3,4,5-trihydroxy-2-methoxy-9,10-dihydrophenanthrene-4-O-β-D-glucopyranoside | 1365254-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5-trihydroxy-2-methoxy-9,10-dihydrophenanthrene-4-O-β-D-glucopyranoside
• 英文别名: marylaurencinoside A；(2S,3R,4S,5S,6R)-2-[(3,5-dihydroxy-2-methoxy-9,10-dihydrophenanthren-4-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1365254-85-8
• 化学式: C₂₁H₂₄O₉
• 分子量: 420.416
• InChiKey: CAYDEEUWOXCJSB-AQZWWPQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,5-trihydroxy-2-methoxy-9,10-dihydrophenanthrene-4-O-β-D-glucopyranoside 在 硫酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 葡萄糖
  参考文献：
  名称：

  Phenanthrene Derivatives from Cymbidium Great Flower Marie Laurencin and Their Biological Activities

  摘要：

  A new phenanthrendione, ephemeranthoquinone B (1), two phenanthrenes, marylaurencinols A (2) and B (3), and a phenanthrene glucoside, marylaurencinoside A (4), Laurencin, along with six known phenanthrenes, 5-10. The were isolated from the roots of Cymbidium Great Flower Marie structures of these compounds were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analysis and chemical degradation. The compounds were tested for antibacterial activities against Bacillus subtilis and Klebsiella pneumoniae and for cytotoxic activity against the human promyelocytic leukemia (HL-60) cell line. Compounds 1, 3, and 6 showed antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 4.88 to 65.10 mu M. Notably, ephemeranthoquinone B (1) had a strong antibacterial effect on B. subtilis. Furthermore, 1 exhibited moderate cytotoxic activity (IC50 2.8 mu M) against HL-60 cells. Compounds 4-9 also showed weak cytotoxic activity against the HL-60 cell line with IC50 values of 19.3-52.4 mu M.

  DOI：

  10.1021/np200788u

文献信息

• Phenanthrene Derivatives from <i>Cymbidium</i> Great Flower Marie Laurencin and Their Biological Activities
  作者：Kazuko Yoshikawa、Takuya Ito、Kanako Iseki、Chihiro Baba、Hiroshi Imagawa、Yasuyuki Yagi、Hiroshi Morita、Yoshinori Asakawa、Sachiko Kawano、Toshihiro Hashimoto

  DOI：10.1021/np200788u

  日期：2012.4.27

  A new phenanthrendione, ephemeranthoquinone B (1), two phenanthrenes, marylaurencinols A (2) and B (3), and a phenanthrene glucoside, marylaurencinoside A (4), Laurencin, along with six known phenanthrenes, 5-10. The were isolated from the roots of Cymbidium Great Flower Marie structures of these compounds were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analysis and chemical degradation. The compounds were tested for antibacterial activities against Bacillus subtilis and Klebsiella pneumoniae and for cytotoxic activity against the human promyelocytic leukemia (HL-60) cell line. Compounds 1, 3, and 6 showed antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 4.88 to 65.10 mu M. Notably, ephemeranthoquinone B (1) had a strong antibacterial effect on B. subtilis. Furthermore, 1 exhibited moderate cytotoxic activity (IC50 2.8 mu M) against HL-60 cells. Compounds 4-9 also showed weak cytotoxic activity against the HL-60 cell line with IC50 values of 19.3-52.4 mu M.