α-D-maltosyl-(1⤏4)piceid | 1388012-60-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: α-D-maltosyl-(1⤏4)piceid
• CAS: 1388012-60-9
• 化学式: C₃₂H₄₂O₁₈
• 分子量: 714.675
• InChiKey: FFOHSSCRXOXWTG-GGFKGIIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  298.14
• 氢给体数：
  12.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  α-D-maltosyl-(1⤏4)piceid 以 aq. buffer 为溶剂， 反应 0.5h， 生成 glucose 、 虎杖甙
  参考文献：
  名称：

  Enzymatic Synthesis of Piceid Glucosides Using Maltosyltransferase from Caldicellulosiruptor bescii DSM 6725

  摘要：

  Piceid is widely used in food, cosmetics, and pharmaceuticals because of its therapeutic benefits. However, the use of piceid as a drug is limited because of its low solubility. To increase solubility, we synthesized piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii. The MTase gene was cloned and expressed in Escherichia coli. The enzyme had a unique transfer specificity to the transfer of maltosyl units. Four piceid transglycosylation products were present and identified by thin-layer chromatography and recycling preparative high-performance liquid chromatography. The major product was purified by C-18 and gel filtration chromatography, and its molecular structure was determined using nuclear magnetic resonance spectroscopy to be alpha-D-maltosyl-(1 -> 4)-piceid. The solubility of maltosyl piceid was 8.54 x 10(3) and 1.86 x 10(3) times those of natural resveratrol and piceid, respectively, suggesting that the transglycosylation greatly increased the water solubility. This suggests that dietary intake of this compound can enhance the bioavailability of resveratrol in the human body.

  DOI：

  10.1021/jf302127a
• 作为产物：
  描述：

  麦芽三糖 、 虎杖甙 在 Caldicellulosiruptor bescii DSM 6725 maltosyltransferase 作用下， 以 aq. buffer 为溶剂， 反应 0.83h， 生成 α-D-maltosyl-(1⤏4)piceid
  参考文献：
  名称：

  Enzymatic Synthesis of Piceid Glucosides Using Maltosyltransferase from Caldicellulosiruptor bescii DSM 6725

  摘要：

  Piceid is widely used in food, cosmetics, and pharmaceuticals because of its therapeutic benefits. However, the use of piceid as a drug is limited because of its low solubility. To increase solubility, we synthesized piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii. The MTase gene was cloned and expressed in Escherichia coli. The enzyme had a unique transfer specificity to the transfer of maltosyl units. Four piceid transglycosylation products were present and identified by thin-layer chromatography and recycling preparative high-performance liquid chromatography. The major product was purified by C-18 and gel filtration chromatography, and its molecular structure was determined using nuclear magnetic resonance spectroscopy to be alpha-D-maltosyl-(1 -> 4)-piceid. The solubility of maltosyl piceid was 8.54 x 10(3) and 1.86 x 10(3) times those of natural resveratrol and piceid, respectively, suggesting that the transglycosylation greatly increased the water solubility. This suggests that dietary intake of this compound can enhance the bioavailability of resveratrol in the human body.

  DOI：

  10.1021/jf302127a