1'-O-((E)-3-O-β-D-glucopyranosyl-caffeoyl) α-L-xylopyranosyl-(4''-2')-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1'-O-((E)-3-O-β-D-glucopyranosyl-caffeoyl) α-L-xylopyranosyl-(4''-2')-β-D-glucopyranoside
• 英文别名: hydrangeifolin II；[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3S,4S,5S,6R)-4,5,6-trihydroxyoxan-3-yl]oxyoxan-2-yl] (E)-3-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoate
• 化学式: C₂₆H₃₆O₁₈
• 分子量: 636.561
• InChiKey: ULXNZIXJJLKCPD-JSPXEMGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  295
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1'-O-((E)-3-O-β-D-glucopyranosyl-caffeoyl) α-L-xylopyranosyl-(4''-2')-β-D-glucopyranoside 在 盐酸 作用下， 反应 0.5h， 以3.5 mg的产率得到TRANS-咖啡酸
  参考文献：
  名称：

  Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae)

  摘要：

  Phenylpropanoid glycosides, 1 '-O-benzyl-alpha-(L)-rhamnopyranosyl-(1 ''-> 6 ')-beta-(D)-glucopyranoside (1) and alpha-(L)-Xylopyranosyl(4 '', 2 ')-(3-O-beta-(D)-glucopyranosyl)-1 '-O-E-caffeoyl-beta-(D)-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl- beta-(D)-glucopyrano side (3), 1-O-(E)-caffeoyl-beta-(D)-glucopyranoside (4) and 1-O-(E)-feruloyl-beta-(D)-glucopyranoside (5), were isolated from leaves of Coussarea hydrangeifolia. Their structures were determined by IR, HRESIMS, and I D and 2D NMR experiments, and their antioxidant activities, evaluated by assaying the free radical scavenging capacity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical as substrate. The antioxidant activities of 3 and 4 (IC50 values of 15.0 and 19.2 mu M, respectively) were comparable to that of the standard positive control caffeic acid, whilst 2 and 5 were only weakly active and 1 was inactive. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2005.06.019

文献信息

• Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae)
  作者：Lidilhone Hamerski、Mauro Dionei Bomm、Dulce Helena Siqueira Silva、Maria Cláudia Marx Young、Maysa Furlan、Marcos Nogueira Eberlin、Ian Castro-Gamboa、Alberto José Cavalheiro、Vanderlan da Silva Bolzani

  DOI：10.1016/j.phytochem.2005.06.019

  日期：2005.8

  Phenylpropanoid glycosides, 1 '-O-benzyl-alpha-(L)-rhamnopyranosyl-(1 ''-> 6 ')-beta-(D)-glucopyranoside (1) and alpha-(L)-Xylopyranosyl(4 '', 2 ')-(3-O-beta-(D)-glucopyranosyl)-1 '-O-E-caffeoyl-beta-(D)-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl- beta-(D)-glucopyrano side (3), 1-O-(E)-caffeoyl-beta-(D)-glucopyranoside (4) and 1-O-(E)-feruloyl-beta-(D)-glucopyranoside (5), were isolated from leaves of Coussarea hydrangeifolia. Their structures were determined by IR, HRESIMS, and I D and 2D NMR experiments, and their antioxidant activities, evaluated by assaying the free radical scavenging capacity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical as substrate. The antioxidant activities of 3 and 4 (IC50 values of 15.0 and 19.2 mu M, respectively) were comparable to that of the standard positive control caffeic acid, whilst 2 and 5 were only weakly active and 1 was inactive. (c) 2005 Elsevier Ltd. All rights reserved.