(3R)-(+)-isomucronulatol-2'-O-β-D-glucopyranoside

• 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: (3R)-(+)-isomucronulatol-2'-O-β-D-glucopyranoside
• 化学式: C₂₃H₂₈O₁₀
• 分子量: 464.469
• InChiKey: PTMFWXXHLUSFEC-AWAQQNJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  147.3
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3R)-(+)-isomucronulatol-2'-O-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 葡萄糖 、 (3R)-7,2'-二羟基-3',4'-二甲氧基异黄烷
  参考文献：
  名称：

  Nitric oxide inhibitory flavonoids from traditional Chinese medicine formula Baoyuan Decoction

  摘要：

  Three new flavonoid glycosides, (3R)-(+)-isomucronulatol-2'-O-beta-D-glucopyranoside (I), (3R)-(-)-isomucronulatol-7-O-beta-D-apiofuranosyl(1 --> 2)-beta-D-glucopyranoside (2), and (2S)-(-)-7,8-dihydroxylflavanone-4'-O-beta-D-apiofuranosyl(1 --> 2)-beta-D-glucopyranoside (3), along with eight flavanones (4, 8, 10, 12, 15, 16, 21, and 24), four isoflavones (5, 11, 13, and 23), four chalcones (6, 14, 17, and 18), two isoflavans (19-20), one flavone (7), one flavonol (9), and one dihydrochalcone (22) were isolated from Baoyuan Decoction (BYD), a traditional Chinese medicine formula. The structures of the new compounds were established by detailed analysis of NMR and HRESIMS spectroscopic data, and their absolute configurations were determined by electronic circular dichroism (ECD) data. The inhibitory effects of the isolates were evaluated on nitric oxide production in lipopolysaccharide activated RAW 264.7 macrophage cells. Compounds 6, 9, and 10 showed the significant inhibitory activities, with IC50 values of 1.4, 13.8, and 9.3 mu M, respectively, comparable to or even better than the positive control, quercetin (IC50, 16.5 mu M). The assignment of these isolated flavonoids was achieved using UPLC-Q-trap-MS, and the results suggested that they were originated from Astragalus membranaceus and Glycyrrhiza uralensis. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2015.04.011

文献信息

• Nitric oxide inhibitory flavonoids from traditional Chinese medicine formula Baoyuan Decoction
  作者：Xiaoli Ma、Qian Yu、Xiaoyu Guo、Kewu Zeng、Mingbo Zhao、Pengfei Tu、Yong Jiang

  DOI：10.1016/j.fitote.2015.04.011

  日期：2015.6

  Three new flavonoid glycosides, (3R)-(+)-isomucronulatol-2'-O-beta-D-glucopyranoside (I), (3R)-(-)-isomucronulatol-7-O-beta-D-apiofuranosyl(1 --> 2)-beta-D-glucopyranoside (2), and (2S)-(-)-7,8-dihydroxylflavanone-4'-O-beta-D-apiofuranosyl(1 --> 2)-beta-D-glucopyranoside (3), along with eight flavanones (4, 8, 10, 12, 15, 16, 21, and 24), four isoflavones (5, 11, 13, and 23), four chalcones (6, 14, 17, and 18), two isoflavans (19-20), one flavone (7), one flavonol (9), and one dihydrochalcone (22) were isolated from Baoyuan Decoction (BYD), a traditional Chinese medicine formula. The structures of the new compounds were established by detailed analysis of NMR and HRESIMS spectroscopic data, and their absolute configurations were determined by electronic circular dichroism (ECD) data. The inhibitory effects of the isolates were evaluated on nitric oxide production in lipopolysaccharide activated RAW 264.7 macrophage cells. Compounds 6, 9, and 10 showed the significant inhibitory activities, with IC50 values of 1.4, 13.8, and 9.3 mu M, respectively, comparable to or even better than the positive control, quercetin (IC50, 16.5 mu M). The assignment of these isolated flavonoids was achieved using UPLC-Q-trap-MS, and the results suggested that they were originated from Astragalus membranaceus and Glycyrrhiza uralensis. (C) 2015 Elsevier B.V. All rights reserved.