7-O-glucopyranosyl-isoprunetin | 128856-77-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-O-glucopyranosyl-isoprunetin
• 英文别名: 3-(4-hydroxyphenyl)-5-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 128856-77-9
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: KSVVGBSBNPMXJF-RECXWPGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  7-O-glucopyranosyl-isoprunetin 在 sulfonated graphene oxide nanosheets 作用下， 以 水 、 乙二醇 为溶剂， 反应 8.0h， 以68.8%的产率得到异樱黄素
  参考文献：
  名称：

  基于石墨烯纳米片的高反应性酸催化剂新方法

  摘要：

  氧化石墨烯和磺化氧化石墨烯纳米片的固体酸催化剂已经通过使用改良的悍马和磺化方法制备。物理表征表明，一些官能团如的 COOH， OH， Ò ，和 SO 3 H，分别引入到所合成的纳米片的表面上。在糖苷键的水解和费歇尔酯化反应中评估了合成催化剂的催化性能。实验结果表明，磺化氧化石墨烯的催化活性优于其他具有相同或更高酸强度的固体酸催化剂，并超过了H。2 SO 4的酸强度是磺化氧化石墨烯的9.1倍。高反应性可归因于石墨烯片和其表面上的含氧基团的结合，从而形成疏水腔，这可能有助于催化剂与反应物锚定并促进质子的侵袭。

  DOI：

  10.1002/cctc.201402100
• 作为产物：
  描述：

  isoprunetin-7-O-β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside 在 盐酸 作用下， 生成 7-O-glucopyranosyl-isoprunetin
  参考文献：
  名称：

  Polyprenylated isoflavanone and isoflavonoids from Ormosia henryi and their cytotoxicity and anti-oxidation activity

  摘要：

  A rare naturally-occurring polyprenylated isoflavanone, designated ormosinol (1), and a new isoflavonoid glycoside, named ormosinoside (2), along with 21 known compounds were isolated from the root bark of Ormosia henryi Prain. The structures of compounds 1 and 2 were determined as 5,7,2',4'-tetrahydroxyl-6,8,5'-tri-( gamma,-gamma-dimethylallyl)isoflavanone and isoprunetin-7-O-beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranoside on the basis of a combination of 1D-, 2D-NMR and mass spectroscopic measurements. Compound 1 showed significant anti-oxidation activity against DPPH radicals (IC50 28.5 mu M) and cancer cell line (A549, LAC, and HepG2) growth inhibitory activity with IC50 ranging from 425 to 7.09 mu M, while compound 2 found to be inactive to both testing systems. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2011.10.007

文献信息

• Isoflavonoid glycosides from eriosema tuberosum
  作者：Wei Guang Ma、Yukiharu Fukushi、Kurt Hostettmann、Satoshi Tahara

  DOI：10.1016/s0031-9422(97)00950-3

  日期：1998.9

  Abstract Five isoflavonoid glycosides together with the corresponding aglycones have been isolated from the n-BuOH-soluble fraction of a methanol extract of the roots of Eriosema tuberosum. One compound is new and its structure has been established by spectroscopic analyses and chemical methods as 5-O-methylgenistein 7-O-β- d -apiofuranosyl-(1 → 6)-O-β- d -glucopyranoside.

  摘要 从马尾草根甲醇提取物的 n-BuOH 可溶部分中分离出五种异黄酮苷和相应的苷元。一种化合物是新化合物，其结构已通过光谱分析和化学方法确定为 5-O-甲基染料木黄酮 7-O-β- d -apiofuranosyl-(1 → 6)-O-β- d -glupyranoside。
• A New Approach Towards Acid Catalysts with High Reactivity Based on Graphene Nanosheets
  作者：Zuojun Wei、Yao Yang、Yaxin Hou、Yingxin Liu、Xiaodong He、Shuguang Deng

  DOI：10.1002/cctc.201402100

  日期：2014.8

  catalytic activity of the sulfonated graphene oxide was superior to that of other solid acid catalysts with the same or higher acid strength and has also exceeded that of H2SO4 with 9.1 times of acid strength than that of the sulfonated graphene oxide. The high reactivity can be ascribed to the formation of hydrophobic cavities through the combination of graphene sheet and the oxygen‐containing groups

  氧化石墨烯和磺化氧化石墨烯纳米片的固体酸催化剂已经通过使用改良的悍马和磺化方法制备。物理表征表明，一些官能团如的 COOH， OH， Ò ，和 SO 3 H，分别引入到所合成的纳米片的表面上。在糖苷键的水解和费歇尔酯化反应中评估了合成催化剂的催化性能。实验结果表明，磺化氧化石墨烯的催化活性优于其他具有相同或更高酸强度的固体酸催化剂，并超过了H。2 SO 4的酸强度是磺化氧化石墨烯的9.1倍。高反应性可归因于石墨烯片和其表面上的含氧基团的结合，从而形成疏水腔，这可能有助于催化剂与反应物锚定并促进质子的侵袭。
• Polyprenylated isoflavanone and isoflavonoids from Ormosia henryi and their cytotoxicity and anti-oxidation activity
  作者：Shixiu Feng、Jing Hao、Zhifang Xu、Tao Chen、Samuel X. (Shengxiang) Qiu

  DOI：10.1016/j.fitote.2011.10.007

  日期：2012.1

  A rare naturally-occurring polyprenylated isoflavanone, designated ormosinol (1), and a new isoflavonoid glycoside, named ormosinoside (2), along with 21 known compounds were isolated from the root bark of Ormosia henryi Prain. The structures of compounds 1 and 2 were determined as 5,7,2',4'-tetrahydroxyl-6,8,5'-tri-( gamma,-gamma-dimethylallyl)isoflavanone and isoprunetin-7-O-beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranoside on the basis of a combination of 1D-, 2D-NMR and mass spectroscopic measurements. Compound 1 showed significant anti-oxidation activity against DPPH radicals (IC50 28.5 mu M) and cancer cell line (A549, LAC, and HepG2) growth inhibitory activity with IC50 ranging from 425 to 7.09 mu M, while compound 2 found to be inactive to both testing systems. (C) 2011 Elsevier B.V. All rights reserved.