(R)-2'-hydroxy-justirumalin

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: (R)-2'-hydroxy-justirumalin
• 英文别名: 6-hydroxy-10-(6-hydroxy-1,3-benzodioxol-5-yl)-7H-[2]benzofuro[5,6-g][1,3]benzodioxol-9-one
• 化学式: C₂₀H₁₂O₈
• 分子量: 380.31
• InChiKey: PNHNOLIAAROUDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  10-(6-hydroxy-1,3-benzodioxol-5-yl)-6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-7H-[2]benzofuro[5,6-g][1,3]benzodioxol-9-one 在 hesperidinase 作用下， 反应 48.0h， 以96.1%的产率得到(R)-2'-hydroxy-justirumalin
  参考文献：
  名称：

  Glycosides of arylnaphthalene lignans from Acanthus mollis having axial chirality

  摘要：

  Glycosides of arylnaphthalene lignans having axial chirality were isolated from Acanthus mollis. Owing to the axial chirality, their structure, including absolute configuration, was determined by means of extensive spectroscopic data such as UV, IR, MS, I D and 21) NMR spectra, and computational chiroptical methods. A compound, 2',4-dihydroxyretrohelioxanthin (2'-hydroxy-justirumalin), has a structure containing two aromatic moieties with substituents hindering rotation about the biaryl axis. The aglycone was connected to a saccharide moiety linked at C-4 or C-2' and made up of one or four sugars (rhamnose or quinovose, and tetrasaccharide 4-O-beta-D-xylopyranosyl-(1 ''''-6 '')-O-[beta-D-rhamnopyranosyl-(1 ''''-3 '')]-O-beta-D-apiofuranosyl-(1 ''''-2 '')-O-beta-D-glucopyranoside and quinovose). Two mono- and one tetraglycoside gave positive results in the sea urchin eggs test (Paracentrotus lividus) of cytotoxicity and in a crown gall tumor on potato disks test (Agrobacterium tumefociens). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.05.016

文献信息

• Glycosides of arylnaphthalene lignans from Acanthus mollis having axial chirality
  作者：Tomáš Řezanka、Pavel Řezanka、Karel Sigler

  DOI：10.1016/j.phytochem.2009.05.016

  日期：2009.5

  Glycosides of arylnaphthalene lignans having axial chirality were isolated from Acanthus mollis. Owing to the axial chirality, their structure, including absolute configuration, was determined by means of extensive spectroscopic data such as UV, IR, MS, I D and 21) NMR spectra, and computational chiroptical methods. A compound, 2',4-dihydroxyretrohelioxanthin (2'-hydroxy-justirumalin), has a structure containing two aromatic moieties with substituents hindering rotation about the biaryl axis. The aglycone was connected to a saccharide moiety linked at C-4 or C-2' and made up of one or four sugars (rhamnose or quinovose, and tetrasaccharide 4-O-beta-D-xylopyranosyl-(1 ''''-6 '')-O-[beta-D-rhamnopyranosyl-(1 ''''-3 '')]-O-beta-D-apiofuranosyl-(1 ''''-2 '')-O-beta-D-glucopyranoside and quinovose). Two mono- and one tetraglycoside gave positive results in the sea urchin eggs test (Paracentrotus lividus) of cytotoxicity and in a crown gall tumor on potato disks test (Agrobacterium tumefociens). (C) 2009 Elsevier Ltd. All rights reserved.