6-hydroxy-galanthindole 6-O-[α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside]

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 6-hydroxy-galanthindole 6-O-[α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside]
• 英文别名: 6-hydroxy-galanthindolyloside B；(2S,3R,4R,5R,6R)-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[7-[6-(hydroxymethyl)-1,3-benzodioxol-5-yl]-1-methylindol-6-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• 化学式: C₂₉H₃₅NO₁₃
• 分子量: 605.596
• InChiKey: IXECJUBVZQTAPE-JOWZXHQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  202
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-hydroxy-galanthindole 6-O-[α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside] 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 L-鼠李糖 、 葡萄糖 、 7-(6'-(hydroxymethyl)benzo[d][1',3']dioxol-5'-yl)-1-methyl-1H-indol-6-ol
  参考文献：
  名称：

  Glycosides of benzodioxole-indole alkaloids from Narcissus having axial chirality

  摘要：

  Glycosides of benzodioxole-indole alkaloid 6-hydroxy-galanthindole (7-(6'-(hydroxymethyl)benzo[d] [1',3']dioxol-5'-yl)-1-methyl-1H-indol-6-ol) having axial chirality were isolated from Narcissus cultivar 'Dutch Master'. The structure, including absolute configuration, was determined by means of extensive spectroscopic data such as UV, IR, CD, MS, 1D and 2D NMR spectra, and computational chiroptical methods. The aglycone has a structure containing two aromatic moieties with substituents hindering rotation about the biaryl axis and is connected to a saccharide moiety linked at C-6 and made up of one, two, or three sugars (glucose, alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranose, and trisaccharide ([beta-D-xylopyranosyl(1 -> 2)]-[alpha-L-rhamnopyranosyl-(1 -> 6)]-beta-D-glucopyranose). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.10.016

文献信息

• Glycosides of benzodioxole-indole alkaloids from Narcissus having axial chirality
  作者：Tomáš Řezanka、Pavel Řezanka、Karel Sigler

  DOI：10.1016/j.phytochem.2009.10.016

  日期：2010.2

  Glycosides of benzodioxole-indole alkaloid 6-hydroxy-galanthindole (7-(6'-(hydroxymethyl)benzo[d] [1',3']dioxol-5'-yl)-1-methyl-1H-indol-6-ol) having axial chirality were isolated from Narcissus cultivar 'Dutch Master'. The structure, including absolute configuration, was determined by means of extensive spectroscopic data such as UV, IR, CD, MS, 1D and 2D NMR spectra, and computational chiroptical methods. The aglycone has a structure containing two aromatic moieties with substituents hindering rotation about the biaryl axis and is connected to a saccharide moiety linked at C-6 and made up of one, two, or three sugars (glucose, alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranose, and trisaccharide ([beta-D-xylopyranosyl(1 -> 2)]-[alpha-L-rhamnopyranosyl-(1 -> 6)]-beta-D-glucopyranose). (C) 2009 Elsevier Ltd. All rights reserved.