4-methoxy-2,5,9R-trihydroxy-9,10-dihydrophenanthrene 2-O-β-D-glucopyranoside | 1469730-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxy-2,5,9R-trihydroxy-9,10-dihydrophenanthrene 2-O-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[[(9R)-5,9-dihydroxy-4-methoxy-9,10-dihydrophenanthren-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1469730-22-0
• 化学式: C₂₁H₂₄O₉
• 分子量: 420.416
• InChiKey: LNGRTDFDFZLFCC-UXZCKQNASA-N

物化性质

• 沸点：
  760.7±60.0 °C(Predicted)
• 密度：
  1.542±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：

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

  Anti-inflammatory phenanthrene derivatives from stems of Dendrobium denneanum

  摘要：

  Cultivated Dendrobium denneanum has been substituted for other endangered Dendrobium species in recent years, but there have been few studies regarding either its chemical constituents or pharmacological effects. In this study, three phenanthrene glycosides, three 9,10-dihydrophenanthrenes, two 9,10-dihydrophenanthrenes glycosides, and four known phenanthrene derivatives, were isolated from the stems of D. denneanum. Their structures were elucidated on the basis of MS and NMR spectroscopic data. Ten compounds were found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse macrophage RAW264.7 cells with IC50 values of 0.7-41.5 mu M, and exhibited no cytotoxicity in RAW264.7, HeLa, or HepG2 cells. Additionally, it was found that 2,5-dihydroxy-4-methoxy-phenanthrene 2-O-beta-D-glucopyranoside, and 5-methoxy-2,4,7,9S-tetrahydroxy-9,10-dihydrophenanthrene suppressed LPS-induced expression of inducible NO synthase (iNOS) inhibited phosphorylation of p38, JNK as well as mitogen-activated protein kinase (MAPK), and inhibitory kappa B-alpha (I kappa B alpha). This indicated that both compounds exert anti-inflammatory effects by inhibiting MAPKs and nuclear factor kappa B (NF-kappa B) pathways. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.008

文献信息

• Anti-inflammatory phenanthrene derivatives from stems of Dendrobium denneanum
  作者：Yuan Lin、Fei Wang、Li-juan Yang、Ze Chun、Jin-ku Bao、Guo-lin Zhang

  DOI：10.1016/j.phytochem.2013.08.008

  日期：2013.11

  Cultivated Dendrobium denneanum has been substituted for other endangered Dendrobium species in recent years, but there have been few studies regarding either its chemical constituents or pharmacological effects. In this study, three phenanthrene glycosides, three 9,10-dihydrophenanthrenes, two 9,10-dihydrophenanthrenes glycosides, and four known phenanthrene derivatives, were isolated from the stems of D. denneanum. Their structures were elucidated on the basis of MS and NMR spectroscopic data. Ten compounds were found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse macrophage RAW264.7 cells with IC50 values of 0.7-41.5 mu M, and exhibited no cytotoxicity in RAW264.7, HeLa, or HepG2 cells. Additionally, it was found that 2,5-dihydroxy-4-methoxy-phenanthrene 2-O-beta-D-glucopyranoside, and 5-methoxy-2,4,7,9S-tetrahydroxy-9,10-dihydrophenanthrene suppressed LPS-induced expression of inducible NO synthase (iNOS) inhibited phosphorylation of p38, JNK as well as mitogen-activated protein kinase (MAPK), and inhibitory kappa B-alpha (I kappa B alpha). This indicated that both compounds exert anti-inflammatory effects by inhibiting MAPKs and nuclear factor kappa B (NF-kappa B) pathways. (C) 2013 Elsevier Ltd. All rights reserved.