2-[1'(R)-(β-D-glucopyranosyloxy)-4'-methylpent-3'-en-1'-yl]-5,8-dihydroxy-1,4-naphthoquinone | 1388845-74-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-[1'(R)-(β-D-glucopyranosyloxy)-4'-methylpent-3'-en-1'-yl]-5,8-dihydroxy-1,4-naphthoquinone
• 英文别名: shikonin-1'-O-β-D-glucopyranoside
• CAS: 1388845-74-6
• 化学式: C₂₂H₂₆O₁₀
• 分子量: 450.442
• InChiKey: JNCRNECCFFPBMR-ZMXKCYIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  173.98
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2-[1'(R)-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4'-methylpent-3'-en-1'-yl]-5,8-dihydroxy-1,4-naphthoquinone 在 甲醇 、 sodium methylate 作用下， 以75%的产率得到2-[1'(R)-(β-D-glucopyranosyloxy)-4'-methylpent-3'-en-1'-yl]-5,8-dihydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  Glycosylation of Shikonin by the Helferich method

  摘要：

  DOI：

  10.1007/s10600-009-9286-1

文献信息

• Biosynthesis of Novel Shikonin Glucosides by Enzymatic Glycosylation
  作者：Bohan Li、Meilin Zhu、Hui Ma、Tao Ma、Yiqun Dai、Hongmei Li、Yu Li、Cheng-Zhu Wu

  DOI：10.1248/cpb.c19-00284

  日期：2019.10.1

  Shikonin, a natural naphthoquinone, has attracted much attention due to its various biological activities. Two shikonin glucosides, shikonin-1′,8-di-O-β-D-glucopyranoside (1) and shikonin-1′-O-β-D-glucopyranoside (2), were biosynthesized through in vitro enzymatic glycosylation and their structures were elucidated using spectroscopic techniques. The water-solubility and stability of compounds 1 and 2 were significantly higher than those of the parent compound. Furthermore, compound 2 showed moderate cytotoxicity against six cancer cell lines, with IC50 values ranging from 36.10 to 67.47 µM. This research indicated that in vitro enzymatic glycosylation of shikonin is an effective strategy to improve it water solubility and chemical stability.

  志贺宁是一种天然萘醌，因其多种生物活性而备受关注。通过体外酶糖基化技术，生物合成了两种志贺宁葡糖苷，即志贺宁-1′,8-二-O-β-D-吡喃葡萄糖苷（1）和志贺宁-1′-O-β-D-吡喃葡萄糖苷（2），并利用光谱技术阐明了它们的结构。化合物 1 和 2 的水溶性和稳定性明显高于母体化合物。此外，化合物 2 对六种癌细胞株具有中等程度的细胞毒性，IC50 值在 36.10 至 67.47 µM 之间。这项研究表明，对志贺宁进行体外酶糖基化是提高其水溶性和化学稳定性的有效策略。