glycinol-3-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: glycinol-3-O-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[[(6aS,11aS)-6a,9-dihydroxy-6,11a-dihydro-[1]benzofuro[3,2-c]chromen-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₁H₂₂O₁₀
• 分子量: 434.4
• InChiKey: ALOAVZSNXPGUGM-VKPOMUGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  glycinol-3-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以0.95 mg的产率得到3,6,9-三羟基紫檀素
  参考文献：
  名称：

  Anti-osteoporotic and antioxidant activities of chemical constituents of the aerial parts of Ducrosia ismaelis

  摘要：

  A new pterocarpan glycoside, glycino1-3-O-beta-D-glucopyranoside (1), and a new dihydrochalcone glycoside, ismaeloside A (2), were isolated together with 13 known compounds, including several flavonoids (3-8), lignans (9-11), and phenolic compounds (12-15), from the methanol extract of the aerial parts of Ducrosia ismaelis. The chemical structures of these compounds were elucidated from spectroscopic data and by comparison of these data with previously published results. The anti-osteoporotic and antioxidant activities of the isolated compounds were assessed using tartrate-resistant acid phosphatase (TRAP), oxygen radical absorbance capacity (ORAC), and reducing capacity assays. Compound 15 exhibited a dose-dependent inhibition of osteoclastic TRAP activity with a TRAP value of 86.05 +/- 6.55% of the control at a concentration of 10 mu M. Compounds 1,3-5, and 8 showed potent peroxyl radical-scavenging capacities with ORAC values of 22.79 +/- 0.90, 25.57 +/- 0.49, 20.41 +/- 0.63, 26.55 +/- 0.42, and 24.83 +/- 0.12 mu M Trolox equivalents (TE) at 10 mu M, respectively. Only compound 9 was able to significantly reduce Cu(I) with 23.44 mu M TE at a concentration of 10 mu M. All of the aforementioned compounds were isolated for the first time from a Ducrosia species. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.077

文献信息

• Anti-osteoporotic and antioxidant activities of chemical constituents of the aerial parts of Ducrosia ismaelis
  作者：Abubaker M.A. Morgan、Hyun Woo Lee、Sang-Hyun Lee、Chi-Hwan Lim、Hae-Dong Jang、Young Ho Kim

  DOI：10.1016/j.bmcl.2014.05.077

  日期：2014.8

  A new pterocarpan glycoside, glycino1-3-O-beta-D-glucopyranoside (1), and a new dihydrochalcone glycoside, ismaeloside A (2), were isolated together with 13 known compounds, including several flavonoids (3-8), lignans (9-11), and phenolic compounds (12-15), from the methanol extract of the aerial parts of Ducrosia ismaelis. The chemical structures of these compounds were elucidated from spectroscopic data and by comparison of these data with previously published results. The anti-osteoporotic and antioxidant activities of the isolated compounds were assessed using tartrate-resistant acid phosphatase (TRAP), oxygen radical absorbance capacity (ORAC), and reducing capacity assays. Compound 15 exhibited a dose-dependent inhibition of osteoclastic TRAP activity with a TRAP value of 86.05 +/- 6.55% of the control at a concentration of 10 mu M. Compounds 1,3-5, and 8 showed potent peroxyl radical-scavenging capacities with ORAC values of 22.79 +/- 0.90, 25.57 +/- 0.49, 20.41 +/- 0.63, 26.55 +/- 0.42, and 24.83 +/- 0.12 mu M Trolox equivalents (TE) at 10 mu M, respectively. Only compound 9 was able to significantly reduce Cu(I) with 23.44 mu M TE at a concentration of 10 mu M. All of the aforementioned compounds were isolated for the first time from a Ducrosia species. (C) 2014 Elsevier Ltd. All rights reserved.