a potent α-glucosidase inhibitor
  作者：Peng Wang、Jiejie Hao、Xiuli Zhang、Cong Wang、Huashi Guan、Ming Li

  DOI：10.1039/c6ob01766e

  日期：——

  A convenient approach to the synthesis of furostanol glycosides has been developed with the features of both highly efficient incorporation of a 26-O-β-D-glucopyranosyl unit and ready formation of hemiketal ring E. The total syntheses of seven furostanol saponins including funlioside B, lilioglycoside, protobioside I, protodioscin, pallidifloside I, coreajaponins A and parisaponin I are efficiently

  已经开发了一种方便的合成糠醛甾醇糖苷的方法，该方法具有高效掺入26- O- β- D-吡喃葡萄糖基单元和易于形成半缩酮环E的特点。七种糠醛甾醇皂苷的总合成包括fun素B使用容易获得的16β-乙酰氧基-22-氧代-26-羟基胆甾醇衍生物作为有效的构建基块可有效地获得，，，，，、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、还评估了合成皂苷的α-葡萄糖苷酶抑制活性，这表明fun药苷B是开发α-葡萄糖苷酶抑制剂的高度潜在的先导。