(-)-catechin-8-C-β-D-glucopyranosyl-(4->1)-O-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (-)-catechin-8-C-β-D-glucopyranosyl-(4->1)-O-α-D-glucopyranoside
• 英文别名: (2S,3R)-8-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₂₇H₃₄O₁₆
• 分子量: 614.557
• InChiKey: YFICVQVWJBXLKL-PYSKGHFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  280
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  麦芽糖 、 表儿茶素 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 0.17h， 生成 (-)-catechin-8-C-β-D-glucopyranosyl-(4->1)-O-α-D-glucopyranoside 、 (-)-epicatechin-8-C-β-D-glucopyranosyl-(4->1)-O-α-D-glucopyranoside 、 (-)-catechin-6-C-β-D-glucopyranosyl-(4->1)-O-α-D-glucopyranoside
  参考文献：
  名称：

  Nonenzymatic C-Glycosylation of Flavan-3-ols by Oligo- and Polysaccharides

  摘要：

  Model reactions between the polysaccharide amylose and the polyphenol (-)-epicatechin followed by partial enzymatic hydrolysis of the reaction products formed led to the detection of mono- and oligo-C-glucosylated flavan-3-ols by means of LC-MS/MS experiments. To confirm the structure of these putative flavan-3-ol/oligosaccharide conjugates, (-)-epicatechin was reacted with maltose and maltotriose, respectively, giving rise to a series of previously unreported flavan-3-ol/maltose and flavan-3-ol/maltotriose conjugates, namely, (-)-epicatechin-8-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, (-)-catechin-C- 8-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, (-)-catechin-6-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, (-)-catechin-8-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, (-)-catechin-6-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, and (-)-epicatechin-6/8-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside. Furthermore, quantitative analysis of flavan-3-ol-C-glucosides in an enzymatic total hydrolysate using a newly developed stable isotope dilution assay (SIDA) enabled a first insight into the yield of the formation of polyphenol/polysaccharide cross-links, for example, an amount of 14.0, 9.0, and 0.15 mu mol of flavan-3-ol-6-C-beta-D-glucopyranoside, flavan-3-ol-8-C-beta-D-glucopyranoside, and flavan-3-ol-6-C,8-C- beta-D-glucopyranoside were per mmol (-)-epicatechin when reacted with amylose.

  DOI：

  10.1021/jf0719508

文献信息

• Nonenzymatic <i>C</i>-Glycosylation of Flavan-3-ols by Oligo- and Polysaccharides
  作者：Timo Stark、Daniela Keller、Kerstin Wenker、Hedda Hillmann、Thomas Hofmann

  DOI：10.1021/jf0719508

  日期：2007.11.1

  Model reactions between the polysaccharide amylose and the polyphenol (-)-epicatechin followed by partial enzymatic hydrolysis of the reaction products formed led to the detection of mono- and oligo-C-glucosylated flavan-3-ols by means of LC-MS/MS experiments. To confirm the structure of these putative flavan-3-ol/oligosaccharide conjugates, (-)-epicatechin was reacted with maltose and maltotriose, respectively, giving rise to a series of previously unreported flavan-3-ol/maltose and flavan-3-ol/maltotriose conjugates, namely, (-)-epicatechin-8-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, (-)-catechin-C- 8-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, (-)-catechin-6-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, (-)-catechin-8-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, (-)-catechin-6-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside, and (-)-epicatechin-6/8-C-beta-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranosyl-(4 -> 1)-O-alpha-D-glucopyranoside. Furthermore, quantitative analysis of flavan-3-ol-C-glucosides in an enzymatic total hydrolysate using a newly developed stable isotope dilution assay (SIDA) enabled a first insight into the yield of the formation of polyphenol/polysaccharide cross-links, for example, an amount of 14.0, 9.0, and 0.15 mu mol of flavan-3-ol-6-C-beta-D-glucopyranoside, flavan-3-ol-8-C-beta-D-glucopyranoside, and flavan-3-ol-6-C,8-C- beta-D-glucopyranoside were per mmol (-)-epicatechin when reacted with amylose.