leonoside E | 1360075-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: leonoside E
• 英文别名: leonosides E；2-(3-methoxyl-4-hydroxyphenyl)ethyl-O-α-L-arabinopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranoside；(2S,3R,4S,5S)-2-[(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 1360075-77-9
• 化学式: C₂₆H₄₀O₁₆
• 分子量: 608.594
• InChiKey: IAANPVYFEGUURA-LNQUZLCYSA-N

物化性质

• 沸点：
  883.9±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  247
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  leonoside E 在 硫酸 、 水 作用下， 反应 2.0h， 生成 D-葡萄糖 、 L-rhamnopyranose
  参考文献：
  名称：

  Hepatoprotective glycosides from Leonurus japonicus Houtt.

  摘要：

  Two new phenylethanoid glycosides 1 and 2 named leonoside E and leonoside F, and one new sesquiterpene glycoside (3) identified as 7 alpha (H)-eudesmane-4,11 (12)-diene-3-one-2 beta-hydroxy-13-beta-D-glucopyranoside, together with seven known glycosides (4-10), were isolated from the aerial part of Leonurus japonicus Houtt. Their structures were elucidated on the basis of spectroscopic data and chemical evidence. When tested in in vitro assays, compounds 1, 2, 4, and 6 exhibited potent hepatoprotective activity against D-galactosamine-induced toxicity in HL-7702 cells at concentration of 1 x 10(-5) M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.10.034
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1→2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2,4,6-tri-O-acetyl-D-glucopyranosyl trichloroacetimidate 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 leonoside E
  参考文献：
  名称：

  Synthesis of Leonosides E and F derived from Leonurus japonicas Houtt

  摘要：

  Leonosides E and F, two natural phenylethanoid glycosides derived from Leonurus japonicas Houtt, which bear different trisaccharide moieties-one linear and one branched, were totally synthesized via a direct transglycosylation strategy. After trisaccharyl trichloroacetimidates 3 and 4 were prepared as glycosyl donors, they were coupled with the homovanillyl aglycon via silver triflate-promoted transglycosylation to successfully furnish the fully protected glycosides, which were globally deprotected to afford the target molecules in 6.77% and 10.08% overall yields for the longest linear synthetic sequence starting from 6 and 14. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.07.012

文献信息

• Remote Activation of Disarmed Thioglycosides in Latent-Active Glycosylation via Interrupted Pummerer Reaction
  作者：Xiong Xiao、Yueqi Zhao、Penghua Shu、Xiang Zhao、Yan Liu、Jiuchang Sun、Qian Zhang、Jing Zeng、Qian Wan

  DOI：10.1021/jacs.6b08305

  日期：2016.10.12

  yields. Meanwhile, observation of thiosulfinate, thiosulfonate, and disulfide suggested that the leaving group was activated via an interrupted Pummerer reaction. The disarmed SPSB thioglycosyl donors could be selectively activated in the presence of various thioglycosides with remote activation mode. Finally, two natural hepatoprotective glycosides, Leonoside E and Leonuriside B, were efficiently synthesized

  S-糖苷，即 S-2-(2-丙硫基) 苄基 (SPTB) 糖苷，通过简单的选择性氧化被转化为相应的氧化糖基供体 S-2-(2-丙基亚磺酰基) 苄基 (SPSB) 糖苷。用三氟甲磺酸酐处理解除武装的 SPSB 供体和各种受体，以良好到极好的产率提供所需的糖苷。同时，对硫代亚磺酸盐、硫代磺酸盐和二硫化物的观察表明离去基团是通过中断的普默勒反应激活的。解除武装的 SPSB 硫糖基供体可以在各种硫糖苷的存在下以远程激活模式被选择性地激活。最后，使用这种新开发的方法以收敛的方式有效地合成了两种天然的保肝糖苷，Leonoside E 和 Leonuriside B。
• Synthesis of Leonosides E and F derived from Leonurus japonicas Houtt
  作者：Guofeng Gu、Yisheng Zhao、Zhongwu Guo

  DOI：10.1016/j.carres.2013.07.012

  日期：2013.10

  Leonosides E and F, two natural phenylethanoid glycosides derived from Leonurus japonicas Houtt, which bear different trisaccharide moieties-one linear and one branched, were totally synthesized via a direct transglycosylation strategy. After trisaccharyl trichloroacetimidates 3 and 4 were prepared as glycosyl donors, they were coupled with the homovanillyl aglycon via silver triflate-promoted transglycosylation to successfully furnish the fully protected glycosides, which were globally deprotected to afford the target molecules in 6.77% and 10.08% overall yields for the longest linear synthetic sequence starting from 6 and 14. (C) 2013 Elsevier Ltd. All rights reserved.
• Hepatoprotective glycosides from Leonurus japonicus Houtt.
  作者：Yixiu Li、Zhong Chen、Ziming Feng、Yanan Yang、Jianshuang Jiang、Peicheng Zhang

  DOI：10.1016/j.carres.2011.10.034

  日期：2012.2

  Two new phenylethanoid glycosides 1 and 2 named leonoside E and leonoside F, and one new sesquiterpene glycoside (3) identified as 7 alpha (H)-eudesmane-4,11 (12)-diene-3-one-2 beta-hydroxy-13-beta-D-glucopyranoside, together with seven known glycosides (4-10), were isolated from the aerial part of Leonurus japonicus Houtt. Their structures were elucidated on the basis of spectroscopic data and chemical evidence. When tested in in vitro assays, compounds 1, 2, 4, and 6 exhibited potent hepatoprotective activity against D-galactosamine-induced toxicity in HL-7702 cells at concentration of 1 x 10(-5) M. (C) 2011 Elsevier Ltd. All rights reserved.