coreajaponins A | 1297292-55-7

• 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: coreajaponins A
• 英文别名: (25R)-26-[(β-D-glucopyranosyl)oxy]-22α-hydroxyfurost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1->2)-O-[α-L-arabinopyranosyl-(1->4)]-β-D-glucopyranoside；coreajaponin A；(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,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 1297292-55-7
• 化学式: C₅₀H₈₂O₂₂
• 分子量: 1035.19
• InChiKey: SVCOZYRNFNGOCW-SHFRDDTKSA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Predicted)

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：

  甲醇 、 coreajaponins A 反应 15.0h， 生成 (25R)-26-[(β-D-glucopyranosyl)oxy]-22α-methoxyfurost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1->2)-O-[α-L-arabinopyranosyl-(1->4)]-β-D-glucopyranoside
  参考文献：
  名称：

  Furostanol saponins from the rhizomes of Dioscorea japonica and their effects on NGF induction

  摘要：

  The rhizome of Dioscorea japonica is a food and medicinal source known as 'San Yak' in Korea. Two new furostanol saponins, coreajaponins A (1) and B (2), together with 10 known compounds (3-12) were isolated from the rhizomes of D. japonica. Their structures were determined by spectroscopic methods, including 1D and 2D NMR techniques, HRMS, and chemical methods. Nerve growth factor (NGF), a crucial factor for neuronal survival and differentiation, can potentially improve neurodegenerative diseases and diabetic polyneuropathy. We evaluated the effects of isolates (1-12) on NGF induction in a C6 rat glioma cell line. Coreajaponin B (2) upregulated NGF content without significant cell toxicity, as did 6, 8, 9, and 11. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.003
• 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-L-arabinopyranosyl)-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63%的产率得到coreajaponins A
  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

• 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。
• Furostanol saponins from the rhizomes of Dioscorea japonica and their effects on NGF induction
  作者：Ki Hyun Kim、Min Ah Kim、Eunjung Moon、Sun Yeou Kim、Sang Zin Choi、Mi Won Son、Kang Ro Lee

  DOI：10.1016/j.bmcl.2011.02.003

  日期：2011.4

  The rhizome of Dioscorea japonica is a food and medicinal source known as 'San Yak' in Korea. Two new furostanol saponins, coreajaponins A (1) and B (2), together with 10 known compounds (3-12) were isolated from the rhizomes of D. japonica. Their structures were determined by spectroscopic methods, including 1D and 2D NMR techniques, HRMS, and chemical methods. Nerve growth factor (NGF), a crucial factor for neuronal survival and differentiation, can potentially improve neurodegenerative diseases and diabetic polyneuropathy. We evaluated the effects of isolates (1-12) on NGF induction in a C6 rat glioma cell line. Coreajaponin B (2) upregulated NGF content without significant cell toxicity, as did 6, 8, 9, and 11. (C) 2011 Elsevier Ltd. All rights reserved.