4-hydroxy-2,7-dimethylnaphthylene-1-O-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-2,7-dimethylnaphthylene-1-O-β-D-glucopyranoside
• 英文别名: 2,7-Dimethyl-1,4-dihydroxynaphthalene 1-O-glucoside；(2S,3R,4S,5S,6R)-2-(4-hydroxy-2,7-dimethylnaphthalen-1-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₂₂O₇
• 分子量: 350.368
• InChiKey: ZMEFPRRKVCVENF-QFXBJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-hydroxy-2,7-dimethylnaphthylene-1-O-β-D-glucopyranoside 在 乙酰氯 作用下， 反应 2.0h， 生成 甲基-Alpha-D-吡喃葡糖苷
  参考文献：
  名称：

  Antimycobacterial 1,4-napthoquinone natural products from Moneses uniflora

  摘要：

  new 1,4-naphthoquinone derivative, 5,8-dihydro-3-hydroxychimaphilin (4) and five known compounds (1, 2 and 5-7) were isolated from an extract of the Canadian medicinal plant Moneses uniflora that significantly inhibited the growth of Mycobacterium tuberculosis H37Ra. The structure of 4 was established through analysis of NMR and MS data and the absolute configuration of the glycone of 5 was determined by chemical transformation and comparison with standards prepared from D- and L-glucose. All compounds isolated were screened against Mycobacterium tuberculosis (H37Ra) and the mammalian HEK 293 cell line and, with the exception of compounds 5 and 7, exhibited marked selectivity in their bioactivity: Compound 1 exhibited potent antimycobacterial activity (IC50 of 5.4 mu M) and moderate cytotoxicity (IC50 of 30 mu M); compounds 2, 4 and 6 showed moderate antimycobacterial activity (IC50 values from 28 to 47 mu M) without affecting the viability of mammalian cells; compound 5 displayed moderate activity in both assays (IC50 values of 44 and 55 mu M respectively); and compound 7 was not active in either assay. These data suggest that the Moneses napthaquinone derivatives elicit biological responses in mycobacterial and mammalian cells through disparate modes of action that warrant further investigation.

  DOI：

  10.1016/j.phytol.2018.07.032

文献信息

• Antimycobacterial 1,4-napthoquinone natural products from Moneses uniflora
  作者：Haoxin Li、Allyson Bos、Stéphanie Jean、Duncan Webster、Gilles A. Robichaud、John A. Johnson、Christopher A. Gray

  DOI：10.1016/j.phytol.2018.07.032

  日期：2018.10

  new 1,4-naphthoquinone derivative, 5,8-dihydro-3-hydroxychimaphilin (4) and five known compounds (1, 2 and 5-7) were isolated from an extract of the Canadian medicinal plant Moneses uniflora that significantly inhibited the growth of Mycobacterium tuberculosis H37Ra. The structure of 4 was established through analysis of NMR and MS data and the absolute configuration of the glycone of 5 was determined by chemical transformation and comparison with standards prepared from D- and L-glucose. All compounds isolated were screened against Mycobacterium tuberculosis (H37Ra) and the mammalian HEK 293 cell line and, with the exception of compounds 5 and 7, exhibited marked selectivity in their bioactivity: Compound 1 exhibited potent antimycobacterial activity (IC50 of 5.4 mu M) and moderate cytotoxicity (IC50 of 30 mu M); compounds 2, 4 and 6 showed moderate antimycobacterial activity (IC50 values from 28 to 47 mu M) without affecting the viability of mammalian cells; compound 5 displayed moderate activity in both assays (IC50 values of 44 and 55 mu M respectively); and compound 7 was not active in either assay. These data suggest that the Moneses napthaquinone derivatives elicit biological responses in mycobacterial and mammalian cells through disparate modes of action that warrant further investigation.